Jake's Diary - a onling Work in Progress

bartenderjake

Really Experienced
Joined
Jun 6, 2013
Posts
220
So who am I?

At 30 years old I have been a good number of things.

I come from a wealthy family. Dad is a lawyer and mom is well, married to another rich guy who is not my father now.

I joined the Air Force right out of college and knocked out my first degree, and then ended up in the Military Policy in Iraq. Finished my first tour, got my second degree and went right back over to do my duty.

Ended up in the sand once again, heading for a long career. The work was interesting and it kept me out of trouble for the most part.

Everything was going along swimmingly, until one night when I broke up a drunken party, and broke the arm of a soon to be Senator and then shit-headed Captain.

So thus ended that part of my life.

I’m home now, doing the only other thing I know which is tending bar at an Irish Pub at a local hotel. The money is good, and people basically leave me alone, and did I mention the constant buffet of business woman, college co-eds and lonely housewife’s to play with?

Living at home with my dad again. Which is sort of like being back in high school because even before mom split he and I were more like roommates than family. He does his thing and I do mine.

My father’s current “thing” is his new fiancée, Diane. Dad always had good taste in women. Diane was his executive secretary at his law firm, and I strongly believe that she might have been the reason that mom did take off. Too many unexplained long hours, and probably too much lipstick on the collar.

My current thing is working nights at the bar, descending ever farther into my alcoholism and perfecting my recreational cocaine habit. All the while trying to fuck anything that moves; it seems to be working for both of us.

So what worked for me last night as getting off shift at 3 AM and going over to an after-work party, frequented by waitresses, bartenders and other creatures of the night.

I had found the perfect level, a half case of beer and four lines of blow. Not sloppy and certainly not giving a fuck. It was the kind of buzz where you could still get a nice hard erection but cumming was usually the issue.

That was the case last evening. Her name was Julie. She was pushing 40. Still wished she was 20 and never missed a party. She ended up with her legs behind her ears while I fucked her like a pile driver for nearly two hours before finally giving up – neither of us were getting off tonight.

So fast forward to the ass-crack of noon.

My motorcycle found its way home on it own, as it usually did most mornings. I had only slept on and off for a few hours and had another beer to level out before heading home. I wanted a hot shower and to sleep it off before my shift started in a couple hours. And fuck me if I didn’t have the worst case of blue balls ever.

I never kept track of who was home at any given time. Hell, dad’s house was so fucking big you could go days without seeing anyone. I lost my garage door opener so I parked my bike on the sidewalk outside and went in through the kitchen.

No one around.

Awesome for my hangover.

I stripped off my clothes and headed into the shower. I was a little wobbly as I headed in, maybe a bath.

The sound of running water always relaxed me after a bender. I closed my eyes and put a cold washcloth over my eyes. I stretched out in the tub and let the sounds of the facet take hold. At least maybe I wouldn’t be grinding my teeth at work all night.

Thankfully I didn’t have the drain closed all the way or I might have flooded the house. Not sure how long I had been out but I was definitely feeling better, and definitely ready to take care of my blue-balls.

A little soap and remembering the fucking that I had given Julie a few hours before had my cock hard in my hand almost immediately.

I had been told that I was a little bigger than average, just under eight inches. And being a guy I figured it was always just something that girls said to make you feel better about being average. I leaned back against the tub and put the cloth back on my eyes, slowly stroking my cock. With my free hand I cupped and squeezed my balls. It was still going to take some doing to get myself off.

I thought about past fucks, good porno and kinky desires and my cock pounded in my hand.

Then I got that feeling. You know the one, where you had just been caught jerking off for the first time by your mom.

I opened up my eyes slowly and pushed the washcloth down. My cock still firmly throbbing in my soapy fingers – just please don’t let it be dad.
Turns out it wasn’t him.

I forgot to mention that Diane had a daughter, my soon to be step-sister, named Rachel.

She and I didn’t talk too much usually; she was just 19 and taking classes as some community college so we didn’t have too much in common. Plus she seemed like she was always on her way somewhere, or too busy.

Well there she was, wrapped in a white towel standing in the doorway of the bathroom. Guess I forgot to lock that in my fucked-up state of mind.

Note to self – lock the bathroom door.

She was definitely her mother’s daughter, a tall redhead with a dark tan, thin waist and the best set of tits money could buy. I knew she was a trainer at the gym that I went to but she was never out on the floor, too busy with personal sessions I always figured.

Well from what I could see of her legs under the towel she was definitely a fit girl. Not an ounce of fat on her. And the towel barely covered her breasts. Under the bathroom lights I took immediately notice of the freckles that covered her chest and arms and just how dark red her curly hair was.

I also took notice that she was grinning wryly and never stopped staring at my soapy cock.

I was slightly frozen.

She was not. She gave me a look as if to say, don’t stop on my account.

