Ted/Teddi Sue and his wife of 8 years started down a path of crossdressing that eventually led towards going out to dinner at times with Teddi dressed up.
 

---

Admin Note: Originally Posted on BigCloset ClassicThursday, August 01, 2002 - 08:41 AM, migrated to BigCloset TopShelf by JOANNE206.
 

[email protected]

My heartfelt thanks goes to the real Teddi Sue for translating my English into Standard English, and her friendship.

Thanks to Brandy Dewinter for her story 'Reasonable' - this story is a twist on the best.

This is a work of fiction. Any resemblance to actual persons or events is unintended.

I grant permission to post this on any site that will not charge the end user to read it. All other postings or use require my explicit permission. I would appreciate having any Webmaster or Web Mistress notify me when posting this story.

Any comments are welcome.

This story contains adult situations, describes sexual activities, and deals with cross-dressing. If such material upsets you, or if it's illegal for you to read this - DON'T.

---

 
1.
 
After eight years, you would think I'd be used to it. I mean really. But no, it still gets under my skin. I guess I shouldn't blame Ted too much; it's only human nature. The one thing I wouldn't do became a preoccupation of his. I knew that he was faithful - he loved me too much to stray, and besides I could read him like a book.

But there he was, standing by the BBQ, gawking at Linda, our neighbor in the next house. She was poured into a slinky black dress, barely able to walk in her heels. Her husband had to help her into the car; with that skirt there was no way she could step in by herself. Nothing would make Ted happier than to see me helpless like her. As if!

It isn't that he doesn't like the way I look; I mean, what's not to like? I'm five eight, one hundred, and twenty-five pounds, with a really nice shape that I work very hard to keep. I'm a slacks and jeans gal, and I have the butt and long legs that really attract attention. Not to mention a healthy chest that provides more than a handful of shapely delight for Ted and me. I used to model, and have a face that graced dozens of ads and several magazine covers. I guess that's why I really don't like to dress up; I did entirely too much of it as a fashion model.

I was still a tiny bit miffed while getting ready for bed, but one of our rules is not to take our problems to bed. Work 'em out, or forget 'em. Well, I couldn't see any way we would work this problem out given Ted's male nature, so I decided to make sure we had a "good" night. The compromise I found years ago was long sexy nighties. They are really comfortable, and Ted's male brain kinda thinks they are slinky dresses. You know, it really gets him in the mood. Men are such visual creatures!

So there I am checking myself out in our large bedroom mirrors - I can hear his footsteps on the stairs - when I get this crazy idea. But just then, Ted came in, and his eyes opened so wide I thought they would roll out of the sockets. Truthfully, his reaction made my nipples as hard as his cock had become, and I forgot about anything but...

You have to understand, I'm not a morning person. So, while Ted works out on the Nautilus, I make the coffee and have my first cup. I brought the thermos carafe into the exercise room - really part of the basement - and kissed Ted good morning. Then we put on a tape, and did an aerobic dance together, had a cup of coffee, and did another tape. Now you might think that is strange for a man, but it really is a good workout, and best of all, we do it together. When we were first married, Ted just watched me, but then I mentioned that he probably couldn't do it anyhow. Well, you know how men are, and the funniest thing was that he couldn't! He fell all over himself. That just made him mad, so he kept at it. Now he is really good, even graceful, and loves it when I find a new workout tape. I have this one tape we use on Saturday or Sunday, when we have time, where we exercise holding one another - you can imagine what that leads to!

Anyhow, we were aerobic dancing together when I remembered my crazy idea - the room doesn't look like a basement room, what with the lighting and all the mirrors on the walls and ceilings- and I really concentrated on how great Ted looked in all the reflections. Maybe... The devil in me kept thinking about the idea off and on all day. You see, I work at home as an Internet fashion consultant for a large fashion oriented department store, and some days I have lots of time between consultations. We had Linda and Bob over that night for dinner and gin, and now Ted barely glanced at her since she was dressed as I was, in jeans and a blouse. So, my crazy idea slipped into the back into my mind, if you know what I mean.

As I think back on the dinner-dance that night, I know it really wasn't Ted's fault. You can't really expect a man to go against his nature. And to be honest, Bob was staring at me too; grass is greener syndrome, I guess. Linda is a really great person, but she is no beauty. I guess that's why she dresses in those slinky dresses with the daring necklines, to direct eyes away from her face and mousy hair. It's ironic too; she has tiny boobs, and the bra's the thing - if you know what I mean. I wore a pantsuit that was dressy, but I guess Ted could only see tight and slinky. I checked once and he was actually a bit hard. Now I know he would never in a million years trade me for Linda, and he didn't even dance once with her, but that crazy idea came back with a vengeance, and I just couldn't shake it.

