I hung up the phone with Megan.  I was so happy that we were planning to get together on Saturday.  She told me she plans to dress me up again.  And my sister has told me that Megan may want to peg me.  I imagined being dressed up at Megan's, and her putting on a strap-on dildo, bending me over, and sticking it in me.  I wasn't sure what I thought about that, but as I pondered it, I started getting horny again. 

I went over to my mirror so I could admire myself again in my little dress.  I was still looking cute.  Then I heard a knock on my door.  I opened it, and it was Amy.  "So, how did it go with Megan?" she asked.

"Great.  I'm getting together with her Saturday."

"What about Kaylee? Are you going to tell her?"

"Oh, I forgot about that.  I don't know.  Do you suppose you could make plans with her on Saturday?  Then I won't have to worry about that.  Since you like Kaylee, I'm sure you can think of something to do."

Amy got a big smile on her face.  "Sure, I'll help you out and keep Kaylee totally occupied on Saturday.  You just go and have a good time with Megan."

"Thanks, sis.  Amy, would you help me out of this dress?  I think it's time for me to get changed back to Jon.  And help me get this makeup off too."

Amy unbuttoned the dress and I took it off.  I removed the wig.  I saw myself in the mirror with just makeup, bra, and panties.  Having been dressed as a girl most of the day, I looked funny without the wig.  Amy took the dress over to my closet.  She got a hanger and hung the dress in my closet.

I said, "Amy, don't put that in there.  Take it back to your room."

"I said you could keep this dress, Jon.  You never know when you might want to wear it again," she teased.

Amy took me into the bathroom and helped me remove all the makeup.  It is a lot of work getting makeup off the eyes.  But I wanted to be sure to get every trace of it off.

I went back to my room and took off the bra and panties.  I put on a pair of my own underwear and a pair of sweats.  I looked at myself in the mirror and saw plain old Jon once again.  I have to admit I was a little sad to no longer be Bethann.

I went downstairs.  Mom was sitting in the living room watching TV.  When she saw me, she got a big disappointed look on her face, and said, "Oh, Jon.  I was hoping you would still be wearing your dress.  You looked so cute in it."

"Could we just give it a rest, Mom?" I said.

"Sure.  I'm sorry, honey.  I understand it's embarrassing for you.  Have a seat and let's watch some TV."

We watched the end of some reality show Mom had been watching.  It was getting late, and I was tired from a long and eventful day.  I told Mom I was going up to bed.

"Good night, honey," she said.

I went back up to my room, closed the door, and went to bed.  I was really tired, but I couldn't stop thinking about how much fun I had dressed as a girl.  And I thought about seeing Megan on Saturday.  I was afraid I would never fall asleep with all these thought running through my head.

Then there was a knock on the door.  I called out, "Come in."

Amy poked her head in.  "Are you asleep, Jon?"

"No, not yet."

"Good, I brought you a little present.  Since you had so much fun dressed as Bethann today, I thought maybe you would like something feminine to sleep in."  She held up a little baby blue nightie and a pair of matching panties.  These are really cozy, and will be more comfortable, and prettier, than your sweats."

"Very funny, Amy!  No thanks."

"I'm not trying to be funny.  I thought you might like them."  She walked over and set them on my bed.  "Goodnight, Bethann.  Enjoy!"  She closed the door and left.

Just the thought of wearing that nightie got me excited again.  Now I would never get to sleep.  After pondering it for a while, I finally got out of bed and picked up the nightie.  It was a light baby blue color, with little ruffles around the neck and sleeves.  It was so feminine.  I already knew I wouldn't be able to resist putting it on.  So I might as well get it over with.

I took off my sweats and underwear.  I got the little panties and pulled them up my legs.  I pulled the nightie over my head.  It felt wonderful.  I looked at myself in the mirror.  Without the wig, I looked like a boy in his sister's nightie.  I briefly considered putting the wig back on.  It was setting over on my chair.  But I resisted and just got back in bed. 

After a quick masturbation session, I finally went to sleep.

The next morning I woke up to the feel of the soft nightie.  I quickly remembered all the events of yesterday.  I felt embarrassed that I was wearing the nightie.  But why should I be?  I was dressed as a girl most of yesterday, and after all, Amy did bring me the nightie so I could wear it.  It was already 10:00 and I knew Mom would be gone.  But what about Amy?  Part of me wanted to go down for breakfast wearing the nightie, but part of me was scared someone would see me.  Even though Amy had given it to me, I didn't want her to know I had worn it.  And I certainly didn't want her to see me in it.  To be safe, I took it off, and put my sweats back on.  I went down and had breakfast. 

