The Miss-adventures of Michelle Section 2, Chapter

Chapter 4
I awoke late Sunday morning which was not typical for me and went through my usual routine of breakfast and coffee. As I sat in the living room I began to ponder the previous night’s events. Did all of what had happened really happen or did I dream it all? If I did dream it all, why was I dreaming of being dressed up as a woman named Michelle and teasing guys on the streets of the city? If it did happen and was not a dream, what had come over me that caused me to get so turned on by being Michelle and teasing those guys and having Ted take me on the street?
After I finished my coffee, I went back to my master bedroom and found the stockings, heels, half-top, bra, and mini-skirt laying on the floor next to my bed. I gathered up the garments and set about putting them through the wash while I got into the shower and took care of washing myself. After my grooming routine I decided to put on the black sheer thigh-high stockings I had worn the previous weekend and put on the heels to get more practice in walking in them. I decided that was all I was going to wear for the day which caused my cock to swell with excitement.
The rest of the day was uneventful but I had gotten really good at walking in the heels. In fact, as I stood over the sink cleaning the last of the dishes from dinner, I tried to imagine what I must look like standing there in those stockings and heels with nothing else on at all. I then began to think about what other kinds of clothes I could be wearing to not only tease everyone in the group, but to possibly wear out in the city and tease anyone who might see me.
The next day I called Tonya and asked her if she was busy any nights that week. She asked me what I had in mind and I informed her that while I loved having her and Jennifer putting on my make-up for me to transform me into Michelle, I thought I should probably learn how to do it by myself in case there were times when they would not be available to help me. She giggled on the other end of the phone and wondered if I had been thinking about being Michelle permanently or something. I told her I wasn’t having any such thoughts, but to be able to put my own make-up on would be a good skill to have, especially if they were going to continue making me play the role of Michelle. I had also told her that I was thinking about going out shopping for some more clothes and if she had any suggestions on things I should get. All she told me to do was look for things that I thought I would enjoy wearing and would accentuate my ass or show it off as much as possible. She said that she would come by on Wednesday night to help me out with the make-up. She said that she would call Jennifer and see if she wanted to join us and that she would go out and buy some make-up items that I could use and keep at my place for whenever I would ‘lose’ another bet. I told her that sounded great and that I would go shopping before they got here and get a few things. I would show them everything I got when they got here to see if I did alright in picking things out and then get their opinion on any changes in wardrobe.
It was now Tuesday, the day before Tonya and Jennifer would be coming over, and I decided I would go shopping for more items to add to my now growing feminine wardrobe. I called Frederick’s of Hollywood to find out if Bethany was working and fortunately she was the one who answered the phone. She informed me she was the only one working in the store until 4 in the afternoon. I quickly pulled my jeans on over my panties and headed off to the mall to meet up with Bethany and pick out some more items.
The drive to the mall caused me to wonder if I should tell her about the last two weekends or not. I mean, having to wear panties for losing a bet is one thing, but being turned into a woman named Michelle is something entirely different. She really loved the fact that I had lost the bet and had to wear the panties before so I had a feeling she was going to really enjoy the idea of me having to wear a mini-skirt. I relegated my thoughts to telling her about losing another bet and having to dress up but I wouldn’t tell her about Ted fucking me in the middle of the street or all the guys fucking me on the parking structure. I decided to tell her that I lost another bet this past weekend and that I had to go buy some more clothes to wear as my punishment for losing was having to dress up for three weekends in a row. That would at least explain why I was having to buy more outfits and such. I would base what else I would tell her on how she reacted to the story I had concocted to give her. I wasn’t lying to her, I was going to be dressing up for at least three weekends in a row, I just didn’t tell her that two of those weekends had already happened.
I got to the mall and went straight to Frederick’s of Hollywood. Bethany was all smiles when she saw me come into the store.
“You lose another bet and have to buy more panties?” She asked me.
“In a manner of speaking.” I informed her.
She looked at me quizzically and I began to explain the story I had formulated in my mind. Her eyes lit up and her jaw dropped when I told her I was f***ed to dress up as a woman. She couldn’t stop laughing at the idea of me dressed up as a woman and asked what kind of friends I had to make me do such a thing. I told her about the fishnet stockings and the black leather mini-skirt I was wearing this past weekend. She looked me up and down and said that she couldn’t picture that in her mind. She said she would have to see me dressed up in such an outfit to get a real picture of how I looked. I took the hint at what she was wanting which was having me try on outfits in the store in front of her.
I told her I needed some new stockings and a couple of skirts and then a couple of bras to match the stockings and of course a couple of tops. I told her I had two more weekends of having to dress up so I needed at least two different outfits. We first looked at the stockings and I saw a pair of white cotton thigh highs with pink hearts on them as well as a pink bow at the top of each one. They felt more like really thin socks but were thigh-highs. I told her I wanted to try those on and that we needed to find some things to go with them. We picked out a pink bra for me to wear as well as a white skirt that was rather tight and really short. We also picked out a white button up blouse that I could wear long or unbutton the bottom and tie it into a knot to make it into a half-shirt to show off my midsection. I actually loved that outfit and immediately went into the dressing room to try everything on. I was so excited about the outfit, I had completely forgotten to grab a pair of panties to wear with it. But, once I was in the dressing room and sliding those stockings up my legs, I didn’t care anymore. I put on the bra, the top and then finally the skirt. I had taken the panties I was wearing, off so now I was wearing nothing under the skirt. The skirt was tight and would form fit to hug the curves of my ass. I turned around in the mirror and gazed at my ass. I noticed that the skirt covered my ass entirely so I pulled the skirt up to a good level and then rolled down the top a little bit. When I turned around at that point, the bottom of my ass was showing at the bottom of the skirt. I peeked out through the curtain to see if anyone else was in the store before I walked out there to let Bethany get a look at me in the new outfit. Fortunately she was the only person in the store besides me.
