Date: Wed, 6 Jul 2022 13:42:33 -0400
From: rosecoloredglasses78@gmail.com
Subject: My Chaperone Room

Please support Nifty. http://donate.nifty.org/donate.html. Please support
so we can keep reading and writing!!


My Chaperone Room

© 2022


"Can I come work on my essays in your room?" Bounced in the text
message to my iPhone.

"Sure." I responded.

I was the male chaperone for an honor society group at a national
convention. I was a high school teacher at the time, 32, and my charges
were 6 rooms of high school boys. 16 students in total. We were in a
college dorm setup and had a group of 9 rooms and a lounge/common room to
ourselves on one end of the dorm. Above and below us were other boys at
the convention. And on the other side of the building were the floors of
girls. The actual sponsor of the group was my friend Karen who had asked
me to chaperone months ago. Karen was on the girls side. This was a
pretty easy gig as the building also had security guards at night to make
sure that the boys didn't mix with the girls and that one floor from one
school didn't mix with another. My job was simple: keep the boys
relatively quiet after midnight and make sure they were up and dressed
and ready for the day in the morning. Otherwise the security guards made
sure that once everyone was in, they stayed on their floors.

We'd been on campus for 3 days out of 14.. I'd gotten back in the
groove of "meal plan" food, a twin sized bed, and seeing boys running
up and down the halls in their underwear or less. The first night the
boys decided to have a toga party and  walk around from room to room
practicing their speeches for the convention wrapped in their twin bed
sheets. The toga enthusiasts at first turned to telling everyone to "be
authentic" and pretty quickly various kinds of underwear were found up
and down the hall as everyone(?) went commando. By the end of the night
there was a contingency of the older boys advocating for "NOga." The
"noga" was of course exactly what you think it is- the dropping of the
toga to walk around chanting "noga" and wearing your birthday suit.
There were bodies of all shapes and sizes and teenage dicks of all
proportions as well. By the end of the night everyone was naked when I
called lights out at 12:30PM. I was not a participant in the toga/noga
activities, rather sticking to a pair of basketball shorts and a
t-shirt.

Back to the night in question...

A few minutes after the "Can I come to room" text, Josh came bounding
into my dorm room, which must typically be assigned to the RA as it is
just off the main lounge and has its own bathroom and shower set up. The
rest of the hall shared a communal bathroom with 4 or 5 stalls, 3
urinals, and 4 or 5 showers. Josh was a rising senior who had somehow
gotten it in his head that in addition to all of the convention stuff, he
was going to go ahead and write his college essay so it would be done
before school started. Josh was 17, 6'2", very skinny, one might say
lanky, pale features, and a head full of dirty blonde hair. He came into
my room as I was watching TV and was wearing a pair of Fruit of the Loom
tighty whities. He was holding his laptop and what looked like another
pair of underwear in his hand.

"Where are your clothes?" I asked. When I had left the hall and the
common room the boys were all about to watch a movie.

"I lost them," Josh responded. "We started playing strip poker and
I'm not the best at cards. I had to win these back. I was naked for a
hand, Ryan too, he is still trying to win his back."

I chuckled. "And whose are those?" I said as I pointed to the pair of
undies in his hand, "did you win those from somebody?"

"No I thought I'd take a shower in a few minutes, these are pretty
rank," he said as he turned around showing me his cotton covered
behind.

"Josh, is that a skid mark, what are you 6 years old?" I asked.

"When I lost my underwear in the game I had to let everybody wipe their
butt with them in order to win them back. I don't know whose that is?
And they are trying to make Ryan shave his pubes in order to get his
boxers back." Josh laughed.

"Or what? This is some weird strip poker I thought once someone was
naked they lost." I responded.

"That's right," Josh answered, "but once you're naked they are
playing you have to stay naked for the rest of the night or you can win
your clothes back, but since you don't have any clothes, you `bet'
with dares. They dared me to wipe their butts and then put these back on.
So I'm going to need a shower for sure after wearing `em."

"So did you come here to use my shower or work on the essays?" I asked.

Josh smiled, I had joked with the boys at dinner about how nice having my
own shower was and had heard them complaining about the cleanliness and
water pressure of the hall shower, "A little bit of both, but I really
do want to work on the essays some, and you said you were going to watch
Big Brother too." The RA Room was pretty nice with a private bath, a
full/queen sized bed, a couch, and a TV. Some of the students and I had a
shared affinity for the trashy TV show Big Brother, apparently Josh was
one.

