This is a story that I've told piecemeal to a bunch of people here on LPSG.
I've lately been really into The Moth
The Moth - YouTube
and inspired by the storytelling therein, I've decided to write down the story of my first sexual encounter.
Before I get into the story, I'd like to lay some foundations and give a bit of background to it.
Growing up I wanted to be what I thought of as a "man's man". A macho man, a cool guy. A man that would get everything he wanted, the type of man that women couldn't keep their hands off. The kind of guy that would have loads of women each weekend.
Juvenile? But of course. I was just a kid.
None of that ever came to pass, of course.
In hindsight, that's probably just as well. However, at the time (and still, occasionally), it frustrated me that my (albeit vague) goals and my reality were so very far from each other.
During my early teens, I saw people around me start exploring their sexuality as our hormones started to slosh around.
I'll get my chance later, I thought.
School moved forward, but still nothing.
Later. My chance will pop up later.
I went to "high-school" (roughly translated, ages 15-18). We were about 150 guys and maybe 2 girls.
Alright, but I'm planning to go to university so I'm sure it'll sort itself there.
I go to university, get my own student apartment and the whole kit. I spent five years there, going from 19 to 24.
Still nothing.
Except for one time.
Again, I saw how people around me started to get into relationships of various kinds. How some of my pals were having brief encounters at (and after) parties.
A good friend of mine told me about an internet dating site. Being a frugal student I was skeptical.
I was informed that this was a free site. Fool that I was, I thought that seemed like a good idea. It wasn't until later (far too late) that I would realize that pay-gates are there for a reason.
So I got onto this site, made a user, the whole kit. I even had a friend with photography as a hobby take a few pictures of me for use on this site.
I started sending messages to women that caught my eye. I'd heard about the almost mechanical trawling technique that is often used on such sites: make a standard message and basically just copy+paste it to all the women you're after, making small adjustments.
Screw that, I thought. I was going to make an effort. I hand wrote each message, trying my best to be charming without coming on too strong.
I had a 100% rejection rate whenever a woman deigned to reply. Most just ignored my messages.
After having been sexually frustrated for years, this was a pretty nasty blow to my already shaky ego. I thought "fuck this shit", more or less, and pulled away.
But then, one day, I got a message.
A woman had contacted me. Without my first having made contact with her. That is to say, she came to me first. This was a salve to my battered (and more broken than bruised) ego.
We exchanged messages for a time. She only had a user image, and no pictures in her profile. This should've set off warning bells, but I was blinded by somebody actually giving me attention in this way.
At one point, it came out that I had never been in a relationship before and my status as a virgin then slipped through as well. More conversation followed, and I made a joke along the lines of "good looking, hung guy". It was a bit of a gamble, as I reasoned that interesting as this was, it would most likely never go anywhere.
However, this caught her interest, it seemed. More discussions followed, and more or less turned into sexting. We settled on a date for a meet.
At the time it was summer vacation, and I was at my parents' place. I was going to meet the woman in the city where I studied, so the evening before the date I took the train there and slept in my apartment. In the morning I carefully prepared: washing, shaving (upstairs and downstairs), etc.
I was nervous. Not only was I going to meet this stranger, but I was most likely going to have sex with her as well. I set off through the city, walking fast to shake my nerves.
She shared a house with a bunch of people in a part of town I seldom had reason to visit. I had to call her for directions before I arrived. And then I saw her. She would come to codify my tastes in women.
Because she was everything I don't desire.
She was short, plain and fat. Not chubby. Fat. The pale skin of her upper lip was very lightly shaded by the unfortunate placement of some dark down.
She did have nice breasts, though. The type that, even if she wasn't fat, they would most likely still be nice.
I considered turning on my heel and just walking away from all of this. My rational mind was going "Dude, you've been without this long, you can go a few years more. Let's just leave."
But then my dick took over. He basically said "Dude, we may never get another chance. Just go with the flow, man!"
