What’s your gender? Genderqueer / Nonbinary
How old are you? 24
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
What country and/or city do you live in? Netherlands
What’s your current relationship status? Single
What’s your sexual orientation? Mostly gay/lesbian
How many sexual partners have you had in your life (including oral sex)? 70+
How many hookup stories have you here posted before? 3

The Rough Ride

How long ago did this hookup happen? last year

What was your relationship status at the time? Single

How would you best classify this hookup? Short fling

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? Jock (that’s what I like to call him, I don’t even remember his real name) was in his late 40s or maybe early 50s. A rough looking man, tall, skinny, balding, a weathered face with white hair in his scrubby beard and on his chest. He had a stern look on his face, you could imagine that he had been in a few fights in his life. Jock is American and he told me that he was single.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was on holidays in Ecuador when I met Jock on a bus to a small seaside town where we wanted to watch the humpback whales.
The bumpy bus ride took several hours so we had plenty of time to chat. Jock had been a bit reserved at the start, but then he became more friendly. Jock was my type of guy, and I started fantasizing about having sex with him. I had not been with anyone during this trip and had not planned on doing so. Therefore I was pretty horny. Jock did not give me any clues that he is interested in boys, and with all the homophobia in the world, I did not dare to ask.

The bus arrived in the seaside town in the late afternoon. Because we had been sitting next to each other on the bus and chatting for quite a bit it seemed quite natural that we walked around in the town together looking for a hostel. This was the time when I decided to make a move to suggest to Jock that we could share a room. Jock readily agreed and gave me a look that lifted my hopes that intercourse was indeed a possibility.

We got a small room together. It had two single beds, a toilet and a shower. I had an idea on how to test wether Jock was interested in boys. I told him that I needed to get rid of the sweat and the dust of the trip. I stripped naked in front of him, left my towel on the bed and headed into the shower. My body played the part and I already had a bit of an erection. Jock appeared way to intimidating to me to make a more direct approach, so I hoped that this would give him a hint that I am indeed available to him. I showered and wanked myself a bit to make sure that I was erect when I got out of the shower to make sure the message gets across.

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? When I got out of the shower I saw Jock sitting on his bed, completely naked. I was sure of the lust in his eyes as he watched me dry myself. Sex was in the air. I drew attention to my erect penis by drying it very well.
“Come here!” Jock interrupted my show for him. The trick had worked. I walked over to his bed, reached out for him and started rubbing his chest. I leaned forward to kiss Jock, but he turned his face away indicating that he does not want to kiss on the mouth.

I am a very girly gay and I like kissing and cuddling a lot. This was a bit disappointing for me, but I understand that many of the bisexual guys don’t really appreciate the romantic side of sex amongst men. Jock seemed to be of that type. I proceeded to kiss his nipples instead and lick my way down his body. Jock just let it happen and did nothing to caress me. I approached at his dick and started to suck it and lick his hairy balls.

I enjoyed worshipping his cock for a while. Jock got a huge erection and I realised that there might be a problem should Jock want to fuck me. I had not brought any lube or condoms with me on this trip. Even if I allowed Jock to bareback me, it would probably hurt without lube because his penis was big. I realised that Jock was a very selfish lover. I had been sucking at his dick for about 10 minutes and he had not even touched me. I was just sitting in front of him, sucking and licking, touching myself every now and then. I wondered whether I should allow Jock to bareback me. I decided that I would. I had gone this far and there was no turning back. I was a bit afraid that Jock could turn violent if I refused to be barebacked. I wouldn’t even dare to ask whether he had condoms. I knew that this was wrong, but I am a bit of a submissive person and I partly enjoyed the scenario,

Sure enough, Jock interrupted me giving pleasure to him by simply saying: “Come on boy, turn around, let me fuck you”. I just obeyed and sat on the bed in the doggystyle position. There was little point in asking whether that is the position that Jock wanted me to be in. Men like Jock just want to fuck doggystyle, because it is the least personal sexual position. The lovers don’t look at each others faces, it is just humping and pumping.

I felt a shocking stabbing pain when Jock came from behind and just rammed it in. He seemed oblivious that his big penis causes pain. I had hoped he would at least use some spit. The ride was rather painful for me. I did not enjoy it much, only in a messed up sort of emotionally masochistic way. After what seemed like an eternity of dull pain, Jock finally let go of me, informing me that he had blown his load. I started wanking till  I came myself. Jock didn’t do anything to help me with that, he didn’t even bother watching me wank.

We went out to book the whale-watching tour and have dinner. I had hoped that Jock would pay for food and drinks, but that was not the case. It wasn’t about the money, but about the emotional impact. Getting invited would have allowed me to feel more girly about the whole experience. I like the idea of being a girl who gets spoiled by her older lover. All of this did not happen, Jock seemed to be oblivious about what I may want or he just did not care.

