A Practical Joke Made This Boy Into a Happy Woman
by: Steve Matyas

 

As organ music filled the church and penetrated into the small room I was in, I took one last long look at myself in the mirror. I guess it's true what I've always heard about all brides being beautiful. After all, beautiful was the last word you'd use to describe me. But in my flowing white gown and veil, I was beautiful, dammit, no matter what anyone said. I opened the door and stepped out into the church, thinking about my wonderful future and the strange past which had preceded this moment.

I was brought up in a small midwestern town, the second of four kids. We loved each other and fought like tigers depending on the mood at the time. As the oldest of two boys, I won most of the fights.

When I was in the ninth grade, my older sister became friends with Linda, the best-looking and most popular girl in Senior High. I made any excuse I could to be around when Linda was visiting, just so I could look at her and dream about being with her. Of course, she thought of me as her friend's kid brother and mostly ignored me. I often wonder what would have happened if she had never taken enough interest in me to include me in her bizarre scheme.

Linda was strongly in favor of equal rights. She organized boycotts of school clubs and sporting events that only allowed one sex to participate. She wrote editorials for the school paper and tried to get girls to try out for the football team. When she couldn't find any willing to try, she decided to attack a different sport; that's when she sucked me into her plans.

Linda figured if she couldn't get a girl onto a boys' team, the next best thing was to get a boy onto a girls' team. She plotted with my sister to get me to be thier guinea pig. First, Linda started to pay attention to me, telling me how handsome and mature I was and inviting me to go with her and my sister to movies or parties. As I spent more time with her, she began talking about equality and her dream of sexually integrating the school athletic teams. I agreed with her, hoping that by doing so, she would really get to like me. Then one day, she sprung her trap.

We were all sitting around the house, drinking some beer that Linda had stolen from her Dad and smoking pot. As usual, Linda was going on and on about equality and whatnot and I was agreeing heartily. Suddenly my sister said,"You know what we should do? We should get a boy on the girls' field hockey team."

Linda said that was a great idea, but,"Who do we know who's secure enough in his masculinity to do something like that? All the guys I know are too wimpy to try."

The beer and pot made me speak up.

"I'll do it", I said. "After all, how hard can it be?"

They giggled and told me it was a bad idea. But I persisted until Linda finally said,"Maybe it'd be worth a try. After all, Brad's so-o-o-o mature for his age. And nobody on the team would know him. Especially if we dressed him like a girl."

"Wait a minute!", I shouted. "What's this dress him like a girl stuff? I thought the idea was to get a boy on the team."

"It is", Linda replied. "But at first you'd have to pass as a girl. Once you were on the team, you'd reveal who you really are and embarrass the shit out of them. Then we've proved our point about how ridiculous it is to segregate."

"No way", I said.

"I thought you were man enough to do it", Linda said as she approached my chair and sat in my lap. "But I guess not. You're just an immature little wuss like the rest of them."

To show her how much of a man I was, I kissed her deeply, thrusting my tongue into her mouth and moaning. It was the first time I had kissed anyone like this and my head spun and my dick grew rock hard. Linda pulled away, pinched my crotch, and giggled,"Well, I guess you're a man after all. If you help us out, you could get a man's reward."

I was too horny and dizzy to do anything other than agree and Linda said we would start work the next day at her house. She left and as I watched her walk away, she turned and blew me a kiss while she rotated her hips suggestively. I knew I'd do anything she asked.

The next day, I went to Linda's house without my sister. Linda answered the door and led me upstairs to her bedroom where, without saying a word, she dropped to her knees and pulled my dick out from my pants. She stroked and licked it until it got hard, then took it into her mouth. As soon as I felt her warm wet breath on me, I shot my wad. She swallowed it, licked me clean, and stood up, smiling.

"Okay, now you know part of what it is to be a man", she said. "You'll learn the rest later. But first you have to learn to be a girl."

She led me to her closet and picked out a dress. "I think you'll look darling in this", she said. "But first we have to fix you up a little."

She took me to a mirrored table and sat me down. She started applying creams and liquids to my face, followed by lipstick and eye shadow. She produced a wig and pulled it onto my head, then sprayed me with swee-smelling perfume. When she was finished, I didn't look like myself, but I didn't look much like a girl either. I told her I didn't think I could pull it off, but she just shushed me.

"Being a girl is ninety percent attitude", she said. "I'll get you there-don't worry."

She then told me to stand up. When I did, she wrapped something around my chest and ribs and pulled it so tight I couldn't breathe. When I started to protest she giggled and said, "It's just a silly old corset, sweetie. Now hold still while I fasten it."

