First Experience With Another Man

[Escierto]

I remember my first date with a man...It was magical....he was fully aware that I was MTF TG...and that it was my first date with a man. We went out to dinner at a very exclusive restaurant. When placed his hand on the small of my back to guide through the door as he held it open I knew that this is what I wanted my life to be. A few heads turned not because people thought I was trans but because of our age difference. Dan was about 20 years older than me. He order drinks for us. No ask any questions since he looked like a dad buying his daughter a glass of wine, We chatted and talked about where I was going in life, college, etc.
After dinner we went to the theater to watch a presentation of A Christmas Carol. we held hands walking to and from the parking garage. Again be bought us a glass of wine at intermission. All too soon it was over we headed home. It felt so warm and cozy in his car for the hour drive home. We must have sat parked in front of my house for a half an hour saying good night. His first kiss a gentle kiss good night, but I kissed back a bit more passionately. Hearts were racing, hands were roaming and the moment was so arousing for me I that my tiny panties were soaked.
We finally said good nite, and I hobbled back to the house in my hi heels, hoping nothing was running down my legs.
Mom was asleep when I got in the house. Telling about my date had to wait until morning

It sounds like you had a lovely time. Good for you!

 

[HeatherMaureen8065]

In my case a gay male was unobtrusively moving his hand up my thigh while we were talking across the street from where I lived after he'd picked me up hitching a ride. I have no idea how long it took me to notice but by the time I did I was becoming very hard and startig to breathe heavy! no idea what would have happened as a police car slowed as it went by and that scared him off. Practically threw me out of his car but I let him know that I'd need a ride again in two days.
I'd never been with a male or given it any thought being in my last year of high school and while pretending to be very macho in truth I was an extremely closeted transvestite. Yes I'd dress up secretly and think of myself as being girly after I had but this was the first time a male had shown any interest in me. Of course no one but me knew that at the time! The closest I'd come to being out was using the garage to dress up and furtively scurrying down the back alley late at night a few times.
His hand had felt so incredibly arousing I couldn't stop thinking about it which may be why I'd blurted out that I'd need a ride from the same spot in two days. If it had felt that incredible thru my blue jeans I kept wondering how it would feel if I was smooth,hairless and wearing nylons like a girl would be.
To make a longer story short I got him to stop at a gas station where I finished transforming myself into my femme self before getting into his car. Worried that he might reject my girly side I was overjoyed when he smiled at me, drove to his place after introducing me to exhibitionism and I spent the night discovering what it was like to be caressed, fondled, kissed, undressed and fucked by a man! Oh yes we did suck each other along the way.
More the seducee then the seducer but that was how it happened that I became his sissy slut for the next year before he moved to a different city for his work.

 

[Lighthousenorth]

Seems like a common problem. Have you tried networking on Silverdaddies? It’s been more successful for me than other websites. Keep after it.

I can confirm that. Silverdaddies is the only site that led to real meetings for me.

 

[Lighthousenorth]

I recognize the feeling. I wrote the story of my first gay experience at https://www.literotica.com/s/finally-we-met

 

[whiskeytangofoxtrot]

Hubby's first time was 40 years ago at a Bachelorette party and I saw it live. Maid of honor hired two guys and hubby thought he was the only one. We had him in the shower while we watched and the other guy joined him. His look was priceless! Lol.

Later they performed separately and jointly for us. It was the best!!!

 

[suck4you]

Over the years I have met a few older guys who say they have no experience, one I met definitely did not have any experience but I got him hard talking to him and rubbing him then on my knees and sucking him he soon forgot about his nerves and shot a good load in my mouth, but others I have met have told me they have no experience then once we get together they want to fuck me as well, bonus for me bonus for him LOL

 

[ChrissyCD64]

Can't talk about my first experience due to Lit rules.

 

[SPARTAN047]

Hehehe, I see so many references to... This.

I did watch porn a bit outside the rules.

 

[CuriousinPennsylvania]

Very hot.

Simular to my very first time too. I was divorced, bored, horny, and found my self at an adult bookstore.

I thought the video booths were only for watching movies! Another guy gave me a blow job I still remember today.

When I got ready to cum, he just broke off making love to my cock long enough to say, "give me everything".

Really amazing mixture of nervousness, pleasure, smells, and relief to give me a #10 orgasm.

Been to the video booths at ABSs many times, only to watch movies, but somehow, almost every time was there I wound up getting a blowjob. Those damned cocksuckers.

The smell of the bleach used to clean up the floors, mixed with the smell of cum, elicits thoughts of what has happened in those booths.

 

[Ciceri]

Is Grindr app still a thing? My first meeting wasn't for sex at all. I did contract work for an older gentleman and after a month he confessed his attraction to me. That wasn't a big surprise. Still, I wasn't biting the hook. His questions got bolder. He asked if I'd ever been in drag. I confessed I had been. Soon, my secret was revealed: I was wearing panties under my Carhartt pants. And I showed him. Everything changed after that moment. That's the cue he was looking for

 

[Escierto]

Is Grindr app still a thing? My first meeting wasn't for sex at all. I did contract work for an older gentleman and after a month he confessed his attraction to me. That wasn't a big surprise. Still, I wasn't biting the hook. His questions got bolder. He asked if I'd ever been in drag. I confessed I had been. Soon, my secret was revealed: I was wearing panties under my Carhartt pants. And I showed him. Everything changed after that moment. That's the cue he was looking for

I used Grindr years ago to try to meet transgender women. All I got were dick pics from a lot of horny guys.

 

[Ciceri]

I used Grindr years ago to try to meet transgender women. All I got were dick pics from a lot of horny guys.

The idea was to meet up. That's a burn

 

[Crios]

Been to the video booths at ABSs many times, only to watch movies, but somehow, almost every time was there I wound up getting a blowjob. Those damned cocksuckers.

The smell of the bleach used to clean up the floors, mixed with the smell of cum, elicits thoughts of what has happened in those booths.

They say few things elicit memories like smell. Breathing in the ABS booth smell you described always, and I mean always, got me hard.