Step-Mom Secrets Pt. 01

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Right behind Dad's back, My Step-Mom is making me her sissy.
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I grabbed the small tissue box from my nightstand and went for it. This was my special routine nightly routine before bed. For a nineteen year old at his peak, this was my ultimate release. I always felt so wrong doing this for some reason. Who really cares what I did alone in my room? I shouldn't be punished for satisfying my own desires.

I didn't notice my bedroom door being pushed open.

"Oh my God, what the hell are you doing?!"

My Step-Mom dropped the laundry basket, spilling the clean clothes everywhere. When she bent down to pick up the clothes, her bathrobe fell wide open. She quickly belted it back, covering up her perfect voluptuous breasts.

I wasn't able to grab a tissue in time, and accidentally shot my load all over the place.

She picked up the laundry basket, and put it back up on my dresser. She looked back at me with disappointment in her eyes, and closed the bedroom door behind her. It was a good thing my dad was a deep sleeper because he would have killed me.

I was still rock hard and dripping down on my thigh. Now I couldn't get the image of her out of my stupid hormonal mind. Up until now, I never even realized how attractive she was. Usually, she would cover up so you couldn't see much. I reached under my blanket and closed my eyes. I dreamt of gently touching on those succulent breasts. I dreamt of nibbling and sucking on those perfect nipples of hers.

I guess its ok for me to dream, but I knew it was wrong.

I couldn't help but rub one out the next morning. I was doing my best to calm down before I started fantasying about her again. I still couldn't get the image of her juicy breasts out of my mind. I finished myself off in a Kleenex, and got dressed. I headed downstairs to the kitchen to sit with the family, and have our weekly Sunday brunch.

During brunch, I kept sneaking glances at her from across the table. Her nipples poked out of her white bathrobe, and were encircled by her perfect areolas. I glanced down and ate my grilled cheese, doing my best to ignore my raging hard-on. My Dad was so busy talking about his work that she didn't even notice me staring at her. I was almost sure she caught me peeking up at her.

After brunch my dad put on his jacket and left to walk the dog. My Step-Mom and I sat at the kitchen table and had our third coffee. She put her mug down on the table, and interrupted the awkward silence.

"How come a guy like you doesn't have a girl?"

She had to continue the speech everyone gave me. This was the speech where every adult needed to know my personal business. I couldn't help having curly blonde hair and bright blue eyes. I was constantly working out, and had near perfect physique.

"If I was a nineteen your old girl, I'd jump all over you"

I turned beet red and tried to get up to leave. She could tell I was getting uncomfortable. She stood up from her chair, and walked to where I was sitting. She pushed her hand down on my shoulder, pushing me so I couldn't get up. She leaned in and kissed my under my left ear.

"Besides, you have a really nice big cock"

That's was a very surprising thing to hear from her. I never knew her to talk like that. She pushed my chair aside, and sat down on my lap. She reached up, and slowly undid the belt to her robe. She gently squeezed her breasts, toying with her nipples until they hardened. She let go of her breasts, and gently squeezed my crotch.

She continued, "You like these tits, don't you?"

"They're pretty nice" I stammered, still in shock.

She took my hands and placed them on her. Her pretty pink lips were inches away from my lips as I gently squeezed them. Her lips were so close I could feel her warm breath on my mouth. She pressed her lips against mine, and started to nervously kiss each other. She probably knew I had no clue what I was doing.

We were interrupted by a howling at the door. Ugh, how I hated that scruffy old mutt. That smelly old dog was always causing problems. It was always chewing up the furniture, making howling noises and now ruining a perfect moment.

She pushed my hands down on my lap, and closed her robe. She gave me a quick sloppy kiss on the cheek, and went to answer the door. I knew I couldn't get up just yet. I didn't want my Dad to notice my hard-on. Or even worse, the little bit of lipstick on my mouth.

Luckily, my dad and the dog were both soaking wet. They had been caught in a surprise thunderstorm. In typical mutt fashion, the dog shook water all over the front entrance. Then ran up to me and started sniffing at my crotch.

I cleaned up the doorway mess, and helped put the dishes away. We grabbed some snacks and sat down on the couch to watch TV. The mutt sat in the middle of the floor panting like a pig on hot day. I tried to ignore him, and find anything worth watching. It wasn't the channels that got my attention. It was the curvaceous middle-aged woman sitting next to me on the couch. Just as I finally settled in, my Dad had to interrupt me.