I sometimes have a one-track mind, so the day after the dinner-dance, I made a list. I examined it from every angle and decided to do it. It would be expensive, but I figured two weeks of my pay was worth it. At the very least it would show Ted how much his looking at someone else bothered me - in a non- bitchy way. I leaned back thinking, 'I'm going to win this one!'

Boxes and packages began arriving and I put them in the guestroom; even with my discounts it really added up. 'Better make that three weeks pay,' I thought.

Thinking that this should show Ted how much I really love him, I continued to make preparations. By the time everything arrived and I checked it, reading instructions where necessary, and picked up last minute items - three weeks had passed! Well I didn't choose express shipping; that is really expensive! But the Saturday after everything arrived, Ted had a long-standing golf date with some of his business associates; I was meeting them and their wives for dinner; and on Sunday we had to attend a christening for my sister Peggy's new daughter. Next weekend was free; next weekend was it! D-day!

After our aerobic dancing we went to the kitchen for brunch and Ted asked, "Anything planned for today?"

"Yes, as a matter of fact. I thought we would do something different together."

He got up from the table and hugged me, giving me THAT look, "What did you have in mind?"

Since we had done 'that' last night, what he had in mind didn't seem that much different, but I was pleased that he wanted me again, so I hugged him back. Now, pumped up, and coated with perspiration as we were, things could have easily gotten out of hand. However, I kept my focus and said, "Easy now lover. Come upstairs and I'll show you what I have planned."

He followed me as I jogged upstairs; the image he brought to mind was that of an eager puppy dog scampering behind me.

First we went into the bath for our shower, another thing we did together most days. I don't know whether it was my anticipation or what, but as we soaped each other you could cut the sexual tension with a knife. Most mornings it was just very pleasant to be together doing little things for one another. Somehow, I kept myself in check, but obviously Ted was more than ready if given the least little bit of encouragement. But first things first, so I controlled myself.

I had tried a little smear of the cream on the back of Ted's calf two weeks ago, saying I thought I saw an insect bite. That was just before the second aerobic tape we did, and it washed off cleanly in the shower about twenty minutes later - with no sign of a rash, or hair, on that little spot.

"Honey, would you like to try something new?"

He had THAT glint in his eye when he answered, "Sure, what do you have in mind?"

"First, let me put this cream all over you, and you can put some on me too. THEN, I have a video I want to watch with you. OK?"

He gave me a big smile, "That sounds pretty kinky; I'm up for it."

And was he ever, but I did my best not to think about THAT. I was enjoying his anticipation now, and that made it a little easier to keep myself in check. The jar had no label, but I put on a thin rubber glove and smeared it all over Ted's legs, butt, tummy, chest, and underarms - even over his beard. Well, the label had said it was super-gentle and suitable for a man's beard; it should be at the price! Then I had him do the same for my legs and underarms, even though I really didn't really need it. I almost lost it when he brushed against me down THERE, but I managed to hold my self together. But I could tell he could smell me.

We have a TV in the master bathroom; Ted bought it for me as a joke when we first moved in. He thought I spent a lot of time in the bathroom, but when a game was on, he made use of it himself. Anyhow, it could show tapes playing on our bedroom VCR, so I started a tape he liked with the remote. We occasionally watched raunchy videos, but this tape was sure to interest him. It was from my modeling days, and showed a fashion show I was in that was devoted to eveningwear. He complained a bit about a slight burning, but he was so distracted by the video that he didn't fuss. I had to drag him back into the shower so we could rinse off. He could still see the TV and I don't think he noticed what remained of his body hair going down the drain. I noticed though, and saw that he had great legs - and I was very turned on by his androgynous look. I hadn't really expected that. After I rinsed off, I melted into him and we kissed deeply.

When we came up for air he said, "Wow you feel super nice, what's in that cream?"

"It's not the cream dear, it's just that neither of us has any body hair. It feels really nice to me too; maybe we can keep it this way?"

"What?" He looked down at himself; his cock and balls looked enormous. He touched his skin and continued, "Christ almighty, I feel like you!"

"Is that so bad?" I asked with a well-practiced pout.

"No, not on you. What will the guys say?"

"Since when do you sleep with them?"

"Of course I don't, but what if my friends see me?"

"Where will they see you?"

"The locker room at the club, when I go swimming. I wear short sleeve shirts in the summer."

"At the golf club all you do is change your shoes, and since it's October now, you're not wearing short sleeve shirts anyway. When summer rolls around, and if you like it this way, just tell them you are swimming against the clock, and keeping your skin smooth to make the best time. Otherwise, just let the hair grow back."

