Updated! Monique - Birth of a Satin Transvestite
Monique - Birth of a Satin Transvestite
Chapter 1 - Start of a Fetish
I have had a strange attraction for satin for as long as I remember. when I was about 4 years old I remember being fascinated by the look and feel of one of my baby sister's dresses, which was of course made of satin. My mum (who left home when I was 5) also had a cream coloured faux fur coat with white satin lining and I remember constantly fondling and stroking and loving the feel of the satin against my skin. When my mum left home, she left some of her old clothes behind and I found the coat while rummaging around our spare room when I was off sick from school. I was still very young, but my dad had to work full time to support me and my older brother, so with my brother at school I was alone in the house.
When I found the coat, I got very excited and aroused. I took it into my bedroom, stripped off and got into bed with the coat. I started touching, then caressing the satin lining and eventually started rubbing it over my naked body and genitals. I think I had my first and several pre puberty non ejaculatory orgasms. Needless to say, I enjoyed it and after did it every chance I could get.
I began to notice that every time I saw a woman wearing satin, especially while watching old movies with the old Hollywood starlets like Monroe, Harlow etc. wearing gorgeous satin dresses and gowns, I would get an erection and would have to disappear and have a session with 'the lining'. One Saturday afternoon when I was about 11, I was watching an old black and white movie in the lounge while my brother was out and dad was in the garden mowing the lawn. Suddenly the lady in the film swept onto the nightclub stage floor and started singing and dancing while wearing an amazingly sexy long slitted black satin dress with long black satin gloves... I actually came in my pants, and not the dry kind either. In fact, it was my first proper ejaculation and at first, I was worried because of the wet, sticky liquid that pumped out. The lady in the film was the actress Rita Hayworth and the movie was 'Gilda', one of my now favorite movie scenes and masturbatory fantasies. (https://www.youtube.com/watch?v=xBILSCFMg8M).
I also remember every Saturday morning having to go shopping for groceries with my dad. Once, while in the Co-op supermarket one day, as we were walking between the aisles, as I turned a corner, I bumped into a red-haired middle-aged woman wearing a 50's style satin dress. It was silvery white, with tiny black polka dots, sleeveless, very tight. I think they call them 'wiggle' dresses now. Apart from the excitement of seeing her in it, I actually felt it as we bumped into each other. Another instant orgasm! Unfortunately, I had to carry on shopping with wet and sticky underpants, however it didn't bother me because I spent the rest of the outing in a daze, thinking about that woman and her amazingly sexy dress. When I got home, I rushed upstairs to my room grabbed the satin lined coat and 'wanked' myself silly.
Of course, as I got older, I learned about masturbation and realized that was in fact what I was doing. However, what I really couldn't understand was that while most boys ‘wanked’ to some form of pornography, I was masturbating to either a piece of satin material or images of women in satin clothing. I did have access to lots of porn. My dad (and later my brother) had a fairly large supply stashed under their beds and although the images did arouse me, nothing quite did it as much as satin. I did however gain a lot of knowledge about sex etc. from reading the articles and stories in the magazines.
I had my first real girlfriend (Jackie) when I was about 12 and we ended up dating for the next 5 years. Due to my exposure to pornography at a fairly early age it wasn't long before we got into heavy petting and had a regular 'nookie' session every Sunday night at my house when we would sneak up to my bedroom and 'listen to records'.
One night when Jackie came round, she was wearing a long-sleeved white satin blouse that did up at the back, that she'd borrowed off her mum and I was previously unaware of. It was the 70’s at the time when retro fashion from the 40/50’s became popular. When she took her coat off and I saw it for the first time my eyes nearly popped out of my head and I got an instant erection. I practically dragged her upstairs and into my room and ravished her severely.
Once Jackie realized how turned on, I got when she wore satin, she got hold of as much as she could, blouses, dresses, skirts, lingerie, often raiding her mom's wardrobe and underwear drawer. Also, when she was about 14, she really got into the retro look and started wearing stockings, stilettos, retro lingerie, Pencil skirts...I loved it. However, her dad was very strict... almost Quaker-esque and didn't approve at all, so she started leaving her stuff at my place. I used to really look forward to Sunday nights.. made having to face Mondays and school bearable.
Unfortunately (or fortunately, depending on how you look at it) one Sunday afternoon when we were both at Jackie's house, just as we were getting ready to leave for my place, her dad noticed her wearing makeup and stopped her coming round. I remember being furious and seething while I walked home alone.
When I got in, I went straight up to my room, put some records on and just laid on my bed looking at the ceiling feeling very angry and sexually frustrated. After a while I started to calm down but still felt really horny which led of course to me fondling myself. For some reason though it wasn't really working but then I remembered Jackie's stash in my cupboard.
Initially I was just going to get something satiny and just strip off and rub the material over my body and crotch until I came... however while going through her stuff I found her red satin suspender belt and black seamed nylon stockings. I felt so horny thinking about her silky legs rubbing against me in those stockings, something compelled me to put them on.
When I did, my cock got even harder, and after a few strokes and almost to the point of cumming, I looked at the other clothes she left there... that blouse. White, smooth, shiny... I didn't think it would fit me and trembling inside with excitement, I slipped it on. I was so surprised that it fit me! Jackie was a size 14, quite a big built girl, not fat. In fact, she was gorgeous...but this fitted me. So, I did the little buttons up on the cuffs and the one behind my neck and just looked at myself in the mirror on my cupboard door and run my hands over the material, over my chest, arms. I even nuzzled my mouth to my shoulder and kissed the satin!
My cock was almost exploding and I hadn't even touched it after putting the blouse on. It was dripping precum and my hand moved down and lightly brushed its tip feeling the warm wet precum on my fingers... then for some unknown reason I put it to my lips...and then got more, all over my fingers and sucked them, licking the juice off... I then started to stroke and BANG! My spunk shot out like water from a fire hose... all over the mirror... when I see the cum running down the mirror something made me go to my knees and lick it off... I'd never tasted my own cum before and was almost overwhelmed as I lapped it up, all the while still pumping cum from my cock.
When I had finished cumming I sat back on the bed. my emotions were all over the place and as I looked at myself in the mirror, I felt sort of disgusted and guilty for what I'd done, so I pulled the clothes off as quickly as I could and shoved them back in the cupboard, almost slamming the door, ashamed of what I'd done. I quickly ran out to the bath room and washed myself. I think I was trying to wash the perversion off. I wasn't a poof! I'm not queer! These things were rushing through my head. I was really worried that there was something terrible wrong with me and vowed to myself I'd never do it again.
So much for that vow... a day or so later, the thoughts wormed their way back into my head... and when they did a warm feeling spread from the pit of my stomach...the stirrings of excitement...my cock tingled at the thought of wearing that satin and stockings etc. again...
As the days went by, the feelings got much stronger and I eventually gave in to my craving again as soon as I got home from school. My Dad was still at work and wouldn't be in for another hour at least so I went to my room, closed the door, stripped off and got the clothes from the wardrobe. this time adding Jackie's silky knickers...she had also left a pair of kitten heels too. Black.. very pointy toes. and... I thought I'd try them on. She was a size 6(UK) and although having ridiculously small feet, I was a size 7 and a 1/2... I still managed to squeeze the shoes on. They were agony but I ignored the pain. I strutted around the room, walking backwards and forwards in front of the mirror, hands on hips, trying to walk with a wiggle like a sexy woman.
My cock was bulging against the silky knickers... and precum was oozing out and soaking them. I stopped in front of the mirror and started to run my hands over the satin, sat on the bed and stroked my hands up my stockings as I'd seen women do in the movies when they're smoothing them... I was so incredibly turned on... I didn't realize it, but I was more turned on then than I would have been if Jackie was there wearing it all for me... needless to say, I masturbated and came profusely.
And this was how it went on...me getting the urge, dressing as soon as I could, masturbating, cumming and feeling terribly guilty afterwards although, the guilt had started to wane gradually as I kind of accepted it was my little secret, and so long as I didn't get caught. where was the harm? I still thought it was wrong on so many levels but I was sort of accepting it was my 'dark side'. As time went on, I managed to get Jackie to buy even more stuff to leave at my house, satin skirts, dresses, lingerie and so on, until I'd built up quite a collection of her clothes in my wardrobe, some of which I still have today!
Jackie and I eventually split up when I was nearing 18. We'd both left school, started working and for reasons I won't go into (nothing to do with my Dark side) went our separate ways. I really missed the female company and the sex, of course, but, huge bonus, she left all her stuff at my place so I was still able to dress up when the urge struck, which it did often. Most of the time it was just random thoughts as I went through my day that would kick it off, but if I saw a woman wearing satin, in real life, on tv, even pictures in magazines and the newspapers (which I started to cut out and collect) I would have to go an 'have a session' as soon as I could.
