My Fiancée’s Best Friend



What’s your gender? Man
How old are you? 31
What’s your race/ethnicity? Black
What continent do you live on? North America
What country and/or city do you live in? Miami
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Business developer
What’s your current relationship status? Dating casually
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 20+
How many hookup stories have you here posted before? None

My fiancée’s best friend

How long ago did this hookup happen? 6 months back

What was your relationship status at the time? Engaged/Married (monogamous)

How would you best classify this hookup? Fuck-buddies / Booty call

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? From the first time I saw her, I liked her, she is my fiancée’s best friend. They have been friends for years. She’s Portuguese, tall, dark hair, green eyes, a mysterious yet sexy look, with a divine body. she reminds me of Monica belucci who was my ultimate crush.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? My fiancée lives with me so she used to come through on weekends and they would chill by the pool or go out while I’m busy working or in another country for business. So I used to see her and chat to her which as pretty innocent but I knew she could sense that I liked her. I got her phone number from my fiancée’s phone and texted her ‘holla, its me’ and she replied by saying ‘it took you 2 years to text me 3 words?’ Then we kicked it from there, we texted each other a lot when I was away on business…even video calling each other. She would send me pictures of her throughout the day, I was obsessed with her face, she was so gorgeous. My fiancée had to go in Paris for a week for work and I stayed behind so one night I asked if we could go watch basketball downtown and grab some food. She accepted so we went. It was a great night, we had good food, good wine that she picked (surprisingly) we spoke a lot and even kissed a few times, she making fun at how she is always the tallest in her relationships but she looked so short next to me, because I’m quite tall and muscular. We laughed then we went to her place.

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?  As soon as we got to her place, we started making out heavily. It was really passionate like all these years we liked each other and were both hiding it. I told her I didn’t want to rush to sex but enjoy every bit of her so I undressed her and asked if she had anything I could spread over her entire body because I wanted to lick her. She suggested chocolate cream, so I gently lay her on the floor on top of a sheet not to make mess. Then I covered her entire body with chocolate cream from neck to toes while kissing her gently. We were both naked and I started licking it off, I licked her neck, breast, stomach, made my way to her clit, then her legs, her feet, then back to her clit again, she was so wet and shaking at the same time, I flipped her over then covered her back, her ass with chocolate cream them licked it all off, I even licked her anus, then made my way to her pussy until she squirted in my mouth. Then I carried her to the bathroom and I cleaned her while licking her some more, she asked if she could have me, I told her to wait, I then took her to her bed and I told her to eat me, she started kissing and licking me all over she gave one of the best blow job I had in my life. She was amazed at the size of my dick which is nearly 7 inches, her tiny mouth had only nearly half of it in. She was licking my cock, my balls, I was fingering her then we 69’ed until she came again. Her pussy was so wet and her moans so sweet like she was about to cry. She then begged me to fuck her. She said she wanted me raw, so I went raw. As soon as I slide in her she started moaning heavily, I could tell that she was in pain and very tight but she wanted me deeper. I was on top of her, going deep and slow, her juice was flowing. She was licking my nipples and talking in Spanish which really turned me on and I started going faster. We did lot of different positions for nearly 4 hours. I came inside of her 4 times that night and she came and squirted 5 or 6 times. We really made love to one another that night. We then took a bath together then spoke until the early morning. I slept over at her place naked in her arms that night. In the morning she brought me breakfast in bed, and we had sex the following morning. I ended up spending the following day at her place. It was really what I wanted to do to her all these years.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than 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? Well…we are still seeing each other. As I’m writing this, I’m laying in her bed. She is the one who told me about this website so I thought I will share this story. I’m still with my fiancée, and she is expecting too but for some strange reasons, I’m still with her friend and we developed something deeper in such a small amount of time due to our casual encounter. She is also in a relationship so its messed up. But we enjoying every minutes together and thats all that matters.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Discussed STI testing history, Exchanged recent STI test results

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

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

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 spoke to my best friend about it, he wasn’t really impressed with me even worse that this hookup is turning into something frequent.

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? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? I got to satisfy my desire of having her after so many years of looking at each other and not doing anything about it.

What was the WORST thing about this hookup? Well she is my fiancée best friend, if my fiancée finds out about this she will be very sad and disappointed which might end their 15 years friendship. On the other, my fiancée is expecting our first child and here I am fucking her best friend. So it’s messed up.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It makes me feel like an asshole at times and I feel bad about not being able to end it. I feel like there is a huge storm waiting to happen.

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

All things considered, how NEGATIVE was this experience? A little 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? Random sex with someone you have a connection with is always better.

What do you think about the Casual Sex Project? This site is great. I’ve been reading different stories and at the end of the day, there is always a little satisfaction on both side.

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