Caution: This True Sex Story contains strong sexual content, including Ma/Fa, Fa/Fa, Ma/Ma, Mult, Consensual, Coercion, BiSexual, TransGender, CrossDressing, Shemale, True Story, Safe Sex, Oral Sex, Anal Sex, Masturbation, Petting, Sex Toys, BBW, Foot Fetish, Leg Fetish, Transformation, .
Desc: True Sex Story: Chapter 1 - I am mature, part-time transvestite who has had many meetings with other transvestites, male admirers, transsexuals and women. I have decided to tell my readers about some of these encounters in a series of short vignettes, which I hope you will delight in. All of the stories are true, although I'm sure there will be some dissenters who claim they are fiction. Please enjoy my True Stories.
Before I begin to tell you the story of my first sexual encounter whilst dressed as a woman I would like to tell you a little about myself. For those of you who have read my essay "Why Some Men Prefer Transvestites" you may think I have repeated myself but I haven't; there is a lot more detail here.
For those of you just here for a wank; skip the first six pages and head straight for the sex.
To set the scene, I am a forty-something, married, businessman who also happens to be a part time Transvestite. That is I like to dress like a woman and experience sex with men, other Transvestites, Crossdressers and women. I do NOT want to be woman, I don't stay dressed as a woman all day every day, nor am I interested in sex with men unless I am dressed as a woman. I used to consider myself a 'Crossdresser' until a few years ago. To explain; that means I used to dress in female clothing, which I had acquired here and there, and wear a bit of makeup occasionally, but made no real effort to feminise myself when dressed. I started to really like what I was doing and got turned on and started to fantasise about having sex whilst dressed and I spent a lot of time looking at TG websites on the web. After a year or so I got serious and bought my own clothes, shoes, wigs, etcetera, and put some effort into learning to use makeup and to feminise myself whilst dressed and I also lost some weight. I now look quite passable (in my humble opinion) as a Transvestite, that is to say I no longer look like a bloke in his wife's clothes.
I have always had a fetish for nylon stockings, pantyhose and lingerie and this eventually grew into transvestism in my late thirties. I had had numerous sexual experiences with my nylon and lingerie fetish, including a few encounters with Transsexuals, but I never experienced sex with a man until I became the Transvestite, Michele. Before I tell you of some of my encounters; I thought I might share with you some musings and inspirations that I have. Even though I have only been 'active' as a Transvestite for a few years and am 'in the closet', I believe that some of the following is worthy of discussion and would welcome any responses to my email address.
Clothes & Makeup
I discuss clothes and makeup at some length in my Yahoo Group and provide some advice to beginners and closet TVs and CDs. One of the main things that I think attracts men to Transvestites is the way we dress and make ourselves up; we wear the sort of clothing and makeup that mature men find exciting. I have to say that most of the women's fashions today are not to my taste; too many pant suits, shorts, midriff tops, and sensible shoes. The makeup is bland and natural skin tones rule. Well fuck natural! Bring back ruby red lipstick, black eyeliner and mascara, coloured eyeshadow and high, rouged cheekbones; bring back the eighties makeup style I say!
Mature men (at least the type I fancy) like short skirts, high heels, stockings, pantyhose and silky blouses; not jeans, shorts, long peasant skirts and pant suits in boring shades of brown. Living in a hot climate like Australia makes it even harder to spot a girl dressed the way I like them because most of the women dress casually, if not downright daggy. I'm convinced the national dress for women in my country is becoming khaki shorts, tank tops and flat sandals.
My only advice in this essay to Crossdressers who are just starting out is to look at the pictures of Transvestites on such websites as KTMGirls, TVChix and other quality Transvestite places on the net. You will find that the better (more convincing) girls pay attention to detail and match their wardrobe and wear heavy makeup, but take the time to apply it so that it looks professional. There are some great websites with good advice on makeup but most advice in women's fashion magazines does not suit male skin types and again tends towards the more conservative natural look of today. It takes time and practice sure, but just go out and buy some cheap makeup and practice until you get a look that suits you. Except for lipstick (I use a two coat, Max Factor EverLites ®, because it stays on during heavy kissing and fellatio), otherwise all my makeup comes from the $2 shop. If you want to see my progression from tubby Crossdresser to sexy Transvestite look at my page in my Yahoo website; it took me about two years to get a look I'm really happy with.
I used to have a large wardrobe or clothes, makeup, shoes, lingerie and accessories until I threw it all out in a hissy fit and vowed never to crossdress again after a bad experience with an Admirer (which I will tell you about later). An Admirer for those of you who do not know is a man who finds Transvestites and Crossdressers to his taste. I now find that I can get by with a smaller wardrobe that I can mix and match and with the makeup and accessories that I find suit me best. I do occasionally buy clothes off the rack in department stores but I get most of them from Opportunity and charity shops.
Should A Girl Wear Pantyhose Or Stockings?
