Bitch Maker Ch. 04

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Reluctant Tim chooses to be a bitch for Sammie.
4.2k words
4.62
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Part 4 of the 4 part series

Updated 10/20/2022
Created 04/02/2006
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YANKEE DAN
YANKEE DAN
928 Followers

"Fuck you Excel." I muttered.

It was Monday morning and I was at work, but I hadn't managed to do much. I had to get cell G14 to show the total of B2 through B10 divided by B12 plus the total of C2 through C10 divided by C12 but every time the box just displayed a bunch of Xs. I had done this kind of thing before but something was off. I should probably just have asked Thomas from accounting but he already thought he was too smart.

I was also distracted by the fact that I had sex with two trannies over the weekend and I wasn't really aware of what I was getting into or sure I wanted to. I had been back and forth about it during the sex as well. At first it was hot, but they wanted to fuck me and I wasn't ready. 'No' wasn't an answer they had wanted to hear however.

It wasn't like I was going to the police either, the last thing I needed was everybody in the office knowing I had been fucked in the ass by a female co-worker. I decided the best thing to do was go on a break. Cause if you're not being productive the best way to get productive is snack machines.

I opened the fridge in the break room and retrieved my salad. I got a soda and candy bar from the machines and sat down. Just as I was taking my first bite Thomas walked in. Thomas is about twenty four years old, with a scruffy beard and short hair. Some call him, "The Chin" because his chin is ridiculously pronounced.

He sat down next to me and began texting on his cell phone. Then Sammie walked in.

I lowered my eyes to my salad, immediately feeling awkward, hoping she would be in and out.

"How was your weekend Thomas?" She said as she sat down next to me.

"Eh, it was fine." He replied.

"What about you Tim?" Sammie asked me.

"It was fine." I mumbled.

"Ah, you probably just won't tell us about all the wild parties you go to so we can't show up at them and find out what a fag you are. Same goes for you Thomas."

"Yeah," Thomas said, still typing on his cell, "I love the dick, don't tell the others."

I ate my salad in silence; Sammie smiled at me and got up, leaving the room.

When I got back to my desk I still couldn't work, I still couldn't stop thinking about Sammie and Alex, and what I had done, and had done to me. Before long I pulled up Google and started searching. Shemales, tyranny's, hermaphrodites, cross-dresses... subjects I hadn't really looked into before. I had always thought shemale just meant guy in drag... I wondered what Sammie's story was.

After about thirty minutes I was gravitating more towards pornographic sites than informational ones. I clicked on one picture of a shemale on her knees giving head and a video popped up.

"Shit..." I whispered and was turning down the volume just as Sammie walked in.

"What's that noise?" She asked, smirking.

"Just YouTube." I said.

The computer choose that moment to become unresponsive naturally and my clicking on the exit button did nothing, the video was mute but still playing as Sam stepped up beside my desk and looked at the screen.

"Shit Tim, at work? Really?" She laughed. "Let's see what you got here."

Sammie knelt next to me and looked at the screen for a second. "So, which one do you want to be in this scene?"

As she spoke she put her hand in my lap and started rubbing my dick through my pants. My rational mind wanted to push her away, but my id was rearing its head and proving stronger. While we watched the girl on the screen bob her head Sammie's hand reached into my pants and started stroking my dick.

"You like that?" She asked quietly.

"Yeah." I said, breathing deeply.

"Are you gonna come to the house tonight?" She was smirking at me, I hated it but... I didn't have any place to stay and her fingers on my balls seemed to be an irresistible invitation.

"Uhh... I don't know. What's gonna happen if I do?"

"I'm gonna fuck you." She said matter of fact like. She pulled her hand back spit on it, then wrapped her hand around my cock and started pumping.

I didn't want to get fucked really, but I was getting hot seeing this t-girl suck dick...

"Can I blow you instead?" I asked.

"Sure." She said, and pulled back her hand.

As she walked out I whined and she looked back saying, "You gotta wait until tonight to finish."

***

I sat in her driveway for a good twenty minutes debating whether I should go in or not.

Everything was jumbled up in my head. I tried to sort out what was happening to me and where I wanted to go with it. I had dressed like a girl and thought it was fun fooling around with Alex... but I hadn't known she was a he. I had been disgusted and mesmerized at once when I found out. Some sick compulsion had led me to get down on my knees and start servicing Sam when she asked me to... but then they had taken my further then I wanted to go, had basically raped me.

