Grieving Boy and his Step Mother

Editor's note: this story contains scenes of incest or incest content.

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My mother left my father and me suddenly when I was in my teens. Over the next several years, my father dated a few different women. The one woman who I liked the most was Samantha. My father had introduced me to her after they'd been out a few times. She was a tall, voluptuous woman with wide hips and huge boobs. She and I hit it off immediately. She didn't immediately try to treat me as if I were her son. But she had a gentle, maternal way about her that I found to be very pleasant.

During the time immediately after my high school graduation, I began to feel a strange tension in my house. My father began acting differently. I couldn't put my finger on what it was, but there was something happening that I wasn't aware of. Soon afterward, it was announced he would be marrying Samantha. The wedding was put together very quickly and they were wed only 3 months later.

They decided against going on a honeymoon and I quickly learned why. About 5 weeks after they were married, my father and Samantha sat me down and told me my father had been diagnosed with cancer. 6 months later he passed away.

His passing seemed so sudden. I wasn't at all ready for him to leave. But thankfully Samantha was there, we grieved together and that event brought us closer together. She and I spent those terrible months after his death growing extremely close to one another. We cried together, we laughed together, we grieved his passing until it hurt much less on a daily basis.

I put off college indefinitely. I kept the job I'd had through high school and spent my free time at home with Samantha. All my friends had left for college, so I really had no one else to spend time with. Not that I really wanted to, Samantha had proven to be a very good friend and stepmother.

Over time, I learned she was very open about sexuality. We had long talks about hetero, homo, and bisexuality. She loved to talk about fetishes, domination, submission, and exhibitionism were her favorites. She must've known when she began going into details about different fetishes, my mind was absorbing all she said. I used those little talks as fantasies during my alone times at night.

While heading to bed one evening, I stopped and kissed her goodnight. She sat there on the couch and looked up from the show she was watching. She asked if I was going to masturbate. I blushed, nodded my head and in a soft voice, told I was. She smiled and told me to take the box of tissues from the bathroom to clean up. She also told me to go pee afterward so I wouldn't get a bladder infection.

I stumbled out of the room with humiliation burning to my core. Samantha knew I was going to masturbate! She asked and I told her I was going to play with myself! I was so embarrassed. But at the same time, my penis was rock-hard in my pants! I was mortified, but I did move the box of tissues to my bedside before I began. And I followed her instructions about using the bathroom afterward.

The next morning, I walked into the kitchen and while she poured me a glass of juice, she asked if I had a nice orgasm before falling asleep. I blushed and smiled, then told her I had a very nice orgasm. Over breakfast that morning, we had a long talk about masturbation. She reminded me it was a natural thing and I shouldn't be ashamed of it.

That same afternoon, after walking out of the bathroom, she called my name and I found her in the living room watching one of her favorite talk shows. She muted the TV and while I stood right in front of her, she asked why I took so long in the bathroom. I blushed and mumbled something I knew she couldn't hear. She asked if I had gone in there to masturbate. Blushing even deeper, I nodded my head.

She reminded me that I needn't be embarrassed. And as a matter-of-fact, she would like me to begin announcing my intention to masturbate before I left the room. The concept of telling Samantha that I was going to go masturbate every time I did it was frightening. She would probably think I was a freak if she knew how often I played with myself! I did it a lot!

That evening, as I was getting up to go to bed, I leaned down and kissed her goodnight. I then stood up straight, and with humiliation surging through my body, I told her I was going to masturbate and then go to sleep. She leaned forward, patted my bottom with her large open palm and said, "Good boy. Have fun and don't forget to go potty when you're finished."

The following morning at breakfast, I apologized because I'd masturbated before joining her that morning. She smiled, told me it was okay. And that she was happy I'd been honest with her. She then asked if I'd woken up with a stiffie. I told her I had. She asked if I got naked when I masturbated. I told her I usually just lowered my pants and underpants and pulled my shirt up. She then asked if I would try something new. She asked me to promise I'd get completely naked every time I played with myself. Orgasms are a very special thing and they are made so much better when naked.

