I’ve always wanted to write a chronicle of sorts about my sexual adventures over the years and this seems like a great place to start. I’m calling the series Facts&Fantasies as it will include both real and “I wish” experiences. I’ll be sure to make it clear if I’m talking about a Fact or a Fantasy. I’ll use real first names (no last names) to make it more personal for me.
“My first time” seems like the obvious place to start but I recently shared that in a post called “My First Time…. In Detail”. If it’s ok I’d like to repost it here as a kickoff to the series. You can skip it if you’ve already read it but I hope you’ll check back as I hope to post more stories.
FACT (story is 100% true):
Jim C. was a college classmate and pretty good friend as we were a close knit group of a dozen students in this particular area of study (unnamed to protect identities). He was 19 and a couple inches taller than me but thin as a rail, probably 5’-10” and no more than 135 lbs. At the time I’d just turned 21, was 5’-8” and also around 135 lbs. I confess here that I thought about him sometimes when masturbating as he had a great ass and the type of twink body I was really attracted to. I was also highly closeted (and frustrated!).
Jim was a little bit effeminate, so it was no great surprise when he very nervously came out of the closet to me one night. He was very grateful I didn't freak out. The next night we went out for a late dinner (at TGI Fridays I remember!). He was telling me that he'd been attracted to guys ever since junior high school and finally decided to just admit to himself and others he was gay. Eventually there was a pause in the conversation and I quietly told him "Jim, we have a lot in common". He dropped his fork and about fell over. After he recovered some composure, I asked if he'd ever thought about having sex with me and he said yes, MANY times, and while masturbating. I was secretly very turned on that he thought about me while jacking off. I asked if we could maybe go try something right that night. He suggested we wait a day or two for a better time (we both had roommates) but my adrenaline was running too high. So I convinced him and we decided to go to the office where I had a part time job, it would be empty and dark that time of night and it had a lounge room in the back we could use.
On the drive over he asked if I ever thought about HIM when I was masturbating. I was SO nervous (and shocked that someone actually thought I masturbated!) but I answered yes, I did have fantasies about him. He asked what I thought about and I truthfully said I thought a lot about what it would be like to sit and make out with him. He was amazed and said that's the same thing he thought about doing with me when he was masturbating. He asked if there were any other guys at school I was attracted to. I said yes and he immediately said “Todd?”, my then roommate and good friend. I said yes, but that's another story I hope to share later.
We got to my office and went to the back room. It was carpeted with couches, and only a couple of high up windows that let in just enough street light so we could clearly see everything. Up to this point we hadn't touched each other at all. He sat down on a couch and I sat next to him, close but not touching. I hesitated for a second but then turned, put my arm around his shoulder and went in for a kiss. Our lips locked in an open mouth kiss, he took my head in his free hand and immediately pushed his tongue into my mouth. WOW, talk about sensory overload! I'd fantasized for years about what it would be like to kiss another boy and the experience was mind blowing! Even better than I'd imagined. I kind of flinched at the feel of his tongue on my tongue but gladly reciprocated almost immediately. We just held that position for a LONG time, the only movements of our bodies were our tongues intertwining. His tongue felt so alive and sensual in my mouth!
After a while we pulled apart and instinctively we both took our shirts off then went right back to the same kissing position. Only now the sensation was magnified because we could feel each other's bare skin. The feeling of my chest against his, my hand on the side of his bare ribcage, too nervous to move it, such an intense feeling. We just held that position and made out for a long time, savoring each other’s tongues and warmth of our bodies. Eventually his hand started moving around my shoulders and down my arm so I moved mine up and down the side of his torso. He felt amazing, so slim and smooth. I even let my hand move up so my thumb caught a brief "accidental" feel of his armpit hair. I couldn't believe this was happening and it felt so GOOD! We switched positions without breaking the kiss so I was leaning back into the couch and he was turned to face me. He started running his hand along my face, neck, and down to my chest. He gently felt my chest, circling a finger over each nipple, then moved his hand down across my stomach. All this while working our tongues as far into each others mouth as we could, both making small moaning sounds. He then pulled his mouth away from mine and looked down to watch his hand as he gently placed it over the bulge in my white painters pants (I was barely half hard, too nervous!). He softly squeezed my bulge for a few seconds and said "In class there are times when all I can think about was what it would be like to reach over and start feeling your cock." This was all too much but I loved it.
