My Feminine Side

Theresa had me stand up, adjusted my dress, and then we stood side-by-side and looked into the big mirror attached to her dresser.

"You're beautiful," Theresa said.

I had to agree. I hardly recognized myself and I was pretty sure even people I knew wouldn't recognize me. I thought to myself that I was much more attractive as a girl than I was as a boy. And I felt incredibly sexy. I loved the way I felt in Theresa's clothes. The panties and stockings felt amazing, and the dress looked and felt great as well. I wasn't quite sure of the bra and heels yet, but decided I could get used to them. The funny thing was I felt more confident dressed this way as well.

"I love it," I said after a couple of minutes looking at my reflection.

"Great!" Theresa exclaimed. "Let's go out."

Suddenly I didn't feel so confident. "Go out where?" I asked.

"A movie," Theresa said, "at the mall. We can go down to the mall and show you off, get something to eat, and then go to a movie."

"I don't know," I began, but Theresa cut me off.

"Too late, we're going," she said. "Sit there and look pretty while I freshen up."

Theresa started toward the bathroom with a black dress in hand.

"Wait a second," I said.

"What now?" Theresa replied.

"I had to change in front of you. I think it's only fair if you change in front of me."

"You made me turn around."

"Yeah, but you watched in the mirror anyway." I said, ending the argument.

Theresa laughed and reached back to unzip her long black dress. Then she stepped out of it and stood looking at me with her hands on her hips. As I said before, I had seen her naked in the past. I was aware that she had a nice body, but I never really thought about her in a sexual way. We had been close friends for such a long time, both of us were gay, and it just wasn't something I had ever thought about before. When I looked at her on that day, I wanted her desperately.

Theresa was wearing a bright red lace push-up bra that made her tits look much bigger than they actually were. Her matching red thong left very little to the imagination, covering only a small triangle in her crotch. She spun around and I realized that her ass was perfect. It wasn't big, but her cheeks were round and not boyish like many of the girls her age. I thought she was perfect.

"You're perfect," I said as she spun back around to face me.

Theresa blushed. "Thank you," she said. "Far from it, but thank you."

She stepped into her dress, which was also black, but this one was a mini dress as well. It had long sleeves and covered her up to the neck, but it did expose her perfect legs. After that she touched up her makeup, pulled on a pair of combat boots, and pronounced she was ready.

"What's your girl name?" Theresa asked as she picked out a small black purse for me to carry.

I hadn't even thought about it, and asked her for a suggestion.

"How about Karla?" She suggested. "I had a huge crush on a girl named Karla in the 8th grade."

"I'll be Karla for you," I replied with a smile.

"Thanks, Karla," Theresa answered and kissed me on the cheek. "How's your cock, by the way?

"Still hard, you perv," I replied with a laugh.

"Aren't you supposed to call your doctor if you've had an erection for like, four hours or something? You know, like they always say in those commercials?"

"Very funny. It hasn't been four hours yet."

"Well, I'll keep checking. In case we have to take you to the emergency room or something."

We both laughed and went out to her car. I was walking a little gingerly in the high heels, and my confidence was pretty shaky.

"Are you sure about this, Theresa?" I asked after climbing into the car and my skirt hiking up to my waist.

"You can't get in the car like a boy, you goof," she said. "Get out and let me show you."

Theresa showed me how to get in and out of the car a couple of times, and then watched while I practiced. I screwed up completely the first couple of times, but with her guidance I soon had it down pat.

"Remember, we sit down to pee also," Theresa said, and then laughed at the look on my face. "Relax; you're going to be great."

I tried to relax, but between my erection and my nervousness about being in public dressed like a girl, I was pretty much a nervous wreck when we pulled into the mall parking lot.

Theresa looked at me and smiled. "We don't have to do this if you don't want too," she said.

"I want too," I replied, "but I'm not sure I can pull this off. I mean, I know I look like a girl, but acting like one is a lot harder."

"We can try another time," Theresa said, smiling gently.

"No," I replied, "let's do it. I don't know if it would be any better another night, but if we pull this off tonight we've got it made."

"Great!" Theresa exclaimed. "How's your hard-on?"

"Not hard," I replied, wondering when that had happened.

