Section II: The Emergence of Michelle
Chapter 1
A week had gone by since the weekend I was used as a play-toy by John, Ted, Dan, Simon, Matthew, James, and Ben. Every night my dreams were filled with images of me bent over on the back deck with my hands tied to the railing. Standing behind me would be John, sliding his monster sized cock in and out of me while the others stood around me in a semi-circle stroking their cocks. One by one they each took turns fucking me. Some of them fast and hard and others slower and more methodical. In the dream I would see Tonya and Jennifer watching from the doorway of the back door leading out onto the deck. Both of them would be smiling and grinning. In reality I was blindfolded and unable to see a thing, but I could feel each hard cock as it slid in and out of my tight ass. I could feel each one spank my ass in succession. I could feel each cock explode and fill my ass with their hot cum and at other times unload a torrent of cum all over my back and ass.
Each night I would wake up in a cold sweat and a hard-on that seemed like it would never go down. I fought off the urge each and every night to stroke my cock as I didn’t want to break my promise to Tonya. It also didn’t help matters that she would call me every day to check on me to make sure I wasn’t doing anything I wasn’t supposed to do. If I had done something I wasn’t supposed to do, she would definitely hear it in the tone of my voice. The last thing I wanted to do was disappoint this goddess that was in my home only two weeks earlier spanking my ass and grabbing my hard cock while directing me to suck each of the four guys’ cocks until they came in my mouth. Of course, the problem I had was every time I heard her voice, I would be reminded of that night. How incredible she looked when she was naked, leaning back on my sofa, playing with herself while watching Jennifer getting fucked by John. She would ask me with each phone call if I enjoyed the night with the guys and the previous weekend with her in charge. I couldn’t lie to her. I told her I truly did enjoy it. The first time she called me that week she said she had no idea John was bringing three other guys with him to my place. But, she said she was very proud of me and completely turned on that I was able to please each and every one of them multiple times. She would tell me that she wished she was there to have witnessed all the events that transpired that night. She knew exactly what she was doing with each phone call as she was tormenting me and causing my cock to grow to extreme proportions and yet, there would be no relief in sight.
It came to be Friday, in the early afternoon the week after the guys were at my house and I received a phone call from John. He had called to ask if everyone could come by on Saturday for the games and of course…another bet. He told me the girls would be there as well and Tonya would be coming along with them. I told him all of them were welcome anytime.
“Are the girls going to be deciding the fate of the loser or losers again?” I asked him.
“Yeah, I do believe we’re going to do that. I think they really enjoyed it and it gets them involved instead of just sitting idly by and watching.” He replied to me.
“Well, they certainly did a lot of watching last time they were here. Well, for the most part anyway.” I said back to him.
“Yeah, but you loved every minute of it. I’m not sure which you loved more…going down on all of us or having Tonya and Jennifer telling you what to do and who to do next.” John said back to me.
“I guess we’ll never know.” I said back to him half chuckling.
“Well, in any case, we’ll see you tomorrow. Later sexy ass.” John replied prior to hanging up the phone.
It seemed that ‘sexy ass’ was going to be my new nickname with the group since John, as well as Ted were now calling me that. It actually made me feel good about myself that they would consider me sexy. Of course, I would then wonder if it was just my ass they found sexy due to the name. In any case, I was happy with it and wasn’t about to complain about a nickname such as that.
Saturday was finally upon us and as usual, sl**p had evaded me the previous night. The dreams haunted me once more which caused a lack of sl**p, but it was more of the excitement of what was to come that evening. While I got everything ready in the house, as well as all the food and drinks, I was thinking about whether or not I would lose the bet on purpose. A part of me wanted to win so the girls would have to come up with something for all their boyfriends to do. But, there was the part of me that was actually turned on more at the thought of losing and being ‘punished’ in whatever manner the girls saw fit. I had resolved myself to losing that night as the excitement of not knowing what my punishment would be was more exciting.
Everyone started arriving around noon and as usual, they were all wearing shorts and t-shirts. The girls looked delicious in their skimpy little shorts and tank tops which most of them were wearing. Tonya had even gone so far as to wear a tank top that was super tight and had cut the neck down a bit further to reveal more of her ample cleavage and refused to wear a bra. The sight of her dressed in that fashion caused my cock to spring to full erection. When she noticed this she reached down and asked if she had caused such a stirring or if the guys had caused it. I told her that she was the cause of it. I told her that after two weeks of not being allowed to cum and then seeing her was certainly having an effect on me. She would just giggle and tell me that I was doing very good at refusing temptation and would soon be rewarded.
