Crystal's StorySite


Stupid Mistake

by Donna Williams


I first discovered the sensual feeling of nylon nighties while detailed to clean out my parents basement. These nighties were my mothers when she was a teenager. They had a musty smell from their storage in the damp basement, and I really have no idea what possessed me to try them on. However, once on, I had my first erection and, after a few minutes, my first orgasm. I then found a couple of dresses and skirts, and tried them on also.

At some point I realized that the thought and fear of getting caught in these clothes increased the intensity of my orgasms, and I would do various things to heighten these feelings. One of the stupidest being to insert a 12 inch knife, point up, into the ground a few feet from a swing tied to a tree, and jump from the swing over the knife while in the skirts. Luckily I had no accidents and no one saw me outside in feminine attire. I had no sisters so anyone seeing a "girl" on my swing would have been suspicious.

I never did grow out of these feelings due to tempting fate at getting caught. One time, while fully dressed and in the kitchen, one of my brothers came home unexpectedly with a couple of his friends. Luckily I was skinny enough to fit in the cabinet where the broom was kept. My mother caught me in one of her bras one time, but my parents didn't try to find out why I was wearing it, other than ask why. I simply said "I don't know" and the subject was dropped. Other than that, no one had any idea of my fetish.

My wife had no idea I would try on her clothes while she was at work, or shopping; and I would again tempt fate by waiting until the last minute to change. Sometimes this would be when I heard her pull into the garage.

One Saturday afternoon, I was so caught up in masturbating, I didn't hear her come home. It didn't help matters that she parked in the driveway instead of the garage. I later found out this was because she wanted to wash the car. I was standing at the toilet, skirt raised and panties showing, cleaning up, when she walked in on me.

"What the hell!?" she shouted. I quickly dropped the skirt and flushed. Turning around to face her I was speechless. "Explain this, this. . .!" she yelled.

"I'm sorry dear," I finally got out. "Please, let me explain."

"I already told you to explain, stupid! Get out of there! Well!?"

I stumbled to the bed, sat down, and, while she paced back and forth, recounted what I have discussed above.

"So, you do this to get off? I'm not satisfying your urges?" she asked.

"Please, its just different. You satisfy all my other urges, this is just different." I responded.

"God, look at you. Those are all my clothes! I can't believe you fit in my clothes. I got to get a drink. Don't move, don't go anywhere!" she said as she went to the den to get a drink.

She was gone a while, I don't know how long, but it seemed to be hours. "So, you said the thought of getting caught made getting off stronger?" she asked returning to the bedroom.

Startled, I quietly responded, "Yes, dear."

"So, now that you've been caught, you'll finally quit?" She asked.

"I don't know." I said, "I like the feel of the clothes too. That's what got me started." Looking back I think I should have just said "yes" even though I knew I couldn't. At least the fear of getting caught again might have been just as bewitching.


"I see." she said. "I need to think about this." She turned to leave, stopped, and said, "There's groceries in the back seat. Go bring them in."

I kicked of the heels and stood, to get changed and heard, "I didn't say you could change!"


"You said you liked the rush you get from the fear of getting caught, so let's see how going out to the car still dressed affects you!"

"But. . ."

"No buts. Put the heels back on and do as I said, or your mother will be the first person I call."

Having no other choice, I scurried to the car, hoping against hope no one would see me. Luckily (?) I only had to make two trips. After setting all the bags on the kitchen counter, my wife (Mary) came in and told me to put them all away. She then sat at the dining table as watched as I moved about doing as she instructed. Once I finished, I noticed she had a slight smile on her face. I wondered what she was thinking, but didn't ask.

"Tonight was supposed to be your poker night, wasn't it?" she asked.

"Yeees," I slowly responded.

"Then you'd better straighten the living room, including vacuuming. Then clean both bathrooms. When you're done you can get the snacks together. I need to run out again, forgot to get the beer," she said. She grabbed her keys and headed for the door. "Oh, and no changing until I get back," she said. She stopped and reached behind the kitchen door, and pulled out a frilly apron. Throwing it at me, she said, "Put this on. You're starting to make a good maid."

While preparing the snacks, Mary returned with the beer and told me to put them on ice, then get the poker table out, and set out the chips. As I was doing this, she went back to the car and brought in some shopping bags, taking it straight to the bedroom. She returned a few minutes later, and once I had everything set up, she told me, "You had better go change before the boys get here, unless you want them to see you in my dress."

As I headed to the bedroom to change she called out, "Your clothes are already laid out on the bed!"

