This is a true story of how my Mom feminized me as a teenager. She had caught me wearing her pantyhose the summer before seventh grade. I got the surprise of my life the first Sunday of junior high, when she started encouraging me to wear them -- Tracy

Several months later, Char and Mom decided to swap kids for a month or two during the summer. I was so excited when I heard that – I could get to dress with Char! Unbeknownst to me, she had already told Mom, “I’ll have him in a skirt by the second day!”

The day before we left, Mom came home from the store with two bottles of Nair. She handed it to me and said, “You should clean up your legs in case you want to wear a skirt up there. Nair will get you a lot closer than shaving. Tonight after supper I’ll show you how to use it. You’ll probably want to shave your underarms too. I also got some extra for you to take with you, you’ll probably need to use it once a week or so.”

After supper I took a shower, and Mom showed me how to use the Nair, and how to not leave it on too long. I couldn’t believe how smooth and sexy my legs were afterward! Then we packed for me, putting in camis and panties to sleep in, and a few pairs of No Nonsense Sheer To Waist pantyhose for dress up. She went in the bathroom and got my Correctol out of the vanity drawer. She said, “I’m packing your Correctol, in case you get constipated on the trip like before.”

On the trip up, I wore shorts, and every time the sun shone on my Naired legs, they were so shiny and smooth! I kept running my fingertips over them. When we met Charlene in Windsor, we used the restroom, then small talked for a few minutes.

Mom said, “Last night I had him Nair his legs and shave his underarms, so he’s all ready for you,” as I blushed.

“That’s great,” Char said, smiling. “We’re going to have a lot of fun.”

We girl talked all the way back to Toronto. After we got to her house, we put my suitcase in the spare bedroom and she said, “I’ve got some cute things for you to wear. Want to see them?”

“Sure,” I said.

She opened a dresser drawer and pulled out some things. “I got you some cute girl’s shorts and a top and a training bra. I’ve got some low heeled sandals you can wear with them, they’re in the closet. Go ahead and put them on. After supper we’ll do your nails.”

I changed into the outfit, and walked down the hallway to the kitchen. I helped make dinner and clean up afterward, loving to hear the clicking my sandals were making on the hardwood floor. After dinner we went downstairs to the family room, where she was sitting on the couch with her nail things. I sat down and we made small talk while she trimmed my nails and then put two coats of pink polish on them. As I was blowing on them to dry them, she said, “Now take off your sandals and let me see your feet.”

I reluctantly took off my cute sandals and put my feet up in her lap, and she gave my toenails the same treatment. As I was looking at my nails and my legs, remembering what we had been doing for the last hour, she touched my smooth bare leg, and I ejaculated, gasping. I was so embarrassed. I stammered, “Um, Char, um, I think I have a big problem, I think I just made a mess,” unsnapping my shorts and opening them so I wouldn’t get anything more on them, and exposed my dripping dick, which made me even more embarrassed.

She quickly jumped up. “Don’t worry, just sit still and I’ll get a towel.”

She came back a few minutes later with a wet washcloth and a towel. She wiped my cum off of my tummy and dried me as I just sat there, paralyzed, not knowing what to do or say. When she was done, she said, “There, don’t worry about it. Now, what would you like to watch on TV?”

We snuggled together and watched TV for a while, with our smooth shaved legs touching. Finally it was time to go to bed, and I went up and changed into a cami to wear to bed.

I woke up the next morning with the sun streaming into my room. I laid there, just staring at my polished fingernails, thinking how great this day was going to be! Finally I got up and got dressed in my girl clothes from yesterday. This was a new feeling – casual girl clothes and not hose and high heels. After I put everything on, I looked at myself in the mirror and couldn’t believe how much I looked like a girl! It felt so sexy to wear a bra. I sashayed out into the kitchen where Char was making breakfast.

“Oh look at you! You’re adorable!" she said. "After breakfast we’ll get some makeup on you.”

After breakfast, she got dressed, and then called me into the bathroom. “You don’t want too much makeup on for casual, but some basics.” She showed me how to put on eye liner and shadow, and then handed me a lipstick. “Here, this is light pink, just the thing for casual.” She took out one of her lipsticks, and said, “Here, do it like me. We’ll practice.”

I quickly got the hang of it. When we got done, she said, “Now you need something to put your things in.” She went into her bedroom and came out with a small denim purse. “Here, put your lipstick and some tissues in here. Keep it with you at all times, don’t lose it,” she warned. “Ready to go have fun? I thought we’d go to the market first and go shopping, then maybe go to the park.”

We hung out all day and had so much fun. We were like sisters. Every time I looked down and saw our smooth shaved legs and our cute feet and our painted toes in our sandals, I felt so cute and sexy!

Later after dinner, she surprised me by asking, “So how would you like to come to work with me tomorrow? I asked my boss if you could help out, do filing and things like that. You’d have to get dressed up though, wear a skirt and hose.”

Wear a skirt and hose! Great! I smiled coyly, “OK, I guess.”

Around nine, we were starting to yawn. Char said, “Come on, I’ve got something a little different for you to sleep in.”

We walked back up stairs to her room, and she opened her dresser drawer and pulled out a short pink chemise, handing it to me. I went to my room and changed into it. A few minutes later, as I was admiring myself in the mirror, she knocked lightly and came in. “Ready for bed?” she asked.

“I think so, this has been such a fun day. I had a ball,” I giggled.

She turned back the bed, and motioned for me to get in. “Sweet dreams,” she said. “We’ll have fun tomorrow.” She kissed me on the forehead, then turned out the light and shut the door. I luxuriated in bed in the satiny smoothness of the nightie. My dick got so hard. I reached inside the nightie and slowly jacked off, exploding in passion as I came. As I drifted off to sleep I passed a small fart, and remembered that I hadn’t done my push job all day. I hoped I wasn’t getting constipated.