A Decision to Make

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A CD man is magically changed into a woman... has 48hrs.
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I had a trip planned at the end of the month so that I could dress and be myself, little did I know the next few days could change me for the rest of my life.

It started when I planned the trip two months ago back in November, I knew that the whole thing would be a ruse so I could spend an entire week dressed as a woman and sucking and fucking cock like the little slut I enjoyed being. I started by booking the hotel in my female name, Jamie Maddox. I then ordered an ID from china and had one of my credit cards put in that name to avoid having to outwardly reveal my gender to anyone. As the weeks went by I purchased more clothes and prosthetics so I could be the best girl I could be, since this was going to be the first time in my 30 years of life, that I would be living in my feminine form for longer than a few hours. I posted an ad on cragislist a month before I even checked into my hotel to start finding a man (or men) to take me on dates and really treat me like a woman. About a week before I was scheduled to leave, I got an email from a gentleman who wished to take me out for a night I would remember forever! We texted emailed and talked on the phone, seeming very compatible from the start. From his photos he was tall, black, 35 years old and well-built with a monster between his legs! He told me that he wanted to take me out for a night of bowling and then a nice dinner and dancing before we would retire back to my hotel for a little adult fun. I loved all these ideas and planned out my outfits and all the nasty things I wanted to do with him.

We spoke nearly every day before my trip and were both rather excited to spend time together. As the morning of my trip arrived, my wife and son left for the day and I began the process of going from John to Jamie. First I showered and removed all my body hair from head to toe, then slipped on my gaff and butt padded panty with a pair of pink cotton hipster panties. Once the lower regions were tucked and ready I slid into my yoga pants, pulled on my socks and my black Uggs. I leaned over the mirror and began the process of my makeup, foundation, eyes, cover-up, lips and then the hair to complete the ensemble. I strode my way out to my car, and began the 4 hour drive north. Along the way I stopped for gas, and some lunch and didn't seem to stand out. I checked in without a hitch or any seeming sideways look. I called Jacob when I got to my room and told him the good news; we planned on going out that night.

For bowling I would wear my low-rise boot cut jeans, with a white shelf tank and my loose fit grey crop-top with my knee high 4 inch heeled boots. I thought twice about the heels, but figured that I would need to put on bowling shoes anyway, so what did it matter. Since we would pass my hotel before dinner and dancing, I convinced him to stop back at the hotel so I could change into something more appropriate.

Jacob arrived promptly at 6:00pm just as we planned. He knocked on my hotel room door and I opened it to see a 6 foot 5 inch black man, with toned arms broad shoulders and nicely protruding pecks wearing a blue polo, nice looking loose fitting jeans and a nice pair of Gucci square toed shoes. If he was as nice in person as he was sexy, I was in some serious trouble. As I began to greet him, he held out a bouquet of fresh roses with light baby's breath. I took them from him and laid them on the dresser before walking out of the room for our night.

As we rode the elevator it was rather silent, but I could see already the considerable bulge in his pants and was excited to unwrap that package later. We made small talk on the ride to the bowling ally but the entire time I couldn't help but continue glancing at the cock bulge in his pants. He began my telling me about how his family came over from Congo and that he was the first of his family to be born in America. His mother was the town medic and his father was the religious shaman for the area that they lived in. I told him more about my job back home and what drove me to be the cross dresser he saw before him. We got to the bowling ally, rented our shoes and began the night off right. He let me win the first game, but swore that he didn't. He clobbered me the second game and we decided we were too hungry to play anymore.

As we climbed in his small Mazda for the trip back to the hotel I realized he had forgotten to zip his pants after using the men's room. I gracefully reached my hand over to undo the button of his pants as well. I worked his semi-hard snake from its cage and gasped with shock when I realized it was even bigger then it looked in pictures. I slowly worked my hand up and down his massive shaft while he drove. I wanted to taste it, but this was as much as a tease for me as it was for him, and I enjoyed it.

