Caught For the Last Time Ch. 04

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A new opportunity arises.
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4.56
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Part 4 of the 9 part series

Updated 06/07/2023
Created 02/05/2015
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TGJamie
TGJamie
449 Followers

So here we are in the early fall. Another three months have passed and all I can say is what a summer. My dressing at home had calmed down a bit and was now pretty normal. I could actually get dressed and not get a raging hard on every time. I actually liked that.

We modified some of the dressing at home rules to make both our lives easier.

If during the week I arrived home from work earlier than she did, and I wanted to put on a skirt and top, I could. Knowing that my car was in the driveway was at least a heads up to her that I may be dressed. Not that I was, but I may be.

Weekends at home were still about the same with one added plus. On Saturdays or Sundays I was usually dressed while we worked around the house and every so often I could change into the loungewear or chemise at night to relax if we were staying in.

It was fun and sometimes playful, but never more than that. A squeeze, a hug, a touch, a tease.

I did not dress every day and that was OK with me, and apparently with her was well. Our sex was good sex. We were active and she was playful. She was amazing in bed, or in the living room, or the kitchen, wherever.

But I was still yet to have sex with her while dressed.

Strangely, that was no longer a burning desire of mine because I could wear almost whatever I liked whenever I liked. And I never wanted dressing to interfere with our sex life, and I could see how it could if I pushed it.

I think she knew that it frustrated me. I had pretty much resigned myself to taking matters into my own hands. I was still masturbating a couple of times a week while dressed so that at least satisfied those yearnings.

On the positive front, I was also able to purchase several more items over the summer through mutual consent, mostly because I think she was tired of seeing me in the same clothes when I did dress. I purchased a nice denim skirt with a bit of a stretch to it, and went back to Kohl's to purchase some camisoles tops.

I think I had gotten a bit too cavalier in my shopping because when I was at Kohl's buying the camisoles the same cute sales associate Erin came over to me and asked, "Back again?

"You remember?"

"Sure. I especially remember all my guy customers. We get a lot. As I remember you were buying some bras and panties last time. What do you need now?"

I tried to roll right along with the conversation and said, "Erin, I'm looking for some camisoles. Do you have any suggestions?"

She said, "Personally, I like these. They're cute, have a nice band of lace on the bottom so they are fun to wear out over your jeans. And they have adjustable straps so they should fit you no problem. I'm guessing you're a large, maybe an extra large because of the length."

She started looking for some different ones and helped me find a few.

"Oh, and Maidenform has some too, didn't you buy a pink Maidenform bra? I love pink camisoles."

"How do you remember all this?"

She just smiled and whispered, "Everyone buys a pink bra."

We walked over and got one and she said it will match perfectly. I had never even through the matching aspect.

"What are these?"

"Oh, those are rompers. They are like camis, but longer with legs. They are so cute. I've got a couple of those as well and love them. Do you want to try it on to see if they will fit? They're kind of tricky to size"

This was amazing as she grabbed three different ones. All I could say was, "Thanks, that's a good idea." She pointed out a neutral changing room to me that I didn't even know existed and tried the rompers on as well as the camis.

I loved the rompers. I decided on getting one of those and 2 camisoles, the pink one and a black one.

When I came out I thanked her for the suggestions and she said, "Anytime. Seriously, I have a lot of male customers and fitting is always a challenge. I'm glad to help you anytime."

The entire purchase cost $35. I found that I even could wear the camis even without a bra if I wanted. They were cute and easy to pop on and off. And my wife approved as well.

When my wife saw the romper she said, "A romper, what a great idea! Did you get me one? I love these". I wish I had known.

Some of the more fun memories of the summer would be her coming home a little later than me at night when I was preparing the dinner. I might have on the black skirt and just a camisole top. She would walk over and from behind me, squeeze my butt...or slide her hands around the front and cup both of my breasts.

It would hardly ever go much further than that, but it was always a thrill to have it done. And yes, the nipples would get hard and she would always tease me about that...like..."You are such a girl."

