It seems I'm always looking for a new thrill, sexually. And whenever I find one, it finds its way into my masturbation sessions. Of course.
When my marriage was breaking up, I had an affair. It was some of the greatest sex I've ever had. It was definitely the most fun sex I'd ever had. It was pure fun, with no strings at all. We fucked and sucked. We played for hours. And we laughed. It was just great.
Lisa, as I'll call her, was tall, about 5'9', and thin, with short brown hair, smallish tits (maybe 34A), which I loved, long, gorgeous legs, and a beautiful cunt, surrounded by the softest hair I've ever seen on a woman's pussy. She was totally un-self-conscious, free and easy in bed. We made love whenever and however, and we masturbated together all the time, too.
I don't remember quite how or why it happened. Lisa used to like to nip at me when we made love. One time, while I was wanking, I think, she started chewing on my nipples. I'm not sure I remember all the details, but I do remember that it felt incredible. I started moaning loudly, and Lisa just started nibbling harder. As I got closer and closer, she bit harder and harder, and then, all of a sudden, I just exploded, my cum flying so far up my body that it hit her in the cheek. It tells you all you need to know about Lisa, sexually speaking, that she then used her fingers to scoop my cum into her mouth.
After that, Lisa took to biting my nipples, which are very small, all the time. My new wife, whom I met a while later, does, too, at my request, and actually likes to bite me quite a lot. I often seem to have hickeys these days. But, as I said, once I discovered how much pleasure I derive from my nipples' being bitten, it was only a matter of time before I found a way to work it into wanking by myself.
The obvious thing, of course, was to tweak and pinch my titties, and I started doing that very soon after Lisa introduced me to the pleasure. But I found that doing so distracted me, to some extent, from whatever else I was doing. It was very hard to keep the pressure on my nipples when I was near orgasm. But there was an obvious solution to that problem too, and I found them in my washroom: Clothespins.
It took a while, actually, to get them properly adjusted. Most of them were too stiff, and hurt a bit too much for my taste. But it only took a little dismantling and stretching of the springs to get the pins to the right tension. Once I had them right that first day, I put three of them on each tit: One right on the nipple, and two on either side, pulling on the areola. I lay there for quite a while, not touching my cock, but just concentrating on the intense sensation. I pulled the pins off now and again, and put them back on differently. My cock was soon was hard and dripping, but I did not touch it. I imagined Lisa telling me I couldn't, not until my nipples had their fill. 'How long will that be?' I asked my imaginary lover. 'Fifteen minutes', came the reply. I set the alarm, and lay there in the bed, my eyes closed, my hands grasping the headboard as if they were tied to it. My dick was still dripping, and I fucked the air, my cock bouncing up and down on my abdomen as I did. A strand of my precum was flying around off the tip of my cock.
When the alarm went off, my hands flew to my cock and stroked it furiously. I came right away.
The next several days saw variations on that theme. I played out the same story, but with a butt plug in my ass. The next, most wonderful step came a few months later, when I hadn't used the pins for a while.
My wife was away, and I was feeling incredibly horny. None of my usual methods of wanking were giving me any real satisfaction, so I decided to try the pins again. That was good, but not enough, so I decided to try something I'd considered before, but never actually had the nerve to try: Putting pins on my cock and balls. The thought had been in my mind for a little while, ever since I'd stumbled across some pictures on the web of a woman masturbating with pins on her pussy. She seemed to be enjoying herself, and I found it hard to imagine what exactly it would feel like to have those sorts of sensations in my most sensitive parts. It intrigued me.
The answer was that it hurt, of course, but the sensation was intense, and once I started to adjust a little bit to the feeling, it was pleasurable, too. When I put the pins on my dick, I was not hard at all, because I was kind of nervous, but once they were on, my cock grew pretty quickly. It took a little bit of experimentation to figure out where the balance of pleasure and pain was best. After a while, though, I started to get some sense for that, and found that I liked having a lot of the pins on my dick. I've often had four or five lined up along the ridge on the underside of my cock, with a few more attached to my scrotum.
Of course, it's pretty hard to masturbate with all those clothespins on my dick. So mostly, I just lie on the bed and concentrate on those sensations, sometimes setting the alarm, as I described above, and imagining I'm tied to the bed, at Lisa's mercy. (She is always the one who figures in these sorts of fantasies.) When the alarm goes off, I'll pull the pins off my cock, rub it hard and fast, and spray my cum all over myself. And then I'll remember what Lisa looked like scooping it into her mouth.
