I was told I looked pretty good.

I just want to get this out of the way first, before anything else. I am a dude - 100% male. I just like dressing up in girl's clothes

My name is Jack, an abbreviation of my grandad’s name Jackson.
At times, I think or maybe hope that I'm a bit more of girl to look at than I am a boy. Dressed in sexy clothes, with makeup on and my hair done, I make a pretty good girl. I'm thin and I have long legs that look great when I shave them and I have heels on. Guys hit on me when I'm dressed like a girl, and I love the attention. As a boy, I'm simply ordinary. Average looks, very thin, can't grow a beard, and while I run every day, I'm thin and look at least as much feminine as masculine.
I got teased a lot in high school. I was always too small to play football and basketball, wasn't strong enough to wrestle, even though they had a lightweight class that I thought I could try. I was on the track team, but while I have been running since I was 11, I don't run very fast. Some of the girls thought I was cute. The guys all called me a fag, homo, girly boy, and queer. The fact that I am gay didn't make any difference for me -- no one knew except my best friend -- and she wasn't telling. For a long time, I was more wondering and wandering as to my sexuality … but in the end I put myself in the ‘gay’ box.
My best friend Anita and I have known each other since kindergarten. She lived next door to me and we attended the same schools until we graduated from high school. We were inseparable, and she knew all my secrets just as I knew all of hers. I always thought she was beautiful, but no one else seemed to. Anita was also a bit of an outsider, especially in high school. She smoked and was into drugs, and when we started high school she was really into the Goth lifestyle. She didn't really fit in at the mostly white, mostly well-to-do, public high school we attended south of Atlanta, Georgia.
Anita got me started wearing girl's clothes. It was quite by accident, as most significant life changes tend to be. Walking home together one afternoon, a couple of the nastier bullies from our school confronted us. They called me several awful names, which had stopped bothering me some time before, but when one of them called Anita a slut, I found some courage and punched him as hard as I could in the face.
I weigh 120 pounds soaking wet. He weighed about 250 and was the starting tight end on the football team. While my punch didn't even make him flinch, the beating he and his friend administered left me bruised and sore for days. Fortunately they didn't hit me in the face, but my torso would be covered in fist shaped bruises later. To add insult to injury, they threw me into a muddy ditch on the side of the road.
Anita helped me to her house, where she helped me strip me out of my muddy clothes and told me to get in the shower. I was proud of myself for not crying while they had been beating me, but when I was alone in the shower the tears poured down my face. Not because of the pain, which was pretty significant, but because I hadn't been able to defend Anita.
When I finished in the shower, I went into Anita's room with a towel wrapped around my waist. She was sitting on her bed watching TV and she smiled at me when I walked in.
"How are you feeling?" She asked, concern obvious in her voice.
"Okay, I guess," I answered. "now I know how a punching bag feels."
"I put your clothes in the washer," she said. "I have some clothes you can wear if you want, or you can just hang out in the towel."
While Anita and I had seen each other naked on a couple of occasions, I wasn't comfortable enough with my body to hang out with her wearing only a towel.
"Let's see what you've got," I said.
Anita smiled mischievously, and held up a pair of purple panties. "You can start with these," she said.
"I'm not gonna wear your panties!" I said, horrified. "You don't even wear those."
"That's why I'm offering them to you," Anita said, laughing. "I got these two years ago. They don't fit me anymore and all my new stuff will be too big on you. And they're boy shorts, so not really panties."
She tossed them to me and I caught them but my towel fell to the floor. Anita took a look and smiled while I quickly covered up with the purple panties.
"Turn around," I said.
"It's not like I haven't seen it before," Anita laughed, but she turned around.
I lifted the skimpy panties up to take a closer look. They did look a little like the briefs I wore, but they were made out of a mesh material with a lace waistband. I held them up, stretched the waistband, and realized they would probably fit. I shrugged, bent over, and slipped them on. I pulled them up as I straightened.
I instantly loved the way they felt on me. The mesh material felt strange but somehow nice against my balls and cock, and especially on my ass. I looked in the mirror mounted on the dresser, and my first thought was that the boy shorts looked really good on me. I turned around so I could see my ass, and I was stunned. I had to stand on tip-toe to see, and that made my ass cheeks clench, and I couldn't help thinking that I had a pretty amazing ass.
