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Pleasant surprises and disappointments in first gay experiences

Travler99921 said:
I was a late bloomer. I was over 50 when I had my first gay encounter. I was surprised how much I enjoyed some things while other things were disappointing. I could not believe how good it felt just to touch another man's cock. I expected to enjoy having my cock sucked, but it was much better than I expected. The same was true of sucking another man's cock. After the first time there was no doubt I was a cocksucker.

The biggest disappointment was 69. It was not bad, but I much preferred taking turns. Kssing a man was another disappointment.


I am not sure if it was a disappointment or a blessing, but I failed to develop any emotional connections with my male sex partners. That is true to this day. There was sometimes a bit of an afterglow, but it did not last long. I remain hetroromantic to this day.
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Pleasant surprises: How good it felt when he leaned over and kissed me, then sucked my cock until I finished in his mouth.

Even Better: How natural it felt to suck his hard, fat cock, until he finished in my mouth, and I swallowed.

Disappointments: I had to wait a whole week to suck him off again.
 
Thought about being with another guy for years and decided to give myself a 50th birthday present. On line chat with another local married guy led to a meeting and agreement to meet at a motel. Nervous as hell but determined to do it. In the room, sitting on the bed, I said I wasn't sure what to do next and he leaned over and kissed me.
Surprised at how much I liked kissing him. Even more surprised at how much I liked sucking his cock. He was surprised at how good I was for a first timer ( Years of fantasy probably explains that). I wasn't ready to let him cum in my mouth but I strokes him off and liked watching and hearing him cum.
Definitely not surprised at how much I enjoyed being naked with another man and liked him sucking me. Disappointed that I could not cum (nerves again)
Not at all disappointed that he wanted to get together again. Very happy that it became a regular FWB relationship that lasted for years. The nervousness disappeared.
Disappointed that I have never found another friend like him
 
HOT!! Nice job getting out there and making it happen? I’m a 46 muscular & masculine bi wm and need to take your advice!
 
My first gay experience as an adult occurred when I was in my early Thirties. I met up with a gay friend of the family who was a few years older than me. I asked him to take me home and have his way with me. We went right to his bedroom and got naked.

He asked me what I wanted to try. Of course I wanted to suck his cock. He made me kneel in front of him and service his cock and balls for quite some time. I was drooling all over myself and has fat dick as I did so. He would occasionally reach down and play with my ass.

He asked me if I wanted to experience him penetrating me. I jumped on his bed, putting my head down and my ass up. He slowly began to rub my hole and work a finger then two into me. He was very patient working lubricant into me. I was begging for his cock in short order.

He slowly slid into my tight virgin hole inch by inch until I felt his belly against my back. Painful at first but he worked me through it and eventually had me slide back to meet his thrusts. He was in my for quite some time before he pulled out and came on my back.

I loved every minute of this experience and have duplicated many times in the past twenty years.
 
Travler99921 said:
I was a late bloomer. I was over 50 when I had my first gay encounter. I was surprised how much I enjoyed some things while other things were disappointing. I could not believe how good it felt just to touch another man's cock. I expected to enjoy having my cock sucked, but it was much better than I expected. The same was true of sucking another man's cock. After the first time there was no doubt I was a cocksucker.

The biggest disappointment was 69. It was not bad, but I much preferred taking turns. Kssing a man was another disappointment.


I am not sure if it was a disappointment or a blessing, but I failed to develop any emotional connections with my male sex partners. That is true to this day. There was sometimes a bit of an afterglow, but it did not last long. I remain hetroromantic to this day.
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I hope you don't mind, but I am going to Hijack this thread ever so slightly as some of these posts have reminded me...

Pleasant surprises and disappointments in first gay experiences with a certain new guy

I met this guy online and after a week of chatting and one quick coffee meeting we agreed to meet the following day after work at a hotel that I could procure for the night. We were both admitted total bottoms, and we both loved to suck so we figured we could still have a fun evening together without any anal sex. He made his excuse at home to be late and assured me he could not stay the night... no big deal to me.

I arrived around 4:00 PM and got settled in the room. I had brought several bottles of wine and glasses from home (yes, I am a romantic), but I decided to hit the hotel bar to have a little "relaxation first." After a few warmup glasses, I went back to the room to shower, text him my room number, and get ready for his 5:15 arrival. Right on time he knocked, and I let him in. He asked to shower (Thank Goodness) and he had bought a travel size shaving cream and disposable razor to be nice and smooth for me. When he left the bathroom, I handed him a glass of wine, and we toasted new friends!

I will save you all the lucid details of the next two hours of fun, but let's just say we sucked, jerked, and sucked each other completely dry. He left after a quick shower to wash off any evidence before returning home to his family. I rinsed off quickly after he left and returned to the hotel bar to watch some hoops and have another few drinks.

When I woke the next morning, I had 15-20 emails and texts from him. (There were none when I went to sleep around 11:00) The general gist of his messages was that he had a GREAT time last night, and he could not wait to meet up again. OK good!

Then he said he could not wait to feel me FILL him, to make him my girl...

Excuse me? I am a total bottom, I don't fill anything, except some days my hand with a small dribble of cum. I am not interested in topping ANYONE, no matter how much fun last night was.

Did I miss the memo? Needless to say, I never communicated with him again.

Thanks to the OP for letting me rant slightly off topic!
 
Cabeza said:
Pleasant: I never considered how much fun it could be to stroke and suck a cock. Way back when, I assumed men only did this so the other guy would reciprocate. But playing with penises is awesome.

Disappointment: None of the guys I was ever with made much attempt to make me feel good. They all fit the male stereotype of wanting to get off / get fucked and then roll over and go to sleep .
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Do not like men who want just a one sided time.

I really enjoy playing with and being played with, yet my experience is that not many of the guys want to return the experience.
 
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