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What’s your gender? Man
How old are you? 26
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Atlanta
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Realaror
What’s your current relationship status? Single
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Bisexual
How many sexual partners have you had in your life (including oral sex)? 35
How many hookup stories have you here posted before? 0

First Gay Cum

How long ago did this hookup happen? 9 years ago

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? I had been curious about guys since I was 13. I knew l liked girls, but I often found myself watching gay open and fantasizing about being with a guy. I really found older guys exciting while jacking off, but that desire would go away after I would cum. I spent a lot of time on the internet googling whatever I could find about gay sex with and older man. When I was 15 I found some m4m chat rooms and began chatting with guys about sex. A lot of guys sent me their picture and I often blew my load looking and then and thinking about being with them, but was always too scared to do anything more. One day I started chatting with a guy who was in his 40s and lived close to me. He told me he was married, but and liked younger guys. He sent me some pictures and he was incredibly good looking. He was pretty muscular and had a huge dick. I blew my load fantasizing about being with him then stopped chatting. A few days later I got back on and he had sent me more pictures of himself. We started chatting again and he asked me to call him. I had never talked to a guy on the phone before, but was so horny I decided to call him. He had a deep manly voice and seemed incredibly nice on the phone. We talked for a little about sex and I grew hornier than i had ever been. We talked for about 15 minutes and he asked if I wanted to meet him the next day after school. I was so horny at the time I agreed to meet him. I immediately blew my load after we hung up.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The next day after school, I walked to the spark by his house where we agreed to meet. I was having some second thoughts, but figured, I would just get there early and leave if I didn’t feel like meeting. He called me shortly after I showed up and told me he was on his way. I decided to stay and he pulled up in a nice Mercedes a few minutes later. I walked up to his car and got in. He shook my hand and introduced himself. He looked exactly like he did in the pictures he sent me, except he was wearing some gym shorts and a t-shirt now. We pulled away and made small talk. I was incredibly nervous and began to think I had made a mistake. We pulled up to a red light and he reached over and put his hand on my leg. I was frozen and didn’t know what to do. He slid his hand up my thing to my crotch, then gave it a little squeeze. He continued to run his hand up my stomach and chest, then around to my shoulder and massaged my shoulder until the light turned green. He told me to relax and assured me that we wouldn’t do anything I didn’t want to do. He asked of I was nervous and I told him I was. We pulled up to his house and pulled in the garage. He shut the garage door behind us and asked if I just wanted to sit in the car and talk for awhile before going in. I told him that would be nice. He reached over and massaged my shoulder and started asking me questions. He was so kind and reassuring that I began to relax. His questions grew more sexual and began asking me about what sexual thing I had done before. He told me about his sex life too with his wife and about his first time with another guy. As he was telling his story, I was really relaxed now and he slid his hand slowly back down my chest and stomach and to my crotch. He began to Slowly squeeze my soft dock and balls. It felt really good and I started to get hard. As I grew harder he rubbed my shaft over my pants. I was now completely relaxed and totally comfortable with my decision to come to his house.

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? He leaned over and gently kissed my lips then slowly stuck his tongue in my mouth. I kissed back and it was a completely different feeling having a grown man’s tongue in my mouth instead of a teenage girls like I was used to. We kissed for a couple minutes then he pulled back and asked if I was ready to come inside. I looked down and saw his huge bulge in his gym shorts and smiled and told him I was ready. He led me upstairs to his bedroom. It was a little strange seeing pictures of him and his wife in his house knowing I just had his tongue in my mouth and I was going to do more with him. Once in his bedroom he pulled me into him and we kissed again. I could feel his hard dock pressing against me as we kissed. He pulled my shirt off over my head and caressed my chest and squeezed my nipples. He then leaned over and licked my chest and nipples.

I had the chills but it felt amazing. He undid the button on my pants and pulled them down to my ankles. I stepped out of them the he reached down the front of underwear waist band and grabbed my cock. I was as hard as if ever been. He slowly stroked me and we began to kiss again. He then pushed me back on the bed and pulled his shirt off. He was in great shape for being in his mid 40s. I could see his dock was now sticking straight out in his gym shorts. He slid off his shorts and underwear at the same time and his cock sprung forward. It was definitely bigger than mine and had a big upward curve to it that I didn’t see in his pictures. He reached out and pulled my underwear off and my rock hard cock sprang out too.he crawled on top of me and we began kissing again. His cock was grinding against mine and he was slowly thrusting himself into me. As we kissed longer his trusts grew stronger and was really grinding himself into me.

