First Time Stories

TigerJock

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Does anyone have a really hot first-time with guy stories?

Years ago this guy wrote this book. It is basically a compilation of first-time with guy stories that guys wrote to him. He took his favorite ones and made them into a 5 volume book. There are some really hot stories here.

Here is the first volume. If anyone wants the other 4 volumes I could upload those too.

My First Time by Jack Hart, Volume 1.pdf


"The publisher and I solicited stories by placing notices in gay newspapers around the country, asking gay men to write about their first consensual same-sex experience. Then, I sat back and waited to see what came in.
While waiting, I admit that I had some misgivings. Would a whole book of these stories prove repetitive? But I needn't have worried. As you're about to see, there's an enormous variety here. The earliest accounts are set back in the 1930s; the latest, in 1994. Sometimes the first-timer is seduced; other times he takes the initiative. Most of the stories carry a sense of delight; a few convey pain. Many are sexy, or exciting,
or romantic."

"I left it to contributors to define "first-time." Did casual adolescent sex play with their peers count? As you'll see, men interpreted the phrase differently, but a large number independently arrived at the same criteria: they selected the experience with which they came to think of themselves as gay, or different, or at least when they realized that male sex had an emotional component for them that wasn't felt by other boys who were just messing around."

"I never changed content, even if I or someone else might disagree with it. Several contributors conclude that their first experience might have made them gay. I'm skeptical that sexual orientation is determined this way, but if that's what they believe, they're entitled to say so here. Originally I planned to arrange these stories according to each contributor's age at the time. I later decided it was more revealing to break them up based on the era when each one took place. It was too late at that point to contact everyone who had not included a date in their story."


"As we began soliciting stories, I wondered if a lot of men would make up something fun, rather than describe their actual first experience, which may not have gone as they had hoped. A few accounts did have all the flavor of a porn magazine submission: The coach and the high school football quarterback in the deserted locker room, for example. I omitted these stories. My apologies to the former quarterback if, in fact, this all really took place. In that case, you've had more than your share of good fortune in life, and I trust you won't be too hurt at being left out of this Book."

"For the most part, my sixth sense tells me the accounts I received and have included are all true. There are too many unexpected details and nuances. Take this - from one of my favorite stories, set in the 1930s after a sixteen-year-old boy finishes an encounter with a Bible salesman on the bus:"

"He gave me a vest pocket Testament bound in artificial red leather and told me, 'Have a good life.' I thanked him, but thought it a mite peculiar that a Bible man was the first person, besides myself, to jack me off. I still have the Testament. It's not been used much."

"If that was made up, then somebody missed a promising career as a novelist!"



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BlueBearCub

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My First Time Bottoming:

Back in my college days roughly 2009 was the first time I experienced anal sex as the receptive partner. I was still deep in the closet, so my only gay experiences have been with hookups on the popular gay "dating" apps like Adam4Adam and the personal sections of Craigslist. (Yeah I know really dangerous) I have topped once or twice, but really wanted to try bottoming. I had a previous experience where I tried bottoming for a guy, but could just not relax for the guy and he eventually gave up. Wanting to redeem myself from that moment, I decided my next hookup I would finally lose by bottom cherry.

Fast forward weeks later and I am in my room and of course horny as fuck. I decide to make a post on the personal section of craigslist detailing that I am a virgin looking to bottom for the first time. This type of ad always led to my inbox flooding with messages from lots of guys. Finding someone who actually looked attractive and also sounded normal was the hard part. This was not my first time doing this, but I never gave up hope finding the right person.

As I waited for the ad to become public and the responses to start arriving, I wondered what would I do if I actually found someone worth meeting. I still was very nervous to bottoming, but my horniness was overriding by anxiety and fears.

Once my ad posted and became public I started getting responses within minutes from a wide arrange of men; old, young, skinny, fat, etc. I find myself a very open guy and open to various ages and body types, but something about it being my first time I was looking for someone who I found to be very attractive in my eyes.

I probably talked with about 10-20 guys, but either they would be really sketchy, not share enough pictures to get a good feel of what they looked like, or would just not be my type.

I was starting to lose hope and started contemplating if I should just jerk off and go to bed. It was already getting late around 10-11pm and the chances of getting someone still wanting to meet up this late was getting slim. As I was just about to give up I receive a response to my ad from this guy. He sends me his stats, 6ft 4 210lbs black muscular/athletic build 8in cut. I am stunned by these stats and assume they are exaggerated. I ask him of course to send pics to prove some of this. He quickly sends back pics and I was surprised to see how accurate they were. My first thought was, how is this stud of a man interested in me? No way he could want to actually meet and hookup with me.

We quickly share a few messages back and forth and he seems truly interested and also open to the fact it would be my first time and that we would need to take it slow. Before I even had a chance to think, he sent me his address and said to come over now. I was like oh shit this is actually going to happen and the ball is in my court. Being a 19 year old horny guy I immediately jump in shower and get in the car to start heading to this guys place.

The whole ride to his place, I am shaking with nerves. Was I really about to give up my virginity to this guy I only said maybe 5-10 sentences to? What if I was being catfished or what if something else?

My nerves did not let up and I was almost visibly shaking as I got to his door. With me throwing all fear to the side I message him that I am at his place. Within moments the door opens and I am surprised to look up at exactly the same muscular athletic tall from the pictures. He was wearing basketball shorts and a t-shirt. He quickly greets me and pulls me inside. He tells me his roommate is asleep and that we have to stay in his room and not be to loud.