We settled in for the games during the afternoon and I assumed my position on the floor at Tonya’s feet. She did as she had done two weeks prior by dr****g her legs over my shoulders. My cock was in a constant state of arousal the entire afternoon and I could not focus on the football games at all. I couldn’t even tell which teams were playing and who was winning as I wasn’t paying attention. My mind was not on football but rather focused on pleasing this goddess of a woman and everyone else that was there. I was focusing more on ensuring that I would lose.
“So, we all betting on this game?” I heard John ask as his voice brought me out of my daydream.
“Sounds good to me.” Ted replied.
“Remember guys…us girls decide the fate of the loser.” Jennifer chimed in.
“Or losers.” I replied emphasizing the ‘s’ at the end of the world trying to show them all that I wasn’t trying to lose on purpose.
“Yeah, yeah, yeah. We’ll see about that.” Ted said back to me.
I focused my attention on the TV and recognized which teams were playing and knew which one should win. I knew this was my chance but I had to make it seem like I was trying to win and not lose.
“How about this?” I asked, “If my team wins, and they are a huge underdog, then the girls have to decide something for you guys to do not only tonight, but next week as well.”
“Oh no,” John shot back at me, “no way am I betting on that.”
“What are you worried about John? My team is at least a 20 point underdog. If we’re going to bet on this game then someone has to take the underdog. There has to be some kind of incentive or else there won’t be a bet.” I said back to him trying to make sense of the situation.
“He has a point John.” Tonya said from behind me.
“How about this,” Jennifer said in response, “If Mike wins, then you guys have to do whatever we want tonight and next week. But, Mike, if they win, you have to do something for the entire week and are released when we show up next weekend. Does that sound fair?”
“What the hell could I possibly do for an entire week? I’m not driving out anywhere to clean floors or anything like that.” I said back to her.
“We’ll come up with something easy and not too harsh.” Tonya said to me as she ran her fingers through my hair trying to entice me into agreeing.
I thought about it a few moments trying to give the impression that I was contemplating Jennifer’s idea. Inside I was wanting to immediately shout out that I accepted the terms of the wager. “Ok, I will agree to that. But on one condition…the guys have to start as soon as the game is over since this is an afternoon game and not wait until tonight to pay up. Plus, they have to continue doing whatever you want the rest of the day and night and then continue it as soon as everyone gets here next weekend until the end of the night game when the next bet is settled.”
“I think that’s fair.” Jennifer said. “What do you guys think?”
John looked at the other guys and they thought about it for a second or two and then finally nodded their heads in agreement. With the terms of the wager now set, we all settled in to watch the game. During the pre-game show, it was noted that the team I was betting on that day was a 21 point underdog. I decided to use this to my advantage to continue the ruse of trying to win. Even if my team had lost, as long as they covered the spread, then I would win the bet. I knew already they would not go for that as they would all complain that covering the spread was not part of the terms. I would finally have to agree with them, but like I said, I needed to make it appear like I was trying to win.
When the final whistle blew, my team had lost 14 points. I sat there smiling from ear to ear and trying to look all smug.
“What the hell are you smiling at Mike? You just lost. Or were you trying to lose on purpose.” Ted asked me.
“What are you talking about?” I responded angrily, “My team covered the spread. If I had bet money on this game in Vegas, I would have won. My team was a 21 point underdog and they lost by only 14. That means I win.”
“Oh hell no. Covering the spread was never mentioned at the beginning of the game when we set the terms. That should have been discussed.” John said back to me.
“It’s a given damn it. Anyone who has ever bet on sporting events, especially in Vegas knows that if a team loses a game, but covers the spread, anyone who bet on that team actually wins.” I said back to him trying to show him the error of his ways. All the while I was laughing inside as I knew this was playing out just like I wanted.
“I’m sorry Mike, but we weren’t betting money. It was just a win or lose bet. And John is right, there was nothing ever discussed about covering the spread when we set the terms.” Dana said back to me trying to defend John and Ted.
“Ok, ok, ok…I don’t want to argue and cause a fight. You’re right. We didn’t say anything about covering the spread at the beginning. I will admit to that if you all will agree that from now on whenever we bet, the spread is now a part of the wager.” I replied trying to make it seem like I was making peace.
“I’ll agree to that.” John said. “You guys ok with that?”
“Yeah, that sounds fair.” Ted replied as Dan and Simon just nodded in agreement.
“Ok. Now that we have that settled, what is it I have to do for the next week?” I asked.