I pulled the curtain back and began to walk through the store to the counter where Bethany was working. When she saw me walking up to her, her jaw dropped and she stared. I twirled around to show her my ass and how it looked in the skirt. When I twirled back around she was still dumbfounded and wasn’t saying anything.
“Well? What do you think?” I asked her.
“I’m jealous. I wish my ass looked that good in a mini-skirt.” She said back to me. “I really love the stockings you picked out. Really feminine but give off a sense of innocence. You are going to turn some heads for sure.”
“I don’t know about all that.” I said back to her. “But do you like it? Is it ok?”
“I think it’s perfect.”
“You aren’t just saying that because you want to make a sale are you?” I asked her sarcastically.
“No way. I don’t care if you buy anything or not. I’m just glad I got to see what your friends saw. I think you look hot in that. I can just imagine how sexy and slutty you looked in the leather mini and black stockings.” She said back to me.
“Well, I did forget to grab a pair of panties so I unfortunately don’t have any on under this.” I said back to her.
“You don’t wear panties with that. It’s too tight and would show a panty line. If anyone sees you in this they are going to wonder if you’re wearing any at all or if you have on a thong.” She said back to me.
“Good point. I didn’t think about that.” I said back to her before I went back to the dressing room to remove what was going to be one of my new outfits.
Once I removed the outfit, I put on my jeans and shirt and went back into the store. I started looking around for something else to wear. I really liked the skirt so I decided to find another one in another color and decided on black. I then grabbed a pair of black thigh high stockings with a lace design embroidered on them as well as a black lace bra and a sheer black button up top. I chose the sheer top so that my bra would be visible while I was wearing it. I didn’t think I needed to try that outfit on so I set that outfit on the counter along with the first one. Bethany looked a little disappointed since I didn’t try on the second outfit for her. She then informed me that she had an idea for something else if I was interested in seeing it. I told her I was and she led me to another section of the store and showed me a PVC skirt. She showed me how it could actually come apart into two pieces as it buckled at the sides and was open on the sides. She said that it was short like I wanted and I should try it on to see if I like it.
I decided I would give it a try as I did like the idea of it being open on both sides like the black leather mini-skirt I had that weekend. I went into the dressing room but rather than close the curtain, I left it open. Bethany noticed this and stood there watching as I tried it on. I removed my jeans and panties and my cock began to swell as she stood there watching me. I put the skirt on and then looked in the mirror. The only downside to the skirt was that with the two buckles on each side, the openings on the sides were not very high. I then tried to flip the back of the skirt up but it wouldn’t go up that far due to the constraints of the buckles. I told her I liked it, but it wasn’t slutty enough. She told me to wait right there and went back to the section and then came back with another skirt for me to try on.
What she brought me wasn’t so much a skirt however. It was a belt with two flaps of PVC fabric, one in the front and one in the back. I looked it over standing there while wearing nothing at all at the time and my cock grew to full proportion from examining it.
“Looks to me like you enjoy that skirt.” Bethany said to me staring at my erect cock.
“Well, let’s see how it looks when it’s on.” I said back to her.
I unbuckled it and wrapped it around my waist. I twisted it into the proper position with the buckle on my left hip and secured it together. My cock was fully erect so it propped the front of the skirt straight out from my body. I knew that I couldn’t wear that skirt out unless I was wearing a pair of panties or secured my cock in some fashion that it wouldn’t poke the front out from my body. I did like the fact that the back could be flipped up quite easily for access to my ass. For a moment I forgot where I was and when I had flipped the back of the skirt up over my waist, I bent over and put my hands on the little bench in the dressing room and looked at my profile in the mirror. I then spread my legs apart and loved how the front flap of the skirt would hang straight down and expose my cock. I then felt a hand smack my ass and then Bethany asking me what I was doing. I immediately stood up and looked at her but couldn’t get any words to come out of my mouth. She stood there smiling at me.
“Lost a bet huh? Are you sure that’s why you’re here? Looks to me like you were looking to see how easy it would be to give someone access to that cute ass of yours while wearing the skirt.” She said to me.
“No, really, I did lose a bet. I can give you my phone and call someone to see if I had lost a bet and had to dress up this past weekend.” I said back to her.
“Oh honey, I don’t judge. Not in the least. I think you look great in the outfit. Especially when you bend over like that. It makes me want to have my way with you right here.” She said to me giggling.
“That sounds like fun.” I said back to her winking.
“Oh stop. Ok, we need to find some stockings and a top for that.”
“Couldn’t I just wear the sheer top with this?” I asked her.
“Actually, yeah, that would look good. Well, if you keep this skirt in black. If you want a different color then we would need to get something else.” She said back to me.
“Well, I could always get another pair of stockings with a different design on them or no design at all and keep the black lace bra and sheer top to wear with this.”
“I think fishnets would look great with this skirt in my opinion. That or thigh high boots.” She said back to me.
“I am not going to buy some thigh high boots to wear one time for having lost a bet. That’s too much money to be spending. I think a pair of fishnets would be good though.” I said back to her. In the back of my mind though I was wondering about the thigh high boots. I never thought about that but I wasn’t sure how far Tonya and Jennifer were going to take this so I didn’t think about those boots anymore.
Bethany grabbed the fishnets and handed them to me and I set them on the bench as I unbuckled the skirt. I removed the skirt and stood there completely naked with my hard cock sticking straight out from my body. I looked over at Bethany who was still standing at the entrance to the dressing room. She was standing there biting her bottom lip and staring directly at my hard cock. I tried to play it off like I wasn’t noticing that she was staring at me and slid my jeans up my legs and then concealed my hard cock. I put the panties I wore into the store in my pocket and gathered up the rest of my clothes and went to go to the counter. Bethany followed closely behind me and grabbed my ass and fondled it while following me to the counter. When I got there and set the clothes down, she reached around and grabbed my hard cock through my jeans. I nearly shot a load of cum through my jeans when she did that.
