Recently I have started looking online for woman’s clothes that I could wear incognito. I am on the larger size so I was searching plus size stores when I found something on one of the websites. It was a black lace bandeau which seems to be a bra-like garment that you can wear without straps. It seemed very sexy and I thought, perfect, no straps and it should be tight enough that no one would notice.

I couldn’t order and have it shipped to the house for fear of getting caught by my family. Then I saw that they could ship it to the store. Maybe that would work, I thought, so I ordered it. A week or so later I got the notice that it had arrived. Going into a women’s store to buy something for myself was very exciting. That morning, as I got ready for work, I was feeling very feminine and couldn’t wait to go to the store.

I went to work for a few hours and then took an early lunch and went to the mall. I entered the store not long after it opened, hoping not many ladies would be there. I had only taken a few steps into the store when an associate came over and asked if I needed any help. She introduced herself as Rachel.

I said that I was pleased to meet her and I had an order that had come in. She said to follow her and so I did. We went toward the dressing rooms to an area that housed the online orders. She looked through the stack and found my package. She asked if I wanted to check to see if it was the item I ordered. I nodded and opened it up. When I pulled it out, she gave me a smile then asked if I wanted to try it on.

I said, “Really? I can do that?”

She said, “yes, the store isn’t busy and there won’t be any ladies in the dressing area for a little while.” She showed me a dressing room and after closing the door I took my shirt off in order to put the bandeau on. Once I had it on, I was looking at how I looked from every angle. It felt sexy to have an article of female clothing on.

About a minute later, she knocked and asked if everything was ok. I told her that I was good and didn’t need anything. After I looked at myself a little more I went ahead and put my shirt back on and stepped out, still wearing the bandeau.

“So how long I have been buying and wearing women’s clothes?” she asked.

“This is the first time that I had bought anything other than some panties.”

She then looked around the store. I was not sure what she was doing but then she turned to me and asked, “Do you want to try some things on? I am sure I can find something that you would like.”

Just that thought was making me hard. Since I didn’t give her an answer right away, I guess she took that as a yes and off she went. A few minutes later she handed me two dresses, one was quite long and one really short. I tried the long one on and loved the way it looked with a tight-fitting upper and the bottom that had light flowing material. It was white which I thought was very sexy and I loved the way it made me feel.

The short one was a little too short and showed too much of my manly legs. When I told Rachel that, she disappeared again and returned with some sexy lace leggings that she said would hide my legs. I put them on and they looked very sexy to me but I preferred the long dress so I took them off, thinking that I might come back another time to buy them. I told her that I liked the way the long dress made me feel.

“Hold on, I have something else I want you to try one.”

Soon she was handing me a pair of boy short panties that were pink with white polka dots. She said the color of the panties wouldn’t show through the white dress. That is something that I, being a man, had never thought about, whether you could see my underwear through my clothes.

I put them on and instantly my cock started growing. Rachel suggested that I take off the bandeau as the black lace would be able to be seen through the white dress. I decided that I was not going out in public so I didn’t need to take it off and so I left it on, under the white dress.

She asked me to step out of the dressing room.

“What? What if someone sees me?”

“There is no one in the store except the two of us.”

When I hesitated coming out she gave me that innocent, “please.” Opening the door very apprehensively, I looked around to see that the store was empty.

When I stepped out and she said, “Surprisingly, that looks really good on you.” That gave me a funny feeling inside. Then it hit me, she was trying to make a sale on a slow day.

The dress was touching the ground, so she walked around the corner and brought back a pair of colorful wedges with straps. No way, I thought. There is no way I could walk in those shoes. They were only about two to three inches, but I didn’t think I stood a chance, (pardon the pun) of being able to walk in them.

“Please try them on for me, pretty please,” she said in that sweet, innocent tone.

I sat down with my back to the dressing room and put the shoes on my feet. When I stood up I noticed that the color in the shoes really gave the white dress a spark. I asked her what she thought but she was nowhere around.

Then she came out of the backroom. That was weird, I thought. Why had she gone back there, I asked myself?

“Those shoes make you look even better.”

I stood in front of the mirror and thought, WOW, I like the way this dress looks. Now there is no way I would ever pass as a woman, but I thought I looked pretty damn good standing in front of the mirror with a white dress on with the colorful wedges. If you looked hard enough you could see the polka dots on the panties. And it made me hard knowing that I was in a women’s store with women’s clothes on.

Then I noticed that you could see my erection if you caught it at the right angle. I thought if I was ever to wear this in public that would be a problem but since I had no intention of doing that I didn’t worry about it as I was getting ready to go back into the dressing room to take it off.

About that time a lady walked in the store and Rachel said, “I need to go help her. Stay right there, I will be right back,” and away she went. I hurried back into the dressing room so as not to be seen. My clothes were not in the dressing room. Maybe I went to the wrong room, I thought, so I checked the next room. Nothing. I frantically checked all of them and nothing. Now I was freaking out. TOTALLY freaking out.

I waited until I saw the lady leave the store and then walked up as fast as I could in heels, which wasn’t very fast at all, up to the counter where Rachel was. I was so freaked out that I wasn’t thinking that I was wearing a dress and heels and in the middle of the mall store.

