My First Online Meetup

This post is sponsored by The T Bar.


What’s your gender? Man
How old are you? 52
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Washington DC
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your current relationship status? Engaged/Married (open)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 3
How many hookup stories have you here posted before? 0

My First Online Meetup

How long ago did this hookup happen? 3 weeks

What was your relationship status at the time? In a relationship (open)

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? Dave, we had never hooked up or met. He is married and was curious as was I when we met and began to chat through an online swinger site where we both have profiles with our spouses. We seemed to hit it off and our conversations turned personal quickly. We decided to meet for a cup of coffee one afternoon to discuss getting together as couples and ended up going to his house nearby where things turned incredibly erotic quickly. Dave is slightly younger than I am in great physical shape at 5’10” and weighing 190 pounds with a very chiseled muscular build and strong features.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We met online for planing to hookup for drinks as couples when our conversations turned personal talking about desires and fantasy. There was no plan for our meeting to get physical and we planned to meet up face to face over coffee at a local coffee shop to discuss getting our spouses together for a drink to see if there was chemistry.

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? Dave and I had met for a cup of coffee and immediately hit it off with a hidden mutual attraction. He asked if I wanted to see where he lived and I said yes and followed him to his house planning on only being away from work for less than an hour.

Once we were inside he showed me around and offered a bottle of water which I accepted as we stood in his kitchen talking about getting together again for drinks. Dave leaned in and kissed me by surprise. It was the first man I had ever kissed but I enjoyed it and embraced him until he broke away and said “Sorry, I don’t know where that came from. I have never done anything like that before but could not resist.” Dave and I were both dressed in business suits complete with tie and jacket as we stood silent for a moment. Dave spoke up again “I hope I didn’t make you uncomfortable…… I guess we better head out.” I replied “No, I enjoyed it.”

He laughed uncomfortably and said “Me too.” I reached and lightly brushed his crotch with my hand almost impulsively and he stepped forward and began to kiss me again as my hand returned to his groin feeling the unmistakable bulge if his hard cock underneath. Without speaking when our kiss broke he led me upstairs by the hand into a spare bedroom as we both began undressing each other with our clothes falling to the floor around our feet. I was standing in my underwear as I grasped Dave’s briefs and began pushing them off his hips and went down to my knees taking his cock into my mouth as I sucked the first cock of my life. Dave had a nice cock probably 5-6” long with his pubic hair very closely trimmed. Dave moaned and his head tilted back as I heard him say “you are an amazing cock sucker” before moaning more with his hands on either side of my head. I sucked him for several minutes before I heard him say I was going to make him cum and he picked me up underneath my arms and almost threw me onto my back on the bed before going down and taking my cock into his mouth. His hands ran over my chest and stomach as he sucked me.

Dave sat up in the bed between my legs and picked my legs up by the ankles and pushed them back over my head before going back down and licking my balls and rimming my ass as I grasped the sheets in my hands. I had never been with a man and I was going crazy with desire as Dave knelt and kissed me again with his hard cock nestled between my cheeks poking at my ass. I ground my hips feeling his cock pressed against me and as he kissed me reached down and guided the head of his cock to my virgin hole as my hips pushed against him and I felt him begin to penetrate me. It was painful but I wanted it and continued as Dave began pushing his hips to push himself inside me deeper and deeper until he was fully impaled into me. I told him to wait a moment before thrusting to allow for me to adjust and then he began to fuck me. I could hear the sound of our flesh slapping together with each thrust and the discomfort quickly turned to pleasure as the motion continued for the next five minutes or more as my legs were on Dave’s shoulders until he began grunting and reached climax shooting his load of cum deeply inside me.

Once he pulled his limpening cock out he went back down and began sucking me and it did not take long before I told him I was ready to cum and he continued allowing me to fill his mouth with my load and he struggled to swallow it all. Once I was finished he moved and kissed me again saying “That was one hell of a massive load.” I was still breathing deeply as I felt his cum draining from my ass and looked at the clock radio realizing it had been an hour and a half since I had left the office. We both dressed quickly and had to leave since it was the middle of the work day.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, 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? The experience ran through my head the entire afternoon at work as I still had several hours before going home. It was exciting and I loved it but wondered how it happened. We have talked each day since and are planing to meet at his house again this next week for an afternoon with more time to spend.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Discussed STI testing history, Exchanged recent STI test results

What were your motives for this hookup? Making new friends

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? Somewhat

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

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

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? I was able to explore a part of my sexuality that I had never entertained before. I don’t know if I will ever repeat it with anyone else but it is a possiblity.

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

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

Anything else you want to add about this hookup? Never say never

What do you think about the Casual Sex Project? I have enjoyed reading other peoples experiences.

You have a hookup story to share? Submit it here!