Stories : Alexander The Great

I’ll remember that spring day 5 years ago for the rest of my life.  My boss, our company’s CEO, called a meeting for the management team at 4pm that Friday afternoon…and here’s how it all went down.

We all suspected something was up because of the number of closed door meetings, so we were all hopeful that we’d find out what was going on.  I have worked at this company for ten years (ever since graduating college) and had just recently been promoted into the management ranks.  I knew that our CEO didn’t really owe anything to me at that point to let me in on what was going on, but damn, I was really curious. There’d been a bunch of new faces around the office, most of whom had been wearing suits and ties or sports jackets which is definitely not the norm around our mostly blue collar manufacturing company.  So 4pm came and we all assembled around the board table – present were our CEO Walt, David our Operations Manager, Steve in Quality, Laura in HR, Carl in Finance, and me, Avi, our Sales Manager.  And joining us were two of the new faces I’ve seen around the office the last month or so plus one new one.

First a little more about me…I’m a 30 year old married guy, and, admittedly, I have had some experiences with guys before.  You know, the high school curiosity kinda things…college frat brother when drunk, etc.  I definitely never considered myself gay, but even to this day I can appreciate a good looking dude.  And it has been close to ten years since I’ve been intimate with anyone besides my wife, let alone with another guy.  I still think that I’m a pretty good looking guy – about 6’1”, dark Mediterranean complexion, curly brown hair and a masculine appearance.  I’m the kind of guy that can grow a beard in one day and have that perfect 5 o’clock shadow by noon.  Between work and family life, working out is one of the few things I still have for myself, but I don’t do it as much as I want to.  I no longer have the six pack abs, but you can tell I was athletic in my past.

Walt, our CEO, kicked off the meeting.  It was a long speech; he was clearly nervous, but surprisingly excited at the same time.  After beating around the bush for a few minutes with talking about where we’ve come from as a management team, he finally revealed what has been going on…we’ve been sold.  The three gentlemen around the table were the investors who just bought our company.  There was Paul, the most senior guy, about 50, 6’3, slim and very distinguished looking.  You can tell he was the leader, though he was clearly distracted as he kept looking at his blackberry. John, who must have been the number two guy, introduced himself next.  Just like Paul, he was a double-ivy (undergrad and MBA), a bit younger, maybe late 30s.  It was clear he would be the one spending the most time with our company.  He and Paul took turns and talked about our future potential, operational plans, sales plans, and on for about 15 minutes.  To be honest, I heard every third word they said as I couldn’t keep my eyes and attention off their 3^rd team member – Alexander. Wow!

Alexander was as close to a Greek god I’ve ever seen.  And I’ve been to the beaches of Mykonos and Santorini, and while those guys were damn good looking, Alexander had them all beat.  And yes, it was Alexander, not Alex – which befit his godlike appearance.  He was about 25, tall, about 6’3”, had perfect medium-dark olive complexion like he’s been laying out in the sun for just the right amount of time.  Not a hair was out of place on his head, and his beautiful green eyes with crazy long eyelashes drew you in so you couldn’t look away.  Alexander was dressed to the nines from his Gucci loafers to his custom shirts monogrammed on the sleeves.  Unlike Paul and John, Alexander forewent the undershirt and so you could see the top of his chest hair peeking out from under his square jaw.

The meeting ended quickly after John spoke – they gave Alexander about 2 minutes to give his brief introduction – 3 years on Wall Street, just started with the investment firm a few months ago, really looking forward to getting to know us and working with us.  From then on, we should expect to talk to them every week and see them at quarterly board meetings and likely more frequently than that (I hoped!)

And so it began.  As I had suspected, Paul would show up for board meetings and that was about it.  He was clearly much too busy chasing all of their new deals to get into the detail of our business.  John definitely was the most present of the three, which was really fine by me because he was strictly financial driven.  His meetings were mostly with Walt and Carl, and I know he drove Carl up a wall asking for every kind of financial report possible.  The good thing for me was that he would try and bring Alexander with him whenever he came out to give the kid some hands-on training.  Of course, I was dreaming of giving Alexander a different kind of hands-on training.  As it turned out, I would have to bide my time.

