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Pegging Delight

It was when I got a call from Jennifer later that afternoon that I became aware that Holly wanted them to join us as well. "Holly told me she wanted to fuck you in the ass. And, since she hadn't seen Jerry as Jessica, she wanted to fuck you while you sucked Jerry off as Jessica. Well, that and a few other things. She's really trying to make up for lost time. I told her that we all would love whatever she had in mind tonight. See you tonight."

I just sat there with a smile on my face as I hung up the phone from our conversation. Holly really wanted to experience her fantasies. Well, I still had three hours before I would head out of the office and it took all I had to concentrate on work and not about the upcoming evening. I left the office at five-thirty that evening and headed home.

When I arrived home, there was a box on my porch. Good thing it made it. I had ordered more lube, Anal-Ese, and a few new toys on line and figured that the ordered must have showed up. I had actually ordered the items for the upcoming monthly party two weeks away but very glad that I ordered early.

I pulled into the garage and got out of my car, placed my briefcase next to the door and walked around to the front door to retrieve the package. I smiled when I read the return address was from the company that I had placed my order. I walked down to the mailbox and saw Jerry turn onto our street and waived. I got the customary "honk of the horn" and a smile as he past by and pulled into their driveway. I walked back to my garage as his car disappeared into theirs. I pressed the down button, letting the garage door slowly close as I entered the house.

Once in the house, I placed my briefcase at the door to the den and walked back into the kitchen. I knew I had better eat something. I nuked a healthy brand name frozen dinner and turned on the news as a distraction. After eating and cleaning up, I opened the box. It was all there including the lube, Anal-Ese, and two new lifelike dildos, both made for strap-on harnesses. The incredible things they had been able to do with lifelike cocks these days. The things they can do with new materials. One was a six-inch and the other an eight-inch. I knew that these would get broken in this evening.

The phone rang catching me off guard. It was Jerry. "I heard we are coming over. Jen wants me to dress for tonight because Holly hasn't seen me as Jessica. Problem is, the kids will not be in bed in time for me to dress here. Jen wants me to come over early and get started and she'll help with makeup after putting the kids down. She'll bring the monitor over just in case. What do you think?"

It only took a few seconds to respond, "If you come over after dinner, you can shave me and I'll shave you. What do you think of that answer?"

"l will see you soon. She's already laid out the outfit. You will like it, sultry and slutty."

"I'm looking forward to it. See you soon." Now, I needed to go upstairs and change the sheets from my night with Holly. I remember smiling when I thought about adding the restraints to the bedposts. I was already getting hard from the thought.

Jerry and Jennifer had keys to enter the house on their own. That allowed me to start stripping down the bed without having to worry about going back downstairs to open the door. I grabbed the red satin sheets and pillowcases from the linen closet and then the restraints from the trunk in my walk-in closet. I had completed changing the sheets and attached one of the foot restraints when Jerry arrived. I heard the door chime announcing an opened and then closed door. I had placed the second foot restraint on when Jerry appeared at the door with an overnight bag I knew contained his wardrobe for the evening, cosmetics and wig.

"So, who do you have planned to be in the restraints tonight?"

I smiled back and responded, "I have a pretty good feeling it is going to be me at Holly's request. And, she was really turned on by the idea of fucking me in the ass tonight. Pleasure all the way around."

Jerry helped me finish attaching the hand restraints to the head rail and I told him I would get ready and start the shower. Jerry already had a nearly hairless body, smooth and very tight. The shaving was just for touch ups and making sure he was squeaky clean.

I walked back into the bathroom and stripped. I took a few minutes to fill my anal douche with some warm water and laid a towel down on the tile floor. I wanted to be squeaky clean for my ass fucking. I sat down on the towel, leaned back, pulled my knees back and reached under to insert the thin head in my soon to be pegged ass. It slid in easily. I slowly squeezed the ball letting the warm water enter my ass. I stood up and sat down immediately on the toilet to evacuate the first rinse. I repeated twice, enough to make my evening a more enjoyable one for all of us.

I started the shower and peaked around the corner to let him know the water was ready as he was placing his ensemble out on the bed. All black tonight with his fair skin. His transformation is always something to watch.

Jerry entered the bathroom as I finished cleaning up my rinse and smiled, "I did that already. I am looking forward to this evening. Jen said Holly is intent on another fuck-fest tomorrow evening when Nick gets back too."

All I could do was grin. I reached into the shower to test the water and found that it was ready. I entered and Jerry followed me into my large walk-in shower. I took the razor and soap from the shelf, ready for any touch ups required. I began by soaping up Jerry's cock and balls and took my time to make sure there was no hair. He turned around and I checked his awesome tight ass cheeks and he was slick there as well. He smiled at me and noted, "I know I'm already clean and slick. I just wanted to have a few minutes in the shower with you."

