I neither crossdressed nor had any desire to until I was in my late-twenties. Let me tell you how it all began.
I arrived home one evening to find my wife dressed in a "magician suit". "What's going on?" I asked.
"The costume party. Remember?"
"Oh. Sure, now that you mention it."
"How do I look?"
"Great."
"Think anyone will know me?"
"Hardly. My dinner ready?"
"In the micro. Just heat it for a minute. Well, I'm off to pick up Elaine."
"Have a good time. See you when you get home." I kissed her good-bye as she went out the door. Now, for a quick meal and a relaxing evening. Undisturbed.
I'd more or less just settled back in my chair in front of the television when Lisa returned. "Problem?" I asked.
"Yes. Elaine is sick. She can't make it."
"So?"
"I can't go without her. I need a partner. You know that."
"So, what are you going to do? Get another girl at this late date?"
"I've got an hour. That should be long enough."
"I suppose." I turned my attention back to the program.
"Well?"
"Well, what?"
"Get out of that chair and upstairs."
"What for? Surely not sex."
"No. I've got an hour to dress you and get back to the party before my act goes on."
"Dress me? In what?"
"Elaine's costume. YOU'RE going to be my assistant."
"What? You're kidding."
"No! I'm NOT kidding. Come on, get upstairs. We haven't got all night."
I showered and shampooed. She styled my hair into a feminine style while I sat naked on a stool. The hair done, she painted my toe nails. "I got these on the way home," she said gluing long, false nails to my finger nails. She trimmed and painted the nails.
I sat quietly while she worked on my face for twenty minutes. "There," she said. "Done. And, you look great."
Looking into the mirror I had to agree with her. The eyes were slightly exaggerated, but all in all I looked great. Not like Elaine, but certainly VERY feminine.
"So," I asked, "what next?"
"Into your costume. I picked up what Elaine was going to wear."
In the bedroom she held out the low-cut, backless gold one-piece swimming suit styled costume Elaine had planned to wear.
"I don't think I'll make it in that. No boobs."
"No problem. I took a pair out of stock." Lisa sells fake boobs. Mastectomy forms for women who have had one or more breasts removed surgically. They are great imitations of the real thing and difficult to tell from the real thing when they're on.
I stood patiently while she cemented a pair of the realistic forms in place on my chest. Once they were in place she helped me into a pair of pantyhose and the costume. Black patent heels completed the outfit. I had to admit, looking into the full-length mirror I looked pretty good. I doubted that anyone in the audience would suspect I wasn't a female. I would just have to be careful when moving to move more effeminate then usual. "One small problem," I said.
"What's that?"
"I have a bulge Elaine doesn't have."
"Oh damn. I'll have to do something about that. Wait here."
She returned from her office a few minutes later with a piece of polyurethane cut in the shape of a bicycle seat -- with a long tail. I wriggled part way out of the suit, put the pad in place and then pulled the suit back into place. "There," she said appraising my look, "no problem now."
I had to agree.
We made it to the party with minutes to spare before our act went on. On stage I stood around looking pretty, distracting to the audience's attention slightly from Lisa's tricks. Most of the tricks were simple and fairly basic. We spent about thirty minutes on stage as the closing act.
Back-stage Lisa put a wrap-around skirt on me which matched the gold suit I was wearing. "What's this?" I asked.
"You can't very well mingle with the others wearing ONLY your stage costume."
"Mingle? You mean I'll have to stay and talk to people?"
"Of course. I'm here to have a good time. I can't just rush home."
"Well, take me home and then come back."
"I have to stay and get my award. So, as long as we're here we'll stay. You've been curious about what goes on at these things. Now's your chance to find out."
I mingled. Several women caught on I wasn't a woman and I explained Lisa had pressed me into service as her stage assistant. When Lisa received her award she introduced me as her husband and explained why I was dressed as I was.
All things considered I had a pretty good time at the party. We were slightly bombed by champagne by the time we started home.
Once home Lisa undressed and hung the rented costume on its hanger. Then she slipped into a VERY sexy, almost solidly lace nightie before helping me out of my costume. In a few minutes I was naked, except for the false breasts.