He pulls me into his dimly lit room and closes the door. I was so nervous I didn't really know what to do. Sensing my nervousness he comes up to me and pulls me toward him and starts to passionately kiss me. I am stunned by the quickness, but that quickly fades because I am so turned on. I was making out with one of the most attractive men I have ever seen. I couldn't believe how lucky I was. We started shedding our clothes and seeing him shirtless just turned me on more. His muscular build was stunning and I could not get enough exploring it with my hands while we made out passionately.

We quickly moved to his bed and nothing could have felt better to have this stud on top of me. Feeling his muscular body on top of mine was amazing and I could not get enough of his arms. As our bodies rubbed together, we both were getting rock hard. I could feel his large dick rubbing against mine and I wanted to see more. Before I could even ask, he straddles my chest and I am face first with his amazingly large rod. Without any hesitation I open my mouth and start to suck his thick cock enjoying every second. Not wanting that to end he quickly pulls his cock out of my mouth and moves down to mine. He immediately takes me in his mouth and I am in heaven. I am so turned on that I cant even comprehend how good everything was feeling.

Before I knew it he is lifting my legs up exposing my hole. Not sure what he is about to do, he goes face first and starts to rim my whole deeply. This was the first time ever having a man eat my whole and I was experiencing a world wind of ecstasy. He had me moaning so much I couldn't handle it. He rimmed me for what felt like forever, but was most likely a few mins.

He pulled his tongue out of me and I knew he was ready for more. This was the moment I was wanting for soo long, but I was still nervous. Would I be able to relax, would he fit, would it hurt? He grabbed a condom and some lube and started to get himself ready to to fuck me. He lubed himself up and then my hole and started to slowly tease my whole with his cock. AS he teased he started to slowly insert into my virgin hole slowly opening me up. He may have been about an inch or so in when I started to get nervous and started to hold his hips back a little. He told me to relax and that he would go slow but I was still nervous and kept my hand on his hip. He started to kiss me and as he kissed me he took my hands and held them above my head. I was still nervous and said please go slow and he kept slowly pushing deeper inside me. I was scared it was going to start hurting especially since he was so large, but all of a sudden i feel his hips touch my ass. He was fully inside me all 8 inches of his thick cock. I was surprised and never felt anything like it before. The feeling of fullness and that tingle feeling of your prostate being hit.

He slowly started to thrust in and out and with each thrust he started to go a little faster and faster. Every thrust I was sent a shock of sheer pleasure throughout my body and I was in absolute Ecstasy. This man was fucking me and I could not get enough. What made it even better was he was fucking me and jerking me off at the same time which is a feeling like no other. Before I knew it I was blowing my load all over us and then he was shooting his load into his condom inside me.

We cleaned up and chatted briefly and then I was walked out. Such an intense first experience I had with such a stud of a man.
 

BlueBearCub

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Here is image of what guy kind of looked like:

sensual-picture-id93274602
 

TigerJock

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My First Time Bottoming:

Back in my college days roughly 2009 was the first time I experienced anal sex as the receptive partner. I was still deep in the closet, so my only gay experiences have been with hookups on the popular gay "dating" apps like Adam4Adam and the personal sections of Craigslist. (Yeah I know really dangerous) I have topped once or twice, but really wanted to try bottoming. I had a previous experience where I tried bottoming for a guy, but could just not relax for the guy and he eventually gave up. Wanting to redeem myself from that moment, I decided my next hookup I would finally lose by bottom cherry.

Fast forward weeks later and I am in my room and of course horny as fuck. I decide to make a post on the personal section of craigslist detailing that I am a virgin looking to bottom for the first time. This type of ad always led to my inbox flooding with messages from lots of guys. Finding someone who actually looked attractive and also sounded normal was the hard part. This was not my first time doing this, but I never gave up hope finding the right person.

As I waited for the ad to become public and the responses to start arriving, I wondered what would I do if I actually found someone worth meeting. I still was very nervous to bottoming, but my horniness was overriding by anxiety and fears.

Once my ad posted and became public I started getting responses within minutes from a wide arrange of men; old, young, skinny, fat, etc. I find myself a very open guy and open to various ages and body types, but something about it being my first time I was looking for someone who I found to be very attractive in my eyes.



We cleaned up and chatted briefly and then I was walked out. Such an intense first experience I had with such a stud of a man.


Sounds hot man. I miss craigslist and a4a, lol. Funny how hooking up with a guy on one of those sites seemed way more efficient than the endless back and forth on the apps that people use today. My first time was with this 6 4' guy from my gym. It seriously felt like I was fucking a blonde Superman, lol.


867CA28E-3217-4B69-898A-756E6F37643D.jpeg
 

BlueBearCub

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Sounds hot man. I miss craigslist and a4a, lol. Funny how hooking up with a guy on one of those sites seemed way more efficient than the endless back and forth on the apps that people use today. My first time was with this 6 4' guy from my gym. It seriously felt like I was fucking a blonde Superman, lol.


View attachment 16927751

yeah it definitely was easier. Great looking guy!!
 

manunlisted

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My First Time Bottoming:

Back in my college days roughly 2009 was the first time I experienced anal sex as the receptive partner. I was still deep in the closet, so my only gay experiences have been with hookups on the popular gay "dating" apps like Adam4Adam and the personal sections of Craigslist. (Yeah I know really dangerous) I have topped once or twice, but really wanted to try bottoming. I had a previous experience where I tried bottoming for a guy, but could just not relax for the guy and he eventually gave up. Wanting to redeem myself from that moment, I decided my next hookup I would finally lose by bottom cherry.