I tilted my head to the side, still figuring that I was addled from the booze and blow.

As if to punctuate her intent she let her towel open slightly, giving me the perfect view of her little freckled pussy. Completely shaven and already glistening.

Well fuck.

She slipped a finger down over her stomach and started gently caressing herself.

I joined in, slowly stroking my cock, getting more soap and making it nice and slick between my fingers.

We never said a word.

She sat on the toilet seat next to the tub so I could see her fingers playing over her wet pussy. She rolled her head side to side as the towel opened fully.

I was stroking harder now, watching her every move. My breath was coming out ragged and quick.

She cupped one of her impossibly firm breasts and squeezed the dark brown nipple. I saw her ass lift off the toilet seat as a spasm of pleasure ran through her muscular body. Here eyes were locked on my hand and cock.

I was close and so was she.

She worked her pussy furiously now, her fingers dripping with wetness. She moaned now licking her lips and pulling roughly at her nipple.

I felt it coming. The first splash of my own hot cum shot up like a geyser on my chest.

I kept stroking, all the way up and down my shaft, another spurt and another.

She came hard, thrashing and arching her back, I could see every part of her body tense and release and then her fingers finally coming to rest between her parted legs.

I lay there breathing hard with my softening cock lying over my thigh my chest covered in three ribbons of cum.

She took a moment and composed herself. She never covered her naked form with the towel only turned and walked out of the bathroom giving me the parting shot of her firm tanned ass as she departed.

……<to be continued>
 
I didn’t even want to go home with her.

She was 18, two days on the job as a hostess at my bar and a student at an ivy league college in town.

Really I didn’t want to.

So there I am in her dorm room shower eating her ass while she clawed at the tile walls in what I could only imagine was sheer ecstasy and terror.

She was pretty cute, if I was an 18 year old frat boy. She was a tennis player, so she told me over and over after a couple drinks. She had the body for it too, nice tanned legs, tight abs and a pert ass that didn’t even jiggle when I slapped it. Downside, maybe a A cup.

Meh, I was just trying to get the image of my soon to be step-sister out of my mind. The encounter earlier had rendered me pretty much useless at work this evening, and this newly hired jailbait was entirely too eager.

She gave a pretty good blow job, I’m sure that all the boys at her high school were tripping over themselves to finger-fuck her at the prom. All in all, she was a little too gentle for my liking. Probably because I was usually fucked up when I was getting blown I liked the full on down your throat, two hands jerking and a nice firm ball squeezing.

Not to mention that I always preferred my cock to be slapped off a nice set of tits, and honestly if a girl spit on my cock in the most whorish of fashion I was in heaven. But again, she was just a distraction tonight.

I even gave her a courtesy moan, and pulled my cock out of her mouth with the obligatory “Not too much, baby or I might cum too soon.” No chance of that, but what the hell, no sense in ruining her evening.

She was wearing a cute little pair of Hello Kitty panties when I finally eased her tight black work-pants down over her legs. I tore them off her as I pushed her down into the bed. She panted and moaned as I slowly eased my tongue along her bald pussy.

You had to love young girls, always with the porn star shave.

She did taste incredible, like sweet candy, and I lingered between her legs bringing her to the edge. She was loud, and there was no mistaking what she liked. I figured at any moment the Resident Advisor was going to knock on the door and tell us to keep it down.

As I flicked her little clit she clawed at the bed sheets and bucked her pussy into my face. I thoroughly enjoyed her wetness dripping off my chin as I finally pulled away and kissed her.

The shower was her idea. I think she liked the idea of it more than the actual implementation.

Fucking the shower always seemed like a good idea at the time, but it was usually too small, too slippery and rarely were two people the right height to just bend over and have a proper fuck. At 6’1” I was entirely too tall for her 5’1” body.

Finally it was my frustration that led me to broaden her horizons. I pressed her into the cool tile and heard the sharp intake of breath as her nipples pressed into the wall. I kissed down the back of her neck slowly, following the trails of water as they washed down over her back.

My hands kneaded those perfectly firm ass cheeks. She tensed, and I moved slowly, kissing her lower back. Then my fingers dug into her flesh and parted her cheeks as I slipped my tongue down over her tight asshole with one long lick. I felt her knees go weak and heard her almost scream.

To her credit she didn’t pull away and actually started pushing back into me when I began rimming her in earnest. I could tell it was like nothing she had ever had before. She wanted to pull away, to be disgusted but it felt too fucking good. Soon I had my tongue buried deep and her firm ass cheeks on either side of my face.

Then it was back to the bed, dripping wet.

She crawled into the bed and I told her to get on all fours. It wasn’t a request. My cock was aching pretty badly and I needed my release.

She gripped the headboard of her bed as I eased behind her. I gripped the base of my cock and ran the head slowly over her tight puffy pussy lips. Fuck she was going to be tight.

