Girlfriend’s Best Friend

by The Bad Guy

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? STL
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Office Manager
What’s your current relationship status? Engaged/Married (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? Easy?
How many sexual partners have you had in your life (including oral sex)? 25ish
How many hookup stories have you here posted before? Two

Girlfriend’s Best Friend

How long ago did this hookup happen? 22 years

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

How would you best classify this hookup? Short fling

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? She was a beautiful blonde with curvy hips, a smaller waist, and a perfect chest. She had a naturally seductive face and was always quick with a sly smile or wink. This was all in high school, we knew each other from Freshman year on. She had previously dated one of my best friends, but we were always really chummy. For years it felt more like a snarky brother sister thing, until quickly it didn’t. She had even introduced me to my then-girlfriend as they were best friends.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? My girlfriend had moved away with her family over the summer before senior year. We both missed her. My hook up had just broken up with her kinda crappy boyfriend too. For a few weeks, we hung out together, at the expense of my male friends. When I dropped her off at her place one night, we were in the middle of one of those long teen conversations about everything. We started walking the neighborhood instead of going inside. Without anything really specific causing it, we started making out. We were physically close in a dark area and it just started happening. She was, to date, the best kisser I’ve ever experienced. It was electric. For a few more weeks we hung out every night and made out.

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? Finally, one night we were watching a movie together in the basement. My parents were home but they always gave me a wide berth. Before she left, my girlfriend and I fucked a lot in that situation. I don’t remember why but it had been a long day and we were both in sweat pants. I was in a t-shirt and she was in a sweat shirt. We started a movie and cuddled under a blanket. We started making out at an angle, she was on her back and I was on my side against the back of the couch. For the first time since we started making out, I tried to fondle her, sliding my hand under her top to find she wasn’t wearing a bra. We continued to kiss as I explored her breasts with my hand. Soon, she took my hand and guided it down to her waist. Taking the hint, I slid my hand easily under her sweats and panties and started playing with her pussy. I was inexperienced, my girlfriend didn’t like oral or hands so I hadn’t learned anything. My hook up was cool, though, soon using her hand to show me where and how to rub and apply pressure. Then she guided my fingertips inside, verbally telling me when I had the right rhythm. She was extremely wet and all I could think about was fucking her. That’s all I was used to, but she was a virgin and I knew that, so I never said or pushed more. As I worked her, our making out stopped and she gave these soft perfect littles moans that I could almost taste as our faces were so close. When she came, she covered her mouth to keep quiet. Despite all the sex my girlfriend and I had had in the prior few months, this was the most I had ever been turned on. I was hard against her hip with precum soaking into my sweats.

As I said, she was a virgin and I wasn’t sure what she was used to. When she finished and started calming down I just waited to see what she wanted to do. Eyes wide open and trembling from excitement and nerves, I had been holding back. I was trying to talk myself down in case she didn’t want to go further, but fortunately, that wasn’t an issue. After a few minutes, her hands found my cock and started playing with it, tugging a little over my sweats before stroking it after I pulled the waist off my hips. I knew I had already made her hands sticky, but she brought one hand up and suggestively licked her palm to moisten it. Then she started really stroking it with the new improvised lubrication. I probably could have cum that way, but the position and being under covers became more awkward for a handjob then they were for a fingering. She asked me to move to a chair a few feet away. I did and my sweats were pulled down. She knelt between my legs and started with a hand job. Stroking, licking her hand for more moisture, going faster, giving these seductive little looks. I thought I was going to cum all over her. I’d seen it in porn but my girlfriend always wanted me to cum inside her during sex. All of this was racing in my brain – first handjob, her sexy face, a cumshot – when unprovoked she leaned over and put her mouth on me just past the tip. My girlfriend hated blowjobs, and I had never had one. I’m not sure if you’d call this one either because once I felt he warm lips and could sense he tongue give my head a little swirl I came, hard, and a lot. At the time, I was embarrassed because I didn’t know her experience. In hindsight, it makes me think she had plenty because she took a mouthful without any issue and made almost a performance from swallowing it. I still think of it as a top ten sexual experience and it’s probably the fastest I’ve climaxed.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, one

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 slipped my pants back on and felt a rush of energy. We went back under the covers and cuddled tighter than we had before. We actually fell asleep together and one of my parents had to wake us up at 11 so my hook up could get home properly. The next week was very busy for both of us and it was hard to get together. When we did, we still made out but didn’t have a chance for more. Within a week, though, I fucked the whole thing up. We got into an argument about something and I realize now she was hoping to become a couple. I made it clear I still had a girlfriend, that this just “was”. That abruptly ended it. She left our school senior year within months, and I haven’t seen or heard of her in decades. Months later, I ended up getting with another of my girlfriend’s friends and this time left her.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, I don’t know if my partner was on any (other) method, No penetrative sex happened

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection, 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 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? First, a few friends. They already knew what was going on and they encouraged it. Years later, I ended up telling my ex girlfriend when we reconnected to apologize for it. By that point, she didn’t care.

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

Did you get emotionally hurt as a result of this hookup? Somewhat

Did your partner get emotionally hurt as a result of this hookup? Very

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? It was a learning experience with some firsts. Looking back I realize I loved my partner and found her very attractive…the moment was perfect.

What was the WORST thing about this hookup? The fallout. Not breaking up with my girlfriend and moving forward with my hook up. Not speaking to her again.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It’s a powerful act with many outcomes and angles. It has to be wielded carefully.

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

All things considered, how NEGATIVE was this experience? Somewhat negative

Anything else you want to add about this hookup? A top five regret. I love my wife, and I met her shortly after this. If I hadn’t fucked this up my love life would have gone a different way. I know I’m happy now, but what would that have been like?

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