u/Strict-Gazelle2783

At the time of this story, I was 18 years old, 1.65m tall, and weighed 60 kg. My hair is dark brown, and I have a naturally hairless chest. I'm quite shy and always looked young for my age, which meant I never had much luck with girls as a teenager. While watching porn for hours as a frustrated teen, I stumbled across bi-porn, which eventually led me to "real" gay porn.

When I moved from my hometown to a larger city for school and still didn't have much luck with girls, the thought of trying it with a man wouldn't leave me alone. I even created an account on a gay dating site a couple of times, but I always thought, "I'm not gay, I can't have my first time with a man." After a short time, I always deleted my account.

A few weeks after my 18th birthday, frustrated that I was still a virgin, I signed up again on that gay dating site with a profile titled something like, "Inexperienced but curious guy looking to have his first experience with a man." I received a lot of messages, but most were along the lines of "Hey, wanna have sex?" or something similar, and they got impatient pretty quickly if I didn't want to meet up right away.

One man, however, was different from most of the others. At first, I was skeptical because of his age (he was 45), but he didn't pressure me to meet him immediately or send him nudes after just two messages. He wasn't from my city and was staying in a hotel here the following weekend. Naturally, he invited me to visit him there fairly soon after. I was very unsure about meeting anyone because I didn't want anyone to find out about me. The deciding factor for me was the fact that he was from a different city and so much older than me. This meant that the likelihood of our social circles overlapping was low. So, a once-in-a-lifetime opportunity for me.

My lust became too much, and I agreed to meet him at his hotel. I figured if I tried it, maybe the craving would finally subside. We agreed that I only wanted to "experiment a little," maybe give him a blowjob. He told me he was a total top and wasn't interested in my penis at all. That was fine with me, since I mainly wanted to touch and play with another man's penis.

On the day of the meeting, I almost got cold feet, but I had made sure not to masturbate the day before, which made me incredibly horny, and I told myself, "Now or never." I was to come to the hotel lobby, and he would get me. On the way there and during the few minutes I had to wait, I felt like everyone knew where I was going and what I was planning. When he stepped out of the elevator, I was relieved to see he looked even better than in his pictures: light gray hair and pretty much a prototypical dad bod. I was grateful he kept the greeting brief, leading me straight into the elevator and to his room. He sensed my nervousness, and we chatted for a while on the sofa. At one point, I mentioned that I was gay, but not gay, to which he just grinned. Talking about sex in real life felt strange because I was used to only typing that stuff in chat rooms.

Finally, he stood up and told me to do what I'd come for. I had to open his pants and take out his already hard cock. The feeling of another man's cock was very strange, completely different from my own. At 17 cm, his cock was also considerably larger than my 12 cm. I played with it for a while when he said he thought I knew what to do when you're kneeling in front of a man like that. Of course, he was right, and I thought, okay, there's no going back now, I'm going to be a real cock sucker.

I slowly started licking his penis and taking it in my mouth, trying to imitate everything I'd seen in porn. He was very encouraging and told me how best to please him. It was also very important to him that I wasn't allowed to touch myself. As I got more and more into it, he pulled me away and said I was doing a great job and asked if I was enjoying it. He knew, of course, that I was, and said it would feel even better if I were naked. He'd also been waiting to really see my body.

This was the first time anyone other than my mother had ever actually seen me naked. At first, I kept my underwear on, but he just laughed and told me to take everything off. I was embarrassed because I was already hard, which was, of course, the first thing he commented on. He said that for a straight boy, I was getting pretty turned on, sucking a man's penis. I had to turn around and show him my body, which he said was a dream for men like him.

Then I had to get back on my knees and keep sucking him. He was right that giving a blowjob naked felt better. Being so exposed made me feel like a sexy little slut.

He stopped me again and said he'd come soon if I kept going like that. He wanted to take care of me too, and I was supposed to sit on the bed. I found it strange that he wanted to give me a blowjob because he'd insisted he wasn't interested in penises, but I went along with it. It turned out he didn't want to give me a blowjob at all, and he lifted my feet and started licking my hole. At first, I wanted to protest, but it felt surprisingly good, and I let him continue. Maybe that was an understatement; it was the hottest feeling I'd ever had, and I wanted him to keep going. I felt like I was giving him access to my most intimate parts, like a little slut.

Then he suddenly stopped and apologized, saying he remembered I didn't want to do anything more than give him a blowjob. I said it was okay, that I loved the feeling, and that he shouldn't stop. He insisted we stick to what we had agreed on, which almost made me beg him to continue. He said if I was open-minded, we could go further, but that would mean I had to trust him, and he would show me what real male sex was like, but only if I was sure I wanted it.

