My first time gay sex with a man. How it went wrong, and what I learned from it.

in my early 20s I started to become curious about men. It was mostly a sexual interest. I had been watching a lot of porn and found myself looking at the cocks in the videos more and more. Eventually I decided that I might like to try giving a man a blowjob so I posted an ad on Craigslist stating that I was new to gay sexuality and I was looking for somebody to experiment with. I got a lot of replies from a lot of men so I sifted through them and Picked one. he sent me a face and cock picture and I thought he wasn't a bad looking guy, he said he had kids and was divorced, he also had a handsome penis. so I agreed to meet him at a plaza at about midnight to give him a blowjob in his car. so I got there and he was already waiting, I walked up to his car and waved at him through the window and I heard the door unlock so I opened it and got in. He was polite and he asked me if it was really my first time doing this and I said "yeah I'm just curious" so he said "okay, do you want to see it" so I said "yes" then he asked if I wanted to undo his belt and take it out myself, and I did, so I did. I didn't expect it to be so soft/squishy and warm, even though I have a penis I guess I never really thought about how somebody elses penis would feel. I jerked him for about 30 seconds until he was hard, then he said " do you want to try sucking it now?' so I said "okay" and I leaned over and licked the tip a little before putting it in my mouth. It felt good, sucking the tip was nice, it was soft and warm. I thought the taste and smell of his body was kinda sexy. He put his hand on my head and pushed me down a little, I felt the tip touch the back of my throat and I gagged a little. I took him out of my mouth and realized that I only had about half of him in my mouth. He asked "u okay? too much for you?" and I said " I donno, its okay" then he said "I want you to try to make me cum" so I put him back in my mouth and started sucking him like the way I saw people do it in the porn I watched. After a few minutes his breathing became heavy and he started to squirm a little so I knew I was doing good, then he said " are you ready for some cum?" and I was like "mhmm" then a few seconds later I felt his penis get bigger in my mouth then he said " I'm cumming!" and I felt his cum shoot into my mouth. it was like 3 contractions and he filled my mouth. That made me feel so fucking sexy and hot like my body temp was going up. I swallowed his cum and I just kept sucking. I ended up making him cum 2 more times until he said he couldn't take anymore so I stopped. he asked if I wanted to meet again and I said "maybe". I got out of his car and he pulled away and that was my First gay experience. I went home and jerked off and for the rest of the night I could still taste him in my mouth and almost feel the tip of his cock on the roof of my mouth, I knew I wanted to do it again. For some reason he didn't respond to my emails after that. I was disappointed so I started looking for another guy.

This is the part where I fucked up.

I made a new ad stating that I wanted to have sex with a man for the first time and more specifically I wanted to be fucked by a man and treated like a girl. I got a lot more replies so I sifted through and Picked one. the guy that caught my attention had a slightly larger cock than the one I had sucked a few weeks prior but I thought it would be okay, he called me baby girl and said he wanted to pop my cherry and that kinda turned me on so we made an arrangement to do it at his apartment. I went through the trouble of going to the drugstore and buying a enema bulb, lube and condoms. I did like 3 rounds of "flushing" prior to meeting him. when I got into his car he called me slut and pulled his cock out and told me to "warm him up" while we drove to his place, so I did, he kept pushing me down on his cock and gagging me but I was okay with it at this point. then when we got into his apartment he had his hands all over me. he reached down my pants and grabbed my cock and said it was small and called it a "bitch clit" he then grabbed me by the arm and pulled me into his bedroom and started pulling my clothes off. This was the point where I started to feel nervous, it was going way faster than I thought it would. so next thing I knew I was naked and on my knees sucking him, he was being rough and gagging me and pulling his cock out and wiping my saliva on my face. then he told me to get up on to the bed and he took his pants off and took his belt out and turned me around and put my hands behind my back, put his belt around my wrists and tightened his belt until it hurt and tied it so tight I couldn't pull my hands out. At this point I started to feel really vulnerable and I started to shake. then he picked up the lube that I had put on the bed and he squeezed some out onto my ass and then shoved a finger in. I asked him to go slow and he didn't say anything. then after a few seconds of fingering my ass he pushed me forward so I was face down on the bed and pulled me to the edge. then I felt his cock push up against my ass. the tip felt warm and soft but also really big. he then did a hard thrust and I felt a jolt of pain in my ass and I said " ow fuck, Go slow it really fuckin hurts" to which he replied " you said you wanted to be treated like a girl" he then thrust again and I felt the tip slip in, it hurt so fucking bad I tried to get up but he held me down and forced the rest of his cock in my ass and then just started pounding me I started freaking out and shouting until he said if I didn't shut up he was going to choke me out. I was scared for my life, and I felt like If I didn't shut up I was going to end up unconscious and then I wouldn't be able to do anything to help myself. so I ended up having to wait it out, hyperventilating and sobbing. He fucked me for about 15 minutes before he eventually came in my ass and pulled his cock out. he then tried to roll me over and put his cock in my mouth but I bit him and started screaming "TAKE THE BELT OFF!" repetitively until he did. as soon as I was free I got up and tried to hit him but he grabbed me and pushed me into his dresser and the corner of it hit my ribs and kinda knocked the wind out of me, he backed up a little and I grabbed some of my clothes that were closest to me and ran out of the apartment, down the stairs and out into the parking lot. when I got out of the building I put my shirt and briefs on the started running down the street and then into a park, I made to to the jungle gym and looked around to see if he was following me but he wasn't so I just stood there for a while crying and screaming at my self. I spent most of the night there crying and thinking about all the things I did wrong that resulted in myself being raped, then I remembered that he didn't touch the box of condoms that I brought so then I knew that he had cum inside me and I was then panicking about the possibility of getting a std. I got home at around 4:30am and went in the shower and tried to wash my extremely sore ass out. I wasn't able to sleep until like midnight the next night. I had considered going to the police but I was scared to because I didn't want my family to know that I was having sex with men so I just tried to go on with my life, I looked up stds on google and read something that said to wait a couple months to get tested because It could result in a false positive or false negative if done to early so I waited a about a month and a half and went to a walk in clinic and got a blood test done, not mentioning that I was raped. my test came back a few days later and it said I was negative on all tests, I got tested again a month later even though the doctor said it wasn't necessary and it again came back negative.

