Aunt Karen Shopping (www ) Author unknown
Aunt Karen Shopping (www ) Author unknown
We were on our way to the mall when Aunt Karen started talking to me about the
“rules.” I don’t remember exactly how she put it, but she talked about how she
knew we had both been having fun for the last few days and that she wanted us
both to feel comfortable and continue having fun. But she was concerned about
my being only 14 years old and that certain things were i*****l for her to do
with someone my age. She said she would feel more comfortable if we set out
some rules that would protect us both. So the rules ended up going something
We could not touch each other in a sexual way – which meant that I couldn’t
intentionally touch or caress her breasts, her ass, or her pussy; and that she
couldn’t intentionally touch my penis or my ass. She said that it would not be
right for her to masturbate in front of me since she was an adult. But said she
thought it was okay, since I was a horny young man, that if I needed to relieve
myself that it would be okay as long as I didn’t expose my penis to her. That
pretty much covered what she thought we shouldn’t do.
Then she talked about what she though would be acceptable. It was okay for us
to express affection as in the way of a hug or a short kiss. It was okay for us
to see each other naked or to see sexual body parts exposed, as long as it was
not a “display.” I wasn’t too clear about this at first, but the idea that I
got was that we weren’t to prance around in front of each other naked, but if it
happened in the normal course of events, it was okay. It was okay with her if I
ever wanted to go into her bedroom closet and “enjoy her lingerie” as long as I
asked her first. And she said that we could talk about these rules any time, to
make sure we had the same understanding about them. She said that the rules
should never be broken, but that stretching them a little was okay.
I felt better after hearing her rules because now the unspoken had been spoken.
We rode in the car together toward the mall. She wore the short stretchy dress
that we had decided on earlier. As she worked the pedals of the car, her dress
rode up higher and higher. When we stopped at a stop light, she asked me to
look under her seat to see if I could find some lipstick that she was missing.
I leaned over and reached under her seat. As I did this, my head was next to
her knee and I looked up her thigh to the crotch of her white nylon panties.
The light turned green and when she took her foot off the brake, her legs spread
wider apart. “Nothing?” she said. “Un Uh,” I answered. She reached under her
seat as she drove saying, “It must be under here somewhere. It’s the only place
I can think it would be.” Her legs were spread even wider to make room as she
fished under the seat. The dress had now slipped up to her round hips, exposing
the bottom half of her panties. I kept fishing for her lipstick to no avail. I
was thoroughly enjoying the view. I was hard as a rock! Then she said, “Maybe
it’s on the seat. I’m probably sitting on it. I’ll lift up and you check.”
She grabbed my hand which had been under the seat and moved it between her legs.
I moved my hand under her ass and felt around on the seat. Since she had moved
my hand between her legs rather than reaching under from the side, my forearm
rubbed against her pussy as I felt around on the seat. Her pussy felt hot and
moist against my arm. She lowered her butt back down so that I could feel her
soft ass cheeks rubbing against the back of my hand. She ground her pussy ever
so slightly into my forearm.
I said, “Isn’t this against your rules about touching?” wanting to make sure I
had understood them.
“No,” she said. “The rules is that you can’t intentionally touch me in a sexual
way. You’re just looking for my lipstick, aren’t you?” She had a slight smirk
on her lips.
“I guess you’re right,” I answered, now understanding that she intended to push
the rules to the limit. And the game was on! I continued feeling around under
her ass for her lipstick, my forearm rubbing against her pantied pussy. This
continued for a minute longer. I noticed Aunt Karen’s breathing became short
and a few beads of perspiration appeared on her upper lip. She must have been
very aroused. Then she said, “Here we are!” And she turned into the mall
parking lot. She sat back down on her seat and I moved my hand away.
When we were parked, Aunt Karen got up on the seat on her knees and leaned over
into the back seat. “Maybe it fell back here,” she said. She was kneeling on
the middle of the bench seat, right next to me. Her ass stuck up in the air as
she bent down into the back seat. Her dress was now up around her waist, her
panties completely exposed. I grabbed at my erection as I watched her ass
wiggle around next to me. My balls were starting to ache from having a constant
erection. She turned her ass toward me as she reached back down on the floor.
Her ass was now right in my face. I could see a wet spot forming at the crotch
of her panties. I could smell her mixture of perfume and sweet excitement.
“Nope. It’s not back here either,” she said as she lifted herself back up and
turned around in the seat. She looked down at her exposed panties and said “Hey
you’re supposed to be watching out for me so that doesn’t happen!” Then she
pulled the dress down over her panties to her thighs.
