Pleasant surprises and disappointments in first gay experiences

[Travler99921]

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.

 

[Sweepup50]

I first sucked a cock in my thirties it was during a game between my best friend and my wife and I got a forfiet to suck his cock for one minute. I was drunk so it didn't seem that much of a big deal. A decade past as my sex life diminished to zero and I thought more and more that I wanted to suck a cock while sober. The opportunity arose and I became a cock sucker, I did do 69 with a guy and I agree it was disappointing as I tried to concentrate on sucking his cock while also trying to enjoy him sucking mine.

 

[kLangleybi]

This is posted in another thread on this site but I can't remember which one. So, here goes.

It was strange because until this occasion I never wanted anal but it 'happened'. We met on another site and after talking things over we arranged to meet at a motorway service station for coffee and see if we wanted to take things further. Throughout all the chat leading to the meet, and indeed over coffee, it had been made plain I was not interested in anal sex either way. No problem there and we decided to get a room at the on-site Premier Inn. To cut a long story short we were wanking and sucking each other when I felt an obviously lubed finger stroking around my hole. Where I thought I would react and stop him I found that it felt so hot I let him continue. His finger slipped in and oh my days it felt fantastic. After a time he whispered that he now had three fingers inside me sawing in and out. No pain at all. Well, it was ace and I heard a voice that I didn't even recognise as my own saying " fuck me, please fuck me". I was begging him to fuck me, much to my surprise. I was mad for it!


He donned a condom, had me kneel on the edge of the bed and entered me. Jeez, but I was loving it. I was being properly fucked like a slut and I wanted it to never end. Cum was leaking out of me as his cock passed back and forth over my prostate. And I mean cum. Not precum but thick ropes of cum. I seemed to be in a perpetual state of orgasm and just wanted him to keep going. Up until then, I'd experienced no pain at all apart from a very brief 'sting' as his mushroom head pushed past my sphincter, only deep pleasure. However, he then took it up a notch and pulled out only to plunge forcefully back into me. His rather large helmet hurt big time in both directions and I was no longer enjoying this. Wasn't long before he withdrew, removed the condom and finished by spraying hot cum over my arse and balls whilst remarking upon all my spunk on the sheet. So a great although unexpected experience was somewhat spoiled by his over-exuberance. Shame really because overall I had thoroughly enjoyed being his 'girl'. That came as a real shock to me.


So there you have the story of my only experience of anal sex. Would I succumb again? I suspect with the right man I could easily let a man take me. The issue is first finding a man for any kind of sexual interaction. I've found it impossible. This was not my first gay experience. I had sucked a couple of cocks prior to this event but not to completion. Still haven't.

 

[Cabeza]

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 .

 

[whiteasianlvr]

I was a very late bloomer, too. I can't say the sex was phenomenal, but the relief of letting go and letting another man take me was what I remember most. Having been wired since my earliest memory to desire to be overshadowed by another man, I simply felt overjoyed when it happened even though, surprisingly, I can't remember IF I came. What I do remember was seeing the face of the younger, Vietnamese man as he slipped into me - he looked so dominant as if he were taking my manhood. The psychological effect still resonates in me - hence, my attraction to Asians and to the reality of being only and forever a bottom.

 

[Burstplayer]

Pleasant surprises: How much I loved sucking cock and how good I was!. Another was how good all 3 of my encounters were to date. All tasted good and I could swallow their loads with ease.

Disappointments: Finding guys who just want to receive oral (that's why I'm doing gloryholes now...) and finding a top for anal. Seems there are way more bottoms than tops in the places that I look

 

[CharlieBoker]

This is posted in another thread on this site but I can't remember which one. So, here goes.

It was strange because until this occasion I never wanted anal but it 'happened'. We met on another site and after talking things over we arranged to meet at a motorway service station for coffee and see if we wanted to take things further. Throughout all the chat leading to the meet, and indeed over coffee, it had been made plain I was not interested in anal sex either way. No problem there and we decided to get a room at the on-site Premier Inn. To cut a long story short we were wanking and sucking each other when I felt an obviously lubed finger stroking around my hole. Where I thought I would react and stop him I found that it felt so hot I let him continue. His finger slipped in and oh my days it felt fantastic. After a time he whispered that he now had three fingers inside me sawing in and out. No pain at all. Well, it was ace and I heard a voice that I didn't even recognise as my own saying " fuck me, please fuck me". I was begging him to fuck me, much to my surprise. I was mad for it!


He donned a condom, had me kneel on the edge of the bed and entered me. Jeez, but I was loving it. I was being properly fucked like a slut and I wanted it to never end. Cum was leaking out of me as his cock passed back and forth over my prostate. And I mean cum. Not precum but thick ropes of cum. I seemed to be in a perpetual state of orgasm and just wanted him to keep going. Up until then, I'd experienced no pain at all apart from a very brief 'sting' as his mushroom head pushed past my sphincter, only deep pleasure. However, he then took it up a notch and pulled out only to plunge forcefully back into me. His rather large helmet hurt big time in both directions and I was no longer enjoying this. Wasn't long before he withdrew, removed the condom and finished by spraying hot cum over my arse and balls whilst remarking upon all my spunk on the sheet. So a great although unexpected experience was somewhat spoiled by his over-exuberance. Shame really because overall I had thoroughly enjoyed being his 'girl'. That came as a real shock to me.


