The Miss-adventures of Michelle Section 2, Chapter

Chapter 2
It was Saturday morning, the last day of having to wear panties as per the terms of the bet I lost the previous weekend. I had just finished getting the house in order and took my time in the shower making sure everything on my body was perfectly smooth. I once again applied the scented lotion to my body to give it that extra smooth feeling that felt so nice. I had decided on wearing the red Brazilian style panties the rest of the day and nothing else. I had to do exactly what Jennifer told me the previous day at our lunch date and to be quite frank, I was thrilled with having to wear them and nothing else in front of everyone. After all, I had to do it the previous weekend anyway once I lost so it wasn’t anything new to everyone.
I was parading around the house putting the final touches on things when the doorbell rang. I quickly slid my fingers under the backside of the panties and pulled them up a little more to expose more of my ass. I looked through the window and saw that John, Jennifer, and Tonya were on the other side of the door. I opened the door and invited them in. Eric said nothing once he saw me in the panties. Jennifer simply smiled and told me “good boy” for doing what she said to do.
“What are you doing wearing nothing but panties?” Tonya asked me.
“Jennifer told me yesterday at lunch this is how I had to be dressed today until a new bet was made and a winner declared.” I said back to her.
Tonya looked over at Jennifer and smiled while nodding approvingly at her decision. Everyone gathered in the kitchen to get themselves a drink and wait on the rest of the group to arrive. Ted and Dana were a few minutes behind Eric and were soon admiring the red Brazilian panties I was wearing. Ted couldn’t resist running his fingers over my ass and feeling the material pressed up against me showing off the curves of my ass.
“I have to admit Mike…you have a nicer ass than most women. The curves are fantastic. Don’t you agree Dana?” Ted said as he removed his hand from my ass.
“Yeah, I have to admit, I am a bit jealous. Not flabby at all, nice and tight, and such nice curves.” Dana said as she cupped each cheek of my ass and squeezed.
Tonya and Jennifer were smiling from ear to ear. I looked into their eyes and could see the wheels turning. I knew they were planning something, what it was though, I didn’t know. The only thing on my mind at that moment was the feeling of Dana’s hands cupping and squeezing my ass and then moaning with delight. Dan, Mary, Simon, and Tina finally arrived approximately thirty minutes later. The girls shrieked with delight when they saw me wearing the red panties and couldn’t resist grabbing onto my ass as Dana had done when she first saw them. Once we all sat down in the living room, Tonya told me to tell everyone the story of what happened when I went shopping. I blushed a little bit and smiled and then proceeded to tell the story of my shopping experience at Frederick’s of Hollywood on Monday morning. Once I finished the story, Tina asked me to go get the panties to show them to her. She said she wanted to see what kind of taste I had for panties and if I had done a good job in picking them out. I reminded her that I had some help but went into my bedroom and retrieved all the panties I had bought earlier in the week.
It seemed as though the girls were the only ones who were interested in the panties. The guys just sat there drinking and watching TV. Of course, once Tonya told me I should put each pair on and model them for everyone, the guys perked up real quick and paid close attention. I started to make my way to the bedroom to put on the first pair but Tonya stopped me. She told me to stay in the living room and put each one on. She reminded me that everyone there had seen me naked already anyway so why should I care about trying on different pairs of panties. She had a point, but the main reason I was wanting to leave the room was because I knew if I stood there in front them naked, I would get so excited that each pair of panties would no longer contain my fully erect cock.
I stood in the middle of the living room and peeled off the red Brazilian pair of panties and just as I thought, my cock sprang to full erection. I saw Ted reach down and grab his cock through his shorts as he stared at me standing there naked in the living room. The girls were all sitting on the floor in a semi-circle around me while the guys occupied their typical places on the sofa and loveseat. I kicked off the panties and took the pair that Tonya was handing to me. It was the thong and I knew that my cock would not be contained within them. I stepped into them and pulled them up. I pulled them tight into my ass and just as I thought, my cock was completely exposed from the front. Once I did a little twirl in the living room so everyone could see me wearing them, I took them off and tried on the next pair. Just as I was about to bend over and step into them, Eric told me to turn so my back was to them. I did so and as I bent over, I could feel their eyes on me. I could feel their gaze on my smooth, tight ass. Knowing this, I took my time in pulling them up and standing upright. Once I had them on, I cocked my hip to one side and curled my arms behind my head trying to pose as close to the supermodel pose as I could. With each pair that I tried on, the more feminine I acted.
“Wow, you’re really getting into this aren’t you?” Jennifer said as I tried on the third pair and walked around the living room swaying my ass back and forth with each step I took.
