Girlfriend’s Best Friend Again

by Shawn

What’s your gender? Man
How old are you? 37
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Los Angeles
Highest education received: High school diploma
What’s your occupation? Welder
What’s your current relationship status? Engaged/Married (monogamous)
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 8
How many hookup stories have you here posted before? 1

Girlfriend’s Best Friend Again

How long ago did this hookup happen? Friday

What was your relationship status at the time? In a relationship (monogamous)

How would you best classify this hookup? Short fling

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? Kari was a hot redhead with green eyes. She was also my fiance’s best friend. She gave me a good blowjob about a week ago. I always thought she was very cute and funny.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? My fiance Kaylee, babysat for Kari’s son, so she came over to pick him up and Kaylee went with her sisters’ place to go babysit her sister’s kid for a few hours so her sister could go on a date with her husband.

Kari came to pickup her son and asked where Kaylee was. I told her she took off for a while. Kari told me, “I can’t stop thinking about your dick.” I was like, “what about it?” Kari said: “I want to fuck you. I’ve been thinking about it since I gave you a blowjob.” I told her I wasn’t sure.

She asked if I wanted to have sex with her, and I said yes. She then said: “you liked my blowjob right?” I said yes. She told me she’s been told that she’s great in bed too. That got me turned on. She put on a movie and told her son we had to talk in my bedroom.

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? Kari followed me in my room and she locked my bedroom door. Then she stared at me and she came up to me and kissed me on the lips. Then we continued kissing and she started french kissing me. She got down on her hands and knees and undid my belt, then she unbuttoned my pants and pulled them down to my knees. She grabbed my dick and started stroking it and she put the tip in her mouth. She continued sucking my dick, bobbing her head up and down. I told her to stop before I came in her mouth. She got off of me and she took off her tee shirt, shoes, and socks. She was standing in front of me in her pink bra and her jeans.

I took off my pants, boxers, and my t-shirt, so I was naked in front of Kari. I started kissing her again, then I slid my fingers under her pants and panties and started fingering her. She was so wet and very tight. I told her to get undressed, so she took off her pants followed by her bra. I finally got to see her big tits, and her nipples were hard. I started feeling her tits and then I started sucking on her hard nipples. While I was playing with her tits, she took off her panties. She had a nice strip of dark red pubic hair between her thighs.

I told her to lay on my bed as I went to get a condom out of my dresser. She said not to worry about it since she was on birth control. So I climbed on top of her and slowly started sliding my cock up and down her slit, getting the tip of my cock wet with her pussy juices. Then, I slowly pushed the tip of my cock into her. I fucked her for a while and then I told her to get on top of me. She asked if she should face me or face away from me. I told her to do reverse cowgirl and she got on top of me and grabbed my cock and lowered herself onto it. I was playing with her ass and watching her pussy ride my cock. Then, I could see her put her hand in between her legs and she started playing with her pussy as she was riding. I was getting close to cumming though, so I needed to do something to hold off.

So I asked Kari if I could fuck her ass. I told her I would be gentle and that if it hurt too much we could stop. She said fine and so I pulled out some lube, put a little on the head of my dick, and told her to get on her hands and knees. I put a little lube on my pinky and slid the tip slowly into her ass untll I was knuckle deep. After loosening her up for a while with my finger, I put the tip of my dick against her asshole and slowly tried to push the head in, but her ass was tight. I tried again and I could feel the head of my cock getting squeezed as it was trying to enter her ass. I slowly went back and forth a few times, pushing in a little further each time. Her ass was so fucking nice and tight and after she relaxed enough, I could feel her ass cheeks spreading apart as I was going back and forth. I thrusted deeper when I noticed her playing with her pussy. I was squeezing her tits then I moved my hand from her tits and I smacked her ass. She told me she was close to cuming. I kissed her neck and gave her a little hickey while she orgasmed.

That was enough for me. I told her I was about to cum, I pulled my dick out of her and told her I was gonna cum on her tits. She said okay, that’s fine and turned to face me. I told her to jack me off and she started stroking my cock. I couldn’t hold back anymore, I felt my dick getting ready to explode. Then it happened, I came all over Kari’s big tits and some landed on her chest too. We started kissing again, then I gave Kari some baby wipes to clean up with and she wiped up the cum. Then we both got dressed and she told me to tell Kaylee she stopped by. Then she left.

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? I felt horrible I cheated on my fiance. The next day all I could think about was Kari and our hookup. I don’t what else the future holds, if anything, as this was not planned, it just kind of happened. I feel more attracted to Kari, but the feeling I have also with my fiance will never change.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Withdrawal, Birth control pill / patch / ring / injection / implant

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

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

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

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? No one I did not want to risk anyone knowing and messing up my relationship with my fiance.

Did you get emotionally hurt as a result of this hookup? A little bit

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

Do you regret this hookup? A little bit

Why do you regret this hookup? Because I have fiance and would hate to have her find out.

What was the BEST thing about this hookup? We both wanted more with each other.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No

All things considered, how POSITIVE was this experience? Somewhat positive.

All things considered, how NEGATIVE was this experience? Not at all negative.

Anything else you want to add about this hookup? If there is a next time, I will have to try to go down on her. In all of our hookups, only she has done oral to me.

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