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.