Down on His Luck

I've had several stories that I started, then set aside. This is one, as was my last one 'Punished'. I have a few more and may see what I can do with them before tackling something wholly new. I hope you enjoy.

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Celia

My brother Kent was always something of a shit. He was always pulling pranks on people including me. I am Celia, his little sister. Now you would think that a big brother should be protective of his little sister, but Kent never was. I think I was the butt of more of his pranks than anyone else, and he really enjoyed humiliating me in all sorts of ways.

Once he went off to college, my life got easier, and when I went to college, I made sure to go far away from where he was. Now you'd think that during summer break I might still see him, but I did my damnedest to avoid going home during summer break. I could not avoid seeing him around the holidays and he tried to make up for lost time then.

Once he was finished with college, he got a high paying finance job in the city, but seemed to spend money just as fast as he made it. I got an IT job and made sure to stay at least half the country away from him. As it turned out, I ended up on the west coast, while he had his cushy east coast job. I tried to schedule my visits to the family when I could be sure he wouldn't be there.

They say all good things come to an end. I don't know about that, but I heard through family and friends that Kent had lost his job. He seemed to be having trouble finding something else suitable, and given his high living ways was starting to have serious money problems. Given how much he had tormented me, I had trouble feeling much sympathy for him. It was a shock then, when Kent showed up at my door asking for help.

"Celia -- sis -- I need help. I've got bad problems."

"Give me one good reason why I should help you."

"I'm your brother. Doesn't that mean anything to you?"

"It didn't seem to mean anything to you growing up except that I was an easy target for you."

"I did stupid things when I was younger."

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Stupid things, he called them. I called them things which humiliated me beyond belief. I remembered right after my 18th birthday, I had been out for a run. I got home and Kent and some of his friends were there. I was covered in sweat, to the point where it was literally dripping off me. I grabbed a change of clothes and headed to the bathroom to shower.

I locked the door -- the knob locks, that's all we had on interior doors in our house. I turned the water on very cool, took off my running clothes and got in the shower. I heard nothing, but stepped out of the shower a little later to find my running clothes, my change of clothes, and all the bath towels missing from the bathroom.

Interior knob locks are easy to open, and Kent had quietly come in the bathroom while I was showering and taken everything except a little hand towel. I dried myself off as best I could with that little towel, then stood quietly at the door to the bathroom trying to listen to hear if anyone was nearby. I listened for a few minutes and heard absolutely nothing.

I was naked, with nothing but a tiny hand towel, but decided to make a break for my bedroom in hopes of getting there unseen. Foolish me. Kent and three of his friends were waiting quietly in the hallway between the bathroom and my bedroom. I stepped into the hallway, and not only did they block me from getting to my bedroom, they kept me from getting back into the bathroom.

One of them grabbed the little hand towel that I was vainly trying to cover myself with. I saw the flash as they shot some pix of me naked in the hallway. I did manage to get by them, but not without having them fondle my boobs and ass. I kept one hand firmly over my pussy, so they couldn't get to that, though they'd have messed with that too, if they could have.

After that, I never showered with Kent and his friends in the house, no matter how hot, hot sweaty, or how dirty I might have been. Unfortunately they found other ways to humiliate me.

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One summer day, Kent and his friends were off doing something. I wasn't sure what, but was happy they were not there. I put on my bikini and went out to the pool to get some sun. I guess I dozed off while lying on my stomach, and Kent came back while I snoozed. My bikini had string ties and he sneakily untied them, then tied the strings to the slats of the lounge chair I was on.

I woke up to ice cold water being poured on my back and jumped up, not realizing what he'd done. Again, I was naked, and my bikini was tied firmly to the chair. Kent and his friends laughed and got a few more pix of me naked before I was able to run in the house, again with them grabbing my body along the way.

After that, I was careful never to sleep by the pool, and avoided being around the pool if I thought there were much chance of Kent or his friends being around. On another occasion, I was actually in the pool swimming when Kent and his friends showed up. I tried to stay as far away from them as I could, then a couple of them jumped in the pool, cornered me, and pulled my suit off me.

