My New Stepmom

Three years after my mom died my dad decided to hit the dating scene, I was looking for a job after college without success so I moved back home. I was working at Starbucks so I has some spending money.

I remember the first time he brought her home because she was as young as me. Little did I realize that six short months later she would be my new stepmom. After the wedding she moved in. When we were alone she told me to call her mommy but no way was I ever going to call her that.

I always thought there was something wrong with her but I couldn't figure it out. Even when I heard her and my dad having sex it sounded wrong but all I heard was my dad moaning, muffled voices and slapping so I wasn't sure what was wrong.

Over the holidays we decided to take a "family" vacation, just the three of us. Thankfully I could afford my own room and privacy. We stopped at a hotel for the night on the way to Florida. While we were eating dinner across the street my dad got a call from the office. When he got off the phone he told us that he had to fly home now but would meet us in Florida in a few days. Kyla, my new stepmom, drove him to the airport and I went to my room to jerk off.

Now picture me; naked on the bed, jerking my cock, sniffing my stepmom's panties, while watching porn with lube & anal beads on the table. And in walks my new stepmom!

"Tommy what are you doing with my panties? Give me those now!" she screamed. I knew she was mad so I looked down as I handed them over.

"Wait until I tell your father young man!" she told me.

"No please Kyla I will do anything, please don't tell him." I pleaded.

"Anything, we will see. I could have fun with you. So what were you watching on your laptop?" she asked.

She opened up my laptop and demanded the password. I hung my head in shame when I knew what she would find, gay porn. She asked if I ever had gay sex. I told her just fooling around with mutual hand jobs in college.

"I am going to teach you how to have sex with a woman like me." I got so excited until she told me "But first you will be punished for stealing my panties" as she sat on the bed and told me to lie over her lap.

I knew she was going to spank me and I am too old for spankings. I stood my ground for a minute trying to turn the tables on her. "Kyla, What are you doing in my room anyways? I am free to jerk off anywhere I want!"

"A water pipe broke in my room and the hotel is sold out, the manager knows we are family and your room has two beds. But that doesn't excuse you from stealing my panties! Now get over my knee!"

I resigned myself to the punishment so I lay over her lap. "What's my name?" she asked. Of course I replied "Kyla". Her hand hit my ass as she said "Wrong, What's my name?" Another slap on my ass hit and I yelped out like a girl. I refused to call her mommy so she kept spanking me. My ass was turning bright red and very sore. I begged her to stop but she just continued to spank me calling me names and telling me the new rules of the house as she spanked me. She would pause and rub my ass while tickling my balls and teasing my asshole, I thought it was strange but it felt good.

"Please stop mommy!" I finally yelled out and she stopped spanking me. She was rubbing my ass telling me it would be okay. Occasionally her finger would brush across my asshole causing me to jump, she would giggle when that happened and tell me that I must be very sensitive. That's when she noticed the beads on the table.

"Oh what do we have there?" She told me to stand up, get the beads and lube. I got back over her lap like a good boy. She dripped some lube in between my ass cheeks and then started spreading it over my asshole using her finger. Then she stopped.

"You are a dirty boy, let's clean you up first!" as she pushed me off her lap. She grabbed me by the ear and dragged me to the bathroom. She told me to get on my hands and knees for a good cleaning. She left the bathroom and came back with a huge syringe filled with water; at first I thought she was going to squirt me with it but when I felt her insert it into my ass I realized it was an enema syringe. She slowly filled me with water and I squirmed, I think she enjoyed my squirming and helplessness. I hadn't had an enema since I was a little kid and I kept asking why but she just said I had to be clean.

When it was empty she told me to sit on the toilet. She left the room while I released the water. I cleaned myself up and came out of the bathroom. She sternly told me to get back in there and that she wasn't done with me. She had another full syringe in her hand. She filled me up again but very slowly while rubbing my belly. After I was full she left the room and I got on the toilet. I was thinking that this was a lot of cleaning for just my beads. I just use them and just clean them after.

