Caught For the Last Time Ch. 06

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Jamie gets her name and his wife enjoys his feminine side.
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Part 6 of the 9 part series

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

That afternoon we drove for about a half an hour over to the small mountain range and took a walk on one of the trails. As we walked, we talked about last night. The talk was a lot less awkward than I thought it was going to be.

"The sex was good last night, real good," she said as she was holding my arm.

"It really was," I replied. "I never knew I could get that excited in certain parts of my body, like my nipples. I've always loved your teasing, but this went well beyond that."

I continued, "And not being inside you actually made it so much easier for me to hang on longer, a lot longer. I was not expecting that at all. That was real nice."

And she replied, "Hey, it was nice for me as well. I don't remember ever having that many orgasms in a row. My head is still spinning."

"That almost sounds bad." I replied.

"Not at all. When you're in me, my orgasms are like explosions....really big explosions. But when I was on top of you, I could control myself a little more and for a lot longer....they were more like waves that kept rolling over me...one after another, after another, after another. It was wonderful getting into that groove."

She gave me a big squeeze of my arm as she finished the sentence.

"So, given this mutual positive experience, we can leave the door open to doing this again...sometime?" I held my breath as I waiting for her answer.

"Absolutely. Last night was definitely an unusual night. But even discounting the new clothes, the wig, the wine, it was still great. I just think that if it becomes too often or too planned, it might not be a great idea."

"I was thinking the same thing. Plus, my nipples definitely need a major recovery period."

We laughed and she said, "Welcome to my world."

On our walk, she also said, "And dinner with you last night was so nice as well. Let's not forget about that. You looked so nice all dressed up. Those outfits are just so classic and fit you so well. Plus I got to dress up as well. I like to dress up at home too, you know."

She then said, "Too bad Sally couldn't see you dressed like that."

That caused me to pause but I quickly discounted any thought of having anyone see me dressed but my wife.

She went on, "You know, she really supports you. She has lived through this with her brother and she may be a good person to stay in touch with."

"What do you say if we invite her over next weekend for dinner? You could wear one of the outfits she gave you and we could do the whole thing, complete with the wig and make-up."

My reaction was still no, but the more we walked and discussed it, the more intriguing it became. Sally did have a lot of good stories about her brother and might be able to shed more insight. By the end of the walk, I agreed and we decided to ask her.

We grabbed a quick bite to eat on the way home at one of our favorite places and held hands we walked back to the car. It was such a nice, relaxing afternoon.

When we were just a few minutes from home she started stretching out a bit in the car and ran her hands down her body to her thighs.

"Are you still frisky?" she asked.

"Why? What did you have in mind?"

She said, "I loved what we did last night but I think I could use a real good pounding right about now and I know just the person I want to give it to me."

Toying with me she was now focusing her attention just on her pelvis and lifting her hips up to her hands. She kept it up and reached over with her left hand and began slightly caressing me through my pants. This was a playful side of her I had not seen in a while.

We barely got into the house and never made it upstairs. We stripped the clothes off each other and she drew me down on top of her on the living room rug.

I could tell from her panties that she was already wet before we even started. Lying on her back, she wrapped her legs around me as I penetrated her. I went right in.

While on her back, she kept banging the floor with her arms as she was driving her body up into mine.

She was so ready. I could tell by her deep moaning and quivering that she was having a huge orgasm. This afternoon was all about her and I kept at it, holding my breath at times just so I wouldn't go off first.

Then, she collapsed right back down on her back. I was finishing right at the same time and she exclaimed....."I needed that so freaking bad!"

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

I never changed back into any of Sally's clothes that night. Somehow it did not seem that important. We both slept commando that night and the last thing I remembered was that she softly kissed my nipples good night.

Monday morning came way too soon, but I happily changed into a pair of panties before I headed off to work. With all new my clothes, I was sad it was all I could wear. When I returned home from work, my wife greeted me with a big kiss and said,

"Sally is free on Saturday night. Let's plan a delightful dinner for her."