I ended up making another naked mad dash for the house, with hands grabbing me along the way and a few more pix of me naked. I don't want to go on at length, but trust me there was a lot more of the same, any time Kent could find a time and means to get me naked in front of his friends. A few of those pix made their way around school during my senior year, humiliating me further.

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So now, some years later, after humiliating me many times, my brother Kent wants my help.

"Kent, you made my life a living hell when we were younger."

"Please, Celia, I'm sorry, and I'll do anything I can to make things up to you."

"I don't have the kind of money you need, and don't think I should lend it even if I did."

"I've lost my condo and all but one car. I need a place to stay while I try to find work and get back on my feet."

"You want me to let you stay here after all the times you humiliated me when we lived at home?"

"Please. I promise I won't do anything like that again. I'm desperate. I'll do anything you want if you'll let me stay."

"Anything I want, huh?"

"I swear."

"And what if I want to humiliate you, to make up for the times you humiliated me?"

Kent's face turned very white as he thought about it. He was trembling as he looked at me. "I suppose I deserve it."

"No shit."

"What -- what did you want to do to me?"

My mind went into overdrive, as I tried to think of things that would humiliate and embarrass him. I opened the door and waved him in. He walked in, still looking very nervous. I waved him over to the sofa and he sat down.

"If you're staying here, then you have to pay your way by being the maid and keeping the place clean."

"That's reasonable."

"And you have to do it while dressed as a maid."

"What do you mean?"

"What the fuck does it sound like I mean? You're going to wear a maid's outfit -- a short skirt, a frilly blouse, the works."

"Shit, sis, don't do this to me."

"You got me stripped naked in front of your friends, not once, but many times. Be damned glad I'm not doing worse."

"I don't know if I can -- "

"Then get your ass out of here and find some other place to stay."

"I don't have any place else to go."

"Then follow me and do what I damned well say."

I'm not a small girl. I'm 5'8" 120 pounds with nice boobs and a cute ass, or so I've been told. Kent was a lean 5'10" and 140 pounds. I had a French maid outfit that I'd worn to a costume party a while back. It was kind of stretchy, so I figured we could squeeze Kent into it. I led him into my bedroom and opened the closet and pulled out the maid outfit. Kent turned white again.

"Okay, bro, get naked."

"You're not really going to do this are you?"

"You bet your ass, I'm doing it, now take off those damned clothes."

I laid the maid outfit on the bed and began rummaging in my dresser as Kent slowly took off most of his clothes. He stripped down to his boxer shorts and stood there, as I pulled a lacy bra and panties from my dresser.

"Lose the boxers, bitch."

"You're going to put me in -- "

"Yeah, I am."

He took off his boxers and stood there, and I noticed his chest and leg hair. I grabbed his hand and led him into the bathroom.

"You need to lose the hair to do this right."

"Fuck, no."

"Fuck, yeah." I shaved his underarms and made him shave his legs and chest. He had a little back hair and I shaved that off. He shaved his face again, then I led him back into the bedroom. I put him in the panties and bra, then padded the bra to look like he had boobs. Then I got my phone and took a pic of him in bra and panties.

I put him in the French maid outfit, which stretched just enough for him to get in, then shot another pic. Then I sat him down, and began to brush out and style his hair. His hair was longish, so I styled it more feminine and trimmed it here and there to make it look better, then put makeup on him including lipstick, eye shadow, the works.

Once I was done, I shot another couple of pix of him in full regalia. The skirt was barely long enough to cover his panties, and the top was low cut, showing the cleavage he didn't really have. "This, dear brother, is how you will look when you are around my apartment. When you go out for job interviews you can wear something more normal."

"I need to change and bring my stuff in from my car."

"No, you can bring your stuff in dressed exactly like that."

"I have to go to my car looking like this?"

"Exactly, now get that cute little ass moving and bring your stuff in. Spare bedroom is over there."

"Maybe I'll wait."

"You will bring your stuff in, dressed like that, whether you do it now or later."

"Shit, Celia. Why are you doing this to me?"

"Payback is a bitch."

"So I have to clean, then sit around your place wearing this?"

"More than that. I have two friends coming over, you'll be serving us snacks and drinks dressed like that."

"Please, I'm begging you. Don't do that."

