This is a print version of story Becoming Emily - Part I by taboo_daddy from xHamster.com

Becoming Emily - Part I

The premise for this story came from a discussion I had with a female friend. She had posed the question "What would you do if you woke up one morning and you were a girl?" The story may move a little slow for some but it will pick up.

I have been called a lot of things over the years. Pervert. Dog. Man-whore. All of these would be very accurate descriptions. I made it a goal in life to fuck as much as humanly possible and I’ve done rather well over the years. You might say that I take Wilt Chamberlain’s claim of sl**ping with 10,000 women as a personal challenge.

I’m rather picky about who I fuck and I certainly have a type. I prefer younger females myself. There is just something about the feel of a smooth, young, firm body hat simply cannot be faked with silicone, Botox or any other form of cosmetic surgery. Don’t get me wrong, I’ve never f***ed anyone to do anything but I certainly did everything within my power to make it easier for them to submit. This was my life, or at least it was.

I am getting older and despite keeping myself in good condition the years had started to catch up with me and when you’re almost pushing 40 there are days when you wake up feeling less than spectacular. I woke up that morning feeling surprisingly great. I gave a deep stretch and instinctively reached down to greet my usually stiff cock but instead of the rigid 9 inches I only feel a small patch of hair. Then a mound. Lips? A pussy? I threw the blanket from my body and stared in disbelief.

“What the fuck?!?!” I screamed in a voice that wasn‘t mine.

I bolted to the bathroom and stared at the young girl looking back at me in he mirror. Her actions matched mine. I touched my face, she touched hers. I stuck out my tongue, she did likewise. My mind flew into frenzy. There was no logic way that I can go to bed as a male and wake up female. This was just some weird twisted dream. A nightmare. I began to hyperventilate.

“Good morning Mr. Kane.” the words were thick with a Chinese accent. I spun around to find the source and there sitting in the corner of my bedroom was a rather old, rather small woman.

“Who the fuck are you and what the fuck is going on here? Did you d**g me? Is that it? Some sort of hallucinogenic?”

“Quiet!” she stared at me with a look of pure fury and something deep in my being told me it would be best to heed her words.

“My name is not important. What is important is that you have brought shame upon my f****y. One that cannot be righted.”

“Listen lady, I don’t know you. I have no idea what the fuck is going on but if you don’t….” my words trailed off when she flashed that furious glare at me again.

“You have taken something Mr. Kane. Something that did not belong to you.”

“You must have the wrong man. I’ve never stolen anything in my life.”
“Tell me Mr. Kane, do you remember a girl by the name of Mai?”

My mind went into search mode. Trying to recall. Trying to remember this one girl amongst a sea of others. It suddenly clicked in mind and I remembered a beautiful young Chinese girl that I had met well over a year ago. She was a freshman at a local college and was experiencing life away from her f****y for the first time. It took some serious convincing but eventually she gave in. I popped her cherry on the very bed I was now sitting on. My jaw dropped and I could only nod my head.

“You have stolen my great-granddaughter’s virtue and soiled my f****y in the process and that cannot go unpunished.”

“What have you done to me?”

“You might call it a curse. You have become the very object that you desire and you will remain that way until your first cycle. At that time I will return and judge whether or not you have learned your lesson. If I feel that you have changed your ways then I will relieve you of this curse, otherwise you will stay like this for the rest of your days.” she began to walk away and I was quick to follow.

“Wait, please! Let’s talk about this. Can’t we come to some sort of financial resolution? Just give me a number.” my rather healthy bank account has gotten me out of a lot of trouble in the past and I could only hope that it worked it’s magic again.

“I am not interested in your money Mr. Kane.” and with that she was out the door. I started to run after but realized that not only was a naked but I was also now a female. I tried to wrap my mind around what had just taken place but there really is no way to grasp the idea of a gender change like this. My head began to pound and I felt a sudden exhaustion. I crawled back into bed again hoping that when I woke up this would all be just some sick dream. I awoke 2 hours later with a clear head and the affirmation that this was in fact not a dream and that I had to piss so fucking bad.