Slowly, just the tip at first I pushed inside of her.

She moaned and bit her lip. “Oh my god”, she panted.

I thrust forward, one long deep stroke deep into her center, her pussy stretched and gripped my cock like a vice.

“Goddamn you’re fucking tight.”

She didn’t say anything just held on to the headboard for dear life as I start to fuck.

Long deep strokes in and out of her tight pussy, harder and harder until I was slamming into her with so much force that her ass clapped against my pelvis.

She looked back at me, half moaning and half screaming.
“That’s it, daddy, fuck my tight pussy.”

I was almost taken back by her outburst. Who the fuck says that.

“Come on daddy, you know you want to fuck my little pussy, give me all that big cock.”

I obliged.

I could feel her quivering, launching off in to a massive orgasm.

“Oh my god, oh my god, I love your hard cock in my pussy, daddy.”

It was too much I pulled my throbbing, spasming cock out of her tight body and spurt a huge load of cum on her amazing ass.

She was hanging on to the headboard in the midst of her own orgasm as I knelt behind her stroking out ever drop of cum onto her ass and back.

Finally she collapsed in the bed, unable to move.

I found my clothes on the floor and let myself out.
 
Not many nights find my entire family home, and when it does it usually sucked.

I don’t get along with my dad’s new wife-to-be, and my step sister and I basically saw each in passing since our little encounter in the shower. And by in passing I mean I usually had to excuse myself because of the throbbing erection I instantly got when I saw her.

Tonight was no exception, after some small talk in the kitchen the parental units decided to stay in and watch a movie, and my step-sister and I were left to our own devices in the house.

I retired to my bedroom. It was the middle of the week, and I was off work and didn’t feel much like doing anything except well….nothing.

The night was fairly uneventful until close to one in the morning..

One of the joys of being me, and alcoholic, is that on those nights when I choose not to drink I usually can’t sleep.

As the clock was still ticking away and I was wide awake, I figured it might be time to resort to a tried and true method of getting to sleep…jerking off.

Usually a nice slow tug to some porn or a Cinemax after-hours special was just enough to let me drift off to sleep.

I checked the hallway first; I could hear that the TV was off in the living room, so at least dad was sleep.

Cinemax was pretty good too, well by my standards anything with Nicole Sheridan was pretty good and usually got my cock hard and throbbing one or two minutes into any scene she was in.

There I lay top my sheets, cock in hand and idly stroking while watching Nicole Sheridan take it doggy style. A little pre-cum for lube and I leaned back in my pillows and closed my eyes for a moment. It was building up to be a pretty good pop-shot, I might actually sleep well.

You ever get that feeling that you are being watched…..

Well I did, right then…again

And I was.

There she was, standing in my doorway.

Rachel had one finger in her mouth watching intently. She was wearing a white terrycloth robe; the kinds that were so short you could see the bottoms of the girl’s ass cheeks. Except that hers was hanging open.

My step-sister, the fucking voyeur

I, of course, didn’t stop stroking. Fuck it, she wanted to see again, and I remembered how hard I came the last time she was peeking.

She stepped into the room, dropping the robe on the floor.

I didn’t stop. My fingers squeezed at my pulsating shaft as she neared the edge of the bed.

“Don’t stop, Jake.”

I nodded as she eased herself into the bed next to me.

She was long, sleek and slender and I almost came as I saw her toned, freckled body laid out before me.

“Don’t touch…just keep going.”

She eased her head back and I watched her slender fingers descend between her legs, teasing at her smooth pussy.

I took every inch of her in at once, her open mouth, the swell of her tanned perfectly formed tits, the flutter of her stomach and the glistening wetness on her fingers.

She ran one hand up over her breasts and pinched her hard nipple fiercely, pulling at it as she rubbed her swollen clit, there was no question as to whether or not she was enjoying.

I was cupping my balls now, squeezing harder with each stroke of my cock. Pre-cum was dripping from the tip and her eyes seems transfixed on the sight.

She moaned out as her fingers caressed her body.

I could see her back arching and her body trembling.

It wasn’t me per say that was turning her on; it was the sight of a man stroking his cock. I had the feeling that she would have been laying next to someone else tonight if not me. And her detachment and pure look of pleasure made my cock ache.

It was just about getting off, whatever the means.

I pounded my thick cock harder, watching every inch of her body at once.
Here eyes never left my cock.

She never made a move to touch me, and I never made a move towards her. It was purely visual, purely getting off watching someone else as they got off.

We were in unison. Moans escaping our lips, the climax building within us both.

Her fingers were drenched and her knees opened and closed as she fought back her orgasm.

She finally exclaimed “Fucking cum with me, I want to see your hot fucking cum.”

And it was too much for me to handle.

Those words coming out of her mouth made my cock explode with such force that it showered us both with a splash of cum.

