Caught For the Last Time Ch. 07

Within an hour of mom leaving for work, Tommy had changed into a simple skirt and blouse, along with bra and panties, he applied some light make-up and with the wig on headed down stairs.

He started in the kitchen by doing the dishes and had just started the laundry when mom walked in and said,

"Good news! They sent us all home."

When she saw Tommy all dressed she was a bit surprised but not upset. Tommy was feeling real comfortable, but tried to act a bit embarrassed and said "Sally said I could wear some of her clothes. I just felt like wearing them today while I did some chores. I hope this is OK with you mom?"

"OK? I think it's wonderful. I was afraid that you were embarrassed the other night when Sally was home and we spent the night together. I have been fretting about it ever since." She gave him a big hug.

That began a long and different relationship between my mom and Tommy. In the two weeks building up to Christmas break, he dressed a couple of more times at home, usually on weekends with mom's help. He really spent a lot of time with her and their relationship got better.

When the Christmas break came and I hauled all my clothes back from college. I went through them and told my mom that Tommy could have some that I know longer needed at college.

As a special treat at Christmas, she and I actually bought him two sets of bras that fit him and matching panties to put under the tree so that they could really be his. I think he liked that a lot.

Tommy started dressing a tad more unisex after that so as the winter became the spring, he was comfortable being at home with mom is whatever clothes he had on.

My dad became more and more distance in our lives and by the summer, mom said that they decided to separate for a while until he figured some things out. She took it pretty hard.

Then Sally, wanting to end on a high note, said, "So, one of the other reasons I wanted to come over was that I got a call from Tommy just this week. He has a business trip coming up very soon to this area. I'd like him to meet you."

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It wasn't but two weeks later that Kelsey got a call from Sally letting us know that Tommy would be flying in the following Sunday and was wondering if it would fit our calendar. We had talked about it and decided this would be a good step for me. I realistically had no one to talk to besides Kelsey and Sally.

We decided to meet a restaurant for dinner on the Sunday night he arrived. It would be just the four of us at dinner and to clarify, we were all dressed in our respective male and female attire. I have to say we all looked good that night.

We had a great time getting to know each other. Tommy was everything Sally described. He shared that he has a successful career in the aerospace industry and loves his work environment.

Several of his coworkers knew of his crossdressing but he never dressed openly at work. He said he had no compulsion to do so as he enjoys being a guy. He just likes going out and presenting as a female sometimes.

Going out dressed was something really foreign and scary to me so I asked him, "May I ask where do you go and how often?"

He said "When I first moved to Chicago it was big and unknown to me. But I had a good job and it was a good career move."

"I checked the internet and found a lot of different transgender or crossdressing groups so I began researching which ones were active and where the members hung out. I actually went to a few of the locations in stealth male mode on nights when the groups were meeting just to get the feel of the group."

"For example, one group met in the corner of a small bar and were dressed in clubbing type clothes. Another group met at a nice local restaurant and were dressed nicely and conducted themselves as ladies, barely giving rise to any patrons."

"It took a couple of months of checking things out before I ventured out anywhere. I also shopped at all of the Dress Barns, Lane Bryant, specialty shops, etc., bought a few things here or there and asked the sales staff. They had so many male clients that they were always helpful in giving me thoughts on where to go out."

"I remember my first outing was in the suburbs in the restaurant setting. I had contacted the group and asked if I could attend. They were so happy I did and eagerly invited me."

"They told me all the little things like it was a family restaurant, dress appropriately, etc., but I already knew that. It was one of the places I stopped at early and had checked them out. But I let them fully explain it. And it was a weeknight so my first dining out experience in Chicago would be easy."

"That night I wore a very conservative button up the front blouse, no cleavage, a skirt just below my knees, low heels, and really worked on my make-up to give me that every day look."

"After dressing for years and with the help of Sally, I was really good with my make-up and my outfits were really nice. My poise and confidence levels were also high so I had no problem arriving at the restaurant, talking to the hostess and walking through the restaurant to the table."

"I introduced myself and met some really nice people that evening. The conversation that evening was all about me, the "new girl", so I told them about my wonderful sister and some of the fun things we did growing up. I did not disclose too much about my everyday job but it was nice to hear that I was in the company of a doctor, attorney, architect and another engineer."

"As we talked, they asked if I had been anywhere else in Chicago and I said no, mostly staying in, but I asked if they had any recommendations?"

"They started listing the places they went to. Sometimes they would go as a group of 4-5 and other times just a couple of them. Two of them were headed out on that Friday night to a club downtown that had alternative lifestyle night and thought I might like that. I got their email addresses and said I would think about it."

"The idea of trying a new place was intriguing and hanging with new friends would be good as well. I'm not into solo action in a new city. I checked out the club's website and got some ideas as to what I would wear and decided to have a go of it. But I was still unsure."

"Checking out a website versus reality leaves a lot to be desired. So I drove by the place one night and realized that if it looked as bad in the inside as the outside, I was not going in. I contacted one of my new friends who told me the inside was amazing and I should definitely dress for a club scene."

"I went into my closet and start putting together an outfit. Actually two outfits that night. One to drive in and another to wear at club. My driving outfit had to be easy to remove...a front buttoned blouse, a ¾ length skirt and some flats."

"Since I had to walk out of my condo association I wanted to draw as little attention to myself as possible."

