• Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • TS Sexy-Tary

TS Sexy-Tary

I had taken the decision to live full-time as Georgia about 5 years ago and now, in my late 20's almost 30, I have finally allowed myself to be who I really am – a fun-loving, dead-sexy Tgirl who wouldn't change anything I have, or am, for anything in the world. As an example of that, the following is an example of how my life has evolved and the full-on sexy fun I am encountering as a result of it...

Gabi was a very well-to-do woman, in her mid-thirties, and ran a rather successful PR consultancy; I worked for her for about a year or so while I was working out what I wanted to do with my career before moving on. During that time I was employed as her PA and kept a very officious little routine going. The best thing was, she wasn't aware of my "other talents" shall we say. I had managed to get the job through a friend of mine who already worked there and knew that I was looking for a high-class position as a PA and thought this would suit...as it turned out it suited beautifully. My friend Ida knew of my "other life" and was keen to get me out and about, convinced of course that I passed very acceptably as a young woman.

I had been in the job for about six months and during that time I had a few encounters with Ida in the women's bathroom and the office itself a few times when we worked late. Mmmm, when I think of the amount of times I had Ida kneeling between my silky legs sucking on my hard throbbing girlie-cock, or with her bent over the boardroom table getting royally fucked, with our clothes all bunched up and dishevelled, I get so hard and horny I just have to go and relieve myself in the Ladies - but I digress....

You see although Gabi never made any direct pass at me or gave me any impression that she was the slightest bit "that way" she would always comment on my dress sense or tap me lightly on the butt or place a caring hand at the small of my back as we passed through a door or into the elevator. On this particular day I decided to be a little haughty with my dress sense and arrived at the office wearing a sexy little short skirt in dark navy blue with small white polka-dots all over it. The skirt had a lot of flare to it and was finely pleated in very lightweight rayon. It had an almost see-through quality to it. I chose a simple white long-sleeve button up blouse with small pearl buttons and under this I was wearing a white camisole with a nice lace panel across the breast area. The cami was clearly visible under the blouse. I had on very sheer white pantyhose that had a nice sheen to them with simple, classic dark navy pumps with a nice 4" heel. Covering and protecting my girlie-cock was a nice white panty-shaper...so tight 'my bits' were able to be held in check under the loose skirt.

All day Ida kept brushing her hand up under my skirt and teasing me when the other girls weren't looking. In fact all the other girls knew about Ida and I, only they thought we were a pair of lesbians and didn't mind one bit...well we were in a way I suppose. Due to Ida's attempts to get into my panties so to speak, I was feeling considerably horny and was just about to head to the bathroom to "take care of things" - again, when Gabi called me in to her office.

"Ah Georgia, thanks for sparing the time. I'd like to have a little talk to you about a few things, could you umm, close the door please?"

Curiously I turned and as I closed it I noticed Ida giving me a wink and a knowing smile, "wonder what this is all about?" I thought to myself. I sat in the chair in front of Gabi's desk and looked into her eyes, for some reason she seemed distant and hesitant.

"You've been with me now for about six months I believe Georgia," she stated, "and in that short time I have come to get to know you quite well and umm, well...this is going to be a little difficult for me, so bear with me....umm, I have to admit, with you around the office...well, aaahhh - oh shit! Look, simple fact of the matter is, you turn me on something fierce!" she just blurted it out! "There are plenty of good-looking young ladies that work here Georgia, but you...you are special for sure."

I looked at her stunned and thought, "god does she know what she is getting herself into here?" So I said, "Gabi, before you say anything else there is something you should know."

"Oh you mean that under all those sexy outfits and that feminine demeanour, you're actually a guy?" I was stunned!! My mouth nearly hit the floor and I was completely at a loss for words, just stammering and trying to come up with a response, any response to hide my blushing and obvious embarrassment. "Don't worry; I've known about that for a few months....Ida told me. And don't get cross at her, I begged her to tell me – I noticed something different about you the day you started and it wasn't just a confidence about you. You carried yourself differently than the other girls. And then I started noticing the relationship between you and Ida and I know she isn't gay – well, not in the strictest sense of the word anyway. I have to be honest, she didn't betray any confidentialities easily, but a few glasses of wine later, a bit of giggly girl-talk and some minor 'play' - which was rather enjoyable I might add – and she spilled the beans on you. You see that is what turns me on more than anything! The fact that you have been swanning around here and hardly anybody has noticed...you and Ida must have some serious fun when I'm interstate or while you are working late?!"

By this stage I could feel some familiar stirrings in my panties that I was finding hard to ignore. Gabi is an incredibly attractive woman, confident, rich, and impeccably dressed at all times - the typical corporate power-woman. Here I was being told that my persona was acceptable to her and that it actually turned her on!! I was getting so hard it was really difficult to hide...but then I don't think she would have wanted me to hide it anyway!