Later that morning, Mom and Amy came home.  I was prepared for more teasing about my dressing as a girl.  But thankfully, nothing was said about it.  It was just a normal day.  That is, until Margo arrived.

It was around 2:00 in the afternoon, when our doorbell rang.  I was upstairs in my room.  Mom called me down, and I saw Margo holding a bag.  She said, "Hey Jon, I need to get my cheer uniform back from you.  I need it for practice tonight."

Mom got the biggest smile on her face.  She said to Margo, "It was so nice for you to let Jon wear it.  They had me fooled for a while.  He looked just like his sister!"

"Oh, I know," said Margo.  "Wasn't he pretty?"

"He sure was.  And I understand he had worn one of your dresses earlier.  Last night, he wore one of Amy's dresses."

"Oh, did he?  Well, I'm sure he was cute as a button!"  They both just giggled, and I blushed.

Mom said, "Margo, it was so nice of you girls to help Jon, or should I say Bethann, get to be a girl for the day.  I know he enjoyed it so much.  He's lucky to have such open-minded and understanding friends as you."

"Oh, it was a pleasure.  He was a delightful and well-mannered girl for us."

"I expect he will be dressing up a lot more now that it's all out in the open.  Did you know that Amy said he could borrow her clothes anytime he wants?  And she even gave him a dress to have as his own."

"Isn't that sweet!" said Margo.  And speaking of his dresses, I have one here to give him too."  She took the dress out of her bag.  "This is the dress he wore at my house yesterday.  And I told him he could keep it."

Mom took the dress and held it up against my body.  "Oh, it's lovely, Margo.  Thanks so much.  I know he really appreciates it.  Jon, why don't you take your new dress up to your room, and bring down Margo's cheer uniform."

"Oh, and Jon, you can also keep the wig, and the bra and panties you wore yesterday.  I wore that wig for Halloween a couple of years ago, and I don't really need it.  I'm sure you will get much more use out of it.  And since you now have two dresses, you will need a bra and panty set," Margo teased.

I was so embarrassed by the whole conversation.  I blushed a deep red.  I took the dress Margo had given me up to my room and hung it in my closet with the dress Amy gave me.  I brought down Margo's cheer uniform and gave it back to her.  She put it in her bag, said her goodbyes, and left.

I quickly went back to my room, so as to avoid any further conversations with Mom on the subject.

That night, I once again wore the little blue nightie Amy gave me, got excited and masturbated, and had a good night's sleep.

The next day was Saturday, and I had my date with Megan.  I was really looking forward to seeing her again.  I knew she planned to dress me up, so I got a head start by wearing the panties and bra Margo had given me.  I put on my regular clothes over top of them.  I checked myself in the mirror to make sure the bra did not show through. I also put the wig in a bag and brought it along.  I arrived at Megan's right on time.

"Come in, Jon," Megan said when she opened the door.  "I've been looking forward to our little session today.  Let's go right up to my room and get started."  She took my hand and led me upstairs.  With her parents out of town and no other friends around, it was just the two of us.  I was expecting us to start kissing when we got to her room, but she had other plans.  She was ready for my next makeover into Bethann.

She had set out on her bed a pair of panties, bra, stockings, a little necklace, and a bracelet.  On the floor, she had a pair of black high heel shoes.  And hanging on a hook outside her closet was a little dress.  It was black with pink and white flowers on it.  It had a white peter pan collar with little ruffles, and it had puffy sleeves with white ruffles.  It was a beautiful dress for a young girl of 12 or 13, but clearly, she had set it out for me.

Megan noticed me admiring the dress, and she said, "You looked so cute in Margo's and Amy's little girl dresses, so I thought you would look adorable in mine.  It seems we all have a little girl dress or two that we never wear.  But you look so cute in them!"

I just blushed, imagining myself putting on Megan's dress.  I have to admit that I really did want to wear it.

"OK, off with those clothes.  Let's get you dressed and made up."

Forgetting for the moment that I was wearing panties and bra beneath my clothes, I took off my shoes, socks, shirt, and pants. 

"Oh, isn't that cute," she gushed.  "You're already wearing girls' underwear.  But I picked out some of mine that I really wanted you to wear.  Do you mind changing into that?"

I removed the panties and bra and put on the things Megan had set out for me.  Megan helped me roll the stockings up my legs.  Megan opened the bag I had brought and pulled out the wig.  "Good girl.  You remembered to bring your wig."  She put the wig on me and brushed out the hair till it was all smooth, hanging down on my neck.  I loved the feel of the long hair tickling my neck and ears.

