tagTranssexuals & CrossdressersFirst Sexual Crossdress Experience

First Sexual Crossdress Experience

bymarshall11111©

How my secretary found out I'm a bi TV and how me and my TV friend educate her into some of the more zany aspects of TV sex.

***

As I laid back against the wall of the toilet with my nylon-clad thighs spread wide and my erect cock jutting up lewdly from between them, the wooden door in front of me slowly opened to admit the guy from the stall next to mine.

"Oh yessss!" the guy hissed quietly, slowly wanking his rigid cock and bolting the door behind him as he took in the erotic sight of me lying back in front of him, me now totally exposing my sexy undies to his gaze, "That's nice -- very nice!"

"Hi, I'm Suzy!" I smiled in a low voice, "What would you like to do to me?"

"I'd like to... fuck you -- and then watch you sucking me off!" he replied.

"Mmmm! D'you want to fuck me lying on my back, or doggie-style?" I asked.

"Just like you are now -- on yer back!" he replied, "With yer legs up and over my shoulders, so's I can push my cock deep inside you."

I reached down and took hold of my nylon-clad legs behind my knees, and pulled them up to my chest -- squashing them against my 36b hormone induced tits.

"Like this?" I smiled.

"Yeah... exactly like that!" he grinned.

He stepped forward and positioned his knob-end up against my puckered ring before slowly easing the purple bulbous end of his cock past my sphincter- muscles and easily sliding it inside me. Having been fucked many times before, I'd taken the trouble to dilate my sphincter-muscles by using a dildo on myself, and also liberally lubricating myself with some KY gel before coming out that evening.

"Christ, that feels good!" he gasped as he slowly sank all the way into me so's he pressed his pubic hairs up against my ass, "Nice and tight!"

"It'll feel even better when you start fucking me!" I breathed, "Slide that beautiful cock of yours in and out of me and don't stop until you've filled me with your cum!"

He placed my legs over his shoulders and did as I said -- sliding deep and powerfully into my suctioning ass with his hot cock!

"Oh yeah... fuck me! Fuck me and fill me, you bastard," I whispered hoarsely.

He laid over my folded body -- slamming his rigid cock into my willing ass and gasping for breath with the effort of thrusting into me!

I quickly reached down and unbuttoned my blouse -- flinging the material aside before undoing the clasp of my front-fastening bra -- the two lacy cups snapping apart to lie limply at my sides and totally exposing my now naked tits to the guy's gaze!

"Ohhh... spurt your hot cum deep inside me!" I urged him as I caressed and squeezed my firm tits with my hands, "I want to feel your cock throbbing and jerking inside my ass as you spurt your thick and creamy spunk deep inside my guts!"

I'd learned in the past that 'talking dirty' to a guy that was fucking me, soon had him coming and increased the lust he was feeling as he pounded into me!

Sure enough, a few moments later he gasped that he was getting very near to coming and that I'd soon be feeling him emptying the sticky contents of his balls deep inside my guts -- just as I'd wanted! A few seconds later I felt his cock harden and swell even more than it was already -- a sure sign he was about to come!

"NOW!" he gasped suddenly, "I'M COMING... NOWWWWWWWWW!"

I could feel his cock jerking deep inside me as he spurted his cum into me -- him no longer sliding all the way in and out of me, but now fucking his throbbing cock into me with short, sharp thrusts and gasping out loud and in time with each spurt!

He then slowed to a stop and laid over me, fighting for his breath before slowly pulling out of me and standing between my splayed thighs.

His semi-hard cock was now dangling between his thighs and slowly dripping cum before I quickly sat up and sucked the cum-coated knob-end into my mouth -- saving the precious fluid and swallowing it down!

"We don't want to waste any of your gorgeous cum -- do we?" I grinned as I pulled off him and licked my lips as I looked up at him.

"Don't worry, there'll be plenty more for you to drink!" he grinned back at me, "Just you wait and see!"

I grinned broadly at him before I sucked his cum-coated cock back into my mouth and 'deep-throated' him -- his cock once more beginning to stiffen and grow larger.

He stood before me and slowly 'face-fucked' me as I leant forward and wanked on my own rigid cock -- his own cock now rapidly growing in my mouth so's I couldn't easily deep-throat him any more.

