Fantasy vs Reality?

[starfish71]

Long time lurker, first time poster...

So who else has had early experiences that did not quite live up to the fantasies in your mind? I initial experience with a guy was not bad, but not all that either... is the next time different? Of is it more of a journey? Here is how it went....

I had been having gay fantasies since my teenage years… looking at victoria secret catalogs imagining how soft and sexy the outfits would be to wear, looking at porn mags like any teenage boy would, but also wondering what it would be like to be on the receiving end of a cock… the closest things came at the time to playing any of this out was some toying around with a cousin, rubbing our dicks together under the sheets, or in the shower… there was one fleeting attempt at oral, but it ended as awkwardly as it started…

I dated girls in high school, college, and beyond, successfully and happily, but the fantasies remained, and intensified… I explored various porn… mostly straight and some trans (I don’t find gay porn particularly stimulating), imagining I was on the receiving end. I eventually worked up the nerve to buy a toy or two, and some lingerie that I would get dressed up in and masturbate.

This continued for quite some time… even while happily married… but the fantasies remained, and intensified, the toy was not enough… I wanted a real cock in me… I’m not quite sure how, but I stumbled upon Sniffies, and stated looking around… anomalously at first, then set up a profile with a picture of my best angle, in red panties… Let’s say that this generated some interesting attention… everything from “tell me where you are, I’m gonna pound that ass”, to several offers of three-ways, to several sincere chats… a few appeared to have some promise of leading to some sort of play, but always fizzled out… it looked like the one was going to go that way too… after the exchange of the “what are you in to, what are you looking for?” chats, and the exchange of some mouth watering pics, we agreed to meet up… the time was somewhat dependent on work (was on a business trip)… it was either going to be before a dinner engagement if the day’s meetings wrapped up early, or after… well meetings didn’t wrap up, and dinner went long and he was not around, so that night didn’t work out, and I was leaving the next day so it looked like it was going to be a bust too… the next morning, figuring there wasn’t enough time to meet up, I went about packing, and got in one last toy session of the trip and was about to head out to lunch when a message popped up from my paramour… he apologized for not responding the night before, that he had fallen asleep, and wondered if I had time… I decided I could skip lunch and I said I had about an hour and a half before I had to head out… he said he could be at my hotel in about 30 min… I said ok… he asked if I had any of the outfits with me that I had sent in the pictures, which I did… so I quickly put it on and sent him a pic… through discussion he knew I was a virgin, and asked if he should bring something to loosen me up… I told him I had already dildo’d myself that morning, so was ought to be good… he liked that, and asked if I could lube up before he got there… I said yes, and sent him a pic of my shiny hole… His next request was for me to put my dildo in and keep it in until he got there, so I dutifully inserted it balls deep, secured it in place with my thong, and sent him another pic… I think this all made him drive faster since he got there in about 20min… he im’d me when he got to the lobby, and I gave him the room number… I waited anxiously at the door wearing nothing but my black thong, a garter belt and fishnets… then can the knock on the door… housekeeping… wtf… not now thank you!... Then there was the ding of the elevator… I saw a guy coming towards my door… it was now or never… he was no Ryan Reynolds, but not the hunchback of notre dame either, so fuck it, here we go… there’s the knock… I open the door… he is pleased with my presentation… he immediately starts rubbing my ass and crotch… I immediately start rubbing his crotch… nice package… I close the door and we move in to the room, to the seating area, where I help him out of his shirt, and undo the waste on his pants… he peels them off leaving him with just his boxer briefs on… I dropped to my knees in front of him and pull them down releasing his semi-erect cock… my goal was to remove the semi part as quickly as possible…I took his cock in my mouth and began to suck… it was the first real time with cock in my mouth and I was savoring it… I took the head out and worked the shaft to the base, then the balls, then back to the head… it did not take long for him to be a fully erect 7”… he pulled my up from my knees and asked if I wanted to go further, to which I just nodded… he led me over to the bed, and laid me on my back and I spread my legs… he rubbed my cock and ass a little, then inserted his finger in my hole… I came… a lot… he scooped up my cum with his finger and proceeded to massage it into my waiting hole… he put on a condom, and asked one last more time if I wanted to continue… I told him I wanted his cock… he then pressed his head to my hole… the moment of truth… and he was in… he started slow… holding my legs apart in the air, then picked up the pace… putting my legs on his chest/shoulders… he fucked me for probably five minutes this way, then asked me to roll over and stand up, I complied… He then bent me over the bed and entered me again, and fucked me from behind for another five minutes… his pace quickened, and he came with some final thrusts…

Though all of it I was in somewhat of a trance… I was certainly there, and experiencing it, participating in it, not not enjoying it, but not fully enjoying it either… it didn’t feel bad or hurt, but it didn’t feel great… just ok… when it was all done, he wiped up… asked if I wanted to try anything else, which had I had more time I might have, but I said no, and he got dressed and left… I hopped in the shower, then packed up and checked out of the room… I didn’t feel awkward, or regret or remorse, but also was wondering if the experience had lived up to the fantasies? I’m still not sure… I still have them… I still spend time on Sniffies looking for opportunities to explore more, but the logistics have not worked out yet (though I have received several offers and some delicious dick pics ;-) )… time will tell.

