Loading...The plane journey to London was uneventful, a bit choppy, but otherwise fine. I decided to make my trip a working holiday and convince my boss to give me the following week off. Two days for the World Travel Market then twelve holiday days.
It would be the last year at the Earl’s Court venue, which was a shame; I always enjoyed it there. But anyway, to work! I had to somehow try to sell our services as a web design agency.
Wednesday was quite good. I made a lot of contacts and had a lot of possibilities, however, it was not until Thursday that something good happened.
“Ah hello.” I said to the man. “I see you operate in the US. Do you have a website at all?”
“Yes I do.” The man stared oddly at my nametag. “Gary? Gary Slater? Do you write stories on the Literotica board?”
“Erm…yes I do. Have we spoken before?”
“Yes, by email. My name’s Jason; I also write stories there. I wrote to you once.” He said, smiling. I remembered!
“Yeah! Sorry, hi! How are you?”
“Not so bad. What are you doing here?”
“Trying to sell websites.” I said. “Don’t want one do you?”
“Sorry, we just had ours redesigned. But I’ll keep you in mind. What are you doing after the show?”
“Nothing I suppose. Back to the hotel, then begin my twelve days of holiday.”
“Well, you have to come round to my hotel for a drink with me and the wife. We’re also making this a holiday. We leave in two weeks.”
“Sure. Well I’ll meet you after the show and we can share a taxi!”
“Great, say…erm…five-thirty?”
“See you then!”
I felt good to meet someone I knew, well, sort of knew. I didn’t know anyone else in London. I walked round some more of the show and at five-thirty I met Jason. We shared the taxi home. He told me he already spoke to his wife and told her I was coming.
“Come up to the room with me and let me get changed. Then we can go down to the bar if you like.”
“Okay.”
He opened the room door, and called out. “Sarah. Are you here?”
“Just a moment honey. I’m in the bathroom.”
“Take a seat.” He said.
Sarah came out of the bathroom. She was dressed in patent leather trousers and matching tank-top.
“Hi! I’m Sarah. I’ve read your stories. Nice.”
“Thanks.”
“Are they true?”
I laughed. “I wish! No. None of them are. One of them, the one about the flatmate, that almost came true, but none of us had the guts.”
“So you’ve never been with a guy?”
“Nope.”
“That’s a shame. Well anyway, I liked your stories a lot! And so did Jason here.”
I just smiled, embarrassed by all the attention.
She continued to speak. “So what’s the plan?”
Jason shrugged. “Well, we can go down to the bar and have a couple of drinks, or we can sit up here and order drinks. Up to Gary here.”
“Whatever you two want to do, it’s up to you.”
Jason looked at Sarah. “Well I’m happy to stay up here if you are?”
“Yeah, fine by me.” She replied.
So we ordered drinks and talked. It was gone ten when I started on the non-alcoholic stuff.
“So going back to your stories Gary. You wrote those ones about forced feminisation, but have you every tried on woman’s clothes?” said Sarah.
I blushed and smiled. “Heh. Yeah, once or twice.”
“Did you like it?”
“Yeah, it felt nice. More probably because it felt like something kinky.”
“Do you want to try some of mine?”
I almost choked on my drink. “Erm, no, but thanks for the offer.”
Sarah got up and went to the bathroom. When she came out she was wearing latex gloves and was carrying a paddle.
“Maybe I should force you to do it.”
I looked over at Jason to see he was smiling. I relaxed a little, seeing that Jason was okay with everything.
“Yes, maybe you should.”
She pulled me up and made me take off my trousers and underpants. Then she paddled my ass repeatedly. I heard Jason undress and began to worry. I remember him telling me he was bi-sexual, but I had never tried it. I wanted to but at the same time didn’t.
Jason walked over to his wife and kissed her. He was totally naked and looked like he worked out. He was actually really sexy…for a guy. He then pulled her away and whispered something into her ear. She smiled, nodded and walked into the bathroom and closet.
