A Shemale Vacation Ch. 03

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Tom must be Tamsyn once more to cross the border.
5.5k words
4.63
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Part 3 of the 3 part series

Updated 10/31/2022
Created 03/08/2009
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britneyfan
britneyfan
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At the French border, it was discovered that we had no passports. We were taken from the train and into a room for questioning. All four of us, Josh, Olly, Harry and myself, were terrified. Sure, we'd been in a sticky situation before on this trip, sticky particularly for me rather than the others, when we'd found we had no money in the Amsterdam brothel, but this was worse. This time we were in trouble with the authorities. I thought that we wouldn't be able to cheat or bribe or persuade our way out this time.

The room we were in was bare except for a table and chairs, there were no windows and the door was locked. We were trapped in here with no escape. Sitting across the table from us were three French border control officials with angry, frowning faces. They were big, tough guys and none of them looked like they were about to be sympathetic to our story.

"So, you try to sneak into our country," said the man in the middle, the biggest, most broad shouldered of the three and, presumably, the man in charge.

"No, no, we just lost our passports," Josh said, "We were robbed. They took all our money, cards, passports. Everything."

"So, then, how did you pay to get here if all your money was taken?" said the man on the left, a guy with a heavy frown and thick dark hair, eyebrows and a beard.

This was exactly the question I didn't want asked. I didn't want to admit what I had had to do to get the money for the rest of our trip. That pile of banknotes in Josh's bag was a permanent reminder that I had prostituted my body, dressed as a slut and got fucked time and again to get us on our way. Sure, I had loved the feel of dressing as a sexy woman and feeling that hard manhood thrusting inside me, but I was embarrassed as well. I didn't want the world to know, especially not these hard, serious guards.

"We were able to borrow some money," I said, quickly, not giving the others a chance to answer.

We sat in that room answering questions for about an hour, getting no nearer to any conclusion. Finally, they decided to search us, going through our bags, seeing if we had anything to smuggle into the country. They found nothing until they got to Josh's extra bag. The one that he had brought from Amsterdam, from the brothel, the one filled with all the money I had made as a whore.

Before opening the bag, Josh began to talk to the guards in French. None of the rest of us understood French but Josh seemed to be doing a decent job. He sounded very persuasive and the guards seemed quite receptive to what he was saying. I imagined that he was probably offering to bribe them with the money that was in the bag he was holding out to them, only he also seemed to be pointing at me. Whatever he was offering, they appeared to agree to it. He turned back to talk to us.

"Guys, I think I've got them to come to an agreement here," he said, "I think I've got a way out of this. I told them about the money in this bag and how we got it and offered them a deal."

"You offered to bribe them?" I said, excited.

"In a way," he agreed, "Look, I told them what you did to make the money, told them about Tamsyn's skills and success and they asked for a demonstration. If you let them have a free go then they'll let us go free."

"Again?" I said, "Come on guys, is there nothing any of you can do to help this time?"

"No," Josh replied, "It's got to be Tamsyn. Saskia and Edgar told me what a good whore you made. You're the only one that can get us out of this."

"We'll be really in your debt if you do this, man," Harry persuaded, "What other choice do we have?"

"Besides," smirked Olly with a nasty edge, "Didn't you like it? We could all hear your screams of delight from downstairs!"

"OK, fine," I agreed, resigned to the fact that once more I had no choice but to turn whore to help my friends and me out. And Olly was right, I had enjoyed it last time, "But I'm just Tom. I can't be Tamsyn without clothes."

"Don't worry about that," Josh said, "I thought these might come in handy," he opened the money bag, it was full of feminine clothing, "Saskia said that you'd probably want some of this at some point so I decided to take it with us."

To be honest, I felt a little annoyed and betrayed at this going on behind my back, at the sense that my friends thought that this would not be the end of my time as Tamsyn. After all, I had only done it the first time for them. However, I had already admitted that I had enjoyed the experience, and the sight of all those sexy clothes brought a lot of those feelings back. I would be lying if I said I was totally reluctant to agree to dressing and acting like Tamsyn the whore again.

