Tommy - The Trials and Tribulations of a Girl? - Chapter 10

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Tommy
The Trials and Tribulations of a Girl?

A Novel By Teddie S.

Copyright © 2017 Teddie S.
All Rights Reserved.


Chapter 10

New hair and a trip.

A couple of days later, as Amy and I walked into the house, my mother said, “Hi Kids.”

Amy and I both said, “Hi mom.”

That put a smile on my mother’s face. Then she said, “Tom. There’s something on your bed for you.”

“What?”, I asked.

“Just go and look.”

Amy and I walked back to my room, and there was a bag, from the store where my mom works, on my bed. I walked over to it, looked inside, and there was a box inside. I took the box out, set it on my bed, and removed the top.

Amy was looking over my shoulder, and said, “Those look almost real.”

“Yeah they do,”, I replied. “I saw them at the lingerie store when you, Maria, and I were shopping, and I said something to my mom about them.”

“So, she bought these for you?”

“Yeah. Mom shouldn't have. She said something about them being more natural than what I use.”

“Oh. Those things with the glass beads in them.”

“Yeah. These have a liquid of some kind in them.”

“Going to try them?”

“Sure.”

I stripped down to my underpants, found one of my bras, and put it on. I looked again at the box, and there was a little instruction sheet. It cautioned to protect the forms from sharp objects and also said that there was a left and right form. So, I picked it up the left form, and it had some weight to it. I said to Amy, “These are much heavier than my other forms.”

Amy took the form from me, hefted it, and said, “These do have some weight to them.”

She gave me the form back, and I placed it in my left bra cup. I felt the weight pull on my bra strap. I took the other form and placed it in my other bra cup. Then I started walking towards my closet to pick out a blouse, I stopped, and said, “Wow. Now that is different.”

“What?”, Amy asked.

“They moved with me.”

“That’s what the ladies at the store told me.”, my mother said.

I turned, looked at my room door, and my mother was standing there. My mother continued with, “They said that they moved just like real breasts.”

“Breasts move like this?”, I asked.

“I guess since I don't know how those move. Just realize that breasts are tissue and move as the woman moves.”

Amy giggled a little. Mom just headed back to the kitchen. I grinned at Amy, and said, “Take off your blouse and bra. I’m curious and want to see how yours feel.”

“You are just so bad.”, Amy said. “And no I’m not taking my blouse and bra off. You’ve already checked them out.”

“A guy can try, can’t he.”

She walked over to me, reached up and grabbed my breasts. She grinned, and said, “These feel good, maybe a little soft, but not bad.”

I kissed her, then said, “Now look who’s being bad.”

She grinned, and said, “Finish getting changed. I’m going to help mom with dinner.”

I finished changing and went into the kitchen, as I walked in, my mother saw me, and asked, “Well. Do you like them?”

“They feel different and better than the old ones.”, I replied. “It's going to take a little while to get used to their weight and how they move. But I think they're much better. Thanks, mom. But you shouldn't have. They had to be expensive.”

“Yes. But in a way, you paid for them.”

“I did?”

My mother continued with, “Amy. I'm also telling you this because one day you’ll be Tom's wife.”

Looking back at me, my mother said, “Now, there’s something that your father and I think it’s time that you know. Your Grandmother and Grandfather Young set up a trust fund for you and your cousins on your father’s side of the family. And you’re not supposed to receive any of it until your twenty-five, or twenty-one and married.

“But your father and I decided that you could use some of that money before then for school and other things. So, we’re using some of our money as something like a no-interest loan. We’re paying for a lot of things, like your college, and some other things. The only thing that we ask of you is when you receive your trust that you pay us back.

“We should have told you first, but we just did it. We hope that you understand.”

“Mom.”, I said. “I understand. But you guys didn’t need to do that. I’m still working part-time for Uncle Mark. And I have money.”

“We know honey. You’re paying for some of your school expenses out of what you're earning, and for your car.” Then looking at Amy, she added, “And we know that you have other special expenses.”

“Special expenses?”

“Like the ring you gave Amy. And other nice things you do for her.”

“You’re right. And I will pay you guys back.”

“Honey. I know you will.”

We both gave my mother a big hug and then went into the den. I sat there quietly for a while, then Amy asked, “Honey what's wrong?”

