It Really Was Her First



What’s your gender? Man
How old are you? 25
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Australia
Highest education received: College degree (eg., BA, BS)
What’s your current relationship status? Dating casually
What’s your sexual orientation? Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 14
How many hookup stories have you here posted before? 3

It Really Was Her First

How long ago did this hookup happen? 8

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

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? T was short and busty and had shoulder-length red hair. She often wore these low cut shorts that showed off what a great bum and a t-shirt that was modest, but tight enough that you could make out her great chest. T and I met through hockey, but though she’d since stopped playing, we kept in touch. She was a year or two older and very witty. T had recently ended a relationship and we’d talked about if there was anything between us. I’d already cheated on my girlfriend (and I’d told T).

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? After texting back and forth about random stuff and a party a few days beforehand where we’d cuddled and there had been an incident where a bikini-clad T sat in my lap, T and I were planning to hang out. I think both of us were hoping to move forward, but neither of us was willing to come out and talk about the fact that I was in a relationship. I guess in an attempt to pick a fight with my girl, I told her I was going to T’s place. No response. Eventually, at T’s place, we were watching a movie, cuddled up on one of those L shaped couches. T was wearing a summer dress and I’d stolen a few glances at her legs and cleavage.

I was laying against the back of the couch, with T in front of me, pressed up against me. As the movie went on, I had an arm resting on her, and a raging hard-on. I suddenly got a text from my girl. I had my phone out to read it and T could see the screen. It was the start of another fight. I knew I’d provoked it but it still pissed me off. I told T I didn’t know why I kept it going. She said it was maybe because I didn’t have a better offer. I laughed and asked if there was one. T turned to look up at me and told me that I just needed to look…like I’d been doing down her top!

I turned red and T laughed at my expense. As she pressed her bum against my hard-on and asked if I’d seen her undies. I confessed I’d looked, but hadn’t managed a peek. She laughed again and told me there weren’t any undies to see, grabbing my hand and putting it between her legs.

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? T pulled the hem of her dress out of the way, rubbing my hand against her. At the same time, I was grinding my cock into her bum. T adjusted her position, giving my cock access between her legs. She whispered that she couldn’t reach my fly and that she was ready when I was. With some awkward shuffling, I got my pants off and my dick out. I could feel T was soaked and I was rock hard. The angles didn’t quite work out so T rolled onto her stomach, warning me to make sure I went in the right hole.

I pulled the dress out of the way and slipped inside her. The molten heat and the grip of her slippery pussy around my cock was amazing. She arched her back as I started to thrust in and out, pushing back to meet my thrusts. I slowed down, kissing T’s neck and biting gently. She turned her head, telling me not to worry about her and to cum when I was ready. I picked up speed again and came inside her, laying on top of her in that post-orgasmic stupor. My cock still inside her. Eventually, I got it together and rolled off her. T sat up, my cum dribbling out of her pussy. Now you owe me an orgasm, she said. I paid up a few hours later!

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, 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? T and I had occasional sex, often after she’d been on a date with someone else or I’d once again been teased to bursting point and then denied by my girlfriend.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Fertility awareness (days counting, temperature)

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, To cheer myself up, Revenge / Getting even

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? Somewhat

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

Do you regret this hookup? Not at all

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!