By Dr. Ziggy for ASN Lifestyle Magazine
This story is real, it did happen, so I thought that I would share it with you.
“I have thought about it often,” said the woman sitting next to me at the bar of the couple’s club that evening, “but I’m not sure how feasible is it? It seems complicated, too much going on, too many things that can go wrong. Plus, my husband doesn’t seem to be too keen on it, but I would love to give it a try at least once. A girl-friend of mine told me that she did it and it was fantastic.”
The woman’s name was Judy, and the conversation had started innocuously enough. We were chatting about fantasies and realities of sex in the context of the lifestyle when the topic of double penetration came up (no pun intended here). She asked me what sort of sexual fantasies I had realized through swinging. I mentioned that I once engaged in double penetration, something that I had often fantasized about, and I had enjoyed it tremendously.
“So, this situation you talk about, did it just sort of happen, or was it planned?” she asked. I grinned and said, “perhaps I better tell you the whole story. It wasn’t necessarily a planned event.” “I’m all ears, go for it, entice me,” she said with a sheepish smile. She sipped her wine, all the while running her lips around the edge of the glass.
“OK, you asked for it,” I retorted with a devilish look on my face. I had told the story countless times, and the results had always been interesting.
My Double Penetration Story
“It all started at a Halloween party put on by a friend of mine who had theme-like wildish parties every year. But let me set the scenario for you. The house was designed as a party house since they were truly wealthy “lifestylers” and did entertain quite often. There were “theme” rooms included a mirrored room with a large sex swing in the middle, a very a large party room in the basement with plush carpeting, one with a large screen TV that played sex tapes non-stop, and one with several leather couches sprinkled about that provided for a comfortable and cozy sensual atmosphere. There was a deck lounging area outside that featured a large hot tub that could fit 12 people. Overall, this was a lair of sin and debauchery. In any case, at this party, I was hanging out with a friend of mine, Danny, a short Irishman with a cock as thick as a bat and a smile that gave away his devilish intentions. He and his wife were frequent visitors to the place, so I knew them well. We were chatting when a new couple came in and were introduced to the rest of the group by the host. There were about fifteen couples there by then, and I paid little attention to the newcomers since I was engaged in an animated conversation with Danny.
A little while later, I saw the new couple go downstairs to the TV room, and Danny and I followed them there. The woman (found out her name was Alice) was standing near one of the sofas, staring intensively at the action taking place on the screen. Alice was a rather slender woman, wearing a dress probably more fitting for a library worker than a swingers’ party (I found out that this was her first swingers’ event… she was a newbie). On the screen, two men were ravishing an ecstatic woman; their hands and mouths were all over her body, licking, nibbling, biting, while she alternated between them, taking their cocks in her mouth, rubbing, kissing, licking, taking their lengths down her throat, milking their balls with her hands, and running her nails down their chest. The action had come to the point where each man had penetrated the woman, first in her pussy, then in her inviting asshole. Each, in turn, kept a rhythm of to and fro, juices running out of her pussy lips and down her thighs, causing an ever-widening wet spot on the sheets of the bed where they were playing.
‘Are you enjoying the view’ I asked Alice as I stood behind her with my hands resting on her shoulders? ‘Very much so,’ she whispered shyly.
By now, Danny was standing next to her, running his fingers up and down her arm in a playful manner. She grabbed his hand and squeezed it tight. The action on the screen had progressed to a full DP. Both men were moving in unison in and out of the woman’s pussy and ass, going deeper with each thrust till their balls were making a slapping sound against the flesh of her.
I heard Alice gasp. I put my arms around her waist and whispered in her ear, ‘have you ever done that before?’ ‘No, but I would love to,’ she replied. ‘Well, perhaps we can help you with that,’ Danny said. Before long, Danny and I were exploring Alice, while Alice was exploring us. We slid her dress down her shoulders 'til it fell on the floor and realized she wasn’t wearing any panties. Soon after that, we removed her bra, liberating her breasts from their silky confines. We were now lost in a sea of passion as we suckled on her breasts, explored her thighs, fingering her now wet holes, both of us pleasing her, caressing her, kissing every inch of her body. She returned the caresses, getting down on her knees and taking our cocks into her mouth, just like the woman on the screen. And finally, we were both inside of her, moving in and out just like the men in the movie. Now, I have to tell you — it had been a long time since I had seen anyone cum as hard and often as Alice did. She made this sort of throaty noise when she came — a long, strained grunt of pleasure while she grabbed both of our cocks with the muscles of both her openings, and she kept cumming and grunting and grunting and cumming. When we finally couldn’t hold back any longer, she matched our orgasms with a final squeeze of her insides, fluid oozing out of her pussy as though someone had turned on a faucet and forgot to turn it off. Wow, there wasn’t much left of either of us, squeezed to the last drop, you could say.”
Judy is Inspired!
I watched to see what reaction my story had on my chat companion’s face. She kept crossing her legs and rubbing them together as though she was trying to prevent something from creeping into her crotch and was moving her hands in a rhythmic fashion over her thighs as if she was caressing herself, all whilst licking the rim of the wine glass. “And what did she say after all of that?” she asked. “Well, I found that that not only was this her first swinging experience, it was also her first DP experience and her first anal experience. Talk about a night of “firsts,” I joked. “You really got me going with your story. I do want to try it sometime, but it has to be with someone I trust; it’s important to me,” Judy said. “Well, let me know if I can be of some help,” I said with a wicked smile. Judy squeezed my hand and moved on. “I better go find my husband. He must be wondering what I’m up to.”
I have seen Judy a few times since our conversation, but I’m not sure if she ever did follow through on her fantasy. Let me assure you — I think she will sometime when the conditions are right. To tell you the truth, she would be someone I wouldn’t mind sharing “double occupancy” with.
This article originally appeared in the June 2020 issue of ASN Lifestyle Magazine.