"Here, let me toss myself off into your mouth!" he said, taking hold of his now rigid cock, "I want to watch my cum spurting into your mouth and then you swallowing it!"

I slowly slid off the toilet seat to kneel in front of him before upturning my head, so's my open mouth was directly facing his swollen knob-end.

"Is this okay?" I asked him.

"You just stay like that, and I'll direct my cum right inside your mouth!" he replied.

"Shall I keep my mouth open until you've stopped coming so's you can see your cum lying inside before I swallow it?" I asked.

"Yeah... Yeah, that'd be great!" he grinned.

His fist rapidly slid up and down the length of his rigid cock and his face contorted with the effort of him wanking on his hard cock. Then it changed and he told me he was getting near to coming and for me to get ready for his second load of cum!

I dutifully opened my mouth as wide as I could and he pointed his purple knob-end directly at it -- a thick spurt of thick and creamy cum suddenly jetting from the end and landing on my tongue before being quickly followed by another, and another!

In all there were five good spurts of his thick and creamy cum now resting in my open mouth, and so I raised myself up and proudly showed him the load I now had there.

"Swallow it... slowly!" he said quietly, "Then show me your empty mouth!"

I closed my lips and rolled back my head before swallowing his cum and letting him see my throat moving as the slimy load slid down to my belly -- only then did I look back at him and open my mouth wide to show his cum had gone!

"Beautiful!" I grinned, licking my lips clean of cum, "I could drink that forever!"

"You're a horny bitch -- I'll say that for you!" he grinned, "And a great fuck!"

"Thank you. I hope we meet up again -- real soon!" I smiled.

"Mmmm, you can bet on it!" he smiled before he turned and walked out of the stall.

I left the door unlocked and tidied myself up before settling back for a ciggy and waiting for another cock to suck or get fucked by.

Before I continue with some more of my experiences as a bi transvestite, I'd like to tell the reader a little about myself and my background, so's you can have a mental picture of me when I'm describing some more of the things I've done in the past.

Although I call myself Suzy when I'm dressed as a woman, my real name's John.

I live alone in a very large house on a landed estate -- inherited from my late mother and father after their untimely and tragic death in a road accident three years ago.

I have over twenty general staff that help me run the estate and see to the everyday needs of caring for 3,000 acres of woodland, rolling moors and hillsides, with one estate manager who is in overall control and who is directed by me in estate matters.

The main incomes are from the shooting rights of the estate, the three tenanted dairy farms, and from the overall forestry management.

As far as the house is concerned, I have two housekeepers that cook, clean and run the house for me, and a secretary called Anne that deals with the business side of things with me. She is the one I spend most of my time with in my office -- and it has to be said that we've become very good friends as well as co- workers. She deals with the legal stuff and farms it out to my solicitors and accountants after I've made the decisions and passed them on to the various workers. (She also makes an excellent cup of coffee!)

Now more about my personal life...

I'm 25, very slightly built with long dark brown hair that's tied back during working hours in a short pony- tail. This means that I can have my own hair done in a feminine style when dressed as Suzy -- something that now only takes me half an hour to do.

After taking a course of female hormones, I now have a pair of firm 36b tits with perky nipples that fill my bra-cups beautifully, but aren't too prominent during the day when I'm forced to wear a shirt and jacket.

Because of my position on the estate and my standing in the shooting fraternity, I keep both my bisexuality and my intense passion of wearing women's sexy undies a closely guarded secret -- the only other person knowing both of my bisexuality and love of wearing feminine things, and also who I am in everyday life, being another trannie called Michelle.

'She' frequently visits me when everyone's gone home in the evenings, and we have had many sexual escapades together, sometimes us walking around the estate together whilst dressed in our sexy stuff and with us usually ending up in the woods, where she gives me the best fuckings I've ever had!

The reason is, that she has the most fantastic cock and truly massive knob-end I've ever seen on a cock in my life -- really big and bulbous! As if that wasn't enough, she can come six or seven times in one hour -- each 'come' having enough thick and creamy cum to nearly fill a teacup! Michelle would rather fuck than be fucked -- the exact opposite of myself -- so you won't be surprised when I tell you that I've walked all the way back from the woods hundreds of times with her cum still oozing from my gaping ass, with loads of it still dribbling down my nylon-clad thighs when we've walked through the front door of the house!