As we pulled into the hotel, I asked him to wait while I ran upstairs to change. I told him I would only be 15 or 20 minutes. I got into my hotel room stripped off my clothes, changed into my black gaff and put my black lace thong on over it. Pulled off my bra and ensured my breast forms were secure since I planned on going braless. I slipped my ruffled long sleeve halter on over my 36C breast forms and rolled my sheer tan thigh highs up, slipped my high waist knee length pencil skirt on and finally slipped into my 3 inch strapped heels. Before walking out the door I touched up my makeup, sprayed some candy apple body spray and added a little gloss to my lips. As I walked across the parking lot to the car, I could see him smile and as I got closer I could see he was stroking his rock solid erection.

I sat down in the car, and ignored his cock that was bouncing up and down with every bump as we drove because I knew that if I even felt it in my hand my lips would be wrapped around it and soon my boy-pussy would too.

Once at dinner he was a gentleman and pulled my seat out for me and everything. We ate quickly, and decided to skip dancing for the night, and to just take it back to my hotel room.

As we opened the door to the room, he picked me up by my waist and carried me near the bed. He stood in front of me and leaned down pressing his lips to mine. Softly pressing his tongue on to mine he guided me on to the bed. While still kissing me hiked my skirt above my waist revealing my thong and gaff. He pulled the fabric aside and began by licking my hole. Driving his tongue inside me, I started to grind my hips to his face, while he got on his knees and continued to lick me. As I started to feel the scratch of his beard on my cheeks, I pulled away and dropped to my belly with my head hanging off the edge of the bed. He rose to his feet and dropped his jeans and boxers to the floor with his cock hanging in my face. I open my mouth to silently ask for the taste that my mouth has been watering for all night. He lifts his cock and gently places the head on my tongue, its even bigger in my mouth than it looked or felt in my hands. I taste the hint of sweat and feel it stiffen in my mouth as I start to take the ten inch shaft into my throat. I feel the large thick veins against my lips and start to run my tongue along them. He takes his hand and places it on the back my head and begins to press it down onto his rock hard dick, pummeling the back of my throat with the head of his massive cock. My eyes start to water, but I open them and look up at him, while I cup his balls with my right hand and start to massage them and his taint. As he pulls his cock from my mouth, I feel it "pop" from my lips. He slaps me with his hard cock. "You fucking slut! You want me to fuck you? You should earn it!" So I take him back into my mouth and gag myself on his long hard dick! I feel it start to twitch, but before I can unleash his jisim he pulls out again and grabs my shoulders to turn me around, exposing my boi-pussy again. I can hear him building up a mouthful of spit just before I feel it smack down on my hole. He grabs my ass with one hand, and he forces himself into my pussy! It feels like a tear at first but as he is thrusting his Red Bull can thick member in and out, pulling the head out with each thrust and reinserting it with more force each time. Following about 30-40 thrusts, his cock starts to pulse in my hole and he pulls it out to keep from exploding inside me. After pulling it out of my ass, he looks down and momentarily admires his work seeing my previously tight puckered hole spread wide open to the point that you can see my insides along with the small traces of blood from tearing me open. It's only seconds before I spin around and force his thick black rod into my mouth again. Only seconds later, it explodes in my mouth filling my tongue and throat with warm spunk built up from a night of teasing! I open my mouth to let him have a look at the gift I have been given, then quickly swallow it. He pulls me close and holds me on the bed in a warm embrace.

A few moments later he had to pee and said he wanted me to help. He instructed that I follow him to the bathroom, and I did. As I sauntered into the bathroom, he stood over the toilet and pushed my shoulders to the ground and told me to put his cock in my mouth. Just as my lips touched the tip he said "this is going to be magical." He released a steady stream of bitter liquid in my mouth. As he filled my mouth I could taste it on my tongue and began to drool his piss over my lips. As he finished and shook his member in my face, splattering a few droplets on my chin, nose and cheeks he told me to swallow and I did with eager joy, if only to please him. Once I licked the urine from my lips and wiped it from my neck and chest we returned to bed where he wrapped his arms around me and whispered in my ear "you're my good little piss and cum slut. That's how I like it. You should stay like this forever." I rolled over to face him and replied "If only I could."

