Sam's Story

Jacky loved it. We'd sometimes go to the market and buy really cheap, sleazy undies for each other. It was fun especially when we got home and modelled the latest outfits for our mutual pleasure. I found him a pair of very sheer panties once that were so thin they must have been made from the same nylon as glossy stockings.

He liked them so much that when he put them on the first time, he almost came. He looked great too with his cock and balls so visible in them. I watched as he touched himself, mesmerized by how excited he was. I knelt down and licked at his cock through his panties and in seconds cum was spilling through the nylon and all over my face.

We went back to the market stall the next week and bought each other several more pairs of different colours. It's hard to describe why these knickers were so nice but I think it was mostly because the material was so tactile and enhanced the sensation of being touched through them.

During my gap year I worked in an office and I travelled in by train. I often wore quite short skirts and I'd sit surrounded by people and rest a broadsheet newspaper on my lap and surreptitiously slip my hand up my skirt so that I could lightly stroke my clit through these lovely knickers. It was quite hard not to give the game away when I came but I'm pretty sure no-one ever knew what I was doing.

One day I told Jacky I'd like to see him being fucked by another guy. If he was shocked by this, he didn't show it but instead asked me questions about it, probing my mind to find out just how the fantasy would play out. I described it all in detail and then we made very passionate love. I took this as a sign that he would be willing to try this out some time. It had clearly turned him on a lot.

I've often tried to analyse this fantasy but I can't really tell you why I find the idea such a turn-on. It just is. Maybe it's because it seems so fucking filthy to me.

Not long after I'd told him about my fantasy, Jacky bought a video. We sat and watched it that night and I'd never seen anything like it. I knew about transgendered people but I'd never seen any. Jacky was the closest thing and since he didn't have a female form (apart from when he wore falsies and a corset), this was all new to me. I sat in silence through most of the movie. It showed guys fucking TGs, TGs fucking other TGs, TGs fucking girls and even girls fucking TGs. It really turned me on.

Jacky sat with a stiff cock all the way through it too and if the idea behind watching the film was to put me to the test, I passed with flying colours. I gave Jacky's arse extra attention that night and we fucked for hours.

Over the years, Jacky has made friends with a lot of other cross-dressers and we occasionally go to a gay bar that's a regular haunt for TVs. It's good in there because Jacky can dress how he wants without getting a hard time from anyone.

He's got it down to a fine art now and the taxi drivers that take us there and bring us home never appear to notice that Jacky is a guy. One driver tried to chat Jacky up one night. We thought it was hilarious imagining how he'd react once Jacky had stripped off. That's one of the qualities I love about Jacky, he seems so comfortable with himself that he never gets upset with people no matter how they react to him.

So we went to the gay bar one night with the specific intention of drawing another CD into the fold. We weren't looking for someone to become a permanent fixture in our relationship, just a living sex toy for one night only.

Jacky has a particularly interesting friend called Chrissie who is a TV that lives the lifestyle 24/7. You wouldn't know she's a guy. She's worked really hard at her female identity and you can tell from the way I'm writing about her that we don't think of her as being male at all. She's very self-assured and has a demure elegance that people find very attractive. Her dress-sense is impeccable and she never dresses like the stereotypical 1950's Barbie-doll TV that people often think of when describing cross-dressers.

We found her in the corner of the bar with some of her 'girlfriends' and joined the group. We all knew each other so no invite was necessary. Most of Chrissie's friends moved away and eventually we had her to ourselves. It was the perfect opportunity to seduce her. If you talked to Chrissie about her sexual preferences, she would dismiss the subject with a wave of her hand and claim that sexual orientation was just semantics. It didn't matter to her what a person's inclination was; sex was just sex whoever or whatever you chose to have it with.

When the evening was drawing to a close we invited Chrissie home for a night cap. She accepted and we all climbed into a cab and made our way home.

When we got in, I poured three glasses of wine and we sat on the sofa and talked and laughed and had a lot of fun.

Jacky got up and put some music on. It was a collection of dance tunes and when the second track came on, Jacky jumped up telling us it was his favourite and started to dance. He asked us to join him so we all three stood in close proximity and jiggled to the music.

I remember looking deep into Chrissie's eyes and thinking she was looking a little turned on so I moved towards her and started to dance more provocatively. Jacky was shouting his encouragement and called out 'Give her a lap dance!' with a big grin on his face. I didn't give Chrissie time to think about it before pushing her carefully back on to the sofa. Jacky put a slow rock song on and I started to bump and grind in front of Chrissie. I was conscious that Jacky ought to be doing this but I was having fun and anyway, I'd make sure we switched later if things started to get serious.

