White Collar Tales

White Collar Tales: No Profile Pic Bill Drake (billdrake@hotmail.com)

WARNING: The following is for adults only. It contains depiction of sexual acts between men. If this offends you or is inappropriate for you to read, go no further.

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White Collar Tales #24

NO PROFILE PIC by Bill Drake

I wasn't sure I wanted to move to Chicago, but the company that was flying me there for the interview was one of the better places to work for and even as a holder of a newly minted Harvard MBA, I knew this would be an incredible job to land. Executive leadership track, and high-paying in a medium cost of living city.

It wasn't like I was eager to leave Boston, either. I'd had a good bit of luck as a younger man into topping older, exec types. Between the middle-aged professional gay men and the straightish dudes looking to play with a guy, I had achieved a nice mix of regular fuckbuddies and new conquests over two years. Some provided oral service only, and that was great, while some let me fuck them. I didn't think of myself as a shallow asshole, but maybe with sex I was, getting off on the fact these older, successful men would drop things for me to take care of my needs.

Maybe the only drawback was that New England reserve. During my college years at Clemson, I'd gotten very used to a needy, hungry type of Southern daddy. I wouldn't say those years turned me onto older bottoms, but they cemented my love of a 40- or 50-something masculine man with a submissive side. I found my share of bottom dads in Boston, but few really wanted to embrace or indulge the kind of submissiveness that really got me going.

When I started my MBA program, I had my sights set on New York, of course. Even if less than 1% of those hot Wall Street types were bottoms, that was still a lot to have fun with. About once every couple of months, I'd take the train down and line up a couple of hot hookups that put those Boston execs to shame.

But I was starting be realistic. I sent some applications to a number of New York companies and had some initial interviews, but I wasn't going to land an opportunity like William Blair.

So I bought a new interview suit, on the conservative side of conservative business dress, and a new, equally conservative, tie, and I flew out to Chicago. They were putting me up for two nights in a hotel in the Loop, and I decided to tack on a third night to enjoy the city and do a little reconnoissance.

After a delayed flight, I thought maybe I'd just keep that first afternoon and evening low key. Walk around downtown a little, grab a bite somewhere, that kind of thing. As a Southern boy, I'll admit I wasn't keen on the idea of Chicago weather, but spring had sprung in the best way for my arrival. I checked in to my hotel and freshened up. When I stepped out again, the city's energy gave me a second wind. Best of all there were a fuck ton of hot guys walking around, some in business casual, some in suits. A lot with that cornfed Midwestern look that I decided I liked.

That's why I pulled up the apps. I knew I'd love have a hot older guy sucking me or bending over for me that evening. Perfect way to see what Chicago was about, I figured.

Of course, there's often that disconnect between the hotness you see walking around and the guys available on the apps. Don't get me wrong: some other dude would have been happy enough with what I saw. But there was a sea of regular "jocky" gay men that didn't push my buttons, and a good majority of the older guys who did listed total top or top vers. I had a profile that was specific in who I was and what I wanted: total top, very verbal, into fit/regular professional/executive men 40+, love submissive guys, but newbies/DL guys OK. In reality, if the guy was hot enough, I'd ease back on the dom talk, and in Boston that seemed to happen a lot, but that was on a case-by-case basis.

I checked out Sniffies for a few prospects. But either I didn't hear back from them or nothing clicked. I got a few hits myself. Two were not my type at all, one was more a "not now but maybe later" groundwork chat.

I grabbed some dinner in a restaurant bar. The happy crowd was still lingering and I had a good sightline to a couple of middle aged businessmen at the other end of the bar. Blond, beefy, tall... Chicago certainly gave me some welcome eye candy.

I enjoyed the surreptitious bone I was forming sitting at the bar. Maybe I had a libido that could spill over into sex addiction, but it had been a solid week since I'd had a business daddy suck me, and the number of hot business guys in the airport and walking around downtown Chicago had my imagination running wild.

