This is a print version of story Becoming Emily - Part II by taboo_daddy from

Becoming Emily - Part II

Thirty minutes and one mind shattering orgasm later and I was starting to feel somewhat satisfied. It was my intent to just lounge in bed all day but when my cell phone alerted me to a text message, that plan flew out the window. As I read it my heart sank.

Eric, don’t forget that I will be stopping by to pick up that contract while I’m in your area. I’ll be there in about 15 minutes.

It was from Mitchell Ross. I had met him a few years ago when we both worked for the same company. I had found out after one rather wild office party that he and his wife were swingers. He pulled me aside and danced around the subject of me joining him and his wife Julia in a threesome. At first I was apprehensive because I wasn’t exactly certain as to his orientation but after he assured me that there would be no man on man action I was on board. Julia was, after all, incredibly sexy. When we all got down to fun I was taken aback at the size of Mitchell Ross’ cock. The man was freaking huge. The wheels of thought about broke from the effort when I tried to think of an excuse not to be home. I needed him to sign off on the documents for the land sale but couldn’t rightly conduct business as Emily.

Hey Mitch. I’m out of town right now but my house sitter should be home. I will call her and have her get the contracts for you. As long as everything is in order you can just sign and mail them back. Sorry I couldn’t be there.

I surged through the trunk in my closet in search of something to wear. Almost everything was either the wrong size or just down right slutty looking. Finally I had found a white pleated skirt that was probably a little too short but it would have to do. I coupled that with the t-shirt I had found yesterday, since it was the only one that actually fit me. I decided that after Mitch Ross left I would have to go do some shopping. I had just tied my hair back when the doorbell rang. As I answered the door I felt his eyes on me.

“Hi. Mr. Ross?”

“Yes. Mitchell Ross. I’m looking for Eric?”

“Mr. Kane is out of town for a f****y emergency but he told me you were dropping by. Didn’t you get his text?”

“No. Sorry. My phone tends to get terrible reception out this way.”

“Oh. I’m Emily. I’m house sitting while Mr. Kane is away. Come in and I’ll get you the documents he left for you.” he followed me inside and I could sense that he was staring at my ass. The skirt covered it but not by a whole lot and it certainly showed off my legs, which were incredible by the way. When I turned to had him the large manila envelope his gaze drifted up to my tits and I felt a strange tingle running through my body. I have never been even remotely attracted to another man so I began to wonder if the physical transformation I had undergone had also altered me psychologically. My mind flashed back to the night we shared his wife and I became fixated on the site of his huge cock pumping into her pussy.

“Here they are. He mentioned that you should go over them and if they are OK you can mail them back.” he took the package and we both just sort of stood there silent for a moment.

“Can I get you a coffee? I just brewed a pot.”

“Um, yeah I think I have time for a cup.” he flashed a smile and followed me into the kitchen. We chatted while we had our coffee. I explained how I was new to the area and didn’t really know too many people yet.

“Well Emily, thanks for the coffee but I have to get going. Here is my card. I have a business meeting tomorrow so I’ll be in town tonight. If you find yourself bored or in need of some company feel free to give me a call.”

I accepted his card and walked him to the door and as soon as he was gone I readied myself for a little shopping. The only shoes I could find were flip flops that someone must have left behind back in the Summer. Again this wasn’t exactly the greatest option as Autumn had just started to settle in but it would have to do.

Initially I planned on only getting the essentials. No sense in spending money on clothes that I wouldn’t need in a few weeks but as my shopping excursion went along I found myself buying a lot more than I had intended, some cute stuff but mainly items that I found to be sexy. It took some trial and error but eventually I figured out my various sizes. I also found myself lured into the notion of a spa and I soon realized the fascination women have with getting their nails done. I returned home a few hours later and after putting away all my new clothes I went about preparing for the absence of my normal life.

I composed an e-mail to explain why I wouldn’t be into the office on Monday. Being self employed I had no bosses to answer to but I did have an office staff to contend with. I decided that I had been called away for a f****y emergency even though I didn’t have any f****y and that if there were anything that needed my immediate attention that I could be reached by text or e-mail only.

