The Car Crash

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A long adventurous night, Stephanie shows she is a Libertine.
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Chapter 1

Travelling north on El Camino Real on the San Francisco Peninsula through the endless car dealerships, shopping centres, convenience stores and bars, punctuated by traffic lights, I realized I was going past where there used to be a bar called the HipHugger, which I had visited many years ago while trying to convince myself unsuccessfully that I was a real man.

I moved my head to look forward just a little too late, the sound of the tyres failing to grip on the pavement like sacks being dragged along staccato style as the ABS failed to stop me. The red tail lights of the car in front seemingly immune to the traffic light being green, getting closer with every millisecond, each millisecond lasting a minute, the elegant court shoe pressing hard on the brake pedal clearly not going to prevent the impact. The sound of twisting metal cut short by the white fabric of the airbag enveloping my face. The world moved surprisingly slowly and apparently gently.

The little Nissan hire car that I was driving crumpling into steel origami with staggering ease even though I had not been travelling that fast. The big Mercedes in front of me, that had tried to move forwards as I'd approached, moved across and parked the other side of the junction, not even apparently scratched. I sat there dazed for a minute. Everything now silent. I pushed the door open, picked up my handbag from the footwell; luckily it was zipped closed so hadn't strewn its contents around the car, and I went to speak to the driver, then we saw a police car pulling up behind us.

Earlier that Wednesday afternoon I had checked in to the same hotel as I always did on my business trips to the Bay Area. Greeted by name by the handsome tall black receptionist who always smiled at me, at least since I had managed to lock myself out of my room wearing a tight burgundy bodycon mini dress.

"We have your favourite room near the pool, Mr. Reeves, with the private garden."

"Thank you, good to be back."

There aren't many places in the world where a T-girl can allow her two worlds to merge without worrying, and I was thrilled that I got to travel to one of them so often.

I had slept pretty well on the long-haul flight from London in Virgin Upper Class, starting the flight with a gin and tonic at the inflight bar, admiring the crisp cut of the flight attendants' bright red uniforms and, as every time I flew, wishing we could change places. Even so, I knew that I should get some sleep, as my body was already telling me it was night-time.

As I always did, I quickly unpacked, hanging my dresses and blouses in the wardrobe, filling the chest of drawers with my lingerie, arranging my makeup in the bathroom and placing my drab everyday clothes in the last drawer. I stripped off my clothes, putting them in the linen bag in the bottom of the wardrobe, then in the bathroom I shook the pink aerosol and sprayed the white foam thickly over my body from the neck down.

A few minutes later, always a couple of minutes longer than they say on the can, I stepped into the shower. Luxuriating in the hot water and expensive body wash and shampoo, I washed away the flight along with what little hair had grown since I was last here a couple of weeks ago. Patting myself dry with the soft towels and smoothing the expensive body lotion into my smooth skin, I drew the blackout curtains, slipped on my gold satin and black lace nightdress, and curled up in the huge bed for a few hours sleep. I set my alarm for 5:30pm, so I could have two hours to get ready for my date with Richard this evening, I sent Richard a quick mail confirming I'd landed, then drifted off listening to the sound of the fountains in the gardens.

The sound of my phone alarm pierced through my deep sleep. As much as I travel, I don't think I'll ever get used to that; still, I don't have too many issues with jetlag. I went to the curtains and opened them wide, allowing the late afternoon sun into the room. One of the things I love about those garden rooms is the level of privacy: even with the curtains wide open there was no one that would be looking in. I put a capsule of coffee in the machine and hopped back in the shower, to wake up.

I went to my wardrobe to choose what to wear tonight. I settled on my gold bandage dress from French Connection; it's made of a really heavy fabric and always fits beautifully. It is a little low cut, but I know Richard likes that.

Choosing the right lingerie to go with that meant my new low-cut Triumph body. It's got enough shaping in it to give me the right curves, the bra cups are designed to boost a girl's "assets" yet it allows for a lot of cleavage to be on display. Despite having poppers on the gusset of the body I first pulled up my skin-tone dancers' gaff, pushing my balls home at the same time, and pulling my small penis back between my legs. Pulling the body on is always a little of a struggle, but always worth it, and as it settled on my waist and I pulled the straps up over my shoulders I could happily bid farewell to Mr. Simon Reeves for the night.

