A Helping Hand

It was late on a Friday night when I heard my parents arguing. It always happened whenever they were getting ready to throw a big party. My mother played the role of party planner and handled all of the details, but between caterers, musicians, and the other help something always went haywire. My father would get upset that something wasn't perfect and they would spend the days leading up to the party yelling at each other. Normally I would steer clear of their arguments but this time sounded more heated than most so I decided to intervene to see if I could calm things down a little.

"What going on guys?"

"Don't worry about it son. Your mother is just trying to ruin our big spring party."

"Me? How does this have anything to do with me?"

"Well, you're in charge of getting the help."

"It's not my fault that Martine is leaving the country!"

"You must have known about this for months. Why don't you just get someone else to fill in."

"You don't think I've tried? The party is next weekend and on this short notice everybody is booked up. We'll just have to set up the appetizers on a buffet table."

"Buffet table? What do you think this is? We can't have our guests serve themselves. You need to get someone to serve the food and clean up after everyone. Or else the party is off, end of story!"

"So you guys need some help for the party next weekend?" I cautiously entered the fray.

"I'll think of something."

"I could use some extra money, how much does the job pay?"

"You? No son of mine will be seen serving food at my party!"

"Why not? I can wear a tux, I'll fit right in with the other help."

"No way!"

My father is very old fashioned in his ways. His family made their fortune building railroads in the west and have been a part of high society ever since. Generations of selective breeding and grooming have left his side of the family very inflexible in their ways and I've learned over the years to back down when he really gets angry. This was one of those times.

"Ok, it's up to you." I turned to my mother before leaving them "Let me know if there is anything I can do to help."

"Thanks, your very kind, but I have to figure this thing out on my own."

I slipped out of the living room to leave them to sort out their problems. I always felt bad for my mother when one of their parties came up. She would spend weeks planning everything and would stress out over every single detail. The parties were always a big success but I wondered if it was worth all the fighting. Up in my room I spent the rest of the night working on a school project while trying to drown out their arguing with my stereo. At eighteen years old I felt like I needed to get out of my parents house and experience the world on my own. After graduating high school my grades were terrible so I enrolled in a community college to get my grades up. My plan was to eventually transfer to a better school on east coast.

It was past midnight when I heard a soft knock on my door. My mother wanted to talk but didn't want to wake me up. I figured that she just wanted to vent about the party but it turned out that she had another idea.

"Sorry to bother you so late Danny"

"It's ok mom. I was just working on a school project. What's up?"

"Well, you know we have this party coming up right?"

"Yeah, I heard." I immediately felt bad for sounding so sarcastic.

"Well, Martine usually helps us out serving food and doing some light cleaning during the party. She's leaving the country for a few months and I can't find anyone else to fill in for her."

She seemed a little nervous as she continued.

"So I know you're looking to make some money. I was wondering if you wanted to help your mother out this one time."

"I'd be happy to, but you heard dad. No son of mine... blah blah blah."

"Yeah, I heard. He said no son of his will be seen serving food at my party, but what if you're not seen?"

Confused I replied "huh?"

"Well, since you were in the drama club I thought that maybe this could be more of an acting job for you."

"I'm not sure I understand."

"All it would take is a wig and some makeup and nobody would recognize you."

I couldn't believe what my mom was suggesting.

"You want me to dress up as a girl?"

"It's just one night, and you would be acting right?"

My heart was pounding at the thought of dressing up as a girl, even for just one night. I secretly had a thing for wearing women's clothes and this would be the opportunity of a lifetime for me. It started when I played Mary Sunshine in my high school's production of Chicago. I had never thought of wearing women's clothes before, but something about the costumes got me really horny. Ever since then I would sometimes sneak away with one of my mom's Victoria's Secret catalogues and marvel at all of the sexy outfits. Secretly I was a little jealous that girls got to wear such soft and silky underwear. I didn't consider myself gay and I didn't want to wear women's clothes all the time, but something about it always made me horny. I knew that I had to play my cards right with the party. If she was really serious about this I would have to hide my excitement.

