A Day of Firsts



What’s your gender? Man
How old are you? Early 60s
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
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Retired
What’s your current relationship status? Single
Religious affiliation: Agnostic
How religious are you? Not at all
What’s your sexual orientation? Bisexual
Any other term(s) that describe your sexuality or sexual identity? Open minded
How many sexual partners have you had in your life (including oral sex)? More than I can remember
How many hookup stories have you here posted before? 1

A Day of Firsts

How long ago did this hookup happen? Yesterday

What was your relationship status at the time? Single

How would you best classify this hookup? Fuck-buddies / Booty call

How long did you know the person before this hookup? For less than a year

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? Age 18 is what he claimed. But, he is in high school and looked younger. 6 foot tall, maybe 135 lbs. Baby-faced, attractive. Very skinny, clean-cut, LARGE Dick with a pronounced downward curve. We had met up for car sex about a year ago from an ad on CL. Lost touch for awhile, until he contacted me via mail. I was attracted to him immediately. Although I’m a masculine man, I always was a bottom, somewhat sub to males. Always used protection. Never into kissing or romantic stuff. Just the way I was after discovering my interest in men 40 years ago.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? John emailed me a couple of months ago, asking if I wanted to meet up again. I said yes but, was out of the country for a month so, it had to wait until I returned. I contacted him later and we discussed meeting at my home. I had to pick him up as he did not have a vehicle. The only other time we had hooked up was for a quickie in my truck. At that time, I sucked him and he fucked me laying over the back seat with a condom on. The whole encounter was 45 minutes. I told him I’d like to have more time to explore.

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 picked up John and brought him to my home. I sat on the edge of the bed and lowered his trousers. He was already hard. John’s cock is very thick, about 8 inches. Halfway down his cock, it takes a sharp curve toward the floor so, when fully erect, it actually points at the floor. I’ve never seen one like that before.

I rubbed his skinny body with hand and took the head of his cock into my mouth. Cupped his tight ball sack while sucking him. Very soon, I was deep sucking him as best I could, getting 6 inches into my mouth before the gag reflex hit me. He is very thick as well as long, so there was no way I could take him balls deep.

While I was gagging on John’s dick, we unzipped me. I stood and dropped my clothes to the floor. Standing, we rubbed our bodies together, cock to cock. I was as hard as John, though a much smaller 6 inches. John stroked my cock while kissing my neck and sucking my nipples. I was extremely excited.

He pushed me back on the bed and began sucking my cock, playing with my asshole with his fingers. Then, he rose over me, laid on top and leaned forward to kiss me. In all my years, I had never kissed another man – it just didn’t interest me until yesterday. I truly wanted to please John at that moment so, I locked mouth with him and we began kissing, soft at first and then full-on mouths. I was caught up in the erotic feeling. I told John to let me know what he wanted to do, to give me instructions.

We rolled into a 69 position with me on the bottom. His cock was fed to me easily because of the natural down curve. He was sucking my hard dick while I took his as deep as possible. Then, I began rimming his slightly hairy taint and probing his hole hard with my tongue. He was moaning hard, clearly enjoying this. I felt he was near to cumming so, I stopped and rolled him to his side. John asked if I was ready to be fucked. I told him absolutely.

I laid on my back and John told me he wanted to fuck me bareback. Although I never did that before, I was so excited, I waited while he pushed a lot of lube into my ass and inserted one, then two fingers, pushing the lube deep into me. I also coated his dick with more lube, knowing taking that cock was not going to be easy. John raised my knees and leaned over me, placing his cockhead against my opening. He was very gentle, pushing the tip into me slowly. I felt some pain as he slipped past the ring, and told him to wait until I adjusted. He leaned forward and we began kissing again – I wanted that from him.

We kissed passionately while John forced his large penis into me. I felt my intestines being rearranged as he was fully into my ass. I asked him to wait for a minute. As we again began to kiss, I willed my self to forget the pain and felt his cock begin to move in me. I had never felt a cock so deep. John began slow and short strokes and gained speed as I told him it was no longer painful. He withdrew and began plunging into my ass harder. I wanted more and, grabbed his ass to pull him into me as deep as possible.