The girls huddled together in the kitchen and I could hear Tonya and Jennifer leading the conversation as their voices were the only ones I heard until Tina, Dana, and Mary start laughing. When they finally returned to the living room, Jennifer stood over me smiling while Dana, Mary, and Tina joined their boyfriends on the sofa and loveseat. For some reason Tonya wasn’t with them.
“The first thing you need to do Mike, is stand up and strip off those clothes.” Jennifer ordered.
I did as she said and handed her my clothes. My hard cock was sticking straight out from my body. The head of my cock was a dark purple from not being allowed to cum for two weeks and having been erect for the entire afternoon. Once I was completely naked and handed Jennifer my clothes, Tonya then came back into the living room.
“What you have to do Mike,” Tonya started to say as she reached out her hand to give me something, “is that you have to wear these for the rest of the day. You will also have to go buy some more tomorrow to wear for the rest of the week. You will have lunch with me or someone else every day next week so that person can inspect and make sure you are living up to the terms of the bet.”
When I took the item from her hand, I then realized she was handing me a pair of panties.
“Well, put them on.” Tonya instructed me. “I want to see how they fit.”
I slid on the pair of light blue lace panties. The panties could not contain my hard cock as it stuck straight out from the top. They were not a size I could wear properly so they slid up in between my ass and caused my ass to poke out from both sides and the bottom. Tonya reached over and ran her fingers across my ass and the panties that I was now wearing.
“You will wear these the rest of the day and night and nothing else. You will serve us drinks and such the rest of the day. You won’t have to do anything else. Well, not exactly now that I think about it. You need to go to each person and allow them to see how those panties feel while they are on you. You will let them run their fingers across them as much as they want. They can fondle your ass, your cock, or both if they want. Oh, and when you and I have lunch on Monday, you will bring these back to me as I will want them back. You will bring them back freshly cleaned.” Tonya said to me smiling the whole time while continuing to run her fingers across my ass and then my cock restrained by those small panties. “I suggest you go somewhere tomorrow and get some to wear the rest of the week that actually fit properly.”
It was then I realized where Tonya had disappeared to when the other girls came back into the living room. She had stepped out of the kitchen or went around the corner to take these off and put her shorts back on. These were her panties that I was wearing. When I realized that I was wearing her panties, I nearly exploded right there in front of all of them without even touching my cock. I wasn’t sure if it was the excitement of wearing women’s panties and being paraded around in front of everyone while wearing them or if it was the fact they were Tonya’s panties that she had worn and was now without. Or it could be the fact that I now knew Tonya wasn’t wearing panties under her shorts. I didn’t realize it then, but I would have my answer to that question, along with all the other questions I had been posing to myself over the last couple of weeks.
I did as Tonya instructed and walked around the living room and stopped in front of each person so they could have a full inspection of my new attire for the day. The hands that roamed all over my ass and my cock constrained by those light blue panties was enough to make me cum right there on someone. As usual, my cock was aching to spew forth the vast amount of cum that had been built up over the last two weeks. My thoughts drifted to the previous weekend with all the guys and being tied up on the back deck. I started wondering what it would have been like to have been out there tied up wearing a pair of panties which they would pull to the side and fuck me. I would then catch myself having those thoughts and began to question what it was that was happening to me. I dismissed those thoughts and tried to focus on other things. I then started to look over my shoulder at Tonya and smile as she watched me getting fondled and listening to all the comments such as: “Such a nice ass in these panties.” Or “It feels so good rubbing on this cock through lace panties.”
Once everyone had their chance of fondling my ass and cock through the panties I was now wearing, I sat back down at Tonya’s feet. My cock was still fully erect and clearly visible out the top of the panties. I was then subjected to serving drinks and snacks for the rest of the night to everyone and each time I brought someone a drink or something to eat, they would have me stand there holding the drink while they fondled me again. Once they were satisfied, they would then take the drink and send me back to my place at Tonya’s feet. This same scenario played out the remainder of the night until I told Tonya that I needed to get in the kitchen and clean things up before everyone left for the night. She allowed me to go into the kitchen and clean up as I had requested. She joined me a few minutes later carrying her empty glass.
“You doing ok in here?” She asked me.
“Yeah, I’m doing ok. Did you need another drink?” I asked her.
“No, nothing more for me thanks. I think you need a drink though.” She said while rubbing my ass once more as I stood at the sink cleaning some of the glasses.
“No, I think I’ve had enough to drink tonight.” I said back to her.
“I wasn’t talking about an actual drink.” She said back to me as her hand slid around my waist and grasped my cock.
