Ever since I was a kid, I've been really stealthy. I was obsessed with being an ultra cool ninja. I wasn't so great when I first started. I would sneak around the house, following studs in the floorboards to avoid the hardwood creaking. I would hide in closets listening in on people and try to sneak downstairs past my bed time. I always made sure I had camouflage at the ready. Camouflage pants and ninja outfits were my look. I got great at finding hiding places, and if I didn't want to be found, well, lets just say the cops and my Mom were very worried that day.
I got caught a lot too. Hiding under the bed, stepping on the wrong floorboard and my Mom would come crashing in to send me back to wherever I was supposed to be. She was pretty stern and insisted I go to school every day they said I was supposed to. I made all my mistakes back then. Where camo's worked and where they didn't, where I could be quiet and where I couldn't. Most kids, they give up because it gets too hard, they think it's too risky. Grounded, detention, all that stuff. But there is no risk if you learn where the risk is. Getting from point A to point B unnoticed isn't always possible no matter how skilled you are. Learning that limit is what makes someone stealthy or not. I learned that stealth is more about opportunity and timing than simply being quiet.
As I grew up, I moved on. I became more interested in Subterfuge, distractions, alibi. My life got more complicated, more was expected of me, and as a result I needed to drastically improve my stealth abilities. I was still obsessed with being stealthy (I loved the feeling most of all) but needed something to show for it. I started to get interested in pick pocketing. I could practice on friends in school all I wanted with little risk. It was much harder, but I remembered the lessons I had already learned.
Patience, timing.
I learned that a good pickpocket- they pickpocket all day, and yet for only a split second as well. And over time I just got better and better at it. I became proactive about it; better with my light touch. Planning and preparation were key, I now created my own opportunities. I would take more and more, causing my own distractions. More importantly, I was caught less and less. Everyone around me joked about how I 'used to be such a sneaky ninja.' About how I'd outgrown my childhood phase. What they didn't realize is that they didn't see me when I was wearing my camouflage, they never saw me doing anything anymore. But I had their cellphones, their watches.
My own mother looked very confused when one day she stopped doing dishes, took her wedding ring off her left hand, looked at it in a confused manner and then put it back on her right hand. I had only dropped my homework to make her think I had done it, but couldn't resist having some fun with her. When they think it's impossible, they never blame me. They blame themselves.
Around this time I had also started to become obsessed with sex- all the time like most guys I suppose. And inevitably my obsessions mixed. I always knew about sex. All my sneaking had lead to overhearing awkward conversations when my Mom was talking to her girlfriends about it.
Sneaking and sex went together pretty good. Plenty of sex objects became mine to take. Pairs of panties from the hottest girls, a pair of pink heels, the very private web history of the hottest girl in school. I listened in on girls gossiping about sex. I was watching and waiting, horny as all hell.
And I'll admit, I'm a shy kind of guy. Introverted and hardly social. I have an average build and look okay I guess. I knew none of these girls I plundered, none of them even knew my name and just as I was about to go off to college, I still had not been laid. Much to my chagrin, I had watched the girls of my high school get laid by other boys, snatching their cellphones and reading about the secretive places they planned to meet- with the headlights off in some beat up sedan.
I would get the occasional feel of a butt, the outline of a breast. But their are limits.
I was pushing those limits further than I ever thought possible though, and I was getting better all the time.
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I was just about to go off to college and my Mom was helping me pack, making sure I didn't miss anything. We had been at it for hours, and I got the feeling that she was dawdling, trying to drag it out since she wouldn't be seeing me for several months.
In the hot summer heat, I had grown more than appreciative while looking at her. She was in a short yellow sundress and leaning over packing all manner of boxes. My Mom looked great for her age, and I didn't need to imagine how she looked naked. I had seen her large pendulous breasts, and her still-very-nice-behind being soaped up and dried many times before. I had watched her masturbate with night vision goggles on a stormy night. I had crept up under the covers and smelled her musky vagina afterwards.
I had jerked off to her a lot. I was more familiar with my moms sex life and her desires than any other woman I knew. The constant proximity and the ease at which I could spy on her in her most sexual moments had given me a huge kink for mothers. Any mother I suppose, but my own had definitely captured my attention.
So much so, that I was planning to do something today that would go beyond what I even thought was possible. I could sneak into damn near anywhere by this point. Being unnoticed had become effortless to me.