"What's the matter my dear? Cat got your tongue?" she asked as I sat there totally dumbfounded, somewhat less embarrassed and just slightly turned on all at the same time. I had just assumed that Gabi was seeing someone and, of course, you have no idea what anyone likes unless they actually come out and say it, or show you, I suppose – you just never know.

Gabi looked at me and smiled, then said, "Here, let's make this very simple - why don't you come round here in front of me Georgia?" I got up slowly and went around her desk as she asked; she pushed her chair back to allow me to stand with my butt resting against her large desk – standing directly in front of her. I noticed it had been cleared of the usual clutter...all those fantasies I had had about Gabi and I on this great desk may just about come true. I was resting back against her desk, my legs slightly apart; Gabi was sitting in front of me, her long lean legs, shiny in their black sheer pantyhose stretching out in front of her, with her feet crossed just between mine. Her simple black skirt pulled tightly across her thighs and, in mind, it begged to be bunched up around her waist. Her jacket was open revealing a lacy bodysuit covering her ample breasts. My hands were at my sides, on the desk, supporting my trembling legs.

"Such gorgeous and sexy legs for a guy, you must really take care of them to have them looking so good. And your choice of clothes I must say is very sexy and classy. You really do make an effort don't you Georgia? If only all the girls in the office would take a leaf out of your book. We could have one of the best looking PR companies around." 

Looking down I managed to find my voice and offered, "Technically, I suppose I am male, but in my mind and my view of myself and the person I project, is and always has been female. For instance, my breasts aren't implants, they're naturally grown – a little on the small side maybe, but they are all mine. My hair is mine – been growing that for many years. The only thing that is still male really...well, you know...and quite frankly Gabi, I wouldn't change that for anything in the world."

As Gabi was listening to me her hands were lightly stroking up and down my pantyhosed covered legs, her fingers and her legs rubbing against mine, felt electric to the touch. She looked up into my eyes and asked, "I believe you believe that you're a woman, but tell me, surely there's an element of erotica involved? It must get you hard sometimes right? I mean the dressing, isn't that also a part of satisfying a sexual urge or fetish too?" The whole time Gabi was talking to me, her hands never left my legs, and they kept slipping up between them as well. I started telling her that I loved everything about being a woman, and that yes, the sensation of being dressed and having sex while dressed was very real. She smiled and started pressing her fingers into my crotch. Then she asked, "Do you think about having your cock sucked while in your pretty outfits, hmmm? I bet you'd love to have a nice hard cock up your arse wouldn't you Georgia? Sexy little sluts like you must dream of a good fuck all the time."

There are moments in a Tgirl's life that just happen – and when that moment happens you just know that you've got to run with it and make the most of it – this was one of those moments. I simply smiled and offered, "more than you could know Gabi – more than you could know."

Gabi's hands had started to alternate between my sheer legs and her full breasts, her jacket was wide open and I could see her breasts heaving under the confines of her lacy cami. Her legs were opening and closing tight against each other, as she was obviously getting hot and wet deep inside herself.

"Why don't you lift your skirt my dear and show me what you have under there?"

I slowly inched the hem of my skirt up to reveal the tight panty-shaper I was wearing. Gabi's hands literally flew to it as she began to run them all over the tight material. "Oh myyyy!! Look how hard you are! I have to see it, can I see it please? I want to feel it too. Will you let me suck you please Georgia!? Please?!?" She literally begged me – I couldn't believe it.

Looking down at her I felt a sense of power and thought, what the fuck, she started this, so I told her, "if you want to see it, you'll have to take them off yourself, but...I want you to kiss and worship my panties as you take them off. I want to see your lipstick marks all over them as you take them down...and I want you to do it slowly, so I can see you actually enjoying it!" Gabi began to slowly inch the tight panties down over my butt and thighs, as she did this her hot mouth blew sexy kisses and licks all around my throbbing girlie-cock and hips till she had them pulled right down to my feet. She leant down and pulled them over my shoes. She studied them for a short while and murmured something about getting herself a pair. Her face came back level with my girlie-cock, which by now was starting to leak drops of pre-cum.

Looking at her I ordered, "Now you little slut, you wanna suck me off and taste my girliejuices? Then lick me through my pantyhose. Your mouth and tongue aren't good enough yet to touch my girlie-cock directly. I want you to make me cum through my pantyhose and then I want you to lick me clean, and suck all the cum from them before I even think about whether I will fuck you okay?!!"

