Once Upon a First Time

"You were supposed to get your mess on the towel. That is what I brought it out for. Now you will have to learn to obey me and what I expect."

I started to put my underwear on when in very scary and demanding voice she said, "Who told you you could put your clothes on? You think we are finished? No! No! This is just the beginning."

"Have you ever seen a naked woman, besides your Mom that is?" she asked as she started to remove her tank top.

I immediately said, "Yes".

"You haven't had you? I bet you are a virgin too?" She stared at me.

"No, I mean yes." I stammered not wanting to admit it.

As she took off her top exposing these big pale tits that were not really round not really anything like I had seen in my magazines except for these enormous large areolas with big eraser-head nipples poking out. She had no bra on underneath and her belly pushed out a little on the sides of her shorts with a couple small rolls of fat. She pulled down her shorts and I saw hair work it's way ever so slightly from her belly button down to what was exposed as a thick forest of dark brown hair. She turned around as she put her clothes on the couch and I got a quick glimpse of her ass and I could see even along her crack there was hair growing there as well, just like what I saw before with Marty's ass.. Her ass was really big compared to these magazines, hell even compared to the only other Woman I had seen naked, Marty! Now naked she walked up to me and took my cock in her hand and told me that tonight I was gonna become a man even if I was hung like a boy. My cock had shriveled down and was covered in a mixture of cum and oil. She held my cock between her thumb and fingers and slid her index finger over the head using the lube mixture. She put the index finger over the tip and I jerked away as it was really sensitive still. She took my dick in her hand as we walked down the hallway to her bedroom she guided me by pulling my cock.

She had a big four poster bed that sat high off the floor. She had me sit on the edge.... My feet did not touch the floor and she got on the bed and spun me around. My feet in the air, my cock slightly getting hard and my ass exposed up in the air, she crawled up between my legs and started licking my balls. She held my legs up in the air and spread as her tongue made it's way from the rim of my ass to the base of my balls and then sucked each one into her mouth. As my cock grew hard right above her nose she said, "I can't get over how small your cock is compared to your balls. But don't worry, I love it just the same." I really was not aware if my dick was small or not, aside from what I saw in my magazines and everyone knew about John Holmes so I had no idea. She started sucking my cock into her mouth. What an incredible sensation feeling her hot mouth and tongue wrap itself around my cock as she buried her face in my pubic hair as she sucked my cock deep into her throat and then back out again. I already felt as if I was gonna cum when she squeezed the base of my cock real hard and held it.

"You can't cum yet." She said. "Now I am gonna teach you how to eat pussy." This whole concept was a mystery. I had heard guys talk about it but I did not know, so I dove in as if I did licking her engorged lips, licking her ass and anything else I could find with hair on it. But most assuredly I was not hitting her clit as she in mild frustration pointed out. So she slowed me down and guided me through it having me back up and use my fingers to examine her pussy and see the wonders of what she was talking about. I was amazed at how wet she was and my face was covered in her juices as if I had bit into a ripe peach. She patted the bed and told me to sit here. I sat on my knees about half way up her body and she told me to straddle her facing her feet.

I climbed over her nearly kicking her in the head as I moved my feet over her head. "Now eat my pussy." She said as I buried my face in that bush. She in turn pulled at my hips pulling me back and I felt her mouth on my cock and my head jerked up in surprise. she slapped my ass and then kept spreading my ass cheeks open as I couldn't help myself trying to keep my tongue going on her clit and find a rhythm of her sucking and my humping her mouth. And then she throws me completely off as I feel her fingers sliding along my crack along my butt hole. As soon as she touched my anus I started coming and she nearly bench pressed me off of her as she must not have been prepared for it and my cum was a mess on her face. Laughing she rolled over and fell on top of me and kissed me. "Well, you are still a virgin. Technically, but I am sure we will change that soon. It was the first time she was smiling and happy it seemed.

We lay there on top of the covers of her bed. I felt very uncomfortable with nothing to say. She played with my cock flipping it about and rolling my balls between her fingers.

I was not getting excited and my mind was racing a mile a minute. Oh the stories I could brag about. Or could I?

