Bring A Condom, Just In Case



What’s your gender? Man
How old are you? 22
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Africa
Highest education received: Post-graduate degree (currently pursuing)
What’s your occupation? Health
What’s your current relationship status? Single
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Bisexual
Any other term(s) that describe your sexuality or sexual identity? Vers switch
How many sexual partners have you had in your life (including oral sex)? 4
How many hookup stories have you here posted before? 0

Bring A Condom, Just In Case

How long ago did this hookup happen? 2 days

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

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

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? An older guy, just south of 40, normally the kind of guy I’m into. Met on Grindr, wouldn’t send a face pic other than a blurry pixelated one on the profile itself (guess that was an indication of how it would go). Didn’t really know much about each other, other than both had been tested recently. In the past, I had only had and given oral to a guy once, so when we hit it off over the course of a few hours I committed to meeting him.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I couldn’t host and I’m not that mobile, so he offered to meet up in a local nature reserve that has some animals but is quite safe and offers a lot of hiking trails. Just before he left, I bit the bullet and suggested he bring a condom and lube just in case. I had wanted to try being fucked for quite some time, from before my recent ex-girlfriend and decided that if we hit things off it would be okay. He assured me he had a “few years of experience” and I figured why not. So 30 minutes later, I had walked to the trail and found a place, and he joined shortly after.

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? We met, he didn’t look like the photo’s he had sent other than the somewhat blurry face pic and was a bit bigger waist wise than expected. But seemed like a decent guy. We walked around a bit because he wasn’t completely happy with the spot. Once we found the spot he asked why I wanted to try mess around with guys, I explained and then said he would need to initiate if anything were to happen because I was somewhat nervous and not too sure what to do with dudes or what he would like. So he reached out suddenly and grabbed my crotch, was really awkward in the approach and abruptness of it being mid-sentence. But hey, went along with it.

He then tried to undo my shorts, which I eventually took over. He then wanked me a bit and bent down and took my cock in his mouth. Every now and then he stopped and asked how it was – asked him twice to use less teeth, eventually said it was good. Honestly, the teeth kind of killed it for me experienced better in the past and was kind of expecting this to be better, being sober and all in a heightened situation. But then he sucked my balls and nibbled on that bit of skin between them – I hadn’t experienced this before, and have to admit that was great. He also grabbed my ass and rubbed my hole which felt great.

He then abruptly stopped, which wasn’t necessarily a bad thing and then promptly asked why me and my girl had broken up. Which was exactly what I wanted to be thinking about when a guy’s finger was up my ass… Suffice it to say I went limp pretty quick and he didn’t take the hint that that was a touchy topic. He tried to suck me off again, got me hard with some play with my balls and ass and then unbuttoned his pants and pulled them down.

He wasn’t uncut as he had said and had a fair amount of smegma built up. Which I wiped off with my thumb whilst jerking him a bit. He then said I should return the favour. Which was fine, I had sucked myself off once or twice and enjoyed the experience on both sides, so figured I would enjoy this as well. Went down, and took his cock into my mouth. Suffice it to say it tasted markedly different to what I had expected and very different to my own. But hey two dicks cant really tell you what the majority taste like? I went down and surprised myself when I managed to take his entire cock down my throat, held it there for a few seconds and rotated my head side to side licking the underside of his cock whilst playing with his balls. Within 30 seconds or so, he grabbed my hair and pulled me off his cock said he was too close to cumming. I was kind of glad thinking it was almost over, it was a strange experience to suck his cock, but probably something to do with the taste was off for me. He turned me around and started fingering my ass some more, spat on his fingers and was rubbing my arms, sides and ass. Licked my neck and ear which was quite hot and turned me on, I leaned back and kissed him which was great. He had three fingers in my hole, which felt decent and then said I’d fit hit cock. At this point, whenever he moved his fingers it felt great so I agreed to trying to get fucked.
He put the condom on and told me to suck it for a bit, which I did. He stopped me again quite quickly breathing heavily. Turned me around and told me to back up onto him.

I told him to put some lube on first, which he then pretended to do. Honestly no idea why. When we finished the lube’s seal hadn’t been broken…

He then pulled me back slowly and I had his cock at my back door. It was an interesting experience to sit / slide it in. Initially it hurt like a ton of bricks, he told me to hold still, which was hard with my one leg shaking like it was. As the pain changed to a burning yet pleasurable pain, I came the first time. Kind of embarrassing to say that I came just because some guy’s cock was up my hole and I hadn’t touched myself, but hey guess I was right about the bi-thing afterall or maybe just really like my hole being played with.

Either way, as I came, my ass contracted and pushed his cock out completely. I’ve always felt kind of guilty after I cum to gay or bi porn, but didn’t experience that feeling now. I sat back down and we waited a few seconds and he started moving back and forth a bit, grabbing my hips and forcing them back and forth.

The thing that turned me on the most was the way he was pushing and pulling, in effect using me as I tried to help out. Was a major turn on. Around 15 minutes through this, I came again and my ass contracting made him blow his load. Down side was the lack of lube which really built up some friction and burnt somewhat.

How sexually satisfying was this hookup? A little

Did you have an orgasm? Yes, more than 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? He pulled his pants on asked if I would be okay to finish off. Offered me a tissue which was decent and then answered a phone call. Rinsed my mouth out a few times, could still smell and taste what I assumed was smegma (I’m cut and haven’t ever had dick cheese before so not too sure, maybe he was just a bit unclean or its his natural state?).

Came home had a shower, didn’t feel too sore, and my ass didn’t hurt.

Fast forward 2 days, I don’t feel crap about having hooked up and don’t regret it. Willing to give it a shot with another dude to see if it’s better. Found two guys we have chatted and facetimed and they are as their pics show them. Both taller than me, much better built and older which is a turn on, and into similar things I did with my girlfriend that I’d like to experience from the other end.

So it didn’t really change too much losing my anal V card, other than make me want to experience it again, and decide if its something for me or not.

Don’t think I will meet up with the guy again, but may be willing to in the future depending on how things go. He is really a nice guy, just no idea what the fuck happened with the lube?

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

What were your motives for this hookup? Fun, pleasure, horniness, Learning new things, experimenting, Thought it was an important experience to have, 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? Somewhat

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 as of yet.

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? A little bit

Why do you regret this hookup? Feel like I should have waited out for one of the guys I’m chatting to now, who I hit it off with better.

What was the BEST thing about this hookup? Knowing I like anal and give decent head.

What was the WORST thing about this hookup? No lube.
Talking about my ex girlfriend whilst a guy’s fingers were up my ass.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yeah, made me think more along the lines that I am bi, but that I’d need to experiment a bit more to decide fully. Either that or I’m into things up my ass but don’t think thats it, I’m sexually attracted to certain guys.

Casual sex – not at all, would do it again in a flash.

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

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

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