I let out a deep breath and closed my eyes as her fingers clinched tightly around my cock. She set the glass down on the counter next to me and then turned me around to face her. She slid her fingers into the waistband of the panties and pushed them down below my balls to expose my cock in its entirety. She then grasped my cock and began stroking it up and down. Pre-cum was dripping from the tip of my cock and was f***ed up and down my cock from the motion of her hand.
“I think two weeks is long enough to have waited to cum. I think you deserve a treat. Especially since you were so nice about the bet and gave in to the others even though I think you had a valid point and should have won.” She said while gazing into my eyes.
“Then why didn’t you say anything?” I asked her.
“Because I have plans for you and I wanted you to be wearing my panties. I wanted you to feel the lace against your skin while I stroked your cock. I planned all of this ahead of time in case you lost the bet. When I heard your argument about winning, I thought my plans for you were spoiled. Thankfully the others fought to keep the win and I was even more thankful that you agreed to what they said. I wanted to stroke your cock while you were wearing my panties. I want you to enjoy the feeling of the panties against your skin and sliding up your ass while you cum. I want you to associate having an orgasm with wearing panties. That way, whenever you wear some, your cock gets nice and hard for me or whomever it is that you are there to please that night.” She said back to me while continuing to stroke my cock.
“Oh, you dirty girl. I love it.” I said back to her smiling now understanding why she wanted me in the panties.
“Plus, I wanted to see your sexy ass in these panties anyway. I didn’t plan on stroking your cock until I saw you wearing them. Once I saw you wearing my panties and how hard your cock was once you had them on, my pussy started getting wet. It was all I could do to keep myself from playing with my pussy right there and then. The rest of the idea came to me while we were sitting around. I noticed that your cock never softened and I began to realize that you were enjoying wearing them.” She said back to me.
“Well, I think it’s the fact that they are your panties I have on which has me so turned on. But, it could be the simple fact that I’m wearing panties that has me turned on. I’m not sure which it is, but either one is fine with me.” I said back to her.
“So you like wearing them do you? I think you’re going to enjoy the next week then aren’t you?” She said back to me grinning and continuing to stroke my cock coaxing more pre-cum to drip from the tip.
I moaned with pleasure at her stroking my cock. The sheer fact that my cock was finally getting the attention it had been craving for the last two weeks was a relief. I ran my hands down her back and grabbed her ass. She immediately removed my hands from her ass and placed them on the countertop. I understood what she wanted me to do. She wanted me to stand there and just enjoy the feeling of her stroking my cock. My moaning was increasing and my breathing was labored. My eyes were shut as I enjoyed the sensation of her hands on my cock and the knowledge that she was going to allow me to cum. I grasped the countertop with my hands and bucked my hips forward. She knew I was about to cum and told me to just let go and cum. I did as she instructed and just as I started to cum, I felt something else bump into my cock. I didn’t care what it was at that moment. I was engrossed in the feeling of finally being allowed to cum, I paid no attention to anything else.
“That’s it sweetie. Shoot that load. I want it all honey. Damn, are you ever going to stop? You really needed this didn’t you?” She said to me as I continued exploding warm sweet cum from my cock. “Good boy.” She said once the hot cum had subsided from shooting out. “My god I’ve never seen so much cum at one time from one cock. You are certainly in for a treat now.”
Once I finally came back down from the exquisite feeling of finally having some release, I looked at her with a look of complete satisfaction on my face. I then asked her, “What do you mean I’m in for a treat?” At this point she held up the glass which contained all the hot cum I had just spewed forth from my cock. I instantly knew what it was she wanted me to do and I had no issue with doing that at all. She did allow me to cum after all and I would have done anything she wanted because she had given me such pleasure and satisfaction. She handed me the glass and I brought it up to my lips without any hesitation and tipped it back. I swallowed it down as it slid into my mouth and then slid my tongue into the glass as far as I could get it to go to try and clean the glass out completely. All the while, Tonya was still grasping my cock and stroking it. Not surprisingly, my cock never softened. It remained completely erect and Tonya used her fingers to wipe up the remnants of cum that was still trickling out of my cock and then brought them up to my mouth to suck clean.
“I hope you enjoyed that sweetheart. I want you to know how good it feels to play along with my ideas. You’re going to feel things and experience things you never knew possible.” She said to me as she withdrew her fingers from my mouth. She then reached down and pulled the panties back up as far as they would go which was not far enough to cover my hard cock by any stretch of the imagination.
We both went back into the living room and everyone was staring at us.
“What the hell were you two doing in there?” Jennifer asked.
“Just cleaning dishes and such.” I said back to her.
“I was about to think you were doing something more but since your cock is still rock hard I’m thinking you didn’t. What a pity.” She said back to me.