I opened Grindr again. Nothing caught my eye, but as I browsed Sniffies I got a message. The profile was a shell that had no picture, showing up about 4 blocks away, but the stats listed sounded up my alley: 58, 6'2" 195# bottom, corporate/clean cut married looking for corporate/bro/jock/son. Not hosting.

His tone was perfect, too: "Hi man. Fucking hot profile. Long day in meetings and I need to let off some steam..."

I didn't have pictures of him to go by, but was willing to engage. "How would you do that?" I asked.

The response was immediate. "It's been too long since I sucked a cock."

OK, I wanted pictures. "Pics?"

He sent me a few. No face, but there was one framing a chin/mouth shot and the top of a shirt/tie combo, all drenched in dripping cum. Very nice jawline and, I dunno, he had a hot mouth. The other was a mirror selfie of his body. He might be 58 but had that fit-daddy look, like a man who lifts and runs and plays racquetball regularly. He had my attention a big way.

"Hot profile yourself," I typed back. The man was about two blocks away. "I can send you more pics if you want," I typed.

"Feel free," he wrote. "But your cock is enough man. I wanna take care of that."

OK, I was rockhard beneath the bar ledge. I'd have to think of something unsexy to be less obscene when I left. I had more than a prospect, I had a pretty sure thing.

"I don't recripocate," I clarified. As much as I put on my preferences and expectations on the profile, some dudes had reading comprehension problems, or liked to play cute by pushing their luck.

"I just like being on my knees for a guy like you." Goddam. "I just can't host."

"I'm staying at a hotel," I typed back. "When can we make this happen?"

"Give me 45 minutes? I still have some work bullshit to tend to."

"Sounds great," I typed him my hotel and room number, then flagged the bartender to pay my check.

I was getting so turned on by the time I got back to my room. Maybe I shouldn't let it go a week between blowjobs, but even with the apps and overall having the goods that attracted men, it wasn't always feasible to get the service I wanted. I'll be honest: the more luck I had, the pickier I got about the kind of older men I wanted.

I told myself not to get too excited for this hookup. Maybe the guy was a bullshitter, or maybe he wouldn't be as hot as the corporate daddy in my mind. Still, I was feeding off his submissive vibe and wanted to set the tone for the encounter. Once in my room, I stripped down naked.

I took a look in the mirror to check my appearance. I had an athletic build, from years of playing tennis, including on the Clemson men's tennis team, and in my last couple of years I'd kept up my game and a regular gym routine. Maybe it helped being into older men, but that's just how I was wired. My first time with another guy was with my high school tennis coach, and I hadn't looked back.

A knock came at the door. I went and peeked through the peephole to make sure it wasn't housekeeping or anyone else. Indeed, a suited handsome daddy stood outside. I didn't get a great view of him that way, but I opened the door, and let him in.

Up close, he was just incredible. Executive cut brown hair showing some wisps of gray at the temples, upright posture, a trim but muscular body that filled out a clearly expensive and well tailored suit.

His eyes widened and he laughed a little when he saw I was completely naked.

I took the initiative though. "You said you were here to take care of me, right?"

He nodded, looking down at my erection. "Definitely," he said. Then without fanfare the exec got onto his knees and started to kiss and nuzzle my dong, while letting out a soft, deep grunt.

I actually loved this give and take. When an older man so clearly is there to service me. But I also loved for a cocksucker to enjoy my dick in the way that turns him on. Exec Daddy liked the slow approach, working me to steel hardness with his tongue and fingers before actually taking me in between his lips.

I was curious how long it had been for the guy, he was just attacking my bone like an addict getting a needed fix. Deep descent onto my cock with each bob, and getting deeper. He gagged a little before settling into the pace. That was hot as fuck.

He took the liberty of running his hands along my hairy thighs and curling around the hamstrings for leverage and balance as he really got into it. It was starting to feel real good. This was gonna be a blowjob to make me forget my last five. There was just no comparison.