She must have caught on to whatever signals I was putting out as she sat up and said we need to talk, "No one must know of what we are doing, it is our little secret, you want to keep having fun don't ya?

I nodded oh yeah I do.

The next day was Sunday and all day long I hung outside shooting hoops and hanging out hoping I would see her. Too chicken to just go over and knock on her door. I was a walking hard on all day and was so tempted to lock myself in the bathroom and take care of things.

Just after dinner I was outside throwing the football off our roof when her garage door abruptly started to open. I looked up and her car was just entering her driveway, she waved at me and smiled just like any other day. I was definitely disappointed when the garage door shut and she had not said anything to me.

I went in the house disappointed and to my room. As I reached for the light I saw out of the corner of my eye that Myra was standing naked in her window across from me. Her fingers buried in that dark brown triangle of bush. I stood and stared as my dick started to get hard. She fondled her tits and pinched her nipples. With her left hand she made a jerking motion and I knew she wanted to see me jerk off like before. I was a bit paranoid about my parents walking in as it was still early and they were awake and nodded my head that I couldn't do it.

She made a mad face and put her hands on her hips staring at me. I could see her mouth moving but could not hear what she was saying. She pointed at me and then at herself and then wiggled her finger in a beckoning manner.

I pushed out the screen and went out my window and hopped over the fence. She met me at her back door and all I could see was her outline from the glare as I approached. As I opened the door and went inside, there she was standing completely naked in front of me. I just stood staring mesmerized by her tits and then I would look down at her mesh of hair around her pussy back to her tits and finally up at her eyes.

"When I tell you to come over here I expect you to obey. When I tell you to jerk off for me in the window, you jerk off. And right now we will have a new rule, anytime you are in my house you will not wear any clothing unless I approve it. For now on you will do whatever I ask you to do. Understand?" While she was speaking she had walked over to me staring me straight in the eye as she spoke. I felt very intimidated by her. "Next time I have to ask you twice to do something or you disobey you will be punished and you will not like it, believe me!" I had lost concentration on what she was saying as I was staring at her erect nipples, the large brown areolas just begging to be licked and sucked. Suddenly she grabbed my left wrist and pulled down and turned me and before I knew it she had swatted my ass about 5 times hard. "Are you paying attention now?" She asked again staring at me with those eyes.

"Y-yes" I stammered.

"Apparently not! You are in my house and you still have your clothing on!" she said as if in disgust. She then turned on her heels and walked away from me across the room and down the hall.

I stood there flabbergasted not sure what to do. I took my t-shirt off and then my shorts and underwear. I stood there naked tugging on my flaccid penis as it seems to be as nervous as I was and I didn't want to be told how small I was again. So I tried, in vain, to make it bigger.

"Come here, now! She yelled from somewhere down the hall.

I walked down the hall and found her sitting on the edge of her bed. She patted the bed and told me to sit next to her. As I sat down she reached across my lap grabbing my cock in her fingers and pulling on it stretching it. "Oh my goodness, it looks even smaller than yesterday." Sitting on the bed hunched like that did make it look smaller of course. "Come out and play little pee pee." She said as she pulled on my cock some more. Flicking it away frustrated she said, "well we are gonna have to teach you to respond better than this if you are gonna please me. But there are lots of things we can do." She turned toward me and pushed me back on the bed. She started to kiss me, sticking her tongue deep into my mouth as she lay astride me. She then sat up and straddled me sitting right on my limp cock placing her hands on my chest and then she leaned forward. "Suck my nipples, honey." As she leaned forward I grasped each breast in my hand and squeezed them bringing each one to my mouth for me to suck on. I could feel her nipples hard against my lips and tongue. She leaned further forward and started to kiss me more. As she leaned forward her weight came off my cock as it started to grow and get hard. As she sat back down she felt my cock poking her in the ass and reached back behind her.

"Well, hello there. I see you are ready to be a man now." Reaching back with right hand she grasped my cock in her hand while she balanced on my chest with her left. She lifted her ass off of me and squatted over my cock holding it erect right under her pussy lips, teasing herself with my cock head. "Are you ready to feel a wet pussy?" All I could do was nod my head, God yes I wanted to feel it.