"Wow!" I heard Anita say. I turned to her and she was staring at me with her eyes wide.
"Those look amazing on you," she continued. "They never looked that fucking good on me."
"You think so?" I asked, checking myself out in the mirror again.
"If you were a girl, I'd do you," Anita said with a laugh.
I may have failed to mention that Anita is a lesbian. I think that's why our bond was so strong. Neither of us had ever had sex, but we both knew that we were gay, and we guarded each other's secrets like they were the Crown Jewels.
I suddenly realized that my cock was semi-erect and still growing, so I turned away from Anita.
"Too late," she said, "I already saw it. You're turned on wearing my panties, aren't you?"
"Yes," I said. I had never lied to her before and wasn't going to start now. "And they're boy shorts, not panties."
"Right, I forgot," she said, hiding her smile. Anita had a pair of gym shorts and a t-shirt for me but instead of tossing them she stood up and walked over to me.
"I wonder if you would do something for me," she said, somewhat hesitantly.
"What?" I replied, suspiciously. I knew that tone and that look -- she was going to ask me to do something she thought I wouldn't like.
"I'd like you to try on some of my old clothes," she said.
My first instinct was to say no and be done with it. I opened my mouth to decline, and then I had second thoughts. The boy shorts did feel pretty good, and I was suddenly curious to know what it would feel like to wear some of Anita's sexier clothes. Before her Goth phase, she had always dressed very fashionably and, I thought, very sexy. I was thinking of one particular mini dress that I had always thought she looked incredible in.
"Only because you asked so nice," I finally replied. "And because I love you. But if you ever tell a soul I will hunt you down.
"Have I ever told anyone your secrets?" She asked, feigning hurt that I would even think such a thing.
"No, you haven't," I said, laughing at her pouty face.
Anita went to her closet and started looking for something for me to try on. I checked myself out in the mirror again and once again thought I looked pretty sexy in the boy shorts. My cock was fully erect, and I tried to reposition it so it wasn't so obvious, but all I could do was pull it straight back against my belly where the waistband of the shorts held it in place. When I looked up, Anita was watching me with a smile on her face. I instantly turned bright red.
"Got everything where you want it?" She asked.
"Funny," I replied.
Anita held up the same black mini dress I had just been thinking about. It had looked amazing on her.
"You always liked when I wore this one," she said. "It doesn't fit me anymore and we were going to give it to Goodwill. Glad I still have it."
Anita took the dress off the hanger and held it up against my chest, nodding as she realized it would probably fit. She held it out to me. I took it in my hands, liking the feel of the lace, but I realized I had no idea how to go about putting it on. It suddenly seemed very complicated.
"Uhhh, a little help?" I said, and Anita laughed. She took the dress from me and told me to raise my arms over my head. I did and she bunched the dress up and then slipped it down over my arms and head, slipping the sleeve over my left hand. She continued tugging it down past my shoulders, where it was a little snug but the material was stretchy, and then down over my body and finally past my hips, tugging it and straightening it as she went.
"Holy shit!" Anita exclaimed.
"What?" I replied.
"Just look at yourself," Anita said, turning me toward the mirror.
I looked, and I couldn't believe I was looking at myself. The dress was very sexy. It was short, about mid-thigh on me, with a spandex lining on the inside and lace on the outer part. It had one lace sleeve for the left arm, and the right arm was bare. The left shoulder was covered about halfway, and the dress was cut down at an angle to go under the right armpit, leaving my right arm and shoulder bare, as well as a good portion of my upper right chest and my back to below the shoulder blade. The lining ended a couple of inches higher up than the lace on my legs.
"Wow," I whispered.
"Wow is an understatement," Anita said excitedly. "You look amazing."
"You think so?" I asked skeptically.
"Sexy and very feminine," Anita said, nodding her head. "I think with a stuffed bra, some sheer stockings, and some heels, you could pass for a girl. We'd have to put some makeup on you and maybe a wig, but yeah, you look amazing."
I eyed myself critically. I had to admit, I looked pretty good. My facial features had always been a little feminine, which, along with my small stature, was the reason for all the teasing and bullying. I tried to imagine what I would look like with the other stuff Anita had mentioned, but having never really thought about it before, the mental image I conjured was more clown-like than passable girl. I shook my head.