 

[AlexBailey]

Sweet story.

If it were me I'd need more connection to get the synergy flowing.

 

[Professor360]

Long time lurker, first time poster...

So who else has had early experiences that did not quite live up to the fantasies in your mind? I initial experience with a guy was not bad, but not all that either... is the next time different? Of is it more of a journey? Here is how it went....

I had been having gay fantasies since my teenage years… looking at victoria secret catalogs imagining how soft and sexy the outfits would be to wear, looking at porn mags like any teenage boy would, but also wondering what it would be like to be on the receiving end of a cock… the closest things came at the time to playing any of this out was some toying around with a cousin, rubbing our dicks together under the sheets, or in the shower… there was one fleeting attempt at oral, but it ended as awkwardly as it started…

I dated girls in high school, college, and beyond, successfully and happily, but the fantasies remained, and intensified… I explored various porn… mostly straight and some trans (I don’t find gay porn particularly stimulating), imagining I was on the receiving end. I eventually worked up the nerve to buy a toy or two, and some lingerie that I would get dressed up in and masturbate.

This continued for quite some time… even while happily married… but the fantasies remained, and intensified, the toy was not enough… I wanted a real cock in me… I’m not quite sure how, but I stumbled upon Sniffies, and stated looking around… anomalously at first, then set up a profile with a picture of my best angle, in red panties… Let’s say that this generated some interesting attention… everything from “tell me where you are, I’m gonna pound that ass”, to several offers of three-ways, to several sincere chats… a few appeared to have some promise of leading to some sort of play, but always fizzled out… it looked like the one was going to go that way too… after the exchange of the “what are you in to, what are you looking for?” chats, and the exchange of some mouth watering pics, we agreed to meet up… the time was somewhat dependent on work (was on a business trip)… it was either going to be before a dinner engagement if the day’s meetings wrapped up early, or after… well meetings didn’t wrap up, and dinner went long and he was not around, so that night didn’t work out, and I was leaving the next day so it looked like it was going to be a bust too… the next morning, figuring there wasn’t enough time to meet up, I went about packing, and got in one last toy session of the trip and was about to head out to lunch when a message popped up from my paramour… he apologized for not responding the night before, that he had fallen asleep, and wondered if I had time… I decided I could skip lunch and I said I had about an hour and a half before I had to head out… he said he could be at my hotel in about 30 min… I said ok… he asked if I had any of the outfits with me that I had sent in the pictures, which I did… so I quickly put it on and sent him a pic… through discussion he knew I was a virgin, and asked if he should bring something to loosen me up… I told him I had already dildo’d myself that morning, so was ought to be good… he liked that, and asked if I could lube up before he got there… I said yes, and sent him a pic of my shiny hole… His next request was for me to put my dildo in and keep it in until he got there, so I dutifully inserted it balls deep, secured it in place with my thong, and sent him another pic… I think this all made him drive faster since he got there in about 20min… he im’d me when he got to the lobby, and I gave him the room number… I waited anxiously at the door wearing nothing but my black thong, a garter belt and fishnets… then can the knock on the door… housekeeping… wtf… not now thank you!... Then there was the ding of the elevator… I saw a guy coming towards my door… it was now or never… he was no Ryan Reynolds, but not the hunchback of notre dame either, so fuck it, here we go… there’s the knock… I open the door… he is pleased with my presentation… he immediately starts rubbing my ass and crotch… I immediately start rubbing his crotch… nice package… I close the door and we move in to the room, to the seating area, where I help him out of his shirt, and undo the waste on his pants… he peels them off leaving him with just his boxer briefs on… I dropped to my knees in front of him and pull them down releasing his semi-erect cock… my goal was to remove the semi part as quickly as possible…I took his cock in my mouth and began to suck… it was the first real time with cock in my mouth and I was savoring it… I took the head out and worked the shaft to the base, then the balls, then back to the head… it did not take long for him to be a fully erect 7”… he pulled my up from my knees and asked if I wanted to go further, to which I just nodded… he led me over to the bed, and laid me on my back and I spread my legs… he rubbed my cock and ass a little, then inserted his finger in my hole… I came… a lot… he scooped up my cum with his finger and proceeded to massage it into my waiting hole… he put on a condom, and asked one last more time if I wanted to continue… I told him I wanted his cock… he then pressed his head to my hole… the moment of truth… and he was in… he started slow… holding my legs apart in the air, then picked up the pace… putting my legs on his chest/shoulders… he fucked me for probably five minutes this way, then asked me to roll over and stand up, I complied… He then bent me over the bed and entered me again, and fucked me from behind for another five minutes… his pace quickened, and he came with some final thrusts…

