Caught For the Last Time Ch. 05


In the morning I woke up in a much better state of mind. Less confusion and perhaps a better outlook on what had happened the prior night with Sally.

Still, I was not all that comfortable with someone else knowing about my crossdressing, but at the same time, having someone for my wife to talk to was better than the way it was before, way better.

We had a real quick breakfast and my wife said, “Let’s see what she brought. I truly have no idea.”

We opened up all three bags in the living room. There were skirts, blouses, tops, dresses, sweaters, slips, nightgowns, jewelry…and wigs. Sally did have amazing taste in clothes and my wife was looking at the labels she said, “These must have cost her literally hundreds of dollars.”

I was like a kid at Christmas looking at everything and holding them up.

My wife said, “Why don’t you go upstairs and change into your bra and panties? Looks like we’re going to be here for a while.”

By now I was a seasoned pro in terms of what to wear. I tossed on the neutral colored bra and panties. No need to have pink ruin the look of anything I was going to be trying on. When I got downstairs she already had an ivory top in her hands.

“Let’s start with this cute top while you try on the skirts.” She then handed me one skirt at a time to first see if they fit, and then determine if I wanted to keep them.

Skirts are always fun to try on and easy fit. I even had brought down my slides on for a little extra lift and loved how the long skirts just flowed. There were 5 skirts in total ranging from floor length to a mini…they all fit perfectly. And, we both loved them all. They were all were keepers.

My wife helped match up three tunic tops with two different skirts and was able to mix and match to come up with several different outfits. They looked great on. Unfortunately not all the tops she gave me fit because of the shoulders. I just needed a little more stretch in them up top. But still there were six other tops, ranging from a pretty stretch lace to button up ¾ length sleeve blouses that worked.

While I was doing all this changing my wife was brushing out the two wigs. One was a short bob with auburn highlights and the other one was shoulder length and had a dirty blonde look to it. I had never had a wig on before.

When I was standing there in one of the outfits my wife said…”Hold still. Let me brush this out on you and see what we have.” When she was done all she could say was, “Oh my.”

“Stay right there one more minute and don’t look.” She quickly got some of her lipstick and said she needed to add a little just to give my face some balance. It was probably one of the few times in my life when I was glad I was relatively fair skinned and not a lot of facial hair.

When she finally let me look at myself in the full length mirror, I had the first glimpse at what I had been imagining all my life. I actually looked like a female, not a guy wearing women’s clothes. I loved it!

We kept going through piles of clothing. The dresses were really nice. The dress lines Sally like were long. No horizontal patterns, no silly abstracts, just class. One did not fit as it was too tight in the bodice, but next three fit perfectly. I especially liked the one with the stretch lace bodice and empire waist. Five dresses were ideal.

We switched off the wigs on each outfit and my wife said how nice different jewelry would look on each one…sometimes holding up a long necklace and sometime a short one.

The slips were fine and the sweaters were great as well.

Last up were the nightgowns. The nightgowns were long and sexy in the purest sense of the word. One of them had a gown with a robe that flowed to the ground. I loved how it looked as I walked across the room…almost in slow motion!

“Hmmm.” She said.

“You like it?”

“Yes and no,” as she walked around me, fixed the robe a bit and slid her hands across my back and down my sides.

“Yes?” I asked.

“Yes, because it really, really looks nice on you, especially with the wig.”

“And no?”

“No, because it really, really looks nice on you, especially with the wig.”

We both laughed. She walked behind me, placed her head against me and quietly gave me a real long squeeze. She just stood there for a moment holding me.

For the first time this morning, my excitement from wearing these clothes showed. I tried to hide it a bit and she said softly, “We’ll have time for that later on. We have a few more nighties to try on.”

The other 3 nighties were gorgeous and fit as well.

I changed back into one of the more casual dresses and kept checking myself out in the mirror. I then turned and said,

“I never expected all this and I’m so glad you suggested waiting until morning. I really love these fatih escort clothes and this look.”