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

And perhaps one of the scariest days of the summer for me came one early evening while sitting at the kitchen table. I was wearing a pair of my shorts and Tshirt over my bra and panties. My wife was outside in the garden while I was going through the mail. It was a beautiful early night and one of her friends stopped by as she was driving by the house.

I never heard the car door close and it was not until the kitchen door opened and they both walked in that I heard..."Honey. Guess who stopped by? My good friend Sally."

Crap. The good news was that I was not in a skirt. But, the Tshirt was a bit tight and girlish so I tried to sit to minimize the exposure as I sat there in kind of a bit of a defensive position. They chatted about how nice the yard looked and my wife commented on how helpful I had been on keeping it up in the hot summer months.

My wife then tried to move their conversation into another room but Sally asked me how work was? It was kind of hard not to answer her direct questions. I tried to make the answers short and sweet, but the more I did that, the more she asked.

I could not help but notice that her eyes kept glancing down towards my Tshirt every so often. It was more of a quisical look than a stare. Part of me wanted to crawl under the table and the other part of me wanted to ask where she buys her lingerie. She always dressed so well.

Regardless, the conversation finally ended and they headed into another room. I basically did as well and headed the basement. While my wife and I chuckled over it at dinner, I was still very nervous about anyone else finding out.

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

And there was one night when I was sitting there in one my softer Tshirts, bra and panties over my jeans and she said, let's go out to the movies. It was one of those lazy Saturday nights, at the end of the summer, and the nights were just beginning to turn cool.

I had kind of settled in but I said, "Sure, let me change and we can go."

She then tossed me my light nylon windbreaker and said, "Not tonight. We're going to see a chick flick and what better way than wearing your bra and panties. It'll be fun. Besides, no one will know but us."

I was a bit hesitant about this but was thrilled she suggested it. She then said, "Look, you wear panties to work on some days, don't you? How much harder will this be?"

It's true, and I had no problem with that. So off we went.

She drove and on the drive over she kept teasing me about being outside in my bra. I actually kind of liked being teased and loved how the car's shoulder seat belt split my breasts and gave me a little more cleavage. I sat there feeling a little prouder as we drove through town.

When we arrived at the theater I tossed my jacket on but left it unzipped. It covered me just fine but there was the fun of being a little exposed. There were 2 movies playing at our theater and she wanted to see the chick flick.

And what a surprise, the chick flick was attended by a lot of chicks, and not just young ones. I must have been one of the only 10 guys there.

As we waiting in line for tickets, I was real apprehensive. But as I looked around I could tell that no one was really looking at me or my chest, so I felt more comfortable.

While we waited in the lobby, my wife kept asking me things like..."Do you like her skirt?... Her top is adorable don't you think?... Look at that camisole, that is so cute. It's like yours. ...And that dress...she is about your size...let me go ask where she bought it."

It became like a mini fashion show. We were having so much fun it was almost a shame we had to go into a theater. Once inside I found the confidence to remove my jacket as we were sitting down in the slightly darkened theater.

This felt good until people starting coming into our aisle and I had to keep standing up to let them by. I am not sure anyone noticed I was wearing a bra when I stood up but it was fun.

The movie was a lot more enjoyable than I thought it was going to be and it did have some racy moments in it including a time when the husband surprised his wife by wearing her panties to bed and had real passionate sex. Awkward, but it got a good chuckle out of both of us.

In one of the more intimate romantic scenes, my wife actually reached over and slid her hand under my shirt and inside my bra and whispered, "That's how a girl likes to be touched". It was no surprise that my nipples were hard at that point. I'm so glad that scene lasted for several minutes. She kept softly caressing my breasts and lightly squeezing my nipples through the whole scene.

It was probably the one time I wish I was wearing a skirt in public as well! But what happens at the dark theater stays in the dark theater. And other than the suggestion we do this again sometime, there was no reruns of the bra scene when we got home. There was still that line that apparently only she could cross but not me.

