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  • Caught For the Last Time Ch. 08

Caught For the Last Time Ch. 08

12

In the week that followed Tommy's leaving, I kind of felt that a void was created. Seeing him and speaking with him as both Tommy and Tammi, rather than just hearing stories of him, had a profound impact on me. It made me a little jealous and a little sad.

I was basically dwelling on the question of, now what? I can dress at home whenever I want, have an overly supportive wife, our sex is good, no, it is great, I can shop almost at will and I've been out dressed and survived.

Kelsey was sensing this in me as I did not dress as much during the week. I was also a bit distant in my thoughts, so she asked me one night,

"What's up. I've been seeing a little less of Jamie. I don't mind that, but that little bounce in your step is not there."

I shared with her my thoughts and she said,

"Maybe we need to do something different."

"How so?"

"When we went out with Tammi and Sally to the restaurant, you first felt nervous, then excited and then comfortable."

"Yes. It ended up being a lot easier than I thought."

"Why was that do you suppose?"

"Well, going to a place where no one knew us was a plus, and Tammi gave me encouragement. You know, if she could do it, I could do it."

"Anything else?"

"I got to stay be Jamie from when we left the house that night, then to Sally's and then the restaurant and home. It was probably 5 hours being Jamie in front of other people while being out. That made a difference."

"It was a big step and you did well."

Kelsey then added, "What if we took a trip somewhere where you could be Jamie for a long period of time again, maybe several days in a row?"

I thought for a minute and replied, "That might be fun. You know, going to work all day, and coming home and changing for a few hours is great and all. But being able to be dressed and being Jamie for an extended period of time might be a good solution to the funk I am in right now."

Kelsey then added, "Truthfully, I don't have any real desire to go to Chicago where Tommy lives, but maybe we could get a nice package deal for some place fun like Las Vegas for a few days. We both have enough vacation time accumulated."

We talked through the idea a while and then Kelsey, the consummate planner began looking at dates and found that we could get good airfare to Vegas just over a month from now. Anything closer was way too expensive plus too difficult to get off from work.

While she was looking at that, I sent an email to Tommy, asking if he had any ideas. Tommy replied with an essay of ideas. He had been to Vegas a number of times.

He said in one part, "The biggest challenge in Vegas is deciding where to stay. Staying at the Bellagio is awesome, but changing in your room, taking an elevator with other people to the lobby, walking a mile through the casino dressed, returning to the hotel, walking another mile, showing your room key to hotel security and knowing you are on a ton of casino cameras is a big step. I personally love it now but it was a challenge for me at first. Make that your second trip "

That paragraph resonated with me. Realistically, I had trouble walking 100 feet through a restaurant hiding behind him. Walking through a casino with all those beautiful people could be a challenge I wasn't ready for.

So we began looking at other casinos to stay at. In Vegas, it probably didn't matter which one we stayed in for location purposes because we were renting a car to get around. Las Vegas was just so big.

While Kelsey worked on the travel arrangements, I started to "train." I now had a goal.

It was like the Rocky training scenes as I began thinking through every day and night, figuring out what to wear, pretending that I was ...no, not pretending, but being Jamie each day and night.

First up, I realized that I needed to get out more as Jamie. As excited as I was about taking a trip, I had only been out of the house once.

I shared this thought with Kelsey and said, "We're going out this Tuesday night again to that same restaurant, but I'm taking the role of Tammi."

"I like that," she replied. "Plus you know the hostess and they were all friendly. Good idea."

Since we now knew the style of clothes they wore in that restaurant, I took my outfit down a notch to a nice casual dress. That would blend in better with the patrons. We were a bit overdressed the first time.

The same hostess greeted us, took my hand, complimented me and the Kelsey on our outfits and sat us at a nice table. "I am so glad you came back. I hope you two become regulars."

The restaurant was much easier to walk through this time and I loved it this time.

I tried to never once think of myself as anyone but Jamie and that made me feel that much more comfortable being there. In fact, at one time my wife leaned in and asked, "Are you flirting with our waiter?"

"I didn't think I was," I replied, "I'm really sorry if it seemed that way."

