Chapter 5

After we all had some coffee, Patty and Lena carried my clothes outside. I had no idea what they had planned, but once outside, I was handed the black thigh high stockings and was told to put them on.

They had moved the chair toward the top of the steps and I had to sit there in view of whoever came by and put girl’s stockings on. Once I had them on, Lena said, “Can we have him go like this? He can finish dressing before we get to where we are going.”

Patty thought about it and said, “Yes, that might be good Lena. I’ll drive and he can sit between us so we can play on the way. Don, let’s go.”

I followed them down the stairs and watched as Patty got in, then I had to slide in from the passenger side. I got I and slid over to the middle to sit next to Patty while Lena got in. She reached for my cock immediately, but Patty had her hand on it already. My other clothes were put in the back seat.

Once we were all in, Patty let go of my cock so she could drive and Lena took over holding my cock. Patty told her not to make me cum, but wanted her to keep me hard. I had no idea where we were going, but figured I would be exposed more before the day was over.

We drove for a while and Patty pulled into one of those drive through places to get us some breakfast to eat while we traveled. We each got a couple sausage, egg and cheese biscuits and we were off again. I don’t think anyone at the drive through saw I was half naked, but if they did, nothing was said.

While Patty drove us to the destination, we ate and Lena played with my cock, keeping me hard, but not allowing me to cum. It was torture for me, but I enjoyed having her hand on me. Most of the time she just held it in her hand, but occasionally, she would stroke it a few times.

Patty saw a place to pull over and when she stopped, Lena got out and told me to get out and get in the back seat. Once I was there, and Lena had returned to the front, Patty started driving again. Lena turned to me and said, “We want you to get dressed now and don’t forget your panties.”

They both laughed at that. Guys don’t wear panties, but since they are in charge of me, I wear them all the time now. I pulled the panties on and then finished dressing with a button up shirt and pair of pants. I was dressed and put my shoes back on.

It wasn’t long and I found out where we were going. Patty pulled into a small shopping center and parked. She turned to me and said, “I expect you to do everything we say today, no matter what it is. You said you enjoy humiliation, so today we will humiliate you as much as we can. If you want to stop playing, just tell us and we won’t do any more with you. The games will stop forever.”

I said, “No, I have asked for that and will do as you and Lena want. I don’t want to stop allowing the 2 of you to use me for your pleasure. I don’t know what you have planned, but I’m ready to play.”

“Good, so let’s go have some fun.” She said to us.

We all got out of the car and walked toward the stores. I wasn’t sure why we were here and not shopping closer to home, but figured there was a good reason for it. I should have asked why, but knew neither one would tell me, so just walked with them toward one of the shops.

I wasn’t paying too much attention to what store we were heading for because Lena was talking with me and my mind was on her. I didn’t notice the store we went into until we were inside. Patty said, “Lena, you and Don go look around. I need to talk to the clerk for a moment and will join you soon.”

I walked with Lena, who was holding my hand now and all I saw was girl’s clothing. I figured they were getting themselves some new clothes and just went with the flow. Lena saw some skirts and blouses she liked and asked me if I liked them. I told they were nice, so she had me carry them for her while she continued looking around.

She had given me 2 skirts and 2 blouses and all of them were pretty. I thought they would look good on her. She doesn’t normally wear things like that so I figured she was going to start dressing up more. We walked some more as she started looking at dresses.

Patty joined us shortly after and she said, “We won’t have a problem doing what we wanted Lena. What did you find?”

Lena had me show Patty the clothes she had picked out and Patty agreed that they were the right ones. They both looked at some dresses and Patty picked out one that was red and Lena found one that was pink. They both said they were perfect.

Then Lena found a little black dress with a gold zipper up the front. The zipper went from the top to the bottom. I liked it and told them I did. Patty said, “Good, we will get it.”

Then, they led me to the back where the dressing rooms are and I figured they would try on the clothes and decide if they would get them or not. but, I soon found out that they had something different in mind.

Patty looked around and said, “The clerk has no problem if we don’t use the rooms, as long as we are back here and not in view of the front of the store. You ready Lena?”