She somehow forced the corset even tighter and tied it in back of me. I looked down at my chest and was surprised to see two small lumps formed by the corset where a gorl's breasts would be.

"It's a start", Linda giggled. "But you definitely need a padded bra."

She went to a dresser, pulled open a drawer, and came back with a frilly bra and matching panties. She put them on me and as I felt the silky texture of the panties riding up my thighs, my dick started getting hard again. Linda giggled and said, "Don't worry, you'll get used to it."

She finished off my wardrobe with a pair of thigh-high nylons, a frilly slip, and a short tight skirt. She told me to put on a pair of high heels and go into the bathroom for a look. I tottered on the heels, but finally made it to a full-length mirror. Linda was right, I did look like a girl; except for the bulge in my crotch, anyway.

Linda came up behind me and kissed me on the neck as she stroked my thighs and ass. The feel of her rubbing against the silk and nylon almost made me cum. When she heard my breathing become fast and ragged, Linda said, "Go ahead. Jack yourself off. It'll help you get used to the sensations. And I'll even help."

She went to her bed and knelt on it, facing me. She pulled her sweater up and her skirt down and began running her hands all over her body, moaning softly. My dick was in my hand and shooting into the air before I knew it. Linda giggled, told me to clean it up, and left the room.

I found a washcloth and cleaned every drop of cum I could find off the floor. As I finished, Linda came back in and told me I could change and go home.

"First, though," she said, "why don't you try some of my dessert?"

She had a bowl of pudding with mounds of whipped cream on it. She scraped some of the cream off with her finger and stuck it into my mouth, encouraging me to suck on it. The cream was delicious, so I sucked eagerly. Linda giggled, smeared cream around my mouth and down my chin, and told me to get changed.

Linda came up behind me as I stripped out of the girl's clothes and pinched my ass.

"Think today was fun?", she whispered into my ear. "Just wait until tomorrow."

When I got home I locked myself in my room and scrubbed my face repeatedly. No matter how hard I tried, I felt like I couldn't get the fiery red lipstick off my mouth. When my Mom called me down to dinner, I felt like everybody was staring at me. Of course, it didn't help that my sister kept making faces at me and winking when no one else was looking. I made up my mind then and there that I wouldn't have anything more to do with Linda and her insane plan.

As I was leaving school the next day, Linda came roaring up in her hot new convertible and invited me to get in. I didn't want to go with her, but all my friends were staring open-mouthed, so I got in. She drove me to her house, chattering all the way about her plan and how she had decided on a female name for me. I told her I wasn't going to go along anymore, but she just smiled and told me she was sure I'd change my mind.

When we got to her house, she told me I was perfectly free to go as soon as I had seen something. She took me into the house and led me upstairs. In her room, she stuck a tape into a VCR and I saw myself on the television screen, sitting in a chair and having makeup applied to my face. That scene was followed by shots of me putting on a wig and girl's clothes. Then I saw myself masturbating and licking cream off my lips and chin. Linda was nowhere to be seen in any of the shots.

"My brother Ray took these", she said when the tape was finished. "He's not a bad photographer for a hood. Now, SHARI, should we get busy or do you want this tape shown at the next assembly?"

I knew her brother and realized that he was capable of beaming a tape into an all-class assembly. He had done it before. So I reluctantly agreed to cooperate.

Linda took me into her bathroom and ordered me to strip while she filled the tub with water and flowery bubble bath. She told me to get into the tub and reminded me that Ray was taping everything. When I was in the tub, she scrubbed me all over and then produced a razor and shaved all the hair off my body. Once she had me clean shaven, she told me to get out and powder myself. I slapped sweet-smelling powder onto my body and followed her into the bedroom.

She had laid out a set of girl's clothing on her bed and she ordered me to put them on without any help. She laughed as I struggled with the bra and pantyhose, and said it would get easier all the time. She kept calling me Shari, saying I would get used to that too. Then she told me to put on a wig and follow her instructions in applying makeup.

"Don't worry, Shari,"she said. "All us girls have trouble with these things at first. But you'll be fine."

When I was fully dressed and made up, she looked me over and said, "Not bad. There's only one problem."

She knelt in front of me, pulled down my pantyhose and frilly panties, and released my erect cock. I hadn't realized how excited the feel of silk and nylon was against my newly shaven skin, but the effects were obvious. Linda sucked me off and said as she tucked my cock back into my panties, "I hope you learn to control that. I'd hate to have to gaff you."

I didn't know what she meant, but she said not to worry about it for now. We spent the next two hours watching videos of models walking and talking, Linda pointing out to me the special ways they moved and gestures they used. Finally she said I could change and go home.