after several years I did eventually meet another guy but that time I told him nothing was going to happen unless we met some place public and I got to know him a little. He turned out to be a really nice guy. we ended up getting together frequently, the sex was amazing. It was everything I had originally expected it to be. we were in a Friends with benefits type relationship for a while before we decided to adopt the label "boyfriends", I came out as BI to my sister, my mom and my best friend and they were all supportive and positive about it. Its been about 6 years since that God awful night. The only people who know what happened to me that night are myself, my boyfriend and that piece of shit psycho.

here are the things that I learned from all of these experiences.

1. Don't meet random strangers on the internet for sex.
2. If you do, don't go to a place you aren't familiar with.
3. Do not put your self in a situation where you can become trapped.
4. If something like this happens to you Call the police.

5. Talk about it with somebody you trust.

   These points I make may already seem like common sense but sometimes I find "common sense" is not so common.

If you found my story some kind of entertaining then your welcome, Feel free to comment ask questions or share your own experiences.

James.

Submitted September 05, 2021 at 12:37AM

in my early 20s I started to become curious about men. It was mostly a sexual interest. I had been watching a lot of porn and found myself looking at the cocks in the videos more and more. Eventually I decided that I might like to try giving a man a blowjob so I posted an ad on Craigslist stating that I was new to gay sexuality and I was looking for somebody to experiment with. I got a lot of replies from a lot of men so I sifted through them and Picked one. he sent me a face and cock picture and I thought he wasn't a bad looking guy, he said he had kids and was divorced, he also had a handsome penis. so I agreed to meet him at a plaza at about midnight to give him a blowjob in his car. so I got there and he was already waiting, I walked up to his car and waved at him through the window and I heard the door unlock so I opened it and got in. He was polite and he asked me if it was really my first time doing this and I said "yeah I'm just curious" so he said "okay, do you want to see it" so I said "yes" then he asked if I wanted to undo his belt and take it out myself, and I did, so I did. I didn't expect it to be so soft/squishy and warm, even though I have a penis I guess I never really thought about how somebody elses penis would feel. I jerked him for about 30 seconds until he was hard, then he said " do you want to try sucking it now?' so I said "okay" and I leaned over and licked the tip a little before putting it in my mouth. It felt good, sucking the tip was nice, it was soft and warm. I thought the taste and smell of his body was kinda sexy. He put his hand on my head and pushed me down a little, I felt the tip touch the back of my throat and I gagged a little. I took him out of my mouth and realized that I only had about half of him in my mouth. He asked "u okay? too much for you?" and I said " I donno, its okay" then he said "I want you to try to make me cum" so I put him back in my mouth and started sucking him like the way I saw people do it in the porn I watched. After a few minutes his breathing became heavy and he started to squirm a little so I knew I was doing good, then he said " are you ready for some cum?" and I was like "mhmm" then a few seconds later I felt his penis get bigger in my mouth then he said " I'm cumming!" and I felt his cum shoot into my mouth. it was like 3 contractions and he filled my mouth. That made me feel so fucking sexy and hot like my body temp was going up. I swallowed his cum and I just kept sucking. I ended up making him cum 2 more times until he said he couldn't take anymore so I stopped. he asked if I wanted to meet again and I said "maybe". I got out of his car and he pulled away and that was my First gay experience. I went home and jerked off and for the rest of the night I could still taste him in my mouth and almost feel the tip of his cock on the roof of my mouth, I knew I wanted to do it again. For some reason he didn't respond to my emails after that. I was disappointed so I started looking for another guy.This is the part where I fucked up.I made a new ad stating that I wanted to have sex with a man for the first time and more specifically I wanted to be fucked by a man and treated like a girl. I got a lot more replies so I sifted through and Picked one. the guy that caught my attention had a slightly larger cock than the one I had sucked a few weeks prior but I thought it would be okay, he called me baby girl and said he wanted to pop my cherry and that kinda turned me on so we made an arrangement to do it at his apartment. I went through the trouble of going to the drugstore and buying a enema bulb, lube and condoms. I did like 3 rounds of "flushing" prior to meeting him. when I got into his car he called me slut and pulled his cock out and told me to "warm him up" while we drove to his place, so I did, he kept pushing me down on his