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Author's Notes

"In the last part of this story, Jon is feminized and dressed as a girl by his girlfriend and her friends.  They dress him as a cheerleader and take him home to fool his mom.  His Mom insists that he put on a dress so she can see him.  His sister, Amy, agrees to help him with the little problem in his panties."

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 chair and scooted it up beside me, and sat down.  "OK, Bethann, lift up your dress and pull down your panties."

I could see myself in her mirror as I lifted up my dress, exposing my panties and my throbbing erection beneath.  I pulled my panties down just enough for my dick to spring out, bouncing up and down.  I was so ready for her to take it in her hand, when she said, "Go ahead, sweetie, start stroking."

"What? I thought you were going to do it for me."

"I said I would help you, but not do it for you," Amy teased.  "So get going.  We don't have all day."

Well, this was not what I expected. I guess she wanted me to masturbate while she watched.  I tentatively gripped my dick and started to slowly stroke it up and down.  I was so embarrassed masturbating as my sister watched.  As I stroked, Amy started giggling and then laughing at me.  I stopped stroking and said, "Amy stop laughing."

"I just wanted to see if you'd do it.  I didn't think you would," she giggled.  "Of course I'm going to do it for you, you silly girl.  Now, hold that dress up.  I don't want to get it messy."  Amy was seated next to me as I stood there holding up my dress with my hard penis sticking out.  She reached out and gently gripped it and began a slow up and down movement.  She masturbated me slowly and gently, and I was so turned on, yet still so embarrassed.

I watched in the mirror as my sister masturbated me.  She was looking up at me with her big brown eyes as she stroked.  She picked up the pink panties she had brought over and got them ready to catch my cum.  She could tell I was getting close, and she slowed down, prolonging my pleasure.  She said, "Do you want to cum, Bethann?"

"Yes."

"Then you'll need to ask me nicely."

"Please make me cum, Amy," I pleaded.

I felt like I could shoot any second, but she stroked so slowly and gently.  When I masturbate myself, I usually go fast at the end.  But going slowly at the end felt so much better.  I would have to remember this for the next time I masturbate.

Finally, I could feel I had hit the point of no return and the pleasure was so intense, as my dick began to swell and shake.  I whispered, "Amy, I'm going to cum now."

She held the panties up to catch the cum as the first shot came spewing out.  I squirted shot after shot of cum into her panties.  She lightly squeezed the head of my dick, milking out every drop.  She used the panties to wipe it clean.  "OK, that takes care of your little problem.  Now let's get you sorted and we will go down and show Mom how cute you look in your new dress."

She ran a brush through my hair, examined my face, and then touched up my lip gloss.  "Are you ready for your big unveiling?"

I checked myself in the mirror one last time, and said, "OK, let's go."

Amy opened her door and we stepped out into the hallway.  As we started walking, I heard the clicking sound of my heels on the hardwood floor.  I felt the little dress swishing across my legs.  The dress was even shorter than the cheer skirt I had worn before, so I was exposing a lot of leg as I walked.  We went downstairs.  Amy told me to wait in the living room for a moment.

I was nervous about Mom seeing me in the dress - I didn't know why; she had already seen me dressed as a cheerleader, after all.  I was also embarrassed knowing that, only a few minutes ago, Amy had masturbated me to an orgasm.  I hoped Mom had not heard us.

Amy went into the kitchen and announced in the voice of a Master of Ceremony, "And now I present to you the beautiful Bethann!"

I poked my head around the door and saw them standing there watching with anticipation for me to enter.  "Come on in, Bethann.  Let me get a good look at you," said Mom.

I walked in with my heels clicking on the floor trying my best to look confident.  But I definitely did not feel confident.  Mom and Amy clapped as I entered.  Mom said, "Oh, Bethann, you look adorable.  That's such a cute dress!  You look like Amy when she was younger.  Give us a little curtsy!"

"Oh, Mom," I complained.

Amy said, "Yes, Bethann, show us a curtsy.  You know, like you did over at Margo's."

Feeling defeated, I dropped one leg back, held the hem of my dress and dropped down in a little curtsy.  Amy and Mom clapped and cheered.

"Alright, enough of that," I said. "Could we just eat dinner now?"

"OK, sweetie. Thanks for being such a good sport," said Mom.  "Bethann, come and help me serve the dinner.  Amy, you take a seat."  While Amy sat at the table, Mom and I served the dinner.  We all sat and ate. 