"No, it was actually cute. You seem so at ease to night. I love seeing that."

After a wonderful night at the restaurant, Kelsey suggested we take a walk through a nice area of the downtown area. I was nervous but agreed.

The shops had just closed up and there was very little foot traffic. We did some window shopping, stopping and looking along the way. It was such a nice night to be out.

That little walk was more important than I though. I could now see a reflection of all of me in the large store windows as we walked and stopped at different windows.

I was shocked to see how much I looked like guy standing there in my reflection as compared with my wife. Depression immediately set in.

"What am I doing wrong?" I asked.

Realistically, I knew I was never going to look like Kelsey, but I could definitely do better than this.

"Hun, try keeping your shoulders back further for starters." That little adjustment made a big difference.

I did that for a couple of minutes, then quickly forgot and slipped out of that posture back to my comfortable guy stance.

My reflection got worse again. Why didn't my reflection look like I felt? This was not easy.

We made other adjustments as well, like learning how to hold my shoulder purse strap with my right hand in order to keep my guy elbows closer to my body. "Closer, no, even closer, that's better," she would say.

The large windows caused me to continually check and re-check my posture and poise. It must have been annoying for my wife.

But as we continued the walk, the "me" in the windows slowly looked at least a little better.

"Looking good girl," my wife said as I kept trying to work on my posture. She was so encouraging. There were signs of progress.

At home that night, I was more upbeat having been out and having added walking to my experience. But I really wanted to keep the Jamie theme going. I quietly slipped into one of my prettier nightgowns and waited in bed for Kelsey.

I took a real passive role that night and as Kelsey ravished every inch of me, I made sure than I was expressing myself vocally to her. "I love it when you play with my nipples."

"So my girl likes this. I love hearing that," she said as she lightly kissed and bit my nipples through the nightie.

"You always feel so good when you're on me," I whispered as she stayed on top of me, grinding her pelvis into me.

I knew there was a passionate Jamie deeper inside me and I wanted so bad for her to come out. I just needed to take more positive steps on my own and give her voice.

++++++++++++++++++++

Getting out to restaurants then became a weekly thing. Mid-weeks were an easy night because of smaller crowds, and we got a list from Tammi of places her friends recommended. They were perfect choices.

We always added in a stroll somewhere, either at the beginning or end of the night, just to work on my poise. This was an ongoing process, even at home. I watched women walk when we were out as well as on TV. There were so many different styles and I needed to find mine.

I vividly remember one night when we were out walking that Kelsey secretly videotaped me for about 10 seconds and then showed me. I looked awful.

I then said, "I want a do over." Even with me focusing on my walking, I still need improvement after she shot another sequence. This was not easy.

"Let's do it again," I said. We critiqued each walk. I swear I walked down that same block ten times before I began to feel even comfortable with what it looked like.

Truthfully, I really felt that I was already exaggerating my movements, but it wasn't until I saw the final video that I realized I needed to go that bold to look right. Feeling like a girl and looking like one when walking are two different things. Maybe Vegas was a bad idea.

On another night, we hit a younger place that Tommy suggested. We made that a real casual jeans night as this place had booths and great music. For some shape, I had put on the hip pads and the body shaper which really helped me in the middle and push out my boobs.

I loved this casual look and so did a few of the female wait staff who commented with phrases like, "I hate you girl. You've got better curves that me."

That evening was a quick meal so we ventured into our first store together after dinner.

It was one of those exterior mall complexes, so walking about was so easy, like window shopping. We selected two shops to visit. Lane Bryant and Chicos. I had been to both in guy mode before but never dressed.

Lane Bryant was easy, and realistically, not the place I needed to shop, but could. "Shoulders back hun," Kelsey whispered as we were about to enter the store. This girl stuff was not easy.

As soon as we entered we were greeted with, "Good evening ladies!"

Wow, that was so nice.

"Is there something special we can help you with?" they both asked almost together.

"We're going to Vegas in two weeks and Jamie needs a dress that will just pop! Any suggestions?"

