Sam's Story

Hi. My name is Samantha but you can call me Sam. Everyone else does. I won't tell you my surname because, well, it's a rather an ugly name. I think of it as my most unglamorous aspect but then, modesty was never my strongest point.

I've just turned twenty seven and I am in a very happy relationship with a guy I met at university. I'll tell you more about him later. I have long dark hair that really shines in the sunlight. It's very straight and feels like silk to the touch. I have a pretty face. Not ultra-beautiful like a model but cute. I look innocent even now. I like this because it hides my passionate nature and fools people into thinking I'm a girl-next-door type. But in truth, I'm what you might call a really kinky bitch. I love sex and I'm very open-minded.

I have a nice hour-glass figure with breasts that aren't too big but nevertheless get me more than my fair share of attention. I have long legs that end in a very shapely bottom. All in all, I'm very lucky to have been born with such good genes. My Mum's a beauty too, even now and we look very similar. People often think we are sisters because she doesn't look her age at all.

Before I went to uni I was seeing this guy, Archie. He was my first love. One of the best things about Archie was that he taught me so much in bed. He had a very sensitive nature and he was incredibly caring and sensual. He was also very persuasive and I found it impossible to refuse him anything.

That's how I got to really know my body and what turned me on. I found myself sucked into his sexuality and tried all number of different, delicious things.

I remember one night when I was sleeping. It must have been three or four in the morning and I woke lying on my side facing away from Archie. He was lying on his side too, facing me and I felt his fingers in me and his cock pressing against my bumhole. We'd never had anal sex and I wasn't sure what to do. I was a feeling very drowsy and his fingers were really turning me on.

I don't know why but I started pushing back against his cock. Our juices were lubricating my arse and he pushed into me just and inch or so as my muscles relaxed. I remember him breathing very heavily in my ear and then his cock slid a little deeper into my passage and I groaned and pushed back so that he went deeper. I didn't know what to expect.

I suppose it should have hurt but I didn't notice anything other than an extremely sensual feeling of fullness. He started to fuck me, very slowly and very carefully. He didn't force his whole cock into me and he settled into a slow rhythm, still fingering me. I reached between my legs and stroked my clit as he continued to finger me. The movement of his hand was in perfect rhythm with his cock. I felt my orgasm slowly growing and I went with it, letting it build at its own pace.

As I came, Archie continued to fuck me slowly and it made my orgasm stretch out for what felt like an age. When I had finished, Archie removed his fingers and held my hips. I stopped touching myself and concentrated on the sensations in my back passage.

What I felt was unique for me at that time. I still have trouble describing the sensation because it felt like he was in my cunt but not. I know he was behind my vagina but that doesn't quite describe it either. It was the most intimate moment of my life. Archie began to thrust faster and deeper. I felt a little pain but it was ok; quite nice in its own way.

What happened next really took me by surprise. Without any direct stimulation of my cunt, I came. It was incredible and I never would have imagined it possible if Archie hadn't have done this to me. I could feel my juices rolling over my leg as my body exploded into an orgasm that spurred Archie on to climax.

When his orgasm subsided, he eased himself out of me at such an imperceptible pace that I hardly noticed until the last moment when my sphincter tightened involuntarily, propelling the tip of his cock out of me. So that was the moment that I fell in love with anal sex and our lovemaking took a turn for the better that allowed me another avenue to explore and exploit.

On another occasion, we had just had a bath and Archie was leaning over, emptying the water. I knelt behind him and run my tongue over his bum cheek. He froze instantly and I thought he wasn't enjoying it but then he let out a little groan and told me it felt nice.

I made spirals over his skin with the tip of my tongue and brushed my lips against him, stopping from time to time to kiss him gently. I slipped my hand between his legs and felt his hardening member. As I stroked his cock I became more adventurous with my mouth, moving from one cheek to the other and sometimes lingering on his crack but not touching his hole.

After a few minutes of this I went full out for his hole. I started slowly and lightly before pressing harder and lapping at his ring. His cock was beginning to throb and he was moaning quietly. I pushed my tongue into him. I'd never done this before and the soft texture of his anus felt sensual around my tongue.