The next few days were the same. Linda would pick me up at school, take me to her house, make me put on girl's clothes and instruct me on how to walk and talk. After about a week of this, she said I was ready to go out in public. I protested, but she reminded me of all the videotape her brother had shot and I consented.

Linda told me to pick out my own outfit, so I selected the longest, least feminine dress I could find and a pair of flat shoes. I wanted to look as inconspicuous as possible. She shook her head disappointedly at my choice, but didn't say anything. She took charge of making me up and used the brightest lip gloss and eyeshadow she had. She completed my costume with a long blonde wig and silver hoop earrings. She handed me a purse and led me outside.

We drove to a local hangout and went inside. Linda kept reminding to walk like I was a girl and not to look so embarrassed. No one paid much attention tom us as we found a booth and sat down.

We ordered some burgers and shakes. Linda kept calling out to people she knew and waving, but I tried to keep from being seen by any one. There were people I knew there, too, but fortunately they didn't seem to recognize me.

While we were eating, my sister came in with her boyfriend and made a beeline for our booth. She and Linda exchanged greetings and Linda introduced me as her cousin Shari from Detroit. My sister winked at me as she shook my hand and said, "Nice to meet you, Shari." Her boyfriend leered at me and gave me a kiss on the cheek, whispering into my ear,"Hey, sweet thing. Where've you been all my life?"

I felt my cheeks burn with shame as Linda, my sister, and her boyfriend all laughed.

My embarrassment only grew when my sister asked Linda if she had a spare tampon.

"I don't", Linda said. "But I'm sure Shari has some in her purse."

My sister told me I was a lifesaver and said I should go to the ladies' room with her. I could hear her boyfriend snickering as we walked away.

Once we were in the bathroom, she told me she really didn't need a tampon, she just wanted see how I was doing. I told her I hated her and Linda for doing this to me and I wanted to quit, but was afraid of Ray's videos. She told me I should go along with Linda for awhile and she would get bored and let me quit.

We went back out and finished eating. Linda said we should get going and I quickly agreed. As we walked out I felt a pinch on my ass and turned to see a friend of mine grinning at me stupidly. I walked over to him and slapped him hard across the face, to the amusement of everyone there. I put on my most feminine walk as Linda and I left.

A few days after that, Linda informed me that from then on, I should start going out with a boy. She said her brother had a friend who was dying to meet me and she had arranged a blind date for us. Again my protests were met with threats of exposure in front of the whole school, and I had to go along.

Ray's friend picked me up at Linda's house and drove me to a movie. I almost slugged him when he put his arm around me, but at least he didn't try anything else. When he dropped me off, he gave me a quick kiss on the lips and sped away. Linda rewarded me for my cooperation with another of her super blow jobs.

At last, field hockey season rolled around and the end of my nightmare was in sight. I had spent countless hours dressing and acting like a girl; I had gone out with several boys and had tongues stuck down my throat and hands groping under my skirt. And I had had a number of mind-blowing blow jobs from Linda and had masturbated time and again as she stroked herself in front of me. But now at last it was almost over.

Ray had hacked into the school computers and established a record for a transfer student named Shari Green. As the morning of my first day at school dawned, I was extremely nervous. Just because I had fooled some people at night didn't mean I could pull off being a girl full-time during the day. My hands shook as I applied conservative lipstick and mascara. I ruined three pairs of pantyhose before I finally got one on without running it and I changed skirts at least six times before deciding on a knee-length suede one.

Linda drove me to school and dropped me off. As I approached the main door with my books held in front of my chest like Linda had taught me, I heard laughter and was sure it was directed at me. I blushed furiously and looked at the ground as I passed a group of students and entered the school.

Classes that day were a blur as I concentrated on sitting and talking like a real girl. I had to go to the bathroom at least twenty times, and the first time I headed instinctively for the boys' room, only to be headed off by hoots and laughter. Once I got accustomed to using the girls' room, I relaxed and joined in the gossip sessions constantly in session in front of the mirrors. And I have to admit, the girls' bathrooms were much cleaner and nicer than the boys'.

At the end of the day, I changed into sweats in the bathroom and headed to thr gym for field hockey tryouts. As I looked around, I knew I'd have no trouble making the team, as the only girl close to my ability athletically was Amy, the returning star from last year's team. I easily breezed through the drills Coach Ross put us through and headed home happy.

When the team roster was posted later that week, as expected, I was listed as a starter. At practice that day I told Coach Ross that my mother was sick and I would have to leave right after practice every day, skipping a shower until I got home. He looked at me suspiciously, but consented.