Arranging Encounters And Risk Management
The most exciting but also the most dangerous part of being a bisexual Transvestite is arranging meetings, especially when you first start 'playing the game'; for me it is doubly dangerous because I am married and 'in the closet'. I advertise my availability on transgender websites, matchmaking websites (such as ALT.com, Adult Matchmaker etc) and occasionally in local sex shops. I am contactable by email or cellular telephone. (God, how did trannies meet before the internet and mobile cellular phones?) I keep my hotmail account separate to my other email accounts and my 'Michele-phone' is never used for any other purpose; that way I can ensure that Michele never enters into my 'real' life. If I am contacted by email I prefer to exchange pictures and if possible to chat online before meeting. I always insist; I mean ALWAYS INSIST on talking to the potential playmate on the phone at some length before a meet. I have found that when talking to someone on the phone you can usually tell if they are sincere and more importantly if they might be dangerous or a potential loony. It's not foolproof, as I can testify, but it works for me more often than not.
To start with I refuse to meet with anyone under 35, most Admirers and other TVs tend to be older anyway but young men are often still confused about their sexuality and are usually the ones who waste my time. Being a Transvestite (I'm sure other 'active' girls reading this will agree), the reality is that you are plagued by timewasters; men who send you emails or call you up on the phone looking for a meet but never show. They either chicken out or just get excited looking at your pictures and talking to you. Nothing pisses me off more than getting all dressed up and sitting there waiting for the phone to ring to pass on the address where we will meet and then ending up being stood up. It takes me from one, to one and half hours to transform into Michele (read my stories to see the ritual I go through to transform — the ritual is pretty much the same in all of my stories and that's what I do in real life) so to all you timewasters out there; go to any of the websites listed above, look at my pictures and have a wank; don't call me for a meet unless you really want to!
Once I have established trust I will then arrange a first meeting; always at a place of my choosing. I am fortunate enough to have a discreet address that I can sometimes use, or I may use a hotel room. I never meet at an Admirer's place for the first meeting. I also never give out the address of the meet until I am dressed and ready to receive the punter; I have the suitor call me to arrange the meet, get dressed, and then provide the address by phone when I am ready to receive him. Another thing that some of you Admirers need to get into your heads, is that I do not sit around 24 hours a day dressed as Michele waiting to satisfy your sexual fantasies; I lead a busy life and Michele's antics have to be fitted in around it, and then only when I am in the mood. So many punters ring up out of the blue and expect you to meet them right there and then!
I always insist on a return phone number too. If the caller rings on a 'Private Number' cell phone or from a public phone box he is shit out of luck as it's just too risky. I don't want to know too much about a punter or another TV (except that they are clean and disease free), they can use false names if they like; but I at least want to know that I can call them to call off the meet if necessary and it's also another way to verify their bonafides.
Some Transvestites and punters like to meet in a public place like a bar or café first and I can understand why; but I never meet Admirers unless I am fully dressed and made up. I am lucky that when I am Michele I look nothing like my male counterpart. I never ever, ever, ever, meet Admirers whilst I am dressed in drab (as a man), as I do not want to meet a punter at a social or business function and be recognised. I will, and have met other Transvestites at their place though, and of course I have to go there in drab and dress at the venue. In this case the other Transvestite is taking most of the risk initially so I don't mind. My advice to closet TVs and CDs who are yet to meet 'playmates' but yearning to so, is to do the best you can to ensure your safety, and the discretion and sincerity of the other party before you meet; especially when meeting male Admirers for the first time.
Sex With Men Women Transvestites and Transsexuals
I have had intimate meetings with men, women, Transvestites, Crossdressers and transsexuals in my short but exciting career. There is nothing more erotic than kissing another Transvestite; as your soft lipsticked lips mesh and your hands disappear under each other's skirts and slide up stockinged thighs; it's just the best. So sex with another Transvestite is my favourite; although I also love to be treated as a woman by mature male Admirers. I think the other reason men like Transvestites is the old adage that "men know what men like" is true. Transvestites dress and wear makeup the way men fantasise that women should, and also Transvestites know exactly how men like to be turned on and how to satisfy them; well in my humble opinion anyway.
I have been with transsexuals, but only 'professionals' (prostitutes) and in my experience, except for prostitutes, transsexuals really don't have much time for Transvestites anyway. I have included an encounter I had with a transsexual in the true stories section later in this essay. Michele has also been with a woman; again a prostitute, and again I have included the interlude later in this essay. I do like having sex with women whilst I am Michele, but as a Crossdresser, unless you have an understanding wife or girlfriend your only recourse to have sex with woman whilst you are dressed may be a professional lady.
Top or Bottom?
When meeting someone for the first time I always ask if they prefer to top or bottom. I prefer to bottom and I do have an opinion as to general rules of thumb based on my experiences. Transvestites usually like to bottom, but when together are usually very compatible and will often change roles from top to bottom and back again during a sexual encounter. I have one Transvestite girlfriend who prefers to remain the top or bottom throughout an encounter and then we change roles when we next meet. I have only been with a couple of women, but they were also willing to bottom or top; I prefer women to top as I can always have a woman bottom in my male alter ego. Most men that I have been with start out topping and some prefer to top only; but increasingly I find that they like to get a good fucking and are seldom averse to sucking my cock (I refuse to refer to my sex organs as a "my man clitty" or "my ass pussy" and other such nonsense). When men play the submissive role they will tend to 'top from the bottom' if you know what I mean (that is they remain the dominant partner) even when being fucked or performing fellatio.
