Security by Greg

Working nights on a sixth month software project in a boring assed city on the west coast was not my idea of fun.  That I worked nights at a smallish office building doing trouble shooting and support for said software project did not help either since I was awake when almost no one else was unless you counted the team oversees.  Since most of the offices who may have needed my help were closed while I was in the office, I didn’t have a lot to do and man was I bored.  I had already mastered the intricacies of the World of Warcraft.  Honestly though, I can only play so many video games and read so many books while waiting for a call before going a bit nuts.  So I spent most of my time fantasizing about one of the security guards in the building.  Greg.  

Yes, I fully admit had a major crush on Greg.  There was just something about him that really got me going, all he had to do was poke his head into my office and my dick stated panting for attention. He was probably in his mid thirties a couple inches taller than my own six feet but with a solid ex-football player.   Just my type since I personally resembled a beanpole.  His face was all angles and he always looked like he needed a good shave.  But it was his lopsided smile and dimples that got to me.  The things I dreamt of doing to that man with my tongue.  

Alas, it was not to be though as he had a live in girlfriend he seemed pretty happy with.  It didn’t mean I couldn’t dream though?  It also didn’t hurt that Greg was well aware of just how attractive I found him and would occasionally comment on it with that toothsome grin.  Greg really was an incorrigible flirt and would even go so far as to innocently brush up against me once in a while or ask if his uniform pants made his ass look fat.  As if, his ass was amazing even in the ugly uniform pants he had to wear.  All of this of course just made me want him all the more.  

He was also just as bored as I was for the most part so we would hang out in my office and chat during our slow times.  Hell, he was in there for almost half his shift most nights as most of the time neither of us had much to do.  I had a small beat up couch in my office for him to lounge on.  Bold as fuck, he would stretch back and spread his legs while we talked while pretending to be all innocent when my eyes wandered as he adjusted himself.   Laughing, he would tell me eyes up and said with a wink he would consider taking me up on the offer if he was ever single.  This continued on a for  a few months in good clean suggestive fun.

Then one Monday, he seemed a bit off.  At first he was quiet and somewhat reserved around me but he insisted everything was okay.  Normally, he would spend at least an hour or two chatting with me but nothing.  By Wednesday, he was back to normal though, well, almost normal.  The flirting went had gone up a notch, a big notch.  He even leaned over my shoulder, pushing his crotch into my shoulder, one night as he leaned over to look at a game I was playing.  I so wanted to lean back into him but stopped myself but found myself wondering what exactly had happened.  Because I knew something had happened, since it was so odd.  Casual flirting was one thing but this was way, way over that line.  

He came in that Friday night and did his usual flop down on to the little couch to kick back.  Except this time, did more than just spread his legs a little too far.  Greg was actually gently rubbing himself through his ugly uniform pants.  My pulse kicked into high gear and I could not get off the phone fast enough.  I didn’t want to get my hopes up but my dick had other ideas and was already half hard.  

Finally, hanging up I asked.  “What’s up Greg?  Though it came out as more of a croak than a definitive question.  I was having trouble though keeping my eyes on his face and not staring at him massaging his junk. 

“What’s up?”  He echoed back and gave me his little lopsided smirk as he continued.  “I am.  And I was hoping you could help a buddy out.  It’s not like you aren’t attracted to me.  I’ve been so fucking horny and I could use a helping hand or…”  And he let his words sort of drift off.  I was more than a little shocked, the arrogant fucker was lounging back on my office couch and asking me for a blow job.  As much as I would have loved to give him a quick blow and go, I had a few rules I stuck too.   

“Even as hot as I find you, I don’t help guys cheat on their girlfriend.  Or boyfriend.  Ever.”  I shot back.  That elicited a growl.

“Cindy and I broke up, so I am completely and totally one hundred percent single.”  Greg answered tersely with a scowl that quickly changed to a smile.  “So come on.. you know you want me?” were his next words as gave his crotch a squeeze.  