We discussed it a bit more, but it was undeniably a very sensuous change for the better for both of us; a benefit I really hadn't considered. We covered each other with moisturizing body cream, and Ted really didn't notice the scent, he was back engrossed in the fashion show. We were at that luscious plateau of desire, where we were each toying with the other to raise it a notch higher.

I waited for the tape to finish to ask, "Do you trust me?"

"I love you."

"Do you trust me?" I asked again.

"Yes, although that was pretty sneaky trick to remove my body hair."

"Worked out great though, didn't it?"

"Let me see." As he hugged me, we both fell on to the bed. Oh my God, I didn't want this just yet. His skin felt so great next to mine; it was as if a barrier had been removed. He must have felt the same way because he said, "Honey, I can't believe how good you feel. It's absolutely incredible." Somehow, I found the strength to keep him from completing his quest, but it was something I wanted, desperately wanted, too. Yes, I confess to a couple of little orgasms - but that only left me wanting more, many more.

Finally, we were back on our feet again and I led him into the guest room. On the closet door was a killer black evening dress; it was velvet and satin, with a low cut, off the shoulder design, that said, "Fuck me!" Hell it even made me wet. Well wetter. I thought Ted was going to pant with his tongue dragging on the floor. "Oh Cathy, are you going to wear that for me?" He put his arm around my waist.

I kissed him and said, "I'll wear that dress for dinner and dancing tonight, if you will wear an identical dress."

"What?"

"I said, I will have dinner and dance with you here, wearing that dress, if you will wear an identical dress at the same time with me." I spoke very plainly, and judging by his eyes, he understood me perfectly.

I thought he would say no, and I guess I really couldn't blame him. He just stood there for several minutes, looking at me, and then looking at the dress - back and forth. "You want me to understand what a big deal it is to get ready for a evening out, and what a pain it is to wear a dress like that, don't you?"

"Yes, and there is another reason, but I would like to tell you that later."

"You realize that there is no way I can fit in your clothes; remember the time I ripped your shirt trying to put it on by mistake?"

"The outfit I got for you is identical to mine, except it is properly sized to fit you. Are you game?"

He took the dress from the door and held it up in front of me, I could tell by his stiffening cock the answer before he said it. "Okay, but we won't leave the house, and we won't let anyone in that might see me. Is that alright with you?"

"Of course, this is only for you and me."

I wanted to get him used to the heels; so first, we both put on a lace up merry widow with a built in strapless bra. I showed him a pair of breast forms, actually a full 'C' cup, and explained that with his additional height, it would be in proportion compared to my scant 'C' size. He laced me snug, and I did the same for him, explaining that he needed it more than I did to make the dress look right. Actually I didn't need it at all, but wow! I couldn't believe how sexy I looked. I inserted the breast forms, using a little of the special adhesive to keep them from moving about. Then I rolled the sheer black stockings on him, hooked them to the widow's garters, and followed them with the heels. He had a far away look on his face as I rubbed his legs through the sheer silky stockings. I asked him to kneel down and roll my stockings on. Usually he took mine off me, but he had the idea, and it was very sensual. Next, I placed a wig on his head that I had ordered just for him. I wear my hair in a style that falls just short of shoulder length, and the wig I ordered was a very similar style and color. Once that was pinned securely to his hair, I said, "These heels are only three inches and the heel is blocky. I know you like the higher, sleeker, spike heels on me, but I didn't think you could manage them the first time. Let's walk around together so you can get used to them."

We ice skated frequently in winter, so he was pretty stable - I was counting on that. As we walked out to the hall, I showed him how to walk in heels, up and down the hall several times, our heels clicking on the wood flooring. God but it was sexy; the both of us dressed like this. His cock was rock solid and didn't even bounce. The whispering sound of our stockings as we walked gave me a wicked idea. I wondered how he would take the next step in dressing for the evening, but first...

As we walked back into our bedroom I hung back a little, and when Ted caught sight of his image in the mirrors, it was as if he were transfixed. I came up behind him and said, "You will never be able to wear a tight dress with THAT," holding his shaft to emphasize the point. It didn't take much encouragement to get to the bed, and since we were both panty less...

God he was like a stallion, a wonderful hairless stallion pounding into me. I guess the widows restricted our breathing, and I think it prolonged our passion - another unexpected benefit.

We napped for over an hour, and I awoke first. Boy, it was weird; it was like being in bed with a girl, a husband-girl, I giggled. My gaze traveled down; definitely a husband-girl! Our stockinged legs were intertwined. This was so definitely hot. Finally, Ted awakened. At first he was disoriented, but after a moment he said, "This is some idea you had, do you want to continue?"

