Date: Wed, 18 Oct 2023 15:03:05 -0500
From: Deadpan Don <deadpandon13@gmail.com>
Subject: Donny and Friends Chapter 9

Author's Notes:

This is a work of fiction - just a story from my addled imagination.
If you are sexually active, please be safe and use protection.

This story takes place in the 1990s.  While the 'when' really isn't
important, you will likely notice the absence of smartphones and the
internet.  Such were the breaks of growing up Gen X.

Nifty needs your donations to provide these wonderful stories.  Please
give what you can to keep this site going and free for all.
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Do not repost or redistribute without my permission.
Feedback is very much appreciated.  Please send to
deadpandon13@gmail.com.

----------

Donny and Friends
Chapter 9

Later that night, after a rest and refreshment break, we were laying on
Jack's bed together where we'd moved because it was a full-sized bed and
had more room compared to Toby's twin-sized.  I was on my back between
the two brothers who were laying on their sides on either side of me
propped up on their elbows.  We were all chatting and the boys each had a
hand on my chest absentmindedly tracing my pecs and abdominal muscles
with their fingers.  I had each of my hands on one of their thighs.

"Jack," Toby said, after a moment's lull in the conversation, "can I ask
you a personal question."

"After what we just did in front of each other tonight, I don't see why
not," Jack answered with a smirk.

"You, um..." Toby asked, falteringly, "seem to have a lot of, uh...
experience... with gay sex..."

"Are you gonna land that plane, or just circle for a while?" Jack chided
his brother.

Toby pulled a frustrated expression.  I figured I knew what he wanted to
ask so I did it for him.  "Are you gay, Jack?" I asked.

Jack winked at me, then turning his attention back to Toby, he said, "No,
I don't think I'm gay.  Not like our boy here is," and he patted me on
the tummy as he said it.  "I'm very attracted to girls," he continued,
"and I love having sex with them.  And I have - several times, with
several different girls.  Hell, I'd love to get married one day and have
a family.  But, I can appreciate a dude's handsome face and toned body -
beauty is beauty.  Plus, sex with guys - the RIGHT guys - is just
easier.  And usually more satisfying.  No girl can give head better than
a guy!  You can take that to the bank."

Toby nodded thinking over Jack's answer.

"I read up on that Kinsey guy you told me about," Jack continued.  "Makes
a lot of what I'd already been thinking... feeling... make more sense."

"Like what?" I asked curiously.

"Like the fact that I can get it up for any hot chick you put in front of
me, even though I know she's probably not worth the trouble, and that sex
with guys is usually better.  But for me to hook up with a guy... well, I
have to already have some kind of connection with him - know him on some
level deeper than just an acquaintance.  I couldn't just meet up with a
stranger and suck his dick, no matter how much of a stud he might be.  It
doesn't work like that for me."

I glanced at Toby who was taking in everything his big brother was saying
thoughtfully.

"So you like sucking cock," Toby said.  It was more of a statement than a
question.

Jack raised a finger and said, "It depends on the cock, and more
importantly, the guy it's attached to.  What I actually enjoy is knowing
how I'm making my partner feel, rather than the act itself."  And once
he'd said that his hand drifted down my abdomen to my flaccid cock and
began to fondle it.  It did not stay flaccid for long.

Toby watched Jack's hand manipulate my cock for a minute or two, then
asked, "Do you also..."  His voice tailed off, unable to complete the
question, I guess.

"Do I also... what?" Jack asked.  "Take it up the ass?" he finished with a
chuckle.

Toby nodded.

"Yes, Toby, I do," Jack said, sincerely and with no trace of shame or
embarrassment.  "A guy who knows what he's doing can really make you feel
good back there, true fact."

I spread my legs a little as Toby now joined Jack caressing my nether
regions.

"It's also made me feel really close to the few guys that I've let in
back there," Jack continued.  "I haven't bent over for every guy I've
been with, no, just a few that I have a special bond with.  And it's made
our bond... deeper.  No pun intended," he finished with a grin.