Though all of it I was in somewhat of a trance… I was certainly there, and experiencing it, participating in it, not not enjoying it, but not fully enjoying it either… it didn’t feel bad or hurt, but it didn’t feel great… just ok… when it was all done, he wiped up… asked if I wanted to try anything else, which had I had more time I might have, but I said no, and he got dressed and left… I hopped in the shower, then packed up and checked out of the room… I didn’t feel awkward, or regret or remorse, but also was wondering if the experience had lived up to the fantasies? I’m still not sure… I still have them… I still spend time on Sniffies looking for opportunities to explore more, but the logistics have not worked out yet (though I have received several offers and some delicious dick pics ;-) )… time will tell.

I totally understand your feelings during your encounter. First you probably were in "sub space" where you allowed yourself to submit. Second, often reality does not match our fantasies especially if we play them over and over in our heads. Try it again and see what happens! Yo

 

[Escierto]

My experience was exactly the opposite. I had long fantasized about what it would be like to be fucked. When it finally happened with a transgender woman, it was everything that I had fantasized about and more. I knew that I would never be able to go back to sex with a cisgender woman.

 

[none2_none2]

I have always found that oral sex is way overrated vs the pics, vids and stories about it. Guys just aren't nearly as good at it as they claim to be. On the other hand from the very first time I penetrated a man it was divine! It is just too bad that it isn't possible to impregnate a man to create life as that would be the topping on the cake...

Now with a bad case of ED, I don't get to fuck anymore, but I think of it ALL the time. Sinking inside a man makes me feel like there is a merger that takes place between the two of you even if it is brief. I always wished I were hung like a horse and could fall asleep with my cock still inside a man. Sadly, I am only average, and it sure shrivels up after I would get off.

I could love a woman, and I do not find them unattractive. However, the need to have another man's trust, love, and respect was always far too great. Luckily, my guy fits the description. He is all man, but has a big heart. We have our ups and downs, but he has stood by me through thick and thin. He is faithful as am I.

When sex is a problem (my ED), you see whether your relationship is founded on love or sex. Had it been just about sex, then I'm sure we wouldn't have had an enduring bond. He was by my side when I almost died in 2018 from West Nile. I was by his side when he had 5 by-passes years earlier. Even as great as fucking a man has always been for me, having a man's heart and devotion tops even that.

 

[starfish71]

Sweet story.

If it were me I'd need more connection to get the synergy flowing.

That may have helped... we will see what the next time brings...

 

[yukonnights]

Sweet story.

If it were me I'd need more connection to get the synergy flowing.

This need for more of a connection before intimacy is true of myself too. Unfortunately, in my experience it is the rare man who shares these desires/needs. This is the one thing that perturbs me the most about exploring m+m relationships

I really have zero desire for a casual/anonymous hook-up.

 

[peter49parker]

Long time lurker, first time poster...

So who else has had early experiences that did not quite live up to the fantasies in your mind? I initial experience with a guy was not bad, but not all that either... is the next time different? Of is it more of a journey? Here is how it went....

I had been having gay fantasies since my teenage years… looking at victoria secret catalogs imagining how soft and sexy the outfits would be to wear, looking at porn mags like any teenage boy would, but also wondering what it would be like to be on the receiving end of a cock… the closest things came at the time to playing any of this out was some toying around with a cousin, rubbing our dicks together under the sheets, or in the shower… there was one fleeting attempt at oral, but it ended as awkwardly as it started…

I dated girls in high school, college, and beyond, successfully and happily, but the fantasies remained, and intensified… I explored various porn… mostly straight and some trans (I don’t find gay porn particularly stimulating), imagining I was on the receiving end. I eventually worked up the nerve to buy a toy or two, and some lingerie that I would get dressed up in and masturbate.