Alexander and I hit it off great from the start.  I was the only management member within twenty years of his age, so he and I would spend more time together than he would probably have spent with most sales managers.  When he came in town, he and I would outlast everyone else at the happy hours and became fast buds.  Alexander had a cocky demeanor, like that of the frat president of the coolest fraternity on campus.  But at the same time he was great at making you feel like his best friend.  He had an infectious smile and laughed all the time.

The problem was I was not getting any attraction vibes from him that gave me any courage to be more aggressive with my coming ons.  Every now and then after a few beers, I’d put my arm around him like a “bro” to see what he would do, and I even tried changing into a tight t-shrit one night before going out to see if he would stare me up.  Nothing.

This went on for two years – I pretty much gave up on anything ever happening, but at least I felt like I got a good friend out of it.  Now don’t get me wrong – I still went home and jerked it every time after seeing him.  There were times when I couldn’t take it any more and went to the bathroom where ever we were and did it there.  Yes- he was that hot!

It definitely took me by surprise about 2.5 years later when I found out Alexander was leaving the investment firm to go back and get his MBA.  I knew that our next board meeting in New York (at their offices) would be the last time I saw him in a while.  This trip started out like all the rest – we had our board meeting from noon until about four in the afternoon and then all departed for the hotel before dinner.  About 5:30 we all met down at the hotel bar for happy hour.  Of course, Alexander and I were the first ones there and got started with our drinks quickly.  He ordered a margarita and I gave him crap for drinking like a fairy and he laughed it off and told me I wished he was a fairy.  Whoah! It took me aback and I didn’t know how the hell to respond to that, so I didn’t.  And thankfully others started coming down to the bar so I didn’t have to.  He didn’t push me on it and just let that comment go away.  Between drinks and then wine at dinner, we were all feeling sufficiently buzzed.  What really topped it off was that some of us went back to the hotel bar for post-dinner drinks to celebrate our great quarter.  What started with one or two more with the rest of the team, turned into a two hour good-bye session to Alexander that ended with just the two of us – like always!

Now this is where the story starts to deviate from our prior board meeting nights out.  We usually don’t do the board meetings in New York so I’m usually the one heading home and Alexander heads to the hotel.  Alexander was all worried about missing breakfast in the morning since his apartment was 45 minutes to an hour away by subway, so he asked if he could crash in my room. Ummm, fuck yeah!  Unfortunately, I had a two queen bed room so we wouldn’t be forced to share a bed.  But what the fuck, I would definitely get to see this Adonis way more in the flesh than I ever had before (other than in my mind while jerking off).

I got in the room, stripped down to my boxers and undershirt and announced I was going to jump in the shower.  Alexander had just propped himself on the bed in his full clothing and was clearly a bit tipsy from all the drinking we had been doing.  One of the benefits to traveling for this company, is they put us up in nice hotels – you know the ones with fancy bath products and really plush robes.  So when I was done with my shower, I put my boxers back on and slipped on one of the robes before heading out to the sleeping area.  When I got out there, Alexander was still on the bed in his clothes, but his hand was down his pants and he was clearly rubbing his dick.

“You finally get what you want you bastard,” Alexander barked at me.  “I told you earlier I knew you were hoping I was a fairy.”

“What the fuck is wrong with you, bud? Go the fuck to sleep, we need to be up early,” I replied hastily, realizing mid sentence that maybe I should be more open to his fucking around.

“I know you’ve been trying to get in these pants since you first saw me.  Don’t worry, most people are – dudes, bitches…it doesn’t matter.  I know when I have someone hooked, bro,” he said in quite the cocky tone.  Problem was, he was dead on and I was at a loss for words.  “I’m gonna get my rocks off tonight, Avi.  It’s either gonna be watching SportsCenter or in your mouth.  You pick!”

“Where the fuck was all this the last two years?  If you knew, I wouldn’t have had to go home and jerk it,” was the best I could come back with.

“Dude stop being a bitch.  You know you want this!” Alexander then proceeded to unzip his fly and let a 4” flaccid dick plop out.  I have a big dick – 7.5” and pretty thick when hard, but, goddamn, I had never seen a soft dick this big.  Holy fuck, the thing was everything I had imagined and more.   It was perfectly shaped with a nice cut head and you can just make out the dark brown trimmed pubes that were still trapped under his pants.  I was definitely frozen with no idea what to do next.

