Dreaming of Cheers Standing Up to Life: Book 3 Part 23 of 23 by Tiffany Shar

Intro by Carla Ann

“Tiffany, I’ve asked you how everything is going with people and the activities you’re involved in, but you haven’t mentioned how you are coping with everything.” She emphasized the ‘you,’ when she asked that.

“Well, better than I was last year,” I started. “Way better than last year… I have a lot of friends now, and I’m not getting picked on every day.” I saw her eyes boring into me looking for something else. “Alright, I don’t know how I’m doing right now.” I told her honestly.

“What do you mean?” She asked.

“Well for one I’m really tired of everyone guessing I’m five if I wear the wrong clothes.” I told her hesitantly. I was sure my parents had filled her in with everything anyway, “Tuesday was pajama day. Mom and I had found some cute pajamas with feet on them that would fit Amy and me, so we wore them for pajama day. We really did look cute dressed like that, and I was having a lot of fun with it. That was until the sub in English class thought that I was someone’s little sister that had come them to school that day.”

I was really surprised Dr. Reynolds didn’t laugh about it, but I continued, “Then the next day the whole squad was wearing shortalls and our hair done in pigtails and I looked to be about five again. One of my best friends even brought a doll to school to play a joke on the sub that we’d had. I don’t think she knew that it really upset me though. I’m not five, I’m twelve! Amy has grown about five inches here in the last couple months, but I’m still the same height I was last year. It’s good for cheerleading stuff because people can toss me so easily… but…” I was doing my best to not go into tears over all of this. “as long as we’ve got my puberty stopped then I won’t be doing much growing. That’s all on top of the fact that I’m never going to be able to have periods like my friends… and I’m stuck with this stupid thing between my legs,” I told her with a great deal of exasperation. “I’m so tired of having to look at it, or hide it, every time I turn around. I know you can’t do anything about it till I’m eighteen – but I wish it could be gone now!” I had gone to tears now.

Dreaming of Cheers Standing Up to Life: Book 3 Part 22 of 23 by Tiffany Shar

Intro by Carla Ann

“Tiffany, I’ve asked you how everything is going with people and the activities you’re involved in, but you haven’t mentioned how you are coping with everything.” She emphasized the ‘you,’ when she asked that.

“Well, better than I was last year,” I started. “Way better than last year… I have a lot of friends now, and I’m not getting picked on every day.” I saw her eyes boring into me looking for something else. “Alright, I don’t know how I’m doing right now.” I told her honestly.

“What do you mean?” She asked.

“Well for one I’m really tired of everyone guessing I’m five if I wear the wrong clothes.” I told her hesitantly. I was sure my parents had filled her in with everything anyway, “Tuesday was pajama day. Mom and I had found some cute pajamas with feet on them that would fit Amy and me, so we wore them for pajama day. We really did look cute dressed like that, and I was having a lot of fun with it. That was until the sub in English class thought that I was someone’s little sister that had come them to school that day.”

I was really surprised Dr. Reynolds didn’t laugh about it, but I continued, “Then the next day the whole squad was wearing shortalls and our hair done in pigtails and I looked to be about five again. One of my best friends even brought a doll to school to play a joke on the sub that we’d had. I don’t think she knew that it really upset me though. I’m not five, I’m twelve! Amy has grown about five inches here in the last couple months, but I’m still the same height I was last year. It’s good for cheerleading stuff because people can toss me so easily… but…” I was doing my best to not go into tears over all of this. “as long as we’ve got my puberty stopped then I won’t be doing much growing. That’s all on top of the fact that I’m never going to be able to have periods like my friends… and I’m stuck with this stupid thing between my legs,” I told her with a great deal of exasperation. “I’m so tired of having to look at it, or hide it, every time I turn around. I know you can’t do anything about it till I’m eighteen – but I wish it could be gone now!” I had gone to tears now.

This chapter explores Michelle's transvestism in greater depth and touches upon some of the 'mysteries' of the sissy farms.

The Sissy Farm

Chapter 5.

List of Characters.

Me. Michelle A Natural transvestite sissy.
Janice My Younger sister
Aunty Bev Janice and My mother’s Sister.
Mistress Janet Headmistress of the young lady’s academy
Doctor Shirley Williams. My endocrinologist.
Miranda. A very effeminate Sissy sales assistant.
Miss Stern Miranda’s mistress who owns the shop.
Peregrine My transvestite uncle

Chapter 4 explores more of Michelle's transgenderism and and shopping fun.

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4Sissy Farm
The Sissy Farm

Chapter 4

List of Characters.

Me. Michelle A Natural transvestite sissy.

Janice My Younger sister

Aunty Bev Janice and My mother’s Sister.

Mistress Janet Headmistress of the young lady’s academy

Doctor Shirley Williams. My endocrinologist.

Miranda. A very effeminate Sissy sales assistant.

Dreaming of Cheers Standing Up to Life: Book 3 Part 21 of 23 by Tiffany Shar

Intro by Carla Ann

“Tiffany, I’ve asked you how everything is going with people and the activities you’re involved in, but you haven’t mentioned how you are coping with everything.” She emphasized the ‘you,’ when she asked that.

