Dressing Continues and Gets Hotter

It is good to know that you don't find my journey too boring. Thank you for the input. I am not a professional writer nor do I ever hope to be, just sharing my trip through life. Although these are in sequence, they can be enjoyed individually.

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As I had made a promise to Sherry I knew that I would have to keep. Sherry spent the week not letting me forget that commitment. Whenever she could she would whisper in my ear telling me I was going to be a good slut Friday night. She kept the pressure up telling me she was going to find a big cocked guy for me, maybe even a black man. For my part, I was both nervous and excited. I loved the attention given to me by the guys when they think I'm a girl and loved even more, the sharing with my hot gal at the end of the night. On one hand, I viewed myself as heterosexual, not bi, not a crossdresser or transvestite. This was something that my girl and I did together. On the other hand (when I was honest with myself), I also enjoyed the feeling of control that I had when a guy was hitting on me. I remembered the lessons that Sherry had taught me after my first encounter in the parking lot. On hindsight, the whole thing was sexy in a manner I can't describe.

The week was a paradox, sometimes flying by too fast and other times it felt that it would never end. Friday finally arrived. I finished my classes and returned to my dorm room to find out that my roommate was packed to leave for the weekend. A quick call to Sherry and she was on her way to meet up with me. She told me to shower and shave, everywhere, before she got there.

When she arrived she had brought along with her a small suitcase with her "supplies" for the evening. Sherry was dressed in a tight blue miniskirt, a white tube top showcasing her beautiful breasts and tight stomach and a pair of 3" heels. Once inside my dorm room, she locked the door, tossed her suitcase on my bed and told me to strip, now.

Once I was naked, Sherry tossed me a bottle of floral scented body lotion and had me apply it to my entire body. She came and helped with my back and even ran her fingers down into the crack of my ass. This caused my cock to expand which made her laugh and call me a slut. After the lotion was absorbed into my skin, she handed me royal blue bustier and instructed me to put it on. Next out, came a realistic set of 34C breast forms made out of some fantastic silicone. These were much nicer than the set she had used to "enhance" herself and I had worn in the past. On these she had put some adhesive to the back so that they were adhered to my smooth chest. I can't even describe how it felt to have the weight of these prosthetic breasts on my chest and the way they moved around when I did. What a turn on! My next items to put on were a pair of silky white nylons. As I carefully rolled these up my legs, my already rock hard dick felt like it was going to burst. I clipped the garters from the bustier onto first one leg and then the next. At this time Sherry sat on the bed and pulled me by my cock to her. She gobbled down my rod to the base as if this was her last meal. I'm sorry to say it didn't take very long before I shot copious amounts of sperm into her mouth. She quickly stood up and kissed me sticking her tongue, and plenty of my load, into my mouth. Feeling her beautiful breasts mashed against my tits was unbelievable. As our tongues battled for supremacy, she was cupping my ass and running her finger up and down my crack. She even slipped a lubed finger into my tight back door.

Sherry finally broke our kiss but did not release my ass cheeks from her hands. She then said we still have much work to do if we are going to make this night special. She reminded me that this was "her" night and that I had better keep my promise or there wouldn't be any more repeat performances like I had just received nor would I ever be granted access to her superb ass again. With having said that, she then reached behind me into her bag and fumbled around for something. Sherry finally let me go, turned me around as she continued her search while keeping one hand on my ass cheek. "There it is" she finally said. With that she leaned into me putting those fine mounds into my back while continuing to caress my ass. She then brought her finger to my puckered hole and started to push it in. I was beginning to develop another hard on. As she continued to apply pressure it dawned on me that this couldn't be her finger as it was getting bigger as it went deeper. I asked her what was she doing and she just shushed me. Just when I didn't think I could take the pressure anymore, whatever she was pushing into me just sort of popped inside me, slid a little deeper and settled into place. My boner which had started to wilt sprung back to life. Sherry then told me that it was a small butt plug and that it would give a definitive wiggle to my walk. With that she then gave me a matching blue thong and had me put it on over the garter straps. She told me that was the way real sluts wore their panties so that when they dropped them they could still leave their nylons on for a sexy look.

