My Best Friend’s BFF

by ceejay

What’s your gender? Man
How old are you? 30
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 current relationship status? Single
Religious affiliation: Atheist
How religious are you? Not at all
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? 2

My Best Friend’s BFF

How long ago did this hookup happen? 11yrs

What was your relationship status at the time? Same as current status

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? For less than a week

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, who I’ll call Kelly was fairly tall 5’7″ at least, very slim body, legs for days, small perky breasts, long brunette hair and blue eyes with a pretty smile. She was fairly shy and quiet for the most part, she was my best friend’s childhood BFF. I barely knew her, she was cute but she had a boyfriend so i didn’t really give her much thought.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? She was in town visiting my best friend, they’d grown up together in some small town and were closer than most sisters. She was in town for the week and this was the first time I’d met her, despite my friend having a boyfriend, me and her spent majority of our free time together so i spent the week getting to know her somewhat shy best friend, she seemed friendly but was fairly quiet. The weekend rolled around and there wasn’t much going on so we spent our Saturday in my friends basement with a 12 pack of beer and bottle of rum and a movie, I started to notice the more Kelly drank the chattier she got, then I started to catch her staring at me but she had a boyfriend so I left it alone. It was about 1am and we’d all passed out, I woke up and had to piss so I went to the washroom down the hall, did my business and when I came out Kelly was standing there, before I had a chance to step out she pushed me back in and closed the door behind her, we were inches apart and she was staring up at me with a big grin on her face when she asks “So I know she has a boyfriend, but there’s nothing going on between you two is there?”, I shook my head and told her we were just friends, then before I could ask why, she stepped in closer, gave me a kiss as she began to unbutton my jeans and says “You’re able to keep a secret right?” I nodded yes and she gave me another kiss and said “Good, ’cause I’m really horny and I have a boyfriend but I really want to fuck you.”

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 attacked each other and she reached down my pants and began jerking me off, I slipped a hand down her pants to find she was smooth and soaking wet, she gasped as I ran a finger between her lips, we began making out passionately. Then she broke our kiss, spun around, bent over the counter and peeled off the yoga pants that hugged her ass so nicely, I pushed my jeans down grabbed my cock and lined up behind her, teasing my cock through her lips a few times before pushing my head in, she gasped and clenched the counter, I watched in the mirror as her eyes rolled back and her mouth dropped open then she moaned out “HOLY FUCK!” as I pushed my cock all the way inside her, she asked me to stop for a minute then says, “If I get loud just cover my mouth and fuck me harder, ok?” and with that I began slamming my cock into her and with in a few minutes she was grabbing at my hand to cover her mouth and then she started matching my thrusts, it only took a few minutes before I felt it building. In the heat of the moment we hadn’t really considered condoms or where I’d finish, but she was getting wetter with each thrust and despite my hand on her mouth her muffled moans were getting louder, then it hit me like a freight train, I placed both hands on her hips as she bit her lips and I power fucked her as hard and fast as i could, her legs gave out as her orgasm hit and i unloaded inside of her. The whole session took less than ten minutes but it was explosive, we returned to our seemingly oblivious friend still passed out on the couch, Kelly woke her up and told her it was time to go to bed upstairs and helped her to her room.

I had laid down on the couch and was just about to fall asleep when I got a text from an unknown number. “It’s Kelly, one more time?” I quickly responded with a yes and within seconds she was coming down the stairs and we were going at it again, our second round went on for quite a while thanks to the booze and having already cum once although she didn’t seem to mind, I finished in her again then she returned to her room upstairs.

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? We all went for breakfast the next morning, aside from some glances nothing was said about our night and our friend was seemingly oblivious to the whole situation. She had a boyfriend and lived several hours away, i had no expectations.

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

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

How intoxicated were you? Drunk/high but not wasted

What substances did you consume? Alcohol

How intoxicated was your partner? Drunk/high but not wasted

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? A little bit

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? At first I didn’t tell anyone, then a few weeks later Kelly spilled to our friend about us hooking up. She didn’t seem to mind

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? spontaneous sneaky sex

What was the WORST thing about this hookup? it was a one time thing

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

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

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