A Few Regrets
I'm 26 years old, I'm in good shape and I've been married for four years. I love my husband, but lately we've been fighting a lot and haven't been making love very often. Not even make up sex.
Not getting laid always drives me crazy and I'd been hanging out a bars with some of my single girlfriends looking for guys to possibly hook up with, but I always got too nervous when the moment finally came to go home with anyone. Having my friends watching and waiting to gossip about me didn't help either.
My whole world changed when Donna, one of my married friends, confided to me that she cheated on her husband through an online dating site. She said whenever she feels like it she finds a new lover to have an affair with and fucks him regularly until she feels guilty enough to break it off, which is usually about a month. Regardless of how much she wanted to be faithful, she felt she cheated out of necessity rather than adventure. It was obvious that I was interested right away and she provided enough encouragement and advice so I could do it myself.
I was so excited and nervous when I arranged my first online date I felt like I was a virgin again. I narrowed down my choices (there were a lot of guys to pick from) and eventually chose Jeff. He was 24, also married, and just as inexperienced as I was when it came to cheating (or at least he said he was).
I was surprised to find from our conversations before we met fact to face that we went to the same gym. Naturally it became our neutral meeting place. I go to a very large gym and at fairly specific times so I didn't expect that I had ever seen my soon to be lover there before. I was shocked when I figured out who he was and I couldn't believe my luck. I'd seen him many times and I'd already fantasized about fucking him! To say he was gorgeous was an understatement. We'd never talked, but he told me later that he'd noticed me as well, and especially enjoyed checking out my ass while I used the ellipse machine.
For our first date we worked out together, he was working on his chest and arms and I spotted for him- making sure he got a good look at my breasts as I helped with his last couple of reps. I don't usually work out very much with weights, but this time I made an exception and whenever I caught him glancing at my ass or my tits my pussy throbbed uncontrollably. I was so turned on I couldn't wait to get him home.
After our workout I thought we'd have to get a hotel room, but instead we went to his place because his wife was gone for the weekend. I went with him in his car and our conversation really heated up as he drove.
Once we were safely inside his house he gave me a little tour that ended in his bedroom. We didn't start pawing each other right away, I playfully seduced him by starting a little strip show on his bed. I never actually finished stripping because I took my panties off first and before I knew it his head was under my skirt and I was coming all over his face.
I don't think I've ever had an orgasm that fast, part of the reason must have been my overall excitement of cheating on my husband, but he definitely knew how to please a woman, and there's nothing better than having a magic tongue work on my clit. What was also a bit weird was that I responded positively when he slipped a finger in my ass as I arched my back in a heated frenzy. I hate anal sex and it had been ten years since I'd had anything up there. It wasn't exactly comfortable, and I would have stopped him, but I was too busy having an orgasm to do anything about it!
When my body stopped convulsing uncontrollably he rammed his cock all the way inside my pussy with one thrust and I didn't get a chance to totally appreciate the size of his cock until we were fucking like crazy. It was pure lust and I gave myself to him completely.
I didn't come while getting fucked, but that's normal for me. Even though I enjoy it immensely, it never takes me over the edge. When he finally came he pulled out and begged me to swallow for him. I don't usually let my husband come in my mouth, and actually I don't normally give head after getting fucked because I don't like the taste of my pussy, but for Jeff I jumped at the chance to please him and soon as my lips passed over the head of his cock he filled my mouth with a salty prize.
It tasted really bitter, but I don't regret doing it. Sometimes I still fantasize about that moment when I masturbate. There's something primal about having a healthy cock throb in my mouth.
After that I relaxed on top of him in a loving embrace as I silently contemplated where our relationship would go from here. I'd initially thought I'd only fuck Jeff once, but what I'd experienced was so good, I was already looking forward to seeing him again.
Pillow talk with Jeff was very relaxed, and we had fun poking at little things we'd noticed about each other. The conversation took a sidestep when he mentioned how obvious it was I liked having his finger up my ass. He was very surprised to find out I wasn't experienced with anything being up my ass and when I told him I've only had anal sex once before in my life I felt his cock get rock hard against my stomach. I don't know if I believe him, but he said his wife loved it and every time they had sex she demanded to have her ass fucked. Actually, I'm sure he was lying now, and it was a ploy to seduce me into letting him fuck my ass, but it worked. He convinced me he could give me an even better orgasm than the one I had while he had his finger up there, and that he was so experienced with anal sex he could make it not hurt.
It was something I seriously regret doing. He was gentle enough, and he used a lot of lube, but my ass was just way too small for his cock. When he first put it in, it didn't slip inside me like he promised- he wedged it up there and then eventually fucked it with strokes that were deep and hard. It hurt, not as much as I thought it would, but besides the pain, it was one of the grossest sensations I've ever experienced. Even though I've had anal sex before, I've never had my ass fucked as hard or as deep.
The only benefit was the sense of pride I got for turning him on so much, and I don't know how to put this, a sense of being nasty for the sake of being nasty. He was beyond into it, and thankfully he came a lot faster than I thought he would. All I could think about when he was done was what my husband would do if he knew what I'd just let this man do to me. I felt used. It didn't seem right.
It took us a couple of minutes to compose ourselves afterwards and Jeff couldn't stop thanking me for letting him do me in the ass. I really didn't know what to say to that. We parted on an awkward note, but it helped that we didn't have very much time. I had less than half an hour to shower and get back to my car so I'd be home in time to make supper for my husband. I made it with just minutes to spare. Jeff offered to meet again anytime I want, and I might, but if I get that desperate again I decided I'd try hooking up with someone else from the Net instead.
I'm satisfied enough with reminiscing about my first kinky affair, but next time, I'm going to be careful about getting talked into anything.
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