“Nor did I. When Sally told me she had some things, I was thinking a few like, 3. You have an entire fall wardrobe.”

Then I asked, “Given the circumstances, would it be possible for me to stay dressed for the whole weekend?”

As she had been watching me in the mirror playing with my hair and looking at myself from all directions, she said, “I think that would be a good idea…for both of us. I need to get more used to this full look as well.”

It was difficult to figure out what to do the rest of the day. My brain was truly scattered.

One thing for sure was that I had to figure out where to keep all this. This was not the same as buying 3 bras at Kohls. For now, the least I could do was bring it upstairs to the bedroom and go from there.

My wife called Sally later that day and thanked her for both us. I heard her describe in detail the process of what fit and what didn’t. It was almost like hearing a Tommy story all over again. Over and over again she explained how happy I was.

My wife seemed comfortable speaking to her about me the whole time and even the responses to Sally’s questions, were upbeat, some laughing, some serious like…”Absolutely”, “That would be fun”, “Definitely could see that”, “He sure did”, “We can only wait and see”, “Adorable”, and “Perhaps.”

After she hung up, she came over and gave me a big hug and said “Sally is real happy for you and is glad so many items fit you, and that you like them.”

“I had misjudged Sally,” I replied, “You’ve got a good friend.”

Around 3PM, as I was standing in front of the mirror, again, my wife said, “I’m going out to do a little shopping. I’ll just leave you two alone.”

We both chuckled at that one and off she went.

While she was out I tried on a few more combinations and settled into a nice skirt and longer top for the evening. I found some jewelry that worked and literally was floating around the house looking for things to do and catch myself in mirrors.

I set up the table for a nice meal and really enjoyed the full experience of being dressed. I really felt like the woman of the house and just loved the idea of being fully dressed.

My wife arrived back home in one of those secretive…you have to wait and see…moods. I always loved those.

All throughout the dinner that I had prepared, she kept looking at me. I knew something was different. Maybe it was the way I was acting…trying to be as feminine as possible or maybe it was just seeing me in a wig and make-up that made a difference to her. Whatever it was I was liking it.

We sat and chatted, mostly about clothes and how much fun they were. And then she suggested we call it an early night. That was generally her code word for let’s have sex, but tonight I hated the idea of getting changed back to the other me.

We both headed upstairs and as I started to remove the wig in the bathroom she asked, “Aren’t you wearing the wig with one of the new nightgowns to bed?”

“I really wasn’t sure how you would feel about it.”

“Well, when you asked me if you could stay dressed for the whole weekend I really thought you meant the whole weekend.”

“Sorry, I just wasn’t sure.”

“Seriously, it’s OK with me if you wear them. I’ve been kind of getting ready for this during the day and figure there’s no better time than tonight.”

As I headed over to where I had placed the nightgowns she said, “I’ll be right back.”

I was now looking at the four nightgowns in a whole different light. I tried to pick one that was sexy but also a bit conservative. The good news was that these from Sally were all a bit conservative. The one I finally selected was ivory and had a soft lace bodice with long slit up the front and matching panties.

When she came up to the bedroom she was carrying a chilled bottle of white wine and two glasses. “I think we could each use this after these last 24 hours. Maybe I should have brought up 2 bottles?” she joked.

She looked over at the bed where I had laid out my selection and she said, “I had hoped you were wearing that one…I love it!”

She then popped the cork and poured out the two glasses. She then walked over, gave me a kiss and handed me the glass of wine and said, “Here’s to a new beginning.”

We each had a sip and she whispered, “Let me go change as well.”

I got changed with renewed excitement. Wearing the gown with the wig and make-up made such a difference. I stood there sipping the wine and looking at myself in the mirror. What I saw was what I was hoping for. I could feel my nipples getting hard and I let myself enjoy the feeling as I waited.

