The Runt of the Litter... Pt. 04

I chose Transsexuals & Crossdressers again as the category, while it's still man on man sex, I thought the theme was more about transformation from male to female than gay sex. If this offends you, please don't read any further. I'm happy to continue if there is any expressed interest in the comment section. I welcome any ideas or twists you may wish to suggest or contribute.

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Dinner was just me and my mom, dad was at the office working late again and my brothers all had dates or other obligations. While I was the last sibling still living at the house, my brothers were pretty much regulars when the dinner bell rang. My parents always welcomed them and their dates if they wanted a home cooked meal.

Okay, so getting to sleep that night was pretty tough. After dinner, I went straight to my room and had a quick jerk off session behind my locked door. I intended to make it a long one, but I was so horned up after the day's activities, that I came in just a few minutes. So 30 minutes later. I jacked off again and the second time I really rubbed out a slow sensual one.

Then I laid in bed, trying to doze off while browsing the Internet for pics of hard cocks being sucked by cross dressers for hours and got horny again. I fantasized about being dressed up like a hot little vixen and sucking those hard cocks. As if the two previous jack off sessions weren't enough, after laying in bed unable to fall asleep, I beat off my cock one more time and finally crashed.

I dreamt of cocks and woke up with cocks on my mind. I was turning into such a cock slut that I scared myself, just kidding. Finding myself home alone, I made myself an English muffin and used my self control not to call Samantha too early, but at 9AM, I found myself dialing her number.

I obviously woke her up and she sweetly scolded me for calling her so early.

"Nicky, it's so early, I'm sleeping sweetie, you know I closed last night. I didn't leave the club til almost 3AM. Your Uncle Ronnie made me give him some ass before he let me leave, and he took his time. My little booty hole is so sore today, I can hardly sit on it." she giggled.

"I'm sorry Samantha, I'm just so excited about today, I'm sorry, I tried to hold off calling you, I really did, but I'm just so excited. Do you want me to call back later?" I asked hoping she would say no.

"Yea Nicky, give me an hour to shower and have some coffee, then call me back. Your uncle told me to take off today and get you sorted out. So it looks like a girl's day for you and me." she giggled again.

After I hung up, that hour seemed to last forever, but at 10AM on the dot, I called her back.

"You awake now Samantha?" I asked as she answered the phone.

"Good Lord Nicky, get your hormones under control." she teased me. "Give me your address and I'll be there at 10:30 sharp."

I started looking out my window 15 minutes earlier than she was expected and when I saw a brand new shiny silver Audi pull up to the curb, I flew out the door.

Samantha looked amazing in the daylight in her new car. So sexy, so pretty, so fucking hot. Covering her blonde hair with a long raven black haired wig and she was dressed in full female sexy mode. Such a pretty face, sexy brown eyes, pouty lips, a sleek model's nose, what a hottie. A pair of tight stretchy beige yoga pants, that somehow hid her bulge completely, but showed all the curves she possessed on her thin frame. Brown soft very expensive looking 4" heeled knee high boots. A tight brown leather top, that matched her boots. Sleeveless and zippered up the chest, it concealed what appeared to be the two most perfect breasts ever, and her makeup was amazing looking. She was a dream boat if ever I saw one. Nobody would have ever believed that she was a guy and had a big fat cock hidden in her panties.

"Girl, I am worn out, last night was kind of a tough one for me. Having Tito as my second customer to start with really wore me out for the rest of the night. I gave up my ass 5 times last night, not including your Uncle Ronnie's freebie. Don't get me wrong, I love my ass fucked and I made almost $1,100 last night. Still, while most of the guys weren't so big, Tito and one of my regulars, who is bigger than Tito, destroyed my butt. I didn't really want your uncle to fuck it, cause he's pretty freaking big himself, but you don't tell Mr. Anderson no."

"You have a regular bigger than Tito?" I asked astonished.

"Ooooh honey, you're in for quite a shock my little one. I have several customers bigger than Tito. According to them, I give my ass up way better than the other girls do. That's them talking, not me bragging. They tell me that I'm the only one that can take them all the way to the root and not fight their deep dick poundings." she said with a hint of pride in her voice.

"So, tell me about this Mr. Big." I asked dying to hear the details.