“Nothing. I guess.”, I said. “I’m just thinking about this trust fund. And my mom and dad using their money for me.”

“Honey. It’s what parents do for their children. Help them. My parents, along with some college loans, are paying for my college.”

“You’re right. But I want to be sure to pay my folks back.”

“If I know you, and I think I do, that won’t be a problem. After being around you like I have, you are a great son.”

“Or, a daughter.”, I said with a smile.

“Yeah. Or, a daughter.”

When my dad came home, I met him in the kitchen, gave him a big hug, a kiss on the cheek, and said, “Thanks, Daddy.”

“For what?”, he said. “I didn’t do anything.”

“Mom told me about the trust fund today.”

After dinner, Amy and I were helping my mother clean the kitchen. My mother asked, “You’ve been letting your hair grow. Haven’t you?”

“Yes.”, I replied.

“It’s because you’d like to use your hair for Tammy. Am I right?”

“Yeah. The only thing is, switching from a boy's style to a girl's style.”

“That could be a problem.”

“Guys are beginning to wear their hair longer, but I don’t know if I could let it grow long enough to look good in a girl’s style. And I’m thinking of getting it cut.”

“Honey.”, Amy said. “Just let it grow, and we’ll see what we can do with it.”

“We’ll see.”

My mother asked, “How old is your wig?”

“Well, it’s the one that Aunt Linda gave me like six years ago.”

“You’ve taken good care of it, and it still looks nice.”

“It’s real hair, so taking care of it has been fairly easy.”

“Would you like a new one?”

“Sure. But aren’t real hair wigs expensive?”

“Yes, but the store is having a sale on them. And if you also take my employee discount, it won’t be too bad.”

“How can I get one?”

“One of the hairdressers is a good friend. She's the one that's worked on your wig after we had the car accident and you wanted to be Tammy again.”

“She knows. Doesn’t she?”

“Yes. She guessed after the accident. And she won’t say anything.”

“Honey.”, Amy said. “You know, a new wig would allow you to have some of the newer styles.”

“Yeah.”, I replied. “I guess you’re right. When can we do it.”

“Let me talk to her, and we’ll see what we can set up.

Three days later we, mom, Amy, and the Tammy me, were walking into mom’s store at nine in the morning. It was an hour before the store opened, so we used the employee’s entrance.

We went up to the floor where the beauty shop was, and mom introduced us to Mrs. Taylor. The first thing she did, was to look at both Amy and me with a puzzled look. Then she said to my mother, “Jean. Are you pulling my leg?”

“What do you mean Helen?”

“Isn’t one of these two supposed to be your son?”

I saw mom smile, and then say, “Interesting isn’t it? He can look so good as a girl, that no one can tell him from a real girl. Even when he’s standing next to a real girl.”

“Okay. Which one of you isn’t a real girl?”

I slowly raised my hand. Mrs. Taylor shook her head, and said, “No way.”

I reached up and removed my wig.

“Jean.”, Mrs. Taylor said. “You showed me the pictures when I worked on the wig, and I couldn’t believe it. Now, she’s standing in front of me, and I still don’t believe it.”

Then Mrs. Taylor, looking at me, and said, “Honey. Before you took that wig off, I didn't see any sign of a boy. I had two beautiful, blue-eyed, blond, girls standing in front of me.

“So, you would like a new wig?”

“It would be nice.”, I replied. “I'd like to use my hair, and switch between a boy's look and a girl's look. But until it grows out enough a wig would be good.”

“You even sound like a girl.” Then looking at Amy, she asked, “And who is this pretty young thing?”

Amy smiled, and said, “I’m Amy. I’m Tom’s fiancee.”

“Fiancee! My dear. He’s so lucky to have a girl like you. That, if I’m correct, enjoys this side of him.”

“Yes, ma'am. I do.”

“Let’s drop the formalities. Call me Helen.” Looking at me again, she said, “So, it’s Tammy right?”

“Yes.”, I replied.

“Are you looking for something in the same color?

“Yes, or as close to it as possible.”

“Maybe with some highlights?”

“That might look good.”

“And you want to be able to put it into some different styles?”

“Yes, sometimes I wore my old wig with a ponytail, and I'd like to do that again. Plus do other styles.”

Then Helen, as she started walking out of her work area, said, “When your mother said that you were coming in, I ordered a couple of wigs in and I think I have just what the doctor ordered. And I think it will look nice on you. I’ll be right back.”