She launched off into her own orgasm, racing her fingers back and forth over her clit, moaning and biting her lips.

I kept stroking madly, more and more cum gushing out.

She finally jerked to a halt and breathed deeply.

My cum had splashed on her perfect fake tits and was oozing between the fleshy mounds.

She looked over at me one last time and smiled wide, never touching the cum on her tits.

“See ya later.”

And then she left my room, without another word.

“Fuck. I muttered. “I am in trouble.”
 
You know when people have no way of describing a fat girl they always say “well, she has a pretty face.”

Well this slut had a beautiful face.

And as you might infer, the rest of her was a hot mess. Not really the sloppy fat, but the just plain big fat. There were curves, but when you were used to size one and two, a size 16 is a striking contrast.

I’m also talking the kind of fat girl that likes to wear the clothes that are super trendy, about two sizes too small and who thinks that guys love them because their tits are so big.

Well fuck, sweetie, everything is fucking big.

But as they say, big girls need lovin’ too.

This girls name was Mindy or Misty or Mandy…..some fucking thing.

She had recently moved home from college with master’s degree in environmental sciences and, of course, was managing the local Hollister store in the mall. Which is funny because she looked like she ate four or five of the models for that store. That’s not entirely fair, she wasn’t terrible looking…or at least nothing that forty pounds wouldn’t take care of.

Ok she was a pig.

She was at the dive bar I frequented after work most nights when I got off early.

She was fun and flirty and I have to admit that after my fourth or fifth Johnny Walker Red, her big sloppy tits, which were crammed into two-size too small shirt were looking pretty good.

She was pretty open about everything, from partying to school to threesomes to her parents divorce to enjoying a good cock in the ass. It all came out with a few drinks; as blunt as could be.

By the end of the night her big ass was sitting next to me at the bar and she had one hand in my lap feeling my cock through my pants. I knew where I stood when she leaned over to me at last call and whispered “Can I have that cock tonight, or are you not drunk enough.”

She was eager, and sort of knew her place in the world.

Her attitude was the hottest thing about her actually. Nothing wrong with a little no strings attached fuck and forget.

I followed her to her parent’s house of all things.

I made sure to take my own car, because I had no intention of staying the night or depending on her for a ride home…or worse yet, having to give her a ride home.

She was looking passable now at 3AM, at 10AM I was going to be scrubbing my cock with steel-wool trying to forget.

Her parents were older and apparently didn’t bother her in the basement / apartment she currently inhabited. She made sure to let me know at numerous points during the night that her apartment was soundproof, and that she was a bit of a screamer.

We no sooner got a drink and sat on the couch and she was straddling me.

Aggressive was an understatement, she put her tongue down my throat and ground into my lap like she was never going to get a cock again.

I never did mind rough.

She didn’t have bad technique; she worked her hips back and forth, rubbing her pussy into my throbbing cock pretty good. And that was through jeans and her thin black pants.

She was wearing a low-cut, v-neck shirt and I pulled it off over her head and was almost knocked out by the sheer size of her breast. They were massive; barely contained by the black bra that she wore. I could see that her nipples were already hard and poking through the black lace. The mounds of flesh jiggled just right and leaned my head down to suck each hard pink nipple right through the lace. Each time I drug my teeth over the sensitive buds she ground harder into my cock and moaned sharply, putting her hands in my hair and pulling my mouth against her tits harder.

When she had enough of that teasing she slipped off my lap and got on her knees in front of me. Licking her lips she smiled wide.

“All the guys tell me that I suck a really good cock.”

She was bragging. And part of me did wonder just how many other guys had dumped their load in this cum dumpster.

Didn’t really matter, she had my cock out of my pants and was slowly stroking up and down the shaft. Good firm hands and a nice caress of the head.

And then she put me so far down her throat I think I grazed her tonsils.

She didn’t gag, or even breathe hard as she pulled the cock out of her throat. Strands of saliva ran from her lips to my cock. And it was my turn to tangle my fingers in her hair as she did it again and again.
Soon her saliva was running down over my balls and making a mess of her face and she just kept going like a champ.

I reached down her back and unclipped her bra.

She came up from my cock smiling, still stroking my shaft.

“Do you want to put it between my tits?”

“You’re fucking right I do.”

She clamped her massive tits around my dick and started stroking up and down….hard. It felt like fucking a tight pussy. Every time my cock popped out between the globes she flicked her tongue over the tip, wiping away the pre-cum that was forming on the tip.

So now I was totally getting into it.

She slapped my cock against her big tits and it made a wet smacking sound.

She wiggled out of her huge black panties as I shucked out of my shirt and jeans.

She was on her hands and knees in the middle of her living room floor as I come up behind her. What a sight, her wide ass shaking at me. I gripped the base of my cock and ran it along her wet slit…I think. Who really knows at that point, but she started moaning and kept pushing.