"Sit down over here," said Megan, motioning towards her chair and makeup table.  "Let's do your makeup."  She used a couple of hair clips to hold my hair out of my face.  As she was making up my face, she said, "I was talking to Amy yesterday, and she told me she gave you a little nightie for bedtime.  Have you been wearing it in bed, Bethann?"

"Oh, Megan!" I blushed.

"No need to be embarrassed about your nightie.  I mean, here you are wearing bra and panties and letting me put makeup on you.  I think it's fine that you wear a nightie.  Promise me that you'll wear it.  I think it's cute that you have your own nightie."

She continued with my makeup, doing my eyes, lashes, cheeks, and lips.  When it was complete, she had me look in the mirror.  I looked just as cute as I did the other day when I was made up.  Then she attached the necklace and the bracelet.  "Next, your dress and your shoes," she said.

Megan took the pretty black dress with flowers and ruffles off the hanger.  She handed it to me and said, "Since you are going to be wearing dresses more often now, you really need to learn how to zip one up yourself.  Put it on and reach around and try to do the zipper."

I stepped into the dress.  I reached around back and zipped up the zipper as far as I could.  She told me to reach over my shoulder and pull it the rest of the way.  Then I used both hands around my neck to hook the little clasp.  It was nice to know I could do it myself, which also meant I could get it off without any help.  Then I sat down and slipped on the shoes Megan had set out for me.

"Come and see yourself in the mirror.  You look so cute!"  I walked over to the mirror and saw the pretty girl looking back at me.  I really liked how I looked.  This dressing up could become addictive, I feared.  Megan came up behind me and put her arms around me.  She nuzzled me from behind and started rubbing against my butt.  "You look beautiful, Bethann.  I think I like you this way."

I turned around to face her.  Our eyes met, and we looked at each other for a few moments.  Then she closed her eyes, puckered her lips, and leaned in for a kiss.  Our lips met first, then our tongues.  We stood there making out for several minutes.  When our kiss ended, she took my hand and led me over to the bed.  We sat down together and continued kissing.

Megan pulled me backwards and we laid down together.  We continued kissing and started to explore each other's bodies.  She reached up under my dress, and rubbed my boner through my panties, and I rubbed her pussy through her little shorts.  After a few minutes of this, she got up and went over to her dresser.  She said, "Now I want us to play a little game.  This is called role reversal.  You will be the girl, and I'll be the guy."

She opened her drawer and pulled out a strap-on dildo.  "Don't be alarmed, Bethann.  I have a special surprise for you.  You'll love it, I promise.  Since Amy had already told me about the strap-on, I wasn't alarmed.  Even though I was a bit afraid, I was so horny, and I had been looking forward to doing this with Megan.  She took off her shorts and top and stood there in her bra and panties.  She was so pretty and sexy.

Megan attached the dildo around her waist.  She got a tube of lubrication, and slowly walked over to me.  I just watched in fascination as she approached.  She was so confident, yet so cute.  "Do you know what I'm going to do with this?"

"Yes, I think so," I replied.

"Tell me."

"You're going to fuck me with that dildo."

"That's right!  But actually, it's called pegging.  And you're going to love it."

"Oh, OK, pegging."

"So, it's Ok with you, then? That I peg you in the butt?"

"If you say I'll enjoy it, I trust you."

"Good girl.  First, get down on your knees."  She walked over and stood in front of me with her dildo inches from my face.  "Now, suck on it," she commanded.  "Get it all wet and slippery so it will slide in easier."

I reached out and gripped the base of the dildo, brought my mouth up, and started to suck on it.  I used some of the techniques I had seen girls in sex videos use.  It was so erotic, sucking on the dildo.  I felt so feminine and submissive.  It got me even more horny.

Then Megan pulled away.  She told me to lean over the bed and stick my butt out.  She lifted up the back of my dress, got some lube, and applied it to my little butt hole.  She used her fingers to penetrate me, pushing in some of the lube.  Then I could feel the tip of her dildo against my butt.  "This will hurt a little at first.  But please stick with it, and it will start feeling really good soon. Just relax and let it happen."

She stuck the tip in very slowly.  It did hurt at first, but not too bad.  She slowly worked it in inch by inch.  She soon hit a spot that sent waves of pleasure throughout my body.  She pulled it back, and then pushed in again.  Every time she hit that spot, it felt better and better.  Soon I was moaning from the pleasure.

"See, I told you that you would love it."

"Oh my Gosh, Megan, please don't stop!  This feels so wonderful!"

After a few minutes of glorious pegging, she pulled it all the way out.

"Don't stop, Megan, Give me more."

"Don't worry, we're not done yet.  Roll over and lie on your back.  Put your legs up."  I did as I was told, and she got on top of me and entered my butt again, now facing me.  As she pegged me, she leaned...