Helen was back in a few minutes carrying a very long blond wig, and it already had highlights. She set it down, then placed a wig cap over my head.

I asked, “What’s that for?”

“It’s a wig cap. You should use one. It protects your hair from the wig. It also flattens your hair, and you can tuck your hair under it. Plus, it gives the wig something to grip. It may also make the wig feel better.”

“Okay. I’ll try it.”

Then Helen placed the wig cap on me, pushed my hair up under it, then she placed the wig on my head. She fussed with it a little, stood back, and ask my mom and Amy, “Well ladies. How does this look on her?”

Amy was smiling, actually grinning. My mother said, “That looks wonderful. It’s close to her old one, but looks so much better.”

“This is a lace cap wig, and it’s much longer than the old one. I wouldn't trim this wig at all. The length looks good for the longer hairstyles. It falls well below her shoulders and will be easy to put into a lot of different styles. Now, let me show you a couple of styles that will look nice.”


Helen showed us some cute styles, and the one that looked really cute, but was a little formal, was a low ponytail, with strands of hair coming down in front of my ears. She called it a beehive. Mom and Amy loved it. Then she showed us a few other styles that looked really nice.

The last style that she showed us was another ponytail, that came down and covered my ears. I really liked it, and since I was going to wear the new wig, I had her leave it in.

Helen finally told us that if I ever needed a fancy hairstyle, either with the wig or my hair, to come back and see her.

We thanked her, and mom paid her for the wig. Helen turned down a tip that my mother offered her. Then she put my old wig on a foam head, placed it in a box, and told me to keep the new wig on the form when I wasn’t wearing it.

I hugged Helen and thanked her for her work.

Then my mother walked with us to where she was working that day. As we were getting ready to say goodbye, my mother said, “Honey. Those glasses are cute on you. But, they’re really out of style.”

I looked at Amy, and she said, “Your mother's right. You need a new pair of glasses that are up to date.”

We hugged my mother goodbye, and Amy and I headed home. With a stop at a costume shop to find me a new pair of glasses.

The rest of winter quarter went really well for both Amy and me. Our grades were very good. Also, no more blizzards.

In the short, two-week, break between winter and spring quarters, Amy and I did our usual things. Even though it was late March, and still cold, we hiked in the park. I think hiking in the woods was one of our favorite things to do together. Maybe we'll need to take up backpacking, and go camping. I do like sharing a sleeping bag with her.

We were able to go shopping with Maria again. She hadn’t seen the new wig until that day, and she just loved the way it changed my look. Then we ran into Larry at the five and dime’s lunch counter.

He walked up to us, and said, “Hi guys.”

Amy, said, “Hi Larry. What are you up to?”

“We just finished lunch and are going to a movie.”

Amy looked around, and said, “We?”

“Kelly. My date. She’s in the ladies.”

Just then his cute redheaded girlfriend walked up to us, grabbed Larry’s arm, and said, “Hi honey. Who’s this?”

“These are friends from high school. Kelly, this is Amy, she's engaged to my best friend, Tom. Maria is another friend. And, this is Tammy, she's not from around here and is Tom's cousin. Everyone this is Kelly O'Brien. She's a second-year psych major.”

We exchanged greetings. But I think Kelly wasn’t happy that she found Larry talking to three girls, as she said, “Honey. We’d better go, or we’ll miss the movie.”

“Okay. Catch you guys later.”, Larry said.

As they walked away, I said, “Hmm. The older woman. And I think I see something more there than just a date.”

“I think you’re right.”, Amy said. “That ‘honey’ had some feeling to it.”

“And the way he put his arm around her was cute.”

“Guys.”, Maria said. “There’s something that I need to tell you.”

“Is something wrong?”, Amy asked.

“Ah. No. Something’s right.”

“Something’s right?”

“Yeah. Mark Roberts and I have been seeing each other for a while, and it’s going ... shall we say, it’s going very well.”

Mark Roberts was a friend from school and has a twin brother, Max.

“Just when were you going to tell us this?”

“I guess now.”

“Well, any time you two want to double, let us know.”

One day when we were at Amy’s house, and the mail came, so being a gentleman, yes, I was Tom, I went out and brought it in. Amy looked through the mail, and she had a letter from Polly Smyth. That’s the girl from Minnesota, where Amy had lived for those four years, and she was having the wedding that Amy is supposed to be a bride's maid for.