At that point, I was so turned on by sucking his cock and feeling like a slut that I figured I might as well try a little more. When would I get another chance like this? He then explained what he meant by "male sex," which was, of course, anal, and that a submissive should prepare by douching, etc. He had even prepared things for it in the bathroom.

I'll skip the details, but when I came out of the bathroom, he had also undressed and told me to get back on my knees. We had both gone somewhat limp in the meantime, but that quickly changed as his cock grew in my mouth, which also turned me on immensely. After a few minutes, he had me lie on the edge of the bed and started licking me again. When I heard the lube tube open, I knew what was coming next. He gently massaged my hole with his tongue and added a finger. First, he circled my hole, then he slid his finger right over it and finally pressed it down, applying gentle pressure. I had expected it to hurt, but surprisingly, it only felt a little strange, not really painful. He fingered me like that for a while and added another finger. After three fingers and a lot of licking, he said I was ready. If I wanted to stop, this was my last chance.

My arousal had only intensified with the foreplay, and I was now more turned on than I'd ever been in my life. I simply said, "Please continue." He smiled, and I had to put the condom on him and lube his penis. It felt strangely submissive; I had to prepare the penis that was about to take my virginity.

I got on all fours on the bed, like I'd seen women do in porn, and arched my back as much as I could. Then he said that when he took my virginity and entered me for the first time, he wanted to see my face. He had me lie on my back with my legs spread, oh boy I was rock hard and then he kissed me and went in. It hurt but I got used to it and I started moaning rolling my eyes back. He fucked me for a while and then he cam inside me leaking cum as his penis was leaving my hole. I ended up sleeping over at the hotel with him and left in the morning but really I enjoyed that night and I will never forget it!

At the time of this story, I was 18 years old, 1.65m tall, and weighed 60 kg. My hair is dark brown, and I have a naturally hairless chest. I'm quite shy and always looked young for my age, which meant I never had much luck with girls as a teenager. While watching porn for hours as a frustrated teen, I stumbled across bi-porn, which eventually led me to "real" gay porn.

When I moved from my hometown to a larger city for school and still didn't have much luck with girls, the thought of trying it with a man wouldn't leave me alone. I even created an account on a gay dating site a couple of times, but I always thought, "I'm not gay, I can't have my first time with a man." After a short time, I always deleted my account.

A few weeks after my 18th birthday, frustrated that I was still a virgin, I signed up again on that gay dating site with a profile titled something like, "Inexperienced but curious guy looking to have his first experience with a man." I received a lot of messages, but most were along the lines of "Hey, wanna have sex?" or something similar, and they got impatient pretty quickly if I didn't want to meet up right away.

One man, however, was different from most of the others. At first, I was skeptical because of his age (he was 45), but he didn't pressure me to meet him immediately or send him nudes after just two messages. He wasn't from my city and was staying in a hotel here the following weekend. Naturally, he invited me to visit him there fairly soon after. I was very unsure about meeting anyone because I didn't want anyone to find out about me. The deciding factor for me was the fact that he was from a different city and so much older than me. This meant that the likelihood of our social circles overlapping was low. So, a once-in-a-lifetime opportunity for me.

My lust became too much, and I agreed to meet him at his hotel. I figured if I tried it, maybe the craving would finally subside. We agreed that I only wanted to "experiment a little," maybe give him a blowjob. He told me he was a total top and wasn't interested in my penis at all. That was fine with me, since I mainly wanted to touch and play with another man's penis.

On the day of the meeting, I almost got cold feet, but I had made sure not to masturbate the day before, which made me incredibly horny, and I told myself, "Now or never." I was to come to the hotel lobby, and he would get me. On the way there and during the few minutes I had to wait, I felt like everyone knew where I was going and what I was planning. When he stepped out of the elevator, I was relieved to see he looked even better than in his pictures: light gray hair and pretty much a prototypical dad bod. I was grateful he kept the greeting brief, leading me straight into the elevator and to his room. He sensed my nervousness, and we chatted for a while on the sofa. At one point, I mentioned that I was gay, but not gay, to which he just grinned. Talking about sex in real life felt strange because I was used to only typing that stuff in chat rooms.

Finally, he stood up and told me to do what I'd come for. I had to open his pants and take out his already hard cock. The feeling of another man's cock was very strange, completely different from my own. At 17 cm, his cock was also considerably larger than my 12 cm. I played with it for a while when he said he thought I knew what to do when you're kneeling in front of a man like that. Of course, he was right, and I thought, okay, there's no going back now, I'm going to be a real cock sucker.