"Essays or shower first? Big Brother doesn't come on for an hour." I
responded.

"Essays." Josh said as he confidently opened his computer.

I motioned for Josh to sit on the couch and moved and sat next to him. As
I did I noticed a gap between the opening of the underwear and his leg.
Like I said he was skinny, I'm guessing he needed a size medium in the
Fruit of the looms, but his legs couldn't be that lanky as to not fill
out the opening. "Don't lose the one eyed monster," I said as I
pointed to his uncut dick head peeking out through the leg opening.

"Oh, sorry," Josh responded, while pushing his dick back towards the
center of the pouch, "They also made me put my underwear on my head, I
guess I stretched out the opening."

"Y'all all seem so sweet, but this strip poker is a whole other level I
didn't know you had in you." I joked.

Josh agreed and we got to work on his essay. He had already started as he
and I had talked about the topic on the drive to campus.  He unlocked his
computer and handed me his laptop to read what he had worked on. I gave
him a few pointers after I read the first paragraph and he scooted closer
to me on the couch. I put the laptop in his lap and pointed out a few
places where he could improve. My arm in between us having nowhere to go
but around his back or to his lap, I went around his back. I put my hand
on his back and softly moved my hand across his naked back. We continued
to brainstorm ideas for the next part of the easy.

He turned towards me on the couch sitting in a criss-cross applesauce
style and I moved to face him with my legs on either side of his body.
With his laptop in his lap covering his crotch, he seemed to be naked
even though I knew he was wearing underwear I took in the sight. Our
naked legs occasionally touching or him putting his hand on my knee fed
into the illusion that he was naked. We laughed about several options and
finally he settled on an idea. I told him to work for 10 or 15 minutes
and then take a shower so he could enjoy the TV show. I told him we could
work the next day during a break or the next night.

Staying on the couch he turned away from me to lay on his stomach. His
long legs stretching his feet into my lap. I grabbed a nearby book to
read, worried that I might just stare at his body the entire time, but
definitely not wanting to lose physical contact with him. I rubbed his
feet a bit as I read and he commented that it felt good after wearing
dress shoes all day. I reminded him that tomorrow was a casual day and he
looked back at me relieved. I turned my body so that I was leaning
against the arm of the couch. I stretched one leg to the floor and the
other ahead of me on the couch. It was positioned right beside Josh's
cotton covered butt. Right beside Josh's  butt, covered in dirty, skid
mark cotton. I wasn't sure if I believed the story about the brown
streak belonging to someone else. I'd had a friend in college who was
just so frantic and lazy that he never wiped his ass well. Could this be
Josh?

I had stopped the messaging of Josh's feet so they were just sitting in
my lap. I noticed him moving his feet around in my lap. I moved one of
his feet to what he was searching for...my dick. I held his foot there
with one hand and let him feel that I had gotten hard. While we were
moving things around I adjusted his leg to be on the outside of our
encounter so my outstretched foot could have access to his ass. Keeping
one of his feet on my crotch and now my foot at his backside I started to
use my toes on his undies.

I first nudged at his taint with my toes. I was trying to figure out
where his ass crack was.

He adjusted how his crotch was laying on the couch, I imagine he had
gotten hard himself and was making an adjustment.

He stopped typing and I concentrated on my book for a moment. I kept
slightly moving my foot around his underwear. I found his balls with my
big toe and bounced them a little. Josh reached back and pulled the waist
of his underwear down below his butt cheeks. I moved my foot and made
contact with his hairless bottom. I shoved my toe into his crack. He
started slightly humping the couch, if he wasn't before. I suddenly felt
him press down with his foot on my erection. I guessed at what he wanted
and pulled my shorts down under my balls and grabbed his foot pressing
against the flesh of my erection.

Josh looked over his shoulder and our eyes locked. I wasn't fully sure
what this was we were doing.

"Keep working for five more minutes," I ordered. He turned around and
continued to type while rubbing his foot against my dick. I continued to
use my foot on his naked ass.

"Is your dick as long as my foot?" Josh asked without turning around.

"Not quite," I answered, holding the two side by side.

"But it's big," Josh responded.

"Sure," I answered. "So is your foot."

"You know what they say about people with big feet?" Josh retorted,
still face down and facing away from me. He continued to hump the couch
which also meant my big toe was working in and out of his crack.

