Sex with My Best Friend’s Ex



What’s your gender? Man
How old are you? 25
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Shelton, Washington
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Manager
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 43
How many hookup stories have you here posted before? 0

Sex with My Best Friend’s Ex

How long ago did this hookup happen? 3 Years Ago

What was your relationship status at the time? Single

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? For more than 3 years

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? I grew up in a lake community, with other kids from all around the lake, who always brought along friends and such.
The girl, “R”, was a friend of my neighbor, T. She was blonde with blue eyes, a beautiful smile, about 5’8” and in great shape, with long legs, a firm ass, and perky little tits.
She dated my best friend for 2 years or so, and naturally, the 4 of us all hung out a lot together.
Prior to dating my friend, my neighbor had tried to hook me up with R. We texted and flirted and kissed once when we all hung out, but it eventually fizzled because she didn’t live nearby, and none of us were old enough to drive at that time. Years passed, and R and my friend had since split. He married another gal, I moved into a place of my own, and she went off to college.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It was a few days before Christmas, and I was at a Christmas party when I got a random text from R saying: “Hey! Back in town for the holidays. Really miss you and everyone else. It’s been awhile! Let’s catch up?!” I replied, and we planned to meet later that night for some drinks and to bullshit. I gave her the address to my house and told her where the spare key was, in case she beat me there. I got home, and there she was, just as cute as ever, and so happy to see me. We talked for hours and drank a lot. Eventually, we were in my kitchen, and R was showing me pictures of random things she’d done or seen lately on her phone. She scrolled to a video, and as soon as it started playing she swiped passed it. I said, “Hey, what was that?” Just out of curiousity. She smiled, looked at me, and said: “Well, I guess you’ve seen boobs before.” Then played the video, which was of her and a friend flashing at a party in college. Her tits were perfect, and I was surprised she showed me.
Soon afterward, she said she was tired, and I was too. My house was only two bedrooms, and my roommate was home that night, conveniently leaving only my bed or the couch. R said we’d just bunk up, but she needed the room to change first. I waited, and she came out wearing a tank top, glasses, and yoga pants. We headed to bed, and I jokingly spread out completely right away. She laughed and told me to stay on my side of the bed. I went back to my side, but she scooted closer to me, and we eventually met in the middle. I put my hand on her shoulder, in a friendly way, and she put her cold feet on mine. She then backed her ass right into my cock, and asked: “Do you have a boner?!”. Mortified, I broke the awkwardness with humor, and said: “Sorry, it’s what happens when I sleep.” She just said, “huh” sort of devilishly, and pushed her ass back more. All that separated our skin was a thin layer of clothing.
After laying there contemplating my next move for forever, I finally got the courage to go for it.
I pushed my hand down her shirt and said “these must be those boobs in that video” expecting a sarcastic response. R rolled right over to face me, shoved her hand down my pants, and we instantly started making out.

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 stroked me up and down, and said: “My god you have a huge dick!” (10” on a normal day). I pulled her yoga pants down, and she spread her legs, almost begging me to touch her perfectly shaven pussy. I fingered her for a minute, and then she started taking off all of our clothes. Her body was perfect, and she had the most perfect tits. They were even pierced. Still making out, she pulled back, and asked: “Should we be doing this?” I took one look at her naked body, glistening wet pussy, and the grip she had on my throbbing cock, and told her to shut up. I grabbed a condom, and she rolled it onto me. She then grabbed a hold of me by the dick, and pulled me down to her, slowly easing me into her tight warm pussy. I fucked her slowly, easing her into taking my cock, which she enjoyed more and more. I pulled out, bent her over, and crammed my cock back inside her, making her moan loudly. Her ass jiggled while I fucked her harder and harder. I eventually laid down on the bed and told her to get on top of me. Her arms were on my shoulders, and her blonder hair was in my face while I slammed my cock in and out of her deeply, making her perfect tits bounce up and down. She started yelling “Oh My GOD!”, and I saw her close her eyes. Her pussy tightened up around my cock, and then I felt it loosen, and release her warm cum all over. I fucked her harder, and she came 3 more times, squirting her warm juices all down my balls, and my hips. I slowed down to let her catch her breath, and she looked at me and smiled. “Your turn!”, was all she said.
I knew what I needed, so I laid her on her back and put her legs up on my shoulders. Just before I pushed back into her soaked pussy, she reached down and pulled the condom off.
Her pussy felt so much better bareback. I knew I wasn’t too far away from finishing. I pushed back and forth, grabbing a boob with one hand, and one of her tiny little feet with the other, so I could suck on her toes. She’s obviously never had that before because I felt her start to cum again. This made me go over the edge, and I felt my body start to tense up. I pulled out just as she finished, and watched her pussy squirt even more as she shivered. She reached down, and barely stroked me, making my beat red cock explode. The first shot hit her right in the face and hair, then again. Next it hit her tits, her stomach, and finally just oozed onto her hand. She was covered, and in utter shock. I smiled and pulled my hair back, catching my breath, looking at the huge mess I’d made all over her. She exhaled, looked at the cum on her hand, and licked it right off.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, multiple

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? The next day wasn’t awkward at all. We agreed to not say anything, then she said she had told T, my old neighbor and kinda laughed about it. I tried to have sex again that morning, but she said she was too sore. My friend eventually found out, but couldn’t really be that mad, because he was already married to another gal. I’ve seen R once since, and she acted normal, but I know we both always think of that night when we see each other.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Withdrawal, Condoms

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, Intoxication, Just happened, I don’t know why, just went along with it, It was easy / convenient

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? A little tipsy/high

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? Somewhat

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? I told another mutual friend of ours, and he was blown away. He actually said he was jealous because he’d always thought R was super hot.

How would you best summarize people’s reactions about this hookup? Mixed (Some positive, some negative)

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? The “girl next door” vibe she’d always given me, and how well we worked with each other.

What was the WORST thing about this hookup? The awkward fact that my friend had dated her, and then found out we hooked up.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not really, I’ve always been super open minded, and about free love.

All things considered, how POSITIVE was this experience? Fairly positive

All things considered, how NEGATIVE was this experience? Somewhat negative

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? I’ve hurt a lot of feelings for the sake of sex, and had a blatant disregard for people’s feelings, just for my own reward. It’s the greatest thing if there’s no drama or bullshit, but there always is with women. They’re the ones that make it hard to stay “casual”.

What do you think about the Casual Sex Project? Awesome. Love reading and posting.

You have a hookup story to share? Submit it here!