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What’s your gender? Man
How old are you? 45
What continent do you live on? North America
What country and/or city do you live in? United States
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? College Professor
What’s your current relationship status? Engaged/Married (monogamous)
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 16
How many hookup stories have you here posted before? 3

Leilani

How long ago did this hookup happen? Last week

What was your relationship status at the time? Same as current status

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

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? Leilani (“Lani” for short) is part Hispanic, part-Asian, and part-Polynesian 5ʻ3 with shoulder length brown hair. She keeps herself in shape with firm boobs and a tight ass. She is a long-term relationship with a guy for the last 7 years, and have three children together, but they havenʻt gotten married. Lani and I are in different departments, but we occasionally have lunch together and she comes by to talk — especially when things arenʻt going well in her relationship or with her children. Our relationship has always been platonic, though I have lusted for her secretly ever since we met a few years ago.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Last Friday, I got an email from her asking me if I was going to be in my office at 4:30 because she encountered an unexpected rough patch in her life and she wanted to get my take on it. I told her Iʻd wait for her to drop by when she got off work. She came by shortly after 4:30 and it looked like she had been crying. I gave her a hug and asked her what was wrong? She told me that she had been thinking of leaving her live-in BF for awhile and finally decided to do it. Her BF didnʻt want her to leave and begged her to stay, and her family and friends were giving her grief about being selfish and not thinking of her BF and the kids. She asked me if I thought she was doing the right thing? I told her that I wasnʻt in a position to say yes or no because I didnʻt know all the details, but as a parent myself, my first thought was about her 3 children. And then I asked her if there was another man in the picture? Lani said there was no other man, and the reason she wanted to leave was because she had dropped out of school when she had her 1st child, and wanted to go back to school to pursue her ambition of being a nurse. She said she was 30 years old and she felt that the longer she waited, the less likely it would be that she would ever go back to school to become a nurse. As she talked, she started to cry. I gave her some tissues, held her close, patted her back, and whispered in her ear that everything would be alright.

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? As I held her, she turned her head and kissed me on the lips, which immediately turned in a passionate kiss. It caught me by surprise but my cock immediately responded and I know she felt my bulge because she started to rub it back and forth as we continued to kiss. I began to knead her butt and pull her closer as we kissed, and I felt her hands loosen my belt and unbutton my pants. In turn, I unbuttoned her jeans and slid my hand into her pants to feel for her pussy. As soon as my middle finger felt her slit, I knew she was wet and so I eased my middle finger in her to get it moist, and then started to massage her clit gently as we continued to kiss. It was clear that we were going to fuck so I broke our kiss and locked my door and closed all the blinds. Being a Friday. everyone was gone but I still wanted to make sure we werenʻt disturbed. I have a folding cot that I keep in my office in case I want to take a nap, so I unfolded it and Lani and I lay on it. We continued kissing and touching and I asked her if I could taste her? She nodded and I started to kiss and lick down her tummy and ran my nose of her trimmed bush. I could smell her essence and I neared her pussy entrance — and as I spread her lips, I could see her glistening. I licked her entrance in long, slow strokes from bottom to top, alternating between the left and right sides, and going deeper with each stroke of my tongue. Lani moaned softly and put her hands on the back of my head to encourage me. I started to lick gently around her clit and this really got her going. Her moans grew louder and her hips started to rock back and forth, and then she told me to suck her clit. “Harder, harder” she said as I sucked on her clit and then she just exploded in an orgasm. She clamped the sides of my head with her thighs and just gyrated her hips as she rode out her orgasm. Before she got a chance to calm down, I got into a missionary position and entered her with one firm push. She gasped as I entered her but began moaning as I fucked her — in and out slowly at first, but then harder and faster at her urging. I felt myself coming, and knowing that I wasnʻt wearing a condom, I asked her if she was protected. She said her tubes were tied after her last child so it was ok to cum in her. As soon as she told me that, I erupted in her squirting my cum in as deeply as I could. “Oh! Oh! Oh!” she said as she felt me cumming in her.

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? After cumming in her, I collapsed on her, both of us panting. Then we lay next to each other and cuddled and kissed — her fingers gently rubbing my back and my fingers gently rubbing hers. “Thank you,” she said, “I really needed that.” “Thank YOU,” I said, “Iʻve wanted you ever since we met but thought you were unavailable.” “Well,” Lani said, “Iʻll be even more available after I leave “Chris” (her BF) so maybe we can do this again and more often?” “Iʻd love that,” I said, as we got dressed to go home for the weekend.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Attraction to partner(s), Emotional intimacy, closeness, connection

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? No one.

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? Being with Lani for the first time.

What was the WORST thing about this hookup? Nothing.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No

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!

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