“Did you take my clothes and wallet?”

She said that someone had turned a wallet in and showed it to me.

“That’s mine!” I said loudly.

She looked inside and asked me what my name was, and I told her. She said she couldn’t give it to me without proof. What could I do? I couldn’t call the cops, that would be totally embarrassing. I told her that I had no proof because she had my ID.

“How did you get to the mall this morning?”

“I drove her in my truck.”

“Maybe if you could show me the registration and it matched then I could give you the wallet.”

What?

“How am I going to go to my truck without any clothes?”

“You have clothes on.”

“What are you talking about, I can’t go out there like this?” No matter how much I begged and pleaded with her she would not give me my wallet without the “proof” that was outside the mall. I had no other choice than to walk halfway through the mall to get to my truck, so off I went, apprehensively.

Walking in those heels wasn’t too hard when I was in the dressing area where I was surrounded by walls that I could hold on to, but now walking in the mall I was struggling, to say the least. I thought I was going to fall but didn’t, even though I came close three different times. Props to the ladies who wear heels every day without incident.

Finally, I made it to the outside without too much trouble although I did hear a little girl ask her mom, “why that man was wearing a dress?” Her mom changed the subject rather quickly as I passed them. Luckily, I have keyless entry or else I would have had to go back to the store to get the key. Once I found the registration I headed back in. On the way back in there were a few teenage boys that were calling me all kinds of names. Just let it go and get back inside, I kept telling myself.

By now the new shoes were getting uncomfortable. I had no choice, so I kept going. Then I saw the store, I made it, I thought. Then I looked up and saw something that sent a chill down my back. It was my coworker, Rick. Oh, crap!

I made a quick right turn and almost fell off the heels. He didn’t see me or at least I hope he didn’t. I watched him until I thought it was safe and then made my way back into the store.

I can finally get this ordeal over, I thought as I walked into the store. I looked around the store but didn’t see Rachel. Then a voice from my left startled me when she said,

“My name is Jessica; can I help you?” she said as she looked me up one side and down the other.

“I need to see Rachel.”

“Rachel has gone on her break to the food court.”

“Great, just what I needed. I guess I will have to wait until her break ended.”

“You must be Mark, Rachel said you would be looking for her. She said to tell you to meet her in the food court.”

“No, I will just wait until she gets back. “

“Rachel said you might say that. She also said to tell you that if you didn’t come out there she might forget or misplace the items she has for you. You may just want to go out there to get it.”

I was screwed. Did I want to walk out into the food court in a dress? Hell, no. Did I want my wallet to go missing? No. What else could I do, call the cops? And be made the fool? No. I decided the best and quickest way to get this over with was to humiliate myself and walk out there. I checked my watch, it was 12:30.

“Great! The food court will be full of people eating lunch,” I said as I headed out of the store and made my way to the food court.

As I approached the food court I could see Rachel. She was sitting in the dead center of the area, surrounded by people. I think she sat there on purpose to make me walk by all those people. By now I was getting a little angry, to say the least.

I had almost gotten to her table when a scrawny teenage jerk slid a chair in front of me and I caught my foot on it causing me to stumble, which made me knock a few empty chairs around, making all kinds of noise. Everyone, or least it seemed like everyone, turned around to see what was happening. I was about fifty shades of red. I finally regained my composure and sat down at the table to put my head down.

“I have humiliated myself by coming out here, are you happy? Can I please have my wallet and put an end to this game?”

“Calm down, everything is going to be all right.”

I was fuming and said, “how can you say that? I am a man, in a dress, in the middle of the mall food court.” I was trying not to be too loud but I wanted her to know that I was done with this fiasco.

“Has anyone you know seen you? If not, then these are just a lot of random people that you will never see again.”

That didn’t make me feel better, whatsoever. After a few moments of silence, she told me to look at the guy two tables over. “Do you think he is nice looking?” she asked.

“What? What guy?” I asked.

“The guy with the muscles bulging out of his royal blue shirt.”

I finally figured out who she was talking about. “Yeah, I guess he looks good.”

“Can you imagine being with him?”

“What?!”

“Can you imagine being with him, you know, like boyfriend and boyfriend?”

“What are you talking about, I never said I was gay.”

“You are sitting in the mall food court with a dress on, are you not?”

“That’s different, I was tricked.”

“No one tricked you into putting that dress on, did they?”

“Can we just go back to the store so I can get my things and get out of here?”

She was still on her break and in no hurry to get back to work so she said that we could just sit and chat for a little while. I was getting so mad that my emotions took over and my eyes started to tear up. Then a tear rolled down my cheek.

“Are you crying? Why are you crying?” She said it so loud that a few people turned around to look at me.

I wanted to die right there. The embarrassment didn’t help to stop the tears so I started wiping my eyes. We sat there for another ten to fifteen minutes with her doing most of the talking. Then she said she had to go back to work.

“Finally!”

“Oh no, not you. You need to sit here for another half hour before you come to the store. I don’t want my coworker to think we have a thing going on.”

I was flabbergasted. Ok, I will play along, I thought, it is only another thirty minutes.

