Guided Masturbation Stories

Caught and Tamed

a contribution by member openthedoor2fun. He is also the moderator of the very relevant Yahoo group Mature_Masturbators

Jan 2005


When I was 13 or 14 I did some housework for a woman my parents 
knew. She & her husband were pretty cool people and they had bought 
a really nice home on a big lot in the woods. Her husband had some 
important job and was always working or off on some work trip so I 
got a summer job being the yard boy. I mowed and raked and clipped 
and moved stuff around. I was a tall kid and she enjoyed having me 
dust, clean or move things on upper shelves. I occasionally caught 
her watching me as I mowed the lawn or did other yardwork, she would 
always just smile at me or give me a wave or 'thumbs up' for my work.

Pat was a good looking woman, and since I had always desired older 
women, a passion that has only increased over the years, I liked 
being around her. She was very open, always dressed casually but to 
the point of being quite sexy to a young teen and she seemed to 
enjoy talking with me, often asking about if I had any girlfriends 
and other somewhat personal questions. She always did it in such a 
natural way I always enjoyed it, even when her questions made me a 
bit uncomfortable. I wasn't old enough to drive and her house was 
so far away she would pick me up and drive me home, so we had many 
discussions and over the summer became quite familiar with each 
other. We became good friends and her questions never felt akward.

Every day after working in the yard or house she would take a shower 
before taking me home, I sat in the family room and drank sodas and 
watched TV. It was a very open house and the family room was 
centrally located, down the hall just past the family room was the 
bathroom where she showered. From my usual seat I could see the 
door and would always see her enter and leave the bathroom, usually 
in some sort of robe or covered by a large towel.

Now this woman was very attractive, maybe late 40's or so, short, 
dark, curley hair, a wonderful smile, beautiful breasts, large but 
not too large and while her ass was a tad big it had a beautiful 
round shape to it and always looked good in her shorts. Hell, she 
looked good in anything. And, I imagined, she would look fine out 
of them as well.

So I would sit and always try to catch a peek of her as she passed 
in my view. The first few times she caught me looking and I tried 
to look away nonchalantly. But she always knew and she would always 
smile so I made no effort to hide my obvious watching her.

Of course every time I looked at her going into or out from the 
shower, I would get a boner and would play with it through my 
shorts, never actually to the point of orgasm, that would come later 
at home, in my own bed at night, thinking of her.

As the summer went on I was getting hornier and hornier every day 
and started timing how long her showers lasted and once comfortable 
with my 'free time' I started pulling down my shorts and giving 
myself a fine handjob imagining what part she was washing right 
then. I started to feel very at home with this routine and became 
braver and more daring as time went on, eventually stroking myself 
to the edge, regaining composure and shorts just as she exited the 
bathroom and finished up into a paper towel after she went into her 
bedroom to dress, ah yes, one last sight of her on the way out, when 
she was most visible, and then I'd get my nut off in a right dandy 
manner.

Well one day I didn't time it just right and/or she was much quicker 
than usual and she popped from the bathroom door and as she gave me 
her usual smile she saw me with my shorts to my ankles and me 
stroking my cock for all it was worth. I'm not sure who's eyes were 
bigger but the smile never left her face and she just walked in and 
dressed like any other day. We didn't talk much until about half 
way home when she said "I hope I didn't interrupt you." I just sort 
of smiled and hesitantly said "No." She looked at me with a 
different smile than I'd seen on her face before.

The next day she popped out early as well but I had been scared into 
not touching my dick at all and I think she was a bit disappointed 
to not see me in such an embarassing situation. The next few days 
were like that, her timing was never the same but she never caught 
me stroking it.

The next week I was back and when she entered the bathroom 
she 'accidently' left the door cracked a little. My eyes were glued 
to that gap as I looked through the 2 inch slot at a huge mirror 
where her nude body was clearly visable. The angle couldn't have 
been better and I watched her shower behind a clear shower curtain, 
exit and towel herself dry. My bone was hurting to be touched but I 
never moved. I watched as she wrapped up in a towel and opened the 
door like always, looking at me with a big smile. Now this went on 
for a couple days and my cock just couldn't take it, I had to stroke 
it while she was in the shower. 