She said “Yes, let’s do it.”

I figured she would remove her clothes and try them on while we watched her, but that is not what happened. Patty then said, “Don, we need to take off your shirt, pants and shoes so you can try on these new clothes.”

My heart stopped beating and I thought this was the end of the world for me. They were going to make me show my stockings and panties in a public store, plus I was going to be putting girl’s clothes on. This is not right, but if I don’t, then the games will stop and I’ll never get everything I want.

So, as I stood there in view of anyone looking, I removed my clothes and handed them to Patty. Once I had those off, the clerk came back and said, “I like that. Mind if I watch the rest of the show. No one else is here, so I don’t have to be up front.”

Patty said, “Not a problem. You can give your opinion too.”

Lena then handed me one of the skirts and a blouse. I had no other choice, except to put them on. I never thought about wearing girl’s clothes before, but for some reason, I was getting excited and my cock was getting hard.

Lena said, “Wait before you put them on Mr. Don.” Then she looked at the clerk and asked, “You want to see what this is doing to him?”

The clerk said “Of course.”

Then Lena said, “Pull your panties down so she can see what the humiliation does to your cock.

I did as she instructed and once again, someone new was looking at my hard cock. And she as able to see more of it now, because there was no hair around it. Once she saw it I was told to pull my panties back up and try on the clothes.

I put the skirt and blouse on and was told to walk around so they could see me better. I did as they said and when I got back, I was told to take those off and put on the other one. I changed to the other skirt and blouse and modeled them for the 3 girls. The first skirt was about knee length but this one was a mini skirt and showed more of my legs. It was almost to the top of the stockings.

They liked that too and I had to try on the dresses next. I put the red one on, followed by the pink one. They all agreed they looked good on me. Then, I had to put the little black dress on.

Once I had it on and zipped up, all of them loved it and Patty said, “If we cut the tag off, can he wear it home?”

The clerk said, “I will allow that, but I want to see that cock again. Really, I would like to see him naked if you don’t mind.”

Patty said “That is not a problem, but he can’t have sex. We can’t stay to long because we have a few more places to take him. But we have time for him to get naked for you.”

Lena giggled and said, “Mr. Don, get naked for the nice lady and let her see what we see all the time.”

I had no other choice because if I said no, we would leave and go home and they would never play games with me again and I wanted more of what they were doing with me. So, I took the dress off, followed by my panties and then the stockings they made me wear.

Once naked, I stood before the clerk and she had a good look at all of me. Being hairless like I was, everything seemed to show more. She just looked and then got her phone out and snapped a couple pictures of me. She said, “I don’t think anyone will believe what you all did today, so need some proof.”

Patty said, “That’s ok, he doesn’t mind. Would you like a picture with my husband?”

“Sure, then everyone will know what I saw is true.” She said.

Patty took her phone and had the clerk stand right next to me and she snapped a few pictures. Then she said, “Got an idea. Why don’t you hold his cock and I’ll get pictures of you doing it?”

Well, that’s all it took for the clerk to reach out and grab my cock. It twitched when she first touched it, but it did feel good. Patty took several more pictures of the clerk holding my cock as I stood naked next to her. She was completely dressed and I was completely naked.

Once they finished with the pictures, the clerk said, if you want, I’ll take whatever clothes you want up to the counter and ring them up. I’ll bring the black dress back without the tags and he can get dressed so you can take him wherever you planned.”

Patty said, “That will be good. Thank you. Don, start putting your stocking and panties on.”

The clerk left and I started getting redressed. I didn’t see what other clothes they were getting and only knew of the black dress, which they say I will wear out of here and into some other public stores. It will be very humiliating to walk around in public dressed as a girl. Everyone would know I was a guy dressed as a girl, but that is what they wanted today. I wondered how many other times I will have to be dressed as a girl.

I had finished putting the stockings and panties on when the clerk came back and handed me the black dress. I took it and put it on, zipped it up and then put my shoes on. I looked foolish, or thought I did anyway.

