Her name was Judy, and the conversation had started innocuous enough, we were chatting about the fantasies and realities of sex in the context of the Lifestyle when the topic of “double penetration” sort of came up (no pun intended….). She asked me what sort of sexual fantasies had I realized through swinging and I mentioned that I had once engaged in DP situation, something that I had fantasized about, and that I had enjoyed it tremendously.
“So, this situation you talk about, did it just sort of happened or was it planned?” she asked.
“Well, my dear, perhaps I better tell you the whole story…” I grinned.
“I’m all ears, go for it… entice me…”, she said with a smile, while sipping her white wine.
“OK, you asked for it” I retorted with a devilish grin on my face. I had told the story countless times and the results had always been interesting.
It all started at the annual Halloween party put on by a friend of ours. Let me set the scenario. The house was designed as a party house since they were true wealthy lifestylers, and did entertain quite often; there were six theme rooms including a mirrored sex swing room, a large party room in the basement with plush carpeting, a large screen TV played sex tapes non-stop, and several leather couches sprinkled about provided for a comfortable and sexy atmosphere. There was an outdoor hot tub that fit 12 couples, and a deck lounging area.
In any case, at this particular part I was hanging out with a friend of mine, Danny, a short Irishman with a cock as thick as a bat and a smile to match. Him and his wife were frequent visitors so we knew them well. A new couple came in and was introduced to the rest of the group. There were about fifteen couples present by then, I paid little attention to the newcomers since I was engaged in an animated conversation with Danny.
Later on we saw them go downstairs to the TV room downstairs and Danny and I followed them. The woman (found out her name was Alice) was standing near of the sofas, staring intensively at the “action” taking place on the screen. Alice was a rather slender woman; she was wearing a dress probably more fitting for a librarian than a swinger (I found out that this was her first swingers’ event…a newbie). On the screen two men were ravishing a woman, their hands and mouths were all over her body, meanwhile she alternate between the two of them, taking their cocks in her mouth, rubbing, kissing….
“Are you enjoying the ‘view?'” I asked as I stood behind Alice, my hands resting on her shoulders.
“Very much” 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. I felt her gasp. I put my arms around her waist and whispered in her ear “Have you ever done that before?”
“No”, she replied…”…but I would love to…”
“Well, perhaps we can help you with that…”
As things turned out, before long Danny and I were exploring Alice, while Alice was exploring both of us… we were lost in a sea of passion, both of us pleasing her, caressing her, kissing every inch of her body; and finally we were both inside of her, moving in and out just the men on the screen. Now, I have to tell you, it had been a long time since I saw anyone cum as hard and often as Alice did. She made this sort of throaty noise when she came, sort of a long, strained grunt of pleasure while she grabbed both of our cocks with the muscles of both her openings…and she kept cuming and grunting, and grunting and cumming… and when we finally couldn’t hold back any longer she matched or orgasms with a final squeeze of her insides…till there wasn’t much left of either of us, squeezed to the last drop, you could say.
By this point I was watching the reaction that my story had of my chat companion, Judy. She kept crossing a legs and rubbing them together has though she was trying to prevent something from creeping into her crotch, her hands moved in a rhythmic fashion over her thighs as if she was caressing herself….
”And, what did she say after all of that?” she asked.
“Well, I found out 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 now…sometime… but it has to be with someone I trust…it’s important to me….”
“Well, let me know if I can be of some help…”
Judy squeezed my hand and moved on. “I better go find my husband…he must be wondering what I’m up to…”
I saw Judy a few times since our conversation, not sure if she did ever followed through on her fantasy , but let me assure you, she would be someone I wouldn’t mind sharing double occupancy with….
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