“Damn I wish I could have this right now. I am so horny I can’t stand it.” She said to me.
“I wish we could as well. But since you’re the only one working, we would be running a big risk of getting caught.” I said back to her.
Ironically, just as I finished that statement, someone came walking into the store.
“See what I mean.” I said to her.
Bethany released her grasp on my cock and walked around the counter. I heard her sigh and I knew the frustration she was feeling as I was feeling the same thing at that moment. She folded all the clothes and put them in the bag and I handed her my credit card. She ran everything through and then I noticed that the price for everything wasn’t what I expected it to be. I looked at the receipt and Bethany told me that as long as I promise to come back to her and her alone if I lose anymore bets…she would continue to give me a discount. I told her it was a deal and that she would be the only one I buy anything from and would always call to make sure she was working before coming up there. Just before I left the store, I leaned in close to her and whispered into her ear.
“Just so you know. When they dressed me up in these clothes the first time, they told me that I was going to be called Michelle from then on. I took that to mean that every time I lose a bet, Michelle would have to come out and play.”
“Damn. Are you serious? What all does she have to do?” Bethany asked me as she leaned over the counter staring me with an unfettered lustful curiosity.
“Anything they want me to do. Not to mention I have to let them do anything they want to me.” I responded.
“Oh shit that’s hot. I have to meet Michelle. I don’t mean just you coming in and trying things on. I want Michelle to come in and do some shopping. I want to see you completely dressed up.” Bethany told me.
“Well, if it ever comes that, I’ll be sure to make that happen for you.” I said back to her.
“I can’t wait.” Bethany said back to me as I smiled at her and headed out of the store.
Once I got back to my house, I immediately took everything out of the bag. I removed the tags that were still present on each item and put each one through the wash. I was so excited about having bought my own sets of women’s clothes, I didn’t even want to wait for them to finish washing before putting them on. My cock was rock hard from anticipation and then I realized it would be better to model the items for Tonya and Jennifer when they came over the next day. I would wait until I had my make-up on and then introduce them to the items I had bought and model for them instead of just showing them the items.
The rest of the day and night and even through Wednesday, my cock ached and dripped pre-cum from the excitement of putting on those slutty outfits and modeling them for the girls. I couldn’t wait to see what their reactions would be. In a sense, I was hoping they would pick out one of my new outfits for me to wear for everyone on Saturday already having reserved myself to losing on purpose if any new bet was made. But there was also another side of me that was more excited about seeing what they had in mind for me to wear. If the previous two weekends were any indication, I’m sure I would love it and immerse myself fully into the role of Michelle. As I laid out all of my new clothes onto my bed to admire and figure out what combinations I could dream up with for the few outfits I had, I realized that I only had the one pair of high heels. I then realized that I definitely needed another pair of heels to match the white stockings and stretch cotton skirt I had bought the previous day. I looked at the clock and realized that I still had several hours before the girls would arrive and quickly drove up to the mall to find a pair of white heels to add to my growing collection.
I made it to the mall and went into one of the many shoe stores and looked around. One of the girls in the store asked me if she could help me find anything but I told her I was just looking around for something for my girlfriend. She then told me that if I needed any help, to let her know to which I smiled and said thank you.
I browsed the selections and finally found a pair of stiletto white heels that caught my eye. I looked at the size on the box and fortunately they were very close to my size. I looked around to see if anyone was watching and then quickly slipped off my shoes and tried on the pair from the box. They were unfortunately a bit small, but not by much. I knew I needed a size that was only about half a size bigger. I put my shoes back on and then found the girl working in the store and asked her if I could get a bigger size of that style. When she returned and handed me the box I then asked her if there was some kind of return policy if they didn’t fit as I was buying them for someone else. She said that as long as the shoes were not damaged and I had the receipt, I could exchange them for another size if I had to do so. I thanked her, paid for the shoes, and rushed home. Once I got home, I quickly removed my shoes and tried on my new stilettos. To my surprise, they fit perfectly. I then took my new shoes off, removed my clothes, put on a pair of stockings and my new heels. I wanted to spend time walking around in them and breaking them in before the weekend would arrive in case I had to wear these out and about if we did go out again. Prior to the girls arriving, I made sure to put some of my everyday clothes on instead of the stockings and panties. I put all my new clothes back in their place in the walk-in closet and waited for the girls to arrive.
It got to be about seven in the evening when the girls got to my place. We went through our typical greeting of a hug and a kiss and I offered them a drink as we sat around for a little while talking. I was regaled with stories of how their week was going thus far and how they really needed the weekend to get here quickly. Once they started talking about the weekend, they both looked at me and smiled.
“So, did you have a good time last weekend?” Jennifer asked me.
“Oh yeah. I loved it. I’m actually hoping something like that will happen again.” I responded.
“What was your favorite part of the weekend?” Tonya asked me.
“I would have to say it was you two pushing me up against the wall and Ted fucking me right there on the street. While I really enjoyed the parking structure and everyone having a turn, on the street was great. Especially when I looked back and saw that Ted had removed his pants. I really liked you two telling me all the things you were saying as well.” I said to her.
“Well, we’ll have to be sure to keep you in that role of a cum slut whore then.” Jennifer said to me. My cock swelled to full erection the instant she said that and the girls did not fail to take notice of that fact and simply giggled.
“Let’s get started on this training session and see you putting on all the make-up yourself.” Tonya said to me.