I have had satisfactory sex with prostitutes; both transsexual and female, but my one encounter with a male prostitute was a disaster. He wanted me to undress and couldn't understand that I only like sex with men whilst I am dressed as a woman. He couldn't keep hard because I was a woman as far as he was concerned, and as he was gay, he could only have satisfactory sex with other men. Although flattered that I was woman enough to turn off a gay man; it didn't do much for my sexual frustration. For those girls out there still in the closet and that are yet to have their first sexual encounter as a Crossdresser, an understanding Transsexual or Transvestite prostitute is probably your safest bet; also there is less worry about discretion or safety.
Kissing Sucking and Fucking
I love kissing; it is just so much the best foreplay! I have yet to have an encounter where I didn't get involved in heavy petting and kissing before engaging in sexual activity. Even those men I have met who were having their first time with a Transvestite have enjoyed kissing me. A word of warning here to beginners, always ensure you shave as close as possible before applying your makeup when you are about to have a meet. Nothing is more off-putting than kissing a Crossdresser with a 5 o'clock shadow; make sure that you get every skerrick of hair removed off your face, especially around lips; run your fingers all around your face and if there is any rasping at all, shave again. And for god sake trim your nose hair!
Fellatio is probably the stock-in-trade for most Transvestites; I won't bore you with techniques as most of you will have your own tricks. I like to 69 of course but I sometimes find that being fellated interferes with my concentration when I am sucking. My favourite position is, like any good girl, on my knees sucking a hard cock and looking lovingly up into my lover's eyes. Most Admirers love this and will reward you with a mouthful. Another position Admirers like, is them lying on their back whilst you straddle them top to tail so that they can look up your skirt whilst you fellate them. When I am with another Transvestite I prefer to take turns fellating each other rather than 69.
I love it when the other person comes! Yes I swallow; if you haven't tried it don't knock it! I also love it when my partner comes on me; I love it over my face and love to see semen spattered on my skirt and stockings. Just one thing for those of you who have never swallowed; yes it's true that just like in my stories the penis you are sucking on will throb just prior to and during ejaculation; but when he comes in your mouth it feels like your mouth is just flooding with come, you can't actually feel the individual spurts in your mouth as I describe in detail in my stories. Also semen is not salty; as it is so often described in fiction, it is actually a bit starchy but quite pleasant to taste. Obviously the subtleties of taste vary from man to man.
Ok the truth; fucking hurts! The first time I let myself be fucked it took me ages to get relaxed enough to get a cock inside me and then it was only achieved with a little pain and lots of lube. Ok the truth; fucking is ecstasy! Once I get a cock into me and I am suitably lubricated I just love being fucked; I can come whilst being fucked without even being touched down there; in fact sometimes I come almost straight away and then again a second time if the fucking lasts a while; I don't even have to be hard! The advice I offer here is make sure you take it slowly, especially the first time (I don't care if you regularly ram a dildo up your arse; the real thing invokes a different mindset and you will have to concentrate on relaxing) and use as much lube as possible. Always make sure you are clean down there and of course: "If it's not on; it's not on"! My preferred position is on my back looking him or her in the eyes, although a good dose of 'doggy' in front of a mirror is also a real turn on. I also like to ride him sitting down or to be taken from behind whilst standing and leaning over a chair or table. Oh lets just face it; I just love to be fucked any way I can get it!
I have had the pleasure of several group sex encounters at both Transvestites only, and also Transvestites and Admirers parties. Group sex parties are not easily arranged but are well worth the effort. The good thing about having many people engaging in sex is that you can experience all those fantasises that us girls dream of: sucking two cocks at once, sucking a cock whilst wanking another, giving and receiving oral pleasure etc; the list goes on and is limited only by your imagination. You will note that in just about all my stories (Be Careful In The Park, Lady In The House, Michele And The Predator, My Brother My Sister, etc) contain at least one group sex scene.
Another good thing about group sex is that most of the participants will be at various stages of stimulation ranging from arousal to orgasm to recovery and on to arousal again; this usually ensures there are enough hard cocks to keep everyone satisfied. This is particularly the case when there are several Transvestites who usually prefer to bottom; it is to the satisfaction of all participants when roles can be shared, reversed. Also once you achieve orgasm, you can take a rest whilst someone else satisfies the person who just satisfied you without feeling guilty.
The only drawback I can think of at a group sex party was when there was a Transvestite present who was more attractive and feminine than the others, and initially most of the punters wanted to be with her and were not as attentive to the other girls present. The situation soon resolves itself though; as men being men, their sexual desires overrode their patience and soon everyone was happily servicing or being serviced.
Of course there are some risks involved in group sex, especially when meeting Admirers for the first time, but the risks are mitigated when there is more than one Transvestite present (there is safety in numbers girls). My preference is to meet in a nice big hotel room and for the girls to get there first. That way I can dress, makeup (again you note my rule of never meeting Admirers unless I am dressed and made up), ensure I look as feminine as possible and have a drink and a natter with the other girls before the Admirers arrive. I find this is more relaxing, far less risky, and of course better for the Admirer who does not need to see 'Steven' transform into 'Stephanie' before his eyes; far better for Admirers not to know all of our secrets girls!