We got out of the car and went into the mall. We went straight to a department
store, and into the lingerie section. The store was very quiet. There was a
woman hanging things on a rack on the other side of the room. Other than that,
we seemed to be pretty much alone. I followed Aunt Karen as she walked around
the maze of racks of slips, panties, bras, and nightgowns. The silky material
of the lingerie brushed against my arms as I followed her, watching as her dress
rode up higher and higher. When she bent down to a lower rack, I caught a look
up her dress. When she stood back up, her dress was up higher. I pointed out
to her that I could see her panties. She had several items in her hands at this
point, that she had picked up off the racks. So she asked me if I wouldn’t mind
pulling her dress back down for her. Of course I was happy to oblige, and took
my time stretching the dress down over her round hips and ass. She thanked me
for keeping an eye on her hemline and continued browsing the racks and selecting
items. She said if I saw anything that I’d like her to try on, that I should
pick it up and that she’d take it into the dressing room with her other things.
So as I followed her, I did pick up a few things for Aunt Karen to try on. I
hoped that I would somehow get to see her in these things. I had deliberately
selected several items that I knew wouldn’t fit right. I knew that she wore a
size 8 panty, so I selected a size 6 and a size 10 for her to try on. I wanted
to see her trying to squirm into the ones that were too small for her. And
there was something erotic about the thought of seeing her in a pair of big
silky nylon panties that were too big on her. Then when we passed the bras, I
selected one that I knew would be too small. She wore a 40D, and I selected a
38B, knowing there was no way she could squeeze her big breasts into the small
cups. She had selected several nightgowns, slips, and panties to try on.
As she led me toward the fitting rooms, I noticed her looking around the
department. The sales lady was far on the other side and around a corner. She
couldn’t see us. Aunt Karen said, “why don’t you give me a hand with these
things,” and led me into the farthest fitting room.
The room was very small. It was square – about 4 feet wide and 4 feet long.
There was a full-length mirror on the back wall and a hook on the side wall to
hang your garments. There was a small stool in the corner. She handed me the
things she had in her arms and asked me to hang them on the hook. The room was
so small that it seemed impossible for us to keep from bumping into each other.
When I turned back around, she had her dress up over her head as she was taking
it off. She stood before me in her high-heels, her white nylon briefs, and a
white bra that had big thick lace covered cups covering her breasts. I was
staring at her bra as she pulled her dress off the top of her head. When she
shook her hair out after removing the dress, her breasts wobbled from side to
side despite the big utilitarian bra holding them in place.
I think I had sported a constant erection since we were in the car. I had
pulled my penis upright so that it wouldn’t be so obvious. But I’m sure she
could still notice the bulge in the front of my pants. She turned around and
bent over to pick her dress up off the floor, and as she bent over, she pushed
her panty-covered ass into me, rubbing it against my erection. “These rooms
were definitely not made for two!” she said. I agreed.
“Why don’t I try on that nightgown first,” she said, pointing to the garments on
the hook. I handed her the gown. It was mint green and very sheer. She
slipped it on over her head and pulled it down over her breasts and hips. The
diaphanous material was almost invisible. It hung loosely to the ground.
“Ooooo, this feels nice,” she said. “Here. Feel,” she said, taking my hand and
placing it on her hip, then running it up her side and back down to her hip
again. “Yes, that does feel nice,” I agreed. I allowed my hand to stay there
after she let go of it. I rubbed her hip from the waist of her panties to the
elastic leg band and back again. Feeling the way the sheer nightgown slid
against the fabric of her panties. “Very nice.”
She turned to face the mirror. Having to stand in the center of the small room
to see herself, my back was against the wall and she pressed her hip against my
crotch as she stood there admiring herself in the mirror. My penis throbbed and
I thought I was about to come. “Yes. I like this. I think I’ll get this one,”
she said. She moved from in front of the mirror, relieving the pressure on my
penis before I came in my pants.
Next she tried on some panties. She had selected two different pairs. She
asked me to hand her the pair that had a flowered print all over it. Then she
asked me to hold them for her for a moment while she took off her panties. She
slid her fingers into the waist of her white nylon briefs and began pulling them
down. She pulled them down over her hips and her ass and when they got to her
mid thigh, she was stuck. With both of us in the room, there wasn’t room enough
for her to bend down all the way to take them off. She stood before me with her
panties down around her thighs, her pussy exposed to me, and said, “I think I’m
going to need your help. I can’t bend over that far in here.”
I got down on my knees and held onto her legs briefly to steady myself as I did
so. I knelt between her and the garments that were still hanging on the wall.
Her exposed pussy was just inches from my face. The hair was neatly trimmed but
not completely shaven. “You know what?” she said. I looked up at her as she
peered down at me over the shelf of her breasts. “I think I’ll try on these
other ones first.” She reached to the hook on the wall above and behind me.
