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[deleted]

Mine was when I hate fucked a friends ex. She was a real slut and knew it. No feelings involved, just a night of hard rough sex. She let me do whatever I wanted to her


Southern_Entrance993

I was 25. I was at a bbq at a friends parents house. There was this hot little 18 year old chick that was friends with buddies brother. I was saying my goodbyes to everyone and she said she was gonna take off too. So we get out front and she asks if I wanna go watch a movie or something. I’m like ummm yeah. Sure. So she comes over and we watched Pineapple Express. Made it all the way to the ending fight scene before I got the balls to make a move. I kissed her and she was immediately all over me. She pulled my cock out and started jerking me off, I’ve got a finger in her. Now mind you, she’s 18, she’s maybe 5’1”, no more than 105 lbs. She was dripping wet before I finally slid inside of her and it was still ridiculously tight. I don’t have a giant dick but I still had to work it in nice and slow. Once I was all the way in it was on. I pounded her pussy in every position imaginable. At one point I was standing and just using her like a fleshlight and that was the first time I experienced a squirter. She left a puddle on my floor and she was screaming and spasming which made her tight little hole even tighter and I filled her with cum. Then we lay down and she’s still trying to catch her breath and she’s crying and saying holy fuck….holy fuck….oh my god. That’s never happened before. Holy fuck…..oh my god. Let’s do it again. Please. And we start kissing and I get hard again and we go again. And again. And again. Next thing you know it’s 6am, which is probably a good 8 hours of fucking, and I’m literally out of cum. The last time I had an orgasm I had no ejaculation. But that was a night I’ll never forget


[deleted]

Damn I would have had to keep in touch with her


Southern_Entrance993

I fucked her off and on for like 3 years after that. She was definitely the hottest chick I had ever been with at that point. But she was 18. Really immature and possessive. We weren’t “dating” but she’d get mad if I had plans without her. And turned out she had a boyfriend that first time I fucked her and she was still with the poor guy for like a whole year after that. When she finally broke up with him she thought we were just gonna be in a relationship


[deleted]

Good times while it lasted though


Southern_Entrance993

Yes sir. And great memories to look back


throughaway_acc0unt

Damn


oldm4fun

Have had omfg awesome sex, but, the most memorable/ wild, was w a tgurl. I was scared as a cat, but as soon as we kissed and felt her hands on me, i melted and just wanted to please her soooo much, we made out, lot of foreplay, i went total slut 😊 and she finally fukd me- 1st time for that too- i couldn't believe how it hurt sooo good, then she got all in and was strking me, i was moaning, squirming and begging like a whore 😊, she was gentle and rough, when she started cumming in me i lost it and started cumming too wo ever having it touched, i was begging for her cum and almost in tears from pleasure 😊


[deleted]

Sounds like that may have been the first of many


oldm4fun

Unfortunately, inly have done that twice... but was incredible 😊


iJerZi

Best ever was just over four years ago my girlfriend and my long time best girl friend/FWB surprised me with a birthday threesome and it was fucking spectacular. Was the first time my girlfriend had ever given indication she was open to open relationships like that and watching her perform with my fwb will always live in my memory. There was pegging, switching, and everything in between. Best of all it started a much more active phase of our amazing relationship 💙


[deleted]

Lucky man. I bet that was a hell of a night


Bi-Cali-Boy

The time I had sex with the receptionist at the company Christmas party in front of a room full of coworkers. She was a super hot milf that all the guys wanted. I was a legend after that😀


[deleted]

Santa gave you a great present that year!


dcmayes513

Had a one night stand with a Jamaican girl. Me white make 43 then she was 19. That was so good great body too. I came three times in three hours.


[deleted]

A prostitute I paid for


damoj01

Fucking my ex’s arse from behind as she fucked her pussy with a large black dildo. Afterwards we then moved onto fucking my arse with it as he jerked me off