Mother and Daughter Training

By Juliet

Published on Aug 3, 2014

Transgender

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I am slim and petite. More of a female than a male. My body hair is much longer than it should be. I am not sure whether to call it an accident or blessing of birth. Both of my parents were of small stature, of Italian descent. I guess that is where I get my dark hair and smoldering features.

I grew up in south Philadelphia, in and around rough neighborhoods. This was the early 80's. I was no stranger to the dark side of people, and the seedy areas not far from me taught me a lot about the perversions that now pass for normal in my life.

Fresh out of high school, I got a job at a fast food joint several blocks from my home. I lived with my mother, and my father had passed away about a year before. My mother still looked good for her age (38), and she was interested in several men in the neighborhood.

I still had not figured out my own interests yet. I admired the beauty of women, and the masculinity of men. I think it's fair to say that both turned me on. All of my fantasies at that time involved me being submissive to either a woman or a man or both. Needless to say, I was a very horny person at this time.

I was working the evening shift at the drive up window at work. It was boring and repetitious, but I often got to glance down at the occupants of the vehicles, and this often allowed me to see down low-cut blouses and glance at the bulges of hot looking guys. This evening was uneventful. Even though it was late summer, and people should have been dressed lightly, there were only a few worth gawking at. One hot guy in I guessed his mid 40's pulled up and I got to stare at the bulge in the tight shorts he was wearing. I could see the outline of his hard cock. I was flustered and I think he caught me staring. He winked at me before he pulled away.

I got out of work and had to walk through a seedy part of town to get home. I was walking down the sidewalk of one of the nameless boulevards, when a siren caught my attention and I turned to look in that direction. At that moment, someone walked out of one of the adult establishments, and I walked directly into them. It was like walking into a brick wall with my small size.

I hit the ground and looked up to apologize. It was the hot guy from before. He was staring down at me with a goofy smile on his handsome face. He had been coming out of one of the more perverse adult book stores in the area. The kind that I was too scared to even contemplate going near.

"Hi there." He said. "We meet again I think. You were working the drive-though earlier." A hungry smile came to his face. "Now I remember, you were checking me out. I thought you were a girl at first."

I turned beet red and got to my feet in front of him. He was almost standing over me, and he stood very close directly in front of me. He was well over six foot tall, and being only 5"3", I barely came halfway up his chest. I stared up at him.

"I-I-I-I'm sorry. I wasn't looking, I didn't mean to . . ."

"Relax kid. I am not too upset." He said down to me in a rich deep voice. "You live around here? Come one, I'll give you a ride home." His tone was not one of offering, but of command.

He turned and started walking towards his car a few spots down. I automatically followed him without thinking. I didn't even know his name or who he was, but I was scurrying to follow his lead.

"This one." He gestured to his car as he made his way to the other side. I tried the handle and it was locked. He was driving one of those large 70's cars. He got in and reached over and unlocked the door. I pulled the door open, and was about to slide in when I hesitated.

"Hurry up kid, I don't have all night. Get in." His words made me practically jump into the bench seat, and I pulled the door closed behind me.

"What's you name?" He asked as he slid his key into the ignition.

"Micky. I'm sorry for bumping into you. I was just walking home . . ." I sorta just trailed off. I was a ball of nerves at this point. I just got into a car with a man twice my size and I was in awe of him. I could barely keep from shaking. I was half turned towards him, and I could feel his masculinity radiating from him. He was clean shaven, with close cropped light brown hair. His eyes were hazel, and were hypnotic. He wore a tight shirt that showed off his thickly muscled arms, and his shorts showed off his tan hairy legs. He kinda reminded me of a lifeguard.

"I'm Carlos, but you can call me Carl, cutie" He hit the gas and we pulled out into traffic.

"Yep, I made you right away Micky. No doubt about that. You were eying my cock earlier weren't you?"

I was speechless. Carl turn his gaze to me. I couldn't keep eye contact, so I lowered my eyes, and they happen to rest upon his crotch. His cock was straining the front of his shorts.