“I think he’s enjoying this. I think he loves modeling panties for us.” Tonya said to Jennifer.
“I don’t think he’s the only one enjoying this.” Jennifer said as she looked at the guys who now how had their cocks out and were stroking them. “I think they’re getting into seeing Mike model the panties and acting feminine.”
“Put those away damn it. There won’t be any playing right now. That will come later on tonight.” Tonya scolded them.
I had finished modeling every pair of panties and had returned to my red Brazilian pair and put the others away in my bedroom. I came back out and the guys had put their cocks back in their shorts which did nothing to hide how hard and excited they were. We all set about eating a late lunch and watching the games on TV awaiting the night game which everyone had decided would be the one to bet on. When the time came, I knew I was going to be betting on what I was sure would be the losing team. If there was ever any doubt about that, the modeling job the girls made me do earlier in the day solidified my idea of losing on purpose.
The night game finally came and all the guys agreed they were betting on one team and I instantly played it off as I was sure they were going to lose and voiced my decision to bet on the other team. I looked over at Tonya who gave me a questioning look but I just smiled back at her. I had a feeling she was on to my little ploy and knew that I was planning on losing on purpose.
“You do realize that if you’re doing what I think you’re doing, I’m going to come up with something really special for you as punishment.” Tonya whispered into my ear so that no one else could hear her.
My cock twitched in anticipation of what Tonya would come up with for me to do. It would only be better if her and Jennifer got together and came up with something. My mind was racing with ideas. Would I be f***ed to go down on everyone again? Perhaps I would get used like the weekend I was tied to the railing on the deck only this time the girls would get to see everything happen. The excitement grew and grew within me with each passing moment of the game. The clock was ticking down and as I looked at the score, my cock grew with excitement as I knew it was only a matter of time before I would be paying up yet another bet.
The final whistle came and I had lost yet another bet. I tried my best to look disappointed, but the sight of my erect cock showing out the top of my panties gave off another emotion. I leaned forward and buried my face in my hands trying to look as displeased as possible all the while smiling from ear to ear behind my hands. Tonya ran her fingers down my bare back and then through my hair.
“Alright, what is it I have to do?” I asked aloud as I slowly removed my hands from my face while maintaining a downward gaze.
“Let’s go girls. We have some brainstorming to do.” Jennifer said as she stood up from her place on the loveseat.
The girls all got up and huddled together in the kitchen. After a moment or two, they started walking out the front door. “Where are you all going?” Ted asked.
“We’re just going out to the car for a moment. We’re still coming up with what Mike has to do.” Jennifer said as she closed the door behind her.
Why were they going out to the car? What on earth were they up to? I sat there in the living room and as I glanced around the room out the corner of my eye, I could see the bulges taking shape in each of the guys’ shorts. I knew they were getting excited about what was to happen just as much as I was at that moment. It took every bit of concentration I had to keep myself from reaching down and stroking my cock through those panties. Just as I was about to give in to the temptation, the front door opened and the girls were walking back in laughing almost uncontrollably. Jennifer was the last one to come in to the house and in her hands was a backpack stuffed full of something or another.
“Come with us Mike.” Tonya said to me as she held out her hand to me.
“We’ll be back in a little while guys. You all just sit there and relax for the time being.” Dana said to the guys as I was being led through the kitchen to my master bedroom.
Tonya told me to sit on the edge of the bed as Jennifer walked behind me to the other side of the bed and began taking things out of the backpack.
“Jennifer and I came up with something that I think you will truly love my dear.” Tonya said looking down at me. “Tonight, you will no longer go by the name of Mike. Tonight your new name is going to be Michelle. We have some things that you are going to wear and show off to the guys. Once we get you dressed up in your new clothes, you will then go model for the guys and then take all orders from Jennifer as to what you will do next.”
Michelle? Were they planning on doing what I think they were going to do? Were they going to make me dress up in women’s clothes and pretend to be a woman? My heart began racing and my mouth went dry. There was a part of me that started to wonder if all these bets had gotten out of hand and were spiraling out of control. But when I felt my cock twitch and ache to be fondled, I realized there was another part of me that was completely intrigued and excited about the idea.
“Here.” Tonya said to me, “Put these on first. But take off those panties as you won’t be wearing those anymore tonight.”
She handed me a pair of black thigh stockings. I stood up and took off the red panties I was wearing and my cock stuck straight out from my body. I sat back down on the edge of the bed and struggled with putting on the stockings. Tonya giggled and then showed me how to put them on properly by rolling them and then slipping my foot in and then pulling them up my legs to full length. I finally got both of them on my legs and I have to admit, the feeling was incredible. The softness of those stockings against my legs was intoxicating. I couldn’t resist rubbing my legs together and feel the sensation. Tonya then handed me a black garter belt and showed me how to put that on and attach the stockings to it. As she knelt in front of me, my cock brushed against her cheek leaving a streak of pre-cum. When she stood up, she turned her face to show me her cheek. I knew what it was she wanted so I removed the pre-cum from her cheek with my tongue.