Now I felt that same sick compulsion to go in there and suck Sammie's cock. I imagined rimming her while I jerked her off and my dick strained in my pants. I had never had sex with men before this, but then Sammie and Alex weren't exactly men...

If I went back in there knowing what I'd be doing, probably in drag, would I be a man anymore?

I got out of the car and walked to the front door, knocking three times. I felt nervous waiting on the porch, like I needed to look around and make sure nobody saw me going in. Sammie opened the door dressed in tan khakis and a striped v-cut shirt that was quite tight on her. It showed her athletic frame well. She had great body, she didn't look 'mannish' but she did look very fit. I looked down at her feet, I felt pathetic knowing what a soft body I had, if she wanted to fuck me then she could hold me down I was sure, and here I was coming back into her home.

"Come inside." She said in a casual tone, as if the air wasn't choking me with the tension!

She walked down the hall not even motioning for me to follow. I walked down the hallway slowly, feeling like an inmate walking to the electric chair, but still... my cock was hard and my heart was beating fast.

She sat back on her bed and picked up the channel changer, turning the TV's volume up. I started to crawl into bed.

"I don't think so bitch." Sam said, pushing me off with one foot. "Do I look like I need some sissy guy? Get pretty if you wanna get in bed with me."

I turned to walk out.

"Hey Tim!"

I stopped and looked back.

With some genuine concern in her voice she said, "If you just need a room to crash that's cool go to your room and put the clothes in your closet in the living room."

I nodded and walked to the guest bedroom where I had been tied down and violated over the weekend. A rather modest outfit was on the bed. It was a black dress with a flowing skirt, coming down well past the knees. It had a pattern of bright flowers going up and down the sides.

When I picked it up the cock cage fell from inside it onto the floor. I groaned. That thing I really didn't want on me. I debated for a moment. If she put it here it was part of my outfit and I didn't want her to punish me. I had no choice if I wanted to go through with this, I put it on. It was already open when I picked it up, but once closed I couldn't get to my dick anymore, and without the key my cock belonged to Sammie.

I sat at the vanity and put on make-up, doing my best to make it look natural, not like a hooker. I put a mild shade of pink on my nails and gazed at myself in the mirror. I wasn't the beauty that Sammie and Alex were, but the loose fitting dress helped hide the fact that I wasn't as curvy as them, and the long hair of the wig I found on the vanity framed my face well.

"Oh my God." I said to myself, realizing how much effort I was now putting into making myself look feminine. Was this just me going to ridiculous lengths to get my dick sucked? I remembered Sammie asking me which actor I wanted to be in the porn scene today. Did I want to be the shemale on her knees sucking cock?

"You look pretty." Sammie said as she glanced at me when I crawled into bed beside her. I lay next to her and she turned on her side facing me. Her hand reached out and took hold of the back of my neck, pulling my face to hers. It kissed me softly on the lips and looked into my eyes, I felt my legs start to tremble, I was gonna be fucked in the ass for sure! I was being treated as a woman not a man, Sammie's gender neutral clothing had been a statement I thought, and it said I was the bitch in this bed.

Sammie broke the kiss and asked, "You want my cock Tim?"

"Yes I want to suck you cock so bad!"

"I'm changing your name, from now on in this house it's Tammy. Will you be my little bitch Tammy?"

I gulped, "Make me your bitch Sammie please!"

Sammie pulled me closer, her breast pressing against me and her kiss becoming deeper. I parted my lips to allow her tongue in my mouth. She was forceful and demanding, her hands exploring my body. My head was swimming, this was different I quickly realized. The whole tone wasn't like before... this wasn't what I expected. I thought she would drop her pants and tell me to suck her off immediately, this was somehow more intimate, and it made me feel vulnerable.

She pinched my nipples through the fabric of my dress and I moaned into her mouth. She bit my lip and then my neck, making me sequel like a girl. I slid my hands under her shirt, she raised her arms and I pulled it over her head, letting her bare tits fall free. Sammie grabbed the back of my head and pulled me to her tits. I opened my mouth and begin kissing around the flesh of those smooth globes, the soft skin feeling delicious on my tongue.