I stood up and started taking my pants off, he did the same. We both wore bikini undies back then, mine were light blue, his were white. We sat back down and resumed making out. Man, the feeling of his full nearly nude body up against mine, legs entwining, felt so nice. I remember we didn't let our hands move down to feel each other's bulges but I loved just running my hands up and down his back, side, and shoulders - so warm, lean, and smooth. He had his free hand up cradling my head so I let my free hand move back to his armpit again. I had a thing for armpits back then, they were a mostly hidden, semi-intimate part of a guy's body. I loved catching glimpses up the sleeve of guys I thought were sexy to see how much hair they had. It was a sneak peak into what their pubic hair probably looked like. Jim didn't seem to mind that I was exploring with my fingers, I loved it.
After a bit we came up for air and he said, "Obviously you want to go first." I didn't object. He pulled his legs up and slipped off his undies while I knelt down on the floor between his legs. THIS was a huge moment for me. I couldn't believe I was going to feel what it was like to take another boys penis into my mouth like I'd been fantasizing for years. I took both my hands and moved them under him so I could cradle his PERFECT ass. For some reason I was too scared to actually look at his cock (it was pretty dark anyway), so I closed my eyes, opened my mouth, and went down. Amazingly, my aim was good and it slipped directly into my mouth. I just froze, didn't move a muscle. He was ROCK hard and his cock felt so warm and smooth with no scent or flavor that I remember. It just felt and tasted right. He didn't have the biggest cock in the world, in fact it was fairly small, but it was the PERFECT size for sucking - not big and gagging like some can be. It felt really comfortable in my mouth. I could easily take in the whole thing so my nose was buried in his cute little twink patch of pubic hair.
I eventually unfroze and started actually sucking and moving my tongue all over his cock. At one point he said, "watch the teeth". What did I know? It was my first time! But I was into it!! I don't remember how long I sucked him but after a bit he said "My turn". We switched places and I peeled off my undies while he knelt down. My cock was getting hard by now and he took it in his hand, holding it like a microphone, and without hesitation put his lips around the exposed shaft and cock head. I'd had so many mind blowing sensations already that night but the feel of my cock in another boy’s mouth was too much. I let out the loudest moan of the night, the feeling was indescribable. That "first time" feeling only happens once and it was awesome.
I've gone on too long. The rest of the experience was spent kissing and sucking. I'll never forget the look on his face as he ran his tongue up and down the length of my shaft. Or the sound of his moaning when I used just the tip of my tongue to explore the tip of his cock, trying to find his pee hole, and when I did it was also his "sensitive spot". Most of the kissing time was spent either standing or laying with him on top with both my hands cupping and fondling his incredible ass. SO perfect. When he laid on top I liked to wrap my legs around him and since he was taller I could feel the tip of his hard cock nudging up against my asshole.
Towards the "unfortunate" ending of the experience, I told him I wanted him to sit on my face, which kind of shocked him I think. But I begged, saying "Come on! I've always wanted to try that!" So I laid down on my back and he got down to straddle my face. I opened my mouth and planted it directly over his hole. Again I froze, freezing for a second, before sticking my tongue out and flicking it lightly and quickly over his asshole. This REALLY made him moan. I was getting up the nerve to actually take a long, deep lick of his asshole when.....
.....we heard a door slam somewhere upstairs. Crap....someone was in the building. It was like midnight. We high tailed it out the back door. I drove him back to his dorm and he was understandably a little put off that I was so unvocal about things. I was simply too immature (and stupid)(and freaked out) to deal with it so the next day I told him it wasn't for me. What a STUPID lie that was. I masturbated every night for months thinking about the experience. Why didn't I ask him for another chance so we could "finish up"? I SO wanted to taste his cum in my mouth and give him a long, intense rimming. We both graduated and moved on. Sad, really.
