The Sissy of Hawthorne Ch. 03

Mrs Talbert is a widower. She has a daughter my age that lives out of state. She brings can goods to church every Sunday to donate for those in need. She bakes cookies and hands them out to all of her neighbors, me included. She is always hoping her daughter will move back, and she says she will set us up when that happens. I always smile.

Of course it was Mrs Talbert walking up the stairs precisely when I scurried down them. Scurried down them in a blue dress that barely covered anything on my body, and wearing full makeup. I even tripped on my heels in front of her. To say she looked shocked would be an understatement. I didn't slow down. I had to be on time. I ran the best I could in heels through the parking lot and into Frank's neighborhood. It seemed like every house had a man working in the front yard. Did they notice me? I don't know. I didn't take the time to look.

A small S10 pickup pulled up next to me and slowed down. The driver rolled down the window and glared at me. I looked straight ahead and tried not to look at him, but I could feel his eyes on me. My legs trembled as I walked in my high heels. What was this guy with a backwards hat going to do.

"Fucking faggot!" I heard him yell before he sped off. He nearly hit me in the process. It was definitely on purpose.

I thought about taking off my heels and running barefoot, but decided not to. I was close to Frank's house. Frank's street was quiet. I got up to the door and Frank opened it.

Frank led me into the house. He looked me up and down and said, "I'm sure people saw you. Did anybody recognize you?"

"Yes sir. An older widow in my apartment building." I said.

"Very nice." Frank replied.

Frank ran his hands up my body. He found my plug when he lifted my dress, "What do we have here? I didn't tell you to bring a butt plug. I wonder why you disobeyed my instructions." Frank said.

"I'm sorry sir. I'm just so used to wearing it, now." I said.

"Did anyone say anything to you as you walked over?" Frank asked as he ran his hands over my whole body.

I said, "One guy called me a faggot from his truck. He sped away afterwards."

"Hmmm. Well, you kind of have to expect that around here. Do you dress like this and still go by Jim, or do you fancy a different name?" Frank asked.

"Ashley, sir. My real name is Ashley." I replied.

It just dawned on me that Frank, the person I started this journey with, didn't even know my name.

"Your real name is Ashley, huh. Says that on your Drivers License?" Frank sneered.

"Yes, it does. James Ashley Tanner." I said.

"Okay, Ashley, what are you interested in? What do you want to get out of this?" Frank asked., with a smile.

"I want, um, I want to, um, sex... I mean fuck you. I mean that, my ass and you. And I also I'm, I....want to do spanking, um, with you., if you like that...." I stumbled through.

Frank l just stared at me. I'm such a fucking idiot. I always do this stupid shit. Word salad comes out of my mouth when I'm on the spot like this.

I corrected myself by saying, "I mean, I'm sorry. I mean that.... I mean that I want you to fuck me and I want you to spank me. Brad spanked me and I have had fantasies of you spanking me ever since. That's what I meant, sir."

Frank nodded and asked, "How did he spank you?"

"With his hand. I was over his lap. And then he used his belt." I told Frank.

"In an apartment? Did anyone hear?" Frank asked, surprised.

I blushed. "Yes, the Chinese Takeout driver heard and saw me bent over the couch while Brad paid. He congratulated Brad on doing good work." I said.

Frank smiled and asked, "I didn't see any marks. Did it hurt the next day, did it leave a mark?"

"Yes sir, my butt was sore for a couple days. It was very red when he finished." I told Frank.

"He went easy on you." Frank replied.

"It didn't feel easy. The belt hurt like hell." I said, in a matter of fact tone.

"Talking back, huh." Frank said.

"I'm sorry." I said.

Frank grabbed me and pulled me close into his masculine arms. I felt light headed as he ran his hands all over my body. His house phone rang. Frank let it go to the machine.

"Frank! This is Janet Wiechert. Tom and all of the kids were driving to the Festival. I don't know what happened, but they got into an accident. It's bad Frank. That's all I know. They are in a hospital outside of Savannah....." The voice on the answering machine said before Frank picked up the phone frantically.

"Janet, this is Frank." Frank said and told her, "I'm getting in the car now. Yes, yes. Thank you. Still at home. I'm going to.... Where exactly.... Sure, yes, that makes sense. I will pick you up right away."

"I'm sorry Ashley. I have to go." Frank said as he hung up the phone.