So, it was with mixed feelings that I went through the clothing in the bag to find an outfit that I liked, while Josh turned to the guards interrogating us and told them that I had agreed to their request. I found something that I liked in a little red dress a black satin panties.

I couldn't leave the room to change so I just had to take the bag into the corner and strip naked, leaving my male clothes in a pile. I felt embarrassed and self conscious showing my thin naked body and small cock before my friends and the three tough guards. Even more embarrassing was watching them watch as I slid the sexy satin panties up my legs and noticing their reaction as they saw the feel of the smooth material made my cock quiver with excitement.

Fortunately, my body tends to be pretty hairless and had remained smooth since I shaved it prior to my first experience as a cross dressed hooker. Still, I decided to make my legs even smoother and sexier with some black sheer stockings. As I rolled them up my legs I was conscious of the leers of the guards and the inquisitive glances of my friends but I was also starting to enjoy the feel of turning back into Tamsyn.

The dress was a halter neck and I decided to do without a bra. I slipped it over my head and attached the strap behind my neck. It clung tightly to my chest and waist but the skirt fluttered lightly and sensually around my thighs. It was very short and just brushed the lacy tops of my stockings. Unlike the brothel, which had been full of mirrors, here I just had to guess how I looked, but the appreciative noises made by the French interrogators made me start to feel pretty good.

Rummaging further in the bag, I found my wig, the same platinum blonde bob as before, and some makeup. Without experience and without a mirror I couldn't do much with that, but at least made sure to paint my lips a lurid shade of scarlet so they would look especially sexily feminine as they went down on a hard cock.

"You make a very good girl, Tamsyn," said the lead guard, "Now you will let us fuck you before we let you go."

As he said this, he was unzipping his trousers, closely followed in this act by his two partners. They were still sitting in their chairs but had moved back so they were facing towards where I was changing in the corner rather than the table. I walked over to the three of them, trying to avoid the amazed gaze of my friends who had never seen anything like this from me. Although they had been aware of what I had done in the Amsterdam brothel, that was different from actually seeing me do the same before their eyes.

The three French guards had now pulled out their cocks, each had their hand wrapped around their meat, jerking it off as their eyes devoured me hungrily. I gave the same sort of lustful looks to the three cocks pointed in my direction. As I would have predicted from three such masculine looking men, their dicks were equally impressive and large, much more so than mine. In particular, the huge guy in the middle had a thick manhood that looked like it could almost match that of Saskia, the busty black tranny whore whose cock had been the first I sucked.

Just as with that beautiful black meat, I was drawn in towards these three throbbing French cocks. I desired them with every fibre of my body and I knew that without any further encouragement or incentive, I would still be getting down on my knees like I was now. I would still be leaning in and licking my lips. I would still be reaching out my hand to feel that alive warm hardness become stiffer and more excited at my dainty touch.

I took the two cocks either side of me in my hands, the hairy bearded guy and the younger blond who seemed a little nervous. Meanwhile, in the middle and right in front of my eyes, the thickest and longest, the dick belonging to the lead guard, dangled enticingly before my mouth, with the guard stroking it and waving it at me as if daring me to taste it. As I stroked my hands rhythmically along the trembling shafts of his two companions, I leant in even further and let my tongue play around the thick, bulging head of his manhood.

"Come on, whore, suck my cock," he said, his big manly face leaning intimidatingly over me.

I licked right up the length of that huge, veiny shaft, now certainly approaching Saskia's eight inches as it solidified to its true length, covering it with my saliva, making it slick and wet. All this time I was continuing to stroke his friends' cocks and now I turned my attention left to lick around the younger guy's dick for a few seconds causing him to sigh with pleasure. His cock was not as large as his superior but it was pretty impressive, uncut with a huge mushroom head that I slid between my lips and played my tongue over, leaving a smudge of my red lipstick around it.

I switched right and took the hairy guy's thick dick in my mouth next. I licked along the shaft as I stroked it, opening my lips to let the head play between them. As I did this, the man grabbed the back of my head and pushed his cock right in causing me to gag momentarily. For a few seconds he pounded his cock in and out of my mouth, fucking my face, before I could come up for air.