The rest of the week we discussed the menu, what to wear, topics of conversation, how to sit, everything. The closer Saturday came the more excited we got.

On Friday night we did a dry run of exactly what I was going to wear. I must have tried on every outfit I had! After mixing and matching outfits, we decided on the ¾ length skirt, the ivory tunic top, a long necklace, some bangly bracelets and the slingback heels.

I missed having the make-up on but we still had fun pretending. As I had the wig on and turned around and modeled the final selection, my wife kept looking at me and said you need something else.

"Here's what you should do tomorrow. Run over to Kohl's and get a 38C bra. I know the B's are great for around here, but with that tunic top, your "girls" could use a bit more perkiness."

"And while you are there, Maidenform has some body shapers that will help pull you in around the middle and pop you out a bit on top. Look for one of those as well. They are really tight to get on but can work wonders."

On Saturday I was all nerves, not because of Kohl's but because Sally was coming over. Dressing at home was easy, but being in front of Sally, or anyone, this was a whole new level.

I hit Kohl's first thing and you know who was there. Erin.

I walked up to her and asked, "Do you ever leave?"

"It's retail, what can I say? What brings you in so early this morning?"

"Do you have a minute? It's a long story."

"Look around, there is no one here. I'm all ears."

I explained what I needed and why, and Erin said, "Wow, that is amazing. I think I know just the thing."

She walked over to the Maidenform bras, picked out a neutral colored 38C and handed it to me like we had been doing this all our lives.

"Let's see, body shapers, body shapers....here, let's try these two."

"Oh, and one more thing, come here for a second." From behind the counter she pulled out two silicon breast inserts.

"I sell a lot of these, especially to the guys. They will make you look and feel natural, they are much better than socks. And once you wear them once, you will never not wear them.....trust me...I know first hand."

I did my best not to look down at her but I just had. "Yup," she said, "I'm just a little girl underneath....could you tell?"

I was deep red by then and just kind of murmured "I had no idea."

"Come. Let's try these on." We walked over to the ladies fitting area and she said, "No one is in yet so let's get a larger room. You're going to need help with these. Just keep your voice down in case someone comes in. We don't need to worry the female customers."

She told me to remove my shirt and turn around. Very professionally, Erin reached around me and slid the bra over my arms and attached the strap.

"Wow, you really are a perfect 38C in this brand. And I love those panties you're wearing. I can see them peeking over the top of your jeans...Soma?"

Not wanting to speak I nodded. "Class, real class", she said.

"OK, open the silicon box for me." As I turned to get it off the bench, she quietly slid her top off and I almost said something when I turned around and saw her in just her bra.

"Shhhh" she said.

"Now, do what I do." She literally removed her insert and said, "Place the concave side of it against yourself like this, and make sure the angle follows the flow of your body."

I could not believe she was showing me how to do it.

"The wrong way would look like this....the right way like this. Make sense?"

She was making me laugh with her faces as she showed me each way which kept the discussion fun and not sexually arousing.

Once in place she reached over and gave each one of mine a little push. "They feel good," she said.

She also did the same with hers and said, "See, these girls are not going anywhere.....look." She bounced up and down a few times and wiggled side to side.

I whispered, "They look so real."

"They do and you really forget they are even on after about 10 seconds. And now the body shaper. This is not as easy. Please put your hands up and let's pull this down over your head."

This was tough. She worked the back of it while I pulled the front down. There was actually not much of a front because the design of it was to push you in on the sides and move your breasts up and out.

Erin helped move everything around until she finally said, "Damn girl, you look great!"

My little C's looked fantastic. I actually had cleavage. Erin put her top back on and I struggled out of the body shaper with her help and finished getting dressed.

She opened the door, looked around and said, "Let's go, the coast in clear."

On the way to the checkout she said "And I want to see pictures."

"Really?" I asked.

"Yes really. I think you are going to look spectacular from both what you have told me and what I see here," she said with a wink.

"You should see the different shapes of men that come in for bra fittings or to try things on. They think that a guy the size of a middle linebacker can look like a size 5 Victoria Secret model. Realistically, that is not happening. But, in their mind they do and that is the most important for all my customers, male or female. I love my job and my customers."

