Regrets? Missed connections? What would you do if you had a second chance?

[Hitchiker69]

My favorite fantasies often involve the 'what if' factor of missed sexual opportunities.

Example: What if I had hit on that guy who was obviously interested in me... the cute one I saw on my way to the laundromat?

What if I had taken up the invitation to spend the next day with the guy I'd slept with in Watsonville?

How about my boss in California, from that restaurant job? He was gay, and wanted me, but I wasn't ready.

Do you ever wonder what might have happened, if only....?

 

[Experiencedguy]

Of course, we all do. These are called fond memories, or bad regrets. Almost all of us experience more of these in our lives than we can remember. My favorite is from over forty years ago. I still (occasionally) dream about that person, and the what if, and still have great rememberances of the brief time we were together.

We were just too inmature.

 

[Nimbikarana]

Regrets? I've had a few, but then again, too few to mention

 

[Hitchiker69]

What might have been...

Here's what I like to think might have happened...

Facts: I was wearing only a pair of running shorts and sandals. I was in very buff condition, having worked construction for years. I caught his eye...he was sitting at a sidewalk cafe by himself. He was exactly my type...slight build, kind of fem looking, clearly gay and out.

Fantasy: So I come out of the laundromat and sit at his table. I say "see something you like?" as I spread my legs and look him in the eyes, with a smile. "I've got an itch that needs to be scratched...can you help?” “Oh yes”, he stammers. I suggest we go to my place, half a block away. He finishes his drink, leaves a few dollars on the table, and we
walk towards my apartment. There’s a short alley on the way, very private. I grab his ass when we get there, give him a kiss and place his hand on my hard cock. He’s taken aback by how horny and aggressive I’m being, but he doesn’t resist...I think he actually swooned.
We get to my place, quickly and without words we enter the bedroom, and I drop my shorts immediately. I grab him, kissing as I remove his shirt. He kicks off his shoes. I kiss his nipples as I remove his pants. We lay down, he on his back, me above. I present my cock to his mouth, He takes it eagerly and deeply. He clearly knows what he’s doing. I reach back and stroke his cock as he sucks me.

For the next few hours we proceed to please each other, enjoy each other, satisfy each other, and completely appreciate each other’s manhood. Sucking, stroking, kissing, fucking…the passion was intense, and the sex went on and on. Every position and move we could think of… I came at least 4 times, and so did he. His ass was really tight, his cock hard and meaty. He was a very skilled lover. The room reeked of sweat and cum. I’ve never been more completely spent and satisfied.

As the sun went down he got up and dressed. He left me his card, as he asked “Can I see you again on Tuesday? I’d like to introduce you to some friends.” I said yes, and promised to call him. As I drifted off to sleep I thought about the prospects of going to bed with him and a few friends…a bed full of hard cocks, soft mouths and tight butts…and I reflected how glad I was to be a bisexual man.

So that's my fantasy...what's yours?

 

[woman_inside]

when i was still an anal virgin i saw an personal ad on a gay site saying something like 'i'll treat u like a lady first and then prove to you that you have a litttle whore inside that wants to be humiliated.' he mentioned his huge cock size. i chickened out of arranging a meet, but i wonder what it would have been like to have lost my virginity to him.

 

[HerLittlePiggy]

Regrets. I have a few. I wish my ex and I had explored our fantasies more and lived more out before the arguing got the better of us.

In a perfect world we would have met whe we were both single. But life aint perfect.

 

[OpenlyClosed]

Missed out on exploring more in college. I had just barely admitted to myself that there was a part of me interested in men, but was too insecure in myself to act on it. Now, years later, it is hard to have the same anything goes life. My loss-I've stayed inexperienced as a result.

 

[longnmguy]

Wish I'd had her inside me

I met up with an incredible (and regrettably, now deceased) TS in San Francisco. We sucked each other and I fucked her, and had some of the most amazing and hot sex I'd ever experienced.

But I didn't ask her to fuck me and I wish I had. I still think back to that wonderful experience.

But one of these days...

 

[amnesiac_1]

I enjoy nude beaches, and drove to Austin for Hippie Hollow one weekend when I lived in Dallas. It was Labor Day weekend, which is a big party at HH. Anyway, I was laying out and a guy maybe 30 feet away struck up a conversation with me and asked if he could join me. I said sure and we talked a little and I learned he was from another part of the Dallas metroplex. I was nervous just talking to him because I had never been with a guy before. We went swimming together to cool off because it was very hot that weekend. After swimming, we laid out some more and I was so nervous I told him I was too hot and had to leave. He wanted to exchange phone numbers, but I made up some wussy excuse and bailed.

He would have been a perfect first time friend. Handsome, good body, around my age, slightly smallish cock when soft, who knows what it was like hard. I wish I did.

If I could do it again, I would love to have enjoyed some more time with him, naked on the rocks of Lake Travis. Then drive back to one of our apartments, grill up some food, take a shower (together) and have all kinds of hot sex all evening long.

I can still picture his cock, red pubic hair, smooth chest and handsome smile to this day. That was over 10 years ago and I obviously still regret it.