She came back in with another smaller syringe. I asked her what it was and she slapped my dick, said shut up and to get down on my hands and knees again. She inserted it into my ass and I felt something creamy inject into my ass. Then she told me it was a lube injection.

She told me to clean up in the shower and when done to come out. When I was done I walked out with a towel around my waist. She ripped it off me causing me to get a chill and to cover myself. She laughed and told me to get over her lap again.

She started to rub me all over almost tickling me. She picked up the beads and said "Let's see how many will fit!" She started inserting them. I used them before but this was the first time someone else did it to me. She slowly inserted them and then would pull one or two out. It felt good but weird since I wasn't doing it.

She pushed all of them into my ass causing me to moan. She laughed and said wait until later and she will really make me moan. She grabbed her purse but I couldn't see what she was getting. She slowly pulled out the beads and then pushed something else, something bigger into my asshole causing me moan like a girl as she inserted it into my ass. It was much larger than anything I ever had in my ass.

When it was all the way in she would tap the base causing it to move in my ass. She pulled it back out slowly. When just the tip remained she started to push it back in, I cried out "Please stop mommy!" but she just laughed and said "No, this is too much fun" as she pushed it back into me pressing it deep with her thumb. As I was lying across her lap I was helpless as she fucked me with the toy causing me to moan like a girl.

She was laughing with an evil laugh like in the movies. After fucking me with the toy she pulled it out. I felt so empty but not for long. She started inserting something else that was very big. It hurt going in but then it popped into my ass causing me to yelp. The base was much skinnier so I got some relief. She told me she put a butt plug into me. Then she told me to stand up and to sit on the chair.

She told me that since I sound so much like a girl maybe I should look like one. That's when she started putting makeup on me, I didn't like it but what choice did I have. I mean I couldn't run out of the room, naked with a butt plug up my ass.

She started to put lipstick on me and told me it will be good to measure with the lipstick. I didn't understand what she was talking about. When she was done she told me to look in the mirror and I saw myself with makeup and bright red lips. I was wondering what was going on but I was excited.

She starting calling me her baby and told me to get up and that she had to check on my boypussy. I asked her what she meant but she just slapped my ass and told me to shut up. She had me bend over and put my hands on the desk. She grabbed the base of the plug and pulled it out causing me to moan and bend further over. Then she inserted something else but when I felt the creamy injection I knew it was more lube. Then she pushed the butt plug back into me, it did slip in easier this time but I still moaned.

"Since you like my panties so much put them on!" she commanded as she handed me the panties that she caught me smelling earlier.

She slapped my ass and told me it was time to learn how to please a woman like her. She told me to sit on the bed and she sat next to me. She started kissing me but she was definitely the aggressor. She took charge as she told me where to put my hands and to rub or squeeze. When I would try to put my hands somewhere else she would stop kissing me and squeeze my dick telling me to obey her.

She pushed me back onto the bed and told me it was time for next lesson and to pay careful attention. That is when she started going down on me taking my dick into her mouth. I gasped with pleasure. She was so good sucking and licking in all of the right spots. At the same time she was moving the butt plug in my ass. I was in heaven. She brought me to the edge and stopped. She told me to look at my dick and see that her lipstick was at the base of my dick. My dick is average so I didn't know what to say since most girls can swallow me whole.

She told me to get up and that it was her turn. She got a pillow off the bed and put it on the floor telling me to kneel. As she sat on the bed in front of me she grabbed my chin and told me she hopes I was paying attention to my blowjob. I told her I have licked lots of pussy and I would do everything to please her. "Will you lick my ass?" she asked.

"Yes, Kyla" I quickly said not realizing my mistake. "What did you call me?" as she raised her hand. "Sorry mommy"

She told me to stay like that while she washed up. She went into the bathroom and closed the door. When she was in the bathroom I put my hand to my asshole feeling for the butt plug. I wanted to pull it out and see how big it was but I knew I would get into trouble and what if I couldn't get it back in.

She walked out of the bathroom and caught me feeling my butt plug. "It is best that you leave that in to stretch you, baby" she said.

