11 comments/ 21616 views/ 21 favorites A Decision to Make By: butterflyjamie84 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. A Decision to Make He looks at me, and with sadness in his eyes he takes my phone from my hand and enters his number into the keypad. "Well I hope to hear from you soon. I promise you won't regret it." At the end of this statement, he winks at me and looks me up and down one more time. As he walks away I open the trunk and finally throw all my bags in. I can't wait to get back to the hotel, lay it all out and admire my take for the day, but I can't seem to stop thinking about how big his cock must be. I arrive back at the hotel, strut through the lobby with bags on my arms and the desk attendant gets my attention and waves me over to the desk. "Miss Maddox, there is a gentleman at our restaurant bar who asked me to send you in when you arrived again." Puzzled, I ask what he looked like. "Ummm I would say just under six feet tall, average weight, white, short grey hair, in his late forties early fifties, pretty good looking actually." I reply "Ok, well I am going to go upstairs and drop my stuff, then I will meet up with him." I walk into my room, drop my bags then check my hair and make-up before heading back down to the bar to see who my mystery guest is. Walking into the bar, I start to feel a tingle in my chest, almost as if my nipples are being played with, and then the tightness in my crotch returns again but there is no immediate release of pressure. I find it difficult to walk as the muscles get tighter with each step. There are only two people in the bar, a woman sitting alone with a glass of wine and the gentleman, as described, sitting at the bar. As I approach, he turns in his seat and sees me walking up. He look familiar, but I can't pin point why. "I heard you were looking for me?" "Yes, Miss Maddox, Jacob sent me to see how you were doing, and to see if you liked your situation. I won't lie, I have no idea what that means, but he said he was unable to come himself, but wanted me to check in on you." "I am fine, and tell Jacob, to kiss my ass! Having to make this choice is the hardest thing I will ever have to do and it is his fault!" I walk out of the bar, and head back up to my room. While I leave and as I enter the elevator, I feel all the pressure in between my legs release, it's moist again, but not like when I was around Mike in the parking lot at the mall. I unlock my room and go back inside, my panties seem to be stuck to me from all my wetness today, so I kick my Uggs off unbutton my jeans and head for the bathroom. I catch a glimpse of myself in the mirror and still have a feeling of utter shock that I am a real full functioning woman! Simultaneously I pull my jeans and panties down while I squat to sit on the toilet. I push a little and release a steady stream of pee and as I do this I inspect my underwear and notice that it's almost crusty but sticky, this must be from the dried juices of my pussy. I wipe myself clean and remove my pants and panties as I stand up. Now bottomless I walk through the room to all the bags that I dropped on the floor earlier. I lift them all to the bed and empty them one by one. First the new jeans and a few t-shirts that I picked up from Abercrombie, then the blue and white trimmed long sleeve, pleated, knee high dress with a plunge neckline I got from forever21 with the thigh high stockings and cute white strap, open-toe platform heels. I picked up a few bras and pairs of underwear from Victoria's Secret. Bikini cuts, boy shorts and thongs. In the bag from Aeropostle I have two skirts and various tops to go with them. I grab my bag from DSW and remove my three new pairs of shoes, a pair of knee high boots, a pair of peep-toe stiletto heels and pair of cute Tom's in pink and purple. From Ann Taylor bag I pull out the full length evening dress with the slit that runs up to my mid-thigh spaghetti straps and a built in bra support so I can wear it more freely. I used to be a size 10 in both clothes and shoes, but now I am a size 6/7 in my clothes and a 7.5 in shoes. As I reach for my phone to check my messages, I feel the dildo from Jacob and I am reminded that it is massive! It's about nine inches long and must be an inch and a half in diameter. It has a suction cup and balls at the base and a small button to turn on the vibrate feature. I feel the shaft in my hands and instantly am reminded of that twinge in my gut then an instant ache from my pussy, like it is begging to be fucked. I feel it quickly clench then release over and over again, then find myself with a hand on this massive dong and my other hand between my legs feeling the instantly wet lips between them. My vagina has a sensation like it is opening wider to receive this cock so I sit back on the couch and open my legs and attempt to slide it inside myself. Even with how wet I have become, it doesn't slide in easily because of the material and its gigantic size. I take the dong to my mouth and taste