Jill was blonde, 37, and had a cute but motherly face. Dad was gone, and she regularly had fantasies about finding another lover to take her. But after 18 years, she still hadn't found anyone to fit that bill. A few had kind of worked out when I was a kid which gave her time to raise me, but they didn't stick around. She kept in great shape as a result and had an online dating profile. Though the last five or six years, I'd been regularly logging into it and deleting her prospects. But to keep her from being too proactive, I had been letting only jerks message her. All the dates she had, even if they did get lucky or make a good impression- soon fizzled out. She hadn't logged in in several months now after a long string of losers and assholes.
She had become pretty somber about it and I could tell she was getting very lonely. She was writing on a self-help forum online. I created an account and told her to always turn to family in times of crisis. A few posts later and I had become her pen pal and Mom was spilling her guts to me. Nothing I didn't already know, but plenty of chances to drive home that she needed to spend time with me. She had really started to drag conversations out as a result. The smallest details had to be discussed at length from how my social life was going to what I was going to wear today. It was honestly annoying as hell, but it was all part of the plan.
We had a storage room in our house that was kind of like an attic or garage. Boxes and old furniture and Christmas decorations were piled high everywhere. Jill was leaning over a large trunk of sorts sitting on a desk, her arms digging through a sea of loosely sorted memorabilia. Her butt was thrust outward ever so slightly.
My mom had just found an old photo album while digging through some of my old books.
"Oh look honey, do you remember this hike we took? You were only 5 here."
"What, where?"
"Come here deary." I walked over to see what she was doing and she handed me an old picture.
"Oh wow, yeah, I remember that one. Oh crap." I dropped the photo to the floor.
My mother distractedly moved to pick it up and with a quick pinch and a squeeze through her dress her panties slid off and dropped to the floor.
Silently, silky, friction-less. She felt nothing, saw nothing.
A flurry of touches distracted her, not real touches, but scratches and itches created at just the right time. The kind you feel when you feel nothing. Off one leg and as she teetered back from picking it up, I had the other leg free as well.
My Mom put the photo back in a large album. I put her panties to my nostrils and breathed in silently. Perfumey, musky, motherly. I had smelled plenty of panties but I enjoyed Jill's the most.
I leaned over her shoulder to look at more of the photos she was showing me. A bit of small talk while her panties slipped into my pocket.
"Oh wow, that was a long time ago." My fingers raised her dress higher exposing the lower part of her butt. Though my pants looked like jeans, the legs had been shined, thinned, and coated in a silky fabric that felt just as light and smooth as a dress. I pressed into her.
My mom excitedly showed me a picture of us at the grand canyon. My fingers danced over her sex, lightly tapping and spreading her folds, imitating her panties with my fingertips. I simply stared slack jawed at the picture.
"You look stunned sweety, I bet you don't even remember that. You were only one year old." My cock was rock hard and her voice played on my ears. Her remembrances were stoking my arousal to incredible heights and I couldn't resist pulling my dick out.
Let me tell you about my cock. It's very stealthy. The zipper on my jeans is perfectly silent. You wont find that in your average discount store. They were custom made- and expensive. I could jack off in complete silence and my orgasms were controlled and discrete.
"Tell me about the Grand Canyon Mom."
I pressed myself firmly into my mothers backside. My cock was resting at her entrance. Her voice twittered on about all the details. I rubbed my penis up and down her sex in the most innocuous way as she told me about the winding trails.
"It was so hot out that day. I got so tired from carrying you." She turned the page.
"Hey Mom, what's that." I pointed to a small bag deep in the chest. She leaned in to grab it and as the chest pushed up against her breasts I grabbed her globes hard, imitating the hard edge expertly. I pretend to try and help her retrieve the baggy which helped me grab her tits even harder.
My mother gasped in joy.
"Wow it's..." I slowly snuck the head of my cock into her vagina.
"A lock of your hair from when you were a baby." The rest of my penis slithered in unnoticed.
I was firmly planted deep in the vagina of my own mother. I relented on her breasts as she took the lock of hair out and ran it under her nose.
"That's cool Mom, I didn't know you kept that"
"It's because I love you honey. I cherish everything about you." She very carefully resealed the hair into the baggy. My cock pulsed. Her insides were so unexpectedly warm and sexual. Her folds enveloped me slippery and wet and it took so much effort not to just start violently slamming in and out of her. She was being so motherly and affectionate yet her cunt was pleasuring me like any whores would.
"In fact, I'm going to miss you once you go off to college." My Mom was getting a bit choked up as she tried to stifle the emotions at the same time.
"I'll miss you too Mom." I slowly withdrew my penis from her and very slowly put it back in.
"Ah, thank you." She had no idea that she had once more taken her own sons penis inside of her.
"Hey Mom, do you have any photos of you I could borrow to remember you by?" I began to slowly fuck my own mother. Hardly moving in her folds, letting her vagina lightly jerk my foreskin but not actually stretching her precious lips to the point where she could notice. But deep inside the head of my penis was in heaven as it twirled within her folds.