Jennifer grabbed the ever familiar backpack and emptied the contents onto my coffee table. She set up a make-up mirror that had lights on the sides and explained to me that overhead light was not ideal for putting on make-up and that I needed light from the side to make sure everything would be perfect. Once it was set up, they explained all the different brushes and colors and how I would use each item. The lesson continued for several hours with them directing me and me applying each layer until the transformation would be complete. I would then be told to wash everything off and start again. This happened several times and each time they would give less and less direction. It finally got to the point when I was able to put everything on without any direction. They both applauded me on how well I learned to do it all myself. I looked in the mirror after having completed the last application and then stood up. I told them to stay right there as I had something to show them.
I went into my bedroom and quickly removed my clothes. I grabbed the fishnet stockings and put them on as well as the black heels the girls had given me. I then put on the black lace bra, sheer top, and the black cotton-lycra mini-skirt. I then grabbed the black PVC skirt and carried that with me as I walked back into the living room. Both Tonya and Jennifer grinned from ear to ear as they saw me in my new outfit. I twirled around showing off my ass and how it looked in that tight mini-skirt. I then showed them the PVC skirt and they told me to put it on immediately. I stripped off the cotton-lycra mini and put on the PVC skirt. They both loved that skirt and said it was very slutty and perfect for Michelle. I then told them I had one more outfit to show them.
I went into the bedroom and took off my current outfit and quickly put on the white ensemble that I had bought. I went back into the living room and they couldn’t stop staring and talking about how cute the outfit was as well as sexy. They loved the stockings especially with the pink bows and pink hearts. I made sure to mention the new white heels that I was wearing. They asked me how I was able to buy a pair of heels without giving off any alarm bells in the store. I explained how I pulled it off and they applauded me for my deception and ability to get the items.
“So, did I do a good job in picking out clothes?” I asked them.
“You did very well sweetheart. I love them. It definitely gives us an idea of how far you’ll go with all of this and what we can get you dressed up in for the next time. I’m sure we can come up with something really good for this weekend. You do plan on losing again don’t you?” Jennifer asked me.
“If I get to continue playing the role of Michelle, you better believe I’ll keep losing. Besides, I think the guys really enjoy me losing as well.” I replied.
“I think you’re right. I think they really love Michelle so we’ll have to give them more of her. That reminds me, I’m going to talk to John and see if he would be willing to take you someplace special. You’ll have to go as Mike first and if it goes well, I’m sure you could go as Michelle.” Jennifer said to me.
“Take me where?” I asked her.
“I’m not going to tell you. I’m going to let him just take you there. I’ll be sure to talk to him and tell him to take you in two weeks. I’m sure Tonya would agree that you should not play with your cock or cum until then either. It will make your experience all that more enjoyable.” Jennifer said to me.
“Take him where Jen? What are you talking about?” Tonya asked.
“I’ll fill you in on the way home. Once I tell you it might give you some ideas as to what we could do with Michelle in the weeks to come.” Jennifer responded laughing.
“Well, I’m going to get out of these new clothes and put them away until the weekend. Unless of course you bring something else for me to wear.” I told the girls.
“I have an idea of something, but I need to discuss it with Tonya first. We’ll be sure to let you know sweetie. You really are loving this aren’t you?” Jennifer said.
“I have to admit that I am. Does that make me seem strange?” I asked.
“Yes it does.” Tonya responded sarcastically. “But it makes us strange as well since we love making you do it and watching you experience everything you have so far. I personally think it’s a matter of perception.”
“What do you mean?” I asked her.
“Well, one person may view something as strange or taboo or not normal while another person may view it as merely an expression of oneself and living life to the fullest. They want to experience everything life has to offer no matter what others may think. I personally like those people better because they don’t allow what mainstream society says is normal to dictate their own lives.” Tonya responded philosophically.
“Beautiful, sexy, kinky, and intelligent. I know I’m in love now.” I said back to her with a wink as I started for the bedroom to change.
After I had changed and gone back to the living room, the girls told me they were giving me all the make-up and the mirror to have so I could practice and experiment with different shades and such before the weekend. They told me I needed to get really good at it as I would be the one putting everything on this weekend by myself. They told me I had to make it perfect as they were coming up with something really good that I would thoroughly enjoy.
They then gathered up their personal belongings and I e****ted them out to the car. I gave each one a hug and a kiss and waved goodbye as they drove off down the road. Once I was back in the house and relaxing in the couch, I began to think about what Tonya had said earlier. Everything she said made perfect sense to me. I was beginning to come completely out of the shell that I had been living in for so many years and finally experiencing something more. There was a part of me that wondered if fate had intervened on my behalf when I met John and Ted at the bar those several months ago. I began to wonder if I was being f***ed into something new or if I was merely in a position to allow some subconscious desires to surface and be experienced. Could that be why everything they were making me do was such a turn on and why I was attempting to play the role of Michelle as best as I could? Or could it be that Michelle is actually a part of who I am, a part of my being? In any case, I found it difficult to contain my excitement of things to come on the weekend. There was no longer any nervousness on my part, no more anxiety, just excitement. The hardest thing I had to do was exhibit the patience required to wait until the weekend to do anything, which included me being prevented from playing with my cock and allowing myself to cum.
The next two days were difficult for me as I would get more and more excited about Saturday. The closer it got, the more distant it seemed to be and the slower time seemed to pass. I spent those two days walking around the house in my new heels. I put on the white stockings and would admire myself in the mirror. I would practice little dances and putting myself into various positions while wearing them in anticipation of being f***ed into those positions by the girls and the guys. I would bend over chairs and counter-tops. I would also practice squatting straight down instead of kneeling in case I was told to suck on more cock while wearing those heels. I even went so far as to practice standing on one leg with my other leg propped up something in anticipation of being put into that position and taking a nice big cock in my ass. I became so accustomed to the stilettos that it actually felt strange to put on a pair of sneakers or sandals. Being able to walk around and maneuver myself in those heels was the only consolation for having to wait until Saturday to have some more ‘fun’ with everyone.