I made sure the cups were positioned well over my own very modest breasts and pulled the gusset together, pressing the pop fasteners and creating an absolutely flat front, my maleness gone. My own breasts, just under an A cup, were not enough for the dress I was planning, so I took out my large self-adhesive breast enhancers, Carefully positioning them, I ensured that my own breasts created the cleavage, and my breast forms filled the cups, giving a perfect illusion of large breasts: I knew Richard loved it!

Before starting on my make-up, I opened my Mac to check on the plans for this evening. I opened the reply from Richard. He has a penchant for rather public displays of affection and I never knew quite what to expect. What I hadn't expected was that unfortunately he was unwell, and his doctor had recommended he stay home in bed. Disappointed, I wondered what to do; open a bottle of wine and spend the evening in the garden? Invite the guy from reception over... probably not. See if another of my friends and occasional suitors were available for the evening?

I decided that was the best choice, and quickly sent mails to a gurlfriend who lived in Los Gatos and two gentlemen friends from the San Jose area. I knew they would get back to me fairly quickly so decided to use the time to do my make-up, I looked at the clock and saw it was 6:15, so still early.

Not knowing what I was going to be doing that evening, I decided not to be too dramatic with my make-up; a standard evening look, first some good foundation and contouring, including my cleavage, smokey eyes, with white eyeliner on the wet line of my eye to open them up, lengthening mascara, and a dark burgundy lipstick rather than a bright red. I finished my lips off with a plumping gloss coat and then just a very light dap of silver eyeshadow on the centre of my lower lip and a little brush of highlight powder on the swell of each breast.

Happy with the way my makeup looked I went to check on my messages. Vicky was at her holiday home that week, and of the two men only Laurence had replied. He was busy, but he'd be happy to play this weekend. He is a local Dom and dates with him always involved my bondage and spanking or flogging in some way. I sent him back a quick reply that I was booked into a hotel in San Francisco so may see him in the city. Then I opened up Craigslist. I quickly wrote a post saying I was an English T-Girl in town, who was interested in a date for the evening. If nothing else, it would give me a few interesting replies to read through with a glass of wine later.

I opened a new packet of black lace-top hold-ups and slid them up my legs, always relishing the feel of the nylon however many times I wore them. I made sure the lace from the top band was straight, with the seam at the back and that they were pulled up high enough not to show under the short dress I was planning. I lifted my dress from the hanger and carefully lowered it over my head, making sure I did not damage my makeup. I adjusted the shoulder straps, smoothed the skirt down and checked that my cleavage was on show, but not my underwear or breast forms. Next I brushed out my favourite wig and settled it in place.

Throwing my hair back, I looked in the mirror and mouthed "good to see you again". I quickly put on my jewellery and adjusted my delicate watch. I slipped my feet into a favourite pair of shoes, some leopard print courts with a 4 inch heel: high, but low enough that I could easily drive and walk anywhere. Then I sat at the desk and painted my long finger nails the same very dark red that I had painted my toes before I left. I always keep my nails long, at least 4 mm past the end of my fingers, and although colleagues very occasionally comment it's definitely worth it for moments like this, just like it's worth having my eyebrows regularly threaded: not too thin, but fairly high and arched, just androgynous enough to get away with.

Once they were touch dry, I went back over to my mail: another reply from Laurence, saying he'd let me know about the weekend. Nothing from my other friend. There were also about 30 replies to my Craigslist post; lots from guys much too young for me. I'm sorry, but I don't like being with someone that makes me feel old. Some more from guys who've never been with a T-Girl before, "but can I teach them..." or some that say they will "dress up in my clothes for me if I'd like..." I wouldn't like. I put those all in the trash. Quite a few who thought a three word reply and a picture of a dick, clearly cut and pasted as a reply to every "available" ad they saw counted as the clear face photo I'd asked for. They went in the trash too.

