What If?

by

Karen J. Roush

   

Prologue: What if life had been different? What if had been born a female rather than male? Or perhaps even more confusing what if I found myself female in certain situations with full female consciousness, awareness, and knowledge like I had been born and raised that way and had simply progressed to that point of my life yet fully aware of my maleness and male life?

I got to thinking about all of this just last year at my 35^th high school reunion observing the women I knew way back when.. Remembering them as they were, seeing them as they are now, and knowing what they have and are going through to maintain their youthful looks. This first chapter will involve that reunion with me now as a 52 year old woman totally aware of her life yet totally conscious of my male life.

This is just my ramblings and the names will be changed to protect the innocent. If I get positive responses I will probably explore many other key points in a woman's life yet still aware of my maleness. Some of these points could include growing up, dating, losing my virginity, marriage, getting and being pregnant, childbirth, divorce, working, raising children, or even suggestions from you readers. Let me know what you think!

The Reunion

I woke up that Saturday morning and while everything looked somewhat familiar to my condo, it was definitely different. I brushed the hair away from my face and then it hit me. What am I doing brushing hair away from my face? I am bald and have been for several years and kept my hair quite short. I sat up and then I felt the weight on my chest, what the hell? I reached down and felt the silky material and under it were breasts and good sized ones at that. Yes I could feel they were pretty saggy but still a rack nonetheless!

I jumped up out of bed and raced to the mirror on the vanity. As I peered into it I was greeted by a definitely female face with almost shoulder length auburn hair. I could see the pink nightgown I was wearing and quickly reached for my crotch. That too was gone and replaced by what I presumed to be a vagina and a sticky one at that! What the hell is going on I thought as I sat down on the stool in front of the vanity. Last night I went to bed a 52 year old man planning on attending his 35^th high school reunion today and here I wake up an obviously middle aged, well maybe even a little more, woman.

I sat there for a minute or so before I glanced around the room. In the corner were a bra, panties, and pantyhose hanging from the shower rod that presumably I had worn yesterday. The room was a soft pink and definitely a woman's room. I saw the purse on the dresser and presuming it to be mine or at least the woman that occupied this body yesterday I went over and opened it. I saw the wallet and looked inside and there was a driver's license for Karen Jane Connors. It had my birthday on it and the picture was definitely me, well the me I was for this second. Let's see I am 52 years old, height was 5'4", and weight said I was one hundred and , well let us just say I could stand to lose a few pounds.

What is going on? Yes all my life I had been a cross dresser, that was what broke up my marriage, and yes I had wondered what it would be like to be female, even dreamt it at times but this is too much! I need a cup of coffee I thought as I looked around and saw the pink terry cloth scuff slippers and the pink robe. I pulled on the robe and slipped the slippers on and opened the door to my room. I could smell the coffee, I must have set it to go on automatically last night I thought. I walked into the kitchen and stopped dead in my tracks. Standing there at the counter buttering a bagel was my youngest daughter Heather in just a pair of panties and a t-shirt!

Hi Mom," she smiled. "I thought I heard you come in late last night and made your coffee for you."

"Thanks Heather" I mumbled trying hard not to stare at her prominent nipples protruding from the thin t-shirt.

"How was your date last night", she smiled as she joined me at the table. I didn't go to bed until after 2 and you still weren't home, you were a good girl weren't you Mom?" she snickered.

"Of course I was," I snapped knowing only too well from the stickiness on my upper thighs and in my crotch that was far from the truth. "I swear is that all you young girls think about, sex?"

"Oh knock it off," she sneered. "I heard that hum from your bedroom the other night. Don't tell me you weren't using your vibrator."

"Young lady that is none of your business," I snapped at her.

"Hey don't get your panties in a bunch Mom," she said as she reached over and gave me a hug. "We all have needs, even old ladies like you. I have to get dressed I am meeting Jen at the library so we can work on our project for government class and you have to get going too. Isn't your appointment at the salon for 11:30? After all you want to dazzle them at that reunion tonight."

"Yep" I replied as she left the kitchen.