Eventually I started to accumulate my own supply of clothing in addition to the stuff I’d obtained via Jackie. The first time I actually went and bought something from a shop that sold women's wear, on my own, was odd if not embarrassing. Although I was 'getting to grips' with women's clothing sizes, bra measurements were still a mystery to me. This usually ended up with me asking a shop assistant that old chestnut 'If it didn't fit HER is it ok to bring it back? ' all the while trying to hide my embarrassment, and most of the time, excitement. I'm certain, that no matter how convincing your cover story is, women have a sixth sense about trannies, so every shop assistant in stores where I've bought stuff, has known I was going to go home and dress up in whatever I bought. Ok it was true, but...
All this time I was dressing up, I was meeting girls, going out with them for a few months, even years, all the while managing to hide my secret from them. Oh, they all knew I had a fetish for satin and stockings, I was always very open about that because, after all, I decided I wasn't attracted to a woman UNLESS she would wear satin for me. Sometimes it caused problems but on the whole, it worked out for me.
I got married in 1980 to a girl I had been dating for about 18 months, unfortunately it failed mainly because she started seeing her previous boyfriend so she left me. I was renting a flat then, just literally around the corner from where I used to live. Which was handy as I could go and visit my dad whenever I wanted to. He was living alone now, and I did really feel sorry for him, so I visited almost every day, or he'd visit me. As I mentioned earlier, my dad used to buy lots of girly magazines, mainly Mayfair and Penthouse, which he used to stash under his bed, and he knew I knew they were there so before I even moved out, he'd started letting me read them. I remember way before I'd split from Jackie, still living at home, I read a story in The Penthouse 'forum' about a woman who'd caught her husband wearing her lingerie. I was really surprised when I read it because I, at that time, naively thought I was the only guy in the world that did this. I'd seriously never heard of transvestites, only what we would then call, in the days before the monster known as political correctness appeared, poofs and queers!
While I was reading it, I started getting very turned on, but when it got to the part where she made him dress up for her and then started bringing guys round to fuck in front of her sissy hubby, my cock was like a Trident missile. As the story progressed, it evolved into her making her hubby into a sissy slave and made him start giving her boyfriend's blow jobs and letting them fuck him. That REALLY turned me on!
I'd never even dreamed of having sex with a man and, never, EVER, wanted to. As far as I was concerned, I was completely hetero and would never look at a guy 'sexually' at all, in fact, it was abhorrent and completely disgusting to me.
Why was I getting so turned on? I was so turned on in fact that I came even before finishing the story...although I finished it hundreds of times afterwards.
When I was living on my own, I'd gone round the corner shops to buy some food etc, when I noticed a small magazine on the top shelf of the news wrack, wedged in with the other 'girly' books. I think it was called 'Transworld' or something. I grabbed a 'Forum' mag that was nearby it, and then quickly grabbed the Transworld book too.. and with a bit of sleight of hand managed to tuck it under my shirt and into the front of my trousers without anyone seeing. I paid for my bits and the Forum mag, and walked briskly from the shop, dreading that I was going to get caught...It would have been bad enough getting caught stealing, but caught stealing a Tranny Mag?
When I got back to the flat, I started reading the mag. I was getting more and more turned on, and so I went into my bedroom, stripped off and put on some women's satin Pajamas and a long satin robe and then for some reason, I latched my front door, and went back into the lounge, put some music on then carried on reading the Tranny magazine... getting soooo turned on reading the stories and looking at the photos of real transvestites. Fuck I was so horny. I fantasized about being with one (or more) of them.
Around this time, I'd also got into filming myself on an old black and white video security camera I'd picked up from a boot sale. I had several tapes hidden away of me dressed up, walking around to some sexy music and wanking and, often I used to watch the tapes and masturbate to them. I didn't think that was me being gay, it was just me getting turned on by what I do. I also used to masturbate to videos/movies where there was someone (anyone) wearing satin. The Gilda tape was almost worn out.
Now I was masturbating while looking at TV's. Nope, I'm still not gay, I was telling myself, I'm turned on by these guys dressing...in silky clothes, sometimes with their cocks out... FUCK I want to have sex with them...No, I'm still Not gay!
The truth is I didn't know what I was. Everything I'd read about Transvestites stated that the majority of TV's were 'Straight'... so although I didn't advertise it, I labelled myself secretly as a Transvestite, or 'Cross Dresser', a new term I'd learned. I KNOW I didn't fancy blokes at all, but I had to admit to fancying Transvestites, although they had to be convincing.
I guess I really fancied Transexuals. And, it wasn't long before I was watching TS videos, in fact, to be completely honest, apart from watching lesbians, 'Normal' porn didn't really do a lot for me anymore.
So I was into T-girls as well as women (in satin), guess I was a bit Bi then, something I kept completely to myself.
After I finished reading the Transworld mag, I remembered the Forum I'd bought. Later, when I wasn't in TV mode, I gave it a read and noticed, apart from a few weak stories, it was predominantly a personal or 'contact' mag. For more of a laugh (or curiosity I suppose) I started reading the 'classifieds'. It wasn't long, which surprised me, before I found a TV related ad. And, I started getting turned on reading them...fantasizing a bit.
There were guys looking for TV's, TV's looking for TV's, Couples etc. etc. Yeah I was fantasizing about putting a contact in...but of course I didn't.. not then anyway.
It was much later, in fact, just prior to my second marriage when I actually did. I was dating a girl who lived in Leeds, which as I’m sure you know, is miles away from Basildon. I'd also moved back in with my dad for several reasons, which I won't go into, and was now learning to drive, and working for the Local Council.
Dating someone from Leeds had its disadvantages, but also meant I had plenty of 'me' time at home between 'dates'.
I'd taken to buying loads more women's clothes..99.9 per cent satin clothes that is, and had a huge wardrobe full of it. I hadn't really started to wear make-up when dressed, and I didn't have any wigs yet. I still had my own hair then, although by the age of 23 it had already started to recede. Thanks Genetics. I only had one pair of high heels that I had 'inherited' from Jackie, but used to dress up, almost fully more and more frequently.
My fantasies were also getting more 'Raunchy', generally involving satin clad women, but more frequently, satin clad T-girls. Occasionally, I would also fantasize about being made to suck a guy's cock, although in my fantasy the guy was very vague, no features or anything, just a 'Guy' or more specifically, just a ‘cock’.
As for being fucked, I mean me receiving 'Anal', I was very curious to what it felt like.
I'd occasionally 'fingered' myself while masturbating, but didn't really know what it felt like to have something 'Dick' sized entering me. Until, one day, curiosity got the better of me and I bought my first Vibrator from a lingerie catalogue. I'd started to subscribe to several, originally because of the pictures of women in satin, but also so I could add stuff to my wardrobe via mail order. I also had several 'normal' catalogues on the go, Littlewoods etc. again, originally for the pictures, but then for buying clothes. It was easier than shopping in women's stores but I did actually get addicted to ordering anything satin I could find. And, getting credit was so easy in those days, I did get myself into shit loads of debt. Another tale perhaps.
Anyway, back to the vibrator. When it arrived, I went out and bought some extra batteries, and a small jar of vaseline. I didn't use it right away, I waited until I went to bed that night before opening the box. When I did, I wasn't that impressed by its look. It was one of those cream coloured, unimaginative bullet shaped things, about 7 inches long. I think it was called a 'non-Doctor'. I put the double A batteries in and switched it on...It was quite loud, and I was worried my dad would be able to hear it. It felt weird vibrating in my hand and I moved it under the bedclothes and pressed it against my flacid cock. Hmmmm.. quite nice, my cock started to harden. Yep, it was turning me on alright. I reached down by the side of my bed and picked up the small jar of vaseline. I placed the vibrator between my thighs just so it was touching my cock and squeezed my legs together, holding it in place while I opened the jar. I put two fingers into the jar and then slid my hand under the covers, trying not to get any of the greasy substance on the bed clothes. I moved my hand down until it was close enough to my anus and slid my fingers inside me. I hadn't used any lube when I fingered myself before and was pleasantly surprised when my fingers slid in so easily. I remember gasping as I pushed my fingers in as far as they could go, feeling my cock twitch, I let the vibrator drop as, if it had stayed in contact with my cock, I would have shot my load then and there.
I slowly withdrew my fingers, retrieved the vibrator and proceeded to smother it in vaseline.
Then came the moment of truth, I moved the vibrator and positioned it's tip gently on my tight little hole. Even that was giving me tons of pleasure just feeling the slightly 'tickly' vibes throbbing at my sphincter, and I noticed I was moaning to myself like a porn star.
I slowly slid the slightly cold plastic into me, centimeter by centimeter. My cock was so hard now and I wasn't even touching it.
It hurt at first as I went deeper but I'd lubed it up enough that I could withdraw it easily if it hurt too much. As pleasure overcame pain, I started slowly fucking myself with this plastic battery powered toy...and I was loving it!
I gently touched my cock and was about to start masturbating when BANG! I came! My cock pulsating as I spurted cum after cum into my bedclothes.