There was something terribly embarrassing about her knowing when I would masturbate. And what was surprising was that I couldn't stop thinking about her knowing. It was driving me crazy and I couldn't remember ever being so horny, so often.

Just after we'd had lunch, I could stand it no longer. I bit my lower lip, looked up into her eyes and told her I was going to my room to masturbate. She pulled me into an embrace, one of her hands was on the back of my head, the other on my extreme lower back, my face resting just above her large, soft breast. She told me to remember to get naked first. She didn't want me wearing a single thing. And after I'd cleaned up and gone potty, I was to get dressed and tell her if I preferred playing with myself clothed or naked.

As soon as she released me, I smiled up at her and dashed off to my room. I locked my door as usual and then quickly stripped off all of my clothes. My smallish penis was already throbbing wildly when I laid on my bed, on top of the covers. I took hold of my penis with my first finger and thumb and slowly slid them up and down. I spread my legs wide and felt so naughty being naked and playing with myself in the middle of the day. It was made even more naughty knowing my stepmother knew exactly what I was doing. Just before my penis squirted out its juice, I imagined my stepmother walking into my room and seeing me like that.

After resting for a few moments, recovering from a very powerful orgasm, I wiped up the mess with tissues. I then rose up off the bed and went to get dressed. But then I remembered what I'd been told. She told me to clean up, go potty and then get dressed. A shiver shot up my spine when I considered following her instructions exactly as she had said them. Having just fantasized about her walking in and seeing me masturbate, it didn't take long for me to do the unthinkable.

Still naked, my penis began to stiffen anew as I reached for my doorknob. Cracking open my door, I heard the TV on in the living room and figured she would be on the couch. I opened the door far enough to step into the hall and quickly tiptoed to the bathroom. Just as I was shutting the door, I heard my stepmother laugh at something that was said on TV. The door shut quietly and I moved to the toilet. I lifted the seat and stood there and peed. It felt so odd going to the bathroom naked without any other clothes in the room and my stepmother in the house!

When I flushed the toilet, I was shocked at how loud it was. I had never realized how loud it was until that moment. I stood naked in the bathroom and waited for the noise to stop. When it did, I unlocked the door and cracked it open. Peeking down the hall, I didn't see her and I still heard the TV. So I quickly stepped back into the hall and rushed to my room. My heart was pounding in my chest and my penis was stiff all over again. I laid on my bed, spread my legs wide and imagined her walking in on me. I considered masturbating again but decided I would do as I'd been told. I would let her know before I masturbated, not after. So I pulled on a white t-shirt, my underpants, and light gray, soft-cotton shorts. Even with my thin, 4-inch penis, it was still obvious it was hard.

I opened my door and walked into the living room. As I'd guessed, she was seated in her usual spot on the couch. I crossed the room and took a seat beside her. She waited until the next commercial before muting the TV and laying her large, soft hand on my thigh. Looking into my eyes, she said, "I love you in these little shorts. You've got the cutest legs for a 20-year-old boy! So, tell me, was it better to play with yourself naked?"

I whimpered softly when her hand squeezed my thigh. I told her it was much better to do that naked. It was so much more intense doing it naked in the middle of the day. When she didn't say anything, I felt like I had to keep talking. So I bashfully shared the fantasy I'd had of her walking in and seeing me. She seemed to enjoy that fact. And when I told her about my naked trip to the bathroom, she squeezed my thigh and whispered two words under her breath, 'good boy'. The last thing I told her was how stiff I got doing all those things and that I almost masturbated again, but decided I needed to tell her before I did.

With her hand still on my thigh, she looked into my eyes and asked if I was still horny? I bit my lip, lowered my chin and told her I was. Lifting my chin with her index finger until we were looking into each other's eyes, she asked if I wanted to masturbate again. I told her I did. The pinky finger of her opposite hand slipped under the hem of my shorts and nearly touched my underpants.

In a soft, but firm voice she said, "Do you want to tell me anything?"

A new and more powerful wave of humiliation flowed through my body. My penis was throbbing wildly under my shorts. Every time I tried to look away from her, she guided my eyes back to hers with her finger under my chin. I had to force myself to speak. And when I did, my voice cracked, "I, I, I am going to go play with myself again."

