Ad Ostra

by Rajah Dodger {rdodger@hotmail.com} (c) 2003, 2009

This work is licensed under the Creative Commons
Attribution-Non-Commercial-Share Alike 3.0 United States License (by-nc-sa). In
jurisdictions where the Creative Commons license is not recognized, United
States copyright and Berne Convention provisions apply; all rights reserved to
Rajah Dodger except that electronic not-for-profit reproduction rights are
explicitly granted with the stipulation that this authorship and permission
note must remain attached.

Abstract: Spying on his best friend's mom puts a young man in a delicate
position

My folks both had to go out of town on respective business conferences, and
rather than leave me in the house by myself (even though I'm really old enough
to manage) they asked me to find someone to stay with. I thought of Jeb; while
he and I aren't exactly best friends, we've kind of knocked around together
since getting into high school. We're both bookish types, and we both like
science fiction, so he seemed like a reasonable guy to ask to bunk with for a
week. I talked with him at school, and he checked with his mother later and
called to let me know it would be cool.

Mrs. Ostra, that's Jeb's mom, is nice. She's maybe in her mid-forties, a little
older than my mother, but still attractive in that way some mature women have.
I don't know what happened to Mr. Ostra, Jeb never talks about him and it
didn't seem polite for me to ask. When my folks dropped me off, she came out to
meet them and discuss house rules. She's pretty strict with Jeb -- he has to be
in bed by 9, and he doesn't have free run of the internet the way I do at home.
But she said it would be okay for me to go by my parents' rules while I was
staying at her house.

Jeb and his mom have a nice two-story house, with bedrooms up on the second
floor either side of a long hallway. I wound up in Jeb's sister's room since
she was off in college. It was okay, other than being all in pink, and had a
nice bay window overlooking the front yard. There was a study across the hall
with a nice collection of biographies and fiction; that's where they kept the
computer for the kids to use. Jeb's room was right next to mine -- I mean his
sister's -- and a shared bathroom connected the two. Way down at the end of the
hall was the master bedroom. His mom made it clear that her end of the hall was
off limits but that I had pretty much the run of the house otherwise.

Outside of not having my folks around, staying with Jeb and his mom was a lot
like being at home. Get up in the morning, have breakfast, brush teeth, off to
school after a big hug and pat from Jeb's mom. Come home, study, eat dinner,
watch some TV if the homework is done, and off to bed. Jeb had to go to bed
about an hour before I did, and his mom pretty much left me alone in the
evening. I used their computer, checked in with my IM friends, and did the
normal teenage guy stuff. The weekend was really fun -- his mother took us both
out to the baseball game. Jeb went out Saturday night on a date, but otherwise
we were together just like brothers.

Monday morning Jeb didn't come down for breakfast. When I asked his mom about
it, she told me he was "indisposed" and wouldn't be attending school. She gave
me a note to give to the attendance office, then gave me the usual big morning
hug and pat on the bottom, and sent me on my way. When I got to school though,
the staff was sending everybody back home -- a construction crew had sliced
open the water main so the bathrooms were out of order. I shrugged my
shoulders, turned around, and came back to the house. I came in through the
back door and got a glass of milk from the kitchen.

While I was drinking, I heard what sounded like raised voices coming from
upstairs. Curious, I set my glass down and went through the living room to the
stairwell. I couldn't make out the words, but it sounded like Mrs. Ostra was
really angry about something. I didn't mean to pry, but Jeb was like my best
friend, so I padded quietly up the stairs to the landing. At the top I peeked
carefully around the corner; the commotion was coming from the master bedroom.
Slipping my shoes off, I tiptoed down the carpeted hall. When I got to Jeb's
room, the door was open and I noticed that his room was empty and the bed
looked freshly made.

I went on more slowly now as I got close to the end of the hall. The door on
the master bedroom was open a crack, and I had to get right up to the opening
before I could make out the conversation. Mrs. Ostra was really ticked off at
Jeb, and just because he had a friend staying in the house didn't mean he was
allowed to skip his duties. He was still part of a family, and he was going to
meet those responsibilities. I didn't know what he had forgotten to do, but it
must have been something really important.

That's when I first heard the slapping sound, followed by a low-pitched moan. I
couldn't believe it -- was Jeb's mom still spanking him at his age? I had to
look. When I edged the door open a hair more, I still couldn't see anything
directly but there was a mirror over the vanity at the rear wall which gave me
a view of the room.

