The Shopping Trip

My girlfriend Ashley has always been a little jealous of the time I spend feminizing men. Even though she knows there’s never any sex involved she resents the attention I give them and places I take them to. I’ve asked her to join me many times but she hasn’t been interested and doesn’t like the idea that they are getting off on this and she feels like its cheating. I finally had enough of these petty arguments and told her to come with me the next time and see exactly what it was all about. I had made plans with Gene for a shopping trip at a local mall and Ashley agreed to join us.

Gene is a thin, young man with long blonde hair and this was to be his first time dressing up and going out in public. I met Gene in the lingerie department of a new boutique and watched him explain to the salesgirls that he was looking for a present for his girlfriend. He was doing very well too. The girl was asking about his friends size and body type and amazingly they were almost the exact same size as his! They were looking at some really cute babydolls and I decided to walk over and give my opinion.

“That black one was is really pretty, do you think she’d like that?”
He was a little surprised but kept calm.
“Yes I do, she has some other ones just like it and I know she likes this style.”
“Do you buy her lingerie often, that’s so considerate, What’s her name?”
He apparently wasn’t as well prepared as he thought and looked confused. He started to blush and seemed to have lost the ability to speak.
I gave the girl a smile and we both knew.
“Are you buying this for yourself, because there’s nothing to be embarrassed about if you are. I think you’ll look adorable in this, maybe you should try it on.”
“I’ll be right back, I, I have to make a call.” And with that said he just about ran out of the store, he even forgot his jacket.
I was just starting to have fun and volunteered to find him and give it back.

I was walking towards the parking lot when I saw him by his car. He had left his keys in his jacket so he knew he had to come back and get them.
“I think you forgot something, did you make your call?”
“Oh thanks, I kind of lost it in there. How did you know?”
“Its a gift, I’m Teresa.”
“Hi, I’m Gene, would, uh you like to talk sometime? I, I, I can really use some help.”
“Sure Gene, I’ll let you buy me a cup of coffee if you have time.”
“That would be great, uh, Teresa, that would be great.”

We kept in touch after that and I told him about Ashley. He emailed me some pictures of himself and asked me if there was any way I could arrange for the three of us to go shopping together. He promised to buy us both a new dress if we would take him, and I said I’d see what I could do. Ashley was starting to become interested and I could see was going to go along with it although I suspected she had something else in the back of her mind. She was being too cool about everything.

“It will be fun Ash, and you can get that new outfit you’ve been talking about from Ann Taylor.”
“Will he really buy me that, its pretty expensive?”
“He’ll buy us whatever we ask for, this is a dream come true for him. So are you in?”
“OK, but first he takes us shopping, then we’ll see.”
“Deal, I’ll set it up for Saturday afternoon, you’re free right?”
“I’ll make sure I am.”

I called Gene and told him it was on. He had to wear what I gave him and do everything we said, and if that was alright we would meet him at the mall at 12:00 the next Saturday. I told him to make sure he was completely shaved, and I would bring something appropriate to shop in. He would be wearing panties and a bra, pantyhose, pink sweat pants, a pink T-shirt and sneakers. He agreed and said he was looking forward to it and thanked me over and over.

He was right on time and I introduced Ashley. She shook his hand and told him to go change in the bathroom. While we waited I could see how excited she was and asked her what she was thinking.
“I want to hold his car keys so he doesn’t get back out.”
“Just ask him hon, I told you he’ll do whatever we say.”
“I plan on testing that Teresa, but first lets go buy some new clothes!”

Gene came out looking a bit tense but with his leather jacket he really didn’t stand out that much. Ashley took his stuff and wanted to put it in the car.

“Why don’t you give me your keys Gene, we’ll be here for hours.”
Why, is that really necessary?”
“Give me the keys and start acting like a good girl or you’re on your own!”
Sure, OK, not a problem. I was just asking.”

While Ashley went outside I told Gene to relax and have fun. “How often do you get to go clothes shopping with 2 beautiful girls?”
Ashley came back with a big smile and patted Gene on the butt.
“Lets go shop Genie!”

