Chloe Redux

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.

I opened the door and introduced myself. He grinned for ear-to-ear and closed to door behind him. Jon was a very big guy. Chloe had described him as big, but he looked like a professional football player, big and buff all over. I am a big guy, but Jon was BIG. He was six-four or five and about 250 lbs.

We had a cocktail or two waiting on Chloe to present herself. I had no idea what she would wear, if anything, seeing as we had both seen her naked before. Rather than be intimidated by his size, I was happy. I knew Chloe had described him as hung and one of my biggest turn-ons is to see a small woman work and struggle to get a big cock inside of her. I didn't want her to injure herself but see the pain turn to pleasure once we were fully ensconced. I hadn't seen Jon's cock, but I was a firm 8" and I had struggled at times to get fully buried in some of the smaller women I had fucked over the years. I felt if he was as large as me, Chloe has her work cut out for her. The biggest turn-on when I was trying to get in Laura's ass was her deep breathing and her holding me back with her hand against my pelvis as she adjusted to my size, all happening with my wife right there.

With my ex-wife, the first time I entered her pussy, I had to eat her pussy and then ease into her even though she wasn't a virgin. She just had never had a cock as big as mine. Chloe had told me that she wanted, during our initial coupling, to try and take Jon in her ass and have me in her pussy. She said she felt she was giving me a gift and wanted to look into my eyes as I penetrated to the deepest, tightest part of her. I could not wait to watch Chloe's reactions as she took us on.

After approximately 30 minutes of me getting to know Jon, Chloe came out of her bedroom dressed in a beautiful purple and black matching panty and bra set. She had on black 4 inch heels. Her breasts rested on the shelf-like bra. Her light cocoa nipples were barely concealed and hard. The panties were cut high on the sides and she looked like a tiny goddess. She didn't seem the least bit embarrassed or nervous. She said,

"Hey, Jon. I hope you are looking forward to tonight."

She moved close to him and rubbed his growing cock through his jeans. Jon smiled at her and took her hand, pulled her close, bent down to her and gently kissed her lips.

"You are stunning, and I cannot wait to do this with you."

With that, Chloe turned to me and kissed me on the mouth, giving me a little swipe of her tongue and asked it me to get her a stiff vodka rocks. As I handed Chloe her drink, I also handed each of them a hit of Ecstasy which we promptly swallowed. She took Jon's hand and led him back to her king-sized bed with me following. Watching her beautiful full ass move back and forth in those sexy panties and her firm muscular legs flex as she walked, made my cock so hard, I could barely walk. Knowing what was about to happen made the eroticism almost unbearable. It was all I could do not to throw her on the bed and fuck her brains out but knowing she was about to let us stuff her full of cock kept me in check. It was a fantasy about to become reality.

She sat down on the edge of the bed and motioned us forward. When our crotches were eye-level to her, she reached for Jon's belt and began taking his pants off. She unzipped him and tugged his jeans over his rock-hard ass. He was commando so his cock sprung up and brushed her lips. He was indeed huge. She smiled as Jon removed his shirt and she grinned up at him and me through sexy, mischievous eyes.

She knew how this turned me on, so she leaned in and, without touching him, lightly licked at the copious amount of pre-cum drooling from the head of his shaft. She then made a show of tasting him, followed by an "Uuummmh." She grasped his engorged cock with her right hand at the base, her left hand above it, squeezed it and leaned in and engulfed the head. Jon rocked back on him heels and in almost a whisper said,

"Fuuuuck!"

Chloe wanted to satisfy and be satisfied. She moaned around his massive shaft. She could barely fit the head in her mouth. She slowly brought the large member to a raging, jerking hardness. The veins were pulsing, and the head looked red and angry. Jon reached for her hair and she said ,

"No, no. I'm in charge tonight."

Jon and I just grinned at each other. She moved over in front of me, peeled off my pants and proceeded to do the same to me. She wrapped both of her tiny hands around me, but I was no match for Jon. With Jon, she could still suck the entire head and several inches into her warm mouth. This went on for 5-10 minutes and the X started kicking in. The feeling of that moment took us to a whole other level. The aura around Chloe and what she was doing to us was exquisite. My cock had never been harder or bigger.