My mind fought an inner battle over fucking things up at the office and finally living my fantasy of getting my hands on this man.  I was weakening though as I saw the outline of a growing hardness showing through his pants.  There was no question about my own dick, it was already rock hard.  After crushing on him for the entire time I’d been on the project my cock got rock hard the second he started rubbing himself through his pants.  Fuck it, I thought to myself.  I was going to have him, even if it was only once.  

I licked my lips and as I started to stand, he gave a triumphant grin.  He knew he had me and started to unbutton his guard shirt revealing the white tee underneath.  Quickly, I got up and moved to lock the door to my office.  I had never done anything like this before and was nervous something would upset this opportunity to actually touch him.  Greg peeled of his tee and he was just the solid type of guy I find so attractive, just a little muscled and rough around the edges.  His chest was mostly smooth with two nice nipples and a line of hair heading south.

I kneeled to help him off with his pants.  Forgetting to take his shoes off in my eagerness, I almost knocked him over.  Finally I had him leaning back on the couch in his black boxer briefs with a nice tent for me to look at.  I ran my hands up and down his thighs and started to lean forward when he stopped me.  

“Aren’t you going to be naked too?”  He asked and my jaw must have hit the ground.  He continued almost sheepishly “It’s just a little weird with only me being naked.”  Not giving him a chance to rethink his comment, I was naked and  back on my knees in front of him in under ten seconds.  Well, almost naked as I still had my socks on.    

Back on my knees I massaged his thighs and leaned in to finally taste him.  I gave little licks and kisses from one of his knees towards his cock, stopping just before I got to his now very hard cock tenting his boxer briefs.  His little moans told me he was having fun.  Looking up his eyes were closed and his hands were clenched at his side. 

I pressed my face into his briefs and inhaled his scent.  It was amazing, musk and man with a hint of some fabric softener leftover from laundry day.  Slowly, I sucked on him through the fabric as my hands massages his thighs, darting in to rub closer and closer to his balls.  Then I snuck one of my hands in and gently rolled his balls with a couple of my fingers.  As I played with his cock with my mouth and balls with another I took my other hand and stroked my way up to one of his nipples.  Giving it a gentle rub to see if he would like it.  He did.  It was time though to see the main course.  

I leaned back on my knees and pulled his briefs off.  His rock hard cock popped into view and it was a beauty.  A solid seven inches with a nice head and just the right amount of hair surrounding his balls.  Wrapping my hand around it, I jacked him ever so slowly and softly.  Greg moaned, trying to hump my hand to go faster but I would have none of that.  I leaned forward and gave the head of his cock a kiss followed by a quick lick. 

“Jesus, please suck me already.” he ground out.  I chuckled and took the head of his cock into my mouth, it was just the right fit as I swirled my tongue around it and worked it into the tip to test the sweetness of his pre-cum.  The sticky liquid tasted as good as it looked and I took a little more of his dick into my mouth with gentle suction.  Bucking up I almost gagged as he tried to get his entire dick into my mouth at once.  

“Bad Greg” I said pulling back. “I’m going to take my time so we both really enjoy this.”  As I gently stroked him.  “Okay?”  He nodded sheepishly.  I lowered my mouth back to his dick and started sucking again.  Working more of his cock into my mouth, I took him all the way down and held him there for a few seconds before coming back up.  He was moaning like a dog in heat as I continued to deep throat him for a minute or two as I played with his balls but I pulled off as I felt his balls start to pull up. Way too soon and I was not done with him.  Not even close. 

“Oh come on.. I was so close.” Greg said, it almost coming out like a soft whine from a teenager.  I just laughed at him and licked one of his balls.  That made him jump and mutter an ‘oh fuck’ so I sucked the entire ball into my mouth and gently suckled it. He started to move his hand to jack himself off but I would have none of that.  