She was wearing a towel around her waist when she sat down on the bed in front of me. She told me that she didn't trust me so she pulled some rope handcuffs out of her purse and tied my hands behind my back. She told me how she wanted me to lick her breasts. When she was satisfied she told me it was time for the main event, she told me to close my eyes and I felt something slip over my face. When I opened my eyes I couldn't see.

She pushed me down and told me to kiss her legs working my way up. I bent down kissing her legs as I worked my way up. I felt her open the towel so I started moving faster but she told me to slow down and take my time. I felt her spread her legs so I took the opportunity to kiss the inside of her thighs. My face hit something hard but also soft, I was wondering if it was another toy but this time for her pussy.

I sensed that it was pulled away so I kept kissing as she spread her legs even wider. I knew I was close and I was wondering if she was shaved. Since I couldn't see I would have to find out with my tongue. That's when my tongue hit something softer than her thighs. I should be at her pussy but it felt different. She grabbed my head and guided me as she told me to start kissing and licking forward and up. Her thigh got hard again as I licked my way up. I thought this was all strange but I kept going.

Then I reached the end and she stopped me. She told me to open wide and then I felt her hands guide my head as if it was a seat on a roller coaster and we just reached the top of the hill. I felt something hard yet soft fill my mouth and she said "Suck it!"

I was thinking strap-on and my ass clenched around the butt plug. I could taste the body wash I use and I was confused why she would have washed it with the body wash. She would press in until I started to gag, she just laughed and said I have to do better and she will teach me. She started moving my head faster and faster which confused me because it's not like she would get pleasure from a strap-on.

She finally pulled me off and told me kneel straight up. My mouth was still open as I was drooling. My throat was so sore that I wanted a drink. She must have sensed it because she grabbed my chin and said "I have some water for you, baby." As she tilted the bottle of water up to my mouth I drank almost the whole bottle.

"Well I am glad to see that you like to swallow." She laughed, which I thought was an odd statement.

I felt her grabbed the hood; I closed my eyes to protect them as she pulled it off. "Open your eyes baby and see what's mommy has for you."

I opened my eyes and I was shocked when I saw that she had a cock. I was so shocked I couldn't say anything and just knelt there with my mouth open. "Close your mouth before I put something in there! Better idea leave it open I do have something to shove in there." she said.

"You have three choices now." she told me.

"1. Move out, leave the house and let your father & I be alone. I will let you get up and get dressed. I will go find another hotel or even sleep in the car. We will never mention this again."

"2. I will un-tie your hands and you will suck me until I cum. You will suck & lick my cock, lick my balls, and even lick my ass! I would have licked your ass earlier but the butt plug was in the way. Also baby you will swallow every drop of my cum or I will spank you so hard you will want to walk to Florida before sitting in a car. There is one more condition; we will change your lipstick color and you have to suck me deeper than before. You can see your lipstick mark from your first time; you have several inches to go before you reach the base like I did for you."

"3. I get to bend you over this bed and fuck your boypussy until I cum. But to warn you I am horny so I will fuck you twice. I will turn you into a girl and teach you how to fuck properly."

"So what is your answer?" she asked me.

"Number two" I quietly said. "Number two, WHAT?" she replied. "Number two mommy" I answered.

She then says "Well since you just sucked my dick I guess I can't call you baby anymore, your new name is Cum Slut!"

She untied my hands and said "Get to sucking, Cum Slut!" as she pushed my head down.

I started doing what feels good to me. I tried to suck all of her cock but I kept gagging, hoping I was going deeper than before. I used my hands as I jerked her cock and played with balls.

"Lick my balls" she commanded, so I pulled off her cock and started on her balls.

"What are you doing!" she shouted. "Licking your balls mommy" That sounded so odd coming out of my mouth.

"You always kiss up and down my dick when you stop or start sucking!" as she pulled my head back up.

I started kissing my way down to her balls. I was pleasing her with my skills because this was more like eating pussy. "That's a good tongue you have, now let's try it in my ass!" she said as she leaned back and lifted her legs. I lifted her balls out of the way and started licking her ass. She was clean and fresh and I have licked girl's asses before so I was right at home. Then she got up into doggy position and told me to keep licking as I stroked her cock.