The day of our first game, I was issued a plaid skirt, knee socks, and a sweater. As the reest of the team headed to the locker room to change, I said, "Omigod, I left my math book in study hall and I need it tonight. I'll be right back."

I ducked into a nearby bathroom and changed in the privacy of a stall. I was really scared that somehow during the game my true sex would be exposed, but Linda had done a super job of binding my dick and securing my wig. Nothing went wrong and we won the game easily, with Amy and I both scoring five goals. There was a celebration in the locker room afterward, but I ducked out, using my excuse of a sick mother.

As the weeks went by, I kept waiting for Linda to tell me it was time to reveal who I really was. The team kept winning and was headed for the state championships and amy and I were clearly the stars. We were elected co-captains and everything.

The day before the regional finals, Linda said that it was time to finalize our scheme. She wanted me to reveal myself the next day right before the game, saying it would freak everybody out so bad they would be sure to lose. But suddenly, I didn't want to go along. After all, we had a good chance of winning the state tournament and I had put a lot of effort into pulling this all off. Besides, I had discovered that a hidden benefit of all that time gossiping in the girls' bathrooms was that I knew which girls thought I was hot. I planned on taking full advantage of that information next year. So I refused to cooperate, telling Linda I didn't care if she exposed me to the whole school; I would make sure she got punished for her role in the whole thing.

She said, "I don't believe it. You really think you're a girl now, don't you?"

I told her I just didn't want to ruin it for the rest of the team and she walked away, shaking her head and laughing.

That afternoon Coach Ross called me to his office and asked me to sit down, calling me "son". I pretended to be confused but he said he had known for a long time that I was really a boy.

"Do you think you're the only guy who likes to wear frilly undies", he asked. "I'm a cross-dressser myself. Besides, you're too valuable to the team to lose now. I just wanted you to know I understand what you're going through."

He told me he wanted to take me somewhere that night and told me to dress "casual but ladylike". When he picked me up at Linda's house, I was wearing a denim jumper and turtleneck sweater. Coach Ross, on the other hand, was wearing a cocktail dress, a red wig, and tons of jewelry. He told me I looked fine and we drove off.

We stopped at a bar and he led me through it, smiling and swinging his hips as the men in the bar whistled at him. We went to a back room and I saw twenty men dressed as women sitting in a circle. Coach Ross told me this was a monthly meeting and I was welcome anytime. I wanted to protest that I really didn't belong there because I didn't WANT to dress like a girl, but I decided to keep quiet. The men gossiped and drank fancy mixed drinks for a couple of hours, then decided to go out dancing. I begged off, saying I had to rest for the big game, and Coach Ross drove me home.

We won the regionals and the sectionals. After every goal that Amy or I scored, she gave me a big hug and patted my ass. I couldn't help responding to her touch, but fortunately my arousal was well concealed. Now the only thing left was to win state.

The final went into two overtimes before we pulled it out on a miraculous goal by Amy. We went wild, jumping on each other and hugging madly. In the locker room after the game, we doused each other with water and had an impromptu wet T-shirt contest. Only after everyone agreed to meet later for pizza did the party break up.

As I got ready to meet the team that night, I knew that this would be my last appearance as Shari. I borrowed Linda's brightest lip gloss and shortest skirt, filling it out with a padded pair of panties which gave me a dynamite ass and hips. I sashayed into the pizza place on six-inch spike heels and swung my hips sexily as I walked up to our table. I knew eveery boy in the place was staring at me and I loved it.

We ate tons of pizza and drank enough wine that we were all a little tipsy. When I got up to leave, Amy said she would walk home with me. We talked and laughed merrily all the way to Linda's house. Once we were there, though, Amy got strangely quiet. As we stood on the porch, she suddenly reached out and pulled me to her kissing me hard and thrusting her tongue into my mouth. When I kissed her back, she moaned,"Oh, God, I was hoping you were a lesbian like me."

She started to reach under my skirt, but I pushed her hand away and laid her down on the porch floor. I reached under her skirt and found her panties were soaking wet. I quickly pulled them down, stuck my head under her skirt, and started to tongue her hungrily. She came several times before I stopped, exhausted. She told me she wanted to return the favor, but I said I was having my period and she could catch me next time. We kissed deeply and she walked off.

When I went into the house, I was surprised to see Linda standing there naked. She said she had seen the whole thing and was incredibly turned on. Somehow I found the energy to tongue her to orgasm before she stripped me and gave me one last blow job. Somehow, now, I had to return to normal.

It was surprisingly easy to get into my old life. I made up stories about my experiences out of state and started dating all the girls who had gossiped about me when they didn't know I was listening. Linda ignored me like usual and I rarely saw Ray. I almost never thought about Shari, but I did admire the trophy "she" had helped win in the school display case. The only thing I felt bad about was Amy. I wished she was interested in boys, but it just wasn't the case.

