What’s your gender? Man
How old are you? 28
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)? 25
How many hookup stories have you here posted before? 0

Virgin BFF Gets Some Benefits

How long ago did this hookup happen? 11yrs

What was your relationship status at the time? Single

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? She was smoking hot and unfortunately for me, she was also my best friend. She was about 5’6″ or so, average weight shoulder length blonde hair with gorgeous blue eyes, she had a nice tight toned body, firm c-cups, great legs and probably one of the nicest asses at our school. We had met early on in high school, she was the quiet emo looking new girl who wore baggy clothes and listened to metal, we had a few classes together and hit it off. As we got older she started to grow into her body she dropped the alt look and slowly developed into a total knockout, which for me sucked cause I was deep in the friend zone, like so bad it didn’t even faze her to strip down to a bra and thong in front of me if she needed to change. In senior year, I was the first one she told about losing her virginity, she shared way more than I wanted to know. I had made a few passes and even asked her out but her girlfriends convinced her it would ruin friendship and all that bullshit but we carried on as friends, she finally ended up with a boyfriend, which again sucked for me, when she started having sex on a regular basis, she would again share more than I wanted to know, at about the same time I started to notice changes about her, she became a total nympho. This was before smart phones so information wasn’t always at our finger tips, I remember one day we were hanging out talking and she asks if she can ask me something serious, I say sure and she asks if guys really walked around naked in the locker room, I laughed and said no then asked where she was going with the question, she hummed and hawed a bit then asked me if four inches was considered big, I chuckle a bit and she explains that she got curious one night and measured her boyfriend’s penis but she didn’t exactly have much to compare against as the other guy she had been with looked about the same, to be honest, I wasn’t really sure either, her next question was equally as messed up just more personal, she asked how long I usual lasted if I was masturbating [she was aware I was a virgin] that question I wasn’t willing to answer and we changed subjects. We were super close and obviously, I wanted to be sleeping with her and dating her but that didn’t seem like it was going to happen.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It happened after school at her house, we hung out at her house all the time I spent more time there than my own house, I got there about 5pm one night, she lived with her mom and younger sister, her mom let me in and said she was in the downstairs, I went down and the door to the spare room was locked, I knocked but no answer, I didn’t think much of it, she’d usually lock the door and put on a set of head phones and listen to music while smoking a joint, something her mom obviously knew about but we didn’t know that, anyway there was another door off the laundry room so I went around to that door, nothing could have prepared me for what I found when I opened that door, she had headphones on but instead of smoking weed she was sitting with her legs spread up on the computer desk and a hand in her thong while watching porn, I stood there absolutely speechless as she rubbed her pussy, she had no idea I had come in the door behind her, I couldn’t believe what I was seeing and I started getting hard as she started moaning, my head was telling me to leave but I couldn’t move.

She started rubbing more aggressively and leaned back some more, so much so she was looking right at me but her eyes were closed, she sounded like she was getting close to orgasm then her eyes opened, she was startled and fell out of the chair, I immediately went to help her up, when she got up she frantically grabbed for her shirt on the ground then pushed me and asked “What the hell you little perv, how long were you watching me?” she said this with a grin but realizing the situation I was embarrassed so quickly apologized and went to leave, but she came after me and grabbed my hand and tells me to stay, I told her I should really go but then she asks “You’re still virgin, Right?” , adding to my embarrassment I nod yes, I thought for sure I misheard when she said “We could change that”, I just looked at her unsure how to respond as I stepped back into the room, she finally said “Well, What is it? Go home and jerk off or have sex with your horny friend?”, my head was still spinning and all I could say was “I don’t have any condoms” She smiled and responded “That’s fine, I have some upstairs….but I’m on the pill now so you don’t have to wear one if you don’t want to”, all I could manage was an ok before she kissed me then went to make sure the doors were both locked this time, we started making out and feeling each other up, I struggled with the clasp on her bra until she finally stepped back and undid it then she dropped her thong, she was even hotter than I had ever imagined, she then instructed me to strip, my boxers were last and when I dropped them she just let out a gasp and her eyes went wide on my erection, she looked back at me then back at my dick and blurted out “Jesus! Dude, what the fuck? Why is your dick so big!?” Hearing that was an ego boost but I wasn’t sure how to respond, she steps towards me and starts touching and jerking it then goes to her desk and digs through a drawer pulling out a ruler, she grabs my dick and places the ruler on it then looks up at me and blurts out ” Seven fucking inches! how the fuck is that possible, that’s like both the guys I’ve been with put together” We both laughed then started going at it again.

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 we made out she stroked my cock and I fingered her slowly, not a clue what I was doing but she was practically dripping wet and didn’t seem to mind, she finally told me to lay down, she straddles me and starts rubbing her pussy against my cock, then grabs it and asks if I’m ready, I nod eagerly and she lowers herself onto me, we both gasped and moan, it felt so go I thought I was going to cum right there, her nails dug into her chest as she pushed herself all the way down, she just sat there for a minute then says “How does it feel to not be a virgin anymore?” I simply told her it felt like heaven, she smiled and told me it was only going to get better, as she started to ride me I grabbed her hips and told her to take it slow, she went slow, mostly grinding against me her nails digging into my chest and she started breathing harder, we were maybe 5 minutes in and I was keeping it together surprisingly when she stopped and told me she was very close but she was going to need to go faster to get herself off, I told her she could do whatever she wanted, she grinned and told me to keep it up for a couple more minutes, I grabbed her ass as she started to ride me faster, she closed her eyes as she started to moan, I closed mine as well doing whatever I could to hold back but it was no use I warned her I was about to cum but she just kept going, my orgasm sent my hips thrusting upwards as I blew my load, she kept riding for a few more seconds until letting out a groan then collapsing and trembling on top of me, we laid there for probably 10mins not speaking until her mom’s voice snapped us back to reality as she yelled from the top of the stairs she was leaving for her shift and there was money on the counter for pizza. We stayed in the basement talking for a bit, I was a little caught off guard when she mentioned how sex was even better without a condom, when I said, “But I thought you were on the pill” she smiled and said “I am….But it’s only been a week, I’ve never actually had a guy cum inside me before”

We went upstairs ordered a pizza and got maybe half way through a movie before she wanted to fuck again, I had a bit more stamina that time around and she told me to take control and fuck her, so I did, but we never did get a chance to finish cause her sister came home and luckily had a blanket and hopped on the couch as if we were cuddling, however I spent the night and being the little nympho, she was she made sure I got off a couple more times that night

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? The next morning her mom asked “did we get up to anything last night?” with a bit of a laugh, she definitely knew we had fucked. She dumped her boyfriend a few weeks later and we continued to be friends with benefits but never actually dated, which was fine by me I came to realize over the years most of her boyfriend’s couldn’t keep up sexually and she cheated on most of them. she moved got married had a kid, we haven’t hooked up in probably 5-8yrs but we still talk.

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), 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? Very

Did you consent to this hookup at the time? I didn’t give a clear ‘yes’, but I didn’t give a ‘no’

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 re t? At first, no one, but after she broke up with her boyfriend we started having sex whenever and where ever so friends eventually figured it out

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

Did you get emotionally hurt as a result of this hookup? A little bit

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? Lost my virginity, I was her first “big cock” and her first unprotected partner

What was the WORST thing about this hookup? nothing

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? made me realize all that crap about ruining friendships with sex is nonsense, if friendships are meant to last, they will, I’ve had plenty that fell apart without sex.

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

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

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