Date: Tue, 9 Mar 2021 12:42:34 -0600
From: Kinky Twinky <kinkytwinky96@gmail.com>
Subject: Training A Virgin Boy

When I was in college, there was an older man that I hooked up with
regularly.  He was 50ish years old, had an athletic build, clean cut, and
absolutely loved playing with college boys.  I had met him online and was
immediately taken by his charm.  The profile picture of his girthy seven
inch erection was certainly a selling point as well.  We wasted no time in
meeting up at his house where he rode me like a stallion.  He would invite
me over every few days to use my boy body for his pleasure.  I was turned
on by his confidence, charm, and charisma.  He liked my slim figure, oral
skills, and tight hole.  After maybe nine months, I stopped hearing from
him as often and figured our fun was coming to an end.  As it turned out,
he had met another boy and told me all about him before asking a favor of
me.  He wanted me to help teach the boy to bottom.

He was an 18 year old virgin and freshman at the college.  They had been
chatting for a couple months and had met up a few times.  There had been a
lot of kissing and touching, but the boy was nervous about bottoming due to
the size of the man's cock.  They would jerk off together and the boy would
play with a dildo the man had bought him.  The idea was that I would join
them and show the boy how it's done.  I was intrigued at the thought.  I
had been with several virgins before, but always guys that wanted to fuck
me.  It was also nice that the man liked my bottoming skills enough to want
me to pass them on.  I agreed to meet with them that weekend.

We all met at the man's house and hung out for a while so I could get to
know the eager virgin.  He was similar to me in stature and it was obvious
the man liked a certain type.  My young prodigy was new to both oral and
anal.  In fact, when they had jerked off together and stroked each other,
it was the first time he had even touched another man's cock.  We did have
one thing in common in that we both discovered our attractions to older men
through porn.  He watched porn and masturbated often.  He liked to play
with his hole while he orgasmed.  His recent introduction to dildos had
added a new sensation to his routine.  He said he liked to slowly insert it
and loved the feeling of it holding his hole open.  After about half an
hour of chatting, it was time to get started.

We would begin with an introduction to sucking cock.  I suggested that we
all get naked to start.  The man sat near the edge of the couch and leaned
back with his legs spread while teacher and student got on our knees in
front of him.  His cock was already rock hard and his balls tight.  There
was no hiding his excitement.  In order to loosen the boy up a bit, I
surprised him by pulling him in for a kiss.  It lasted maybe ten seconds
with some encouraging words from our mutual friend.  The boy seemed more
relaxed already and we were ready to begin.  I told him that it was
important for him to know how a man tastes when you first go down on him.
I held the man's cock up towards his stomach and had the boy slowly lick
the shaft.  His inhibitions were slowly falling away as he said that it
wasn't bad.  I told him that he'd learn to love it.  Next, I showed him how
to hold the base of a cock by putting my hand flat beside it with my thumb
underneath.  We took turns licking his shaft slowly and then move down to
his balls.  He caught on fast and I had him teasing the testicles with his
tongue and gently sucking them in no time.  He liked that positive feedback
of hearing the man moan.  It was time for this boy to take his first cock
in his mouth.

I noticed some precum glistening on the head of the cock.  I rolled my
finger across to gather some and had the boy taste it.  I didn't want him
to be surprised when he got some later.  Since he wouldn't be able to see
everything, I had to explain how I use my lips and tongue to massage a cock
while I suck.  With that, I opened wide and went down.  Once there was a
coat of saliva on the shaft, I put my hand around it near my lips and moved
it up and down with my head.  I was going very slow since I had gotten
another dose of precum and knew the man would cum if I sped up.  Once I
thought I'd shown him enough, it was time for him to try.  I leaned back
and let him take the lead.  He went slow and made sure to follow my
instructions.  I told him to tighten his lips enough to massage his shaft.
He was a quick study and introduced his hand to the mix.  He went a couple
minutes and things seemed to be going well.  I told him to slowly speed up
if he felt comfortable, which he did.  I was impressed that he was still
going, but it occurred to me that I might have to stop him depending on his
answer to a question.  I asked if he wanted the man to cum in his mouth.
He wasn't quite ready for that, so I told him that when the man let him
know it was about to happen, for him to move down to sucking on his balls.

