The Offer

It was not a good day.  When I woke up very late that morning, my head was pounding like someone had given my hellion eight year old nephew a case of red bull and a drum set.   I was wondering what I had done to deserve such a headache like this when the fog started to lift on the details of the previous night out.  And I remembered why I rarely, if ever drank.  And I wondered if I’d really said what I seemed to recall saying.  Fuck this could be bad, really bad.

Years ago, my friend Dave had confessed when he’d first come to town he’d worked briefly as a male escort.  I was one of the only people he had shared this with and I’d always kept that confidence.  I get it.  Sometimes you have to do what you have to do to survive.  Though if I had to be completely honest with myself, Dave had fueled more than a few of my fantasies over the years.  He was tall, athletic, and solid though he could probably stand to lose ten-fifteen pounds or so, that only made him more attractive in my mind.  Even pushing fifty he was my own personal DILF and yes, deep down I admitted to myself I had a secret crush on him. 

But though I had always been very attracted to him, that feeling only went one way.  He had a deep affection for guys in their twenties that were pierced, tattooed and far more urban than I could ever hope to be.  While in pretty damn good shape with great shoulders and a tight flat stomach, I’m an average looking accountant in his early fifties which pretty much says it all.  And that wasn’t counting my rather large balls and thick cock that was a hair under eight inches.  Though my crush had never impacted the friendship though other than my occasional wistful glance or his image sneaking into my nightly jack off fantasies. 

Then last night happened, or at least I seemed to remember it happening.  I think, it was sort of a big blur.  Since it was his birthday so I took him to dinner where we had a drink or two then he wanted to go to a bar in WeHo.  I generally avoided bars and especially bars in WeHo but since it was a special occasion and he was in charge I relented. 

Somewhere between something with vodka and something else with tequila we had one of those deep heart to heart talks that only those who are three sheets to the wind can have.  Mostly, I suspect, because they won’t remember it later.  Dave confessed his personal training business wasn’t doing well and his side business of massage wasn’t really helping.  He spoke of getting older and not being young and hot enough to compete with the other guys in the area.  Which was a bit true I guess, since most of them tended to be walking advertisements for steroids.  And between a bunch of debt and a few big bills coming up he was freaking out. 

After another round of something with a sidecar, my drunk off my ass brain came up with a brilliant idea.  My offer to help him out of his situation.  I let him know if he ever decided to start escorting again, I’d be first in line.  After a moment of his non-reaction, I realized through the booze what I had said.  Oops, well that did not go over well.  This is why I don’t normally drink. 

Well, that put a rather quick end to the evening.  Dave became very quiet and I felt beyond awkward at that point so after finishing our drinks we each took our respective Lyft rides home.  Where I woke up with the mother of all hangovers. 

With the help of a super jumbo ice coffee, a gallon of water and a handful of aspirin I managed to make it through the day.  I was a bit concerned as there wasn’t a a peep from Dave during the day.  Not enough to worry though since he had even less tolerance for booze than me.  The last time he tied one on he didn’t surface for three days.  My plan though was to feign drunken ignorance of anything that had happened after the fifth drink and just hoped that would work.  I’d miss Dave if he freaked out and ghosted me so I also worked up some heartfelt apologies based on what happened when he finally surfaced.

I was giving him some space but towards the end of the week it was still radio silence.  I was about to reach out to Dave when I finally got a text late Thursday night.

“Hows it going?”  Dave asked.

“I’m good, my hangover only lasted two days. You?”  I answered, breathing in a sigh of relief.  I waited for a response but my phone was silent for a long time.  At least it was a start I thought so maybe the situation wasn’t so bad.  Hopefully, he’d forgotten most of that night. 

Ding.  Looking down at my phone I saw another text and my heart leap in my chest. 

“Were you serious?” 

Hell yes, I was serious.  Maybe if I had just one session of balls to the wall sex with him, I would realized how inappropriate my attraction was and I could stop crushing on him.  So I texted him back, “Yes”. 

That was it until my phone rang Friday night, it was Dave.  I quickly decided not to mention anything about the previous weekend, what I said or his texts.  The ball would be completely in his court.   Half an hour later, I was wondering if he was going to mention anything at all.  Our conversation had been pretty much just a catch up for the week and hangover symptom comparisons.  I had been right though, he was still a lightweight and faired far worse.  It was towards the end of the conversation he finally brought it up.

“Can I ask you a question?”  Dave asked.

“Sure.” I answered without my normal sideways comment which usually involved me popping out some random fact like that was the answer.

“The other night you made me an offer.”  At which point he grew very quiet. 

“Yes, but if that made you uncomfortable I apologize.” 

“No, it’s not that.  It was just a surprise and I’m open to it but it’s just, well, there are guys out there so much younger and hotter than me.”  His voice almost quiet.  I could literally feel his insecurity at getting older. 