"I said, you were eying my cock earlier, weren't' you?" He snapped.

I meekly let out a 'uh-ha'.

Carlos chuckled. "That's good enough for me. If there's one thing I can't stand is a chatty fag."

His words hit me like a slap in the face. He though, or rather sensed, that I was different.

"I went into that bookstore to get a blowjob, but the cocksucker wasn't too good. Some days it's hit or miss. Good thing I hit upon you." With that, he made a sharp right turn, and I slid across the seat towards him. The next thing I new, Carlos had placed his big hand on the back of my head and was pulling it towards his crotch. I was off balance, and basically fell/let him force my head there.

"Hahahaha. I can tell you're eager Micky." My face was now in his lap. "I get the impression that this is new to you. Well, it ain't new to me." Another hearty laugh from Carl. "Don't worry sweetie. I'm gonna train you up right. You're too cute for a quickie." His hand mashed my face against his cock and I was too intoxicated by the moment to resist.

I felt the car come to a stop, and Carl released my head. I quickly scrambled upright, totally embarrassed at what had just happened to me. I noticed that we were at a stoplight in a neighborhood that I didn't recognize. It didn't look safe at all.

"Let's play a game." Carl said. "It's an easy game, and we are both going to end up winners. I am going to ask you a question. If I figure that you are telling the truth, then I am going to give you a command that we both will like. If I figure you are lying to me, then I stop the car and dump you out. Believe me, this is no neighborhood that a sexy young thing like you wants to be left alone in." Carl just stared at me with a grin on his face.

The light changed, and he started moving. "The first question is: Where you checking out my cock at the drive-through?"

I was scared and excited. I knew that I had to tell him the truth, so I squeeked out a "Yes."

"Very good." Carl boomed out. "Very good. I like when sexy little things like you do that. Ok, now here's your command for telling the truth. And remember, I can still dump your ass out any time I like. Take off your stupid uniform and toss it in the back."

I was mortified. I think he could see me physically flinch. "Do it now." He said. "And quickly."

I quickly slipped out of my work uniform, and tossed it in the back before I could give myself a chance to think about it. After the last piece of clothing had gone over the seat, it hit me. I was naked in a car with a stranger, totally at his mercy. Carl stopped the car for another stop light and flipped on the interior light. The light was a shock, and I was scared that everyone could see in. By this time, it was dark enough not to be able to see into a car, but with the light on, it was pretty obvious. At least the traffic was light, and there were no cars on either side of us. Carl stared at me with hunger in his eyes.

"How old are you?"

"I-I-I'm 17"

"Hmmmm. Well, old enough I suppose. Legal at least. Good, here is your next command. Slide next to me and get under my arm." Carl raised his arm and gestured form me to slide beneath it. I was scared, but I had no choice. I could feel his arm surround my shoulder and pull me closer. The light changed, and Carl pulled out.

"Next question: have you every sucked cock before, and if so, who and how often?

"No, I've never done anything before. I'm a virgin." I didn't think I could blush more, but it sure felt like it.

"Ok then, here is your command. Spread your legs. Keep one on the floor next to me, and point the other one towards the door."

I felt so dirty. I lifted my right let and pointed it towards the door. I didn't have much hair on my body, and my little cock was starting to get stiff. The lights from the passing street lights slid across my naked body. I was nestled in the crook of Carl's arm, and he ran his hand over my chest and tweaked my nipples. I was too scared to move. Carl's hand slithered down my body and cupped my tiny cock and balls. I knew that I was under-endowed, and I hoped he wouldn't make fun of me.

"Nice. You have the cutest clit." He gave it a gentle squeeze. "I can't think of any more questions at the moment, so I'll just issue commands. Reach over and undo my pants and let me cock out. I want you to take a real good look at what a real man's cock looks like."

I twisted in my place and shakily put my hands on the waistband of his shorts and freed the top button. I lowered his zipper. The sound of it filled the car. He wasn't wearing any underwear, and his cock sorta pushed its way out. It was magnificent. That's the first thought that came to me, and still does whenever I get near his cock.