"I see," Toby said quietly.  "Can I ask who?"

Jack sighed, "No.  I'm sorry, I can't tell you who, Tobes.  Although, you
can probably guess a couple of them.  I promised every one of those guys
I'd keep it a secret, and they promised me, too.  I don't want to break
that promise.  What I will tell you," he said, giving my cock a good
squeeze, "is that our lovely boy here is the only 'Kinsey 6' in the
bunch.  Everyone else I've been with is mostly straight."

"That's hot," I murmured.  They both looked at me. "What?" I exclaimed.
 "Straight guys fucking each other is hot!" With that I reached for
Jack's cock and found it hard and leaking.  I stretched out my other hand
and found Toby's in the same state.  I giggled a little, giving each a
few tugs.

Jack looked at me with that same mischievous expression Toby so often
gets.  "So Donny," he asked, "have you fucked a guy up the ass yet?"

"I wish," I said and chuckled.  "Seriously, though, I wouldn't ask the
guys to do anything they're uncomfortable with, so no.  Hasn't really
been an option."

"Well, that settles it," Jack announced, getting up from the bed.
 "You're going to fuck me."  As he moved toward the door he said,
"Fetching the lube.  Be right back."

I stared after him, my jaw agape.  My head was spinning and to be honest
I didn't even look at Toby to see what his response was.  But I found out
when Jack came back into the room.

"Okay, Donny," Jack was saying as he returned, "It's been a while so it
may take a little extra work to open me up, but we'll get there."  He
walked up to the side of the bed, handed me the tube of KY and started to
tell me just what he wanted me to do to get him loosened up for me.

"Wait," Toby said softly from where he had retreated to at the head of
the bed.

I looked over to him and he had a strange expression on his face that I'd
never seen before.  It was hard to read, confusion, maybe, mixed with
regret?  I wasn't sure, but as I watched him for a moment it resolved
into one of determination, the expression he always had when he'd just
made a decision he'd been struggling with.

"No," Toby said, louder and firmly.  "It needs to be me."

"What?" Jack said, responding to the interruption and looking over to
Toby.

Toby rose from the bed and stepped over to us.  "It needs to be me," he
said again.  He took my face in his hands and slid his fingers into my
hair.  "Donny, I was the first one to penetrate you.  I should be the
first one you get to penetrate as well."

"Toby," I began, smiling back at him.  I placed one of my hands on his
and said, "You don't have to do that.  I never want you to do anything
for me that you don't want to do."

"That's just it," Toby responded, smiling at me reassuringly.  "I do want
to do it... for you.  I'm a little nervous about it, not gonna lie," he
said with a big sigh.  "But I want to be your first."

I stared back into those gentle hazel eyes of his for a moment, then
wrapped my arms around him and pulled him into a long and passionate
kiss.

"Okay, then," Jack commented.  Then he asked, "Toby, since this'll be
Donny's first time... and  yours... are you clean back there?"

Toby broke the kiss and looking at Jack, said, "Clean what?"

Jack chuckled and went on to explain that conscientious guys who are
"expecting company back there," as Jack put it, take a few steps
beforehand to help ensure a more pleasant experience for everyone.  I
tried to hide a slight snicker at Toby's completely blank expression.
Poor boy really had no clue.

"Come with me, brother," Jack said, slipping an arm around Toby's
shoulders and leading him out of the bedroom and down the hall to the
bathroom.

I sat on the bed and waited impatiently for them to return.  Was this
really happening?  It seemed unreal.  Was I really about to get my first
piece of ass?  And Toby's ass at that?  Toby's beautiful, perfect, cherry
ass?  My dick was so hard it hurt.  I had to calm down.

After what felt like forever, but was probably only a few minutes, they
returned.  Toby looked a little shaken.  I don't know if it was from
learning about enemas, getting his first one, or the fact that it was his
older brother teaching him about it and probably helping him out with
it.  I walked up to him and placed my hands on his shoulders.

"Are you sure you're okay with this?" I asked.