He ran his hands over my chest beginning to soap my body, paying very close attention to my cock, balls and ass. He made sure I was nice and slick. At one point, he had my cock in his mouth and a finger in my ass, teasing me. It took all the willpower I had not to cum.

I got out of the shower before I could go any further and allowed Jerry time to begin his transformation. Jennifer would be over soon to assist in putting on the finishing touches. Seeing that Holly hadn't seen Jerry as Jessica yet, it was going to be an interesting evening.

We still had plenty of time before Jennifer would be over allowing me to make sure that the toys were all available for our use. As I lay them out, Jerry came out of the bathroom to begin dressing in his lingerie for the evening. He was meticulous in preparation. He even brought the breast forms. The black corset with garters, black hose with seams up the back and lace tops, black stiletto heels, a black thong over the garters neatly tucking in his pleasure providing cock, and a sheer black ankle-high negligee with a cinched bodice. To top it off, he had a longhaired black wig.

I heard the door alarm chime announcing it had been opened. I walked to the stairs to see Jennifer placing her keys on the end table and look up the stairs to see me smiling back at her. She removed her black trench coat to reveal her awesome body dressed in, a black garter, black stockings with seams akin to the pair that Jerry had put on as well as a similar pair of black stiletto heels. Her sheer black robe outlined the contours of her body. Damn, the girl was amazing, her long red hair down her back and over her shoulders. "I know you like what you see," she commented displaying her gorgeous smile and started up the stairs.

"He's in the bathroom starting on his makeup."

"Well, I chatted with Holly before coming over. She told me about last night's adventures more in detail than our conversation earlier. I wish we were able to watch because she's experiencing more erotic fuck sessions than she's ever experienced up until now. Anyway, I know what she wants to do this evening. Let's just say, what she gets to practice on you this evening, she'll do to Nick tomorrow night and we get to join in."

I smiled at Jennifer. She gave me a quick kiss at the landing and went straight into the master bath to help Jerry put the finishing touches on Jessica. Holly was aware of Jerry's alter ego but hadn't yet seen him dressed. When Jerry and I did Nick and Jennifer had her night with Holly, Jerry was already at my house waiting to surprise Nick. Of course, Nick talked about it and Jerry hadn't dressed since that night. This was going to be a fun evening.

I didn't want to bother Jennifer and Jerry while they were going through the makeup phase so I had taken a bottle of Astroglide and an applicator along with the Anal-Ese and moved to the main upstairs bathroom so that I could prepare. I squirted some of the numbing cream on my fingers and liberally applied it to my asshole, wanting to make sure I was able to enjoy having my ass taken.

Once I felt I had applied enough, I dipped the applicator tube into the Astroglide and filled the tube. I sat down on the toilet seat, leaned back and spread my legs allowing myself the opportunity to insert the applicator in loosening asshole and slowly inject the lube in my ass. A little preparation goes a long way. I was now ready for Holly to take my ass this evening.

I walked back into the master bedroom and made sure the two strap-on harnesses, dildos, and other toys were out and available for Holly and Jennifer. I set them on the love seat in sitting room as Jessica emerged from the master bathroom as hot as ever followed closely by Jennifer. What a pair.

Jennifer smiled and said, "I think we should go ahead and put you in the restraints before she gets here. We were talking about how we want to prep her for this evening and we think this will really tantalize her. You know, us helping her with the harness and such."

"Yeah," Jessica chimed in. "Besides, foreplay is hot."

I climbed up on the bed and Jennifer motioned for me to get on my back. She and Jessica hooked up my wrists to the restraints. Jennifer opened the nightstand and pulled out my favorite butt plug. She climbed up on the bed and with Jessica's assistance, spread my legs. She lubed the plug and placed it at my waiting asshole. My sphincter gave way to the slow but constant pressure and the plug was in. I love the feeling.

"Now, keep those legs spread and we'll hook up those ankle restraints," Jennifer said, smiling.

It was ten minutes after they had secured me with the restraints when the security chime announced the door opening at the kitchen from the garage. Jennifer had left it unlocked for Holly. Jennifer grabbed Jessica's hand and they moved off the bed and out the bedroom door to greet Holly down stairs. I could hear Holly as she first saw Jessica.

"Oh my God, you look so amazing! I never, never ever would have guessed that you were you."

I heard Jennifer respond, "Hot, isn't she? Pirouette for us please baby and show off your assets to Holly."

I heard some mumbling and figured that Jennifer must have helped Holly out of her coat and then some more conversation before they began their way up the stairs.

The lights were dimmed softly in the bedroom and when they walked in, I was smiling at three hot and sexy looking women. Holly smiled and winked, "I promise, I'll be gentle my dear."