She then smiled and told me to go have fun. As I stood and began to cross the room, she told me to leave my bedroom door unlocked this time. A shiver shot up my spine and my little penis throbbed wickedly. And as I approached the hall, she reminded me to get naked first. I quickly reached down and pulled my t-shirt up and over my head. I looked back at her and smiled. She hooted and chanted "Take it off! Take it off! Take it off!"

While still walking toward my room, I dropped my shirt on the floor and quickly hooked my thumbs under my shorts and underpants. Just after I turned the corner out of her line of sight, I dropped my shorts and underpants to the floor and kicked them back out into the living room.

After watching the last of my clothing sail into the room, she called out to me, "You naughty little thing! Leave your bedroom door wide open. And I want you to think about me watching you from the doorway while you play with yourself. Do you understand me, young man?"

I called back to her, "Yes Ma'am! Door wide open!"

I hopped onto my bed, spread my legs as wide as they would go, looking down between my naked thighs, I could see down the hall and it made me so very horny! I'd just looped my finger and thumb around my penis and stroked a few times when she called out to me from the living room. I felt so nasty laying there touching myself and continuing our conversation. She asked if I was touching myself. I shivered and told her I was. A few seconds passed before she called out and asked if it felt good. I called back to her and told her it felt very good. I was getting closer and closer to cumming when she called out to me one last time. She told me to yell out to her and let her know the moment I started cumming. Only a few seconds passed before I felt my orgasm well up inside me. Just before it erupted from my penis, I screamed out, "I'm cumming!!"

I remember looking down the hallway, wishing she would step into the doorway and see me. But she never did. My penis exploded all over my stomach, chest, and shoulder. I lay there exhausted, panting, trying desperately to catch my breath. When my heart rate slowed and I was nearly recovered, I took some tissues from the box and cleaned myself up. I then rose from my bed and gingerly walked down the hall. After closing the bathroom door, relieving myself and flushing, I cracked open the door and peeked down the hall. She was nowhere in sight. I made it halfway to my room when she called out to me again and told me not to forget to wash my hands.

Standing naked in the hallway, in the middle of the day and being reminded to wash my hands was such an amazingly embarrassing and arousing thing to endure. I turned on my toes and walked back to the bathroom. Leaving the door wide open, I washed my hands with soap and dried them on a hand-towel.

I dashed back down the hall and paused outside my door. My stepmother was out of sight, but I could see my shorts, underpants, and t-shirt laying on the living room floor. I stood there and considered my next step. I wanted to run out there naked and sit on the couch beside her. But I wasn't quite ready for that yet. Instead, I called out to her and told her to close her eyes. She asked what I was up to. I told her I needed to get my clothes, but didn't want her to see me naked! When she promised her eyes were closed, I peeked around the corner and saw her facing my direction with her hands over her eyes. I asked if she was peeking. She told me she wasn't. I then stepped into the room with my hands over my penis.

It felt so surreal to be there at that moment. She knew what I'd been up to. She knew I was in the same room naked. I was completely exposed in front of the most important person in my life. It was a feeling that sent shivers up my spine and made goosebumps rise up all over my body. Biting my lower lip, I slowly lowered my hands to my sides. My stepmother sat just across the room with her hands over her eyes and I was completely naked right in front of her!

I took a few steps and then bent to pick up my t-shirt. It was inside-out and twisted around. When I got it untangled, I slipped my wrists into the sleeves and raised it up above my head. And just as my shirt began to fall down my arms, my stepmother lowered her hands and saw me naked for the first time. When I looked over at her and saw her smiling, I squealed and told her she wasn't supposed to look yet. I quickly yanked my t-shirt down and tried to cover my stiff penis, it sort-of worked. I told her to cover her eyes again, she refused. She told me I was too cute not to look at. I quickly debated what my next step should be. I decided to get my shorts on. When I went to pick them up, my stepmother whistled and told me I had a very cute little butt. I quickly stood up, blushing from head to toe.