So there you have the story of my only experience of anal sex. Would I succumb again? I suspect with the right man I could easily let a man take me. The issue is first finding a man for any kind of sexual interaction. I've found it impossible. This was not my first gay experience. I had sucked a couple of cocks prior to this event but not to completion. Still haven't.

Nice post. Horny!!!
It resonated with me as I love being fucked gently and slowly but find it painful to be pounded.
When I was young and bisexually active, I was lucky to have a couple of much older considerate lovers who brought me to some amazing orgasms with their cocks inside me. Not frenzied fucking, just gentle grinding.

 

[SexyInMy60s]

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.

I love kissing men but some of them are awful at it.

 

[bijedi]

I love kissing men but some of them are awful at it.

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.

 

[Clair92]

This is posted in another thread on this site but I can't remember which one. So, here goes.

It was strange because until this occasion I never wanted anal but it 'happened'. We met on another site and after talking things over we arranged to meet at a motorway service station for coffee and see if we wanted to take things further. Throughout all the chat leading to the meet, and indeed over coffee, it had been made plain I was not interested in anal sex either way. No problem there and we decided to get a room at the on-site Premier Inn. To cut a long story short we were wanking and sucking each other when I felt an obviously lubed finger stroking around my hole. Where I thought I would react and stop him I found that it felt so hot I let him continue. His finger slipped in and oh my days it felt fantastic. After a time he whispered that he now had three fingers inside me sawing in and out. No pain at all. Well, it was ace and I heard a voice that I didn't even recognise as my own saying " fuck me, please fuck me". I was begging him to fuck me, much to my surprise. I was mad for it!


He donned a condom, had me kneel on the edge of the bed and entered me. Jeez, but I was loving it. I was being properly fucked like a slut and I wanted it to never end. Cum was leaking out of me as his cock passed back and forth over my prostate. And I mean cum. Not precum but thick ropes of cum. I seemed to be in a perpetual state of orgasm and just wanted him to keep going. Up until then, I'd experienced no pain at all apart from a very brief 'sting' as his mushroom head pushed past my sphincter, only deep pleasure. However, he then took it up a notch and pulled out only to plunge forcefully back into me. His rather large helmet hurt big time in both directions and I was no longer enjoying this. Wasn't long before he withdrew, removed the condom and finished by spraying hot cum over my arse and balls whilst remarking upon all my spunk on the sheet. So a great although unexpected experience was somewhat spoiled by his over-exuberance. Shame really because overall I had thoroughly enjoyed being his 'girl'. That came as a real shock to me.


So there you have the story of my only experience of anal sex. Would I succumb again? I suspect with the right man I could easily let a man take me. The issue is first finding a man for any kind of sexual interaction. I've found it impossible. This was not my first gay experience. I had sucked a couple of cocks prior to this event but not to completion. Still haven't.

I can very much relate to your first anal experience as I have a similar problem with my last boyfriend . I was just so lost in pleasure ,writhing around saying his name kissing passionately and he was so close to making me cum when he suddenly began to pound away as he was cumming. Yes it was lovely to feel the heat inside me but I was angry that he was so selfish. What went from lovemaking to a brutal fucking was such a disappointment .

 

[Bi4Older84]

I love kissing men but some of them are awful at it.

This sounds like my regular buddy. He's amazing at sucking cock and rimming, and is generally a fantastic, attentive lover-but he is an absolutely atrocious kisser. Too aggressive, too much tongue...and I don't think it's a gender thing, just a "him" thing.

It hasn't put me off to the idea of kissing/making out with a guy, but he and I tend to find other, better ways to use our mouths than kissing

 

[Clair92]

Kissing is so important
If I don't that eye closing feeling when I kiss someone I know our love making won't be as passionate .

 

[BiDrew42]

Pleasant surprises include how much I enjoyed kissing and being kissed by him, having my nipples sucked, and how much I enjoyed the taste of his pre-cum, and later, his cum. I had eaten my own many times but his was so much better.

Also surprising was how difficult anal was the first time we tried it. We didn't have any lube and no matter how much I wanted it, I could not relax enough for him to enter me. I wanted his cock inside me so badly. The second time we tried was much more successful (vaseline to the rescue!).

Another surprise was how easily I accepted the fact that I loved being with another guy. I never felt any guilt about it, although he was eaten up by guilt. He would often say we had to stop, but we kept up our sexual activities all through high school and for several more months until I went in the Air Force. I had known I was interested in other boys beginning when I was 11, but I also liked girls. Back then I had no idea what bisexual meant - I just knew I liked both. He told me he had never considered having sex with another guy until the night we first jacked off together.

I can't think of any disappointments, other than that feeling of emptiness after he came in my ass and pulled out. I still experience that feeling to this day.

 

[dingdongditchding]

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.

I want to make out with a dude

 

[ndoorfin]

my first was horrendous I was too young in a public toilet this old (probably 40 lol) tried to fuck me then wanted oral, I nearly choked he came I cried still knew it was what I wanted

 

[easyoff]

I was surprised at how much I enjoyed sucking his cock and the taste of his cum