Her pussy was now touching my face. My nose was buried in her pubic hair. I
smelled a mixture of flowery perfume and her natural musky scent. I breathed in
deeply before she moved away. “Will you take those off for me now?” she asked.
And I slid her panties down her legs.
“Here. Now help me step into these,” she said as she handed me the other pair
of panties. These were ivory colored with a lacey front panel. I held them
open for her as she stepped into them. When I had them up to her mid thigh, she
said she could get them the rest of the way and turned her back to me and bent
over to reach for the waist of the panties. As she bent over, her ass was
pushed out toward my face. I was still on my knees. At its closest point, I
probably could have stuck my tongue out and licked her ass. Then she pulled
them up the rest of the way and asked me what I thought. They were beautiful on
her, hugging her round curves in luxurious femininity. I told her so.
The routine was the same for the second pair of panties. But this time as she
turned around to pull them up from her thighs, she bent over to reach for them,
pushing her ass toward my face, then she seemed to lose her balance. She kind
of hopped and leaned back toward me. As I reached my hands up to steady her, my
nose went right into the crack of her ass. So there I knelt with my hands on
her hips and my face stuck in her ass, her panties still around her thighs. I
thought I had died and gone to heaven! I held my face there as long as I dared.
It was probably only for two or three seconds, but it was wonderful! She
steadied herself and I asked her if she was okay. She was. She thanked me for
After pulling up the flowered panties, she said she had a bra to match them.
She asked me to hand it to her. I grabbed the flowered bra off the hook for her
as she began unclasping the bra she was wearing. I think it had about four
clasps on it. When she was done, she let it fall forward and down her arms.
Her big soft breasts now hung freely. Her nipples were erect and slightly
upturned. The flowered bra was the type that clasps in front. She slipped her
arms into it and pulled the cups around and clasped them under her breasts.
Then she pulled the cups out and away from her chest, allowing her breasts to
fall into the large cups. She reached in the cups and arranged her breasts.
“What do you think?” she asked, turning this way and that, then looking at
herself in the mirror. “Do you think they separate my breasts too much? I like
it when a bra gives me a lot of cleavage!” She squeezed her breasts together as
she said this.
“Well I think it’s beautiful,” I told her.
She turned toward me. “Do you like the way it feels?” she asked. “Go ahead.
I reached up with both hands and caressed her breasts through the cups of her
bra. I could feel her erect nipples pushing at the palms of my hands through
the cups as I caressed and squeezed her. She closed her eyes and let her head
fall back. “They feel very good,” I said. Then I corrected myself. “I mean
the bra feels very good.” My hands were still on her breasts when she opened
“Okay, then it’s decided. I’ll get this bra and panty set too!” she said.
All that was left were the three items I had picked out for her. She asked me
what I had found and I handed her the small pair of briefs. The size 6 pair.
“These might be a little small,” she said as she held them and looked at them.
“Let me get out of these first.” She unclasped her bra and set her breasts
free. As she handed me the bra, her breast brushed my arm. Then she looked
down at her panties. “Can you help me with these again?” she asked. I knelt
down in front of her and pulled her panties down and off her legs. I then stood
in front of her. She was totally naked except for her high-heels. She looked
me directly in the eyes and thanked me for helping her with her shopping. She
told me that she really appreciated how helpful I was being. And then she gave
me a big hug. I held her totally naked body in my arms for just a moment,
feeling her soft breasts pressing against my chest and her naked pussy pressing
against the bulge in my pants. And as she pulled away, I let my hand drift down
to the round cheek of her ass. She held the size 6 panties out to me. “Now
help me get into these.”
I knelt in front of her and held the panties open for her to step in. I pulled
them up to her thighs, then stood back up. She grabbed the waist of the
panties, pulling and jumping and wiggling, trying to squeeze her ass into them.
Her unfettered breasts bounced around as she did so. I couldn’t believe what
she asked me next. The panties were part way up when she stopped. She told me
her breasts hurt when they bounce around that much, and would I mind holding
them while she tried to get the panties on.
So I sunk my fingers into her soft breast flesh and grabbed onto them as she
resumed her bouncing and wiggling. I couldn’t believe the feeling. Her breasts
were so soft and warm! She finally got the panties up and I reluctantly
released her breasts. The panties were on, but were very tight. The waistband
dug into her waist and I could see the outline of her puffy pussy lips at the
crotch. “These are way too small,” she said, looking into the mirror. “Help me
get these off.”
So I knelt in front of her and yanked on the waistband of the panties until I
got them over her hips and down her legs. Once again, she stood before me
totally naked. “Let’s try those other ones you got. Maybe they’ll fit better.