I was then handed a black mini-skirt that was connected at the side by a snap. I wrapped it around my waist and snapped it together. Tonya then grabbed hold of it and spun it around my waist so that the slit was on my left leg. She also pulled it up a little higher and when she did so, I could feel the bottom of the skirt slide past the bottom of my ass. The problem I was having though was that my cock was poking the front of the skirt straight out from my body.
“Seems to me he’s really enjoying this idea so far.” Jennifer said as she came around the bed to admire my new attire thus far.
“He may not once he knows what else is in store for him.” I could hear Tina say from behind me.
“Oh, I don’t know…I have a funny feeling he’s going to love it.” Jennifer said as I felt her fingers fiddling with the back of the skirt and brushing against my ass.
The next item was a black lace bra that Tonya handed me and then reached around me to hook together, then adjust into its proper position. I was then handed a black, sheer, button up, long sleeve blouse to wear. I put the blouse on and buttoned it down. Tonya stood back from me and looked me up and down and then shook her head. She reached over and undid the bottom three buttons. She pulled the blouse up and then tied it into a square knot at the front so that it was tied just below the bra I was wearing. Once she was satisfied with the look, she had me sit down on the edge of the bed once more.
“Ok girls…makeover time.” Tonya said giggling.
The rest of the girls came around the edge of the bed and in their hands were various items of make-up and each one took turns applying it to my face. First there was the foundation that Tina applied, then the blush. Mary went to work on my eyes adding eye-liner and a bit of color. Dana was next and applied the lipstick. Finally Jennifer came around and put a black wig of hair on my head. Once she finished adjusting it and making it fit just the way she wanted, she stood back from the bed. All the girls were standing in front of me and asked me to stand. Tonya then handed me a pair of black high heeled shoes to put on. I put them on and nearly lost my balance.
“I’m actually jealous.” Tina said. “Michelle looks really good.”
“She does, doesn’t she? I think the guys are going to love her. If there wasn’t a big hard cock poking out the front of the skirt, I would swear it was just another hot looking girl standing in front of us.” Mary said in response.
“Ok Michelle, you need to practice walking around the room in those shoes and get accustomed to them. We can’t have you go out there to the guys falling all over the place.” Jennifer told me. “Oh, but you cannot go into the bathroom. I don’t want you seeing what you look like all dressed up in your new clothes and alter ego. I want you to experience the guys’ reactions and judge your own looks based off of them.” She continued.
I tried walking around the room in the high heels and I felt like I was about to break my ankle. I couldn’t figure out how women walked in those damn shoes. After about ten minutes or so, and some coaching from each of the girls, I was finally getting the hang of walking in high heels.
“I’m going to give you this entire outfit. I suggest you practice walking around in those heels as much as possible sweetheart. I have a funny feeling that once the guys get a look at you, they’re going to want to spend a lot more time with Michelle.” Tonya said to me.
Jennifer then left the bedroom but told me to stay put until she got back. She went out to the living room and I could hear her telling something to the guys but I couldn’t make out what it was. I’m sure she was giving them instructions and telling them what was going on and what part they would play. I remained in the bedroom and continued to practice walking in the heels. The girls had me doing turns and various poses to get accustomed to not only the new shoes, but the clothes as well.
Jennifer returned to the bedroom just as I was practicing a bending over pose to show off my ass. She walked in to me bent over in the heels with my ass completely exposed and as I returned to an upright position, I ran my fingers along the stockings on my inner thigh and flicked the skirt up in the front teasingly.
“Oh, that’s good. That’s really good.” Jennifer said as she caught me posing in that fashion. “It’s all set Michelle. You’ll go out into the living room and pose and tease and flirt. They will give you other instructions and things to do once you’re in there. I’m sure they’re going to love you and you’re going to love doing what they want. We’ll be in there in a little bit as we want to sit back and watch the reactions they have.
Jennifer stood by the door and as I gazed through the kitchen to the living room, I could see Dan sitting on the sofa. I began to walk through the kitchen and my heels clicked with each step on the tiled floor. I could see Dan’s eyes get really wide and then shoot his left arm straight out and smack Ted who was sitting next to him. Ted turned to see what he was looking at and when he saw me, his eyes widened and his jaw dropped. I could see his eyes moving up and down my body as I tried to walk into the room as seductively as possible. The problem I was having was that I was concentrating so much on not falling over that I lost all sex appeal in my walk. I made it to the living room and when Simon and Eric got their first looks at me, their eyes widened and they all stared at me disbelief.