my pussy for the first time on its tip, it's sweet but bitter all the same, with a distinct but amazing aroma. I slide the head in my mouth followed by 3 or 4 inches of the shaft before it is pressed against the back of my throat. I open my throat to see if I can accept more but end up choking myself. Now covered in my saliva I take the dong and return it to my now throbbing cunt, it slides in easier but still causes great discomfort as it stretches me open. With about two inches inside of me, I feel a tear and am now in excruciating pain, but continue to push forward and gape my mound until I have the entire toy inside of me. I pull it out to examine it for a moment and notice trace of blood and some kind of tissue, I think I just broke my hymen and wow did it hurt! I wipe the rubber cock off and shove it back in my now wet and lightly bloodied vagina. Working it in and out faster and faster I hit the vibrator button and this kicks me into a whole new gear. With my legs in the air and my hand thrusting this toy inside me I start to feel myself tighten up then my breath shortens and I start to shake. When all of a sudden the door to my room flies open, and standing in the doorway is the man from the bar. He looks me over on the couch, shuts the door and walks to me. I am frozen at this moment, my orgasm is gone, and I am still filled with a rubber dick between my legs and my feet in the air. "So it looks like you were having a good time Jamie. Maybe I can join you? I could use a good time right now too!" Without hesitation I pull the dong from my twat and drop to my knees in front of him, unbutton his pants and remove his semi-hard penis from his pants. I place it in my mouth and feel it grow to about five and a half inches inside my mouth. This will pale in comparison to the toy I just had, but it will also provide me with a little less work to do. "That's it Jamie, suck that fucking cock! You dirty little fucking whore! You were just aching for a deep dicking! I am going to fuck you like you have never been screwed before!" Little did he know, but he was right, I had never been fucked in my pussy before. I took his now hard cock in my mouth and licked his balls while his shaft glided over my tongue. After a few moments of sucking his dick, my pussy ached again, longing for the orgasm that it missed out on when he bust in the door. Remaining on my knees, I turned around and presented myself to him, spread open my ass cheeks and pussy, he got low behind me and pressed his cock against my asshole, then slid the head down to the opening of my hairless muff and slipped himself inside me. "God you really are a little fucking slut! I am going to fill you with my fucking jizz and watch it all leak out of you when I'm done!" I turned my head to look at him and said "NO! You can't cum inside me! I am not on birth control! If you want me to I will swallow your load, but you can't come inside me!" "Whatever slut! I do what I want! Watch this bitch!" Just as he said the word bitch, he pulled his cock from my pussy and tried to shove it in my ass! I screamed in pain, as he got just the tip, and pulled away from him. He grabbed me by the hips and pulled me back to him. "Fucking get back here you little fuck doll! If I can't bust in your pussy! I am going to spray my load in your tight little ass!" With that statement he spit on my anus and shoved his cock back inside me. This time getting the whole head and most of the shaft in one thrust! He pounded in and out of my ass until I felt his penis start to pulse and his strides start to shorten when he abruptly pulls himself from my ass and re-inserts it into my pussy right before exploding all over the inside of my tight wet pussy. "I always get what I want! Now turn around and clean my cock off!" At this point I refuse, stand up and try to push out his cum! Hoping I don't get pregnant and lose my choice this early on. "Get the fuck out of here!" I yell at him. He promptly pulls up his pants, buckles his belt and walks out the door. As I lock it behind him, the tears start to roll down my face. Afraid that I will never get to see my family again, I call it quits and grab the boxers, go to put them on, but something stops me. I head into the bathroom, clean myself out with the douche that I had to clean my anus before the change, and try to get as much of his jizz out of me as I can. Watching myself in the mirror I realize that this could be it. He even ruined me getting to cum! After cleaning up, I go back to the living room, pull my shirt off and unhook my bra, letting it fall to the floor. Now standing naked in front of the full length mirror, I admire my body from head to toe. My dainty little feet, my long soft hairless legs, my perfectly shaped mound of a pussy, flat stomach and my big perky C-cup breasts. My dark brunette hair drapes down over my shoulders and covers the top of my tits, my little jawline, with full pouty lips, and bright green eyes. I am stunning! I turn to the side and have a perfectly