Jessica chimed in, "You will love fucking him. He fucks back and doesn't just lay there."

Holly smiled, "I remember watching him getting fucked by Tom at the party. I know he loves it. I get my turn to be the cock and fuck him." She turned toward Jessica, "You dear, are so hot. I can't get over how you look. Nick said you were hot, but I never imagined this hot."

"Well thank you. I have to admit, I do enjoy it. Maybe not an everyday thing, but I do love the feeling that comes over me when I'm Jessica."

Holly was dressed in a blue shelf topped corset giving her ample breasts some security but showing the tops of her nipples. She had on hose clipped with the garters of the corset, no panties, and a pair of black ankle-high stiletto-heeled boots. She was always a vision.

Jennifer moved to the love seat in the sitting area of the master bedroom just out of sight. She called Holly over and asked Jessica to assist her in preparing Holly. After a few minutes of hearing a few "oh my's" and "oohs", all three returned. Jennifer had helped Holly with the leather harness that left Holly's pussy and ass open for access and the new six-inch life lifelike cock drooping from the harness like a real cock. Jennifer had put on the harness that had an ass plug and a dildo to slide up into her pussy, while the new eight-inch lifelike cock hung from her harness. Jennifer loved that harness.

Jennifer handed Holly the blindfold. Holly then climbed up on the bed and eased herself over to me. She looked me in the eyes and said, "I know you are the experienced one at this but I need a little practice. I hope you enjoy this. I'm dripping wet."

I smiled back at her, "I'm looking forward to you having me. I get to watch you do this to Nick tomorrow night. I know what he's getting."

Holly slid the satin blindfold over my eyes and I could feel her shifting her weight on the bed. Jennifer and Jessica began providing instruction on what to do next, plenty of lube, condom on the dildo, going slow, remembering to think about how you love to be fucked and how your lover uses his cock on you, and more. I felt the bed shift, some moans, and then hands on my body followed by some light flutter kisses up my thighs to my shaved cock, up my stomach to my chest. I was getting kissed and licked by all three.

They created electric sensations coursing through my body like current. My cock was throbbing and hadn't been touched leaving me aching. I could tell that they were playing with each other as well as me leaving my mind to wander between the sensations I was experiencing and the thoughts of what they were doing.

Jennifer told Holly, "Now, like I said, before you ease the butt plug out, place one of those condoms on your cock, then lube yourself up. Makes cleaning up easier."

I could feel them moving around on the bed and I heard the ripping open of the condom wrapper. Jessica must have been helping Holly because she continued to provide instructions.

Someone released my ankle restraints and I felt the butt plug moving before it began to be pulled out. Then, someone spread my legs apart wider and pushed them back while sliding some pillows underneath my back and my hips. When the plug was removed, my ass was still wide open. Jessica provided Holly instructions on how to slide in between my legs and line the cock up with my man-pussy. I felt more lube being applied and the head of the cock begin to enter my ass when an "Oh My" erupted from Holly as she slowly began to ease into me. She held my legs back giving her unabated access.

Both Jennifer and Jessica were cooing her on telling how her hot it looked to see the head disappear and her cock slowly easing into me. My own cock was throbbing as I felt each vein of the cock enter me. Holly moaned, "Oh shit this is so fucking hot."

Jennifer told Jessica to move around on the bed and feed me her rock-hard cock. I felt the shifting on the bed and just as Holly bottomed out in me, Jessica's cock was at my lips, throbbing and a little precum for me as a tease. I let my tongue swirl around the head an then under the shaft before feeling Jess shift to give me better access to completely engulf his throbbing member.

Holly cooed again, "I can't believe I'm watching a gorgeous woman feed her cock to the man I'm fucking with my cock."

Jennifer chimed back, "Just wait till I slide up behind you and feed you my cock into that dripping pussy of yours while you fuck him."

With that comment, I felt the bed shift again as Jennifer must have been lining up behind Holly. "Give me some angle there baby and spread those legs a little. That's it."

I felt Holly easing back out of me and moaning. She must have been sliding back down onto Jennifer's dildo before moving to slide back into me. Holly cooed and moaned as she began fucking me and taking it from Jennifer's cock at the same time. I was also enjoying all of the sensations at once, a cock in me and me sucking on one as well.

Holly's moans were ones leading up to a climax. I could tell she was going to cum as her voice began to quiver while she was telling us all how hot it was to see me sucking a cock on a hot woman, fucking my ass, and getting fucked at the same time.

I told Holly to fuck me with nice long strokes in between Jessica's slowly feeding me her cock. Holly was getting better at using the strap-on now as she was learning how to use it as her own cock.

I felt Holly shudder and the sigh as she came. I knew the feeling of her pussy, as it would grip the cock Jennifer was burying deep in her. Just before Holly's second climax, Jennifer announced she was about to cum. Holly began to grind the dildo and began to exaggerate her thrusts, pulling out all the way so the head left my ass agape before riding back into me to the hilt.