Fast forward weeks later and I am in my room and of course horny as fuck. I decide to make a post on the personal section of craigslist detailing that I am a virgin looking to bottom for the first time. This type of ad always led to my inbox flooding with messages from lots of guys. Finding someone who actually looked attractive and also sounded normal was the hard part. This was not my first time doing this, but I never gave up hope finding the right person.

As I waited for the ad to become public and the responses to start arriving, I wondered what would I do if I actually found someone worth meeting. I still was very nervous to bottoming, but my horniness was overriding by anxiety and fears.

Once my ad posted and became public I started getting responses within minutes from a wide arrange of men; old, young, skinny, fat, etc. I find myself a very open guy and open to various ages and body types, but something about it being my first time I was looking for someone who I found to be very attractive in my eyes.

I probably talked with about 10-20 guys, but either they would be really sketchy, not share enough pictures to get a good feel of what they looked like, or would just not be my type.

I was starting to lose hope and started contemplating if I should just jerk off and go to bed. It was already getting late around 10-11pm and the chances of getting someone still wanting to meet up this late was getting slim. As I was just about to give up I receive a response to my ad from this guy. He sends me his stats, 6ft 4 210lbs black muscular/athletic build 8in cut. I am stunned by these stats and assume they are exaggerated. I ask him of course to send pics to prove some of this. He quickly sends back pics and I was surprised to see how accurate they were. My first thought was, how is this stud of a man interested in me? No way he could want to actually meet and hookup with me.

We quickly share a few messages back and forth and he seems truly interested and also open to the fact it would be my first time and that we would need to take it slow. Before I even had a chance to think, he sent me his address and said to come over now. I was like oh shit this is actually going to happen and the ball is in my court. Being a 19 year old horny guy I immediately jump in shower and get in the car to start heading to this guys place.

The whole ride to his place, I am shaking with nerves. Was I really about to give up my virginity to this guy I only said maybe 5-10 sentences to? What if I was being catfished or what if something else?

My nerves did not let up and I was almost visibly shaking as I got to his door. With me throwing all fear to the side I message him that I am at his place. Within moments the door opens and I am surprised to look up at exactly the same muscular athletic tall from the pictures. He was wearing basketball shorts and a t-shirt. He quickly greets me and pulls me inside. He tells me his roommate is asleep and that we have to stay in his room and not be to loud.

He pulls me into his dimly lit room and closes the door. I was so nervous I didn't really know what to do. Sensing my nervousness he comes up to me and pulls me toward him and starts to passionately kiss me. I am stunned by the quickness, but that quickly fades because I am so turned on. I was making out with one of the most attractive men I have ever seen. I couldn't believe how lucky I was. We started shedding our clothes and seeing him shirtless just turned me on more. His muscular build was stunning and I could not get enough exploring it with my hands while we made out passionately.

We quickly moved to his bed and nothing could have felt better to have this stud on top of me. Feeling his muscular body on top of mine was amazing and I could not get enough of his arms. As our bodies rubbed together, we both were getting rock hard. I could feel his large dick rubbing against mine and I wanted to see more. Before I could even ask, he straddles my chest and I am face first with his amazingly large rod. Without any hesitation I open my mouth and start to suck his thick cock enjoying every second. Not wanting that to end he quickly pulls his cock out of my mouth and moves down to mine. He immediately takes me in his mouth and I am in heaven. I am so turned on that I cant even comprehend how good everything was feeling.

Before I knew it he is lifting my legs up exposing my hole. Not sure what he is about to do, he goes face first and starts to rim my whole deeply. This was the first time ever having a man eat my whole and I was experiencing a world wind of ecstasy. He had me moaning so much I couldn't handle it. He rimmed me for what felt like forever, but was most likely a few mins.

He pulled his tongue out of me and I knew he was ready for more. This was the moment I was wanting for soo long, but I was still nervous. Would I be able to relax, would he fit, would it hurt? He grabbed a condom and some lube and started to get himself ready to to fuck me. He lubed himself up and then my hole and started to slowly tease my whole with his cock. AS he teased he started to slowly insert into my virgin hole slowly opening me up. He may have been about an inch or so in when I started to get nervous and started to hold his hips back a little. He told me to relax and that he would go slow but I was still nervous and kept my hand on his hip. He started to kiss me and as he kissed me he took my hands and held them above my head. I was still nervous and said please go slow and he kept slowly pushing deeper inside me. I was scared it was going to start hurting especially since he was so large, but all of a sudden i feel his hips touch my ass. He was fully inside me all 8 inches of his thick cock. I was surprised and never felt anything like it before. The feeling of fullness and that tingle feeling of your prostate being hit.

He slowly started to thrust in and out and with each thrust he started to go a little faster and faster. Every thrust I was sent a shock of sheer pleasure throughout my body and I was in absolute Ecstasy. This man was fucking me and I could not get enough. What made it even better was he was fucking me and jerking me off at the same time which is a feeling like no other. Before I knew it I was blowing my load all over us and then he was shooting his load into his condom inside me.

We cleaned up and chatted briefly and then I was walked out. Such an intense first experience I had with such a stud of a man.
Did you ever have a follow up visit?
 

BlueBearCub

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First time Meeting Guy:

It was back in the late 2000s and I was just starting college. I was a young barely 18 year old guy getting used to living away from home over a 1000 miles from anyone I knew. I was starting to make friends in school, but still felt like I didn't fit in. I was able to get along with people just fine, but had trouble relating to anyone when it came to dating, girls or relationships in general.

At the time I was already a bit curious about guys, reading forums online, and just being a curious guy not knowing what he was experiencing. My eye was always just drawn to the male physique and it was hard to ignore.