She lowered herself a little and slowly slid down until I was fully in her. She gasped a little and giggled and then moved her hips a bit grinding down on my cock. It felt so warm and so tight and sooooooo good. She placed both her hands on my chest and lifted herself off my cock and then slowly back down. She increased her pace a bit until each time she came down on me a slapping noise was issued. Every time she came down I pumped my hips up into her trying to catch on to the rhythm of her body. It seemed each time we got going fast though and really get going my dick would pop out and ruin our rhythm. It felt terrible flopping in the cold air and I sighed every time she put my cock back in her. She would groan and reach behind her pulling my rock hard cock back under and engulfed in her pussy. The next time I "popped" out she climbed off me and sat astride me. She took my cock in her hands and started stroking it getting it harder.

She let go of it and lay back on her back. She grabbed my arms and positioned me in front of her. She reached out between her legs and grabbed my cock and pulled me towards her. "Fuck me this way." She told me as she slid my cock in. I started fucking away driving my cock into her like a pile driver. Holding my body up as each hand was on each side of her body."Fuck me, baby. Hard.mmmmm. harder, come on fuck me good.""Kiss Me" she whispered to me. And I leaned forward pushing my dick in deeper as she gasped and started to moan a bit. "Right there. Yes! Right there." She started to moan and yell. "Oh! God! Fuck me!" and to kiss me passionately and wildly with her tongue and lips. I was humping for all I was worth and felt her hands on my ass cheeks pushing me into her when before I could give warning that I was cumming I just got numb and started squirting into her pussy. Exhausted I collapsed on top of her, "Oh did my little baby cum inside me? You did really good for your first time. Went longer than I thought you were going to." I just lay drained across her chest laying my head on her shoulder as my cock went limp inside her.

"I have so many things to teach you." She said. My breathing just getting under control I lifted myself off of her as my dick slipped out of its warm cocoon covered in our juices. I lay beside her and she turned putting her arm around me and spooning her ass into my crotch. She seemed to drift off asleep as I laid there thinking how amazing it is to be with this woman, naked. I just got laid!

We lay there silently for quite awhile. I moved my hand so I could cup one of her tits in my hand and as I fingered her nipple she grinded against me moaning softly. As I ran my hands over her skin caressing her soft skin I started to get hard again. I wanted to wake her so we could fuck again, but was afraid I would make her mad. I played with myself for awhile and then tried to relax and let my hard on go down. She rolled back into me and this time she grinded her ass right onto my hard dick crushing it slightly between us. She moaned softly and I saw a hint of a smile on her face. She lifted a leg up over mine and reached down between us grabbing my cock. She pulled on it a few times making it nice and hard and then aimed my cock into her pussy. Both of us laying on our sides I slid my cock in slowly trying to match her grinding her ass back into me. She patted a pillow at the head of the bed the same time she moved her body forward slipping my penis out of her. I lay there wondering why. She told me to sit in front of her. I climbed up the bed and sat where she had placed the pillow with my back to the headboard.

"I want to watch you cum. Jerk it for me like you do at home." With her face about six inches from my cock I slid my right hand down my cock and then licked the palm to get it wet and then started sliding it up and down and over the head. I used my left hand to massage my balls as I kept stroking. "Tell me when you are about to cum." She whispered as I continued pounding my hard meat. In my mind I was thinking that this sucks I could be fucking I could jerk off anytime, but this is what she wants. I picked up the pace, licking my palm occasionally, and then back to masturbating. I felt my orgasm building and told her I was about to cum.

"Cum for me, baby" she said. And right after the first bit of my load shot up in the air she pushed my hand off my cock and clamped her mouth over my cock sucking my cum out. She opened her mouth showing me my cum all over her tongue then she closed it and swallowed opening it again and saying, "all gone." Well I sort of just experience my first time of getting head.