Tonya just laughed, spanked my pantie clad ass, and told me to sit back down. Not much longer after that, everyone said they had to get going. I put on my sandals and nothing else and e****ted each one out to their cars. Tonya smiled and then whispered into my ear that I did a good job at doing that without being told. Once everyone else had left and I was opening the door for Tonya to leave, she leaned in and kissed me and told me that I should meet her at one o’clock on Monday. She said that she would call me and tell me where to meet her and that I better not forget to bring her panties with me to give back to her. I told her I wouldn’t forget and then shut the car door once she was inside. She quickly rolled down the window and told me that I needed to keep those on all day tomorrow as well until I got new ones of my own and that I still wasn’t allowed to cum or play with my cock. She gave me a wink and rolled up the window just as I heard Jennifer saying from the front seat, “Come on. Give the guy a break. It’s been two weeks now.”
I slept so well that night after having finally been allowed to cum. But I could swear I could still feel Tonya’s fingers wrapped around my cock and stroking it. I still had the dreams I had been having, but this night I wasn’t constantly waking up in a cold sweat.
The next day I spent cleaning up the few remaining things from the previous night and did so wearing nothing at all but Tonya’s panties. My cock remained hard the entire time as I still pondered the question of whether it was the mere fact of wearing panties or the fact they were Tonya’s panties that had me so turned on and in a state of constant arousal. By mid-afternoon I decided to try and not ponder that question anymore and relax. My mind started wandering to where I could go to get panties and how could I get away with buying them? In order to get some that would fit me, I would probably have to get some that were a bit larger than what most women would wear. Either that or I could pretend that the woman I was buying them for was not a tiny woman but a curvy woman. I thought the last idea was the best and would utilize that when I went shopping the next day.
That Monday I awoke at my typical early hour and had breakfast and started thinking about where I could go to get my own sets of panties. I decided the best place to go would be the mall as I remember there was a Victoria’s Secret and a Frederick’s of Hollywood in there. I could always go into either one of those stores as there are guys going in there buying things for their girlfriends and wives all the time. I washed Tonya’s panties and put them on in case she called me to say that she wanted to meet earlier than what she had told me on Saturday. I couldn’t very well tell her that I didn’t go shopping on Sunday and not have any panties on. At least this way she would see that I was still owning up to the terms of the bet, but I would have to wait to get her panties back to her. I could also tell her that I enjoy wearing her panties so much that I didn’t want to give them back that day. It didn’t really matter at that point because I had now found myself approaching the entrance to the mall.
It was rather exciting walking around in the mall with a pair of panties on under my jeans. All these people around me in the mall had no idea what I was wearing. If they did know, how would they react? Would they be laughing? Would they be excited? Would they be disgusted? My cock stirred at the thought of it being the second idea of them being excited. My cock was straining against the lace fabric of Tonya’s panties and I decided to go into the first store I came to that I had thought of earlier in the morning.
The first store I came to was Frederick’s of Hollywood. I walked in and noticed the store was empty except for one woman standing behind the counter folding some clothes and preparing them to be put on display on the store. I smiled at her and said hello and began browsing the panties that were hanging up on the wall opposite the counter where the woman was. I had been browsing for a few minutes trying to decide what kind of material to get and what size I should get. I didn’t have a clue and had forgotten to see what size Tonya’s panties were that I had on so I would have an idea of what size I needed. I think the woman behind the counter, could sense my frustration and wonder and came over to me asking if I needed any help with anything.
“Actually…I do. I have no idea what size to get and what the differences are in the material and how they feel and all that. I don’t want to get something she won’t like.” I said to her. I thought that was rather ingenious of me as I wasn’t lying about anything. I truly wasn’t sure what Tonya would like to have me wearing and I really didn’t know what size to get that would fit me. “What kind do you prefer if you don’t mind me asking?”
“Well, it actually depends on the person and it also depends on where they are going to be wearing them. If it’s for everyday wear I suggest satin or maybe even cotton. If she likes feeling sexy all day and a bit naughty, then I would suggest a satin and lace mix or lace. Then of course you need to know what style she would like. Thong? Brazilian? French cut?”
“I had no idea this would be so difficult.” I said back to her. “I’m thinking something a bit naughty and risqué but also comfortable enough for everyday wear.”
“Then I think she might like these or even these.” She said to me as she pointed to a couple different pairs of panties.
I perused the panties she pointed out and saw some that I really liked and thought Tonya would really like me wearing as well. I still had no clue about size though. I finally decided that I would just tell this woman about the bet and laugh it off. I would act like it’s no big deal and hopefully she wouldn’t think I was a freak or something. Not to mention I’m sure they get all kinds in this store and there isn’t anything she hasn’t dealt with.