With my toes, I pinched my shorts and underpants and kicked them into the hall. When I turned around, she whistled again before I reached back and tugged down my shirt to cover my bare cheeks. Once hidden behind the wall, I bent down and picked up my shorts and underpants. I was so embarrassed and turned on and excited. I'd never felt like that before. On some level, I wanted to run back into the living room and take off my t-shirt and show her all of me. But instead, I took my shorts and underpants into my room.

Knowing I wasn't ready to run out there naked again, I debated what I should do. I wanted to keep the momentum of the afternoon going. I was having the time of my life! I soon decided on my next step. After tossing my underpants into the dirty clothes, I slipped on the little gray shorts. Looking at myself in the mirror, my stiff penis was plainly visible. On impulse, I took off my t-shirt and pulled my shorts up so they slipped between my cheeks and made my stiffie even more obvious. Just before leaving my room, I rolled the hem down to make the shorts ride really low on my hips.

Taking a deep breath, I left my bedroom and walked into the living room. While I posed for her, my stepmother smiled and said she loved my new look. She was soon staring at my little hard-on and asking if I needed to go back to my room to take care of my 'problem'. I giggled while crossing the room and sat next to her. I told her it felt good to be hard and I thought I'd leave it that way for a while. I went on to tell her that I was surprised I was able to do it that second time so quickly. She wrapped her large, warm arm around my shoulders and pulled me in close to her. With her fingertips sliding up and down along my arm and naked back, she whispered, "You are such a naughty little thing! I never would have guessed that my sweet little stepson was such an incorrigible tease. If you keep this sort of behavior up, you may find yourself not being allowed to wear clothes."

This routine went on for a few weeks. Every time before I masturbated, I reported to her and told her where I was going and what I was going to do. She always told me to strip naked first, leave my door wide open and don't forget to clean up properly. She would usually ask me questions from the next room while I played with myself and always liked me to announce when I was cumming. Afterward, I always made the trip down the hall to the bathroom naked and eventually began to leave that door open as well.

Sometimes she would tell me to put on as little clothing as possible before coming back out to her. This felt like a challenge. I started out with shorts, she frowned when I walked out in those, she'd already seen me like that. So the next time I stepped out in my newest looking underpants. I was so embarrassed, I thought I was going to faint! But she smiled brightly and snuggled me close to her when I'd joined her on the couch. After that I wasn't sure what to wear, I rummaged through my drawers and wound up stepping into the living room wearing a pristine, white ankle sock on my penis. She rose from the couch and gave me a big hug. Pulling my face into her pillowy, perfumed cleavage, she told me I looked fantastic. And she loved the fact that she could yank that sock off at any moment, leaving me completely naked in front of her.

Later that same week, I was in my room, naked and masturbating with the door wide open. My finger and thumb were sliding up and down my skinny penis when I heard the floor creak. Samantha's voice was nearby when she asked if I was still playing with myself. I heard her footsteps coming in the direction of my room! I told her I was and spread my legs even wider as a huge wave of humiliation washed through my body. I really wanted her to see me like this, but the idea of it was so embarrassing! My penis throbbed wildly and a high-pitched squeak slipped through my lips.

I heard her footsteps stop just outside of my room. She poked her arm into my room and waved at me. She asked if I was still having fun. I whimpered I said, 'Yes.'

She must've leaned against the wall outside of my room. She left her hand in plain sight. She told me she could hear the wet sounds of my fingers on my penis. She asked if I wanted her to step into my room. I told her I did. She asked if I was sure. I moaned back and told her 'yes' again.

She then said the words I'd been both aching to hear and dreading at the same time. She said she was going to walk into my room on the count of three. With every digit she counted off on the had I could see, I couldn't stop myself from jerking off more furiously. When she finally got to three, she stepped into my room! But her back was to me! I came harder than ever before. And Samantha stood in there, facing away from me and listened to it all. When I'd calmed down, she asked if it felt good. I whimpered breathlessly that it was the best one ever. Without even making an effort to peek, she left the room while telling me that after I'd gotten cleaned up, I was to join her wearing only my birthday suit.