"For at the club I had the shortest black flounce skirt, a gold sparkly cowl neck draped top and spiked heels. Just a little different."

"Before I left my condo, I went heavy on the make-up and walked cautiously out of my condo in my conservative clothes. No one even looked twice."

"When I arrived at the club I parked in the adjacent garage and quickly slid my club clothes on. I can do that in a heartbeat, and as a hint...always leave the heels for last."

"I left the parking garage and headed across the street. As I walked into the club, the place was hopping and real classy! There was every lifestyle imaginable. Lots of Goth, dykes, lesbians, crossdressers, gay...and straight as well."

"I fully expected all the attention to be on me but it was just the opposite. Every little group seemed more interested in their own little group. It was an interesting dynamic."

"When I saw my little group of two I recognized them right away but they did not recognize me. I was wearing a blonde wig tonight with heavy make-up rather than the brown wig and light make-up I wore at the restaurant."

"I decided to have some fun and stand near them but not acknowledge them for a while. With my heels I was standing at six feet tall, legs up to my whatever, and looking like Taylor Swift. Not the demure Tammi they met the other night."

"With the music so loud, when I did say hi, they still didn't recognize me as I was shouting out my name. They were all surprised when they realized it was me and got a laugh."

"I met about other 10 other people that night. We had a great time dancing, drinking and chatting. After the evening I headed back to my car and changed back into a more conservative me."

"I always, to this day, get a little nervous about too many people knowing about me, including my neighbors at the condo association. But if they know, they know. I try to low key the outside dressing but am comfortable dressing at home on weekends, getting out with friends and a couple of nights a week if I have time."

With that Tommy asked me "Have you ever been out?"

"Gosh, other than underdressing at the movies that one time and putting on some outfits at various shops, the answer has to be no."

Tommy then said, "Sally told me you look fantastic when you are all made up. How about we all go out to a place far away from here where no one will know you for a dinner one evening?"

"We can all wear wigs, even the ladies, just in case you know someone there. It would be a lot of fun."

Strangely, it sounded interesting and my wife agreed as well.

Tommy continued, "Since I am only here this week, let's go this Tuesday night. I have no meetings that night. I had looked up a few places already and checked with some friends who have frequented your fine city and they recommended these."

The good news is that I had never heard of these restaurants and did not know of anyone living in the nearby towns so I felt a bit more comfortable with the idea.

On Monday night my wife and I spent over an hour deciding what to wear and decided on a Sally outfit...slightly longer skirt, tunic top, lots of drapey jewelry and low heels. My wife decided on similar attire.

We left our house on Tuesday in the cloak of darkness. It was the first time I had been outside dressed.

When we arrived at Sally's to pick them up I was so shocked to see what a transformation Tommy had made into Tammi. If I had not met him before I would not have recognized him.

Sally immediately stepped in and said, "Tammi, I'd like you to meet Jamie." We gave each other a girl hug and air kiss, and complimented each other on our outfits.

We stood around primping a bit while we enjoyed a glass of white wine, took a lot of pictures and then headed out.

Going out with a group of four is so much fun. With Sally and my wife wearing high heels, and Tammi and I wearing lower heels, it helped take the pressure off of us towering over them. Plus having Sally and Kelsey in wigs changed their looks entirely.

At the restaurant my nerves kicked in again. I kept telling myself I looked good, no one knows me and I can do this. I tried to follow Tammi's lead walking in and became like her shadow.

Tammi walked right up to the hostess and gave her our names. With a wonderful smile, she welcomed us and complimented us on how well we all looked this evening. Wow, one hurdle out of the way.

We had our own special table near the windows, which meant we had to walk through the entire restaurant. The restaurant had about 25 tables so it was not huge, but there were enough other diners in there.

Tammi loved every minute of the walk and I was dying a thousand deaths with every step. She glided through the restaurant and the only heads that turned were a few guys who were checking Tammi out. I did not feel like I was gliding but at least I did not trip.

But, we made it to the table. The waitress could not have been nicer and addressed us as ladies all evening.

Throughout the meal, Tammi and Sally shared story after story, including times he visited her at college, to dating some of her guy friends and to the struggles he still has with relationships.

The stories were griping and gave me lots to think about in terms of my own feelings.

We had a wonderful dinner and as we looked around, I think we were the last to leave, so we gave them a nice tip. The hostess came over to us several times during the evening to make sure we were having a wonderful time, and as we left, asked us to please come back again. I assured her we would.

That was the last we would see Tammi or Tommy on his trip, but we agreed that maybe we could take a trip up to Chicago and visit him some long weekend.

Our trip home after dropping Tammi and Sally off was quiet.

"Are you OK babe?" she asked after several minutes of silence.

"I am, and I'm so glad we went out, and I really hope we can do it again. It was more fun than I ever expected and I love being Jamie with you."

That got a nice little squeeze from her.

"But talking to Tommy as Tammi for the whole evening, and not really seeing him inside there, but her was hard for me to process. He was Tammi, not some guy dressed up as Tammi. Does that make sense?"

Quietly she said, "Yes, it does."

"I guess for the first time in a long time, I felt more like a guy in a dress rather than the girl I feel like at home when I'm dressed and with you. I just need time to process this."

"I think we both do," she replied. "And even though it's Tuesday, I think that cute ivory babydoll would be perfect for tonight, don't you?"

"Yes, perfect."