To satisfy my lust for wearing women's clothing and sexy undies, I have a massive collection of clothes and undies secreted in the walk-in wardrobe of my bedroom. These mainly consist of many styles and colours of sexy basques, lacy bra and matching suspender-belt sets, various styles of nylons and several wigs, along with many styles and colours of skirts, tops, and blouses -- a great deal more than most women would have at home to choose from! Of course I have to clean and press everything myself so's my housekeepers don't see them!

I had my first bi encounter when I was 13 and walking in the same woods I use today.

It was a hot summer's evening and I was watching one of the workers. We got talking about things and he asked me if I had a girlfriend? I told him I hadn't and we talked in more depth about sex and obviously, shagging. Things really took off when he pulled out his seemingly massive cock for a piss! Because I'd never seen a fully grown guy's cock, my eyes were riveted to it, and he noticed -- him then asking me if I'd like to hold it for him? I eagerly took hold of the rigid tool and felt my own cock starting to stiffen -- much to my surprise and embarrassment! He noticed that as well and asked me if I liked what I was doing, and the feelings I was experiencing?

I admitted I did like it, and of course one thing led to another with me soon squatting down in front of him and eagerly sucking his cock for him as I wanked him!

He soon shot his thick load in my mouth, and it seemed the most natural thing in the world for me to swallow my first mouthful of cum -- much to his delight!

Needless to say, I was up in the woods almost every day from then on for my daily drink of his cum, and things soon developed to where we went deeper into the woods one day, where I got my first fuck, with his cock spurting deep inside my ass!

It hurt a little for the first few seconds the first time, but it was made easier and less painful by the liberal amount of 'Vaseline' he 'happened' to have with him that day!

From then on I was fucked almost every evening that summer and was firmly hooked on having a guy spurting his thick and creamy cum deep inside my ass!

One weekend when he wasn't working, I tossed myself off and imagined I was being fucked by his massive cock, by pushing the toilet-brush handle in my ass -- a poor but necessary substitute for the real thing!

And because in the past, I'd frequently raided my mum's undies drawer and worn her bras and panties to have a wank in when she and dad were out during the day, my love of undies intensified in the weeks to come, as I imagined myself to be a woman that was getting fucked by a guy as I laid back on the bed wearing nothing but mum's bra and panties, with a courgette or carrot from the fridge wedged firmly up my ass!

When I told him what I'd been doing at the weekends, he asked if he could see me wearing my mum's undies when I next came up for a fuck?

My heart was beating madly as I made my way up to the woods the following evening, not only in anticipation of a good fucking, but also with knowing what I was wearing underneath my clothes for the first time outside my bedroom, and especially because I was going to let someone see me wearing them before they fucked me!

He asked me if I was finally wearing some sexy undies for him and I parted my shirt to show him my mum's black bra underneath. His eyes nearly popped out of his head and he quickly led me to our spot in the woods where I stripped of and proudly stood there, wearing nothing but a black bra and panties!

"Fucking beautiful!" he breathed as he stroked the empty lacy cups of my bra and felt the rigid shaft of my cock through my panties. He immediately undid his pants and took out his rigid cock before telling me to get down on all fours! I wasn't quite sure what he meant because I'd never been fucked this way before and had always laid on my back while he fucked me.

"I want to fuck you like the horny bitch you've become!" he said as he guided me into position, "Now just hold on while I make you nice and slippery!"

I felt him pull my panties to one side and apply some 'Vaseline' to my ass, and then felt his rigid cock sliding all the way inside me -- his balls pressing against my ass and his knob-end butting up hard against the inner walls of my ass!

"Oooo yesssss!" he breathed softly as he gripped my hips and started to fuck his cock in and out of my ass, "Now you not only feel like a woman, you actually look like a woman that wants a good fucking!"

He must've been really turned on by fucking me in my sexy black undies, because he soon came -- violently! And instead of pulling out like he normally did, he left his cock inside me and gave me another great fucking -- straight after the first!

It was as I suddenly came and spurted my own load of cum onto the ground without even touching my cock, that I realised how turned on I'd become whilst getting fucked and wearing mum's sexy undies, and how turned on other guys got as well!