This continued for quite some time… even while happily married… but the fantasies remained, and intensified, the toy was not enough… I wanted a real cock in me… I’m not quite sure how, but I stumbled upon Sniffies, and stated looking around… anomalously at first, then set up a profile with a picture of my best angle, in red panties… Let’s say that this generated some interesting attention… everything from “tell me where you are, I’m gonna pound that ass”, to several offers of three-ways, to several sincere chats… a few appeared to have some promise of leading to some sort of play, but always fizzled out… it looked like the one was going to go that way too… after the exchange of the “what are you in to, what are you looking for?” chats, and the exchange of some mouth watering pics, we agreed to meet up… the time was somewhat dependent on work (was on a business trip)… it was either going to be before a dinner engagement if the day’s meetings wrapped up early, or after… well meetings didn’t wrap up, and dinner went long and he was not around, so that night didn’t work out, and I was leaving the next day so it looked like it was going to be a bust too… the next morning, figuring there wasn’t enough time to meet up, I went about packing, and got in one last toy session of the trip and was about to head out to lunch when a message popped up from my paramour… he apologized for not responding the night before, that he had fallen asleep, and wondered if I had time… I decided I could skip lunch and I said I had about an hour and a half before I had to head out… he said he could be at my hotel in about 30 min… I said ok… he asked if I had any of the outfits with me that I had sent in the pictures, which I did… so I quickly put it on and sent him a pic… through discussion he knew I was a virgin, and asked if he should bring something to loosen me up… I told him I had already dildo’d myself that morning, so was ought to be good… he liked that, and asked if I could lube up before he got there… I said yes, and sent him a pic of my shiny hole… His next request was for me to put my dildo in and keep it in until he got there, so I dutifully inserted it balls deep, secured it in place with my thong, and sent him another pic… I think this all made him drive faster since he got there in about 20min… he im’d me when he got to the lobby, and I gave him the room number… I waited anxiously at the door wearing nothing but my black thong, a garter belt and fishnets… then can the knock on the door… housekeeping… wtf… not now thank you!... Then there was the ding of the elevator… I saw a guy coming towards my door… it was now or never… he was no Ryan Reynolds, but not the hunchback of notre dame either, so fuck it, here we go… there’s the knock… I open the door… he is pleased with my presentation… he immediately starts rubbing my ass and crotch… I immediately start rubbing his crotch… nice package… I close the door and we move in to the room, to the seating area, where I help him out of his shirt, and undo the waste on his pants… he peels them off leaving him with just his boxer briefs on… I dropped to my knees in front of him and pull them down releasing his semi-erect cock… my goal was to remove the semi part as quickly as possible…I took his cock in my mouth and began to suck… it was the first real time with cock in my mouth and I was savoring it… I took the head out and worked the shaft to the base, then the balls, then back to the head… it did not take long for him to be a fully erect 7”… he pulled my up from my knees and asked if I wanted to go further, to which I just nodded… he led me over to the bed, and laid me on my back and I spread my legs… he rubbed my cock and ass a little, then inserted his finger in my hole… I came… a lot… he scooped up my cum with his finger and proceeded to massage it into my waiting hole… he put on a condom, and asked one last more time if I wanted to continue… I told him I wanted his cock… he then pressed his head to my hole… the moment of truth… and he was in… he started slow… holding my legs apart in the air, then picked up the pace… putting my legs on his chest/shoulders… he fucked me for probably five minutes this way, then asked me to roll over and stand up, I complied… He then bent me over the bed and entered me again, and fucked me from behind for another five minutes… his pace quickened, and he came with some final thrusts…

Though all of it I was in somewhat of a trance… I was certainly there, and experiencing it, participating in it, not not enjoying it, but not fully enjoying it either… it didn’t feel bad or hurt, but it didn’t feel great… just ok… when it was all done, he wiped up… asked if I wanted to try anything else, which had I had more time I might have, but I said no, and he got dressed and left… I hopped in the shower, then packed up and checked out of the room… I didn’t feel awkward, or regret or remorse, but also was wondering if the experience had lived up to the fantasies? I’m still not sure… I still have them… I still spend time on Sniffies looking for opportunities to explore more, but the logistics have not worked out yet (though I have received several offers and some delicious dick pics ;-) )… time will tell.

I was a late bloomer (65) and have only ever done oral, so far. What I can say is that all of the anticipation and build up to sucking my first cock was spectacular and the fuel for many masturbation sessions, But the real thing was soooo much better. After my buddy finished me off, I couldn't wait to take my first cock and delicious load of sweet cum. I am looking forward to getting fucked next.

 

[Crios]

This need for more of a connection before intimacy is true of myself too. Unfortunately, in my experience it is the rare man who shares these desires/needs. This is the one thing that perturbs me the most about exploring m+m relationships

I really have zero desire for a casual/anonymous hook-up.

I'd prefer to have my first experience with someone I know. A friend, perhaps. I wouldn't be looking at starting a new relationship. Would be looking for someone I could trust and be able to talk about things afterward.

 

[starfish71]

I'd prefer to have my first experience with someone I know. A friend, perhaps. I wouldn't be looking at starting a new relationship. Would be looking for someone I could trust and be able to talk about things afterward.

I too may have preferred that, but it was not something available, so I took the pull the band aid approach. It was either going to be something I didn't care for and move on from (at least pursuing physically), or something to continue exploring. This experience did not fall in to the former category... we'll see where further exploration leads.

 

[Crios]

I too may have preferred that, but it was not something available, so I took the pull the band aid approach. It was either going to be something I didn't care for and move on from (at least pursuing physically), or something to continue exploring. This experience did not fall in to the former category... we'll see where further exploration leads.