DM me if you want to see a picture of Jim and me at that time. I’ll blur out our faces.
“My first time” seems like the obvious place to start but I recently shared that in a post called “My First Time…. In Detail”. If it’s ok I’d like to repost it here as a kickoff to the series. You can skip it if you’ve already read it but I hope you’ll check back as I hope to post more stories.
FACT (story is 100% true):
Jim C. was a college classmate and pretty good friend as we were a close knit group of a dozen students in this particular area of study (unnamed to protect identities). He was 19 and a couple inches taller than me but thin as a rail, probably 5’-10” and no more than 135 lbs. At the time I’d just turned 21, was 5’-8” and also around 135 lbs. I confess here that I thought about him sometimes when masturbating as he had a great ass and the type of twink body I was really attracted to. I was also highly closeted (and frustrated!).
Jim was a little bit effeminate, so it was no great surprise when he very nervously came out of the closet to me one night. He was very grateful I didn't freak out. The next night we went out for a late dinner (at TGI Fridays I remember!). He was telling me that he'd been attracted to guys ever since junior high school and finally decided to just admit to himself and others he was gay. Eventually there was a pause in the conversation and I quietly told him "Jim, we have a lot in common". He dropped his fork and about fell over. After he recovered some composure, I asked if he'd ever thought about having sex with me and he said yes, MANY times, and while masturbating. I was secretly very turned on that he thought about me while jacking off. I asked if we could maybe go try something right that night. He suggested we wait a day or two for a better time (we both had roommates) but my adrenaline was running too high. So I convinced him and we decided to go to the office where I had a part time job, it would be empty and dark that time of night and it had a lounge room in the back we could use.
On the drive over he asked if I ever thought about HIM when I was masturbating. I was SO nervous (and shocked that someone actually thought I masturbated!) but I answered yes, I did have fantasies about him. He asked what I thought about and I truthfully said I thought a lot about what it would be like to sit and make out with him. He was amazed and said that's the same thing he thought about doing with me when he was masturbating. He asked if there were any other guys at school I was attracted to. I said yes and he immediately said “Todd?”, my then roommate and good friend. I said yes, but that's another story I hope to share later.
We got to my office and went to the back room. It was carpeted with couches, and only a couple of high up windows that let in just enough street light so we could clearly see everything. Up to this point we hadn't touched each other at all. He sat down on a couch and I sat next to him, close but not touching. I hesitated for a second but then turned, put my arm around his shoulder and went in for a kiss. Our lips locked in an open mouth kiss, he took my head in his free hand and immediately pushed his tongue into my mouth. WOW, talk about sensory overload! I'd fantasized for years about what it would be like to kiss another boy and the experience was mind blowing! Even better than I'd imagined. I kind of flinched at the feel of his tongue on my tongue but gladly reciprocated almost immediately. We just held that position for a LONG time, the only movements of our bodies were our tongues intertwining. His tongue felt so alive and sensual in my mouth!
After a while we pulled apart and instinctively we both took our shirts off then went right back to the same kissing position. Only now the sensation was magnified because we could feel each other's bare skin. The feeling of my chest against his, my hand on the side of his bare ribcage, too nervous to move it, such an intense feeling. We just held that position and made out for a long time, savoring each other’s tongues and warmth of our bodies. Eventually his hand started moving around my shoulders and down my arm so I moved mine up and down the side of his torso. He felt amazing, so slim and smooth. I even let my hand move up so my thumb caught a brief "accidental" feel of his armpit hair. I couldn't believe this was happening and it felt so GOOD! We switched positions without breaking the kiss so I was leaning back into the couch and he was turned to face me. He started running his hand along my face, neck, and down to my chest. He gently felt my chest, circling a finger over each nipple, then moved his hand down across my stomach. All this while working our tongues as far into each others mouth as we could, both making small moaning sounds. He then pulled his mouth away from mine and looked down to watch his hand as he gently placed it over the bulge in my white painters pants (I was barely half hard, too nervous!). He softly squeezed my bulge for a few seconds and said "In class there are times when all I can think about was what it would be like to reach over and start feeling your cock." This was all too much but I loved it.