"Good. Tuck it under and between your legs before you get out of the car. That will keep it out of sight unless you get another one of those pesky erections."

I laughed and did as she said, and then we got out of the car. Luckily no one was standing outside my door because I spread my legs wide and got out like I always did. Theresa rolled her eyes and came around and inspected me. She adjusted my bra and messed with my makeup a little, and then pronounced I was perfect. We started toward the mall.

It didn't take long for me to realize that wearing heels sucked. It was about 50 yards to the mall entrance, and my feet hurt like hell before we even got there. I told Theresa I wasn't sure I could keep the heels on, and she told me we would buy some new ones at the first shoe store we came too. I started worrying that I didn't have enough money, but Theresa told me not to worry, she had a credit card. Her family was very wealthy.

There was a security guard at the entrance who opened the door for us, and he obviously checked me out as I walked through the door. I turned back and smiled at him, catching him staring at my ass. He looked up and saw me looking at him and winked at me. I turned back and told Theresa and she laughed and said, "Don't look now, doll, but every guy in the place is checking you out."

I looked around and it was true, guys of all ages were looking in our direction. It made me feel uncomfortable, but also very sexy. I reached down and took Theresa's hand in mine and she squeezed reassuringly.

"You're doing great, Karla," she said. "Let's go into that shoe store up there on the right."

We entered the shoe store and a very attractive salesperson asked if she could help us.

"I'm looking for some new stilettos," I said. "I seem to have outgrown these."

"What size do you wear?" She asked, looking at me curiously.

I looked pleadingly at Theresa. We hadn't exactly anticipated this situation and I didn't have a clue. Theresa took charge.

"I think we need to get her measured," Theresa said. "Why don't you take care of that while I look around?"

The pretty saleswoman smiled at me and led me to a chair, getting on her knees in front of me. I sat and removed my shoes, only fumbling with the straps a little bit. The saleswoman measured my foot and told me it looked like I was a size nine, medium width. Just then Theresa walked over with several different shoes, all with stiletto heels. I liked a pair that was similar to the ones I had worn in but with a slightly less complicated strap. Theresa told the saleswoman that we would try those and pointed out a few more for her to bring out as well. The saleswoman went into the back to find shoes in the correct size.

"Well," I said, "this could be going better. I think she suspects I'm not a girl."

"Don't worry about it," Theresa replied. "She's just in it for the sale. She could care less if you're a boy or a girl."

I thought about it for a moment and realized Theresa was right, as usual. I would probably never see this woman again, and I really didn't care if she knew my secret or not.

The saleswoman returned with several boxes of shoes and set them on the floor next to where I was sitting.

"My name is Barb, by the way," she said with a pretty smile.

"I'm Karla," I replied, smiling back. I was feeling much more confident.

Theresa had wandered off to look at other shoes, and Barb opened the first box and took out a pair of shiny black stilettos. They weren't my first choice, but Barb was already lifting my foot to slip the left one on. I had never been much of a shopper. I usually preferred to go out knowing what I wanted and buy the first thing I found that met my criteria. I hated trying on clothes and especially shoes, but I found this experience rather more pleasurable.

Barb slipped the shoe onto my foot while holding my ankle, and then she slipped the right shoe on. She took her time adjusting the strap, and when she was done she sat back and told me to try them out. I stood carefully, letting my feet settle in and Barb reached out and gently squeezed the side of each shoe.

"That seems to be a pretty good fit," she announced.

"Walk around a little," Theresa yelled from the front of the store.

I did as Theresa suggested, taking a few tentative steps away from the chair, and then walking more confidently around the store, stopping in front of the floor mirrors to admire the shoes. They fit perfectly, and they made my calves look super sexy.

I walked back over to where Barb was kneeling on the floor, watching me carefully.

"You have perfect legs, Karla," she said when I sat back down in front of her.

"Thanks," I replied, very pleased with the compliment.

I tried on six more pairs of shoes. It was the first time in my life I had ever enjoyed shopping like this. Barb was very attentive, and I got the distinct impression that she was letting her fingers linger longer than necessary on my stocking-clad feet and lower legs. I felt my cock stirring again, and hoped it wouldn't get hard.