“And what might your name be?” Ted asked me playing along with the game.
“My name’s Michelle.” I responded in as feminine a voice as I could do.
“Well, it’s certainly nice to see you Michelle. Are you our entertainment for the night?” Ted asked me.
“I’m here for your pleasure.” I responded back to him.
“Sounds good to me. Show us what you have sweetheart?” Eric said to me.
I began to strut around the living room as best as possible. I would try my best to twirl and allow the short skirt to flip up into the air and show off my ass they were so fond of grabbing and spanking. As I continued to walk around the room, I got more and more comfortable walking in the heels. I then stood in front of Ted and Dan and spread my legs apart and bent over at the waist. I looked over my left shoulder as I bent over and I could see Ted’s eyes fixated on my ass. I also took notice of the bulge that was clearly showing through his shorts. I slowly came back to a standing position and as I ran my fingers up through my hair, I looked over at Eric who had pulled his shorts down to his knees and was stroking his big cock. Simon had followed suit with Eric and had removed his shorts completely and sat there stroking his hardened cock. I turned back around and then I saw Ted and Dan had removed all of their clothes and were sitting there stroking their cocks. The more I played the role of Michelle, the more I got into it and had fun with it as I gazed at those four hard cocks. My mouth watered with anticipation of being told to suck on each cock or better yet, to feel each one slide inside me and fuck me. I decided to play the tease role a little more though and swished my ass back and forth as I walked over to Simon and turned around. I bent my legs and grabbed onto this thighs near his knees and pushed his legs apart. I then dropped my ass onto his lap and felt his hard cock press against my ass. I moved my ass back and forth on his cock teasing him. I could feel his pre-cum being slid across my ass with each rotation. After a few minutes of teasing Simon, I stood up and walked over to Eric. I bent over at the waist with my hands on his thighs and dropped my new long hair down onto his monster cock. I moved my head from side to side allowing my hair to trace along his cock and tease it. I brought my mouth down near his cock and allowed him to feel my breath against it. It was so difficult to keep myself from taking his cock into my mouth.
After a few moments of teasing Eric, I moved over to Ted and knelt in front of him. I traced my fingernails along his inner thighs and up towards his hard, thick cock but never touched it. I leaned forward and allowed my nose to bump against his balls and slid it up the underside of his cock and allowed him to feel my breath on it. I could hear Ted moaning and as his hands reached up to grab my hair, I pushed his hands back down to his side. Ted took the hint and kept his hands at his side enjoying the show I was putting on and the teasing I was giving him. Once I felt that I had teased Ted long enough, I moved over to Dan. I spread his legs apart with my legs and spun around. I grabbed the skirt and flipped it up as I stood in front of him showing him my ass before I dropped my ass down onto his lap. I leaned back and pressed my back against his naked chest as I rotated my ass around on his lap feeling his cock press against me. I looked through the kitchen and I could see the girls watching from the master bedroom in the doorway. They were all smiling as they watched me turn into Michelle more and more as I teased each of their boyfriends.
“Ok, that’s enough teasing Michelle. I want you to start with Dan and go down on each one of them.” I heard Tonya say across the house.
I spun off of Dan’s lap and dropped to my knees in front of him. I grasped his cock with my hand then wrapped my lips around him and tasted his pre-cum. My long hair I now had, d****d down onto his lap as I sucked on his hard cock and stroked it with my hand. I could feel the skirt I was wearing had slid up and over my ass making it completely exposed to everyone else in the room. I continued sucking on his cock oblivious to the scene that was unfolding behind me.
As I continued sucking on Dan’s cock, I felt a hand brush my hair away from my ear. I then heard Tonya’s voice as she leaned in close to me. “Keep sucking on Dan’s hard cock. You’re in for a treat while you do that. Take a look.”
I removed my mouth from Dan’s cock and looked behind me. Standing there in the living room were each of the girls, completely naked, except for the strap-on that each one was wearing. They didn’t skimp on the size of each strap-on either. I would estimate each one to have been about ten inches in length and of a medium thickness. All of them stood there with their hands on their hips staring down at me.
“This is what’s going to happen Michelle. Each guy you go down on, his girlfriend is going to fuck you with the strap-on they’re wearing. They will stop when their boyfriend has filled your mouth with cum and you have swallowed it down. Once you have pleased every guy in here, you will then be mine to play with as I see fit.” Tonya said to me while grabbing my hair pulling my head back.
