I have blogged and storied at length about Cindy, her love of cock, sucking cock, fucking cock, (cocks actually, plural, lots of cocks), her pussy, her love of cum and her love of taking on many guys and the lifestyle we created which allowed her to do that and got me a wholesome share of pussy too.
But anal has at best been a little rarely mentioned side dish.
For me, not at all, never done anal, not even with Cindy. Just not my thing, I love pussy, a vagina, a cunt, a set of lips wrapped around my cock.
So although Cindy has more than shared all details of all exploits, well, most details and most exploits, she had been less than forthcoming on stories of getting fucked in the ass, thinking I would disapprove.
I dont disapprove, I just dont do it.
But it’s Cindy’s ass and she is welcome to stick a cock into it and the cock is welcome to drench her ass in cum. Lately it was pleasing her more and more. Occasionally, she used a toy claiming she needed time to accustom her ass to the real thing. In the middle of a party, erect cocks are not particularly patient, or gentle. They just want something to bury themselves in and ejaculate in to.
She wasn’t quite sure the first time it happened, or perhaps she wasn’t quite ready to share that experience with me. She knew that a few people during the party fuck atmosphere had tried. Some had failed, given up, not gone in very far or for very long. Some had contented themselves with ejaculating onto her butt. But at some point, someone got in there, stayed and came. Her first clue, so she told me, was a load of cum dripping from her ass. It felt different to her than cum oozing from her cunt. Initially, she wasn’t really receptive to it. But, at some point, she became ok with it, then decided she might like it and probably needed to “prepare” for it, make it easier for it to happen, and began looking forward to it.
Cindy would entertain me with all of her rituals regarding the preparation of her pussy for fucking prior to a party or even a little personal adventure, and allow me to watch. Same for the great care she went to applying her special glossy, deep red cherry lipstick, a detail that got obliterated when the first cock of the evening penetrated her lips, an event that occured fairly quickly at any gathering. Her rituals for preparing her ass for penetration however stayed hidden.
Still by her account, she preferred a cock in her pussy or even sucking on some guy’s cock. She enjoyed having a guy cum in her cunt because she could feel it. If she was close to an O, it would finish the process. Having a cock cum in her mouth was more personal. Very personal, I would say. At least that’s what she told me, but she has been known to be less than entirely truthful when it comes to what she puts where, who put it there and how many different men…. Oh well, in the end she fesses up, tells me the full story, I get really turned on, instead of upset, then I fuck her like it was the first time.
She had started making sure that her ass was prepared to receive the occasional cock, and truth be known, maybe not all that occasional. She would clean herself fastidiously, every last hair was removed, lotions and or powders were applied. Secondly she had researched and applied lubricants, not just for easing access but enhancing feeling as well as providing a tingly sensation for the cock that went there. She shared with me that a few guys had told her about how good the tingly feeling was.
That little reddish starburst opening not far from the glorious opening to her vagina now had a “Welcome, C’mon in” sign on it.
She was starting to share more information with me on the newly discovered joys of having a cock in her ass. She told me of feeling two cocks, one in her cunt, the other, next door over. It could be a little painful, she would say, but a good painful, and if the cocks were both a tad larger than normal, she might wait for until her final fucks of an evening, but she was gaining an appreciation for it, getting enjoyment. She also seemed to be getting a real turn on for some pain. I wondered where that might lead. Her enjoyment of anal sex, particularly the pain of a larger cock seemed to coincide with her enjoyment of pain in other areas of sex.
She finally got bold enough while she was on top of me one time at a party, to ask me if it was ok for someone else to fuck her ass with me inside her pussy. I had barely muttered: “Ok”, before I started feeling another cock through the thin wall between her pussy and her ass. She must have had that pre arranged with the other guy. It was just too quick to be a coincidence. So quick I had no chance to change my mind, not that I was planning to. I could tell she was experiencing some pain, yet I could also tell she was enjoying the hell out of it, her arms were tensing, her nails digging in my chest, and she was biting her lip as we both thrust into her.
We both came. I guess all three of us came. I must say that I enjoyed that and so did Cindy.
You might think it odd to fuck your own wife at a wife swapping party, but Cindy and I did that more than a few times.