I will now go on to tell you about a few of my (Michele's) experiences, encounters and adventures. I'll break them up into small vignettes and set the scene at the beginning of each short story; I hope you enjoy reading about them as much as I enjoyed having them (well most of them). They are all factual, true experiences; of course some (not all) of the names and places have been changed to protect both my male identity and the identities of the participants. Anyone who reads these stories and recognises themselves (they are all set in Australia so if you are not an Aussie; sorry hun, it didn't happen to you) and not happy with the way you were portrayed can contact me by email or phone and I will remove the story from its parent site or correct the story as appropriate.
I also post my stories in: Fictionmania, Crystal's Storysite, Literotica, and Sexstoriespost. I also post on my own website and a few other TG sites not specifically designed just for TG fiction (or non fiction, as this is).
Story One - Shopping Day — Transsexual Professional Encounter — Michele's First Time
I live in Australia and, as a mid level executive, I travel a lot with my job; this assists me greatly because when I am away from home I can use the hotel room or apartment that I'm staying in for encounters and other fun activities. A few years ago I was in Sydney on business and took the opportunity to do some shopping for Michele's wardrobe. This was the period when I had made the decision to become a serious Crossdresser and acquire all the trappings I needed to lead my double life. I went to a shop in the suburbs called "Glamourworld" which specialises in providing clothing specifically for Transvestites and Crossdressers. The staff there was really helpful and I bought quite a few items including a fabulous suspender belt and matching bra and panty set, a nice red Lycra miniskirt, and a pair of opera gloves. In a Surrey Hills church charity shop I acquired some nice second hand blouses and skirts, including a lovely white Carla Zampatti ® skirt which was my favourite for ages. (Unfortunately I threw the lot out a few years later when I had a hissy fit and vowed to give up crossdressing - but more of that later).
I then moved on to Oxford Street in the city, the gay Mecca of Sydney, and with the assistance of a wonderful understanding shop assistant bought a good quality wig; a shoulder length brunette bob. As it was only just after the gay Mardi Gras the shops were full of trashy tranny gear; at the Mardi Gras parade everyone wants to dress either as a Tranny or a nun for some reason! I purchased a nice pair of black high heels for only forty dollars in a shop called Pricilla's ® (closed down now I think) along with a waist-cincher and some makeup. I headed back to my hotel room after a full day's shopping to check out my purchases and to dress as Michele in her own clothes for the first time.
I had been experimenting with makeup and had hit a number of transgender Internet sites for help with makeup and other crossdressing hints. I locked the door to my room, showered and shaved and went through my purchases which I had laid out on the bed. I went through what as now become my usual ritual in the transformation to become Michele. First I slid my legs into a pair of taupe sheer to the waist pantyhose; I used to love to wear them as a foundation garment as they do so much. Firstly they made my legs look better when I put stockings on over them; they give the tops of my thighs above my stocking-tops a nice tanned smooth look. Secondly they hold my penis out of the way and get rid of the telltale bulge without having to wear a gaff. Thirdly they just feel lovely; I think the best part of dressing is sliding sheer nylons onto my legs and pulling the gossamer panty tight so that it caresses my genitals and buttocks, I always get aroused at this point.
Next I pulled on my new black satin suspender belt and matching bra; I hadn't bought any breastforms (and still don't own any) but with my own tits (I was a bit plumper then) and some padding in the form of some bunched up stockings I had a nice chest. I opened a pair of black, seamed stockings and sat down on the bed to pull them on one at a time. As the sleek stockings slid up my pantyhosed legs the feel of the nylon on nylon sent little electric waves of pleasure into my member. I clipped the garters to the stocking tops: I loved that that suspender belt had three garter straps per leg; so much better than the cheaper two garters per leg version. I then slid on a pair of red nylon panties, becoming further excited as they snuggled against my pantyhosed arse and genitals. They contrasted nicely against the black satin suspender belt.
I sat in front of the mirror and commenced making myself up. I was still a novice in those days but using the Internet tips and the practice I had gained previously from using my wife's makeup I managed a half-decent job. After I had applied my makeup and tried on the wig; I have to say I looked quite nice.
I slipped into my white A-line skirt, a maroon top and into my high heels. By this time I was quite aroused and had trouble hiding the bulge in my panties from showing though the front of my skirt. I thought I looked pretty good as I stood in front of the mirror and of course after a while I couldn't help but start playing with myself. It was quite the sight; this heavily made up slut with her skirt rucked up and her cock in her hand, slowly masturbating herself as she rocked slowly back and forth on her high heels.
I then decided I wanted more than just a self-administered hand-job and forced myself to stop. Being in the city of Sydney I knew there were plenty of Transsexual prostitutes available and decided that I would make one available for myself. As this is a true story I have to tell you that I would love to have arranged for one to come to my hotel room and have her whilst I was dressed. But the truth is that I was too scared that someone would see her come to my room. At this time, although I had been with Transsexuals occasionally before, I had never had sex with another person whilst dressed as Michele.