After I graduated, I moved and got a job as a mechanic. It wasn't great work, but it paid all right and wasn't too difficult. I dated around but never got serious about anybody.

Then, one night as I was sitting in a local watering hole, Ray walked in. He sat down and we talked about people we used to know. He mentioned my time as Shari and we had a good laugh about it. As he was leaving he said, "Oh by the way, I thought you might like to have this."

He pulled a set of video tapes out of his briefcase and handed them to me. When I got home, I put one in and saw pictures of myself putting on makeup, learning to walk and talk like a girl, and playing field hockey. I was fascinated by how much I was actually able to look like a girl. The more I watched, the more curious I got about whether I could do it again.

I spent the next week shopping for women's clothes and selecting makeup. When I had everything ready, I locked my door and carefully shaved my entire body. I made myself up, put on a wig and dress, and looked at myself in the mirror. No doubt about it, I looked like a woman, but could I fool anyone else? Knowing it was ladies' night at the local bar, I slipped on a pair of heels, grabbed a purse, and headed out.

Walking and talking like a girl came back to me easily, and I was soon having a great time, drinking free, dancing, and shooting pool. As it got close to bar time, the owner came up to me and said,"I've been watching you in action. How'd you like to tend bar for me?"

I thiught he was kidding, but he assured me he was serious and called out,"Hey, fellas. How would you like to see this little lady working here?" All the men in the bar roared their approval. I told him I'd think about it and gave him my number.

Stan, the bar owner, called me several times during the week. When I answered, I told him I was Shari's brother and would pass his message along. After a few days, the idea started to intrigue me. After all, there wasn't much future where I was working, and Stan assured me Shari could make a fortune in tips. The next time he called, I spoke to him as Shari and accepted the job.

Before reporting for my first night's duty, I went out and bought myself a curly long blonde wig and a set of false fingernails. I painted the nails fiery red and did my lipstick to match. I stopped at the mall on the way in and had both ears pierced several times. When I got to the bar, Stan looked me over approvingly and handed me my uniform. It consisted of a long sleeved white silk blouse, a black leather miniskirt, fishnet stockings, and a red felt bowtie. I have to admit, I looked extremely hot when I was finished dressing.

I made over two hundred dollars in tips that first night. It didn't take me long to figure out which customers to flirt with and which ones to just lend a sympathetic ear to. I was ecstatic but exhausted when I went home.

The next couple of years passed quickly. I let my hair and nails grow out and started getting my nails done professionally every week. I got to know all the regulars at the bar and dated a few of the men. I didn't get many second dates, though, because I steadfastly refused sex with them. A couple of times, I got drunk enough to suck someone off, but I could never control the impulse to gag and I hated the taste of hot cum. When I needed sex, I cut off my nails and went out as myself, picking up any woman I could. Fortunately, the kind of woman I met readily accepted my story of a rare tropical disease to explain my hairless body.

Then shortly before Thanksgiving last year, my old field hockey teammate Amy came into the bar. She squealed with delight when she saw me, saying she thought I had disappeared forever. We talked about old times and she kept reminding me that she owed me a good pussy lapping. I just laughed and changed the subject each time she brought it up.

At one point, I excused myself to use the bathroom. I didn't realize Amy had followed me in untiul I came out of the stall and she grabed me, pinning me against the sink.

"It's payback time", she purred as she reached under my skirt and yanked down my hose and panties. She knelt down and gasped as she saw my dick come flying to attention.

"Oh, well", she sighed. "I DO owe you."

She took my dick into her mouth and sucked inexpertly, gagging and choking as I had done when I sucked someone off. It was evident that she had never done it before. When I came she tried to swallow it all, but couldn't. She walked out without saying another word and I quickly re-did my makeup and tucked everything back in securely.

Amy was sitting at the bar when I came out and she looked at me sadly and said,"You know, I was really in love with Shari."

I told her I was in love with her too, and we decided to try dating as a lesbian couple. It worked great and we were deliriously happy. I performed oral sex on her whenever she desired and was content masturbating myself afterwards.

Which is how I come to be here in a church, wearing a beautiful white wedding gown and veil. Amy is waiting for me at the alter in a matching gown, looking even more radiant than usual because we did have sex once and she is carrying our child. Of course, everyone assumes she was artifically inseminated. I don't care if we have a boy or a girl; I just know the child will have something else no ither child has: two mothers and a father rolled into one couple.

And, oh yes, guess who my maid of honor is. That's right-Coach Ross!

 

© 2001
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