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…”