Mom wanted to hear all about our day at Margo's, how I came to get feminized, and what we did.  Of course, we could not tell her most of what we did, since we basically just made out with all the girls and had some amazing sex.  But Amy stuck to her story that I had asked to be dressed as a girl.  She was so persistent that I just stopped arguing about it.  She also mentioned to Mom that she had told me I could borrow her clothes anytime I wanted to.  She added that I could keep the dress I was wearing because she never wears it anyway.  The whole conversation was very embarrassing for me.

After dinner, Mom insisted on taking some pictures of me.  I made her promise not to show anyone else, especially Dad.  "Amy, why don't you go up and put on a dress, too?  Then I can get some nice shots of the two of you in your pretty dresses."

When Amy went upstairs, Mom told me to sit down in the living room.  She wanted to have a little talk with me.  I sat on the sofa, smoothing my dress beneath me.  Mom noticed this and gave me a smile.  She sat down beside me and just looked at me.

Feeling quite uncomfortable, I had a hard time looking her in the face.  After waiting for her to start talking, I finally said, "So, you wanted to talk, Mom?"  I could tell by her face that she was thinking hard to find her words.

After a few moments, she said, "So, Bethann…. I guess when you are dressed like this, I'll keep calling you Bethann.  So, Bethann, I just want you to know that it's OK with me that you want to dress like a girl.  I think you are very brave for showing me your feminine side."

"You've got it all wrong, Mom.  I didn't want to wear the girls' clothes.  The other girls really did talk me into it."

"I understand how it's hard to admit, sweetie.  But let's be honest here.  You would never have agreed if you didn't want to.  And you certainly would not have come home dressed like this if you didn't want me to know.  I want to thank you for trusting me with this secret of yours. And I want you to know it's all fine with me."

I had grown tired of arguing about this, so I just said, "Thanks, Mom."

Mom continued, "It's so sweet of your sister to let you wear her clothes whenever you want.  And it's OK with me, too.  It was nice of her to say you can keep this dress you're wearing.  It's such a cute dress and you do look very nice in it.  Honey, you seem so natural and comfortable in the girls' clothes, I am sure this is not the first time you have dressed up.  I imagine you have been borrowing Amy's clothes for a while now.  I'm glad it's all out in the open now.  This dress you're wearing is a bit young for you, but if you like it, that's fine with us.  Perhaps you'd like to go shopping with me, or with Amy, if you prefer, to pick out some girls' clothes of your own.  We could get some things more suitable for your age."

"I don't think so, but thanks for the offer."

"By the way, do any of your friends know about Bethann?  Obviously, all the girls know, but do any of your guy friends know?"

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"No!  And I don't want them to know.  And I don't want Dad to know either."

"Honey, I think your father should be told, but I'll leave that up to you.  And as for your friends, it's your secret to tell when you choose to.  I won't betray your trust."

I was feeling embarrassed and uncomfortable with this whole conversation.  Fortunately, it came to an end, as Amy came down the stairs.  She was wearing the dress she wore to prom last year.  She had put on some makeup and put her hair in a ponytail.  She looked really pretty.

Mom said, "Oh, you look great, Amy.  Absolutely perfect for some pictures with Bethann.  By the way, Bethann and I have been having a little talk while you were upstairs.  I let him know that it's all fine with me if he wants to dress like a girl.  It's fine with me too if he wants to borrow your clothes.  That was so nice of you to offer.  And I told him that maybe one of us could take him shopping sometime so he can pick out some pretty things of his own."

Amy just giggled at the thought of it.  I just sat there and blushed.

Amy said, "Yes, Bethann.  I would be glad to take you shopping.  Maybe Kaylee and some of the other girls would like to come along."

"No thanks," I said.

"Well, the offer stands, whenever you decide you want to."

Then Mom had us pose together for some pictures.  I again emphasized that she could not show them to anyone.

After the photo session, Amy said, "Come on, Bethann.  Let's go upstairs and call Kaylee.  You promised to call her to tell her how everything went when you showed Mom."

Amy and I went upstairs to her room, and Mom went back to the kitchen to do the dishes.  Amy got her phone and we called Kaylee.  We told her all about how I had fooled Mom and now I'm wearing one of Amy's dresses.  Kaylee seemed to think that was wonderful that I was still dressed as a girl, and now in my third outfit for today.  Amy also told her that she had explained to Mom that I had wanted to be dressed as a girl, and Mom had totally believed it.

I again complained about that, and Kaylee said, "Oh, Jon, you know it's true.  You know you wanted it, and you definitely enjoyed it."

After we finished the phone call with Kaylee, I said, "We need to call Megan too.  I told her we would call."

"So, you want to call Megan, do you?", Amy asked in a teasing tone.

"Well, I told her I would."

"If I didn't know better, I would think you have a little crush on Megan."

I quickly denied it, even though it was true.  "No, Kaylee is my girlfriend, not Megan."