“Nope, this is my show, no touching yourself.” I said as I grabbed his hand and pulled it way from his dick.  I kissed the palm of his hand and set it away from his cock.  Greg started to toy with his nipples as he watched me with his eyes half closed in pleasure.  Never breaking eye contact, I went back to licking and sucking his balls.  When my tongue touched his taint he closed his eyes and spread his legs slightly as he moaned in pleasure.  

Taking that as invitation, my tongue continued its trek southward.  I spread his legs a bit more and very slowly started to rim him.  First with long slow strokes up and down his crack before gently kissing and licking his hole.  It was like setting a match to gasoline.  

Greg bucked up and pushed his ass into my face as he spread his legs wider to give me better access.  Using my tongue I pressing into his hole, feeling it open under the gentle pressure, his moaning got louder as I worked my magic.  After a couple minutes, his hole was loosening up and slick with spit.  Man, this was giving me ideas.  While I would have loved to have Greg fuck me senseless, seeing him spread open with his beautiful hole wet with spit and winking hungrily was a revelation.   

I wanted, needed to be inside this man in the worst way, to fuck him, fill him.  My dick was so hard it was ready to burst at just the thought of it.  Sucking a finger into my mouth to get it wet, I slowly started to insert just the tip of my finger into his ass.  He was so focused on the pleasure in his hole, he didn’t seem to notice the change.  I pressed in farther, hitting a little resistance, and he gasped.  Leaning over, I sucked the head of his dick as I moved in a little more, stretching him out.  In and out, in and out.. man, I wanted him so badly.  

Looking up at him, I don’t think I had ever been so turned on in my life.  He mouth was open, his brow beaded with sweat and his fingers working his nipples.  Greg was gorgeous.  I had one hand gently massaging his dick and a finger getting deeper and deeper into his ass with each thrust.  With a deep breath, I quickly disengaged and stood, my rock hard dick bouncing.  

“What?” Greg ground out, almost pained in his expression.  I grabbed the hand lotion off my desk and was quickly on my knees in front of him again.  Popping the top on the bottle, I quickly worked some onto my fingers.  He looked a little nervous so I tried to reassure him.

“Don’t worry, I’m not going to do anything you don’t want.  Trust me.”  I said in my most trust worthy voice.  Closing his eyes, he nodded.   

Ever so slowly, I worked the lotion into his hole, stretching it as gently as I could.   I needed to get him ready for my dick.  I don’t care if he was straight or thought he was straight but this man wanted to get fucked, by me.   The slick heat and tightness from his ass was urging me on but I reigned in my lust to take it slowly.  I wanted his first time to be something he would never forget.  

I added some more lotion to keep his hole slick as I got him ready for a second finger.  Jacking his cock in time with my thrusts, I added another finger and felt him give the smallest wince as I breached his sphincter.  “Do you want me to stop?”  I asked as I ran my tongue up the side of his dick and licked the head a bit.  

Shaking his head in the negative was his only response.  I carefully watched his face as I got him used to the two fingers so see any discomfort there but only saw pleasure.  He was so hot and tight, like silk.  As I snuck in a third finger I angled up a bit and found his prostate.  “Holy fuck, do that again” Greg gasped.  I gave his joy button one more quick poke before pulling out.   

“Come on, roll over for me.”  I said, wanting this man on all fours to make it easier to fuck him.  Greg didn’t look to sure, so gave him my best smile and said “You trust me right?” and hoping beyond hope that he agreed.  Nodding he rolled over to where he was half on, half off  the couch with his ass presented to me.  And what an ass it was, meaty and thick and beautiful.  That little hole all wet and winking at me.  Wow, just wow.  I don’t think I’d ever seen anything hotter in all my life than him on his knees like that waiting for me to fuck him.  

