Date: Wed, 5 May 2021 11:15:12 +0200
From: Wilson Redding <wilsonreddingstories@gmail.com>
Subject: The Escapades - Chapter 1 - Hot Older Guy

The Escapades Chapter 1 - Hot Older Guy

Number 49E. Max looked up at the old, fancy five-story apartment building.
He double-checked the message Daniel had sent him on Grindr, his screen
flashing brightly in the dark of the night. Yes, this was the place. So Max
rang the doorbell and waited.

`Hey', the intercom crackled.

`Hi.'

`All the way up.'

The sound of a buzzer, and Max pushed open the door. A kind voice, he
thought, a good sign. He stepped into the hallway and started to climb the
stairs after discovering there was no elevator. Way above him, he heard the
sound of a door opening. Even though Max was no stranger to exercise, he
walked slowly and deliberately so he wouldn't appear out of breath when he
reached the fifth floor. As he finally rounded the last corner, he looked
up to see Daniel standing in the doorway, looking at him, smiling.

`Hi', said Max again, and he smiled too. `Damn, those stairs are quite
something.'

Daniel chuckled. `You seem to be doing alright. I've had friends come up
here completely out of breath.'

`I'm trying to hide my wheezing.'

While Daniel laughed, Max walked up to him and extended his hand.

`I'm Jesse', he said, using the fake name he always used on Grindr.

`Hi Jesse, I'm Daniel.'

Daniel shook his hand, looking at Max admiringly, apparently he liked what
he saw. Seeing Daniel up close, Max felt the same way. To begin with,
Daniel looked like his profile picture. He was about 45, twenty years older
than Max, but Max had a thing for older guys. He was around the same
height, six feet, well-built, though not overtly muscular, broader than Max
himself. Daniel's dark-brown hair had a slight curl to it, and started to
turn grey at the temples. He was wearing a white t-shirt and dark jeans
that fit him perfectly, his feet bare. Not bad at all, Max thought, this
could definitely work. He walked past Daniel and entered the apartment.

`Nice place.'

These things were always a little awkward.

`Thanks. You can put your coat on the rack. You want a drink?'

`A glass of water, please.'

Daniel disappeared into the kitchen, while Max looked around the apartment.
He liked the style. It was quite large and well-decorated, colorful but a
little cluttered. There were a few pictures on the cabinet next to the
television.

`This is the boyfriend you were talking about?', Max asked as Daniel came
back into the living room with two glasses of water. He held up a framed
photo of Daniel kissing a handsome, slightly younger guy on the cheek.
Daniel nodded and put the glasses on the end-table near the couch.

`Yes, we've been together eight years now.'

`And he's out of town?'

`Yes. You're single, right?'

`Yes I am.'

Max looked at Daniel.

`So only while he's away you're allowed to play with other guys?'

`Yes.'

`And only on the couch, not in the bedroom?'

`That's the rule.'

`I'm fine with that. The couch can be fun.'

Daniel smirked. Max grabbed the glass of water from the end-table and took
a sip. Daniel looked at him expectantly. It was silent for a moment.

`You're really handsome, Jesse.'

`So are you.'

As if that was Daniel's cue, he walked up to Max, took the glass from him,
put it down and then started kissing him. Max, a little surprised, returned
the kiss, opening his mouth to allow Daniel's tongue. Usually there was
some talking involved before a date got down to business, but Max was
absolutely fine with getting right to the point. He put his arms around
Daniel's neck as they both started exploring each other's mouths. Damn, Max
thought immediately, Daniel was a good kisser. He could feel himself
starting to get aroused already, his cock was getting hard. A great kiss
always did that to him, though to be fair, Max didn't need much to get
hard. Meanwhile, Daniel hummed, apparently also appreciating the kiss. His
hands started to explore Max's body, slowly caressing his neck, his chest,
moving around to his back before settling on Max's ass and kneading the
muscle. Daniel hummed again, while Max moved one hand through Daniel's
hair, using the other to pull Daniel closer to him. He could feel Daniel
was getting excited too, their growing bulges rubbing against each other.
MAX grabbed Daniel's ass and noticed it was nice and big. He loved a
beautiful ass.

`Let's get to the couch', Daniel whispered.

