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  • Caught For the Last Time Ch. 07

Caught For the Last Time Ch. 07

12

We awoke in the morning almost identical to how we both fell asleep. I was still in the babydoll nightie she had given me and she was still in her palazzo pants, heels and pony tail, and no top.

"That was quite a night," she said as she sat up and unstrapped her heels. "When was the last time I woke up with heels on?" We both laughed as I shook my head.

Then there was her obligatory nipple touching. "Wow, you barely even flinched. I told you you'd get used to it."

"I'm actually beginning to like it," I replied.

"I was hoping you would. Well, Jamie, what would you like to do today? You've got the whole day ahead of you."

There was a light rain falling outside and it really felt like one of those lazy days.

"After listening to Sally last night and then our amazing time together, I'd like to be Jamie for the day and stay around here. I'm just in that kind of a mood."

"I think that would be perfect and fitting after yesterday and last night," she replied.

I looked around, tried to take an inventory of myself and said, "My face has got to be a wreck so let me do this. I'm going to shower and clean up a bit. Then I would like to make you a really nice breakfast. You relax here in bed and I'll see you downstairs in an hour."

She made one of her infamous, long cat stretches and said, "That would work real nice. Knock yourself out babe."

The shower felt extra nice today and I decided that one of the short chemises with a long robe would be best. I finished a light make-up application on myself downstairs and started making breakfast.

When Kelsey came down she had on a pair of jeans and a nice Tshirt top with no bra. She came up from behind and gave me a real nice squeeze and said, "I'm really liking these mornings...how's my girl doing?"

"I just love it when you do that," I replied.

After a nice breakfast, I cleaned up the dishes, headed upstairs and changed into a skirt and top that would be casual enough for household chores.

The rest of the day I spent cleaning up from the other night with Sally, doing laundry, and trying to arrange all my female clothes into some semblance of order.

By now, my closet at home was beginning to look way too jammed. It was like having storage for two different people. Kelsey actually suggested that we begin keeping Jamie's dresses, skirts and blouses in the spare room closet. I had to agree.

Getting dressed to work each day and grabbing my guy dress shirt from beside my Jamie blouse was a temptation that I did not need to have. I was struggling on how to keep the two worlds separate, and this was a good idea.

After I had moved all the clothing over I was surprised on how much I had gathered in such a short period. As a nice touch, my wife helped and let me use a few of her hangers for some of the more delicate dresses.

Strangely, there was no strong desire for sex that day. There was a lot of hugging, cuddling and small talk. It was fun, and even just sitting around at night in my Soma loungewear outfit from what now seemed so long ago with her while watching Netflix was fun. It was actually nice that sex did not always have to be a part of the crossdressing experience.

The next day we were off to visit some relatives and when I got up I put all my Jamie clothes away and in the hamper, and actually wore a pair of guy underwear and a nice pair of slacks and shirt.

As I was getting dressed, she hugged me and said, "I love Jamie, but I love my guy even more." She put on a cute dress which is rare for a weekend and I had to compliment her on how wonderful she looked. She was beautiful.

We actually had a great time together visiting and had amazing sex that night. It was nice being able to balance the two worlds.

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

From that day on, things at home stabilized. Oh, I still underdressed for work. And there were days when I would be just a regular guy and not even hint at wanting to get dressed.

I limited the full make-up thing to weekends. Realistically, it was a time commitment. But it was easy for me to balance a couple of nights a week being partially dressed with light make-up at home with being fully dressed with lots of make-up. In my mind, at least, I was fully dressed all the time.

With so many clothes from Sally, I didn't need to purchase that many things but I did purchase some cute, stretch jersey tops with little Erin's help at Kohls. They were perfect for at home on top of a pair of jeans with a Tshirt bra and I could also wear them out without a bra. Having some dual purpose tops was a thrill.

My wife even met Erin on that trip and showed her the pictures of me dressed from the night Sally came over. Kelsey really liked Erin and Erin complimented me on being such a perfect gentleman and how lucky Kelsey was to have me as a husband. That was a nice touch.

