Current location: California
Highest education received: College degree (eg., BA, BS)
Relationship status: Married
Religious affiliation: None
How religious are you? Not at all
Sexual orientation: Heterosexual
How many hookup stories have you here posted before? 3
WoW First Time
How long ago did this hookup happen? 10 Years
How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? FWB
Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? Jean was 5’10” brunette, part native american part Caucasian. Pear shaped with nice bubble booty and average B cup breasts (think Amber Rose with long black hair and smaller breasts). She had a little chub on her but not enough to call her even chubby.
We had known each other through the internet and AIM (shows how long ago this was).
We initially met at a Gaming Convention and chatted casually. I had a little crush on her so I contacted her through AIM and began a chat connection with her.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? After chatting online for a month she casually invited me to her place to hang out with her and her friends and to play World of Warcraft (admittedly I did not play much but lied so that I could visit). She lived about an hour away so I packed up and drove over. The night prior I told my co-workers what was going on and they told me to bring a condom just in case. I was still a virgin at this point and didn’t think I had enough game to pull it off. But I bought a three pack anyways and hit it in the depth of my jacket.
After driving there I was able to meet her with a hug and her friends (alot of guys and a few girls including one of her two female roommates). We all had fun chatting and they had set up some computers to play WoW. I wasn’t really into it much but played as well. For the most part I didn’t get a chance to talk to Jean because she was always with her friends.
At one point in the night we ran out of drinks and she said she would go get some more. I told her I would come too and help carry. She agreed and we took off. On the drive there and back we chatted alot, tried to use humor to get her to let her guard down. Although we had similar hobbies I kinda felt she was alot more adult than I was.
We got back with the drinks and everyone shushed us. We asked what was going on. They got quiet and we could hear on the other side of the wall the sounds of a couple having some pretty loud sex. She sighed and said it was her other female roommate. She had apparently come home while we were gone with her boyfriend and went straight into her room.
We all laughed but soon got back to gaming and chatting. Me on the other hand had never heard people having sex so it weighed on my mind. A few minutes later we heard the roommate cum and all did golf claps. Jean laughed and to be honest with the sex going on next door my eyes were all over her tits and ass and legs. At one point our eyes met and I looked away.
As it got closer to 1am most everyone began to head home. I was pretty tired and Jean’s roommate asked how far away I was? I told her an hour and she told me that I could stay the night if I wanted to. I looked at Jean, she smiled and said she was fine with it.
The last of the guests left and all Jean’s roommates went into their rooms. I helped Jean get her computer from the living room and put back into her room. She set back up the computer and turned it back on. She said we could chat as she continued to play WoW. I sat on her bed as we chatted. I was pretty nervous being in her room alone. At first she sat in her chair with her back to me. We talked about the party and gaming in general.
I was pretty tense but decided to ask her some personal questions to see if this was going to go anywhere. I joked about the roommate who was having sex and asked if the roommate had done that before. She paused her game and turned around and looked at me. She bluntly asked if I was interested in her? I paused not knowing how to respond but knew if I had a chance this was it. I told her yes. She got out of her chair and sat on the bed next to me.
What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? She looked me in the eyes and put her hand on mine. We leaned in and kissed. At first I was a little awkward but got into it pretty quick. It was obvious she had alot of experience. As the kiss continued her hand found its way to my raging cock. She touched it and broke the kiss asking if I brought a condom. I said yes. She asked if I was expecting sex. I told her no, that I was told to bring it just in case.
She got up from the bed making me think it was over. She stood in front of me and took off her shirt revealing her bra. She then unbuttoned her pants and dropped to reveal a nice black thong. I bit my lip and eyed her up. She asked what I thought. I told her she was gorgeous and I wanted her. She walked over and straddled my lap, her crotch was right over mine. She began to kiss me. My hands found their way to her perfect ass. I rubbed it sensually. She moaned between each kiss. She grabbed my shirt and pulled it off me.
She then reached up and took her bra off. I marveled at her perfect breasts. As I sucked on her nipples she moaned and began to grind her pussy on my cock. I was losing my mind. She got off my lap and slid down my chest until reaching my crotch. She stared me in the eye as she unbuttoned my pants. My dick popped out. She grabbed it and began to suck. My first blowjob was simply amazing. Her pierced tongue swirled around my shaft. She told me not to cum. I told her I was getting close.
She stopped and stood up. She turned around showing me her ass. Bending down, she removed her thong. Her ass and pussy was on full display. I simply said, “Damn!” She told me to put the condom on. I stood and took off my pants, grabbing my jacket and pulling the condom out. I had never put one on and fumbled putting it on. After a second I got it on. She walked back to me and straddled my lap again. She reached down and grabbed my dick between her index and middle finger. She slowly guided it into her pussy.
It was simply amazing! I never knew how tight a pussy could be. After a moment she began to grind on my cock. She moaned like crazy. So much so I asked if it was alright to be loud. She said she wanted her roommates to hear since her roommate had did the same earlier. I grabbed her ass and fucked her hard. She picked up the moaning. I was getting close and told her I was cumming. She told me to cum. With a groan I let out a huge load.
I fell backwards breathing heavily. She licked her lips and leaned on me. She asked how she was? I told her amazing and that she was my first. A little surprised she smiled asking if it was ok? I told her yes and that I wanted to do more. She smiled and said she was game.
She laid on the bed as I got up to grab another condom. She told me it was fine. Since I was a virgin she wasn’t worried about STI and she was on birth control so she wasn’t worried about pregnancy. I was really hesitate but then she spread her legs and pussy. That juicy pussy just called to me. I got on top of her and fucked her missionary. 5 or so minutes later she came hard. A minute later so did I filling her neatly trimmed pussy with my virgin cum. We collapse breathing hard. We kissed and fell asleep just like that.
Did you have an orgasm? Did your partner(s)? I came twice and she came once
What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? At first a condom but not the second time. She was on birth control. I asked if she did and she told me no.
What were your REASONS for having this hookup? I was crushing and wanted her for my first
Were alcohol or drugs involved? If so, how much? I had only drank a little. She had some sake, rum as well as some others
What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? We woke up the next morning. Cum was still coming out of her. She asked if I wanted a shower? I said yes. She opened the door and peeked out. We ran butt ass naked down the hall to the bathroom. We turned on the water and made out. We had some nice vertical sex in the shower. At one point I had her against the shower door, breasts pressed flat as I grabbed her ass and fucked her pussy from behind. Neither of us came but it felt amazing. We popped out in towels. Her roommate I hadn’t met was there waiting. She smiled and walked past us. I was a little stunned but both of them seemed ok so I kept calm. We went back into her room and made out some more then got dressed. I had to be somewhere so I took off, kissing her and asking if I could call. She said yes.
To whom did you talk about the hookup? How did they react? My co-workers though I left out the virgin part. She had told some of her gamer friends because one of them joked about it the next time I was over.
Was this a consensual and/or wanted experience for you? For your partner? Yes all around
Do you regret this hookup? If so, why? Nope
What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Popped the cherry with a hot nerd. Got to fuck a beautiful woman and made a great friend.
Worst was probably that it didn’t go beyond friendship but oh well
All things considered, how POSITIVE was this experience? Very positive
All things considered, how NEGATIVE was this experience? Not at all negative
Anything else you want to add about this hookup or anything else? We would meet every few months to hang out. We had sex a few more times as well. Once even with one of her roommates watching us which I might talk about in the future. We still chat but nothing has happened sexually for a long time.
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