"I hope they are all right!" I said, holding back the tears for Frank.

I felt horrible as I walked away from Frank's house. He needed to go, I told him I would walk. I didn't want to walk through the neighborhood so I cut through some woods to the main road on the side. It was a lot longer to walk this way but at least it wouldn't have people standing in their yards.

A few cars passed me. I tried to not notice them. I knew my ass hung out of my dress. I knew they could see my ass. No need for me to look at their reaction as they drove by.

A green Jeep Cherokee slowed down and matched speed with me as I walked. It slowly drove in front of me and then pulled off the road. The passenger window lowered as I walked by.

"Need a lift?" The driver asked as he stared at me in my slutty outfit.

I got in. It was a stupid idea, but so was walking down a South Carolina street looking the way I did. The driver was in his fifties. Red hair and balding. Short and overweight. He started driving.

"Usually don't see girls like you in this part of town," he said and asked, "Are you staying at one of the hotels on two-seventy-eight? Do you have a room?"

"I have an apartment." I said.

"Taking a stroll with an incall. That's nice. Where is it?" He replied.

"Do you know the Hawthorne Apartments?" I asked him.

"Yes, I pass them on my way home." He said with a smile.

"Building Two." I said.

He drove me home and parked. I was surprised when he turned off his car and followed me up the stairs. I looked at him strangely, but he still followed. He had gold rim glasses and wore a USC "Go Cocks" shirt. I opened my apartment door and he followed me in. I didn't want to make a scene in the hallway so I froze and let him in.

"What's the damage going to be? I got a good look and I want it all baby." The man said.

"Ummm." I mumbled.

"I can't do more than three hundred, and that would have to be a full hour." He said.

It hit me like a ton of bricks. He thought I was a street walker.

In a panic I nodded, but my brain really couldn't process what had just happened.

"Half up front." He said as he handed me three fifty dollars bills.

He took off his shirt. He had a large belly with grey and red fur. He removed his pants and his tight white briefs. He was hard. He had very thick amber pubic hair. His cock's shaft was even paler than the rest of his pale skin, but his cock head under his foreskin was bright red. He must have been at least seven inches.

I stood still and looked at his cock. It looked kind of weird, with the bright red head. I know I had been paid for sex by Travis before, but that was at least someone I already knew. That also felt different, maybe even like a game. I had been with strangers, but this was still different. He one-hundred percent believed that I was a real hooker. I had already taken some of his money. I would literally be a prostitute if I had sex with him.

He looked at me puzzled and said, "It ain't going to suck itself."

I walked forward towards him and grabbed his penis. I walked towards my bedroom while I held onto his dick. He grabbed my ass cheeks as I walked. I sat him on the edge of my bed and kneeled in front of him. I opened my mouth and decided to become a whore. I took him in. He wasn't very thick so it was easy to work him down my throat. He moaned as I sucked his cock. His thick pubic hair tickled my nose. He didn't smell good. I like the musky smell of men. He had that, but he also smelled like poop. His dick tasted like he didn't shower much. I tried to put it out of my mind and get it over with. I really wanted him to leave my apartment and he wouldn't until he was done.

He waited for me to give a pause and then rolled back onto my bed. His hairy anus pointed at my mouth.

"Eat my ass. Eat it good." He said.

I grabbed a wet wipe from the nightstand real quick. He hadn't wiped well. His hairs were stained. I cleaned everything as good as I could. I was repulsed by the idea. He grabbed me by my hair and yanked my face towards his ass.

"This is what I'm paying you for, eat my ass" He said.

I stuck my tongue out and started to lick his hole. He moaned as I worked my tongue into his ass. He tasted horrible. He really needed a lesson in basic hygiene. I continued to lick and probe with my tongue as he moaned loudly. He ended my misery when he let his legs dropped out of exhaustion.

"Take your clothes off." He said out of breathe.

I took off my dress, heels, and underwear. My little limp cock hung down. He grabbed my little cock and jerked it. He put it in his mouth and sucked on it. I was really turned off and there was no way I would get an erection with this dirty toad of a man.

"You're just a bottom, aren't you? I usually top, but I like to bottom for ladyboys from time to

time. I travel to Thailand at least twice a year." He said.

I got up and grabbed a condom from my toy box. I had tried to put condoms on the toys rather than clean them, but it was more of a hassle than just cleaning them each use.