shaped ass and an amazing hourglass 34-26-34 body. I should have a little more fun with this, it's not like it isn't already too late to avoid pregnancy, if I want to change back anyway. I grab my phone, and take a selfie, of just my naked body, and send it to Mike! He replies instantly with just a smiley face. "Where do you want to get dinner? Is tonight OK?" He replies "Tonight is great! How about Sullivan's in town." "I don't know where that is but I am sure I can find it! 7? Ok?" "Perfect! I can pick you up if you want." "No that's OK, I can meet you there! " I opted to meet him there so I don't get into a situation like I just finished being in. I look at the clock and it is now 2:30pm so I decide it's time to finish what I had started earlier, then maybe a nap before getting ready to go out. I grab the dildo and stuff it in my mouth as I walk across the room! I can taste myself dried on it from earlier and this turns me on. I feel the warmth in my crotch as I suck on this toy cock once again, even though he was small I enjoyed taking the cock from behind so this time, I use the suction cup base and stick it to the wall just above the height of my pussy and back up onto it from my knees. It sides in with relative ease and much less pain than the last time. I start to rock back and forth slipping it in and out of my pussy, I reach down and start to use my finger too, this causes a rush of fluid to my crotch and now I am gliding up and down on this cock with ease. Soon I feel my vagina tighten up around it, then an immense amount of pressure build up just above the dildo, as I keep fingering myself and riding back on the dong, my anus tightens then releases almost instantly! A geyser starts to flow from inside me, my arms begin to shake and can no longer hold me up, my knees buckle beneath me and I am lying face down on the floor in a puddle of some sort, trembling from excitement. I lay there and shiver from the pressure of what just happened, and realize that not only am I a woman, not only am I hot, but I am a squirter too! Curious, I reach down and dip my finger in the puddle of my ejaculate, then bring it to my mouth. It's very bitter, not sweet like what moistens my pussy, but I strangely like it. I rise to my feet, covered in my own cum, walk to the shower, turn it on warm and climb in. As the water runs down me, I start to scrub up with my loofa and pay close attention to my crotch, making sure it is clean. After a few moments in the shower the sound of the water causes me to pee, I feel the warmth dripping down my leg and to my feet and the shower floor. I rinse off, and step from the shower, wrap a towel around my chest and use another one to dry my hair. I walk to the bed and lay down for just a moment. Just as I lay back I feel the weight of my breasts press against me, and once again am reminded that this is all real. I close my eyes, and drift off to sleep. I wake up, now unwrapped from my towel, still naked and realize it is 5:15pm. I have to get ready. I quickly look up Sullivan's on google to see the type of place it is, and how long it will take me to get there. It seems to be along the lines of a Fridays, and is only about 10 minutes away. I first grab my Victoria's Secret bag, select the navy blue demi-bra and the matching lace thong from the bag. I then grab my forever21 dress, thigh highs and head to the bathroom. After about an hour of doing my hair and makeup, I slip into the dress, then pull the thigh highs up. I put my black knee high boots on and walk out the door with my clutch purse in hand. Dinner was uneventful, but we clicked. He was rather focused on after dinner, but so was I. I spent most of the night sitting in wet panties that felt as if I had peed in them, but still couldn't stop thinking about how big his cock was. As we left the restaurant, he offered to go back to his place for drinks, slightly nervous, I accepted his offer, knowing where this was going to lead me. I told him I would follow him, rather than ride together. We sat on his couch with a blue drink that he made, saying I would love it. He was right, it was sweet, and strong! Just how I like both my drinks and my men! After two drinks and a lot of talking about life in general, politics and even a few diversions into sex, I started to feel pretty comfortable. He leaned in for a kiss, and I felt the power of his tongue pressed against mine. As our lips met, I got a very distinct and now familiar feeling in my stomach, then my nipples tingled and eventually that tightening in my pussy. This time though, instead of releasing, the tightening got more and more intense. His hands explored my body, this was really the first time I was having someone grope me and touch me with my pleasure in mind. His strong hands on my abdomen twisted me in knots. It made my skin tingle as he ran his fingers up my thighs, and slowly pulled my dress over my waist, and up my stomach. He gently pressed on the mound under the wet fabric of my thong and rubbed my