Theresa bought two pairs of heels for me. I tried to argue that I only needed one pair, but she was insistent. I ended up picking the same shoe in two different colors, black and red. Theresa and Barb both approved of my choice. I sat down and Barb removed the last pair of shoes I had tried on. She was definitely caressing my foot this time. When I looked down at her she smiled up at me.

"You look terrific, sweetie," she said quietly, "but you need to shave your legs. And don't forget about the hair on your toes. Dead giveaway."

She smiled once more and slipped the black shoes I had selected onto my feet and quickly strapped me in. Giving my calf a last gentle caress, she stood up and carried my purchases to the checkout desk. I stood, somewhat shakily, and joined Theresa as she paid. We thanked Barb and turned to walk out.

"Karla," Barb called and I turned back to her. She handed me a business card. "You look beautiful. Very sexy and very passable except for your legs and feet. I put my cell number on the back. Call me if you'd like my assistance to become perfect."

"Thank you, Barb," I replied. "That's a very kind offer."

I tucked the card into my purse, smiled at her, and then turned and walked to where Theresa was waiting just outside the store.

"What was that all about?" Theresa asked and I explained. When I was finished she said "That sounds kind of creepy."

It sounded kind of creepy to me as well. Theresa and I set off arm in arm through the mall. We did some window shopping, and I was getting very turned on by all the guys who were checking me out. My cock was getting uncomfortably hard and I told Theresa I needed to rearrange things down there. She rolled her eyes and led me to the women's bathroom. I went into a stall and lifted up my dress and pulled my panties down, then pressed my hard cock against my lower belly and pulled the panties back up. It wasn't ideal, but it wasn't sticking straight out any more. I exited the stall and Theresa checked out my crotch, pulled my dress up just a little to add some additional material in the front, and then we went back out into the mall.

Our next stop was Victoria's Secret. Theresa told me she wanted to buy some lingerie for me. The thought of trying on sexy lingerie really had the blood flowing to my crotch.

"We better not stay in here for four hours," I whispered as we walked in.

"Oh, for god's sake!" Theresa exclaimed, immediately understanding my comment. "We need to figure out how to take care of that, and the emergency room is not an option!"

A pretty girl offered to help us when we walked in but Theresa said we were just browsing. She led me immediately to the section with all the sexy panties. I had never been in Victoria's Secret before and was amazed at the selection. I couldn't figure out how anyone could ever make up their mind what they wanted. Theresa was an old pro at panty shopping, however, and she made several selections, and then led me to the bras. In no time we were heading into a changing room.

"Strip," Theresa ordered when we were safely locked inside.

"Ummm, don't you need to wait outside?" I replied.

"This is no time for modesty, sweetie. I won't look if you're that concerned, but I want to see how you look with these things on and it's just easier if I stay in here with you."

I didn't have a witty comeback, so I motioned for her to turn around and pulled the mini dress up and off. Just then I noticed the floor to ceiling mirror on the back of the door and saw Theresa's reflection smiling back at me.

"Oh, all right," I said. "For a lesbian, you sure spend a lot of time trying to look at my cock."

Theresa laughed, and I smiled back at her. She turned around and watched as I removed the bra and then hesitantly slid the panties down and stepped out of them. My fully erect cock stood straight out and was once again leaking pre-cum. I was horrified that I would get it on the panties.

"Shit!" Theresa exclaimed as she stared at my hard cock. "That thing is more trouble than it's worth."

"Let's not get carried away," I replied. "I'm sort of fond of it."

Theresa stood lost in thought for a few moments, then picked up her purse and rifled through it, coming up with a small plastic bag of Kleenex. She handed it to me.

"Jack off," she said.

"What?" I replied, dumbfounded.

"Masturbate. Make yourself come, however you boys do that. I'll go out and look around some more so you're not embarrassed."

"I can't do that even if you're not in here," I replied. "What if someone hears?"

"Why is this so damn hard?" Theresa wondered aloud, and then looked at me. "No pun intended."

"Alright," she said finally after staring at my cock for so long I was starting to feel very self-conscious, "if you ever tell anyone about this I will hunt you down and cut your balls off."

"Tell anyone about what?" I responded, wondering what she was talking about.