The younger sales associated thought for a bit and pulled out 3 different dresses and a couple of tops as well.

"Let me set up a room for you!"

This was freaking awesome.

After each outfit, the associate made me come out and show her. She either made a size change or came back with yet another dress.

While the Lane Bryant dresses did not really do anything for me, I loved one of the tops. It was sparkly, fit my shoulders well and went well with my skinny jeans. We actually took a few pictures of me in it. We did buy it, plus it was on sale.

And the sales associate said, "Please come back any time. You two were a delight!"

Chico's was no different. They have weird sizing and the associate explained I was probably a 3. I was thrilled until I realized they start at zero and go up to a 3. The 3 was my size.

The more I looked and tried a few things on, the more I realized this is probably where Sally shopped. Too many outfits looked like ones I already had so we didn't buy anything there. I guess I was already a Chico's girl. But it was a fun experience none the less.

After our little shopping excursion, my wife suggested that I stop by Kohl's and check with Erin. With Kelsey having met Erin, and vice versus, I think I earned an element of trust.

After work I stopped in at Kohls, and there she was. "Yes, you're back!" she said.

I then said to Erin, "We are heading to Las Vegas where it will be hot and I'm looking for a couple of evening outfits as well as a few day ones. Any ideas?"

Erin located about 4 tops that I liked and a several skirts that worked well with them. One of the tops reminded me of the gold top Tammi told us of in her story, so I had to get that one as well. I tried them on with my bra and panties I was wearing and Erin gave her approval.

"You and your wife are my favorite customers now. You seem to have so much fun together. And now Vegas. Promise me..."

"Pictures...yes, I will bring you lots of them."

Before I left, Erin stopped me and said, "Wait, I have an idea, my friend Joy works at a boutique about 5 miles from here. It's got real nice designer stuff and sometimes amazing sales. She works Thursday through Saturday. I'll send her a text tonight if that's OK with you. And bring pictures, and maybe even your wig and shoes to try things on."

I told Kelsey but she couldn't join me and said, "Go, but don't break the bank."

On Thursday night after work, I slipped on a bra under my work shirt and headed north. The boutique was so small I actually drove by it once by mistake.

When I arrived, there were no customers in the store, just the sales associate...and the store was small, real small. As I wandered in I got a very friendly "Hello, my name is Joy, thank you for stopping by. Is there anything I can help you with?"

Joy reminded me so much of Erin. I liked that a lot.

I introduced myself and told her about my Vegas trip. She said, "Oh good, it's you. Joy texted me the other night. I am so glad you came, she even gave me your size."

I showed her some of my pictures on my phone and she loved them.

"That's wonderful. This is a perfect time to be in. We have some great sales going on. Let me show you around and then you can browse for a while."

"Let's start with the dresses. The size you are looking for are right in this area."

"Over here we have our skirts in all lengths and colors. And over here we have the blouses and tops. They are always popular because you can mix and match and have so much fun."

"On this side of the store we have our special occasion or what I like to call party dresses...we have a big sale on these right now because we are well past the holiday season. And over on these racks are the long, more formal dresses. Some of my favorite designer dresses are in this area."

"I will give you some time to browse first, but feel free to ask me any questions."

Off she went and off I went. For 30 minutes I meticulously went through every dress, skirt and blouse in my size, as well as looking a size up and down because different manufacturers run differently in sizes.

While I was shopping only one person came in and she stayed for all but 10 minutes. In a small store like this, you get to see and hear every conversation.

After a while Joy stopped over and said, "I hope you do not mind but I was trying to imagine which outfits would look the best on you once I saw you and your pictures, and these came to mind."

She then asked, "Is it OK to start with these for a fitting of sorts and we can go from there?"

Did I mind? This was like a dream come true.

"Joy, before we start, I brought a wig and shoes with me, should I get those?"

"Absolutely, that will definitely help with the fit. And that was good thinking on your part to wear your bra tonight."

And I thought the bra could not be seen...oh well.

What's so different about the boutique is that they had this great little area to try things on. Once you changed into the outfit, you were able to step out of your changing room into a common area with lots and lots of mirrors. It was wonderful.