Max nodded, so Daniel took his hand and led him to the couch, sitting down
and looking at Max with a smile. He rubbed the bulge in his jeans.

`I like that', Max said.

`Good.'

Max bent down to sit on Daniel's lap, one knee on each side of Daniel's
body. He started kissing him again, slowly grinding his body against
Daniel's, feeling their arousal. Daniel wasted no time in getting his hands
on Max's ass again, this time sliding his fingers below the jeans. He
groaned as his hands discovered Max was not wearing a boxershort, but a
jockstrap instead.

`You like that?', Max asked softly, smiling at Daniel's obvious approval.

`Love it.'

Max kissed him again, and they both enjoyed exploring each other's bodies
for a while, teasing each other with kisses and touches. Then, Max got to
his feet and stood in front of Daniel. He slowly started unbuttoning his
jeans.

`Little tease', Daniel groaned.

Max said nothing, but slowly pushed down his jeans to reveal a simple grey
jockstrap. His favorite, it made his ass look great. He took off his shoes,
removed his jeans completely, taking off his socks too and stood in front
of Daniel in nothing but his bulging jock and his t-shirt. He turned around
coyly, showing off his long, slender, muscular legs and his nice round
bubble butt.

`That's a fine ass.'

`Glad you like it.'

Max got on his knees in front of Daniel and slowly started to unbutton
Daniel's jeans, revealing his simple black underwear with a very obvious
bulge. Max rubbed the bulge for a moment, feeling the hard dick
underneath. He was happy to discover Daniel hadn't lied on Grindr, he was
indeed large, Max guessed about 7.5 inches, the perfect size for him.

`Stop teasing me, boy', Daniel commanded, suddenly more dominant.

Max laughed and bent forward to give Daniel a deep, playful kiss, before
pulling down his black underwear to reveal one of the best cocks Max had
ever encountered. It was indeed about the size he had guessed, uncut, quite
thick too, perfectly proportioned and pointing straight upwards with a
slight curve. Daniel had trimmed his pubes and balls. Max's mouth watered.

`Fuck, that's a beauty.'

Without further hesitation, Max grabbed Daniel's prick with his left hand,
slowly pulled back the foreskin and started to suck. As soon as his tongue
wrapped around the thick head, Daniel started to moan. Taking that as a
sign of approval, Max started sucking Daniel deeper, licking the shaft and
enjoying the feeling of that beautiful throbbing cock in his mouth. He
could feel his own cock getting harder too, spurred on by Daniel's
enthusiastic moans. Daniel grabbed Max's head with both hands, wrapping his
fingers in Max's dark curls, and slowly started fucking Max's mouth. Max
moaned, trying to take his dick deeper and deeper, even though he wasn't a
deepthroat expert by any means. He gagged a little. Daniel didn't seem to
mind, his breath getting heavier as he slid his glistening dick in and out
of Max's throat.

`Love those big lips wrapped around my pole.'

Max hummed happily, he often received compliments about his full lips. He
kept sucking Daniel, getting hornier by the minute. After a few minutes,
Daniel stopped Max and pulled him up on his lap again. They started
kissing, sloppier now. Max kept grinding against Daniel, loving the feeling
of Daniel's wet cock against his ass, while Daniel grabbed Max's ass,
inching one of his fingers towards Max's asshole. Max stopped him for a
minute to take both their t-shirts off. Max was wearing nothing but his
grey jockstrap now, while Daniel still had his jeans around his
ankles. Daniel's hands roamed Max's body. Max was slender but toned, with
nice muscle definition and a light sprinkling of dark hair on his chest,
around his cock and his asshole. Then, Max took Daniel's right hand and
slowly sucked his middle finger, getting it nice and wet. Daniel grinned,
needing no further instructions he took his finger and started rubbing it
around Max's asshole. Max moaned, feeling his cock jerk a little with every
circle Daniel made around the ring of his hole. Then Daniel slowly pushed
in. Max kissed Daniel deeply, meanwhile backing up his ass against Daniel's
finger, getting it deeper inside. Daniel knew what he was doing, putting
his finger precisely on Max's prostate. Suddenly, Daniel removed his
digit. Max looked at him questioningly.

`I gotta see this perfect little ass. Stand up.'

Max stood up, and Daniel did as well, removing the clothes he was still
wearing.