I stood up and started taking my pants off, he did the same. We both wore bikini undies back then, mine were light blue, his were white. We sat back down and resumed making out. Man, the feeling of his full nearly nude body up against mine, legs entwining, felt so nice. I remember we didn't let our hands move down to feel each other's bulges but I loved just running my hands up and down his back, side, and shoulders - so warm, lean, and smooth. He had his free hand up cradling my head so I let my free hand move back to his armpit again. I had a thing for armpits back then, they were a mostly hidden, semi-intimate part of a guy's body. I loved catching glimpses up the sleeve of guys I thought were sexy to see how much hair they had. It was a sneak peak into what their pubic hair probably looked like. Jim didn't seem to mind that I was exploring with my fingers, I loved it.
After a bit we came up for air and he said, "Obviously you want to go first." I didn't object. He pulled his legs up and slipped off his undies while I knelt down on the floor between his legs. THIS was a huge moment for me. I couldn't believe I was going to feel what it was like to take another boys penis into my mouth like I'd been fantasizing for years. I took both my hands and moved them under him so I could cradle his PERFECT ass. For some reason I was too scared to actually look at his cock (it was pretty dark anyway), so I closed my eyes, opened my mouth, and went down. Amazingly, my aim was good and it slipped directly into my mouth. I just froze, didn't move a muscle. He was ROCK hard and his cock felt so warm and smooth with no scent or flavor that I remember. It just felt and tasted right. He didn't have the biggest cock in the world, in fact it was fairly small, but it was the PERFECT size for sucking - not big and gagging like some can be. It felt really comfortable in my mouth. I could easily take in the whole thing so my nose was buried in his cute little twink patch of pubic hair.
I eventually unfroze and started actually sucking and moving my tongue all over his cock. At one point he said, "watch the teeth". What did I know? It was my first time! But I was into it!! I don't remember how long I sucked him but after a bit he said "My turn". We switched places and I peeled off my undies while he knelt down. My cock was getting hard by now and he took it in his hand, holding it like a microphone, and without hesitation put his lips around the exposed shaft and cock head. I'd had so many mind blowing sensations already that night but the feel of my cock in another boy’s mouth was too much. I let out the loudest moan of the night, the feeling was indescribable. That "first time" feeling only happens once and it was awesome.
I've gone on too long. The rest of the experience was spent kissing and sucking. I'll never forget the look on his face as he ran his tongue up and down the length of my shaft. Or the sound of his moaning when I used just the tip of my tongue to explore the tip of his cock, trying to find his pee hole, and when I did it was also his "sensitive spot". Most of the kissing time was spent either standing or laying with him on top with both my hands cupping and fondling his incredible ass. SO perfect. When he laid on top I liked to wrap my legs around him and since he was taller I could feel the tip of his hard cock nudging up against my asshole.
Towards the "unfortunate" ending of the experience, I told him I wanted him to sit on my face, which kind of shocked him I think. But I begged, saying "Come on! I've always wanted to try that!" So I laid down on my back and he got down to straddle my face. I opened my mouth and planted it directly over his hole. Again I froze, freezing for a second, before sticking my tongue out and flicking it lightly and quickly over his asshole. This REALLY made him moan. I was getting up the nerve to actually take a long, deep lick of his asshole when.....
.....we heard a door slam somewhere upstairs. Crap....someone was in the building. It was like midnight. We high tailed it out the back door. I drove him back to his dorm and he was understandably a little put off that I was so unvocal about things. I was simply too immature (and stupid)(and freaked out) to deal with it so the next day I told him it wasn't for me. What a STUPID lie that was. I masturbated every night for months thinking about the experience. Why didn't I ask him for another chance so we could "finish up"? I SO wanted to taste his cum in my mouth and give him a long, intense rimming. We both graduated and moved on. Sad, really.
DM me if you want to see a picture of Jim and me at that time. I’ll blur out our faces.