Exec Daddy spit out my dick. He swallowed the spit and cleared his throat. "I forgot to ask," he said. "You like to get off fast? Or you prefer me to take my time?"

Both sounded great. But I knew my answer. "Fuck... take your time."

He smiled and muttered, "thanks," before going down on me again. I could tell he was excited to blow me. Maybe excited to blow any guy, but I was the right dude at the right place and time. And though I didn't have his full story, I seemed to fit his type or what he was looking for. Young, bro-jock type in spades.

His sucking now was exquisite torture. Glacial-slow down my hardon, taking in my girth and running his tongue along the tube of the underside. Maybe he was showing off for me, maybe he was just enjoying the opportunity to worship a cock. He neared the base of my prick, then pulled up just as slowly. The third time down he was kissing my pubes.

From there, Exec Daddy worked me up with precision. Even if this guy's technique was lousy, he would have pushed my buttons big time. I ran my fingers through his hair as he picked up speed, keeping the deep throating with each swallow.

The man spit out my dick again, licking up the spit to make sure none got onto his tie. "God, this is a big cock,"" he muttered, not even taking his eyes off it.

"You know how to take it," I hissed. My dick twitched in front of him.

That made the executive smile as he looked up at me. "It takes a good bit to trip my gag reflex, actually."

"Yeah?" I asked, excitedly.

He nodded, reaching forth to gently stroke my hardon. "I mean, I definitely have one and this bad boy would be enough to do it.... fuck...!"

He took the initiative now in sucking me back in. All in one go. I'd never get sick of this view, his expensive suit framing that fit-dad body. I don't know Executive Daddy's story, but he was the real deal all right. And he was giving me some primo head.

I got greedy though. I head onto his skull and started thrusting. It had been too long since I'd used a mouth. I might be putting Exec Daddy's skills to waste but this is what I craved at the moment. My dick can do some damage if I'm not careful, and I heard some choked grunts, then Exec Daddy pushed against my hips to signal a break. I gave it to him.

He swallowed his spit and caught his breath. "If you're gonna do that, let's try on the bed. The angle's better that way," he hissed.

"Fuck yes," I said. I watched excitedly as the man got onto the bed crosswise and lay back with his head over the edge. I gave him a second to get settled then I stepped up. His tongue darted against my cock head, then I felt the warm wetness of his mouth enclose my dick.

I wasn't rough but my entry was direct and insistent. Pushing in to bottom out in one go. Exec Daddy moaned around my cock, but in a good way. I tapped his cheek as a signal I was about to start.

Then I did it. I looked down on this suited middle aged stud and just began fucking his throat. I had restraint in keeping from shoving in too hard but I was deep and steady in my thrusts. It had been too long since I'd found a man who'd let me do this, who was capable of letting me do this.

My height meant I wasn't at the perfect level so I leaned forward to allow me to fuck his mouth like a fleshjack. The noises were obscene, with wet slick moans and a little light gags, but mostly Exec Daddy took it. The angle meant I was penetrating his gullet more deeply, and the wet snugness was gonna milk me off, quick.

The trigger though was his reaction. He was throwing hard in his suit trousers, his spike forming a tent in the wool. Exec Daddy arched his back to accommodate my thrusting. That action made me blast. Six, maybe eight, hard spurts of cum right into his stomach. The man was only going to taste the dribbles on the withdrawal.

His face was red from the blood rushing to his head and he had some spit on his face. The man caught his breath and kissed my wet dong as I slipped out. I let him enjoy this, but it was clear he wasn't going to get off in this session, so I stepped back and gently patted his face.

"Fuck, thanks," I hissed. After a good cum, I generally become more easy going, even after more dominating sex.

He got up and washed his face at the sink. He was still hard as he stepped back, adjusting his shirt in his suit to look presentable. I was naked still, and enjoying his eyes on me. "Glad I logged in today," he said. "It's been a long time since I've played."

