by TNT

Gender: Male
Age: 22
Race/ethnicity: White
Location: Berlin
Highest education received: College degree (eg., BA, BS)
Occupation: Freelancer
Relationship status: Single
Religious affiliation: Agnostic pagan
How religious are you? A little
Sexual orientation: Gay
Any other term(s) that describe your sexual orientation/sexuality better/best? Power bottom
How many sexual partners have you had in your life (including oral sex)? 100+
How many hookup stories have you here posted before? 0

First Time Fister

How long ago did this hookup happen? 1 year

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 off session

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? I was traveling around Europe as a solo backpacker, and in each city I went to I would always log into Grindr and Scruff and all those other gay geo-location apps just to see who was around. I talk to a lot of people, something occasionally comes of it, but not all the time. I was staying with a Couchsurfing host in Zürich, but he had to go to work that day, so he left me in his place and I browsed the profiles and headless torsos that were around me in the city. I’m into old guys, so my favourite app is Scruff. I got a message from an older guy, somewhere in his mid 40’s, I think. He wasn’t conventionally attractive, but I was feeling a bit horny and when it comes to older guys its just more about the rush and the sense of taboo about the age gap that gets me off, rather than any physical attraction. I’d never met him before in my life, but he spoke English very well so we had a decent conversation. I told him I was looking to play, he said I was more than welcome to join him. His stats seemed pretty standard so I figured he was probably just a normal guy like me – except a little older – who wanted to blow off some steam.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I think he initially instigated it, although we were both clearly up for it in the beginning. In the end I asked if he had anything to eat – I was a poor traveller at the time and Zürich is an expensive city, so I was living very frugally – he said he had lots of leftovers and that he would happily feed me as well as fuck me. Sounded like a win-win to me, so I hopped on a tram and traveled to where he lived across town. It probably took me about 20-30 minutes, but I had nothing else to do that day. He said he would meet me at the tram stop. It was all pretty easy really – there was no attitude and no fuss about anything. We walked back to his apartment, and he gave me some water and we sat on his balcony in the sun for a little while. Surprisingly, we didn’t cut straight to the chase, but had more decent conversation. He’d been made redundant, so had a lot of free time. We talked about travelling, our lives, our hobbies, just really general talk, but in the kind of raw depth that you share when you don’t think you’re really ever going to see that person again, so in the end it didn’t really matter. It’s kind of like therapy. He smoked a joint at some point, I can’t remember if that was before or after we had sex the first time. In the end it was a very civilised decision to move to the bedroom and commence having sex.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? Did you have an orgasm? Did your partner(s)? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? He took me to his bedroom, and that was where I saw his sling. I was a little bashful, but he just laughed. We started kissing, very passionately, and disrobed piece by piece, between long, wet kisses, until we were completely naked. He had a decent sized cock, and I sucked on it for a while, then he sucked mine, when we laid on the bed so we could both pleasure each other at the same time. It was very tactile, there was lot of rubbing and holding each others bodies very close. The natural progression went from kissing to licking and sucking – I’m almost always the receptive partner so he turned me over and spent a little while rimming and fingering my ass. When he was finally ready to fuck me, he got out a towel and laid it on top of the bed – silicone based lubricant stains sheets like a absolute bitch. It wasn’t exactly romantic but then I wasn’t there to be romanced. I laid on my back and he fucked. I made myself come while he was still inside me, and then he pulled out and finished on me. We had a brief shower together – him making awkward post-sex conversation and me smiling and laughing politely but not saying much. 

He then offered me the food I had mentioned earlier, and I was starving so I stuck around and ate. It was really nice pasta, actually. We sat back down on the balcony on some soft couches in the sun, still naked. He lived in a place were you couldn’t see into his balcony so it didn’t matter. We chatted some more, this time a bit more about our sexual habits and preferences. He showed me some pictures of him and his previous partner. They had been together for 10 years and were both experienced at the art of fisting. I used to work in a fetish store so I wasn’t at all shocked by what I saw, even though I’m not usually into it myself.