I phoned around (there are plenty of advertisements in the Sydney phone book) and eventually found a girl who lived at Woolloomooloo who was willing to have me come to her apartment and for me to dress up a little and have sex. As I was staying in hotel in Kings Cross and Woolloomooloo is just down the road, this was perfect, so I removed my clothes and makeup and had a shower in preparation for the night's events to follow. I decided that it was too risky for me take a full ensemble, wig, shoes and makeup with me (I was so chicken-shit in those days) but I did risk wearing pantyhose and panties under my jeans.
I arrived at the Transsexual's apartment about ten minutes after I exited my hotel. I knocked on the door and was greeted by a large, but well proportioned, caramel skinned lady in her late thirties or early forties. She was very passable and introduced herself as Tanya. She invited me into her apartment and led me straight to her bedroom apologising for not seating me in the lounge but her flatmate (another Transsexual) was home and did not like customers to linger in the rooms that they both shared in the flat. Tanya put me at me at ease very quickly; she had me seated and got me a drink and let me know it was ok to smoke as she did too. She explained to me how much she charged, that she was capable of topping or bottoming (lots of Transsexuals can't top because their hormone replacement therapy prevents them from maintaining an erection), and asked me what I would like to do and how long I would I like to stay?
I had already explained to Tanya that I liked to crossdress and went on to explain that I was wearing pantyhose and panties under my street clothes. She then went on to ask me about my crossdressing and how far had I gone with it. Tanya made me feel so relaxed that I explained my situation to her; that I had just been out that day buying all my own clothes, makeup, a wig, shoes etc. I further explained that I had never had sex whilst I was dressed as a woman but was so very much looking forward to it. Tanya said that I was silly not to bring around my purchases but that she could understand my reluctance being that I was new to the scene.
Now the next paragraph is going to sound like I made it up, but I promise you the account is factual; and if you don't believe me what do I care?
Tanya told me that she was quite excited about being with a novice Transvestite and that she was willing to do my makeup and lend me a wig; she would also provide me with a negligee and I could try on a pair of her shoes. She apologised for not being willing to lend me any other of her clothes, but of course I understood why. Tanya went on to explain that her day job was as a makeup artist and that she would make me look as good as she could make me. (I told you that you probably wouldn't believe that this part of the story is true; but I swear it is!) She also explained that it was lucky that it was her and not her flatmate who took the booking because her flatmate would have nothing to do with Transvestites or Crossdressers. I paid her for two hours of her time and got undressed feeling more excited than I had for a long time.
Tanya was bigger than me and appeared to be a mulatto of Islander descent; she had long flowing jet black hair and was wearing a dressing gown and slippers. She was wearing little makeup but quite attractive. I explained that I would like her to dress sexy for me and to wear some more makeup so that she would enhance my fantasy. She giggled and explained that my request was common and that of course she would be willing to just that; but first she wanted to feminise me.
I undressed so that I was naked except for my panties and hose; my excitement was obvious from my hard cock pushing out the gusset of my pantyhose and straining at the front of my panties. Tanya stroked me gently through my panties and pulled me to her and kissed me hard, pushing her tongue deep into my mouth. I groaned and pushed myself against her as I wrapped my arms around her ample body. She giggled and eased me away from her. Tanya realised I was close to coming already and teasingly chastised me to slow down and enjoy what lay ahead.
Tanya led me into her ensuite bathroom and sat me on a stool in front of the large mirror; she went back into the bedroom and returned with the largest makeup case I had ever seen (and have ever seen since for that matter). She started to make me up, explaining as she went what she was doing. As the case contained theatrical makeup she was able to apply a base coat of foundation that was perfect for my complexion; also it covered all of my blemishes. Next she applied a thin covering of another foundation that gave my skin a slightly tanned, even appearance. Over this she dusted on face powder which created a glowing, healthy look on my face.
Tanya went to work on my eyes applying eyeliner, eyeshadow, and mascara. I couldn't see exactly how she applied these cosmetics because she was in front of me and for most of the time and she had me half-close my eyes. Tanya did explain what she was doing though, and I did learn a few makeup tricks from her. She was so adept with her various brushes and sponges and she also sometimes blended colours with her fingers; it was so obvious that this girl was an expert.
Next Tanya rouged my cheeks and put on a two-coat lipstick after first applying lip-liner. She explained how to go outside of my lip-line to make my lips look fuller; but not to go too far otherwise it would look silly; like a clown's makeup. It has taken me a long time to get even close to the way she did my lips. (You think it would be easy wouldn't you? But the only thing I find harder is putting on eyeliner.) She finished with a final careful dusting of face powder and made me close my eyes whilst she went into the bedroom again. Tanya told me open my eyes and she was standing in front of me brushing out a long, blonde curly wig. She explained that long blonde curly hair wouldn't suit me too well but that it was the only wig she had here at home. I told her about the brunette bob I had bought that afternoon and she agreed that I had made a wise choice.
Tanya positioned the wig on my head, brushed it in place and adjusted the locks over my forehead; she explained that with a long fringe, I needn't worry too much about my eyebrows and to this day I still have never used an eyebrow pencil. Then she moved out the way and told me to look in the mirror. The transformation was amazing; I looked downright sexy with my hazel eyes glittering out of the dark eye makeup, perfectly matched eyeshadow; my rouged cheeks and plum red lipstick (still my favourite colour). The blonde curls and the longish fringe framed my face perfectly (although I agree blonde is definitely not my colour). I remember my exact words: "God I look so good; do you know what? I'd fuck me!"