Erin loved the pictures so much she to keep one picture to show other people she works with. And we departed with her saying, "Please, both of you come back again. The spring clothes will be coming soon and I have some great ideas for you!"

I think I also became a bit obsessed with my weight and my build. I was now seeing myself dressed in a mirror, a lot. It really made a difference. And now I had pictures as well...good ones and some bad ones. I really needed to work on my posture and my smile.

And Sally. Her coming over was becoming a routine. My nervousness was totally gone with her and I actually enjoyed her company. Sometimes she dropped by on a weeknight when I was just in my guy clothes just to chitchat with my wife. I would be around, but not really part of the conversation.

Other times it was a Saturday afternoon when we were all casual and I could be in a bra that was somewhat noticeable. It never seemed to matter to her or me anymore. I would get a hug and she would always playfully rub my bra strap.

And whenever she came over announced, I always put on a wig and at least some light make-up, but unless it was a fancy evening, it was never a lot of make-up. She would inevitably bring me something she was no longer fond or something she thought I would enjoy. She knew my tastes all too well.

In fact, she had "donated" so many items to me that the extra closet now had about 8 skirts, 6 dresses, a dozen tops, 5 pairs of shoes, and 4 wigs. Plus I moved a small dresser into that room that had two drawers full of different types of nighties.

The other factor that changed was wearing things to bed. My wife seemed to enjoy what she called "Jamie Nights". They tended to be weekend nights, especially Friday after a long week work week.

And the Jamie Nights were not always nights, nor were they always predictable either. I remember one Saturday morning when she headed out for some shopping and I stayed at home doing some work around the house. I was wearing a wig, pair of cut-off jeans over my pink panties and a cute top and matching bra. Nothing outrageous, just cute.

She came back around noon with some groceries and a bag from Nordstrom's. "What did you get?" I asked.

"Nordstrom Rack was having a big sale so I thought I would stop by and look while I was out. I looked at a lot of items and realized there was nothing I really needed...until I went to the nightgown area. Look what I found!"

From the bag she pulled out a beautiful white night gown, with a robe and matching white lace panties. The gown had a long split up the side and was so amazingly soft.

I told her "That is so beautiful and I can't wait to see it on you!!"

"No silly, it's not for me, it's for you! Now go upstairs, try it on and let's have some Jamie time."

"Now?"

She just smiled and nodded, "Do you mind a little Afternoon Delight?"

I did not need much more encouragement and headed up to change. I chose long dark wig and upgraded my make-up. The gown was gorgeous. I stripped down and slid the panties on first. Besides being lace, they had bow ties on the side. I loved that look. The gown fit perfect and the side slit made the cut look sexy as well.

When I gave her the "all ready" call, she walked in wearing new clingy, deep purple loungewear. Apparently she found something for herself as well. The pants fit her hips perfectly and the top was comprised of a camisole like t-shirt and a long flowing top that opened in the front. In her hands she had two long stem glasses and a bottle of chilled wine.

She laid the items on the dressing table where I was sitting and gave me a long deep kiss. Slowly she began caressing my breasts. She really did not need to because my nipples were already hard and pressing though the nightie.

"I can see you like the nightie," she whispered.

With her auburn hair was pulled back in a ponytail, she looked so hot in her outfit. This was her signature look and got me horny every time I saw her like that.

After a few minutes she opened the bottle of wine and poured us each a glass. It was wonderful and we sat on the bench and lightly caressed each other until we had finished two glasses of wine.

She then asked me to put on a little fashion show. With the wig, make-up and white nightgown, I felt like a new bride. I walked, twirled, posed, and played coyly with her in my new gown. The afternoon wine had really loosened us both up.

I then slinked backed over to the bench where she was sitting, hiked the gown up just a bit, and straddled her as she had done with me so many times. Her hands could not have been any more active. Gently, she slid the robe off my shoulders and it softly fell to the floor.

The feeling was amazing...her legs, now between mine were slowly lifting me up and I began grinding downwards towards hers in a rhythmic motion.

