21st Floor Tryst

FUCK!!! What in the hell was he thinking? How fucking inappropriate can one person be and to top it all off the fucking idiot didn’t seem to care. UGGGHHHH!!!!!

Sorry, I should start at the beginning – My name is Gabe and I run a highly successful tech company. I grew up in rural Washington State, realized I like sex very early in my life, and found that both men and women could provide a great deal of pleasure. I got married in my last year of college and had 4 beautiful kids by the time I was 26 (two sets of male identical twins). My wife died during the second set of twins' birth, she had an undetected brain aneurism, so here I was 26, with four kids aged 3 and 1.

I worked out every morning at 5 AM to make sure I got that in, it was/is my way of staying sane. I’m 6’2” tall, have dark brown hair, and green eyes and I would say fairly good-looking. I have had several people fawn over how attractive they think I am, but I don’t see it, so I’ll stick with reasonably attractive. I know I am in killer shape because I work hard at it – weights and diet are key for me. I run around enough without focusing on cardio – volleyball, softball, rock climbing, and skiing (water and snow when I can).

I have a great family network that helps me out and fortunately, for me, I can afford live-in help (Rebecca), to keep up with laundry, meals, cleaning etc. but when I’m home from work my kids are the center of my universe. It took me a good 6 months to get my head right, Bethany and I were supposed to be together forever but I guess God didn’t see fit to let our plans stand. Sorry, a little wallowing…

Ok so back to my small meltdown – my assistant Grant, also my older brother, set me up on a blind date with someone that works, check that used to work for me and he was now sitting outside my office waiting for me to wrap up my day.

Grant was standing there smiling at me like he always did, nothing seemed to faze him and he knew me very well – he is exactly 4 minutes older than me and to this day our family struggles to tell us apart but for fucks sake he drives me insane but he was waiting for me to calm down. “Grant, why are you doing this to me? I’m happy being single and raising my four kids and what were you thinking, Seth of all people…”

Grant cut his brother off – “Gabe you need a night of fun and debauchery. Seth is a perfect candidate for that, he is hot, sexy and from what I know he is great in the sack. You need to get your dick wet and a tube sock with lube is not the same thing as tapping a fine piece of ass.”

Gabe thought he had the perfect out – “Grant I can’t tonight, I gave Rebecca the night off so I have to take care of the kids.”

Grant smiled, chuckled – “Yup, I know that but Uncle Grant and Uncle Joe are set to take care of their gorgeous nephews. Yes, Bethany’s brother and I are dating and want to do this for you. We debated on boy or girl and the boy won out because there is a higher likelihood of sex on the first date. So listen to your older brother, he knows best.”

Gabe shook his head – “You are 4 minutes older than me so kiss my ass , ok stop you know I meant that rhetorically. But why Seth, he so fucking smug and annoys the crap out of me.”

Grant leaned against the desk and looked his brother directly in the eyes – “Seth is cocky, self-assured, gorgeous, and very good at what he does. He is not as good-looking as we are but I doubt very much if he has had many guys turn him down based on his looks. Before you say anything, I’m not expecting this to be a forever thing, I’m expecting you to go to dinner, dancing, and fucking. So, with that in mind, slip into your bathroom and freshen up while I entertain your guest for 5 minutes.

So here I stand in my bathroom cussing out my brother in the mirror. FUCK, why can’t he just leave me be? I am content with my life the way it is right now; I have my health and kids. Why do people keep trying to set me up on dates? I didn’t even see this one coming as my brother made all the arrangements around me and sprung it when my date arrived. Damn him. I opened the door and almost hit Grant in the face with it. He was a bit indignant but I let him know had I known he was on the other side I would have made sure to hit him with the door. Grant rolled with it – “So Gabe, if I had known you could look and smell this good, I would have taken you home and done the deed with you.”

Gabe didn’t find the humor – “You really are twisted. I don’t even know how that would work, two tops that are exactly the same, literally. Now get out of the way so I can get this train wreck of a night over with.”