“Can I be completely honest with you?” I asked her.
“Sure. It would make the shopping easier.” She said back to me.
“Ok, here’s the deal. This past weekend a group of friends and I were all watching football games. We decided to bet on one of the games but it wasn’t a money bet. It was a loser does whatever the wants bet. But, just the guys would have to pay up and the girls would decide the fate of the loser.” I wasn’t about to tell her about the previous weekends so I tried to make it seem like a one-time event and then continued. “Well, as it so happens, I was the only one betting on one team and then the others used a technicality to say I lost the bet. The girls decided that I had to wear panties for the rest of the week. One of them gave me hers to wear that night and yesterday but I had to go buy my own as I have to give hers back to her today.”
Once she heard this story she burst out laughing uncontrollably. Thankfully she had the response I was hoping she would have to my plight.
“So you mean to tell me you’re wearing panties right now? Or do you have them balled up in your pocket to give to her later?” She said to me after looking around the store to make sure no one else was in there and would not hear what she was asking me.
“Yes, I have them on right now. They are a bit small though and I have no idea what size to get.” I said back to her.
“Would you mind if I took a look at the tag and see what size you have on so I know what size to give you?” She said to me smiling.
“That would actually be helpful. You don’t have a problem with that do you?” I asked her.
“Honey please…I’ve seen it all in here. This is the first time I heard about a bet having been lost and then having to wear panties. Are you sure you lost a bet and you’re not just telling me that so I don’t think anything strange about you?” She asked me.
“No, I’m serious. I lost a bet. I can actually give you a number to call to verify it if you want. This isn’t a natural thing for me. Besides, if it was a regular or natural thing for me, I wouldn’t be having so much trouble figuring out size and style and all that.” I said back to her trying to make her see the logic.
“Well, that is a good point. Ok. Come with me. We’ll go back here to the back where I can check the size of the ones you have on and then we can go from there.” She said as she e****ted me to the back of the store.
Once we got to the back of the store, I undid my jeans and allowed them to slide off my ass a bit so she could get a look at the tag. I didn’t allow them to drop all the way down, just far enough to where I thought she would be able to see the tag.
“Ummm…I hate to tell you this, but there’s no tag back here. Do they have the tag in the front?” She asked me.
“No, I don’t think so.” I said back to her.
“Well, that means we’ll just have to get you to try some on. I’ve never had a guy in here trying on panties before so this is a new experience for me. I hope you don’t mind if I get a little giddy at this.” She said back to me giggling.
“No. I don’t mind. I understand. I’m just thankful that you’re being so understanding about this. I wasn’t sure what I was going to do once I got on here.”
She looked me up and down and then said, “Ok, I think you would need a large.” She took some panties off the wall and handed them to me. “I think you might like the satin ones better as they are smooth and not so rough. I also think you would look good in a thong so try these on as well.”
“You think I’ll look good in a thong huh?” I asked her quizzically.
“Well, I did see your ass when I was looking for the tag. I have to admit…you do have a nice ass and I think you should show it off with a thong. But, a Brazilian would look good as well on you. Here, try these on and let me know what you think. Better yet…would you mind modeling them for me? You know, just in case I am ever in a situation like this again if someone else comes in having lost a bet?” She said laughing. “You aren’t shy are you?”
“No, I’m not shy. Besides, I think a woman’s opinion would be helpful and saying what looks good and what doesn’t.” I said back to her even though I was actually getting really turned on by the idea of a woman I didn’t know, eyeballing me in varying pairs of panties.
I went into the dressing room and slid the curtain closed. I purposely left it partially open so she could look in if she wanted but I acted like I didn’t know she could. I took off my shoes and jeans and then removed Tonya’s panties. I first tried on the thong she had handed me. I loved the feel of the thong and how it showed off my ass. The only problem I had was that it did nothing to contain my cock.
“Umm…I don’t think the thong will work.” I said to her from inside the dressing room.
“Why? What’s wrong?” She asked.
“Well, they’re not exactly ‘ideal’ for containing things in the front.” I said back to her.
“Well, that may be a problem with any that you get. Let’s have a look and see how bad it is.” She said as she slid the curtain to the side.
I was standing there in nothing but the thong as I had removed my shirt as well so I could get an idea of how it would look when I was walking around the house in front of everyone again. Once I heard her slide the curtain open, I spun around not expecting it. Her eyes instantly went straight to my cock which was hanging completely out of the thong. Her eyes widened at the sight of my erect cock and she had a hard time figuring out what to say.