"Sure do." Was my simple response. He continued to message my dick with
his foot.Then I reached over to his butt and ran my fingers up and down
his sweet crack. I spread his cheeks a bit to check out his teenage hole.
I blew softly on it and It think it twitched.

"Can I see it?" He asked. I paused. "Your dick, I mean."

"Are you done writing? Let's go into the bathroom," I said, grabbing
the waistband of his Fruit of the looms and pulling them back up. I
wanted to be able to watch him strip in the bathroom. As he stood up he
was obviously tented. He looked down at his teen sized endowment and
smiled at me. "Not too shabby," I retorted. He beamed. I pulled his
crotch to my face and planted my nose right in his tighty whities and
inhaled the "sweet" scent of boy,  If you know what I am talking about,
you know there is more than sweet there. I could smell his sweat, his
piss, his precum. I nuzzled my nose down to that area where his leg met
his crotch and opened the gap of his white undies and let my nose move up
and down that most sweaty of areas. I looked up and his eyes were closed.
He steadied himself while holding my shoulder. Without ceremony, I spun
him around and put my nose in his cotton covered crack. This boy needed a
shower for sure, but I didn't mind. As I stood up, I pulled the
waistband of his underwear out and took a peak at his ass again and then
let it go. I loved hearing that "snap" of his underwear on the top of
his butt.

I pushed him a little toward the bathroom and moved towards the door of
my room to lock it, and just as I got there, there was a knock. "It's
Ryan, can I come in?" The boy spoke from the other side of the door. I
looked at Josh for permission, to see if this was cool, if Ryan was cool.
Josh didn't protest or affirm, he seemed to be thinking "it might be
okay," by his shrug. So I let Ryan in. I opened the door and Ryan came
right in saying "Is Josh here?" As I closed the door behind him.

Ryan was clad in simple blue and red boxer shorts, not boxer briefs, just
boxers. He opened his mouth to speak, and then probably noticed the tent
in Josh's briefs. Josh reached down and tugged on his dick a few times
and then nodded toward me. I put my hand down in my basketball shorts and
obviously was playing with myself. "We were just about to go to into the
bathroom, Josh needs a shower," I said as I moved from the door, past
Ryan, to Josh. "Want to join us?" As I said this I pulled Josh's body
towards mine and lined us up crotch to crotch, dick to dick, with his
body pressed to mine. I was staring at Ryan, over Josh's shoulder.
Josh's backside was facing Ryan.

"Um, I was just coming to tell Josh that they are still playing cards,
but I got my boxers back." Ryan stumbled over his words a bit.

"We've been working, but I haven't taken my shower yet," Josh looked
over his shoulder at Ryan. I put my hands down Josh's underwear and
messaged his butt checks for a  moment. Then I pulled them down so Ryan
could see the pale hiney of his friend. "Come with us, Ryan," Josh half
asked, half told.

"I'm not gay," Ryan objected slightly.

"Me either," Josh responded, turning around and reaching a hand out to
his friend, "I just need a shower and Mr. Martin's dick is huge. I
wanna see it." Ryan thought for a moment and then grabbed Josh's hand.
Josh pulled him into our hug and tried to grind our three crotches
together...awkwardly. I stepped to the side and pushed the two teens
together. I heard one of them give out a little grunt as their cotton
clad cocks found each other. I kept my hand inside of Josh's undies
continuing to rub his butt.  I put my arm around Ryan as I pushed my dick
into his thigh.

"Shower?" I asked both teens. They nodded and I went to lock the door
to the room as they headed into the bathroom. When we got into the
bathroom, Ryan reached into the shower, turned it on, and then stepped
back. I took my shirt off and let my basketball shorts slip to the floor.
I was left standing in a pair of blue nylon briefs. I reached into the
briefs and pulled my erection from pointing out to pointing up. More than
my thick mushroom head was sticking out of the top of my briefs.

"Told you," Josh said.

"Yeah," Ryan responded

"Go ahead," I nodded towards Josh. Josh reached for the side of my
briefs and slowly pulled them down my hairy thighs. Taking them all the
way down to the floor. He looked back up at me, my thick 8 inch erection
between his gaze and mine. He slowly stood up and I stepped out of the
briefs.I reached for his hand, grabbed his wrist, and put his hand on my
dick. He slowly started jacking me off...maybe not maybe more of just
touching.

"It's warm...hot," Josh said looking me in the eyes.

"And these?" I asked moving his hand to my balls. These he messaged.