Oh. My. Gawd... Jeb's mother was standing in the middle of the room, stark
naked, all long strong legs, long auburn hair down to the middle of her back,
and a fine full ass (especially for a woman her age). When she turned around I
saw her breasts. For-real woman's breasts all right, wide and big with dark
nipples and all swinging heavily as she swung her hand around and down. I heard
the slapping sound again, but I couldn't see Jeb from my position. She was
alternating heavy-sounding spanks with biting comments that were still not
completely clear -- something about his being the man of the house since his
dad left, and something else about a girl and protecting the family's
property.

Right then the phone rang, and I almost jumped out of my skin. Mrs. Ostra
turned aside to answer it, and I finally had a glimpse of Jeb. At least, it had
to be Jeb, although all I could see was two legs dangling down off the foot of
the bed, and a rock-hard cock sticking up quivering over a pair of baby-smooth
balls. Big ones, too. I'd seen Jeb in the school showers at PE class, but I'd
never really noticed just how big his equipment was. I stood there with my
mouth hanging open until his mother's conversation finally penetrated into my
brain. "Water main? And you're just now telling me? No, no, I'm sure he'll be
getting back home any time now."

Oh shit! I was in for it now... I turned and half-tiptoed half-scampered down
the hall, swinging around the corner at the landing and almost falling down the
stairs in my rush to get back to the kitchen. I must have set the world's
record for fixing a sandwich so it would look like I'd been innocently
downstairs all this time, ripping it in half and burying one half in the trash.
I was busily chewing on the rest of the sandwich when she showed up a few
minutes later. She was wearing a suspicious look and a light weight dressing
gown that did nothing to hide the curves of her breasts. I gave her my best
innocent face, trying to keep my eyes above her shoulders. "Hi, Mrs. O, there
was a problem at school and they sent us all home. I guess Jeb won't miss any
classes after all." I indicated my sandwich and continued, "I was hungry so I
fixed myself a snack. I'm sorry, I guess I should have called up to let you
know I was back. How's Jeb doing, by the way?"

She just stood in the doorway and regarded me, kind of like you'd look at
something peculiar on your dinner plate. I couldn't help thinking about what
I'd seen upstairs; I was getting an erection for sure, but at least the table
hid it. Finally, she spoke. "You know, Jimmy, you look a little flushed. Are
you sure you're all right? I wouldn't want two boys getting sick on me at the
same time." She crossed the kitchen to where I was sitting, and stood behind me
to feel my forehead with her cool palms. She was leaning against me, and I
could feel the pillowy weight of her breasts cradling the back of my head.
"You're sweating, sweetheart!" I mumbled something about having jogged back
from school, but she wasn't buying it. She went to the pantry and came back
with two blue pills in her hand. "Take these," she said in a tone that brooked
no argument. They were bitter, but the milk washed away most of the taste.
"Finish your snack and get up to bed, young man. You don't want to miss any
more school, and I don't want to have to call your parents to look after you!"

She left me alone then, and I managed to finish the sandwich. Thankfully I made
it up to my room without running into her. I did notice that the door to the
master bedroom appeared solidly closed now, and Jeb's room was still empty. I
ran into the bathroom to relieve my erection, and after flushing and washing my
hands grabbed a math book and flopped down on the bed, trying to figure out
what it all meant. Obviously there was something going on in Jeb's house that
he'd never mentioned to me.

The math was enough to put me back to sleep with one hand still in my pants
pocket, and I woke up a bit later only half alert, hearing Mrs. Ostra calling
me. I poked my head out of the bedroom door, and she was standing in the open
doorway of the master bedroom, still wearing that clingy nightgown and
beckoning me with her index finger. "Jimmy, would you mind terribly coming down
here? Jeb and I have something to discuss with you."

The house seemed awfully quiet as I nervously left my bedroom and walked down
the hall. I glanced down as I passed the landing and noticed my shoes, so there
was no doubt that Mrs. Ostra knew I'd been spying on them. My heart sank --
there weren't words in my vocabulary for how deep the shit was that I must be
in. She stood blocking the doorway until I was right in front of her, then put
out one hand against my chest and stopped me in my tracks. I looked up into her
piercing green eyes.

