A guilty encounter
written by:
London Guy

The guilty encounter

I'd always had a thing for Jenny. Ever since I first saw her when she moved into the house next door she had caught my eye. I didn't know her, I hadn't even spoken to her, but she looked stunning. She had a pretty face, first and foremost, with big eyes which are always a bit of a killer for me. She had an awesome smile, and had a look of general carefreeness when she laughed.

She was always a bit understated, she would wear non-flattering clothes, baggy tops, thick jumpers, and jeans. Nothing revealing at all, but despite that I knew what lay beneath, I could tell just from looking at her that she had a figure which I would utterly love, i.e plenty of meat on her bones to get hold of, big beautiful breasts, luscious thighs and ass...I knew I would love to feel her weight bearing down on me, and it wasn't too long before I started fantasising about her. I would mentally undress her while I was in bed, getting rock hard and stroking myself, daydreaming about undressing her down to her wonderful figure and worshipping it, and her.

That was the start, once I got this into my head I couldn't help myself. Whenever I felt turned on and grabbed the opportunity to masturbate, she would be the object of my desires. This firmly planted her into my head as a real object of my desires.

As time went on and winter/spring turned to summer, we had gotten to know one another a lot better, and we really got on. Neither of us were in a position to enter into a relationship, for one reason or another, so the relationship we did have was purely platonic, just friendship.

We would meet quite regularly as we both had a kid of similar age. I would often go with her and them to the cinema, walk to the park, go for coffee etc. We got close. But despite the obvious fact that nothing could ever happen between us, I couldn't get rid of this yearning for her.

This only became worse over time. Over a period of maybe 3 or 4 years, this 'stalemate' continued, we remained good friends, and only got closer in that regard, but still nothing ever crossed the line. This is despite the yearning in me growing stronger. I would fantasise deeply about her now. When I got the opportunity I would love to think about various scenarios between us, just lying naked and thinking about her, feeling my cock grow harder while visualising her, until I could feel the precum on the tip of my cock and could no longer resist the urge to pull back the foreskin and grip my cock hard, and rub, all the while seeing in my mind my cock entering her wet pussy, whilst looking into those big eyes. Or practically feeling my cock between her beautiful tits, watching her playing with her nipples whilst squeezing her wonderful huge breasts together and enveloping my cock, my precum being more than enough lubrication to slip in and out between the soft mounds, in deep until I was nearly touching her chin with the exposed tip of my cock. I would dream about her taking the tip in her mouth and looking deep into my eyes until I could feel my cock beginning to twitch and the sensations take over my entire body as I could see long strings of my cum firing into her willing mouth and covering her tongue.

As you can see, this fantasy was getting more and more vivid the more I thought about it.

During one summer, we spent a lot of time together and I noticed that instead of wearing very understated clothes, she wore cooler, and looser vest tops, and tighter t-shirts. This drove me utterly utterly mad, as I could clearly see just how big her tits really were, the outline of her bra showed that her tits were barely contained in the struggling bra, and I just wanted more than anything to see her in all her glory.

We would talk about life and the various stresses we were under, we both had a lot on our plate and we understood each other's predicaments. We wanted to genuinely help each other as friends do, and we started to disclose more about the things in life that were affecting us. I wanted to do as much as I could to help her, putting my animal attraction to her body aside, she was such a lovely girl and deserved better.

Cutting a long story somewhat short, I went to her house a couple of times after she had moved and we just sat and chatted, she got me, and understood what I was going through in my life and I felt comfortable. As we sat on her sofa this one time, she started to move herself closer to me on the sofa, until we were touching. Despite this feeling a little unexpected, it felt natural to put my arm around her. Whilst conscious that I couldn't let it show, this close contact made my cock stir, and I could feel it rising slowly under my jeans. I was just hoping she wouldn't see any movement which would give this away, as it was still the case that nothing could happen between us, and we both knew it. I worried intensely that any sign I may be getting turned on by this closeness would result in me being kicked out of the house immediately and would ruin our friendship!

To my total surprise, she took my hand and lowered it to the top of her breast, just below the shoulder blade. I guessed it made her feel secure to have that feeling of being hugged, but the added closeness of my hand to her breast now made my cock ache, and I could see out of the corner of my eye it was now obvious that I was hard. I found it difficult to resist the urge to 'flex' it, which I always do when I'm hard as a rock and something is getting me very turned on. The tell tale rise and fall of my crotch would certainly give the game away, and I didn't want to do that. My boxers were feeling slightly wet with precum which now must have been dripping from the tip of my cock in yearning.