I think my heart skipped a beat when I saw what was laid out. There was the typical short French maid costume, apparently purchased from the local costume shop, complete with multi-layered petticoats, panties with ruffles covering the butt, fishnet pantyhose, black 4 inch heels with ankle straps, breast forms and a blonde pageboy styled wig.

I returned to the living room carrying the maid's uniform, "I can't wear this. I won't!" I argued.

"You can, and will!" she asserted, "and you better hurry up, too, if you want me to help with your makeup to hide your appearance. Or else you'll be standing there looking like a man dressed as a maid. Now, go shave all over, get dressed and call me when you're ready for your makeup!"

"But they're expecting me to play, they won't want to stay without there being a fourth."

"I'll offer to be the fourth, and I don't think they'll object. Now, you don't want me explaining why the game had to be called off do you? And fearing getting caught, just think of the orgasm you'll have later," she persuaded.

Thinking I could possibly get away with this, I returned to the bedroom and did as instructed.

Looking in the mirror, following Mary's expert application of makeup, I could find no trace of my male self.

"Quit admiring yourself. Let's go to the living room so I can give you your instructions, Donna," Mary directed.

"You need to remember to respond to your new name, Donna. When you respond, you are to answer with 'yes mam' or 'yes sir', etc. You are not to use anyone's real name. When the door bell rings you are to answer it, curtsey, and show whoever it is to the poker table. You'll then ask if they would like a beer. During the game I want you standing near me when not serving your, my guests. I think you'll make an interesting distraction, and I might come out a winner tonight," she explained. "You think you can remember all that?"

"Yes mam," I responded.

"Good, now let me see you curtsey!" she ordered.

I had practiced that maneuver in front of mirrors since I was a teenager, so she was satisfied with my curtsey. About then the door bell rang. "Time to get to work Donna!" she said.

As each guy (Steve, Greg and Jim) arrived, I got the same look as I answered the door. One of awe and bewilderment, but no sign of recognition. Of course they appeared to be more interested in my cleavage or legs.

After I had escorted each to the table, Mary surprised me stating, "Tom (me) upset me this afternoon and won't be able to play poker tonight. Since everything has already been set up, and Tom has provided a maid to serve you all, does anyone mind if I play instead?" There were no objections.

"Donna dear, please get the gentlemen a bear, and bring me a white wine," Mary ordered.

"Yes mam," I responded, throwing in a curtsey for good measure.

As the game progressed, Mary appeared to be winning quite easily, and I was kept busy serving everyone. Mary noticed that Jim was becoming a little agitated and said, "Donna dear, Jim looks like he need to relax a little, please go around and give him a neck massage. You don't mind do you Jim?"

"No, not at all. May be just what I need," Jim replied.

Of course, I minded, but no one asked me, and I could say nothing except, "Yes mam."

"See, there will be no losers tonight, except maybe for Tom!" laughed Mary.

As Jim relaxed, Steve asked, "When's it my turn?"

Mary looked at me, smiled and said, "Jim appears te be a somewhat satisfied, for now. Give Steve his turn Donna."

"Yes mam," I said as Jim grabbed my hand kissed it, and handed be his last chip.

"Thanks Donna, makes losing a little easier," said Jim.

I eventually gave each of the guys the same neck massage as they continued to lose to Mary, and I received each one's last chip as a tip.

"You know," remarked Greg, "I think Tom hired this maid to get us distracted. Too bad he wasn't here to see it work. Fastest I've been cleaned out in a while."

"You may be right," said Mary, "but I didn't hear any objections! I'll tell you what, it is quite early, and I did say there wouldn't be any losers tonight, except maybe for Tom. Donna?"

"Yes mam?"

"I don't want the gentlemen to go away unhappy, and I noticed that they all became exited in response to you ministrations, so I would like you to give each of them a long deep kiss before they leave! You guys think you can handle that?"

Stunned, but not dumb, they chorused a resounding "YES!"

I too was quite stunned. "Well? go on Donna! You said you'd follow all my instructions tonight," said Mary.

I gave her my most pleading, puppy dog look, but she just smiled, and said. "Start with Jim, then do Steve and finally Greg, unless you want me to explain your relationship to Tom."

"No mam," I said.

As I kissed Jim the other sheered us on, Mary the loudest I think. Then Jim grabbed my hand again and started rubbing it on his crotch. "Ohh," said Mary, "looks like Jim wants more than a kiss! I see Donna didn't pull away either. Give Steve and Greg their kisses, too."

As I kissed the others Mary had me feel their crotches too. "Well Donna, did you make them all hard with that sexy little mouth?"

"Yes mam," I whispered.