"Hairy." He commented.

"How about yours?" I asked, looking at him in his tighty whities. He
smiled and released his grip on my man balls. I reached over to his
waistband and peaked inside rather than pulling them down. His teen dick
twitched with anticipation. I reached in and found his nuts. They were
grape sized, hairy, and sweaty. I pulled my hand out and smelled my
fingers aggressively, "sweaty...cummy. When is the last time you jacked
off?"

"Don't know," Josh responded.

"Last night," Ryan chimed in, "I saw your hand moving under your
blanket and heard you cum." Ryan had his hand down his boxers but was
keeping a distance from Josh and I.

"Last night, huh?" I asked, Josh nodded in the affirmative, I
continued, "and you haven't taken a shower since? No jerking off
today." Josh shook his head no. "So you have some saved up?" I asked
as I shucked his undies to the floor. This revealed a  5.5 inch boner. He
had light brown pubes, darker than the hair on top of his head.

"I think I might cum right now," Josh smiled as I pulled him into me so
our dicks were touching. "This is cool."

"Sword fight," I gingerly said as I stepped back a bit so we could swat
our dicks at one another. "Wanna play?" I looked over at Ryan.

"Not yet," Ryan responded as he quickly stuff a hand in his boxers to
play with himself.

"Ah, not YET," I emphasized, pulling Josh in close to me. Keeping our
things rubbing together I positioned Josh so his ass was facing Ryan. I
really started pumping my dick into Joshs and he reached between us and
grabbed them both for a moment, then pulled his hand back. Presumably
that was a sensation that was getting him to close to jizzing.

With Josh concentrating on feeling good, but not so good that he would
cum, I set my eyes on Ryan by playing with Joshs ass. His ass was now
facing Ryan and Ryan definitely noticed when I placed my hands on Josh's
pale white hiney. I put one hand on each of his boney cheeks. I pulled
him into me a bit and really thrust forward. Josh moaned. Ryan's
eyebrows raised. I ran a finger up and down Josh's crack. It was
hairless and warm. I spread his cheeks open wide for Ryan to hopefully
get a look at his hole.

I spun Josh around and rubbed my dick around his ass a bit. Not sticking
it in just teasing him. I pulled him in and got my dick hot dog style
running up and down his crack.

"I feel your pubes," Josh said.

"I feel yours too," I said as I played with his dick and balls with one
hand. I licked my thumb and forefinger and tweaked one of his nipples. He
shivered. I licked my palm and really started to jack him.

Ryan stepped close to us and wasn't quite sure what to do. I leaned over
Josh and pecked Ryan on the check with a kiss. He blushed. Josh then did
the same. A little peck.

"Anything look interesting to you?" I asked.

"Kind of. Yeah of course." Ryan smiled. He slipped his underwear down
and stepped out of them, putting his hands over his junk, and then
realizing that want the point.

Standing there naked starring me grinding his friend and jacking him off,
Ryan was gorgeous. Where Josh was skin and bones, Ryan had just a little
softness. A little tummy, the kind that would burn off with a consistent
workout or become a beer belly in the frat house. Just a bit. His nipples
were dime sized, pert, and brown. He had a few sparse chest hairs and a
faint treasure trail.

He had plenty of dark pubes sitting atop a 5  inch dick. He had some
hefty nuts for a 15 or 16 year old.

"Nice," Josh said to his friend.

"Yours is bigger," Ryan said.

"Yours is thicker," Josh responded.

"Jerk off." Josh requested. Ryan moved his hand to his teenage prick
and started to jerk off watching us go at it as well.

After a few moments Ryan spoke while continuing to jerk
himself,"Martini," (that's what the kids called me a take on my last
name Martin) , "will you..." he trailed off. A little embarrassed I
guess.

"Anything," I responded.

"Will you play with my butt like you were with Josh a few minutes ago?"
I practically came right then. This pudgy, pale, gorgeous teenager was
asking me to play with his ass.

Without saying a word, I let go of Josh's hardon and let my dick fall
from between us and moved over to stand in front of Ryan. I looked him up
and down and pulled him in for a deep kiss.  I let my hands explore his
ass, as requested. I jiggled each ample cheek and tried to remember if I
had previously clocked him as having a teenage bubble butt. I smacked one
cheek with my right hand and he giggled. I smacked it again, this time a
grunt. His cheek felt smooth but his crack felt hairy and maybe a little
damp. Although that could have been from the steam of the shower filling
up the room. He reached back and grabbed one of my hands bringing it to
his face. He put one of my fingers in his mouth and sucked on it. A sure
sign to me that he wanted a blow job. To my surprise he turned around and
presented me with his ass.