Satisfied that all my bases were covered I found myself with nothing else to do at the time. Eventually I started to watch internet porn and rub my little pussy through my new pink panties. I started out watching only girl/girl stuff but as the minutes turned into an hour I was watching boy/girl stuff and I became very interested in seeing men cum. I would get disappointed if I watched an entire scene and there was no cum shot. I started to imagine how it must feel to take a hot, creamy load either on my face or inside me. I found a large collection of facial compilations and watched with the same intent I had whilst watching lesbian porn. Needless to say that after a while my thoughts turned to Mitchell Ross and is insanely large cock. It was even bigger than the dildo Sasha had used on my earlier which was now sliding in and out of my mouth. I recalled how it looked banging up into his wife and how it spurted thick ropes of seminal fluid when he came. Before I could change my mind I called his number.

We agreed to meet for dinner at his hotel at 7PM which gave me just enough time to get ready. After a long bath and a few tricky moments with a razor I had chose my outfit for the night. A slinky black little dress that hugged the curves of my body and accentuated my newly begotten feminine assets along with a pair of black platform heels that may have been a tad on the slutty side. Underneath I went with a red lace thong and it’s matching strapless bra. I clumsily applied make-up like the woman at the spa had instructed me. It took a lot longer than I had imagined but the end result was worth it. I checked my look in the mirror and was damn impressed if I do say so myself.

During the drive to his hotel I had many conflicting thoughts and emotions. After all I was a man less than 48 hours ago and yet I found the male aspect of my psyche often being lost in what I can only describe as feminine rational. Physically I was female and I felt the need to be as such but the male part of me was wondering if this was right. I wasn’t gay and had never had any inclinations to such so my mind was at war with itself. Ultimately I decided that anything I did while in this female form was not a reflection of my previous self. In fact I made a conscience effort to block out any male thought processes for the evening and by the time I pulled up to the Regal Inn I was 100% Emily.

Dinner went well even though we did get a few stares from the other patrons. This young girl with an obviously older man. I went through the back story I concocted and watched as he looked at me with a yearning that sent small lightning bolts through my body. By the time dinner was over I found myself wondering just how to proceed. Thankfully he provided the means.

“Maybe we should slip to the bar and have a drink?”

“Well that does sound great but I’m not old enough.”

“How old are you?” his voice almost a whisper.

“18” he smiled.

“Well would you like to head up to my room? I can order a bottle of champagne or wine.”

“Let’s go.”

I’ve always loved a girl that knew what she wanted sexually and wasn’t afraid to go after it and this, I decided, was how Emily would be. For his part all though dinner Mitchell Ross seemed unsure about whether or not he would get laid but as soon as the elevator doors closed he certainly knew because his hand instantly found my ass.

“Find something you like Mr. Ross?”

“I’ve been thinking about this ass all day Emily and you can call me Mitchell.”

“Do I have to? It’s way kinkier if I call you Mr. Ross isn’t it?”

“Are you a kinky girl Emily?” he pulled me close, both hands digging into my fleshy ass.

The elevator doors opened before I could answer and he led me to his room. Once inside the nerves that had been causing my stomach to do back flips gave way to raw sexual need. Mitchell Ross pulled me close again and kissed me hard as his hands roamed my young teenage body. I playfully pushed him away and gave a seductive smile as I turned my back to him.

“Help me with he zipper.” he was methodical in his pace. Taking his time to reach forward and cup my tits as he pulled the zipper down. I pushed away again and slowly allowed my dress to fall to the floor and did my best to pose in a sexy way. He was already kneading his cock through his pants.

“So, what do you think Mr. Ross? Is this 18 year old body what you imagined?”

“More so.”

I teasingly removed my bra but covered my tits with my arms as he groped his erection and moaned in approval when I finally revealed my perfect tits to him for the first time. The bulge in his pants seemed unbelievable huge at this point and that only fueled the fire between my legs. I move din close, my tits pressing up against him as my hand found the throbbing member hidden inside his pants.

“Oh my god Mr. Ross.” I exclaimed as I felt his hard-on for the first time.