So I handed her the size 10’s. She held them out in front of her and they
looked huge! They were thin white nylon panties with no ornamentation. Just
plain, silky smooth, white nylon panties, big enough for even Aunt Karen’s ample
buttocks to seem lost in.
I knelt on the floor holding the big waist open for her. She stepped in and I
slid the big panties easily up to her thighs. She pulled them up the rest of
the way and I stood back up. They fit her very loosely, but not too loosely to
stay up by themselves. The excess of soft nylon material lightly caressed her.
She said, “well these are kind of big, but they feel really good this way! It
feels so soft and silky against my skin.” As she said this, she was touching
herself all over the panties, rubbing them against her ass and her pussy. “Do
you think they look funny this way?” she asked.
“No,” I told her. “They look great like that! And I can imagine how good they
must feel!” She invited me to touch them. And I did, running my hands all over
them, feeling her body through them.
“And is that a bra you got me to try on?” she asked.
I handed it to her. It was obvious that the cups were way too small for her
breasts. She said, “It looks kind of small, but I’ll try it.” She slipped her
arms into the straps and pulled them up over her shoulders. As she reached back
behind herself to do the clasps, it caused her to stick her chest out further,
making her breasts look even larger. I could tell it was a struggle for her. I
offered my help and she let me clasp the bra for her.
When she turned around, the cups were up over the tops of her breasts. Her
breasts were hanging down below the bra. She tried to pull the cups down over
her breasts. And when she did, they flopped out over the top. Then one at a
time she pulled the cups out and lifted her breasts into them. The cups were
way too small and she kept trying to stuff her nipples into them. But they just
kept popping back out. I was enjoying the show tremendously when she finally
gave up and said it was no use.
She had tried on everything. And we had both had a lot of fun with the
situation. At least I know I did! She removed the small bra and the big
panties and got back into her original outfit. And we took the items she was
going to keep, to the check out stand to purchase them. I could tell that
having the new rules was going to be lots of fun! But after all the excitement,
I just wanted to find a place to go relieve my tension.
I followed her as we walked out of the mall. I stayed about three steps behind
her and watched as with almost every step, her dress rode up higher and higher
on her hips. The mall wasn’t too busy, but there were some people about. By
the time we got to the main entrance to the mall, I was able to see a bit of her
white panties peeking out from the bottom of her dress. As we walked out and
into the parking lot, the whole bottom half of her panties were showing. I knew
she must be aware of it. How could she not be? She had to be putting on the
show for my benefit. When she finally stepped into the car, her dress was up
around her waist, her panties totally exposed. A man who had just parked next
to Aunt Karen’s car, got a great show as she walked past and opened her door.
He sat there in his car with his mouth hanging open, watching a woman walk past
him with her dress up around her hips and her panties exposed!
When I got into the car next to her, I had to reach into my pants to rearrange
my erection. As she watched me arrange myself, she said, “that must be really
uncomfortable. If you want, you can take one of the new things I just bought
and touch yourself with it. That might make you feel better. Don’t you think?”
I told her it would make me feel better, but that I thought that was against
her rules. She explained that as long as I didn’t expose my penis to her, that
it wasn’t against the rules.
So I reached into the shopping bag and pulled out the size 10 panties that she
had just bought. I d****d them across my lap and they covered me completely.
As we pulled out of the mall parking lot, I reached under the big panties and
unzipped my pants. I freed my throbbing penis from my pants under the thin
white material of the big brief panties. I could see my penis clearly through
the sheer material of the panties, and I knew that Aunt Karen could too! It
excited me even more, knowing that she could see my penis through the panties as
she kept glancing over at me. Technically I was covered and not “exposing my
penis” to her. But the 6 inch tent in the panties was obvious, and the sheer
material did little to obscure Aunt Karen’s view of my rock hard penis. I began
stroking myself through the silky material. I watched Aunt Karen the whole
time. She kept looking over at my penis as much as she could while she was
driving. I noticed her licking her lips as she watched me. My body started to
stiffen. I was on the verge of my orgasm, as I stroked myself with Aunt Karen’s
She said, “Does that feel good?”
I nodded my head and mumbled “Uh huh,” as I continued stroking.
“Do you like feeling my panties on your cock?”
“Do you want to shoot off in my panties?”
“It’s okay. Go ahead. Shoot your cum in my panties.”
We were stopped at a stoplight. She didn’t take her eyes off of me as I threw
my head back and orgasmed in her new panties. My penis spasmed over and over
again, shooting my cum into her panties, making a huge wet spot where they
covered the head of my penis. I grunted involuntarily as I continued stroking
and shooting my cum in Aunt Karen’s panties while she watched.