Fantasizing a missed opportunity

[tributeb20]

A few years ago I started dating a young girl. I was her first boyfriend. She was a truly virgin. I always had a huge desire for her, but there was a problem: my cock is small. Since we had to see each other in secret most of the time, we didn't have a place to explore our relationship and get to the penetration. In fact, I was always afraid of getting to penetration because of my small dick. I always played with her pussy but I didn't let her touch my dick out of embarrassment.

She was very naughty, we played in public places like emergency stairs and she always got very wet. I even asked her what her desires were and she said she felt like having sex with two people one day. We dated for about 3 years and, believe it or not, we never got to penetration. I took advantage of her body during oral sex but I only let her touch my dick a few times, most close to the end of our relation. Not even a blowjob. We tried penetration once but because I was nervous about getting caught I couldn't continue.

At the time she was already a hottie, everyone wanted her. Skinny, white, dark hair, delicious breasts, a angel face but deep down a real slut. We broke up and I couldn't fuck her. My biggest regret. If you could see how wet she got just from kissing...

To this day I have a huge desire for her and after I found out she started dating again I started masturbating myself imagining her having a real big dick fucking her, doing everything she couldn't do in the 3 years we were together, ridiculing the fact that she dated a guy for all that time without even having fucked her. Everytime I see a photo of her in a party or with some guy I already start to jerk a lot. How I wish to get her again only to tell her I need to see she fucking big guys.

I have her nudes and some photos and I end up sharing them on some sites so that several guys can see her wanting her and I end to masturbate myself. This happens a lot in these years. How I would love to see her fucking, that wonderful face receiving so much pleasure. Just writing this makes me almost cum.

Does anyone have a similar story? Or any comments to talk about this? Any question? I've always wanted to tell about this story but never found a place, until now.

 

[Vincenzo]

A few years ago I started dating a young girl. I was her first boyfriend. She was a truly virgin. I always had a huge desire for her, but there was a problem: my cock is small. Since we had to see each other in secret most of the time, we didn't have a place to explore our relationship and get to the penetration. In fact, I was always afraid of getting to penetration because of my small dick. I always played with her pussy but I didn't let her touch my dick out of embarrassment.

She was very naughty, we played in public places like emergency stairs and she always got very wet. I even asked her what her desires were and she said she felt like having sex with two people one day. We dated for about 3 years and, believe it or not, we never got to penetration. I took advantage of her body during oral sex but I only let her touch my dick a few times, most close to the end of our relation. Not even a blowjob. We tried penetration once but because I was nervous about getting caught I couldn't continue.

At the time she was already a hottie, everyone wanted her. Skinny, white, dark hair, delicious breasts, a angel face but deep down a real slut. We broke up and I couldn't fuck her. My biggest regret. If you could see how wet she got just from kissing...

To this day I have a huge desire for her and after I found out she started dating again I started masturbating myself imagining her having a real big dick fucking her, doing everything she couldn't do in the 3 years we were together, ridiculing the fact that she dated a guy for all that time without even having fucked her. Everytime I see a photo of her in a party or with some guy I already start to jerk a lot. How I wish to get her again only to tell her I need to see she fucking big guys.

I have her nudes and some photos and I end up sharing them on some sites so that several guys can see her wanting her and I end to masturbate myself. This happens a lot in these years. How I would love to see her fucking, that wonderful face receiving so much pleasure. Just writing this makes me almost cum.

Does anyone have a similar story? Or any comments to talk about this? Any question? I've always wanted to tell about this story but never found a place, until now.

If she was truly a virgin as you say, you shouldn't of been concerned about your dick size, as she had never had one before. But most men have fantasies of seeing their GF/wife fucked by a big cock. Many even follow through with it (myself included)

 

[tributeb20]

If she was truly a virgin as you say, you shouldn't of been concerned about your dick size, as she had never had one before. But most men have fantasies of seeing their GF/wife fucked by a big cock. Many even follow through with it (myself included)

Yes, it’s true. I have a lot of regrets. I should tried more. But I didn’t want to mess her first time.