The man deduced that I was going to dive on his cock to take his load and
must've liked the idea of two boys sucking him off because he was ready to
burst ten or fifteen seconds later.  He gave the signal, the boy quickly
moved down between his thighs to suck his balls, and I wrapped my lips
around the shaft just in time to catch the first dose of semen.  The man's
hand cupped my head and pushed me down on him as he let out a roar.  He
nearly filled my mouth before releasing me.  The boy and I sat back.  He
was smiling and seemed giddy having sucked his first cock.  I had another
surprise for him though and pulled him in for another kiss.  The cum flowed
from my mouth to his with some running down our chins.  He didn't pull away
and I knew he liked it.  Once our lips parted, I looked him in the eyes as
I told him that he should lick the last of the cum from the man's cock.  A
good cocksucker always cleans up once he's finished.

As he did that, I went and grabbed some bottles of water for us all.  We
sat on the couch and discussed what we'd done.  He said he really enjoyed
it and that it was hot to randomly taste the precum while he was sucking.
He also liked the taste of the cum.  I told him next time he should take
the load and that it's just something you have to do to get used to.  We
then talked about what we should do next.  I suggested that he use his
dildo for a while as he watched me get fucked and I talk it through with
him.  It was evident that all three of us were turned on by this idea.  The
man's cock was already hard again.  We decided we should move to the
bedroom.

I was really getting into teaching this boy how to be a good bottom.  He
was excited and I loved how much it turned the man on to know he was going
to fuck a virgin boy hole.  I got another idea and had the boy get on his
knees on the bed.  From our previous encounters, I knew the man liked to
tease a boy's hole.  I stood next to the bed to the boy's side so I could
see what was going on and his face while it happened.  The man started by
rubbing the tight sphincter with his thumb as if to coax it into opening
for him.  The boy moaned a little and closed his eyes.  His jaw dropped and
he bucked slightly when the thumb pushed him open and popped inside.  The
man moved his thumb in and out as the boy's body shook.  We were all
smiling from ear to ear.  This was going to be a memorable night for all of
us.  After maybe 30 seconds, the man decided to give the boy another first.
He moved his thumb out of the way and plunged his face between those 18
year old ass cheeks.  The boy gasped as a tongue licked his hole.  He
gasped again moments later as the tongue pushed him slightly open.  He said
it felt amazing.  After a couple minutes, I handed the dildo to the man
with some lube and he slowly pushed it into the boy who was half erect and
oozing a small amount of precum.

The boy was ordered to roll over onto his back as the man held the dildo
inside him.  I was turned on just watching this play out, but I wanted to
be in on the fun.  I climbed onto the bed and started sucking the man's
fully-erect cock.  He'd fucked me dozens of times, but somehow I wanted him
inside me more than ever.  They were both moaning and I wanted to join
them.  After a minute, I spun around and put my butt in the air.  The man
was behind me seconds later rubbing lube on my hole.  I told the boy that
the trick to taking a big cock is just to relax and not fight it.  He's
going to force you open, but if you can just let it happen, it won't hurt
as much.  In time, you learn to enjoy the feeling of being stretched open.
I felt a thick cock pushing on my hole and a second later, he was in me.
He worked up quickly to a good pace.  We were both practically in heat.
The boy watched as the man's cock disappeared into me over and over.  He
was moving his dildo in and out slowly.  Knowing that the man wouldn't last
much longer at his pace, I asked the boy if he wanted to try it and let him
know that he'd go slow.  With a nod, it was time for the main event.