As time went on she taught me how to fuck, different positions, how to eat her pussy and other acts. As the days passed she slowly changed from the thoughtful teacher to a bossy slave driver. She made demands on me and threatened punishments if I did not accept or do what she wanted. Her mood swings varied quite a bit and she became more and more abusive with her verbal attacks on me. Oddly enough I came to enjoy these outbursts and would do things to provoke her. I just never knew what to expect from her and I sensed that either she was getting bored with me and didn't like me anymore or I wasn't pleasing her enough. The idea that outside influences such as guilt, work and life in general never really crossed my mind. I just knew things were changing between us and it happened so quickly it seemed

She had set rules for me to obey. Her first rule being my nudity whenever I was under her roof was established early. She demanded that I come over at least three times a week causing me to be creative not only with my friends, but with my parents as well as to where I was going and who with. My parents were not really that strict however and rarely asked questions. She had demanded that I be at her house at 8pm if I was late there would be punishment. I was to enter from the back door of the house so no one in the neighborhood would notice anything peculiar. At times I would see her in her window looking over at me and sometimes she would beckon me to come over other times she would make me repeat my jerking off on the window performances for her.

Despite the threat of punishment, aside from the quick smacks on my butt I took that one time, she really did not indicate what kind of punishments she would dole out, but I soon found out.

Hanging out with my friends and then trying to make it to her house on time became a chore, despite the thrills of my new found sexual experiences. I arrived back in the neighborhood at nearly nine. I snuck around her back fence and let myself in the back door. I hadn't felt this nervous since the very first time I had come through this door. I immediately started to shed my clothes hoping to find her in a good mood and understanding. The house was silent and no lights were on as I tip-toed across the floor in search of Myra.

"It's about fucking time!" I heard her angry voice state from the darkness as she stood in the hallway her hands on her hips staring at me.

"I... "I stammered.

"Save the excuses. I warned you that you would be punished if you were ever late. Didn't you think I meant it?" she asked still a voice in the darkness.

"I'm sorry, "was all I was able to muster in a shaky voice.

"You're sorry? Bullshit!" she hissed at me.

I had no idea what to do and just stood there staring into the chasm from which her voice emanated. I felt cold and nervous not knowing what to expect. There was a click as she turned on the light next to the couch and she stood there dressed in sweats like she was ready to crash soon.

She sat back down in the middle of the couch and told me to stand before her. My cock shriveled from the cold of the room and the nervous energy.

"I think tonight's punishment will fit the crime. I'm gonna spank your ass raw so you will remember this tomorrow. Maybe next time you will think twice before being late!" she stared at me with ice blue eyes as she said it." Now bend your ass over my knees before I get any madder."

I hesitated, thinking she must be kidding. But the look on her face told me she was dead serious.

I reached out for the end of the couch for balance as I placed my bare bottom face up on her lap. I could feel my penis trapped between her legs as I lay there. She placed on hand on the small of my back and then I felt her right hand caress each of my butt cheeks. She ran a finger gently along my crack sending my body tingling. I heard her take in a sharp breath and steeled myself as her hand smacked down on my left cheek then right as she alternated between cheeks sometimes hitting between then and sometimes hitting down on my thighs. It felt as if my ass was on fire and I could just picture her red hand marks across my ass. I was moaning and crying out with every swat. Without even realizing it the friction of my cock between Myra's legs and the excitement of the spanking I found my dick was rock hard between her legs. Myra felt this too and kept trapping it between her thighs and squeezing before she would hit me with another wallop. She would yell things asking if I would be a good boy and obey her rules for now on as she spanked me. Suddenly she stopped. My ass seemed to throb as well as my cock.

"AH look at your ass so nice and red." She said as she gently ran her hands over my ass cheeks. I felt her spreading my ass cheeks apart as cold air hit my ass hole. My cock remained hard between her legs as I heard her sucking on what I found was her finger apparently getting it wet. As her left hand held my cheeks apart she took her right hand and slowly rubbed around the rim of my ass and then I felt her finger worming its way in my tight virgin hole. I don't know if she made it to the knuckle before I started spasming cumming all over her sweat pants. While I came she wiggled her finger a bit and then pulled it out.