I wouldn't be averse to a surprise encounter. Think I mentioned an almost-encounter in one of the threads a while back. Just before covid hit, my wife and I were traveling home on a Sunday night. I had to pee so we stopped at a rest area (or, as we call them in Wisconsin, a Wayside). Wife stayed in the car. I walked into the rest room and there were two guys in the middle of the room, not even in a stall. The one was on his knees and was taking the other guy's cock out of his pants. They saw me come in, jumped up and took off.

Kicking myself to this day. I should've told them to keep going and, after peeing, I would've asked to watch and maybe have a taste. Wouldn't have been able to do much more since the wife would've wondered what was taking so long.

 

[oneblueye]

hey...

Long time lurker, first time poster...

So who else has had early experiences that did not quite live up to the fantasies in your mind? I initial experience with a guy was not bad, but not all that either... is the next time different? Of is it more of a journey? Here is how it went....

I had been having gay fantasies since my teenage years… looking at victoria secret catalogs imagining how soft and sexy the outfits would be to wear, looking at porn mags like any teenage boy would, but also wondering what it would be like to be on the receiving end of a cock… the closest things came at the time to playing any of this out was some toying around with a cousin, rubbing our dicks together under the sheets, or in the shower… there was one fleeting attempt at oral, but it ended as awkwardly as it started…

I dated girls in high school, college, and beyond, successfully and happily, but the fantasies remained, and intensified… I explored various porn… mostly straight and some trans (I don’t find gay porn particularly stimulating), imagining I was on the receiving end. I eventually worked up the nerve to buy a toy or two, and some lingerie that I would get dressed up in and masturbate.

This continued for quite some time… even while happily married… but the fantasies remained, and intensified, the toy was not enough… I wanted a real cock in me… I’m not quite sure how, but I stumbled upon Sniffies, and stated looking around… anomalously at first, then set up a profile with a picture of my best angle, in red panties… Let’s say that this generated some interesting attention… everything from “tell me where you are, I’m gonna pound that ass”, to several offers of three-ways, to several sincere chats… a few appeared to have some promise of leading to some sort of play, but always fizzled out… it looked like the one was going to go that way too… after the exchange of the “what are you in to, what are you looking for?” chats, and the exchange of some mouth watering pics, we agreed to meet up… the time was somewhat dependent on work (was on a business trip)… it was either going to be before a dinner engagement if the day’s meetings wrapped up early, or after… well meetings didn’t wrap up, and dinner went long and he was not around, so that night didn’t work out, and I was leaving the next day so it looked like it was going to be a bust too… the next morning, figuring there wasn’t enough time to meet up, I went about packing, and got in one last toy session of the trip and was about to head out to lunch when a message popped up from my paramour… he apologized for not responding the night before, that he had fallen asleep, and wondered if I had time… I decided I could skip lunch and I said I had about an hour and a half before I had to head out… he said he could be at my hotel in about 30 min… I said ok… he asked if I had any of the outfits with me that I had sent in the pictures, which I did… so I quickly put it on and sent him a pic… through discussion he knew I was a virgin, and asked if he should bring something to loosen me up… I told him I had already dildo’d myself that morning, so was ought to be good… he liked that, and asked if I could lube up before he got there… I said yes, and sent him a pic of my shiny hole… His next request was for me to put my dildo in and keep it in until he got there, so I dutifully inserted it balls deep, secured it in place with my thong, and sent him another pic… I think this all made him drive faster since he got there in about 20min… he im’d me when he got to the lobby, and I gave him the room number… I waited anxiously at the door wearing nothing but my black thong, a garter belt and fishnets… then can the knock on the door… housekeeping… wtf… not now thank you!... Then there was the ding of the elevator… I saw a guy coming towards my door… it was now or never… he was no Ryan Reynolds, but not the hunchback of notre dame either, so fuck it, here we go… there’s the knock… I open the door… he is pleased with my presentation… he immediately starts rubbing my ass and crotch… I immediately start rubbing his crotch… nice package… I close the door and we move in to the room, to the seating area, where I help him out of his shirt, and undo the waste on his pants… he peels them off leaving him with just his boxer briefs on… I dropped to my knees in front of him and pull them down releasing his semi-erect cock… my goal was to remove the semi part as quickly as possible…I took his cock in my mouth and began to suck… it was the first real time with cock in my mouth and I was savoring it… I took the head out and worked the shaft to the base, then the balls, then back to the head… it did not take long for him to be a fully erect 7”… he pulled my up from my knees and asked if I wanted to go further, to which I just nodded… he led me over to the bed, and laid me on my back and I spread my legs… he rubbed my cock and ass a little, then inserted his finger in my hole… I came… a lot… he scooped up my cum with his finger and proceeded to massage it into my waiting hole… he put on a condom, and asked one last more time if I wanted to continue… I told him I wanted his cock… he then pressed his head to my hole… the moment of truth… and he was in… he started slow… holding my legs apart in the air, then picked up the pace… putting my legs on his chest/shoulders… he fucked me for probably five minutes this way, then asked me to roll over and stand up, I complied… He then bent me over the bed and entered me again, and fucked me from behind for another five minutes… his pace quickened, and he came with some final thrusts…

