My name is Anthony and I am twenty-two years old. I have extra-long dark hair and darker eyes. I tie my hair into a ponytail and have a close trimmed beard. I look handsome and enjoy keeping myself in shape. I am a lucky guy as I have a very sexy girlfriend who is two years older than me.

Zoe and I met at a mutual friend’s party and hit it off right away. She has short blonde hair and blue eyes. Her small beautiful mouth sits beneath a cute button nose. All in all, Zoe is a goddess and I love her.

Our relationship was at an all-time high and I had a key to her flat. I was able to come and go as I pleased and often did, surprising her with dinner when she came home from work. There was also an ulterior motive for going around when she wasn’t home; lingerie.

From my teen years, I had become besotted with girl’s underwear, it was my secret taboo. Lace, silk, cotton and nylon, I loved them all. The feel, the touch even the smell seemed to turn me on. Zoe always seemed to find it interesting that I liked to breathe in her panty covered crotch before I ate her out. She never complained.

It was a normal Monday afternoon and Zoe always worked late on a Monday. I let myself in and walked into her bedroom. I liked her bedroom, it was very girly, with a king size four poster bed. I sat on the bed and then lay back. I was tired. I yawned, looking around and seeing her washing basket. I smiled to myself, maybe there were some treats in there for me.

I raided her basket, taking out a cute pair of blue lace panties. They were soft to the touch and I could feel myself getting hard as I held them. I could not help but think how they were nestled close to Zoe’s wet pussy, the thought turned me on so much.

I stripped off standing naked in front of her full-length mirror, my cock bouncing slightly. I took the panties and slid them on, the feel made me even harder. I stood there in front of the mirror wearing cute panties, my cock peeking out the top unable to be contained.

I went to her basket again searching for the matching bra, I was disappointed to be unable to find it. Of course Zoe often mismatched her underwear so I went to her chest of drawers, and sure enough, it was on top of her file. I took out the bra, wrapping it around my waist. I slipped it on backwards, clasping the back in front of me. Then I slid it around and put my arms through the straps. I looked at myself in the mirror once more, damn I looked good.

I really believed I could pass for a girl, a bit of tweaking here and there and no one would know. My cock needed attention, it looked so good peeking out the top of the panties. I pulled my cock so that it instead came out of the right leg hole and started to stroke myself.

Slow long strokes, savouring the feeling I was giving to myself. I closed my eyes, enjoying myself. I could feel myself getting off, getting close to the brink. I had let go and sit down. Just as I sat down the door opened. To my horror, Zoe walked in. She gasped, taking in the situation.

“I’m, I’m sorry, it’s not what it looks like. I... I... I... ” I stuttered.

She walked over to me, unzipping her skirt, and pulling her top over her head. I gasped when I saw her light pink lace lingerie underneath, making my cock as hard as I have ever known it.

“Anthony, I knew you were jerking off into my underwear, but I didn’t know you were wearing them.”

She sat next to me, wrapping her hand around my cock. She started to jerk me off with fast, forceful strokes. I groaned loudly as she carried on talking.

“If I knew you liked my underwear so much I would have got you some. Anyway, after I make you cum, we are going to dress you up. I’m going to make you into a cute little girl and then we are going to go out to dinner.”

I looked at her in shock. She just smiled back at me.

“Yes, Anthony. We are going to go out to dinner with you dressed and looking like a girl. You’d like that, wouldn’t you?”

I blushed, knowing it would be a big step from wearing her underwear and dressing fully like a girl. The thought did turn me on a hell of a lot and Zoe’s hand kept jerking me off. Zoe pulled my panties to one side, exposing my ass slightly. She licked her finger and then pushed her digit against my ass. We have always played around with ass play and it was not a big deal to me when she pushed her finger deep into my ass.

She milked me and my ass seemed to clench tightly around her finger. She loved making me cum, having a hold over me turned her on. She leant forward, taking my shaft into her mouth. She sucked me hard, taking my cock into her throat. It was too much for me, the mix of her fingering my ass and taking me into her throat pushed me over the edge.

I let out a deep guttural groan and started to shoot my load into her mouth, she sucked hard, hungrily swallowing my load. I held the back of her head, feeling her take me deep into her throat, sucking and swallowing me.

I lay back on the bed, exhausted and spent. I watched Zoe get up and walk out the room. She came back in holding a small bowl a towel my can of shaving cream and my straight razor. She smiled at me and rested the items on the bed.

“Come, baby, let’s give you a shave.”

She took some shaving cream and slow spread it over my face. She slowly started to shave my face, as she had done so many times before. Once I was completely clean-shaven she dabbed some aftershave on my face. She stepped back to admire her work, giving a low whistle.

“Okay Anthony, let’s lose those panties.”

I complied, pulling off her panties. My now flaccid cock still dripping cum.