She said there was one guy from our group of friends who had really wanted to fuck her in the ass. I instantly knew who he was, he had a very large cock. Cindy had decided to try it, in her ass that is. She had more than once had that cock in her pussy and her lips and tongue had spent quite some time with it as well. She had compensated for her inabilty to deep throat his cock by allowing him to cum into her open mouth while flicking the head actively with her tongue, and aggressively stroking him with her hands, and he loved it when she looked him in the eye when she did that. She must have told me that story more than once. His cum had been in her, on her, everywhere but one place. She admitted that though she thought it might be a little painful, the thought of it had turned her on. She had decided to start using her biggest toy for practice. I remember her giddy as a schoolgirl with a new i phone, telling me that she had finally gotten the toy all in. She couldn’t wait for the next party, which was rapidly coming up.
I asked her: “ Why wait for the next party, I know you do him on the side from time to time.”
She was surprised I knew, she didn’t deny it, she just said: “I have my reasons.” then started to giggle.
As we drove to the party, she said that the reason she didn’t just do it as one of her “little adventures” as she called them, is that she thought she should get her ass fucked by a couple of guys with smaller cocks first to loosen up. Neither having been a pitcher nor a catcher in that sport, I wasn’t sure what to say. Besides, how many husbands get to advise their wives about being fucked in the ass by a few guys, or for that matter having an occasional fuckbuddy with a very large cock on the side who loves to ejaculate into her open mouth because she couldn’t get much more than the head into her mouth. It seemed wierd. Still, I did manage to tell her it was a good idea. I also wondered about how occasional these fuck buddies were, I was sure there were others too. Oh well, I had my own little fuckettes from time to time too.
At the party, she immediately went over to the guy with the large cock, chatted and laughed for a few minutes. Then she went over to two other guys and started chatting with them. Distracted for a sec by the lady I was talking to, I looked up and all three had disappeared. I guessed they were the guys with the smaller practice cocks, and they had just headed off to practice.
“Their cocks were not that small, in fact not small at all.” she later injected during her tell all commentary on the evening. She had smiled after telling me that.
Really large cocks rarely get as hard as smaller cocks, so entry into a difficult place can be a problem for them as well as for the person with the difficult place, so the guy with the big cock just waited, drinking coke, avoiding alchohol, waiting for the other guys to loosen things up. I thought about going over to talk to him, but there was a cute lady starting to play with my cock.
As she told me later, it wasn’t long before the practice session ended when the second fellow came into her ass, joining his cum with the cum left over from the first guy and she walked out to the living area, she was naked, cum from two cocks was dripping from her ass and she invited Mr Large Cock back to a bedroom. I was patient when she told her stories, basically because they could really turn me on. She told me that he applied lubricating jelly to his cock, then more to her, mixing it with the cum and lubricant still there. Surprisingly, he had little trouble getting it in, and the initial entry had taken her breath away for an instant. There was obviously some pain, but somehow a good pain, almost enjoyable pain, according to her. He had fucked her for a good long while with his long but slow strokes, her ass up in the air, in a doggy fuck position, her grabbing, clawing, even biting on a pillow. Finally, he came. He then flipped her over and went down on her very wet yet unfucked pussy and brought her to a wonderful O. She was sure that her pussy area, those lips, the clit were coated in the cum of all three guys, yet he seemed not to mind. He was happy, she was happy. They came out of the bedroom giggling, he nodded to me. I nodded back
“Ready to go home now?” I asked.
“Not yet, I have a few rain checks, from previous parties.”
I saw her wave back and smile at a guy with a big grin on his face, another guy was walking towards her, also with a big smile.
“Rain checks I take it?”
“Yup”
“And after them, a couple more rain checks?”
“Maybe, probably.”
“How do you get so many rain checks?” I finally had to ask her.
“Oh, they start fucking me late in the evening, they are tired, they don’t get there, they want to cum back and finish what they started”
“Oh” I said
“Or after fucking me, they hear about my blow jobs,” she stopped to laugh.
“Oh.” I said again, then added: “So those two guys… fuck or blowjob?”
“Blowjobs”
“Gee, no pussy action this evening?”
“There will be, this pussy is not leaving here a virgin.”
She smiled and gave me a quick kiss.
“More cock up your ass?”
She laughed.
“No that road is closed for the evening.”
Time for me to go find the bar, I thought. As usual, I was done for the evening and as usual, she was just getting started.
As I was mixing my drink, I was seeing the guys with the blowjob rain checks with her and already touching her.
Cindy was touching them.
I turned away to grab a slice of lemon. I glanced back, they were gone.
By the time I sat down, I knew that one of those cocks was already in her mouth.
I was pretty sure another was soon in her pussy.
I could go in there and watch. I liked that. She didn’t mind
I could even touch her, play with her tits perhaps as a cock or two were pounding into her, releasing their eruptions of warm salty milky fluid.