“Dude, you are the original DILF.  Do you really not know how attractive you are?”  I explained to reassure him. 

“Maybe I used to be years ago but now… well, thank you.”  Dave answered though I could hear the doubt in his voice.  He seemed honestly surprised someone could find him attractive enough to pay him for sex. 

“If you need money I can lend you some.”  I offered but that only made him cough out a harsh laugh. 

“I’m so broke I could never hope to pay you back.  So how much?”  He asked.  It was my turn to be at a loss for words so I just answered with a question.

“Can I ask how much did you used to charge?”  I asked, since I had no idea what he would consider fair.

He hesitated before finally answering softly, “A couple hundred.”  Then he was quiet again.  Having listened to him talk in the past about problems trying to find ‘skilled tops’ and his habit of wanting me to make decisions for him, I knew what to do.

“Okay, here’s the deal.  I’ll give you a thousand bucks cash for the night with a possible incentive bonus if I’m really happy.”  I said in my gruff adult voice. 

“A grand…” 

“Yes, I’ll book a hotel room so it’s neutral territory.  I’ll text you tomorrow afternoon with details. Okay?”  My voice was stern but soft.

“Yes.”  Dave answered softly. 

“Tomorrow.”  And I hung up, my stomach almost in knots at the idea of finally getting him into bed and worried I might really fuck up our friendship. 

The next afternoon, I got a room in a nearby hotel and got everything ready.  That included a couple of 40 watt bulbs that gave off a warm red light that made everyone look good and would make him look like a God.  Then I texted him instructions and told him to bring any supplies we might need before running out to get some drinks and snacks.

Right on time, there was a soft knock at the door.  Taking a deep breath, I opened the door to let him in.  Dave looked, well, beyond tense to almost terrified as the door closed behind him. 

“Dave, just take a deep breath and relax.  Nothing bad is going to happen.”  I said softly, hoping to get him to relax a bit.

“I know, it’s just I don’t want you to be disappointed.”  His voice quiet and still unsure. 

“I won’t be.  Trust me.” I answered as flicked the little red lights on to set the mood and then turned off the overly bright over overhead lamps.  The change in lighting seemed to help him relax a bit.  Moving farther into the room, Dave kicked off his shoes and tossed his backpack on the chair next to the bed. 

“You want me to put some porn on?”  I asked.  At his nod, I moved to flick on the TV and a minute later two guys were going at it in a garage.  Dave started to pull off his shirt but I stopped him.

“Wait, I want to do that.”  I said as I stepped into his space.  Leaning in, my lips softly grazed his as my hands went to his waste to pull him in closer.  I know he could feel my hardness as our groins met.  My lips gently caressed his before moving to his cheek, his earlobe and his neck.  I breathed in his scent as I flicked my tongue to taste his skin.  With a tiny shudder, his own hands reached around to pull me closer. 

My mouth returned to his and I slowly deepened the kiss, my tongue entering his mouth and making contact with his.  His arms tightened around me as our kiss became deepened and became more fevered.  The taste of him was sending me into overload and my hands ran up under his teeshirt to feel the heat of his muscled back.  After a moment, I broke the kiss to pull his shirt completely off.  He was still as beautiful as I remember from swimming with him a few years ago.  A light dusting of hair spread over his thick chest with that baby spare tire that only made him more attractive.  He truly was the Daddy I was going to fuck.

Pushing him back on to the bed I stripped of my shirt and got on the bed with him.   His arms pulled me down on to him as my mouth met his in another passionate kiss as our bodies ground against each other.  Breaking the kiss, I moved to lick, suck and taste his neck as I started to move down his body.  His own hands weren’t idle, as they roamed my back and through my hair. 

I raised up to look at his face.  With his eyes half lidded, his lips slight swollen from kissing, and skin glowing in the soft red light, he was a work of art.  Something about that craggy face with the beard shadow and smile lines just got to me.  I kept eye contact as I used my mouth and made my way to one of his nipples.

“Wait… I…”  Dave said before hesitating. 

“Don’t worry, I remember.”  I answered, as I ever so gently kissed his nipple.  I could still see the faint scar from his surgery many years ago and understood how careful I needed to be.  With utmost care, I suckled his nipple so as not to hurt him and was rewarded with a hiss of pleasure.   Tasting my way towards my ultimate goal, I pressed my face into the hardness pushing through his pants.  I undid the clasp and unzipped his shorts to pull them open.  His rock hard dick pushed up through his underwear, wanting to be free. 

Pulling his underwear down, his cock popped out.  Hard, beautiful and thick, it was probably just a hair under nine inches.  I jacked his cock a bit before opening my mouth and swallowing the head.  I used my tongue to work my way under the bit of foreskin he had before taking as much of his length down my throat as I could. 

