Brothers In Dress While Mom and Dad Are Away👗💅 (Crossdressing Stories)

 

🎧 Listen to this story

 Two Brothers in Dress.

Hi, I guess I'm the one who should start this story off, or this part of my family's story, since in a way it was my doing that it all started. Not, mind you, that I had the slightest idea of where my initial silly idea would lead or how far it would take my whole family with it. When this started, I was 18 years old, just barely.

My birthday had been only about a month before, and I was officially a legal adult. Not that I necessarily felt any different than I had before. I was still living at home as I attended the local university, and my monetary resources were limited enough to make my adulthood something of a theoretical benefit.

Still, my first semester of college was going well, and my grades were decent, and since I was studying pre-law, I had some hope that eventually my money situation would improve. I'm was a pretty average-looking guy, I guess, about five eleven, with my mother's blonde hair and my dad's skinny body frame, but the girls didn't seem to mind.

I was seeing two girls, in fact, in a casual way. They knew about each other, and I wasn't serious enough with either for it to be a problem. Now, I have two siblings: my younger brother, Ryan, who was 16 at the time of this event, and my sister, Lori, who had just turned 14. The three of us were in the process of coping on our own since our parents were out of town on a business trip.

In fact, they were overseas. Dad is a sales manager for a large Fortune 500 company, and sometimes they needed him to go overseas to Europe for weeks at a time. It was part of the job. When we were younger, Mom would stay home while he went, but now we were old enough my parents felt we could be on our own for a while.

They had, in fact, gone away on trips, leaving me in charge of Ryan and Lori a couple of times before, though only for a week each time. This time, they were going to be gone for over a month. Naturally, we were looking forward to having the house to ourselves for all that time. Mom and Dad were not sure about being gone so long, but since Lori, Ryan, and myself were all in school, it seemed like a good idea not to disrupt our classes, and they'd left us alone for shorter periods, and it had worked out okay, so they decided to risk it.

They did impress on us, especially me, the importance of responsibility. They made it clear they didn't want wild parties as soon as they were out the door, and that they were showing a lot of trust in us by taking this chance. Was their trust justified? Considering how it all turned out, I guess that depends on your point of view.

For about a week, things went normally enough But we did have some arguments about whose turn it was to do what chores, that sort of thing. I was nominally in charge, but my parents had impressed on all of us that they expected us to share the chores and the rest. I knew my supposed authority wouldn't stretch too far with Ryan and Lori, and for that matter, that by simply teaming up to tell our parents some juicy fibs about my actions when Mom and Dad returned, they could probably mess me up pretty good.

So I didn't dare risk trying to push my supposed power far. Well, that was the predicate for what happened the first Friday night after Mom and Dad left for France. It was a rainy, cold, nasty night, and so none of the three of us were going out. Ryan suggested a game of cards, and soon the three of us were gathered at the kitchen table playing poker with chips and pretended money since none of us had a whole lot of cash.

Mom and Dad had left some money for running the household, but we knew we couldn't do much with that if we wanted to continue such luxuries as eating while they were gone. Well, I'm a fair to decent poker player, and I was ahead by a bit, and as the evening went on, we were having quite a bit of fun and joking around a lot, and Ryan happened to suggest we do something we used to do when we were little kids: bet.

The loser had to do whatever the winner said for the whole weekend. Well, like I said, I was pretty confident I was going to win the game, and it suddenly hit me that here was a way to gain some control over my younger siblings that I could count on since the three of us have had a policy of our word is our bond on bets since we were in grade school.

I knew that if I could win a bet with Ryan and Lori, they'd keep their end, and that would give me a chance to offload some of my chores onto them and maybe have a little fun with them. So I suggested that since we had the house to ourselves, we up the ante a bit. I suggested that the winner be in charge of both losers for the entire length of time Mom and Dad were gone.

Well, that floored Ryan and Lori. I could tell they were kind of nervous at the prospect, and I couldn't really blame them. So I started to offer a lesser stake, figuring if I could just win for a week, it would be worthwhile. But I didn't figure on Lori's wild streak. Just as I was about to offer a lesser stake, she said she was game if Ryan was.

Well, Ryan wasn't about to back out on a bet his little sister was game for. It was just too much for his teenage boy pride, I guess, even if he was nervous about the outcome. I think he was pretty sure I would win. I was pretty sure too. I'd been winning consistently all evening. But we shook on the bet and decided to keep playing until one of us had all the chips.

That person would be the winner, and the other two would be the winner's slaves for the next five weeks. At first, I did poorly. I was actually starting to worry as Ryan accumulated chips. He wasn't playing all that well, but he had a couple of lucky hands, including a straight flush. But then I regained the upper hand with a bluff that enabled my handful of trash to beat his two pair.

He was furious when he saw I'd bluffed him, but that regained me my lost chips and then some. I guess I got a little full of myself because I actually teased Ryan and Lori about how hard things were going to be after they lost. They put on a brave face, but I'm pretty sure they thought they were screwed, too.