"But you are different. You are a delight to talk with and to fit. I love your attitude. Trust me, I don't do this little show or tell this too many customers, but I wanted to show you that everything isn't always the way it appears."

She looked down at her slightly enhanced breasts and pouted a bit while she said, "Sometimes even a flat chested little girl like me can look and feel like a model too."

She then stopped, smiled and said, "Your wife is so lucky to have you. Oh, and if she ever comes in with you, I am discreet over what I say so I will follow your lead. "

"Erin, I'm at a loss for words. You are amazing and I will definitely get you some pictures."

"You do that and when you come back next time, I've got some great ideas for some other outfits for you!"

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

Around 5:00 I started getting dressed for a 7:00 dinner...good grief this takes a long time to get dressed. I started with my new bra, inserts and shaper. My wife looked at me and could only say, "Oh my."

I also gave her an abridged Erin story.

She spent a lot of time on my make-up and said that with the dirty blonde wig, the smokey eyes would be a good look for me tonight. Wow! She was right. I finished getting dressed and I seemed to be fussing with my hair every two minutes.

My wife kept saying "Leave it alone....you look fine. Now hold still so I can get some pictures of you so you can show your little Kohl's associate." I think she took 20 pictures from all kinds of angles.

Then the doorbell rang and my nerves kicked in all over again. My wife answered the door and I stayed back in the living room, waiting nervously. Sally walked in dressed in a smartly styled long skirt and a beautiful silk blouse.

I had never seen her dressed up before and with her hair slightly wavy, make-up and heels, she was quite attractive. I had forgotten how I looked because I was too busy looking at her.

She came over to me, took both of my hands and said, "You look amazing in those clothes. Someone has real good taste! And your make-up is just perfect. Truthfully, if I did not know any better, I would not know it was you. Turn around dear and let me see you from all sides."

I was so glad we moved up from a B cup to a C cup. With the wig and more padding here and pulling in there, it was really the look that was missing.

We had some wine before the meal and stood around talking about clothes and shopping and it was such fun. Our dining room looked wonderful with candles, nice china, and pink place settings. It was elegant.

We dined over salad, some light vegetables and wonderfully tender veal. For dessert it was a very light soufflé and with coffee it was perfect.

After dinner we retired to the living room. After a while our conversation drifted over to Tommy. Sally shared that perhaps one of the more interesting times she vividly recalled was about a month after she and Tommy had their little encounter and she gave him her clothes.

"My mom and dad took off for another weekend. Now up until that time, Tommy had been amazingly good to me and by all accounts, stayed out of my clothes. His special drawer had grown by a little as I added a new bra and even a few more panties to it. He had been real nice to me so to be honest, buying him a $5 pair of panties was a nice trade off. I know my mom never expected anything as she never hinted even a word to me."

"The only concern I ever had was that Tommy would now spend a lot more time in his room. And except for that one day, I had never seen him dressed again. And I know he was dressing behind his closed bedroom doors."

"So maybe this weekend would be different." She continued...

On Friday night after my parents left I said, "I've got a surprise for you!" His eyes lit up like before and I asked him to come up to the room.

I went to my closet and pulled out one of my favorite dresses of the past. I know it was one that he liked. Between you and me, I did not wear it anymore but I knew it would fit him. "Here, I want you to have this dress as well. But let's see if it fits first."

He looked a little embarrassed but I encouraged him by saying, "Go put on your favorite bra and panties, get dressed and let's see what it looks like." I think by calling them his bra and his panties I sounded more accepting and I wanted to show my willingness to make this as normal as possible.

He took the items into my closet, which is huge, and he changed. When he stepped out of the closet into the room and I gasped. He looked amazing. The dress fit beautifully and he was standing tall and proud. He immediately went to the full length mirror and kept admiring himself. I asked, "Do you like it?"

"I love it!" he said.

"Come over here and sit down." He slowly walked over and slid his hands behind the dress, straightening it before he sat down....he was good...even crossing his ankles as he sat up straight and tall.