Saturday had finally arrived and the excitement I felt was clearly evident by how hard my cock was all morning. It was extremely difficult to sl**p the previous night but I was not feeling any ill effects of that as I was full of energy. I made sure I took care of my body and ensured everything was completely smooth prior to everyone showing up. I decided on wearing a pair of really short cheerleader shorts that hugged my ass perfectly and accentuated how hard my cock was. I also put on a tank top as the weather was simply beautiful this day.
Everyone arrived around noon and loved seeing me in those tiny shorts. Tonya even commented on how sexy my ass looked and loved feeling on my cock through those shorts. She did warn me about wearing cotton shorts that tight however as the wet spot of pre-cum on the front was becoming more and more visible. I told her it was a matter of seeing her which caused that. I didn’t want her to think it was more of the thought of being dressed up and d**g around the city again that had actually caused it.
We all went through what was now becoming a fairly typical routine of drinks and food and then settling in to watch the games. We all sat around talking and watching the games with nothing out of the ordinary happening. Just before the night game started, Jennifer went out to the car and came back in with her backpack. All the guys smiled and wondered why she had brought it in at that moment instead of later. They began to wonder if she knew something they didn’t. She simply responded that no matter who won, the items in the backpack would be put to use on the loser or losers. Of course, Jennifer, Tonya, and I knew better. I was sure the guys were catching on that as long as they all agreed to pick the favorite, I would always pick the other team. My only saving grace was that we all had decided on adding the spread to the equation which made it a bit more interesting and kept us involved in the game. Tonight though, my team would lose, with the spread, by one point. If my team had not allowed a late score, then I would have won the bet. During the final minutes of the game I would look over at Jennifer with a look of worry and she had the same look.
Once the game was over, she called all the girls together into the kitchen. Jennifer and Tonya led the conversation once more and the others seemed to be content with following their ideas. I had a feeling they were happy with the ideas that were being announced to them. I was also wondering if the other three had been told of the overall plan Jennifer and Tonya had for me and they were merely playing along as if they didn’t know what was happening. Once they had finished, they beckoned me into the kitchen and I was told to go to my room. Jennifer and Tonya were the only ones who followed me and the others went back to the living room grinning from ear to ear. I could hear the guys ask them what was going on and what I was going to have to do but they just smiled and said they would find out later.
Once we were in the room Jennifer emptied the contents of the backpack onto the bed. She laid out the clothes and there before me was a pair of sheer white thigh-high stockings, a short little plaid mini-skirt, a white lace bra, white sheer top, and a blonde wig. I picked up the skirt and noticed that it was connected at the side by a thin strip of Velcro. It could be adjusted to give an even wider slit up the side or a narrow one. I immediately stripped off my tank top and my shorts and stood before the two girls completely naked with my cock sticking straight out from my body. I held the skirt up to my waist to see how it would look. I looked up at the girls and smiled from ear to ear at the thought of wearing these out and about. It was then Jennifer noticed that she had forgotten to pull the panties out of the bag. She rummaged through it and found the white lace bikini style panties and laid them on the bed as well.
“These should help keep things contained as best as possible.” She said to me.
I grabbed the make-up kit and laid it on the bed as the girls watched me intently as I put on my make-up. They smiled and nodded to each other at how well I was doing. They had even commented that I was doing such a good job that I must have been practicing quite a bit in the last couple of days. I told them I had practiced a couple of times but spent more time walking around in the new heels getting accustomed to them. Jennifer mentioned that it was good I had spent a lot of time in those stilettos as I would be wearing them out tonight. I looked up from the mirror and gazed at her. She giggled as did Tonya and I knew they were planning on taking me out into the city once more.
I finished off the make-up with some ruby red lipstick and blotted and stood up to put on my new wardrobe. I rolled the stockings up my legs, slipped on my heels, and then attached the bra. I wrapped the skirt around my waist and connected it with the slit at the side. I pulled on my panties and tucked my cock into them as best as I could. Once I had those on, I adjusted the skirt by expanding the slit on the side to make it a bit wider. The girls giggled at how much skin I was showing on the side and how much of my ass would be visible from the back as I pulled the skirt up a little higher on my waist. I then put on the blouse and decided it would look better rolled up and tied into a knot at the front and the buttons undone to the same level as my bra. I then had Jennifer help me put on the wig which was wavy and hung down passed my shoulders. Once that was firmly in place, the girls stood back and admired how well I looked.
“I think you look a hell of a lot better as a blonde than a brunette Michelle. The guys are going to love this look. Don’t you agree Jen?” Tonya said.
“Hell, I love this look. I want to jump her myself. She looks really hot. She is definitely going to turn heads out there tonight. But, we still have to wait a while before going out though as I am sure there are way too many people out on the streets right now.” Jennifer responded.
“We could always do other things in the car before hitting the streets.” I responded.
“Oh you little slut you. You want to go down on some cock in the car don’t you?” Jennifer asked.
“I’m just offering suggestions of things to do instead of just sitting here for a couple of hours and then going out.” I said back to her.
“I think you just want to get out of the house in your new outfit. That’s what I think. You love letting people see you like this don’t you?” Jennifer said back to me.
I just blushed and smiled at her. We sat there in the room talking for a while longer before going out into the living room. Once we did show ourselves to everyone else, they couldn’t believe the transformation that had occurred.
“Damn. You look really hot Michelle. Love the blonde hair.” John said to me.
“Yeah, but check out that ass. I love getting a little peek of your panties on your hip and how they disappear into your ass at the back.” Ted said.