pussy, causing it to contract and almost pulse from the excitement. He then began kissing the corner of my mouth, then my cheek, my jaw-line and down my neck, making his way to my chest. My body was sensing things I never knew to be possible, my toes curled as his fingers began to explore the inside of my soaking wet pussy and the hair on my arms stood up as he kissed my neck and chest. Although I wanted nothing to do with making him stop, I leaned away and pulled the dress over my head and off. Now sitting there completely venerable in just my bra and panties, his left hand quickly found its way back to my cunt and his mouth to my breasts. With his free hand he ran his fingers up my back and unhooked my bra. Instantly I felt the weight of my boobs fall on my chest and the fabric that covered my nipples now fell, leaving them exposed. He took my left nipple into his mouth, I felt the warmth of his tongue as it brushed back and forth over it while it became erect. The suction from his lips tugging on my skin and causing almost electric like currents to run through my veins. His long fingers delve deeply into my now dripping honeypot and my body tenses up and clenches down around him. In a moment of clarity from this sexual haze I am in, I start to rub his crotch through his pants, and feel his already stiffening cock get harder under my fingers. I wander up to undo his belt and pants button, then lower the zipper. His shaft presses firmly against the inside of his pants and he lifts his ass from the couch to allow me to pull the waistband and his boxer-briefs down to his knees. It's not until nearly there that his staff is fully freed from the prison of his pants. The massive purple and brown head stands erect and easily eleven inches, maybe more, from his abdomen. I gasp out loud and lose my breath for a moment as I see the largest penis I have ever seen. My hand reaches for it and I can only barely touch my thumb and forefinger together around it. While I am still in shock, he looks at me, and asks if I like it. I am speechless, but to show my absolute appreciation for this massive specimen of manhood I lean over and begin caress the tip with my tongue. I can barely open my mouth wide enough to accept his girth, let alone try and take the length as well. I begin to slide my mouth over his shaft and can handle maybe two or three inches before he is scraping my teeth. Not wanting to cause him pain, I pull back and retreat to a plan of licking his shaft up and down and enjoying his equally massive balls. I glide my mouth over the shaft from base to tip over and over again, causing my mouth to salivate and drool all over his massive tool. While I lick and suck his cock his hands continue to wonder my body, slipping in and out of my pussy, pinching my nipples and massaging my tits, occasionally I feel a tug on my hair, as I think he is feeling me out for what I will and won't allow. I finally lay back on the couch and place my hand on his head pushing him down in the direction of my legs. He his receptive and begins his journey to my first time being eaten out. I lay back, close my eyes and allow him to work. I first feel the warmth of his breath on my thighs and my hairless mound, then I feel the pressure of his lips as they press against my lips and his tongue as it separates them and dives deep into my opening. His tongue lapping up what seems like a never ending flow of juices and then instantly a spark as his tongue strikes what I must assume is my clit. Having never been pleasured like this before, all these new feelings are taking over my body, his warm breath on my wetness, and his tongue feverishly flicking my pussy, when all of a sudden I feel a finger slide inside me, pressing on the upper wall of my vagina. My whole body reacts, thrusting my hips into his face, driving his finger deeper into me and pressing his tongue harder against me. My feet drive into the couch and push my whole body up. With this he stands above me, grabs me by the hips and places the throbbing head of his gigantic cock against the opening of my tight wet pussy. I brace myself for the pain I am sure to feel as the tip presses into me, I feel it stretch me open wider and wider as the head slowly presses through, then a pop of relief as the crown enters me. His shaft feels never ending as each thick vein presses on the walls of my sticky little cunny. I start to shudder as I feel him press against what I would assume is the back of my vagina. It starts to hurt, and I push my hands against his chest to tell him to stop. He starts pulling himself from me, and slowly sliding it back in over and over and faster with each stroke. Occasionally striking too deep but continuing to thrust and stretch me out. My legs start to shake and my pussy feels like it is clamping down on his massive rod, just as I start to push myself into him and drive his cock deeper into me, I feel a rush of pressure just then all of a sudden a surge of pressure releases, causing my whole body to shake