I lifted my dress to halfway up my thighs to allow me to climb on to Chrissie's lap but also to show off my stocking tops and to let Chrissie get a good view of my legs. I knelt on the sofa with my legs either side of her lap causing my dress to rise to crotch height. I caught a glimpse of Chrissie staring at my pussy. I was wearing black see-thro knickers and my glistening lips were clearly visible. I hoped she liked what she saw.

I leaned forward so that my hair fell into Chrissie's face and squeezed my boobs, groaning and writhing to the music. Then I leant backwards and stroked my hands along my thighs up towards my crotch, pulling my head forward and fixing my stare on Chrissie's whilst licking my lips and smiling lasciviously.

Jacky sat down beside Chrissie and I stretched over and kissed his mouth, probing him with my tongue but making sure there was a slight distance between our mouths so that Chrissie could get a good view. Then I went back to Chrissie, grinding my pussy slowly into her lap. I could feel her leg pressing back against my cunt. I leaned forward and kissed her, slowly nibbling her full lips. I twitched as she responded and kissed me back. I could feel my pussy juices beginning to flow.

Chrissie's hand slipped between my legs and I sucked air in sharply as her fingernails danced over my pussy. I looked at Chrissie and smiled seductively, stopping to kiss her again before pointedly looking at Jacky. I looked back at Chrissie and whispered that we should get Jacky involved. She smiled at me and gently pulled Jacky over so that she could kiss him too.

As their kiss smouldered, I nuzzled in to Chrissie's neck, kissing her skin and nibbling her earlobe. I unbuttoned her blouse and stroked her chest through the silk vest she wore underneath. I didn't want to break their kiss but I DID want to get all three of us into bed so I stopped caressing her skin and suggested we make a move to the bedroom.

I got off and grabbed them both by the hand and led them to the bedroom. Once there, Chrissie sat on the bed and Jacky dropped down beside her. I slowly peeled my dress off so that I was standing in just my heels, stockings, suspenders and rather soggy knickers. They were both looking at me so I climbed on the bed and helped Jacky remove his dress before turning to Chrissie to help her. We were now just wearing our underwear.

Jacky complimented Chrissie on how sexy she was before kissing her and putting his hand between her legs. He started to stroke her through her pale pink silk knickers and was rewarded by Chrissie's moans and her cock swelling. Chrissie was on her back with Jacky lying half across her kissing her on the lips.

I crawled back off the bed and grabbed the lube. Pulling Jacky's panties to one side, I gently rimmed him before carefully lubing him generously. Even through her panties, I could see Chrissie was quite a big girl and I wanted to make sure it was as comfortable as possible for Jacky when she took him.

Now I could sit back and watch for a while. This was what I'd been waiting for. As I sat at the end of the bed fingering myself, Chrissie pushed Jacky on to his back and took control. She slipped her panties off and her cock sprang out, firm and hard. She put two pillows behind Jacky's head and kneeled over him so that her cock was in his face.

This was the first time Jacky had had a real cock in his mouth and he started tentatively, kissing and licking before encasing Chrissie with his lips. He was clearly enjoying what he was doing and I loved every moment. Chrissie held her cock at a downward angle that ensured he could suck her comfortably and then she started to rock her hips, fucking his mouth slowly.

Jacky's cock was straining inside his tight white satin panties and a pool of pre-cum had oozed through the material and gathered invitingly. I leaned forward and Jacky groaned loudly as I licked it off and kissed his aching cock. I knew Jacky was very close to coming but I wanted Chrissie to fuck him before that happened.

I walked to the side of the bed and leaned down, offering a breast to Chrissie. She sucked hungrily at my nipple as I stroked her arse. Whispering, I asked her to fuck Jacky. Taking her cock from Jacky's hungry mouth, she stood up and told Jacky to kneel on the bed. I pulled his panties down and put some lube on Chrissie's cock. I fingered Jacky to make sure he was nicely lubed and then held Chrissie's cock and slowly eased it, inch by inch, into Jacky's arse.

As her cock head disappeared into Jacky I slipped a finger into myself, cumming immediately. I couldn't believe how horny this was. When fantasies become reality I often expect them not to be as good as I had anticipated but this lived up to my dreams and then some.

Chrissie was holding Jacky's hips and encouraging him to move backwards and forwards so that he could dictate the pace and depth and he started with slow shallow movements that gradually became faster and allowed Chrissie deeper and deeper entry. I stroked Jacky's prick and asked him to describe how Chrissie felt inside him.