The man pulled out, moved over, and pulled the boy closer.  He took the
dildo out and slid it into me as if for safe keeping.  I got on my knees
next to the boy and slowly pumped the dildo with one hand while resting a
reassuring hand on his chest.  His legs were spread and the man was lined
up.  As the man began pushing forward, I had the boy take a long breath.  A
couple seconds later, he gasped as his hole opened to accept the head of
his first cock.  The man paused as a courtesy to make sure the boy was
alright.  With no objection, just some heavy breathing, he slowly pushed
forward.  He was thrusting slightly more into his virgin conquest each
time.  The boy just moaned.  I asked him if he liked the full feeling and
he nodded.  His hands were holding his legs which I'm sure he learned from
porn, but it was a good position.  I was surprised at how well he was
doing.  The man was nearly all the way inside him and he wasn't
complaining.  The man was so happy with himself that he started to speed
up.  I had a passing thought that I immediately acted on.  I wanted the boy
to cum while getting fucked, so I dropped and started sucking his
half-erect boy cock.

As it turned out, he'd never been sucked either.  He let out a long moan as
my head started bobbing and his cock got harder.  The man was really
fucking him now and I knew he was about to explode.  Maybe 30 seconds
later, he bucked his hips a bit, grabbed the sheets, and let out a series
of higher pitch moans as I felt his boy dick pump the first dose of cum
into my mouth.  His orgasm was an achievement for all of us, but it was
obvious that it was one of the biggest he'd ever had.  Even after he
finished feed me his load, I could feel his dick twitch with each thrust
into his boy hole.  I was amazed that the man hadn't cum as well, but I had
an idea that might set him off.  I moved up to kiss the boy and share his
cum.  We kissed passionately and moaned as he took the pounding the man was
now giving him.  The boy was a natural.  His hand ran through my hair as he
pulled me in for more.  The man was now moaning loudly.  It was about to
happen.

"I'm going to breed you, boy!"  He drove his cock deep into the deflowered
hole of our new friend.  I leaned back to watch the boy experience a top
cumming inside him for the first time.  He moaned as the man began
shooting.  I could practically feel it myself as I watched him take thrust
after thrust as the man roared over his conquest.  As the man slowed down,
he remained inside the boy as they both took a moment to breath.  The boy
said it was amazing.  His legs were involuntarily twitching as the man
pulled out.  The man was very proud of himself and let us know that it had
been decades since he fucked a virgin.  I told the boy that he did much
better than I did my first time.

The master bathroom had a large walk-in shower.  The man went in to turn
the water on as I helped the boy off the bed.  I had barely noticed that
the dildo had flopped out of me when I leaned in to suck him earlier.  As
he stood, there was a noticeable amount of cum that ran down his leg.  I
took his hand and we both smiled as we walked to the shower.  The man
wanted to watch us lather each other up.  We spent maybe five minutes
kissing and touching before we switched focus to cleaning the man.  I had
always loved the man's quick recovery time, but this time he barely lost
his erection.  We stroked his manhood with soap as he reached down to grope
both of our butts.  I felt him rubbing my hole for a few seconds before two
fingers slipped inside me.  The boy moaned and I knew he was getting the
same treatment.  There was kissing between all of us as our hands explored
each other.  It was one of the most erotic showers I've experienced.

We finally rinsed off and got some towels.  As we dried off, we talked
about the boy's experience.  He said it was the best orgasm he'd ever had
and that feeling the man cum inside him felt amazing as well.  Any shyness
had vanished.  We got water and relaxed for a bit until the man was ready
to play again.  He sat on the couch and let the boy start sucking him.  The
man coached him some, but the boy was into it and went for more than five
minutes.  The man held the boy's head in place while he fired his third
load of the evening.  The boy gagged a little, but took it all.  We decided
to get some sleep and the three of us cuddled under the blanket all night.

The man and the boy played regularly after that and the boy and I stayed in
touch.  I introduced him to some of the other men I would see.  He became
quite the slut and we loved to share stories of our hook ups, especially if
we'd both been with the man.  I was like his sexual mentor.  It's been
about four years and we still keep in touch, though we now live in
different cities.  I think back on that night with him and our friend
fondly.