Current location: Amsterdam
Highest education received: High school diploma
Relationship status: Polyamorous
Religious affiliation: Agnostic
How religious are you? A little
Sexual orientation: Pansexual
How many sexual partners have you had in your life (including oral sex)? 72
How many hookup stories have you here posted before? 0
How long ago did this hookup happen? Last month
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
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? My partner was a reasonably short, black cis gay man from Aruba. He said he was 38 on his profile, but later admitted to being 48. He looked extremely young for his age though, so he could have fooled me if he hadn’t told me so. His face was cleanly shaven and he was very muscular, with broad shoulders, a strong jawline and big hands. All in all, he was extremely attractive.
As I mentioned, the first time I saw him was on an online dating website. He caught my eye because he had a well written profile and nice pictures. I would lie if I said that his supposed dick size (XXL) didn’t help as well.
His profile was clearly written and he came across as very intelligent, something that was also apparent in his messages. As I usually get a lot of messages consisting of three words or simply asking for ‘dick pics’, this was a welcome change.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? After some messages back and forth, we met up for a drink and I had a most interesting conversation with him. Cis gay men usually tend to bore me relatively soon, if they are even interesting to begin with. I found him to be very articulate and smart, which is a huge turn-on for me. Our “date” only lasted a few hours, but I decided I wanted to see him again. I send him a message the next day and we arranged for a night of awesomeness. He send me nice pictures and videos leading up to it of him masturbating, just to make me more horny (and slightly terrified) at the prospect.
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? At his place, he invited me to get more comfortable by removing my trousers. I was a tad nervous but obliged, and we sat on the couch watching a movie and having a drink. He was very patient and gave me some time to get comfortable, before we started making out and touching each other. He complimented my body, tattoo and piercings, which made me feel even more at ease. I took off his clothes, exposing his chiseled body underneath. I explained to him that due to my sexual history, I would maybe not have an orgasm or even get hard throughout our session, but that should not discourage him. He told me that he would keep that in mind and that took away my last inhibitions. I started stroking his penis, making him hard, and when I took it out of his trousers I finally realized what I was up against. His dick was at least 9 inches long, and with a girth to match. Despite my expert deepthroat skills, his apparatus proved too much for me, but he enjoyed it nonetheless. After a while he put on a condom, and after giving me some drugs and using a significant amount of lube, he slowly pushed inside of my ass. We were lying on our sides, a suggestion made by him, as to make sure he would not go too deeply. I must have moaned so loudly it surprises me I didn’t wake up any neighbours. It was partially pain, mostly pleasure, and after a while I was even countering his slow, careful thrusts with thrust of my own, begging him to fuck me harder and treat me like his fuck toy. This was the signal for him to get on top of me with all this weight and giving me a good fuck. I buried my head in one of his pillows and the combination of pain and intense stimulation of my g-spot made me fly high as a kite. How long this went on I do not remember, but it must have been hours, taking short in between to get some rest. After a while we cuddled a bit and then crashed in seperate beds for some well deserved rest.
Did you have an orgasm? Did your partner(s)? I did not have an orgasm, but this was not an issue. When bottoming, the last thing I think about is actually cumming myself.
He came while fucking me, at least once, possibly twice although I am not sure on that.
What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We had a discussion beforehand on STI’s. I hate using condoms during oral sex, so I took the risk of believing he got tested recently and was found with no STI’s. We used condoms while fucking.
What were your REASONS for having this hookup? When I date cis men, I usually take on a very passive role, bottoming only and making it purely about me being a ‘slut’. He, as 100 % top oriented, was able to give me this feeling, but at the same time being very fun to talk to and being an interesting person. I just felt like this would be a more interesting hook-up than just meeting some random guy in a bar or one of the dozens of guys that send me boring messages every week.
Were alcohol or drugs involved? If so, how much? We had a few drinks before we actually got down and dirty. During sex we were taking respectable amounts of ketamine, to help me relax and be able to allow him inside of me, and it made the whole experience even more pleasurable. It never got to the point where I was not able to think straight though.
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? After falling asleep in his guest room, I woke up the next morning, relatively early and more awake than I had expected to feel. I drank some juice and told my sleeping giant that I would be going home, since I had work to do. He, still half asleep, thanked me for the great night, and after I assured him I could let myself out, I went home. I felt rejuvenated, properly fucked, and with no hangover or sore ass or anything. In short, amazing
To whom did you talk about the hookup? How did they react? I talked about it to my boyfriend and some friends. They all agreed that this must have been a very hot experience.
Was this a consensual and/or wanted experience for you? For your partner? Very much so.
Do you regret this hookup? If so, why? No regrets whatsoever.
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 definitely having some truly enjoyable anal sex with a VERY attractive cis man, as well as proving to myself that I can take a monster cock. No negative side to it that I can think off.
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 or anything else? While I ashamed to admit the hookup was initially for a large part very superficial (the guy was attractive and had a huge dick, something I had wanted to experience for some time), I actually found myself to be really into him. Not enough to see him again anytime soon, but who knows.
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