"That's so. . . sweet of you. Here." My mom was flipping through another album. These were mostly pictures of herself. Her fingers trailed over photos as mine trailed over her nipples in quick darting motions. She was about to select a portrait she had taken of herself recently. My cock throbbed hard within her seeing her all dressed up and with heavy lipstick on.
"Hey let's keep looking." I turned the pages back. her mature figure turned to pictures of her in her thirties at my birthday party. She kept offering commentary as I slowly edged myself inside her. I kept her going back and back. She embarrassingly skipped pictures of her breastfeeding me without comment. And then I was gone.
I thrust as deep into her as as I could while she showed me pictures of her nineteen year old pregnant belly. This was my mother. To the left of those pictures had pictures of her and my Dad. I marveled at one of her in a swimsuit. Her tight eighteen year old body. Her belly was perfectly smooth, pale, flat, and rippled with the slightest hints of abs, ribs and hip bones. She had these small perky globes contained neatly in her bikini. She was stunning.
I felt for a moment that I was enjoying all of these different women. The young, the pregnant, the older. It was a beautiful feeling and it sent me to the edge. I could never go back, could never meet my mother, as a man, as she was then. But I had the talent to take her. I could feel her large motherly breasts in my hands, so unlike the tiny perky ones in the photoes. I came hard sliding my penis up and down her vagina in a calculated way. At the same time I was placing touches and pressure points to distract her, inundating her with complicated questions about which photos I could take. I had taken five and asked her which ones I could keep, making sure they all were key moments she didn't want to lose to a hungry washing machine or a rainy backpack.
"Here, you can have this one" She handed me the picture with the least sentimental value. Not my first steps, or her one year anniversary. I took the photo of her in the bikini and looked closer at it admiring her bright smile.
I deposited my seed at all levels of her vagina. I was depositing my cum in such a way so as to not leave a creampie. I methodically coated her vaginal walls so that she soaked it up as much as possible. My cock slowly slithered out without a sound leaving only a slight wetness.
She seemed to notice something and her hand drifted downward but stopped. She turned around but my jeans were already zipped up. I could see the dawning realization on her face that she had forgotten to put on panties today.
She thought she could remember doing it, I could see the gears turning.
"Well, we. . . We really should finish packing." My mom picked up a box after shutting the trunk full of photos.
She got about ten paces before stopping in her tracks, then putting the box down slowly. I admired her butt all the way down. Seeded fully and on no birth control just as I had planned. I had been keeping track of her cycles and now was the time. I was unsure if she was still fertile, but I was going to give it everything I had. Millions were now swimming around that cute butt trying to do the job for me. I couldn't help but cheer them on as they tried to sneak into one of my Moms eggs undetected.
She had just noticed the slickness between her thighs though. Without my expert touch to distract her and dry her, the ruse had quickly fallen.
"On second thought, lets take a break. I think a need to lie down for a bit." She headed towards the master bedroom walking a little bit too quickly.
"Take your time, I still have a lot of things to pack." I wave her off but she hardly looked back. Super distracted.
I don't like to admit it, but as I looked down at the photo of her in the bikini, I knew who this was truly for. She probably attributed the slickness to seeing so many pictures of dad. At least that's how I would justify it.
The master bedroom had no shower. I turned the main one on. It was a hot day and a long cold shower was realistic. Now she knew where I 'was.' I approached her door and gently tested it. Locked.
I had a few basic spy tools. Nothing too fancy. A few mirrors, a spyglass, some twine. Everything I would need to figure out what my Mom was doing in her bedroom.
And there she was; sundress ridden up, a hand in her crotch. Eyes closed and surely dreaming.
This door always squeaked. Always, it was like an alarm bell. But not when I opened it. A few adjustments and a bit of leverage and it swung open without a sound. The lock, to say the least, was absolutely pulverized.
I took light steps towards the bed where I could hear the small angelic moans of my mother as her fingers played with my seed. Her legs squeezed together around her hand. I responded in kind stroking my cock right in front of her. She was gorgeous like this.
She shifted onto her side and briefly opened her eyes looking right at me. I became one with the drapes. I had planned for this, my clothes looked normal, but they were camo. My Mom looked right past me as if I was part of the room.
"Oh my god, I'm so horny." She mumbled to herself as she clutched sheets around her and shifted away. I wasted no time moving to the bad. I quickly enveloped her, encouraging her with scratches and caresses and an unnatural shifting of the bed she could not detect. I spent all my energy, every ounce of skill I had to make sure she ended on her stomach, masturbating herself with her head pressed into the pillow.