Putting my hand back to work on that dick, I turned my face back to the big guy. Kissing and licking his cock ended up with further smudges of my lipstick all over the dark, hard muscle. I opened my lips and began to take the shaft into my mouth, feeling it working its way down my throat before I let it slide right back across my pouting, red, cocksucking lips.

"Ohh, that's a good little whore," the big guy moaned as I went down on his erect manhood, "Suck me good, my little slut."

I had gone from virgin to cocksucking slut very quickly the other day and gained as much blowjob experience in one afternoon as some girls do in years. However, I had never yet taken more than one cock at once and, frankly, the experience was something else. With the first guys I had loved being the one to get them off, the focus of their desire and lust, but then there was just the two of us. Now, I was the centre of attention for all three of these hung, manly men, all their cocks were hard for me, pointed right at me, getting rubbed and sucked by me. It was quite incredible.

In a moment, I was reminded of the fact that my audience didn't just consist of these three men, either. I heard a groan coming from the other side of the room and remembered that my three friends were also here, sitting across the room from us, just watching the show. I wondered what they thought of it, whether they were enjoying seeing their friend in stockings, panties and a tight, short dress, sucking three big cocks. I wondered whether they were curious or disturbed, whether they were aroused or turned off.

"Oh God, they weren't wrong, Tom really is a bit of a slut," I heard Olly say, "Look how he gobbles that cock. He loves it."

"I think we should really call Tamsyn a she, not he," Harry said, "She looks just like a girl."

"Especially with that dick in her mouth!" Josh joked.

Aware of this further audience, I tried even harder to make my cocksucking not only pleasurable for the guy whose cock was sliding between my painted lips, but also for those watching. I wanted to give head like a porn star. I would suck on the big guy's dick for a while, letting it fill my throat right up, as I stroked off his friends. Then, I would switch to another cock and swirl that around my mouth for a while before moving onto the third.

I continued in this way for a while, getting all three men off with my hands and mouth until their cocks were nearly fit to burst. My own arousal was growing as well, the soft feel of my black satin panties doing nothing to quell the hardness of my dick, such a contrast with the feminine fabric that it rubbed against. I didn't have to worry myself about my panties much longer, however, as I would soon be losing them.

The blond guy turned his head to his superior as I licked the thick manhood of the hairy guy. An exchange of words passed between them in French, before the big guy, the superior, pushed me off his companion's member. He grinned down at me, kneeling on the floor in my hooker wig, smudged lipstick and revealing red dress.

"I think, now, my friend will want to fuck you, little whore," he said.

He stood me up and took me over to the interrogation table in the middle of the room and bent me over it so my head was over one end of the table and my arse sticking up from the other. My legs in their sheer stockings were spread wide and two of the guys flipped up my short skirt around my waist. I could feel the younger man standing behind me, rubbing his hardness along my arse crack, rubbing against the satin of my panties, causing my body to throb with anticipation.

The big guy tore my little satin panties right off and exposed my arse to his companions. At this point I realised that, for the first time, I could see my three friends seated on the other three seats against the opposite wall. My head as it was pushed down against the table was just in a position to line up with their crotches as they sat staring in astoundment at me, just waiting for the moment when they saw their friend's little white arse penetrated by the large dick of a French border control guard.

I couldn't tell what their emotional reaction to the scene was but I knew that each of the three was staring intently at me, they couldn't take their eyes off the dress that hung around my waist, my stocking wearing thighs and my bare arse as the young French guard spread my arse cheeks open and slid his huge mushroom head in between them, pushing it up into my arsehole, making me let out a sigh of pleasure at this eagerly awaited penetration.

I thought I could see signs of uncomfortable, embarrassing erections growing in my three friends' pants, that telltale bulge that all were trying to hide. However, I didn't have enough time to know for sure before my view was once again blocked by the sight of two large, heavyset men waving their own, more obviously bulging, cocks in my face. Once more, I stuck out my tongue to lick the two erections as the third, that belonging to their blond companion, slid up into my arse.