“Come up here onto the bed Gary.” He said to me as he patted the covers. I took off the rest of my clothes and sat next to him. He started to massage my shoulders; it felt amazing. “I actually discussed this with my wife this afternoon. You said you were staying for another two weeks, right? Well I’d like you to stay with us. We’re actually going to rent a holiday apartment on Baker Street tomorrow so we’re not disturbed. What do you think?”
“That’s cool. I’d love to spend my holiday with you guys, but what did you have in mind.” I felt his hands move down my body and start to play with my nipples. He slid behind me and I felt his rock hard 9-inch penis press against my lower back.
“Well, we both know how we are all sexually charged. Hell, my wife more than anybody. But she and I are the dominant type. Now, for tonight, I thought we could just have a normal night making love, just fooling around and stuff. Then from tomorrow you can be our slave for the duration. Sex slave of course. What d’you reckon?”
I thought about it. A sexually holiday. It could be very fun, and these guys were amazing people. Why not? “Okay. Sure.”
“Good.” Was his last word as he pulled my head back so he could kiss me. I realised my dick was rock hard as he grabbed it and started to tug it. Our tongues interlaced for a while then he pulled away from me. “Honey,” he shouted to his wife, “he’s agreed.”
“Great!” She said, as she walked out wearing a sexy red with black lace and lace-up bustier, with matching suspenders but no knickers. She walked over to me and kissed me full on the lips. She picked up a lipstick from the bedside cabinet and applied some to her lips, then she leaned over, and put some on me. “Jason likes the feel of lipstick when our lips are kissing, so you can have some as well. Do you like that?”
I shrugged. “Yeah, sure, it feels good.”
“Okay. We can put more make-up on you later. Let’s just have fun for now.” She pulled me away from Jason and put his penis in her mouth and expertly blew him. Then she pointed it at me. I kneeled down and put it in mouth. I sucked on it exactly how I would want it to feel, then passed it back to Sarah.
“God, that’s amazing.” Jason said, as I sucked him again. As I sucked, I stared into Sarah’s eyes, which were watching me all the time.
“You finish him.” She told me, as she sat her pussy on his face, and watched me. I watched Jason’s tongue dart all over her clit while I sucked away on Jason’s dick.
“Ah! I’m coming.” Shouted Jason, as he bucked his dick right to the back of my throat and came. I swallowed for dear life, and rubbed him to get more out.
“Oh that’s so beautiful, OOOOHHHH!!!!!!” Sarah screamed out her orgasm.
We repositioned ourselves. Jason said he needed time to recharge. Sarah lay down and told me to lie next to her. She grabbed my hand and put it on her right breast. I started to rub it through the red satin material.
“Do you like how it feels?” She smiled and asked.
“You have wonderful breasts. Nice and big.” I replied.
“Thanks, but I meant my underwear.”
I started to blush again. “Oh. Erm, yes, very nice.”
“Oh come on. I know you have a fetish for lingerie. I bet you wish you had this on right now, don’t you?”
I dropped my head. “Yes.” I meekly replied.
“Don’t worry man.” Said Jason. “Later, you can try them all on, and we can get you dressed up like a proper little slut, okay?”
I nodded. Sarah pulled me on top of her. I put my rock hard penis into her pussy and started to fuck her slowly. Behind me, I felt Jason’s fingers rub my asshole. Then I felt him apply lubricant. I moaned in pleasure as his index finger entered me. Suddenly, the finger was pulled out, and Jason’s hard penis was at my hole. He pushed slowly. I felt the head pop in, and I screamed out as a bolt of pain hit me.
“We truly do have a virgin here sweetheart.” He informed his wife.
“Break him in good Jase.” She replied as I tried to push further inside her.
I felt Jason push more and more of his dick in me. Within a few seconds, the pain was replaced by a feeling of being filled up. I felt his pubic hair touch my buttocks.