"Get used to it. You know Kent doesn't work well as a name when you look like that. I think now you're going to be Keri, the maid."

"I'm really sorry for all the things I did to you when we were younger."

"Good, because you're going to make up for it now."

"Can't we work out some other way for me to atone for that?"

"I like this way. Now my friends are going to be here in an hour, so start straightening up and preparing snacks."

"I don't know if I can do this."

"Okay then, march your ass right out the door and find someplace else."

"I'd need my regular clothes back."

"No, if you're going to bail on me, you can wear that out, makeup and all."

Keri stood there looking shocked. Her hands were shaking as she sat down on the sofa.

"Okay, Keri, if you're going, go, otherwise, start to bring the rest of your stuff in from your car. You might as well start getting used to this."

"I never realized just how cruel you could be."

"And who do you think drove me to this?"

Keri brought her stuff in and put it in her bedroom as I prepared some snacks for my friends. As she did, I called and asked them to bring along a couple more friends. Instead of the three of us that I'd originally planned, we'd now have six to see Keri's debut as my live in maid. Now I'd told of couple of my friends about what Kent had done to me in the past and that now Kent was were as Keri.

They seemed to get into the idea of helping me get some revenge for the past and brought some things along for later. I made Keri answer the door to let everyone in as they arrived. Several of them made a point of grabbing Keri's ass as they came in. Keri began serving snacks and drinks with most of the women enjoying feeling her up as she worked.

Keri seemed embarrassed and didn't seem to like what they did, but it was also obvious that she had a hard-on from it all. A little later Joni suggested that we go out dancing as a group, and someone said that Keri should go as well. Keri wanted to change to boy clothes, and Joni said that Keri should go, not Kent.

Joni, as it turned out, had some more standard clothes that fit Keri, but with some caveats. She had a pair of gaff panties that tucked Keri's junk up between her legs, so it was less noticeable. Joni also had a pair of breast forms and medical adhesive to replace the lousy bra stuffing I had given her earlier. Keri wasn't thrilled about that, but Joni insisted.

There was a skirt that came down about six inches above the knees, along with a top that showed off Keri's new boobs to their greatest effect. The more Joni came up with, the less Keri seemed to like the idea, but the six women insisted that Keri come along with us, and that she be dressed as Joni wanted her to. Joni also had some midlevel heels.

Along the way, we took time to paint Keri's toenails and fingernails, then touched up her makeup. Kent has never had a super-masculine face, and by the time we were done, Keri looked more feminine than a couple of the women in our group. Once the nail polish had dried and we had Keri fully dressed for a night out, we took off for some fun.

For some reason, Joni took a particular liking to Keri, bought her a couple of drinks, flirted with her, and danced with her. Keri was almost numb by this point, at least until we found ourselves joined by a group of guys who asked several of us to dance, including Keri. Keri turned and whispered to me.

"I don't really want to dance with some guy."

"Relax, it's not like you're going to go home with him. It's just a dance or two -- enjoy it."

We made it clear that Keri wasn't much into guys, but would dance a bit.

"We'll see if we can't warm this cute little lady up a bit."

The guy took Keri out and began to fast dance with her. Keri started out very stiff, but after a little bit began to relax into the dances. After a few fast dances, a slow number came on. Keri tried to excuse herself, but the guy grabbed her and pulled her close. Keri looked very pained, but between the alcohol and everything else, relaxed into the dance, at least until the guy began to rub Keri's ass.

It was pretty obvious that Keri wanted to get away, but the guy was about 6'3" and 240 pounds and he was holding her pretty firmly. At the end of the dance, he gave Keri a long kiss, as Keri squirmed.

"I -- I have to get back to my friends."

"What's the rush, cutie?"

"It's -- uh -- that time of the month, and I need to get a tampon, before I embarrass myself."

"That's too bad, baby. Maybe we can get together some other time. I'd really like to get a lot closer to you."

The guy gave Keri another kiss, then patted her on the ass as she headed back to where we were hanging out. Keri told me what she'd told the guy and I grabbed my purse and took Keri to the women's restroom. We spent a few minutes in there, as Keri tried to regain her composure.

"I want to go home -- back to your place, I mean."

