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.