Once Tonya pushed me back down onto Dan’s cock and released my hair, I could feel a thick strap-on slowly slide into me. I could feel Mary’s hands on my hips as the tip of the strap-on entered me and she started to slide the entire length of that strap-on into my tight hole. I moaned with Dan’s cock in my mouth as I felt that strap-on fill my ass. I could feel Mary’s thighs against my ass as she slid the entire length of that strap-on into me. As she began to pull back I pulled my mouth up Dan’s cock. Dan grabbed my hair and held it behind my head so he could see me sucking on his cock as he watched his girlfriend fuck me. Mary and I got into a rhythm of meeting each other. As she pushed forward, I moved backward until my ass smacked against her and then immediately rocked myself forward again and down onto Dan’s cock. I looked out the corner of my eye and I could see Ted stroking his cock and the pre-cum forming on the tip of it. I was moaning as loud as I could with a hard cock in my mouth which turned Dan on even more. I could hear Mary behind me moaning and saying how much she loved fucking Michelle’s tight ass. She would ask Dan if he liked the new girl sucking his cock and if she was doing a good job at it. The only responses Dan could muster were moans and groans as I teased the tip of his cock. I finally felt Dan’s cock begin to twitch and I knew it wasn’t going to be long before he filled my mouth with his cum. I could hear Mary behind me saying she was going to cum. Hearing this sent Dan over the edge as he bucked his hips up and f***ed his cock into my mouth to ensure I would take all of his cum. He began shooting load after load of hot cum into my mouth. I swallowed as quickly as I could so that I could get every drop of it down my throat. I continued sucking him dry as Mary had f***ed the strap-on she was wearing all the way into me as an orgasm shuddered through her body. Once Dan’s cock was properly drained and I had cleaned it up completely, I removed my mouth and Mary slowly removed the strap-on.
“Damn Mary. I’m not sure if Dan, Michelle, or you enjoyed that the most.” Jennifer said to her.
“Oh my god you guys. Now I have an idea of how wonderful it must have been on the back deck with all seven of those guys two weeks ago. I never came so hard in my life.” Mary said trying to catch her breath.
“Alright Michelle, one down three to go. Get over there and suck Ted’s cock while Dana takes her turn fucking that cute and sexy ass of yours.” Tonya ordered me.
I crawled over on my hands and knees the short distance from between Dan’s legs to position myself in between Ted’s legs. As I knelt in front of him and grasped his thick cock with my hand, I felt Dana flip my skirt up over my waist exposing my ass entirely. As I took Ted’s thick cock into my mouth, Dana spanked each side of my ass and giggled. She traced her fingers up and down my ass before smacking my ass with that thick strap-on she was wearing. I was finally tasting the pre-cum dripping from Ted’s cock and moaned as the salty sweet flavor filled my mouth.
“Do you want my cock in you Michelle?” Dana asked me as she teased my hole with the head of the strap-on.
“Yes. Fuck me with that big cock of yours. I want to feel you inside me.” I said back to her.
“Ohhhhh, we have a little cock slut here don’t we girls?” I heard Jennifer say as Dana positioned herself to thrust that cock of hers into my ass.
Dana pushed as she grasped my hip with one hand and guided the strap-on into me with the other. The tip of the strap-on passed the entrance to my ass and once Dana was satisfied it was in, she grasped my hips with her other hand. I could feel her shuffle forward so that she was in a comfortable position. I slid my tongue up the underside of Ted’s thick cock from the base to the tip as Dana slowly slid that cock of hers into me. Once she pushed far enough to have the entire length inside me, I wrapped my lips around Ted’s cock. Dana began to slide the strap-on back and then forward once again. Once she got into a rhythm, I allowed her thrusts to dictate my movement on Ted’s cock. My mouth slid up and down his cock as Dana moaned with pleasure at fucking my ass. At times Dana would let go of my hip with one hand and smack my ass. She moaned with pleasure as she would continue to spank my ass. I would lurch forward with each smack and she giggled with delight as she commented on how red my ass was becoming. Once she was satisfied with how red my ass was, she grabbed onto my hips with both hands once more and increased the pace at which she was fucking me.
“Oh honey….now I know why you enjoyed that weekend with all the guys here on the back deck. I can see why you like fucking this tight ass of hers.” Dana said to Ted.