Though all of it I was in somewhat of a trance… I was certainly there, and experiencing it, participating in it, not not enjoying it, but not fully enjoying it either… it didn’t feel bad or hurt, but it didn’t feel great… just ok… when it was all done, he wiped up… asked if I wanted to try anything else, which had I had more time I might have, but I said no, and he got dressed and left… I hopped in the shower, then packed up and checked out of the room… I didn’t feel awkward, or regret or remorse, but also was wondering if the experience had lived up to the fantasies? I’m still not sure… I still have them… I still spend time on Sniffies looking for opportunities to explore more, but the logistics have not worked out yet (though I have received several offers and some delicious dick pics ;-) )… time will tell.

rarely if EVER do the fantasies live up to the Reality where we live
but since according to the physicists, there is no OBJECTIVE REALITY...,
it doesn't matter if the fantasy lives up to the Reality since there is NO reality.

 

[Likeandthey]

To badly paraphrase someone, sex with a partner is just masturbation alongside a partner

 

[dougroundup]

I am unsure just what category officially be filed under...
Many predominantly str8 guys use to use the term Bi-curious. I think that is a way to minimize your own homophobias or denial. I suppose some would even say the whole bisexual category is minimizing the whole gay stigma.... I dunno? I can really only bond and have emotional connections with women, but I have found that I could probably very easily have feelings for a trans person as well. I am very much more attracted to the feminine than the masculine. So much so that I my attraction has always made me very curious and envious of the alluring magical omnipresence power of the female and her magnetic sexual prowess. It has taken me years of exploring soul searching and trying to figure out my strange and strong curiosity to explore having sex with a man? I never really have had an attraction or connection with a man but I kept getting these strong urges to get together with gay men. I would have an illicit hookup about every other year or two.... Always kinda a wham bam anonymous or semi anonymous thing after spending an ever growing amount of time seeking out what was the available scene on chat lines, personal ads and visiting gaybars or cruise spots. Kinda like a spark that grows and begins to flame until it is so hot that it need be extinguished. Over the course of time my tastes and attraction did in fact evolve to where I do now have a very strong physical attraction to cocks. Nice thick fat heavy hung cut cocks that stand perfectly upright at attention with big mushroom head and lots of throbbing veins. But I digress, I suppose we all get that!
As the cycle continued in my life I noticed that many times I most sought out having sex with men happened when I was experiencing failures with my hetero relationships. I also realized I had alot of deep unexplored and repressed submissive tendencies... I began to wonder if it was the submissive itch I was trying to Really scratch, through my seeking out sex with men. Up to this point none of the encounters really ever lived up to my fantasy and really did nothing to rock my boat. I could have some rocking and even crazy wild and mild kinky sex in my hetero world but the ultimate taboo kink of having man sex just wasn't all that I kept fantasizing about. But it did start to get better once I did realize that beyond being a total bottom I had a submissive streak that just wasn't being satisfied with either men and especially not my role with women. As I started to evolve and realize that this was possibly part of what was driving my quest, I started seeking these types of encounters but it was difficult to find just someone who possessed the right stuff to seduce persuade and take from me in just the right ways. I soon learned to seek what I needed and find the right situations. Things improved and I had a couple of satisfactory experiences. But nothing I ever went back to more than once or twice. Although now I wish I would have been less of a one time type of guy. After realizing my attraction mainly to cock, I found myself fascinated with different variations of trans persons and spent much of my attention and developed an attraction to trans. I began to utilize beautiful trans escorts and had some great experience bottoming to some very beautiful professionals. This required a lot of investment of time and many hit n miss experience to find the good from the bad and to appreciate and find respectable , healthy and nice people to work and play with... Most hookups were professionals or with semi-pros or potential pros that I would hit it off with and make friends with enough to not just be a mark or a John. But there were a lot of minefields and pitfalls along they way. You could go down some dark alleys if not careful. It took some learning before finding out how to cultivate my game and be a player within this arena. It is very tough gaining the right and satisfactory experience. It takes a lot of patience, understanding and alot of good karma and sincere caring feelings to get in with this community. Especially if you are a mid aged str8 white guy that is a bottom looking for a hookup. You are typical and a big problem for many within the community. Most have less respect for those they view as a "chaser". A chaser is often taken as either a John or a mark and it is strictly motivated by some sort of transaction, financial or otherwise. I somehow waded my way thru these waters enough to experience a few wonderful and very satisfactory and memorable times with some true unicorns. Some were very professional personal services with very high class providers that showed me how to let go and enjoy, they did all the right things to make me feel real and confident. I learned more about what I needed and wanted and how to let go and trust enough to receive what I may have needed. I was gaining experience and felt confident. I had this naughty part of myself that was beginning to understand some of my likes and dislikes and also I grew in my comfort and acceptance of the diverse identities that people live within nontraditional communities that often are stigmatized and marginalized because of greater society is so hung up on sexualizing everyone and everything, that they don't see the forest thru the trees. Sex is great and sex is fascinating but everything has become judged by the sexualization and objectification of everything yet puts us all in sort of a mixed up dilema between the hypocritical conventional wisdom of right vs wrong.
We are conditioned to be stigmatized by our own instinctive natural predacation to engage in physical and emotional acts of intimacy.
As I begin to discover and reveal more about myself and my true likes and dislikes, I can disassociate conditioning and determine for myself that which is truly disgust and elevate myself beyond the feelings of guilt and remorse and allow for myself to enjoy and let go and seek what I truly want. The fantasies are becoming more real and fully obtainable as I learn what it is I truly want and what I merely only wish for... If I know what I truly want, I prepare to seek it out. If I wish , I will never know or be willing to pay the cost...
In my mind I have sought many things and fantasies. My hard won experiences have conditioned certain aspects of me, but also have given me practice, wisdom and a direction . I have discovered more about my mindset, what makes me tick and allows me insight into others and their possible mindset and motivations. It has provided many surprises as I grow and learn what it is I want to desire and the things I wish as desirable.
I find myself that despite my deep respect, devotion and love for women, I have had a highly sexually charged objectification for the femme form. (My feelings can be viewed as typical chauvinistic male mysoginistic driven hypersexuality of female traits that I have obsessed myself as so desirable. ) The pornographic depiction of a slutty woman dressed as a sex object being submissively and sexually used and pounced upon by a group of heavy hung cock sure dominate males, is the idealized fantasy ang strong curiousity that has taken me to be inquisitive towards seeking out the pleasure of bottoming out and surrendering to a hard cock.
I first found fascination in the powerful phallous. But I needed more than that and found my submissiveness and that which goes along with the many directions and turns in the road. I learned to let go and let another take me to the places I could not freely allowyself. I still couldn't finally relieve that itch until I found the enjoyment of my attraction, the beauty of the femme form, but as the pervy often say the best of both worlds. Seeking that unicorn with beauty, tits and powerful cock willing to subject me to their pleasure... To discover that which I have actually took me to this road,,, the wish to experience the femme sexuality, to wish to know how it feels to be woman. I know I want to Crossdress and roleplay as a woman and be the objectified sissy bitch. To be used and enjoy sex like a super sexed woman and play with all those adornments and the fun of going outside of myself to pretend to be someone and something else. My biggest and greatest fantasy wish would be to have a full transformational makeover with full body and skincare ... Completely soft smooth . To be fitted and dressed to perfection with the right garments and shapewear, makeup and hair to perfection and enough practice and couching to walk the walk and talk the talk . I want to be dressed somewhat classy with a bit more sexy and to go out to the clubs and bars where my sisters and I go to receive the attention we desire. I want to be that CD that has to work her way thru all the chasers and gets to flirt and be seduced and taken by that virile and strong dominating gentlemen. I want to be treated as a gentleman properly shows a lady and when the club and bars close I want to be seduced and taken to his lair where he brings out my inner slut and does things to me that are decadent and over the top.
Making the beautiful CD become his kinky slutty whore, being used and every bit of my manhood disregarded. I am now a pornographic fantasy femme for a weekend to remember.