I slowly started licking his penis and taking it in my mouth, trying to imitate everything I'd seen in porn. He was very encouraging and told me how best to please him. It was also very important to him that I wasn't allowed to touch myself. As I got more and more into it, he pulled me away and said I was doing a great job and asked if I was enjoying it. He knew, of course, that I was, and said it would feel even better if I were naked. He'd also been waiting to really see my body.

This was the first time anyone other than my mother had ever actually seen me naked. At first, I kept my underwear on, but he just laughed and told me to take everything off. I was embarrassed because I was already hard, which was, of course, the first thing he commented on. He said that for a straight boy, I was getting pretty turned on, sucking a man's penis. I had to turn around and show him my body, which he said was a dream for men like him.

Then I had to get back on my knees and keep sucking him. He was right that giving a blowjob naked felt better. Being so exposed made me feel like a sexy little slut.

He stopped me again and said he'd come soon if I kept going like that. He wanted to take care of me too, and I was supposed to sit on the bed. I found it strange that he wanted to give me a blowjob because he'd insisted he wasn't interested in penises, but I went along with it. It turned out he didn't want to give me a blowjob at all, and he lifted my feet and started licking my hole. At first, I wanted to protest, but it felt surprisingly good, and I let him continue. Maybe that was an understatement; it was the hottest feeling I'd ever had, and I wanted him to keep going. I felt like I was giving him access to my most intimate parts, like a little slut.

Then he suddenly stopped and apologized, saying he remembered I didn't want to do anything more than give him a blowjob. I said it was okay, that I loved the feeling, and that he shouldn't stop. He insisted we stick to what we had agreed on, which almost made me beg him to continue. He said if I was open-minded, we could go further, but that would mean I had to trust him, and he would show me what real male sex was like, but only if I was sure I wanted it.

At that point, I was so turned on by sucking his cock and feeling like a slut that I figured I might as well try a little more. When would I get another chance like this? He then explained what he meant by "male sex," which was, of course, anal, and that a submissive should prepare by douching, etc. He had even prepared things for it in the bathroom.

I'll skip the details, but when I came out of the bathroom, he had also undressed and told me to get back on my knees. We had both gone somewhat limp in the meantime, but that quickly changed as his cock grew in my mouth, which also turned me on immensely. After a few minutes, he had me lie on the edge of the bed and started licking me again. When I heard the lube tube open, I knew what was coming next. He gently massaged my hole with his tongue and added a finger. First, he circled my hole, then he slid his finger right over it and finally pressed it down, applying gentle pressure. I had expected it to hurt, but surprisingly, it only felt a little strange, not really painful. He fingered me like that for a while and added another finger. After three fingers and a lot of licking, he said I was ready. If I wanted to stop, this was my last chance.

My arousal had only intensified with the foreplay, and I was now more turned on than I'd ever been in my life. I simply said, "Please continue." He smiled, and I had to put the condom on him and lube his penis. It felt strangely submissive; I had to prepare the penis that was about to take my virginity.

I got on all fours on the bed, like I'd seen women do in porn, and arched my back as much as I could. Then he said that when he took my virginity and entered me for the first time, he wanted to see my face. He had me lie on my back with my legs spread, oh boy I was rock hard and then he kissed me and went in. It hurt but I got used to it and I started moaning rolling my eyes back. He fucked me for a while and then he cam inside me leaking cum as his penis was leaving my hole. I ended up sleeping over at the hotel with him and left in the morning but really I enjoyed that night and I will never forget it!

