by Loveland

Gender: Male
Age: 39
Race/ethnicity: Caucasian
Current location: CO
Highest education received: College degree (eg., BA, BS)
Occupation: Finance
Relationship status: Married
Religious affiliation: None
How religious are you? Not at all
Sexual orientation: Mostly heterosexual
How many hookup stories have you here posted before? 2

The Best Lover

How long ago did this hookup happen? 2 months

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…)? Fuck buddies

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 posted online looking for a lover on the side. She was a single mom who was looking for something too. We exchanged emails for a while before we met the first time, at a hotel the first time, then twice more at her house.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The first time we met at a hotel between us. It was stressful planning it, but when she opened the door I was relieved and very turned on. She was super hot, cute and normal seeming. That time we had amazing, if rushed, sex. She gave me an amazing blowjob, and I loved going down on her, and we finished with a perfect orgasm together.

The next time we met at her house – which was stressful all over again. But I felt like I could trust her and so went anyway. She turned me on so much I didn’t even  notice anything about her house. She led me upstairs to the bedroom, and I was very excited about our second meeting. I am usually very long lasting and we had both come quite quickly the first time. We lay on her bed which was surprisingly high off the ground, and made out. She got off the bed and gave me another incredible, beautiful blowjob. I stopped her and pulled her clothes off and she climbed on to me. She rode me so enthusiastically and noisily that I just could not contain myself and came quicker than I would have liked. I had wanted to go down on her again as with the first time.

We met one more time, again at her house. After some awkward chat, we made out on her couch before I took her shirt and pants off. I took mine off and knelt over her and she sucked my cock so wonderfully, I was so turned on. I sat on the couch and she took off her bra and panties and rode me, on the couch, her lovely breasts in my face, again with such wonderful noise and enthusiasm that I had an incredible orgasm. It felt so good being inside her, feeling her, hearing her. She wanted to go again, but I had to go.

After that time we never met again. We ended it, but I regretted never having time to go again with her. I could have gone down on her, and had her suck my cock forever. She is a fantastic lover.

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? kissing, oral sex, vaginal. No anal. Not her thing.
it was never awkward after the first few minutes.
We ended it after agreeing a covert love affair was a bad idea.

Did you have an orgasm? Did your partner(s)? Yes, both of us each time.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? None. I trusted her that she was clean and I have had a vasectomy and am clean.

What were your REASONS for having this hookup? I wanted some sexual variety in my life, perhaps to be validated that I am a capable lover, and I honestly love sex very much. The excitement and delightful feeling of someone new, being turned on and turning them on, is missing in my life. But I was also adamant about not wanting to hurt anyone. And she seemed to fit the bill.

Were alcohol or drugs involved? If so, how much? Nope.

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? I feel ok about it. Always nervous it would be found out and ruin my kids and wife’s life. I don’t feel it is an inherently bad thing, but wish it could be more out in the open.

To whom did you talk about the hookup? How did they react? Not a soul.

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

Do you regret this hookup? If so, why? No, not at all. In fact,I wish it hadn’t ended.

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? The sex, her enthusiasm, her sexy body and the incredible experience of having sex with her.

Hasn’t changed much I don’t think.

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

All things considered, how NEGATIVE was this experience? Not at all negative

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