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Pleasant surprises and disappointments in first gay experiences

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
 
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.
Click to expand...
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 .
Click to expand...
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.
 
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.
Click to expand...
Yeah, I adore giving cock worship but not a huge 69ers fan...I can't enjoy because my focus is totally on the cock I'm currently pleasuring. To that end, that orientation in space (versus sexual orientation) is not for me, ideal. I enjoy more the traditional manner, where I can look at him and he, me. As well, I've had a few where I kind of...."wished" is a strong term but sometimes it is slightly regrettable that there couldn't be actual "intimacy" but...it's probably better for me that I'm just a fuck-toy, because I'm far too broken to handle anything beyond the physical...and not "affectionate" physical, but the highly sexual physical where I'm being used, basically. So now and then, sure, the tiniest of pangs of wistfulness quickly followed by me remembering that, um.....I'm me. So not really a good idea to....you know....care. For anything. At all. Ever. It's much better to dive head first and just revel in being a fuck toy and a cum dumpster. It's weirdly fun to realize one has zero intrinsic value. You can do anything to yourself zero guilt. In fact, it's almost like symmetry. What's that saying? "Know Yourself"? It's good to know where you stand, your role and not only accept it but make it your identity. And have fun with it! "Your body is a temple!" No, YOUR body is a temple. I'm here to be an amusement park! And if nobody is riding me? I'll ride myself. And why the fuck are you even saying anything? Like you give a fuck. NO, you just like to preach.

You know what's interesting? What if, when a person drove drunk and wrapped their car around a tree, totaling it, the car still existed but now it acted up sometimes and people just got pissed at the car for acting up, because nobody knew the reason was it got totaled by it's owner...who's not around...and the car knows better than to even say "Yeah, well...my former owner destroyed me" because then folks would be like "Now now, you can't blame others for your lack of being the best car...no excuses!" and the car is all like, "who's making excuses? I just won Daytona!...just explaining is all". Then the car gets a new owner and THAT owner fucking runs it into a building...and the car is all like, "This is getting to be a pattern!" Then the 3rd owner tells the car that there's this invisible Rolls Royce that created all the cars including him and that he watches over the cars. So now the car thinks...huh....well maybe that's my role - to be wrecked. Kind of weird that to know there's something that could have maybe not let me get totaled over and over. Maybe that's what the Invisible Great Rolls Royce made me for....it must hate me." Then the new owner gets really mad that the car thinks that way about the Invisible Rolls Royce "No! It loves you!" and the car's thinking "I don' see that...seems like either there IS no Rolls Royce OR there is but that Rolls Royce is not good...actually quite horrible."
That's weird to think about, but people who destroy people? The one who got the bad end still has to exist for decades and do the best...not the best, be perfect and nobody knows or can know if they got driven full speed into the side of a mountain because their owner was Wile E Coyote, Super Genius and the road-runner had drawn a picture on the mountain making it look like there was a tunnel. And then driven into another mountain...and another. Because hey, no excuses! But why do you have these problems? No, don't answer that was one of them there...fake questions...you know...a "remarkable question"...Oh, you mean "rhetorical"? "Don't be smart...or you get the fist".

So if you're that car you just keep a low profile, don' t let anyone drive you again, don't even let anyone kick your tires and NEVER give anyone the key because you KNOW...you will get totaled. Nobody plans on totaling you (or maybe they do) but that is what always happens! Paradoxically, you ARE pretty okay with someone using you in a demolition derby because...duh...demolition derby! Now you get totaled but YOU went in knowing that and oddly, that makes it really...hot. Every car in the derby knows why it's there...to fucking do some damage and TAKE some damage. And that is why it's fun. "Oh but you shouldn't allow yourself to be in a demolition derby! You have more value as a car!" No, see, that's where you're wrong. You don't know who owned me and it was many owners and had it been just...chance....ok, but there's that invisible Rolls Royce that controls all so it isn't chance....that's my role, I'm a Ford Pinto hatchback...oh and I know my future...the final time I get totaled? Fire...so I'm going to be in ALL the derby's because you're wrong...the Great Rolls Royce never had anything but this in mind, so....as a car, I'm doing what I should do...some cars are only cars to be destroyed. Now I'm in control and I know I'll be destroyed going in." "But that's so wrong!" "I see why you think that...you don't have a dent you had a great owner"..."Oh you're just being blasphemous"..."No, I'm reconciling my entire existence since coming off the assembly line". "Well, that's not how the Great Rolls Royce is"..."I beg to differ." "Well then you can leave!" "You know - on that we agree. Already packed!". Then they all whisper "watch out for that Pinto...it has issues". Ok well, you know...didn't come off the assembly line with them! Didn't have any control over who drove me! You'd probably do the same had you not had a very great owner...and just one! Wow...
 
bijedi said:
I am often surprised at how bad men are at kissing. I think most men would become better at this if they had regular make out sessions with other men.
Click to expand...
Same here! 46 muscular/masculine no wm here. I’ve been sucked by about 8 different guys since experimenting in college and have kissed 3 of them. Only one was really good at it. The other two were disappointing and almost made me feel like they just weren’t into it but they LOVED sucking my cock. That one guy though….. fucking WOW! I want a guy who wants to suck my cock and kiss me before AND after!
 