I felt Jessica's cock hardening. I knew, from intimate experience, that it was about to erupt for me. Jessica's moans announced the near arrival of a flood of cum. Holly came again, and yelled out for Jessica to shoot her load. Jessica complied like a good little slut shooting cum into my mouth hitting the back of my throat on the first two eruptions. I let the third shoot across my face for effect. I knew Holly would love it and she did.

Holly continued to deep stroke my ass as I continued to clean up Jessica's cock. Holly told Jessica that it was her turn to suck me off. Jess slowly pulled her cock from my mouth and moved around on the bed. I felt that wonderful tongue and mouth take me. The bed shifted yet again. Holly was really into the rhythm while it appeared that Jennifer was moving around on the bed again. Holly moaned again in pleasure.

"That's it baby, slide that rubber down onto that shaft. I want to see her take it too," Holly cooed.

Jennifer lubed the condom-covered dildo and then began to press the eight inches into Jessica's ass. Holly slowed down her thrusts as she was watching Jennifer penetrate Jessica. I knew what that looked like up close and personal and with my eyes still covered by the blindfold, I could imagine how intensely hot it looked as I was still getting drilled.

The fuck-fest continued. Each time I felt I was about to cum, Jess would back off pulling her mouth, tongue and lips from my member and let my cock pulse. What a tease. Even though I begged to cum, I knew that this was a show for Holly.

I don't remember how much time actually passed, but it was teasingly and erotically slow. I was experiencing pleasure as well as well as all of us enjoying giving Holly a show and gaining some pegging experience. She was becoming an accomplished pegging pro following Jennifer's instruction.

Again, I told them I was about to cum. I was expecting to be teased yet again, when Holly told Jess to let me cum. Jess worked me with earnest and I began to unload my cum, one rope shooting into that hot mouth and the rest onto my chest. Holly road deep into me and held it there buried as my cock shot out the remaining load. My body shook intensely from the climax.

I knew that Jennifer was still ramming it home to Jess as my climax ebbed. Seconds after I quit shaking, I felt Holly ease her cock from my ass. I felt the emptiness as she slid out completely. Holly moved around and pulled the satin blindfold from my eyes and off my head. The dim light gave way to the view of Jessica, head down on all fours with her ass in the air, and Jennifer fucking her. Holly began to lick up the cum on my stomach and chest. She was insatiable.

Jennifer began to shake as she fucked Jess. She had another climax approach, one that you could tell from her face alone; the ecstasy she was having from the double penetration she received from the harness and the ass fucking she was delivering to Jess. Jess's cock began to grow again from the fucking.

Holly began to remove my wrist restraints. Once free, I moved to lie on my side to watch as Holly slid a hand under Jessica to massage her cock. "Jenn, I want to fuck Jess's cock, roll him over on his back and let me get on, please!" Holly pleaded.

Jennifer slid out of Jess's ass, rolled him over onto his back and gave way to Holly. Holly threw a leg over Jess and guided his hardening member into her velvet box, slowly sinking down onto the shaft. Once she settled in, she began to ride. "I am so fucking hot, I can't believe you look as good as you do. Fuck me, fuck me good Jerry."

Jennifer slid off the edge of the bed and came around to me. She motioned for me to get on my back as my cock began to rise again. She slowly slid out of the harness and let it drop to the floor. She climbed back up onto the bed and straddled me, massaging my member as she guided it into her wonderful pussy.

I leaned forward and began to suck on her nipples and giving her wonderful breasts the attention they deserved. She rode me while Holly rode her husband.

Holly climaxed three more times and Jennifer twice, before both Jess and I came. Jennifer's pussy gripped me as I came for the second time that evening and Holly screamed out for Jerry to fill her with his cum. We were all in ecstasy.

We lay there recovering from our fuck-fest chatting about how incredible the sensations we experienced. Holly was excited about having the opportunity to show Nick what she'd learned, especially with friends in attendance. Holly was hooked on learning more sensual experiences.

Jennifer and Jerry gathered their things about midnight and told us that they would see us the next night at Holly's house. Holly fell asleep spooning with me. At about three in the morning, I felt Holly's hand guiding my stiffening cock into her pussy. We were still spooning, but she lifted her right leg up, opening her pussy for my cock and guided me in. We fucked again and came. I awoke at six with the alarm sounding. Holly was still sleeping as I got up to shower. I really was enjoying our relationship as a group and all of the perks.

Now, that night is another story. Nick would experience Holly's newfound skills. Not only was Holly sensually reinvigorated; she was becoming a hot cumslut. We all would get to enjoy the benefits of their sensual and erotic awakening.