“Ok. I…ummmm….I now see what the problem is. I think you’re too…too….large for a pair of panties. Unless you like letting it all hang out like that. I personally don’t have a problem with it.” She said to me stumbling over her words.
“I think I should try something else.” I said to her as I stood there with the curtain open and her staring at me and took off the thong. I was now standing there completely naked in front of this woman I didn’t know in a store where anyone could walk in and see what was going on if they came to the back of the store. I took the Brazilian cut panties and tried them on. They were a bit better, but still didn’t do enough to contain my cock.
“Well, I don’t think you will ever find a pair that will contain that thing.” She said still staring at my hard cock. “But I will say this pair makes your ass look fantastic. What about some boy shorts? Those would actually work well for you. Or perhaps some bikini style. Let me go get some others for you try on and see what you think.”
She quickly ran to the wall and as I watched her it looked like she was just randomly grabbing panties. She returned and handed me several different pairs to try on. At this point there was no need in closing the curtain and she stood there watching me as I tried on each pair of panties. She would say yes or no to each pair and the ones she said no to, she would toss off to the side to pick up later. Once we decided on the sizes for each style and we both were satisfied with them, it was now up to picking out the varying colors. I grabbed a black pair and a red pair of Brazilian panties, a bright red lace bikini style, white lace bikini, purple satin bikini style, two pairs of boy shorts one white and one purple both of which were lace, and then I decided to get one black thong just for the hell of it. I asked her if I could wear the black Brazilian pair out of the store as I had to give the blue lace ones back in less than an hour. She agreed and took the tags off and watched me put them on and then the rest of my clothes. Once I was dressed, she took the remainder of the panties to the register and rang everything up.
“I still can’t believe you lost a bet like that. I will admit though…you being willing to pay off a bet such as this says that you are definitely a person of your word. I admire you for that.” She said to me.
“Well, thank you.” I said back to her.
Once she finished ringing everything up and put it all in a bag and I had paid, she stopped me and said, “If you ever lose another bet and need anything, make sure you come here and see me. My name is Bethany and here is the number for the store. Make sure you call and find out if I’m working, and if not, when I will be working.”
“Uh, ok. Sure. I’m not sure anything like this will ever happen again, but one never knows.” I said to her smiling and then gave her a wink.
She smiled back at me and said goodbye as I walked out the store and back through the mall to get to my truck and leave to meet Tonya for lunch. I was contemplating on whether or not I should bring the bag in with me to show her what I bought. If anyone asked, I could just say that they were for her as a gift and I know she would play along with that. Besides, I wanted to show her what I got and tell her the entire story of my shopping experience. I knew she would get a good laugh out of it and enjoy the story.
I finally made it to the restaurant where I was meeting Tonya for lunch. I decided to bring the back in with me to show her the ‘goodies’ that I had bought earlier that morning. Not to mention, her blue lace panties were in the bag as well. When I got inside I saw that she had gotten a table back in the corner of the restaurant. I had a feeling she chose that table so that I could show her I was indeed wearing panties and not forfeiting the terms of the bet. I sat down next to her and leaned in to give her a kiss which she reciprocated and smiled. No sooner had I sat down at the table, she leaned in and whispered in my ear, “So, are you wearing any? Did you make it to the store and get some to wear for the rest of the week?”
“Actually…I am wearing a pair that I bought today and in the bag I have enough to last me for over a week.” I said back to her.
“Well, let’s take a look then. I want to see what you got.” She said to me grinning.
I quickly glanced around to make sure no one was watching and then undid my jeans and pulled them down to my knees. I showed off the black Brazilian style panties I was wearing before pulling my jeans back up. I then handed Tonya the bag and when she looked inside, her eyes got wide with amazement. She reached into the bag and pulled out the red lace bikini panties. She held them up and admired them and I could tell she was imagining me wearing them. She returned those to the bag and then proceeded to take each one out and admire it in the light before putting it back in the bag.
“You have done very well sweetie. I love these. I can’t wait to see you wearing each and every pair. But, I won’t get to see each one this week unfortunately. I trust you enough to know that you will live up to the terms of the bet. But, don’t be surprised if there is a surprise phone call telling you to go out and meet someone for lunch. That doesn’t mean you quickly throw on a pair just to wear out.” She instructed me.
“You should know me better than that.” I said back to her. “You know that I’ll be wearing a new pair every day and have them on all day.”
“Good. I’m glad to hear it.” She said back to me as she put the bag on the floor in between us.