After a good cull I was down to a half dozen interesting replies. I answered those, asking what they had in mind for the evening. This time I didn't have to wait long. I got replies straight back, obviously surprised at getting an answer in the first place. After another couple of mails I decided I would go and visit a French gentleman apparently called Francois, just a few years older than me, who had moved to the Bay Area to work with a tech firm, and who lived between Sunnyvale and Los Gatos; he seemed fun, he was articulate and had his own place that he was inviting me to.

I went through what I would need in my handbag: lipstick (I was expecting I would need to touch that up), some gloss for good measure, some face powder, a hairbrush, my purse, which I swapped my ID into, a credit card, cash and a room key, my phone, lube, and condoms.. I slipped on my little black faux-leather jacket and I was ready to go: an extra spritz of perfume and I was out of the door.

I hopped into the little silver rental car, put the address into the satnav and headed off. It was around a quarter to eight. The quiet residential street was fairly unassuming, but each house worth well over a million dollars. The house I was going to was a mid-century modern: a lot of glass and wood, but private too. I pulled the car onto the drive beside a new Tesla, and gathering my things went to the front door, where I was met by Francois. I was used to Craigslist throwing up some surprises, but Francois seemed to be pretty much as he had said.

He invited me in, and we chatted a little, about his company, why I went to the Bay Area so often, and Europe. I was enjoying myself and happily accepted a small glass of wine. It was a superb chilled French white. He led me through to his sitting room. The house was very much open-plan and the sitting room was huge. The whole of the wall to the garden was glass and must have been 4 meters high and 12 meters long. The room was exquisitely but sparsely furnished, clearly a bachelor pad. He invited me to join him on his large sofa and he pulled me into his arms, his fingertips running gently up my side. He kissed me gently on the lips and thanked me for choosing him this evening. I told him that I had obviously made the right choice. He raised his glass to mine, and I finished the last of my glass and put it onto the table beside us. He offered me another glass, I was very tempted, but declined as I was driving, and still had jet-lag to contend with.

Francois pressed a button on his remote and a trans porn film started playing on his huge TV. I would have preferred some soft music, but it was his house. He rested his hand on my nylon covered thigh; my short dress had ridden up to show quite a lot of leg as I had sat down He was clearly a little nervous, but when I didn't stop him he started to caress my leg and his fingers found the lace at the top of my stockings. He pulled away very briefly to smile at me, then he said;

"Naughty girl Stephanie."

"That's what you want, isn't it?"

"Yes of course... I don't know quite how to ask this, but... how much do you charge?"

"Do you think I'm a whore then?" I asked, not offended. It wasn't the first time on Craigslist I'd been asked that question, it wasn't the first time that evening: half a dozen of the mails I'd received earlier had asked my rates.

"Well... I don't know, quite a lot of girls on Craigslist are..."

"Would it make a difference to you if I was?"

I toyed with the idea of telling him I was, I'm sure we have all fantasised about that... but that's a story for another day.

"No, honestly, I like you, and I'd just like to know."

"Well I'm not, but don't let that stop you treating me like I am."

With that he pulled me to his lips and kissed me, tentatively at first, then as I opened my soft full lips for him, his tongue invaded my mouth, kissing me deeply, exploring me as I caressed his tongue with mine. I enjoyed the slightly rough feel of his skin against my soft skin. I felt his hand sliding my dress up my thigh so that he could caress the white skin at the top of my thigh, brushing across the lace tops of my stockings before settling on the bare skin. As his lips left mine and he gently kissed his way down to my neck, I lifted my chin to allow him to feast on the pale white skin of my neck and my décolletage.

I slid my hands along his thighs, feeling the bulge in his trousers. I undid his belt and undid his zipper, my hands quickly finding his hot, hard flesh. With my hand I gently explored his cock: not huge, but quite long and thick enough. I was pleased to find he was uncircumcised, it would mean the head of his cock would be so much more sensitive.

I released myself from his embrace and dropped to my knees. I gestured to him to lift slightly and I pulled his trousers off, which he then kicked to the side. Looking him in the eye, I kissed my way along his thigh until I gently kissed the head of his cock. Sliding back his foreskin, the head of his cock glistened. Opening my lips, I welcomed his cock into my hot mouth, squeezing the underside of his shaft with my tongue. I slowly dropped my head down, my hands stroking his skin, one under his shirt up to his nipple. I pulled his foreskin back and rolled my tongue around his sensitive head to a gasp of "Oh my."