"If I buy you something else to wear for me besides your mum's bra and panties, will you wear them for me?" he asked quietly as we lay back to recover.

"Of course I will!" I replied, "What is it?"

"Two things actually... a black suspender-belt, and some nylons!" he replied, "Now seeing you wearing those will be a tremendous turn on for me!"

"Mmmm, and for me as well!" I replied, with a tickle running through my guts!

We sucked and fucked all through that summer and the next, until dad dismissed him for bad timekeeping. I was devastated to say the least, because I'm sure it was him that made me what I am today. He insisted I always took the part of the woman during our fantastic sex romps together, and enhanced my love of wearing women's undies by telling me how sexy I looked in them and explaining to me how my whole personality changed from being that of a horny young lad to me becoming a lusty young slut when wearing them!

From then on I frequently wore my stuff under my everyday clothes and got a real kick out of me knowing how I was dressed when walking through the town or nearby park, in search of guys to fuck me and to share my secret with them.

In an effort to meet up with guys that wanted me to suck them off or fuck me in my undies, I often went down to this park and sat on a bench by the river of an evening whilst wearing nothing but my bra, suspender- belt and nylons under my lightweight raincoat -- the front of which I strategically left partly open, to let anyone that looked close enough see how I was dressed underneath!

I'd had various levels of success by trying this hit and miss method -- sometimes not scoring all week, and then scoring three or four times in one week and getting someone's sticky cum inside me -- from one end or the other!

A considerable benefit also being that I learned from some of the guys about many other places where I could meet guys that'd be more than interested in fucking me whilst wearing my stuff -- two places mentioned most being the toilet block in the Corporation Park at the other end of town, and a quiet lay-by about 5 miles away.

The lay-by was out for the time being because I was still too young to drive, but the toilets gave me many good fucks from the guys (and women) I met there -- Michelle being one of them nearly three years later!

I was standing outside the toilet block and having a ciggy in the gathering gloom one evening, when I saw the figure of this woman walking towards me. She smiled and said hello as she passed me to go inside the toilets, and I returned the greeting.

I was immediately struck by her beauty -- and even though I only got a fleeting glance of her as she passed by, I decided that I'd go and sit in the stall next to hers and peep through the glory-hole to get a sneaky look at her sitting on the loo if nothing else!

My heels 'clip-clopped' on the tiles as I walked across to the stall next to the one with the door closed, and I went inside -- leaving my door unlocked as I usually did.

I removed my coat and leant back on the wall with my legs spread wide and my cock lewdly jutting up from between my nylon-clad thighs as I gently wanked it.

I was just about to lean forward and look through the hole, when I noticed some movement from the other side!

So, she was having a crafty look at me and what I was doing, was she? Well, let's give her something to see, I thought to myself.

I slowly stood up and moved to stand directly in front of the glory-hole before leaning back against the partition and spreading my legs as I started to slowly wank myself!

A few moments later I saw her watching me intently as I blatantly wanked myself, and then plainly heard the jingling of what I assumed to be her charm bracelet, as she squatted there -- obviously strumming and rubbing her clitty!

I then saw a beautiful pair of red lips push up against the hole and her tongue licking them -- an obvious sign that she wanted to suck me off!

So I edged towards the hole and pushed my cock forward -- parting her lips and slipping into her hot mouth! As I thrust my hips back and forth, I felt her sucking on my throbbing cock and making my cum rise rapidly from my balls. A few moments later I was emptying my sticky load into her suctioning mouth!

I was surprised with the speed at which I'd come because I can usually make it last for several minutes -- even when I'm really excited.

It wasn't until I thanked her and she pulled away, that I took a quick look through the hole to see she was dressed only in a lacy white basque, white lace-top nylons, and white high-heels. And as she sat down on the seat, laid back and spread her knees apart, I got the surprise of my life! She was in fact a 'he' and had a truly magnificent thick cock jutting up from between her nylon-clad thighs, surmounted by the biggest knob- end I'd ever seen! It resembled a very large closed-cup mushroom, and was crowning a thickly veined shaft about the size of the cardboard tube from the inside of a kitchen-roll!

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