"You, Joni, and I can go back, and let the other women stay and have some fun."

We had taken two cars so it worked out pretty well. I drove, as Joni sat in the back seat with Keri, stroked her head, and began to kiss her. Now, I knew Joni preferred women, and she knew what Keri had down below, but Keri looked cute enough that I guess Joni didn't really care. By the time we got to my place, Joni and Keri were making out pretty good.

After what we'd already put Keri through, she was ready for something with a woman. Joni was quite ready to have Keri please her. Joni and I had been lovers a few times, though I prefer men, and she mostly wants to be with women. Then again, Keri looked like exactly what she wanted.

They spent some time kissing, before Joni took off her top and her bra and had Keri begin to kiss and suck on her boobs. Keri seemed more than willing to, and got into it very enthusiastically. After a while Joni took off her slacks and boyshorts, and had Keri go down on her. Keri licked Joni's pussy like there was no tomorrow, and quickly brought her to orgasm, then hung in to bring her to two more.

Joni stripped Keri and played with her faux boobs, before digging something more out of what she'd brought with her that night. Joni put on a strap-on and turned Keri over onto her hands and knees. For a moment, Keri seemed not to understand what was going on, until Joni slid the strap-on into Keri's ass. Keri began to protest, then Joni gave her a swat on the ass, and Keri settled down.

Joni used the strap-on to fuck Keri's ass, until Keri came onto the bed. Joni still had the strap-on buried in Keri's ass, as they rolled on their sides, with Keri panting and gasping. Joni kissed the back of Keri's neck, and Keri moaned as Joni stroked Keri's boobs and midriff. Joni finally pulled the strap-on out of Keri's ass, and rolled her over and kissed her some more.

"Now see, baby, that wasn't so bad was it?"

Keri shook her head, and kissed Joni back, both of them moaning. Keri's cock regained its firmness as they made out, before Joni stopped and turned to me where I had been watching.

"Celia, darling, Keri's cock needs a workout, and you know I don't like to do dick. Be a good girl for me and let her get her pleasure too."

"You've done guys, and you've let me fuck you with a strap-on. "

"Do it for me, baby. Please."

"Like hell, that's my brother. I'm not doing her. She got you off, you can get her off."

"Be that way then, bitch."

Joni pushed Keri onto her back, then lowered herself onto Keri's cock and began to slowly fuck her. She pulled out until the cock almost popped free, then plunging it deep inside her, until their pussy hair mingled. Keri put her hands on Joni's hips as she gradually picked up speed, until she was fucking Keri hard and fast.

After cumming on the bed while Joni fucked her ass, Keri's dick held up a lot longer than one might have expected. Finally, Keri grabbed Joni's hips and held her tight as she unloaded her cum deep in Joni's snatch. It almost looked like her eyes had rolled into the back of her head, as she lay there with her prick twitching and leaving the last few drops of cum in Joni.

"You're a bad girl, cumming inside me like that."

"You're protected, aren't you?"

"I am, but you didn't know that when you came inside me."

Joni kissed Keri, then climbed off her. I went to my room, to leave them to their fun. As I later learned, Joni spent the night and she and Keri had even more fun.

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In the morning, Joni and Keri were in the kitchen, both in long tee shirts and panties. Joni was talking to Keri and giving her hell. Keri had her back to me and didn't know I was listening.

"I thought you needed a job."

"I do need a job, but -- "

"You have a car, but how long before they repossess that too?"

"Maybe two months."

"Do you have any idea what the job market is like in this area?"

"I know there's tech companies."

"That don't need what you do."

"Yeah, but the wages you're talking about aren't that great."

"But it's a job, and money, and a chance to hang onto something until you can be and do what you want."

"But only if I work as Keri."

"You're going to be living here as Keri anyhow."

"I didn't think I'd have to be Keri twenty four fucking hours a day."

"You telling me you didn't enjoy what we did last night?"

"I want to be a guy some of the time anyhow."

"You're a guy when you get your dick in a pussy."

"But not any other time."

Keri was surprised when I spoke up. "Get used to it, girl. Joni was being nice sharing her pussy with you. Hell, I don't have to share my apartment with you."

"Celia, please. You misunderstand."