Amy opened the letter, and read it. I could tell by the expression on her face that it must be interesting. When she was done reading it, she said, “Hmm. Not good.”

“What’s wrong.”, I asked.

“It seems that Polly’s mother is running this wedding. I’m not surprised. Her mother is a real bossy person. I know she doesn’t like the guy that Polly is marrying. She also wouldn’t let Polly choose her wedding dress.

“She also said, that the bride's maid dresses aren't great. And that she's hardly had any input into the wedding.”

“That’s not right.”, I said. “It’s Polly’s day. She should be planning it, and making it the way she wants it.”

“I know.”

Spring quarter started, and it was school, studying, hikes in the woods, meeting up with friends, double dating with Mark and Maria, and Larry and Kelly, and doing other stuff that college-age couples do. Of course, there was Tammy time, some shopping, and just having fun.

Spring quarter ended on June 12, and Polly’s wedding was ten days later. So, we had to plan on how to get there. We could drive, and that would take two days, coming and going. That could be fun. We could take the train, but the six-hour layover in Chicago wouldn't be much fun. Not enough time to really do anything. Or, we could fly, and be there in a couple of hours.

Our flight arrived on time, and after retrieving our luggage, we grabbed a taxi. The ride to our hotel took about a half an hour, and it was a really a nice hotel. The bridal party was staying here, and the bride’s parents were paying for the bride’s maids, and the reception was also going to be here.

Amy had me stay with the luggage as she checked us in. When she came back, she said, “We might have a small problem.”

“What?”, I asked. “No rooms.”

“No. Only one room.”

“How come?”

“I may have messed up.”

“How?”

“When I wrote Polly and told her that I would be happy to be a bridesmaid. I told her that I was going to bring a friend, but I didn't tell her that we'd needed two rooms. The hotel is booked up, and they don't have any other rooms. So, we have a room with two beds.”

As she was telling me this, she had a look on her face that told me that she wasn't telling me everything. She has a real problem telling a lie, or even a little white lie, her facial expression gives her away.

I looked at her, and said, “Amylin. You planned this didn’t you?”

“Ah.”, Amy replied. “Maybe.”

“Honey?”

“Yeah. I did.”

I shook my head, and said, “Amy. Amy. Amy. What am I going to do with you? We told our parents that we'd have separate rooms.”

“I’m sorry.” And the tears started.

I took her to the side of the hotel lobby, wiped the tears away, and even though I knew the answer, I asked, “Why?”

“I ... I wanted to spend the night with you.”

“I figured that. We promised your parents that we’d behave, and stay in separate rooms.”

“I know. Hate me?”

“No. I could never hate you.”

“You ... You might after I tell you the rest.”

“What now?”

“Let's go up to the room, and I'll tell you.”

A bellhop took us and our luggage up to our room. A very nice room, with two king-size beds, a large bathroom, television, a nice vanity table with lighted mirror, and a couple of overstuffed chairs. The bellhop hung our two garment bags in an alcove, placed our two suitcases on separate luggage racks, and our overnight cases in the bathroom. And I gave him a nice tip.

After he had left, I said, “Well, we don't have separate rooms. But we do have separate beds.”

Amy didn't say anything but looked a little hurt.

“Then again.”, I said. “We’ve shared a bed before. So, I guess we can do it again.

“Now, what’s this other thing?”

As she sat down on one of the beds, she said, “Open your suitcase.”

I gave her a look of, do I really want to. Then I walked over to my suitcase and opened it. I looked at what was inside, then I looked at Amy, and said, “What the hell!?”

As she whispered, “I’m sorry.” And the tears started.

“Why?”

“I ... I wanted Tammy to come with me.”

“Why?”

“I ... I thought it would be fun. You, the Tammy you, could see a wedding from a girl’s point of view.”

“Amy. I should spank you.”

“You wouldn’t!”

“I just might. When did you switch my clothes for Tammy’s?”

“Yesterday. When you were getting your things ready to pack, and I was sitting there watching you. You had all of your things laid out, but not packed. Then your mother called for you to come and run an errand for her. I’d told you that I’d finish packing for you. I quickly put your stuff back, and packed Tammy’s things.”