Her fingers were dancing on my wet fingertips as my fingers matched her actions from behind. I worked her in exact mimicry of her own devotions to herself. But mine went a bit faster, a bit harder.
I directed her attention to the nightstand. Her pillow forcing her too look at it every time she opened her eyes. She was moaning more insistently, faster and faster. She was going for it and my fingers slowed down. Her own pressed harder into me but couldn't quite give enough pressure to push her over the edge. Her orgasm was fading, her pleasure escaping while her needs grew.
Her eyes bolted open. The nightstand.
Yes. The dildo.
She had bought it under the advice of a 'lady' she talked to online. I had worked on this for months. My mother had a dildo exactly the size of her sons penis. It came highly recommended. My mother trudged herself up and fumbled with the drawer, digging under the magazines to find it neatly wrapped in a towel.
It was summarily slammed into her vagina. In it went, providing finally the increased pressure she craved. She moaned.
"Yeeeeees. Yes yes yes." in almost a whispered voice of delight. The dildo came out of her pussy, and back in. The dildo came out of her pussy. Her grip was tight around the base of it but I waited for weakness.
There!
I switched them out, giving her a cut off dildo with just the base. A prop isn't the most artful part of stealth, but sometimes they are required when options are slim. I was now fucking her with the original dildo while she uselessly thrust a stub in the general direction of her sex. One of my hands was giving her the proper forceful feedback while the other fucked her. She moaned and moaned under my jabs into her pussy.
My dick was at full attention and I lined myself up behind her. The dildo came out of her pussy, all warmed up to body temperature. I thrust into my mother hard to match her ferocity and she let out a long slow moan. It was the most beautiful cry of pleasure I had ever heard her make. Maybe that's just my imagination. Maybe it was a moan like all the others. But my cock was making these ones, and they sounded much fuller, better, louder to my ears. I was proud of these moans.
She was unknowingly guiding my dick, helping me fuck her exactly how she wanted to be fucked. She was teaching me what pleased her and how to move.
I was fucking my mother at a fierce pace. She kept trying to grind herself onto my lap but failed to discover me every time. My reflexes were perfect. Despite all this, she was the only one making noise. I was completely silent, slamming into her while remaining perfectly balanced, without disturbing the bed in the least. I had reinforced hard points that aided in my stealth, the house was rigged with stealthy additions.
Her pace was increasing, her moaning turned to little cute bouts of grunting. And just like that, my Mom was cumming on my dick. I was cumming in my Mom- again.
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Later that day we had the car packed. A couple boxes with room to spare. I had spent most of my time packing her pussy full of cum. It was a long drive ahead of us, since I was attending a college several states over on a full scholarship. My Mom was impressed with how little I was taking. But of course, there's a story behind that.
I wasn't actually going to college. Not yet, anyways. I didn't need a job. Years of cheating off tests had left me far behind my peers. I was great at other things though. Stuff involving cash registers and ducking cameras, or walking off with someones keys. Fraud, impersonation, signature forging. Money was no problem for me. My ambition was Jill.
I was done playing around with her. This was just a little bit of fun while I prepared the real event. I intended to fuck my mom regularly, get her pregnant, and make her orgasm as much as I wanted. In addition to being sneaky, I was a master of disguise!
My Mom had given up on online dating, her self esteem was destroyed despite being very beautiful still. For over a year I had been coaxing her to accept that perhaps she needed to lower her standards and accept less savory individuals into her life. I had been emailing back and forth with her about becoming a sex slave. After so many failed relationships, it was decided that she needed to be treated like an object in the bedroom.
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It was late on a Friday night, we had just had a nice date. I took my mother to a very expensive restaurant, the best for her. She had a beautiful red dress on, gold jewelry and lipstick. I leaned across the table to give her a kiss. Afterwards I adjusted my sunglasses and fake mustache. She was aware of my. . . habits and desires. . . and yet continued to date me. She had no idea I was her son, we were dating as equals. She thought I was around her age.
"Time to end this charade and go home. Time to show me the real you." The light and mirth drained from her eyes, her expression becoming serious, and maybe lustful. I took my mother by the hand and lead her silently to a cab.
When we got home, I had her summarily strip. Off with the dress, the fancy jewelry. I tossed the leather harness at her feet and went to pour myself a drink. Coming back I admired her. My mother waited patiently on all fours, her head face down staring at the floor. She didn't look up when I came in. Large tits were framed by the harness and her distended belly hung down heavy with our child. I had transformed her body just as my father had.