Lisa smiled, and winked at me. Then she turned and took another sexy nightie from her closet. "Put this on," she said smiling and lightly gliding her long nails across my back. I shivered under the touch of her nails. I put the nightie on and we went to bed. We had the greatest session of sex we'd had in a long time. I don't know whether it was the champagne, the nightie, the boobs or a combination of two or more. Who cared at the time? I certainly didn't.
I was slightly hung-over Saturday when I got up -- still wearing the nightie and breasts. I made my way down stairs to find Lisa in the kitchen preparing breakfast. "Hi Lover," she said.
"Hi."
"Have a good time last night?"
"You better believe it. Great, as a matter of fact."
"Me too."
We had no special plans for the day and I expected to just sit around the house tinkering with with my computer. Possibly taking a dip in our pool in the afternoon and catching a few rays to deepen my tan. Lisa showered and winked at me as she said, "Next."
In the bathroom I removed the nightie and dropped it into the laundry hamper. I put on our shower cap and stepped under the warm, refreshing spray.
Back in the bedroom I say Lisa was dressed in pantyhose, shorts, blouse and flats. I was about to reach into my closet to get something casual when she said, "Hey, let's try something. I've wanted to do it for years and now's the perfect opportunity."
"Okay. What?"
Dress you up like you were last night."
"You mean in that gold swimmingsuit?"
"Something like that. Promise me we'll spend the rest of the week-end my way."
After last night ow could I decline? "Sure. Why not?"
"Okay. Let's start with these." She handed me a pair of sheer panties. Cautiously I stepped into them. Next she handed me a pair of sheer pantyhose. It's really a job wriggling into them without tearing them, but I made it. Next came a pair of her short-shorts. Red at that. A loose muscle shirt followed and then a pair of her flats.
Walking around me she pronounced me ready.
"Ready for what?" I asked.
"Why our weekly trip to the market silly."
"Market? You want me to go out like THIS?"
"You did it last night. Why not today?"
"Last night was different. I mean it was dark. No one saw me."
"Only about five hundred people while you were on stage and when I received my award."
"That was in an emergency and a controlled situation. The people I talked to thought it was nice of me to help you. That's how they saw it. Helping you out of a jam."
"No matter. We're going." There was an authoritative tone in her voice. I shrugged and followed her down the stairs and out to the car. Lisa drove us to the market.
We must have spent an hour in the market shopping and waiting in line. Once the groceries were packed in the car she decided we HAD to take a stroll through the mall adjoining the market.
We wandered along the corridors of the mall window shopping until we came to the tall shop where Lisa has to get her things. We entered the shop. In the hour we were there she bought six pair of fantastic panties, a couple of bras, some lacey, sexy slips and half-slips, two dressy and two casual skirts. Some blouses. A couple of slinky, sexy nighties. A garter-belt, in red and some nylon stockings. And, a new one piece bathing suit. Satisfied with her purchases we walked to a shoe store where a sale was in progress. We seated ourselves and she tried on a couple of pair of heels. Finally, she asked for a pair of the highest heels they had in the store. When the clerk brought them Lisa told him to try them on me. They fit. She took them and we left the mall, headed for home.
After getting all the groceries into the cabinets I asked, "What was all that shopping about?"
"For you sweetie. For you."
"Me?"
"I can't have you wearing MY things ALL the time."
"All the time? Just how long do you expect me to dress in feminine things?"
"Whenever you're home. And in panties, perhaps nylons too, under your male things at work."
"You've got to be kidding."
"NO. I'm not. I want to dress that way. And wear your breasts. Oh, you don't have to wear THEM to the office. At least not yet. But you WILL wear them when you're NOT at the office. And you WILL dress in feminine things. Oh, and you're going to do some the lady's work around here. With a gardner working for us there isn't any man's work. So, it's share the lady's work."
She was serious. Good grief, what was happening?
Upstairs she hung my new things away in my closet. Put the new lingerie in my dresser and the shoes on my side of the closet. She changed into her tiny bikini in preparation for a session in the pool and sunning herself. I changed into the new one she'd purchased for me and followed her to the pool. It was a little awkward swimming with the breasts projecting from my chest but, after several laps of the pool I got the hang of it.