When I finally withdrew the vibrator that old feeling of disgust had crept back in... not just for what I was doing but also because not only were my bed clothes covered in spunk, but there was p*o all over the vibrator...and I felt like I URGENTLY needed to poop as I was literally starting to shit myself. I won't go into the details of the clean-up but I will say it wasn't pleasant.
I learnt a couple of lessons there which have stood me in good stead since.
After I had gotten over the disgust feelings, I could categorically say I like having things up my ass, and repeated the process often when having one of my sessions.
Chapter 2 – A Bigger World
So, till trying to convince myself I wasn't gay, I'm fantasizing about gay sex, simulating Anal sex..what's next?
The contact magazine was still tugging at my head, not sure if it was a fully conscious thought yet...but I was intrigued about it and slightly thrilled about the concept of, more or less, anonymous sex with a complete stranger, with no ties...completely secret.. and completely harmless unless someone I knew found out.
With my girlfriend in Leeds, I had plenty of time to myself indulging in my fantasies whilst masturbating. And, I was also having some very erotic dreams while asleep. Although I never thought I would try to make my fantasy real, there of course comes a time when you've got to at least have a peek inside Pandora's box.
I decided to put an ad in a contact mag.
I had at this point bought myself a Polaroid Instant Camera...I don't know if it's a purely Narcissistic thing or what but I enjoyed seeing myself dressed up, so apart from the decidedly bad low quality black and white videos I'd made, Self-timed Polaroid pics were my only option...only because at that stage I was too scared to have normal photos developed in a shop or chemist. I had several what I would call 'pretty good' pics of me dressed. I then went about writing an ad.
'Bi-sexual Satin Clad TV for Same' (Was there such a thing?)
How to start? do I put a name? What should I call myself?
Well, my actual 'male' first name is Nick. I decided to call myself Nikki..
After that I put some stuff about me loving satin and getting horny while wearing and seeing others wearing it, having a large wardrobe, being bi-curious yaddah yaddah..and so on. I sent it to the mag with a couple of my best photos... and waited.
The next issue came out, but my ad wasn't in there. I waited some more.
A few weeks went by, and I started to get letters coming through..ad number at top, then my real name and address written underneath.
With shaking hands, I opened the first letter. There was a photograph of a guy in his 50's wearing a pink, satin bro-peep dress. That was about it. He still had about 2 days growth of beard, bald, a bit on the portly side, but very clearly a man in a dress. Something I hadn't even considered. I try to look as good and as feminine as I can. I had a good figure, and even without make up, with my hair right I still looked pretty convincing, well I thought so anyway. The point is I tried. This bloke clearly hadn't. I thought all TVs were like me and at least tried to look feminine. My heart kind of sank and I didn't even bother to read his letter. It was ripped up and put as far into my bin as I could put it. Ok, there was another...
With dubious thoughts, I opened the other letter. There was no photograph, just a couple of hand written pages. I almost didn't bother to read it as I thought If you can't put a picture of yourself in then you must be truly bad. But I persevered and was quite pleasantly surprised. It was from a guy, who apparently used to dress and didn't have any female clothes now as he'd thrown them out when he was seeing a woman... they'd since split up and he saw my ad in this month's Forum (I didn't even know another copy was out yet).Apparently, He 'Fell in Love' Awwwww... there was a bit more about wanting to dress again and would like to see me, gave me a brief description, which if accurate may look good dressed up, and left a contact number....Hmmmm...
A couple of days passed, a few more letters arrived, but no one I really liked, and a couple were a bit too far away for a meet, for me anyway. I also bought the latest copy of Forum, and lo and behold, there was my ad and picture. There I was dressed in a cream satin blouse and black satin pencil skirt, black stockings and Jackie's black high heels. No make-up but the print was so small you couldn't really tell. I would have contacted me! I also had a look at some of the other contacts in there too..TV contacts, and there were several I would have loved to meet...unfortunately they were in Scotland, Sheffield...none even remotely close enough to me to visit... none that I liked anyway.
I thought about the guy who 'fell in love' with me. I thought maybe if I took a suitcase of satin clothes with me, I could dress him up and...
Fuck it! I decided I'd give him a ring. I didn't have a phone that I would feel comfortable with him ringing me up on out of the blue especially if my dad answered, and mobile phones were still science fiction at that time. So, it would have to be a phone box. Grabbing a pocket full of change I walked round to my corner shop where there was a pay phone. I was shaking when I stood in the phone box. Fear? Nerves? Excitement? Probably a combination of all the above...
I picked up the phone with shaky hand and dialed his number, ready to put the coins in when it started beeping. It rang, and it rang and it rang... FUCK! No answer. I was about to hang up when Beep! Beep! Beep! I frantically albeit clumsily pushed the coin into the slot almost dropping the others when I did. "Hello?" came a voice...
I again have to admit to feeling a wave of multiple emotions all in one go. Surprise, fear, panic and above all else, immense excitement.
My whole body began shaking uncontrollably and I found it almost impossible to speak. My first impulse was to hang up and rush back home but the logical part of my brain kicked in telling me that I really had nothing to lose. The person on the other end of the line had no idea who or where I was, what was the worst thing that could possibly happen? If it all went pear shaped there was no way for him to trace me or anything.
“Hello? Who’s this” The voice came again. After what seemed like several minutes, although in reality was only no more than a couple of seconds, I replied.
“Hi, you answered an ad I put in ‘Forum’? “I stammered out, “My name’s Nikki.”
There was a brief pause, and then, in a voice which was almost as shaky as mine, he said “Oh, erm...Wow!” It suddenly dawned on me that he was probably as freaked out as I was. I nervously chuckled and said “You sound really surprised”.
“To be perfectly honest, I am.” He said. “I didn't really think I would hear back from you. It’s the first time I’ve ever tried something like this.”
“Me too” I said “What made you decide to answer my ad?” My trepidations were starting to dissolve now that I understood that this guy was experiencing feelings and emotions very similar to my own. We were, after all, in opposite ends of the same boat.
“Well, like I said in my letter, I used to dress but haven't in a long while. I started getting the urges again after I split from my girlfriend and more out of curiosity than anything else, picked up a couple of different contact mags,” It sounded as if he was starting to relax too as some of the shakiness seemed to be going out of his voice.
“I sort of trolled through the ads not really thinking any of them were worth bothering with and almost binned the magazines when I found your ad and your picture.”
Bloody hell, I thought. I didn't think there was anything about my ad that made it stand out from the rest. “Not many of the ads had pictures” He continued “which to me, speaks volumes about the advertisers. I mean it doesn't matter what they write about themselves, they can’t be that confident about what they look like if they don’t show a picture. And, even when they do, they usually block out the face or something so you can’t really tell what they look like. You didn't. That and I just thought you looked really sexy” He gave a giggle at that last bit, which I had to say made me feel a bit horny.
Well actually it made me feel a lot horny. I didn't know it at the time, but the thought of someone fancying me dressed up was probably, and still is apart from the satin fetish, my biggest turn on.
We talked for a few more minutes (as long as my money lasted) and after finding out a bit more about each other we decided to meet. He lived in Rayleigh which wasn't that far away from where I lived, and he gave me the address. We set a date and a time and after we said our goodbyes, I hung up the phone and made my way home. I have to admit I was really dizzy with the anticipation and I was in a sort of daze as I walked back to my house.
I can't remember exactly how long it was between the phone call and our actual meeting but suffice to say that time was spent suffering an internal turmoil of various emotions, ranging from blind panic to extreme horniness. I abstained, however, from acting on doing anything about the latter, I.e., dressing up and having a damn good wank, as I wanted to be as horny as I could when meeting up. The reason for this, irrational as it may appear, was because I feared I would ‘chicken out’ and my thinking was that if I was extremely turned on it would ‘force me’ to make good on my commitment. I suppose you could liken it to knowing you’re going for a good meal and not ‘snacking’ beforehand for fear it would ruin your appetite.
As the day got nearer, I picked out a couple of my favorite outfits, wig, lingerie, several pairs of stockings (didn't want to ladder any getting dressed up and have my first face to face with shabby stockings) and shoes and packed the suitcase. We had agreed over the phone that it was impractical for me to turn up dressed because of the risk of Neighbour's seeing a tranny turn up at his place also there was no way I was going to drive there as ‘Nikki’ in case I got pulled over by the Police or had an accident or something equally as embarrassing. We had agreed that I turn up ‘as a guy’ and I would immediately go to his bedroom and get dressed while he waited in the lounge.
As I didn't know Rayleigh very well, I bought a book of maps of Essex and looked up the address, working out the easiest route to his place. Remember, there were no ‘Satnav's’ back in those days.
I don’t think I would be lying if I said I was practically ‘shitting myself’ when I eventually drove to his house. Butterflies were an understatement. My stomach was doing somersaults.
When I arrived at his place, I tentatively knocked on his door. I was so nervous part of me hoped that he wouldn't answer or hadn’t heard the knock and I resolved not to knock a second time. I was on the verge of leaving when the door opened.
