This story is true and is the follow-up event from my posting of "Chloe". I suggest you read that story before reading this because what happened in that event led to what I am now writing about.
I had been seeing Chloe for several months when this story happened. She and I had both gone through divorces in the last several years. Hers produced two children who were both under 10 years of age. My eleven-year marriage had produced no kids. We were both starting over in the Sarasota, Florida area and both worked at the same medical center. Our courtship was fairly new. Chloe was a small, voluptuous brown-haired 28-year-old woman. I was a blonde 37-year-old man at the time, 6'2", 215 lbs and in the best shape of my life due to a program of fitness, including weights and cycling.
Our original hook-up led to an amazing afternoon in bed at her Florida pines home, some 20 miles inland from Sarasota. I lived across the street from the beach in Sarasota. The sex was wonderful that day, especially her ease at anal sex. It happened by mistake but she was experienced and took my sudden, accidental spearing of her ass in stride. In fact, when I suddenly went up her ass her eyes got super wide and rather than scream and tell me to stop, she simply looked me in the eye and breathlessly said in no uncertain terms,
"Don't pull out! Keep fucking me!!"
I had done anal only one time previously. My first anal partner was one of our lady friends with whom my ex and I had swung with. One night the three of us had just finished several hours of non-stop lovemaking when she asked if we had ever done anal. We told her we I had tried but my ex was only 5"0" and I was just too large. The several times we tried it my wife just couldn't relax and accept my large cock. I have to say it was my fault because I didn't know how to relax my wife enough before entering her rectum.
Our friend Laura said her current boyfriend in Germany had taught her and now it was fantastic. We had given up trying to make anal work for us. I coyly asked her if she would let me in her ass and after we both cleared it with my ex, our friend introduced me to the joys of slow, methodical anal sex while my then wife kissed and caressed our friend. It was slow, sensuous and mind-blowing. My point is that I learned to take it slow.
I didn't have to worry so much with Chloe. Chloe and I talked about her ability to take my 8" cock into her back passage with relative ease, without pain and without lubrication. I marveled at this as my experience and other information led me to believe it could be very painful if the man was not extremely patient and gentle and the woman was very relaxed and lubricated. Chloe said that she and her husband had been doing anal for years and she had also experienced anal with other men in their swinging circle. She said she obviously preferred it with lube, but she was comfortable with it regardless, and found it enjoyable in the right circumstances and with the right man. I guess I was the right man because she took me easily without any preparation. She also said she would not do anal with just anyone.
This conversation led to more anal fucking over the next several weeks and to many discussions of our fantasy's. Like Chloe and her ex, my wife and I had participated in various threesomes, foursomes and cuckolding during our marriage. We had mainly been involved with close friends, but Chloe and her ex had been with friends, swing clubs and private parties. She even said they had a threesome with the gentleman whose house was about 300 yards from her place. The threesome went well but the neighbor's wife was not clued in and when the neighbor confessed and tried to get his wife involved, she divorced him over the sex with Chloe. Oops!
I had embarrassingly told Chloe of my fantasy of DP-ing a willing woman and she told me, somewhat embarrassingly of her desire to be gangbanged by 4-5 men but didn't know how to set it up and stay safe. Her ex had evidently been the organizer of their previous sexual escapades. She told me she would think about the DP and who might be willing to have as the other man. She said she fantasized about a DP as well because anal was so pleasurable and easy for her.
She also told me she thought being stuffed full of cock could be erotic as hell. I told her I didn't know that many men in the area because I was new to Sarasota. I asked if she wanted to contact some of her male swinging friends, but she wanted to move on from those people. Partly because her ex was probably still participating in that circle but more because she wanted fresh experiences and new men. She said she wanted the men to be strangers , but with current STD bloodwork papers. She also wanted them, attractive, fit, clean and hung. We decided to place an ad in one of the many swinger publications in the area. She left that up to me. The gangbang is another story.
I could not believe my good fortune in finding this beautiful, sexy woman. My ex was a very sexual person but a reluctant participant in some of our adventures. I know it conflicted with her country-club, conservative upbringing. Finding Chloe fulfilled one of my greatest fantasies; a woman as open-minded and horny as me.
We went for a drink several days after our last get-together and after a couple stiff drinks asked me if I still wanted to fulfill my fantasy of DP-ing her. I said
"Of course."
She then asked if I would have a problem with her asking her neighbor with whom she and her ex had the threesome. I said no, that would not be a problem at all. I asked,
"Why him?" She looked at me with her heavy-lidded, horny eyes and said,
"Because he is very well hung." I looked at her over my glass with raised eyebrows and said,
"Oh, really? You like 'em big. Do you?" laughing. She grinned sheepishly, smiled over her high-ball glass and said ,
"Yep. Why do you think I like you so much?" Well, touche' Chloe.
She talked with her neighbor and set it up for the following Saturday evening when her kids would be with their dad. This guy's name was Jon and he was coming over around 7:00 pm. I arrived around 3:00 in the afternoon for some pre-play and pre-planning. After all, this was going to be a momentous night for all of us. None of us had ever participated in a DP. Obviously, we had done anal, but Jon had never done either. We made love several times in those 4 hours but Chloe, wanting to be fresh for us insisted on stopping around 6:00pm to get a long bath and get ready. She was still getting herself put together when Jon knocked on the door.