"Yeah," he said, regaining his composure and winking at me.  Then he
leaned in and kissed me.  "Donny, do you really do all that?  For us?" he
asked.

I smirked.  "Yeah," I said.  "I mean, I didn't that first time cuz I
wasn't expecting it.  But, yeah, generally.  I mean, whenever I think
there's likely to be some 'club business' to take care of," I said with a
wink.

What was that expression he gave me?  Admiration?

Jack told Toby to get on the bed facing the wall on his hands and knees,
ass towards us.  My beautiful boy complied.  Jack then playfully slapped
Toby's ass and said to me, "I'm guessing you know what to do with this."

I just grinned back at him.

I placed both my hands on Toby's muscular globes and began to caress and
squeeze.  As I leaned in close I pulled them apart exposing Toby's pucker
to me.  His ass and ass crack were hairless and smooth.  I sniffed and
detected the scent of soap and Toby's natural musk that I loved so much.
I reached between his legs and took hold of his flaccid cock and began to
stroke and manipulate it causing it to swell in my hand.  I nuzzled his
balls with my nose and teased them with my tongue, eliciting a small
moan.

After I'd played with his cock and balls for a bit he was fully hard.  I
then moved upwards, dragging my nose and tongue along his taint, stopping
to give the entire area a good tongue bath.  Toby was moaning more steady
now and his cock was leaking precum into my hand.  I released his cock,
and spreading his ass cheeks apart again I licked up the length of his
crack.

Toby jumped and cried out, "Oh, my god!" when my tongue crossed his
sphincter.

Jack chuckled at that.

Taking a tighter hold of Toby's cheeks dove back in for a full assault on
his asshole.  I swirled my tongue round and round the tight ring of
muscle, poking at it occasionally.

Jack was giving us both words of encouragement, telling Toby to relax and
to just let me drive.  Telling me to take my time opening him up.  Jack
being there and guiding us seemed to make it more exciting for me.  My
cock was hard as a rock and aching for action!

After a few minutes of working on that ring of muscle I felt it loosen,
so I shoved my tongue in as far as it would go.  That elicited another,
"Oh, my god!" from Toby.

After another minute or two I pulled back and asked Toby how he was
doing.

"Jesus Fuckin' Christ, Donny!" he exclaimed.  "This is incredible!"

Jack squeezed out a dollop of KY onto my fingers and I lubed them up
good.  Then bringing my hand up to Toby's hole I circled it with my
forefinger and pushed in.

"Oooooh," Toby moaned.

I pushed my lubed finger in up to the knuckle, then began feeling around
inside.  This elicited more moaning from Toby.

"Whatever you're doing back there," Toby began, but before he could
finish the thought I found his prostate.  "HOLY FUCKIN' GOD, DONNY!!" he
yelled!

Jack, who was sitting on the bed now, right beside Toby and keeping a
close eye on everything, chuckled and said, "I told you a guy who knows
what he's doing can really make you feel good back there."

"Jesus Christ!" Toby exclaimed quieter.  His head was now down on the
mattress resting on his folded arms, his eyes closed.  His ass was up in
the air and pushing back on my finger.

I applied more lube and added a second finger to Toby's ass.  He grunted
but continued pushing back.  Then I added a third.  He retreated a little
at that, but I kept the three fingers in him and still until he was
pushing back at me again.

I pushed my fingers in and out of Toby's hole, twisting them around.  I
wasn't sure how wide I needed to get him.  My cock was just average, but
I wanted him to be comfortable when I entered him.

I was so focused on Toby's ass and so distracted by his moans that I
didn't notice Jack get up from the bed until he returned with a shoebox
in his hands.  Sitting back down he opened the shoebox and I could see a
number of butt plugs and a couple dildos inside!  Jack put his finger to
his lips in a 'shhh' sign.  He then picked up one of the butt plugs and
compared it to my cock, shook his head then pulled out another one.
Satisfied with this one he lubed it up and handed it to me.

I pulled my fingers out of Toby eliciting a tiny gasp from him, then I
brought the plug to his anus and slowly pushed it in.