After a few minutes, she whispered that we should move over to the bed. She removed her robe and laid on her back wearing just her camisole top and long pants. I slowly mounted her again and as I had a chance to ride her cowgirl style, she began to slowly lift her hips and legs towards mine. I loved the feeling of being spread legged over her.

As we rolled over in the bed, I moved my back up against the headboard and with my legs spread, held her with her back against me. I now had the chance to caress her breasts with my hands and finger tips.

I slowly moved my hands down her stomach to her pelvis and began massaging her just like she does to herself when she stretches. She loved this and began arching her back and slowly grinding her hips upwards.

The feel of my legs spread apart coupled with her pressing against me with hers as she was arching back was so erotic.

I never penetrated her with my fingers but kept rubbing that spot that she was directing my fingers to. I could tell she was having these long deep orgasms and anytime I tried to move my hands, she repositioned them to exactly the right spot.

This continued for the longest time until she almost collapsed with the deepest of sighs. I was still hard and horny and she knew it. After a few minutes, she rolled over and with my legs still apart, slid down and whispered, "It's Jamie's time now."

I laid there in the white gown and was so glad there was a long split up the front. She slid the panties over to the side and took my cock in her mouth. I so wanted to hold on as long as I could.

"Does Jamie like me playing with her?" she asked, and then went right back to kissing and sucking my cock.

"I do, it feels so wonderful," I quietly replied. I began squeezing my own nipples and lifting my hips.

"Is Jamie going to have an orgasm?"

"I am but I want to wait, but can't. You feel so good," I replied.

"Then let it go Jamie..."

And with that I started driving my hips upwards like she had done for me so many times to me. She was holding me so tight around my butt and staying with me, drinking ever drop. I could not ever recall ever going that long.

The next thing I remember was waking up around 6:00 when she crept back into the bed, all washed and showered and asked if I wanted pizza for dinner.

I looked at her in that awakened stupor and she said, "Yes, my little angel, you've been sleeping for 4 hours."

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

I could almost end the story of Jamie here. And while there were so many more positives to write about, so many fun things we did, there were still things we both knew we needed to explore, but it had to be at the right time. I think the next big step came when Sally dropped by...

It was a late Saturday afternoon when my wife called saying that Sally was coming over. It was a casual day and I was wearing one of her skirts, a cute top, and my short wig with light make-up. I got a big hug when she arrived.

Sally remarked that Tammi had an outfit similar to that one and it reminded her of another story. We all sat at the kitchen table and had some coffee as she began explaining what happened as she was getting ready to leave for college years ago.

"My senior year of high school was full of so much excitement. I never wanted it to end but I was so excited about going to college. Tommy liked the idea as well because it seemed that every time a new school event came up, mom would take me shopping for a new outfit. He could hardly ever wait to see what I had bought"

"We had rules, and he was now really good at keeping them. Unless I gave him express permission, he was not to wear my new clothes. But then again, I gave him permission a lot once the event was over. And frequently I would actually help him dress up or do his make-up so I knew what he was wearing."

"But the reality of it all was...I was heading out to college and it was coming too fast. With spring came summer and soon I was beginning the process of packing up for college."

"My mom was taking it hard as her little girl was leaving. We had been doing so many things together that I was truly going to miss her as well. My dad had become a bit more distance as his work kept him traveling a lot, sometimes at a week on end, and my mom was struggling to do all the chores around the house that he could not get to while he was away."

"One reality that hit me was how Tommy was going to handle keeping his secret while I was away. In my room he had a complete collection of clothes and two full drawers of bras, panties and nighties that he wore on a routine basis."

"We talked at length about possible solutions, and while they would work for a while, he was bound to get caught by mom. We had to somehow get her into the mix."

"Then it was the day for me to officially leave for college. I knew Tommy was going to have a tough time adjusting from having full reign of my clothes to sneaking around again."

"For a while we chatted by phone every day, and then every couple of days. He was doing OK, but his dressing time and washing clothes, etc., was always fraught with a little fear."

"By the time Halloween came near, Tommy and I crafted a plan where he was going to tell mom that he was going to a Halloween party and wanted to go dressed as a girl."

