This story takes place after Holly and Nick's initiation into the group.
Holly called me at work Monday morning after their initiation. She was adamant in coming over to the house that evening at eight. Seems seeing a couple of women fuck her husband with a strap-on at their initiation the week before had her interest and after our fuck session the night before, she really wanted to try out the strap-on. Of course, that is if I was up to it. Now, I have to say, I did have a hard time concentrating on work the remainder of the day.
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. 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 party 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.
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.