I still had to square the words and easygoingness about sex with his boardroom-ready looks. Maybe he was fibbing to assure me he wasn't a slut, but given the quality of the suit, I could very much picture him as the kind of man who indulged his need to suck cock only occasionally.

"Glad you did, too," I said. "You're an incredible cocksucker," I added. Friendly in tone but also asserting his submission to me. "I don't know if you ever do repeats but I'm in town for a few days...."

I could his battling thoughts. But he hadn't gotten off just now and maybe was letting his dick think for him. "I gotta be careful, man," he said. Which was basically a yes.

"Absolutely," I assured him. "I'm totally discreet. I just want your mouth on my dick again, before I head back home."

He asked if I used a certain message app, and I did. We swapped contact info. Part of me wanted to kiss him but felt it wasn't his thing. So we bumped fists at the door as I showed him out.

Fifteen minutes later I got a message. "Thank you for that," he wrote. "You pleased and all drained?"

I felt my dick chub up. "Pleased. Probably could go again to be honest."

"I wanna suck you again. Maybe first thing tomorrow?"

"I have a meeting to go to 8:30," I wrote. "But if before 8 that works.

"Yeah, I'm an early riser." Then, "want your cum to start my work day."

"Well hit me up first thing. I'll be up early to hit the gym." Chicago was only one hour behind, but that meant I'd easily be up before 6.

"I will man. You're so fucking hot."

I didn't fuck Exec Daddy's face the next morning. Instead, I let him show off his skills on me. I'm a morning guy when it comes to sex, so it took maybe 3 minutes from the time he came in till the time he left, my cum as his breakfast.

I felt happy and relaxed and I wondered if the experience had tipped the scales in favor of moving to Chicago. I mean, there were hot men everywhere, but Exec Daddy was my type to a frickin T. Even if he was just an occasional thing, I'd be very into establishing something regular with him.

But that was putting the cart before the horse. I hadn't been offered a job, and hell I had no idea if the middle aged corporate guy was up for anything more than a couple of times.

Still, the experience had me ready to do my best for the interview. I made sure everything was perfect for my suit and tie combo and that my black dress shoes were polished, then made my way across the river to William Blair. I met with HR then had a round of VP interviews. I think I did pretty well, but you never really know. I'd been overconfident in one job interview already. I learned and adapted.

They took me to lunch. Even if I didn't end up landing the job, it was nice to be courted.

At 1:30, they took me to meet the new director of global wealth management, who'd basically be my boss's boss and someone I'd be working with as a member of the leadership mentor program.

It was a nice office with a great view of the river and the Chicago high rises. But as the man stood up, I saw the fear and shock and embarrassment on his face. It was Exec Daddy, who'd blown me just six hours earlier. Robert Lyman was the only member of the leadership team whose photo I hadn't seen; his hire was very recent and his profile page on William Blair's website still lacked a photo.

I knew my own face betrayed a million emotions, too, but I played it cool. "Cole Edwards," I said, extending my hand to shake his. "Nice to meet you, Mr. Lyman."

"You can call me Robert," he said, recovering without too much slipping. "Nice to meet you." He turned to the HR specialist who was my guide for the afternoon. "Give us 30 minutes, Dan?" he asked. The HR guy nodded and backed out, shutting the office door behind him.

I was wrapping my head around the fact that I'd blown my chances at the job. No way would this guy hire me now. At least I'd gotten some hot sex out of it.

"Of all the cocks in Chicago to suck," he laughed, face blushing some.

I leaned back in my seat. Even now, I was getting hard, looking at the man and remembering him going down on me. "Don't worry Robert," I said. "I meant what I said about being discreet."

I wasn't fishing for anything, but after seeming to think things over he said softly. "You texted earlier you'd be up for another blowjob at the end of the day."

I was incredulous. "You still offering?" The man must really be cock crazy. Or Robert realized he'd already cross the line, so why stop?

He grinned. "I have plans I can't get out of," he replied. "But if you want one now..."