A guy answered. He was about my height (six foot), slim. Dark almost black hair which was quite longish, parted on the side. He actually looked a little bit like Bryan Ferry in his lounge lizard days although he wasn’t dressed in a tux or dinner jacket. He was wearing a light long sleeved shirtand dark trousers. Smart casual I guess you’d call it.
I guess he was attractive for a guy although like I said I didn't fancy guys at all. However, I didn't think I wanted him dressed up as a woman either. It was weird, I had no idea what I wanted except I wanted him to fancy me when I got dressed. It was almost like I didn't care what he looked like so long as he ‘wanted’ me.
We almost formally exchanged greetings, all the while not really making eye contact and he showed me upstairs to his bedroom where he left me to change.
Before leaving my house to come here I had the presence of mind to have a long bath so I could do a full body shave, as I didn’t want to take forever to get ready for him. As it was, I must have taken a good 30 to 45 minutes getting dressed and putting on a little light make up which I had recently bought. A bit of foundation, eyeshadow and lipstick. I really didn’t have much idea back then. I put on a pair of black satin panties, a black satin under bust corset which had four suspenders and a pair of Aristoc ‘Nylon’ black seamed stockings. I then put on a black satin bra and put a pair of ‘homemade’ false boobs in (all right, a couple of balloons filled with water). Then I put on a fake pearl necklace. At the time I already wore gold sleeper earrings so I didn't have to worry about those. As I said I had packed a couple of outfits but I opted for a cream satin blouse and a black tightish satin pencil skirt, exactly what I had on in the pic I put in the ad.
I put my wig on. In those days I only owned one, the black, not quite shoulder length, cleopatra bob wig. I squeezed my feet into the 3-inch black stilleto court shoes, and finally, on my right ankle, I put on a gold-plated ankle bracelet I’d picked up from Savacentre, being careful not to ladder the stockings.
With my heart pounding like a trip hammer in my chest I was ready to go. I took a deep breath (apart from being nervous, my corset was really tight and restricted my breathing somewhat) and opened the door. I carefully walked down the stairs, swinging my hips to make myself feel sexier, but also being careful as I hadn't negotiated stairs in heels before and I didn't want to do a comedy Mrs. Doyle and end up rolling arse over fake tits all the way to the bottom.
As I entered the living room I became ‘Nikki’. A sexy seductress, slowly walking, swaying hips and licking shiny red lips. I knew exactly how I wanted to appear and I tried my damnest to be that way. He was sitting on the sofa and he stood up as I came towards him. I walked up to him and slid my arms around his neck and slowly kissed him on the lips. The kiss became passionate very quickly as our tongues intertwined and his hands found my waist then moved down to caress my satin covered bottom. He pulled me tight against him and corny as it sounds, I felt his hard bulge against me. My own bulge was also growing filling my satin panties and already moistening with precum. I was so turned on.
We kissed for ages. It was the first time I had ever kissed another guy, something I would never have even thought of as a guy. It felt a little weird, all the girls I’d kissed in the past never had to shave, as far as I’m aware anyway, and even clean shaven a guy just feels ‘rough’. Nikki however, had taken over and ‘she’ fucking loved it.
I started to move against him, gyrating my hips, rubbing myself against his hard bulge. His kisses became even more passionate and we were both breathing very heavy.
I removed my arms from around his neck and slowly moved down to unbutton his shirt and caress his chest which was very smooth and his skin was very soft and warm. I bent my knees as I stopped kissing his lips and started to move down his body kissing his chest. I slowly continued to move down until eventually I was kneeling in front of him. My face level with his bulge. I leaned in and kissed it feeling how hard it was through his trousers. He started to sigh and then groan.
Nikki was in control.
I undid his belt and unhooked his trousers and slowly undid his zipper. Gravity took over and his trousers slid down to his ankles and I was staring at a pair of red bulging pants with a dark wet stain just below the middle. I leaned forward and kissed and licked the bulge tasting the salty damp patch and he groaned louder and staggered slightly. I thought he was going to come then and there.
It suddenly dawned on me that this was it. I was finally going to suck another man’s cock! Duality reared its ugly head. Half of me wanted to take the cock out and devour it, feel it pumping down my throat, the other half felt disgusted and almost sickened by what was happening. I stopped kissing the bulge and began rubbing over it with my fingers while thoughts about what I was actually going to do next battled inside my head.
Almost as if my hands had minds of their own, my fingers hooked into the waistband of the pants and pulled them down over the bulge releasing the b**st inside. It sprung out and upward, slightly curved but rigid and hard a rock. The helmet was dark and shiny like plastic and there was a large clear bead of precum welling from its small dark hole. I just stared in awe of it. It seemed massive, much bigger than mine which was at least 6 inches at full mast.
Again, my hands moved as if on autopilot and the fingers of my right hand encircled the cock and I could feel how hard he really was. My other hand gently ran from the balls to the tip stroking as if enjoying the texture and softness of the skin. Without thinking about it my head moved forward and I kissed the tip and then gently, slowly kissed up and down the shaft.
I kissed it like I was kissing the face of a woman, kissing something that was beautiful or that I was in love with. I heard groaning again only this time I realized it was me. My lips moved up and down the shaft, making love to the soft silky skin until they went back to the tip and encircled it. Sliding forwards, my tongue running over and around the smooth hard helmet, finding the little hole and tasting the precum which oozed from it.
I had never sucked cock in my life up until that moment so I should not of had a clue as to what I was doing but whatever I was doing my ‘lover’ certainly enjoyed. Ok, I had seen women and a few guys sucking cocks on porn films and obviously experienced a girl giving me a blow job but giving a guy oral sex was totally alien to me. But here I was doing it like a pro on all accounts.
I moved my head back and forth, sliding the cock almost down the back of my throat and then back until slightly encircling the ridge if the helmet. All the while sucking and flicking my tongue around and over the surface of the cock, probing the pee hole, making ‘mmmmmmmmmmmmm’ sounds like I was enjoying an excellent meal.
My ‘lover’ was also very vocal, moaning, groaning and sighing as I worked. My right hand encircled the base of his cock, following my lips back and forth while my other hand slid round to the back of his arse where my fingers gently slid up and down his crack until my middle finger found his hole and slowly but gently started to probe, engendering more groans from my ‘lover’. I felt him starting to pump his hips and his hands moved to the back of my head and I knew he was close. Unfortunately for him, Nikki was really enjoying this and wanted to make it last so I pulled back and slowly stood up. My right hand changed the grip on his cock so that I could lead him. He looked at me earnestly, begging me with his eyes to finish him but I leaned in and kissed him pushing my tongue deep into his mouth letting him taste his own cock juices.
His trousers were still around his ankles but I led him the short distance to the couch by his cock and sat, then laid him down.
When he was laid down flat (luckily it was a three-seater sofa) I knelt next to him on the floor and started to kiss him. First his mouth while my right hand gently stroked up and down his cock, then all over his bared flesh. Kissing, licking and occasionally gently biting. Whenever I ‘nipped’ him I would squeeze his cock mid rub making him twitch. He was already moving his hips, pumping up and down with my strokes.
I was thinking ahead to my next moves. Going back down on his cock, then lifting my skirt and moving my panties to one side to release my own stiff dripping cock, then straddling him and sliding his cock into my arse and riding him like a stallion until he pumped his come into me while I wanked my cock and came all over his chest, when Mount Vesuvius erupted. He let out a loud shout and thrust his hips upward and his come spurted out like a fountain. At least two squirts jetted straight up almost hitting the ceiling and splatting back down over his stomach. Several drops shot to the side as I still pumped going up the wall and some even got in my wig hair.
My hand still pumped up and down, milking every last drop and his body spasmed and convulsed at each ejaculation until he was spent. I still stroked grinning with power until he pleaded with me, breathlessly to stop.
He laid there panting for several minutes until he got his breath back. I just sat there smiling at him and then when he had recovered some composure asked him for a towel, He indicated a box of Kleenex man-sized tissues on a coffee table. I took a few and wiped my hands then passed him the box. He too took several and proceeded to wipe down his belly and several other places where his come had landed. When he was finished, I politely coughed (as in ‘Ahem!) and pointed, grinning to the spots on his wallpaper where come was slowly running down in shiny stripes.
“Oh!” He said, embarrassed. Then quickly pulled his pants and trousers up and refastened them. Then he wiped the semen from the walls. Thank God for vinyl wallpaper.
I got up off the floor and sat on the sofa and he sat down next to me, looking a little awkward. “Um, do you want me to...” He started. I laughed and held up my hand indicating he didn't have to say anything. “It’s Okay” I said “I am still horny, but I know what it’s like when I’ve shot my load so to speak, after dressing especially”.
The look of relief on his face was pretty comical, but I did truly understand. This was his ‘secret’ side, not his norm. He was probably bi-curious and therefore when his ‘urge’ has passed he’s very likely feeling the same guilty, almost shameful feelings that I do and most probably will when I get home, after I’ve had a wank of course.
