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Losing my (M23) virginity (kinda) to a family friend (F36) at a party
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Before you guys laugh and call me out, yes I lost my virginity really late than anyone has or longer than I want. My defense whenever I tell people is that I used to be very big and I was shy and introverted so that never helped me get pussy if I don't talk to get pussy lol. So yea it was my cousin's BF surprise party (gay partners) and he invited his BF's old college roommate who brought her current roommate. She was fair looking and was a thicc girl and way older than me as you see in the title. So as the night went on everyone were taking shots and drinks and I had like 4 mixed drinks and by then 6 shots of Jameson and she had to have been close or above my drinking and shot count. She got to that drunk level just saying what's on her mind so she asked who was single cause she wanted to flirt and be all over somebody and I was the only one really. She joined me in the pool later on and just fucking jumped onto me straddling me while I held her up into pool now face to face with her and I'm still a little shy so this girl on my dick basically in front of all my cousins made me so damn shy and embarrassed. I can spit dirty talking game but not in front of or around family lol and what made it even worse was MY DAD WAS THERE so I just wanted to die cause I didn't want to do this in front of him either. Eventually I ignored all the teasing I got and walked a bit further away from my cousins in the pool still holding her and spat my sex game. I told her I'm. It looking for a relationship but down to have fun if she got what I meant and she giggled and asked if l'd visit her since she lived like 4 hours away and I said I would if her pussy was good enough. She giggled more and said it was so I called her bluff and said I'd need to see for myself right now. She really loved that and started to rub herself on my cock in the pool and asked when was the last time I fucked. At that moment I was deciding to either lie or tell the truth and decided to tell the truth so if we did fuck, l'd have excuse why l'm so bad and not knowing what to do lol. I told her l've only ever gotten a handjoh and was still a virgin and that made her so horny. She asked if she could pop my cherry and my heart was racing cause the time has finally cum (lol) and said yea. I was thinking we would sneak into the house or fuck in my car but she dragged me to another part of the pool kinda out of sight from everyone (pool is designed like a big heart with a hot tube at the top middle so gave cover) and pulled my shorts down and bit and moved her bikini bottom to ride me in the water. I was so scared to get caught by my family especially my dad, I told her to go inside and wait for me in the restroom. She quickly did and I followed a few minutes later. When I knocked on the restroom door, she peaked and saw it was me and dragged me in. We quickly got to work with her jerking my cock to get it hard and then tried to ride me but there were two problems; being wet and then air drying made our skin rough like wet rubber so it was hard to comfortably slip it in and also I was drunk af and I couldn't get really hard LMAO. I was so embarrassed and horny but not hard horny lol so she kinda gave up trying to quickly put it in and just started to suck my cock. It felt good having a mouth finally suck it especially someone older than me which is a kink of mine but she only took like the top half of it which was kinda disappointing cause I wanted her to deepthroat my shit but I think she was too drunk and didn't want to throw up on it by accident if taking too much. She sucked it good and I knew we had to hurry before everyone else got suspicious so I told her to sit on the toilet seat and spread her legs for me so l can eat her out. She did and I dug my face it that shaved meaty pussy and ate her the fuck out like I was starving for it. Spreading her pussy to for my tongue in and then went to licking and sucking that clit while I fingered her. At first I thought I was doing bad because I didn't hear anything but then I heard her breath heavy and started to moan and squirm hard. I guess she held it in but couldn't anymore and let out that big inhale. I tried to get her to squirt and cum but I started to come down from my drunkness and needed to hurry before getting sick since I stopped drinking. She sucked my cock again to get it hard and ride it but still too drunk so I told her to suck me off more and she did and I got hard for a quick while and came inside that silky mouth. I apologized to her about it and she said not to since we were both drunk and sloppy at it but she loved how good l ate pussy and asked if that was my first too and I said it was. She said to keep it up and I'd lock any girl down with that. Later that night i had to leave but I tried to go for a round too cause I got horny again but I think my cousins jokingly teased her about our fuck session in the restroom cause it was obvious and everyone gave us looks so she declined but told me to keep up my pussy eating. I left kinda happy and sad and found her on IG and tried to add her to maybe fuck again one day but declined my friend invite. Even though I didn't get to lose my virginity at the time (I did like a week after which is another story lol) I had an experience and got to fulfill a kink of mine.

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4 months ago