I teased around her areola and looked up at her face; she smiled down approvingly as I stuck out my tongue and flicked it over her hard nipple. She closed her eyes with a sharp intake of breath. I worked all over her breast with my mouth, my cock becoming extremely uncomfortable in its cage. Then Sammie's hands pushed my head lower. I licked over her stomach, kissing lazy circles that spiraled downwards. My fingers unbuttoned her pants and pulled down the zipper. I pushed my face against her panties, black transparent material through which I felt the heat of her cock on my forehead.

I pulled her pants down and squeezed her asscheeks, rubbing my face against her crotch. I was getting into my role, forgetting myself, only wanting to act like a bitch hot for cock. Her panties were thin enough that all I had to do was pull them aside; they looked fucking sexy like that, pulled aside to let her cock fall on my waiting lips. I sucked on the bottom of the shaft, my tongue hanging out I slurped up to the head. I held the cock in my hand and rubbed her member around my lips, making her arch her back as my lips stimulated the tip.

"You like that dick don't you bitch?" Sammie asked.

I nodded as I twirled my tongue around her glans. Sam pressed her foot forward between my legs and felt the cock cage.

"Good girl, now convince me you deserve to have it taken off."

Sammie rolled onto her back and I followed her cock like a dog on a leash. I propped one elbow on the other side of her stomach and, looking down at the feet, started taking her cock into my mouth. The head and the first three inches were comfortable; the next two inches took a little work. I took it as deep as I could, gagging myself, but I kept trying. I gagged, and then backed off. I let myself get used to the five inches then forced my head down, gagging again.

"Uhhh, fuck yea you cocksucker! Gag on my cock!" Sammie curled her hands on the back of my head and pushed me down.

The head of her cock forced itself into my throat and set me choking, but Sammie's strong hands wouldn't let me up. Instead she forced me down until my nose was buried in her pubic hair. I could barely breathe but the scent of her sweaty balls filled my nostrils, the taste of her precum was on my tongue, strong and salty.

Finally she let me up and I took her rod out of my mouth, jerking it with my hand. I crawled down the bed and turned to face up her body. She was playing with her tits as she watched me intently. I began to lick her balls while I stoked her hard cock. It was a magnificent sight from below like that. Veiny, with a beautifully well-formed head, the skin so soft but hard underneath, I squeezed it as hard as I could, liking the feel of it in my hand. My eyes fixed on the lipstick around the base.

When I felt ready to have her in my throat again I let her nuts slide from between my lips and licked up the cock, kissing the tip before diving back down on it. I gagged and started to pull off when she 'helped' me again. Thrusting her hips up and holding my head in place. My eyes watered and I made gurgling noises.

"Oh fuck your throat feels great." Sammie muttered as she started to pump in and out.

I wasn't experienced enough for it but she didn't care. I thrashed about beating my hands on the bed as I started choking and needed air but she just fucked my face without letting up. Finally when my lungs were burning she pushed me off.

Sammie leaned up and took my face in her hands, pulling me up to her. She kissed me softly and held me while my breathing got back to normal. When it had she reached under her pillow and pulled out a key. I reached down and pulled up my skirt to my waist and my dick popped happily free from the cage as she released it, running her hand softly up and down it as she pushed me on my back and slid down my body.

I screamed in pleasure as soon as her lips engulfed my dick. I ran my hands through her hair and bucked with excitement. Sam didn't complain. She took my dick into her throat easily and bobbed quickly. It was even thirty seconds before I felt myself close to cumming.

"I'm gonna cum." I warned her.

Sammie pulled her mouth away. "Well you can't cum yet." She said.

Sammie got up on her knees, leaning over me. I marveled at her tight body. She was muscular but not female body builder freakish and with a cock bigger than mine bouncing over me. She leaned forward and pressed down on me, our cocks rubbing together, precum mixing on my stomach as her tits sent shivers down my spine. We kissed.

"Tammy... Are you ready?" She asked.

"For what?" I asked, playing dumb.

"To have your ass ploughed silly." She said, licking the side of my neck. "That's what little bitches like you are here for."

I was scared like I was sitting down in the dentist chair for a root canal.

"You want this?" Sammie hissed, insistently, moving her body and grinding our cocks together.

Lust overcame me. If letting her fuck me would earn me an orgasm from this unbelievably gorgeous vixen then I would do it.

I gave in and said, "Yes."

I couldn't say no, but I trembled as she shifted me onto my hands and knees. I reached out and pulled both pillows to myself as Sammie poured lubricant on her cock. I squeezed the pillows tight to my chest as I felt the head of her cock sliding around my crack. She was in no hurry and rubbed up and down the valley of my ass, sighing as it brushed across my sphincter. She pulled it back and I felt a finger push itself against my asshole. There was only a moment's pressure before her feminine but strong finger slipped into my rectum. She pushed straight for my prostate, rubbing it in small circles.