I was right.  His beautiful pale smooth globes were split right down the
middle by a crack of Full of dark brown, beautiful hair. In a few years
this boy would have hair everywhere. But for now his crack was the
hairiest part of his body. As I bounced his cheeks he put his hands on
his own ass and opened it for me.

I put my finger in his crack and moved it up and down. I tickled his
rosebud but didn't enter. I nuzzled up right to his ear and whispered,
"is this what you want?" As I shoved my middle finger into him with no
fanfare.

"Absolutely." He responded. He sort of pushed his ass back on my finger
as if to say give me more. So I started fingering this boy like my life
depended on it.

He was in heaven and I was really enjoying turning this supposed straight
boy into something else entirely, so I got on my knees and put my tongue
right at his hole. "Spread `em," I commanded and he complied.

"Oh my god" was his response to the tongue bath I was giving his hole.
He tasted like a boy. Musky, hairy, sweaty, soapy, but not dirty.

At this point, I had forgotten about Josh. I wasn't nearly as attracted
to his skin and bones as I was to Ryan, but why stop at one when you can
have two teenage boys drooling on your dick for the next 12 days? Josh
said, "I want some of that" and he put his ass in my face,  wanting me
to treat him to the same wet, hot, rimming that I was offering his
friend. I knew from my sniff of Josh's ass earlier and skid mark in his
undies that this could get messy. So I stood up, and got right behind
Josh, and shoved my middle finger as far up his ass as I could. I pulled
it out and sure enough it wasn't so clean. I put it to his face and
whipped his mess on his chest.

"Well," he joked, " it's made for things going out, not going in."

Clever. But my response was just as clever. "Not tonight. Watch this."
I shoved a finger in Ryans ass and pulled it out. I put it to Josh's
face and then licked it. "You need to take a shower while Ryan and I
finish up. " I demanded spanking Josh firmly. "Then we will join
you."

Josh stepped into the walk in shower giggling a little bit as Ryan said,
" I never want to finish. "

"This is just round one sexy," I said as I pulled on and juggled his
balls with one hand.

"Good." He said as he kissed me deep. The first kiss he intiated. It
was wet and long. I thought about my next move and knew I had to fuck
him. I wanted to see his face while I slid it in, but like I said this
was just round one and I knew a three way shower would do us all some
good. So I decided to just take his cherry here and worry about a slow
fuck later.

I pushed him against the wall face first and put his hands above his
head. I held his hands up over his head while I sucked on his neck and
went back to fingering his hole.  I found what I was looking for. That
special place in man's ass. I grazed it a few times. And then he nudged
me along with his words, " Is this what your dick would feel like?" He
was breathy and sincerely asking.

"Well, sort of, I have a little more control with my fingers," I
answered honestly. " I can do this," I found his happy place and stayed
there. Moving my middle finger all around his prostate.

"Please fuck me," Ryan howled. I needed no more invitation than that.

I spit on my dick, lined it up with his hole and went right in. He moaned
and screamed a little. I pulled all the way out and went in again.

I pulled out a second time and moved him to bend over the sink. "Tell me
you want it," I begged as I tapped his pink, hairy, teenage hole with my
man cock.

"I want your dick so bad," he said. He started to jerk himself off.

I just started ramming him. It was heaven for me and our eyes locked in
the bathroom mirror. He was loving it. I moved his hand for his prick and
whispered, " let me make you cum." He nodded. I thrust him several
times and eventually cam right IN his ass. He clenched his cheeks on my
dick and I knew he was cumming too. I reached around and felt his wet
dick knowing I was right. I brought my hand to my mouth and licked his
cum. I then got some more and fed him his own seed. We were both still
coming down from the faced paced fucking, but I was still pretty hard
inside him. I cupped his dick. He had shriveled up to not more than a
couple of inches buried in his bush. This was a great reminder of his
youth.

I pulled out and he reached to his ass grabbing the cum pouring out. We
stepped into the shower with Josh and I wondered how much we could get
done before morning.




What happens next? Let me know at rosecoloredglasses78@gmail.com


Support the Nifty archive!!

Support so we can read and create!!

http://donate.nifty.org/donate.html