I ran to the bathroom and stood in front of the bowl and let it go. As I felt a warm liquid running down my thighs and generally making a mess I realized that this was going to take some getting used to. After I cleaned up the floor and took a long, hot shower I stood in front of the bathroom mirror and admired my new form and curse or not that old lady did a hell of a job. I now stood about 5’ 2” with shoulder length dark red hair and emerald green eyes. My skin tone was neither too pale nor too tanned. My tits I estimated to be a C cup and my ass looked like an upside down heart. My belly was smooth and flat and as my hand roamed further down I felt an amazingly smooth, hairless mound. The shock of going to sl**p as a male and waking up as a female was still present but that didn’t stop me from enjoying the feel of my suddenly wet little pussy. Fuck I looked sexy, messaging one tit with my left hand as the right quickly rubbed circles against my clit. My first orgasm as a woman left me light headed and weak in the knees. As I recovered I sat on the edge of the bed unsure about what to do next. Maybe Sasha would know. She is into all that witchcraft mumbo-jumbo. Perhaps she could give some insight to all of this. I started to call but realized that my feminine voice probably wouldn’t do much to convince her that it was me so I fired off a text asking her to meet me at my house as soon as possible. She responded to let me know that she would be by later that evening.

Growing up as an orphan Sasha was the closest thing I ever had to a f****y. I referred to her as my older s****r but the truth was that we were both just fostered by the same f****y for almost 2 years. When she turned 18 we lost contact until we both turned up at the same college a couple years later. I knew from day 1 that she was a lesbian and gravitated towards “alternative religions” so maybe this would be right up her alley so to speak.

I figured I should get dressed but a survey of my closet revealed itself to be stocked with men’s clothes and none that would be even close to fitting my now much smaller frame. Then I remembered the trunk that I kept in the back of the closet. It was filled with things that past conquests had left behind along with a few things that I bought for them to wear for me. Most of the stuff was what you would wear if you were either getting fucked or looking to get fucked. There was a few short skirts, tight tops and even a sexy girl scout outfit. I found a matching bra and panty set that fit like it was made for me (34C bra. I was always a great judge of tit size.) and I found a pair of cotton shorts and t-shirt. I passed the rest of the day by watching TV and masturbating.

It was after 6PM when I heard Sasha let herself into the house. I was scared and nervous and I could only hope that she would be able to help. Her reaction when she first saw me was almost comical.

“Oh hey. I’m sorry I was looking for my b*****r. Oh you girls keep getting younger and younger huh?”

“Sash, it’s me. Eric.”

“Wow that is fucking lame. Listen little girl, I don’t have time for my b*****r’s jokes so could you please, for the love of all that is good, tell him to get his ass in here.”

I went into a length retelling of the morning’s events and about the Chinese woman and the curse. When I was finished she just sat there and stared blankly at me. My stomach was tied up in knots as I waited for her to say something and hoped that it was going to involve a way to undo what had been done.

“That’s a great story but seriously. I don’t have time for these fucking jokes.”

“Sasha I’m serious! It’s me!”

“Oh really? Prove it then. Tell me something that only the two of us would know.” my mind raced as I tried to think of something that she knew that I would never reveal to another soul.
“Cindy Reagan.” I almost screamed. Sasha’s face went ghost white.

“What about her?”

“When I was 15 you caught me with a pair of your panties. You made me wear them and took a Polaroid of it and showed it to the girl I was dating, Cindy Reagan.”

“And what happened after that?”

“She broke up with me and you fucked her the same day!”

“Hell yeah I did.”

“Sasha!”

“Ok, Ok. Calm down. Don’t get your panties in a bunch.”

“Seriously?”

“Oh. Sorry.” I knew from her tone that she wasn’t sorry at all.

“So do you think you can help me? I mean I know you’re into all that Witchcraft stuff.”