He was finding it difficult to talk through his moans of ecstasy but every now and then he'd utter a word or two telling me how good it felt, how full he was and how connected he felt to Chrissie. I climbed onto the bed so that my head was between Jacky's legs. Looking up I could see Chrissie thrusting into him harder and deeper.

Jacky pulled on my legs indicating he wanted to get in a sixty-nine with me. I couldn't get his cock in my mouth from this angle so I pulled him off with my hand whilst he buried his face in my cunt. He pulled my panties to one side and gobbled hungrily at my pussy making me cum again almost immediately.

Then it started; a long slow multiple-orgasm that wouldn't stop as his mouth sucked and licked at my clitoris and his middle finger probed my arsehole. I felt delirious due to all the wonderful sights and sensations that were invading my body and keeping me at my peak.

Chrissie was hammering into Jacky now and I wanked him hard and fast. His cum splattered down my body as Chrissie cried out and released her load into Jacky. She carried on fucking him long after she had cum, gradually slowing down and finally stopping altogether. They both dropped onto the bed panting and sweating and we crawled together and hugged each other motionlessly for ages. I hoped they would recover soon so that they could both fuck me before the night was over.

As I lay there recovering I realised I had two choices – give in to the urge to sleep or make the most of what could be a one-off. There was only one option in my mind so I dragged myself up and went to the bathroom announcing I was just off to clean myself up.

When I'd finished, I pulled Jacky to his feet and got him to do the same. I took the opportunity to have an intimate kiss and cuddle with him before going back and getting Chrissie to clean up. When we were all back in the bedroom I got them both to their feet. Kneeling before them, I took Jacky in my mouth and felt his hardness grow.

I held him in my mouth as long as I could but once his cock was touching the back of my mouth, I had to pull back. I then turned to Chrissie and repeated the act. When they were both hard I started to alternate between them, sucking one and then the other.

Looking up, I said "It's my turn now," with a big grin on my face. I told Jacky to lie on the bed and I climbed on top of him and moved up his body until my pussy was at his mouth. As he started to lick me I moved slightly so that he could concentrate on my arsehole. Chrissie stood beside me and I sucked her prick whilst Jacky worked his magical tongue inside me.

I grabbed the tube of lube and handed it to Jacky, moving away from his face so that he could get me ready. I felt a slippery finger squeeze into my rear and work the lube in. When he had finished, I took the tube from him and massaged some lube into his cock.

We positioned ourselves so that Chrissie was lying on the bed with her cock in my cunt. We were close to the edge of the bed with Chrissie's legs on the floor. Jacky came up behind me and carefully and slowly entered me. Chrissie stayed still whilst Jacky worked himself in.

Then I raised my arse higher into the air so that Chrissie could fuck me properly. And so it started; a stroke into my cunt and a stroke out of my arse. They worked in time together as best they could. Occasionally, they got out of synch and I'd be full of cock both back and front. It was incredible. I could feel my juices trickling down between my legs as they flowed.

I couldn't stop moaning and demanding more. Chrissie's legs were getting tired and she stopped moving. I told Jacky to fuck me really hard. He pounded into me roughly, squeezing my hips as he jammed his cock as far into my arse as he could. Chrissie was moaning under me, getting off on the sensation as Jacky's prick rubbed against hers through my stretched walls. I cried out as my climax ripped through me but Jacky kept pounding away, unable to stop until he was satisfied.

As my orgasm ebbed away I felt Jacky cum, crying out my name as he did so. Chrissie was still hard inside me so I started to fuck her, banging my cunt down hard and fast. Chrissie's body tensed and her back arched as I brought her closer to the edge. She twitched and moaned as her spunk finally spurted into me.

Dripping with sweat I climbed off Chrissie, suddenly realising I hadn't noticed Jacky pull out of me. I lay on the bed laughing. Not a nasty laugh but an elated one because what we had done was so incredible. I looked at Jacky and pulled him to me, kissing him affectionately.

I went to the bathroom and felt cum trickling out of my pussy and my arse. It was very kinky but SO nice...

Jacky and I are still together and although we haven't ever had another threesome, we are still good friends with Chrissie and Jacky has made it clear that he wants to do it again. Next time he wants to see me with another woman. It's only fair I suppose.

I've had a few fantasies about this which have been fuelled by the very graphic account Jacky gave me of what he wants to see me do. I have to admit that the idea of a pretty woman with a strap-on conjures up some vivid images of what she could do to us both...