Even though I was so far away from anyone I knew from back home, I was still absolutely terrified to reveal this information to anyone or anyone to find out. This made me very depressed and hard to have a really close relationship to anyone since I was hiding such an important part of myself. Unfortunately that was something I never overcame in college and it wouldn't be till a good amount of time after that I got the confidence to come out to anyone.

Back to 18 year old me, alone in a new town, trying to understand these strong desires I was having. Being a young single man, with a lot of free time on his hands, I resorted to online chat rooms. I used these chat rooms to chat with other men and role play situations I never had the courage to actually do. Meeting a guy, kissing a guy, making love, etc. You get the picture.

I had convinced myself it would only be fantasy and I would never be able to act it out in real life. Acting it out would only cement that new reality and I would never be able to return to my old life. (Yeah I know a bit dramatic, but that is how I felt at the time)

Fast forward a bit to a night where for some reason I am compelled to try more. I was tired of just role playing and watching porn. I wanted to meet someone and have an experience. I wanted to experience the touch of a man, even a kiss. I ended up finding this guy on the chat room I was one. I believe it was this website called Connexion. We talked for a bit and he lived not to far from me and said he could pick me up and just talk in the back of his car. (Sketchy I know) Being a stupid, horny 18 year old man I agreed.

About 30 mins passed I got a text that he was in my area and was about to arrive. I was absolutely terrified and started to chicken out. I told him every lie in the book and was scared he would come knocking at my door trying to find me. After a scary 5-10mins he ended up leaving and I officially felt like an asshole for ghosting him. This would not be the night.

Fast forward maybe a month from then and I am back in the chat room. This time I start talking with another guy who also lives nearby. He seems much nicer and easier to talk to. We actually chat so much that I gain the confidence to swap pictures with him. He is a decent looking guy in his early 30s. Let's call him Aaron for the sake of the story. Aaron was a really nice guy who understood how new everything was for me and let me control the pace of everything we talked about. This definitely made me feel comfortable to opening up to him.

Over the course of a week or two we discussed the idea of meeting up face to face. I was soo nervous to do it, but I knew if I didn't do it with him, I would never have the courage to do it. The night came and we decided to meet up and just walk around my apartment complex. I was soo nervous, but when he arrived I didn't chicken out and actually went outside to meet him. He looked exactly how he did in his pictures.

He could tell I was nervous and led the conversation so it never go too awkward. We probably walked and talked for two hours talking about different things and just getting to know each other. Looking back it was one of the sweetest things. He really went out of his way to make me feel comfortable and put no pressure on me to do anything but just talk.

We ended the night with a hug and he went back home. I immediately texted him when he told me he arrived home and we agreed to meet up again soon.
 

Sad79

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My First Time Bottoming:

Back in my college days roughly 2009 was the first time I experienced anal sex as the receptive partner. I was still deep in the closet, so my only gay experiences have been with hookups on the popular gay "dating" apps like Adam4Adam and the personal sections of Craigslist. (Yeah I know really dangerous) I have topped once or twice, but really wanted to try bottoming. I had a previous experience where I tried bottoming for a guy, but could just not relax for the guy and he eventually gave up. Wanting to redeem myself from that moment, I decided my next hookup I would finally lose by bottom cherry.

Fast forward weeks later and I am in my room and of course horny as fuck. I decide to make a post on the personal section of craigslist detailing that I am a virgin looking to bottom for the first time. This type of ad always led to my inbox flooding with messages from lots of guys. Finding someone who actually looked attractive and also sounded normal was the hard part. This was not my first time doing this, but I never gave up hope finding the right person.

As I waited for the ad to become public and the responses to start arriving, I wondered what would I do if I actually found someone worth meeting. I still was very nervous to bottoming, but my horniness was overriding by anxiety and fears.

Once my ad posted and became public I started getting responses within minutes from a wide arrange of men; old, young, skinny, fat, etc. I find myself a very open guy and open to various ages and body types, but something about it being my first time I was looking for someone who I found to be very attractive in my eyes.

I probably talked with about 10-20 guys, but either they would be really sketchy, not share enough pictures to get a good feel of what they looked like, or would just not be my type.

I was starting to lose hope and started contemplating if I should just jerk off and go to bed. It was already getting late around 10-11pm and the chances of getting someone still wanting to meet up this late was getting slim. As I was just about to give up I receive a response to my ad from this guy. He sends me his stats, 6ft 4 210lbs black muscular/athletic build 8in cut. I am stunned by these stats and assume they are exaggerated. I ask him of course to send pics to prove some of this. He quickly sends back pics and I was surprised to see how accurate they were. My first thought was, how is this stud of a man interested in me? No way he could want to actually meet and hookup with me.

We quickly share a few messages back and forth and he seems truly interested and also open to the fact it would be my first time and that we would need to take it slow. Before I even had a chance to think, he sent me his address and said to come over now. I was like oh shit this is actually going to happen and the ball is in my court. Being a 19 year old horny guy I immediately jump in shower and get in the car to start heading to this guys place.

The whole ride to his place, I am shaking with nerves. Was I really about to give up my virginity to this guy I only said maybe 5-10 sentences to? What if I was being catfished or what if something else?

My nerves did not let up and I was almost visibly shaking as I got to his door. With me throwing all fear to the side I message him that I am at his place. Within moments the door opens and I am surprised to look up at exactly the same muscular athletic tall from the pictures. He was wearing basketball shorts and a t-shirt. He quickly greets me and pulls me inside. He tells me his roommate is asleep and that we have to stay in his room and not be to loud.