“Wicca! Not Witchcraft.”

“There’s a difference?”

“You know for someone that suddenly sprouted tits you’re being awful mouthy.”

“I’m sorry. I’m just a little freaked out.” I noticed for the first time that Sasha was looking at me in a different way. It was like she was fucking me with her eyes and when I heard a barely audible moan it was confirmed.

“That woman sure did do a good job.” her eyes danced around my tits straining the thin fabric of the t-shirt.

“Sasha! Can we focus here?”

“Well just settle down. I’ll get in touch with a friend of mine. He would know more about this than me. Only downside is that he is unreachable for another week or two. When did that lady say she would be back?”

“On the eve of my first cycle. What ever the hell that means.” Sasha looked at me like I was painted neon green and doing a river dance.

“Um, menstrual cycle maybe?”

“Oh yeah that would make sense.”

“Well I try to get in touch with my friend and do some research myself. Just be patient.”

After Sasha left I wasn’t feeling any better about my situation. sl**p seemed out of the question. I lay there in bed, acutely aware of my new body and in no time I was feeling myself up. These tits were amazing. Firm yet bouncy and my nipples were just the perfect size and not to mention extremely sensitive. I figured I may as well have a little fun with this and soon enough I was panting and moaning as I rubbed my swollen clit against the palm of my hand and then plunged a finger into myself for the first time. The first mini-orgasm ripped through me and even as I pumped cunt down onto my small finger I was thinking about the sex toys I kept in that chest in the closet. I even considered dressing up in one of those slutty outfits, going all out and fucking myself into a stupor but in the end I just grabbed a 6 inch dildo and climbed back into bed.

I teased myself first. Running the head around my lips much the same way I would usually do to one of the many girls I fucked in this bed and much like them I was so worked up I just wanted it inside me. I gasped as I felt the head penetrate my pussy lips. I watched in awe as my greedy little pussy swallowed up as much fake cock as it could until I felt what I can only describe as a blockage.

“A virgin? I’m a fucking virgin?” I almost laughed.

“Well I’ll take care of this situation right now” I thought to myself as I got a towel from the bathroom and laid it on the bed underneath me. Once again I fed the blue sparkly fake cock into my tight hole until I felt my hymen. I braced myself and quickly stabbed at it until I had the toy buried inside me to the base. The pain was different than what I had always imagined but it seemed to subside relatively quickly and before long I was screaming and cumming all over again.

“I popped my own cherry.” I thought to myself as I faded off to sl**p.

************************************************************************

I awoke the next morning with the feeling that someone was watching me and as I shook of the effects of slumber my eyes focused in on a figure. A female form standing at the foot of my bed. I bolted up, the blanket falling away to reveal my tits, and it took a second to register that it was Sasha.

“Morning sunshine. I brought coffee and bagels.” it dawned on me that I hadn’t eaten at all yesterday and I was starving. I happily accepted her offering.

“Ungh. What time is it?”

“6AM. I wanted to come by before work. I let myself in with the key you gave me.”

“So I’m hoping you come with good news.”

“Sorry babe. Like I said my friend is unreachable and I couldn’t find anything that would relate to the situation at hand.”

“Well isn’t that just peachy.” again I caught her staring at my tits but this time I didn’t seem to mind. As I set the coffee on the night table I realized that I had left my dildo sitting there. I suddenly remembered how good it felt to be penetrated by it and was already planning on a repeat performance as soon as I was alone. To my dismay I wasn’t the only one to notice it.

“Well now, looks like someone had a little fun last night. I had one just like it when I was about your age. Speaking of which, how old do you figure you are now?” she had already climbed into bed next to me.

“I don’t know. I would guess maybe 18?”

“MMMM legal. Awesome.” the attention she was supplying felt amazing and I found myself arching my back just enough to accentuate my young tits.

“So what do I do now? I mean it looks like I’m going to be like this for a few weeks.”

“Well have you settled on a new name?”