Two minutes after she left, a middle-aged woman came and sat at the table with me. She took hold of my hand and said, “you don’t have to take that from her. I am sure you could do better than that.” It was then that I realized she thought we were a couple and that Rachel was the dominant one who was abusive.

I didn’t know what to say to this woman so I just stared at her. Then my eyes started watering again and tears rolled down my face. She got up, gave me a hug, “think about what I said, you can do better.” Then she walked away.

Could things get any more humiliating?

Looking at the clock on the wall I saw that I still had twenty minutes to wait so I sat with my head down on the table, trying to hide my face. Fifteen more minutes. Ten more minutes. Five more and this can be over, I thought. As I stood up to head back to the store, I heard a familiar voice behind me.

"Mark?" I turned around to see my coworker Rick standing two feet from me. There was no hiding, so I just sat back down. He sat next to me and we started talking about the way I was dressed and why. I was so embarrassed but I told him the whole story. He could see how embarrassed I was by how red my face was.

“Mark, you have nothing to worry about, I will not tell anyone what I have seen.” I thanked him and told him that I had to go.

“I need to stop by a store on the way out and get back to work.”

“I am not in a hurry, I will walk with you.”

That was the last thing I wanted and tried to talk him out of it. I just wanted to get to the store, get my stuff, changed clothes and get the hell out of there.

He insisted that he should go with me to protect me, after all, I was a single lady in a dress with heels on.

“Whatever,” was my reply and we started towards the store. We were getting weird looks as we walked out of the food court. Funny thing is that even though it was humiliating to me, he didn’t seem to be bothered by it., but then he wasn’t the one in the dress.

Once we got to the store, I told him he could wait outside and then walked in. He didn’t listen to me and was two steps behind me.

I looked and saw Rachel who was waiting on a customer so I waited, acting nonchalantly by looking through the racks of dresses. To my surprise, I saw one that was really pretty and pulled it out to get a better look at. It was a long red dress with pretty flowers on it.

“That dress would look great on you,” Rick said. It startled me and so I immediately put it back. I didn’t even realize he had come into the store. Time seemed to stand still as I waited for Rachel to finish.

Finally, she finished with her customer and asked if she could help me, as if I was a new customer who just walked in the door.

“I am here for my clothes and wallet.”

“Oh yeah, that is right, someone turned in your wallet. Did you get the registration?”

I was starting to breathe fire when Rick stepped in and took the registration out of my hand and politely gave it to Rachel.

She looked at it and then my driver’s license and said, “Yep, that is yours. Here you go.”

I asked about my clothing in a less than friendly voice and she just stared at me. Rick then stepped up and asked her politely about getting my clothes. She smiled at him and said that she had found some clothes in one of the dressing rooms and put them in the back. So away she went, leaving Rick and I standing there at the counter.

I leaned over and told Rick, “thank you for your help, I owe you one.”

“It is my pleasure,” he said.

When she returned with a bag of clothes and shoes I snatched them from her and headed to the dressing room.

“Excuse me, sir, she said, the dressing rooms are for ladies only.”

I was about to go off on her when Rick stepped in to defuse the situation.

Rachel looked me in the eye and said, “if you acted more like your boyfriend then maybe people would be nicer to you.”

My boyfriend?! Did she say, my boyfriend?

Rick could tell that I was at the end of my rope and put his arm around me and guided me out the door.

As we walked in the mall I stumbled in the heels and Rick caught me. He then put his arm around me so that I wouldn’t trip again. I told him that I could walk by myself and no sooner had those words left my mouth, I tripped yet again.

He said," I think it is in your best interest that I have my arm around you to help you steady yourself in those heels."

Realizing that he was probably right, I said, "ok," not wanting to fall flat on my face. And if I fell then it would draw more attention to me as well as get the white dress dirty.

After a few steps, I could really feel Rick’s strong arm around me holding me tight and it started to feel nice. Then I felt my cock starting to get hard. Oh no, he can’t see that, I thought and did my best to walk in a way that he couldn’t see it. I am not sure if he could tell that I had an erection, that would just add to the embarrassment.

We walked along with our arms around each other toward the parking lot. A couple of times I heard some less than nice comments as we walked close.

Then he said something that surprised me, “So what do you think about what Rachel said?”

“What did Rachel say?”

“She said something about me being your boyfriend. Would you like for me to be your boyfriend? I think you look good in that dress and I wouldn’t mind seeing you in other dresses, Like the red one you pulled out at the store. And who knows, maybe some lingerie?”

My mind was blown.

Here is the one guy in our office who could have any woman he wanted, and he is asking me if I wanted him to be my boyfriend.

I didn’t know what to say so we kept walking. He could sense that my mind was spinning, and not wanting me to fall he stopped and sat me down on a cushioned bench. He looked me in the eye and said

“I am serious. Would you like me to be your boyfriend?”

Never before had I thought that I was gay but here I was, at the mall, in a dress, in front of a man’s man, who was asking to be my boyfriend.

Then I heard words come out of my mouth that I never thought I would speak. “Yes, Rick, I would love for you to be my boyfriend.”

With that, he leaned over and pressed his lips to mine and kissed me.