"But I think you would like Megan to be.  It's OK.  You can admit it to me.  If you tell me the truth, I'll tell you a secret about me."

I felt close to my sister, and I did feel I could trust her with this secret.  Plus I wanted to hear her secret.  "OK, yes, I do like Megan," I confessed.  "But I'm going with Kaylee, so nothing can happen with Megan.  So, what's your secret, Amy?"

"OK, my secret."  Amy paused and blushed, trying to find the right words.  "OK, I think I'm gay.  Or at least I'm definitely bi.  But I prefer girls.  You know all the stuff we girls do, practicing kissing and the other stuff?  Well, that was all my idea.  And there's more, too.  I have a crush on a special girl.  Don't flip out, OK?  I have a crush on Kaylee."

"My girlfriend, Kaylee?  You have a crush on her?"

"Yeah.  And I think she likes me too.  I'm sure she is bi.  Sometimes I get together with her and we do stuff together.  You know, it's more than practicing.  We really enjoy each other.  Are you mad at me?  Remember, this is our secret.  And since you like Megan, why don't you let me have Kaylee and you start dating Megan?"

"So, my girlfriend has been cheating on me with my sister.  I really would prefer Megan, so I'm not mad at you.  And it did seem a bit odd that Kaylee didn't mind me kissing all the other girls, and even them sucking my dick.  If she really liked me like a girlfriend should, she never would have allowed all that.  I guess maybe we were both looking for something else."

"Just between you and me, I'll tell you a secret about Megan.  You'll find this interesting.  Megan has a strap-on dildo she likes to use on us.  I really do think Megan is bi too.  Actually, I have a strap-on dildo too, that I use on Kaylee.  But here's the real interesting thing about Megan.  She has told us that she knows a guy from her old school who lets her dress him up like a girl.  She uses the strap-on to peg him in the butt."

"You use a dildo to fuck Kaylee?  I am learning so much about you, and her, today.  So, you two really do have a thing between you?"

"Yes, we do.  But get this.  Megan said her friend really likes to be pegged.  He said it feels even better than fucking a girl.  He loves to get fucked in the butt.  Have you ever been pegged, Bethann?"

"No, of course not," I said.  But I could not help but picture Megan with a strap-on coming up behind me, sticking it in, and pegging me.  I liked Megan so much, I would probably do anything she wanted.  And maybe it would feel good.

Amy said, "If you want, I will get my strap-on and peg you, so you can see what it's like."

"No, that's alright.  I'll pass on that."

"Holding out for Megan to do it, are you?  I understand.  Remember, all this is secret.  Please don't tell anyone I told you these things.  The girls would never trust me again.  And, by the way,  Kaylee already knows you have a crush on Megan.  She knew it before today.  I really think you should go for Megan.  And speaking of Megan, shouldn't you go ahead and call her?  I'll leave you alone so you can talk to her in private.  You should really ask her out."

"OK, I'll go to my room and call her."

I walked out of Amy's room and went into my own room and closed the door.  I admired myself in the mirror wearing my little pink dress.  Then I smoothed out my dress, sat down, and crossed my legs.  I thought for a few minutes about what I would say to Megan.  I picked up my phone and dialed Megan.

When she answered, she was anxious to hear all about when my mom saw me dressed as Bethann.  I told her the whole story, even the part about me now wearing one of Amy's dresses.  I left out the part when Amy jerked me off.  I would never tell anyone about that.  Megan wanted to see me in the dress, and she insisted that we switch to FaceTime, so she could see me.  She had me step back so she could see all of me.  I did a little twirl for her and then a curtsy.  She was delighted that I was still dressed like a girl.

"Bethann, you make such a cute girl," she said.  "I had a great time with you today, as Bethann.  We all did.  But especially me.  I think I like Bethann."

"Well, Bethann likes you too, Megan."  I blushed when I said that.

"You're so cute when you blush.  You have been doing a lot of that today.  You don't need to be embarrassed that you like being Bethann.  And you don't need to be embarrassed that you like me.  I already knew you did.  I was wondering when you would make your move.  Listen, my parents will be out of town this Saturday.  Why don't you come over, and I'll help you dress as Bethann again.  Just you and me.  Then we'll see what happens.  What do you say?"

Here is a dream come true.  A day with Megan.  And she said she likes me.  Well, actually she said she likes Bethann.  But what about me, Jon?  Does she like the real me, or just me as Bethann?  Oh, well, what does it matter?  Either way, I will get to be with her.  And it will be fun to dress up as a girl again.

"I'll be there.  What time?"

"Come over at noon.  I'll be waiting for you.  Bye."

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