I couldn’t help but notice that Dana referred to me in the feminine aspect when she said, ‘hers’. They were referring to me and acting like I was just another girl in the group. I moaned with each thrust of her strap-on into my ass and the feeling of Ted’s thick cock in my mouth. I looked over to my left and saw that Mary had removed her strap-on and was sitting on the sofa rubbing her pussy while sitting next to Dan. My cock was aching and dripping pre-cum from the feeling of Ted’s thick cock in my mouth, the taste of his pre-cum on my tongue, and Dana’s thick, long strap-on in my ass. Dana continued fucking me as I sucked on her boyfriend’s cock. Ted’s moaning mixed with Dana’s filled the living room. I then could hear Dana telling Ted to cum in Michelle’s mouth. She was telling him to fill that little slut’s mouth with his cum. Hearing Dana talk like that and refer to me in that sense was enough to drive me over the edge. I was so close to shooting a load of my own at everything going on. I fought off the urge just as Ted began to unload a torrent of cum into my mouth. I didn’t think Ted would ever stop coming in my mouth. I swallowed and swallowed as quickly as I could. It was so much that I couldn’t keep pace and some of Ted’s cum dripped from the corners of my mouth and down his cock to his balls. Dana, seeing Ted’s hips shift up and thrust his cock into my mouth, caused her to hold her breath and have an orgasm of her own. I could feel Dana slowly slide the strap-on out of my ass while I licked the entire length of Ted’s cock making sure I got every drop of cum that I wasn’t able to keep in my mouth. Once Dana had completely removed her strap-on, Tonya ordered me over to Simon’s cock.
I crawled over to between Simon’s legs with my skirt still flipped up over my waist exposing my ass. I made sure I shook my ass back and forth as hard as I could with each movement of my legs. I took Simon’s cock into my mouth and I knew it wouldn’t take long for him to cum. His balls were tight against his cock and as soon as my tongue licked the underside near the head of his cock, I could feel it twitch. I giggled and told Tina that she wouldn’t be back there long from the look of things.
“No, she probably won’t Michelle. I’m so worked up right now it won’t take long at all.” Simon said to me.
“I guess I better get in there as fast as I can then.” Tina said to me as she spanked the one side of my ass that wasn’t red. “I think we need to balance out the redness of this cute little ass of yours while we’re at it.”
Tina slid the strap-on into me without hesitation and began spanking the left side of my ass. The stinging sensation of her hand smacking my ass caused me to twist my ass around in circles while she kept that strap-on inside me. Once she had the desired redness of my ass, she grabbed my hips and slammed that strap-on into me as hard as she could. It was thrust in with such f***e, I had to release my grasp of Simon’s cock with my mouth and let out a light screams of “Fuck me harder” and “give me that big dick.”
“Oh, I think she likes it rough. I think she likes being treated like a little whore.” Tina said as she slammed the strap-on back into me as hard as she could.
I was right. It didn’t take long for Simon to shoot his load of cum into my mouth. Tina seemed disappointed as she wasn’t able to fuck me long enough to have an orgasm of her own. She told me that I would have to make sure she got her orgasm somehow but she would leave that up to Tonya as to how I would make sure that would happen.
“Oh, don’t worry sweetie. I’ll make sure Michelle gives you that orgasm you need…somehow.” Tonya said to her. “Now get that ass over there and suck on Eric’s cock you little slut.” Tonya then ordered me.
I moved to my left and took Eric’s monster cock into my hand. I slid my tongue up the underside and to the head of his cock and then back down again. Jennifer took her place behind me and guided her strap-on into my ass. Jennifer wasted no time in getting into her own rhythm of fucking me. She reached up and put her hands on my shoulders and then grabbed my hair and held onto that as she bucked forward hard and fast. The pace at which Jennifer was fucking me, made it difficult to get into a rhythm with her so I could suck Eric’s cock in the best way possible. I did the best I could under the circumstances, but I wasn’t complaining at all. Finally I was able to get into some semblance of a rhythm with Jennifer as her pace slowed slightly. I grasped Eric’s cock with my hand and made the long strokes up and down his cock as my mouth clamped down on it. My tongue ran across the underside of his cock as my mouth moved up and down as far as it could go. My mouth was stretched as much as my ass was being stretched. After a while of pure bliss, Eric finally rewarded my efforts and gave me a mouthful of cum that I quickly swallowed down as I was not going to make the same mistake I had made on Ted’s cock. I was able to keep pace with each spurting of his cock and once Eric announced he was coming, Jennifer had her own release but continued fucking me through the orgasm that was thundering through her body.
Once Eric’s cock had thoroughly been drained and Jennifer had removed her strap-on from my ass, Tonya ordered me to the center of the room. She then told Tina that if she really wanted her orgasm, then she should lie down on the floor in front of me.
“Michelle. You were a bad girl for not giving Tina her orgasm earlier. So, you’re going to give it to her now. You’re going to lick her pussy until she is satisfied. If you aren’t doing it right, then you will get a punishment that I don’t think you want. Now get over here and spread those legs apart for me.” Tonya ordered.
