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.
-------------------------------------------------------
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.
