My mil watched me jack off last night. 
she came to stay with us for a few days, and last night her and my wife were watching some stupid chick flick that couldn’t stand to watch. So I kissed my wife and told them I was going to bed early. I was just going to lay down and play on my phone until my wife came to bed. But you know how it goes when you start scrolling, you run across a picture that makes you look for more and before long you wind up on a porn site. So that’s what happened, I was watching a few clips and got horny. I wasn’t sure when my wife was coming to bed and I didn’t want to wait, so I figured I would just rub one out on my own and get it over with. Well, my bedroom door wasn’t closed all the way, and I was already too settled to get up and shut it so I said fuck it and I continued. Well a couple minutes go by and I’m stroking myself slowly, enjoying the clip I was watching when I heard foot steps come down the hall. My mother in law was on her way to the bathroom, and I knew it had to be her because my wife walks like a bull on a rampage everywhere she goes. I knew it wasn’t her. I probably should’ve stopped and covered myself but when I’m horny I get bold and like to push the boundaries. So I pretended that I didn’t notice her and just kept going. I expected her to notice and pretend like nothing happened, she’s too shy to say anything about it afterwards. But I wasn’t expecting to see her stop just past my door and turn to look back. From her angle all she could see was my lower half, my legs parted with my cock in my hand, but she couldn’t see my face so she assumed I couldn’t see her either. Well what she didn’t see was the dresser mirror beside the bed that let me see down the hall where she was. And her eyes were fixed on my cock. I watched her look over her shoulder to make sure my wife was still watching the movie but then she went back to watching me. So I gave her the best show I could. I was shaking it and stroking it hard while watching her out the corner of my eye. She stayed in the hallway watching until I finished. Normally I would just finish in a tissue and keep it clean but since she wanted a show I let myself blast cum into the air and all over my stomach. I could see that she was breathing as hard as I was when I finished. She must have enjoyed what she saw. Then she turned and went to the bathroom and stayed in there for a few minutes before coming out. I don’t know for sure but I like to think she was in there rubbing her pussy after the show. I gave it some time after she returned to the movie and I walked in there pretending I just wanted to get a drink so I could see how she acted, but she ignored me completely. So I walked over and kissed my wife good night. And made it a point to pat her shoulder and gave her a peck on the cheek like I often do just to have a reason to touch her. I was wondering if she would shy away from my dirty hand, but instead she actually gripped it tightly and smiled at me and said good night sweetie. I believe she enjoyed it as much as me. I can’t wait to try that again.

Bend me over and put your foot on my head as u fuck my whore ass

I am a long time lurker, first time confessing something.

The truth is, that I do not have too much to confess, since my sex life has been this vanilla slope, and funny enough, only thing worth mentioning, was my first gf, to whom I didn't even lose my virginity, in a way...

We were seniors in hs, so both legal, and she was this ugly girl, but with a nice body, and great, firm tits, kind of big. From the start she told me she won't have sex before marriage (even though I am old, this was an antiquated way of thinking, even back then). We would make out, she had no problem with me groping her, but only over the clothes. I would try to put her hand on my crotch, but she would back off. It drove me crazy.

One time, I was super excited, so I just said to myself, what the hell, and pulled my cock out. She didn't mind. As she was sitting on my stomach, while kissing me (she was very petite), I jerked off behind her back. She knew what I was doing, since I pressed my cock against her ass in pants, but she did nothing but kissing me, as I pleased myself.

The next step was, I would do it, and she would sit on my cock, while it is pressed against my belly, and slide up and down, until I cum. First time was really tough, since she wore some kind of jeans, but next time, she was this thing, track suit kind of thing, kind of like yoga pants, and it was better, so much so, that she came from all that dry humping.

This went on for a while, until, one time, she came from the dry humping, and I guess her body was just betraying her, so she went down, and took my, already drooling cock in her mouth, and I was done in an instant.

I never got to fuck her, but after that, things heated up, so we would usually just give each other oral. I think the most interesting part of all this was, not just that we were both virgins, hungry for sexual interaction, but the thing that she wanted me inside her, so much, that over time, we did many things just to emulate more and more sexual experiences, except the one we both wanted.

For example, this one time, I was giving her a foot massage, while she was naked on her stomach, and after a lengthy massage, my hands went up, so did I, and it ended up as me licking her ass, while rubbing her clit, until she was done, and she immediately wanted to return the favor, act per act, foot massage, going up... This thing ended up as a deed, I later found out, was colloquially called rusty trombone.

Our relationship ended, when we both went to college. We kept in touch, and were a "long distance item" for two months or so, but since neither of us was able to come visit the other, it ended in a way, that we both just stopped calling each other. Not long after that I lost my virginity to a girl in college, as most of us, at least back then, did.

Never have I ever, after this, had a more intimate relationship with another woman.