Then I felt myself slide in. Now I don’t have a small cock, and some girls would attest that I am bigger than some but nothing special or porn-starish. But fucking this girl was like tossing hotdogs down a hallway. I could barely feel the sides of her pussy as I slammed into her from behind. And I when I mean slam, I mean as hard as I could until our bodies crashed together. Her ass jiggling and wiggling as my pelvis bucked into it.

There was one second where I thought “what the fuck am I doing with this hog”.

That was soon forgotten as she pushed me back on the floor and straddled my cock. She eased down on me until she was settled fully with my deep inside. Then she started working her hips back and forth, my cock sliding in and out of her wide pussy.

She sat upright and started to moan as she rode me. Not too loud at first but as her hips moved back and forth faster and faster she got louder.

My hands her mauling her breast, squeezing and kneading, pinching her hard nipples and pulling at them without mercy as she bounced up and down. Every inch of her un-toned body just wobbled, but fuck if she couldn’t ride a cock. Goddamn.

The rougher I got the harder she ground into me.
She was arching her back down and reaching back cupping my balls as I looked down and watched my cock delve into her pussy over and over.

I could tell she was close. She started diddling her clit with my cock still inside.

“Don’t cum inside me.”

“Where do you want it?”

“Jerk off in my mouth.”

I had no problem with this request. I pushed her on her knees and stood over her. I started stroking hard, up and down the entire length as she knelt before me playing with her pussy and shaking, on the verge of cumming.

I pounded harder, arching my back as the first line of cum splashed on her tongue. She reached up and squeezed my balls hard and I fired another shot into her warm inviting mouth.

She started to cum hard. Her body quivering as she clung to my thighs. My final spurt landed in her hair but she was far too gone to notice. Wetness was dripping down her thighs and she lay back, panting and gasping.

I sat on the edge of the couch, taking a moment to recover.

In a few moments, I heard drunk snoring from the floor where she lay.

Easiest escape ever.
 
Well there are some other things that I might now have divulged about myself with my first couple of entries in my diary.

See, here’s the thing. I have absolutely no shame about being bisexual. In fact, I am so open about the fact that I usually forget to mention it to people. It kind of just is what it is.

Now I don’t go broadcasting my personal life around a whole lot, but if you know me, and certain offers are made, or if I get a certain vibe a cute guy is likely to get propositioned just as easily as a hot girl.

At this time in my life, I was pretty much only acting on my bi impulses with couples. Usually as the “third” for those guys and girls who wanted to spice it up in the bedroom a little, or for some of my swinger friends who needed a DP for the wifey. Not to say that I hadn’t taken a guy home here and there, but just not recently.

Bottom line wasn’t actually going out trying to get dick, but you know, not really turning down a good time either.

So when my friend Samantha approached me with an offer one afternoon at the bar I was kind of taken aback…mostly because I wasn’t sure if I had actually ever told her that I was bisexual. But I drink a lot so I probably did.

Sammi is a striking Asian girl. I say Asian because I think she’s Korean, but I have no fucking clue for sure. She looks like one of those jailbait anime characters; big eyes, hair in pigtails and that tight body that is a cross between a woman and a teenage boy. She is maybe an A cup with a padded bra, but goddamn her ass is impeccable. And usually she was poured into tight jeans. Today was no exception, but when she came in for lunch she was also wearing a sheer, see through blouse and a black bra underneath.

She was looking great I totally checked out her taut stomach through the blouse as she eased into a bar stool.

Sammi was my Saturday night co-bartender. She was cute, competent and knew enough to flirt with the big money customers to get us the tips. We had a good understanding.

My biggest problem with Sammi was that while she was a great kid, and I mean kid, just 21 years old, she usually dated those douche-bag Asian guys who thought that they were street racers and Yakuza. In a year of working together I never found on that I didn’t want to run over in the parking lot.

She usually came in on Tuesdays after classes and hung out for lunch and shot the shit with me about nothing in particular.

Today I could tell she was all about something…I just wasn’t sure what it was.

“Do you have any plans for tonight?” she started as she sipped at a cup of coffee.

“Nope, I get off at six and then was going to see what kind of trouble I could get into. What do you have going on?”

She shrugged, “Nothing much, probably hanging out at my boyfriends apartment.”

“Is this the new guy with the shiny exhaust tip and spoiler on his Honda?”

“Shut the fuck up, Jake. He drives a Beamer.”

“Yeah, that his parent’s bought him!”

“You live in your dad’s mansion, asshole.”

“Touche”

“So is he treating you right?” Not that I cared but I liked when she came in, she was a trust fund brat like I was and she was fun to talk to and usually left a big tip.

“He really is, we go out all the time, and he has his own money so I know he’s not into me for that.”

“Must be those hot Asian sex secrets you lay on him.”

“He doesn’t seem to complain.” She grinned wide.