and my mind to blank out. I come too moments later screaming his name "Mike! Mike! Mike! Fuck me Mike! Fuck me harder! I am coming! Don't stop! Oh fuck! Fuck! Fuck! Don't stop!" As the pressure subsides, I breathe deeply and try to catch my breath as Mike continues to pound away at my fuck hole but before I could get my breathe another wave crashes over me and I am thrown into a second orgasm! Now just screeching in joy, I pull myself off of him and turn around. A Decision to Make I bend over and present my stretched pussy to him, and spread my ass cheeks so he can get a clear few of my pussy from behind as it swallows most of his cock. He drives his rod into my cunt and forces my face into the couch, he then grabs my hair and pulls my head back and forces me back onto his entire rock hard staff. I flinch from the thrust of pain, but then rock back and forth on my knees to service the whole thing! I turn my head back to look into his eyes as he pounds me harder and harder from behind. Just as I feel him start to throb, I slip myself off of him and turn around. My face, perfectly lined up with his cock, dripping with my cum, I smell myself on him as I take it to my lips. With just a few flicks of the tongue, his head pulses, his balls tighten up in my hand and he blows his jizz all over my tongue and face! His load is proportionate to the size of his cock, it's massive. I swallow what landed on my tongue, and use my finger to wipe my face clean. He looks down at me smiles as he says "That's a good little slut! You take my fucking cum! Now suck the rest out!" This change in demeanor surprises but enthralls me. As he speaks those words in his deep voice, and I feel his cock on my lips, my rosebud starts to ache again. I take his cock in my mouth and even flaccid, I can't fit it all in my mouth. While I continue to suck him off, I reach down and begin to finger myself. Running my fingers between my lips and splitting them, before sliding my fingers inside and using my thumb to toy my clit. I love the taste of my pussy on his cock, and I love the taste of his cum as it still slowly continues to seep from the tip. He notices that I am still toying myself, grabs my hair and uses it to direct me to stand up. While I stand, he places his mouth on mine and replaces my fingers with his. He guides me back to the couch and gently pushes me down so I return to the seat I was in as he ate me out before. He drops to his knees and begins to lap up the juices on my cunt, slides two then three fingers inside my now spread open pussy. He curls them upward and jabs at my clit with his tongue. I very quickly rise to the point of almost climaxing, when he pulls back and stops it before I get the chance. Just when my body settles down he returns to the exact spot he was in and pushes me to almost coming again, then backs off. I look at him with disgust, he knows why and responds with: "I will make you beg me for this orgasm! You will beg me before I let you cum!" I look him in the eye just as he rises me to climax for the third time, and I give him what he wants. I beg, I barter and I plead with him. "Mike, baby, please let me cum! Please baby, give me what I need! I will do anything! I will let you do anything too me! I swear! If you want to try and fuck me in the ass, you can! If you want to piss or shit on me? You can! You want me to walk back into my hotel with your cum on my face then to announce that I am your dirty little whore to the public? I will! Please Mike, baby, just let me cum!" With this begging he gets a grin on his face, but finally lets me finish. As he pushes me over the edge, my pussy clamps down on his fingers, my stomach tightens and releases and all of a sudden I am squirting all over his hand. His grin at this point goes from ear to ear and he leans over and kisses me, then shoves his fingers in my mouth so I can clean them for him. "You shouldn't have made those promises. Now you owe me. And I will make it good. Not tonight, but you will be my little cum slut. You will take my piss, you will be covered in my sperm and you will traipse back into your hotel covered in all of it, with my name written on your forehead in sharpie marker. You will be my little cum pig and you will like it. WHORE!" With that statement he slaps me, then leans in and kisses me. I don't regret saying any of it to him, except maybe the shit part of the begging. I will happily be his little whore, from now until forever, as long as the orgasms keep coming like that. We cuddle on the couch for a bit, naked and sweaty, until I decide I am sober enough to go back to my bed in the hotel, and relax for the remainder of the night. I get myself dressed, kiss him goodnight, and head out for my hotel. When I get back to my hotel I shower, and slip into my cotton brief panties a sports bra and a t-shirt, just before climbing into bed. I wake up in the morning, after having numerous strange dreams, and many about my wife and son. I miss them dreadfully. I want to call them, but I