 

[vette19690]

Mistakenly posted in ' Fantasy' forum. It actually belongs in Stag/Vixen?
We were at a New Year's day brunch at a friends house when my wife came up to me and another couple and smiled in an embarrassed manner. "Ron just asked me to meet him for lunch one day and when I declined, he asked if I would be interested in an affair!"

Ron is a widowed friend of ours and the rest of the neighbor hood.



The wife of the other couple tsk tsk'ed and said he did that once before to another woman, but not her. My wife looked at me as she said she told him she wasn't interested and that I was one of his friends and she couldn't do that.



She told us he pressed the request, not too aggressively, saying I didn't have to know; his house was secluded and there was no way anyone would see them and he could arrange things to be safe. She added with a smile that she' hadn't been hit on in years. I am sure she enjoyed the attention even as she tried to deny it.



The other wife thought Ron was way out of line and he should be ashamed, but the other husband just kind if grinned at the story unfolded.

I just smiled at my wife and told he she shouldn't be surprised since she is quite attractive. I think she was more than a little surprised I didn't get angry or respond to this as in insult. I told her it was alright and not to be upset and she quietly sipped her drink. The conversation lagged momentarily until anther guy joined us and stared a different conversation.



I am not really surprised that Ron hit on her. She's a five foot five ash blonde hair cut short to frame her face with blue eyes, a cute nose and sweet looing plump lips. She about 125-130 pounds with a nice trim body; high tight ass and great legs. This particular day she had a light tan cashmere sweater that absolutely clung to her perky 32-C tits. She does have great tits! How could I blame him!



My wife hasn't raised the discussion since then and neither have I. I am not surprised but I can't help wondering if the converstaion isn't bouncing around in her head.

We were at a New Year's day brunch at a friends house when my wife came up to me and another couple and smiled in an embarrassed manner. "Ron just asked me to meet him for lunch one day and when I declined, he asked if I would be interested in an affair!"
Ron is a widowed friend of ours and the rest of the neighbor hood.

The wife of the other couple tsk tsk'ed and said he did that once before to another woman, but not her. My wife looked at me as she said she told him she wasn't interested and that I was one of his friends and she couldn't do that.

She told us he pressed the request, not too aggressively, saying I didn't have to know; his house was secluded and there was no way anyone would see them and he could arrange things to be safe. She added with a smile that she' hadn't been hit on in years. I am sure she enjoyed the attention even as she tried to deny it.

The other wife thought Ron was way out of line and he should be ashamed, but the other husband just kind if grinned at the story unfolded.
I just smiled at my wife and told he she shouldn't be surprised since she is quite attractive. I think she was more than a little surprised I didn't get angry or respond to this as in insult. I told her it was alright and not to be upset and she quietly sipped her drink. The conversation lagged momentarily until anther guy joined us and stared a different conversation.

I am not really surprised that Ron hit on her. She's a five foot five ash blonde hair cut short to frame her face with blue eyes, a cute nose and sweet looking plump lips. She about 125-130 pounds with a nice trim body; high tight ass and great legs. This particular day she had a light tan turtleneck cashmere sweater that absolutely clung to her perky 32-C tits. She does have great tits! How could I blame him!

My wife hasn't raised the discussion since then and neither have I. I am not surprised but I can't help wondering if the conversation isn't bouncing around in her head.

It would have been extremely difficult to encourage her or pursue her feelings with the other couple there, but should I kind of hint about it and maybe re-open the discussion? Maybe with a question about her finding Ron attractive or how does she really feel about having someone proposition her which is what happened)?

Should I hint around how I think she might enjoy another guy or my feelings about watching her get fucked by another guy?
Is this a missed opportunity that I might rectify or is this just my imagination running wild?

Damn I've got a hardon just writing about it and thinking about the possibilities!
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