"I don't know mom."

"Didn't you play a girl in that musical last year?"

"Yeah"

"So this is like the same thing. It's a one time live performance. And I promise nobody will know it's you, especially not your father."

"Do you really think it would work?"

"Well, I don't have any other options right now. You said you wanted to help and here is your chance. Any great actor would jump at the part."

She was playing me like a violin.

"Since you don't have any other options, I guess I'll do it."

"Really?"

"You know I'll do anything for you mom."

"You're amazing! Ok, I've got to start planning it all out. Why don't we talk again in the morning."

"Ok"

My mom rushed up to me and gave me a big bear hug before disappearing down the long dark hallway. That encounter left me too distracted to continue doing work so I spent the next hour struggling to fall asleep.

The next morning I found my parents in the kitchen doing their usually weekend routine. My mother didn't say anything about our conversation so I didn't bring it up either. During breakfast I kept searching my mother's face for any indications that I didn't just dream the whole thing up myself but she acted like it was just another ordinary Saturday morning. After reading his paper, my father got up and left for the country club for the day. As soon as I heard his car door slam shut my mother rushed over to me excitedly and took my arm in her hand.

"Come on, we have a lot of work to do!"

She led me through the house to her studio. Technically, my mom didn't work anymore but she occasionally did some work for her friends as a throwback to her glory days. Before she met my father she was an up and coming fashion designer with a struggling boutique. She managed to get her collection into a few runway shows and was starting to break through when she met my father. His family had so much money that she would never have to work again, and even if she wanted to he would never let her. When they built this house, years later, she convinced him to give her a studio of her own so that she could do alterations for herself and friends. The studio was a large room filled with closets and mirrors. The few times that I've been in there it was covered in sheets of fabric and partially finished dresses. There is a pedestal in one corner of the room that is about two feet off of the ground and surrounded by mirrors. My mother frantically led me to the pedestal and pushed me up the steps.

"Ok, so first we have to get working on your uniform and then we have to work on training you for the role."

Trying to act nonchalant about what was happening to me I said "Whatever you want mom."

"This won't be easy for you, but I know you can pull it off. Now, take off your clothes so I can take some measurements."

"What?" I was starting to get a little embarrassed.

"Come on, don't be shy. You can leave your underwear on but I need to get your measurements right if the uniform is ever going to fit you. Now get to it!"

Her voice had a sharp tone in it and I realized that the stress of the party must be really getting to her. Not wanting to aggravate her any more than she already was I did as I was told and stripped down to my boxers. My mother held up her seamstress tape measure and quickly took measurements for every one of my body parts. I fidgeted a little when she took my inseam which required her hand to press against my inner thigh. She pushed the leg of my boxers up and could feel the coolness of her hand brush against my balls as she took the measurement. Moments later she was done and had written everything down on her little pad. I reached down to grab my pants but was interrupted.

"Not yet young man. You have to try this on first."

She was taking Martine's uniform off of a hanger as she walked over to me. The uniform is a very traditional french maid outfit. It is a small black satin dress with frilly white lace trim. The top of the dress is form fitting with two thin black shoulder straps. The front of the dress is laced up with a thin white satin ribbon to cinch the dress at the waist. The skirt portion of the dress flares out from the hips and is trimmed with white lace around the hem. There is a white satin strap that wraps around the waist and holds up a small white satin apron. My mother indicated that she wanted me to step into the dress and then proceeded to slide it up my legs. With her guidance I put my arms through the straps while she straightened everything out. I am a fairly skinny guy, especially compared to Martine, who really filled out the tight dress. I was also a few inches taller than Martine which left the hem of the dress higher up on my legs than when she wore it. Partly because of the difference in our frames, the dress looked a little ridiculous on me. It practically fit me like a tent, my mom would certainly have her work cut out for her. I was looking myself over in the mirror when I felt her tugging on the straps in the front. She pulled them as tightly as she could and breifly knocked the wind out of me before tying it up. She could tell that I was having a hard time breathing and looked up at me.