Tanya laughed and said something about that not being necessary tonight and led me back into the bedroom. She mooched in her closet and came out with a pair of shiny black high heeled sandals and a black nylon long-sleeved negligee. I sat down and she helped me put on the heels which were a little big, but she joked that I wouldn't be doing too much walking in them tonight. I stood up and she eased the negligee over my head and arms and pulled it down my body; she readjusted the wig and gave it a final brushing. Tanya walked me over to her full length mirror and turned up the light so I could see myself. I was flat-chested without a bra and my tummy was a little too big for my liking but I still looked pretty good; as good as many of the Transvestites I had lusted over on the may websites I frequented.
Tanya told me to relax whilst she looked after herself and went out of the room briefly, returning with a drink for both of us. I sat down, lit a cigarette and practiced sitting with my legs crossed. The feel of my nylon hosiery against the negligee was working its usual magic and my semi-hard penis began to become fully aroused; I couldn't help looking in the mirror and thinking about what was about to happen tonight. I attempted to settle down and drink my drink, smoke my ciggie, and wait patiently for my first sexual encounter as Michele.
Tanya came out of the bathroom about fifteen minutes later looking absolutely stunning in her heavy, but expertly applied makeup. She winked at me and sat on the bed. She rummaged around in her bedside drawers and produced a white basque and a pair of sheer flesh toned stockings. Tanya dropped her robe and I saw that she was quite a big girl with a roll of fat around her girth and large firm breasts (of course they were firm; they were silicon). Her dark skin and her large proportions were such that the extra weight she carried did not detract from her sexiness. She was wearing only gauzy white panties, which were almost see-through, and when I caught a glimpse of her large thick cock through her panties I had my first feelings of trepidation, but I was also very excited. Tanya wasn't even hard yet and her cock looked menacing!
Tanya pushed and pulled herself into the basque and expertly slid the stockings up her legs; she clipped the reinforced stocking-tops to the garters hanging from the basque and went to the wardrobe again where she emerged with a pair of white high-heeled court shoes (pumps for you yanks). She sat back down on the bed and put on her shoes and then stood up and adjusted the bed-lamps to that room was infused with a soft glow. She walked over and posed in front of me with one hip thrust out and said
"Is this what you're looking for?"
(A line I now use with Admirers when they walk into the room to meet me for the first time.)
Tanya looked perfect, a large girl yes; but well proportioned. Being dark-skinned and wearing white lingerie, flesh-toned nylons and white high heels she seemed to glow slightly in the subdued lighting. Tanya's perfectly made up face and luscious big red lips were framed by her dark locks; I couldn't wait to kiss her again! I put down my drink and stood before her and she took me in her arms and kissed me again. She was strong yet soft; her kisses demanding, crushing her lips against mine and her tongue probing incessantly, deeper into my mouth. She pushed her body hard against mine and I felt the delicious feel of feminine lingerie rubbing together for the first time. My cock became erect in my panties and I could feel her thicker, longer member rub against mine through the layers of silky and nylon and I knew that this was exactly what I had dreamt of for so long.
It was obvious from the start that Tanya was going to top; to take the lead and guide me through my first 'Tansbian' encounter. She pushed me back onto the bed and lay on top of me continuing to kiss me and hold me tight. Then she extricated one hand and slid it down my body until it rested over my member, gently caressing it through the layers of negligee, panties and pantyhose; I groaned as she squeezed it firmly. I was running my hands over Tanya's back, luxuriating in the feel of her satin basque; she sensed what I wanted to do and eased herself off me so that she lay beside me, her hand still caressing my genitals through my lingerie.
I moved my hand to the front of her body and stroked her breasts through the basque, feeling her nipples harden; but I didn't linger there. I could play with breasts anytime I wanted to; I wanted to explore between her legs. I slid my hand further down her body until I was stroking the top of her nyloned thigh; god it was so exciting, then I couldn't wait any longer and I pressed my hand against the package she had trapped inside her panties. I stroked her thickening member through her gauzy panties and felt the coiled snake begin to stiffen and its girth expand; this was the first time I had felt another cock and I was thrilled; my own penis hardened.
Tanya rolled onto her back and lifted her hand to my head and firmly began to push my head down her body; I knew what she wanted me to do and I was excited at the prospect of sucking my first cock. I kneeled on the bed and moved my head down her body, kissing her ample form as I went. We ended up top and tail on the bed with Tanya lying on her back and me kneeling over her. I moved my lips down to her groin and a musky but pleasant scent invaded my nostrils. I kissed her tumescent penis through her sheer panties and my excitement mounted further.
"Suck it baby," Tanya groaned and I eased her panties aside and confronted my first ever hard cock.
Tanya's cock was considerably bigger than mine; it was about eight inches long but the girth of her weapon was what impressed me the most. It was thick, veiny and the glans were bulbous and a deep purple colour. I lowered my lips to the exposed member and licked along the shaft, slurping my tongue around the sensitive spot at the base of the glans. Although I was giving my first head job; I knew what I liked and mimicked what women had done to me. It seemed to be working ok because she groaned and again took my head in one hand and her cock in the other and pressed my lips to her manhood.