“Well. I guess I still have my suit, and I can buy a few things while we're here.”

She just shook her head no.

“You didn’t?”, I said.

She just nodded yes. I walked over and opened my garment bag. No suit. Just three of Tammy’s better outfits. I looked at Amy and just shook my head. Then said, “Amylin.”

She looked at me with tears in her eyes. I walked over to my suitcase and started looking at what was there. My wig. My girl’s underwear, bras, and panties. My forms. A garter belt. Nylons. Two skirts. Two pairs of shorts. And a pair of jeans.

Then I walked over to the alcove and looked at what was in my garment bag. Amy had picked my pink suit, a couple of skirts, a couple of blouses, and two sweaters. In the bottom of my garment bag, along with a purse, were three pairs of shoes, my flats, my sneakers, and my dressy tan heels with an ankle strap.

I walked back over, sat down next to her, and put my arm around her. She looked at me, and said, “You’re really mad. Aren’t you?”

“Amy. Love. Why didn’t you say something?”

“Huh?”

“Why didn’t you talk to me about this crazy idea of yours?”

“You would have said no.”

“You think? Maybe I would have thought it would be fun.”

“Really!?”

“Maybe. Now, I don’t have anything dressy to wear for the wedding.”

“Ah. They have stores here too.”

“Oh. So you were planning on a shopping trip with Tammy?”

“Sort of.”

“Won’t I need a pair of dressy shoes?”

“Uh huh. Heels.

“Yeah. I know that they have shoe stores here too. What about makeup?”

“In my overnight bag.”

“Jewelry?”

“In a case, that’s in your suitcase, and your glasses are in it too.”

“Thought of everything. Didn’t you?”

“Uh huh.”

“Did you bring protection with you?”

“No. Did you?”

“I don’t know. Did I?”

“You did. Didn’t you?”

“Of course.”

“Why don’t you unpack, and I’ll call Polly and tell her where here. Then you can find Tammy, and we’ll go shopping.”

“You sure recovered from all that crying really quick.”

She smiled that contagious smile of hers, and said, “Sure. I figured that you’d love the idea. So, I wasn’t too worried.”

“You are just so bad. Just what am I going to do with you?”

“Love me.”

“Wait a minute! Did my mother know anything about this?”

With a sly smile, Amy said, “Maybe.”

“I think she did. It was too much of a coincident that she called me to help her when she did. The errand that she had sent me on wasn’t that important.”

“You’re right. She even helped me pack your things.”

“Wait until I see her.”

As I unpacked, Amy called Polly. The conversation went something like this from Amy’s side.

“Hi, Polly. It's Amy.” ... “Yeah, we’re at the hotel.” ... “Tomorrow at one. Let me write the address down.” ... “Okay. Got it.” ... “Oh yeah. Tommy is taking a summer class, and can't miss any of it, so I brought his cousin Tammy.” ... “Yeah. I think she'd like that.” ... “Okay. We'll see you tomorrow at one at the bridal shop.” ... “Love you to girlfriend.”

“What will Tammy like?”, I asked.

“Oh. To go to the bachelorette party on Friday night.”

“Aren’t those a little wild?”

“I don't know. I've never been to one. Polly is a good Catholic girl and quiet. So, it may not be crazy. Probably, just sitting around talking, and playing games. I think everyone in the bridal party is under twenty-one, so no one should be drinking.”

“I’ve heard it’s the quiet ones that go a little wild at these things. Mary did at hers.”

“Yeah. Was Mary that quiet of a girl?”

“Most of the time.”

“Why don't you find Tammy. Then we'll get some lunch, and afterward see if we can find you a nice dress and some shoes for the wedding. I'd also wear nylons since we'll be shoe shopping.”

I found Tammy. Anymore it was so easy to become her. She just loved to be out and about. I went with the pink skirt, a matching sweater, and the black flats. My usual daytime makeup, and of course my glasses. I just brushed my wig into a nice look.

As we were getting ready to walk out of the room, Amy said, “Don’t forget your engagement ring.”

We had lunch, then stopped at the front desk and asked if there was any place nearby where we could buy an upscale outfit and shoes.

The desk clerk told us that there was a shopping district not too far away. She gave us directions and said that we should find what we were looking for in that area.