Next was a tight mid thigh length black miniskirt. After I wiggled my way into the skirt, Sherry had me sit down at my desk and turn to face her. When I sat down I nearly jumped straight up. The butt plug pushed deeper inside of me and up against my prostate. I was meet with initial shock and pain that was quickly followed by pleasure. Sherry giggled and then proceeded to apply makeup to blend my synthetic breasts into my skin. This was surprisingly easy I thought. A white silk top was next which she tucked into my skirt and cinched a gold belt around my waist. Sherry now went back to putting makeup on my face. She didn't need to do a lot, some eye shadow, a little eyeliner, mascara and lipstick were the major ingredients to her magic. My hair had grown out some so Sherry had an idea. She took some gel and water and slicked my hair back and off to one side which gave me a sophisticated but sexy wet look. Sherry laughingly told me that she didn't want to risk the wig coming off while I was in a compromising position. The final piece of the changeover was a pair of 4" royal blue open heels.

When I sauntered over to look at myself in my full length mirror, I couldn't believe the feelings I was receiving from my ass. The plug definitely made me sway more than usual and the more I swayed the better it felt, what a Catch 22. What I observed looking back at me was a sophisticated and extremely desirable young woman. My pecker grew rock hard again and made for a funny sight in my miniskirt. Again, Sherry came to my rescue to help me reduce some pressure. Once she relieved me of my problem, she tucked me up and out of the way inside my thong. She then applied red nail polish on my fingernails and told me to lay back on the bed as she freshened back up.

This time when we left my dorm room we didn't bother to look and there were a couple of guys just headed out at the same time. They both just nodded their heads and muttered that Craig is the luckiest SOB in the world. Sherry and I held hands and giggled all the way to her car.

Sherry drove us out of town to a club that we were familiar with and parked in a dark spot out the back. It was long walk to the front door and the entire time I could feel the plug working my rectum. As we approached the doorman he made a comment that it looked like us ladies were already having a good time. By this time in my journey I was confident that I passed as a woman and with Sherry as my wing woman, I was likely cocky as well. With an extra emphasis on my hip swing I let the doorman know that we were having a good time and intended for it to get even better. With that I grabbed my sexy girlfriend by the ass and we walked into the club.

Sherry and I took two stools at the bar. It is so hard get up and set down on a stool without putting on a show, and I'm sure that I did show a lot. Even though I hadn't forgotten that the plug was in my dark hole, I had become fairly accustom to having it there but the barstool was firm reminder of my anal invader.

We were laughing and touching each other. I think we were both extremely horny and excited for something to happen. We ordered two Absolutes and cranberries and were sipping our drinks and crowd watching. Sherry was teasing me by asking me what I thought of different guys. She was saying things like, "How about him or him. Do you think he is hung? What type underwear do you think he has on, if any?" We were carrying on like two girlfriends out for a fun night. Then she pointed out a large black man and said that she thought maybe that was the lucky one. I nervously guzzled my drink and when I went to order another, it was complimentary courtesy of the gentleman two seats down. I raised my glass as a thank you and indicated to my girlfriend with a shrug of the shoulders. He nodded and motioned a two finger sign to the bartender indicating that he also had a drink for her as well. Sherry had just turned to me to find out why I wasn't paying attention and saw the interaction. She stuck her tongue in my ear and called me a little slut. With that she then turned my face to hers and locked her hot lips on mine. After reclaiming me as her merchandise, she slipped off her stool and came next to me saying let's go meet him and properly thank him.

If you think getting on a barstool in 4" heels and a miniskirt without showing the world everything, then you should try getting off of one. I'm sure our new friend got quite the look at the top of my white stockings and the garter straps connecting them to my bustier. Add to that the slipping off the chair lodged the plug even deeper in my butt. Sherry said "Way to go babe, keep the fish on the hook and he will keep us in cocktails all night."