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

It was now late-September, and it was getting darker and cooler earlier at night. The summer clothes no longer seemed as appropriate as before. I did not want to bring up the clothing issue, but I was afraid I was going to have to. She was always the one who initiated the conversation on new clothes.

While watching the news on TV, one of the reporters had this real cute fall outfit on and my wife commented how nice she looked. This was my opening.

"Honey, I hate to bring this up, but on certain days, especially in the evening, I feel a bit chilled at home wearing the short skirt along with the short sleeved top. Do you think I could get perhaps a longer skirt and a longer pretty top??" I held my breath.

She said, "I've noticed that you do look a little out of season. I think you're right. Maybe you should have a few items for the cooler weather."

"I'm not sure I could find you that same outfit the cute little size 5 weather girl has on, but give me a few days to think about." We laughed together which was good.

Plus, I said it nicely and the response was relatively positive. At least she had been thinking about it as well. I always liked her plans so who was I to argue.

On that Friday night, I came home and changed into my dark blue bra and panties, and wore a lighter colored jersey top and a pair of skinny jeans. It was probably my best girl look in guy clothes I had. In the mirror I could clearly not only see the dark bra color through the shirt, but it also had this clingy feel that I loved. I was really enjoying this freedom.

And then the phone rang. My wife said she would be home in about 30 minutes and was stopping by with a friend. But she went on to say, "Being a Friday night I can already guess what you are wearing. Why don't you just keep the bra and panties on, but just put on one of your more discreet shirts you used to wear."

I was so glad for the heads up. I quickly changed my shirt right away, checked myself out and relaxed with a book, all the while wondering who was coming over.

So there I was sitting in the living room, casually reading when my wife walked in...with Sally.

Crap, here I am with Sally, the gal with once saw me in the bra and Tshirt at the kitchen table. I'm still wearing a bra and panties but at least this time I was sitting in the love seat and looked fairly guy normal.

"Honey, I caught up with Sally earlier this evening and asked her to come over."

I went to stand up to say hello, but she said, "Oh please don't get up."

Thank goodness because I know she'd be checking me out. She'd probably give me a hug and rub my back as well.

There was some idle talk and then my wife said, "Sally's been a good friend for the last five or six years and we have had lots of girl talk times over the years. One thing she shared with me several years ago was that her younger brother was a crossdresser."

All of the sudden the room got very warm and my face got flushed. I was trapped and I did not feel at all comfortable with where this conversation may be headed.

She then added, "I would like Sally to tell you a little more about him and her experiences."

I felt even more trapped but I trusted my wife and stayed.

Then Sally spoke. And this was a more serious Sally, not the fun loving one I had seen in the past.

"When I was in high school, I was loving life. Being the oldest of two children in the house, and being the only girl had its privileges. My mom and I would go shopping all the time. Between dance and cheerleading, I had a full life and quite a collection of wonderful clothes. I had my own room with a huge walk in closet, a wonderful chest of drawers, and other great girly things in my room."

"I never really thought much about that until one day after I came home from my dance class and showered, I noticed that when I went to my underwear drawer, something seemed a little out of place. Not a lot, but just a little. I shook it off as maybe my mom was looking for something and then I forgot about it. No big deal."

"That was until a few days later after cheerleading practice, the same thing occurred. I again thought it was my mom, but she had been out for the entire day. I was puzzled. I then thought about Tommy, my younger brother, but dismissed this as, no not my brother."

"This routine continued for a few more weeks and the more I looked, the more I found things slightly out of place. A dress hanging in the closet with the hanger facing in the wrong direction. A blouse from my hamper turned inside out. A nightie from my drawer improperly folded. I was now becoming more of a detective every time I entered my room."

"I tried to stay calm and think through how I was going to confront him if it even was Tommy, and what I would say to him. I had read some articles about boys wearing articles of female clothing, but the stories always were the perverted type. I did not want this story to end that way nor did I want to think anything bad of Tommy."

"So I crafted a plan to see if I could catch him in the act. On the kitchen wall we had the family calendar and I had on it a dance class that was really not happening that Tuesday. It had been cancelled."

