"So what are you guys planning to do today?" my girlfriend Kaylee asked me when I picked up the phone. "Well, all the guys are going to the ballgame this afternoon," I replied. "But I'm not going because I want to spend the afternoon with you." "Oh aren't you the sweetest!" she gushed. "I've got the best boyfriend ever!" Deciding to add a little humor to the conversation, I said, "Is he better looking than me?" "Oh yes, h...

"Yes, that's a great idea," said Amy. "What do you think, Kaylee?" All the other girls chimed in, "Yeah Kaylee, come on let's do it!" "Yes for sure," said Kaylee. "Jon, let's see how you look in a dress! Margo, you don't mind if we borrow some of your clothes, do you?" "Not at all," said Margo. "Let's pick out something pretty for him to wear." "That's not a good idea," I said. "I think this has gone far enough." I must a...

"No pictures," I said. "I don't want any of the guys seeing me like this." "We won't show them to anyone, I promise," said Kaylee. "They will be just for us. We will only use my phone and I won't send them to anyone else. Do you trust me, Jon?" "Of course I trust you, Kaylee," I said. "But I still don’t want any pictures." "It will be OK, sweetie. I'll put them in a private folder and no one else will see them." "Oh, alri...

I have had such an amazing afternoon with the girls and being dressed as a girl myself. I didn't want it to end. Dressed as Bethann, I had got to kiss Kaylee and Cindy. I really wanted to try kissing the other girls too. Especially Megan. I've always thought Megan was really cute and sexy. I thought that if Kaylee and I ever broke up, I would go after Megan. Sometimes, and maybe it was just my imagination, I thought I not...

After the girls had a blowjob contest and made me cum, Amy said, "OK, now that you took care of that little problem, I think we're ready to go. Let's see if we can fool Mom." Margo got her car keys and gathered up the empty beer bottles in a trash bag. "OK, let's hit the road." As we headed towards the front door, I was getting very nervous about stepping outside dressed as a girl. I was wearing Margo's cheerleader unifor...

Amy shut the door and locked it. Then she turned back to me and smiled. She started walking slowly toward me, moving her hand in an up-and-down motion that mimicked her stroking a penis. I could hardly believe my sister was actually going to jerk me off. I was so embarrassed, I blushed a deep red. I just stared at her as she approached me. Amy walked over to her dresser and got out a pair of pink panties. Then she got her...

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...

I was exhausted from the pegging and the powerful orgasm. We rolled over and cuddled on the bed for a while. Before long I had fallen asleep. Megan let me sleep for about an hour. I awoke to her spooning me from behind and kissing my neck. I rolled over to face her, and she kissed me tenderly. I felt that I was falling in love with Megan. I would need to decide how to tell Kaylee that I want to see Megan now. Oh well, I w...

After a few minutes of rest, Amy said, "We better get cleaned up. Mom will be home soon." Amy took the dildo back to her room, and Kaylee helped me brush out my hair and fix my makeup. We straightened up the bed sheets and made sure there was no evidence lingering of our pegging session. We decided to go downstairs and watch some TV. I went into the kitchen and got a glass of lemonade for each of us. Kaylee and Amy were s...