She nuzzled herself into me, causing my hand to drop lower on her breast, now only inches from her nipple. As she moved, I sensed something in the way she did so, the shift of her shoulders, and the sound of her breath, there was something else there. I suddenly sensed that she too could feel the sexual tension and, could it be that she was beginning to want my hand to touch her?

At this point, I was so hard it was beginning to hurt. I just did it, despite my head screaming at me not to - I moved my hand lower on to her breast until I could feel her erect nipple under my fingers. She again shifted slightly and breathed in a way that I could just tell she was getting turned on. She didn't look at me, didn't say anything, she just breathed heavily. I could, from her reaction, tell she wanted it, if she didn't, I would have been out the door. Suddenly, I was proved right...with her hand she pressed my hand onto her breast harder, she guided my hand and motioned for me to rub in circular motions around her nipple, and I obliged. Without saying anything, I decided to take the plunge, and I dipped my hand under her top and into the top of her bra, and I grasped her hard nipple between my fingers.

She liked me to be rough with her nipple, which I wasn't used to. She wanted me to press on it, pinch it, flick it, which I did. She began to close her eyes and flick her head from side to side as she was reacting to my touch, getting more turned on herself. I couldn't believe what was happening, on so many levels. But mostly, I was in awe that the object of my desires had become much more than just an object, and my desire to touch her, to hold her breasts, to see her gorgeous soft but utterly full bosom in person, was slowly being fulfilled. This was so alien to me.

Nonetheless I took it further, I motioned for her to lie down on the sofa, and I got on top of her, my crotch between her legs, and I could feel the warmth radiating from her. I pulled down her top and her bra, exposing the breast I had been playing with. My god she had gorgeous tits, they were perfect. She later revealed that they are a FF cup, and I could squeeze them in my hands with plenty to spare. I took the exposed nipple in my mouth and played with it on my tongue. I sucked it hard and ran the tip of my tongue across it, feeling every part of it, feeling how hard it felt. All the time I could see her head moving as she was writhing now. I instinctively began to thrust my pelvis into hers, effectively dry humping, and I was now soaking wet with precum.

This continued for a few minutes before we came round, and I released that I had to leave. She quickly made herself decent, and I left, all too quickly in a flustered state. We knew we had both crossed a line, and felt very guilty about it. I got home, still rock hard and wet from the experience, and I immediately had a shower, all the while thinking about her gorgeous tits and how her nipple felt between my fingers and in my mouth. Before I knew what had happened, I had begun stroking my cock and reached climax so quickly I didn't believe it, I came so so hard, my cock throbbing and blasting the shower wall with about 6 pulses of my cum. It had slowly dripped to the shower floor by the time I could open my eyes again, feeling the last few orgasmic twitches. It felt amazing.

Some time later, probably 4 weeks, I again visited her house, and this time I had the intention of giving her a massage after some really stressful events of the last few days. I thought I could make her feel better, and that's what my aim was. I didn't expect anymore of the same after last time, as we were both aware of how we crossed the line, and both felt pretty shameful about it.

She led me to her bedroom, and I brought the massage oil I'd ordered. She took off her top, and left her bra on and laid down on her front on her bed. Needless to say being in her presence with her wearing so little turned me on so much, and before I knew it I had the most raging hard on again. However this time, I didn't feel the need to hide it away.

She had taken off her jeans as well, and I could see she had a gorgeous ass too. I decided that I didn't want to get covered in massage oil, and so I also removed my t-shirt, and later on my jeans, as I had to climb onto the bed to really rub her back at the correct angle.

My erect cock was causing my boxers to bulge, but I didn't mind as she couldn't see....I just started easing my hands onto her body at the top of her back, and used my fingers and thumb to press down and across, trying to ease her tension. She seemed to enjoy it- I worked on the top of her back and slowly moved down to the base of her spine. I was constantly looking at her amazing body. I could just see the bulges of her beautiful huge tits to either side of her chest. I wanted so much to see them again in the flesh, I pictured them in my mind as I continued with the massage, I wanted them in my mouth again, they were the biggest and most wonderful tits I'd ever seen in person, and my god I wanted them again.

In order to reach her shoulders, I straddled one of her legs, moving her legs apart to accommodate my knee between them. Without her jeans on, I could feel the heat radiating from deep within her, I could literally feel the warmth from her pussy on my skin, and the tension I was now feeling made me start to shake slightly.