She and I had never been too shy around each other, and it was always fun to try to make the other one blush with the most inappropriate shit.

“So you really don’t have any plans for tonight?”

I stopped wiping down the bar came over to her.

“That’s the second time you asked….what’s up?”

“Ok, so I have this question….or maybe it’s more like a request…or I don’t know…”

I was curious as hell now. “What the fuck is it?”

“Listen, swear you won’t say anything.”

“Who in the hell would I tell, I can’t stand anyone else here but you.”

“Seriously, don’t be an asshole.”

I laughed “Ok, seriously.”

“Ok, I think he’s bisexual….or at the least really, really curious.”

I didn’t say anything and tilted my head to the side.

“Like I found bi-porn on his computer last month, and we started talking about it.”

“Like two guys fucking, bi-porn?”

“Yeah, some of it was with a girl but some of it was just two guys fucking.”

“Ok, so he’s a freak, nothing wrong with that.”

“Yeah but we’ve been talking.”

“And”

“And “she breathed deeply and looked over her shoulder to make sure no one was listening “I want to watch him suck another guy…..you know, to see if he likes it.”

I laughed out loud.

“And what if he does.”

She shrugged “Ok, I guess I find the whole idea of it really really …I mean really fucking hot.”

“You want to watch your boy suck his first cock….your little slut.”

She blushed.

“Well here’s the thing….I know…well that…you are….”

“I am what?” I pretended to look hurt.

“Oh my god,” she started to panic. “You’re not…are you?”

“Am I bi?”

“yes” she said meekly

“Relax, I am.” I looked at her quizzically “How did you know, I don’t usually announce it.”

She grinned “Your friend Dani came in to the bar from NYC last month that one night you called off sick with the flu. A couple drinks and she told me just how much you like when she wears her strap-on for you….so I assumed.”

“Well, I will have to thank her for that.”

“No, it’s cool. Do you want to come over tonight?”

“You really think he’s down for it?”

“Totally, he’s been talking about it nonstop and I told him that it had to be a guy I chose.”

“And you picked me.”

“Why not, you’re fun, and I know it doesn’t mean anything to you….and well, you know, if it goes any farther tonight, I assumed you’d be down too.”

“If it goes farther? With just him, or you too.”

She turned bright red in her cheeks. “Well, why shouldn’t I have some fun too.”

I thought about it for a moment …..”What time should I bet there?”


Fast forward to six thirty that night.


Well her boyfriend was doing alright for himself. I think his name was Michael. Sammi and Michael…what kind of Asian names were these I mused to myself; anyway he lived in a very upscale townhouse on the outskirts of town. I was on my motorcycle and pulled up in his driveway next to Sammi’s little red Audi.

She was there; at least she didn’t chicken out. Something told me from the look she had in her eyes today that she was more than willing.

I had two six packs of beer tucked in my backpack and pushed my sunglasses up on my head when I rang the doorbell. By the time she answered I was already drinking one.

She was obvious that she was excited as she was almost bouncing up and down when she opened the door.”

“Jake, I’m so glad you came.”

I noticed immediately that she had already had a few drinks to loosen up and I figured that Michael probably needed them just as much as her.

We walked upstairs into the living room where I met him.

He was your typical Asian guy, not too tall and jet black hair. He had a pretty good build but was still a lot smaller than my 6’1” frame.

We shook hands and I offered him a beer.

“Don’t like beer, “he said almost apologetically. He was drinking spiced rum and cokes.

I drained mine and opened another, tossing my riding jacket in the hallway and finding a spot on the couch.

They had the blinds closed and it reminded me of freshmen year of college. Doing bad things in the dark in the dorms so no one would see you. I also noticed a few lines chopped out on the coffee table.

“You mind? I asked.

“Go ahead, bro.” Michael, the very pleasant host.

I bent down and used the rolled hundred dollar bill that was laying there to take a fatty line off the mirror. Who uses a hundred dollar bill unless you’re trying to make a statement.

I felt it hit and the warm fuzzy feeling creep up my spine.

Sammi hit one next and sat on the floor near my feet when she was finished, a glassy look in her eyes.

She was still wearing the see through blouse and black bra, and I could see down the back of her tight jeans and it didn’t look like she was wearing any panties.

I drained my beer to get that chalky taste out of my throat and had a nice numb feeling going on.

“So, Jake, I take it that you are….experienced?” Michael wasn’t sure how to speak to me.

“Relax brother.” I assured him, “It’s not the first time that I’ve had my cock in another guy’s mouth.”

Sammi giggled and Michael blushed.

“Come sit over here with us, Michael.” She patted the carpet next to her at my feet.

He poured himself another drink and moved to her side.

“How do we? You know, how do we start?”

I smiled wide “How does Sammi start sucking your cock usually?”

I was making a point to use the work cock; I wanted him to know that I was entirely comfortable. I figured it was the only way he was going to get into it.