"I know it's uncomfortable, but it's important that you get used to this. Every woman has to have some curves and this is the only way to do it. Don't worry honey, with a little practice this will feel completely natural."

I couldn't even respond until she finally released me.

"Ok, I've got what I need. You can put your clothes back on."

Even though I looked silly in Martine's uniform I couldn't help getting a little turned on by it at the same time. I was actually wearing women's clothes and the soft material against my skin sent a chill up my spine. I didn't notice that my penis had involuntarily responded to the excitement until I pushed the dress down my legs. There was a distinct bulge in my boxers; I just hoped that my mom wouldn't notice. When she walked over to me to retrieve the dress at my feet she ended up with my crotch right in front of her face because of the elevated platform. I'm still not sure if she noticed my excitement but after picking up the dress she looked right up to me with a wide-eyed smirk before turning away to get something off of the table.

"Ok, we're done here. You can get dressed now."

I quickly reached for my pants and covered up my growing erection. While I pulled my shirt over my head my mother handed me a bag.

"Now you need to begin preparing for your role. Use the razor first and shave off as much hair as you can and then use the gel in the bottle to take care of any stubble. After you're finished you should use the lotion all over to make sure that you don't get any razor burn."

Looking in the bag I saw a pink razor, ladies shaving cream, a bottle of hair remover, and a bottle of lotion.

"But I've already got my own razor; I don't need any of this." It didn't even faze me that she was telling me to shave my body.

"A man's razor won't work. Women's razors are specially contoured to shave legs. Trust me, you don't want to cut yourself. Now, I need to run out and take care of a few things. When I get back I expect you to be all shaved and ready for our first lesson. We only have a week until the party and you have alot to learn before we can pass you off as a girl."

As much as I was turned on by wearing women's clothes, I was starting to have second thoughts about this whole thing. But I knew that I couldn't let my mother down. I was stuck.

"Ok, I'll do my best."

"I know you will, bye honey!"

She turned on her heels and left the studio. I didn't know how long she was going to be gone so I decided to hurry up and get it over with. I wasn't very hairy to begin with so shaving my legs wasn't much of a problem. I took my time though, being extra cautious not to nick myself with all of the contours of my legs. I followed the instructions on the hair remover and left it on for ten minutes before rinsing it off. After the shower I did as I was told and rubbed the lotion all over my body. At first I was a little put off that it was a scented lotion, but by the time I was finished I was starting to enjoy the delicate floral scent and was amazed at how soft it made my skin feel. My skin felt smooth and soft but it was a little weird at first when I put my pants on. I didn't expect it to feel any different but I was now much more aware of the fabric of my pants rubbing against my freshly shaven skin. I spent the next hour trying to work on my project but my head was still in the clouds. When I heard a car door slam shut I anxiously looked out the window to find my mother carrying in several shopping bags. Minutes later she knocked on my door.

"Are you decent?"

"Come on in mom."

She bounded into my room with her arms full of bags and a gleam in her eye. I felt my stomach sink wondering what she had in store for me.

"Since we don't have much time you will need to start rehearsing right away. Normally you would have weeks of rehearsal, but this time is different so I need you to do everything that I tell you to ok?"

"I guess so."

"Danny!" She snapped "I'm being serious. If your father finds out that you are working at the party he will lose it. You need to pull this off."

"Ok, Ok, whatever you say mom."

"I noticed how uncomfortable you were when I tied the uniform up in the front, but you will need to get used to it." She reached into on of the bags and pulled out a large black object with straps hanging off of it.

"I got you this corset to practice with. I want you to wear this every day and each day we will make it a little tighter. By the end of the week you will have a perfect hourglass figure. Now take off your clothes and I'll help you put it on."

I stripped down to my boxers and waited."