The guy behind me plunged his cock right up inside me, until he was rubbing against my arse and the tops of my thighs, his legs pressed against mine, our flesh rubbing together through the thin material of my stockings. Meanwhile, I took the other two dicks back in my hands and pulled them together and into me, so their tips, glistening with pre-cum, were touching each other. I wrapped my mouth around both heads and licked my tongue between the two of them, trying to hold both cocks in my moist wet mouth at once, all while the rod behind me completely impaled the lower half of my body.

With a groan and moan at my tightness, the hung guy behind me pulled out a little and slid back in, beginning to ride my arse with long, slow rhythmic thrusts, pushing my body forward as my tongue played over his companion's cocks. Amidst the gasping and groaning of the guy ploughing my tight little arse, I began to hear my own high pitched girlish moans.

"Oh. Ohhhh. Ohh, ahhh," I sighed, "Oh yes. Oh, fuck me. Fuck my tight arse!"

I heard a stifled gasp and giggle from my surrounding friends and was reminded once more what a strange and new thing this was for them. They were only just getting used to seeing their friend dressed as a girl and taking a cock in his mouth, they had never heard me beg for it like a slut, never really realised quite how much I loved this kind of thing. I gasped and moaned even as my mouth was filled with first one cock then the other of the hard men in front of me.

The young man behind me began to push up deeper and harder inside me, practically lifting my feet from the ground as he thrust into me. His breathing was hot and heavy. I had taken enough men in my arse by now to tell that this all meant that his climax was near and I willed him on, desiring that incredible feeling as a man's firm member shot its warm seed deep inside me. That was the moment I felt most like a real woman getting a real good fucking.

He gasped and groaned as he thrust harder and heavier, beginning to talk, saying things that sounded dirty and sexual in French before letting out one loud cry as he thrust so hard my feet almost slipped out from under me. His cock exploded and I felt that warmth inside my arse that told me he was filling me with his warm white spunk. I felt it running through my arse and dribbling down my thighs over my stocking tops.

As the young blond guy let his dick slide from my sticky arse, his stocky, hairy partner came around behind him to take his place. He ran his hand over my just fucked arse and gave me a slap on my arse cheek that shook my body and caused me to give out a little girlish yelp. He ran his fingers up my arse crack and inside me, beginning to fuck me a little with his first two fingers until they were coated in his friend's warm white sperm. This he scooped from inside me and, leaning over me, shoved it in my face.

"Eat this, whore," he commanded in a thick French accent.

I licked the two fingers just like they were one of the many cocks I had taken in my mouth. The taste and feeling of the slimy ejaculate that coated them just made me more eager. I had to admit that I loved the taste of cum wherever it came from and so had no problem licking completely clean the fingers that had just come from my own arse.

As he fed me his friend's cum from his fingers, his other hand was positioning his thick manhood at the sticky entrance to my tight arse. With the fingers clean, he brought them back and landed another slap on my arse even as he pushed his cock inside me. Grabbing my hips and pulling me back towards him, he ensured that his cock slid right up into me as quick as possible and got me completely impaled.

Even as my whole body felt filled up by this French guard's thick manhood, the whole of my vision as my body pressed against the table was on the even bigger dick belonging to the biggest guy in the room. I loved the feel of that massive hardness stretching out my mouth as my lips glided over the veiny surface of it. I longed to eat it further. As the guy behind me slid his cock back out and, simultaneously, pushed me further forward onto the table, I seized the opportunity to take that monster cock back between my lips.

I was now being penetrated by two huge poles from both ends, feeling helplessly suspended between them like there was one massive pole running through my body, holding me like a spit. My body was just being thrown back from one guy to the other, being used completely for their pleasure and giving me so much pleasure from doing it. I could hardly move my body of my own accord but that didn't much matter given how much it was being shaken about by the two strong, burly men standing over my slender feminine form, draped in a dishevelled red dress.

The big guy behind me was even less gentle than his partner. He was really going for it, completely tearing my arse open and not caring about the consequences. He was ramming inside me with such a force that it wasn't just my body that was shaking, it was the table beneath me. I was even worried that the legs were going to collapse. My own legs, in their sheer stockings, were starting to feel quite wobbly with all the thrill of being screwed like this.

britneyfan
britneyfan
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