“No. I hadn’t really thought that far ahead. In fact I’d just as well prefer to stay locked up at home.”

“I don’t know, maybe you should get out and interact. Live life as a female for a while and see what it’s like. Gain some perspective, isn’t that what that woman told you?” Sasha was right.

“I guess a little interaction would hurt. Maybe you should call me Erica for now?”

“Oh come on. This is your chance to be someone else. Don’t just feminize your old name.”

“Brittany?”

“Yuck!”

“Amber?”

“What are you an 80’s porn star?”

“Stephanie?”

“You don’t really look like a Stephanie.”

“Well what do you suggest?” she took a long deep stare into my eyes and I felt a sexual tension that both scared and excited me. OK so it excited me a lot more than it scared me. After all, Sasha is a damn fine looking woman. She stood about 5’ 6” with a light olive complexion. Her brunette hair had just bit of curl to it and it framed her beautiful features perfectly and hung down just below her still somewhat perky tits.

“Hmmmm, how about….Emily? Yeah you’re totally an Emily.”

“Well I don’t hate it.”

“So Emily it is.” I giggled a bit.

“Aww that’s such a cute little giggle.” she was teasing me but in what felt like a flirtatious manner and for the first time all morning I noticed that she had done herself up more than she usually would when stopping by. Her hair was done up in this quasi-50’s pin-up style and her lips were painted a deep red. I had often imagined them wrapped around my cock but now I found myself wondering how they would look sucking on my tits.

“Damn your tits are fucking perfect. Most girls would kill to have tits like yours. How do they feel?”

“See for yourself.” I turned so that she had complete access. When her hands landed on my tits it was electric. The small trickle of wetness between my thighs turned into a raging river when I felt the heat from her hands.

“Fucking phenomenal! I think I hate you now.” her fingers caressed my tits in a way that any inhibitions I may or may not have had.

“MMMM if you think those are good you should see my pussy.” I blurted it out and almost as soon as I said I wondered if I really should have but the look on Sasha’s face squelched my anxiety. I could only bit my bottom lip as I watched her peel the blanket away from me and reveal my nude body to her for the first time. I had my knees slightly bent and slowly opened my thighs as I watched her watching me. I knew she would undoubtedly see my wetness and I guess I wanted her to. I let instinct take over and I playfully ran a single finger up my slit one time.

“Such a gorgeous little pussy.” she literally moaned as she admired my young slit.

“You naughty little girl, are you wet?” she asked but continued to stare at my cunt instead of looking me in the eyes.

“MMMM why don’t you tell me?” it felt like my entire body was shaking wildly as I watched her hand slide up my smooth thigh and when that finger came to rest on my sopping pussy lips I couldn’t help but moan.

“Ohhhh Sasha!”

“MMMM you are wet.” her finger pressed against my mound, threatening to penetrate. I looked up at her as she leaned her face into mine. I thought she was going in to kiss me so I leaned into her, to my confusion she instead positioned her lips near my ear and began to whisper to me.

“I’m going to ask you a question. Don’t think about it, just answer. OK?” I nodded my head as I pushed my young mound against her finger.

“Do you want me to fuck you or make love to you?”

“Fuck me! Fuck me Sasha!”

“MMMM that’s what I wanted to hear.” she smiled and this time she did kiss me. Her lips pressed hard to mine as I felt her finger slide up into my wet hole. I screamed into her open mouth as a second finger worked it’s way up inside me and I felt Sasha’s tongue dart into my mouth. The feeling of her finger’s gently pumping up into my needy cunt and the sensual kissing was pushing me over the edge faster than I could have imagined and I felt my first orgasm quickly building.

“Ohhhh you going to cum for me baby?”

“Say my name! Oh please say my fucking name!” I had this weird urge for her to say it. I felt her breath hot against my ear when she uttered it.

“Emily. Cum for me Emily. Cum all over your big s****rs fingers.”