"Interesting. You guys liked her mouth on you lips, what about your cocks?" she asked.

Again they chorused a resounding "YES!"

"OK Donna, I want you to take them back to my bedroom, one at a time, of course. You only need to give them head, but if you want to go further, that's up to you. In either case, I get to watch."

Beaten, I reached out for Jim's hand and followed Mary to the bedroom.

In the bedroom Mary started giving me instructions. "Kiss him again Donna. Now kneel and undo his pants. Touch his cock. Gently now. Wrap your right hand around it and fondle his balls with your left. That's a good girl. Now kiss it, then lick off the precum. Mmmmm."

I looked over and Mary was sitting in the easy chair rubbing her clit.

"Now, take it in your mouth. Hold it with your lips and wrap your tongue around the head. How's she doing Jim?"

"Oh shit, that feels sooo good!" he responded.

"Just wait, it gets better. OK Donna, time to suck him in, while lowering you mouth over the whole thing, keeping pressure on it with your tongue, and then raise back up. Establish a smooth rhythm and try to get it into your throat without gagging."

Jim's moans got louder and he finally started to shout, "I'm cumming!"

"Swallow it Donna, Don't miss a drop!" shouted Mary as she too reached her orgasm. "OK Donna, clean him up with your tongue and then redress him."

"That was great Mary. I especially liked the touch of you giving Donna instructions. You'd think it was her first time?!" said Jim.

"It was Jim, it was. But it won't be her last. Show Jim to the door Donna, and don't forget to curtsey as he leaves. Then bring Steve back with you." she ordered.

"Yes mam," I said.

Mary had me repeat the process with both Steve and Greg, and although I now knew how to be a cocksucker, she continued to have me follow her instructions.

As I was fastening Greg's belt, he said, "You know Mary, it's a pity Donna hasn't been taken care of too."

"Well, if you haven't caught on Greg, she's being punished. But if you want to give her oral, I might consent," responded Mary.

"That's not necessary," I quickly said, knowing what Greg would discover if I allowed him to pull down my panties.

"You sound a little scared, Donna. Never had a guy go down on you before?" teased Mary. "I thought fear increased the intensity of your orgasm. That is what you told me, isn't it? That is why you do the things you do, isn't it?"

"Yes, but. . .", I started.

"Well Greg? Do you really want to pleasure Donna?" asked Mary, cutting me off.

"Oh yea, especially if she's not had a guy before! She's so hot!" remarked Greg.

"You heard him Donna, you can't let a compliment like that pass. OK Greg, I'll let you have her if you can follow my instructions, to the letter," she replied.

"YES MAM!" Greg shouted.

"OK then, lay Donna back on the bed, gently now. Kiss her like you really mean it and are in love. You're doing fine Greg. Now crawl around between her legs. I need to tie this scarf around your eyes. Now reach up and grasp her panties on each side of her hip and lower them. Raise your ass Donna so he can get them down. Pull them all the way off Greg and then slide your hands up her stockings,back up to her waist. You're doing great Greg. You follow instructions well. Now, lean forward slowly and open your mouth."

As he did this, Mary raised my cock to align with his mouth. "You're doing fine Greg, just a little more. Finally, he had his mouth over my cock and then his tongue touched the head. He was startled and started to raise up, but Mary forced his mouth all the way down.

"Suck it Greg! Just like he did you! You're already there, so finish the job if you don't want Jim and Steve to find out!" Mary ordered.

Greg soon realized he had no other choice and started sucking my cock. Mary took his scarf off. Mary could see that I was getting close, so she reached up and pulled my wig off, which startled me and I shot my load.

"Swallow it all Greg, just like Tom did you," she laughed.

In a bit Mary said, "OK Tom, put your panties and wig back on and become Donna again. Now, sit beside Greg on the bed, I'm sure he has some questions."

Greg looked at us and simply asked, "Why?"

Mary explained all that had occurred today, and ended the explanation with, "So, you see Greg, I now have a full time maid in Donna, and I need someone like yourself to take her out some nights when I want to enjoy a real man. Do you think you can handle that? I promise to tell no one else, and she'll keep herself pretty for you."

Pausing to think about it, Greg finally replied, "OK Mary, I think I can handle that, as long as no one else finds out, especially Jim and Steve."

"It's a deal then. OK Donna, get your new boyfriend a drink, while I get you a nighty. Greg may want to spend the night and 'test the waters' a little more."

Totally feminized, I replied, "Yes mam," curtsied and went for the drink.


The End




2003 by Donna Williams. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, compilation design) may printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without express written consent of the copyright holder.