Her hair hung down covering her face and I could make out the tattoo on her neck. She hated that tattoo, she resisted me so much on it. But after denying her my dick for a week she begged me for it. She had taught me exactly how she liked to be fucked, and I had learned how to fuck orgasms out of her just like I was picking a locked door. I could make her wildest fantasies come true, and she soon came to realize she could not live without my amazingly stealthy dick. She grudgingly gave me what I wanted even though I had the same name as her son.
I took a sip of whiskey admiring my name on her neck. My mustache dangled from my face. I walked over to her and got down behind her and grabbed the harness, positioning my cock at her entrance. One thrust into her wet cunt and she was already moaning. I took off my sunglasses so I could see my name on her neck better. I leaned over and began fucking her in earnest, cradling her full belly, my chin resting on her shoulder as I jack hammered into her. She was mine fully.
I drew long moans from her.
"Fuck me harder." My mother begged me. I slowed down deliberately instead.
"No, use me like a whore. Like you paid for me." She slammed her ass back into me. She would have none of my teasing, she wanted me to just take pleasure from her. Like I had trained her. I happily complied and began fucking her in earnest.
Her moans resumed.
With a wet plop, my mustache fell to the floor. My Mom looked at it and then quickly turned around looking me in the eyes in a state of shock.
"Jiminy cricket, you're my son!"
I fell backwards, my dick slid out of my mothers vagina. I scrambled for my sunglasses like they could help. My ruse was uncovered, it was no use.
How could I be so sloppy... was it the whiskey?
I sat on the floor, head in my hands. I had ruined it, I had messed up. I was on the brink of tears.
After a few moments I felt my mothers hands on my arms. Bringing them down to expose my face.
"Please. I'm not finished." Her face looked anguished as she raised me up to the couch. I felt her hands positioning my dick as she lowered herself onto my lap.
"Master, please fuck me." I held her hips still with her planted firmly on me.
"You're not mad, Mom?"
"Not now. We can talk later." Her hips were rolling on my lap. She wouldn't meet my eyes.
"I want to talk now." I felt foolish. This wasn't the reaction I expected.
"I don't know what to think. When I love my son and I've been . . . bred by him as well." Her voice choked up and tears formed in her eyes. She looked down and cradled her belly.
My cock stiffened. This wasn't the first time I had made my painslut cry during sex. I could see horror in her eyes as she looked at her belly. I pressed into her, gripping her hips.
"We could stop Mom."
"What am I going to do, ground you or send you to your room? Go back to being mother and son?"
"Well. . . "
"I don't have that authority anymore. You're my Master, you own me, and we both wanted this. I'm not responsible anymore, this is on you." She pats her belly.
"Just fuck me." Her hips rose up and down, her large belly, massive breasts and swollen nipples hung in front of my face. Her tears were falling onto my shoulder as her harness chains jingled back and forth.
She was taking her pleasure, speeding up. My Mom was trying to cum on my dick.
"You're grounded Mom."
"What?"
"Get on the floor." She stood up a bit confused and carefully lay down flat. I stood up, my cock was hard. Too much to drink tonight.
It took me a moment. But slowly my bladder relaxed. I let out a stream of piss onto my mother. I'm not into watersports, I don't get turned on by it. I had never done this to her before.
"Open your mouth." I sprayed her face and zig-zagged all over her body. If this was going to be our relationship, I wanted the rules of it to be clear. I could no longer see her tears.
I put on her collar and leash, a thick chain. She smelled terrible.
"Get on your knees."
I grabbed her head and shoved my cock down her throat. Rougher than I knew she could handle. It only took a few seconds of it before her expensive dinner came up.
Disgusting. It washed over my dick and down onto herself. I kept going hard on her for a bit. I was close. I pulled out and jerked myself off onto her face. She ws gasping for air. The smell of bile made it hardly enjoyable. I painted her face in a workman-like fashion.
My Mother did not look me in the eyes. She knew her place.
I handcuffed her, and put another steel cuff on her leg. I had bolted metal loops into the floor here so I could chain her by the couch. The chain was already there, I simply padlocked it to her cuffs.
I threw an old blanket over her. She was heaving again from the smell. Another stream of gray-brown puke forced its way up past my mothers lips. Adding to her misery.
"You're sleeping here tonight."
I walked away and took a shower. She had been asking me to pee on her for a while now. I wasn't into it. But I felt like I owed her now.
I came back to see her off before going to bed.
"Mom, I'm going to be much harder on you from now on. Now that you know how worthless you are, carrying your own grandchild." Tears were running down her face. The blanket was soaked with piss and puke. I cranked up the heat so that she wouldn't be shivering all night.
"Feel free to masturbate." I headed off to bed as her hands shot down to her nether region.