Whats the best moment in the history of your sex life?

[JoBYY]

The most interesting moment of my sexual life was definitely when my friends order me a prostitute to lose my virginity. I will definitely never forget that in my life.

[nerdybetty]

Probably just after I came out to my wife as trans and she confessed that she'd always sorta known and wanted to make the day rather special for me. I'm a bit of a sub and have always wanted to try out some BDSM stuff; so she no joke hired an escort, a professional dom, to show her the ropes literally and figuratively and she treated me to what was, hands down, the best sexperience of my life.

Knowing that my wife not only fully supports me, not only is she kinkier than I am, but is willing to spend £2k just to have me tied, spanked AND give me some stellar pegging sex all in the same day??! Amazing. 10/10 wife material, I'd marry her twice if I could!
I'll have to write a blog post or story or something about it, it was honestly THE most wholesome and sexiest thing i think I've ever experienced. I think I'm the luckiest specimen alive lol

[joyvenusianarts]

The best moment of my sexual history was the defloration of my anus. It was in a forest and I got fucked in the ass by the boyfriend of a male-to-female transgender woman. She watched me get fucked the whole time. The guy had a very big cock and he fucked me in such a way that since then I can't do without big cocks deep in my slutty ass. From this memorable event, I wanted to feel this first impression again. And every time I use big dildos seven centimeters wide, it's the memory of my anal deflowering that comes to mind. My little ass was tighter then, and it was this wonderful moment that was this first time that made me want to explore the magic of anal pleasure more and more deeply.

[KCallidus]

The girl I first had sex with and dated on and off again through college did two things.

First, after a night of way to much drinking, she was riding my face and intentionally peed in my mouth. It was mind blowing and I loved it.
Second, a couple of months after that, having replayed that scene a few things, she met me later at night during the summer and road my face again. This time feeding me some other dude's cum.

That blue-eyed, red headed, fair skinned, freckled Irish Catholic sexy freak fucked me up for life. I was smart enough to know to never date another red-head again.

Still friends with that minx.

[JerkForThem]

Mine was probably when i dared my wife to wear her PVC dress (images in gallery) on a night out with me to a club. Didn't think she would do it but she did! The whole night guys were staring, groping her on the dancefloor, trying to chat her up etc. I was a walking hard on all night, she knew it too.

It gets to the end of the night and I’m desperate to get her home and fuck her. She has other ideas and drags me round the back of the club, down an alleyway out of sight (or so we thought). I hitch her dress up over her ass, bend her over and slide right in. She was already soaking wet. I cum quite quickly as I've been building it for a few hours watching other guys try it on with her. She turns around to face me and it turns out we are being watched by 3 guys. She kneels down, sucks me dry then stands up, takes my hand and we walk straight past them smiling.

Only regret is that they didn't join in!

[jedjcfvenusianarts-joystardust]

The best moment of my sexual history was the defloration of my anus. It was in a forest and I got fucked in the ass by the boyfriend of a male-to-female transgender woman. She watched me get fucked the whole time. The guy had a very big cock and he fucked me in such a way that since then I can't do without big cocks deep in my slutty ass. From this memorable event, I wanted to feel this first impression again. And every time I use big dildos, it's the memory of my anal deflowering that comes to mind. My little ass was tighter then, and it was this wonderful moment that made me want to explore the magic of anal pleasure more and more deeply.

[johnnyys]

when I tried sex with hot milf. I often hook up with older women via dating site. I wasn’t even looking for a hookup at first, but the site helped me rediscover a side of myself I hadn’t tapped into in years. I matched with someone who shared my interests and my pace. We took our time chatting and getting comfortable, and when we met, everything clicked.

[Sandy_Porn_Collector]

For me it was with a woman I fucked for a year or so. She was a filthy redhead with huge tits who would do pretty much everything, she would let me fuck her face, she would swallow my cum and take it up the ass.

One evening I was out with her as it was her cousins birthday and I had plans for her in the evening. At the time I was a police officer and owned a pair of rigid handcuffs (much better than the handcuffs with a chain). We went out for the evening and after the meal we were having a drink in a pub and I was telling her what I was going to do with her, at one point I was standing against the wall and she was in front of me rubbing my hard cock through my jeans with her hand.

When I got her back to one of the bedrooms at the cousins house I put my plan into action. Firstly I placed a blindfold on her, then I placed her hands behind her back and applied the handcuffs and she was completely at my mercy, then I got her on her hands and knees and stuck my cock inside her tight arse, I then fucked her while she screamed in pleasure before I dumped a load of cum in her willing ass.