After a bit she told me it was time to finish and reminded me of the consequences if I didn't swallow every drop. She sat back on the bed and told me to start at her balls and work up. Again it was a like a roller coaster climbing to the top of the hill but this time I was doing it. When I reached the top I opened wide and started going down on her.

I used my hands and mouth doing everything I could to finish her. When I wanted a pause for my throat I would lick around the head of her cock as I stroked her with my hand. I would also suck very hard trying to please her.

Eventually my new learned talents succeeded and she warned me that she was cumming and also warned me to swallow every drop.

Her cock erupted in my mouth as I swallowed as fast as I could. When I felt she was finished I pulled off quite proud with myself. "Another drop came out, lick it off Cum Slut!" she said while holding her cock. I licked the head of her cock removing the last of her cum.

"Well that was great Cum Slut, now I have to prepare your boypussy." She told me.

"What do you mean mommy?" I made sure I said mommy this time because I was scared. "I picked number two, not three, and I didn't spill one drop!" I said.

"Yes Cum Slut you picked number two not three so I won't fuck your boypussy twice. You took care of some of my needs by sucking my cock but I always cum twice a night, so bend over Cum Slut it's time to get you ready. It's time to turn you into a girl with more than just makeup and panties." She laughed.

"Please mommy let me suck you again!" I pleaded. "No Cum Slut it's time to pop your cherry, you don't want to be a virgin your whole life, do you." It wasn't a question but more of a statement.

"Don't worry I will take my time and prepare you, my cock is a lot bigger than the butt plug." And she was right.

I got into doggy position and she pulled down my panties to my knees. She got some more items from her purse but I couldn't see them. She filled up the lube syringe again. She pulled out the butt plug and again injected me with more lube, now I knew why I needed so much lube.

She inserted another toy until I felt the base on my ass. She was feeling for something when it started vibrating and moving in my ass hitting something inside of me that made me cry out.

"That's your button that will make you cum like a girl." She said "Wait until you feel my cock rubbing your button and I make you cum like a girl!"

I started dripping precum as she stroked my cock and moved the toy around in my ass. "Is my Cum Slut liking this?" she asked. "Yes mommy" I replied completely under her control.

She kept stretching me with various toys when she announced "It's time to lose your cherry Cum Slut. But I will give you one more choice. You can still pick option one. What do you want?"

"Option two, please mommy" I begged. She slapped my ass and told me "NO!"

She kept playing with the toy and I didn't want to leave so I finally said "Fuck me, mommy" That was so strange coming out of my mouth but also a relief.

She stood up and got a condom. She told me to get her dick wet again. Then she started rolling the condom down her cock. She smiled at me with an evil grin. I was scared. She got the bottle of lube and poured some on her cock, stroking it as she smiled at me.

"It's time to lose that cherry." She said as she pulled the toy out of my ass. She told me to push out like I was taking a shit as I felt her cock head at my asshole. I didn't know how it would fit but felt it fit as she pushed forward while grabbing my hips.

I moaned like a girl and put my head down as I felt my asshole being stretched wide. She slowly worked her way into my ass occasionally pulling back and forth like she slowly fucking me. Eventually she worked her entire cock into my ass as I felt her hips on my ass. I felt so full. I moaned and she told me it was time to fuck. She started fucking me slowly with her dick and I moaned.

As I loosened she started speeding up, fucking me harder and faster causing my cry out. She just laughed and told me that all virgins cry.

After fucking for a bit she told me she doesn't like to cum in a condom, at first I was scared but then she told me she is going from my ass to my mouth and I will swallow every drop again. She pulled out, ripped off the condom and shoved her cock into my throat.

"Make me cum and swallow me baby" I was so happy she called me baby again that I worked extra hard for her cum.

Then she gave it to me and I swallowed every drop. I even stayed to lick up any drops coming out at the end.

She patted my head and told me "Good Cum Slut. Tomorrow we will do it again".

"But mommy I chose option two we are done." I cried out.