And he won.
We sat in her garden for a bit, chatting idly. There was some tension there, of course, but at the moment we were just two people exchanging small talk. I think she was checking to see if I could be trusted to follow her up to her room.
As my dick was in full control now, and my rational mind had gone into hiding, I took off my shirt. I reasoned that I might as well put the effort in. It was the hottest day of that summer, and so I asked her if it would be OK to take my shirt off. I wanted to show off my chest. She assented, and there I sat, bare chested.
Some more talk, and finally, she invited me up to her room. I put on my shirt again, and up we went.
I saw a few of her housemates. I still remember one guy. His room was adjacent to her room, and he was sitting on his floor doing something. I gave him a silent nod. I'm pretty sure he knew why I was there. I felt as I imagine a john must feel like in a brothel.
We get into her room, and she closed the door. A bit more talk. She asked me how I was feeling and I said that I was feeling a "physical reaction". A term jokingly used during our message exchanges to indicate that I had gotten an erection.
We started to make out. I can't say I cared for it, but it let me fondle her breasts, which was something, at least.
In time we got naked. I was vaguely dissapointed that she didn't say more about my dick than "Oh" when I flopped it out. We made out some more while I fingered her and she gave me a sort-of handjob.
After a while she decided it was time to suck me off. We had discussed beforehand that as this was my first time, it would probably be wise to start with a quick blowjob to take the edge off, so to speak. We both expected me to pop quickly.
She had a small mouth, and I did enjoy her struggle a bit with my girth. Aside from that I can't say that the blowjob was all that great. What went through my mind was basically something along the lines of "That's it?". It wasn't unpleasant, it just wasn't as good as I thought it would be.
A long while passed, and I think her jaw got tired, or something. She wanted to fuck, now. It was obvious that I wasn't going to pop too soon. It was a bit of an ego boost that she was apparently more eager to fuck than I was.
I struggled to get a condom on. She helped, a bit too roughly for my tastes. Then she got her bulk on me, and almost broke my dick. She was tight, and with her weight suddenly coming down on my dick, too fast, it bent uncomfortably. I had to lift her and manouver her a bit before I could get in properly.
I'll admit that I did take some pleasure in the fact that I was stretching her out. Aside from that, though, I was once again underwhelmed. We shifted through a variety of positions, none of them all that exotic.
The whole act was seriously wet and sticky, this being the hottest day of the summer, and she being a very fat woman. Missionary was not a good idea, as I was in danger of being glued to her by her sweat.
Doggystyle worked best. I remember looking to the side and seeing an old TV, the type with a curved, shiny screen. I could clearly see us reflected in it, and for a few moments I got some strange satisfcation in watching us fuck, like watching a porno that I was starring in.
I remember checking my watch, which I was still wearing. Doing so tickled me, as it is such a forbidden thing to do during sex, and something usually (in comedic situations) done by the woman.
At the time, I was in good condition, and I could keep up a good humping pace. She was impressed. She demonstrated this by reaching orgasm very loudly. Sometimes I wonder if it was real, and I still hope it was. I think it was real because she seemed very embarrassed as to the loudness of her orgasm: all her housemates would've had heard her. The walls were thin.
I kept thrusting away, feeling more and more like a workout, or a chore. All I felt was warm pressure on my dick, and very distantly, a vaguely pleasurable sensation. Was this sex? I'd had wank sessions that were more stimulating.
We had penetrative sex for more than an hour, all told. I think either she got bored, tired or worn out, and she told me that she wasn't going to orgasm again. I asked her about women and multiple orgasms, but she said "she didn't do that". I suspected that she just wasn't enjoying it.
I pulled out and asked her to suck me off the last bit. To finish me orally. She refused. Inside the condom, which I now pulled off, my dick was all sweaty and sticky. She didn't want to suck me off because I had had a condom on. I was dissapointed, but didn't press her. I settled for a finishing handjob.
