Fun With A Lesbian



What’s your gender? Man
How old are you? 40
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Canada
Highest education received: Some college (not currently in college)
What’s your occupation? Business Owner
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Not particularly
How many sexual partners have you had in your life (including oral sex)? 30+
How many hookup stories have you here posted before? 0

Fun With A Lesbian

How long ago did this hookup happen? 6 months ago

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

How would you best classify this hookup? Friends-with-benefits

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? A is a beautiful girl. She is super slender, 5’6, great breasts and body, and is 27 years old. I know her very well. She has an affinity towards women but always had a soft spot for me.

We have hooked up many tines over the last 8 to 10 years. I met A through a friend. A has always been a great friend.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was in A’s town for business. I called her up and asked her if she wanted to spend the night with me in my hotel room, and she agreed.

I instigated it.

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? We had both gotten back from the strip club, and we were making out very heavily over there. When we got back to the hotel room, the sexual tension was rising rapidly. I ran us a Jacuzzi and we both got in. A sat on top of me and we started making out heavily. She lowered herself onto my cock and it was the best feeling ever. We had some very slow passionate sex mixed up with some very quick thrusts. The Jacuzzi was fun, but we decided to move the party to the bedroom. We got to the bed and began performing 69 on eachother. I love her little pussy; she was so wet and smelled incredible. After, we switched positions to missionary and had mind-blowing sex. Her little pussy is so tight and my dick filled it like a glove. As I was getting close, I asked her if I could come inside her and I knew she had never let anyone do that with her before. When she said yes, I started fucking her harder and unleashed my cum inside her pussy. It felt so good. About 20 minutes later, I went down on her and gave her oral for a good 30 minutes. At this point, my dick was super hard again, so we began fucking again. Now, I wanted to try something else with her she had never done so I asked if we could have anal and she agreed. I spit all over my dick and turned her on all fours and slowly penetrated her ass gradually picking up the pace while fingering her pussy and getting her to finger her pussy. I wanted to cum in her ass so bad, but I couldn’t finish. We switched positions to cowgirl and I held her ass firmly and began to fuck her like a jackhammer before I dropped another load in her pussy.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than 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? It felt fantastic. We had to go to the pharmacy to get plan B. A will always be a good friend of mine; there are no expectations or hopes.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, Thought it was an important experience to have, Intoxication

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol, Marijuana, hashish

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? 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? I told a few of my friends. They didn’t say much. They know me too well. Lol

How would you best summarize people’s reactions about this hookup? Relatively positive

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? Cumming inside her pussy and fucking her in the ass

What was the WORST thing about this hookup? I wanted to cum in her ass so bad.. there is always next time

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Nah

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? Would pay $1000 to recreate that evening in a heart beat. It was some of the hottest sex on my life.

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 used to have a lot of casual sex, then I realized I had low self esteem.

What do you think about the Casual Sex Project? I fucking love this site!

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