I finished up my coffee and debated about having a bagel but decided not, don't need to add any extra calories to these hips and thighs. My God, I am thinking just like a woman! I poured myself a second cup of coffee and headed back to my bedroom to get ready for my salon appointment. I looked at the clock on the nightstand and it said 10:25. I had better hurry up, good thing the salon is just around the corner, can't take more than 5 minutes to get there. How did I know that?

It only took me 5 minutes to do my make-up, unlike the cross dresser I used to be where it took at least a half an hour. The hot rollers were in my hair so I proceeded to shuck the nightgown and went into the bathroom. I used a washcloth to wash the stickiness from my thighs and vagina. Hey, that felt kind of nice I thought. I took a long look at the naked form staring back at me from the mirror. This body had definitely seen better days. I had a bit of a tummy, some stretch marks, saggy boobs, and some cellulite on the thighs. Oh well I am sure I had remedies for all of this, yea right!

I opened the top right drawer of my dresser to grab some panties and a bra. Again how did I know that was where they were? It was becoming obvious to me this was some form of a parallel universe where I was female. All I saw were some very plain looking bras, mostly white with a couple of beige ones and one black one. Why not I thought so I grabbed the black one along with a pair of black panties, high cuts but at least they were nylon and not cotton!

I quickly dressed in a pair of jeans and a light sweater pulling on a pair of running shoes. I looked at my watch and it was only 10:50 so I had some time. I picked up the yearbook on the dresser and figured maybe I should take a peek at what a fox I was back in high school. I tried to look up my picture and I was nowhere, there was no one with the name Connors. What a minute that was probably my married name I needed to know what my maiden was. I took a shot and looked up Roush, after all that is what my name used to be and there I was Karen Jane Roush. I wasn't beautiful but definitely cute with my long soft brown hair and mini skirts. Young and thin with a perky set of smallish boobs, not these 38C's that now hung in my bra. I then looked around the room, my bedroom, and saw pictures of three kids, 2 daughters, Heather of course and a picture of another one that appeared to be her graduation picture from college, and a son who looked to be 20 or so. I continued to explore a bit but so it was time to head to the salon so I grabbed my purse and headed out to my mini-van, how soccer mom can you be Karen?

I go to my appointment a few minutes early and was taken right away. I had already set it up for a dye job with some highlighting, a manicure and pedicure, this girl was going all out for her reunion. It took a couple of hours and $125 plus tips but I was finally done. By now my stomach was grumbling when I spied the Mickey D's just down the street. Now that sounds good I thought, a Big Mac with a large fries and a big, thick chocolate shake. I drove over there and what inside.

"Welcome to McDonald's, may I take your order maam?" the high school aged boy behind the counter said as I approached.

"Certainly" I smiled. "I'll have an Asian Chicken Salad and a small Diet Coke."

"Right away maam."

What the hell was I doing? I wanted a Big Mac and I hated diet anything! My God! I wanted to shout out to change the order but I stood there silently fumbling through my change purse for exact change. What the hell was I doing? I knew I wanted more to eat yet my consciousness wouldn't let me order what I wanted. I waited patiently and even said thank you and have a nice day to the kid behind the counter. I quietly took my food and while my brain told me I wanted more the salad was more than I could eat so I finished what I could and headed home.

I got home and Heather was headed out the door telling me she was spending the night at Amy's so Don and I could have some privacy tonight. So it was Don that left my thighs sticky I thought as I headed back to my bedroom. I looked at the clock and it was already after 3 and something in the back of my mind said something about:00 so I stripped and headed to the bathroom to draw myself a bubble bath. I quickly took a peek at my bra and the size read 38C and the panties that had stretched their way across my very ample backside read large.

I laid in the bath taking the scents of the bath oil I had generously poured in. What the hell is going on I thought as I very casually reached for the razor laying there and proceeded to shave my legs and armpits of any stubble there. I even took the time to touch up my pubic hair a bit although there was still definitely a bush there before stepping form the tub and letting the water drain. I patted myself dry with the fluffy peach colored towel before rubbing lotion into my bare skin. I finished up and headed back into the bedroom.

