I Had the Best Sex with My Best Friend



What’s your gender? Woman
How old are you? 24
What continent do you live on? North America
How many sexual partners have you had in your life (including oral sex)? 8
How many hookup stories have you here posted before? 0

I had the best sex with my best friend

How long ago did this hookup happen? 1 month ago

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

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

How long did you know the person before this hookup? For 1 to 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 had known my guy friend for over 2 years. We met at school. We became very close and eventually developed feelings for each other. I first fell for his charm and wit, and later for his beautiful uncut penis. He was the first uncut guy I had been with and now I’m addicted!!! I guess it’s true what they say about skinny guys… he was also one of the biggest I’ve ever been with, and boy did he know how to use it.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The tension had been building for the past couple of months. We had been very flirty and touchy with each other. We had confessed our feelings for each other. One night when we were out drinking with friends, he told me he thought about me naked and that he wanted to see how many times he could make me come. He asked me to come home with him immediately and I said YES!!!!

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 didn’t anticipate us having sex, but once I got to his house it was on like Donkey Kong. I don’t even remember any words or conversation happening. My clothes came off so fast. He was all over me. His mouth and tongue caressed my entire body. He sucked my breasts and fingered my wet pussy. He said he thinks it’s really hot when girls squirt and he wanted to make me do it. I sucked his big, beautiful dick and he said it was the best head he’s ever gotten.

He fucked the back of my throat. He said he wanted to fuck me so he put on a condom even though I have an IUD because he’s super paranoid about stuff like that. Anyways, he fucked me really deep and hard, made me scream because I wasn’t used to being filled up by such a big cock like that. We fucked in all these crazy positions. He fucked me from behind and said how he’s always loved my big ass and thought about fucking me like that. He pulled my hair and slapped my ass. I got on top of him and rocked his world. He said I really know how to ride a dick. He grabbed my tits and put his fingers in my mouth and had the biggest smile on his face as he was watching me bounce up and down on his perfect dick.

He was amazed that his cock was able to stay so hard and erect. Unfortunately he wasn’t able to come because he’s on the Prozac and he said he can’t even make himself come. But he said he wanted to come on my face and tits and someday come inside me because he has never done that before and he trusts me a lot. We fucked pretty much all night, we got back to his place at 11:30 and were up until 4am doing it. You could tell we both really wanted to fuck each other and we had been thinking about it for a long time. He gave me 3 intense orgasms, one of them made my whole body shake. After that I was so tired, he wanted to keep going but I was DONE. So we cuddled and kissed and I fell asleep in his arms. He referred to the events of that evening as “making love”.

I will never forget that night. It was one of the most passionate and incredible experiences I’ve ever had. I want it to happen again but I don’t want to be friends with benefits because I love him.

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? I love him and I want to be with him. He says he has feelings for me too but isn’t ready for a relationship because he has crippling depression and hates himself 🙁 it’s really sad

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more, Thought it was an important experience to have, Intoxication

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

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? Everybody knows lol and they are not surprised

Do you regret this hookup? Not at all

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