Marcie got up early to go to work, and I slept until about eight-thirty when I had to get up to go to one of my part-time jobs. I saw the clothes I had worn still lying on top of the covers, and I picked them up to put them away
Marcie got up early to go to work, and I slept until about eight-thirty when I had to get up to go to one of my part-time jobs. I saw the clothes I had worn still lying on top of the covers, and I picked them up to put them away
I put in my four hours of filing and got back home at about two o’clock. The work I had been doing was mindless, and the only reason they had me as a part-timer was because the secretaries hated doing it.
It was a really tough job market out there. I had recently graduated college, and going on as many interviews as I could schedule, without success. My girlfriend hadn’t had nearly as much trouble and had landed a well-paying job at an advertising firm.
And since we were living together at least I had a roof over my head. I had paid my way through school with a combination of scholarships, loans, and part-time jobs, but I just couldn’t find anything now. It was already well into August, and the only contribution I was making toward our expenses was the little I made at three part-time jobs.
“Dammit, Marcie,” I said to her one evening, “today had to be the most frustrating day of all. I had three interviews, but they were all the same `Sorry, but we don’t think so. We’ll keep your resume on file if something should turn up later.’ Right, like they didn’t trash them as soon as I left.” “Don’t worry, hon,” she said, “I’m sure something will turn up soon.” “I don’t know,” I said, I think I’m a victim of discrimination or something.” “What makes you say that?” she asked, “you’re not a member of a minority group — I think you’re overreacting.”
“I don’t think so, from something I overheard today. I had just walked out of the last interview and I heard one guy I was talking to say to the other, `Too bad — but I didn’t expect it from his name.’ I think if I had been a woman, I would have gotten the job. They were ready to interview a girl named Donald, not a guy.” “I still think you’re overreacting; you probably misunderstood what he said.”
Well, it was three weeks after that night, and still no job. But now I finally had some evidence to support my suspicion. I had just come back from a long interview, and I had really hit it off with the interviewer. I was telling Marcie about it, “Then he said to me, `Donald, I think you’d be perfect for the job, and what I’m going to say is off the record, OK? I’ll deny I ever said it, but, well, my boss set down strict guidelines for hiring.
We can hire guys who are in the top 5% of their class, but because we need to hire more women, we can hire them if they’re in the top third.’ See, Marcie, I told you so, I’m being discriminated against!”
She sympathized with me, but just encouraged me to keep on trying. Another three weeks of no success had me pretty depressed, and we decided to watch some TV to cheer up. I hit the ON button on the remote, and what was playing but “Tootsie”. Dustin Hoffman tried to make it as a guy, but achieved success only after he dressed up as a woman.
“Boy, that’s the right, idea,” I remarked, bitterly, “if you can’t beat ’em, join ‘em.” Marcie looked at me strangely for a minute, then said, “You know, Donald, you’d make a better-looking girl than he does.” “That’s ridiculous,” I said, “I could never get away with that — people would spot me in a minute.” She didn’t say anything, and I switched channels, ending the conversation right there.
A few days later, we were lying in bed together, having just made love, when she brought it up again. “Remember what we talked about when we saw “Tootsie” the other night?” she asked. “Yes, I do — your silly idea that I could get away with dressing like a woman.”
“Well, I still think I’m right, that you’d be cuter than Dustin Hoffman.” I really didn’t feel like talking anymore about it, but she continued, “I’d be willing to bet I’m right.” “Sure,” I said, “bet what? You know I’m broke, and besides, it’s really a dumb idea.
There’s no way I’m going to dress up and go out as a woman.” “Well,” she replied, “we could bet washing the dishes for the next month.” Both of us hated to wash dishes, and we rotated the chore every night. “As much as I’d like to not do dishes for a month,” I said, “because I know I’m right, there’s no way I’m going to make a fool out of myself.”
“What if there were a way, you could try it without any risk? she asked, “Would you still be willing to bet?” I was tired by then and I said, “Sure, no risk, whatever you say.” “So do we have a bet?” she persisted.
“Yes, yes, OK, we have a bet,” I said, and we fell asleep without any more conversation on the subject. I didn’t think about the conversation the next day, and I made us a cold dinner, waiting for Marcie to get home. She had called and said that she was stopping off at her sister’s house and would be a little late.
It was almost eight o’clock when she finally got home, and I told her, “I was starting to get worried about you,” and I gave her a big hug and kiss, relieved that she was alright.