He then whispered and asked if I wanted to taste him. I just shook my head and he scooted forward and straddles my chest with his knees. He leaned forward and his cock thrust towards my face. I grabbed his dock and guided it into my mouth. He slowly thrust himself where so slightly back and forth in my mouth. I was so horny and it was everything I could imagine having him in my mouth. He was incredibly gentle and was thrusting very slow to ease me into sucking him. I sucked him for a little and his thrust became a little stronger, but still not too much for my throat to handle. He then pulled out and slid back between my legs and started sucking me.

He bobbed very slowly up and down and then began to squeeze my balls as he sucked. He sucked longer and then pressed a finger against my butt hole. I wasn’t expecting it but it felt good. He then stopped and walked into the bathroom and came back with a to my bottle. He squirted some in his hand and reached down and stroked my dick. It was very slippery and felt amazing as he did it. He then squirted some in his other hand and started stroking himself as he stroked me. His cock was rock hard and very shiny. He stroked both our cocks for a little then he stopped stroking himself. He grabbed my balls again as he stroked me and the pressed his finger against my butt hole again. I had watched enough gay porn to know what he was doing to me, but it felt so good I just lay there and let him slip his finger in my ass.

He slowly pushed himself into me and I felt some pain and moaned. He slowly began fucking me with his finger. It hurt and first but the pain stopped and he began moving his finger back and forth in me faster. He slipped another finger in me as I loosened up and it hurt even worse than the first finger. He was very gentle and slow, but it still hurt. He asked me to roll over on my stomach and he began finger fuck me again with 2 fingers. He then crawled on top of me and I could feel his cock rubbing between my ass cheeks. I knew what was coming and asked him to be gentle with me. He pressed his cock head against me and it hurt incredibly bad. I tried to move but his weight was on top of me. He slowly pressed his cock,all the way into me and I thought I was gonna split in half. I asked him to stop but he didn’t say anything and kept slowly pumping back and forth. His thrust became faster and it still hurt, but not as bad. He began to kiss the back of my neck as he fucked me and I began to relax more. His thrust became faster and faster, but didn’t hurt nearly as bad.

I could feel his balls slam against me and I started to enjoy it more and more. I thought about what his wife feels like getting fucked by him and for some reason it turned me on so much knowing he was fucking me, a 16 year old guy, instead of his full blown woman wife. He licked my ear as he pumped his cock back and forth faster and I barely felt any pain. I could feel my cock begin to swell with blood and get hard again. He began to grunt and I could feel his muscle tightening against my back as he thrust. He slowed down and asked me to get doggy style on the edge of the bed. He stood behind me and thrust forward. This time he slid right in and began pumping again faster and faster. The sensations of his balls slapping against me and the thought of him screwing me instead of his wife had me rock hard again. He leaned over on me and reached around as he ducked and began stroking my dick again. It felt Amazing. He then stood back up and started thrusting faster and faster. He grabbed my hips and pulled me back to into him as he thrust. It began to hurt again but he wasn’t sowing down. Just as I was looking my hard on, he let out a big moan and one final thrust into me. I knew he had cum in me. He kept his cock,in me for a little and I could feel it throbbing inside me. He then pulled out and asked me to roll over. He squirted more lube in his hand and began quickly stroking my cock. I only lasted about a minute and then began to shake and cum.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, 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? Immediately after I came, he laid next to me on the bed. He asked how my first experience with a man was. I told him it was amazing. We laid next to each other and talked got about 15 minutes. I told him I was turned on by feeling his balls slap me. I also told him, I thought it was incredibly sexy that he was ducking me at that point in time, instead of his attractive wife.

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, Learning new things, experimenting, 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? Very

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? Didn’t tell anyone until in college.

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

Did you get emotionally hurt as a result of this hookup? A little bit

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

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? It was the beginning of a year and a half of messing around with am older guy.

What was the WORST thing about this hookup? We had to stop when I left for college.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Reassured my no curiousity and my strong desire for older guys.

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? We hooked up pretty regularly for a year and a half. A couple times a week, had pick me up from school and take me to,his house. A couple times I wore his wife’s underwear and he pushed them to the side as he fucked me.

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? More acceptance.

What do you think about the Casual Sex Project? Great idea.

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