We spent an hour or so sunning before going in for a light, cold supper.
After supper I washed and put away the dishes before settling down for an evening watching TV.
About midnight we closed up shop and went up to the bedroom. She handed me one of my sexy new nighties and we each were wearing a sexie nightie to bed. Another night of great sex. I guess the lingerie was turning her on and it was beginning to turn me on.
Monday, after my shower Lisa removed my breasts. When dressing for work I put on a pair of pale blue nylon panties covered with lace insets. The soft material felt GREAT caressing my genitals and buttocks. Each time I moved when I sat I was reminded of what I was wearing next to my skin.
At home I found a skirt/blouse outfit and lingerie laid out on my bed. My breasts were in the bathroom, awaiting me.
Lisa complimented me on my appearance when I went down to help with supper.
The routine remained that first week. Panties to work. Skirt, blouse, slip or half-slip, bra, garter-belt and stockings and heels at home. A nightie for bed.
The next week my garter-belt and a pair of stockings were laid out with my panties for work. I covered my nylons with a pair of knee-length men's stockings.
I was enjoying the wardrobe changes and Lisa was teaching to use make-up. The first few times I was clumsy and looked awful, but with practise I became quite adept in its application and looked quite good when done.
We began going out evenings with me in feminine attire.
In a month I could hardly wait to get home so I could change. I was finding my masculine clothing a drag to wear.
One night, in September, I arrived home to find Lisa wearing a square dance outfit. Shirt, skirt, bouffant underslip, panties with rows and rows of ribbon on them and, of course, sheer pantyhose. "There's one upstairs for you. We're going to learn to square dance. Starting tonight."
Since I was, now, quite comfortable with going out dressed I didn't bat an eye at her information. I hurried upstairs to shower and change. I loved the little lingerie with its rows and rows of ribbon and lace, and the short skirt showed my legs to good advantage.
We had an absolute ball at the dance that night. I was surprised how easily I found a male partner and danced with him. We were, naturally, in a beginner's square.
We had tickets to the shows at the Opera House so Lisa bought me several smart evening outfits of long skirts and more formal blouses. With the skirts and blouses I had an almost endless combination of changes, so I wouldn't have to wear the same thing twice in a season. Monday nights were square dancing. Wednesday nights were reserved for the opera house.
I took my two week vacation in November. I planned to spend every minute of every hour of everyday dressed. The first day Lisa suggested we go to the mall. She had a surprise in store for me. We went to jewelry store where my ear lobes were pierced. Lovely little diamond tipped studs went into the holes.
At home Lisa said, "We're going to have to come up with a story for you in case we meet people who know you. From now on, when you're dressed like that, you'll be Donna. Don's twin sister. You're staying with us while your husband, who is in the Navy, is
overseas at some place where he can't have his family. Sound plausible?"
"Yes."
"And, if need be we can always send him to sea so you can visit for months on end. Now, about your vacation. I'm afraid it's down the tube. Susie quit Friday, so I need someone in the office while I'm out making calls. I expect you can handle that. Can't you?"
"I don't see why not."
"Good. Start tomorrow morning. I'll show you the ropes and you take it from there."
"Fine."
I started in the office. The routine was simple. I handled the calls. Set up appointments for Lisa, or one of her distributors. Pulled items from stock and shipped them. The UPS man came everyday to deliver and pick-up. I called orders into the factory. Kept the books. And was generally a Girl Friday -- except I was a girl EVERYday, not just on Friday. I interviewed replacements for Susie, but Lisa didn't like any of the candidates. No replacement by the end of my vacation so I called in for two more weeks.
In bed, after one of our routinely great sexual sessions Lisa said, "I want you to quit your job. I'm making more than enough for the two of us. You can have a territory and sell. That way we'll have more income if we really want it. Or, you can stay in the office. You're the best office manager I've EVER had. We can hire someone to help if you need it. What do you say?"
"I say, let's give it a shot."
"I thought you'd say that. Well, here's to a permanent Donna."
Who could ask for anything more? I was having the time of my life. The best of TWO worlds. Able to dress and pass as a woman -- BE a woman for as many hours of the day as I liked, AND enjoy the sexual pleasures of a man with a dynamite woman.