After this short conversation I drifted off to sleep wrapped in his arms. At some point in the night he left, and I do not know when, but I awoke around 7am. My usual time to get up and he was no where in sight. I realized by the weight on my chest and shoulders. I never removed my breast forms the night before and felt a fullness in my bladder. I got up and sauntered to the bathroom, where I instinctually sat to pee, because when cross dressed I behave as a woman would, to the best of my abilities. I slowly start to push on my bladder to release myself and hear it trickle into the water below, while I complete this process, I start to clear my head and think about what happened the night before. In udder shock that I drank his piss, I reach for my right breast form and tug on it to remove the glue, but it hurts as I squeeze and its not separating from my chest. At this moment I look down to investigate and realize that somehow my forms are now my exact skin tone and even look as if they are real breasts. I slip my hand between my legs to shake my penis after peeing and I am unable to find it. Now more perplexed and scared then ever, I quickly stand up from the seat and dash to the full length mirror in the sitting area of the hotel room.

As I stand in front of the mirror I notice that my breast forms are now breasts! My penis is missing and in its place is a tight hairless mound with a slit down the middle of it...resembling a vagina. Where I wore hip and butt pads are now real full hips and a juicy apple shaped ass. My stomach was thinner and now that I noticed it, I was shorter and my shoulders not as broad as well. I ran my fingers through the hair that looked identical to my wig, and it was real hair. I tugged on it. It hurt, a lot. My clip-on earrings were now pierced and had 2 more holes per ear.

I dropped to my knees and cried. Some tears of joy because this was always my dream, to just wake up a woman. Some of the tears were tears of sorrow, because in this form I could never see my wife or more importantly my son EVER again. I curled up in a ball and cried my self back to sleep.

By the time I woke up, I had dreamed of being fucked in my pussy and of taking Jacob's huge black cock between my real tits and into my mouth. I picked up my cell phone and called him immediately after waking up to realize it wasn't all a dream. I was a woman! I WAS JAMIE MADDOX! The phone rang one time and then was answered by an automated message stating "The number you have reached has been disconnected and is no longer in service." Now angry, I grab a pair of my jeans, a tank-top and pull my hair back. It's at this time I realize my masculine tattoos are gone as well but replaced with a rose tattoo on my hip and a tramp stamp on my lower back.

I step into the bathroom and apply my eye shadow, eyeliner, blush, lip-gloss, my cute J-heart necklace, my clip on diamond studs because although my ears are pierced, I don't have anything but clip-ons and then storm out of my hotel room with my purse in one hand and a hoodie in other. As I pass the front desk, the clerk calls my name.

"Miss Maddox, you have a package that was left for you by a gentleman this morning."

"What did he look like?" I ask. Now realizing that my voice is also changed to a much more feminine sound than anything I could produce yesterday.

The attendant replied "He was tall, dark skinned black gentleman. He said his name was Jacob, and that you would need this before you went out for the day."

As she said these words she held her hands outreached with a medium sized box, about the size of a messenger bag purse. I thanked her, turned it on its side and placed it in my Coach bag. From there, I walked out to my car, sat down and started it in the cold weather. Sitting in the driver's seat I stare at the box that Jacob left me, and wonder what it contains. I lean over pull the package from my purse and cut the tape with a pen. Inside I find a pair of men's boxers, a thong, two dildos and a hand written note. The note said:

"Dear Jamie, last night was amazing, I only wish I could have seen and fucked you in the form you're in now but I had to leave to make the transformation occur. You need to figure out if you wish to stay like this forever or go back to your form as a man. Just know this, if you stay this way all of your existence as a man will vanish. You have become the woman that you see before you through the Voodoo of the Congo. When I urinated in your mouth last night, it gave you the magical elixir needed for this change. The magic is very powerful and will alter the minds of all those you know and love to either forget you or only know you in this form. You will have 48 hours from the moment you read this letter until the change is permanent. Even my magic can't change you back again after that time. If at anytime in the next 48 hours you wish to change back into a man, just put the boxer shorts on and you will soon fall asleep. If you wish to make the change permanent before the 48 hours, you only have to wear the thong and follow the same procedure. The dildos are here so you can play and experiment. If you engage in sexual intercourse be sure to use protection for you are currently ovulating and can get pregnant. Doing so will take away any choice you currently have instantly. If you decide to stay as a woman, you can see me again once you decide, otherwise, this is good bye. You have 48 hours from this moment, so look at the clock and begin to make your choice."