Gabi obviously didn't care what I told her, she just couldn't hold back, her hungry mouth clamped over my throbbing bulge through my sheer pantyhose and quite soon her tongue was licking me furiously. Her saliva and my pre-cum mixed to create a warm, moist patch across the front of my pantyhose. I laid back, spread my legs and let Gabi work her magic. The sounds of her hungry sucking and the sensation of her mouth rubbing my throbbing girlie-cock was too much. I pulled her close to me and mashed her face into my crotch. I wrapped my pantyhose-covered legs around her and pulled her even tighter into me. I leaned forward and struggled to get her out of her jacket. The lacy bodysuit she had on was gorgeous and my hands began to caress the soft material. I reached further down and pulled up her tight skirt, running my hands all over her silky butt. Gabi had come prepared, she wasn't wearing panties!

I locked her tight against me and pushed her face into my rock-hard crotch. I could feel the build-up of an impending orgasm and ordered her, "Take it in your mouth you slut! Suck me, suck me through the pantyhose!"

Gabi gathered the material as best she could and sucked harder and harder managing to get about two-thirds of my shaft down her throat, the sheer pantyhose stretching tightly and creating an electric constricting feeling as her tongue slavered all around it. I started to fuck her mouth, my hips thrusting to meet her head bobbing between my legs. I held her head and looked down to see this gorgeous woman feasting on my girlie-cock. I couldn't hold on any longer, and I didn't give a flying fuck if anyone could hear us...

"FUCK GABI! Suck me, suck me hard! Harder!! Oh yeah! OH FUCK! YES!! Shit, I'm coming, I'M COMING!!!" I yelled as I shot a huge load into my pantyhose and her mouth.

Gabi sucked and sucked me until I could feel myself start to subside. She wouldn't stop though, her mouth and tongue literally sucking and licking me to the point of being too sensitive to touch and I had to pull her away for some relief. She moved up to me and lying against me kissed me hungrily and let me taste my own juices as her tongue searched for mine.

Looking me in the eye, and gasping for breath, she said, "I am so fucking horny right now, you better be able to do something with that, or at least that pretty tongue of yours or I will have to resort to other means!"

I turned her over and laid her on her back on the desk, and tugged her skirt roughly up around her waist, and while I stood there between her legs letting her feel my silky thighs rubbing against hers, I ordered her to play with herself.

"Show me how much you wanna cum Gabi," I teased, "show me what a good little slut you are. Show Georgia just where you want this big hard girlie-cock to go."

As Gabi began to slowly rub her fingers inside and outside of her pantyhose, I inched forward till my bulge was resting against her very wet pussy. I pushed her legs wide and lifted them slightly - I unzipped my skirt up let it drop to my feet, not caring to step out of it (it felt sluttier that way!) and while she continued to masturbate herself, I humped her pussy with my own cum-soaked, pantyhose-covered crotch.

Gabi began to moan and beg me to fuck her... I told her, "In good time, I have to get all nice and hard again you selfish bitch."

That only made her beg me more, and as she continued to talk dirty to me I could feel my girliecock getting harder and harder. I leant over and grabbed a pair of scissors from her desk and cut a slit in the crotch-panel of her pantyhose. Her fingers flew to the hole and eagerly began finger-fucking herself.

"Please Georgia; I need you to fuck me. I want to feel your hard girlie-cock inside me! Fuck me! Fuck me please!!!"

I pushed up between her legs and in one motion, jammed my girliecock deep into her hot cunt – she was so fucking wet I slipped straight in to the hilt!. Gabi gasped and moaned as I pushed hard into her, and immediately she locked her sexy legs around me. She was possessed, her hips humped me furiously, her heels dug into my butt as she attempted to fuck herself on my girlie-cock.

It was honestly only a matter of mere minutes before I could tell she was on about to cum and all of a sudden she was bucking and yelling, "YES! YES!! YES!!! Oh God, OH GOD!! FUCK ME YOU SLUT!! FUCK ME HARDER!!! HARDER!!!"

I pounded into her as hard as I could, trying to get her to cum as hard as she possibly could. Just then I saw the door fling open and Ida and the other three girls stumbled in, totally in awe at the scene unfolding on Gabi's desk. Seeing the knowing smile on Ida's face, and locking eyes with her, I drove into Gabi again and again, feeling her orgasm take charge and her juices literally gush from her soaking wet cunt. She humped and fucked me for ages till she finally calmed down.

During all this, Ida and the other girls had wandered over, curiously interested – Ida had wandered around behind me and was pressing into me, helping me finish fucking Gabi, while running one of her hands over my sheer legs, with her other hand up between the legs of the other girls' skirt, while that girl leaned on the desk beside us, hungrily searching for pussy between some lovely sheer, tan-coloured legs. The other two were locked in a very sexy french-kiss, tugging at their dresses and skirts and undoing buttons – all which suggested that this could well be a very long afternoon......

  • Index
  • /
  • Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • TS Sexy-Tary

All contents © Copyright 1996-2023. Literotica is a registered trademark.

Desktop versionT.O.S.PrivacyReport a ProblemSupport

Version ⁨1.0.2+795cd7d.adb84bd⁩

We are testing a new version of this page. It was made in 98 milliseconds