Over dinner, Jock told me about his sexual escapades. I was right, he is bisexual. Jock told me that he had paid to fuck a boy in Quito he believed was under age. I found that appalling but did not comment how wrong this is. I fully understood that Jock was an arsehole but I still felt strangely attracted. My arse was still hurting, I feared that he would want to penetrate me again that night, but at the same time I had a desire to fulfil all of his wishes.

We walked around in the town for a little bit and I saw a shop that was still open which had some items that you can find in a drug store. I looked for lube but could not find any. Now I was dreading the next fuck session which would surely happen very soon.

Jock suggested that we should go back to the hotel. I knew what that meant. My arse was still hurting, but I was willing to oblige.

I had not packed any female clothes, only one women’s sexy pants. I put it on when we were back in our room in an effort to spice up the sex. Jock took a shower but didn’t seem to be interested in the sexy girl undies I was wearing. He stood naked in front of me. He allowed me to kiss his neck and his shoulders. I licked over his chest again and went down on my knees. I felt better about the hook up at this point; it was pain free and I enjoyed was I was doing. I sucked Jock’s cock while kneeling in front of him. Jock deepthroated me once and fucked my mouth for a bit, but that was fine. I wanked while I was giving pleasure to Jock. Jock’s only attempt to give some pleasure back was to pinch my nipples once. I don’t even particularly like that.

Jock wanted to fuck again. I tried to lube myself using a bit of soap, but of course I had to do that myself. Jock wouldn’t stick his fingers into my arse in an effort to make his pleasure less painful to me. The fucking was doggystyle again, and pretty painful. I told Jock that I wanted to drink his cum this time. This was a little trick to make my torture take less time. Jock pulled out and I got him off with my mouth and hand. I got off myself by jerking.

We had to get up early in the morning, and while lying in bed with my arse hurting, I decided that if Jock still wanted to have sex before we left the hostel, I would only give him a blowjob.

The next morning, I awoke by Jock climbing into my bed. To my surprise, he touched me and felt my body for a bit. “Come on, let’s do it!” he whispered. Of course, “let’s do it” only ended up me doing something, namely sucking Jock’s cock. I got him to cum into my mouth and on my face. Without asking he picked up his camera and took pictures of me naked with his sperm on my face. I started to seriously wonder why I let him do this.

We went on the boat to watch the whales and came back in time for lunch. While we ate lunch, Jock said something that really pissed me off. He let me know that he actually prefers women to boys and only fucks boys when he cannot find a woman. That really ended it for me. I may be a cocksucker and put up with a selfish lover, but at least I want to feel appreciated. Jock made me feel like I was just his last resort. I could not handle the way Jock completely did not care about my sexual needs and my feelings.

After lunch, we walked the town for a bit. Jock suggested we go to the beach and stroll along there. I realised that he wanted to find a hidden spot where he could fuck me yet again. I was not up for this anymore. I did not dare to confront him, however. I told him that I needed to go back to the hostel to pick something up and use our clean toilet. He should wait for me at the bar where we were drinking beer.

I went back to the hostel, packed my stuff in a hurry, sneaked to the main street and took a bus out of the town. I didn’t even care where the bus would take me, as long as it was away from Jock.

How sexually satisfying was this hookup? A little

Did you have an orgasm? Yes, more than 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? I continued with my holiday. During this time, I was always afraid that I might run into Jock again. Luckily I didn’t I haven’t hooked up with anyone else In Ecuador.

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), Submission / Relinquishing power, I didn’t want it but was unable to stop it

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 consented at first, but later on, I just went on with it because I was a little bit scared of my partner and had a messed up idea about enjoying the abuse.

How wanted was this hookup for your partner at the time? I don’t know / I’m not sure

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

To whom did you talk about the hookup? How did they react? I told friends at home. They were shocked and could not believe that I would let that happen to me. They also strongly disapproved that just I let someone fuck me bareback. They insisted that I have to take an HIV test. I did and fortunately, I didn’t catch anything. I agree with them that it was stupid.

How would you best summarize people’s reactions about this hookup? Relatively negative

Did you get emotionally hurt as a result of this hookup? Somewhat

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Very much

Why do you regret this hookup? I let Jock do fuck me even though I didn’t really want to. I allowed him bareback even though it is against my principles. I did that because I was afraid. I should have told him that he cannot do that and simply get another room if he does not get the message.

What was the BEST thing about this hookup? I have to admit that I enjoyed sucking Jock’s dick.

What was the WORST thing about this hookup? The pain in my arse. The feeling of not getting appreciated as a lover. Jock made me feel completely second rate. Any woman would have been better than me in his eyes. I was just his masturbation tool. Jock was incredibly selfish.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I really have to be more careful of what I am getting into and be decisive about getting out of a situation when I realise I don’t want to be in it.

All things considered, how POSITIVE was this experience? A little positive

All things considered, how NEGATIVE was this experience? Fairly negative

Anything else you want to add about this hookup? People, be careful with whom you hook up. If a hook up turns bad, get away. Just tell your partner to stop, no matter what.

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