"Now, Jimmy, I know you've been brought up better than this. And Jeb assures me
you're a good friend and an honest boy." Her voice sharpened. "At least until
now. So you and I and Jeb are going to come in and have a heart-to-heart talk,
just like mature adults do, and we're going to settle some things before you
leave this house."

At that point I think I would rather have had her call my folks and send me
home; I suddenly didn't want to go into that room. But I didn't have a lot of
choice, and after all I'd gotten myself into this in the first place. So when
she backed up a step and waved me in, I gulped and walked through the door.

I stood there in her bedroom, taking everything in, as I heard the snick of the
door lock behind me. Jeb wasn't on the bed any more; he was standing against
the wall stark naked with his legs spread and his head turned down toward the
floor. I couldn't help but check him out -- his cock was dangling softly, even
so it was bigger than mine. Kind of a dark reddish color too, which I didn't
remember ever noticing in the gym showers. Mrs. Ostra slid her hands over my
shoulders and I felt her breasts against the back of my head again, only I
started when I realized I was feeling skin not fabric. She moved her arms down
my chest and held me in place against her while she began to unbutton my shirt.
"Please don't move, Jimmy," she said, "this will take some time to explain and
I don't think you're in a position to argue the point."

Her fingers deftly unfastened and opened my shirt, pulling it out of my
waistband and leaving it open as her hands explored my bare chest. I was
listening to her words, but my eyes were focused on Jeb. He had lifted his head
and his eyes seemed to be following his mother's hands on me. "I know that Jeb
hasn't told you much about his father. The bastard left us when he was only
seven, and since then Jeb and I have had to be very close to keep this family
together. There's nothing that I wouldn't do for my son, and there's nothing
that he won't do for me."

One of her hands was splayed across my stomach, and the other was doing strange
things with my male nipples. I was getting an erection in my pants, and I
couldn't place the look in Jeb's eyes but it worried me. The whole scene was
strange, for that matter, but I couldn't bring myself to do anything about it.

His mother went on, as the hand on my stomach slid down toward the front button
of my pants. "Now Jeb's been behaving like a lot of teenagers, and neglecting
some of his duties around the house lately -- duties of a personal nature. He
knows what his usual punishment for that sort of thing is," and Jeb swallowed
visibly while his cock suddenly jumped, "but with you in the picture I've come
up with an idea that might work better for Jeb... and perhaps for all of us."

My breath caught in my throat as Mrs. Ostra slid down to her knees behind me,
dragging her body against mine as she went, and her hands opened and pulled
down my pants leaving me in white cotton briefs with my erection tenting out
the front. She continued as if nothing out of the ordinary was happening, even
as her hands wound their way sinuously up the sides, fronts and insides of my
legs making shivery feelings race through my body focused in my groin.

"Since Jeb doesn't seem to be willing to handle all of the responsibilities
around here, I've suggested that he find someone else to cover for him. He
seemed to think you'd be willing to offer your services."

Her fingertips toyed along my inner thighs where the legbands of my briefs
ended. I couldn't open my mouth to say anything in response, half wishing she'd
pull down my briefs and wrap her soft woman's hands around my virgin cock, half
wishing I could run and hide somewhere and never come back. Jeb moved then,
walking bow-legged out from the wall toward the two of us, his cock rising more
with each step. Behind me his mother rose and whispered in my ear, "Just say
the word, Jimmy, and you can have a second family whenever you want, just so
long as you take care of what we need."

I stood there with my pants around my ankles as my friend Jeb walked up to me
and slid his hand down the front of my briefs. His hand was slippery with
something, and he curled his fingers around my erection, fisting it slowly
until I had to close my eyes from the sensation. "Say yes, Jimmy," he said
softly. "Please say yes."

Somewhere in the back of my mind there was a voice screaming to get out before
it was too late, but it was masked by the sensuous haze of the new sensations
enveloping me. I felt my briefs being lowered and soft hands cupping my bottom,
moving into that most private area of my person. When I opened my eyes, Jeb was
looking directly into them and I couldn't look away. His hand worked with
intimate knowledge over my desperately aroused cock while his mother stroked
and explored me from behind, and I felt the whole world swirling dizzily around
me as my legs went all stiff and my balls clenched, so different from when I
did myself, and so intense that I couldn't bring myself to ask just what I'd be
expected to do, just give myself to the two bodies sandwiching me as my cock
spurted into my friend's slick hand and his mother's arms kept me from falling
and my lips uttered the single syllable, "yessss..."

/END/