The others didn’t say a word but I could tell from how hard their cocks were, they definitely approved of my new look. I sat down on the chair and allowed the skirt to ride up exposing the tops of my stockings. I slid my ass to the edge of the chair which allowed the skirt to fall away from my legs at the back where the slit was. I knew this was driving the guys crazy as I could see them grabbing at their cocks through their shorts. Tonya took notice of this as well and whispered in my ear that I did a really good job to get them all that excited.
We sat around for another hour or so and then decided to make the drive into the city. It is about a forty minute drive into the city from my house so by the time we got there it was well after two in the morning. Both cars pulled into the parking structure and were parked on the very top level once more. As we exited the car I asked Jennifer if her plan was for things to happen up here like they did last time. She had asked me why and I mentioned my concern about the hotel guests that may not take kindly to such a scene and call the cops. I told her that I thought we were very lucky the previous weekend no one had called them and wasn’t sure if the risk of being arrested was worth it. She agreed and said that nothing would happen on the parking structure.
We walked to the stairs and made our descent down to street level. We reached the bottom and Jennifer commented to me that she was impressed at how well I was doing in those stilettos. I told her that I had been practicing more than just walking in them and winked at her. She giggled and said we would have to see just how much I had practiced.
As we walked down the street to the corner and turned left, like we did last weekend, I looked over and saw the valet standing there at his post in front of the hotel. I asked Tonya if she thought that was the same guy that was there last weekend. She said she wasn’t sure as she wasn’t paying attention to anyone else but me last weekend. As we approached a position where there was a clear view from his station to the sidewalk where we were walking, I purposely dropped my purse and bent over to retrieve it. I made sure that my ass was in a perfect line to the valet so he could get a good look. I felt the cool night air on my ass when I bent over and knew that my skirt had ridden up over my ass to give him a perfect view of my white lace panties and smooth curvy ass. I retrieved my purse and then joined the others who were a few feet in front of me.
“Oh you little tease.” Jennifer said to me. “He couldn’t take his eyes off you. I would bet that if you went up to him he would be hitting on you as hard as he could. I bet he would even let you suck him off right there behind that valet stand.”
“Oh, I can’t do that. If he’s straight and finds out what I really am, that could be a real problem.” I said back to her.
“Fair point.” She said to me. “What if I went over and asked him if he was bisexual or straight? I could tell him that you only go for bisexual guys and not straight guys. Would you do it then?”
“Hell yes.” I said back to her. “If he was truly bi and not just saying that to have a chance with me, I would definitely go over there and suck him off.”
“You are such a slut Michelle.” Tonya said to me. “What am I going to do with you?”
“Anything you want.” I said back to her.
Tonya laughed at my response as she grabbed my arm. The others were laughing as well because they knew I was serious. They knew that after everything I had done, there probably wasn’t much I would not do at this point. We continued walking down the street, Tonya on my left arm and Jennifer walking on my right with the others trailing us by a few feet. They didn’t want to walk too close so they could keep their eyes fixated on my ass that would be more visible with each flutter of my mini-skirt that happened with each step I took. I think they were keeping a good distance so that if anyone passed us going the other direction, they would be able to get a quick look as they walked by as well.
We continued walking for several blocks until we reached the area that was across the street from the bank. Tonya and Jennifer stopped me and told me I had to take off my panties and put them in my purse. I asked them if they were sure as the skirt would do nothing to hide my hard cock by itself. They said they were sure but I had to do it on the other side of the street bench we were standing next to at the time. They said I had to do it because they saw the security guard in the doorway across the street watching us and they wanted me to tease him. I didn’t look across the street to give away what we were up to as I walked around the bench. I set my purse down on the bench and then reached under my skirt and grabbed onto my panties and pulled them down passed my knees. I stood back up slowly and allowed the panties to fall down to my ankles. I stepped out of them with one foot and then the other. I then bent over and picked them up and put them into my purse while I was still bending over. Once I had accomplished that, I looked over at them and realized Dan had his cock out. I sat down on the bench and beckoned Dan to stand in front of me. The others took positions at either side of him and leaning over the bench from behind. I took Dan’s cock into my mouth as I am sure that is what Tonya and Jennifer were wanting me to do. I unbuttoned his jeans and pulled them down just past the base of his ass so that the security guard could get an idea of what was happening. I sucked on his cock for all I was worth right there on the street. I reached around and grabbed onto Dan’s ass while my mouth clamped down onto his cock. I caressed his ass and then dug my nails into each cheek pulling him deeper into my mouth. I could taste the pre-cum dripping from his cock and knew it wouldn’t be much longer before he rewarded me with a nice big load of hot cum down my throat.
“Do you like sucking on that hard cock Michelle? Do you want his cum in your mouth?” Tonya asked me as she leaned in close.
“Give me that cum.” I said as I removed my mouth from Dan’s cock and looked up at him. “I want that hot cum in my mouth.”
I then wrapped my lips around his cock again as he bucked his hips forward thrusting his cock into my mouth. I pushed his pants down past his knees and ran my nails up the back of his thighs to his bare ass. I then reached one hand around and teased the underside of his balls by lightly running my fingernails across them. When I did that it sent Dan over the edge. His cock pulsed in my mouth as load after load of cum filled my mouth. I swallowed it down and continued sucking his cock dry. Once he was finished, I grabbed his jeans and pulled them up so he could fasten them before stepping away from me.
“Good girl Michelle. But we have more for you to do. Get up and stand at the back of the bench.” Jennifer told me.
I did as she instructed and then she told me to bend over and grab the back of the bench. When I did that I could feel a hard cock press against my ass. I looked over my shoulder to see Simon standing there guiding his cock into my ass.