As I leaned forwards to touch her neck, I could sense my cock was digging in to her ass, she must be able to feel it I thought to myself, and she turned her head towards me and smiled with her eyes closed. I continued with the massage.

After a couple of minutes, with my rock hard cock pressing into her naked flesh, I could tell she was feeling turned on as her breathing changed again, and she just became more agitated, more restless. By this time I knew that we were crossing this line again, and neither of us were slowing down. She slowly lifted her body with her forearms, and I could tell she was showing me her tits. She lifted until the nipples were just touching the warm bed sheets, and I could see just how wonderfully full her breasts were. I could not stop myself and I brought both of my hands round the side of her body, and I slowly touched them, I felt the tips of the nipples moving against the palms of my hands, and I caressed both of them in my hands, tightly. The skin was so pale and so soft, I circled her nipples with my fingers, slowly bringing the pressure up, remembering what she loved a few weeks ago. Her breathing increased again, and she was nearly panting now. She told me she wanted to 'feel me', and ushered me to move to her side. As I did so, she reached out with her hand, and pulled my cock from the slip in my boxers. My cock was so hard and so wet with precum now, she grabbed the shaft and moved her hand down to the base and up to the tip a few times, moving my foreskin up and down over the wet tip. She felt the precum with her thumb, as she gently rubbed my tip with her thumb in small circles - this is something that drives me crazy and I do it a lot when I'm taking things into my own hands, so to speak.

She said 'you don't just have to massage my back, you know'. So I told her to turn over. I then got back in between her thighs, with my cock, like a rod of iron now, now poking out through the opening of my boxers. I didn't put it back inside, and instead I took my boxers off.

As I leaned over her, I positioned myself so that my cock would be between my stomach and her pussy. I wanted to put pressure on her clit with my cock as I was leaning into her, now massaging her shoulders from the front, looking into her gorgeous and utterly striking blue eyes.

I leaned down and took her left breast in my mouth, and sucked on the nipple hard, just how she liked it. I could tell from her movement that this is what she wanted. With my other hand, I took the other breast and gently stroked her nipple, circling it with my finger, flicking it with my thumb.

I instinctively and without thinking about it started gently thrusting my pelvis. As I did so, the rough surface of her lace underwear chaffed slightly on the underside of the tip of my cock, where the foreskin had been pulled back by my movement, and it was uncomfortable. I tried pulling the skin and covering the tip, but with every thrust forward my skin would pull back and expose the tip again. I raised myself up slightly, and with my hand I moved her knickers to the side, exposing her soft pussy. I looked down in amazement at what was happening. This was something I had fantasised about for so long, and now it was happening. I was shaking, and my breathing was shallow.

I could see she was totally shaven, and I love that. I love feeling the smoothness against me, and I touched it. She reacted, in a good way, and so I grabbed my rock hard cock, pulled the skin back exposing the wet tip, and I gently ran it up and down between the lips of her pussy, only very very gently. Teasing her.

I then put the underside of my cock against her clit and leaned forward to continue my sucking of her breasts, I wanted the underside of my cock to slide up and down against her clit and the lips of her pussy as I gently thrusted. I could feel the wetness on my cock, and it glided so smoothly over her clit, I could feel the tip of her clit on my balls, and then as I withdrew, felt it move up to the head, and down to my balls again, gently as I thrusted. I wanted to take things nice and slow.

She had other ideas though, and suddenly I saw her hand move down to her pussy. She grabbed the shaft of my cock, and with one movement, placed the tip of my cock against the wet opening. On the next thrust, I was inside her. All the blood came back into my face and hands from the nervousness, and the sensation of the hot wetness of her pussy on my cock was unbelievable. As I entered her on the first thrust, she let out a moan and her head writhed from side to side. I wondered how it felt for her to have my cock stretching her pussy, I knew she hadn't had anyone in a while. I slowly pulled my cock out to the tip, and gently thrust back inside her, again the soft moaning. She had her hands on my chest now, and I thrust inside her again. She gripped my chest, tugging on my hair. I could not believe that this was happening.

This was all too fast for me, and I could tell that I would quickly lose control, and I didn't want to cum straight away. When I gently pulled back, I took my cock all the way out. I could see the space between her lips that my cock had left, and I watched as my cock, shiny and glinting in the light, literally covered in her wetness, bounced up and down after exiting her body. I was the most turned on I'd ever been in my life. I touched my cock and felt her juices, sliding my hand up and down the shaft. She watched me with pleasure.