“Well she usually starts rubbing me through my pants.”

I nodded to him and leaned back into the couch.

Sammi took his hand and slowly made their way up my inner thigh toward my crotch. She was watching him and taking quick glances at me. She was absolutely ready for wat was going to come.

As his fingers brushed my soft dick she leaned over and kissed him hard. I admired her ass as she did so and my cock was not that soft anymore.

He was tentative at first, just rubbing.

She was urging and supportive. And slowly began unbuttoning her blouse so that we could both see.

“It’s ok Michael; I want to see him in your mouth.”

I leaned forward and took off my t-shirt over my head, tossing it somewhere behind the couch.

She slowly undid his shirt buttons so that he was bare chested. He was hiding a six pack of abs under the shirt – not too shabby.

He was becoming more aggressive now, squeezing my dick and feeling it get harder in his fingers.

I was watching her response more than his, she was breathing hard, flush. That little freak. And she was making my cock ache now.

I leaned my head back and let out a soft moan as I reached down and loosened my belt.

Sammi was right there with me, she slowly loosened his belt as he got to his knees, his eyes never leaving my bulge. I heard her unzip his jeans and when I looked down her petite hand was gripped his hard dripping cock. He let out a moan and I thought for sure that he was going to cum right there on the carpet in her hand.

He fumbled with my pants and finally I reached down and slid them off, leaving only my boxer briefs on with the hard outline of my cock in plain view.
He was shaking as he hooked his fingers in my waistband and began easing them down.

“Michael, I am so turned on right now.” Sammi exclaimed as she loosened her bra. Her tiny little tits were topped with two rock hard nipples. “I can’t wait to see you suck his big white cock.”

He was crawling up my lap slowly, moving his face closer. My boxers moving downward, the head of my cock just now visible; a little more, and as his mouth neared I sprang loose, standing upward, fully erect.

“I’m not sure what to do.” He stammered as he was face with the erection.

Before I could instruct Sammi offered her assistant “Here, just like this.”

She slithered into my lap next to him and put her mouth over the head of my cock, swirling her tongue over the mushroomed head. I clenched my ass, trying not to blast a load of cum into her sweet mouth. She worked up and down my shaft slowly until my dick was shining with her saliva. Then she gripped the base and pulled away, pushed my throbbing member against his lips.

“Just let it slide between your lips.” she coached.

I just laid back and watched, still throbbing uncontrollably in her hand from the perfect suck job she just demonstrated.

Slowly he opened his mouth and let the tip of my cock slide past his lips. Not too bad, I felt a shiver in my spine.

“Work the tongue over the tip.” I urged.

He was just using his mouth as Sammi held my cock upright for him but in a few second I felt his tongue flicking over the head. I looked at Sammi and smiled wide. “He’s pretty good.” I was breathing hard now myself.

She left go of my cock and leaned back against the coffee table, kicking off her jeans. His hand replaced hers on the base of my cock and he attempted to put more of my shaft in his mouth. I let out a soft moan and felt myself quivering in his mouth.

“Go ahead; take as much as you can.” I put my fingers gently on his head. He never looked up at my but never stopped working my in and out of his mouth.

Sami was naked now, legs spread wide and she was rubbing her perfectly shaven pussy as she watched the scene unfolding before her. That in turn made my cock throb that much harder in his mouth.

“Enjoying yourself, Sammi?”
“mmmmhummm” was her response as she diddled her dripping pussy.

He was picking up the speed now, and I could tell he was getting into it. Slowly his lips neared the base of my cock with each slurp. Saliva dripping from the corners of his mouth, yet he never came up for air.

I rolled my head back on the couch and let out a louder moan, feeling the pressure starting to build in my balls.

Sammi was moaning louder, and the dark living room was filled with the sounds of sucking and moaning and pleasure.

I felt myself starting to tense.

“Should I give him my load, Sammi?”

“Fuck yes.” She almost screamed.

I gripped the back of his head as I felt myself explode into his eager mouth. He tried to pull away at first and I heard him gag, but then he swallowed, more and more, taking every drop. Never pulling up until I was soft in his mouth.

“Fuck man, that was awesome.” I felt like high fiving him.

Sami was not ready to stop.

“Jake, now suck him.”

I looked down at her as she snorted another fat line and laid down on the carpet, watching us and furiously rubbing her pussy.

I looked at Michael and he was already standing in front of me. We had opened new doors for him and he was eager to continue.

“You owe me, Sammi.” I teased.

Michael didn’t last long. I slipped his hard cock past my lips and started working the shaft and his balls at the same time. I never minded sucking a nice dick and his was probably a little on the small size.

It must have been like his first time with a girl because in a matter of thirty second I felt the warm sticky cum filling my mouth. I swallowed it down and as I felt it hit the back of my throat I slipped a finger against his tight ass. He yelped and blasted me with a second shot of cum.

