As I sat in the meeting I couldn't take my eyes off her. She was young and so cute and she was wearing a short pleated wool skirt. The skirt was a pink and light blue plaid color. She would cross her legs and pull the skirt down being sure not to show too much. When we went on a break many of us went outside. It was a nice comfortable fall day. I watched as she came out and stood by herself. She took out a cigarette, lit it and started to smoke, just enjoying her break. I was surprised she was alone and I wanted to go over a talk to her but I was afraid. But I couldn't stop watching her.
After a couple minutes she walked over to me. She said "Hi what's your name?"
Delighted, I said "Hi my name is Jeff".
She said "Well Jeff, I am Katie. I noticed that you have been watching me all day."
"No I haven't" I said.
"Don't lie to me Jeff. I know you have. Don't be embarrassed. I understand. Men look at me all the time. But you look at me different than most men. I think you are looking at my skirt... aren't you?"
As she said this my eyes went down to her skirt and I knew she was right. But I said "No I haven't."
"Well I just love to wear this skirt. It is so comfortable and it really feels good to have it on. The soft wool material feels so nice. Would you like to touch my skirt, Jeff? Would you like to feel the soft wool?" I just stood there turning every shade of red. I didn't know what to do. So she took my hand in hers and brought it over and brushed it across her skirt. It sent intense feelings throughout my whole body. I felt very embarrassed and yet aroused at the same time. I looked around to see if anyone was watching, but no one seemed to notice what was happening.
Then Katie said "I think you want to wear this skirt, don't you Jeff?"
Trying to ease the tension I just said "I think you look much better in it than I would."
"Oh I don't know about that" she said. "I think you would look really cute in this skirt. And I know I would like to see you in it. So here is what we are going to do. If you want to wear my skirt I want you to meet me right here after the meeting. Now before we go back inside do you want to feel it again?" I looked at her for a long time trying to decide what to do. Finally I reached out and put my hand on her skirt and rubbed around feeling the soft material. "Ah that's what I thought. Now you will be right here waiting for me after the meeting, do you understand?"
"..... Yes" She turned and walked back inside.
Needless to say I couldn't concentrate on anything else for the rest of the meeting. I just kept thinking about Katie and her skirt. I kept thinking I was crazy and I can't do this. I don't even know her... what was she going to do. I could be getting myself in a very embarrassing situation. Every so often she would look over at me and fiddle with her skirt and wink at me. I couldn't wait for the meeting to end. I felt like everyone knew what was going on and were watching me. Finally the meeting came to a close. She stood around talking to some of the other girls. I was sure she was telling them about me and I felt humiliated.
But I just couldn't resist so I went outside and waited for her at the designated place. It seemed like forever before she came outside. When she did, she was with several other girls. They stopped up by the door and she had another cigarette as I stood there watching her. OMG she was a cutie! Finally she walked over to where I was standing and she said "Hi Jeff, are you waiting for someone?"
Surprised by this I hardly knew what to say, but I said "I am waiting for you."
"Oh really... why is that?"
She was acting like we had never talked before. What was going on here? I said "you told me to wait for you here."
"Oh did I? So you're here because I told you? I don't think so. Now tell me Jeff, why are you here?"
Humiliated beyond belief I managed to say "because I want to wear your skirt."
"Oh I see. You want to wear this little skirt I have on, is that what you are saying?"
"Ok" she said "I'm glad we got that straight. Go get in your car and follow me to my apartment."
It seemed like a long drive and I was going nuts thinking about what was about to happen. When we arrived at her complex I parked next to her car and got out. She came over and took my hand and walked me inside. She unlocked her door and we went in. Neither of us spoke a word. I was in a daze. She finally told me to sit down and she went back to the bedroom. After a few minutes she came out wearing a different skirt and she was carrying the skirt she had on before along with a bag of stuff. She came over to me and brushed the skirt across my face and dropped it down onto my lap.
"Is this the skirt you want to wear Jeff" she asked. "Tell me what you want to do." I just sat there frozen in a daze. She said "come on sweetie. We talked about it before. Why have you come here today?"
Finally I said "because I want to wear your skirt Katie."
"Very good" she said. "Now take off your clothes and put on this skirt." She watched as I removed my shirt and pants and shoes. I was standing there in front of her in my underwear. I picked up and skirt and started to slip it on when she said "wait a minute. You can't wear a pretty skirt with that ugly boy underwear." She pulled out of the bag a pair of frilly pink panties. She brought them over to me and dangled them in my face. "If you want to wear my skirt you must put on these pretty girl panties first. Now take off that boy underwear and put on these panties."
I did just as I was told. As I slid the panties up my legs it sent a shiver through my whole body. I pulled them all the way up and they felt so good. I was hard as a rock. Seeing this, Katie said "Well I see you like my panties. Does it feel nice to wear them?"
"Oh yes it does" I said.
"Now the skirt... put it on." I picked up her skirt and stepped into it. I pulled it up over my butt and zipped it up. It was a perfect fit. "The zipper goes in the back" she said as she gently twisted the skirt around on my body. Next she pulled out a fluffy angora sweater from her bag. "This sweater goes great with the skirt" she said. Katie brought the pretty sweater over and brushed it lightly over my nipples. It felt so good and my nipples got hard and tingly. "Oh do you have sensitive nipples Jeff?" She held the sweater over my chest and used her fingers to rub and tickle my nipples through the sweater. I was so excited and about to burst. Then she dropped the sweater and told me to put it on. I quickly pulled the pretty sweater over my head and it fell over my chest as I felt the soft material tickle my nipples.
She produced a pair of stockings and platform high heels and had me put them on too. And lastly she pulled out a shoulder length blond wig and fitted it onto my head. The soft hair hung down on my shoulders and tickled my neck and ears. "I was right" Katie commented. "You do look cute in my skirt, and now that the rest of your outfit is complete, I must say you look just like a sweet little girl! Do you like the way these girl's clothes feel on you? Do you like being dressed like a girl Jeff?"
"Yes I love being dressed like a girl. It's wonderful."
"Now walk over there to my mirror and see how cute you look sweetie." I did my best to walk in the high heels, which wasn't easy. But when I got to the mirror I could not believe my eyes. I did look like a cute little girl. "Does it excite you to be a girl?" she asked. She lifted up my skirt and saw my boner and said that I must really love being a girl.
She told me to stay in front of the mirror as she pulled a chair up close to me and she sat down. She lit a cigarette and said "pull your panties down just a little and release that hard thingy of yours my little girl. Now I want you to masturbate for me while you look at yourself in the mirror."
I was so horny I was already about to shoot. I took it out and began to stroke slowly and gently. She sat back and watched as she smoked. It didn't take long before I shot out all over the mirror. Katie reached out and scooped up some of the cum and lightly smeared it on my lips. "This is your lip gloss sweetie! Now if you are a good little girl and want to come back and play some more dress-up with me you will lick it all up"
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