I fucked him with my tongue, pushing into him as far and as fast as I could. I could see his thighs shaking with pleasure as my long tongue probed him deeply. After a while I could feel him getting close to orgasm so I quickly stopped and turned him around, taking his cock in my mouth. I slipped my middle finger into him and he came almost immediately. The feeling of his arsehole around my finger was fantastic.

I let his cum dribble out of my mouth and onto the floor, standing up as it did so to make sure he could see. It dripped onto my breasts and he grabbed them and massaged the cum into my skin. I felt as horny as hell and ground my pussy against his leg.

He took me to the bedroom and finished me off with a vibrator. Whilst he played with me, I found myself fantasising about fucking him with the vibrator.

When I went to uni, Archie and I split up. It was a very sad time in my life although we knew the distance wouldn't allow us to stay together but I've always been grateful to him for all the things he taught me. I'll never forget him.

Life at uni was good. I was one of a group of students who became friends and we were all obsessed with being liberated. The crowd was about ten strong and everyone had a personal agenda about one thing or another, all of which was to demonstrate that we had cast off the shackles that the rest of the world had to live with.

We had one guy who was pro declassification of drugs, another who took vegetarianism to an extreme and wanted to liberate animals from test labs and another who wanted a radical reform of the political system, and so it went on.

It was at this time that I met Jacky who I thought was the bravest of our liberated crew because he was a transvestite and one day he walked into the Student bar in women's clothes. There were sniggers from a lot of people that night but he sat down with us and carried on as if nothing was wrong. He seemed oblivious to the disapproval of other students.

Jacky looked quite convincing. He had long hair anyway and a slim, boyish figure that allowed him to acquire a feminine appearance almost naturally. I found him fascinating. I'd never met a TV before and he was such a charming guy that I found myself drawn to him. When I got the chance, I sat next to him and mentioned that he looked really good.

We broke into a long conversation about it and Jacky was very open about his feelings. When we got on to the subject of make-up I tactfully suggested that his could be improved if he wanted some help. That was how we ended up back in my room a little later.

Jacky sat at my dressing table, the mirror in front of him with me beside him, cleaning his make-up off and reapplying my own. I used a good foundation that covered his shadow well and then applied a little blusher, mascara and lipstick. He was very please with the way he looked.

It was at this point that I realised how much I fancied him. He was good looking whether he was dressed as a boy or a girl and he had such a wonderful personality that I found myself looking past his outer skin and deep into his soul. I poured us both a glass of wine and we sat on my bed since there was no room for much furniture in my digs.

We talked for ages and lost all track of time. By the time we had our first kiss, the sun was coming up outside. His lips were moist and feminine and I felt myself taking the lead, pushing him down on the bed and climbing on top of him. Jacky was wearing a short, black cocktail dress and I reached behind him and found the zip. He arched his back as I slowly pulled the zip down.

With the dress off his shoulders I lowered my head and sucked his nipple. My hand glided down his dress and when I found the hem, I pulled it up slowly. He was wearing black satin panties underneath the dress and my fingers danced over the material, tickling his cock and balls. He groaned as I did this and I could see sticky precum oozing through the satin as I lowered my head. I found the sight of his groin wrapped in satin very sexy. I'd never thought about it before but now I realised it was something else I wanted to explore.

Jacky's head was resting on a pillow and I could see him staring open-eyed as my lips traced the outline of his stiff cock. I stopped to lick the precum off his knickers and could hear him whimpering. I slipped one hand underneath him so that my thumb knuckle was pressed against his arsehole.

With the other hand I pulled his cock out of the top of his knickers and took him in my mouth. I could feel he was very close to cumming so I stopped what I was doing, stood up and very slowly took my clothes off. I sat down on top of him and moved up his body so that my cunt was above his face.

I felt his hands holding my ass cheeks firmly as he pulled me to his face. His tongue lick hungrily at me and I pressed down on him harder, grinding my cunt into his face. I was on the edge as I pulled away and sat down on his cock. He entered my soaking cunt easily and his hips thrashed wildly as he fucked me. We only fucked for a brief amount of time, but we both came before I dropped back onto the bed beside him. We crawled under the sheets and slept for hours.