As we exited my office Seth stood up, he was a fine specimen of maleness. My dick even twitched, fucking little Benedict Arnold. I reached out to shake Seth’s hand but he pulled me into a hug – “Fuck you smell good, had I known the way to get an actual date with you was to quit, I would have done that a year ago.”

Grant had a shit-eating grin on his face as he looked over Seth’s shoulder – “I arranged for a car for the evening so that you don’t have to worry about Uber or driving after drinking. You have a reservation at 6:15 at Sugo downtown. I have also called ahead to both The Cuff and The Crescent and reserved you a table depending on whether you want to dance or sing karaoke.”

Seth took the bull by the horns – “Or we can go back to my place, order pizza, and fuck ourselves stupid. I’m game for the nice dinner, some dancing, and then going to my place to fuck ourselves stupid. Your choice Gabe.”

Gabe laughed loudly – “So there he is, the smug little bugger that annoyed me to no end when he worked here. How about we just go back into my office and I fuck you on my desk and skip any and all pretense that this is anything other than good hot, hard fuck.”

Seth removed his jacket and headed for Gabe’s office door while unbuttoning his shirt. He glanced over his shoulder, winked at Gabe, and asked him if he was coming. He didn’t wait for an answer as he continued into the office. Grant handed Gabe a box of 12 XL condoms, and lube and made a smart-ass comment – “Well I did say you just needed to get your dick wet, and don’t try to tell me you’re not interested. Your dick is leaking like a faucet and that tent is VERY obvious.”

Gabe grabbed the items offered and flipped his brother off as he walked by. When he opened the door what he saw inside took his breath away, Seth was completely naked, reclining on his credenza, leaning against his 21st-floor window with his knees pulled up and out exposing the most gorgeous ass you could imagine and a tight pink rosebud at the center and a nice 7-inch cock sticking straight up in the air.

As Gabe made his way across the room, he removed his clothes very quickly. He was fumbling with the box of condoms when Seth spoke up – “Gabe, I know you think I’m a smug, arrogant ass that sleeps around a lot. I will agree that in business I am arrogant and smug but so are you, that said I don’t sleep around and the last time I had sex without a condom it was with your brother in college. My test results are there on the desk and I’m on PrEP. If you know you are clean, which I have no doubts about given your marriage and lack of sex lately, I prefer you not use condoms, I want to feel all 9.5 inches in my ass. I guess I’m assuming that your cock is identical to your brother's. It’s up to you but know that I just want you.”

Gabe was caught completely off guard and didn’t know what to say so he dropped the rest of his clothes and the condoms on the floor. He placed the lube on the credenza and grabbed Seth’s right leg and began making love to it. He slowly massaged the soles of the foot and ran his long fingers the complete length from heel to the top of each toe. He then began to lick in the same fashion and when he got to the big toe he sucked into his mouth as his hands began their exploration of Seth’s well-toned calf. Once he finished massaging the calf his tongue began to explore that same skin while his hands went to work on his thigh.

Seth started stroking his cock at this point. Gabe stopped his movement and shifted his eyes to meet Seth’s and gave him a disapproving look and a slight shake of the head which caused Seth to let go of his cock and put his hands behind his back. “Good boy” was all that was said. Seth’s cock was producing more sap than he could ever remember and Gabe had only touched his right leg. He thought to himself, I am going to go insane with this man.

When Gabe had finished massaging his thigh his tongue began to trace the path of his fingers. His hands grasped Seth’s left foot and began the tour of that leg with an extended massage of his foot. As he was wrapping up the massage he trailed his tongue below Seth’s bud and his nose skimmed his taint as he exhaled, the warm air caused Seth’s bud to flex. Seth moaned out – “Fuck me, I’m going to cum without actually touching my cock, balls, or ass. This is the most exquisite torture I have had.”