This made my cock twitch and I sighed. When I had been fucked roughly before I hadn't fully appreciated the feeling that could come from having your insides messaged, and I began to think this would feel good.

Then finger was pulled from me and Sammie lined her cock up with my rectum. Sammie paused to ask me a question.

"Are you my bitch?"

"Yes." I answered into the pillows, and Sammie pushed.

I grunted as the head slowly forced its way in. The stretching of my tight anus was excruciatingly painful. It immediately made me start to go limp and all thought of enjoying being fucked went out the window.

"God it hurts!" I screamed.

"Shhh." Sammie whispered. "You want this, you can take this dick slut just relax."

I bit into a pillow and whimpered.

Sammie pushed in more, the shaft beginning to bury itself in my rear.

"GOD! Take it out!"

"It's so great when a bitch isn't fully broken in yet. Your ass muscles are twitching quite nicely."

I couldn't speak anymore; I just made pathetic whining sounds.

Finally I felt my buttcheeks pressing against Sammie's hips. Sammie sat there unmoving, showing some mercy by letting my ass start to adjust.
When my panting started to slow down and I relaxed my grip on the pillows a bit Sammie started to move. She pulled slowly out until just the tip was in and then pushed back in equally slowly.

I looked over my shoulder to see her eyes closed, hands on my hips. Her tits glistened with sweat. She moved gently, not increasing her pace. I grunted with every soft in stroke, for as gentle as she was being the pain took my breath away; my legs trembled while her balls softly swung against mine.

"How are you?" She asked.

"I'm okay." I said.

Several minutes passed and my dick started to slowly get hard again. I could feel the head of her cock moving over my prostate, and numerous other strange sensations. I had to use the bathroom, I hurt, I felt pleasure, I felt a curious sensation of being penetrated so deep that was both alarming and somehow comforting. It was like I was being stabbed but I wanted the knife deeper.

My grunts started becoming moans. I pushed myself up on my hands and looked back at Sam. She leaned forward and kissed me, her tits rubbing on my back.

My dick was rock hard again.

"Fuck me, oh fuck me Sam fuck me, fuck me, fuck me, oh God Sam fuck me..."

There I was, lipstick and make-up, long black hair tossing about, my skirt pulled up so my hairless legs and ass were available for Sammie's hand to roam, and a hard rod pistoning in and out of my asshole. The pain had faded almost completely, I felt like pleasure was radiating from inside my ass where Sammie was drilling deep into my bowls. Her pace quickened and the room was filled with the sounds of our heavy breathing, along with the SLAP SLAP SLAP as my ass was pounded.

"Uuughh!" I gritted my teeth and pulled at the blankets, my pink nails curling and releasing the sheets.

"Turn over cum slut." Sammie said, pulling her cock out.

I rolled onto my back and Sammie lifted my ass up, stuffing the pillows under me, then she mounted me again, our faces inches apart I looked her in the eyes as she pushed into my ass again. She took my hands in her and our fingers intertwined over my head as she started fucking me faster.

"I love you fucking me Sam!" I screamed.

"Ahh, such a tight ass!" Sammie yelled.

She put one of my hands on my dick. "Jerk yourself off cunt!"

I didn't need encouragement for that and starting stroking myself. At this angle the cum would shoot all over my chest, and possibly my face if I sprayed hard, which I was feeling sure I would. The thought of my face being blasted with my own cum was too hot to bear and I felt it well up in me.

"I'm cumming!" I screamed.

I shot a wad of cum that flew in my open mouth. Another hit my cheek and three more squirted my dress. My legs wrapped around Sammie as she pounded my ass as hard as she could.

I grunted and shook, the taste of my own cum on my tongue, as Sammie shuddered.

"Fill me up Sam, put your spunk in my ass." I whispered, encouraging her.

In a moment, she did just that, firing a large load into me in a series of spurts. My sore asshole felt her cock pulsing.

We lay entangling for several minutes, her lips found mine and we kissed. I slept in the bed with her cuddled against her chest. I felt safe in her arms. I didn't know why I had been thinking that I wouldn't want to be this hot woman's bitch.

YANKEE DAN
YANKEE DAN
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