We lay Chloe back on the bed and began kissing her mouth, breasts and down her stomach. As Jon worked over her upper body, I slid down between her legs and began kissing gently both her open thighs, kissing them, moving from one to the other. She was in heaven. I worked up to her panty-covered pussy and licked at the large wet spot. I covered her mound with my whole mouth and gently blew my warm breath on her. She reacted with increased breathing and gyrating her pelvis against my mouth.

I couldn't take it any longer and I quickly stripped her of her panties and engulfed her sex, sliding my tongue from her asshole up to her clit. Her pubic hair was trimmed shorter than usual and perfectly manicured into a beautiful, nuanced brown triangle. By this time Jon had removed her bra and she had kicked off her heels. Jon hovered over her feeding her his cock.

When I sucked her clit into my lips she moaned loudly around the large member in her mouth. She was a picture of raw, wanton female. Jon squeezed her now freed breasts and roughly tweaked her nipples. She was creaming in my mouth and bucking through the first of many orgasms to come. Before she could calm down, Jon moved me out of the way and pulled her hips about a foot off the bed. He was more than ready and so was Chloe.

She grabbed his cock rubbed it up and down her drooling gash and lined it up on her cunt. He thrust his entire 10 inches into Chloe in one powerful movement and she groaned a sound I had never heard any woman make. Jon threw his head back and held her on his cock. He then looked straight at her and began a slow, purposeful fucking of my girlfriend. His massive meat was pulling the insides of her vagina out several centimeters every time her withdrew. She was throwing her head from side-to-side, the veins on her neck standing out as he pummeled her. I crawled up to her head and kissed her deeply. She went crazy and begged me to stick my cock in her mouth. I did and she proceeded to suck me like my dick was the giver of life. The fucking Jon was giving this woman was epic. It only lasted several minutes as no one could keep up that pace for long. She was mewling around my cock, her eyes rolled back in her head when Jon planted his staff against her cervix and started unloading his cum into the deepest part of her womb. She felt it and paused a second and then began thrashing around, convulsing and racking her body.

This sent me over the edge, and I poured a load into her mouth like never before. She continued sucking and swallowing but it was too much for her tiny mouth. My frothy, white cum poured out around my cock, down her chin, onto her breasts and onto her bed. Jon was in the last throes of his orgasm, continuing to thrust into Chloe until he collapsed onto her, kissing her cum filled mouth. I had never seen nor done that, but it was very hot. He had to know she had my cum in her mouth but he didn't seem to care.

After that athletic exercise we all lay on the bed, catching our breath; Jon and I loving on Chloe as she played with our withering, cum-covered cocks. We took a break and grabbed some more drinks. The Ecstasy was really affecting us now and after several minutes of standing around hugging and fondling a cum covered Chloe, we looked at her and I asked,

"Are you ready for the main event?"

She smiled and said "Oh, yeah!"

We went back to her lair, but Chloe asked Jon to first bring one of her bar stools to the bedroom. I didn't know what she had in mind, but I was game for whatever. It had to be good. She had Jon put the stool in the center of the bedroom, then crawled on the bed. She reached into the nightstand and brought out her vibrators and her lube. She got on her hands and knees with her ass facing us. She looked over her left shoulder and handed me the vibrator and Jon the lube. She said,

"Loosen me up with these."

Holy shit! Jon walked up to her upturned ass, leaned over, spread her cheeks and tongued her little brown rosebud. He then covered his middle finger and her asshole with lube. He slowly began working his large middle finger into her rectum as she put her head down on the bed and began her deep breathing. Jon's finger was nearly as large as her smaller vibrator. Chloe reached back with both hands and spread her ass cheeks apart again.

When she felt comfortable, she said,

"Ok, go ahead with the vibrators."