I lay back panting and he was kneeling on the floor now, trying to collect himself. I licked the last of his cum off my lips and looked down at Sammi who must have cum the same time as her boyfriend.

She was smiling wide as I leaned down and bumped another line of blow.

“He didn’t last too long.”

Michael blushed.

“He recovers quick” Sami smiled wickedly as she quickly got to her knees and started fondling her semi-soft cock.

“A good trait.”

“Are you willing to let him try more?”

I looked at Michael and his cock, once again getting stiff in Sammi’s hand.

“He does fucking get hard quick, doesn’t he.”

“Lay back on the couch, Jake.”

Sami was in control now, and I was letting it happen.

I laid back flat on the couch as she led him over to me. My legs spread I felt her fingers teasing my ass.

“Are you sure? Michael asked

“God I want to see you fuck his ass.” She replied in breathless tones.

“Damn Sammi, you are really a freak.”

“ I am so fucking turned on right now.” She responded.

I leaned my head back and felt his head press against my ass. He was still slick from the blowjob and much smaller than I had had before.

I felt my cock start to harden as he started to nudge himself into my ass. Then I felt Sammi’s lips around the head of my cock, urging me back to a solid state.

I was their plaything and I was ok with it.

He started to pick up the pace, driving his hard cock into me with more force. She teased my balls and jerked my cock into her mouth; the whole time urging him to fuck me harder.

I gripped the sides of the couch and let him pound away. I would have stopped him if we’d have been alone but her sweet lips made it fucking amazing.

He had my hips now, pulling me into his dick harder. He was giving it his all.

I was quivering in her mouth, ready to gush once more.

“Fuck my ass, Michael.” I moaned as I started to spurt into her mouth.

I felt her mouth filling with my sticky mess. And then I felt him slip from my ass and then his own mess exploded on her face as she drained me.

I lay back panting as she came up to kiss me. And she did, deeply with a hot mouthful of my own cum. A special thank you for the playtime.
 
Daylight turned a few of the bartenders I worked with into the creature from the black lagoon. Too much real light and too much make-up at night led to one rough looking slut. This only usually became apparent when I had to go to training during the day.

A bunch of hungover bartender and waitress sitting around learning about responsible alcohol management with their faces hidden behind dark sunglasses or huge cups of coffee.

This particular morning I found my usual spot in the back of the training room opposite the exit. That way I could see everyone coming in and not have to worry about some dipshit behind on next to me trying to talk to me throughout.

The worst were the daytime bartenders who got five or six customers a day and who thought that they were Tom Cruise in Cocktail. Just shut the fuck up.

I was on my second gallon of coffee for 9AM and was assessing the girls as they came into the room, and to be honest, some of the guys too, what the hell, I was usually horny as fuck when I was hungover, and let's just say that I was really, really hungover this morning.

It was a pretty rough looking crowd, myself probably included in that category.

More coffee please.

And then I caught a glimps of some super ass-hugging Adidas workout pants walking in the door. Not a familiar face, must have been from another bar that the owner managed. She was a little rough, probably gorgeous as hell when she was 18 or 20, but now, pushing 40 was my guess, she would give any of the younger girls a run for their money at night when the barlights got dim.

She eyed up the seats and found the one next to me in the back row empty. I nodded and sipped my coffee as she plopped into the seat next to me, tossing her oversized purse onto the floor and sipping at her own cup of coffee.

Now that she was a little closer, I was definately right about the closing in on 40 estimate. She had a slightly angular face, harsh, yet something fucking hot there. But she had this crazy thick mop of long curly dirty blonde hair that she had pulled back into a loose pony tail with one of those big scrunchies.

My immediate thought was fucking her from behind with that ponytail in my hand. Hey, like I said, I was crazy hungover.

But damn if she wasn't wearing an oversized t-shirt for some metal band. I checked her out as she leaned back to dig in her purse. Couldn't tell about the stomache but her tits were something special. They were round and full - hell probably a push-up bra but again, who really gave a fuck.

She looked over at me. "I just got off at 4AM, didn't sleep and now this fucking shit."

I nodded and toasted her with my coffee cup. "Right on, same here. Came right from the bar myself."

She smiled and that showed the age a bit - still hot, but deep lines around the mouth. I wondered if I would notice them if my cock was in her mouth.

I was still trying to figure out the situation of her body when the training started. Had to put a pin in that thought as the training almost put me to sleep.

Mid morning break found us standing in line to the coffee station together. Her name was Andrea, she was 41 with a grandaughter. I got that much from her before I even filled up my cup. She was working at the local roadhouse which was pretty much a meatmarket for the 40 year old plus faction out to prove that their pricks and 30 year old pick up lines still worked.

I was also pretty sure she wasn't wearing any panties from the distinct lack of lines in those tight workout pants.
 
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