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An Introduction to Crossdressing, Pt. 6

"As our evening progresses the fun continues."

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After Steven leaves me at the table with Jackie and his new friend Chandra, I start to fill them in on the details. I tell them, “It’s really Jackie’s fault that I got fucked so good; since he was being so aggressive with his dance partner, I got jealous and grabbed Steven’s ass.” Then I continued with, “This led to Steven grabbing mine beneath my skirt, and then stroking my cock and balls under my panties.”

Jackie interrupted with, “Forget about the dance floor, tell us what happened in the back room.”

I said, “I’m getting to that, just hold your horses - or cocks, as you may prefer.” I told them, “Steven had me right on the edge of cumming, with one hand on my ass and the other stroking my cock. I told him I was about to cum, and then he told me he wanted to suck me.”

Jackie and Chandra both said, “So did he?”

I said, “Yes, he did, and when I came to, I made him fuck me too!”

Jackie interrupted again, “What do you mean came to?”

I told them, “I came so hard that I passed out for a minute or two.” Pausing for a moment I noticed that Jackie and Chandra seemed to be stroking each other under the table. Then I suddenly heard shoes dropping on the floor. Shortly thereafter, I felt two stocking-covered feet starting to rub my crotch.

Chandra then commented, “If you don’t continue the story I’ll stop.”

Chandra must have been wearing the softest stockings ever made, because they felt divine rubbing either side of my cock. So I continued on, “When I awoke he was fingering me to loosen me up for his big cock.”

Jackie piped in with, “How big was it?”

At this point they each had both of their hands in the other’s lap, stroking, fondling or fingering something. Then I heard some more shoes drop, and felt more stocking-covered feet in my crotch. Since they both seemed so interested in rubbing my cock and balls, I pulled my panties to the side and spread my legs wide.

My enjoyment was cut short, however, when they both said, “No story, no rubby.”

Getting back to the story, I continued, “His cock was about eight inches long and two and a half inches across." The stroking of my cock and balls continued, and it was having the desired effect.

Jackie spoke up saying, “How did you get that thing in you - and did it hurt?”

I told them, “Steven was very patient, stretching me good with his fingers first, then slowly working his cock into me.” At this point one of them was trying desperately to push their big toe into my ass, so I slid down in my seat to give them better access and felt that toe wiggle its way into me. I could tell that they were both close to coming, so I finished the story.

“As Steven finally worked fully into me I felt so feminine and full, especially when he filled me with his cum,” I said, as the toe moved deeper into me. As I tried to continue I saw both of their faces twisting as they came, covering the underside of the table and the floor with their juices.

About this time our waitress Susan came to the table and said, “You girls need any refills?”

I spoke up, since the other two were still recovering. “I think we could all use a drink about now to replenish lost fluids; any ideas, Susan?”

She slid in beside me and with a sly grin said, “What lost fluids would those be?” Reaching under my skirt, she was a little surprised to find that my underwear was already pulled to the side. As she gently stroked my baby-smooth cock and balls, she asked, “Would a screaming orgasm replenish those fluids?”

“No, I don’t think so,” I said, “but it sure does sound like fun!”

Susan said, “I’d love to take you two home tonight to give you just that.”

I told her, "I’ll discuss it with Jackie when he is coherent, but in the meantime can you get us some sodas?”

She gave my cock one last squeeze and said, “No problem, I’ll be right back with your drinks, sexy.”

While Susan was away I asked Jackie, “What do you think of her offer?”

He replied, “I don’t know; I was kind of hoping that we could share Chandra.”

“What if we bring Chandra along and have a five-some with Susan and her husband?” I asked.

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Chandra piped up saying, “I don’t know if five-some is a real word but it sure sounds like a fun one.”

I agreed, and said, “Susan won’t be off until closing anyway, so we still have a few hours to have fun here.”

Susan returned with our drinks, and I said, “If we can bring Chandra along, we would love to come over.”

She replied, “That sounds like a whole lotta fun, I'll look forward to it, and I’m sure my husband will too.” Then she added, “I get off at two a.m. and you can follow me to my house, or we can go to your hotel if you’re more comfortable with that.”

I looked at Jackie and he said, “I would prefer it be the hotel.”

I turned back to Susan and said, “The hotel it is.”

She said, “Okay,” and then headed back to the bar to take care of her other customers.

As Susan walked away I looked back at Jackie and Chandra and said, "Now that we have taken care of that, who is going to let me fuck them on the dance floor? My cock is hard as hell, between you two assaulting my cock, balls, and ass with your feet and Susan stroking me while she was here. I need to cum!”

Jackie looked over at Chandra and said, “You stuck your foot up his ass? That is sooo hot!” Then he said, “I’m up for it, but why on the dance floor?”

Chandra jumped in, saying, “Are you kidding me? Doing it in front of all those people makes it even hotter!”

We all got up and headed for a very crowded dance floor and worked our way to the middle. Once we were there we started rubbing all over each other. I worked my way behind Jackie, reaching under his skirt to move his g-string to the side. I then wrapped my left arm around his waist, while lifting both of our skirts with my right hand and resting my cock between his cheeks.

We danced this way for the rest of the song, with my cock rubbing between his ass cheeks. With the beat picking up on the next song, I reached down and lined myself up with his hole. I slowly pushed my way inside until I was resting up against his ass.

When Chandra realized I was deep inside Jackie he moved behind me and started playing with my ass. Then he slipped his hand further forward and cradled my balls, and gently started massaging them.

As Jackie ground back on my cock I slipped both hands around him. I grabbed his right tit with my left hand and turned his face back to me with my right, giving him the deepest kiss I could at that angle. While we were swapping spit I slowly started pumping in and out of him.

While I was slowly fucking Jackie, Chandra decided to get in on the action. He spread my ass cheeks with both hands and eased his cock into me. Given that I had been teased for the last twenty or so minutes, and now had a cock in my ass too, it didn’t take long before I was filling Jackie’s ass with my cum.

As I slipped out of Jackie he turned towards me and we kissed deeply. All the while Chandra continued a steady slow invasion of my bowels. When Jackie and I finished our deep oral probing I said to him, “Why don’t you move behind Chandra and get yours too?” He thought that was an excellent idea, and moved in for the kill.

Shortly after Jackie entered Chandra, he filled my ass with cum and within another minute or so Jackie was filling Chandra’s ass. Now that we had all had our fun we needed to head to the bathroom before the cum ran down to our ankles.

Once we were done cleaning up we all headed back to the table for a little rest and refreshment. Susan must have been reading our minds as she brought over some fresh drinks and an appetizer platter. She said, “Now you girls eat up to regain your strength, it’s only about thirty minutes until closing.”

Before we could thank her she was off and they were announcing last call. We ate and drank quietly for a few minutes, and then started speculating on the events to come.

Published 
Written by stockingluvr
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