"Umph!" Toby groaned and raised his head.  Looking over his shoulder he
asked, "What is that?"

"Just something to help open you up, brother," Jack said and winked at
Toby.

As I worked on getting the toy into Toby's hole, Jack rested his hand on
Toby's ass cheek and began to caress it.  After a couple minutes I had
the plug in all the way and began working it around as well as fucking
him with it.  Toby dropped his head back down to the mattress resting on
his arms and I felt him pushing back at me.

Jack gave me a thumbs up, then squirted a liberal amount of KY into my
free hand for my cock.  As I smeared it on, Jack laid down on his side
beside Toby and propped up on his elbow.  He ran his hand up Toby's back
caressing softly and said, "Okay, Tobes.  Are you ready for Donny to fuck
you?"

"Yes!" Toby hissed in a guttural groan.  I barely recognized his voice.

I never lost my erection through all of this.  I stood up behind Toby and
pulled the butt plug from his ass, leaving his hole gaping for me.  It
was such a pretty shade of pink inside!  I quickly placed my little
five-inch cock at his entrance and pushed.  Our prep-work had been up to
the task and I slid right in with almost no resistance, taking Toby's
cherry in a single motion.  I moaned loudly as Toby's tight warmth
engulfed me.

Toby groaned loudly and pushed back against me.  "Oh, Donny," he cried,
"it feels so good!"

Remembering how quickly it was over for Toby and Marcus their first time
in me, I was determined to last longer.  Tempted as I was, I did not
immediately begin pounding his ass.  I grasped him by the hips and slowly
pulled back out all the way, then I went back in just as slowly.   Toby
and I were both moaning and groaning.  Jack was running his hand up and
down Toby's flexing back muscles.

"You're doing great," Jack whispered to Toby.

I had learned from when Jack fucked me earlier, so I varied my pace and
stopped entirely a couple times to make it last.

"Donny," Toby groaned, "Stop teasing and fuck me!"

That forced a laugh out of me!  My how our roles had reversed!

"Okay, buddy," I said, pulling out completely and taking a step back.
 "On your back, stud.  I wanna see your face when I cum inside you!"

"OH FUCK YEAH!" Toby yelled and flipped himself on the bed, actually
jumping into the air like a gymnast onto his back.  He grabbed his legs
and pulled them way back completely exposing his still gaping hole to me.

I dove on top of him and sank my cock home in an instant!  Toby wrapped
both his arms and legs around me pulling me tight against him as I
pounded away in his ass.  My lips found his and we kissed more
passionately than I thought possible.  At that moment all else ceased to
be for both of us.  There was just Toby and me engaged in a carnal bond
that transcended everything.  We were one.

Toby's hands were everywhere, running up and down my back, tugging on my
ass, grabbing handfuls of my hair, touching my face, all while I pounded
away into him.  Finally I felt my balls pulling up against me as my
orgasm prepared to fire.  I pulled my head up and looked at his face,
staring into those beautiful hazel eyes with their flecks of bright green
when he said it.

"I love you, Donny!  I love you!"  Toby's eyes then rolled back in his
head and every muscle in his body seemed to flex and tighten.  I felt his
ass ring quiver and close on my cock as his cock flooded the space
between us with his cum.  That pushed me over the edge and I exploded
deep inside Toby.  I thrust once, twice more and went rigid as my orgasm
rocked through me.  I collapsed on top of him, Toby's arms and legs still
wrapped tightly around me.

Eventually we rolled over onto our sides, caressing and holding each
other, kissing occasionally, but mostly just staring into each other's
eyes.

"I love you, too, Toby," I said.  "I've loved you forever."  Toby's eyes
sparkled and moistened.  He looked like he was going to say something
more but I stopped him, putting a finger to his lips.  "Shhh," I said.
We repositioned so we were laying on Jack's bed properly but we continued
to cuddle and kiss and just hold each other.  Eventually, I felt Jack
crawl into bed and cuddle up behind me.  He wrapped an arm across both of
us and I drifted off to sleep.

--=TO BE CONTINUED=--