“You like big dicks baby?” he leered as I messaged him.

“MMMM and you’re so fucking hard!”

“I been hard all day Emily. Ever seen you opened that door this morning.”

“Oh really? You been thinking about how good it would feel to have your huge cock in my tight little cunt Mr. Ross?” I slid down to my knees, tracing the outline of his dick with my tongue.

“Oh fuck yes I have.” I had started to undo his pants and slide my hand inside looking for what I needed. He twitched a bit as my small hand struggled to pull his cock free and it felt bigger than I remember it looking. I decided to instead just pull his pants off and when I did his huge, thick cock sprang free and nudged against my face. Thankfully Mitchell Ross was against pubic hair as his entire pubic area was shaved completely.

“Oh fuck Mr. Ross! You’re fucking huge!” my eyes went wide as I used both hands on his massive dick. I remembered how I had sucked on Sasha’s strap-on that morning and how se said I looked so hot doing it. I wanted to elicit the same response from Mr. Ross.

I slide my tongue around the head, twirling it along the ridge before taking his massively swollen head between my lips. I continued to stroke his shaft as I slurped and took inch after inch into my mouth. I had hoped that my practice with Sasha’s big toy would have prepared me for this and maybe I could even deed throat him but there was no way. That didn’t stop me from trying though. I hit my limit and gagged just as I had done earlier.

“MMMM that’s it baby. Gag on my fucking cock.” he moaned.

I pulled back and withdrew him completely. I made sure he was watching as I spit onto his immense tool and gobbled it back down. This time I stopped at what I found to be a comfortable length and started to bob my head up and down, sliding my red painted lips along his length. I caught site of my reflection in a mirror. My tits bouncing as I inhaled his cock, sucking and slurping, feeling saliva and pre-cum dripping from my mouth and onto my tits.

“No hands Emily. Just use that mouth.” I did as instructed and used one of my hands to play with my already needy pussy as I sucked my first real cock.

“That little teen pussy getting wet for me Emily?” I nodded in the affirmative with his thickness still between my lips.

He withdrew from my mouth and pulled me to my feet. I was disappointed at first but moaned loudly as his hand slid between my smooth thighs and rubbed against my panty covered mound. His kiss stifled a scream when his finger pushed inside my thong and slid up into my tight little hole and finger fuck me furiously.

“Oh fuck me Mr. Ross! Fuck me!”

“MMMM is that what you want Emily?”

“Yes! I want you to fuck me Mr. Ross! I want your huge fucking cock up my tight little cunt!”

He pushed me back onto the bed and immediately started to pull my panties off but left my heels on. I felt the air against my raw cunt as he pushed my legs open and rubbed his massive head against my slit. I braced myself for it. I knew it would probably hurt a bit but I didn’t care. I wanted to feel him inside me. I wanted to be a great fuck for that big dick. He began to lick and bite my nipples as he worked himself up inside me. At one point I f***ed myself to silence a scream but Mr. Ross would have none of that.

“Scream little girl. I want to hear you scream for my big dick.” he almost whispered into my ear. I had no idea just how much of him was inside me but when he told me to scream he rammed whatever else was left deep into me and I felt his groin push against me.

“OHHHHH FUCKKKKKK!” I screamed as he filled me up.

“Fuck yes Emily. Damn baby, you’re so fucking tight.” he grunted as he slowly pumped in and out of me.

“Do it Mr. Ross. Do it! Fuck me! Fuck that tight teen pussy!” he began to go in deeper, harder, rougher. I started to loosen up and he pushed my legs open even wider, taking access to me as he grunted and groaned.

“Where is that big dick little girl? Where is that big fucking dick?”

“Inside me Mr. Ross. Oh my god you’re so deep inside me.” any pain was now gone and in it’s place was pure pleasure.

“Give it to Mr. Ross! You dirty old fuck, give me that fat fucking cock.”

“You naughty girl Emily.”

“Yeah fuck me like a naughty little girl. Fuck me like a dirty fucking whore!” my words urging him to do just as I asked. He began to pound into me, his skin slapping loudly against mine. My tits flailing about as I took every inch he had.