Chapter 1 - Start of a Fetish
I have had a strange attraction for satin for as long as I remember. when I was about 4 years old I remember being fascinated by the look and feel of one of my baby sister's dresses, which was of course made of satin. My mum (who left home when I was 5) also had a cream coloured faux fur coat with white satin lining and I remember constantly fondling and stroking and loving the feel of the satin against my skin. When my mum left home, she left some of her old clothes behind and I found the coat while rummaging around our spare room when I was off sick from school. I was still very young, but my dad had to work full time to support me and my older brother, so with my brother at school I was alone in the house.
When I found the coat, I got very excited and aroused. I took it into my bedroom, stripped off and got into bed with the coat. I started touching, then caressing the satin lining and eventually started rubbing it over my naked body and genitals. I think I had my first and several pre puberty non ejaculatory orgasms. Needless to say, I enjoyed it and after did it every chance I could get.
I began to notice that every time I saw a woman wearing satin, especially while watching old movies with the old Hollywood starlets like Monroe, Harlow etc. wearing gorgeous satin dresses and gowns, I would get an erection and would have to disappear and have a session with 'the lining'. One Saturday afternoon when I was about 11, I was watching an old black and white movie in the lounge while my brother was out and dad was in the garden mowing the lawn. Suddenly the lady in the film swept onto the nightclub stage floor and started singing and dancing while wearing an amazingly sexy long slitted black satin dress with long black satin gloves... I actually came in my pants, and not the dry kind either. In fact, it was my first proper ejaculation and at first, I was worried because of the wet, sticky liquid that pumped out. The lady in the film was the actress Rita Hayworth and the movie was 'Gilda', one of my now favorite movie scenes and masturbatory fantasies. (https://www.youtube.com/watch?v=xBILSCFMg8M).
I also remember every Saturday morning having to go shopping for groceries with my dad. Once, while in the Co-op supermarket one day, as we were walking between the aisles, as I turned a corner, I bumped into a red-haired middle-aged woman wearing a 50's style satin dress. It was silvery white, with tiny black polka dots, sleeveless, very tight. I think they call them 'wiggle' dresses now. Apart from the excitement of seeing her in it, I actually felt it as we bumped into each other. Another instant orgasm! Unfortunately, I had to carry on shopping with wet and sticky underpants, however it didn't bother me because I spent the rest of the outing in a daze, thinking about that woman and her amazingly sexy dress. When I got home, I rushed upstairs to my room grabbed the satin lined coat and 'wanked' myself silly.
Of course, as I got older, I learned about masturbation and realized that was in fact what I was doing. However, what I really couldn't understand was that while most boys ‘wanked’ to some form of pornography, I was masturbating to either a piece of satin material or images of women in satin clothing. I did have access to lots of porn. My dad (and later my brother) had a fairly large supply stashed under their beds and although the images did arouse me, nothing quite did it as much as satin. I did however gain a lot of knowledge about sex etc. from reading the articles and stories in the magazines.
I had my first real girlfriend (Jackie) when I was about 12 and we ended up dating for the next 5 years. Due to my exposure to pornography at a fairly early age it wasn't long before we got into heavy petting and had a regular 'nookie' session every Sunday night at my house when we would sneak up to my bedroom and 'listen to records'.
One night when Jackie came round, she was wearing a long-sleeved white satin blouse that did up at the back, that she'd borrowed off her mum and I was previously unaware of. It was the 70’s at the time when retro fashion from the 40/50’s became popular. When she took her coat off and I saw it for the first time my eyes nearly popped out of my head and I got an instant erection. I practically dragged her upstairs and into my room and ravished her severely.
Once Jackie realized how turned on, I got when she wore satin, she got hold of as much as she could, blouses, dresses, skirts, lingerie, often raiding her mom's wardrobe and underwear drawer. Also, when she was about 14, she really got into the retro look and started wearing stockings, stilettos, retro lingerie, Pencil skirts...I loved it. However, her dad was very strict... almost Quaker-esque and didn't approve at all, so she started leaving her stuff at my place. I used to really look forward to Sunday nights.. made having to face Mondays and school bearable.
Unfortunately (or fortunately, depending on how you look at it) one Sunday afternoon when we were both at Jackie's house, just as we were getting ready to leave for my place, her dad noticed her wearing makeup and stopped her coming round. I remember being furious and seething while I walked home alone.
When I got in, I went straight up to my room, put some records on and just laid on my bed looking at the ceiling feeling very angry and sexually frustrated. After a while I started to calm down but still felt really horny which led of course to me fondling myself. For some reason though it wasn't really working but then I remembered Jackie's stash in my cupboard.
Initially I was just going to get something satiny and just strip off and rub the material over my body and crotch until I came... however while going through her stuff I found her red satin suspender belt and black seamed nylon stockings. I felt so horny thinking about her silky legs rubbing against me in those stockings, something compelled me to put them on.
When I did, my cock got even harder, and after a few strokes and almost to the point of cumming, I looked at the other clothes she left there... that blouse. White, smooth, shiny... I didn't think it would fit me and trembling inside with excitement, I slipped it on. I was so surprised that it fit me! Jackie was a size 14, quite a big built girl, not fat. In fact, she was gorgeous...but this fitted me. So, I did the little buttons up on the cuffs and the one behind my neck and just looked at myself in the mirror on my cupboard door and run my hands over the material, over my chest, arms. I even nuzzled my mouth to my shoulder and kissed the satin!
My cock was almost exploding and I hadn't even touched it after putting the blouse on. It was dripping precum and my hand moved down and lightly brushed its tip feeling the warm wet precum on my fingers... then for some unknown reason I put it to my lips...and then got more, all over my fingers and sucked them, licking the juice off... I then started to stroke and BANG! My spunk shot out like water from a fire hose... all over the mirror... when I see the cum running down the mirror something made me go to my knees and lick it off... I'd never tasted my own cum before and was almost overwhelmed as I lapped it up, all the while still pumping cum from my cock.
When I had finished cumming I sat back on the bed. my emotions were all over the place and as I looked at myself in the mirror, I felt sort of disgusted and guilty for what I'd done, so I pulled the clothes off as quickly as I could and shoved them back in the cupboard, almost slamming the door, ashamed of what I'd done. I quickly ran out to the bath room and washed myself. I think I was trying to wash the perversion off. I wasn't a poof! I'm not queer! These things were rushing through my head. I was really worried that there was something terrible wrong with me and vowed to myself I'd never do it again.
So much for that vow... a day or so later, the thoughts wormed their way back into my head... and when they did a warm feeling spread from the pit of my stomach...the stirrings of excitement...my cock tingled at the thought of wearing that satin and stockings etc. again...
As the days went by, the feelings got much stronger and I eventually gave in to my craving again as soon as I got home from school. My Dad was still at work and wouldn't be in for another hour at least so I went to my room, closed the door, stripped off and got the clothes from the wardrobe. this time adding Jackie's silky knickers...she had also left a pair of kitten heels too. Black.. very pointy toes. and... I thought I'd try them on. She was a size 6(UK) and although having ridiculously small feet, I was a size 7 and a 1/2... I still managed to squeeze the shoes on. They were agony but I ignored the pain. I strutted around the room, walking backwards and forwards in front of the mirror, hands on hips, trying to walk with a wiggle like a sexy woman.
My cock was bulging against the silky knickers... and precum was oozing out and soaking them. I stopped in front of the mirror and started to run my hands over the satin, sat on the bed and stroked my hands up my stockings as I'd seen women do in the movies when they're smoothing them... I was so incredibly turned on... I didn't realize it, but I was more turned on then than I would have been if Jackie was there wearing it all for me... needless to say, I masturbated and came profusely.
And this was how it went on...me getting the urge, dressing as soon as I could, masturbating, cumming and feeling terribly guilty afterwards although, the guilt had started to wane gradually as I kind of accepted it was my little secret, and so long as I didn't get caught. where was the harm? I still thought it was wrong on so many levels but I was sort of accepting it was my 'dark side'. As time went on, I managed to get Jackie to buy even more stuff to leave at my house, satin skirts, dresses, lingerie and so on, until I'd built up quite a collection of her clothes in my wardrobe, some of which I still have today!
Jackie and I eventually split up when I was nearing 18. We'd both left school, started working and for reasons I won't go into (nothing to do with my Dark side) went our separate ways. I really missed the female company and the sex, of course, but, huge bonus, she left all her stuff at my place so I was still able to dress up when the urge struck, which it did often. Most of the time it was just random thoughts as I went through my day that would kick it off, but if I saw a woman wearing satin, in real life, on tv, even pictures in magazines and the newspapers (which I started to cut out and collect) I would have to go an 'have a session' as soon as I could.