"Tommy, you look great and you look so natural. Here is what I would like to do this weekend. I want to pretend that you are my younger sister Tammi. And we are going to have sister fun, starting with you changing into one of your skirts and blouses and meeting me downstairs. Does that sound like a plan?"

Of course he loved it. This was now going to be like a little game of pretend so now dressing in front of me was more fun than embarrassing.

He was changed and downstairs in a flash. We cleaned up the kitchen from our dinner meal....watched some TV....some silly girl shows and he sat on the sofa with his legs tucked up himself and loved it. A little later that evening I gave him another surprise....a new nightie.

It was a cute pink baby doll with matching panties, not too revealing but cute. What he did not know is I bought myself one as well. I asked him to go into his room, put his clothes away and meet me in my room in his new nightie.

I changed as well and got ready for the next part of the night. When he walked in wearing the nightie, I just said" Hi" like it was no big deal and asked, "Let me see your toes. Oh my, they need a new coat of polish."

Of course, they were not polished at all so he kind of laughed. He first objected and then agreed when I promised him that the nail polish would come off.

"Do you think this pink nail polish will match your new nightie? Or maybe this color?" When he finally decided which color, I shaped this nails and gave him a mani and pedi. He just stared at this hands and feet for the longest time. Plus the smell of nail polish was wonderful to him.

We chit chatted for a while, watched TV together on the couch and then we said good night. "I will see you in the morning and I want you to come to breakfast in your nightie...you can't do that while mom and dad are home."

In the morning he came down as requested and he was so giddy. I had made a little breakfast and we sat down to discuss the day. I didn't mention it but I noticed he was wearing a different pair of panties than the matching set he was wearing at night. I had a real strong feeling he really enjoyed wearing the new nightie to bed.

After breakfast I told him to shower, put on a skirt and blouse as we had some morning chores to do. It was so much fun. Once the chores were finished I told him he had the afternoon to do anything he wanted but at 5:00 I had another surprise for him.

One thing he opted for in the afternoon was to get his homework out of the way and that involved a lot of reading. So there he was, sitting downstairs, curled up on the couch in his skirt and blouse doing his homework...he was so adorable.

At 5:00 he sort of hinted it was time and we headed upstairs. I asked him to take off just the skirt and blouse, put on one of my robes, and sit at my dressing table. I looked him straight in the eye and said..."You need a little make-up to freshen up your face. Hold still while I put a little on." He never even objected in the least.

A little make-up took me 30 minutes as I explained everything I was doing. He did tell me that other than some lipstick, he had never used any make-up so this was finally a real first. Finally!

When I was comfortable with the look I reached over and pulled a shoulder length wig from a bag. This was total surprise to him as well. After brushing it out I slowly placed it on his head, adjusted it and brushed it until it was perfect.

I sat back, admired my own work and he was no longer Tommy. Then I added some clip-on earrings. He wanted to see himself sooo bad. "No peeking yet," I said.

"Now, put on the new dress I gave you yesterday. And no peeking! And toss on my slides in closet....you need a little lift and they should fit you."

I then took him by the hand....."Keep your eyes close until I tell you." I walked him to in front of the full length mirror, stepped away and said, "Alright, you may now open your eyes."

He never moved once he saw himself. He just stood there and stared, and admired, and turned his head left and right. It was like an awakening.

"Tammi, you look beautiful." He twirled, spun around and looked at himself from every direction. He loved it and I did too.

After about 10 minutes of Tammi enjoying her new look, I said,

"I told mom I was going to make my closet a priority this weekend and was going to go through everything in it. What I did not tell her is that we were going to do it together. Would you like to help?"

That evening we both tried on every single dress, skirt, and blouse in my closet. We were primping with each other, mixing and matching outfits, and having such girl fun.

There was even one time early on that I said...."It looks like Tommy really likes that dress"....emphasizing the name Tommy as he was getting a tad too excited in one of my slinky dresses.

TGJamie
TGJamie
449 Followers
12