At one point, I had reduced Lori to two chips and Ryan to one, but then Ryan got another fantastic hand, drawing in a bunch of my stash, and the next hand up, Lori did well. She had four queens, and all of a sudden it was anyone's game again. Well, to make a long story and a long game, we played until 1:00 AM, short, when the smoke cleared and the trash talk was said and done, Lori won.

On our 19th round, Lori cleaned Ryan and me out, which meant that she'd won our bet. I have to admit, as I staggered to my bed that night, that I was more than a little nervous. That first week wasn't so bad, really. I'd lost bets with both Ryan and Lori before, though usually for only a day or two, and always with Mom and Dad around to make sure things stayed pretty tame.

Also, of course, that had been years before. The last time we made a bet, I had been 13, younger than Lori was now, and the last time I'd lost one had been when I was 11. But a bet is a bet, and over the course of the following week, Ryan and I discovered the joys of extra chores, the joys of having your sister tell you what do to, what you can watch on TV, pretty much anything that struck her whim.

She was loving every second of it, and she didn't mind inviting over some of her friends her age to let them enjoy watching her boss us around, too. But things took a scarier and also more interesting turn the following weekend. I knew Lori was up to something. She was giggling and teasing Ryan and me constantly about it, but we didn't find out what our wicked little sister was planning for us until Friday night.

She'd told us both to make no plans for the weekend. I had to cancel a movie date with one of my semi-significant others. But a bet was a bet, and Lori had spoken. Instead, she told me to come directly home from class on Friday night and to plan to spend the whole weekend at home. Well, I was pretty nervous that night as I pulled my car up to the house and went inside, but I couldn't help but be kind of curious, too.

Just what did my little sister have in mind that had her so amused? When I came into the house through the back door, Lori was waiting for me at the kitchen table, dressed in blue jeans, a T-shirt, and bare feet. She jumped to her feet and said, "About time you got here, Todd. I've been waiting forever." I glanced at the clock.

I was home about when I would be expected to be given my last class, so I knew she was just exaggerating. "Anyway," Lori said, tossing her blonde hair with a giggle, "let's get you ready." Surely she wasn't serious. "You heard me, big brother," Lori giggled. "But I..." "A bet is a bet, Todd." I sighed. She had me there. I just couldn't go back on my promise.

It just wasn't something I could do once I'd given it. "I said clean shave your body hair now." At that time, there is nothing I can do. After that, I went to bathroom and clean shave all my body hair and come outside. "Okay, Todd," she said. "Let's go get you dressed. Follow me." And she led me to my room where I saw, lying on my bed, the outfit she had in mind for me.

"No way," I protested. "You can't be serious. This isn't funny, Lori." "Oh, but I think it is, Todd. A bet is a bet, and you shook on it, remember?" I sighed. "Yeah, but I sure never imagined anything like this." "Oh, give me a break," Lori said, rolling her blue eyes in a 14-year-old way. "If I'd lost the bet, you or Ryan would have run me crazy, and you know it, so stop whining and let's get you dressed."

The outfit in question was a maid uniform. Not a normal real world kind of maid uniform, though, but a French maid costume. I couldn't even imagine where Lori had gotten it, and she refused to tell me. To my amazement, it actually fit me, which only made the question of where she got it more puzzling.

Surely, this was some nightmare and I would wake up soon. After the panties came the garters and stockings, which Lori showed me how to get on properly. They were silky and sheer and semi-transparent, but left my legs looking brown. I hated to admit it, but the silky feeling was kind of interesting. At least they weren't itchy or the like.

When I had the stockings secured, Lori gave me a bra and helped me get it on. I teased her that this must be something she had some experience at, and she glared at me before giggling. "Maybe once or twice," she admitted. Lori made me put on the uniform itself, which consisted of a black top and a short, short black skirt with white ruffles that came down to my thighs.

The top clung, but the costume was made in such a way as to hide the fact that I had no feminine waist. I thought the humiliation was almost over, but no, Lori was going whole hog. My footsteps now silent in my stockinged feet, and sat me down at her dressed where she proceeded to apply makeup. I didn't know what half the stuff she was putting on me was, but I tried to protest the lipstick to no avail.

When she finished, I looked in the mirror and gasped. I saw a girl looking back. Not bad, Lori said critically. You'll do for now. Let's get you finished. I was just about protested out. I knew whatever my sister had in mind was going to happen, so I didn't put up too much of an argument as she finished off my outfit with white socks over my stockinged feet and black Mary Jane flats.

A white apron went around my waist, covering the skirt front, and a white headpiece and a wig completed the illusion. I'd been made in a maid. I stared into the mirror for a while. I couldn't believe how completely I looked like a real female. Okay, Todd, she ordered me. Go down to the living room with Ryan and wait for me.

I went downstairs, grateful at least that I had not been made to wear high heels. And when I saw Ryan, my jaw dropped. He was dressed more or less like me, except that his outfit had a longer skirt, and his was pink where mine was black. Other than that, my younger brother was now my younger sister to all appearances.

He looked at me and gasped too. I guess I was as big a shock to Ryan as he was to me. That's it for today.