`Get on your knees on the couch. Ass towards me.'

Max looked admiringly at Daniel, who stood in front of him now completely
naked. He had a nice body, not as toned or tight as Max's, but with broad
shoulders, a nice hairy chest, a flat stomach and thick legs. He was
obviously aroused, his big dick hard and pointing outwards. The perfect guy
for me, Max thought as he turned around and got on the couch on his knees,
his ass towards Daniel.

`Arch you back.'

Max did so without question. He loved this position, something about it
always made him feel so horny. His dick agreed, as he looked down he saw
the outline of his hard cock straining against the elastic band of his
jockstrap, a little spot of precum had formed on the fabric. He wiggled his
ass teasingly, begging Daniel to come over, which he did
immediately. Daniel knelt down, and grabbed Max's ass with both hands. Max
moaned as Daniel started licking his asshole.

`Fuck, that feels good.'

Daniel continued rimming him, sticking his tongue in Max's hole and
simultaneously rubbing Max's bulge. Max grabbed Daniel's hair and pushed
him against his ass, urging Daniel to tongue him even deeper. A groan
rumbled from Daniel's chest, as he finally pushed the pouch of Max's jock
aside to release his cock, which was in serious need of some
attention. Max's dick was also uncut, about 7 inches, slightly smaller than
Daniel's, but girthy and with a fat head. Daniel seemed to want to get a
closer look, because he starting licking Max's taint, his balls and then
pulled Max's dick down to take it in his mouth, licking off the precum
first. Max groaned, Daniel was a good cocksucker too, he sucked Max's dick
fast and hard. Finally Daniel stopped, he pushed Max down and gave him a
wet and sloppy kiss.

`Come with me, I need to fuck you.'

Even though he very much was looking forward to getting fucked, Max looked
at him questioningly. At risk of killing the mood:

`To the bedroom?'

`Yes, I don't care', Daniel groaned as he stroked his hard dick, `Come on.'

Daniel extended his hand, Max took it and Daniel led him to the bedroom. It
was small and seemed well-decorated, but Max didn't have much time to look
around before Daniel pushed him onto the bed. Max laughed as he sprawled on
the sheets.

`So how do you want to fuck me?'

Daniel didn't need much time to think.

`Get on all fours, doggy style.'

Max smiled, turned around and got on his hands and knees, his ass towards
Daniel. He spread his knees, arched his back and looked back at Daniel,
teasingly. He knew the jockstrap would give Daniel a great view. Daniel
groaned in appreciation.

`You're a sexy little fucker.'

`Get a condom and come here.'

Daniel walked quickly to the cabinet next to the bed, his erect dick
bouncing, and he grabbed some lube, a condom and a towel. He got on the bed
and ripped the condom wrapper open.

`You wanna put it on?'

`Sure', Max said as he turned around. Daniel handed Max the condom and got
closer. Max checked the condom to see which way it unrolled, and then
placed in on the tip of Daniel's perfect cock, slowly rolling the condom
down to the base. He moaned in appreciation, and jerked Daniel a few times.

`Your dick is amazing.'

Daniel chuckled, while Max grabbed the lube and applied it liberally to the
condom. Once he was done, he put some lube on his middle finger and
fingered his own asshole, making sure it was ready. Daniel's cock twitched
as he saw Max's finger pushing in and out. Then Max spread the towel on the
bed, got on all fours again, presenting his ass to Daniel.

`Go slowly at first, okay? You're big.'

`I will.'

Daniel grabbed Max's hips and slapped his lubed cock a few times against
Max's asshole. Max pushed back. He suppressed a moan, the anticipation was
killing him. His cock, which had flagged a little, jerked right back up.

`Go on.'

Max felt Daniel push the tip of his thick rod slowly against Max's asshole,
and he groaned in pleasure and a little bit of discomfort as he felt Daniel
breaching the ring of muscle. Fuck, Daniel was big, even these first inches
were tough.

`You okay?'

`Just a second.'

With his face in the sheets, Max waited for a few seconds until the
discomfort subsided. Luckily he had lubed himself up well, so when he
slowly started moving again, Daniel's cock slid in a little more easily. He
was about halfway in now.