I was having an excellent wank watching her tanned body in the 
mirror and as she got out and started to dry off my mind went into a 
spin, my eyes rolled back in my head and I had the most intense 
orgasm my young body had ever felt. When I came out of my sex 
induced trance I was surprised to see that the bathroom door was 
wide open and the light off. She had to have seen me when she 
walked out, and oh man, this one was going to end my summer job I 
feared.

Again, we didn't talk much but just before she dropped me off at 
home she said "I didn't want to inturrupt you" and gave me another 
one of 'those' smiles.

Things were back to normal for a couple of days but then
one day things changed. We knocked off earlier than usual and she 
and I sat on the patio drinking ice tea and talked about what we 
should do the next day. Then she started asking questions about me, 
again if I had a girlfriend (no) and if I liked girls or if I got 
nervous around them and on and on, the line of questioning was 
getting rather ticklish. 

Then she asked me if I masturbated. Good one I thought, how am I 
going to answer this? Before I could she told me that she thought 
there was nothing wrong with masturbation and she figured that all 
boys did it. Heck, even girls did it, she said to my ever widening 
eyes.

"So, do you?" she asked again. 

"Well, yeah, sometimes," I replied meekly.

"Where do you usually do it?"

"Where? Ah, in my bedroom."

"Is that all?"

"Well....." I tried to get out of my mouth. But she just went on 
with her questions.

"Does it make you feel good?"

"Yeah" I stammered.

"Then good for you," she said and got up. I helped her carry the 
glasses back into the kitchen and she said she was going to shower 
and that I could watch TV.

Wondering what she might have planned I eagerly jumped to my usual 
seat and anticipated the 'mirror dance' as I called it. I sat there 
for much longer that usual when I finally heard her bedroom door 
open from farther down the hall. As I looked up she walked into the 
family room wearing the sexiest getup I'd ever seen. She looked 
like a lingere model in white; high heels, hose, garter, tiny 
panties, sheer bra and a full length see through wrap. She had that 
wicked smile on her face and as she approached a now open mouthed, 
wide eyed kid she said "This is new, how do I look in it?"

I blurted out every adjective for beauty I knew as my eyes crawled 
from tip to toe and back again, and again, and she smiled wide as 
she spun and did her best runway model impersonation. She came 
closer and as she twirled she held out her arms and dragged the 
sheer white cloth over my head. I was speachless, stunned and was 
sporting the hardest hard on I'd ever had. She slowly strutted away 
and sat on the big chair across from me.

"Do you think I'm pretty?" she asked.

I couldn't find enough words to express how beautiful I thought she 
was. She smiled as she adjusted her position and ran her hands over 
her body, breasts and legs.

"Will you masturbate tonight?"

"Yes, yes, tonight."

"Would you like to right now?" she then asked me, looking straight 
into my eyes with a look in later life I have discovered to be that 
of pure lust.

"Right now?" I whispered from a now dry mouth.

----------------

"Right here? Now?" I asked her.

"Yes, right here, right now. Wouldn't you like to do that?"

"Well, I..." 

She broke my stammering with what I took as a command "Stand up. 
Yes, stand up."

I slowly stood and it was plain as day that my tent pole was up in 
my shorts, bent and damn uncomfortable but I didn't reach to adjust 
myself.

"Hmmm, it looks like you really do like my outfit. Are those shorts 
uncomfortable?"

I'm sure my face could have served as the posterboy for the 
terminally lost and confused as I told her that it was indeed 
uncomfortable. "Well then, why don't you take them off?"

"Right here, right now?" I gulped out.

"Yes, yes, right here and now," she laughed back at me. "Or should 
I go into the bathroom so you can peek on me?"

"No, I mean I..."

"Oh, I know you were peeking on me, you're a naughty little boy. 
Did you like what you saw?" I nodded yes. "And you jacked off 
didn't you?" Again, all I could do was nod. "Right here in this 
very room, correct?" Mr. Bobbinghead continued to nod blankly at 
her. "Then why not do it now? Go ahead, pull down your shorts so I 
can get a better look at the toy you were playing with."

I looked around the room, wondering if I could escape (which I 
couldn't anyway) or if anyone else would be watching me. Then as 
she repositioned herself and stroked her silky lingere across her 
superb body, I slowly pulled down my shorts. My young bone 
stretched my underwear and she told me to take them off as well, and 
my t-shirt while I was at it.