Instead of answering, Theresa knelt in front of me and took my cock in her hand. I stared down in shock as she moved her head forward and wrapped her lips around my cock.

"Theresa!" I hissed. "What are you doing?"

She pulled back enough to say, "Taking care of our little problem. You should feel honored; I have never done this before and never will again. Let me know if I'm doing it right."

"How would I know if you're doing it right," I muttered as she placed her lips around my cock once again and started bobbing her head up and down.

Despite my shock and fear of getting caught, it felt absolutely amazing. Her mouth was warm and moist and felt incredible. I was thinking that there couldn't possibly be anything that felt better than this when I suddenly came in her mouth, spurting several jets of warm cum. I tried to pull back but Theresa had her hands on the backs of my thighs and held me in place while she swallowed my cum.

I was horrified that I had come so fast and hadn't even warned her and that I had come in her mouth. Granted, I had never imagined I would be coming less than two minutes after she started, but I had been masturbating for years and I had always been able to sense when I was about to spurt.

Theresa was still gently sucking on my cock as it slowly went limp. I looked down at her and we made eye contact, and she winked at me.

"I'm so sorry," I said and then was immediately sorry I had spoken, because she removed my cock from her warm mouth.

"For what?" Theresa asked.

"For what?" I exclaimed. "For that! For coming in your mouth."

Theresa was gently squeezing my cock and lapped up the cum that oozed out of my urethra.

"It's okay," she replied. "It was a little unexpected, but I don't mind. It actually tastes much better than I thought it would."

Theresa continued to lick the remnants of my ejaculation as they oozed out of me. Even that felt incredible. I caught my breath as she continued to clean me up and she finally gave my cock one last squeeze, kissed the head, and stood up, smiling brightly.

"Problem solved," she announced and kissed me lightly on the lips. Her face was flushed and she was breathing a little heavily. "I wonder if that's what they do at the hospital when you show up with a four hour erection."

"I'm sure they have specially trained nurses to do that," I replied, laughing "That sounds like a good summer job for you!"

A brief image of a line of men with Viagra induced erections lining up at a cubicle where I waited to ease their suffering flashed into my mind.

"That does sound like the job for me," I replied with a smile.

"You're such a homo," Theresa said affectionately, and kissed me again on the lips.

There was a knock at the door and someone said, "Is everything alright in there?"

We both giggled and Theresa said, "Everything is perfect!"

"Well, let me know if you need anything," the voice offered.

"Will do," Theresa said, rolling her eyes comically. "I wonder if she would be so helpful if we told her we needed her to give you a blowjob so you could try on these panties."

We both laughed loudly, and Theresa wiped my cock with some Kleenex and told me to try on the panties. The first pair was called "Body by Victoria Seamless Little Lace Hiphugger."

As I slipped them on I said, "You'd think they could come up with a shorter name for something with so little material."

Theresa laughed and stood back to check me out in the light blue lace panties. They felt amazing, and Theresa obviously approved. They were much more modest than the thong I had been wearing, but still looked and felt very sexy.

"How do they feel?" Theresa asked.

"Amazing," I replied. "Perfect fit."

"They look good on you," Theresa said and handed me another pair.

These were white lace and carried the grand name "Fabulous by Victoria's Secret Hiphugger Panty." They were even skimpier than the first pair. I slipped the blue panties off and stepped into the white ones. Theresa watched intently as I pulled them up. I was starting to enjoy being naked and trying on clothes in front of her. It wasn't really a sexual feeling; more like an "I'm one of the girls" feeling. I liked the intimacy we were sharing.

The next pair was called "Cotton Lingerie Ruch-Backed Hiphugger Panty" and had solid material in the front and waistband with lace on the butt cheeks. The way they were designed actually enhanced the appearance of my ass, Theresa said, and I loved the way they felt. Following that I tried on a little pink pair of "Flawless by Victoria's Secret Hiphugger Panty," and then a navy blue "Very Sexy Chantilly Lace Hipkini," and finally a pair of blue with white polka dots and lace leg openings "Body by Victoria Cheekini Panty." Fancy names all.

Theresa told me to wait in the changing room for a few minutes and went out. I locked the door after her and looked at all the sexy panties I had tried on. I loved the way they all felt on me and how they looked on me as well.