As I moved to the center of the living room, I looked over at the strap-on Tonya was wearing. It wasn’t the same size as the others. This one was a lot bigger. This strap-on was bigger than Eric’s cock. If I didn’t know better, I would swear it was a mold of a horse’s cock. I got into the position I was told to be in and leaned forward to Tina’s pussy. I flicked my tongue across her clit and she moaned with pleasure. At least I knew from her reaction that she wasn’t going to fake not having an orgasm just to see me get a more severe punishment. Tonya got behind me and slowly pushed that huge cock into my ass. I wasn’t sure I was going to be able to take that monster of a cock into my ass but Tonya was persistent in making sure I did. My ass was almost straight up in the air and Tonya adjusted my knees to lower my ass down to a comfortable level for her to fuck me. Once Tonya had the tip of that cock in my ass, she grabbed my hips and slowly f***ed as much of that cock into me as she thought I could take. Tina was grabbing my hair and holding it away from her pussy as I slid my tongue from her ass to her clit. I pushed my tongue inside her pussy and tasted her. When I did that she moaned even louder.
“Damn. If she sucks cock as well as she licks pussy, I can see why you guys love her giving you blowjobs.” Tina said breathing heavily.
I decided that I would take it a step further with Tina and I slid my finger inside her pussy as I sucked her clit in between my lips. I sucked on her clit and slid my finger up inside her until I found that magic spot that I knew would drive her over the edge. I rolled my finger back and forth inside her and then side to side on that spot. Her moans were getting louder and louder and I knew everyone was wondering what I was doing to have this kind of an effect on her. Tonya took notice of this and rather than fuck me hard and fast like Jennifer had done, she kept the pace at a slow and methodical one. However, she did try and get more of that monster cock into me with each thrust.
I knew Tina wasn’t going to last much longer as I could feel her body shuddering and her pussy tightening. I continued teasing her clit by flicking my tongue back and forth across it and then sucking on it again. I felt her body begin to convulse and I knew she was about to have an orgasm. I continued using my finger on that special spot in her pussy and just as she screamed, I removed my finger. Her hips thrust upwards and she began to have an orgasm that caused her to squirt all over my face. Just as she began to squirt, I could feel Tonya’s thrusting into my ass stop. I wasn’t sure why she stopped, but I stayed in that position and let Tina squirt all over my face. I then buried my face on her pussy once more and teased her clit. It finally got to the point where she couldn’t take it anymore and pushed me away from her pussy. She lied there on the floor trying to catch her breath.
“Holy shit. That has never happened to me before. What the fuck did you do to me?” Tina asked me.
“It’s a secret. I can make any woman do that.” I said back to her smiling.
“I think you need to prove that Michelle.” Jennifer said to me.
I looked up and could see everyone staring in disbelief at what had just transpired. Tonya said that she was even impressed. But, she also said that she was going to get hers as well. She removed the strap-on from my ass, took it off her body, and then she moved around and lied down in front of me and instructed me to do the same thing to her. I did as she asked and began with licking her pussy. I teased her clit with my tongue and even slid my tongue down to her ass and back up again. I then slid my finger inside her pussy and used it to fuck her for a few minutes. I wanted to savor this moment as I was finally getting the opportunity to lick Tonya’s pussy and give her an orgasm. I was finally able to repay the favor of her allowing me to cum the previous weekend when she had me wearing her panties.
I found the spot in her pussy and began teasing it. Once I hit the spot, I could hear Tonya moan.
“Oh, he has the spot now doesn’t he?” Tina asked her.
“Oh shit yes. Don’t stop. Oh damn that feels so good.” Tonya responded.
I continued teasing her pussy and sliding my finger in and out of her and then back to the spot where I would tease her and work the magic on her. It didn’t take long for Tonya’s body to tighten up and I knew she was about to do the same thing Tina had done. Just as she screamed and thrust her hips upwards off the floor, I removed my finger and her pussy exploded all over my face just as Tina had done. I could hear a holy shit from someone in the room watching but it was soon drowned out by Tonya’s screams of pleasure. I went back down on her and teased her clit and sucked on it. She was so sensitive at this point that she too had to push me away from her pussy. I sat up and let my ass rest against the back of my legs while I stared at her. Once she had somewhat caught her breath, she motioned for me to lean down to her. She wrapped her arms around me and pulled me down and kissed me deeply. I then helped her sit up on the floor and then brushed her hair back away from her face.