Together we stepped around the one patron between us and our new benefactor. Sherry introduced us both, giving our names and apologizing to our new friend saying that I was a little tongue tied at the moment. She then asked him (Wayne) to excuse us for a moment and turned to me. She put her hand around the back of my neck and pulled my face to hers and proceeded to give me a scorching open mouthed kiss. At the same time she was running her hand up the side of my top coming to the side of my bra. It felt like she was trying to rip my tonsils out with her tongue. With a quick swat of my ass she broke the kiss and turned to Wayne saying, "There, I think I untied her tongue now."

Wayne had a smile on his face and a noticeable bulge in his trousers. He said, "It's a good thing it wasn't something seriously wrong with her or you might have gotten tossed out of this place!" It was the perfect thing to say as it broke the ice as we all laughed. Sherry and I took up space on either side of our new buddy. It was obvious that he was enjoying the attention of two good looking young women. We chatted about the usual get to know you stuff and found out he had been in town for the week and was due to fly out the next day in the late morning. Sherry was being very flirty and touchy/feely with Wayne. Every once in awhile she would reach around behind his chair and run her hand over my ass. Our new friend did indeed keep us in alcohol including a couple of shots. When he ordered the third shot, I begged off. Sherry however did not. When it arrive she stuck her finger in it and reached across in front of Wayne and offered her finger to my mouth telling me that I should at least taste it. She had her luscious tits pressed into Wayne's side, her right hand high on his inner thigh, her hair and the side of her face right in front of his and left hand in front of my face. I thought, okay, two can play at this game. I puckered my lipstick coated lips and gave her finger a kiss. I then snuck my tongue out and licked her finger from the bottom to the top before wrapping my tongue around it. Next I slipped the tip between my puckered lips and slowly worked my way to the bottom of her digit. When I got to the bottom, I stuck my tongue out and licked further down her hand before sliding my mouth back up her finger. One more trip down and up and I released her finger with a pop. I then told Sherry that is was yummy but a little cold and not very much volume.

All of this happened within a foot or less of Wayne's face. At this point of the night I had already consumed three vodka and cranberries and two shots and was starting to feel the effects of the alcohol. Sherry grabbed me be the hand and led me to the dance floor. There was an up tempo song playing and we started dancing and grinding on one another. She got behind me and I thrust my ass into her crotch. She put her hands around my stomach and started running them up and down from the bottom of my breasts to the top of my skirt. I looked back over my shoulder at her and she took one hand and pulled my face to hers. Once again we locked lips and worked our tongues into each other's mouths. As the kiss got hotter, I turned to face her and we were essentially breast to breasts and crotch to crotch on the floor. I'm not sure we were even dancing anymore, just making out and grinding. As a slow song came on, I broke the kiss and we just each held each other tight and swayed to the beat. Sherry was nibbling at my ear and telling me that we just really put on a show for Wayne and that it wasn't fair to him to be sitting there all alone. When the song ended we went and took up our positions on each side of his barstool. Wayne had more cocktails waiting on us and I pretty much just slammed mine down which was just as quickly replaced with a new one.

We were both leaning into him. He must have thought that he was in heaven with a woman on each side, firm boobs pressing into both of his arms and a different woman's hand stroking each leg. Wayne remarked that we were really into each other, to which Sherry replied that he didn't have any idea how deep that I got into her sometimes. Wayne inquired whether we only liked girls. My little devil of a girlfriend then told Wayne that while she liked girls and sometimes men, that I had almost zero experience with guys before. Shit, she was telling the truth, he just didn't know all the facts. Wayne got a large smile on his face and told us that he felt he should give me something to compare and consider with. Sherry just smiled and said maybe, meanwhile I started to panic a little.

Wayne ordered three more shots, "Too new experiences!" Those were quickly followed by three more. Now I knew for sure that I was feeling the effects of the booze and told Sherry as much and that I was concerned about us driving home. Wayne piped up that he had a room across the street with an coffee maker and that we could pop over and have a cup to sober up before heading home.

Sherry, ever the eager beaver, jumped right on his offer. Me, well I had to go along, but I kind of figured out where this was headed. I was excited, nervous (make that extremely nervous), a little ashamed, powerful and most of all, horny.