He pulls me into his dimly lit room and closes the door. I was so nervous I didn't really know what to do. Sensing my nervousness he comes up to me and pulls me toward him and starts to passionately kiss me. I am stunned by the quickness, but that quickly fades because I am so turned on. I was making out with one of the most attractive men I have ever seen. I couldn't believe how lucky I was. We started shedding our clothes and seeing him shirtless just turned me on more. His muscular build was stunning and I could not get enough exploring it with my hands while we made out passionately.

We quickly moved to his bed and nothing could have felt better to have this stud on top of me. Feeling his muscular body on top of mine was amazing and I could not get enough of his arms. As our bodies rubbed together, we both were getting rock hard. I could feel his large dick rubbing against mine and I wanted to see more. Before I could even ask, he straddles my chest and I am face first with his amazingly large rod. Without any hesitation I open my mouth and start to suck his thick cock enjoying every second. Not wanting that to end he quickly pulls his cock out of my mouth and moves down to mine. He immediately takes me in his mouth and I am in heaven. I am so turned on that I cant even comprehend how good everything was feeling.

Before I knew it he is lifting my legs up exposing my hole. Not sure what he is about to do, he goes face first and starts to rim my whole deeply. This was the first time ever having a man eat my whole and I was experiencing a world wind of ecstasy. He had me moaning so much I couldn't handle it. He rimmed me for what felt like forever, but was most likely a few mins.

He pulled his tongue out of me and I knew he was ready for more. This was the moment I was wanting for soo long, but I was still nervous. Would I be able to relax, would he fit, would it hurt? He grabbed a condom and some lube and started to get himself ready to to fuck me. He lubed himself up and then my hole and started to slowly tease my whole with his cock. AS he teased he started to slowly insert into my virgin hole slowly opening me up. He may have been about an inch or so in when I started to get nervous and started to hold his hips back a little. He told me to relax and that he would go slow but I was still nervous and kept my hand on his hip. He started to kiss me and as he kissed me he took my hands and held them above my head. I was still nervous and said please go slow and he kept slowly pushing deeper inside me. I was scared it was going to start hurting especially since he was so large, but all of a sudden i feel his hips touch my ass. He was fully inside me all 8 inches of his thick cock. I was surprised and never felt anything like it before. The feeling of fullness and that tingle feeling of your prostate being hit.

He slowly started to thrust in and out and with each thrust he started to go a little faster and faster. Every thrust I was sent a shock of sheer pleasure throughout my body and I was in absolute Ecstasy. This man was fucking me and I could not get enough. What made it even better was he was fucking me and jerking me off at the same time which is a feeling like no other. Before I knew it I was blowing my load all over us and then he was shooting his load into his condom inside me.

We cleaned up and chatted briefly and then I was walked out. Such an intense first experience I had with such a stud of a man.

Did you guys happen to ever meet up again?
 

kcdave

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would love to see the other volumes two through five.


Does anyone have a really hot first-time with guy stories?

Years ago this guy wrote this book. It is basically a compilation of first-time with guy stories that guys wrote to him. He took his favorite ones and made them into a 5 volume book. There are some really hot stories here.

Here is the first volume. If anyone wants the other 4 volumes I could upload those too.

My First Time by Jack Hart, Volume 1.pdf


"The publisher and I solicited stories by placing notices in gay newspapers around the country, asking gay men to write about their first consensual same-sex experience. Then, I sat back and waited to see what came in.
While waiting, I admit that I had some misgivings. Would a whole book of these stories prove repetitive? But I needn't have worried. As you're about to see, there's an enormous variety here. The earliest accounts are set back in the 1930s; the latest, in 1994. Sometimes the first-timer is seduced; other times he takes the initiative. Most of the stories carry a sense of delight; a few convey pain. Many are sexy, or exciting,
or romantic."

"I left it to contributors to define "first-time." Did casual adolescent sex play with their peers count? As you'll see, men interpreted the phrase differently, but a large number independently arrived at the same criteria: they selected the experience with which they came to think of themselves as gay, or different, or at least when they realized that male sex had an emotional component for them that wasn't felt by other boys who were just messing around."

"I never changed content, even if I or someone else might disagree with it. Several contributors conclude that their first experience might have made them gay. I'm skeptical that sexual orientation is determined this way, but if that's what they believe, they're entitled to say so here. Originally I planned to arrange these stories according to each contributor's age at the time. I later decided it was more revealing to break them up based on the era when each one took place. It was too late at that point to contact everyone who had not included a date in their story."


"As we began soliciting stories, I wondered if a lot of men would make up something fun, rather than describe their actual first experience, which may not have gone as they had hoped. A few accounts did have all the flavor of a porn magazine submission: The coach and the high school football quarterback in the deserted locker room, for example. I omitted these stories. My apologies to the former quarterback if, in fact, this all really took place. In that case, you've had more than your share of good fortune in life, and I trust you won't be too hurt at being left out of this Book."

"For the most part, my sixth sense tells me the accounts I received and have included are all true. There are too many unexpected details and nuances. Take this - from one of my favorite stories, set in the 1930s after a sixteen-year-old boy finishes an encounter with a Bible salesman on the bus:"

"He gave me a vest pocket Testament bound in artificial red leather and told me, 'Have a good life.' I thanked him, but thought it a mite peculiar that a Bible man was the first person, besides myself, to jack me off. I still have the Testament. It's not been used much."

"If that was made up, then somebody missed a promising career as a novelist!"