"Aaron, can you help me in the garage?"

We got busy cutting a stack of wood into two by fours. We had spent the last month working on building our deck. My dad always had these never ending projects around the house. I really didn't want this with him. I wanted to be gently touching her breasts again. I knew she was sitting alone upstairs, and how much of an opportunity I had. He stopped cutting, and turned off the electric saw.

"You want to see why I married your step-mom?" he said, pulling his phone out of his jeans pocket.

He opened his phone up, and showed me a very candid picture of her. She was wearing black three inch heels and fishnet stockings. Her dark red lingerie was outlined with black lace. Her big breasts were barely covered, and her nipples were peeking through. Her panties were so clear that you could see everything.

"So, would you jerk off to that?" He asked.

"No, she's my fucking step-mom." I was clearly lying.

He turned red with embarrassment, realizing what he just showed me. She was wearing the same red lingerie, and he was bent over on all fours. She was tightly grabbing his sides. Her black heel was pressing into his back, and she was pushing a strap-on inside him. You couldn't tell if he was enjoying it because of the ball-gag stuffed into his mouth.

"You tell anyone and I'll kill you!" He said, quickly putting his phone away.

Without saying a word, we went back to work. My step-mom came down to the garage, but we didn't hear her over the electric saw. She placed two cold beers on the table where we were working. Noticing her, he turned the electric saw off. My dad grabbed her ass through the bathrobe, squeezing her hard. She turned beet red and jokingly smacked his burly chest.

"She's a fucking fox, isn't she?" ugh, he just wouldn't stop.

I took a quick peek at her while she walked up the stairs. He was right, she truly was a fox! I was so jealous of him, and I wanted to grab her ass so badly. My Dad was really a lucky guy. I tried to focus on the work we were doing, and not slice my fingers off.

We spent the next few hours carrying the wood to the back of the house. We finally called it quits. We both concluded that it was way too hot to work outside. We decided to leave the work for another day.

I was sweating head to toe, and really needed to shower. I took my work-boots off and headed inside the house. After inhaling a glass of lemonade, I headed up to my room to take a shower. My dad tried to go up to shower, but passed out on the sofa.

I turned the water on, and soaped myself up and down. I continued humming to myself, and thought about her lingerie clad body. Of course, I was trying to get that weird image of my dad out of my head. It wasn't long before I jerked a thick load off in the shower. I hummed along and dried myself off, still somehow dripping on the towel.

I didn't notice her peeking at me the whole time. I didn't notice that she was standing in my doorway, peeking in and touching herself. I didn't notice the soft moan coming from her just as I came. If only I knew she had been there the whole time.

I headed out of my bathroom to get changed. I reached into my drawer to grab some clean underwear. There was a pair of purple satin panties in the drawer. 'Put them on under you clothes' the note next to them read. Why the fuck would anyone want that?

I slid them on over my long dangling cock. The soft satin fabric brushed lightly against my long shaft. I took a minute to glance in the dresser mirror. My cock and balls pushed through, it didn't look terrible at all. Was she trying to turn me into something? Was it a sick fantasy she was going for?

I reached into my second drawer, and put on a pair of gym shorts and a T-shirt. I pulled the shorts down again and admired the panties in the mirror. I pulled the shorts back up, and headed downstairs to watch TV. I grabbed a cold beer from the fridge, and sat down next to my step-mom. She was watching one of her boring soap operas. My dad was sitting in his big green chair, snoring away.

"Let me see them on you" she said, smiling at me.

I was terrified my dad would wake up. How on earth could I explain wearing ladies panties to him? I pulled my gym shorts down for her to see. She gently caressed the outside of the soft panties.

"You look good in those." She said, sliding her long fingers against my balls.

Just as she took her hands out of my shorts, my dad woke up. Whew, that was a close call! Making sure he was asleep, she leaned forward and whispered in my ear.

"Go up to your room and come inside them for me"

I was really being some sort of animal today. Even for a nineteen year old, how many times could I possibly come in a day? She smiled at me as I got up of the couch. Then she undid her bathrobe, giving me quick peek at her chest. What kind of sick person was she?