We spent the next two hours at several different stores. First Ann Taylor For Ashley then Victoria’s Secret for me. Then we helped Gene buy himself all kinds of lingerie and a cute little red three-quarter sleeve pleated dress at Macy’s.

“Lets put this stuff in the car and go look at some earrings before we go.” Ashley announced.
She let Gene hold his new dress which he seemed so proud of. That was fine with me because I was getting tired and kind of bored with the whole thing. I really just wanted to show her how harmless these trips can be.

When we came back into the mall Ashley said she wanted to go to JC Penny which was right there. She led the way and I realized we had passed the jewelry section but followed her anyway.

“I need some conditioner, lets show Genie the salon here.”
The three of us walked in and were greeted with smiles all around.

“Hi Ash, you finally made it! We thought you made the whole thing up.”
“Girls, this is Genie! Are we on time?”
“Just right, but it turns out you didn’t need that appointment after all, we’re not very busy today.”

“What appointment?” I said having a good idea who it was for.
Lisa began to explain.
“Ashley made a reservation for her friend Genie for the works. Hair, makeup, manicure, and pedicure. We cant wait, why don’t you have a seat right here Genie and let us take a look at you.”

Gene looked at me like a scared rabbit, “What’s going on? We were about to go home.”

“Sit right here Genie, you asked us for help and we’re going to help you. Lets show them the new dress you bought.”

Ashley had planned it all out and planned it well. As she unwrapped the dress Gene looked at me for help and I just smiled.
You have to admit Gene that something has to be done with your hair, go try on the dress and lets all see how you look in it.”
“But Teresa, I cant do this, please lets go.”

“Isn’t this dress gorgeous? Here Genie, go change in the back, Lisa will show you where.”
“Please Ashley, don’t make me do this.”


He looked around the room and saw there was no way out of it, people had heard Ashley yelling and were starting to come over and see what was going on. Lisa took his hand and led him into the back room to change. He followed her like he was going to the electric chair.

When he finally came out he stood there in his new dress and stockings and didn’t move.

“Don’t worry Genie, I had the girls bring in some heels for you, I think you’ll find that those red pumps will fit you perfectly. Let me help you.”

Ashley sat him down in the nearest chair and the shoes completed the outfit nicely. Gene was as red as his dress and had a visible bulge that he couldn’t hide.

“What do you think girls, is she precious or what? Walk for us Genie, show everyone those sexy legs! I think that by the end of the day you’ll be absolutely stunning! Sit here and you can tell them what you want.”

Now it was my turn. “Why don’t you tell them what you told me. How you used to wear your mothers clothes when she wasn’t home, and that you’ve always wanted to be a girl. Go ahead honey, we wont laugh.”

Gene couldn’t talk, and just sat there staring into the mirror while they put the cape over him.

“What we were thinking ,is that she needs some highlights, right Teresa? And when you do her makeup maybe you could make her look like that picture in the window, smokey eyes, long lashes, and bright red lipstick. And her fingernails should definitely match the lipstick, don’t you agree Genie?

We waited to see what he would say and saw a few more people looking in after Ashley yelled again.


“Yes what Genie, ask them if they can do your hair and makeup and make you look pretty, go ahead.”

“please make me pretty”

“And you want them to paint your nails and pierce your ears and teach you to talk like a lady, right Genie?

Again Gene was speechless.


“please make me pretty, and money is no object.”

“Close enough, alright ladies she’s all yours. Teresa and I are going home. Like Genie said, do whatever you have to do to make her pretty.
Oh, and Genie, I’m going to leave your keys with security by the front doors. I’ll tell them you’ll be there in a few hours. Thanks for the clothes-it was a pleasure meeting you. We’ll have to do this again real soon. Bye girls, have fun!

I heard from Gene a couple of days later. He thanked me and asked if we were interested in another shopping trip. I told him I’d ask Ashley, and I would, eventually.

Leave a Comment

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out / Change )

Twitter picture

You are commenting using your Twitter account. Log Out / Change )

Facebook photo

You are commenting using your Facebook account. Log Out / Change )

Google+ photo

You are commenting using your Google+ account. Log Out / Change )

Connecting to %s