by Craves_for_Semen

Gender: male
Age: 41
Race/ethnicity: European
Current location: Australia
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: tutor
Relationship status: married
Religious affiliation: none
How religious are you?: Not at all
Sexual orientation: Bisexual
How many sexual partners have you had in your life (including oral sex)?: 21
How many hookup stories have you here posted before?: 3

A Special Kind of Threesome

How long ago did this hookup happen? 15 years ago

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…)? short fling

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? Carlos was a short stocky Latino man in his late 40s. He was not fat and had a hairy chest. His penis was remarkably fat.  Carlos had told me that he was an architect. He also revealed that he had been married with two children. The reason for the divorce was that he preferred to have sex with young men. Javiera was a young Latina in her mid 20s I guess. She had long black hair, dark tone skin, slim body and nice boobs. Her pussy was shaven. I was 26 when this story happened. I was pretty skinny and had a shaved head. I guess I still qualified as a twink.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? This hookup happened during my “Latin American years”. I was in Mexico City. I had noticed that straight porn cinemas still existed there  and decided to visit one just in order to have access to porn for jerking off. So I went in and took a seat, carefully checking that no man was sitting too close to me. the movie shown was just some average straight porn, but arousing enough to make me want to masturbate. I felt pretty uneasy about opening up my pants because someone could see me. I tried to hide my act with my clothes. I noticed a guy taking seat on my aisle and looking towards me. I immediately stopped masturbating. The guy got up and took the seat next to me. I was horrified, considered looking away. Then I noticed that there were a few people sitting next to each other, which seemed strange at first. Then it dawned on my why that was and stayed seated. The man pulled out his penis and started to masturbate. I got mine out too. His hand reached over, stroking my cock. What an adrenaline rush! I enjoyed his treatment for a while and looked at him. He was older, not fat, so my kind of man, really. I quickly went down on his lap and put his penis into my mouth. The man started to hold my head and caress me. I was very aroused by this, but also wanted to watch the movie, so I started to masturbate hard. In the process, I went down on him two or three more times until I had blown my load. The guy had not. When he saw that I had ejaculated, he tapped me on the shoulder, got up and left. I followed him. Outside, he introduced himself as Carlos and invited me to have a snack with him. He asked me to go home with him because he wanted to fuck me. I thought that was a reasonable request and agreed to it. We took the subway to his house. Upon arrival, I pretty much undressed immediately. I started to give him blowjob. He was a very tender lover and caressed and kissed my body, touching me and licking my anus. Carlos brought out lube and condoms, prepared me and took me from behind. He fucked me until he came inside my arse while I came by masturbating in the process. After this great sensation, he told me that he still had some work to do so we got dressed. Before I left, Carlos asked me whether I wanted to watch him fuck a girl. Of course, I would not let the opportunity to have such an incredible experience go by and agreed. We arranged to meet at his place the following evening.

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 returned to Carlos flat the next evening. There was no woman there, but Carlos told me she would come. We had some wine and snacks and chatted. I had already started to have doubts about the whole story with the girl when the doorbell rang and Javiera came in, greeting the much older Carlos with a kiss. She sat down next to him on the sofa joining in with the drinks. Carlos and Javiera soon started making out. I just sat in the armchair opposite them and watched, sipping my wine. I really wondered what their relationship was. I was sure she already knew what was on the agenda. I found it strange that she did not mind me around while she was kissing this man who was obviously almost double her age. (As was I.) I did not dare to pose that question, so I just sat there. She soon undressed and got out his penis. Seemingly unashamed of me, she put it into her mouth. As the girl was sucking, Carlos told me to stop being idle and do my part. So I went close to them nibbled on his balls while Javiera sucked. She apparently found that very funny and laughed out loud. I seized the opportunity and took Carlos penis from her and started to blow him myself. Javiera was almost hysteric about that and had a fit of laughter. She watched me play with the old man’s penis for a bit but soon took back the dick. She allowed him to deep throat mouth fuck her. Carlos undressed, put a condom on and told Javiera to lie on the sofa so he could fuck her. She followed suit and spread her legs wide, offering him her dripping pussy. Carlos penis slipped inside and began to fuck. They kissed while fucking and Javiera genuinely seemed to enjoy it. Which again made me wonder about their arrangement. But I got very aroused by that sight and did not care any more, unashamedly pulling out my dick and commencing with the masturbation. Javiera saw me and laughed at me so hard that Carlos almost had to stop fucking her. They kept on fornicating and it was so hot that I had to restrain my masturbation so I would not ejaculate early. Javiera shrieked, and Carlos finally pulled out his dick, stripped of the condom and sprayed his sperm all over Javieras glorious tits! What a sight to behold! I stopped masturbating. Carlos told me to lick Javiera clean. I approached her and she started giggling again. I licked the sperm off her breasts and belly, went down on her and also briefly swirled my tongue over her vagina and anus. Carlos told Javiera that I would not fuck her because I was only a wanker. He then told me to lick his penis clean, too. I knelt before him and obeyed his demand. I masturbated and came. Javiera giggled uncontrolably. Javiera got dressed again and was set to leave. Carlos gave her some money. She parted, giving Carlos a kiss and a hug for me. She was still laughing about the encounter as she went through the door. Carlos asked me to get naked because now it was my turn. I was a bit surprised that he would be able to do me but happily complied and went to the bedroom. Carlos was very tender again, and this time we also kissed on the mouth. After a while, I managed to get Carlos’ dick stiff again by means of a prolonged blowjob. He put on condom and lube and penetrated me, this time in the missionary position. While he was fucking me, he kept on telling me how great my arsehole feels and how much he prefers that over a woman. Carlos pulled out and told me he had come. He watched me masturbate until I came whilst playing with my balls and caressing my body.

Did you have an orgasm? Did your partner(s)? Carlos and I had several orgasms, I am sure Javiera came, too.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Carlos used condoms when fucking me and Javiera.

What were your REASONS for having this hookup? Well, it was a great opportunity for both Carlos and me. Javiera got paid, but I believe she enjoyed the sex with Carlos.

Were alcohol or drugs involved? If so, how much? There was wine, but it didn’t play any role in the decision making.

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 the sex Carlos invited me to stay at his place over night since it has already gotten late and the streets are dangerous at night time. We had a lot of wine together, chatted and ate. We played some chess. I won, but I think he was a decent player. Since I was still very curious about the relationship between Carlos and Javiera I asked Carlos about this subject. He explained to me that she was indeed a sex worker, but they had been friends for a while now. He claimed that he really liked her work, especially when she was with him. We went to bed together and I gave him a good night blowjob until he came into my mouth. We had anal sex again in the morning. After that I left the house never to see Carlos again.

To whom did you talk about the hookup? How did they react? I have not told the story with anyone, the humiliation was so perfect.

Was this a consensual and/or wanted experience for you? For your partner? yes

Do you regret this hookup? If so, why? No regrets whatsoever. My arse hurt for a couple of days because I got penetrated so often, but that was worth it.

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? Watching a couple fuck and getting humiliated by both of them.

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

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

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