“It took me longer than I thought it would,” she said, “but we finally got done.” “Done?” I asked, “What were you doing?” “Getting ready for our bet,” she said. I noticed that she had two shopping bags with her. “What’s in the bags?” I asked her. And she proceeded to lay out her plan.
“There’s an office Halloween party coming up, and that’s where I’m going to win our bet. There’ll be a million people there, clients, agency people, friends, and vendors, and hardly anyone will know anybody.
I spent the evening at Patty’s getting your costume.” I hadn’t taken her bet seriously last night, but obviously, she had!
“What do you mean, my costume?” I said, suspecting the worst, and her answer confirmed it.
“You can dress up as a woman for a Halloween party without any risk — lots of guys do. And since no one from the office knows you, no risk, just like you agreed to.” I tried to argue her out of it, but there was no way she was going to cancel the bet. I resigned myself to the fact that she had the costume I was going to wear in the shopping bags.
We sat down and ate, and we avoided the topic until she said, “C’mon, be a sport, you did agree to the bet, and it was only for one night for the party.
I don’t want to make you feel bad, though, so I’m willing to cancel the bet if you insist.” “No, we made the bet,” I told her, “and guys just don’t cancel bets. I’ll go along with it, though I’ll feel silly as hell, and everyone will know I’m a guy.
Besides, when I win the bet, I’ll enjoy watching you wash dishes every night for a month. Who knows, maybe you get to like it, and you’ll want to wash them all the time!” “Fat chance, buddy,” she retorted, “and I still think that you’ll be the one with dishpan hands! Speaking of which, it’s your turn tonight.”
Sighing to myself, I got up and washed everything while she went inside.
When I had finished, I joined her, and she turned off the TV she had been watching. “You know,” she said, “you really have to try your best not to be discovered, if this is going to be a fair bet,” I said that if I did anything that would deliberately make me win, I would lose.
“Is that fair enough for you?” “Well, almost,” she said, “but not quite.” “What do you mean, not quite?”
“Girls learn how to be girls as they grow up, years and years of becoming ladies,” she said. “You can’t just learn it overnight. To be really fair, you should practice.”
“C’mon,” I said, “fair is fair, I agreed to one night, not `years and years of practice’. Besides, there’s only two weeks until the party.” “OK, I’ll settle for two weeks of practice,” — although I hadn’t agreed to any practice at all!
“Let’s get started, there’s no time to waste.” She took the shopping bags in one hand, and my hand in the other and led me upstairs.
In short order, I found myself standing naked in the middle of the bedroom, watching Marcie pulling clothes out of one of the bags. “I wasn’t exactly sure about sizes, so I got a whole bunch of Patty’s things — she’s more your size than I am.” It was true, I’m quite a bit bigger than Marcie, while her sister Patty is nearly as tall as my 5' 9" and has a larger frame than her petite sister. I have a very slender build, though, for a guy, and I guessed that we were probably about the same size.
As often as Marcie and I had made love, it still felt strange to be standing naked in front of her while she was doing something else, and I found that I was getting an erection. When she saw it, she laughed, and began to stroke it, teasing me, “Don’t tell me that thinking about dressing as a woman is turning you on?” “N, no, don’t be silly, it’s just be naked while you’re still dressed,” I said.
“Well, we have to do something about this,” she said, continuing to stroke me, “or else you’ll have a bulge in your panties.” She knelt down in front of me, and took me into her mouth, quickly bringing me to a climax, while thoughts of how I would soon be dressed disturbingly ran through my mind.
“OK, now that THAT’s out of the way, slip into these,” she said, handing me a pair of white panties. They felt strange going on over my legs and nestling around my groin, but I told myself that was to be expected, these weren’t exactly my usual jockey shorts!
Marcie helped me put on a matching white bra, stuffing the cups with a couple of pairs of her panties after she fastened the hooks in the back. She sat me down on the bed, and, as I followed her instructions for putting on pantyhose without causing runs, the bra felt really weird on my chest.
The pantyhose felt even more strange, covering my entire legs with the feeling of the sheer material. “These are just regular daytime things,” Marcie said, “I hoped that I’d be able to convince you to practice.” She was really serious about winning this bet, I could see and had planned the whole thing out. I stood up, feeling the tickling sensation of the nylon against my leg hairs, and pulled the slip she handed me over my head.
