by DJ

Gender: Male
Age: 30
Race/ethnicity: White
Current location: Connecticut
Highest education received: Some college (currently in college)
Relationship status: Married
How religious are you? Not at all
Sexual orientation: Bisexual
Any other term(s) that describe your sexual orientation/sexuality better/best? Bisexual recovering sex addict
How many sexual partners have you had in your life (including oral sex)? 45
How many hookup stories have you here posted before? 11

Hat Trick – Part 1

How long ago did this hookup happen? Two years ago

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? One-time fling

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? E was an 18 year old college student who lived an hour and a half away. She was a nerdy, shy girl who definitely didn’t radiate sex appeal, but she was extremely horny and really wanted me to “teach” her. She had a great bubble butt, was about 5’3″ 135 lbs and perfectly perky tits.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We met online and flirted a lot and fantasized about getting a hotel room and covering the room in squirt, since she had been able to make herself squirt, though no man had been able to yet. I pride myself on making a woman squirt so I was pretty sure I’d be able to. So we made arrangements for me to pick her up after her class around noon and go to a hotel. I picked her up on the sidewalk outside her class.

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 made small talk and kissed lightly then made our way to the hotel. I could tell she was pretty nervous so I started rubbing her legs gently with my right hand while I drove.

When we got to the motel (I was poor at the time so I couldn’t get much of a room) I led her into the room. We joked about how much cum was probably stuck to the walls and sheets and made remarks about black lights and whatnot. But to break the ice, because I’m not very patient, I started to kiss her.

It wasn’t long before we started to disrobe. I removed here shirt, exposing her cute tits. She wasn’t wearing a bra so I sucked her nipples while I ran my fingers down her back and slid my hands into her pants. I removed her pants and turned her around so I could study her ass. It was absolutely fantastic – perfectly round, and bouncy.

I removed my clothes and went down on her. I licked my way down to her pussy and began to nibble on her clit. My fingers rubbed her wet pussy while she squirmed in my mouth. She was very apprehensive about receiving oral even though her pussy was beautifully shaped. She had no reason to be self conscious. But she was. So I knew I just needed to take her and get her out of her own head.

I continued to lick her until she came, and then came again and then again. She could cum over and over. She said she wanted to suck my cock, so I brought her down in front of me and slid my cock into her throat while I held her head by the scruff of her hair. Her mouth slurped back and forth on me as I fucked her throat. She gagged a few times but kept going.

After a while, I stood her up, looked her in the eyes, kissed her deeply and turned her around. I pressed her against the wall, face first and pulled her ass out to me. I fingered her pussy a bit, then slid my cock inside her. She let out a gasp as my cock entered her. I fucked her standing for a while until her knees gave out in orgasmic ecstasy.

I picked her up and threw her onto the bed. I didn’t have any lube, which is helpful when trying to get a girl to squirt, but I knew I didn’t need any with her. She was so wet, there was no need. So I spread her legs and slid my cock back into her dripping pussy.

I began to fuck her over and over, harder and faster, with her legs in my hands. As I fucked her, I could feel the signature wetness and tight building wave of a woman about to squirt. I pulled out and began to rub my cock tip on her swollen clit and between her lips. As I rubbed back and forth fast and hard, I she exploded. I felt squirt hitting my chest and dripping down my already sweating body.

I was in awe and she was shaking. Her body trembled as she lay there and we both caught our breath. I began to thrust in and out of her soaking pussy again. I could feel she still had plenty left in her, so I fucked her to climax again. She screamed as my cock rubbed her pussy until she shot a huge stream of cum over my shoulder and in my face. It was like getting blasted by a fire hose. I turned around to see the wall covered in squirt.

I wasn’t done. I wanted more. So I turned her over onto her hands and knees and fucked her hard from behind. I loved watching her bubbly ass bouncing on my hips and see her pussy sliding back and forth on my shaft. She told me to fuck her harder so I did. I pounded her until I could feel another orgasm. I pulled out and slapped her clit with my tip until she collapsed on the bed in a puddle of her own squirt.

I turned her onto her back, knelt next to her face and shot a massive load on her face.

Did you have an orgasm? Did your partner(s)? She had several and I had one.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Condoms

What were your REASONS for having this hookup? I was horny and she was sexy.

Were alcohol or drugs involved? If so, how much? No

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? Afterwards, I brought her to the train station and dropped her off. She wanted to see me again but since I couldn’t afford to get another hotel room so soon, I had to decline, which pissed her off. I haven’t talked to her since.

To whom did you talk about the hookup? How did they react? My online friend. She just laughed.

Was this a consensual and/or wanted experience for you? For your partner? Yes

Do you regret this hookup? If so, why? No

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Best was how sexy she was and how much she came. Worst was how nervous and self-conscious she was.

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

All things considered, how NEGATIVE was this experience? A little negative

Anything else you want to add about this hookup or anything else? This is part one of a three part story called Hat Trick, about a day that I had sex with three different women seperately. I only had one planned but the second and third just happened by chance. I’ll go into detail about how those happened in future posts.