He started to pull out then push in. We built up a slow rhythm as I fucked Sarah and Jason fucked me. Soon we were going at it like animals. I had my face next to Sarah’s and Jason had his hands on the headboard. We were both pumping to the second. In and out. I looked back at Jason on his knees, bottom going forward and backward at tremendous rate.
“OH GOD!!!!” Sarah came, and quickly pulled away from me. Pushed me forward so he could get a better hold of the headboard. I noticed Sarah had the video camera out and was film us. “This is so sexy!” She said.
Jason spun me around so I was on my back and continued to pump in and out of my hole, still holding the headboard. I could believe anyone could move so fast, he must have been well fit! He stopped and dropped his lips down to my lipstick-covered lips.
“I need a breather for a few seconds. While I’m fucking you, masturbate, okay?” He said.
“Sure.” I replied.
We kissed, tongues mingling. Then he grabbed the headboard again.
“Ready?”
“Yep.” I replied.
He started pumping in and out of me again, this time with fresh energy, he seemed faster than before! I rubbed my dick for all my might. Then I came all over his chest and stomach.
I felt Jason increase speed, he flung his head back and gave one last severe ram up my ass, further than it went before, and I felt his hot cum shoot all the way up me. He collapsed next to me and we kissed. Sarah joined us.
“So what did you think of you first fucking?” She asked. “As good as you wrote?”
“Fuck! Much better than I ever imagined!!! That was the best thing to ever happen to me.” We all laughed.
“Well,” said Jason, “they’ll be more where that came from, from me and from Sarah’s dildo!”
“First, let’s get you kitted out in some nice underwear.” Announced Sarah.
She literally dressed me up in the same thing she was wearing, satin red bustier with black lace, and a lace-up front. However, she didn’t seem happy with it and told me to take it off and go into the shower.
I spent about ten minutes in the shower, when Sarah came in with two tubes of hair remover. She rubbed it all over my body, even my face, except my head. Fifteen minutes later, she used the plastic knife to scrape the cream off me, followed by a shower to get the rest off. She then rubbed baby-oil all over me to stop a reaction. I was completely free of any body hair!
“That’s much better. Hey, you know what?” She asked.
“What?” I replied.
“You really have a feminine body. Your legs are perfect, long thin, yet curvy, just like models legs, and you have a small bottom, and a flat tummy.”
“Well thanks. At least I’ll like good for you and Jason.”
“Yeah. You’re gonna look sexy in that underwear now. And I have the perfect wig for you to wear!”
I put the bustier and stockings back on, but left off the panties just as Sarah had done. Sarah then applied plenty of foundation and makeup to my face, and then the dark brown, long straight wig. She adjusted the wig so that a few of the hairs fell forward over the left side of my face. She turned me to face the mirror.
“Tada!” She said. “What do you think?”
I was in shock! “Fuck me I’m sexy! Wow. Even my eyes look sexy.”
She suddenly remembered something. “Eyebrows. I forgot to pluck your eyebrows!” She thinned them out, pulling away at them, very painful indeed. However, when she’d finished, I looked even better. If it weren’t for my long thick eight and a half inches between my legs, you wouldn’t have known I was a man!
“Come on, let’s see what Jason thinks.” She said, walking with me into the bedroom.
Jason was sat on the bed waiting. I watched as his erection instantly returned. “WOW!” He said. “I want a piece of that!”
“Nope.” Said Sarah. She was strapping on a long thick black dildo, and inserting something into her pussy. “She’s mine first. But you can suck her cock while I fuck her ass.”
“Sure!”
Sarah positioned me onto the bed, hands gripping the headboard, bottom sticking out. Sarah got behind and rubbed lube on my hole and on her dildo, the placed her left hand next to mine on the headboard and used her right hand to guide the fake cock into my ass. Once the head was in, she put her right hand next to mine and began to push the cock up me.
At the same time, Jason had slid under me and began slowly sucking my cock. Sarah didn’t fuck me with such speed and strength as Jason, but she was slow and passionate, all the time sucking and kissing my neck.