Once we finished our lunch, I walked her out to her car. I opened the door for her and prior to her getting in, she wrapped her arms around and gave me a nice hug and kiss on the cheek.
“I would love to take another look at those panties you’re wearing. The light inside wasn’t very good and I didn’t get a good look.” She said whispering in my ear with her arms still wrapped around me.
I set the bag down on the ground and then looked around to see if anyone else was in the parking lot that could see us. I unbuttoned my jeans and peeled them open for her to see the black panties I was wearing.
“Oh come on. I need a better look than that.” She said back to me as she stood back a little bit.
I then proceeded to slide my jeans down my thighs to my knees. She instructed me to give her a little twirl so she could see my ass. I spun around slowly knowing that if I went too fast, she would have me do it again. As I turned, I could feel her fingers brushing against the fabric and then my skin. My cock instantly sprang to attention as I turned to face her and felt her fingers brush against my cock through the fabric.
“Oh, that reminds me…you aren’t allowed to cum for the rest of the week.” She said to me laughing. “I forgot to tell you that this weekend. I want you to build it up once again. Trust me, you won’t regret it.”
“Actually, you did tell me that. Remember? Jennifer even said that you should give me a break as it had already been two weeks. She didn’t know about the kitchen and what you did for me in there.” I said back to her.
“Oh yeah, that’s right.” She said before she kissed me one more time and got into her car. I pulled my jeans up and fastened them and then grabbed the bag of panties. I waved goodbye to her and then went back to my truck to leave. I drove back home with a full hard-on pressed against the panties. Was it the thought of not being allowed to cum again until she told me I could? Was it that she was in control and ordering me to wear panties all week? Or was it the mere fact of wearing the panties? My mind flashed back to the store and that of Bethany gazing at my erect cock poking through each pair of panties she had me try on. The feeling of her fingers brushing against my ass and under the panties as she adjusted them to fit just right caused my cock to start showing signs of pre-cum through my jeans. At this point I didn’t really care what it was. I was having a good time and experiencing things I never experienced before. I finally resolved to simply enjoy the moment and all the things that have happened and were yet to happen.
The rest of the week went fairly the same way as the previous weeks with the addition of wearing the panties. I was so turned on that I actually wore nothing but the panties during the day when doing things around the house. Anytime I went anywhere, my new panties were being worn under whatever clothes I wore that day. Each time I had to meet someone for lunch to prove that I was wearing them, I would get excited. I was excited at the thought of showing off the panties that I was wearing and wanting to see the reaction that person would have.
On Friday, Jennifer had called me to meet her for lunch. I was wearing the purple satin bikini style panties this day and knew that Jennifer would actually like them. I met her for lunch and she couldn’t stop smiling once she saw the purple panties I was wearing. I proceeded to tell her the events that transpired at Frederick’s of Hollywood to which her jaw dropped in shock as well as amazement. She giggled at the thought of me telling as well as showing someone else outside the group what I was willing to do. We talked for a while longer and discussed the facts that we needed to keep things somewhat confidential and contained within the group as best as possible. Little did I know, she was setting me up for later events and attempting to keep me at ease what with all the games her and Tonya were dreaming up for me. Unbeknownst to her however, I felt a little bit disappointed at the thought of keeping things hushed and confidential. It was the exhibitionist that was starting to come through again. I felt it at the store and then again in the restaurant with Tonya, then once again in the parking lot with Tonya and finally today with Jennifer as I showed her the purple panties I was wearing.
“Just so you know….Tonya and I have come up with a really good idea for whoever loses tomorrow. It’s going to be so much fun.” She finally said to me.
“You shouldn’t have told me that Jen. Saying it’s going to be so much fun makes me want to lose just so I could have fun.” I said back to her.
“It will be fun for us girls, not the loser.” She said with a wink.
My mind was racing with thoughts of what types of things I would have to do should I lose tomorrow. I found it difficult to focus on the conversation we were having and to this day I can’t remember what we talked about during the rest of our lunch together. When we finally finished our lunch and walked towards the parking lot, she told me that I should wear a pair of really sexy panties tomorrow and nothing else. She reminded me that the bet wasn’t over until a new winner was pronounced. I nodded in agreement and walked back to my truck with my cock pressed firmly against the panties under my pants. The rest of the night I continued to imagine all the things they would have planned for me and make me do should I lose. At the time though, I was unaware of exactly what Tonya and Jennifer had planned for me. I think they had an idea that I was losing on purpose and were taking full advantage of that fact. What had planned for me was the next stage of their plan to make me into something they wanted. Or was it that they were merely bring something out that lay dormant within me?