Eventually I started to accumulate my own supply of clothing in addition to the stuff I’d obtained via Jackie. The first time I actually went and bought something from a shop that sold women's wear, on my own, was odd if not embarrassing. Although I was 'getting to grips' with women's clothing sizes, bra measurements were still a mystery to me. This usually ended up with me asking a shop assistant that old chestnut 'If it didn't fit HER is it ok to bring it back? ' all the while trying to hide my embarrassment, and most of the time, excitement. I'm certain, that no matter how convincing your cover story is, women have a sixth sense about trannies, so every shop assistant in stores where I've bought stuff, has known I was going to go home and dress up in whatever I bought. Ok it was true, but...
All this time I was dressing up, I was meeting girls, going out with them for a few months, even years, all the while managing to hide my secret from them. Oh, they all knew I had a fetish for satin and stockings, I was always very open about that because, after all, I decided I wasn't attracted to a woman UNLESS she would wear satin for me. Sometimes it caused problems but on the whole, it worked out for me.
I got married in 1980 to a girl I had been dating for about 18 months, unfortunately it failed mainly because she started seeing her previous boyfriend so she left me. I was renting a flat then, just literally around the corner from where I used to live. Which was handy as I could go and visit my dad whenever I wanted to. He was living alone now, and I did really feel sorry for him, so I visited almost every day, or he'd visit me. As I mentioned earlier, my dad used to buy lots of girly magazines, mainly Mayfair and Penthouse, which he used to stash under his bed, and he knew I knew they were there so before I even moved out, he'd started letting me read them. I remember way before I'd split from Jackie, still living at home, I read a story in The Penthouse 'forum' about a woman who'd caught her husband wearing her lingerie. I was really surprised when I read it because I, at that time, naively thought I was the only guy in the world that did this. I'd seriously never heard of transvestites, only what we would then call, in the days before the monster known as political correctness appeared, poofs and queers!
While I was reading it, I started getting very turned on, but when it got to the part where she made him dress up for her and then started bringing guys round to fuck in front of her sissy hubby, my cock was like a Trident missile. As the story progressed, it evolved into her making her hubby into a sissy slave and made him start giving her boyfriend's blow jobs and letting them fuck him. That REALLY turned me on!
I'd never even dreamed of having sex with a man and, never, EVER, wanted to. As far as I was concerned, I was completely hetero and would never look at a guy 'sexually' at all, in fact, it was abhorrent and completely disgusting to me.
Why was I getting so turned on? I was so turned on in fact that I came even before finishing the story...although I finished it hundreds of times afterwards.
When I was living on my own, I'd gone round the corner shops to buy some food etc, when I noticed a small magazine on the top shelf of the news wrack, wedged in with the other 'girly' books. I think it was called 'Transworld' or something. I grabbed a 'Forum' mag that was nearby it, and then quickly grabbed the Transworld book too.. and with a bit of sleight of hand managed to tuck it under my shirt and into the front of my trousers without anyone seeing. I paid for my bits and the Forum mag, and walked briskly from the shop, dreading that I was going to get caught...It would have been bad enough getting caught stealing, but caught stealing a Tranny Mag?
When I got back to the flat, I started reading the mag. I was getting more and more turned on, and so I went into my bedroom, stripped off and put on some women's satin Pajamas and a long satin robe and then for some reason, I latched my front door, and went back into the lounge, put some music on then carried on reading the Tranny magazine... getting soooo turned on reading the stories and looking at the photos of real transvestites. Fuck I was so horny. I fantasized about being with one (or more) of them.
Around this time, I'd also got into filming myself on an old black and white video security camera I'd picked up from a boot sale. I had several tapes hidden away of me dressed up, walking around to some sexy music and wanking and, often I used to watch the tapes and masturbate to them. I didn't think that was me being gay, it was just me getting turned on by what I do. I also used to masturbate to videos/movies where there was someone (anyone) wearing satin. The Gilda tape was almost worn out.
Now I was masturbating while looking at TV's. Nope, I'm still not gay, I was telling myself, I'm turned on by these guys dressing...in silky clothes, sometimes with their cocks out... FUCK I want to have sex with them...No, I'm still Not gay!
The truth is I didn't know what I was. Everything I'd read about Transvestites stated that the majority of TV's were 'Straight'... so although I didn't advertise it, I labelled myself secretly as a Transvestite, or 'Cross Dresser', a new term I'd learned. I KNOW I didn't fancy blokes at all, but I had to admit to fancying Transvestites, although they had to be convincing.
I guess I really fancied Transexuals. And, it wasn't long before I was watching TS videos, in fact, to be completely honest, apart from watching lesbians, 'Normal' porn didn't really do a lot for me anymore.
So I was into T-girls as well as women (in satin), guess I was a bit Bi then, something I kept completely to myself.
After I finished reading the Transworld mag, I remembered the Forum I'd bought. Later, when I wasn't in TV mode, I gave it a read and noticed, apart from a few weak stories, it was predominantly a personal or 'contact' mag. For more of a laugh (or curiosity I suppose) I started reading the 'classifieds'. It wasn't long, which surprised me, before I found a TV related ad. And, I started getting turned on reading them...fantasizing a bit.
There were guys looking for TV's, TV's looking for TV's, Couples etc. etc. Yeah I was fantasizing about putting a contact in...but of course I didn't.. not then anyway.
It was much later, in fact, just prior to my second marriage when I actually did. I was dating a girl who lived in Leeds, which as I’m sure you know, is miles away from Basildon. I'd also moved back in with my dad for several reasons, which I won't go into, and was now learning to drive, and working for the Local Council.
Dating someone from Leeds had its disadvantages, but also meant I had plenty of 'me' time at home between 'dates'.
I'd taken to buying loads more women's clothes..99.9 per cent satin clothes that is, and had a huge wardrobe full of it. I hadn't really started to wear make-up when dressed, and I didn't have any wigs yet. I still had my own hair then, although by the age of 23 it had already started to recede. Thanks Genetics. I only had one pair of high heels that I had 'inherited' from Jackie, but used to dress up, almost fully more and more frequently.
My fantasies were also getting more 'Raunchy', generally involving satin clad women, but more frequently, satin clad T-girls. Occasionally, I would also fantasize about being made to suck a guy's cock, although in my fantasy the guy was very vague, no features or anything, just a 'Guy' or more specifically, just a ‘cock’.
As for being fucked, I mean me receiving 'Anal', I was very curious to what it felt like.
I'd occasionally 'fingered' myself while masturbating, but didn't really know what it felt like to have something 'Dick' sized entering me. Until, one day, curiosity got the better of me and I bought my first Vibrator from a lingerie catalogue. I'd started to subscribe to several, originally because of the pictures of women in satin, but also so I could add stuff to my wardrobe via mail order. I also had several 'normal' catalogues on the go, Littlewoods etc. again, originally for the pictures, but then for buying clothes. It was easier than shopping in women's stores but I did actually get addicted to ordering anything satin I could find. And, getting credit was so easy in those days, I did get myself into shit loads of debt. Another tale perhaps.
Anyway, back to the vibrator. When it arrived, I went out and bought some extra batteries, and a small jar of vaseline. I didn't use it right away, I waited until I went to bed that night before opening the box. When I did, I wasn't that impressed by its look. It was one of those cream coloured, unimaginative bullet shaped things, about 7 inches long. I think it was called a 'non-Doctor'. I put the double A batteries in and switched it on...It was quite loud, and I was worried my dad would be able to hear it. It felt weird vibrating in my hand and I moved it under the bedclothes and pressed it against my flacid cock. Hmmmm.. quite nice, my cock started to harden. Yep, it was turning me on alright. I reached down by the side of my bed and picked up the small jar of vaseline. I placed the vibrator between my thighs just so it was touching my cock and squeezed my legs together, holding it in place while I opened the jar. I put two fingers into the jar and then slid my hand under the covers, trying not to get any of the greasy substance on the bed clothes. I moved my hand down until it was close enough to my anus and slid my fingers inside me. I hadn't used any lube when I fingered myself before and was pleasantly surprised when my fingers slid in so easily. I remember gasping as I pushed my fingers in as far as they could go, feeling my cock twitch, I let the vibrator drop as, if it had stayed in contact with my cock, I would have shot my load then and there.
I slowly withdrew my fingers, retrieved the vibrator and proceeded to smother it in vaseline.
Then came the moment of truth, I moved the vibrator and positioned it's tip gently on my tight little hole. Even that was giving me tons of pleasure just feeling the slightly 'tickly' vibes throbbing at my sphincter, and I noticed I was moaning to myself like a porn star.
I slowly slid the slightly cold plastic into me, centimeter by centimeter. My cock was so hard now and I wasn't even touching it.
It hurt at first as I went deeper but I'd lubed it up enough that I could withdraw it easily if it hurt too much. As pleasure overcame pain, I started slowly fucking myself with this plastic battery powered toy...and I was loving it!
I gently touched my cock and was about to start masturbating when BANG! I came! My cock pulsating as I spurted cum after cum into my bedclothes.