I hung around long enough that in the end we went around two. There was less oral and lead up this him, and he entered me doggy style to mix it up a little bit. Positions weren’t that important, but after that we were exhausted. We showered again, and at one point during or after he put his fingers in mine and said “You have such lovely hands, you know?”
I gave him a sceptical look. “What are you trying to say?”
He asked if I would be interested in fisting him. I had a very “try anything once” attitude, and after my work experience in the fetish store I was too fascinated to say no. He had a douche system attached to his shower, so we both used it to… ahem, clear ourselves out. It was the most powerful one I’d ever used before. We waited about half an hour before starting anything else, and luckily so because I ended up feeling a bit sick and had to run back to the bathroom – turned out I hadn’t expelled all the water out of my ass, the water had gotten right up in there!

So we returned to his room and approached the sling. I had to cut my fingernails and take my ring off, and he provided me with disposable black latex/rubber gloves. The lubricant many people use for fisting is Crisco, the same stuff they use for cooking. He had a jar that he uses for himself, which I could directly dip my hands into, and a separate one for other people, which he could scoop out enough Crisco into beforehand and place in a separate bowl. He climbed into the sling and positioned himself. I sat on a stool at the end of the sling, taking directions from him as I went. First I had to lather the gloves in Crisco. Then I had to take a small dollop of the substance and push the whole thing inside him – apparently you have to completely lube up the inside to protect the delicate anal tissues and everything in there. I slowly did all this, and then gradually edged my fingers in, starting with one, then two, then three, switching between hands. There was a bucket underneath the edge of the sling, and at one point a little bit of left over douche water dribbled out. I remember being mildly horrified until I realised I was about to put my whole hand in his ass anyway. I did four fingers, two on one hand and two on the other. Then four on one hand. Four fingers isn’t too extreme, I’ve had previous boyfriends do that to me during casual play. This guy seemed to be really enjoying it, but I had to get the go-ahead from him before I did anything else. I slowly edged my hand forward. I could feel his anus muscles stretching over my knuckles, and at first I was scared I was going to tear something. I have pretty average sized hands, but still. Once it got past the knuckles, it was like kicking over the engine. My thumb and the the rest of my hand slipped in up to my wrist. 

Once it was in there, I was at a bit of a loss of what to do. I don’t even normally put my own dick in guys asses, let alone my hand. I just kinda wiggled my fingers around, moving them around inside him. He was grunting and moaning with pleasure, so I must have done something right. He asked me sexily, “Yeah, do you like it?” and I just kinda smiled and thought “This is all you, buddy.” I was fascinated by the whole thing, but I wasn’t exactly turned on. The longer my hand was in there, the bolder I got about it. I went a bit deeper, pushing my hands to the sides, and even pushing upwards. I could create little bulges in his abdomen when I pressed upwards from the inside. It was like a game to me, more than anything, but it was driving him wild. I didn’t like thrusting though – it felt too much like I was punch fucking him, and that just evoked violent images I’m not comfortable with. I was slow and probably pretty gentle, giggling and squeezing things while he jerked himself off. At one point I went in up to my forearm, and I lost sight of the end of the glove. I freaked out for a minute, but I figured I was already that far in a might as well enjoy the right. 

I continued and he jerked himself off until he came. When, he did, the force of his anus clenching around my forearm was almost painful. I very slowly, very gently, withdrew my hand – it hurts if guys pull their dicks out too fast, I can only imagine what a hand would feel like. The sight of his asshole afterwards wasn’t exactly pretty – it wasn’t inside out, but it didn’t look not painful. He seemed very pleased though, and thanked me profusely. In the end I also climbed into the sling, and he used the Crisco to play with and finger my ass for a little while. I enjoyed that, but since he had already fucked me twice that afternoon I wasn’t in the mood to attempt a fist for the first time. He was fine with that though, and he pleasured me until I was too exhausted to keep going, and too spent to come. 