I then moved up her body and began playing with her wonderful tits again. I was in heaven as I had my head between them, she would press them together around my head. She held them together as I looked down, and my god they looked unbelievably huge as she squeezed them together. The nipples were now close together, so I simulatneously flicked them both with my tongue over and over again.

With my free hand, I slowly moved down her body to her pussy. I brushed across her pubic bone and felt how smooth it was. It was also wet with my and her juices after I was thrusting just now, it was slippery. I ran my fingers along the edges of her pussy lips, just teasing them open with the tips of my fingers. I wanted to slow everything right down, and I avoided placing them inside her pussy. I brushed past her ass, and back up to the pubic bone, just barely touching her pussy each time. And each time I came close to touching her, she writhed again and I could feel her moving down the bed, trying to get her pussy to make contact with my searching fingers. She wanted me inside her, she was so turned on and I was driving her wild. Her breathing was now so shallow and she was so caught up in the moment, every part of her body was now moving in rhythm with my hand. But I kept on teasing her, I wanted to heighten her senses.

Gradally, I parted her lips further, and I pressed my finger onto her now soaking wet hole, I sucked her nipple and bit down on it very gently as I pushed my two middle fingers deep into her. I took them out and spread the wetness all over her pussy, her clit was now so slippery with her wetness, and I began gently rubbing it in circular motions, and using my two middle fingers on each side of it, rubbing the short shaft of her clit. She responded to everything I did. I kept up the attention on her breasts, I was so turned on my licking and sucking them both, and just feeling their size.

I moved my hand away from her pussy, and up to her tits again, I used my soaking wet fingers to glide her wetness all over both nipples, making them so slippery and wet too. I rubbed both nipples with my fingers, gently pinching them, all the while watching her face. I then licked her juices from my fingers and from her nipples. She tasted good, and she watched me do this with a look of yearning on her face. She mouthed the word 'fuck' and 'oh my god', I was in ecstacy. Not only is my fantasy coming true, but she was enjoying every second of it.

After licking my fingers clean of her juices, I knew how good she tasted. I slowly moved my mouth from her nipples, and adjusted my body. She could tell what I was doing, and she opened her legs wide with her knees almost touching the bed sheets so I had all the space I needed.

When I was there, I could feel the heat on my face, and then on my lips as I moved closer. I could smell her pussy now, and I just wanted it so badly. I started by licking between her lips, from her beckoning hole, up to her clit, up and down slowly, teasing her. I gently moved my fingers and rested them against her opening. I then alternated between thrusting my two fingers deep into her up to the knuckles, and then, when I withdrew them, putting my face right into her pussy and pushing my tongue into her hole. This was amazing, I reached deep into her with my tongue as far as I could go, all the while nearly suffocating as my nose was pressed into her clit. She reacted, as I flicked my tongue while still inside her pussy, I stayed as long as I could before I needed to breathe, and I went back to fingering her and licking her pussy lips. The sensation of my tongue being inside her as far as I could go was beautiful.

I then took her clit in between my lips, and I sucked. I sucked hard, then soft, hard then soft, rhythimcally drawing her clit into my mouth, and pushing it back out again, over and over, quikcly. I felt her arching her back and groaning, and when I looked up I could she she had her tits in her hand and she was playing with them at the same time. My cock poked hard into the bed now and it hurt, I needed to be inside her.

I continued with the sucking of her clit, and slowly introduced my fingers into her pussy, deep, with my palm facing upwards. I slowly began to use my fingers in the classic 'come here' motion to rub the front wall of her pussy while I was sucking her clit. I suddenly felt her hand on the back of my head, pressure at first, and then she grabbed a fistful of hair. She just gripped my head, holding it there as I heard her moans intensify. She was practically screaming now, and her other hand was gripping her breast so tightly, I knew she was getting close.

I sucked her clit harder and faster, and I could feel her pussy begin to tighten slightly around my fingers, gripping them, then relaxing again, then gripping, then relaxing. At the same time she went silent, holding her breath and writhing around. Her clit began to throb between my lips and I knew she was cumming. I kept my fingers deep inside her, and I sucked her clit fairly hard, holding it into my mouth between my lips as I felt it twitching very fast, and felt her whole body reaching orgasm. Her clit was throbbing quickly and firmly in between my lips, twitching, and her pussy still throbbing on my fingers. Gradually it all slowed down, and her back stopped arching, and her hand gripping her breast relaxed and fell to her side. She let go of my hair. She was done....I withdrew my fingers, and could see strings of her cum on and in between my fingers, I let go of her clit with my mouth. I tasted her.