She dropped to her knees in front of me, rubbing more shaving cream over my cock and balls. I guessed what was about to happen, so I just closed my eyes and let her work. Knowing there was a sharp razor so close to my soldier didn’t help my blood pressure, so I kept my eyes closed and let Zoe get on with it.

“Okay, you can open your eyes now.”

I opened my eyes to see that my cock and balls were as bald as can be. She had left a little hair above my penis in the shape of a heart. I loved it. I reached down and cupped my own balls, it felt amazing, a sensation I had never felt before.

“Okay Anthea, we need to go have a shower before we really pretty you up.”

I looked at her a little confused, she laughed and gave me a peck on the lips.

“I am going to dress you up, I am going to make you look like the girl you want to be. We will go out with you dressed as a girl, I will address you as Anthea. We can’t have you in a sexy dress and call you Anthony, can we?”

I blushed but smiled. She led me into the bathroom and pulled the elastic band holding my ponytail. My hair cascaded down to my shoulders. We went into the bathroom and I stepped into the shower while Zoe undressed. She joined me in the shower, stroking my cock slowly.

Zoe lovingly washed my body, taking extra care of my bald cock and balls. She shampooed my hair and kissed me passionately as we washed. I took the opportunity to finger her, getting her off within a minute or so. I know how to push her buttons.

Once out the shower, we both dried off. Zoe put on some basic underwear before looking for something proper for me. She gave a squeal when she pulled something from her drawers, I could see why and started to get hard once more.

She walked over to me with a bra and panty set. It was black with red flowers embroidered on it, it really did look sexy. She told me to lift my foot, and she gently slipped the panties up my leg. She stood behind me, reaching between my legs, pulling my cock pulling the panties up. She smiled, sliding her fingers over my crotch.

“There, Anthea. Now you have a camel toe.” She giggled.

She helped me with my bra, shoving paper towels inside the cups to fill them up.

“Don’t worry, the dress I’ll give you will cover you up enough.”

She put a garter belt on me, it matched the lingerie I was already wearing. She then helped me put on stocking, the feeling of them on my bare skin was intense, if my cock wasn’t trapped under my ass by her panties I would have cum right away.

She rummaged in her wardrobe for a minute, while I sat there touching and feeling my new underwear. She caught me and laughed, she kissed me on the lips and lay something on the bed next to me.

“Stand up sexy, let’s get you into this dress.”

I stood up, as she held open a short black dress with a zip down the centre. I was about to put my arms through when she laughed, almost falling to the floor.

“No, no, no. You put it on from the front, the zip does up in the back, silly.”

I blushed putting my arms forward and stepping into the dress. She turned me around and I could feel it tightening around me. It was a very tight fit but felt great to wear. I looked in the mirror, the dress looked amazing. It was short, riding up my thigh. It had long sleeves It covered my chest like Zoe said, but had an open neck and a large collar.

I was admiring myself in the mirror as Zoe came up behind me with the of her hair iron things. She wrapped my hair around this baton-like device, then letting it go. I watched in fascination as my usually straight hair started to curl. Bit by bit, she curled my hair till I looked completely different. It was like an out of body experience.

Zoe sat me down in front of her dresser. She pulled up a chair in front on me and opened her makeup bag. She pulled out a pair of tweezers and held my head tight. I grunted as she slowly started to pluck my eyebrows, making them neater and slightly more defined; feminine. She then started to put makeup on me. First a base and a blusher, then highlights defining my cheekbones. She sat in front of me for a good ten minutes using half of her makeup bag on me. Finally, she smiled with approval.

She got up and picked up her phone from the bedside table and took a couple of pics. She stood in front of me and put on some matching lingerie and a sheer and lace blue dress and sat down to do her own makeup.

While Zoe was getting ready I stood up to look in the mirror once again. What I saw in front of me was the cutest thing I had ever set eyes on. The cute girl in front of me had dark hair that seemed to curl forever, deep sexy dark eyes and sweet wet glossy lips that I just wanted to kiss. I was hot.

Zoe laughed when she caught me staring.

“Yes Anthea, you are hot as fuck, and together we are going to make all the heads turn. Come, baby, let’s go to dinner.”

She gave me a pair of her flat office shoes and let me out the front door. As we walked slowly to one of the many restaurants in town, Zoe spoke softly to me.

“Anthea is going to come out every Monday with me. We’ll go have dinner, then go to a club to dance together. If you really like it will start buying you sexier lingerie and outfits.”

I had to say I liked the sound of that, my first real foray into cross-dressing was great.

------

It has been three months since I first went out as Anthea and now I do it every week. Zoe and I make love and then she shaves me clean. We shower and she dresses me. She had bought me a special padding to go in my bra and new sexy lingerie and dresses.

I love being Anthea and look forward to Mondays all week.