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What’s your gender? Man
How old are you? 37
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA
What’s your current relationship status? Single
What’s your sexual orientation? Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 7
How many hookup stories have you here posted before? 0

Amazing Sex With Young Tinder Match

How long ago did this hookup happen? 3 days ago

What was your relationship status at the time? Single

How would you best classify this hookup? Paid sex

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? I met B via Tinder while traveling. She is a curvaceous and glamorous young woman. She is 20. Great sense of style, clothing, and makeup. Full-figured, gorgeous, with a beautiful face and clothing that showed off her very impressive bosom. Long dark hair. Dark eyes. Somewhat dark / goth aesthetic. Very sexy. We matched on Tinder. Her profile mentioned that she was actively looking for a sugar daddy. This gave me an idea…

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I proposed that I could be her “short term sugar daddy”. To my shock, she responded with interest and the conversation quickly turned to logistics. I proposed that I would love to make out with her, undress her, touch her all over, give her oral sex, receive oral sex, penetrate her vaginally and maybe anally. Maybe cum in her mouth or on her body. Her response was that she would not do anal and that I could “cum all over her”. I proposed a dollar amount for our encounter and she agreed with no bargaining. We decided on meeting at a hotel. It was all happening so fast! My heart was pounding with excitement.

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 had been traveling and was exhausted and way out of it. After grabbing some lube, a Red Bull, and the cash that I had promised her, I checked in at the hotel. We texted back and forth about how she needed to go to a party within 45 minutes or so while I checked in for what felt like forever with a hotel clerk that had no idea that I was about to be serviced sexually by an incredibly hot young woman.

I met her in the parking lot. She was wearing a low-cut blouse, a skirt, thigh-high stockings, and glamorous eye makeup. I was feeling pretty nervous and shy because this was not only my first Tinder hookup but also my first time paying someone for sex. She seemed cool and emotionally detached and greeted me with a hug that I received maybe a bit awkwardly. We entered the room, I paid her the promised amount, and she immediately climbed on to the bed and asked me to turn on the TV to create noise to mask the sound of what was to follow.

I asked her if I could cuddle her. We did so for a bit. I laid next to her, cuddling against her for a bit. My hand first rested on her shoulder then moved to rest on her upper chest. After the cuddling helped me feel a little less wired and nervous, I quickly gave into my excitement and asked her if I could kiss her. I could sense that she was not as into the kissing as I was at first. My probing with my tongue met resistance from her lips that stayed somewhat closed. I started stroking her arms and bare thighs and held back on using my tongue. Eventually she relaxed and seemed to start enjoying it, allowing my tongue to briefly touch hers. We made out for a while with me laying beside her, then I moved between her legs and started grinding against her crotch while continuing to kiss her.

I started groping the exposed part of her breasts above her bra. They were very large and marvelously soft. Craving more, I lifted her shirt up to discover that her bra had a front clasp. I briefly tried to work it but couldn’t figure out how to release it. Amused, she offered to help. She undid the clasp but I held the bra cups over the mounds of her breasts and then after savoring the moment, let the cups fall to the sides, exposing the expanse of her quivering and incredibly soft breasts. I moaned in pleasure as I took her large, pink, left nipple into my mouth, feeling it quickly harden. Her areolae were about two inches wide and her nipples were large and perfect for sucking. I alternated sucking one breast and then the other and then lifted up her right breast to her mouth and asked her to suck it. She sucked it with what seemed like genuine relish while I sucked her left nipple. Then I made her suck her left nipple and asked her to lick it while I also licked it.

Ready for more, I removed my shirt and continued grinding against her. I undid my pants, then removed them. We both quickly removed more clothes and then, while she continued to lay on her back, I placed my semi-erect penis into her warm wet mouth. The sensation was amazing, but I wanted to watch her go down on me while I laid on my back. She crouched beside me and started bobbing her hot and wet mouth on rapidly hardening shaft. I asked her to go deep and she took almost all of my 7 inches into her mouth and throat before gagging. After gagging she sat up briefly and a stream of clear, wet, saliva poured out of her mouth. I asked her if she could sit up while I penetrated her mouth and she agreed.

I quickly placed my hand on the back of her head and guided my cock into her warm mouth and asked her to go deep again. Again, she gagged. A shadow passed over her face and I asked her if this was too much. She responded “a little bit” so I decided to stop penetrating her mouth. I asked her if I could penetrate her vaginally and she agreed. In my travel exhaustion and nervousness my penis wasn’t super hard but I still managed to put on a condom and penetrate her. She was quite wet. (The timeline is fuzzy, but I did eat her out for quite a while, focusing on licking her clit. She seemed to genuinely enjoy this, moaning quietly). When I started fucking her 20 year old pussy she started moaning quite audibly. Unfortunately for me, between my exhaustion and her wetness I felt very little sensation. I pushed her legs together to try to increase the tightness. No dice. I asked her to get on all fours, spanked her a bit after asking her if she wanted to get spanked and penetrated her from behind. Still no dice. At this point I was conscious of her needing to leave to go to a party. So we checked the time. Fifteen minutes left. At the beginning of our sexual encounter I had showed her how to stroke my uncut cock. I was pretty sure that she could get me off that way. Still no dice. Finally, I took matters into my own hands. She was laying on her back and I was straddling her. Her gorgeous breasts and face were on full display for me. I stroked myself for a while and only started to harden after I asked her to play with my balls. Finally! I reached the point that I knew that I could make myself cum so I asked her to switch to jerking me off. She then proceeded to jerk me off hard and fast with her right hand while I massaged her breasts. Her right hand tired so she switched to her left. As I felt my orgasm approaching I asked her to look at me. She locked her eyes with mine. I could feel a massive orgasm slowly slowly building. I asked her to squeeze my cock harder and harder and jerk me faster and faster. Once I knew that I was going to cum on her, I asked her to watch me cum. She obeyed and watched the largest load I have produced in quite some time erupt with great force onto her cleavage and neck. I think I moaned loudly. The pleasure was so intense!

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? I stepped away from her and she asked me for a towel. She cleaned off my huge load and we both started dressing. I noticed that she had actually missed some of my cum on her chest and neck (it was a lot!) so I tenderly offered to wipe up the rest. She joked that it would have been awkward to show up to a party wearing my cum. She gave me a hug and a peck on the cheek, wished me good luck with my travels and left. Later that night I texted her in thanks for the lovely evening and she responded to get in touch if I am ever in the area again. I have a fantasy about either taking her anally or asking her to arrange a threesome with another female friend for me. I wanted to cum on B’s face really bad but I knew that she was going to go to a party and didn’t want to ruin her makeup.

I went home after the hookup and could smell the body lotion that she was wearing on her body and breast on my face and hands. I kept sniffing my hands and marveling at what just happened. I could feel the intensity of my orgasm that night and into the next morning. I was so charged with sexual energy that I had to jerk off a second time that evening.

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? I don’t know

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? I don’t know / I’m not sure

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? No one yet! Wondering who I should tell.

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? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Getting to play with an incredibly sexy 20 year old college student with a gorgeous face, gorgeous body, and enormous breasts with incredible nipples. Getting the best handjob of my life and squirting a huge load onto a young woman.

What was the WORST thing about this hookup? Not knowing what was going on in B’s head. I checked in with her often. Her moans of pleasure did seem genuine but I was not sure how she felt about the overall encounter.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes. I feel more confident about having casual sex. I am obsessed with arranging another hookup right now, though.

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!