can't with this voice. I lay in bed and I cry. I do not know what to do. I love being a woman, I love feeling like I can finally be who I want to be, but I also cannot fathom living my life without the love of my life and my amazing little boy. Three hours of tears later, I get myself together, and put some clothes on to just head out and enjoy the day. Today is either the last day I will ever have as a woman, or the second day of my new life. I grab my purple and orange boy-shorts, a black tank-top with a shelf bra and throw on a hoodie and boyfriend jeans with my Tom's. I am not in the mood to do my make-up, so I just put on some mascara, lip gloss and eyeliner, pull my hair back and walk out the door. I decide I need to go get myself something to eat. So I find a local restaurant, a pizzeria, grab two slices and a coke, then continue about my day. I decide I am going to head out to the mall, and find one more outfit, it is Friday, and my last night as a woman, will be spent dancing the night away in a club, with a lot of alcohol and a lot of attention from men. After walking around to a few stores I, find myself at Gap trying on a body conforming little black dress. It has halter shoulder straps and two inch sleeves just below the shoulder line and an off the shoulder neckline that runs right across my chest. It will have me pulling it up all night, but will make my ass and my tits look great! I have shoes that will go with it, but decide to go to Aldo and buy new ones anyway. I walk in and the first pair of shoes I see are the ones I fall in love with. A pair of black leather, five inch, peep-toe heels with diamond studs along the ankle and toe straps. I ask for them in a seven and a half. I am attempting to pay, the 19 year old, pimple faced, associate looks at me from toe to head and says "If you show me your tits, I will give you twenty percent off!" At first I am disgusted, but consider the fun that can be had here. I reply "well how much off if I just blow you?" "You can just have them if you let me fuck you." I consider this offer, I have the money to pay for them, but why not add another cock to my two day total? "OK. Where and when?" "Really? Like for serious? You are going to fuck me to get a pair of shoes?" "Yeah, why not? Like I said where and when?" "I get my break in five minutes, we can just go in the back room." "Ok, can I wait back there for you? I'll get myself good and ready." "Sure, just lock the door. I have the key, so I can get in." I head to the back room, lock the door behind me, and find a spot in the corner, on a rolling desk chair. Pull my shoes, sweatshirt and jeans off, but leave my boy-shorts and tank-top on. For his pleasure I pull my boobs from the tank-top and let them freely hang over the shirt. Now sitting with one leg up on the chair and one holding my balance on the floor, I move the boy-shorts to the side and start to play with myself. Slowly working one finger between my lips, then firmly rubbing my clit, I spread myself open and slide two fingers in. I feel the pressure building as I get myself wet, then begin to play with my breasts. Just after I get myself nice and wet, the door opens slightly and his lanky body slides in the door. He is greeted by the sight of my 34C breasts and three fingers buried inside me. I instantly see his erection form in his pants. Nothing special, but good enough to get the job done. He walks over and goes to eat me out, I tell him "No, the deal was you get to fuck me, then the shoes are free. No foreplay. We don't have time for that." At this he unbuttons and unzips his pants, pulls himself out, and sticks it in my face. I put the tip in my mouth and swallow the five and a half inches he is giving me, get it lubed up with my spit and lick it to a rock hard condition, then take it in my hand and guide it to my pussy. As I press his cock against my wet lips, he pushes himself into me. Thrusting in and out, he pounds away at my pussy unrelentingly until I feel him start to pulse, as I feel his cock pound like a heartbeat inside my vagina, I look him in the face and tell him "Cum on my face or in my mouth! Don't cum in my pussy!" He pulls his cock out of me, and begins to jerk it until I get my lips wrapped around his still rock hard member! When I feel it pulse again, he pulls it out of my mouth and sprays a ton of cum all over my face. Up my nose, in my eye, and all over my cheeks, forehead and even dripped down to my tits. He put his cock in his pants and then said "Since I couldn't fill your pussy, you don't get a towel. I want you to walk out of the store, with my jizz all over your face." I look him in the eye, "you're crazy. I will just use my sweatshirt." He then winds up and slaps me right across my tit. "NO! You will leave my spunk on your fucking face you gutter whore! Seriously. You are a fucking whore. You fucked me for a pair of shoes. If you think I won't call the cops and say you stole them, you are sorely mistaken." He shakes his head and slaps my boobs from