 

[xt600e]

I was a late bloomer (65) and have only ever done oral, so far. What I can say is that all of the anticipation and build up to sucking my first cock was spectacular and the fuel for many masturbation sessions, But the real thing was soooo much better. After my buddy finished me off, I couldn't wait to take my first cock and delicious load of sweet cum. I am looking forward to getting fucked next.

Let me know how it goes.

 

[PG564E]

Long time lurker, first time poster...

So who else has had early experiences that did not quite live up to the fantasies in your mind? I initial experience with a guy was not bad, but not all that either... is the next time different? Of is it more of a journey? Here is how it went....

I had been having gay fantasies since my teenage years… looking at victoria secret catalogs imagining how soft and sexy the outfits would be to wear, looking at porn mags like any teenage boy would, but also wondering what it would be like to be on the receiving end of a cock… the closest things came at the time to playing any of this out was some toying around with a cousin, rubbing our dicks together under the sheets, or in the shower… there was one fleeting attempt at oral, but it ended as awkwardly as it started…

I dated girls in high school, college, and beyond, successfully and happily, but the fantasies remained, and intensified… I explored various porn… mostly straight and some trans (I don’t find gay porn particularly stimulating), imagining I was on the receiving end. I eventually worked up the nerve to buy a toy or two, and some lingerie that I would get dressed up in and masturbate.