The craziest session I ever had of this kind came about a year ago. Sarah was away again, and I was feeling really desperate for some serious sex with myself. I'd been fucking my ass a lot the preceding few weeks, and I'd been lamenting the fact that I have to move my arm so much when I do so. I'd tried attaching a dildo to various things in the house, but nothing seemed to work. My intention this particular week was to find something that would work.
The solution ended up being a combination of a broomstick, a Workmate workbench, and a jelly vibrator whose mechanism had given out. I ripped the end off the vibe, pulled out the now broken vibrating egg, and so was left with a semi-hollow jelly dildo. It went over the end of the broomstick, and that was held in place by the Workmates, so the dildo stuck out horizontally a bit more than a foot off the floor. A perfect height.
The sight of the thing made me hard. I got naked, lubed my ass, and got down on my hands and knees. Feeling really horny, I first gave my pink lover a blow job. I've never sucked a real dick, but have often fantasized about it, and love to practice, as it were. I can take a good sized dildo all the way down my throat, and that's what I did this day, too. I rocked back and forth and let my pink lover fuck my mouth. 'Don't come, lover,' I thought to myself. 'I need you in my ass.'
I turned around and found that I'd gotten the height just right: I backed up, and found the tip of my lover's cock pressing right against my asshole. All I had to do was keep backing up, and my sphincter parted, allowing him to slide right into my butt. It was a wonderful feeling, unlike what it usually feels like to slide a dildo into myself: This felt much a lot more like someone else was slipping into me. I held very still for a while, and enjoyed the feeling.
Slowly, then, I started to rock back and forth. It was wonderful! I'd always yearned to be fucked, and now I was very much being fucked. My pink lover was sliding deep into my butt, then back out again, and deep in again, bumping against my prostate each time. I was moaning loudly, and really getting into the fantasy. 'Fuck me, Sean', I kept saying, choosing without thinking a friend of my wife's from work who I knew liked to cross-dress and about whom she'd teased me more than once. 'Fuck my little asshole. Fuck me!' My cock was rock hard, bouncing up and down as I moved back and forth on the dildo, but it was very much not my focus.
I kept at that for quite a while. It was good. Very good. But now I was starting to feel the need to cum. I then had a true brainstorm. What I needed to do was intensify the sensation. I knew how to do it, too: Get the clothespins.
So I did, and I mounted them all over my body. I put a few on each of my tits, and I put a few more on my cock and scrotum. Then I backed myself onto the dildo again. The moment I began to move back and forth over it again, I knew this was a good idea. The pins bounced back and forth with my movement, pulling nastily on my tits, yanking on my cock and balls. It hurt, but it felt so damn good that I just started to go nuts fucking that pink cock, moaning and crying out, with pain and pleasure and who knows what the hell else. I paused for a bit and reached around to slap my ass hard, several times, hard enough, I would find later, to leave hand prints. But that too served only to intensify the sensation.
I rearranged some of the pins, which had started to fall off, and just held still for a moment, to feel the pink cock buried deep in my ass, the pins squeezing my tits, and their weight on my nuts and aching dick. I looked down and noticed it dripping. There was a puddle of precum under me, and even my stomach was slick with it, from my cock's bouncing up against it. I was close, and I knew it, and I wanted it bad. But first, I thought, one more good fucking. So I started at it again. Slowly, at first, but speeding up quickly. My ass, by now, was loose, and the pink dick was sliding in and out of my butt easily, all the way to the hilt, and then almost all the way out, sometimes even all the way out, and then back into me. I was moaning again, and talking dirty to my imaginary butt-fucking boyfriend, when an image suddenly came into my mind. It was Sarah, on the floor right in front of me, fucking her ass with a thick dildo and saying, 'Yeah, fuck his butt with your hot cock, Sean!' That did it, and, much to my surprise, I started coming, my cock spraying cum all over the floor in front of me. I just kept moving back and forth on that pink dick, and my cock just kept on spraying, for what seemed a very long time.
When the orgasm stopped, I just settled back onto my dildo, stayed there a few moments, and then removed the pins, which were starting to hurt. But I was still horny enough to get down on the floor and lick up some of my cum.