In about five minutes she returned wearing çapa escort just a new black robe with just matching black string bikini panties with cute side ties. Her robe was open and her breasts were just asking to be kissed. She was gorgeous.

“Let me refresh your glass first,” she said. Mine was barely down a notch but hers was empty already.

She gave me a deep kiss, caressed my nipples, thought for a moment and said, “I’ll be right back.”

In another five minutes she returned in another new outfit. She was in all black. She was now in loungewear with these sexy long leggings that flared at the bottom. Her matching top clung against her body. Every curve showed and she knew it.

She was wearing black heels and had her hair tied back in a ponytail. She looked so freaking hot. She reminded me of Courtney Cox in a Charlie’s Angels fight scene.

She reached over and poured herself some more wine and asked if I wanted any more.

She took me by my hand and we both sat on the bed facing each other. She began to caress my arms and my thighs gently with her hand. There was a soft kiss on my shoulders and then on my back as she crawled around behind me like a cat.

“When I saw you in the wig today, it got me so excited.” She continued to kiss and caress me.

She reached around in front of me and caressed my breasts as she kissed my shoulders and back.

“You looked so radiant and excited as you tried on each outfit. I could tell, just from your face.”

More kisses, more circling around me.

“It was like the wig transformed you, not just in your eyes, but mine as well.” She kissed my shoulders and then crawled around in front of me.

“I may have been mistaken, but never once, until you put on the nightgown did you even get aroused. Maybe you did but I didn’t notice. You seemed so natural.”

I closed my eyes and started drifting away as she played with my nipples.

“But for that entire time, as you were trying on outfit after outfit, you and I were both seeing a different side of you. A side, like you had told me so many times, that has always been there. Perhaps a side that does not need to be there all the time, but one that wants to come out fully on occasion…like tonight”

She then took my hands and looked me straight in the eyes.

“And seeing you like that brought up feelings and memories that I had not had in almost ten years. And they were good memories, not bad.” She continued,

“I’ve never shared this with you, but when I was in college I played volleyball.” She kissed me deeply and I replied,

“Yes, I knew that. And you were awesome.”

“And I had some great teammates and they were all awesome and very fit.”

“Yes, I’ve seen the pictures, and you looked hot, especially in those tight volleyball pants,” I replied.

“I know, and so did my teammates. In fact, we all kind of thought we were all hot.”

“And to me, I thought Stef was the hottest. She was a sophomore and cute as could be. I was a junior and was all about my fitness, my core, my crunches.”

“Stef had long, dark curly hair, was one of our diggers, and she had a great pair of breasts. I liked mine and all, but hers were just so damn perfect.”

She began sighing deeply and fondling her own breasts, and then reached over to mine again. I could sense the wine kicking in.

“We trained together, traveled together, celebrated our wins together, and cried over our defeats together. She was my roommate on the road and at times we actually had to share the same double or queen bed on the road.”

“It started innocently after a tough defeat when we were both crying and we hugged each other, and then the passions rose. It was that night that we became more that just teammates. For that season and for most of the rest of the year, we were intimate with each other. Not all the time, but on occasion. It was almost always when we traveled as a team, and then some other times on campus.”

“Stef enjoyed being the passive one and I loved the active role. And with those breasts, who could blame me?” She kissed me again and began stroking my hair and face.

“Stef and her magnificent breasts transferred to another school the following year and I became interested in boys again, and then I met you. Stef was just a brief moment in my life, but an important one as I look back. I realized that I was not always the person I thought I was.”

“Over the years that we have been married, I realized that I have been acting like a prude when it comes to you wanting to wear lingerie every so often. I had been hiding my past and afraid of letting you live something that I kind of did. It was my own defense mechanism I guess.”

“I had not felt this way until I saw you in the wig. I saw how genuinely sarıyer escort excited you were about being someone different.”

“I don’t ever want you to stop being my guy husband, I love him, but if being this other you every so often will work for both of us, let’s do it. I can handle it.”