“Oh my god that was so damn good. You really can make any woman do that. I’ve never done that before in my life. That was the most intense orgasm I have ever had.” Tonya said to me. “I think you need to do that to Jennifer and Dana and let them experience that feeling. Go ahead girls. Let Michelle give you the most intense orgasm you have ever had.”
“You don’t need to ask me twice.” Jennifer said as she pushed her ass to the edge of the loveseat and leaned back.
I then proceeded to do the same thing to both Jennifer and Dana. By the time I was finished, I was soaking wet from each woman squirting all over me. I not only had gotten fucked by all of these beautiful and sexy women, but I also got four huge loads of cum from each guy and then given each woman the most intense orgasm they have ever had. Once everyone had caught their breath and finally composed themselves, Jennifer and Tonya told me to follow them back to the room.
My cock was still causing the front of my skirt to stick straight out from my body and was aching for some kind of release. Once we made it back to the bedroom, Tonya and Jennifer told me to strip off the clothes as they were soaking wet. They then proceeded to give me the creams and soaps to remove all the make-up. I went into the bathroom once they had removed my wig and I was stripped down to nothing but the make-up. They had told me they didn’t want me to see exactly what I looked like as Michelle until I learned to put on my own make-up. I went into the bathroom and washed my face clean which did nothing for my aching cock. When I walked out of the bathroom and looked at the bed, there was Tonya and Jennifer both lying back, still completely naked, waiting on me. I wanted so bad to jump into the bed with them and have my way with them right then and there. When they took notice I was no longer in the bathroom, they told me how good that was and that I was no longer paying off the bet.
“This has been an incredible night. I have to admit that I loved how much you got into the role of being Michelle and doing the teasing and dancing for the guys. But, I’m not going to let you cum tonight. I want you to save it. In fact, you can’t cum all of next week either. I know you lost tonight’s bet on purpose. I’m glad you did, but I would like for you to win once in a while too.” Tonya said to me.
“Well, if we all bet on the same teams every weekend, then there will never be any winners or losers. Someone has to take the other team.” I said back to her.
“That’s true. But I have a funny feeling you enjoy losing. Don’t you?” Jennifer said to me.
“Yeah, I have to admit…it is kind of fun and I love the new ideas you come up with each time. I never would have suspected you would dress me up as a woman let alone use the strap-on.” I said back to her.
“I think we’ll have to do the Michelle routine again sometime soon then.” Tonya said back to me.
“How about next weekend?” I asked her.
Both girls laughed at that and then smiled at me and simply responded, “You never know.” After that both girls got up from the bed and we all walked back through the kitchen to the living room. I couldn’t help but stare at Tonya’s perfect ass. My cock was aching to press against her and slide into her. I didn’t care if Jennifer sat there and watched, I wanted to bend Tonya over the bed and fuck her so bad.
Once we made it back to the living room, we all sat around talking for a while longer and all the guys couldn’t stop talking about the transformation that happened. They all agreed that if Michelle came up to them on the street, and hid the hard cock somehow, they would have thought Michelle to be another good looking woman. Tonya kissed me on the cheek as we both were sitting on the floor and Tonya was behind me with her arms wrapped around me. Her tits felt wonderful pressed against my back which did nothing to appease the aching in my cock which had not softened all night long.
When everyone said it was time they get going, they all got up and gathered their clothes. It was Jennifer who spoke up and suggested they all have some fun and drive home naked. Tonya was all for it and everyone else perked up with interest at the idea. They finally all agreed and didn’t put their clothes on. I e****ted each car load out to their car and waved goodbye. I gave Tonya and extra-long kiss at Eric’s car just so I could feel my cock pressed up against her. Once she got into the car and waved goodbye, I went back inside and did what little cleaning up I felt up to doing that night. I collapsed into my bed and soon found myself sound asl**p.
The next day I called Tonya and thanked her for last night. She said that she felt like she had to be the one thanking me. She told me that I would have to do that again for her. At the time I thought she was talking about the orgasm I gave her from me going down on her. I would find out the next weekend that I was only partially correct in my assumption. I then asked her how I should wash the clothes they had me wearing as they needed to be washed badly after last night. She told me and then said that we needed to get together for lunch at some point during the week. I agreed and told her to merely tell me the day, location, and time and I would be there. Once we got off the phone, I decided that I would continue wearing the panties and when I met Tonya for lunch, I would show her and see what kind of reaction I would get. If it was a good one, then I would continue wearing them as I enjoyed the feeling of wearing panties under my clothes. It made me feel a bit naughty and slutty. I would find out later in the week when I met her for lunch, Jennifer would be joining us and they both would enjoy the sight of me still wearing the panties. I didn’t realize it then, but it set the wheels turning in their minds and their plotting for the upcoming weekend had commenced.