Wayne settled up his (our) tab with the bartender and walked out of the club with a sexy woman on each arm. He kept letting his hand slide down to the top of my ass and I kept reaching back and raising his hand back up. When his hand wasn't on my ass he was stroking up and down my back feeling and occasionally tugging at the laces of my bustier.

Finally we got to Wayne's room. It was a pleasant room with a king bed, a full size couch, big television, coffee table and true to his word, a coffee maker. Wayne made Sherry and I a cup of coffee and got himself a beer from the mini-bar. Sherry and I had sat on the sofa. We were side by side and essentially cuddling. Wayne brought the coffee to the table and asked if there was room for him too? Sherry, minx!, scooted down the couch a little and patted the cushion between us.

He sat between us with my right leg against his left and Sherry's left leg against his right. We sipped our drinks and made small talk. Wayne finished his beer and sat back against the cushions. Sherry and I were sipping our hot coffee. Wayne had spread his arms out and essentially had an arm around each of us. Sherry sat her coffee down, then reached over and took mine out of my hands and put it on the coffee table as well. She then leaned across Wayne's legs and started kissing me. She put one hand on Wayne's leg and the other on mine. She was stroking my nylon covered leg from my knee to up under my mini skirt to my stoking tops. Wayne, not to be totally left out this time had one hand in each of our hair. Sherry's hand left my leg and traveled up my stomach to my breasts which she started to massage and knead.

She was really working me up. I was leaking pre-cum, panting and moaning. Sherry pulled back from the kiss but Wayne never took his hand off of my head or out of my hair. He turned my head to him and bent forward taking my lips with his. This was sooo different than my first time in the back of the car. This was sensual, deep, hot and wrong. How could I like kissing another guy in front of my girlfriend? How could I be enjoying another guy kissing me at all? About that time he nibbled on my bottom lip and I opened my mouth in a moan. Wayne saw this as an invitation to slip his tongue into my mouth. I was now lost in the moment and the kiss. I reached around his neck with one hand and pulled his mouth to mine. Later Sherry recounted to me that when that happened I spread my legs so far that she thought I was going to pull a muscle. More of a guy reaction, than ladylike she told me.

Wayne finally released my mouth. I was a panting, heaving mess. My skirt, already short, had ridden up until you could see the white lace of my stocking tops, my lipstick was smeared and I was both confused and conflicted. Wayne, having released my lips, then turned and started kissing Sherry. More confusing emotions rushed through my body. Initially I was pissed and wanted to kick his ass, then I realized that I was turned on as well seeing him possessing her mouth like he had mine. Then I realized that I just did the same thing and how could I be pissed. Sometime during that confusion, Wayne had placed his hand on my leg and was stroking me from above the knee to the top of my stockings. Every second or third stroke he would give my garter strap a little tweak. He had now worked my skirt to just above my stocking tops. This too was confusing to me. It felt so good to have my nylon covered legs caressed, to be desired but also so wrong as I was a guy and he was a guy. I was totally mind warped!

The next really cognizant thought that I had was Sherry leaning towards me and gently kissing me. I know I had drunk too much but I also was almost freaked out. Sherry's gentle kisses grounded me. Wayne had sat back again except now he had one hand on both Sherry and my leg. He was stroking and edging higher. I became aware that he was actually coming above my stocking top and petting my bare skin. It was electrifying but I couldn't let him get any higher, so I put one hand in my lap preventing him from getting to my panties. It dawned on me that I didn't stop him from what he was doing, it just felt too damn good.

When Sherry broke our kiss, Wayne then said, "Well?"

"Well what" was my response.

"Do you like being kissed by a man? I wasn't so bad, was I? From your reaction I wouldn't think so."

I couldn't answer. I was stumbling and bumbling. Wayne just chuckled and said, "I've got plenty of more new experiences for you." About that time I noticed that Sherry was rubbing his crotch and his obvious hard on. I had a momentary out of body experience or maybe it was a transfer type experience as I could imagine how he felt. Sitting in his hotel room, swapping spit with two sexy women, stroking their legs as one is stroking him. He must have felt like a king. I know I would have.