“So tonight,” reaching over and taking another long sip of wine, “is your night.”

She crawled on top of me and began to kiss me from my neck down. I felt like I was wisked away to another planet. My back arched up to have my nipples thrust in her mouth. She was massaging my other breast with her hand through the nightie.

As she kissed me, she spread my legs apart with hers. I knew she was strong but never imagined her getting between me would feel so good. I now understood why she changed her outfit, she wanted to be the dominant one tonight.

She was grinding her body all over mine. She kept driving her pelvis into mine and I thought I was going to explode.

With my legs spread open, the nightgown had now fallen open to either side of me. Choosing the nightgown one with the slit front was now a wonderful idea. As I reached down to put my hands under my hips, I loved the soft feel of the nightie around me.

It was wonderful being underneath her. I could just enjoy every minute as she stayed on top of me. She kept kissing, sucking and biting on my nipples while all the time sliding her body up and down on me. I had all I could do from exploding all over her.

She sensed it and slowed down the pace and began a long slow thrusting motion, almost like I was getting laid. I did my best to wrap my legs around her as she continued faster and harder. At times I thought I was going to split apart. I couldn’t hold it and I knew she could feel the heat pulsing through her clothes as I became to cum.

She never stopped and she began to moan deeper and deeper. Then with one long passionate moan she collapsed in my arms and her body became so relaxed. I just held onto her and lightly caressed her back.

She rolled over on her back and said, “That was so freaking amazing! You are definitely keeping that nightie.”

I’m not sure how long we just lied there, but we were not in any rush to move. Finally, she rolled over and whispered “I’m taking a quick shower and will be right back.”

Seeing her walking away in her black lounge pants and tight top just reinforced what had just happened. I was really hoping that this was not the last time.

I used her shower time to make a quick assessment of myself. My panties were still on but drenched. I tried not to move too much but I knew my cock was deep purple from holding on so long. My nipples were beet red and wonderfully sore. My hips almost felt out of place. This was awesome!!

She returned wearing the first robe and panties she had on tonight, gave me a cute kiss and I headed in to the shower next. I could barely stand. The hot shower felt so good.

As I was toweling off I noticed there was one of Sally’s nighties and panties hanging on the back of the bathroom door. Since they weren’t there when I started, I assumed it was her way of saying, please wear this one to bed.

When I got into bed, there wasn’t a word as she cuddled up to me and fell asleep.


Needless to say, we got a real late start on Sunday. I still awoke before she did and took a long shower. Waking up beside my wife while wearing a nightie was wonderful…so much more fun that by myself when she was away. But my breasts were real tender.

I still wanted to stay dressed today and get used to a few of the new outfits. I decided to go casual at first and put on a skirt with one of the buttoned blouses and the other wig. I loved that look as well.

I went to the kitchen and started preparing a real nice breakfast, practically a brunch by now. It must have been the smell that woke her up.

“Isn’t this nice?”, she said as she almost stumbled into the kitchen in her robe. I got a big kiss followed by a long hug.

She continued, “I could get used to mornings like this. Did you enjoy last night?”

“It was better than I ever expected. You were amazing. I loved your new outfit too, both of them. That was a nice touch.”

“I just had to get them. I thought the look would be appropriate for the night. And how are those nipples, girl?”

“Does it hurt you this much the day after?” I asked.

“Maybe not as much as it does you this morning, but you’ll get used to it.”

As the day went on, I kept wandering around the house looking for things to do. I know I was going to drive my wife crazy if all I did was look at myself in the mirror so I said,

“Can we just get out of here for a while? I’m not sure I can take this for a whole day. Let me just clean up a bit, toss on one of my softer bras, a shirt and pants and just head out. I can always dress later on tonight.”

She laughed and said, “That sounds like a plan.” She then came up behind me and playfully squeezed my breasts again as I winced in pain. She whispered, “Oh yeah, we had a good night…”

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