I put the condom on him and lubed his covered cock up. I put some lube in my backdoor and got on the bed on my hands and knees. He got behind me. I felt his bright red cock head slide between my cheeks. He pushed in. He slipped in easily. I felt so cheap. He fucked me slowly. I don't think he could physically go faster. He panted hard. He pulled out and collapsed on my bed.

"Get on top." He said.

I straddled him and lowered myself on his pole. I wanted this over so I worked his cock hard. I grinded up and down, my little cock flapped in circles as I fucked his cock with my ass. I leaned back and put my arms down to hold myself up. I lifted myself with my legs. I fucked him as hard and fast as I could. He only lasted for a couple minutes and came in his condom.

"You're a good fuck. You need to work on rinming. That could have been better. You should also use viagra so your clients can play with your cock. I usually save my money for Thailand, but you were a good gamble." He said as he handed me the rest of the money. He was there for a total of twenty minutes.

I gargled a bottle of Listerine and threw my toothbrush away after I brushed my tongue and whole mouth. It wouldn't have bothered me to taste some ass, but he was dirty. I felt sorry for all the ladyboys in Thailand.

I looked at my bed. There were brown stains where he had sat and laid on my bed. I was beyond repulsed. I took the sheets off and washed them. I took a shower and tried to rub his smell all of me. I felt dirty, no matter how much soap I used. I put the money with all the money I had collected from Travis.

My phone rang. It was Frank's number.

"Hello." I said.

"Hey Ashley. I just wanted you to know that my kids were going to be in the hospital for a couple more days before I can take them home. I guess their friends dad was playing with his iPod dock and he somehow went across the median and hit another car with a lady, nearly head on. The dad and the driver of the other car are in serious condition, but the kids weren't as bad. It will take some time, but the doctors think all of the kids will fully recover. They both had multiple fractures and concussions. I'm with them now. They are okay. Sorry we couldn't hang out." Frank said.

"I'm glad they are okay. Let me know if I can do anything to help." I said.

"Thanks Ashley. Good bye." Frank said and hung up.

Frank would be caring for his kids for awhile now. I didn't see me having any play time with him for months, if even.

It felt like it was late at night, but it was only six-thirty in the evening. My work phone rang. It was Travis. The office had given him my phone number a couple weeks ago.

I answered the phone.

"Jamie!" Travis nearly shouted into the phone. "I need you to stop what you're doing and come to my house right now. Dress like a very slutty girl. If you don't have girl clothes then buy some and bring me the receipts. Come at once, you will get paid well." Travis said and hung up.

Travis was inadvertently responsible for most of my income at this point. My duties at work were mostly his account. He also paid cash for extras. I don't know if he would hold that over my head, but I didn't see any point in testing him on that tonight. I did my makeup and hair again. I put on a similar dress to what I wore before, but this one was black with fine mesh side panels that went up the entire dress. I wore sandals because I was done with heels for the day.

Travis greeted me at his door. There were two other men there.

"Jamie, this is Dr. Whittier and this is Mark Huger, Mark is security for tonight."

"Nice to meet you, my name is Ashley." I said to them. Travis smiled.

"If you don't mind me asking, have you considered Hormone Therapy, Ashley?" Dr Whittier asked.

"Yes, I just don't no where to start." I said.

"You start with me. I'm an endocrinologist. If your serious, I can help cut through some of the red tape and get you started quickly. You would just need to do some blood work, and we would schedule you an appointment with a friend of mine for a referral. But that would just be a formality. We can get started this week." Dr. Whittier said.

"Yes yes yes, good doctor. That will will help, but for tonight I need Jamie, I mean Ashley, just like she is." Travis said as he led me to a room downstairs.

Travis showed me inside the room. The room was lit with black lights. There was a bed, a harnesses that hung from the ceiling by a rope, and a big bottle of lube on a nightstand.

I looked around as Travis explained to me what had happened, "The Doctor had arranged to bring a transsexual pornstar that is a patient of his for tonight, but she got in a car accident outside of Savannah. Head on collision. She is is serious condition. I have several men coming who are all like minded. They will love you. We will have a gentleman's party upstairs. It's a poker game. It's a big poker game. The buy in is a quarter million dollars. You are tonight's extra entertainment. Mark will watch the door and collect payment. You will do whatever the man wants for around a half hour. Mark will watch the time. There are condoms in the drawer if he wants to use one, but only if he wants to use one. You do exactly as he wishes. You will receive $200 per man. The rest goes to Mark and I. Use the bathroom to cleanup between men."