“Oh yes! Yes! Yes! Oh fuck me Sasha yesssss!” I screamed as the pleasure shot through me. Sasha kept finger fucking me, building in speed and intensity and I was going insane with lust. I opened my previously closed eyes just in time to see my little pussy gush all over her skillful hand. I had to clamp my hands around her wrist to stop the onslaught of my now sensitive little hole. I pulled her drenched hand up to my mouth and lewdly sucked both fingers clean. As soon as I pulled them from my mouth Sasha was already kissing me. I clawed at her shirt in a feeble attempt to get it free from her and to my disappointment she pulled away from me.

“MMMM play with yourself Emily. Rub that sweet little cunt while I strip.” her fingers had already began to nimbly unbutton her shirt. I had only seen her naked once in my life and that was when we were much younger but I can honestly say that time had been very, very nice to Sasha over the years. Her skin felt smooth and taught as she slid back into bed and on top of me. My hands roamed down her back and over her shapely ass.

“I hope you remember how to eat pussy little girl.” I flashed what felt like a wicked smile and f***ed her onto her back. I quickly got on top of her and began kissing my way down her body. I took time and sucked and nibbled on each tit making her moan. My tongue worked it’s way down her tummy to the thin little landing strip of pubic hair. I could already feel the heat emanating from between her thighs and sell her aroma. When my nipple lightly brushed against her swollen clit Sasha arched her back and when my tongue found that same clit she screamed.

“Oh fuck yes! Lick my fucking cunt Emily!” her ass raised of the bed to offer me her sweet pussy. I flicked my tongue against her swollen clit as I spread her lips open and pushed two fingers deep inside. Her moaning telling me that I was hitting all the right spots.

“Suck my clit baby. Suck me and fuck me.” my lips suckled against her clit as I pumped my fingers hard into her sopping hole. Sasha began to thrash when I gently bite her clit, holding it between my teeth and flicking my tongue against it rapidly.

“Oh fuck! Oh fuck! Oh fuck! Emily! You’re going to make me cum! Make me fucking cum! Do it! Do it you little slut! Make me cum!” she was now holding my head and grinding her mound against my mouth and sure enough I was soon rewarded with her sweet nectar. After her first orgasm she pulled me up and we began kissing again. Sasha tasting herself on my lips.

“Your turn now little s****r.” she grinned and rolled me onto my back and began to give me the same treatment I had just given her. I was softly gyrating my hips as she held me open and took long licks up and down my pussy. I felt her rudely spit on my snatch and it felt so fucking hot to be so slutty.

“Look at this pretty little pussy. I bet you need a big stiff cock buried in there don’t you?”

“Oh god yes Sasha.”

“Say it Emily. Tell me what my little s****r needs.”

“Use my toy and fuck me. Fuck me hard and deep.” I had retrieved my dildo from the side table and offered it to her. She only smiled and tossed it aside.

“Oh I think I can do better than that. Much, much better actually.” she reached into her bag and pulled out a rather large strap on. My eyes must have bulged when I saw the size of it. The thing had to be every bit of 8 inches long and really thick. I was a little scared at first but seeing her wearing it made me want to take it all.

“You want this baby? You want your big s****rs cock?” she was stroking it as she spoke. I was rubbing my clit and biting my lip as I watched her slide her hand up and down the fake cock. I nodded my head in affirmation even though I had some apprehension about that big thing going inside me.

“Get down on your knees you little bitch and suck this fat fucking cock.” the harshness in her voice seemed to only fuel the fire that was burning inside my pussy and I was quick to comply. Sasha looked down at me as I wrapped one hand around the shaft and slowly stroked it up and down.

“Spit on it Emily. Make it nice and sloppy.” Sasha moaned as I lewdly spit on the massive head and began to twirl my tongue around it before licking up and down the shaft. Now I had never sucked a cock in my life but I have had mine sucked more than I can even begin to count so I just tried to mimic the techniques that girls have used on me over the years. I held the shaft up and licked down the length to the fake balls. I took them into my mouth and moaned before slurping my way back up. I made sure that she was watching as I opened my mouth and slowly inhaled as much as I could. Maybe I got a little over zealous because I took just a but more than I could and started to gag.

