Regrets Only: The One(s) That Got Away...

[HornyVikingMN]

For some reason the encounters I almost had, but didn't, have always been the thoughts that fuel my fantasies.

Have you ever passed on a chance to have sex with someone new - either an anonymous fling or a naughty moment between friends - and regretted it later? Do tell!

Who was it? What were the circumstances? Why did you decline? If you could turn the clock back, what would you do differently?

 

[Afterhours22]

one in particular

I dated a girl about 15 years ago that was the absolute perfect girl in every way. She was sweet, beautiful and was open to anything sexually with me. The girl literally rocked my world. Unfortunately, at the time, I let my jealous side get to me. She was friends with many of her exes and even though she was faithful to me, I didn't think she would after a long term relationship. I was stupid and broke it off with her, shattering 2 hearts that still love each other to this day. She is now married to another man, but I still get occasional email from her, saying she still thinks about us and "what if." YES I AM ONE STUPID SON OF A BITCH!

 

[ViolentSkye]

I dated a girl about 15 years ago that was the absolute perfect girl in every way. She was sweet, beautiful and was open to anything sexually with me. The girl literally rocked my world. Unfortunately, at the time, I let my jealous side get to me. She was friends with many of her exes and even though she was faithful to me, I didn't think she would after a long term relationship. I was stupid and broke it off with her, shattering 2 hearts that still love each other to this day. She is now married to another man, but I still get occasional email from her, saying she still thinks about us and "what if." YES I AM ONE STUPID SON OF A BITCH!

If she's still emailing you now that shes married, maybe you were right all along?

 

[Hidden_Icarus]

If she's still emailing you now that shes married, maybe you were right all along?

http://th574.photobucket.com/albums/ss184/Nicxtrem99/th_csi_yeah_skyline.jpg

Also, hi!

 

[jmarx20102012]

I regret not having a one night stand with someone I flirted pretty heavily with for years. Saw her in a bar once and she wanted to go home with me but I was just too tired which never happens. She is married now and so am I so...

 

[Afterhours22]

You have a point....

If she's still emailing you now that shes married, maybe you were right all along?

or it could be that she, like me, has never let go of what we felt for each other... they say you only truly love one person in your life.. I'm sure that is not always the case with everyone, but I think for her and I, it is.

 

[HornyVikingMN]

I regret not having a one night stand with someone I flirted pretty heavily with for years. Saw her in a bar once and she wanted to go home with me but I was just too tired which never happens. She is married now and so am I so...

You must have been REALLY tired!

 

[CR_from_BR]

My ex used to post pics on lit and she got chatting with a guy from London through PMs. We'd been talking about threesomes and I always thought it would be SO hot to see her with another guy, that when the suggestion came up of us all meeting up together I immediately went for it! We drove and met him halfway between Bristol and London to meet up at a neutral location just to see if we clicked. We said beforehand that nothing would happen on this particular occasion, so we just relaxed and chatted. Eventually there was a bit of flirting between her and him, and I thought we were going to break the rules and go for it, but she said not this time but we'd talk about it. In the car on the way home we discussed it both said we wanted it to happen and that we would arrange to meet up again sometime. Sadly, we broke up a few weeks later and it never happened. This has been a huge fantasy of mine ever since, and I often imagine what would have happened if we had either just said "to hell with it" and broken the rules right there, or made some other plans to meet up at a later date. I have a huge cuckold fetish, and the idea of watching her sucking on his cock and him fucking her, the image of her being taken by the two of us together... Wow, it makes me so hot, and I can't believe we came SO close!

 

[citychick29]

For some reason the encounters I almost had, but didn't, have always been the thoughts that fuel my fantasies.

Have you ever passed on a chance to have sex with someone new - either an anonymous fling or a naughty moment between friends - and regretted it later? Do tell!

Who was it? What were the circumstances? Why did you decline? If you could turn the clock back, what would you do differently?

How about you share yours with us?

 

[HornyVikingMN]

OK, CityChick...

Here's one that got away. Sorry for the lengthy example, but I think some will appreciate the detail.

I was in Europe on business, and had worked for several days with small group, including a German woman from the client organization. She was very attractive, fun to work with, and sexy. On the last night we were to be there, the plan was for our small group to go to dinner together. The other two women were local, and conflicts came up for them so it ended up being just the German woman and myself.

Before dinner we took a long walk along the shore of the lake we were near. As the sun began to set, we made our way back toward the hotel and stopped for dinner at an informal place on the water. We had a very nice dinner and a great conversation. The food, the wine, the cool outdoor air and my charming dinner partner all contributed to a wonderful time. If it's possible to have a romantic evening with someone you barely know, this was it.

We walked back to the hotel and said our goodbyes. While I wasn't quite ready to end the evening, she had an early morning flight, so we both retired to our rooms - which just happened to be right next to each other.

Not long after we parted, there was a knock on my door. I opened it, and she asked me if I was going to be up for a few more minutes because she had something for me and wanted to show me some pictures we had talked about earlier. I said, "Of course." She handed me a small item that was rolled up in paper and said, "I made this and I want you to have it. Open it, and I'll be right back with the pictures." Removing the paper, I found a bar of homemade soap. It struck me as a bit odd, almost like it was a spur of the moment decision to give it to me.

When she returned, she had removed the long-sleeved shirt she had worn, revealing the red spaghetti tank underneath. She sat down on the small love seat in my room and motioned for me to sit as well. We were sitting quite close as we looked at the pictures she brought in. The tension was thick, and it began to get a little awkward.

My mind was racing. I was adding up the signs - the wine, the laughter, the tank top (it was cool in the room - not hot), the soap, and the flimsy reason to come back to my room to show me the photos. I also weighed the consequences. I'm married, she works for my company's most important client, etc. In the end, I let the moment pass.

I'm convinced that had a just grabbed her hand and kissed her we would have ended the night using the soap she brought to me and her racing off to the airport. As soon as the door closed when she left my room I began to regret not pursuing the moment. Of course, in my fantasies the story ends much differently.

Oh... and to make matters worse, she eventually left my client's company and the company ceased being a client. Of course!