Sarah began to increase the pace. I could see in the mirror she was looking down and concentrating on her fake dick up my ass. Her orgasm was starting. She flung her head back and pulled hard on the headboard as she pumped faster and faster up my ass. She screamed in delight. “This is wonderful!” I could feel my orgasm coming. Just as Sarah orgasmed, I came in Jason’s mouth; cum dribbled down his cheek as what seemed like pints came out of me.
We all collapsed on the bed, exhausted. What a night! I told Jason and Sarah that I should go back to my hotel and pack.
“I’m sure the management here wouldn’t like an extra person in the room without paying, anyway.”
They smiled. “Yeah, true.” Said Jason. He kissed me on the lips, as did Sarah. “Well keep the underwear on under your normal clothes. Sarah will give you the address of the apartment and we’ll meet you there at ten?”
“Okay. I’ll go and wash this makeup off.”
“Sure.”
I went to the bathroom and washed up. Then I got dressed and made to leave. Jason and Sarah met me at the door.
“It was an enjoyable night.” Said Sarah. “I’m looking forward to your first day as our sex slave tomorrow.”
“Me too.” I said, meaning it.
They both gave me long deep kisses, and I left their hotel, officially a bi-sexual transvestite sex slave.
It was on the Underground back to my hotel that I finally came to my senses and realised I was wearing a white shirt. My suit jacket covered most of my underwear, but if one were paying close attention then one would notice the red and black quite clearly.
A young man was sitting opposite me. He didn’t once look at me however. But at the next stop he got off, only to be replaced by a sexy young woman. She sat reading a magazine, then suddenly dropped it to her legs and looked straight at my chest. Oh fuck! I thought. She looked up at my face, and then moved next to me.
“Are you wearing women’s underwear?” She asked in a whisper.
I got nervous. “Erm…yes.” I gulped.
“That makes me so horny. Thank you.”
“Oh, er, you’re welcome.”
She moved back opposite me and just stared. She got off at the same stop as me. In fact, she came back all the way to the hotel with me. In the lift, she spoke again.
“It seems we’re in the same hotel. Were you at the Travel Market?”
“Yes, I was.”
“Do you want to come back to my room and fuck?” It was a direct offer, and I gave a direct reply.
“Yes.”
Back in her room she and I stripped. However, she told me to leave the underwear on. “I want to feel it.” She’d said.
She than put on her own bustier, a black one, then she sat her pussy on my rock hard cock. She rocked back and forth on the cock, at the same time feeling the satin against my body.
“God, I’ve always wanted to fuck a transvestite.” I didn’t have the heart to tell her that I wasn’t actually a transvestite. “Once I’ve come, I’ll do your arse, okay?”
“Yeah,” I said between breaths, “sure.”
Her hand movements over my satin covered chest and stomach were quicker and quicker as she brought herself to an orgasm. “OOOOOHHHHHHHHH!!!! That was amazing. Quick, let me get my strap-on.”
She put on a very large black strap-on dildo; it had to have been eleven inches long and very thick. She rubbed Vaseline all over it, and inside my arse as far as she could go. Then she made me go on all fours and she place the dildo at my entrance and pushed it right in without stopping. It felt like it was all in but she told me it was only about eight inches in. It felt amazing as she rocked back and forth; I really felt I was bi-sexual now, as I really loved the feeling of dick up my arse!
I clenched down on the dildo with my ass muscle as I shot cum all over her bedclothes. She continued to fuck my ass until she reached an orgasm, and it took her ages. I had sort of lost my appetite for anal sex and it started to be uncomfortable, but she carried on until she came.
We didn’t once kiss. I just gathered my clothes, said bye and ran across the landing to my room, hoping nobody would see me covered in dry cum and dressed in women’s underwear. I didn’t even get her name.
In the morning I showered and put the underwear back on. I dressed in a loose fitting t-shirt and a thick sweater, took my things and went to Baker Street. As promised, Jason and Sarah were waiting for me.