“I told you to stop being a bitch.  Don’t act like you’ve never seen one before.  I know your wife doesn’t have one of these, but I know you know what to do with it.”  He then started jerking it off nice and slowly.  “I told you, I’m going to get off tonight with or without you.  I think I know which way you want it.”

“I don’t know yet.  Let me see the whole thing,” I came back with trying to mimic his cocky tone.  I then dropped my boxers and robe so I was standing there totally buck naked.  My 7.5” dick was at full attention – definitely no hiding that.

“Not bad Avi…I pictured you having a smaller dick.”

“Fuck you!” I yelled at him as I jumped in bed next to the object of all my desires the last two years.  I grabbed his dick like it was something I did on a regular basis and started stroking it.  The thing grew to the perfect fuck stick – about an inch longer than mine and the girth of a nice sized cucumber.

“Taste it!”  That was all I needed to hear to drop my head down in his lap and take his 8.5” dick in my mouth.  I unbuckled his belt and undid his button to let the whole dick out and give me better access.  Alexander pulled his pants and boxers all the way down which gave me the perfect view of his toned thighs and legs.  He had the build of every sexy soccer player, albeit a bit taller.  Nice lean muscles that he definitely spends time sculpting in the gym.  As I gagged a bit on his cock I reached my hands up his dress shirt to feel his abs and chest.  Quickly I unbuttoned his shirt which he took off completely so we were both in his bed, totally naked.

“Gag on it, bud.  I like it when I know you have to struggle, ha!” he laughed while ordering me to deep throat his big dick.  As if I needed motivation, I went all the way down on it while grabbing up for his nipples and giving them a squeeze.  “Easy there…don’t want to hurt me or you’ll really get it.”  Kinda curious what that meant, I squeezed even harder and Alexander laughed.  “Damn boy, you’re not shy.”

I couldn’t much get any words out while choking on his dick, but I managed to gurgle out, “fuck my mouth!”  I guess that’s all he needed to hear to start thrusting down my throat.  I loved every second of it. I could taste his pre-cum as he kept treating me like a little freshman frat kid that had to worship god Alexander.  “Take it all Avi!” “Suck it bitch!”  I really didn’t give a fuck what he was saying, this was living up to every fantasy I had of him.  I started to rub my own dick since he hadn’t been paying any attention to my needs.  As soon as he saw me do this, he told me I better not cum before he does.  I took my hands off my dick and kept sucking as he was thrusting into my face.

“Lay on your back, buddy!” he said sort of nicely to me this time.  I let out his cock and flipped over to be on my back.  Alexander then squatted over my face and angled his big dick down my throat.  This must be all he needed because a few pumps later he was cumming down my face.  I started to gag and spit his dick out, but he would have none of it.

“Don’t even think about letting go, Avi.  Take all that cum and like it.”  I had never swallowed before so this was a new sensation.  I don’t know that I liked it, but for Alexander, everything was that much hotter.  When he was done cumming, he finally pulled his dick out of my mouth and laid down next to me, grabbing my throbbing cock in his hand for the first time.

He gave a few squeezes and then told me, “I’m gonna jump in the shower.  You really messed me up.  If I come out and you have touched your dick once, you’re in fucking trouble!”

With that command, I laid there trying to process what just happened.  The hottest guy I’ve ever seen just worked my mouth like a little bitch’s.  I was curious what he had in store for me so I just laid there with my hands under my ass so I could refuse every urge I had to satisfy myself.

Alexander came out of the shower dripping wet with his hair out of place for the first time I’ve ever seen.  “Damn boy, you could really suck a nice dick.  I knew you would be a good friend.”  He then jumped back in bed and laid down next to me, back to his happy, cocky attitude.  The whole domineering side seemed to disappear down the drain of his shower.  As we both laid there naked, he leaned over and started making out with me.  It was sensual and passionate.  Our tongues found each others’ and we just laid there, making out for about 15 minutes, not saying a word.  He held me in his arms and explored my body as I did to him.  My mind was racing with every fantasy I had of Alexander for the past 15 years.