"But, how many men, how many men am I supposed to sleep with?" I protested. This scenario frightened me.

"They are older gentlemen, they are captains of industry and former captains of industry. Most of these men have big egos and small cocks. Some of them can't get it up anymore. Most of them take Viagra as if they were vitamins. They all married women and had families so they looked the part. They get excited when they are with what they really want. They don't last long when excited and they pay very well. Everyone coming here did screening with Dr. Whittier weeks ago. They are all clean. A lot of them will pass out as the night goes on. Mark will take care of removing them. You love cock so just enjoy yourself. Dr. Whittier is going to do a quick examination. Don't worry." Travis said and then hurried out of the room.

Dr. Whittier walked in and turned the normal lights on. He looked at me and said, "Raise your skirt and drop your panties."

I did as I was told. The doctor inspected my penis. "Have you ever put this inside of anyone?" He asked.

"No sir." I said.

The doctor slowly stroked my cock. The Doctor had really kind eyes and looked at me intensely.

"I need your cock nice and hard for our examination." The Doctor said.

My cock got hard after he stroked it for awhile. The doctor looked at it closely and said, "Very nice, very clean. I see why you're a girl now," and then laughed, "Not going to give anyone an orgasm with that."

"How many men have you been anally penetrated by?" The Doctor asked.

"Only three." I said.

"How many of those men paid you for the encounter?" He asked.

"Two." I replied.

"How many wore a condom?" The Doctor asked.

"One." I told him.

"Was the one who wore a condom a client?" Dr Whittier asked.

"Yes." I said.

"Was Travis the other paying client?" He asked.

"Yes sir." I said.

The Doctor pricked my finger tip and collected a couple drops of blood and asked, "The guy who wasn't a client, was he gay or was he straight? Is he older or younger?"

"He lives in my apartment. He has a live-in girlfriend. He has cheated on her a couple times. Usually with girls. One time with me. He is my age." I responded.

"How long ago?" The Doctor asked.

"It's been a month." I said.

"That was a newer HIV test that is still being evaluated. I'm one of the few doctors that have access to the trail run. It will give us a result in a few minutes. It's accuracy is very high, it just isn't sensitive enough to detect the virus in under a week or so from transmission. Travis is clean, and it sound likes the only risky sex you had is with the guy from your apartment building, but that was long enough ago for us to get a positive. Bend over and spread your little cheeks. I need to inspect you from that side." The Doctor said and instructed.

I did as he said. He didn't put on gloves. I felt his lubed finger penetrate me. He worked his finger around my opening and pushed it inside of me.

"Very clean, and your test came back negative. I'm going to use a different tool to inspect you, to make sure you're okay." The Doctor said as I heard the unmistakable sound of a zipper going down. I heard him fidget with a few things behind me and then felt a cock at my opening.

The doctor grunted as he pushed inside of me. I stood in the center of the room, bent over, with my hands holding onto my knees for support while Dr. Whittier sodomized me.

"You're a tight girl. You're definitely going to need weekly appointments for your therapy." The Doctor said as he picked up the pace.

I did my best to hold my position as the doctor started to fuck me. He had a long cock, but he was able to bury it inside of me with relative ease. He grabbed me by the waist and pulled me onto his cock as he thrust. The doctor felt good inside of me.

"Fuck, weekly appointments sounds great." I thought as the good doctor inspected me more.

I hated every second with the dirty guy earlier, but the doctor could have me whenever he wanted.

"Holy shit Ashley, I'm cumming." The Doctor said as I felt his cock pump his seed deep inside of me.

The Doctor pulled out, slapped his cock on my ass a few times, and put his cock back in his trousers. He said, "Just wipe what drips out after each guy. You want to keep as much lube and cum inside of you as you can as extra lubricant. You do not want to get torn tonight. The men are clean, so don't worry about trying to flush the cum out."

"Yes sir, thank you." I said.

"We will examine you tomorrow at my house. Life is Beachy will pay for your treatments, kind of like insurance. You will just have a copay each visit, which will be similar to how you just paid me for this checkup. I will update your charts remotely. I will take you back to my place once the party is done with you. You can rest and then have your first checkup." The Doctor told me.