Calvin was afraid as he walked into a store and looked around. He was a guy so he wasn’t sure what he was doing, but he was determined to do it. He braced himself as he saw an assistant approached him saying, “May I help you sir?”

“Yes, I need a dress.” He was deliberately being vague. He knew he would have to say it sooner or later.

“There are many fine dresses and gowns here. Do you know her size?” It was annoying work especially when a guy came in trying to buy a nice gown or dress for his girlfriend. They often didn’t know their girlfriends size and it made her work far more difficult and frustrating. She hoped this young man knew something that could help her find the right dress for her.

He smiled, decided to stop being afraid. If he was going to do this then he needed to do it. It was his choice after all. If he was going to blush and be a coward about it, he may as well walk away. He looked right into the woman s eyes, smiled softly and said, “You don't misunderstand ma'am. I want the dress for me. I have no clue about these sizes so I need help with finding a dress that will fit me and look beautiful. I usually wear a size 36 to 38 jeans, extra large tops. As you see, I am large and very athletic. I do wrestling and boxing. So can you help me?”

She kept her professional outlook and smiled softly back. So this young man was one of those. She had helped them too. Crossdressers or beginners who wanted to try it. “Alright sir, lets get some measurements and then process from there. Follow me to the dressing rooms.

This was one of the reasons he went here. High class stores like this usually had people willing to help and not judge or laugh at him. He needed someone who could help him find what he wanted. He took off his clothes and she took some measurements of his chest and hips and legs. Then she asked him, “Do you know what kind of dress you want?”

“What do you mean,” He asked her.

“Sir, do you want a gown, something like for a date, evening to look good and facy. Or something for the every day to wear casually?”

That was a question. This was going to be his big day so he decided to go all out. “I want something fancy and beautiful. Very formal if you don’t mind. I want to be stunning for her?”

Now she was wondering what was going on. Was he dating a woman that put him up to this? It was none of her business so she said, “We have many formal gowns here. Do you know what kind of gown you want to wear?”

“Um, let me see them. What kinds are there?”

This was the frustrating part of her job now. “Do you want a ball gown, princess, Empire, Sheek, Lace, Chiffon, baby doll, Halter, one shoulder, sleeves or sleevless?”

He looked bewildered by the choices. She almost laughed but held it in check. This was most obviously his first shopping trip for a dress. She said gently, “lets go examine your choices and go from there.” They went to the formal gowns and she showed him the selections and carefully told him of the differences between an empire gown and a princess gown. What a chiffon and baby doll were and how they all worked. They were all so beautiful he didn’t know which one to choose. But eventually he choose the sheek look. A pink gown that clung to all of the curves he didn’t have. It was a full length gown. It was over four hundred dollars and he wasn’t done yet. “Now I think I need some heels.”

She tried to talk him out of it when he chose a pair of six inch spiked stilettos. She said, “We never wear those. Wouldn’t you prefer these more comfortable four inch.”

He was adamant and said, “No that is alright.”

She smirked and let him have the six inch. He would learn the hard way. That was alright, many teenage girls had to also learn the hard way when moving up to wearing heels. They were too hard headed to take their mothers warning and tried wearing six inch heels for long periods of time just to look sexy and grown up. They paid for it and realized to heed their mothers warning. Obviously this man didn’t have a mother who decided to teach her son about wearing heels and stuff she would teach a daughter. He would have to learn it all on his own. He finished the trip with buying another paid of heels, a red and black peep toe six inch heels. “Thank you, I will be beautiful.” The young man walked out and she was just wondering what was going on. He had obviously prepared for it. He tried to move femininely and didn’t really do a good job of it. He was trying to move his hips and do gentle gestures of a woman. He had a man’s hair but he looked like he was growing it out and trying to make it more womanly.

Calvin headed toward a lingerie store now for some sexy undergarments. If buying a few formal gowns was embarrassing, this would be worse. He boldly walked in and looked at everything. He walked along the aisles trying to decide what he needed. He got a few undergarments already to wear under his gown, but he wanted something very sexy now.

He looked at the panties and bras. He decided he wanted one of the thongs and then looked at the bras. He wanted something more like women wore under a beautiful gown when their trying to be very sexy. Something like, that. A teddy with garter straps hanging down and he would probably need a waist clincher to give him a more feminine shape.

He approached a store attendant and said, “I need help choosing one of these. Can you help me find my size.” He blushed as she looked at him and told him to follow her. She measured his chest and bust area and they found the proper size.

She told him gently, “Don’t be embarrassed sir, many men do this.”

He smiled and nodded and selected five different thongs and panties and then chose some stockings to wear. Now he needed some cosmetics and jewelry.