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Player_01

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I’d love to read about guys who didn’t have an experience until later
How much is later? I was well into college and met him online. I had a panic attack and had to stop hyperventilating before we could continue. And that was losing my virginity (fucking a guy for the first time)

I didn't try again for a few years after that. :laughing:
 

Thom Hewson

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I’d love to read about guys who didn’t have an experience until later
@Miamired1982 how about later like age 54?
i wasn't latent, just delayed..stunted...by religious guilt and marriage and two sons.
long story short, a 38 yr old native Polish software engineer approached me on silverdaddies. we talked, we met for a drink (imagine he worked in the building next door!). we met up for the first time in the afternoon at a nearby hotel downtown where he was staying before an evening dinner meeting downtown. i was a bit awed when he got naked, awesome build with solid shoulders, thick arms and sturdy legs, POLONIA tattoed on his right ass. and that cock... thick and uncut with a drill head tip like he was just made for fucking.
we made out and 69'd the first time, he knew i wasn't ready to fuck yet. we talked about cleaning out and how he liked to bottom too! which was amazing. after we came together, on each other, i felt the heavy burden of all that guilt absolutely vaporized. i was a new man thanks to him...on the day after my 54th birthday.
there were many next times at numerous other hotels. we flip fucked as hot and passionately as any porno, mostly he topped... he loved to gently push me to the bed and lay on my back as he eased in... i could feel him throb inside as he grunted a bit, and i loved feeling him melt like butter when he came.... the one time i came in him he texted back that he felt himself leaking daddy baby batter on the way home, which gave me a huge boost...
he always got a room, which felt extravagant to me.. and much as i tried he never really wanted me to reciprocate in any way ... he thought i was 'crazy' for bringing wine (he loves wine) and small snacks in between rounds (we usually did come twice). At least once he came to my house when i was for once home alone. we met up probably 4 to 6 times a year over 4 years. Eventually he walked away when he met someone. i was pretty attached to him at that point.

sequel: i helped him once with a work project once and FFwd 4 years he finally friended me on Facebook and even texted hello the other day. , so the whole thing felt resolved. i don't know if I'll ever actually see him again, but I'll always remember him as my first. I am tempted to share an anonymous pic but out of respect i will refrain...i don't know how he's aged since then but i will enjoy remembering him as the hottest man on the planet for the times we were together...

in the years following, i met: a dashing Puerto Rican physician who introduced me to my true love over dinner and a 3-way at his home... my love is my age (the doc is younger like my first), but he is married too and now lives 2 hours away. we chat every day and meet up when he comes into town to see family. we have taken a couple overnights together, he drove 12 hours to camp out for 3 days near me while i was visiting my family in upstate NY. i snuck out of the house at night to spend the night with him in his camper and we had a lovely day hiking the park together....we have a close emotional bond and i remain awed by his virile response for a man of 60, and i am so grateful for his passion and kindness...we both know we would be together if our lives were different but they're not, at least now, and i respect his inability and unwillingness to leave his marriage because he would probably even lose his pension over it (he's a parish school teacher). so we get by the best we can...it's awkward sometimes to articulate just wanting to come home to him and cuddle on the couch together ... to visualize things that don't seem like they will ever be.. but they connote the level of connectedness we have as soul mates...if he were mine there would be nobody else...
In the long months in between our meetings, i also met the most physically awesome man i will ever be with. he is a true Large Penis, like probably 9 x 6.5 which requires BoyButter to get in but thankfully that works wonders! again out of respect i will refrain from posting even just his hard cock but suffice to say i happily roll over when he thwacks it on his palm ... we are truly FWBs, i am glad to meet a mature guy who appreciates having a true friendly connection to enjoy naked time together (the first man was all business which ultimately was rather disconcerting... ) i am emotionally in a good place about this and uplifted by his attraction to me even as i am awed by his Michelangelo David frame, over 6' tall, his boyishly sweet face , the passion with which he makes out, and the way he even hangs large in the shower afterward... i can't even imagine how nuclear hot he would have been at 38! ...
i love the way he tenses up like he's lifting a huge stack of iron in the moment before he shoots... and i love flipping around and sucking him the moment after he shoots, getting every last drop as he reels while i intensify his orgasm with multiple aftershocks with my lips and tongue...i am in total peace being held by his big strong muscles while we cuddle and even nod off after he is totally spent..... at night i dream what it would be like to wake up to him sliding into me...
i don't expect the FWB will last forever, but that's ok. i have no idea what the future holds for me with my true love. i guess you can say i just made up for lost time.
 

kcdave

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You are a very eloquent writer. Needless to say your words are my fantasy to meet some nice guys as friends with benefits like you described.

@Miamired1982 how about later like age 54?
i wasn't latent, just delayed..stunted...by religious guilt and marriage and two sons.
long story short, a 38 yr old native Polish software engineer approached me on silverdaddies. we talked, we met for a drink (imagine he worked in the building next door!). we met up for the first time in the afternoon at a nearby hotel downtown where he was staying before an evening dinner meeting downtown. i was a bit awed when he got naked, awesome build with solid shoulders, thick arms and sturdy legs, POLONIA tattoed on his right ass. and that cock... thick and uncut with a drill head tip like he was just made for fucking.
we made out and 69'd the first time, he knew i wasn't ready to fuck yet. we talked about cleaning out and how he liked to bottom too! which was amazing. after we came together, on each other, i felt the heavy burden of all that guilt absolutely vaporized. i was a new man thanks to him...on the day after my 54th birthday.
there were many next times at numerous other hotels. we flip fucked as hot and passionately as any porno, mostly he topped... he loved to gently push me to the bed and lay on my back as he eased in... i could feel him throb inside as he grunted a bit, and i loved feeling him melt like butter when he came.... the one time i came in him he texted back that he felt himself leaking daddy baby batter on the way home, which gave me a huge boost...
he always got a room, which felt extravagant to me.. and much as i tried he never really wanted me to reciprocate in any way ... he thought i was 'crazy' for bringing wine (he loves wine) and small snacks in between rounds (we usually did come twice). At least once he came to my house when i was for once home alone. we met up probably 4 to 6 times a year over 4 years. Eventually he walked away when he met someone. i was pretty attached to him at that point.

