Dreaming of Cheers Standing Up to Life: Book 3 Part 5 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.

CHAPTER 5
A Son’s Farewell

That summer I spent with John at Martha’s Vineyard was the last time I would be in control of my own life. But at the time, I didn’t know it.

When I returned home, I simply spent one week packing to leave for Chicago where I would be starting college in the fall. It was now late July and I had a lot of things to do before fall term began. As a graduation present, my parents gave me a brand-new car, so I packed, said my farewells and drove off to Chicago.

Now I always thought myself a normal regular bloke, nice house, nice car, pretty wife etc. but this past year things have got very interesting.

CHAPTER 3
The Road to Cross Dressing

One of the best moments for a cross dresser is to imagine the time he’ll have to enjoy his female clothes. The expectation of the feeling of the fabrics against his skin is something difficult to explain in words. The best analogy I can think of, is this: thinking about the moment you’ll be wearing women’s clothing is like thinking about the beer you’ll be drinking after you finish a 20 mile hike across the desert.

INTRODUCTION

As I write these lines, I can’t help but think of the extraordinary events that have brought me here, and one question keeps popping into my head: what makes a man be a man, and what makes a woman be a woman?

You see, we may think that because a man has a penis, that makes him a man. But in reality, there are times when women are born as men, and they don’t realize that until someone comes along to show them the way.

At times, that way can be glorious, wonderful and exhilarating.

Other times, it can be a rude awakening.

This chapter describes the developments at Rosy Cottage as the extended family matures and expands. The subjects are quite diverse and touch upon some relatively contentious issues by occidental mores.

Boy hates teacher, teacher dislikes boy, boy becomes girl, girl's a senior, here's the story

Dreaming of Cheers Standing Up to Life: Book 3 Part 4 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 Thoughtstorm is when your mind randomly goes in many directions, but not like a brainstorm... rather kind of aimlessly...

One night in a small town

Its not always easy to be a small town lawyer. Unlike the big city, I actually know most of my clients away from the courthouse, and it can create some very embarrassing moments. But nothing had prepared me for this particular night.

I got a call to come to the jailhouse, and found James Mallery, who was normally a deputy, behind bars. But that wasn’t the most shocking thing. It was how he was dressed. What he was wearing would have looked good at a fancy dress dance, assuming the wearer was a girl.

In a field, there was an oak at one end, and a willow-tree at the other.

Whenever a wind moved through the field, the willow swayed in the wind, while the oak remained unmoved.

When this happened, the willow said to itself, “I wish I was as strong as the Oak, instead of bending over with every breeze“ then one day a large windstorm whipped through the field.