It was like I was having an out of body experience. Here I was obviously female yet full conscious of my originally being male as I pulled things from the dresser. First came the Hanes Barely Black Sheer Indulgence pantyhose which was obviously control top followed by the black Wonderbra strapless bra, both of which were brand new as I had to remove tags. Obviously Karen had planned out her reunion outfit in advance I thought as I opened the closet. I grabbed the new, tags still attached, black velvet dress with the spaghetti straps and matching jacket and pulled it on. I grabbed the black pettislip from the drawer and worked up into place over my big bottom and took a look in the full length mirror on the closet door. That tummy needs help girl I thought as I peered at the reflection. I reached into the bag on the closet floor and grabbed the girdle and after cutting the tags off I squirmed my way into it.

After I had worked the tight girdle over my big butt I took another peek in the mirror, that's better I thought as I sat back down at the vanity. I redid my make-up in a more dramatic style more appropriate for evening before sliding my jewelry on and putting in a pair of diamond stud earrings. Then I headed back to the closet and pulled out a pair of new crushed velvet black sandals with a very high heel. Karen had given this reunion I thought as I buckled up the ankle straps. The final touch was a white gold ankle bracelet which shone brilliantly against the black nylons. A quick couple of sprites of perfume, I smell pretty good now. Another peek in the mirror told me I was ready to go so I loaded up the black velvet clutch purse and headed back downstairs.

It was 12 minutes to 5 according to the clock in the living room so I poured myself a vodka and tonic and sat down. I thumbed through the Redbook on the table for a few minutes before the doorbell rang. I got up as if I was expecting someone and there stood a very handsome man in his late 50's or even early 60's. Without saying a word he leaned in and gave me a peck on the cheek. Obviously this was Don I surmised, the one that had left me the sticky thighs from last night.

"You look ravishing Karen," he smiled. "Ready for dinner?"

"Of course," I smiled back and grabbed my purse and out the door we went.

What the hell am I doing smiling at this guy? I know what he wants and believe me he is not getting it! Don was oblivious to the fact that 24 hours ago I had a cock just like he does, all he seemed to see was me as Karen. I do have to admit he was a gentleman opening the car door for me. I could feel the coolness of the leather seats on my nylon clad thighs as my dress skid up while I positioned myself and buckled my seat belt. I quickly tugged at the hem to pull it down, no sense in giving him any ideas. Don had made reservations at a very nice Italian restaurant and dinner was very nice, complete with a couple glasses of wine. I was shocked I couldn't even come close to finishing my dinner and asked for a doggie bag while saying no to dessert. Just 24 hours I would have wolfed down the meal and had a dessert too!

When we left the restaurant Don again was a perfect gentleman. He pulled the chair away so I could stand easily, held the door for me as we left and again held the car door for me as I got in. I could have done without the wolf whistle he gave me as the hem of the dress slid up as I sat down but if I suppose as a 52 year old divorced woman I could have don a lot worse for companionship. Still the thought of having sex with him was repulsive, I guess my maleness was shining through.

We got to the reunion and got our name badges, his just had my name on it with a note he was my escort while mine showed my current and maiden name. We entered the hall and while Don went to get us a drink I looked around at all the faces. It shocked me how many I recognized. We roamed through the hall for a few minutes after he returned with the drinks saying hello to a few people, all of whom seemed totally unphased by the fact I was now a female. I finished the drink and realized I had to go to the restroom. I left telling him I would be back in a minute to which he replied "Of course" with a silly smile.

I almost inadvertently walked into the men's room, hey 52 years of the sameness was tough to overcome, but caught myself and found the ladies room. As I entered it I was taken back at how nice it was and how nice it smelled, much better than any men's room I had ever been in. I found an empty stall and proceeded to do my business with some difficulty. I found wiggling out of the girdle and pantyhose a pain in the small confinements of the stall not to mention having to hold my dress and slip up as I went. After I finished my business I took a small wad of toilet paper and wiped myself then proceeded to wiggle the pantyhose and girdle back into place, and I thought wiggling out of them was a pain!

I exited the stall and went to the mirror and like it was a reflex of years I proceeded to touch up my shiny nose and lipstick. I was just situating everything back into the small purse when I heard a voice call out.

"Karen, is that you?"

I turned to see a much more overweight than I was middle aged woman with blonde hair and a huge set of boobs. I looked for a second and it came to me who she was, Nancy Wells. I remember her well as I had dated her in high school, took her to the senior prom, even lost my virginity to her in the back seat of my car.