She settled it around me properly, making the smooth nylon rub over my whole torso. She then lifted a pink and white striped dress over me, and I raised my arms so it would slip down into position. I began to button up the front of the shirtwaist dress, fumbling because the buttons were on the “wrong” side.
“Well, you don’t have much of a figure, dear, but at least everything fits pretty well. Except for the waist, of course.” My waist did stretch out the waistband of the dress, and I said, “See, I told you this wasn’t going to work.”
“Don’t worry, we’ll take care of that when the time comes,” she said, “after all, not every woman has a perfect figure.” I didn’t have a chance to ask what she meant, because she was handing me a pair of medium-high heels to put on. The swishing, swirling feelings of the feminine materials against each other and my body felt extremely strange as I walked over to the bed and sat down to put on the shoes.
“You’re lucky my sister has big feet,” she commented when I had put them on, and tried to stand up. I almost fell over because of the tilt they gave my body, but Marcie steadied me. “OK, practice walking around a little,” she said. I did, feeling more silly than ever when she began to coach me on how to walk in a ladylike manner.
“A little more hip sway, but not too much,” she said when I exaggerated my hip motion. “You’re not going to be a hooker, just a real lady.”
She made me wear the clothes until it was bedtime, and I had almost gotten used to the heels, but not to the feeling of the soft, silky clothes against me. I had an erection again, unusual for me, since I was strictly a “once-a-day” guy, and the oral sex Marcie had given me would have ordinarily finished me off for the night. Were these unusual clothes, and the way they felt on me the cause of it, I wondered. Marcie helped me get undressed, and I managed to hide my cock inside my robe as I went in for a shower.
I came out, and Marcie went in for hers, and I found myself touching the things I had been wearing. I heard the door open, and feeling my face flush at almost being caught touching the feminine finery, I shut off the light. She hopped into bed next to me, and asked me, “That really wasn’t so bad, was it?” “N, no, I guess not, just strange is all.”
“Well, remember your promise, you have to practice every night until the party,” she said, curling up against me. “You really did look pretty cute in the dress, not to mention in your bra and panties,” she teased. “Oh, cut it out, I looked exactly like what I was, a guy in drag. You know, I’m more convinced than ever that I’m going to win this bet.”
“We’ll see,” she said, kissing me goodnight and turning over, “we’ll see.” I lay awake for a while waiting for my erection to go down, thinking about how the clothes had felt on me. The sensations of the smooth, silky clothing persisted in my mind, and a random thought came to me, about how lucky girls were to have all those nice-feeling things to wear, while guys had all the masculine, rough fabrics. My hard-on never did go down as I lay there, but I eventually fell asleep anyway.
Marcie got up early to go to work, and I slept until about eight-thirty when I had to get up to go to one of my part-time jobs. I saw the clothes I had worn still lying on top of the covers, and I picked them up to put them away. The silky panties seemed to have a life of their own as the smooth material caressed my hand, and I sat there, just experiencing it until I realized that I would have to hurry to get to work on time.
I put in my four hours of filing and got back home at about two o’clock. The work I had been doing was mindless, and the only reason they had me as a part-timer was because the secretaries hated doing it.
I did a few chores around the house, as I always did; since Marcie was earning the money it was only fair that I do most of the housework — except for the splitting of the dishwashing, that is. I finished most of it up and went to the bedroom, where I was going to make up the bed. I saw the clothes still lying there, and with the best of intentions, I started putting them away. I hung up the dress in the closet, but then I faced the dilemma of where to put the undies.
If I put them in Marcie’s drawer, they’d mix in with her things and could cause a problem when she rushed to get dressed one morning. I didn’t want to leave them lying around, so I made room in my underwear drawer, neatly folded them up, and put them in there. Again, the smooth material sent strange sensations through me, and as I walked out of the room, I found myself with another erection.
“This is ridiculous,” I said to myself, “women’s undies are only exciting with women inside them.” But a nagging voice in my head raised a disturbing doubt about that, “Are you sure?” I dismissed the voice and began to prepare dinner for us. When Marcie got home, she asked me how my day had been, and I told her pretty much the usual, commenting on how the secretaries at work had been giggling to each other about something for most of the time I was there.
“Probably just girl-talk,” Marcie said, “somebody fooling around with somebody, or someone having problems with a boyfriend.”
READ THE ENTIRE STORY— The Women’s Job — Part-Time Job