I lay down on my pillow and closed my eyes. I pulled my down, and I reached between my legs. I slowly jerked myself up and down. I dreamt about her perfect breasts and soft kisses. I pushed my cock back at forth against the soft panties

I didn't realize she had snuck up the stairs behind me (again). I pulled my shorts back up and was about to head downstairs. She was just outside my doorway waiting for me.

"Good job" she said, reaching for my cock.

She crouched down on her knees, and pulled my gym shorts halfway down. She licked the panties up and down until they were soaking wet. She stood up and kissed me again. While we kissed, she took my hand and guided me between her thighs. She pulled my shorts back up, and headed back downstairs. As she walked downstairs she undid her robe, revealing her perfect naked backside.

She knew she had to be a little more careful sneaking around with me. My dad was awake from his long Sunday nap, and was busy preparing dinner. She was smart enough to put her robe back on, just in time.

Even though my dad was an excellent cook, I was barely eating anything. I was distracted by her sliding her toes against me under the table. I slid my fork into the food, still smelling her on my hand. After a few too many beers, my dad headed to the dining room and passed out in his chair. That was usually the case after Sunday night dinners. The mutt followed him, and fell asleep at his feet. It was almost comical how similar they looked.

My Step-Mom and I sat on the couch, and each had a small bowl of Ice-Cream for dessert. Once she was sure he was fast asleep, she stood up and went behind his chair.

She opened her bathrobe, and dropped it to her floor. She was wearing the same see trough panties I had seen in the picture. I couldn't believe how crazy she was. She pointed at my crotch, and I knew exactly what she wanted. If my Dad woke up I would need to cover up fast. I made sure I had pillow nearby, and I pulled my shorts down. She smiled as I exposed the panties to her. She slowly pushed her panties down to the floor.

She had thick perfect pussy lips, covered by a thin layer of hair. She beckoned at me to come over to her. I quickly pulled up my shorts and went behind my dad's chair to join her.

She got down on her knees behind the chair. She reached up and pulled my shorts down. She pulled the panties to the side, and pulled my cock out. She slowly sucked me up and down, until my cock hit the back of her throat. She was easily able to fit the whole thing in and out of her mouth. I was so nervous that I was shaking. I was worried that her soft gags and my moaning would wake up my Dad. I closed my eyes as her pretty blonde hair bobbed up and down on me. She pushed the panties I was wearing down to the floor. She sucked me faster and faster, pressing her thin pink lips against my balls. She stopped, and a stream of saliva dripped onto the floor. She gently stroked my cock up and down, and stood up next to me. With her soft hand still stroking me, she whispered in my ear.

"Let's switch panties for the night"

She put her bathrobe back on, and she pulled my shorts back up. Squeezing my ass hard, she whispered in my ear.

"Sweet dreams, sissy boy"

I guess there's worth things I could have been called.

I stayed awake the whole night wondering what she would do next. I guess she wasn't able to do much because my dad was around. I drifted off to sleep with my hands inside the switched panties.

The next morning, I woke up to a new pile of clothes on my dresser. A small note was on top of the clothes 'put these on and come downstairs'. I wasn't ever sure how to put this stuff on. Also, why the heck did she want me to keep wear ladies clothing? What if my dad found out? I can't imagine he'd be ok seeing his teenage son in woman's clothing? Well, then again he knew I had some pretty serious blackmail.

I put on the pink satin slip and the lace purple underwear. I glanced in the mirror at my smooth muscular body underneath the clothes. I stood up and struggled to get the black stockings and the three inch heels on. I stopped for a second and turned around. I lifted up the satin slip, and checked out my ass in the panties.

"Hello my little beauty" She said, interrupting me.

She came close to me, and pressed her naked body against mine. She placed her hand on crotch, and gave me a sloppy tongue-filled kiss.

"You're already hard, you fucking pervert" She said, gently slapping my face.

She crouched down on her knees and lifted up the slip. She pulled the panties sideways, and pulled my long hard cock out. She sucked me up and down faster and faster. She face pressed back and forth against the panties. Holy shit! She was fucking good at this. I tried to keep my balance while she rocked my body back and forth. She pushed the panties back, and kissed me again.

"From now on you're my little sissy." She declared.

She stood up and pushed my head between her juicy breasts. She let go of my head and slid her nipples in and out of her mouth. I was weak at the knees, and wearing heels for the first time. It was clear that I could barely stand.