"I don't see it," I said. "I mean, the dress does look good on me but I don't think anyone would mistake me for a girl."
"I guarantee you I can make you look so much like a girl no one will ever know." Anita said. She went to her dresser and rifled through it, coming up with a pair of sheer black stockings and a black bra.
"Take off the dress," she ordered, "and we'll start from scratch."
I removed the dress and laid it on the bed. Anita walked over and told me to hold up my arms, and when I complied she slipped the bra on pulling the straps onto my shoulders and adjusting it so it was tight. She still wasn't satisfied, and went back to her drawer and returned with a couple of pairs of cotton panties, which she stuffed into the cups. She was smiling as she worked, and I smiled back at her. She readjusted the bra, nodded her head, and said "that’ll do."
She told me how to put on the stockings so I sat on the bed, bunched one of them up and slipped my toes into it. Then I started pulling it up my leg.
"Not too fast," Anita said as she watched. "You have to go slow or you can get a run in them."
"What's a run?" I asked, slowing down. "Sounds bad, whatever it is."
Anita laughed. "It's like a tear, only the material doesn't come completely apart. It looks terrible and you have to throw the stocking away if you get a run in them."
"Definitely bad," I said, laughing with her. I continued pulling the stocking up slowly over my ankle, then my calf. I was amazed at how good it felt.
"This feels pretty damn good," I said as I eased the stocking over my knee. Anita was biting her lower lip as she watched. I pulled the stocking up as far as it would go. There was a band of black material at the top which was tight and I assumed was there to hold the stocking in place. When I asked, Anita confirmed that was the case. When I was finished adjusting the first one, I pulled on the second one.
"Those purple panties won't do," Anita said when I was finished putting on the stockings.
"Boy shorts," I replied.
"Right. Sorry," she continued. "Let me find something black to match your outfit."
Anita went back to her dresser and quickly found something black.
"Take off your boy shorts," Anita said, smiling.
"Turn around," I said, taking the panties she held out to me.
"Oh, come on," she said, "I've already seen it once today. It's not like I'm going to faint or something."
"But I might," I said with a laugh. "Besides, it's different than when you saw it before. It's hard now."
"I can see that," she said, pointing down to where the head of my cock was visible above the waistband of the panties. I was horrified to see a drop of clear pre-cum oozing out of my urethra. I spun away from her and almost fell.
"Alright," Anita laughed. "I can see you almost fainted. I won't look."
I looked over my shoulder and she had indeed turned around. I set the black panties on the bed and removed the boy shorts, sliding them down over the stockings carefully. Then I held up the black panties and looked them over. There was no mistaking these for boy shorts. Anita had given me a lacy black thong.
"Doesn't leave much to the imagination," I grumbled as I sorted out how to put them on.
"Imagination is all I have right now," Anita said over her shoulder. "Hurry up, would ya?"
"Patience," I replied. "I've never had to put on a piece of string before."
Anita laughed as I put my right foot through what I assumed was the correct opening. Then I stepped through with my left foot and pulled the panties up, proud of myself for getting it right the first time. I tried to arrange my cock so it would not be visible, but it wasn't possible while I was erect. Once again, the head poked out above the waistband. I stood up and looked in the mirror, and noticed Anita's reflection looking back at me. She was smiling wickedly and she laughed when she saw the expression on my face.
"Saw the whole show, did you?" I asked, smiling, unable to be mad at her.
"Yep," she replied.
"Pervert."
"Yep."
"You might as well turn around then," I said, and she did.
"You look really hot," Anita said when she had given me a close look. "Especially that little turtle head sticking out of your panties!"
She laughed and danced back out of the way as I swung a punch at her arm. I was laughing as well, and I chased her back into a corner and smacked her on the ass a couple of times.
"You really are a perv," I said as I stepped back.
"I am," she admitted. "A bonafide perv. I'd probably be in jail if anyone knew about my perviness."
"I know all about your perviness."
"Said the boy dressed in girl's clothes," Anita laughed again. I loved the sound of her laughter. "I think you are the winner in the perviness category."
"I think you're right," I said. "But it sure feels good – even when you use the word pervy."