I pulled off my shirt first and holding it in one hand put my thumbs 
in my skiv's and slowly bent forwad as I pushed them to the floor. 
As I just as slowly rose back up I looked at her and her devilish 
smile gleamed at me. I stood up and held my shirt wadded in front 
of my stiffy. "Now drop the shirt" she said, and I tossed it aside 
while covering myself with my hands. "Oh no, don't hide it, show it 
to me." And I did, looking down as I put my hands at my side.

"Well that's very nice," she said, "come closer so I can get a good 
look." I took steps towards her and as I did my eyes slid back over 
her body, and just like that both my big head and my little head 
forgot everything except that I was in the presence of the most 
beautiful woman, the most real woman, the most naked woman that I 
had ever seen. Her skin was smooth and her all white lingere made 
each of her fine attributes look like, well, a young boy's wet dream.

I stood in front of her, hands at my sides, as she leaned closer to 
look at my young body. I could feel her breath on me as she moved 
in for a close up examination of my cock and balls, but as close as 
she was, she never touched me. Then she stood up slowly, visually 
eating me up as she did. I stood still as she started to circle my 
body, walking around me, inspecting what felt like every pore on my 
body, alternatly stooping or squating to check the lower half and 
standing to check the top. Her face came so close I could feel her 
hair brush against me and I could smell the perfume on her as well. 
My eyes followerd her as she moved and I was getting an eyefull. 
her white bra was sheer enough that I could easily make out her dark 
nipples and I could have dived into her healthy cleavage.

"You'll be shaving soon, and you'll be growing a lot more hair here 
as well," she remarked as she sat on the ende of her seat and found 
herself eye to eye with my still rock hard cock, now throbbing and 
desperatly wanting release. "You're very hard, show me how you do 
it."

I looked into her eyes questioningly, "Yes, show me how you play 
with yourself." My right hand reached up and my fingers slowly 
wrapped around my shaft. I moved my hand a little, nervously. "Oh 
come now, we can't have any fun like that, stroke it like you do in 
your bedroom." She sat back and relaxed, opening her legs and 
running her hands from her knees up her thighs, over her pussy and 
stomach, and then cupped her breasts before leaning back to watch 
me. That was enough to motivate me and soon I was stroking my cock 
at my usual tempo. It wasn't going to take much and I tried to 
control myself. I wasn't aware what 'edging' was and I'm sure from 
the look on my face and the swollen purple knot on my cock she was 
aware that I was going to pop soon. "Are you going to cum?" she 
asked sweetly. 

"Yes," my jittery voice sputtered out.

"Where do you usually shoot your juice?"

"On a paper towel or in the garbage or..." I could hardly get out of 
my mouth.

"Well, uh, here," she said as she laid newspaper out on the 
floor. "Next time we'll get something better."

"Next time?!" bounced through my head and with that I was off, 
turning to squirt at the paper on the floor. I hadn't 
been 'cumming' for that long, and in fact the first time I did I was 
shocked, but my sperm count must have been in overdrive and this was 
the biggest load I'd ever seen come out of me. Maybe it was because 
I'd never been standing for it but I was shocked to see how far it 
squirted. Pat was too and she laughed with delight and made some 
funny remark about how little had actually hit the paper.

I stood there, dazed, cock still in hand, twitching. She got up and 
walked down the hall as she told me to please clean and help myself 
to another ice tea.

I just stood there for a few minutes, stunned at what had just 
happened, then I put my clothes back on, picked up the newspaper, 
tried to rub away the globs on the carpet and took it to the 
garbage. I poured myself a big ice tea and went back out on the 
patio where I sat and just stared off into space for I don't know 
how long. I should have checked the time to know for sure, but when 
Pat finally came out onto the patio it was quite awhile. She had 
showered and was wearing a pretty summer dress along with a very 
happy smile. I shyly looked up at her and she asked me "Did you 
enjoy that?"

"Yeah, I did."

"That's good, so did I. Now let's get you home, you can tell you 
folks you worked late today." I checked the time in her car and was 
surprised to see that the whole afternoon had blown away in a 
daze. "And just what took HER so long to shower?" I thought to 
myself. As I opened the car door in front of my house she slipped 
me a $5 (I got paid every Friday and today was Monday??) and 
said "See you tomorrow morning" as she drove away.

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Hope you enjoyed that. Did this really happen? Sort of, I take the 
literary license to adjust story to reader. Might there be other 
parts? Mayhaps. 
fred