Gabe moved his mouth to the left foot and repeated the process that was done to the right. The nibbling and tonguing of his inner thighs had him begging for Gabe’s cock but Gabe ignored him. He continued the massage and tongue bath up Seth’s body, Gabe made certain to lick up all of the nectar from Seth’s abs and belly button without actually touching his cock. When Gabe bit down on Seth’s right nipple and pushed his cock head into his taint Seth unloaded a huge amount of cum on both of their chest and abs. Gabe sucked up what he could into his mouth as he stared into Gabe’s blue eyes.

Gabe stood up, took a step forward and placed the head of his cock in Gabe’s cleft, and smeared his own slick over his rosebud. He kept running his cock up and down his cleft, over his bud, across his taint, and into his balls. Seth was squirming with desire and was still hard as a rock. On his next pass, Gabe pushed forward so half of his mushroom head was inside Seth’s opening. He slowly released Seth’s cum from his mouth and dropped it on his cock as he slowly pushed inside of his velvet inferno.

He was fully buried inside of Seth when they locked eyes. Seth’s eyes were hooded in lust, want, and desire. Gabe flexed his cock inside of Seth’s tunnel causing a deep guttural moan to escape his lips. Gabe slowly pulled out to where the head of his cock was the only thing left inside Seth, he slowly sank back into his depths, flexing his cock as it moved over Seth’s sacred spot causing Seth’s cock to coat his stomach in nectar. Gabe repeated this motion over and over until Seth exploded from all the pleasure, cum was flying everywhere with some landing on the window of Seth’s shoulder. Once Seth’s orgasm subsided, Gabe slid all the way into Seth, leaned down, and kissed him full on the mouth. He whispered in Seth’s ear asking if he could continue, to which Seth replied only if you will help me to my bed when you take me home.

Gabe nibbled on his ear – “I will certainly make sure you enjoy the rest of the night and get you to your bed when we finish.” Gabe started cleaning Seth’s cum up and occasionally sharing a cum filled kiss all the while flexing his cock in Seth’s ass.  Seth started to push his ass down on Gabe’s stiff member giving the go-ahead to resume the fuck fest they were enjoying. Gabe leaned in – “I hate to admit it but I could get used to this.” Seth groaned as Gabe continued to flex his cock – “I’m not sure I could survive this much pleasure every night but fuuucck, I would die a happy man if nothing else.”

Gabe began a painfully slow long dicking of Seth’s hole, dropping his hips on the inward thrust which drove the head of his cock into his nut milking out more and more nectar. Seth was well on his way to his third orgasm when Gabe pushed Seth’s legs up in the air dropped his hips and punched Seth’s nut until he was spewing another load onto his chest and stomach. Gabe did not stop at this point, he wrapped Seth’s legs loosely around his waist and started to power fuck Seth, sawing his cock in and all the way out before pushing all the way in again.

Seth’s eyes rolled into the back of his head while Gabe pounded away, this time when Seth started cumming, Gabe was unloading a huge load of cum deep in his tunnel. Once Gabe was finished unloading he started to withdraw and push in over and over until they both came one last time. Gabe slowly withdrew his cock from Seth’s well-used hole. Seth did everything he could to tighten his hole quickly to trap the cum inside which for the most part he was successful. Some did leak out which Gabe licked from his pucker. “You are a dirty thing, aren’t you?”

Gabe smiled – “I can be especially when I have been so wrong about someone and they give everything they have to me while making love. You are exquisite, your body, mind, and the fucking little hole of yours, unngghhh. If I didn’t think I would break you, I would drive you home and fuck you until the sun comes up but I know that would be selfish of me. Will you allow me to take you on a proper date and see if we can get along without being naked?”

Seth smiled – “I will agree to a date only if you let me cook for you, that and you help me dress as I don’t have the strength to do that for myself.”

Gabe smiled as he gathered Seth’s clothes and began helping him get dressed. Once he had completed that task, he started to put his clothes on but Seth grabbed his underwear and inhaled them deeply – “These are mine. I can’t believe how much your scent turns me on.”

Gabe chuckled and shook his head – “Now who’s the dirty little thing?”