cock and gagging me but I was okay with it at this point. then when we got into his apartment he had his hands all over me. he reached down my pants and grabbed my cock and said it was small and called it a "bitch clit" he then grabbed me by the arm and pulled me into his bedroom and started pulling my clothes off. This was the point where I started to feel nervous, it was going way faster than I thought it would. so next thing I knew I was naked and on my knees sucking him, he was being rough and gagging me and pulling his cock out and wiping my saliva on my face. then he told me to get up on to the bed and he took his pants off and took his belt out and turned me around and put my hands behind my back, put his belt around my wrists and tightened his belt until it hurt and tied it so tight I couldn't pull my hands out. At this point I started to feel really vulnerable and I started to shake. then he picked up the lube that I had put on the bed and he squeezed some out onto my ass and then shoved a finger in. I asked him to go slow and he didn't say anything. then after a few seconds of fingering my ass he pushed me forward so I was face down on the bed and pulled me to the edge. then I felt his cock push up against my ass. the tip felt warm and soft but also really big. he then did a hard thrust and I felt a jolt of pain in my ass and I said " ow fuck, Go slow it really fuckin hurts" to which he replied " you said you wanted to be treated like a girl" he then thrust again and I felt the tip slip in, it hurt so fucking bad I tried to get up but he held me down and forced the rest of his cock in my ass and then just started pounding me I started freaking out and shouting until he said if I didn't shut up he was going to choke me out. I was scared for my life, and I felt like If I didn't shut up I was going to end up unconscious and then I wouldn't be able to do anything to help myself. so I ended up having to wait it out, hyperventilating and sobbing. He fucked me for about 15 minutes before he eventually came in my ass and pulled his cock out. he then tried to roll me over and put his cock in my mouth but I bit him and started screaming "TAKE THE BELT OFF!" repetitively until he did. as soon as I was free I got up and tried to hit him but he grabbed me and pushed me into his dresser and the corner of it hit my ribs and kinda knocked the wind out of me, he backed up a little and I grabbed some of my clothes that were closest to me and ran out of the apartment, down the stairs and out into the parking lot. when I got out of the building I put my shirt and briefs on the started running down the street and then into a park, I made to to the jungle gym and looked around to see if he was following me but he wasn't so I just stood there for a while crying and screaming at my self. I spent most of the night there crying and thinking about all the things I did wrong that resulted in myself being raped, then I remembered that he didn't touch the box of condoms that I brought so then I knew that he had cum inside me and I was then panicking about the possibility of getting a std. I got home at around 4:30am and went in the shower and tried to wash my extremely sore ass out. I wasn't able to sleep until like midnight the next night. I had considered going to the police but I was scared to because I didn't want my family to know that I was having sex with men so I just tried to go on with my life, I looked up stds on google and read something that said to wait a couple months to get tested because It could result in a false positive or false negative if done to early so I waited a about a month and a half and went to a walk in clinic and got a blood test done, not mentioning that I was raped. my test came back a few days later and it said I was negative on all tests, I got tested again a month later even though the doctor said it wasn't necessary and it again came back negative.after several years I did eventually meet another guy but that time I told him nothing was going to happen unless we met some place public and I got to know him a little. He turned out to be a really nice guy. we ended up getting together frequently, the sex was amazing. It was everything I had originally expected it to be. we were in a Friends with benefits type relationship for a while before we decided to adopt the label "boyfriends", I came out as BI to my sister, my mom and my best friend and they were all supportive and positive about it. Its been about 6 years since that God awful night. The only people who know what happened to me that night are myself, my boyfriend and that piece of shit psycho.here are the things that I learned from all of these experiences.Don't meet random strangers on the internet for sex.If you do, don't go to a place you aren't familiar with.Do not put your self in a situation where you can become trapped.If something like this happens to you Call the police.Talk about it with somebody you trust.These points I make may already seem like common sense but sometimes I find "common sense" is not so common.If you found my story some kind of entertaining then your welcome, Feel free to comment ask questions or share your own experiences.James.