I caressed both ass cheeks kissing them to relax her more, covered the smaller dimpled, cock-like vibrator with lube and turned it on. I placed the tip at her winking asshole and began slowly working it into her, pulsing it against her hole and rotating it slowly. She moaned, quietly, saying

"Oh, yeah! Oh my God..." and her asshole blossomed open.

Her ass seemed to actually suck the gel cock into her butt. I then started moving it in and out of her ass and rotating it as she deep-breathed, willing herself to relax her sphincter. She was having small, almost continuous mini-climaxes while this was going on and her pussy was streaming down her thighs. Without asking, I picked up the large nine inch dildo and slid it into her pussy. She grunted again and started repeating,

"Oh yeah...oh, yeah...oh, yeah..."

Jon and I looked at each other with wonder in our eyes. What a woman!

Shortly she squeezed her ass muscles to expel the vibrator and it slid out of her ass, falling and buzzing on the bed. I turned it off and extracted to larger vibrator from her cunt. Soon she was ready.

She led Jon over to the stool and had him sit, naked, his cock standing huge and straight. She leaned over and fluffed him a bit with her mouth, to get him super-hard. She reached for the lube and coated his cock then worked a glob of lube into her asshole with her fingers. She then stood on the footrests on either side of the stool facing away from him. She took his cock, eyes closed and lined it up with her asshole. Jon was holding her ass up to support her while she gave into her lewd desires. It took her several tries, but she was able to get his cockhead past her sphincter.

When the head of his cock pierced her anus, her eyes opened wide, then she bit her lower lip and closed her eyes and let herself settle down on his raging boner. As she controlled her descent onto him, she pursed her lips and breathed in and out rapidly as she took more and more of him into her ass. At a certain point she had about half of his rock-hard cock up her ass. She looked at me and smiled, took in a deep breathe and, blowing out, lowered herself the rest of the way until his balls were the only thing I could see below her drooling gash.

She sat still, adjusting to the monster, licking her lips and willing herself to begin fucking herself on Jon's mighty pole. Her pussy lips were swollen, and her cunt was blossomed, wide open. She began to gently and slowly move up and down on his greasy pole. The look on her face was angelic. She was in her own heaven. She moved up and down on him really getting into the rush of the X and his cock sliding in and out of her back passage.

After several minutes and many micro-orgasms, she stopped moving and looked at me and patted pussy. That was my signal. I walked forward, her head just slightly lower that my face and proceeded to kiss her deeply, pinching and fondling her tits. She leaned over and took the head of my cock into her mouth and sucked gently, making me extremely rigid. All this time Jon is buried in her ass and kissing her neck.

I have always wanted to lick a woman's pussy while impaled with another man's cock to see the woman's reaction to that much stimulation. I had done it with my wife while her ass or cunt was filled with a large vibrator. I would worship her clit, sending her into orbit then, if the vibrator was in her ass, shove my hard cock balls-deep into her cunt. She loved it.

However, I had never done it when a live cock was in the woman. I didn't know how Jon would react, but I had no desire to touch him, but it might happen on accident. My lust was so strong, I didn't even think, I just dropped to my knees and slurped at Chloe's pussy, sucking on her swollen clit. She immediately grabbed me by my hair and started cumming. She was bathing my face in her feminine juices and spreading her legs and curling her toes in orgasmic bliss. Jon was cool but I never really touched his cock, thank God.

I ate Chloe for maybe a minute, then stood, reached behind her knees and pulled both her thighs outward and upward toward her chest at about a 45-degree angle. Jon grabbed her behind the knees holding her open. I moved forward and rested my cock on her beautiful opening to get myself slick with her juices. She knew what was coming and reached both her hands up around and behind Jon's head. She was wide open, stuffed in her ass with a huge cock and ready to experience her first true DP. I let my cockhead slid down to her open flower and in one slow, gently thrust, I buried myself in her. Her eyes opened wide, she took in a huge breath and started shivering and flexing her entire body. Her nipples were like erasers. I touch them and twisted them with just enough force to elicit an