"Well Nicky, I don't know his bio." she said feigning annoyance at my question. "You know how the room is set up. It's hard to see anyone clearly. He's huge though." as she spread her hands apart about 2 feet and snickered.

"Oh you're full of it, nobody is that big, are they?" I stupidly asked her.

"Okay, I'm exaggerating, but he's at least 10 inches, no actually more than that I'm sure, and it's a total prime grade A beef all American whopper. An older guy, he's white, circumcised, thick, gets super hard, always smells really good and is a total sweetie, very polite. He reminds me of your uncle a lot, and introduced himself to me as T.A. All the girls adore when he visits them. Is that enough of the gory details for you?" she went on laughing. I wanted to hear more, but didn't press it.

"Okay Miss Horny , enough about cocks, we have a lot to do today. We are gonna buy you a few sets of glue on nails and show you how to apply and remove them. We are gonna get you a good expensive wig at Hair by Cher and that will set you back $300. We are gonna get you at lease 6 sets of panties and bras, heavily padded, and all the makeup, perfume, nail polish, lipstick, lingerie, blah, blah, blah, necessary to transform you into a sexy little hottie. You're going in the hole over $1,000 today." she laughed.

"Samantha, I don't have any money." I fretted.

"No worries sweet cheeks, your Uncle Ronnie told me to pay for them with cash, bring him the receipts and he would reimburse me. You will pay him off in 1 or 2 nights. Quit worrying, we got you covered darling." she explained.

Once we got to the mall, Samantha flitted from store to store like she had done this a million times before. I was so proud to be with her as I watched guys smile and stare at her every move. She knew exactly what she was doing and made most of the buying decisions herself, but did ask me what perfume I liked best and what color I liked most on the painted fake nails, which I picked blood red.

We finally arrived at Hair By Cher and she told me this was a very personal decision that I should make myself. I was attracted to the head mannequin that held a bright blonde wig with very straight shoulder length hair and untrimmed bangs that just barely went over the eyebrows. It just reminded me of a sexy summer surfer girl, wild and carefree. I almost felt like it spoke to me and said "buy me", as it surely made my cock hard.

We got take out from Taco Cabana on the way to her house and when I walked in her studio apartment behind her, I was flabbergasted at how it looked. It reminded me of those show homes I would see in my mother's magazines. Everything was so fresh, clean and stylish. We gabbed while I nibbled on my food, nervous about getting transformed, my appetite wasn't that big.

I hadn't developed anything that needed shaving on my face yet. I had no facial hair, but still she instructed me shave it closely before I showered, taking care to trim my sideburns very high. She also gave me a bottle of Nair hair remover and instructed me on how to use it. Finally stepping out of the shower, I was amazed how soft my legs were with all my peach fuzz removed. The most erotic feeling, was my now smooth cock and balls. I just loved the way they looked all smooth and clean.

Samantha started with my eyebrows, plucking and sculpting them a bit with tweezers, but not too much that my parents might notice. As we sat at her dining room table, Samantha worked her magic starting with a foundation base on my face but not allowing me to see her progress. She worked on me for at least 30 minutes, gushing the whole time about how hot I looked and finally opened the package with the wig. I just sat there totally excited and aroused as my cock stood at attention.

As she straightened the wig on my head, so my bangs just touched the very top of my eyebrows, she told me to pick out a pair of panties and a padded bra from the assortment on the table. I chose the bright red lacy ensemble and slipped them on over my erection while she helped me with the bra. Samantha gave me two spritzs of my Dolce Gabbana Intense perfume on my shoulders and neck and took one last look.

"Nicky, go in the bathroom and look in the mirror. Tell me who you see." she said with a confidence that made me tingle.

I almost ran to her bathroom and stared at the person in the mirror, frozen in my tracks, I couldn't move. Looking back at me, was one of the hottest girls I have ever seen in my life, so fucking sexy. This girl was a totally unreal, sexy, fine ass bitch, and this girl was me. I never felt more confident in myself or thought I looked so desirable in my whole life.

Samantha came in and stood behind me, pressing her yoga pants erect covered cock firmly against my ass, just smiling at her work. "What do you think Nicky, pretty hot huh, do you think anybody would recognize you now?" she almost bragged.

"Ooooh my God Samantha, I don't even recognize myself. You are the Michelangelo of transformations. I cannot believe how hot I look." I gushed, embarrassed that I just complimented myself.