We got up around noon and went back to Jacky's so that he could get changed. His apartment was huge. It turned out that his parents were very well off and they set him up in a flat just off campus. He seemed to have everything.

He had several wardrobes in his bedroom and lots of clothes – both everyday 'guy' clothes and lots of dresses, skirts and blouses. He had about twenty five pairs of shoes ranging from hiking boots to very spiky high heels.

We both undressed and showered together. This was the first time I had seen his body really properly. His legs were shaved and his pubic hair was shaped and trimmed. In fact, that small patch of pubic hair was all the body hair he had. We fooled around in the shower and then got dressed.

Jacky's underwear drawer was full of lingerie. Most items were either satin or sheer with the occasionally lacy item. He had lots of tights and stockings too and I started to dress him in my mind. Planning what I'd like to see him wearing. I decided I'd work on that later.

He slipped on a pair of sheer white panties. His cock was visible through the material and I felt a tingle between my legs as I looked at him. He put on a pair of jeans, a t-shirt and a pair of trainers.

We were starving hungry so we went into town and got a bite to eat. By the time we got back to Jacky's apartment, it was nearly seven o'clock. Jacky poured a glass of wine and we listened to some music. I ran a bath and we lay in it, drinking wine, talking, laughing and caressing each other. I looked down and noticed my pussy needed a trim.

I think Jacky's well groomed patch made me a little conscious and when I mentioned it, Jacky was more than happy to help out. He got a little carried away and the next thing I knew, I had no pussy hair at all. Jacky grinned at me as he admired his handy work. I didn't mind at all. It's quite nice to be completely bald sometimes.

When we got out of the bath and dried off, I went to the bedroom and opened his underwear drawer. I took out two pairs of satin panties of the same style and put one on the bed and wore the other pair. I then found a matching suspender belt and glossy stockings. Finally I found a cami top that matched and put that on the bed too.

When Jacky walked in I said I hoped he didn't mind me wearing his knickers and he smiled at me and told me I can take my pick anytime. I asked him if he'd like to wear the lingerie on the bed and he was happy to do so. He asked me to dress him so I did. I slipped the panties up his legs and packed him in as best as possible. I loved the way the material gave him such a glossy bulge. It looked great.

I tucked his cock in so that it was pointing sideways and I wanted to stroke and play with him there and then but I waited until his suspender belt, stockings and cami top were on. I'd never dressed a man before – not in any type of clothing and it was an extraordinarily sensual moment and the air felt charged with eroticism.

I stroked his chest through his top and gently squeezed his nipples to erection. Jacky was standing in front of me and I pulled him to me as I sat on the bed. Lifting his top slightly, I kissed his belly and ran my hands over his bum. His firm cheeks felt delicious through his panties and I curled my fingers between them making sure I pressed against his hole. I leaned my face forward and kissed the tip of his stiffening cock through the white satin. He groaned his encouragement as my tongue moistened the material.

His cock was completely stiff now, pressing hard against his panties and my mouth. I slowly pulled his panties down and stroked his smooth legs through his stockings before bringing my hands between his legs and stroking his balls. A tear developed on the tip of his cock so I leaned forward and licked it off with the very tip of my tongue.

Standing up, I lifted Jacky's cami top over his head and dropped it to the floor. I laid him on his belly on the bed and picked his discarded panties up off the carpet. Sitting beside him, I ran his panties over his legs and his back. His face was resting to one side so I tickled the exposed part of his face with the satin material. The glistening pre-cum in his knickers touched his lips and a small drop clung to his skin. I watched as he licked his lips, tasting himself.

I ran the panties back down his body and flopped them onto his bum and between his legs. He arched his back slightly as the material tickled his skin and I took the opportunity to slide them over his exposed hole. He groaned and twitched as the material brushed over the nerve endings at his entrance. I leaned forward and began licking him as I had done that first time with Archie. I probed his hole and continued to stroke his skin with his knickers.