We showered and chatted a little bit more. He had another two friends coming over later that evening – they were all going to have more sex, apparently. One of them arrived, a tall older gentleman. I told him I would get going and leave them to it. 
“Well, you don’t have to,” said the new arrival. I found him quite attractive actually, but I did have to get going. I had spent several hours there doing our various sex acts. 

He gave me his name and his number on a business card, and said to stay in touch. I never called him since I was leaving the country, but I still have him as a Favourite on my Scruff profile, and every once in a while we exchange brief messages. So I guess you could say we keep in touch.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? He was very proactive with safe sex. Condoms were non-negotiable for him, which was nice because I hate always having to be the one to tell them to put it on. The fisting was also very safe with the gloves and the assurance that no Crisco was cross-contaminated. Even the douche system had an alcohol wash that cleaned the device between users. Needless to say, this guy was very experienced in playing safely with others.

What were your REASONS for having this hookup? I was bored, and I was very horny. The whole fisting scenario was not pre-planned though. I’m not sure I would have gone through with it if it had been proposed as a condition from the beginning, but at the beginning he had made it clear he would be happy to just have regular, non-kinky sex. 

But my primal reason was I am a guy that likes to have sex. Nothing more, nothing less.

Were alcohol or drugs involved? If so, how much? No alcohol, and he smoked maybe one joint at some point throughout the sessions. It played no major part in the afternoon at all.

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 felt like I had done something absolutely crazy. I had theoretical knowledge of fisting, and I had put it into practice. I had once thought that maybe I would even consider being the receptive partner in fisting, but after seeing what his asshole looked like afterwards, I have pretty much scrapped that from the sexual bucket list. I left feeling extremely satisfied and a little more worldly. My feelings for him were pretty indifferent – it was unlikely I would ever meet him again, and to this day I feel pretty neutrally about it. Though if I met him again I’m not so sure I would be up for a round two. Unlike him, I didn’t have a desire to turn it into a habit. But he was a nice enough man.

To whom did you talk about the hookup? How did they react? At first I thought I would never tell anyone. Then I told a couple of my close friends, via Facebook since I was still travelling. They were all mildly horrified, pretty shocked, but in the end not that surprised, given my work history and my open, sexual nature. Now it’s that shocking story I tell at parties when everyone is super drunk, or when I want to one-up someone on a sex story that they think is pretty crazy. A few people take it better than most, with a chuckle and a raised eyebrow – those people are usually slightly familiar with kink themselves. Worst reactions are people claiming they’re going to be ill – I don’t really spare the details – but they just laugh it off. I don’t tell people if I think they would actually have a problem with it, not because I’m afraid of being judged but because I’d rather not portray negative stereotypes about something that is apparently a legitimate sexual hobby. Most people never look at me the same way again, for better or for worse. I don’t really mind.

Was this a consensual and/or wanted experience for you? For your partner? Completely consensual on both sides. I was a little nervous, and didn’t get off on the fisting part, but I was willing to take part simply for the sake of being able to tell the story later. And all the regular sex was fine as well.

Do you regret this hookup? If so, why? No regrets. It was a one off experience that I might never have had the opportunity for again, without having to go searching for it myself, which would probably be less inclined to do.

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? The best thing was the free lunch. No, just kidding. The best thing was that what I thought was going to be a quick fuck turned out to be a day of hanging out and conversations and having company in a city that I was largely alone in, as well as some great sex and new experiences. The worst bit was probably the little bit of water dribbling out of his ass when I started fisting him, but hey, shit happens… or, doesn’t happen, I guess, is the point of douching.

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

Anything else you want to add about this hookup or anything else? I think the lesson to be learnt here is that you can have had more sexual partners than you can ever remember, doing more things than you would care to publicly admit, but despite all that you can STILL find new sexual experiences that will shock you, shake you, transform you, and open your eyes to a world far beyond what you already know.

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