I've lately been really into The Moth
The Moth - YouTube
and inspired by the storytelling therein, I've decided to write down the story of my first sexual encounter.
Before I get into the story, I'd like to lay some foundations and give a bit of background to it.
Growing up I wanted to be what I thought of as a "man's man". A macho man, a cool guy. A man that would get everything he wanted, the type of man that women couldn't keep their hands off. The kind of guy that would have loads of women each weekend.
Juvenile? But of course. I was just a kid.
None of that ever came to pass, of course.
In hindsight, that's probably just as well. However, at the time (and still, occasionally), it frustrated me that my (albeit vague) goals and my reality were so very far from each other.
During my early teens, I saw people around me start exploring their sexuality as our hormones started to slosh around.
I'll get my chance later, I thought.
School moved forward, but still nothing.
Later. My chance will pop up later.
I went to "high-school" (roughly translated, ages 15-18). We were about 150 guys and maybe 2 girls.
Alright, but I'm planning to go to university so I'm sure it'll sort itself there.
I go to university, get my own student apartment and the whole kit. I spent five years there, going from 19 to 24.
Still nothing.
Except for one time.
Again, I saw how people around me started to get into relationships of various kinds. How some of my pals were having brief encounters at (and after) parties.
A good friend of mine told me about an internet dating site. Being a frugal student I was skeptical.
I was informed that this was a free site. Fool that I was, I thought that seemed like a good idea. It wasn't until later (far too late) that I would realize that pay-gates are there for a reason.
So I got onto this site, made a user, the whole kit. I even had a friend with photography as a hobby take a few pictures of me for use on this site.
I started sending messages to women that caught my eye. I'd heard about the almost mechanical trawling technique that is often used on such sites: make a standard message and basically just copy+paste it to all the women you're after, making small adjustments.
Screw that, I thought. I was going to make an effort. I hand wrote each message, trying my best to be charming without coming on too strong.
I had a 100% rejection rate whenever a woman deigned to reply. Most just ignored my messages.
After having been sexually frustrated for years, this was a pretty nasty blow to my already shaky ego. I thought "fuck this shit", more or less, and pulled away.
But then, one day, I got a message.
A woman had contacted me. Without my first having made contact with her. That is to say, she came to me first. This was a salve to my battered (and more broken than bruised) ego.
We exchanged messages for a time. She only had a user image, and no pictures in her profile. This should've set off warning bells, but I was blinded by somebody actually giving me attention in this way.
At one point, it came out that I had never been in a relationship before and my status as a virgin then slipped through as well. More conversation followed, and I made a joke along the lines of "good looking, hung guy". It was a bit of a gamble, as I reasoned that interesting as this was, it would most likely never go anywhere.
However, this caught her interest, it seemed. More discussions followed, and more or less turned into sexting. We settled on a date for a meet.
At the time it was summer vacation, and I was at my parents' place. I was going to meet the woman in the city where I studied, so the evening before the date I took the train there and slept in my apartment. In the morning I carefully prepared: washing, shaving (upstairs and downstairs), etc.
I was nervous. Not only was I going to meet this stranger, but I was most likely going to have sex with her as well. I set off through the city, walking fast to shake my nerves.
She shared a house with a bunch of people in a part of town I seldom had reason to visit. I had to call her for directions before I arrived. And then I saw her. She would come to codify my tastes in women.
Because she was everything I don't desire.
She was short, plain and fat. Not chubby. Fat. The pale skin of her upper lip was very lightly shaded by the unfortunate placement of some dark down.
She did have nice breasts, though. The type that, even if she wasn't fat, they would most likely still be nice.
I considered turning on my heel and just walking away from all of this. My rational mind was going "Dude, you've been without this long, you can go a few years more. Let's just leave."
But then my dick took over. He basically said "Dude, we may never get another chance. Just go with the flow, man!"