“Are you wearing your underwear?” Sarah asked on the way into the apartment.
“Yes Mistress.” I replied.
“Very good reply.” She said. “Well for your duration with us, we can’t call you Gary if you are going to be a transvestite, what name would you prefer?”
I thought about it. “Julia, Madame.” I replied.
“That’s a nice name. So Julia it is then. Come with me and I’ll give you clothes to wear.”
I followed Sarah into the large bedroom. She dressed me up in a fresh bustier, this time dark blue, with matching dark blue panties and dark blue suspenders. She then gave me a blue rubber micro-skirt to put on.
“We’ll leave it like that. Seeing the top of you lingerie makes you look even sexier. Now let’s put some makeup on you and the wig, pierce your eyes and maybe even your nose and tongue, and paint your nails.” So we did, and she did end up piercing my left nostril and tongue too. “It’ll be good for oral.” She explained. “We’ll have your belly button pierced tomorrow.”
“Okay.”
We went back into the living room to find Jason was gone somewhere. Sarah explained he’d gone to get some porn movies.
“Well, you can lick my pussy while he’s away.” So I got between her legs and licked her sweet pussy till she came in my mouth. “Very good slave.”
I almost cringed when my mobile phone went off. I fished it out of my back and picked it up. “Hello?”
“Hello Gary? This is Kelly, we ahem met yesterday?” The familiar voice said.
“Oh hi. How did you get this number?”
“One of your business cards fell out of your suit yesterday. I was wondering if we could meet again?”
“Oh, I’m afraid I can’t anymore. I’m with friends on holiday in London.”
“Well, maybe we could all meet together? Are they transvestites too?”
“Er, not exactly. Well, I suppose it’s okay to tell you. I am going to be sex slave to an American couple here in London for the next couple of weeks.”
There was a long silence. “Oh, my, god! Are you serious?”
“Yes.” Sarah looked at me puzzled.
“Can you put one of them on the phone?” I handed Kelly over to Sarah.
“Hello. Sarah speaking.” Sarah asked.
“Hi, I’m Kelly. I met Gary last night. We slept together. I’d be interested in being your sex slave too. If that’s okay?”
“Yeah, sure! That’d be great. Come on round.” Sarah gave the address and talked some more, then hung up. She pointed to me, got up and picked up a large studded leather paddle. “You! Over my knee! NOW!”
She lifted my skirt, pulled down my panties and paddled my ass really hard over and over again.
“THAT’S FOR SLEEPING WITH OTHER WOMEN WITHOUT MY PERMISSION! BITCH!!!! YOU WHORE!!!! YOU FUCKING TART!!!” She screamed. Tears ran down my eyes as I came suddenly on her PVC skirt. “Lick that up!”
“Yes Mistress.” I liked up my cum and completely licked clean her skirt.
As I was licking the skirt, I heard Jason come in.
“That’s how I like to see my women, ass in air!” He said, as he pulled his hardening dick out and began to stroke it hard. Mistress Sarah directed my head to her pussy, and I licked. Moments later I felt Jason’s penis enter me. Oh it felt so good to have a penis in me again. He wrapped both arms around me and leaned in as one of his hands pumped my dick. He pump my dick and thrusted in and out of me like a mad dog.
“Oh yes master, fuck my little girly ass.” I said. The doorbell went and Sarah went to answer it. Master Jason put me over the arm of the sofa and continued to fuck my ass.
“Jason?” Jason looked up at Sarah who had walked in with Kelly, but he didn’t stop fucking me like a mad man. “This is slave Kelly.” A massive smile formed on Jason’s face. Kelly didn’t look at him. She just stared at me in a wig and women’s clothing being bum-fucked like a gay fuck-toy.
“OH!” She shouted as her legs quivered. Cum ran down her legs.
Seeing this sent Jason over the top and started to ram my ass harder than ever before. Suddenly my insides were was out with hot cum. Jason collapsed on my back.
This was only the beginning of an amazing adventure.