Lena then said, “Mr. Don, you are one hot girl today. That dress is perfect for you, but you need to have some nice shoes to go with it. Is there a shoe store near here?”

The clerk said, “Yes there is. It is about 3 doors down and I know the girl in there. I’ll call her and let her know you are coming in and what to expect.”

Patty said, “Thank you. If we ever make it back this way, we will look you up and maybe my husband might want to lick you. Would you enjoy that?”

“I sure would. Anything else I could get from him?” The clerk asked.

Patty said, “Well for right now I allow him to go down on some girls and maybe give him a blow job, but no sex with anyone but me. Doing oral, isn’t considered sex, at least that’s what one of our presidents said.”

Lena and the clerk both giggled and Lena said, “I’ll have to remember that Ms. Patty, just in case some boy wants something from me. But we should be going now so we can finish our shopping. I’m getting hungry too.”

Well, it looks like I will be taken to get some new girl shoes and whatever else they want me to have and it sounds like we will be getting something to eat soon. I just hope it is from a drive through and not a sit-down restaurant. But, I’ll will go and do whatever pleases them.

We left the store and walked down to the shoe store. As soon as we walked in, a girl greeted us and said, “Damn, I didn’t believe Carol when she said a guy in girl’s clothes would be in,

but, here you are. How can I help you?”

Lena spoke up and said, “Our boy here, needs some nice shoes to go with his dress. I think maybe a nice pair of lady’s heels. The heel should only be a bout 2 inches because he hasn’t learned how to wear them yet.”

This girl looked shocked about the request and then Patty added, “I also want to try a pair with a higher heel. That way, he can work up to wearing them to get used to having them on his feet.”

The clerk said, “Ok, what size does he wear. Never mind, I’ll measure his feet and get the right ones for him. Would you want a 3 or 4-inch heel with the others?”

Patty thought about and asked Lena, “So, what do you think Lena? Maybe a nice pair of both the 3 and 4.”

Lena said, “I think both would be good. We can get him started with the 2 inch today and later have him practice with the others.”

“Very good. We will get 3 pair today.” Patty told the girl.

The young girl said, “That is good. I have his size and will be right back.”

She left and Patty said, “So Don, are you getting what you wanted? Have we humiliated you enough today or do you want more. Be careful how you answer.”

I thought it over and even if I had been humiliated beyond my expectations, I was thinking more would be good. No one has ever done anything like this with me before. So, I said, “Well, even if I am totally embarrassed by all of this, I am curious as to what else you might make me do today. So, yes, I want to continue.”

By then the girl was back with a bunch of boxes and nothing more was said. I took my shoes off and the girl put the 2 inch heels on me and they fit good. Then I had to stand up and walk in them and that was the hard part. I almost fell down, and the clerk said, “Wait, sit back down and take those off. I’ll be right back.”

When she came back this time she had some other shoes. She put them on my feet and even if they were 2 inch heels it was easier to walk in them. These had a platform for the heel instead of the spike like the other ones.

I walked around in them and they all thought these were great and I could work up to wearing the other ones at home.

So, they were all paid for and I wore the new 2 inch heels out of the store. Patty said, “Almost done with the makeover. We just need a nice little purse since he can’t carry his keys and wallet in that.”

Lena added, “Yes, and maybe a little makeup so he looks more the part.”

They saw another shop not far from the shoe store and decided we should go in there. I followed them into the store and it carried a lot of things. It was more like a store I would shop in, but I wouldn’t be there in a dress and heels. They promised humiliation today and they are doing great giving it to me.

Inside the store, they found the ladies section and then the purses. They liked a lot of them and made me hold them to see how they looked. They went through about 6 purses before they found the right one. I had to carry it to the check out and pay for it. But on the way, we stopped at the makeup aisle.

They knew just what they wanted so, I had no say in what they got for me. They picked up some things to put on my face and something for my eyebrows, but I had no clue what they were called. Hell, I never put any kind of makeup on. I thought I looked good enough without having to cover anything up. Then they went to the lipstick area and picked out a bright red tube.