“MMMM yeah that’s a good little girl. Gag on that fucking cock.” I tried a few more times to take more of it and each time resulted in a few more inches down my throat but also more gagging. I admit that at first sucking her strap-on was a means to an end. I wanted her to fuck me with it and had no real desire to suck it but as I knelt there bobbing my head up and down I became aware of the fact that I was enjoying it. I was loving the way it felt sliding between my lips, the way it nudged at the back of my throat and how is felt when it would slip in a little deeper. I was stroking it with one hand and sliding my lips up and down with the other.

“Oh look at you go. You like sucking cock don’t you?” I looked up and nodded my head with a mouthful of strap-on.

“Well I think it’s time to fuck. You ready baby? You ready to get that pink little pussy stretched?”

I reluctantly pulled her plastic cock free of my mouth, dripping with saliva, and coyly made my way up to the bed. I positioned myself on my back, legs spread wide and watched as Sasha knelt between my legs. I moaned as I felt her slap the thick head against my drenched slit then slowly push against my tiny hole. She felt the resistance from my tightness and paused.

“Oh do it Sasha. Please. Fuck me. Fuck me with that fat cock. Fuck your horny little s****r!”

“You sure you’re ready Emily? You sure your little cunt can take it?” I felt the head slip inside me.

“Ohhhhhh! Make me! Make me take it Sasha! Make me take your big dick! Fuck me!” she slowly gave it a few strokes, going in a little deeper each time.

“Oh you’re so fucking tight! I don’t want to hurt you baby.” each word was accentuated by a short stroke inside me. As for me, I craved the feeling of it stretching me. I wanted her to bury that toy as deep in my young snatch as possible.

“OHHHHHHH! Do it! Do it Sasha! Hurt me with that big fucking cock! Fuck me!” she smiled in a manner that can only be described as wickedly sexy and rammed the remainder of that strap-on up into my accepting fuckhole and started to piston in and out in long, deep, hard strokes.

“Oh fuck yeah! Take it little girl! Take this big fucking cock. You like having your big s****r’s dick inside you?” the feeling of being filled like this was indescribable. I could only nod and grunt as she held my legs open and continued to slam it deeper and deeper into me.

“Fuck me Sasha! Fuck me! Fuck your little s****r’s creamy cunt! Make me a little cock whore!” the words flew mindlessly from my mouth as I clawed at my own tits. Beads of sweat formed on Sasha body and her tits bounced wildly as she slammed into me over and over again. Her beautiful face scrunched in effort as her only purpose at that moment was to pleasure me. My body began to convulse as I felt the biggest orgasm I had ever had up to that point in my life begin to hit me.

“I’m cumming! I’m cumming! Oh my god yes! Fuck me! Fuck me! Fuck meeeeee!!!!” I wrapped my legs around Sasha to prevent her from moving as I flooded her fake dick with my juices. My head almost instantly began to spin as sheer pleasure coursed through every nerve ending. Sasha leaned down onto me and held me as my orgasm wreaked it’s wonderful havoc through my body.

“Is it your turn now?” I playfully teased as I explored her ass with my hands.

“Sorry baby. I have to go open the shop. Raincheck?” even as she pulled out of me I felt an emptiness between my thighs that I knew would have to be filled again soon. One that my 6 inch dildo, which seemed so big to me last night, wouldn’t be able to satisfy.

“Hey! Leave the toy? You know….for practice?”

“MMMM I do think I may have created a monster.” she leaned down and kissed my lips before leaving.

As I heard the door close and the house fell silent once again I stretched and checked the clock. Only 8:30? What was I going to do the rest of the morning? I eyed the 8 inch cock laying on my bed and grabbed it.

“MMMM well hey there big boy.”


Story URL: http://xhamster.com/user/taboo_daddy/posts/131337.html