I pulled his foreskin up and teased my tongue inside between the head and his foreskin. It was delicious. Rolling my tongue around pushing his foreskin out as I found the ridge with the underside of my tongue and circled around it making his the head noticeably enlarge. I realised it and took the sensitive helmet, right in the back of my mouth, sliding past my gag reflex, my nose was against him, so I slowly started to raise my head before dropping again all the time caressing him with my tongue.

I felt his hands push the shoulder straps of my dress to the side, allowing the top of my dress to drop. Without breaking rhythm, I quickly stood and slid my dress off, allowing it to drop to the floor. Now just wearing my deep burgundy plunging lace body and my stockings and heels, I dropped straight back to my knees and started to increase the speed of the rhythm of my sucking. I kept eye contact with Francois, seeing him take in what I was wearing, and watching my lips around his cock. Briefly I lifted my mouth, licked the tip of his cock, licked my lips and then swallowed his cock deeply. I felt him start to pulse as his orgasm built. Then the first pulse, the jet of sperm filling my mouth, I closed my mouth to keep all his seed as he pumped me full, slowing then as he softened. I kissed the tip of his cock as I looked up at Francois and I let a little dribble of his seed run down my chin, dripping down to my cleavage.

Francois pulled me up to him on the sofa and into an embrace. I sensed he was having a slight post-orgasm guilt moment, so I just cuddled up to him while it subsided, and sure enough after a few minutes he turned to me and kissed me, although not deeply. He stood and refilled both our glasses and held mine out to me. Raising them, he whispered "thank you." I had one mouthful of the wine and enjoyed the sensation of it mixing with the remnants of his spunk in my mouth before swallowing it. I put my glass back on the side, aware that I had to drive back to the hotel shortly.

I curled up in Francois' arms as the porno kept playing. His hands started to caress me again, his fingers pushing inside the bra cups of my underwear. I could tell he was used to T-girls as he deftly found my own nipples beneath the breast forms, teasing them, causing them to grow and harden. We kissed deeply as his hand caressed my legs and stroked my arse, his fingers tracing the edge of my lingerie. My own hands were caressing his cock as it hardened again. I felt his fingers find the poppers on the gusset of my lingerie, then in one smooth motion he pulled them open, sliding the delicate fabric away.

His skilled hands quickly pushing aside the thong back of my gaff, he found my rosebud and gently started to work me open. Soon he pushed me back until I was laying on my back on the sofa. My head dropped back briefly, and I realized we were pointed straight at the porno where a shemale was being serviced by two guys. Francois pushed my legs up and wide, resting them over his shoulders. Quickly I reached beside me to my bag and pulled out a condom and lube. I made sure I was wet, while rolling the condom onto his shaft. I felt the tip of his cock opening me up as I looked into his eyes. Behind me I could hear the sounds of the girl being fucked as Francois slid himself deeply into me. His sizeable head split open my inner ring, filling me up and arousing my prostate. I knew that as he had recently cum he was likely to last a while, so I enjoyed the sensation of being truly fucked. I loved the way being on my back with my legs open allowed me to look into his eyes as he fucked me. He built his rhythm and continued to pound me. On screen, the guys had clearly cum all over the girl and Francois flipped us around so that he was laying down and I was riding him. I was impressed that he'd managed to do that whilst keeping buried deep inside me. I let him lay back as I fucked him with my arse, twisting as I moved up and down, squeezing him with my sphincter as his balls slapped into me.

He roughly pulled the tiny straps of my body down, then discarding the forms started to tease and twist my own breasts. I could sense that he was again close, so I lowered my breasts to his mouth, feeling his rough skin as he sucked and bit my tits. He urgently flipped me onto my back again, pushing my legs wide open. He pumped his pulsing cock hard into me and started to come. His second orgasm was more forceful than the first as I felt his cock pumping in my filling the condom nearly to the breaking point. I regretted that I had to use one, wishing that I could feel him filling me. As his orgasm was subsiding, he pulled out of me and discarding the condom he aimed the last couple of jets at my face and breasts. Then he pulled me into an embrace: no guilt this time.