His body tensed and he groaned out loud as my tongue pushed deep into him. His hips writhed in time to the movement of my tongue as Jacky became lost in the sensations he was feeling. I kept a slow purposeful rhythm not wanting to go too far too quickly but also to give myself the time to enjoy the smooth tight skin that encompassed my tongue.

I could feel myself tingling with excitement as I lifted my head and massaged his hole with my finger. He told me to stop a moment and leaned over to a drawer by the bed. Leaving the drawer open, he passed me a tube of lube. The drawer was full of toys, condoms and oils. I saw a glass dildo that I immediately wanted to use on him but I waited. First I wanted to enjoy the sensation of his tight hole wrapped around my finger.

I squeezed some lube onto his arse and then my finger. I began to slowly work my finger into him moving in and out up to the first knuckle then the second and finally my whole finger. His hips pushed back at me as I pressed into him, pushing my fingertip against his prostrate. He groaned loudly every time my finger hit the spot, encouraging me to go deeper and harder.

I told Jacky to pass the glass dildo which he did without question. He was breathing very heavily as I pressed the glass against his hole. I'd never fucked a man before and was so excited, I felt close to cumming.

The dildo was shaped liked a cock – it even had glass veins running over it and it felt great in my hands. It was about six inches long and quite thick. I had to push hard to get it into him but after the head had disappeared there was no effort needed from there in. Jacky was groaning uncontrollably, thrashing his hips up and down as I fucked him harder and faster. I found myself wishing it was a real cock pounding into him. Wishing there was another guy here to do this whilst I sucked and fucked Jacky.

With the dildo still in him, I rolled Jacky over and got myself into a sixty-nine position. I could feel him licking my pussy through my now soaked knickers. His stiff cock was oozing as I continued to fuck his arse. Taking him in my mouth, I tasted the deliciously salty goo that oozed from him.

Then he pulled my panties to one side and buried his tongue in me, licking and sucking me for all he was worth. My orgasm exploded onto his face and I wailed like a Banshee as his tongue hungrily fucked me.

Sensations roared through my body, keeping me in climax for ages. I couldn't do anything for Jacky at that point, being unable to concentrate on anything but the extraordinary orgasm that gripped my body.

As it began to subside, I lowered my head and rested it on his belly. I kissed the skin and stroked his hips through his suspender belt. The dildo had slipped out of his arse so I pressed it back into him and began fucking him whilst taking his cock in my mouth. He began to fuck me, his cock pushing to the back of my mouth and then coming almost out again before thrusting back.

I started to fuck him very hard with the dildo and felt his cock swell before he shot into my mouth. I swallowed his load and slowly brought him back down but I kept fucking him. I didn't want to stop yet. His cock remained hard in my mouth and I felt him resume his attention to my pussy.

Then his tongue slipped over my perineum and onto my arsehole. This was the best sex I'd ever had. I'd fucked a guy in the arse and now I was going to get the favour returned. I couldn't wait to feel him in me.

A lubed finger slipped into me followed by a second. He started to finger fuck me and lick my pussy at the same time. I groaned appreciatively as his fingers increased their speed. I slowly pulled my arse way from him then got off, pulled my panties off and sat down on his lap facing him. I eased his cock into my tight arse and pressed my weight down on him.

The sudden sensation of fullness took my breath away and I started to rise up and down his pole more quickly than I had planned but at a pace that my aching body demanded. I still had my panties in one hand and I rubbed the sodden crotch into Jacky's mouth so that he could taste my pussy whilst I fucked him.

His eyes were closed and he was lost in the moment. I started to fuck him faster and faster, feeling his cock stretch me inside, pressing against the inside of my cunt. Suddenly, it hit just the right spot and my orgasm brewed up inside me. I could feel Jacky was with me so I fucked him furiously and brought us both to a shuddering orgasm. I lay on Jacky panting and exhausted, felt his arms wrap around me, holding me as he nuzzled into my neck. This was when I knew I had met my soul mate.

I'd never thought of underwear as being so integral to sex before but being with Jacky and seeing how it turned him on made me see things differently. I chucked out all my old cotton undies and replaced them with raunchy g-strings and panties and tight bodies made of satin, lace and see-thru material.