`That's it', Daniel groaned in pleasure. Max felt his asshole opening up,
he was getting more comfortable taking Daniel's girth. He pushed back a
little, signaling Daniel to go deeper. Slowly, Daniel pushed in, filling up
Max's inch by inch. Finally Daniel's cock was in completely. Max moaned,
his eyes closed.

`Oh my god, that feels fucking good.'

Daniel pulled out a little, and pushed back in, eliciting another moan from
Max. Slowly, Daniel started fucking Max harder.

`Yes, fuck me.'

That was all the encouragement Daniel needed. He pulled his cock out
completely and slid it back in quickly, and started fucking Max with
strong, deep strokes, his balls slapping Max's ass with every one of
them. He grabbed the band of Max's jockstrap, his breathing getting more
labored, his grunts mixing with Max's moans every time he slammed into
him. Then Daniel grabbed Max's dark curls and pushed his head into the
mattress, getting dominant again.

`Keep that ass up.'

Max happily complied, loving the feeling of Daniel's thick throbbing cock
sliding in and out of his ass, fucking him harder and harder. He begged for
more, and Daniel kept giving it to him. After a while, though, the pace
changed. Daniel wrapped his arms around Max and held him tightly, suddenly
fucking him slower and more tenderly. Max turned his head and kissed Daniel
hungrily, while the sweat on his back mixed with that of Daniel's
stomach. He felt Daniel's long cock inside him, rubbing that spot that made
Max's cock leak precum like it was a leaky faucet. They both moaned,
kissing and appreciating this sudden lull in their hard fucking. Max
grabbed Daniel's hands and Daniel responded by intertwining their
fingers. Suddenly it felt very romantic, especially compared to the rough
fucking from a minute ago.

`Let me ride you', Max whispered into Daniel's mouth.

Daniel grunted in reply, and then slowly pulled his cock out of Max's
hole. He fell back onto the bed and stretched out his legs, sweaty and a
little tired. He exhaled loudly.

`Damn, hard work.'

Max laughed and patted him on the leg, meanwhile loving the sight of this
handsome man, lying down with his big hard cock resting on his stomach.

`Then let me do the work now, old man. Where's the lube?'

Daniel huffed jokingly, but then looked around, spotted the bottle and
handed it to Max. Max put some fresh lube on his asshole, tossed the bottle
and then climbed on top of Daniel. They kissed for a while, deep and with
plenty of tongue. Max rutted against Daniel's body and felt Daniel's lubed
cock sliding between his buttcrack. Finally, Max broke off the kiss. He put
his hands on Daniel's chest and pushed up, now sitting on Daniel's lower
stomach, with one leg to each side. Max looked at Daniel but said nothing
as he grabbed behind him, took Daniel's dick, which was still rock-hard,
and guided it towards his asshole. He got up a little and slowly sat down
when he felt the head push against his hole. This time, his body was used
to the size and he easily pushed Daniel's cock inside him, down to the
base. Daniel groaned.

`Fuck, that ass.'

Max smirked and started moving, riding Daniel. Slowly at first, but soon
his pace quickened. Daniel grabbed Max's ass and guided him up and down his
cock. Max felt his asshole stretch every time he pushed himself all the way
down. He arched his back and thumbed Daniel's hard nipples. His own cock,
hard and straining, bopped up and down. Daniel licked his hand and started
jerking Max's cock. Max moaned, loving it. While doggy was his favorite
position, he also really enjoyed riding a man like this, being in complete
control. Daniel seemed to love it too, his groans were getting louder and
louder while Max rode him. Max thumbed Daniel's nipple again. Suddenly,
Daniel, stopped him and held him in place, his cock about halfway inside
Max. Max felt it throbbing.

`Don't move, I'm close. Give me a second.'

Max smiled and bent forward to kiss him again, Daniel answered
hungrily. They tried to keep still, so Daniel could keep from
coming. Playfully, Max bit Daniel's lower lip, perhaps a little too
hard. Daniel looked at him in surprise. Max returned his look with a
devilish grin and suddenly started riding Daniel again, quickly sliding up
and down the length of his cock. Daniel was not prepared.

`Fuck, fuck, fuck, you bastard, fuck yes, I'm coming!'

Max laughed softly and kept riding him, feeling Daniel's cock pulse inside
him. He moaned while Daniel grunted loudly, and started jerking his own
cock. He was close too, and feeling Daniel push wildly inside him put him
over the edge.