I sat back and pressed my head against the headrest. I thought long and hard about this. Knowing that I could change back, I was no longer angry or upset but would need to think about how to proceed.

I packed up the boxers, thong, letter and dildos in my purse and headed back up to my room.

Once I returned to my room, I found it to be time to explore my new body and see what this was all about.

I laid back in the hotel bed and still dressed and ran my much smaller and daintier left hand into my pants and over my panties. I started to rub myself with just a small amount of pressure, feeling the puffy mound of my virgin pussy open up and pulse for more. Still through my cotton panties I spread my lips and pressed just slightly into the hole that opened, it felt amazing! I pulled the soft cotton to the side and slipped a finger inside myself. I could feel my vagina opening and stretching from just one finger, I slipped in two then three fingers. My breathing hastened. My back arched off the bed. My right hand ran up my shirt and under my bra to find my hardened nipple. I twisted and pulled at it until I felt a rush of power come over me. It caused me to hold my breath as the rush of my first orgasm ran through me. Within seconds I was too sensitive to even pull my own hand out without shuttering.

After a few moments of recovery I felt the urge to pee, so I got to my feet and rushed my way to the toilet. It is an odd feeling to have to pull some paper and dab myself dry. I head into the bedroom again. Considering I have 48 hours to make my decision, I will enjoy the time I have and see what it is like as a real woman without feeling like I am being stared at for being a freak, no fear of rejection or of being found out. I look through my clothes that I brought with me and decide I will wear my jeans, my Uggs and my purple V-neck sweater. I have boobs, why not show them off. I grab my purse and head out the door.

I get in the car with no idea where I am even going, I have to adjust the seat and mirrors for my new height, and this kind of pleases me. I start off driving around a strange town that I haven't been to before by starting up the GPS and looking for a mall. If I am going to have this body and have this opportunity I am going to enjoy, and will look amazing!

I pull into the parking lot at the mall, park and head inside. As I walk through the door of Sears, I see a tall and very muscular black man, in his early forties, walking out the door. He looks me in the eye, nods his head and follows my ass as it sways into the store. I smile wryly to show him I noticed and we continue on our separate ways. I find myself browsing the shoe section first but think I should find an outfit before I pick out shoes.

The clothes I am wearing currently are sized to my male cross dresser body at a size 10 and hang off of me, so I don't even know what size I would consider myself to be. I look around the women's section of Sears and find nothing that strikes my interest. I venture into the mall to find the perfect outfit, or outfits.

A few hours and about $1,000 later I'm walking to the car with bag after bag draped over my arms and notice the black man from earlier standing at my car. First puzzled by how he knew my car, and then by how long he was standing there waiting for me. I slowly approached, I tried to ignore him, but he wouldn't be ignored. He stepped between the car and I and told me that he had been waiting for me to finish shopping since he saw me get out of the car earlier. Starting to get scared, I begin to back away so I can go back inside, he steps forward and places his large hand on my upper arm.

"Don't be afraid, I won't hurt you. Unless you want me to. My name is Mike."

It's at this moment I truly realize how much smaller I am now, compared to when I went to bed last night. He towers over me, must be at least six and a half feet tall, the top of my head is just below his chest. I can't help but to look up at him and think about how big his cock is. I start to get a twisted feeling in my stomach as he starts to rub his hand on my arm as he reassures me that he isn't going to hurt me.

"I swear, I won't hurt you. I just couldn't get your body out of my mind and I would love to take you out to dinner and maybe a movie or something fun?"

I try to calmly slip away from his grip and he tightens it around my arm, as he does this I feel a tightening in my crotch, then as I step back I can feel my vagina muscles release and then there is an slow moistening feeling, almost like I've just slowly urinated myself. I think I just got wet for the first time. I look up into his eyes and ask him for his number, and tell him I will think about it.