“Well, better than I was last year,” I started. “Way better than last year… I have a lot of friends now, and I’m not getting picked on every day.” I saw her eyes boring into me looking for something else. “Alright, I don’t know how I’m doing right now.” I told her honestly.

“What do you mean?” She asked.

“Well for one I’m really tired of everyone guessing I’m five if I wear the wrong clothes.” I told her hesitantly. I was sure my parents had filled her in with everything anyway, “Tuesday was pajama day. Mom and I had found some cute pajamas with feet on them that would fit Amy and me, so we wore them for pajama day. We really did look cute dressed like that, and I was having a lot of fun with it. That was until the sub in English class thought that I was someone’s little sister that had come them to school that day.”

I was really surprised Dr. Reynolds didn’t laugh about it, but I continued, “Then the next day the whole squad was wearing shortalls and our hair done in pigtails and I looked to be about five again. One of my best friends even brought a doll to school to play a joke on the sub that we’d had. I don’t think she knew that it really upset me though. I’m not five, I’m twelve! Amy has grown about five inches here in the last couple months, but I’m still the same height I was last year. It’s good for cheerleading stuff because people can toss me so easily… but…” I was doing my best to not go into tears over all of this. “as long as we’ve got my puberty stopped then I won’t be doing much growing. That’s all on top of the fact that I’m never going to be able to have periods like my friends… and I’m stuck with this stupid thing between my legs,” I told her with a great deal of exasperation. “I’m so tired of having to look at it, or hide it, every time I turn around. I know you can’t do anything about it till I’m eighteen – but I wish it could be gone now!” I had gone to tears now.

A story about a family with two boys aged 10 and 13, in which choice is a delusion and gender, an illusion. So far we have learned that Blair likes dressing up as a girl and that Kirk doesn't like having a New Age preacher mistake him for one.

A Teacher’s Choice

“Mommy, can I change into my play clothes?”

A story about a family with two boys aged 10 and 13, in which choice is a delusion and gender, an illusion. In the last chapter, Kirk openly and noisily shopped as a boy for clothes in the girls' department in order to distract the clerks from Blair's more furtive shopping expedition.

Chapter 4, Part 4 --- A Preacher’s Choice

Dreaming of Cheers Standing Up to Life: Book 3 Part 20 of 23 by Tiffany Shar

Intro by Carla Ann

“Tiffany, I’ve asked you how everything is going with people and the activities you’re involved in, but you haven’t mentioned how you are coping with everything.” She emphasized the ‘you,’ when she asked that.

“Well, better than I was last year,” I started. “Way better than last year… I have a lot of friends now, and I’m not getting picked on every day.” I saw her eyes boring into me looking for something else. “Alright, I don’t know how I’m doing right now.” I told her honestly.

“What do you mean?” She asked.

“Well for one I’m really tired of everyone guessing I’m five if I wear the wrong clothes.” I told her hesitantly. I was sure my parents had filled her in with everything anyway, “Tuesday was pajama day. Mom and I had found some cute pajamas with feet on them that would fit Amy and me, so we wore them for pajama day. We really did look cute dressed like that, and I was having a lot of fun with it. That was until the sub in English class thought that I was someone’s little sister that had come them to school that day.”

I was really surprised Dr. Reynolds didn’t laugh about it, but I continued, “Then the next day the whole squad was wearing shortalls and our hair done in pigtails and I looked to be about five again. One of my best friends even brought a doll to school to play a joke on the sub that we’d had. I don’t think she knew that it really upset me though. I’m not five, I’m twelve! Amy has grown about five inches here in the last couple months, but I’m still the same height I was last year. It’s good for cheerleading stuff because people can toss me so easily… but…” I was doing my best to not go into tears over all of this. “as long as we’ve got my puberty stopped then I won’t be doing much growing. That’s all on top of the fact that I’m never going to be able to have periods like my friends… and I’m stuck with this stupid thing between my legs,” I told her with a great deal of exasperation. “I’m so tired of having to look at it, or hide it, every time I turn around. I know you can’t do anything about it till I’m eighteen – but I wish it could be gone now!” I had gone to tears now.

I pushed the wheelbarrow filled with dirt over to my grandmother's flower garden.

A story about a family with two boys aged 10 and 13, in which choice is a delusion and gender, an illusion. In Chapter 1, Maggie used her sexual wiles to "persuade" her husband Laird to let her transform Blair, his effeminate younger son, into the daughter she craves.

Part 2, Chapter 2 Pierre’s Choice

The Beach House

This has got to be the craziest thing I've ever done.

I've been dressing for quite some time. I've been to parties and functions with friends dressed.

I'd been seeing a therapist for a few months. She had done a good job helping me sort things out. Am I a crossdresser? Am I transgendered?

Am I "a woman trapped in a man's body?" I could use every cliche in the book to describe the fact that I've struggled with my gender identity since I was in elementary school, maybe younger.

Chapter 2

My grandmother never needed an alarm clock to get me or Jack out of bed.

My Summer with Meg: The Age of Discovery

Chapter 1

I always looked forward to spending two weeks each summer with my grandmother at her home by the Elk River.