With a moan and a soft “more” Dave pushed his hips up as I continued to suck his cock.  While I wanted to keep sucking, I wanted him naked even more.  Getting up on my knees, I finished pulling off the rest of his clothes before removing my own.  Seeing him like that, naked and hard waiting for me made my hunger for him grow.  I gave the scars on his knee a quick kiss as I settled back down between his legs. 

Pushing his legs a bit farther apart, I took each ball into my mouth to give them a gentle massage and sucking before slowly, ever so slowly.  The taste and scent of his skin were heady.  Then I moved on to licking up the shaft of his cock to the head.  I focused on sucking the head of his and jacking him as I swallowed more and more of his dick.  Finally with a bit of effort, I was able to get almost all of his length down my throat.  His moans of pleasure and fingers running through my hair encouraged me I continued to suck his cock. 

It was when Dave’s breathing grew labored and his cock grew harder that I pulled off.  As much as I would have loved to swallow his load I did not want this man to climax too soon. 

“Damn dude, I was so close.”  Dave said with the tiniest bit of a pout.  It was sexy as hell.  I moved up to kiss that luscious mouth again as our hard cocks ground together.

“Patience,  I want to make you crazy with pleasure tonight.”  I said as I rolled off on to my side and reached to stroke his cock.  Dave leaned over to kiss me again while his hand stroked my chest before moving down to feel my own dick.  The sensation of finally feeling his touch made me moan into the kiss.  His hand continued exploring to caress and play with my balls.

“Damn,  those are some nice balls.”  Dave said as he lifted his mouth from mine.   He began his own trek south stopping at my nipples, kissing my stomach and then down to my cock for a quick suck.

“And you know I like big balls”  He said as he began to lick and suck each ball in turn while one of his hands jacked my cock.  It was my turn to moan as I had never had anyone pay that much attention to my nuts.  Dave spent the next several minutes moving between lavishing his affections on my balls with an occasional trip to my cock and the feeling was so intense I was getting close. 

As his mouth once again closed over the head of my cock I realized I was far too close and even as much as I pained me, I asked him to stop. 

“Everything okay?”  He asked, looking uncertain as he raised his head.  Just seeing him there between my legs with his lips slick and a tiny bit puffy from using them to pleasure me shot something deep through me. 

“Very okay, but it’s too soon.”  I said as I reached to pull him back up and into another kiss.  I could taste a hint of myself on his tongue.  We continued to kiss and grind against each other as our hands roamed, touched and pleasured.  Using my hand to gently caress his neck while I made line of little kisses to his ear. 

“Tell me what you want.”  I whispered as I traced my tongue along the outer rim of his ear.  With a tiny shudder, he just pulled me closer.  Deep down, I knew what he wanted but also was afraid to ask for.  With his height, build and size of his dick guys always wanted him to top when he would really rather bottom.  I remembered the online ad I wasn’t supposed to see. 

"I’ll tell you want you want, you want me to fuck you.”  I said as I ran my hand down to that beautiful thick meaty ass and gave it a squeeze before running a finger down to tease his hole.  I could almost feel it give my finger a gentle nibble.

“Yes.” Dave said with a barely audible hiss causing my dick to jump in anticipation. 

“Roll over.”  I said as I moved to straddle him.  Sitting astride him with my rock hard cock nestled against his ass, I gently massaged his shoulders for a moment.  I leaned down to kiss, lick and taste his neck as I rubbed my body against his in anticipation of what was to come.  As good as this felt with my skin rubbing against his, this was not how I wanted to fuck him the first time.   I wanted him on all fours so I could fuck him deep, hard and fast.  I already knew I was not going to last long once my dick was inside him. 

I game him a gentle back rub before hopping off him and standing next to the bed.  Looking down at him laying there face down and ass up sent a secret thrill to my dick, he was just beautiful.  His back was lightly muscled with a sprinkling of hair, no waxing for him.  Dave’s ass raised up just enough to show he never skipped doing squats at the gym, wow. 

“Dave, move here to the edge of the bed.”  I said, indicating the position I wanted him to take.  After giving me the raised eyebrow letting me know he wasn’t to sure about this. 

“Trust me.”  I said with my best salesmen voice.  With a slight eye roll Dave assumed the position.  Oh yeah, he knew just the position I wanted him in I thought with an inward chuckle.

On all fours at the edge of the bed with back arched and his ass in the air, Dave was a fantasy come to life.  His ass was meaty and solid with just the right amount of bounce.  The smooth skin warn under my hand as I stroked him.  Moving forward, I rubbed my cock up and down his crack while my hands wandered his muscled back.  I stepped back and took in the beautiful view of him like that with his balls hanging down and ass offered up, wow.  Dropping to my knees, I spread his cheeks to get a closer look at that little wrinkled pucker, damn.