But she wasn't done with me.

"Bend over you little sissy!"

She pushed me forward and bent me down on my bedroom floor.

We were interrupted by the doorbell, and the stupid mutts incessant barking. She put her robe back on, covering up her naked body. Before she went to answer the door, she gave me another order.

"Go up to my room and wait on all fours on my bed...oh and you keep those heels on"

She went to answer the door, and I went up to her bedroom. It turned out to be a Jehovah's Witness. I guess we were already going to hell. She told them she had to leave for work, and quickly got rid of them. When she came back to the room, I was bent over waiting for her. The heels were painfully digging into her bed.

She gently spanked me over and over. She started spanking me so hard my body rocked back and forth on the bed. I'm sure she was spanking me hard enough to leave handprints.

"Who's my little step-sissy?!" She yelled over and over.

"I'm your little step-sissy!" I finally yelled back, starting to enjoy it.

She grabbed my head and pulled me back towards her body. She reached around and squeezed pinched my nipples through the slip. She reached down and squeezed my balls as hard she could, she pushed my head deep into the pillow.

She lifted the pink lingerie slip up, and pulled the panties down just under my ass. She tried to push her finger in my ass, but it just wouldn't work. She realized that I was way too tight. She grabbed my ass, and spread my toned cheeks apart. She licked in and out of my ass, while slowly pushing her fingers inside. Fuck! She knew what she was doing. She stopped for a second and pulled my body back towards her naked chest.

"Want me to fuck you like your daddy likes?" She whispered, while driving her fingers deep in me.

Oh shit! Did she know I saw the picture with her and my dad? She pushed her lubed up finger in and out until she was able to slide in.

She grabbed something from the bedside drawer and wrapped it around her waist. She pushed me back into the pillow, and smacked both my ass cheeks hard. She put some lube on the strap-on and slowly pushed inside me.

Ouch! It really hurt, but I wanted to show her what I could handle. Even though I was wearing ladies clothing, I wanted to show her I was the man of the house. I turned around and watch her smile, with voluptuous breasts bouncing up and down. She grabbed my waist and went a bit harder in me.

.

"Who's my little sissy?" She yelled, pushing further in me.

Realizing I was way too tight, she slowly pulled out again. She put more lube on the end, and pushed in and out a few more times. It was starting to feel pretty amazing. She pushed further in and I couldn't help but let out a load moan.

"Fuck me!" I yelled, between soft even moans.

"Get on your back Step-Sissy!" she ordered, squeezing my ass hard.

I moaned like crazy, as she slowly pulled out of me. She took the Strap-on off her waist, and removed the 'dildo' from it. She pushed the dildo in and out of my mouth, making me choke while she fingered my asshole.

With all her strength, she threw me on my back.

She spread her legs and squatted down on my face. I could barely breathe with her juicy pussy lips pressing down on my face. I eagerly pushed my tongue deep inside her. It slid in easily, because she was soaking wet.

She leaned back and rode my face back and forth, smacking her pussy lips up and down on my tongue. I could feel her oozing on my face as she smacked harder against my mouth. She stopped for a second and let out a soft moan. With my lips buried in her soaking wet Pussy, she started to shake like crazy. A small stream slid down my mouth onto my neck. I guess I did a pretty good job.

She stopped shaking and leaned forward, gagging on my cock. My tongue was still buried inside her. I reached down to jerk myself into her mouth, but she was having none of it. She pushed my hand away, and pushed the dildo inside my hole. I could feel my cock pulsating back and forth. I knew she could taste that I wasn't far from coming.

She pulled the panties all the way down. She got off my face, and pushed the dildo deeper inside my hole. She went on her hands and knees next to me, and slammed her face into my cock. I reached down and jerked myself up and down inside her mouth. I couldn't hold out much longer.

She stopped and went on top of me. She pushed my hand away and bit my lip hard. She leaned forward and kissed the side of neck. I grabbed my cock and went faster and faster. She pushed my hand away again, and grabbed my cock. Spreading her legs wide, she slowly slid down on me.

She shoved the dildo inside me, as she pushed her body all the way down on my erect cock. I grabbed her waist as hard as I could, as her ass slapped against me. Was I really about to come inside my Step-Mom? She didn't seem to mind.

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