When I finally withdrew the vibrator that old feeling of disgust had crept back in... not just for what I was doing but also because not only were my bed clothes covered in spunk, but there was p*o all over the vibrator...and I felt like I URGENTLY needed to poop as I was literally starting to shit myself. I won't go into the details of the clean-up but I will say it wasn't pleasant.
I learnt a couple of lessons there which have stood me in good stead since.
After I had gotten over the disgust feelings, I could categorically say I like having things up my ass, and repeated the process often when having one of my sessions.
Chapter 2 – A Bigger World
So, till trying to convince myself I wasn't gay, I'm fantasizing about gay sex, simulating Anal sex..what's next?
The contact magazine was still tugging at my head, not sure if it was a fully conscious thought yet...but I was intrigued about it and slightly thrilled about the concept of, more or less, anonymous sex with a complete stranger, with no ties...completely secret.. and completely harmless unless someone I knew found out.
With my girlfriend in Leeds, I had plenty of time to myself indulging in my fantasies whilst masturbating. And, I was also having some very erotic dreams while asleep. Although I never thought I would try to make my fantasy real, there of course comes a time when you've got to at least have a peek inside Pandora's box.
I decided to put an ad in a contact mag.
I had at this point bought myself a Polaroid Instant Camera...I don't know if it's a purely Narcissistic thing or what but I enjoyed seeing myself dressed up, so apart from the decidedly bad low quality black and white videos I'd made, Self-timed Polaroid pics were my only option...only because at that stage I was too scared to have normal photos developed in a shop or chemist. I had several what I would call 'pretty good' pics of me dressed. I then went about writing an ad.
'Bi-sexual Satin Clad TV for Same' (Was there such a thing?)
How to start? do I put a name? What should I call myself?
Well, my actual 'male' first name is Nick. I decided to call myself Nikki..
After that I put some stuff about me loving satin and getting horny while wearing and seeing others wearing it, having a large wardrobe, being bi-curious yaddah yaddah..and so on. I sent it to the mag with a couple of my best photos... and waited.
The next issue came out, but my ad wasn't in there. I waited some more.
A few weeks went by, and I started to get letters coming through..ad number at top, then my real name and address written underneath.
With shaking hands, I opened the first letter. There was a photograph of a guy in his 50's wearing a pink, satin bro-peep dress. That was about it. He still had about 2 days growth of beard, bald, a bit on the portly side, but very clearly a man in a dress. Something I hadn't even considered. I try to look as good and as feminine as I can. I had a good figure, and even without make up, with my hair right I still looked pretty convincing, well I thought so anyway. The point is I tried. This bloke clearly hadn't. I thought all TVs were like me and at least tried to look feminine. My heart kind of sank and I didn't even bother to read his letter. It was ripped up and put as far into my bin as I could put it. Ok, there was another...
With dubious thoughts, I opened the other letter. There was no photograph, just a couple of hand written pages. I almost didn't bother to read it as I thought If you can't put a picture of yourself in then you must be truly bad. But I persevered and was quite pleasantly surprised. It was from a guy, who apparently used to dress and didn't have any female clothes now as he'd thrown them out when he was seeing a woman... they'd since split up and he saw my ad in this month's Forum (I didn't even know another copy was out yet).Apparently, He 'Fell in Love' Awwwww... there was a bit more about wanting to dress again and would like to see me, gave me a brief description, which if accurate may look good dressed up, and left a contact number....Hmmmm...
A couple of days passed, a few more letters arrived, but no one I really liked, and a couple were a bit too far away for a meet, for me anyway. I also bought the latest copy of Forum, and lo and behold, there was my ad and picture. There I was dressed in a cream satin blouse and black satin pencil skirt, black stockings and Jackie's black high heels. No make-up but the print was so small you couldn't really tell. I would have contacted me! I also had a look at some of the other contacts in there too..TV contacts, and there were several I would have loved to meet...unfortunately they were in Scotland, Sheffield...none even remotely close enough to me to visit... none that I liked anyway.
I thought about the guy who 'fell in love' with me. I thought maybe if I took a suitcase of satin clothes with me, I could dress him up and...
Fuck it! I decided I'd give him a ring. I didn't have a phone that I would feel comfortable with him ringing me up on out of the blue especially if my dad answered, and mobile phones were still science fiction at that time. So, it would have to be a phone box. Grabbing a pocket full of change I walked round to my corner shop where there was a pay phone. I was shaking when I stood in the phone box. Fear? Nerves? Excitement? Probably a combination of all the above...
I picked up the phone with shaky hand and dialed his number, ready to put the coins in when it started beeping. It rang, and it rang and it rang... FUCK! No answer. I was about to hang up when Beep! Beep! Beep! I frantically albeit clumsily pushed the coin into the slot almost dropping the others when I did. "Hello?" came a voice...
I again have to admit to feeling a wave of multiple emotions all in one go. Surprise, fear, panic and above all else, immense excitement.
My whole body began shaking uncontrollably and I found it almost impossible to speak. My first impulse was to hang up and rush back home but the logical part of my brain kicked in telling me that I really had nothing to lose. The person on the other end of the line had no idea who or where I was, what was the worst thing that could possibly happen? If it all went pear shaped there was no way for him to trace me or anything.
“Hello? Who’s this” The voice came again. After what seemed like several minutes, although in reality was only no more than a couple of seconds, I replied.
“Hi, you answered an ad I put in ‘Forum’? “I stammered out, “My name’s Nikki.”
There was a brief pause, and then, in a voice which was almost as shaky as mine, he said “Oh, erm...Wow!” It suddenly dawned on me that he was probably as freaked out as I was. I nervously chuckled and said “You sound really surprised”.
“To be perfectly honest, I am.” He said. “I didn't really think I would hear back from you. It’s the first time I’ve ever tried something like this.”
“Me too” I said “What made you decide to answer my ad?” My trepidations were starting to dissolve now that I understood that this guy was experiencing feelings and emotions very similar to my own. We were, after all, in opposite ends of the same boat.
“Well, like I said in my letter, I used to dress but haven't in a long while. I started getting the urges again after I split from my girlfriend and more out of curiosity than anything else, picked up a couple of different contact mags,” It sounded as if he was starting to relax too as some of the shakiness seemed to be going out of his voice.
“I sort of trolled through the ads not really thinking any of them were worth bothering with and almost binned the magazines when I found your ad and your picture.”
Bloody hell, I thought. I didn't think there was anything about my ad that made it stand out from the rest. “Not many of the ads had pictures” He continued “which to me, speaks volumes about the advertisers. I mean it doesn't matter what they write about themselves, they can’t be that confident about what they look like if they don’t show a picture. And, even when they do, they usually block out the face or something so you can’t really tell what they look like. You didn't. That and I just thought you looked really sexy” He gave a giggle at that last bit, which I had to say made me feel a bit horny.
Well actually it made me feel a lot horny. I didn't know it at the time, but the thought of someone fancying me dressed up was probably, and still is apart from the satin fetish, my biggest turn on.
We talked for a few more minutes (as long as my money lasted) and after finding out a bit more about each other we decided to meet. He lived in Rayleigh which wasn't that far away from where I lived, and he gave me the address. We set a date and a time and after we said our goodbyes, I hung up the phone and made my way home. I have to admit I was really dizzy with the anticipation and I was in a sort of daze as I walked back to my house.
I can't remember exactly how long it was between the phone call and our actual meeting but suffice to say that time was spent suffering an internal turmoil of various emotions, ranging from blind panic to extreme horniness. I abstained, however, from acting on doing anything about the latter, I.e., dressing up and having a damn good wank, as I wanted to be as horny as I could when meeting up. The reason for this, irrational as it may appear, was because I feared I would ‘chicken out’ and my thinking was that if I was extremely turned on it would ‘force me’ to make good on my commitment. I suppose you could liken it to knowing you’re going for a good meal and not ‘snacking’ beforehand for fear it would ruin your appetite.
As the day got nearer, I picked out a couple of my favorite outfits, wig, lingerie, several pairs of stockings (didn't want to ladder any getting dressed up and have my first face to face with shabby stockings) and shoes and packed the suitcase. We had agreed over the phone that it was impractical for me to turn up dressed because of the risk of Neighbour's seeing a tranny turn up at his place also there was no way I was going to drive there as ‘Nikki’ in case I got pulled over by the Police or had an accident or something equally as embarrassing. We had agreed that I turn up ‘as a guy’ and I would immediately go to his bedroom and get dressed while he waited in the lounge.
As I didn't know Rayleigh very well, I bought a book of maps of Essex and looked up the address, working out the easiest route to his place. Remember, there were no ‘Satnav's’ back in those days.
I don’t think I would be lying if I said I was practically ‘shitting myself’ when I eventually drove to his house. Butterflies were an understatement. My stomach was doing somersaults.
When I arrived at his place, I tentatively knocked on his door. I was so nervous part of me hoped that he wouldn't answer or hadn’t heard the knock and I resolved not to knock a second time. I was on the verge of leaving when the door opened.