Yes," I smiled back. "Nice to see you Nancy."

"Come on girl," she said. "Is that best you have for what used to be your best friend?"

"Sorry," I said. "You just surprised me."

"I understand, you here with anyone else."

"My boyfriend is here."

"That isn't what I meant," she smiled. "Are you two sitting with anyone?"

"No we haven't found a table yet," I answered trying to avoid too much information.

"We have one near the back, why don't you wait for me and the two of you can join us," she said as she entered the stall I had vacated just a minute ago."

"Sure," I replied as I rechecked my make-up.

She was exiting the stall as I was fussing with the strapless bra which felt like it was slipping down. She smiled as she washed her hands and touched up her make-up.

"They are a pain in the ass aren't they?" she said as she fidgeted with her own obviously strapless bra judging by the red dress she had on. "You think yours is bad you should try being a 40DD and even trying one to find one!"

"Yes they are, and I thought being a 38C was bad enough," I sighed.

As we exited the rest room I remembered how stacked Nancy had been back in high school, I think she may have been the only D cup In my entire class! After I the introductions between her husband and Don we followed them through the crowd to a table near the back. There sat Debbi Murphy and Brenda Wilson with their husbands. I had dated both of them back in high school, I even got to third base with Brenda but never further and Debbi had been the first girl to ever give me a blow job. Now here I find out I was part of their clique back then. After the introductions we kind of rearranged the seating so we four ladies were together and could talk easily.

As we chatted it became apparent time had been nicer to Debbi and Brenda than Nancy when it came to figure but both had definitely put some weight on. Then again remembering the yearbook photos of me so had I. I was surprised how easy the chatter was as we talked about lives, kids, even gossiped about the girls and guys here at the reunion. I felt very at ease like I had been there as Karen and my whole life was as her. Then I was stopped dead in my tracks by a voice.

"Hello Karen, you look very nice tonight," the handsome gentleman said as his steely blue eyes stared down at my cleavage.

"Hi Mike," I gulped almost like a schoolgirl with a crush. "You look good as well."

"I saw you across the room and had to say hello," he smiled.

We chatted for a few minutes and all the time my heart was racing and I could even feel a dampness in the crotch of my pantyhose. I realized that this hunk, the guy who was a football player back then and still good looking was the guy I had lost my virginity to. It was like it was yesterday, I remembered exact details of how we were both dressed, how we were petting in the back seat of his father's Buick, how we eventually were both naked, and even him entering me. I remember the pain of being penetrated for the first time but the pleasure I felt as he pumped away at my virginity taking it from me and making me a woman.

After a bit the DJ started spinning and Don asked me to dance which I eagerly accepted. The first couple were definitely fast ones from our high school days and I was shocked how graceful I was dancing as I had never been a good dancer and now I was even in 4" heels. We danced those and then the first slow one before we went back to the table for more girl talk. After a bit and yet another scotch and water, I think that made four so far, Don was driving so it wasn't an issue.

The drinks combined with the pressure of the girdle were telling me it was time to go. Surprisingly rather than just simply getting up and excusing myself I looked at the other girls and asked if any else had to "powder their nose", to which they all said they did so the four of us headed off to the rest room. Why is it women have to go in groups I thought as we walked across the room while when I was a man I was perfectly capable of handling it by myself?

I was surprised how a simple task I had taken for granted for years was in reality a social event. We chatted, even dissed about some of the women; "How could she wear a dress like that?" "Didn't she look in a mirror before she left the house?" "She could certainly use a good girdle?" and so on. I was shocked to find out I wasn't the only that had wiggled my fat ass into a girdle for tonight, all of them had one on of some sort although Brenda said this was the first time she had worn one. Fat chance I thought as I touched up my lipstick, with those hips and thighs of hers if this was the first time she wore one it shouldn't be that last! What the hell is going on I thought as we exited the rest room and started back towards the table. I am thinking just like a woman!