"I've liked everything so far, how about you?"

"Yes... And I really want to have dinner with you in that dress. I mean with you wearing that dress, even if I have to too." He had grin from ear to ear. "I never knew how nice stockings feel against hairless skin. What don't you like about this?"

"When you put it that way, nothing. I guess it's just that I wore them all the time, and you have to be really careful or they will run; sometimes they get baggy; the seams are a pain to keep straight..."

"But this feels pretty darn good to you too? Now I mean?"

I giggled and snuggled. We got up and I had him put on a special panty girdle with a tube sewn in to hold his cock back between his legs. His balls actually popped back into his body like that website said, and the result was a flat front just like mine. We put on identical peignoirs and he shook his head in amazement as he looked at our reflection.

Actually, I didn't think it would do much good on his face, but I applied a clay mask to him and showed him how to do me. I tactfully didn't remind him that he hated to see me in a mask. Then I put his hair up in rollers, again for the experience, and had him do mine under my careful direction. We did each other's nails; both of our nails were pretty short, but we applied tips, finishing them up with nail polish and gloss. It was fun for me, and I think for him too. Before I knew it almost three hours had passed. Ted was very careful and I found myself chatting with him about putting all this together, we discussed things we never had before. My biggest surprise was that Ted had really paid attention to me - he might only say, 'you look great babe,' but he noticed details - frankly, I was shocked. This was going so differently than I had planned.

We washed the mask off, and I did my makeup explaining the steps; then I did his - except that I let him fill in his lips after I outlined them. I looked at his face - well in dim light it would pass for an unattractive girl. As I brushed out his hair I could see things to do, like shape his eyebrows - but not for tonight; this was good enough. When he brushed out my hair, he was very gentle, and I loved it.

As we walked into the guest room for the evening gowns I gave him pointers on how to hold his hands. He was standing straight and looked pretty good. The gowns were gorgeous. They were last year's style, so I got a real good deal - a little over a hundred dollars each. I opened my peignoir and let it drop to the floor in a dramatic gesture. Ted brought my gown over and unzipped it, holding it close to the floor as I stepped into it. He zipped me up saying, "Baby, this was made for you." He stepped back, "So nice. You look so very nice." It's a good thing I had a panty liner.

I went to the closet to get Ted's gown, and seeing it he said, "You really did it." Then he let his peignoir fall to the floor just as I had, and waited for me to arrange his gown. As he stepped into it, just like I had, I started to giggle, and damned if he didn't too. I was worried that it might not fit, but it was perfect. The off the shoulder design felt very strange to him, but I told him it felt strange to me too. I finished the look with complete sets of identical costume jewelry, including tiaras, for each of us. Ted insisted on putting mine on me, as I had his on him.

Returning to the bedroom, again, I held back to see Ted's reaction to the complete package. He goggled at his own image in a slinky sexy gown. It was THE gown! I really could rest easy. Then he started to move and twirl, with little dance steps. He looked at me and said, "Come join me." We waltzed in front of the mirrors until the doorbell rang.

"I'll get it. It's the caterers with dinner." Going downstairs carefully, mindful of my dress, I let the caterers in. I had used them in the past, and they quickly set the table, left the food in a cart by the sideboard, and left. Getting our instant camera, I went back upstairs for Ted. We took a few pictures and then had dinner.

I thought I had gotten Ted a few times at dinner; it certainly wasn't how he usually ate. He had to be careful not to smudge his makeup, drip gravy on his bosom, and keep from pushing errant hairs. One time I said, "Dammit Teddi, your hair is supposed to come down like that - it bugs me too, but you always tell me it's sexy."

He stuck his tongue out at me like a little girl, but stopped fiddling with it after that. I found myself calling him Teddi Sue the rest of the night. Well, looking like that Ted didn't sound right, and my best friend in grammar school was Teddi Sue - it just sounded right to me.

When we went to the powder room, I doubled up with laughter as Teddi Sue raised the tight skirt and adjusted stuff just to sit down and pee. We fixed our makeup after I tended to nature, giving Teddi a laugh too - well; it was almost as hard for me. I pointed out with glee that we had spent fifteen minutes in the powder room doing that simple thing, but we had talked a lot too!

So, you ask, was it worth the trouble and expense. How much would you spend for the best sex of your life? We had it that night, at least up to then. We now dress for dinner every month or so and last week, we actually had dinner out. Yes, out! Now that was exciting, and when we got home Ted was an animal. A real nice animal, but I thought he would split me in two! We talk to each other now, about lots of little things - over and above what we always did; what's that worth?

Yes, most of the time we wear the same nighties, it gives us a little extra tingle...

---

 

[email protected]