“Oh yeah. Fuck me Simon. Give me that hard cock.” I said to him.
Simon’s cock entered my ass and was thrust all the way into me. He grabbed onto my hips and began thrusting faster and faster into me. I fixed my gaze across the street and could see the security guard trying to hide on the side of the glass door. I could see him watching me getting fucked. For all he knew, I was just some hot girl getting fucked on the street. I stared in his direction and licked my lips and rolled my eyes. I wasn’t sure if he could see my facial expressions, but Tonya and Jennifer took notice. Out the corner of my eye I could see Jennifer nudge John and I knew he was watching my facial expressions as well.
It didn’t take Simon long to fill my ass with his cum. I felt his cock pulse and send wave after wave of hot cum into me. I moaned with pleasure and threw my head back at the feeling of his cock inside me. Once he had finished, he slowly withdrew his cock and then pulled up his shorts. Tonya then grabbed my arm and we headed off down the street.
“Did you see the security guard trying to hide behind the side of the doorway at the bank?” I asked Tonya.
“Yeah, I saw him. Jennifer pointed him out to me. We could barely make it out, but we are both sure he was stroking his cock while watching you.” She said to me.
“I thought he might be but I couldn’t be sure.” I told her. “In any case, I had to tease him by making those faces at him.”
“Yeah, we saw that too. That was good on your part. The question now is, are you ready for more?” She said to me.
“I’m ready for anything.” I said back to her.
We continued walking and then turned left down a side street. It was a one-way street with s**ttered street lamps. Finally we got to a point where we were directly under one of the street lamps. Tonya pushed me to the wall and told me to face the wall. She reached behind me and lifted up my skirt to expose my ass. Her other hand reached under my skirt and grasped my hard cock. I moaned with pleasure at feeling her hand on my cock. I glanced over my shoulder and could see Ted approaching me. He had his shorts off and his hard thick cock was in his hand.
“Oh yes, give me that cock baby. I want to feel your cock in me.” I said to him.
“What do you want this cock to do baby?” Ted asked me.
“I want you to fuck me. Right here and now. Slide that cock into me and fuck me.” I said back to him.
“Why is that?” Ted said to me as he teased my ass by slapping his cock against each cheek.
“Because I’m such a slut and I love cock.” I said back to him.
Once I said that, Ted slid his cock into my ass. He grabbed my hips and pushed as hard as he could to get his cock all the way into me. The street lamp illuminated the area and seemed like a spotlight was cast upon us. The sound of my ass smacking against Ted with each thrust of his cock bounced off the walls of the building we were against. Tonya could sense I was close to shooting a load of cum myself and released her grasp of my cock.
“Take it bitch. Take that cock in your ass. We’re going to treat you like the whore you are.” Ted said to me as he continued to pump his thick cock into my ass.
“You like that baby? You like being treated like a whore?” Jennifer asked me.
“Yes. I love being treated like a whore. I love serving all these cocks.” I said back to her in between the moans that were escaping my mouth.
Ted reached up and grabbed my shoulders with both hands and continued slamming his cock into me as hard as he could. I could tell he was getting close to shooting his load from the sound of his moans.
“I want that cum in my mouth.” I said to him. “I want you to come in my mouth.”
Ted continued fucking me against the wall until I felt him withdraw his cock from my ass. I quickly spun around and squatted down with my mouth open. Ted grasped his cock and stroked it a couple of times then started unloading cum that had been building up inside him for the last week. He shot so much that a lot of it ended up on my face as well as in my mouth. When his cock started to subside from unloading all over my face, I wrapped my lips around his thick cock and sucked him dry to make sure I got every last drop of cum he had to offer at that moment. Once I was satisfied he was fully drained, I allowed his cock to slip from my mouth. I stood up and smiled at him. His cum was still on my face dripping from my cheek and chin and forehead. I didn’t bother to clean it off but rather left it there as he put his shorts back on and we continued walking down the street.
We walked another few blocks and then turned left again. This one-way street was dimly lit with parking lots placed sporadically along the street bordering various buildings. As we approached one of the parking lots that was surrounded by a chain link fence, I felt hands grab me and f***e me up against the fence. I pressed against it, unable to move from the f***e and weight of another body pressed up against mine. I felt hands roaming over my body and then grasp my skirt and rip it off completely. I then felt the monster sized cock of John pressed against my ass. With one hand on the back of my hand and another on my waist, he pushed my face against the fence and pulled my waist back. I grabbed the fenced wrapping my fingers through the chain links so I could hold on.
“So you like being a whore? Well, as Ted said, we’re going to treat you like one.” John said as he slammed his monster cock into my tight ass.
He began pumping all eleven inches into my tight ass while still pressing me against the fence with one hand and pulling my waist back to him as he thrust forward with his hips. I moaned and tried to subdue the scream that I wanted to let out when he slammed his cock all the way into me. My eyes were closed and my fingers curled around the links of the fence as I moaned in both pleasure and pain. I then felt hands spanking each side of my ass while John fucked me. I opened my eyes slightly and could see Jennifer standing there to my left as the right side of my face was pressed against the fence by John’s hand. I couldn’t see who was on my right and spanking my ass but if I had to guess I would say it was Tonya.
“Take that big dick you little slut.” Jennifer said to me angrily into my ear.