When I was younger my sisters friends always told me I had a butt like a girls. I do have a bubble but and when I was younger I would check out my butt and play with my cheeks. I stayed the night a friends house one night and he had an older sister that was donating some clothes and asked if she thought my sister would like them. I took the clothes and found some thongs and booty shorts in the pile and kept them and hid them. I tried on the thongs and other things alone in my room. I was curious about taking something in my butt but didn’t wanna use a random object, I actually had a physical and the DR had a big finger and lube put a glove and shoved his finger put my butt and moved it around a bit. I have a big butt so when he put his hand in I watch as my butt cheeks but pushed to the side and I was so turned on. I went home later that night and found a smooth handle plastic spoon and used to to play with my ass for a good hour that night I was so turned on. I used random objects to play with for about a year till I turned 18. On my 18th birthday I went and picked up a 6in dildo and locked myself in my room and road that dildo fast and slow all night for hours till my ass creamed. I was super turned on and knew I had to eventually try the real deal. I made a Grindr account 1 week after turned 18 and looked around and found a 50 year old white guy with a nice cut cock. I was scared to meet up but was so horny I had too. I took a nice shower played with my dildo a bit to get ready I oiled up my butt and leg after a fresh shave in the shower. I put on my thing and booty shorts and some sweatpants over it so my family didn’t see. I told them I was going to hang out with friends then drove to the guys house. When I got down the street I pulled over got out and took off the sweatpants. I remember feeling the cold breeze come across my legs and the feeling of the thing pressed between my cheeks. A neighbor came outside as I was taking them off and actually his eyes glued to my ass and a smile and he said hi. I quickly got back in my car and drove to the guys house and walked up to his door ass out in my small shorts. He open the door with his nice 7.5in dick I’m hand. He took my over to his couch and sat down and put me in his knees I was just 18 and he was 50 he was trying to show me how to suck dick good for about 10 mins. He then stood me up and started kissing my ass cheeks and thighs and bent me over and started to eat my ass. It felt so good and I was trying to run away from it lol. Then he bent me over and arched my back. He slowly shoved his nice cock in my ass and it hurt at first. He then started going deeper and faster. I was looking back ass my big nice bubble but was getting pounded by a older man when I was freshly 18. Then room was dark with just one dim light on and all I can do was look back and watch my ass clap ass he tells me how good I feel. My legs started to shake and I couldn’t help me let out load moans and say fuck. My thighs were getting weak and it felt so good and wet. I got bent over and fucked hard for about 30 mins legs shaking and all. Dude busted a nut deep in my ass and then put my shorts back on me as I layed there shaking. He was telling me how cute I was and how nice my ass was and that I need to be careful if I meet with older guys as they might hurt me. I then drove home shaking as his cum was dripping out my ass and down my cheeks. I went home and played with his cum in my ass and jerked off till I cam. I met up with him one more time after.

When I was younger my sisters friends always told me I had a butt like a girls. I do have a bubble but and when I was younger I would check out my butt and play with my cheeks. I stayed the night a friends house one night and he had an older sister that was donating some clothes and asked if she thought my sister would like them. I took the clothes and found some thongs and booty shorts in the pile and kept them and hid them. I tried on the thongs and other things alone in my room. I was curious about taking something in my butt but didn’t wanna use a random object, I actually had a physical and the DR had a big finger and lube put a glove and shoved his finger put my butt and moved it around a bit. I have a big butt so when he put his hand in I watch as my butt cheeks but pushed to the side and I was so turned on. I went home later that night and found a smooth handle plastic spoon and used to to play with my ass for a good hour that night I was so turned on. I used random objects to play with for about a year till I turned 18. On my 18th birthday I went and picked up a 6in dildo and locked myself in my room and road that dildo fast and slow all night for hours till my ass creamed. I was super turned on and knew I had to eventually try the real deal. I made a Grindr account 1 week after turned 18 and looked around and found a 50 year old white guy with a nice cut cock. I was scared to meet up but was so horny I had too. I took a nice shower played with my dildo a bit to get ready I oiled up my butt and leg after a fresh shave in the shower. I put on my thing and booty shorts and some sweatpants over it so my family didn’t see. I told them I was going to hang out with friends then drove to the guys house. When I got down the street I pulled over got out and took off the sweatpants. I remember feeling the cold breeze come across my legs and the feeling of the thing pressed between my cheeks. A neighbor came outside as I was taking them off and actually his eyes glued to my ass and a smile and he said hi. I quickly got back in my car and drove to the guys house and walked up to his door ass out in my small shorts. He open the door with his nice 7.5in dick I’m hand. He took my over to his couch and sat down and put me in his knees I was just 18 and he was 50 he was trying to show me how to suck dick good for about 10 mins. He then stood me up and started kissing my ass cheeks and thighs and bent me over and started to eat my ass. It felt so good and I was trying to run away from it lol. Then he bent me over and arched my back. He slowly shoved his nice cock in my ass and it hurt at first. He then started going deeper and faster. I was looking back ass my big nice bubble but was getting pounded by a older man when I was freshly 18. Then room was dark with just one dim light on and all I can do was look back and watch my ass clap ass he tells me how good I feel. My legs started to shake and I couldn’t help me let out load moans and say fuck. My thighs were getting weak and it felt so good and wet. I got bent over and fucked hard for about 30 mins legs shaking and all. Dude busted a nut deep in my ass and then put my shorts back on me as I layed there shaking. He was telling me how cute I was and how nice my ass was and that I need to be careful if I meet with older guys as they might hurt me. I then drove home shaking as his cum was dripping out my ass and down my cheeks. I went home and played with his cum in my ass and jerked off till I cam. I met up with him one more time after.