My cock made it all the way to erect in my new suit. "God yes," I hissed. Reaching down to undo my belt.

"Let me lock the door," he said as he bounded up. I liked his suit yesterday better, but this one was equally expensive and perfectly tailored. I unzipped and hauled out my cock and watched him walk back, a naughty grin on his face.

Right there, in his own office, he got down on his knees on the carpet and scooted in between my spread legs. This was just about the best sex I'd ever had. The emotional power of having this subservient exec going down on me, the fucked up situation, and the amazing cocksucking technique. Blowjob #1 had been about me fucking his face, #2 about him doing all the work. Blowjob #3 was a mix, him bobbing and me assertively pressing his head down on each downstroke. He was probably getting some spit on my trousers, and I hoped to hell I'd be able to pat it dry before my next appointment.

"Shit!" I growled in a whisper as I fed him his second meal of cum in a day. He slurped and suckled and licked my dick as I rode the aftershocks.

He finally pulled back, a proud smile on his face. I still couldn't believe a man that powerful and handsome had made me cum three times in less than 24 hours. He got up and walked back to his desk as I did my best to tuck in.

"You need a napkin?" he asked.

"Yeah," I said. Then tried blotting the spit wetness from the charcoal gray fabric.

"We have about 20 minutes," he finally said. "Let's talk about why you think you'd be leadership material at William Blair."

I still didn't know where I stood. Robert Lyman could kill my application with the lift of his finger, I knew. If I were him, that's what I'd do. I was an HR nightmare waiting for him to step on if I joined the firm.

So as I got to my hotel room that night, I was a little moody. But I still replayed those blowjobs in my head. Especially #3. Feeling I'd already done the best - and worse - that I could for the interview, I typed Robert a message.

"My only regret was that I couldn't fuck you." I normally felt a guy out longer or waited for him to bring it up. At least if he was a married with kids type like Robert. With gay daddies you didn't have to be so coy. I was now feeling like I had nothing more to lose.

I expected radio silence, actually, but got a reply within ten minutes. "It's been a long time since I've done that."

I was hard again. "I'd go easy on you. Scout's honor."

"LOL. I think I prefer cocksucking, but you would be the kind of man to persuade me otherwise."

"What kind of man is that?"

"Jock next door type. Hung. Horny," he wrote. Then, "Your accent drives me wild, too."

I smirked. "I look forward to the chance to let you hear it again."

He took a minute to reply. I wondered if he was with his family, maybe having a late dinner, or watching TV. "You still trying to interview for the job?"

"I'm more interested in interviewing you for a good sub dad," I answered truthfully.

He didn't reply.

"May I speak to Cole Edwards?" the woman said. I had gotten so used to not answering phone calls, because of the spam robocalls, but the area code was a Chicago one.

"Speaking," I said. I'd just gotten back from the courts where I'd played a game of tennis one of the finance professors. He wasn't a sub daddy, and was even on the younger side of what I normally went for at 38. But he was extremely handsome and extremely open to giving me head. He sucked me off in the seat of his SUV before dropping me off at my apartment building.

"I am calling with good news, Mr. Edwards. William Blair was very impressed with your interview and would like to offer you the position."

The rest of the conversation was short but sweet. She gave me the basics of the offer - compensation, expected hire date, and the next steps. I'd have a week to give my decision. I thanked her and hung up. I was thrilled. I'd been going over the pros and the cons of the job and of Chicago, and I'd practically talked myself into thinking I didn't even want it. But now the offer was there, I realized how amazing this opportunity would be.

I wondered if Robert had pulled some strings, or if I'd gotten the position on my own merits. I thought of texting him, but figured now that I would actually be working at the company, I'd have to play it safe.

But within an hour I got a message from him. "Did I pass the interview?" was his message.

I smirked and typed back. "It's a start." I set down my phone and stripped down to shower up.

Fuck, I was gonna love Chicago.