As the evening progressed the DJ went from mostly fast music to slower music and Don and I danced a lot, obviously he enjoyed it and unlike I was just like last night, I was now a good dancer who enjoyed it too! We were on the dance floor having just boogied to "The Doobie Brothers' China Grove" when the DJ started spinning "Herman's Hermits' There's A Kind of Hush". Don grabbed me by the hand, pulled me close, and we started to dance. I felt his hand slip from my waist to my tush and he whispered in my ear.

"Nice tight butt," he cooed. "The new girdle?"

"Yes," I whispered back. "It will be good to get out of it."

"I'm looking forward to that," he cooed back and kissed my earlobe.

He pulled me tighter into his body and although I wanted to scream out I laid my head on his shoulder as we slowly swayed. I could feel him grinding his pelvis into mine and what was worse I could feel his manhood getting stiff! My God! This guy is getting turned on and I know he wants to take me home and screw my brains out! What was even worse I could feel the dampness returning to my own crotch! I was appalled at the thought of him trying to impale with his cock yet my own body was betraying my mind!

The rest of the evening was more of the same, dancing with Don, chatting with the girls, and soon it was time to leave. We parted with the kisses on the cheek and promises to get together but we all knew it wouldn't be until the next reunion. Soon I was seated in Don's car, after he opened the door for me of course, and we were on our way back to my place. At a stoplight he leaned over and gave me a kiss and took my hand and placed it on his lap. I could feel his stiffening member through his pants and shorts,. I wanted to pull it away and scream "I am a guy!" but instead I softly massaged it as I felt it grow and saw him smile. Soon we were home and in we went.

"Help yourself to a drink and pour me one too," I said as I slid the heels off. "My feet are killing me and I need to get out of this girdle"

"And slip into something more comfortable?" he cooed as he lightly kissed me on the cheek.

"You'd like that, wouldn't you?" I whispered back as I reached down and softly rubbed his once again rising member through his pants.

"You know I would," he smiled back.

As I turned to leave he softly patted me on the tush and I headed up the stairs. Once inside my bedroom I closed the door and sat on the bed. What the hell am I doing I thought. Here I am a guy, well at least I used to be, yet I was coming to this man and leading him on to believe he was going to get something tonight. A part of me was screaming in my head, "You're a GUY and you are not gay" yet another part of me was feeling all warm and fuzzy, well all except my vagina which was again wet with anticipation.

I remembered what I had come up here for so I took off the dress and hung it up on its hanger. I then stripped off all my underclothes and took them into the bathroom and put them in the hamper to rinse out later. This is certainly different I thought as I again sat to relieve my kidneys. As a guy I would have just tossed everything anywhere and gathered them up in the morning, as a woman I was obviously a neat freak. I glanced at my now naked body in the mirror before I left the bathroom, I guess for a woman my age I wasn't bad but certainly this body was not going to ever pass for 18 again.

I went over to the dresser and opened the bottom right drawer and there before my eyes lay a bevy of obviously sexy lingerie. Instinctively I rummaged through and found a black lace chemise nightgown which came to mid thigh and with its open lace left little to the imagination. I then headed to the closet and grabbed a pair of marabou slide slippers with a 2" heel and slid into them. I gave my face a quick peek in the mirror and after freshening up my lipstick and a dab of powder on my shiny nose I headed back to the stairs.

As I could hear the heels clicking on the hardwood floor as I descended the steps I thought to myself this is sick! I am not a fag, I don't want any part of this guy, all I want is for him to get the hell out of here and leave me alone. As I entered the living room I could see Don had removed his tie and jacket and was sitting on the sofa and on the coffee table in front of him sat two drinks. After doing a model like twirl to his approval I crossed the room, sat down on the sofa next to Don and took a sip of my drink.

"I love you in that nightie Karen," Don whispered in my ear as he reached over and softly kneaded my nipple prominently showing through the black lace.

"You love me out of too," I sighed back and again reached for his member.

It took a matter of seconds and Don and I were lip locked. I could feel his tongue in my mouth and I eagerly reciprocated. As we kissed he began gently massaging my breasts and I found his zipper and fished out his cock and was softly massaging it. We stayed that way for several minutes before we finally separated our faces and I bent down and gave his cock a kiss and licked the droplet of precum that had formed at the head.

"Don't you think we would be more comfortable in my boudoir" I said as I looked back at his smiling face.

"I thought you would never ask," he smiled from ear to ear.