“I want your cum. I want you cum all over my face. Shoot your hot fucking cum all over my face!” he pulled out and I thought he was going to give me what I wanted but instead he pulled from the bed and moved me over to the dresser.

“Bend the fuck over you little fucking slut!” he demanded and made me bend over the short dresser. I could see him the mirror as he got behind me and I felt him ram his cock back up inside my hungry cunt. His hands reaching forward to grab my tits as he fucked me from behind. Watching my own expressions while feeling his 10 inch cock plowing into me was euphoric. So much so that I didn’t hear him when he told me he was going to cum. I became aware of that fact when he pulled out and jerked me around. I get the point and dropped to my knees as he stroked himself off.

“Oh yes Mr. Ross, give me your cum. I want your dirty load all over my face.” he pumped his length a few timers then aimed directly at my face as he exploded. I think I was more shocked at the sheer velocity of it than I was at the actual amount. Not that there wasn’t a lot of it because there certainly was. I felt steam after stream of hot stick jizz splatter against my face. It landed on my cheeks, on my lips, some went into my mouth and was soon dripping down to my tits, and onto my upper thighs. As soon as the stream slowed to a trickle I swallowed his cock in an attempt to milk every last drop but Mr. Ross was too sensitive and pushed me away.

“Fuck if you aren’t a cum hungry little girl Emily.” he chuckled.

“MMMM you’re delicious Mr. Ross.” I teased as I scooped up his cum from my face and tasted him.

“Whew, I think I need to sit down for a minute.” he plopped down on the bed and watched me devour the cum that was s**ttered across my body. I noticed that his cock never actually went soft. It did start to droop but was still semi-hard when he laid onto his back. I crawled over and slid up onto his lap and straddled him.

“So was I as good as you imagined?” I had already began to grind my wet pussy against his semi-hard cock.

“Oh yeah, even better.” I felt him stiffening.

“MMMM my young little teen pussy feel good on your cock Mr.?” his hands reached and groped my tits.

“How would your wife feel knowing that you had this big fat cock deep inside a tiny little 18 year old cunt?” I pulled his left hand up and licked around his wedding ring.

“She would probably be trying to get between your legs to.” he chuckled.

“MMMM I think I might like that.” his cock was fully hard now and I held it in my hand and guided my creamy cunt down onto him.

“You going to tell her about me? You going to tell her about you fucked this little teenage slut and blew your load all over her pretty face?” I teased as I rode him as I reached back and messaged his balls.

“Oh fuck! Emily, I won’t last long like this.” he warned as I bounced up and down on his prick.

“Maybe she’d like to fuck me up my virgin ass with a strap-on while you pound my slutty little fuckhole?”

“Oh fuck Emily, don’t stop.” I didn’t know if he meant the dirty talk or the way I was fucking his cock. I continued on with both but soon enough my own orgasm made talking almost impossible.

“Emily! I’m close baby! I’m so fucking close!” my pussy tightened and began to spasm as I came around his massive pole and there was no way I could stop.

“Cum inside me Mr. Ross, I don’t care just don’t make me stop!”

“Take my fucking load little girl.” he began pushing up inside me as I slammed my ass down against his thighs and he really seemed to be turned on about cumming inside me.

“Ohhhhh yes do it Mr. Ross! Shoot that nasty cream deep in my little cunt! Fill me up!” he grabbed my waist and slammed me down to him and held me there as I felt his cock twitching and I could feel it spurt his seed into me. He held me there until he went completely soft. Finally I rolled off and watched his cum leaked from my freshly used pussy.

“Don’t worry. I’ve been fixed so you won’t get pregnant.” he offered, not that I was worried about that as I didn’t plan on being female long enough for that to be an issue.

We laid there awkwardly for the next 15 minutes or so before I got dressed and left. I did the “Walk of Shame” through the hotel but truth be told it was kind of a turn on. I drove home feeling Mr. Ross’ cum still drooling fro my little pussy and soaking my thong and I drifted off to sl**p that night wondering about the possibilities of the next day.

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