She looked at me and her face was so flushed and she was panting, I didn't wait any longer, I moved up, pulled the foreskin back on my hard cock and I pressed it onto her clit. I stroked it up and down her pussy a few times to get covered in some of her glorious wetness before I thrust inside her, deep inside her. Her senses were obviously heightened after her orgasm, and she was so wet that my cock glided easily into her, despite her feeling really tight. With each thrust of my cock into her soaking wet pussy, I could feel that I was getting covered in her cum and juices, it felt unbelievable.

I knew I wasn't going to last long - I'd wanted to cum when I was inside her before - so I made sure I filled her pussy deep with my cock. I pulled her legs so that we were both at the foot of the bed, and I could press my feet against the footboard. I then lifted her legs so that they were over my shoulders. She knew what was coming and wanted me. I'd never felt someone wanting me so badly and the feeling was amazing.

I entered her again, but this time I leant right over the top of her, looking into her face with her knees now nearly touching her own breasts. I thrust deep and hard, pushing against the footboard with my feet. I wanted to get all of my cock so deep inside her. She was loud, very vocal, and I picked up the tempo, now thrusting hard and fast, pounding into her pussy. I could feel and hear my balls slapping against her ass so loudly, rhythmically, fast, slap, slap, slap and with each slap, another groan from her. She was tensing up again, she gripped onto her own calfs with her hand and her eyes were now tight shut - I could tell she was going to cum. Suddenly her pussy got so tight that it nearly pushed me out, and she let out a huge groan and a sharp exhale of breath. I stopped thrusting and kept my cock inside her, and felt her pussy twitch like a rubber band around the base of my cock, squeezing it over and over. Once the squeezing stopped, I thrust hard again.

She told me she wasn't on any birth control, and that I must pull out. This to me was a major turn on. I love the taboo, and hearing this nearly made me cum. I told her ok, and asked her where she wanted me to cum. 'My tits, come on my tits, I want to feel the warmth of your cum running down them'.

I told her I wanted to cum inside her, I needed to cum inside her. 'OK', she said, 'cum inside me. Put your cock inside me Andy, and fuck me til you cum'. 'Fuck me Andy, fuck me til you cum, I want to feel it inside me'....this was too much. I could feel my body beginning to react, I could feel the tingling running up my arms and into my head, the feeling I get only when I have the most intense orgasm.

I knew I couldn't cum inside her, it was too risky, but hearing her beg me for it was one of the most unbelievably sexy things I'd ever heard. I was getting close. I longed to cum inside her, I love nothing more than burying my cock deep inside and cumming, feeling the pussy filling up and feeling the hotness. With each thrust I could now feel the exposed tip of my cock brushing against the opening of her pussy and I couldn't hold back any more, my senses were in overdrive.

I fought the urge to thrust even deeper, whenever I cum I thrust that 10% deeper than I ever can during sex itself, my body just needs to be that bit deeper inside at the point of orgasm. I felt my cock start to twitch and I slowed down. She could obviously feel it to, and sense that I may pull out, she grabbed my ass and pulled me close to her. I pulled against her, but she wanted me inside her when I came.

I broke free, and pulled out on the third or fourth twitch of my cock, just in time to watch the biggest strand of cum I'd ever shot spray out across her pussy and pubic bone. I grabbed my cock and pulled the skin back, ready for more, and I shot 4 or 5 times across her body, up to her tits and across her belly. I covered her, I was so turned on, and I couldn't believe how hard she had made me cum by wanting me, begging me, to cum inside her. She looked at her body, now covered in long strands of my cum, and just watched it start to run down her flesh.

As the orgasm finished, I swore quite alot, in pleasure, it was intense, and the smaller twitches of my cock continued for a good 10 or 20 seconds while I held my foreskin back, and I finally squeezed the last few drops from my cock, watching them leave the tip and fall onto her now gaping pussy.

I sank back onto my haunches, and we just stayed there for a while, looking at each other. She admired the mess I'd made, and rubbed some into her tits. I eventually got up and grabbed a towel from the radiator and helped clean up the mess. We then laid down together and chatted for a while.

We both knew we had done the wrong thing, but for me this was one of the greatest experiences of my life, I was in shock that it even happened in the first place, and I was so delighted that it went so well. I was spent.

I didn't want to fall asleep, so I got up and got dressed. We parted knowing that this was something neither of us would ever forget, and to this day I think back on it quite regularly wondering if it will ever be as good as that again.