the other side. "Also if you think I won't just slap the shit out of you, you're crazy! Just put your fucking tits away, put your pants on and fucking leave!" I actually feel abused. I open up my shirt and put my boobs back in. I straighten out my underwear, and pull my pants up before putting my shoes back on. I reach for my hoodie, and move to put it on, as he pulls back and slaps me across my face, then wipes the seaman that he just got on his hand all over my black tank-top. "You think you can wipe it off on your sweatshirt while you put it on didn't you?" "Yeah, so fucking what? Jesus fucking Christ! Just let me leave!" "You can leave, but you will do so the way I tell you to! Now get the fuck out slut!" On that note, I grab my hoodie, purse, bag from Gap, my new shoes and walk out the door. Cum faced, now stained shirt, sore boobs and all. I walk out of the store, and into the main concourse of the mall covered in cum. After getting over the rude way he treated me, I start to get turned on by the fact that the whole world knows that I am a little cum slut. After walking a few stores down, I wipe my face clean and make a line for the car. I park my car around the back of the hotel, and get back to my room to quickly shower, then take a nap. I wake up from my nap, and it is already 4:00pm. I order some dinner, and relax to watch some TV. My Chinese food arrives around 4:30 and I answer the door in nothing but a pair of panties and a bra. The delivery driver is unable to speak as he hands me the food and this makes me laugh. I tip him generously and close the door behind me. After dinner, I lay in bed and watch some more TV. There isn't anything particularly interesting, but end up watching "The Other Woman" and just relaxing. I know this could be my last night with this body and I plan to enjoy it. When the movie ends, I pull out my laptop and pull up www.youporn.com, I search their videos, and find one that peaks my interest. "BBC Gang Bang White Slut." As I start the video, I slip my hand into my panties and begin to rub my clit through my now prickly haired mound, using my middle finger I apply pressure to the little cum button, and start to feel the wetness seeping onto my other fingers. I slip my index finger inside myself, and continue to watch as this tiny waist blonde on her knees, takes a massive cock in her mouth, just before two more dicks enter the shot and fill her hands. I close my eyes and picture myself in the scene. Each hand stroking a fuck stick while my mouth pleasures another. I open my eyes again to see two more very well endowed black men slide into the scene. As the scene continues with now five men fucking one woman I close my eyes again and loose myself in my own fantasy. The black cock in my mouth pulls out and maneuvers to slide inside my pussy, while two move into place at my face. Alternating between the two cocks, I suck them both with fervor and joy, with one in each hand and the first one now pumping in and out of my twat. After moments of sucking one cock, they all collaborate and lay me face down on on top of the man inside my pussy, and one of them stands between my legs, primes his cock just before pressing it into my tight unsuspecting asshole. Both men in opposite rhythm pumping in and out of both my holes, a third cock appears in my face, I place it in my mouth and am now as full as I have ever been. Three massive black cocks in filling my ass, pussy and mouth, while I jerk off two more. As I dream about being fucked in ways that only happen in movies, I start to feel my asshole pulsing, almost begging for attention. I reach to the nightstand and grab both dildos that Jacob left for me. I slide one in my pussy, then suck on the other before sliding it in my anus. Just as my body starts to tremble from all of the pleasure and the pain at once, they pull out of me and flip me over again. Now switching places. Still leaving all my holes filled, only now I face upwards. Simultaneously shoving a dildo in my pussy and my ass I start to feel a pushing in my lower abdomen, I clench both my holes around the toys and begin to press my clit again. After moments of fucking and sucking the man in my mouth pulls himself from my lips and blows his load all over my face and breasts. He is quickly replaced by another in my mouth. As this happens the cock in my pussy pulls out and shoots his load all over my stomach, and is also replaced. Now with a dick in my ass, in my pussy and in my mouth, the three men start to fuck in rhythm. Deep in my ass and mouth when shallow in my cunt and rimming my lips and anus when buried in my pussy. Suddenly all three pull out of their warm fuck caves and jerk their hot jizz all over my face, tits and stomach at once. As they climax in my dream, I start to cum. The rush and charge of being fucked in such a manner sends tingles and jolts of electric charges though my body. My toes curl, my fist clenches around a dildo and I bite down on my lip while releasing all the pressure from my