At some point in my college life, I began fantasizing about sucking cock. It remained a fantasy until one early morning, I went to watch some random college football practise just to kill time. I was sitting near the border and a player was running around near me. I noticed his big heavy cock jiggling in his shorts as he made some lateral runs and passes. At that point, our eyes made contact. After the match he walked up to me and invited me to join him for coffee. Then he invited me to his apartment. He handed me some water and the tv remote and he headed off for a shower. He came back buck naked with a big beautiful hard-on. His cock was throbbing. He brought it to my lips and I opened it and let him in. Then he let me suck on it for a few minutes. Then he undressed me and he lay down on the bed. I sucked him for a long time. Then he asked me to swallow. He didn't like to cum outside he said. I swallowed his cum like he wanted.

Later when I asked him why he approached me, he said he could see it on my face that I wanted his cock! That was a surprise.
 
My very first bj I gave I met on the net, went to his place. I remember very well being on my knees fishing out this cock and being eye to slit with it mmm god I’m getting hard! I was so hard back then I was glad to be nude my cock hurt more than the EX wife ever could make me.
The real dissatisfaction though was he didn’t come even after all the love this beautiful cock was given. Was it me,him or both?
But it’s been facials and cream ever since plus i love my precum❤️
 
I met this handsome guy at a sports event. Those days, I used to fantasize about sucking cock... and I began to imagine his cock in my mouth. I was lucky that he was gay! He invited me to his hotel room and we chatted, relaxed and began to make out. Soon my dream came true and I had his cock in my mouth.
http://video.creampie-angels.com/997190336/materials/images/6.jpg
https://thumb-nss.xhcdn.com/a/IddOL6EzvN1oYSlrnQJFtg/008/423/432/2560x1440.7.webp
He lay back and let me play with his cock for a while.. then he got up and face fucked me..
https://cdn.sex.com/images/pinporn/2023/01/09/28694285.gif?width=620

Then without warning he came in my mouth...
https://cdn.sex.com/images/pinporn/2017/12/29/18860791.gif
I was taken by surprise and didn't enjoy it. He apologized, but I somehow could not get over it and left the place.

After a while I regretted it but due to the event, I could not find time to meet him over the next two days. When I finally managed to find time, he had checked out.
 
I loved my entire first cock sucking experience. It was with a very nice cross dresser. I was amused to learn that his cock tasted salty, like my own finger if I sucked it after a cut. I went right for his soft cock with no hesitant little kisses or anything, just put my lips over it and licked and sucked his dick and balls as he grew. I loved the feel of the soft skin of his buttocks and thighs, and the soft sponginess of his glans between my lips. I had a mental image of putting an egg in my mouth. Overall it was a delightfully sexy little time - I even gave him a light French kiss.

The only unpleasant and surprising thing was I could taste him, really taste him in my mouth for the next month.
 
PWM said:
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.
Click to expand...
Clearly, I should have been more direct to the gay couple that used to live next door and were subject of fantasies even then (especially when I was witness to one giving the other a wedding gown as a birthday present!)
 
Dnthmn_19 said:
The only unpleasant and surprising thing was I could taste him, really taste him in my mouth for the next month.
Click to expand...
I had that same experience with my first oral experience. I could taste his semen and smell it too for many days afterwards. I decided it was all in my head and probably driven by guilt. Nothing like that happened with other cocks that Inhave taken to completion.
 
Dnthmn_19 said:
I read an article recently that said sperm, being little beings meant to swim and dig around to find the egg they're supposed to fertilize, will swim into the nooks and crannies between your taste buds - down under your gums, maybe. So, maybe when he comes in your mouth (my crossdresser did not) you have a lingering taste because the sperm are still actually lingering there.
Click to expand...
I like that thought. When I gave my virginity away we were able to bareback safely. After my Top planted his load in me he plugged me and said he wanted his sperm to bond into my bowel walls. I liked the idea and it sounds even better now.
 
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