sequel: i helped him once with a work project once and FFwd 4 years he finally friended me on Facebook and even texted hello the other day. , so the whole thing felt resolved. i don't know if I'll ever actually see him again, but I'll always remember him as my first. I am tempted to share an anonymous pic but out of respect i will refrain...i don't know how he's aged since then but i will enjoy remembering him as the hottest man on the planet for the times we were together...

in the years following, i met: a dashing Puerto Rican physician who introduced me to my true love over dinner and a 3-way at his home... my love is my age (the doc is younger like my first), but he is married too and now lives 2 hours away. we chat every day and meet up when he comes into town to see family. we have taken a couple overnights together, he drove 12 hours to camp out for 3 days near me while i was visiting my family in upstate NY. i snuck out of the house at night to spend the night with him in his camper and we had a lovely day hiking the park together....we have a close emotional bond and i remain awed by his virile response for a man of 60, and i am so grateful for his passion and kindness...we both know we would be together if our lives were different but they're not, at least now, and i respect his inability and unwillingness to leave his marriage because he would probably even lose his pension over it (he's a parish school teacher). so we get by the best we can...it's awkward sometimes to articulate just wanting to come home to him and cuddle on the couch together ... to visualize things that don't seem like they will ever be.. but they connote the level of connectedness we have as soul mates...if he were mine there would be nobody else...
In the long months in between our meetings, i also met the most physically awesome man i will ever be with. he is a true Large Penis, like probably 9 x 6.5 which requires BoyButter to get in but thankfully that works wonders! again out of respect i will refrain from posting even just his hard cock but suffice to say i happily roll over when he thwacks it on his palm ... we are truly FWBs, i am glad to meet a mature guy who appreciates having a true friendly connection to enjoy naked time together (the first man was all business which ultimately was rather disconcerting... ) i am emotionally in a good place about this and uplifted by his attraction to me even as i am awed by his Michelangelo David frame, over 6' tall, his boyishly sweet face , the passion with which he makes out, and the way he even hangs large in the shower afterward... i can't even imagine how nuclear hot he would have been at 38! ...
i love the way he tenses up like he's lifting a huge stack of iron in the moment before he shoots... and i love flipping around and sucking him the moment after he shoots, getting every last drop as he reels while i intensify his orgasm with multiple aftershocks with my lips and tongue...i am in total peace being held by his big strong muscles while we cuddle and even nod off after he is totally spent..... at night i dream what it would be like to wake up to him sliding into me...
i don't expect the FWB will last forever, but that's ok. i have no idea what the future holds for me with my true love. i guess you can say i just made up for lost time.
 

Petelong9898

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How much is later? I was well into college and met him online. I had a panic attack and had to stop hyperventilating before we could continue. And that was losing my virginity (fucking a guy for the first time)

I didn't try again for a few years after that. :laughing:
Nice
 
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You are a very eloquent writer. Needless to say your words are my fantasy to meet some nice guys as friends with benefits like you described.
Wow, incredibly hot stories man
@Miamired1982 how about later like age 54?
i wasn't latent, just delayed..stunted...by religious guilt and marriage and two sons.
long story short, a 38 yr old native Polish software engineer approached me on silverdaddies. we talked, we met for a drink (imagine he worked in the building next door!). we met up for the first time in the afternoon at a nearby hotel downtown where he was staying before an evening dinner meeting downtown. i was a bit awed when he got naked, awesome build with solid shoulders, thick arms and sturdy legs, POLONIA tattoed on his right ass. and that cock... thick and uncut with a drill head tip like he was just made for fucking.
we made out and 69'd the first time, he knew i wasn't ready to fuck yet. we talked about cleaning out and how he liked to bottom too! which was amazing. after we came together, on each other, i felt the heavy burden of all that guilt absolutely vaporized. i was a new man thanks to him...on the day after my 54th birthday.
there were many next times at numerous other hotels. we flip fucked as hot and passionately as any porno, mostly he topped... he loved to gently push me to the bed and lay on my back as he eased in... i could feel him throb inside as he grunted a bit, and i loved feeling him melt like butter when he came.... the one time i came in him he texted back that he felt himself leaking daddy baby batter on the way home, which gave me a huge boost...
he always got a room, which felt extravagant to me.. and much as i tried he never really wanted me to reciprocate in any way ... he thought i was 'crazy' for bringing wine (he loves wine) and small snacks in between rounds (we usually did come twice). At least once he came to my house when i was for once home alone. we met up probably 4 to 6 times a year over 4 years. Eventually he walked away when he met someone. i was pretty attached to him at that point.

sequel: i helped him once with a work project once and FFwd 4 years he finally friended me on Facebook and even texted hello the other day. , so the whole thing felt resolved. i don't know if I'll ever actually see him again, but I'll always remember him as my first. I am tempted to share an anonymous pic but out of respect i will refrain...i don't know how he's aged since then but i will enjoy remembering him as the hottest man on the planet for the times we were together...