"Suck it for me honey," she uttered, and who was I to argue.
I wrapped my lips around the swollen head and sucked about three inches of her penis into my mouth.
The member felt spongy and alive, it was warm and tactile; I loved the taste and feel of it in my mouth; I knew then that I was a born cock sucker and that I had not been mistaken when I fantasised that sucking cock would be wonderful. I moved my mouth up and down on Tanya's cock, sucking it and lashing my tongue around the head as I did so. I kept this up for a few minutes and she groaned and writhed as I did so; I knew from her response that I was doing ok for my first effort at fellatio.
Tanya then placed both her hands on my head and began to force my head further and further down on her cock as she fucked my mouth. The rampant member filled my mouth and I had trouble breathing through my nose and when it struck the back of my throat I started to gag and had to quickly move my head away as I choked and sputtered. I apologised and reminded Tanya that it was my first time; Tanya apologised also and told me to take a break and then to start again when I was ready and to just take as much cock as I could comfortably suck on. She was definitely in control but very considerate. Then she reached out and pushed my panties aside and slid a sharp fingernail into the crotch of my pantyhose and ripped a gaping hole.
My cock had deflated and was semi-hard now even though I was excited to the extreme. She remedied that by taking my penis into her mouth; she gobbled it all the way in and gave it a concentrated tongue lashing as she sucked on it. My erection came back very quickly but Tanya had no problem keeping all of me in her mouth as she sucked me right down to the base of my member.
I bent my head and went back to sucking Tanya's hard penis. I gave my complete attention to fellating her and eventually I was able to get about half of her comfortably into my mouth without choking. I built up a steady rhythm and started to really like what I was doing; enjoying the experience of the fullness of her in my mouth and the taste and texture of her hard cock. I was feeling quite happy with myself, knowing that what I was doing was giving her pleasure. Then she said the words that both enthused and terrified me!
"Would you like me to fuck you?" she asked.
It took me about millisecond to respond, "Yes please."
I had earlier explained to Tanya that I was a virgin but that I had fucked myself with vibrators and dildos on many occasions and she explained to me that getting fucked by a cock was totally different, especially the first time. Tanya eased herself from under me and positioned me on my knees with my head down on the pillows and my arse high in the air. If she told me to relax once then she told me a thousand times over the minutes that followed. Tanya lifted my negligee out of the way and pushed my panties to one side exposing my buttocks. She ripped open my pantyhose even further and I felt the cool air on my exposed buttocks.
Tanya reached over, took a large tube of lubricant off the bedside table and thoroughly lubricated the area around my anal bud. She massaged away gently and then I felt her start to slide a finger inside me and it was felt like heaven. She reached under me with her free hand and slowly squeezed and stroked my cock as she slowly worked her finger in and out of me, working it slowly deeper inside me. She complimented me on our progress so far and again reminded me to relax as she extricated her finger and I heard her unwrap a condom and fiddle about a bit behind me. I looked around in trepidation at what may be coming next and saw that she had slid the condom onto a medium sized dildo and was busy smearing lubricant all over it.
I put my head down again and tried to relax as I felt the hard plastic instrument against my rear entrance. I have to tell you that try as I might, I could not get relaxed enough for the implement to slide in easy. The tip slid in easy enough but as the wider girth of the dildo began to pass through my sphincter the pain started to mount. It was not a sharp pain, more like a stretching, burning pain. Tanya was as gentle as she could be and took her time and on several occasions asked me if I wanted her to stop. I refused to give in though; I wanted to be fucked tonight! Eventually after several winces and muffled groans the dildo was most of the way inside me. Tanya had had to remove it a few times and apply more lubricant until I would let her continue but once it was in me and she started to ease it back and forth I was able to relax sufficiently enough to start to enjoy the experience.
Tanya fucked me for several minutes with the dildo, gently milking my semi-erect cock as she did so. I never did get fully hard (and seldom do even now when being fucked) but it still felt wonderful. What I was experiencing now was similar to what I experience when I fuck myself; all of the other sensations become amplified. The feel of the nylons on my legs, my panties scrunched up around my buttocks, and the negligee rubbing its silkiness on my body. I also love taste of my makeup in these situations; the taste of my lipstick in particular; enhanced by the feel of my hair on my face, I feel very feminine and submissive. This time though, someone else was administering the dildo, and that made the experience even more intense.,
"Are you ready?" she asked me the fateful question.
I knew what she meant and of course and I answered.
The dildo slid out of me very easily and then there was again the awkward experience of kneeling there with my buttocks in the air and my head down on the bed whilst Tanya fumbled with another condom wrapper and applied yet more lubricant to my sphincter. (A position that I am now quite familiar with!) Then I felt the bed stir and heard it squeak as Tanya positioned herself behind me and between my legs. She pushed my feet further apart so that she could get right in close and I felt her position herself close against my upraised buttocks and finally felt the tip of her glans against my sphincter. For about the hundredth time she told me to relax and then she slowly pushed forward. I screamed in pain.
"Take it out! Take it out!" I moaned.
