Note: Nearly 5 years ago I wrote a 2-part story called "Watching Cindy" about how I shared my sexy wife Cindy with a very well-endowed stranger we deliberately met in a hotel bar. It was an unforgettable experience, but since then until recently we had returned our sexual lives to "normal", at least insofar as monogamous is really normal. I've never really been sure about that....
If you've read "Watching Cindy" please bear (bare?) with me as I introduce Cindy and myself again:
Cindy and I have been happily married for more than 20 years. We are both successful professional people. Cindy is 46 now. I am several years older. Cindy keeps herself in great shape with regular workouts, tennis, skiing, running and bike riding. She has the toned body of a woman many years younger, and a very pretty face, with bright blue eyes and prominent high cheek bones. She is 5'9" with stylishly cut blond hair. Her legs are long, lean and shapely, topped off by my favorite kind of butt... not too large yet full and round. Cindy's ass moves sensuously (and obviously) when she walks. Cindy's breasts are medium-sized, firm and wonderful to touch with prominent nipples. I keep myself in top shape too.
From the very first night we met we have enjoyed great sex, but for some time I was uncomfortable talking about Cindy's very active sex life before we'd met. I was still a bit insecure I guess. Basically what we'd each done before was off limits. Until we'd been married for a couple of years we never discussed it at all. Then that began to change. We enjoyed watching porn movies together every couple of months. I began to be aroused by the notion that Cindy was sexually stimulated by seeing other men, naked, erect, well endowed.
I started to comment, saying things like: "Wow! That guy has a big dick! And he is really aroused. I bet you like that, don't you lover?"
Cindy at first would reply a bit shyly, saying "yes, his is really big, but I love your penis, dear."
Over time Cindy's comments became much bolder. She realized it turned me on to hear her comment admiringly about an especially large or especially hard-looking cock on a porn actor. She began to initiate comments, her always deep sexy voice breathlessly saying things like: "Oh my god! Joe, will you look at the hard-on on that guy! His cock is huge! And SO aroused. I can imagine how he'd fill me up!" I'd encourage her, feeling my penis swelling as I listened to her lewd remarks about other men's cocks.
One night five years after we married we had a spontaneous sexual adventure with another couple, neighbors and very good friends. "Alcohol was involved" as they say but so was long-time attraction to each others' spouses. The best part for me was being right there as my friend fucked Cindy as I fucked his wife just inches apart. The sounds of Cindy's orgasms are my sweetest memory of the night, a one-time thing as it turned out.
I began to seek out stories about her many past lovers. She gradually became more open. These conversations were a form of verbal foreplay for us, a sexy conversation over wine that would be a prelude to scorching sex. We were clearly moving in a new, erotic direction, jealousy gone, more secure in our relationship, sexually and in general.
Then several years ago we began to incorporate the theme of "the other man" into the sexual fantasies we acted out. I bought Cindy several dildos (the first as a Valentine's Day gift), going for more and more realistic ones. A favorite of us both is a very life-like 8" model, thick, smooth, complete with a set of balls, realistic coloring, veins: the complete package. In our "threesomes" Cindy might suck me, bending over in a standing position next to the bed while she is taken in the pussy by the dildo stuck to the adjacent wall. This is powerfully erotic to me and to her. Another favorite is for her to suck the other man while I fuck her, at times with my face right next to hers, with his penis being worked over by her hot mouth, close up. She acts well and makes it realistic.
We gave the "other man" names. Both of us contributed suggestions, created characters. A particular treat for me was fucking Cindy's hot, tight ass and pussy simultaneously with me taking one hot opening and "him" the other. I loved feeling our cocks rub together as we fucked her. I also loved to sometimes just watch Cindy "do it" with the other man. She has a way of making it seem real, teasing herself (and me) as she licks, strokes and sucks his cock, and penetrates herself, ever so sensuously, calculated to drive me wild as I masturbate watching her, listening to her vivid reactions and filthy talk, and most exiting of all watching and listening to her explosive orgasms.
Five years ago I raised the idea of Cindy really fucking another man again, this time while I watched. She laughed it off at first, saying she had no real interest in anyone else, that it was a great fantasy for her but nothing more. Just talking about it was a major turn-on, and gradually her response began to change. She'd ask if I really wanted that, and we began to think of how we could actually go about getting another man, safely and anonymously. I began to realize that my #1 fantasy might actually happen.
Finally, as detailed in "Watching Cindy" we did it! It was super intense, fantastic, and has fired our sex lives since even though until recently we hadn't indulged in sharing Cindy again.
But the idea was never far away and my desire to again experience sharing Cindy, having her be royally fucked by another man or men only grew over time. I have been connecting with other men, and a few women who enjoyed my stories and shared my interest in sharing, or if you will, being "cuckolded". Their support and encouragement gave me a push toward making it real again.
We'd scheduled a vacation to a "clothing optional" resort in the tropics that we had been to before and both loved. Though not promoted so much as a "swingers" (we hate that word!) type of place we knew that there were all types of people there, couples and singles alike, all ages and orientations, and that the atmosphere was uninhibited generally.
I began to talk up the idea that it would be great for Cindy to have another sexual "fling" while we were far away on vacation. Somewhat to my surprise she was quickly agreeable to the idea. I told her that it would be up to her once we were there, but that I would love nothing better than for her to seek out other men for sex. We agreed that unlike the last time with Steve, this time it would be too limiting to have me involved as that could scare off many potential men Cindy might hook up with. We agreed that the only condition was that after the fact she would tell me all about her experiences, holding nothing back. In effect I gave her complete freedom to do what she wanted, and she eagerly accepted the offer! My heart rate was through the roof as I realized what could happen.
We arrived at the resort on a Friday night. This is a resort where the entire resort is "clothing optional" so nudity is the norm, everywhere, not just on the beach as it had been at other similar resorts we've visited. Cindy and I took our bags into our room and got undressed to go out for dinner, me stripping completely, Cindy putting on a sarong low on her hips, a topless look that was very sexy.