John withdrew his cock from me and asked me to ride him, reverse cowgirl style. He laid on his back and I stood over him, lowering my ass to his cock, slowly dropping until he was fully up me again. I placed my hands on his knees and began fucking him harder. This position allowed his dick even deeper and the pain returned for a while. But, I wanted to be fucked harder and forced myself to rise and fall on his engorged cock. I have never been fucked harder or deeper. My legs were actually trembling, feeling his length and girth so far up my ass. We fucked like this for several minutes until I told John I needed a rest.

We laid side by side and chatted about our lives, his school, my kids. My cock had deflated but he remained hard. After about ten minutes, I reached over and began stroking his wet dick, marveling at its shape. John asked if I was ready again.

He asked me to get on my knees because he wanted to fuck me from behind. He rose behind me and relubed my hole. I felt his cock enter me and push deep into my gut, even deeper that before. I felt pain and he pushed all in and asked him to wait. We remained locked, without moving, until I felt his urge to fuck me. I dropped my heat to the bed and John began fucking me with earnest, Long deep strokes, rearranging me inside. I was just adjusting to him when I pushed very hard with his hips. Deeper than ever and causing a fair amount of pain. It was a pain I wanted so, I told him to fuck me deep. I asked that he cum in me – a feeling I had never had before.

John pounded my hole for another 15 minutes, using deep, hard strokes. As I was about to ask him to take another rest, his movements increased speed. I knew he was getting close. Another 10 strokes and I felt him increase in size within me and he pushed as far into me ass possible, holding his cock still while he ejaculated up my ass. No, I didn’t “feel” the cum, but I knew it had happened. John pulled out of my hole and laid back on the bed. I touched my sloppy hole and smelled a mixture of lube and the unmistakable smell of cum.

We again relaxed and talked for a half hour. I rose and started a shower, telling him he could go first. I waited for a few minutes while John showered. He seemed to be taking a long time and I felt the need to clean up myself. I asked John if I could join him, he agreed. Of course, once inside the stall, I began to play with his body, rubbing the soap over him, I dropped to my knees and tried to bring his dick back to life. That wasn’t going to happen this soon and he remained at half mast. I hadn’t cum yet, so John masturbated my cock with his hand. I was very hard and felt I would soon cum. John rubbed soap on my cock and faced the wall. He asked me to fuck him.

I had never before fucked a man’s ass but, I stood behind John and pushed my 6 inches hard into his ass. He showed no pain, so I began pushing into him harder, feeling the incredible warmth of his insides and his ring clamping onto my shaft. Within a minute, I felt my cum begin to rise and fucked him as hard and deep as possible. I came hard, shooting sperm deep into John’s hole. We stood under the waterfall of the shower, me grasping him around the waist, and waited until my deflated cock slipped from me. I dropped to my knees behind him, parted his cheeks and lapped cum and soap from his hole.

We finished showering together. As I toweled him off, John was fully hard again. He asked if I wanted more. We had been at this for one and a half hours, my legs were wobbling, my asshole was totally sore and I had just cum hard in his ass. I laughed and politely declined his generous offer.

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? That would be today. My ass is still slightly sore but, I am at the moment aroused and plan to jack off momentarily. Yesterday was really a first for me in several ways. I had kissed a man with passion. I had been barebacked for over an hour. I had cum in a guy’s ass for the first time.

John will be leaving to another state this summer but, will return once in a while. I made it clear I’d like another play day before he left and told him I’d gladly pay him a visit.

There is no “future” for the relationship other than hookups when we find the time. After all, I am in my 60’s and John maybe 19, possibly younger. I enjoy his company, his personality, and his body.

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection, Thought it was an important experience to have, To feel more desirable, Power / Dominance, Submission / Relinquishing power

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? This site is my only confession.

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? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Doing things with a man I had never done before.

What was the WORST thing about this hookup? Nothing at all.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No, other than I found it enjoyable to fuck a man’s ass and intend to do that again.

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? After recounting this story for your readers, I desperately am in need of masturbating.

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? As a single man in his 60’s, I find it easier to hook up with men now. Casual sex is fun for me. I guess I would say I have become much more open to experimenting with any type of sex.

What do you think about the Casual Sex Project? I read your posts daily and find the stories interesting.

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