abdomen. I feel the rush of my pussy squirting again. This time it feels endless and unrelenting. Just as the orgasm subsides I close my eyes, and drift off to sleep. I awaken around 8:00pm. I climb out of bed, refreshed, still wet and sticky from falling asleep in my myriad cum. I head to the shower, where I shave my armpits, and manage the prickly hair I found while masturbating earlier. I cover my mound in cream, and slowly but firmly drag the razor along the outer part my vagina, then carefully open it exposing my lips and shave the inside near the labia. I scrub myself clean, wash my hair and get out. Once dry, I begin to style my hair and do my make-up. When done, I grab my new dress, slip it on over my head, slide my arms through the shoulders and high sleeves, and let it fall to my thighs. I tuck my boobs into the support provided and slip on a black lace thong. I slide my feet into my new shoes, that I really earned and add my "J" necklace with various studs in my ear holes. I add the heart anklet and a few silver bangles to complete the ensemble. I look in the mirror and am fully impressed at the woman I see before me. I decide for my own safety, I should take a cab. The driver pulls up, I climb in and direct him to take me to The Metropolitan. Reviews, say it is the hottest spot on Friday nights, so that is where I want to be. As I arrive, I pay the cabbie and walk for the door of the club, I decide to try and just "get in" since I know I am hot, and usually the hottest women don't wait to get in the club. The bouncer sees me, opens the rope and lets me enter the club. Once inside I go right to the bar, drink two shots of tequila and order a margarita. Once my drink is done, I make my way to the dance floor. The alcohol is already hitting me, and my hips begin to move to the bass heavy music. A man walks up behind me, and begins to grind on my ass, and quickly another joins in front of me. Soon I am surrounded by four men all trying to press themselves against me. One offers to buy me a drink, I accept and follow him off the floor. I tell him I am drinking tequila, either shots or margaritas. He orders two shots, a margarita and a beer. We drink the shots, then converse for a bit. He introduces himself as Rocco, he's 24. He asks what my plans are after the club tonight and I tell him none exist yet. He grins and says "you can come back to my place if you want." "Oh yeah? What will happen at your place?" "I don't know, more drinks, maybe a little fun time?" "We'll see. I was hoping for a good time, but I am not sure I want to leave with just you." "What?" "I was hoping for more of a group thing tonight." "Oh ok, well my place is perfect if you find enough people to fill your group." "Thanks." We finish the drinks, and head back out to the dance floor. He and I seem to click, so I keep him close. As I start to feel more and more drunk, the room starts to get fuzzy. I dance with Rocco, when a sexy, twenty-something, redhead walks up and slides in his place. She was dressed in a ruffled grey crop top, with a maroon ruffled mini skirt and sexy kitten heels. She gets close to me and before I know what's going on, her lips are pressed against mine. I close my eyes and allow my tongue to explore her mouth while holding her lips in place. Her hand wanders to my lower back and pulls me close. I briefly open my eyes to see Rocco and three other guys grinning while they watch us make out. I later came to find out her name was Amber. The night continued on, making out and dancing with Amber, Rocco, Matt and Peter. The latter two joined us on the dance floor later in the night. Matt was 22, very tall, olive toned skin with brown hair and Peter was a 28 year old blonde, with thick tight muscles. As the lights began to rise in the club, Rocco reiterated his offer to come back to his place. The three others and I agreed. Amber and I took a cab that followed Rocco's car and the separate cab with Peter and Matt in it by ourselves, since there wasn't one that would comfortably fit four people. In the cab, we continued to kiss and began exploring each other's bodies. Her hands soft and small like mine found themselves pulling the neckline of my dress down and exposing one of my boobs. She suckled at my tit for what seemed like forever but not long enough. The intense tonguing she gave my nipple had it erect and hardened. I felt the warmth in my legs and longed for her to lick me from tit to twat, but knew that it would have to wait. I was unable, do to her clothing choice for the night, to return the nipple licking favor, but was able to run my hand up her skirt and press fingers to her muff over her panties. I slipped my hand under the fabric and realized that she left a small runway patch of hair on her pussy. I played with the patch of hair momentarily until sliding my fingers down to part the curtains of her sex garden. I slipped my finger inside her and used my thumb to rub her clit. While I fingered her, our mouths met and allowed our tongues to dance.