The Backroom and the Boss

It had been more than a week after confessing to wanting to watch me get fucked, and I was working on that happening. Everything at the office was running as usual and he didn’t speak of what happened at the book store except once to to quietly inquire about his request.

As I didn’t really have a regular playmate I wasn’t a hundred percent sure how to make it happen. With my uncertainty as to whether he wanted to just watch or maybe, just maybe participate made it a bit more confusing. Some guys were just not really into exhibitionism. And what was I supposed to tell the guy, that my newly bi-curious boss wants to watch? I wasn’t giving up though, I really was turned on by the idea of him sitting back in a chair and jacking off while I got fucked. I was trying not to fantasize about him joining in though but it wasn’t easy.

Pondering this late one night, I realized a solution to my conundrum. Hire an escort and I had just the guy in mind, Kevin. I’d hired him a couple times and well, he was a great fuck. I think he might fit the bill perfectly. In more ways than one hopefully. Kevin was in his early thirties and still resembled the hot all American frat boy he had been years before. I sent him an email asking if he would be interested.

As I lay in bed that night the images of Kevin fucking me while my boss watched had me hard beyond words. Knowing I needed to blow off some steam to be able to fall asleep, I started to jack off. My hands weren’t enough though so I lubed up a small vibrating butt plug and started to go wild. The gentle vibrations shot pleasure through my body as I stroked myself and I was close already, so close. Closing my eyes, my mind conjured the image of my boss watching Kevin and I kiss. Breaking the kiss, Kevin puts gentle pressure on my shoulders to tell me it’s time to drop to my knees.

With a quick stop to suck on each nipple, I lower myself to my knees and take his hard cock in my mouth. I glance at my boss a couple feet away in the chair as I start to suck and swallow him in earnest. Kevin’s hands come around to back of my head as he gently begins to rhythmically slide his length deep in and out of my throat. From just out of the corner of my eye, I see my boss has taken his cock out and is jacking himself off.

My fantasy shifts to me on my knees sucking on my boss’s cock as he kicks back in the chair. Kevin moves behind me to slowly slide his cock into my hungry ass and begins to fuck me.

The mental image of my being spit roasted by Kevin and my boss had me shooting a massive load all over my stomach as my hole clenched with need.

I needed to make this happen and soon.

Kevin had been more than open to my email and so I made all the arrangements. I’d tried to get more of a concrete idea from my boss as to details of what he wanted but that was a no go. While he’d never been an overly talkative man in the office when it came to this was beyond vague. Since I didn’t want to jinx it, I left it alone. After I gave him the time and date he gave a silent nod of agreement.

I was a little nervous but also really excited when the day came. I had been fantasizing more and more about what happen but was afraid of getting my expectations too high. There was a chair set up near the bed for boss man and I had just lit some incense when the buzzer sounded. Dressed only in a pair of old boxers I opened the door to let Kevin in. I had asked him to come a bit early so we could chat.

He was even better looking than I remembered. With a quick kiss and hug we went into the bedroom where he took off his clothes and made himself comfortable on the bed.

“So is he still just watching or wanting to join in?” He asked.

“Not a clue, the only thing he has been willing to admit to is he wanted to watch me get fucked.”

With a wry smile, Kevin answered “Well, that could mean a few different things.. “ pausing for a moment, “Maybe he wants to fuck you or he might want to get fucked.”

“I have to admit, ever since I discovered even the possibility of his playing around with other men I would love to have him fuck me. To feel him inside me, though I would’t mind fucking him either.” I answered softly, watching Kevin stretch out with his hands behind his head as he spread his legs a bit to show off his half hard cock .

“Though he could also just be someone who gets his jollies off watching. Is his name Chance the gardener?” Kevin added which made me chuckle, as I knew just what he was referring to.

“Don’t worry, it’s all good. I’ll put on a good show and see if I can help him out of his shell. ” He said just as the buzzer rang. Leaving Kevin on the bed, I answered the door to let in my boss in. In just a tank top and shorts, I had never seen him dressed so casually. And I didn’t realize just how fit he was with his lean muscled arms and shoulders. Wow, I’d always thought he was attractive but this was just well, damn.

With barely a word he followed me in to the bedroom where Kevin lay, still with his hands behind his head and his legs spread to show off his hard eight inch dick. A softly whispered ‘wow’ was my bosses only reaction as he quickly sat in the chair.

Stripping off my shorts, my dick was already rock hard and eager to play. Wanting to put on a show for the boss man, I climbed onto the foot of the bed to work my way up to the prize. I kissed and licked my way up from his ankles to his groin. Spreading Kevin’s legs a bit more, I gently licked each of his nuts before sucking each ball into my mouth.