And he won.
We sat in her garden for a bit, chatting idly. There was some tension there, of course, but at the moment we were just two people exchanging small talk. I think she was checking to see if I could be trusted to follow her up to her room.
As my dick was in full control now, and my rational mind had gone into hiding, I took off my shirt. I reasoned that I might as well put the effort in. It was the hottest day of that summer, and so I asked her if it would be OK to take my shirt off. I wanted to show off my chest. She assented, and there I sat, bare chested.
Some more talk, and finally, she invited me up to her room. I put on my shirt again, and up we went.
I saw a few of her housemates. I still remember one guy. His room was adjacent to her room, and he was sitting on his floor doing something. I gave him a silent nod. I'm pretty sure he knew why I was there. I felt as I imagine a john must feel like in a brothel.
We get into her room, and she closed the door. A bit more talk. She asked me how I was feeling and I said that I was feeling a "physical reaction". A term jokingly used during our message exchanges to indicate that I had gotten an erection.
We started to make out. I can't say I cared for it, but it let me fondle her breasts, which was something, at least.
In time we got naked. I was vaguely dissapointed that she didn't say more about my dick than "Oh" when I flopped it out. We made out some more while I fingered her and she gave me a sort-of handjob.
After a while she decided it was time to suck me off. We had discussed beforehand that as this was my first time, it would probably be wise to start with a quick blowjob to take the edge off, so to speak. We both expected me to pop quickly.
She had a small mouth, and I did enjoy her struggle a bit with my girth. Aside from that I can't say that the blowjob was all that great. What went through my mind was basically something along the lines of "That's it?". It wasn't unpleasant, it just wasn't as good as I thought it would be.
A long while passed, and I think her jaw got tired, or something. She wanted to fuck, now. It was obvious that I wasn't going to pop too soon. It was a bit of an ego boost that she was apparently more eager to fuck than I was.
I struggled to get a condom on. She helped, a bit too roughly for my tastes. Then she got her bulk on me, and almost broke my dick. She was tight, and with her weight suddenly coming down on my dick, too fast, it bent uncomfortably. I had to lift her and manouver her a bit before I could get in properly.
I'll admit that I did take some pleasure in the fact that I was stretching her out. Aside from that, though, I was once again underwhelmed. We shifted through a variety of positions, none of them all that exotic.
The whole act was seriously wet and sticky, this being the hottest day of the summer, and she being a very fat woman. Missionary was not a good idea, as I was in danger of being glued to her by her sweat.
Doggystyle worked best. I remember looking to the side and seeing an old TV, the type with a curved, shiny screen. I could clearly see us reflected in it, and for a few moments I got some strange satisfcation in watching us fuck, like watching a porno that I was starring in.
I remember checking my watch, which I was still wearing. Doing so tickled me, as it is such a forbidden thing to do during sex, and something usually (in comedic situations) done by the woman.
At the time, I was in good condition, and I could keep up a good humping pace. She was impressed. She demonstrated this by reaching orgasm very loudly. Sometimes I wonder if it was real, and I still hope it was. I think it was real because she seemed very embarrassed as to the loudness of her orgasm: all her housemates would've had heard her. The walls were thin.
I kept thrusting away, feeling more and more like a workout, or a chore. All I felt was warm pressure on my dick, and very distantly, a vaguely pleasurable sensation. Was this sex? I'd had wank sessions that were more stimulating.
We had penetrative sex for more than an hour, all told. I think either she got bored, tired or worn out, and she told me that she wasn't going to orgasm again. I asked her about women and multiple orgasms, but she said "she didn't do that". I suspected that she just wasn't enjoying it.
I pulled out and asked her to suck me off the last bit. To finish me orally. She refused. Inside the condom, which I now pulled off, my dick was all sweaty and sticky. She didn't want to suck me off because I had had a condom on. I was dissapointed, but didn't press her. I settled for a finishing handjob.