Jennifer then reached down and smacked my hard cock. My cock was so hard, it barely moved. Jennifer took notice of this and decided to smack it harder. John slammed his dick into me with such ferocity that I thought he was going to split me in two. He would slam his cock into me as far as he could, then pause for a moment before slowly pulling it back only slam it back into me as fast and hard as he could. This continued for what I thought was just a short period of time but in fact, this went on for about ten minutes or so. I look back now and am still amazed at how quickly time goes by when you’re enjoying yourself. Finally John slammed his cock all the way into me one last time and pumped all his cum into me. He held his cock in me as his cock sent wave after wave of cum into my ass and then as I thought he was about to pull his cock out, he pushed it back in. He continued fucking me as his cock never softened. He released his hand from my head and grabbed the other side of my waist with it. I clung to the fence as I felt his monster cock continue to fuck me for what was about another five minutes or so. He finally withdrew his cock from my ass, pulled me upright, turned me to face down the street where I could see the parking structure a few blocks away, and told me to get going and get to the cars. I looked around to find my skirt that John had ripped off of me, but I couldn’t find it.
“You don’t get the skirt back until you make it to the cars.” John said to me.
A look of fear came over my face as I was standing there in white stilettos, white thigh high stockings, sheer white blouse tied up in a knot at the base of my white lace bra that shown through the blouse, the blonde wig, and nothing else. Jennifer smacked my ass and told me to get moving. My hard cock bounced with each step I took and the sound of my heels clicking on the concrete sidewalk echoed on the street. I was afraid that someone would see me and then call the police. But the excitement of being seen or caught overwhelmed the fear. I slowed the pace at which I was walking and then decided to have some fun with it. I stopped, spun around, through my arms up behind my head and cocked my hips to one side as I stepped to the left with my left leg. I then spun again so that my ass was facing the group. I bent over slightly and looked over my right shoulder as I reached back with my right hand and spanked my ass at them before wiggling it from side to side. I then started walking towards the parking structure again making sure I crossed one foot over the other with each step making sure my ass shook with each step.
When I reached the intersection with the parking structure directly across the street, I leaned back against the wall of the building and allowed my blonde hair to hang down and barely cover my eyes. I looked back at the group who were about twenty steps behind me. Once they all caught up to me, I walked slowly across the street, pausing in the middle of the street to spread my legs and bend over showing off my ass to the others. As they caught up to me, Tonya spanked my ass and told me to get going as she giggled aloud.
“I think we’ve created a monster.” I heard Tonya say behind me as I reached the other side of the street.
I walked through the parking structure’s first level towards the stairs which were on the other side. Just as I was about to step onto the first step of the stairs, I heard a car door close. I quickly looked around as my heart raced and felt like it was about to jump out of chest. I looked over my shoulder and could see the valet from earlier walking away from one of the cars. My friends were about the same distance away from me as he was. I looked at my friends and smiled and slowly stepped onto the stairs. It felt like I was walking in slow motion as I wanted to tease the valet as much as possible if he happened to see me. Plus, I wanted to go as slow as possible to make sure he did see me.
The others were now on the stairs walking up behind me. Tonya and Jennifer grabbed both of my arms and started pulling me up the stairs laughing the whole way.
“Oh my god you’re horrible. The valet saw you and when he did, he just stood there watching. I looked over at him and smiled and waved to him. Then I ran over and asked him if he liked what he saw.” Jennifer said to me.
“You didn’t?” I responded.
“Yes I did. I also told him that you would only talk to him if he was bisexual and willing to prove it.” Jennifer said back to me.
“What did he say?” I asked her.
“He said he didn’t switch hit.” Jennifer said back to me. “He looked really disappointed when I told him the bisexual thing.”
We all laughed aloud as we continued walking up the stairs. We finally made it to the cars and climbed inside. On the ride home, Jennifer and Tonya both took turns stroking my cock in the car. I thought I was going to shoot a load of cum any second from that glorious feeling of them playing with my cock. Just as I thought they were going to give me some relief, they would stop. They would then talk about something completely off topic and off the wall as if nothing happened. It was pure hell what they were doing to me.
Once we made it back to my place, I climbed out of the car, still without my skirt, and took my keys out of my purse which Tonya had been holding since the street bench. I unlocked the door and let everyone inside. Once everyone was inside, I was expecting to go back and clean up right away. Instead, I was told to sit down.
“Ok Michelle…how did you enjoy tonight?” Jennifer asked me.
“I had fun tonight. John really threw me for a loop when he told me to go back to the parking structure without my skirt on though.” I said back to her.
“You didn’t seem to mind that much.” John said to me.
“No k**ding. You really got into the role didn’t you?” Ted asked me.
“I was scared as hell at first. But once I started walking and made it as far as I did, the fear left me and I got more excited. I decided I would have some fun with it.” I said back to them.
“I can’t believe you still have Ted’s cum all over your face.” Tonya said to me.
“Badge of honor.” I said back to her.
“More like a badge of a slut.” Jennifer said aloud jokingly causing everyone to laugh.
“Did you have a problem with what John did?” Jennifer asked.
“Actually, I didn’t. I thought it was hot as hell. Being f***ed against the fence like that and taken like I was nothing more than a plaything was kinky as hell. I loved it.” I said back to her.
“Good to know. I’ll be sure to remember that.” John said.
After we talked for a while longer, everyone said they had to get going. I e****ted everyone out to their cars, still without my skirt. I gave all the girls a hug as none of them wanted to kiss me with Ted’s cum having dried on my face. I giggled at that and said it was ok. Tonya and Jennifer didn’t seem to mind though as they both kissed me deeply on the lips. I was told I wasn’t allowed to play with my cock or make myself cum at all for the next week. Jennifer also said she would call me about next weekend after she had a discussion with a certain someone. I could read between the lines and understood that she had not talked with John yet about what she had mentioned on Wednesday night. I just smiled and waved goodbye as they drove off.
Once I got back into the house, I removed what little bit of clothing I still had on and got in the shower. I made sure I washed all the make-up off and then dried and crawled into bed. I was unable to fall asl**p right away and tossed and turned as my mind repeatedly flashed back to the events of the night. I couldn’t wait for the next exotic adventure Michelle would be thrust into.