"That's it girl, now take it in your hands. I'm going to teach you how to make my cock happy. Get up on your knees and lean over and get a closer look. You and my cock are gonna be real good friends."

I did as he said, and I was face to face with a real mans cock. It was huge by comparison. It was circumcised, and had a large bulbous head. It was pretty thick, and it looked like he shaved it. His balls were overly large just like the rest of him. They nestled between his thighs.

"Now, wrap your sissy hand around it and slowly pump it."

It felt hot when I touched it. My little hand had a hard time trying to fit around it and I settled for just holding it as best as I could. I slowly pumped it.

"Mmmmm. Good sissy. Squeeze a little tighter. Milk it."

I did as instructed with Carl giving me tips on what he liked. There was a large drop of precum ready to drip off the head of his cock. I could smell it. Carl took his finger and wiped it up.

"Open up and suck my finger. This is your reward for doing so well so far."

I opened my mouth and he stuck his finger in and laid it on my tongue. I closed my lips around his finger and sucked on it. I didn't know if it was wrong or right, but it just felt so natural. I enjoyed the taste of his precum, and squeezed and milked his cock hoping for Carl to feed me more.

Carl took his finger from my mouth and put it on the back of my head. I knew what was next, but I needed him to push me to do it.

"Your next treat is going to be right front the tap. Use your tongue and lick out as much as you can from the head of my cock."

I could hear us both let out a moan as I wrapped my lips around the head of his cock. This was the first time I had over had a cock in my mouth and it was perfect. I milked his cock and ran my tongue over the head while licking out the hole. I started using suction to get as much of his precum as I could. Carl put pressure on the back of my head, and I responded by taking as much of his cock as I could. His taste filled my mouth and I started salivating. I was so enthralled by what I was doing.

"Keep going sissy. Keep pumping me and sucking as me as deep as you can. I'll control your pace."

My head bobbed up and down in time with the pumping of my hand. I was loving it. I hoped Carl was too. I was salivating so much that it was running down his cock and all over my hand. I could hear Carl moaning. I felt the car stop, and I started to pull away, but Carl now used both hands to hold my head down on his cock. He pushed it deep enough so that the head of his cock hit the back of my throat and I started to gag.

"That's it sweetie, keep going. Don't stop. I have a real big present for you. You're gonna want to swallow every drop. We both know you were made for this."

I felt Carl's legs tense, and his hips started thrusting up forcing his cock deeper into my little mouth. His cock started pumping on it's own, and I could feel his cum as it shot out with a lot of force into the back of my mouth. I swallowed reflexively. Four or five big squirts and then he started to slow down. I kept sucking and pumping like a good girl would. I felt his body relax and the grip on my head loosen.

"Keep milking me sissy. Get every last drop while I just relax for a minute."

I kept milking him as his cock deflated a little bit. I finally got to taste his cum, and it was wonderful. I think I was hooked on Carl's cum from that moment on.

After a couple of minutes, Carl pulled me off of his cock. I sat there feeling weird while he looked at me.

With a smile he said, "We're gonna have a lot of fun together. I hope you enjoyed your first lesson. There are going to be many more."

I felt giddy when he said that. This was the first time I had ever had praise and felt wanted. I flushed.

"Now, put my cock back and zip up my shorts."

I did so, feeling happy the whole time. The fact that I was naked in a car with a stranger no longer bothered me. For the first time, I felt happy and alive.

Carl started driving. He asked me my address and I gave it to him. All the way there he asked me about myself, my homelife, and general stuff. I answered truthfully. He seemed particularly interested that I didn't have a father and lived with my mother.

When we got to my neighborhood, he told me to crawl in the back and get dressed. He slapped my ass as I crawled over the seat. He pulled up in front of my house. I waited for him to tell me to get out, but when he did, he got out too. I didn't know what was going on or what he was going to do. My mom was home, and the idea of her catching me with a guy scared me.

End Part 1

Next: Chapter 2


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