After 15 minutes, Alexander got to my ass and started to caress it while his tongue was still deep in my mouth.  Caressing quickly turned to something more as he broke off our kiss to lick his fingers.  I could tell at this point that he was starting to build his hard-on back up, not that I minded feeling his large limp, recently worked-out cock between my fingers.  After he licked his fingers, he went right back to my ass where he slipped one finger into my hole.

Since messing around with my friends in high school and college, I’ve always been keen to my ass being played with.  Unfortunately, I’ve never built up the courage to share this with my wife, so I haven’t had anyone fondle me in over ten years.  That doesn’t mean I wasn’t ready – I still love to jerk off while sticking things up my ass.

I think Alexander got the message quickly that I was liking what he was doing because I was squiring in pleasure around his finger.  He quickly upped it to two and then three digits up my ass, thrusting as we continued to make out.

“Get on your stomach, Avi!” he commanded again, though this time much more gently and not with nearly as much “I’m the boss” macho attitude as before.  As soon as I lay down on my stomach, Alexander straddled my legs and brought me up to all fours.  With barely a second passing, he lunged at my ass and started eating me out.  Now this was a first for me – I’ve never had my ass eaten, but holy fuck! The feeling was amazing.  It took every ounce of willpower not to cum right then, knowing that Alexander was back there eating my ass.  I kept looking through my legs to see him on his knees, straddled over my calves with his hard dick hanging down and his beautiful chest pressed against the back of my thighs.

Alexander took a break, spit on his hands, and rubbed his dick.  All of a sudden he stood up and I could feel that he was about to try and fuck me.  Slowly, I felt the head of his wet dick push against my tight hole.  He leaned over so that his chest was laying on my back and he grabbed hold of my hair.

“You want this boy? I know you do!” he whispered gently in my ear.

“I want it all Alexander! Fuck me, man. Fuck me!” I replied pretty unsure of what I was saying.  I was really ready for him to be inside me, feeling every inch of him glide through my ass like I’ve dreamed of any time I’ve played with my ass over the last couple years.  But I was also a bit freaked by being fucked by his big cock since I’ve never had anything that size in me before.

Alexander grabbed hold of my hair and slowly guided his dick into my ass, one big fat inch at a time.  I was shocked into silence, likely screaming into the pillow I had lowered my face into, grabbing both ends of it with all my might to keep from waking the whole hotel up with my screams.  He grabbed my hair a bit tighter and very slowly slid each inch in my ass until he was balls deep.

“Hang on, bud!” he laughed, with that familiar cocky tone of voice like he owned me.  Funny thing was, at this point of time, he did.  He started to fuck me a bit faster, pumping his muscular legs against mine with every thrust.  I was answering by thrusting my ass against his dick, smacking his groin with every move.  It was hot, sweaty, and by now was feeling so good – the sharp pain of the initial fuck long gone.

I knew I wasn’t going to last long, so I spoke up, “dude I’m going to cum soon.”

“Sweet, bud, let it go.  I wanna see it fly out!”  Sooner he said those words, that with one last thrust, I started to cum everywhere.  As soon as I did, my ass clenched, but Alexander wouldn’t stop pounding me.

“Fuck yea, man! I’m gonna cum to.”  As soon as I was going to tell him to cum on my chest instead of in my ass, I was too late.  I felt his hot load fill my ass.  At that moment, it was the most intense pleasure I have ever felt in my life.  Alexander turned me back over, laid his cum-filled dick on mine and started making out again.  I held him close and we just laid in each other’s arms for the rest of the night.  It must’ve only been a few minutes before both of us were asleep for good.

The alarm went off early the next morning to give us time to get ready for breakfast.  Alexander got up, quickly put on his clothes and told me he was taking off.

“Be well, dude! Let’s keep in touch.  I’m going to be at school in Chicago, so if you’re ever nearby, you better fucking hit me up.”

“What about breakfast,” I questioned.

“Ha, dude! I was never going to breakfast.”  And with that, he took off, leaving me to know that he had the whole night planned.  That fucker!