"I told Tommy that Tuesday morning that I would see him at night and headed out to school that day as normal. After school, I hung around with friends for a while and planned to hit the house after he arrived home from school but before the time my mom would arrive home from work."

"I quietly entered the house and went upstairs. I peeked in my room and as expected, there he was. He was standing in front of my full length mirror in one of my tops and skirts. He was pretending to me, talking to the mirror, swaying left and right, checking himself out from all the angles. It was actually kind of cute."

"He then did a full twirl and spotted me at the door."

"Sally! What are you doing home so early?"

"I sternly replied...never mind that, what are you doing in my clothes?"

"Tommy was so embarrassed and stammered out some lame excuse that wasn't even a sentence. I walked over, sat in my chair, folded my arms and told him to take off my blouse of right away. He said he would and started walking into my closet to do it.

"No. Take it off right here and now, or I will tell mom and dad." Pouting a bit, he undid the blouse and handed it to me.

When he did, he was now standing there in my black bra with a black skirt. This made him even more embarrassed if that was even possible. But between you and me, he looked kind of cute!"

"Now the skirt I said. Reluctantly he unzipped the skirt and as it fell to the floor, I was at least glad to see he was wearing matching panties...but I didn't let him know that either."

"I then had a sisterly talk with him as he stood there in my bra and panties. I told him I did not like him violating my space and if he ever did it again, he would wish he hadn't. He apologized a dozen times, and after probably the longest 10 minutes of his life, I told him to remove the bra."

"This was the part that amazed me the most. He reached his hands behind his back, undid the strap with amazing ease and handed me the bra. He did that better than most girls...this was not his first time he had removed a bra. Or even worse...my bra! Now, go into your room and change and then put the panties into the hamper in here."

By now, I was fascinated by Sally's story. I now had a totally different perspective on her. I then asked her..."Did he ever go into your room again?"

"Not for a few weeks. And even at that it was very periodic so I let it slide. I really loved this kid and I needed to really think through what my next steps would be. I could see that he was now being extra nice to me all the time, even complimenting me at times on how nice I looked...seriously, a brother complimenting his older sister. It was a good feeling."

"Then one weekend my parents were going away and I was to watch over Tommy. I had done it before so it was not an issue. But I wanted to use this time to have some more meaningful discussions with him. I knew he was still getting into my clothes. I think he was trying on a few outfits from my closet and probably some under things from the hamper, but he was being very discreet."

"So on the Friday night that my parents were leaving, we all had dinner together and we gave them hugs goodbye. Tommy and I finished up the dishes and decided to watch a movie at home. It was a funny one and one of his favorites. It left him in a good mood."

"When it was over I asked him if he would help me move something up in my room. He agreed and when we walked in the room, I am sure that he could not help but notice what I had laid out on the bed as we moved a small piece of furniture."

"In a nice orderly pattern, I had placed five pair of my panties and two of my bras on my bed. I saw him glance over at them more than once and then I made a simple statement like...

"I've been getting the feeling that you have been trying real hard not to wear any of my clothes these past two months. But you have been, shall we say, struggling a bit."

Sheepishly he agreed. "The feeling is there he said...a lot. Try as I might, I am still attracted by them."

Then being nice, and not accusatory, I told him "I think I am beginning to understand. The fact that you are wearing my clothing when I am not here still bothers me so I have come up with this plan. Do you see those bras and panties on the bed?"

"Yes" he replied.

"From now on they are yours."

His eyes lit up and his embarrassment was replaced with surprise..."Really?"

"Yes. What I am going to do is put them in the third drawer in this other small dresser we just moved. You can keep them in here when you are not wearing them. That way mom will not find them stashed away in your room and go crazy on you."

"And in my closet, I put together two of my skirts that I do not wear all that much, several tops and two simple sundresses. I am putting them together on the right side of the closet. Feel free to wear them as often as you like and then neatly hang them up again. And just this side of the closet...got it?"

TGJamie
TGJamie
449 Followers
12