“What are…” Dave started to ask as I leaned in to kiss his hole, causing his voice to change to a softly whispered moan.  Ever so gently, I used my tongue to kiss and lick that perfect circle.  The taste was sensuous, male and one hundred percent pure Dave.  I loved it and from the soft noise that escaped Dave, he loved it just as much. 

Over the next few minutes, I ate his ass with a sense of desire I didn’t know I had.  Using my tongue to circle and tease his hole, I felt it loosen and grow slick as Dave moaned louder and pushed back against me.  My leaking cock was so hard it almost hurt, I was so turned on.

Standing, I quickly grabbed the lube and slicked up my cock.  Not wanting to hurt him with a rough thrust, I gently slid my dick into his welcoming hole.  The warm slick heat was like nothing I had ever experienced.  Once I was balls deep inside him, I gave him a moment.  It wasn’t easy though, I had to fight the urge to pound him hard and fast before breeding that perfect hungry hole.  Glancing down I saw the tight ring of his clenching hole clutch hungrily at my dick as I started with slow gentle thrusts. 

Then I pulled almost all the way out before sliding all the way in a bit faster, causing Dave to let out a softly moaned “Yes, fuck me….” 

“Fuck Dave, your ass feels so good.  Your ass was made to be fucked, you… you were made to be fucked.”  I said with a rough groan as I started to pick up the pace of my thrusts.  His only response was only a muttered yes followed by what I thought was ‘more’.  Grabbing his hips firmly I started to fuck him harder as my balls slapped against his.  I was so so close to blowing my load deep inside that perfect ass. 

“I’m gonna cum.”  I growled out as I picked up the pace.

You ready for my load Dave?” My voice harsh.

“Fuck… yes… give me that load…. breed me.”  Dave groaned as he fucked himself back on to my cock.  Hearing those words from him, made me lose it.  My cock exploded and spurt after spurt of my jizz filled his hungry ass.  Even after my balls had completely emptied, I just kept pounding myself into him. 

Finally running out of steam, I gently pulled myself out of his well fucked ass.  I reached down with on hand to feel his own rock hard cock as I rubbed his back.   

“So…  do you want to fuck me?”  I asked as I leaned down give his back a kiss and continued to stroke his dick ever so lightly. 

“Well, I can if you want…”  Dave answered hesitantly.  Moving up on the bed he rolled over on to his back with that beautiful cock still standing at attention.  In the soft red light, his sweat dampened skin positively glowed.  Though I had just shot a minute before my desire was not yet sated.  I leaned over and slowly kissed, licked and tasted the salt of his skin on his chest and abs.  A hand came to rest on my shoulder and stroked me in gentle affection.  Hearing his hesitation, I knew what I had long suspected was true.  For all his swagger and talk of being almost exclusively a top, Dave was a bottom at heart. 

I moved to give him a kiss, our tongues circling and gliding against each other  as I slowly stroked the length of his cock with my hand.  I broke the kiss and locked my gaze on his.

Straddling him, I gently kissed his face, then to each ear and his neck.  Tiny sucking kisses on his neck led me to his nipples once again.  Then across his chest and stomach, including lazy kisses around his navel.  Finally, I was again at that rock hard cock. 

I slowly sucked his cock, working on the head and then finally all the way down my throat.  Dave moaned and ran his fingers through my hair as I picked up the pace. I wanted, needed to taste this man’s cum.  Using my index finger, I traced the outline of his slick leaking hole to tease him.  Even as his hands grew more frenzied in pulling my face on to his cock, he spread his legs to give me better access. 

I used two fingers to fuck him while I concentrated on sucking his cock.  I wanted this man to explode in an orgasm he would never forget and knew just how to do it.  I thrust my fingers deeper inside him taking direct aim at his prostate.  With the second poke to his joy button Dave let out a howl as he rammed his cock all the way down my throat and unload.  Jets of his cum shot straight into my stomach but I needed to taste him.

Pulling off just enough to feel the last couple of shots of his cum directly on my cum, I finally realized my fantasy of tasting his load.  It was warm, salty and savory all at the same time.  As I licked him clean, I looked up to see Dave breathing so heavily I might have thought he was hyperventilating. 

“Dude, that was, just fucking wow.  I have no words.”  He said as his breathing slowly returned to normal. 

“Good, that was the plan.”  I answered with a smile as I flopped down next to him.  Dave moved to kiss me before snuggling up against me. 

“Do you think you might want to fuck me again?”  Dave asked softly.  I kissed the top of the head and smiled.

“Hell, yes.”  I answered as I pulled him closer.  This was going to be one hell of a night.