Girlfriend’s Best Friend

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? 0

Girlfriend’s Best Friend

How long ago did this hookup happen? Last Week

What was your relationship status at the time? Engaged/Married (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? She was a 24 year old hot redhead with green eyes. I knew her very well Kari we would watch Kari’s son for her during the week. She is also my wife’s best friend. I had never hooked up with her prior never even crossed my mind. I always thought she was very cute.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The hook up began at my house. We were supposed to watch her son. My wife had left to go run our kids to school. Kari stopped by with her son. To drop him off before she went to work like always.

We started talking and she was telling me how she was struggling to pay us since she was a single mom. I told Kari if she needed help I could help her out. She asked what I meant. I told her I just got paid I could loan her $100 that’s how much my wife charges for a week.

She said I feel bad I told her don’t worry about it if you need help just ask. She thanked me. She asked me where Kaylee was she is my wife. I told her she just left to take the kids to school she should be back in about 45 minutes.

Kari asked me if she gave me a blowjob if she could keep her money. I knew she was struggling. I was really shocked by what she said. I asked her what did you just say to make sure I heard her right. She said I can help you for helping out me.

I said I suppose do but how can we do this with your son in here. Kari suggested why don’t we put something on TV for him in the living room. I told her ok and she found something for him to watch. Then I told Kari to come to our room with me.

She followed me in there. She told me to lock the door which I did. I didn’t want her son catching us. She told me to take off my pants and I did followed by my boxers. Then she told me to lay down on my bed.

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? I did and she got on the bed beside me and she grabbed my dick and started stroking it. Then she said You have to promise me something you can never tell anyone about this. I told her I know I don’t want anyone finding out or Kaylee could break up with me. Then she said I can’t believe I am going to really do this. Then she licked my dick up the side. She then put the head of my dick in her mouth and she started moving her mouth up and down on my cock. I was getting big she pulled her mouth away from my dick and said, I had a nice dick it was one of the biggest she has seen.

I told her that’s great and she went back down on me sucking my dick. It felt amazing she knew how to work her lips and tongue. She kept thrusting her face up and down on my cock only going about halfway down. Then she grabbed my balls and started to play with them. She had been blowing my dick for about five minutes and she asked can I make you cum. I said yeah she said ok and went back to sucking. She said we need to hurry I don’t want to get caught by Kaylee. I said ok I know. I said I could probably cum quicker Kari if you take off your sweatshirt. She was stunned she looked like she didn’t know what to do or say.

Then she said I am just taking off my sweatshirt and she took it off she was wearing a blue bra. She had a nice stomach. She said I am not taking off my bra so don’t even ask. I said ok and she started stroking my cock again then I watched her go down on me again. She continued stroking my cock while sucking my dick it felt amazing. I put my hands on the back of her head and felt her head moving back and forth on my dick.

I was very happy I was getting really close to cummin as she was going down on me sucking my dick and playing with it she said we have to hurry. I said Kari can I play with your tits and I bet it won’t take me long at all she said yes but keep my bra on me. She went back to sucking my dick and I felt her tits under her bra. They were amazing her nipples were nice and hard under her bra too. I was getting close I asked Kari where she wanted me to cum. She said cum on my stomach on my belly. I asked her if she likes to swallow. She said sometimes. I said Kari can you just swallow for me I will never get to have another experience like this again. She said fine just hurry up and cum I gotta go to work and Kaylee’s gonna come home. I said get up and lay done on my bed on your back and she did. I said open your mouth I got on top of her and started jacking off.

I said I hope you’re ready for it she said I am I told her to jack me off and she started jacking me off then I could feel I was gonna start cumming I said stop. I want to cum I started jacking off on her then I said stick out your tongue and she did I started to cum I made sure it was gonna hit her mouth. Some went in her mouth and some hit her cleavage and her face. But most of it went in her mouth. She tried to swallow but gagged a couple of times trying to get it all down.

She told me she needed to clean up I gave her baby wipes then she wiped off her cleavage and face. I gave her sweatshirt back to her. We both kinda looked at each other and smiled. I told her thanks for making my day and she said she was happy to help me out. She put on her shirt as I put on my pants and boxers. She said I can’t believe Kaylee never mentioned anything to me about the size your dick. I said probably wanted it all for herself lol. We both walked out of the bedroom to find her son sleeping on the couch.

Kari was like I have to go to work I don’t want to be late, tell Kaylee I will be back to get him at five. I said ok will do have a great day at work she said she would try and she opened the door then she walked out and looked at me and smiled and waved as she was walking out I smiled and waved back as she left.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? No

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? We never talked about it again. After the hookup, we are closer that’s for sure. The next day I felt ashamed. I don’t know about the future I would love to do more with Kari but don’t want to ruin my relationship. Also, don’t know if we will have another moment alone like this.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) No penetrative sex happened

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, 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? 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? No one we don’t want anyone to find out.

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

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? A little bit

Why do you regret this hookup? No

What was the BEST thing about this hookup? It was with someone other than my girlfriend and I guess it made it cool getting together with her best friend.

What was the WORST thing about this hookup? I didn’t have time to please her too

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not really

All things considered, how POSITIVE was this experience? A little positive

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

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