Tanya slid the miniscule amount of penis that she had forced inside me out and apologised for the pain she had caused me. She was so considerate and asked me if I wanted to stop what we were doing but I was resolved to my purpose. I would like to report that the next few minutes were painless and that once she was fully inside me I was overcome with pleasure but I'm afraid the truth is that the next few minutes were very painful. (Unlike in most of my stories where once Michele has been entered; even against her will, she immediately experiences intense pleasure.)
After several attempts and half a tube of lubricant Tanya eventually had the head of her cock and some shaft inside me. We rested like that and I was able to relax my interior muscles and enjoy the fullness or Tanya's cock inside of me. When she sensed that all was ok, Tanya commenced to slowly fuck me; easing more and more of herself into me with each thrust. Now I really started to feel pleasure; the fullness of her member was particularly nice and even covered in the latex sheath of the condom, the feel of a real penis was so different to the rubber substitutes with which I had pleasured myself on numerous occasions previously.
The most intense pleasure was coming from where my sphincter was stretched around her pole and where the head of her cock rubbed against my postrate; but I was also receiving stimulation from all along the walls of my back passage. I now started to rock back and forth in time with Tanya's thrusts and was wrapped up in the bliss of actually being fucked for the first time. Again all the senses of my body became more acute and I was so aware of my lingerie, makeup, shoes and wig; the sensuousness of my pantyhose and panties were particularly heightened when Tanya thrust against me and her body made contact with my legs and buttocks. I licked my lips and tasted my lipstick and swung my head slowly from side to side feel the soft caress of my long blonde hair on my face, neck and shoulders.
After about ten minutes of slow, solid fucking I was close to orgasm and Tanya had settled into a steady rhythm which was gradually increasing in tempo. Occasionally a thrust would be mistimed and cause me slight discomfort but mostly I was experiencing a wonderful ride. Tanya then stopped and asked me if I would like to experience being fucked whilst I was on my back and I eagerly agreed to the proposal. She remained in control but was so thoughtful; how lucky I was to experience my first Transvestite sexual experience with such a caring person.
Tanya eased me onto my back and placed several pillows under me so that my groin was lifted up and positioned nicely for her to regain entry to me. It took a little while for me to relax again and her entry was slow but far less painful than before. We had soon regained our rhythm and now I was really getting aroused. Tanya lifted my legs right up high and spread them wide, but once she was comfortably deep inside me she lowered them and pushed my calves back so that my heels were near my shoulders, my legs wide, and her body leaning over mine.
Now she could lean forward and kiss me as she fucked me and I also loved the feel of her hands pressing on the backs of my nyloned thighs as she pushed my thighs down. She asked me if I was close to coming because she was close herself. Then she said something that I agree with and disagree with at the same time.
"Orgasm during anal sex is mostly mental you know" she said.
I agree that the brain is the biggest sex organ in the body, but I have to tell you I love the feeling of being fucked. She also asked if it was ok for her to come inside me; again being considerate. I indicated my acceptance and she began to fuck me earnestly.
I could sense her orgasm approaching as she thrust into me faster and deeper and I did my best, restricted by the position I was in, to fuck her back and meet her thrusts. Then the most earth shattering orgasm I had ever experienced shook my body. I could feel her cock throbbing inside me, and her thrusting cock sent wave after wave of pleasure through my whole back passage and particularly my sphincter and prostate from which I felt the most intense pleasure. My cock, which had remained flaccid throughout most of the fucking, suddenly became semi-erect and shot stream after stream of hot semen onto my belly.
Tanya squealed with joy and thrust hard into me, and although I couldn't feel the jets of her ejaculation through the condom, I could feel her cock pulsate inside me. She was panting and mewing and along with the extraordinary pleasure I was receiving from my own I orgasm; I also a real sense of accomplishment because I had made this Transsexual prostitute come. After we had both come down from our respective orgasmic highs, Tanya eased herself out of me and I was delighted to glimpse the tip of the condom hanging from her now shrinking hard-on was filled with creamy sperm; she wasn't faking it at all!
Tanya helped me undress and remove my makeup and allowed me to shower. We shared a drink and a cigarette whilst I slowly dressed and we discussed how the evening had gone. She gave me a few more makeup tips and then it was time to leave. I thanked her profusely for leading me through my first sexual encounter as Michele and she said she did enjoy it, even though it was 'work'. I left her apartment and went back to my hotel where I re-lived the event in my mind and masturbated before I fell asleep utterly content.
I swear to you good readers that the above account is true (as best as I recollect it anyway). I have been with other Transsexuals since, but it has never as good as it was in Sydney with Tanya. I have enjoyed the encounters, but the girls have always been unable to gain or maintain an erection; and lets face it girls, us Trannies love a big hard cock!
I thought my musings would be able to be kept to one single article; but as usual I have babbled on and this essay is already sixteen A4 pages long. I will publish part two a little later and include my experiences with a woman, my first experience with another Transvestite, a couple of experiences with male Admirers and one of my group sex encounters. If my reading audience is not happy with this form of writing though, please provide me with feedback and I will cease and desist.
To all of you who have provided feedback to me; I thank you all. Feel free to email me and I might even send you a picture or two of me at play! Once again thank you all for reading my stories.