Joy kept my enthusiasm level high even when the dress did not look good on me or did not fit. What was nice is that Joy always made it the dress's fault if it did not look good on me. She was good.

We tried different colors and different lengths and styles. After trying on a half dozen dresses she said "It seems that the A line dresses fit you best, with a bit of an empire style to it."

After over an hour, we decided on one dress and kept another one aside as a back-up. I was very pleased and could have easily selected five dresses, but I only needed one.

I can best describe my selection as a little black cocktail dress. It had cute straps, cut a little shorter than I expected would look good on me...especially with the heels, and had some subtle glitter on it.

"But before you go", Joy asked, "I have a favor ask. Would you try on several of these longer formal outfits? Some of these just came in and I have yet to see them on anyone. I think someone with your height would look great in them."

Let's see I thought. You are asking me if I wouldn't mind trying on ultra-expensive designer dresses? I smiled and said, "I would be delighted to do it."

For nearly an hour I tried on 8 different gowns. From full frontal coverage to spaghetti straps, they were absolutely gorgeous. And with each one, Joy spent time critiquing each dress for me. What she liked about each one and what she did not like.

And she also helped with my poise. Try and move your shoulders back a bit more. If you can, squeeze your elbows in closer to your body. Stand sideways and turn your head this way. Try walking by placing one foot directly in front of the other and that will make your hips swing a bit more. All things I thought I was already doing. Oh well. This was going to be a long process.

She then told me I had a real knack at being a model and she would love to have me in more often to try on her new arrivals as well as some of her own designs. I did not know if she was serious or not, but I did not care...I loved the attention.

When I arrived home, Kelsey was as excited to hear about my story as well as see the new dress. I quickly tossed it on with my wig and heels, and she said it was elegant and the fit was perfect. Then she said coyly, "Let's try it tomorrow night at home with some real nice make-up. I think we could each use a Jamie night."

Tomorrow could not come soon enough. Shortly after I got home from work and had a bite to eat, I changed into my black bra and panties. Kelsey worked on my make-up. She was really going for the sultry evening look. Even standing there with just my wig, make-up, with the black bra with my silicon inserts and panties, I was excited.

Kelsey stood up beside me and began caressing my body just as I would hers. "I love you even in just these."

She then helped me slide on the hip pads and body shaper, and then the dress. This looked better than I ever imagined. Kelsey took dozens pictures, including some of my holding a glass of wine in different settings. We took simple pictures and sexy ones. It was so much fun. But we also deleted dozens and took more until I felt that I had each pose down. It's tough looking into a camera and smiling.

"Let's go for a drive," she said.

"But it's early."

"All the better."

As we started out, Kelsey drove and simply said, walking around Vegas in that outfit will turn heads. Let's get used to it a little bit." I was a bit panicked.

As we drove, we talked more about Vegas. I then realized she was heading in the direction of the boutique shop.

"Are we going back to the boutique?"

"Yes we are."

Kelsey purposely parked across the street and we had to walk about a block to get to the store.

"Look at the babe in the windows," she exclaimed.

I could not believe it but I was actually pulling it off. It almost looked like two girls walking down the street. The heels, the dress, and the excitement of being out was now all coming together.

When we walked in I was surprised to see both Joy and Erin from Kohl's there. "We wanted to surprise you, and see you all dressed. Let's see!"

I modeled the outfit for them and they took a bunch of pictures.

Joy then said, "Erin and I talked on last night and wanted your wife to see you in some of the gowns you tried on. Hope you don't mind. You looked so good in them."

"I've selected these four outfits for you to try on first. The first is a bridesmaid dress. Given your color scheme I have tried a deep purple and the fabric is a soft, free flowing jersey. There is some ruching at the bodice and I think the lines will work well with you.

I felt like I was on Say Yes to the Dress. My wife and Erin were sitting outside in the viewing area and Joy was working with me getting everything perfect. It is so nice when someone knows your size and what style works best on you. I have seen brides and bridesmaids walk out in ridiculous gowns on those shows because that style did not fit their body. Joy knew what would work.

12
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