First Time Anal Was Spontaneous & HOT

by Gene

Gender: Male
Age: 54
Race/ethnicity: White
Current location: West Coast United States
Highest education received: Post-graduate degree (currently pursuing)
Occupation: Education
Relationship status: Married
Religious affiliation: Atheist
How religious are you? Not at all
Sexual orientation: Bisexual
Any other term(s) that describe your sexual orientation/sexuality better/best? Autoerotic exhibitionist
How many sexual partners have you had in your life (including oral sex)? 15
How many hookup stories have you here posted before? none

First Time Anal Was Spontaneous & HOT

How long ago did this hookup happen? Last night

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 night stand that may develop into a fuck buddy

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? 50 yo divorced white male, professional, about 5’11”, 180 lbs., slightly balding, dark close cropped hair, four day scruff, glasses, moderately hairy body, slightly smaller that average cock with a slight bend, clean smelling.

I had never met him before. I met him in response to his CL ad. I felt neutral about him before the hookup.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Our meeting happened because I responsed to his CL ad looking for someone who fit my description, the gist of which was, “seeking married, 40 – 60 y/o, bi, not promiscuous, into hand/job and oral.” I responded to his ad within 25 minutes of posting. We then exchanged underwear pics, and agreed to meet at an intersection in his neighborhood about an hour later to assess if we wanted to go forward with the hookup.

I was prepared to let it go if it didn’t feel right. However, as soon as I shook his hand and looked into his eyes, I felt a total “yes.” He invited me to follow him to his house, where I parked in his driveway and followed him inside.

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? He offered me a beer, but I took a glass of water. We sat on his sofa for a few minutes, awkwardly discussing our sexual health, and what we were interested in doing / fantasizing about, and where we’d like to be for our encounter. I told him that I was really into touching, oral, and that I have long been into anal self stimulation. We migrated up to a small bed within about 5 minutes, and each of us quickly undressed to our underwear and laid down on the bed facing each other. He asked if he could touch me, I gave the go ahead, enjoying his hand rubbing my still flacid dick through my boxer briefs. After a few moments, I reached over and did the same, finding his hardness growing in his underwear. He suddenly kissed me passionately and even though he had a scruffy face, I kissed him back. I quickly became rock hard. I lay on my back and he climbed on top of me, still with our underwear on, grinding and kissing. I grabbed and squeezed his ass and pulled his hips into mine. He flipped onto his back and I climbed on top of him, still kissing and grinding, touching all over. I reached for his cock, and we tore off our underwear. We moved into a brief 69 position, and I began to lick his smallish cock and balls, and then gave the first real blow job of my life! He thrust madly and I took him all the way in with only minor gag reflex, easier than I had imagined. It felt so hot. He got some coconut oil, and I straddled him as we lubed our cocks. He stroked both our dicks together for a while, then I rubbed my ass on his balls and the base of his cock while we both stroked madly. He needed to change positions, so he got up and brought over some pillows, one under my head, one under my ass. I really wanted to feel him inside me. I chose to trust his word that he was healthy, but I did ask him to not come inside me. He asked me to put my legs up, and soon he was sliding into my throbbing ass. I found out that getting fucked by a man in the ass feels every bit as good as I had imagined, as good or better than my oft repeated self-stimulation. He was very respectful and a hot lover. Our fucking, grinding, and stroking came to a steamy sweaty climax with both of us coming simultaneously all over my belly. He graciously fetched me a deliciously warm wet towel and a dry towel so that I could clean up. We both got dressed, thanked each other, and expressed mutual interest in reconnecting. We talked a bit about our lives with partners and work, and about our mutual surprise at how far we had gone together. I was on my way home less than an hour after we met.

Did you have an orgasm? Did your partner(s)? We both had intense orgasms.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We assured one another that we were disease free. He reassured me during the encounter

What were your REASONS for having this hookup? My wife is away on a trip for the week. She and I have not had sex in months due to relationship issues. I love her very much, but have been feeling increasingly frustrated sexually. Meanwhile, I’ve fantasized about having sex with a man since I was 18. Prior to this experience, I’d had a couple of mutual touch encounters with friends and once with another CL man from out of town, but I’d never done oral or anal. I found myself looking at the CL M4M ads for years, and this one was one of the rare ads I’ve ever responded to, and only the second that I’ve ever acted on.

Were alcohol or drugs involved? If so, how much? not that I know of

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 drove down the street for a block toward home, and felt a build up of mucous in my throat from sucking his cock so deeply. I pulled over and expectorated several times, almost throwing up, but still feeling satisfied and grateful that I’d allowed myself to have an experience I’d always wanted to have. No more self-denial, within reason, with discretion and respect for others! I  hope to hook up again with him, at least once. I respect him, and think he is an interesting man who I’d like to get to know better. I’m open to having a discreet, occasional  “fuck buddy” relationship with him.

To whom did you talk about the hookup? How did they react? only this forum thus far

Was this a consensual and/or wanted experience for you? For your partner? yes, mutual

Do you regret this hookup? If so, why? not at all

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? it felt natural and exciting, very nervous at first, but great to have this experience. I feel more confident about what I want sexually.

The worst is that I don’t feel comfortable telling my wife or my friends. I know that it would likely be upsetting to others.

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

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

Anything else you want to add about this hookup or anything else? I occasionally broadcast on

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