"Tommy would ask mom if she would call me at school and ask if it would be OK for him to use some of my older clothes that I no longer wore."

"It seemed like a good plan, but my mom thought that I would never agree to it. But, at least agreed to call me and ask."

"She did call, and after a phone call or two, Mom and I agreed on a couple of different outfits and I gave mom some hints. I tried to be genuinely surprised, but generally supportive of this idea, explaining that I knew of guys that did that for Halloween."

"Several days prior to the party, mom laid out all the items I suggested on my bed. Dresses, skirts, blouses, bras and panties, even shoes and a wig. She was truly nervous about this whole idea."

"Tommy's role was to fake his understanding of girl's clothes and to act embarrassed but excited all at the same time. He did not disappoint."

"Mom first had Tommy go into my closet and try an outfit on to make sure it fit before she attempted any make-up. Tommy had already worn everything he was trying on so that was a really no brainer."

"Mom then told him to come out in the outfit and he did, but he was shy. She then did his make-up using the colors I suggested."

"Once she brushed out the wig and put it on, mom nearly cried. She told him how much he looked like me. It was not quite the reaction he was expecting."

"Mom made a few adjustments and he tried on the other outfits I had suggested. He could not decide which one he like more and neither could mom. Tommy then tried on everything again, loving every moment of it."

"She then said, "Tommy, any of those three will work. Why don't you just clean up, change and come down when you're ready. I have a few more things to do downstairs for dinner.""

Tommy spent a little more time in my room and had a chance to try on a few other things he had missed wearing since I was away. He did go downstairs but mom did not talk too much about it.

Just prior to Halloween, mom and I talked again and I kept asking her how he looked. She kept saying how nice he looked and I kept prodding her to let Tommy know as well. He needs your reassurance.

When Halloween arrived, she helped get him all dressed and dropped him off at the party. As it turned out, Tommy never went into the party but walked around trick or treating instead. That was the plan anyway.

That night when he came back in Mom told him again how good he looked dressed up as me. And how no one even knew it was him.

He then sheepishly confided in her that he actually enjoyed it more than he thought. And, that girls were so lucky to have such nice clothes all the time. He did not rush to change out of the clothes that night as he told mom all about the party (that really did not happen).

With dad away a lot, mom and Tommy got a lot closer. They didn't talk much about Halloween and dressing up, but they did get closer.

Thanksgiving break was just around the corner and I could not wait to get home from college. On the Friday after Thanksgiving, dad flew out on another trip and the three of us we were chatting in the afternoon. Mom brought up Halloween and said how wonderful Tommy looked all dressed up. I then had an idea.

Since I never had a chance to see Tommy made up for Halloween, I said, "Let's do it tonight! And then we can have dinner together. It's just the three of us. And it will be a dress-up night for all of us!"

Tommy thought it was a "dumb idea" but "reluctantly" agreed. I offered to do his make-up.

At dinner the three of us were wearing real pretty dresses. I asked. "Mom, give him some advice like you used to tell me."

She smiled and said, "Please sit taller, keep your legs together, take smaller bites."

It was fake basic training all over again. Mom was really getting into it.

After dinner we chatted some more, watched TV and just before retiring for bed I ran upstairs and got one of the nighties that was earmarked in Tommy's drawer and brought it down.

"If you're going to wear a pretty dress you might as well sleep in a pretty nightie as well."

Both mom and Tommy looked shocked at my offer. Mom then broke the silence and said..."Why not Tommy? Do it for your sister."

Before I headed back to school I told mom and Tommy, together, that I would see them at Christmas break, and that Tommy had permission to wear anything he wants at any time...and maybe we can do it again when I came back at break.

That really opened up the door for Tommy. He used that opening to bring in one bra, a pair of panties and a nightie into his room and kept them in his top drawer. Mom never said anything but I'm sure she saw them.

But then, it wasn't but a week later that there was a small freak snow storm in December that cancelled school, so Tommy was going to stay home alone. Mom said she had to go to work but maybe they would close early.

12
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