I stood up and took him by the hand and up the stairs we went. We went into the bedroom and I closed the door behind us and went over to the nightstand and lit the candle there, leaving the rest of the lights off. I sauntered back to Don as sexy as I could and started to help him out of his clothes. What the hell am I doing the back of my brain screamed out! Here I was helping a man out of his clothes as I longed for his cock. I am not a queer, am I? Soon Don was naked and his manhood pointing straight out. I got down on my knees In front of him and as my hands played with his obviously full balls I took his cock in my mouth and began to give him a blow job.

He was obviously enjoying It as I could hear him moan but what was worse I was too as I could feel myself getting wetter. After a minute or so I stood up but kept my hand on his cock softly massaging it. I gave him a kiss on the cheek then leaned up on my tiptoes.

"I know you love a good blow job," I cooed in his ear, "But I really want you In me tonight."

"I know he said as he reached behind me lifting the hem of my nightie and softly rubbed my fat cheeks. "Come on to bed and If you are a good little girl I will let you have the trouser snake."

We walked to the bad and I turned the bedspread and sheets down before I laid down. Don got In the other side of the bed and in a matter of seconds I was stroking his cock with my hand and he had two fingers in my sopping wet pussy and had my left breast bared and was sucking on the nipple. We stayed that way for several minutes before he rolled over and I instinctively spread my legs. He pushed the hem of my nightie up and I could feel his cock enter my almost trembling slit. There was a part of me that wanted to throw up yet more of me was thoroughly enjoying the pumping action. I was partly repulsed by the thought of a man on top of me having his way yet as I could feel his balls slap Into my fleshy cheeks I was getting hotter.

We stayed like that for several minutes with him thrusting his manliness into me and I thrusting back before I put my hands on his shoulders and gently pushed him up. He leaned back and his cock slid out and I slid over on the bed. I guided him onto his back where I had been laying and swung a leg over his prone frame. I dangled the lacy hem of my nightie on his steeliness for a second before I reached under me and guided him back into my now needing pussy. I knew I had been a man but at this second I was a woman and I wanted to orgasm, I needed to orgasm!

I plunged down and felt a warmth as I bottomed against Don's body. I could tell by the smile he had he was enjoying this and he reached up and began to massage my breasts which heightened my pleasure. As I worked myself up and down on his love pole he thrusted back and worked my breasts. I was getting warmer and more tingly by second and then suddenly I felt it. It was magnificent as my whole body shuddered in pleasure I could see by the smile Don was enjoying my orgasm almost as I was. I could feel the waves of pleasure got through me but I was a good woman and kept working his cock knowing he needed relief too. It took only 30 seconds or so and as I began to return to an almost normal rate I could see his tense his face and feel his cock grow even a bit stiffer. Suddenly I could feel him pulse in my loins and him breathe hard. As I continued I could feel the spurts of his juice mingle with mine.

Finally his cock was done throbbing in my slit and his breathing was returning. I leaned down and gave him a huge kiss before getting up and heading to the bathroom. I peeled off the black lace nightie whose hem was wet with a mixture of my juices and Don's cum. I took a wash rag and wiped of my pussy and slid on the plain pink knee length nightgown which was hanging on the back of the door before I rinsed out the wash rag and took it out and wiped Don's now softening member clean and gave it a kiss. By the time it took me to take the wash rag back to the bathroom, rinse it out, and return to my bed Don had slid over to the other side.

I slid into bed and pulled the sheet up over myself and Don. I rolled over on my side and laid my head on his shoulder after giving him a kiss on the cheek. He slid his arm under me and around my shoulder drawing me tighter to him.

"You know how I hate sleeping in the wet spot," I cooed and again kissed him on the cheek.

"I know," he smiled, "but you certainly enjoy what it takes to get that wet spot there my little minx."

"Heavens yes," I cooed.

Don leaned over and blew out the candle and I laid there with my eyes closed and could feel him slipping into a sleep. I have no idea how or why I am a woman today but I do know if this is what I have been missing all my life I intend to make up for lost time quickly!

  

  

  

*********************************************
© 2007 by Karen Jane Roush. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, and compilation design) may be printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without the express written consent of StorySite and the copyright holder.