It did feel good. I loved the way the stockings felt on my legs. I had thought the thin material of the thong would be uncomfortable in my butt crack, but it actually felt pretty sexy. And I loved the way the lacy mesh cupped my balls and pressed against my cock. I could feel pre-cum oozing out again. I looked up at Anita to see if she had noticed, and it was obvious that she had. She was staring down at my dripping cock. I was about to say something witty when Anita bent over and licked the pre-cum off the head of my cock. When her tongue touched me it was like a bolt of electricity.
“No, I don’t think I want to do that. You’re quite a lot girl – but not enough … yet maybe. Sometime in the future I might really wish you were a girl," she said, a little bit huskily.
"Right now," I replied, "I really wish you were a boy!"
We both laughed, the moment gone. Anita adjusted my bra again, and then told me to put the dress back on while she went back to her closet. This time I managed to get the dress on by myself, and when Anita returned with a pair of really high heels, I was just finishing tugging the dress down. She stopped dead in her tracks and when I looked up at her, her mouth was hanging open.
"What?" I asked.
"You look pretty good," Anita replied.
"Thanks," I said. "I have to admit, I feel pretty sexy."
"You look sexy. Sexier than I ever did in that dress."
"No way," I replied, secretly very pleased.
Anita handed me the heels, black three inch stilettos.
"I'll kill myself if I try to walk in these," I said, holding them up.
"Sit on the bed," Anita ordered.
I sat down and Anita slipped the shoes onto my feet. They were a little tight, since my feet were the only part of me that was actually bigger than Anita. Well, besides my cock, but that didn't really count. Anita adjusted the complicated looking straps that went up above my ankles, then stepped back and held her hands out to me.
"Slowly!" She said.
I took her hands and slowly stood up. With her support and not moving, it wasn't too bad. The shoes were definitely too tight, but not by much. We stood there holding hands for a few moments, smiling at each other. Anita told me again how sexy I looked.
"Okay," she said, "let's take a step. Look down at your feet at first and make sure you plant the lower part of the shoe flat on the floor. If your ankles roll you're in trouble, okay?"
"I guess so," I said, suddenly not so enthusiastic.
"Alright, I'm going to step back with my left leg. You step forward with your right."
I did as she instructed, looking down from my much loftier perch. The first step went smoothly, and Anita stepped back with her right foot and I followed with my left. We managed to make the four steps to the wall without me killing myself. Anita got us turned around, and we repeated the process back toward the bed.
We practiced walking around the bedroom several times with Anita leading and me following. Then she asked me if I was ready to try it on my own.
"Not really," I replied, but let go of her hands. I stood still for a few moments and then took a hesitant step. When I didn't fall, I took another step, and before long I was walking around the room.
"We need to work on your sexy walk," Anita said. "You look like somebody shoved a stick up your ass."
I thought I had been doing pretty well, but when Anita said that I burst out laughing, my right ankle rolled outward, and down I went.
I lay on the floor laughing, and Anita was laughing also.
"That's definitely not a sexy walk!" Anita said breathlessly, bringing on a fresh round of laughter.
Anita helped me up and then put on some heels of her own. After that I followed her around the room and tried to mimic her walk, which I have to admit, was pretty sexy. Then she followed me around for awhile, giving me additional tips on how to walk sexy, and then we went out and tried the stairs. I had a death grip on the handrail at first, but before long I was going up and down the stairs like an old pro. Anita followed me up the last time.
"Great ass," she said.
"Glad you like it," I replied.
Back in her room, she rummaged in her closet for some makeup. Everything she had on her makeup table was black and white, and it took her awhile to find something not so Goth. She finally found a box containing all the makeup she had packed away and told me to sit down at the makeup table. I did as she instructed and she pulled another chair over and started going through the box. She set several items out on the table and then told me to look at her.
"We'll keep it simple for starters," Anita said, and then proceeded to apply makeup in what I thought was a far from simple process. It took about 10 minutes before she said she was done, sat back and looked at me critically, and then smiled. I looked in the mirror and was absolutely stunned at the transformation. Anita used a blow dryer and a brush and tried a couple of different things with my hair, and settled on a part on the left and brushing most of my hair over to the right. When I looked in the mirror again, I was once again stunned at the way I looked.
That was the first time I got dressed up. I have the pictures hidden deep in my computer.
It was some time until the next …

I've had this story hanging around for a few years now - I think it's based on another story I dimly remember.