A guy answered. He was about my height (six foot), slim. Dark almost black hair which was quite longish, parted on the side. He actually looked a little bit like Bryan Ferry in his lounge lizard days although he wasn’t dressed in a tux or dinner jacket. He was wearing a light long sleeved shirtand dark trousers. Smart casual I guess you’d call it.
I guess he was attractive for a guy although like I said I didn't fancy guys at all. However, I didn't think I wanted him dressed up as a woman either. It was weird, I had no idea what I wanted except I wanted him to fancy me when I got dressed. It was almost like I didn't care what he looked like so long as he ‘wanted’ me.
We almost formally exchanged greetings, all the while not really making eye contact and he showed me upstairs to his bedroom where he left me to change.
Before leaving my house to come here I had the presence of mind to have a long bath so I could do a full body shave, as I didn’t want to take forever to get ready for him. As it was, I must have taken a good 30 to 45 minutes getting dressed and putting on a little light make up which I had recently bought. A bit of foundation, eyeshadow and lipstick. I really didn’t have much idea back then. I put on a pair of black satin panties, a black satin under bust corset which had four suspenders and a pair of Aristoc ‘Nylon’ black seamed stockings. I then put on a black satin bra and put a pair of ‘homemade’ false boobs in (all right, a couple of balloons filled with water). Then I put on a fake pearl necklace. At the time I already wore gold sleeper earrings so I didn't have to worry about those. As I said I had packed a couple of outfits but I opted for a cream satin blouse and a black tightish satin pencil skirt, exactly what I had on in the pic I put in the ad.
I put my wig on. In those days I only owned one, the black, not quite shoulder length, cleopatra bob wig. I squeezed my feet into the 3-inch black stilleto court shoes, and finally, on my right ankle, I put on a gold-plated ankle bracelet I’d picked up from Savacentre, being careful not to ladder the stockings.
With my heart pounding like a trip hammer in my chest I was ready to go. I took a deep breath (apart from being nervous, my corset was really tight and restricted my breathing somewhat) and opened the door. I carefully walked down the stairs, swinging my hips to make myself feel sexier, but also being careful as I hadn't negotiated stairs in heels before and I didn't want to do a comedy Mrs. Doyle and end up rolling arse over fake tits all the way to the bottom.
As I entered the living room I became ‘Nikki’. A sexy seductress, slowly walking, swaying hips and licking shiny red lips. I knew exactly how I wanted to appear and I tried my damnest to be that way. He was sitting on the sofa and he stood up as I came towards him. I walked up to him and slid my arms around his neck and slowly kissed him on the lips. The kiss became passionate very quickly as our tongues intertwined and his hands found my waist then moved down to caress my satin covered bottom. He pulled me tight against him and corny as it sounds, I felt his hard bulge against me. My own bulge was also growing filling my satin panties and already moistening with precum. I was so turned on.
We kissed for ages. It was the first time I had ever kissed another guy, something I would never have even thought of as a guy. It felt a little weird, all the girls I’d kissed in the past never had to shave, as far as I’m aware anyway, and even clean shaven a guy just feels ‘rough’. Nikki however, had taken over and ‘she’ fucking loved it.
I started to move against him, gyrating my hips, rubbing myself against his hard bulge. His kisses became even more passionate and we were both breathing very heavy.
I removed my arms from around his neck and slowly moved down to unbutton his shirt and caress his chest which was very smooth and his skin was very soft and warm. I bent my knees as I stopped kissing his lips and started to move down his body kissing his chest. I slowly continued to move down until eventually I was kneeling in front of him. My face level with his bulge. I leaned in and kissed it feeling how hard it was through his trousers. He started to sigh and then groan.
Nikki was in control.
I undid his belt and unhooked his trousers and slowly undid his zipper. Gravity took over and his trousers slid down to his ankles and I was staring at a pair of red bulging pants with a dark wet stain just below the middle. I leaned forward and kissed and licked the bulge tasting the salty damp patch and he groaned louder and staggered slightly. I thought he was going to come then and there.
It suddenly dawned on me that this was it. I was finally going to suck another man’s cock! Duality reared its ugly head. Half of me wanted to take the cock out and devour it, feel it pumping down my throat, the other half felt disgusted and almost sickened by what was happening. I stopped kissing the bulge and began rubbing over it with my fingers while thoughts about what I was actually going to do next battled inside my head.
Almost as if my hands had minds of their own, my fingers hooked into the waistband of the pants and pulled them down over the bulge releasing the b**st inside. It sprung out and upward, slightly curved but rigid and hard a rock. The helmet was dark and shiny like plastic and there was a large clear bead of precum welling from its small dark hole. I just stared in awe of it. It seemed massive, much bigger than mine which was at least 6 inches at full mast.
Again, my hands moved as if on autopilot and the fingers of my right hand encircled the cock and I could feel how hard he really was. My other hand gently ran from the balls to the tip stroking as if enjoying the texture and softness of the skin. Without thinking about it my head moved forward and I kissed the tip and then gently, slowly kissed up and down the shaft.
I kissed it like I was kissing the face of a woman, kissing something that was beautiful or that I was in love with. I heard groaning again only this time I realized it was me. My lips moved up and down the shaft, making love to the soft silky skin until they went back to the tip and encircled it. Sliding forwards, my tongue running over and around the smooth hard helmet, finding the little hole and tasting the precum which oozed from it.
I had never sucked cock in my life up until that moment so I should not of had a clue as to what I was doing but whatever I was doing my ‘lover’ certainly enjoyed. Ok, I had seen women and a few guys sucking cocks on porn films and obviously experienced a girl giving me a blow job but giving a guy oral sex was totally alien to me. But here I was doing it like a pro on all accounts.
I moved my head back and forth, sliding the cock almost down the back of my throat and then back until slightly encircling the ridge if the helmet. All the while sucking and flicking my tongue around and over the surface of the cock, probing the pee hole, making ‘mmmmmmmmmmmmm’ sounds like I was enjoying an excellent meal.
My ‘lover’ was also very vocal, moaning, groaning and sighing as I worked. My right hand encircled the base of his cock, following my lips back and forth while my other hand slid round to the back of his arse where my fingers gently slid up and down his crack until my middle finger found his hole and slowly but gently started to probe, engendering more groans from my ‘lover’. I felt him starting to pump his hips and his hands moved to the back of my head and I knew he was close. Unfortunately for him, Nikki was really enjoying this and wanted to make it last so I pulled back and slowly stood up. My right hand changed the grip on his cock so that I could lead him. He looked at me earnestly, begging me with his eyes to finish him but I leaned in and kissed him pushing my tongue deep into his mouth letting him taste his own cock juices.
His trousers were still around his ankles but I led him the short distance to the couch by his cock and sat, then laid him down.
When he was laid down flat (luckily it was a three-seater sofa) I knelt next to him on the floor and started to kiss him. First his mouth while my right hand gently stroked up and down his cock, then all over his bared flesh. Kissing, licking and occasionally gently biting. Whenever I ‘nipped’ him I would squeeze his cock mid rub making him twitch. He was already moving his hips, pumping up and down with my strokes.
I was thinking ahead to my next moves. Going back down on his cock, then lifting my skirt and moving my panties to one side to release my own stiff dripping cock, then straddling him and sliding his cock into my arse and riding him like a stallion until he pumped his come into me while I wanked my cock and came all over his chest, when Mount Vesuvius erupted. He let out a loud shout and thrust his hips upward and his come spurted out like a fountain. At least two squirts jetted straight up almost hitting the ceiling and splatting back down over his stomach. Several drops shot to the side as I still pumped going up the wall and some even got in my wig hair.
My hand still pumped up and down, milking every last drop and his body spasmed and convulsed at each ejaculation until he was spent. I still stroked grinning with power until he pleaded with me, breathlessly to stop.
He laid there panting for several minutes until he got his breath back. I just sat there smiling at him and then when he had recovered some composure asked him for a towel, He indicated a box of Kleenex man-sized tissues on a coffee table. I took a few and wiped my hands then passed him the box. He too took several and proceeded to wipe down his belly and several other places where his come had landed. When he was finished, I politely coughed (as in ‘Ahem!) and pointed, grinning to the spots on his wallpaper where come was slowly running down in shiny stripes.
“Oh!” He said, embarrassed. Then quickly pulled his pants and trousers up and refastened them. Then he wiped the semen from the walls. Thank God for vinyl wallpaper.
I got up off the floor and sat on the sofa and he sat down next to me, looking a little awkward. “Um, do you want me to...” He started. I laughed and held up my hand indicating he didn't have to say anything. “It’s Okay” I said “I am still horny, but I know what it’s like when I’ve shot my load so to speak, after dressing especially”.
The look of relief on his face was pretty comical, but I did truly understand. This was his ‘secret’ side, not his norm. He was probably bi-curious and therefore when his ‘urge’ has passed he’s very likely feeling the same guilty, almost shameful feelings that I do and most probably will when I get home, after I’ve had a wank of course.
2 años atrás