“Yes, lick those balls.” Kevin hissed through half lidded eyes. From there I slowly tongued my way up his shaft to his head. I swirled my tongue around the head before taking him into my mouth. I loved the tasted and feel of him in my mount.

“Suck it, suck that dick. Swallow it all the way down.” Kevin commanded as I proceeded to do just that. Taking more and more of his hard cock down my throat stretched out as I hit bottom. I took him I deep throated him for a couple minutes as he moaned before I pulled off to make my way north.

With just a glance over at my boss who was massaging his own hardness through his shorts, I used my tongue to taste Kevin as I made my way to his chest. Each nipple received its own sucking kiss. Continuing to make my way, my tongue caressed his neck and then gave a quick lick through each armpit.

Finally, my lips brushed Kevin’s and his hands stroked my hair and ears as the kissed deepened and our tongues entwined. He took the lead as he sat up and pushed me on to my back. His own journey mirrored my own as he gave gentle bites to each nipple before swallowing my leaking cock. My boss was almost forgotten as I let out an audible moan, Kevin was an amazing cocksucker.

He spun around to give me access to his cock and for the next couple of minutes we greedily sucked each other. I spread my legs as Kevin stroked his fingers over my hole before pushing in just a bit. I moaned around his cock as he pushed farther in with his finger.

Kevin’s cock slipped out of my mouth as he sat almost straight up to reach for the lube on the nightstand. With a glob of lube, he started to stretch me out in anticipation of taking his cock. Little gasps of pleasure escaped me as his fingers worked their magic. The angle of how he was playing with my ass gave me the perfect opportunity.

Just a few inches away was Kevin’s smooth puckered hole begging for a taste. I used my hands to caress those muscular cheeks while raising my head up just a bit to kiss that beautiful ring. My tongue flicked back and forth as I started to eat his ass. The taste was masculine, male and so very Kevin. I dove in for more.

“Fuck that feels good, eat that ass.” Kevin moaned as he pushed back against my mouth as my tongue continued its assault.

A minute later Kevin moved off me, telling me to get on all fours. Of course he positioned me so I was facing my boss, still sitting in the chair though now his shirt and shorts had been shed and he was jacking off. His chest was muscled with just a light dusting of hair and he was just stunning naked. His beautiful cock was rock hard and leaking. The look of intensity and lust on his face was a huge turn on for me.

Behind me, Kevin used more lube to stretch me out a bit more before sliding his dick into me. I moaned with joy as he sank all eight inches in with one long steady thrust. Grasping my hips, he slowly started to fuck me.

“This what you wanted? To watch him get fucked.” Kevin asked my boss as he sat there silently playing with himself.

“Yes.” Was his one word response, followed up a few seconds later “Harder.” Kevin picked up the pass of his pounding my hole. Each thrust causing me to let out a small gasp of pleasure.

“You got it boss.” Kevin answered by almost pulling out and thrusting all the way back in with one long shove.

“He really does love a cock up that hungry hole of his.” Kevin said as he started taking aim at my prostate over and over again causing me to moan loudly. The idea my boss was getting off watching me get fucked had my dick so hard I was already close to orgasm.

“Fuck me… feels so good.” Was all I could manage as I closed my eyes in pleasure. For the next few moments the only sounds in the room were our breathing the slap of flesh upon flesh. Then I something changed, looking up I saw my boss’s hard cock inches from my face.

“Suck it. Swallow my cock.” My boss said, his voice raw. Without a seconds hesitation, I swallowed the head as he moved forward allowing me to take his entire cock down my throat. It was a perfect fit.

“You like this? Getting a hard cock in each hole at the same time?” Kevin said, knowing that I like dirty talk. I could only mumble in agreement since my mouth was full.

“Fuck that ass.” My boss’s voice said with almost a deep growl. Then with his hands holding my head in place he started to fuck my face as Kevin worked over my ass. I was lost in a sea of sensation.

“I’m close, gonna blow my load inside him. Then I want you to do the same. I want to watch you breed his hungry ass.” Kevin said before starting to pickup speed. With a rough thrust I felt my hole grow slicker as he emptied himself inside me.

My boss quickly moved behind me and thrust his own cock in me and it felt better than good. I was finally getting what I wanted. My boss inside me, fucking me hard.

His grasp on my hips grew tight as his thrusts grew faster and his breathing uneven. Then I felt him orgasm, spurt after spurt blowing deep inside me. After he pulled out, I rolled over on to my back to catch my breath. My rock hard dick was quickly swallowed by Kevin and then a second later my boss went down on me as well.

Watching the two of them licking and sucking my dick at the same time made me blow and my orgasm was so powerful it physically hurt. Resting my eyes for a moment as my breathing calmed I felt a gentle pair of lips on mine. The close cropped beard let me know it wasn’t Kevin.

I deepened the kiss as I pulled him closer to me as I looked forward to round two.