This continued for quite some time… even while happily married… but the fantasies remained, and intensified, the toy was not enough… I wanted a real cock in me… I’m not quite sure how, but I stumbled upon Sniffies, and stated looking around… anomalously at first, then set up a profile with a picture of my best angle, in red panties… Let’s say that this generated some interesting attention… everything from “tell me where you are, I’m gonna pound that ass”, to several offers of three-ways, to several sincere chats… a few appeared to have some promise of leading to some sort of play, but always fizzled out… it looked like the one was going to go that way too… after the exchange of the “what are you in to, what are you looking for?” chats, and the exchange of some mouth watering pics, we agreed to meet up… the time was somewhat dependent on work (was on a business trip)… it was either going to be before a dinner engagement if the day’s meetings wrapped up early, or after… well meetings didn’t wrap up, and dinner went long and he was not around, so that night didn’t work out, and I was leaving the next day so it looked like it was going to be a bust too… the next morning, figuring there wasn’t enough time to meet up, I went about packing, and got in one last toy session of the trip and was about to head out to lunch when a message popped up from my paramour… he apologized for not responding the night before, that he had fallen asleep, and wondered if I had time… I decided I could skip lunch and I said I had about an hour and a half before I had to head out… he said he could be at my hotel in about 30 min… I said ok… he asked if I had any of the outfits with me that I had sent in the pictures, which I did… so I quickly put it on and sent him a pic… through discussion he knew I was a virgin, and asked if he should bring something to loosen me up… I told him I had already dildo’d myself that morning, so was ought to be good… he liked that, and asked if I could lube up before he got there… I said yes, and sent him a pic of my shiny hole… His next request was for me to put my dildo in and keep it in until he got there, so I dutifully inserted it balls deep, secured it in place with my thong, and sent him another pic… I think this all made him drive faster since he got there in about 20min… he im’d me when he got to the lobby, and I gave him the room number… I waited anxiously at the door wearing nothing but my black thong, a garter belt and fishnets… then can the knock on the door… housekeeping… wtf… not now thank you!... Then there was the ding of the elevator… I saw a guy coming towards my door… it was now or never… he was no Ryan Reynolds, but not the hunchback of notre dame either, so fuck it, here we go… there’s the knock… I open the door… he is pleased with my presentation… he immediately starts rubbing my ass and crotch… I immediately start rubbing his crotch… nice package… I close the door and we move in to the room, to the seating area, where I help him out of his shirt, and undo the waste on his pants… he peels them off leaving him with just his boxer briefs on… I dropped to my knees in front of him and pull them down releasing his semi-erect cock… my goal was to remove the semi part as quickly as possible…I took his cock in my mouth and began to suck… it was the first real time with cock in my mouth and I was savoring it… I took the head out and worked the shaft to the base, then the balls, then back to the head… it did not take long for him to be a fully erect 7”… he pulled my up from my knees and asked if I wanted to go further, to which I just nodded… he led me over to the bed, and laid me on my back and I spread my legs… he rubbed my cock and ass a little, then inserted his finger in my hole… I came… a lot… he scooped up my cum with his finger and proceeded to massage it into my waiting hole… he put on a condom, and asked one last more time if I wanted to continue… I told him I wanted his cock… he then pressed his head to my hole… the moment of truth… and he was in… he started slow… holding my legs apart in the air, then picked up the pace… putting my legs on his chest/shoulders… he fucked me for probably five minutes this way, then asked me to roll over and stand up, I complied… He then bent me over the bed and entered me again, and fucked me from behind for another five minutes… his pace quickened, and he came with some final thrusts…

Though all of it I was in somewhat of a trance… I was certainly there, and experiencing it, participating in it, not not enjoying it, but not fully enjoying it either… it didn’t feel bad or hurt, but it didn’t feel great… just ok… when it was all done, he wiped up… asked if I wanted to try anything else, which had I had more time I might have, but I said no, and he got dressed and left… I hopped in the shower, then packed up and checked out of the room… I didn’t feel awkward, or regret or remorse, but also was wondering if the experience had lived up to the fantasies? I’m still not sure… I still have them… I still spend time on Sniffies looking for opportunities to explore more, but the logistics have not worked out yet (though I have received several offers and some delicious dick pics ;-) )… time will tell.

Extremely sexy - thank for sharing your experience. This is very hot.

 

[2tallpaul]

I've been fortunate to be with a woman that makes any fantasy work. I've been willing and any remote idea has surpassed my expectations. Of any fantasy was after being pegged, what did a real one feel like, that was the best. Having a partner that wants to share has made it happen.

 

[ZacharyFagg]

I think for that real, fantasy like awesome sex, chemistry is very important. While random hookups can be hot, they aren't always what we imagine. My hottest sexual encounters have almost always been with regular that I had amazing sexual chemistry with, or guys that I had chatted with for a long time before meeting.