Samantha's face beamed as she adjusted my bra straps and smoothed my hair in a few spots. "I hope you paid careful attention, because you need to be able do your own makeup and dress yourself now."

"Samantha, I don't know how I can thank you. I adore this look, I feel like I have found my calling in life." I said as I kissed her softly on the cheek.

"I know how you can Nicky. Come suck on my cock for me. I'm so horny after seeing you." as she took me by the hand and led me to her bedroom.

Samantha dropped her clothes in record time and crawled into the center of the bed, with her 7 inch cock standing proud and upright off her flat tummy. Propped up against her mountain of frilly pillows, Samantha beckoned me with her index finger to crawl between her legs.

As I started to undress, Samantha said, "No, no, no, leave it on, all of it, let me enjoy my creation." she giggled.

My little cock was so swollen, peeking out the top of my panties, I was so aroused. As I knelt between her splayed legs, adjusting myself into the lotus position, I felt like I was in my natural environment. Trying to be feminine and girlish, I leaned over til my mouth enveloped just the tip of her cock. It was so warm in my mouth. Her tip had per cum seepage leaking from it and I relished the taste.

Her little manicured pubic hair patch of a heart looked so pretty, that I decided right then, that as my hair grows back out, I'm gonna trim it to a matching heart like hers. It felt so good to take her cock in my mouth. I nursed on about 4 inches, just softly massaging the underside with my slobbery tongue, occasionally backing off to just the tip and sucking on it hard looking for more precum.

I loved how my bangs fell into my eyes and how my long blonde hair felt on the side of my face as I sucked her. The blood red lipstick made perfect little imprints on her hard cock and it made me feel like I was marking my territory like a predator. I loved the way I smelled and the lacy panties were driving me insane as I basked in the glow of worshipping her cock.

I lowered my face to her balls and gently nibbled on her ball sac. I just nipped the wrinkly skin between my front teeth hard enough so she would groan each time I repeated that. I gingerly took her balls into my mouth and softly nursed on them, massaging them with my slippery tongue as if they were the most fragile things in the world.

Samantha's eyes were closed as she made soft humming noises. I myself mewed little kitten moans as I finally managed to draw both her swollen balls into my mouth at the same time. I reluctantly released them and scooted myself into a laying down position flat on the bed now. I got my hands under her knees and pushed them up to her chest, exposing her tight little pink asshole.

She knew what I was going for and locked her own forearms under her knees, scooting her ass more up towards me, exposing her sphincter muscle as much as possible. Pulling her knees apart, as wide as she could, she gave me perfect access to her pink wrinkled rose bud.

I dove into it and it smelled so fresh and clean. I smelt soap, lotion, powder and perfume as I got lost in the clean sweet scent of her ass. Opening my mouth as wide as I could, I locked down directly on her hole with my lips. The ring of her sphincter felt like a hard circle of muscle, but surrounded by the smoothest softest skin in the world. I locked my lips down on it hard, with my mouth wide open and just massaged that ring with my tongue. I slurped and licked all over it, making my tongue into a pointy tip and teasing her as Samantha groaned and I felt her anal ring twitch to my manipulations.

I took my teeth and nibbled on it gently, making her squeal and writhe to my manipulations. When I gently chewed on it, she really started squirming and tried to open her legs even wider so I could get access to more of it. I hate to sound cocky, I'm not a braggart, but I really felt like I was talented and had some innate ability to read people's sexual reactions and please them. While just a few days ago, the thought of putting my mouth on a man's ass, even one that looked as much of a woman as Samantha did, I would have been revolted and disgusted by the act. But now, it was like my life's calling to please.

"Nicky, please girl, come suck my cock. I need it sucked now, and rub your cock for me, that turns me on." Samantha panted.

As I sat back up on my butt, again in the lotus position, to lean over her lap and work on her cock, I stopped for a brief second to utter, "Samantha, I can't touch it, I can't, if I do, I will cum all over with just a few rubs."

"I will tell you when I'm ready to cum, I want you to stroke it and cum with me at the same time, okay?" Samantha instructed me.

I leaned down and locked onto her dripping hard cock head, sliding my mouth straight down til my lips mashed hard into her stomach. Once it was lodged firmly in my throat, I just held my ground and tried to extend my tongue to massage the underside of her shaft.