"Sorry Danny, not this time... Take it all off."

I pushed my boxers down my smooth legs and sheepishly tried to cover my manhood.

"You don't have to be embarrassed around me. It's nothing I haven't seen before."

After a brief pause she turned around and left my room in a rush. "That won't do!"

She reappeared moments later with the pink razor and shaving cream in one hand and a towel in the other.

"I told you to shave off everything! You need to play the part starting today."

She sprayed some shaving cream into her hand and before I could react was spreading it on my balls. My mother crouched in front of me and deftly began shaving me. Her hands made short work of the job as they danced around my crotch. I felt my penis growing when she lifted up my cock in one hand so that she could shave underneath it with the other. She didn't seem bothered by the fact that my cock quickly became rock hard in her hand while she finished the job. Using the towel she cleaned off the excess shaving cream. Finally she squirted some of the lotion into her hand and slowly rubbed it all over my cock and balls. I stood frozen as her hand started at the base of my cock and slowly moved up the length of my penis until she circled the tip. Her hand was gently squeezing me while she massaged the lotion into my skin.

"Now don't forget to use the hair remover next time you shower. I expect you to shave yourself every day until the party. And the lotion is very important, it will make your skin as soft as mine. Ok?"

"Ok, mom." I replied meekly.

My mother walked over to me and slid my arms through the arm straps of the corset and then wrapped it around my torso. She turned me around and played with the straps pulling them tight.

"Tell me when it's too tight."

"Unggh..." I could only get out a little grunt.

She took the hint and barely loosened the corset before tying it off. I was struggling to breathe but she didn't seem too concerned. The corset was made of a black elastic material with stiff ribbing going up the length of my torso. The ribbing was covered in strips of bright pink satin. The shoulder straps were accented with pink lace and the cleavage of the corset was covered in pink lace ruffles topped with a pink satin bow in the middle. The bottom of the corset was trimmed with the same pink ruffles as the cleavage. Four thin black straps hung down from the corset, two in the front and two in the back. After securing the corset my mother pulled two rubber objects from one of her bags. She slipped one into each of the cups of the corset and stood back to examine the results.

"Not too shabby."

I reached up and squeezed my new fake breasts through the corset.

"Since you will be wearing stockings for the party you should start getting used to them. You will have to learn how to put them on yourself so pay attention."

My mother, Rebecca although most people call her Becky, is in her early forties but still has a spectacular body. I've never fantasized about her before but it would be impossible for a teenage boy not to notice that she is hot even though she is my mom. She is pretty tall, about 5'8", with long blonde hair with light brown highlights. Her large breasts were showing signs of her age and had developed a slight sag. She often wore dresses around the house and I suspected that she rarely wore a bra, although I didn't spend much time thinking about it either way. That day she was wearing a long thin dress that covered her almost to the floor. It was light green with a peach and brown tropical print. The top of her dress revealed the swell of her breasts and had a ruffled trim below the neck.

"You should sit down to make it easier."

I took a seat on the corner of my bed while she searched through the bags. She took out two small packages and handed one to me. It was a pair of sheer black thigh high stockings. She took hers out of the packaging and told me to pay attention. She reached behind her head and tugged on the spaghetti strap that held her dress up.

"Since it's just us girls here." She gave me a devious wink before releasing her dress. It fluttered to the ground landing in a heap at her feet and in an instant my mother was standing before me wearing nothing but a pair of small red panties. She leaned forward and stepped into one of the stockings. Her breasts fell away from her body and rocked back and forth as she pulled it up her leg smoothing it out as she went.

"See, the trick is to bunch it all up before you step into it. And be very careful, these are delicate and will rip easily." She stepped into the second one just as easily as the first and pulled it up her leg in one motion.

"That's it, now your turn."

I expected her to put her dress back on but when I saw that she wasn't moving I pulled my stockings out of the package. I tried to follow everything that she did and managed to pull both of them up my legs.