`Me too', Max moaned loudly, while quickly stroking his own cock and still
frantically riding Daniel's.

Thick, white spurts of cum sprayed all over Daniel's chest, almost hitting
his face. Max always came a lot, especially with a dick in his ass. Panting
as he came down from his orgasm and the last few drops of cum landed on
Daniel's chest, Max slowed his rhythm, now moving up and down Daniel's pole
slowly to allow Daniel to enjoy the last moments of his own ejaculation.

`Jesus Christ', Daniel exhaled blissfully.

Max couldn't do anything but laugh. He gave Daniel a quick kiss before
letting the now softening dick slide out of his ass. He wanted to stand up
and grab the towel to wipe off, but Daniel took his arm.

`Come here.'

He pulled Max next to him and wrapped his arm around him.

'I need a minute of this.'

`Okay', said Max, feeling completely sated after this perfect round of
sex. He couldn't remember the last time he had sex this good. He laid down
next to Daniel, while Daniel used his other hand to take off the condom,
now filled with his seed. He tied a knot into it and threw it on the
floor. For a while, they lay there, Max wrapped in Daniel's arm, saying
nothing to each other, the cum on their bodies turning sticky. Daniel
started burrowing his fingers through Max's curls. It was strangely
intimate. Max always thought these moments right after sex with someone you
just met were strange. It felt a little different with Daniel however, more
meaningful somehow. It was nice, but Max remembered Daniel had a long-term
boyfriend, and nothing could really happen here. So finally, after a few
more moments, Max got up, and used the towel to wipe the cum from his
hands, then gave the towel to Daniel, who subsequently wiped the mess from
his chest and stomach.

`Want to take a shower?', Daniel asked.

Max hesitated, but decided he was feeling a little too comfortable in
Daniel's presence.

`No, thanks. I'll take one at home.'

`You sure?'

`Yeah, but thanks.'

He gave Daniel a quick kiss to hide his discomfort and then started looking
around for his clothes, the next second remembering they were all in the
living room.

`Gotta get my clothes', Max said awkwardly.

He walked to the living room and started to dress. A few moments later,
Daniel came in, still naked, his dick now soft, and apparently completely
comfortable.

`I really enjoyed that', he said as he leaned against the doorway.

`Me too', answered Max, without looking at Daniel, as he pulled up his
pants. He looked around for his t-shirt, but Daniel came up to him and
wrapped his arms around Max. He got close and kissed Max deeply. The kiss
didn't have the same urgency as before, but Max was happy to discover
Daniel was still a great kisser even when he wasn't horny anymore. Max let
his hands slide down Daniel's naked body, grabbing his big round ass. He
felt his own cock twitch a little, almost ready for a second round, but
then stopped the kissing. He smiled at Daniel, then turned to find his
shirt.

`I gotta go.'

`If you say so, mister.'

Max discovered his shirt and socks on the couch, and put them on, then tied
his shoelaces. The glass of water still stood on the end-table, barely
touched, so Max drank it now. He got up, walked past Daniel to the hallway
and put on his jacket. Once he did, he looked at Daniel, with some
hesitation.

`So... this was fun. When is your boyfriend coming back?'

`Tomorrow.'

`So this won't happen again for a while?'

`I don't think so. Maybe in a few months.'

Max nodded, hiding his disappointment.

`That's okay. Let me know when he's out of town again.'

`I definitely will, Jesse.'

Max smiled, gave Daniel one last kiss and then opened the door. He heard
Daniel say a soft goodbye before closing the door, as Max descended all
those stairs. Once outside, he looked around, trying to find his bearings
before he remembered where he parked his car. While he walked, he noticed a
slight twinge of pain in his ass. He didn't mind it, actually enjoyed the
feeling, remembering Daniel's perfect cock. He got to his car and opened
the door, but then felt his phone buzz. Taking it out of his pocket, he saw
a notification from Grindr. He opened the app, and was surprised to see it
was from Daniel. It read:

`I don't think I want to wait a few months actually. Maybe we can arrange
something sooner?'

Max couldn't hide a smile, then replied:

`I would like that.'

He got into his car and drove off, very happy with how this evening had
turned out. And even if it was just sex, he already couldn't wait to see
Daniel again.

The end, for now