Samantha scrutinized my technique curiously and seemingly amazed, then spoke, "Nicky, how do you do that? You don't gag at all, not a bit, how do you do that? I know I don't have the biggest cock in the world, or the thickest, but I'm not tiny either. I usually gag most of my lovers when they suck my cock. I saw you with your uncle, he's pretty fucking big and would gag anybody, me included, but I saw you the other day slide your throat up and down to his root with no gagging whatsoever. You're fucking amazing, you are gonna be very popular with the big dick guys at work that want deep throat. Honestly, your oral skills are one in a million."

I may have blushed at that, I did feel my face redden somewhat, I was certainly proud of her comment. I was wanted to show off a little bit for her now, so I slowly drew my lips back to the tip of her cock, sucked on it for just a few seconds and then slowly lowered my throat back down on her hard cock all the way to the root. I didn't even gag a tiny bit, not a flinch, I just used my throat like a sex machine and did this over and over.

Samantha groaned every time I bottomed out and then shivered every time I nursed and teased the tip. I got a steady rhythm going up and down, like I was a fuck toy milking her cock. I could feel her cock getting stiffer and stiffer, while there was more sweet precum drooling out of the head when I nursed on it. Samantha was getting close, I could tell. Her stomach muscles were flexing up, the knuckles on her closed fists were turning white, her legs were beginning to tremble involuntarily and her panting was ragged.

"Now Nicole, cum with me, stroke your cock." Samantha stuttered out the command.

I gripped my sensitive cock and within 5 strokes, I was squirting spray after spray onto her tight nut sack and cock. It was too much for Samantha as she watched me shake and quiver, while still trying not to interrupt my rhythm for her until she blew. I scrambled to stay with it as the throes of my own orgasm made me groan and lose my body control. I was having trouble keeping a steady rhythm up and down her cock as I got real jerky from the spasms, but I hung in there and my girl screamed.

"Eat my cum Nicky, eat my cum, oooh fuck, oooh fuck...of Good Lord fuck, I'm cumming." Samantha cried out. As her cock spasms started, I felt pulse after pulse of hot cum jetting out. I kept my up and down pace going, still locking onto the head of her cock with my lips and swirling my tongue on it for a second on the up swing. The spray was intense, I felt the spasms of each squirt as she filled my throat and mouth. The best one was when I had just the very tip of her cock locked onto with my lips tightly, massaging my tongue into her pee hole. She spurted so hard on that one, that it squirted out like an unclogged hose and actually went sideways onto my cheek.

As we both basked in the afterglow of our orgasms, I was still hungry and nursed on her softening cock.

"Clean it up Nicole, you know you want to." Samantha commanded.

I leaned over as far as I could and started liking up both her spilt cum and my load that had splattered all over her balls and stomach. I had tasted my own cum before, this was not a first for me, and it was delicious. After she was cleaned up by my tongue and mouth, she patted the pillow next to her and I crawled up there and put my head on her shoulder. We both just held each other and rested when her phoned chimed an incoming text.

Samantha read it and replied, then kissed me so softly on the lips, that I thought she might be a real life angel. Never happier in my life, I nodded off as she replied to another text. After a nice little nap, Samantha shook my shoulder and said, "Get up Nicky, we need to fix your makeup, your uncle will be here in 30 minutes. Read these as she showed me a series of texts."

"Sam, did you hook up with Nicole?"

"Yes, she's here now."

"How does she look?"

"OMG!! You won't believe, she's totally hot."

"Really? How much did you spend?"

"Close to $1,300 and that should cover her."

"That's cool, I'm coming over, be there in 30."

I had woken up fresh after my little nap and Samantha told me to go the bathroom and compose myself. She helped me touch up my make and not a minute too soon, as there was a knock on her door.

"Stay in the bedroom, I will tell you when to walk in, I want to give him the full effect all at once and surprise him." Samantha instructed me.

I don't know why I was so nervous about Uncle Ronnie's approval, but I had butterflies in my stomach as I heard them talking while waiting for her to call me in.

"Nicky, come on out here." I heard Uncle Ronnie holler impatiently.

As I walked into the room, Uncle Ronnie just stared at me in disbelief. I almost felt like he was thinking, who is that, where is Nicole.