in the years following, i met: a dashing Puerto Rican physician who introduced me to my true love over dinner and a 3-way at his home... my love is my age (the doc is younger like my first), but he is married too and now lives 2 hours away. we chat every day and meet up when he comes into town to see family. we have taken a couple overnights together, he drove 12 hours to camp out for 3 days near me while i was visiting my family in upstate NY. i snuck out of the house at night to spend the night with him in his camper and we had a lovely day hiking the park together....we have a close emotional bond and i remain awed by his virile response for a man of 60, and i am so grateful for his passion and kindness...we both know we would be together if our lives were different but they're not, at least now, and i respect his inability and unwillingness to leave his marriage because he would probably even lose his pension over it (he's a parish school teacher). so we get by the best we can...it's awkward sometimes to articulate just wanting to come home to him and cuddle on the couch together ... to visualize things that don't seem like they will ever be.. but they connote the level of connectedness we have as soul mates...if he were mine there would be nobody else...
In the long months in between our meetings, i also met the most physically awesome man i will ever be with. he is a true Large Penis, like probably 9 x 6.5 which requires BoyButter to get in but thankfully that works wonders! again out of respect i will refrain from posting even just his hard cock but suffice to say i happily roll over when he thwacks it on his palm ... we are truly FWBs, i am glad to meet a mature guy who appreciates having a true friendly connection to enjoy naked time together (the first man was all business which ultimately was rather disconcerting... ) i am emotionally in a good place about this and uplifted by his attraction to me even as i am awed by his Michelangelo David frame, over 6' tall, his boyishly sweet face , the passion with which he makes out, and the way he even hangs large in the shower afterward... i can't even imagine how nuclear hot he would have been at 38! ...
i love the way he tenses up like he's lifting a huge stack of iron in the moment before he shoots... and i love flipping around and sucking him the moment after he shoots, getting every last drop as he reels while i intensify his orgasm with multiple aftershocks with my lips and tongue...i am in total peace being held by his big strong muscles while we cuddle and even nod off after he is totally spent..... at night i dream what it would be like to wake up to him sliding into me...
i don't expect the FWB will last forever, but that's ok. i have no idea what the future holds for me with my true love. i guess you can say i just made up for lost time.

fuck man, great story. id give anything to meet an older muscle daddy fwb lol. im too picky and paranoid
 

Thom Hewson

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Wow, incredibly hot stories man


fuck man, great story. id give anything to meet an older muscle daddy fwb lol. im too picky and paranoid
@Miamired1982 @kcdave thank you... yeah i think real life is hotter than fiction.... i do sincerely appreciate the compliments about my writing though.
i paused for a minute...just a minute.. before meeting Mr Large Penis... even though my love and I have no exclusive commitment i had to pause and think about complicating my life, health safety, and other concerns. but in the end it was the right decision to play with him... i truly had no idea how physically magnificent he would be til his clothes came off and then i just...gasped. at every inch of him up and down, back and front. i honestly thought men like that only exist in pornos or at the whim of Photoshop. The truly amazing part was connecting with a good human being... I did eventually get over the first guy and the dissonance of being more emotionally invested in him than he was in me (yeah i was in love, but it wasn't that, it was regarding him as a true friend when he was in fact just acting in a friendly way...).

the true healing part was meeting the kind of man you thought you'd only ever jerk off to in your dreams then discovering he's actually a decent guy who found me attractive and valued a personal connection..even for just a physical relationship. the only reason it's not more is because of the limitations of my life circumstance, not his...

none of this is to diminish my true love... we have built the kind of emotional bond that stands the test of time. he just is not physically available. and we are both vers (or i taught him to be vers as the first man inside him), which suits me better. i find myself actually channeling a different, more submissive side of myself, yearning for his big strong comfort and the safety and security of being his muscly arms... when only bottoming for LP... and i probably would have to think about that if he became The One. With my love, we are both comforting and comforted by each other. i feel stronger with him, and love holding and comforting him.... and yet i am comforted by even the sound of his reassuring voice.

Moral of the story.... It's just so wonderful to know a total top who's not a total dick. !!!!
 

adamwest123

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My first time story is sady kind of embarrassing :D.

While still a virgin I read that men might have trouble gettig an erection when feeling nervous. I couldn't believe it, after all I was getting boners in the most awkward situations.
Later I met my first bf. After couple of dates we finally decided to make our relationship more physical.

On the fateful day I was travelling by train to meet my bf. As the train was approaching the town he lived in my nervosity was rising. By the time I exited the train I felt like a lamb heading to a slaughter. I can't recall feeling that nervous ever since.

The night, needless to say, turned into a complete disaster. The condom was too tight, couldn't keep an erection.

It became obvious nothing was going to happen that night, so we went to sleep. Thankfully my bf was understanding, still, I felt super bad.

I was hugging the guy the whole night - it must have calmed me down because in the morning my vigor returned and I wasn't a virgin anymore :).
 

Thom Hewson

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You are a very eloquent writer. Needless to say your words are my fantasy to meet some nice guys as friends with benefits like you described.

@kcdave thank you. As it turns out six months later, my love came to make love and tell me he wasn't sure when I'd see him again.. he had to work on his marriage and mentioned something about getting snared by the phone bill ...
My He-Man playmate is still very interested and around but rather sporadic... he has a full schedule owning two optometric practices and elderly mom in WI an hour away. He's there every weekend. I believe he's doing a lot of clearing out and helping her but I can't help thinking he must be seeing someone there too... it is what it is. No way I'm in any position to lay any claim to him, just appreciate being liked.
Interestingly, I met a 28 yo nursing student who seems like a very nice guy. We've texted a lot but haven't met. He's hot AF and vers which is me too as long as my meds work. Going to give him a go...