Christmas Eve

by Cool Teacher

What’s your gender? Man
How old are you? 33
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Buffalo, NY
Highest education received: Post-graduate degree (currently pursuing)
What’s your occupation? Teacher
What’s your current relationship status? Dating casually
Religious affiliation: Agnostic
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)? 27
How many hookup stories have you here posted before? 0

Christmas Eve

How long ago did this hookup happen? Christmas 2018

What was your relationship status at the time? Dating casually

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

How long did you know the person before this hookup? Just met that day

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? My family lives about 4 hours away and I always visit for holidays. While I’m in town, I go on Tinder and swipe just for fun. Nothing usually comes of it. I get a few matches, I message them with my intentions and usually get a polite “no thanks” or no response. Other times, I don’t hear back from them until I’m out of town, but this time was different.

I was in town for Christmas and matched with “Shelby” on Tinder. She was a pretty blonde in her mid 20s and a first grade teacher. I was going to head out to a bar to watch the Bills game and invited her to join me. She couldn’t make it, but seemed interested. I made a comment about how the bar was packed and if she had come along, she would have had to sit on my lap. She mentioned how much she would love that and feeling my cock when she sat on me and it was on from there. I was visiting friends that night, but we agreed to meet up the next night, which was Christmas Eve.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It was pretty clear that I was going to her place for sex. She indicated she was pretty much addicted to sex. That day, she texted me a photo of her ass after she got out of the shower, and we both were looking forward to meeting up.

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? I arrived at her house and went inside to find her wearing just a onesie, of all things. We went to the bedroom and talked on her bed for a few minutes. I quickly made my move and we were all over each other. I took off her onesie and revealed a sexy petite body with pierced nipples. I showed her body the love and passion it deserved as I made my way down. I kissed her thighs and as I made my way slowly to her pussy, I discovered she also had a pierced clit, which was a first for me. Her piercing said “eat me”, which turned out to be the perfect choice. I licked her to an intense orgasm, then sat back as she returned the favor on me. She was very enthusiastic about sucking my cock, and very skilled.

I eventually pulled her off, held her down, and entered her missionary style. I started slow and deep then got faster and faster. She rode me for a bit, before we switched to doggy style. Pounding her from behind and slamming into her sexy little ass was eventually too much, and I finally pulled out and came all over her back, since she wasn’t on birth control.

We laid there for a while, caressing each other, having pillow talk, etc. I knew round 2 could be a possibility. After a while, we went at it again for even longer this time since I usually can’t do two rounds, but when I do, it takes a lot for me to cum the second time. We laid together some more and even went at it for a 3rd round, which I believe was a first for me. She was really impressed (and so was I), but she was incredibly sexy and just couldn’t get enough of me, so that helped a lot.

If I have free time the next time I’m in town, I’ll definitely reach out to her.

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? She set a timer and I had to leave when it went off, which I told her was pretty funny since I wasn’t planning on staying the night anyway. She is 4 hours away, so a relationship is out of the question, but the sex was incredible and it was very satisfying to find a girl who was this attracted to me.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Withdrawal

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, To feel better about myself, 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? I talked to my buddy about it, he was happy for me.

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? She was enthusiastic, passionate, and sexy. We’re both teachers and we both needed to indulge the other side of our personas.

What was the WORST thing about this hookup? She’s four hours away.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not really

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!