I quickly slicked my dick with a bit more lotion.  I lined my cock up for entry and ran my hands up his back affectionately and rubbed his shoulders a bit as I rubbed my cock up up and down his crack.  Then I lined up the head of my cock and slipped the head inside.  The muscles in his shoulders tightened and he made a sound somewhere between a gasp and a moan.  It was all I could do not to ram into him in one long stroke but dear heaven it was difficult.  The hot moist heat surrounding my dick was sucking me into a spiral of lust.    

“You doing okay?” I asked gruffly as I kept just couple inches inside him.  I think I would have died if he changed his mind or said it was too much.  

“Oh yeah, I’m way past okay.”  he responded, and I pushed in deeper, loving how he was opening up for me.  It seemed to take hours but was probably no more than a couple of minutes but finally I was balls deep inside Greg, the man I had been crushing on for ages.  

Withdrawing just a bit I started to gently fuck him, occasionally taking aim at his prostate.  Each time my dick made contact he gasped in pleasure.  I picked up my pace a bit but still careful to keep my my strokes gentle.  I already felt my balls starting to tighten but I wanted this to last since as long as possible, it may have been my only chance with him.   

I ran my hands all over his back and shoulders, before reaching down to gently stroke his dick a bit.  “Don’t” he muttered, pushing my hand way from his dick.  “Too soon.”  The little devil in me reared his head and I pulled almost all the way out, just keeping the head of my dick inside him with the tiniest of thrusts.  That got a response.

“Fuck you dude, come on!”  Greg groaned at me, and pushing back against me.  I could have cum just at the thought of him trying to get my dick inside him.  With my hands on his hips I held him from pushing back though.  

“Fuck me?  You sure about that?” I replied with a smile.  He groaned back and spoke almost pleadingly, “Fuck me!  Please, fuck me.”  I thrust back in hard, all the way in with my balls slapping against his.  

“Yes” he moaned and so I started to long dick him, pulling almost all the way out before thrusting back in.  Again and again.  

“You like my dick Greg?  You want me to fuck you?  Tell me how much you want my dick.”  I said as I continued to slide in and out.  

“Harder, please.  Fuck me harder. Damn that feels good.” all fell from his lips as I pounded into him.  Already warm in the small office with the heat of our bodies and exertion, my skin grew slick.  Leaning down, I used my tongue to kiss and lick my way across his shoulders as he pushed back against me.  

God, I could have fucked this man for hours but I was already close to coming.  Leaning close, I whispered in his ear “You close, I’m about to cum.”  He nodded and reached down to start jacking himself.  

I wrapped myself around him and fucked for all I was worth.  With a near feral grunt, I came, filling his ass with my cum.  Just as I shot, I felt him groan and his ass tighten around my dick almost painfully as his own orgasm rocked him.  I laid my face against his back for just a second, wanting this moment to last.  The image of spooning this man after hot sex floated through my mind.  

I pulled out slowly then jumped up to grab some wipes to clean us up.  I was suddenly awkward in the silence.  I had no idea what to say, I had just fucked someone from work in my office.  Deep down though, I knew it was worth it even if somehow the higher ups found out.  I just wished for well, more of the same.

He stood up and once again, his naked closeness made my softening dick twitch.  As handsome as he was fully clothed, he was a hundred times hotter without his clothes.  Handing him some wipes, we cleaned ourselves up.  Not sure how to act I smiled sheepishly and quietly said I had fun and hoped he did too.  “Hell yes, I had fun.  In fact I have a favor to ask.” Greg said with his trademark smirk.

I couldn’t get a word out I was so sort of gave him the “And” face that is universal guy speak.  

“Well, when Cindy and I broke up, she kind of kicked me out and I was wondering if I could bunk with you…” was all he got out as I grabbed him and pulled him close, my hands wandering over his back and shoulders.  Greg’s hands held me tight as well and his hands slid down to my ass, pulling me closer.  Then my mouth met his for a kiss and it was electric.  His mouth opened, my tongue explored his mouth and his mine.  Wow, could he kiss.  After a moment, he broke off the kiss and spoke.

“I take it that’s a yes?”