He went to Macys and loaded up on cosmetics. Calivin was bewildered by the selection of nail polishes, foundations, lipsticks, moisturizers, cake creams, cold creams, blushes, mascaras, eye shadows, lip gloss, and eyebrow pencils. He found a few websites that explained makeup to him so he selected the ones he thought best suited him. Then he bought some bracelets, some rings, earrings, and a necklaces. In all, he spent nearly 900 dollars that day and went home to try them all on.

He bathed in some soft back oil to moisturize his body and the shaved his whole body down as good as he could. Then he did his nails. Following the directions on a woman’s website to help him with nail maintenance. Calvin polished his nails carefully. He primed it, sanded the edges and put a primer coat on then a bright red coating to finish his toenails. Each toenail was separated with a soft foam separator as he proceeded to do his fingernails next. He sat and let it dry before he dressed himself. The tight waist clincher went first and he struggled to trim at least three inches off his waist. He tied it and then put on his sexy pink teddy and slowly rolled the stockings up his leg and attached it to the garter straps. He carefully stepped into his beautiful evening gown and posed. Calvin was not yet finished.

He had to do his face now. He had already shaved his face down so now he put a soft moisturizer cream on first and then a heavy coat of foundation cream. He did his best to cover the creases in his face. Then he applied the eye shadow. He put on a heavy lilac color on his eyelids and heavy eye eyeliner and some false eyelashes finished his eyes. He applied a heavy red coat of lip gloss and blush.

He posed and figured he was as good as he could look. He made the phone call and a woman’s voice answered.

“Hello Angie. I miss you my love.”

“Oh Hi Calvin. I was just thinking about you this morning. I love you.”

“I love you too, Can you come over now. I want to see you so bad.”

“Sure, I just got off from work. Do you mean right now?

“Yes, I cant wait. Please,” He pleaded and she agreed.

He just sat in the recliner and waited for his girlfriend of two years to arrive. She only lived fifteen minutes away so he waited. He heard her car pull into his driveway and her heels taping on the walkway up to his house. She knocked and he stood up in the doorway trying a feminine pose as he said come in.

She walked in, looked at her boyfriend. She looked bewildered and said, “Calvin, what the hell is this!”

“what,” he said innocently. “Don’t you think I am beautiful?

She thought for about ten seconds and said, “No you look stupid. What are you doing?”

“I want to look beautiful like a woman. What’s wrong with that? Cant a guy try to find his feminine side. I was hoping we could go to the hair salon to get my hair styled. I cant do that on my own,” He said challenging.

“No, you look stupid. Your foundation is all wrong, your colors don’t match. You obviously didn’t shave very well for the foundation to cover. And what is up with that grown. Pink. Sorry, Calvin. You don’t look like a woman, you look like a sissified man trying. Lets clean it all off and I will help you. You look like an idiot, sorry calvin. Lets do it again together and then we can get your hair styled. How do you want it?”

“I was thinking, curls. A beautiful updue. What do you think?”

She sighed, “Well of course. That’s going to take several hours. They have to wash your hair, put the curlers in and let it dry for about an hour and then take them out. This is going to be fun.” She shook her had as she proceeded to show him how to do it all right. “We better find a better dress for you, something more casual. A shopping trip then we can do your hair. A shampoo and set. We better make an appointment. Its not like your old barber trips you could just walk in. These things have to be carefully scheduled. They take a while. Lets get started.”

She gave him about the closest shave a man could get without taking a layer of skin off. She showed him how to do the foundation better. “See, you need smooth surface for the foundation.” She applied a pancake foundation on his face. “See how smooth and beautiful that is. She applied a heavy coat of mascara and eye shadow to give him a dark exotic look “We will be using real eyeliner for you. “

Then she helped him in his clothes and put his jewelry on. He looked like a beautiful lady. She asked seriously, “Calvin what is all about?”

“Well, I want to attend the final semester of college as a girl. Can you call me, Caitlyn?”

“Okay Caitlyn. You mean full time, what about your job?”

He shook his head, “That wont work. They have strict rules and they pay me. I can attend classes and such at college. That wont hurt anything and I pay good money to attend. Full time except my job.”

“Why are you doing this?” She was worried. She did want a boyfriend not a girlfriend.

He shrugged. “I just want to experience what it’s like. I am not a transsexual. I just want the experience of being a woman. Are you okay with that?”

“Sure,” She said. “We can work with that, I was worried.”

Then he asked, “If I did actually want to start the real process of changing myself to a woman, what would you think?”

“I woldnt like it,” She admitted. “I would have a problem with that. It isn’t a bigotry. Its simple sexual attraction, I like you as a man, calvin. We couldn’t be in a relationship anymore. I would still be your friend and support you though the process. Maybe we could double date? She gave him a sly grin.

He laughed. “Its not me and I don’t want to become a woman. Its just an experience. I am glad to have your support.

“Good, lets go shopping, Caitlyn.” They got in her car and she suddenly said, “Not so much pink now. You are an adult woman, not a little girl. Got it. We wear other colors for gods sake.” She laughed.