It was a short distance from the hotel, to the shopping district and it was a nice day, so we decided to walk. Once we were in the shopping area, we window shopped. As we were walking past a lingerie shop, Amy stopped and looked at something in the window.

“What’s so interesting?”, I asked.

“You know that Tammy’s one problem is that you don’t have a girl’s hips or butt?”, she replied.

“Yeah.”

“See these.”, she said pointing at the window. “These would give you what you’re missing.”

I looked in the window, and saw what she was pointing at, and asked, “What are they?”

“They’re called a booty booster. It will lift your booty, and add inches to your hips. They’d make everything that you wear look better.”

“Interesting.”

“Want to check them out?”

“Sure.”

We went into the shop and looked at all kinds of things that can, as Amy said, boost your booty. We settled on one that lifts and separates your bum, and with padding that adds inches to both your hips and bum. We bought it, and they let me use a changing room to put it on. When I came back out of the changing room, Amy had me spin around. When I was facing her again, she smiled, and said, “Nice. Very nice. It really adds to your look.”

We walked a little further down the street and looked in the windows of a couple of dress shops. It was at the third store that we saw it. I think Amy and I saw it at the same time. It was a satin, navy blue, midi dress with three-quarter sleeves. The skirt was flared and knee length. It had buttons from the hem to the collar. Amy said, “I love it.”

“Me too.”, I replied.

We went into the store and found that they had it in my size. I tried it on and modeled it for Amy. She smiled, and said, “That's it.”

That was the quickest that I’ve ever found anything that I liked.

Also, we were in luck that this store also carried shoes, and we found a pair of three-inch pumps that would go great with this dress. I also found that I was going to need to practice in these shoes before Saturday. I'd never worn heels this high before and felt unstable in them.

We also found something that Amy thought was downright cute. She called them booties. They were like a half boot, they had a pointy toe, low heel, and came up just over the ankle. The pair that I picked out was tan with a buckle across the front.

If we had time, later on, we'd be back. This shop had a lot of cute things.

We took everything that we purchased back to the hotel, and once back there I tried walking in the heels. It was really a different experience. It gave me a feeling of walking on my toes. Amy told me to try taking shorter steps and placing one foot in front of the other.

Then Amy said, “Remember. You’ll probably have to dance in them.”

~o~O~o~

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Comments

That wig style is sooo 60's

I'm guessing that there will be some further surprises at the party and the wedding. Partners like Amy are must be rarer then hen's teeth. Tom is a lucky guy/girl. Fun story that startles me back to remembering that era when some of the lifestyle is described.

Thanks, Wendy K.

Thanks, Wendy K.

It's been fun writing it and remembering those times.

Teddie

SOMEbody

TheCropredyKid's picture

...is gonna get grabby at the reception, and Tammy and/or Amy is gonna lay him out.

As to which of them will be the grabbee - as the bookie on "Bullwinkle" said about the "upcoming big contest" - "Woild War T'ree? Six to five and pick 'em."

Also, now that i think, the bachelorette party is fraught with possibilities...

 
 
 
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Enjoy This Story

My5InchFMHeels's picture

I really have enjoyed this story and all the twists and turns that Mary, Mom, Amy and Maria have come up with for Tammy. Something about the bachlorette party that caught my attention though was the mention of Age. I grew up in the 70's and I remember it being 18 to drink at the time, It made me wonder if that wasn't out of place, of if it had changed between the 60s and 70s and reverted back later in the 80's.

It depends on where you live

It depends on where you live in the US. Until the 26th Amendment was ratified in 1971 it was anywhere from 18 to 21. I remembered it as being 21.

The stinkers

Jamie Lee's picture

Mom and Amy knew Tom would nix the idea of Tammy going to the wedding. So, send the boy on a fools earned and do as mom and Amy did. Tammy was going to the wedding, only she didn't know it yet.

Maybe Amy could do with a spanking for her roll in getting Tammy to the wedding. But that might lead to Tom having to take care of other business.

"Maybe," seems to be the minx's one word which denotes that she's been caught doing something which get Tammy involved. And it's cute, it's not admitting guilt but not denying it either. Wonder what Tom is going to say to his mom for her duplicity in getting Tammy to the wedding?

Dance? Amy said dance? Oh isn't Tammy in a panic now? Amy better chain her to something solid in the room. Or stay with Tammy at r he wedding.

Others have feelings too.