The Boss I Never Knew I Needed

I was 23 years old when I had my first gay experience. I hadn't come out until I was 24, so like most first experiences, I was still in the closet. I wish I could say I've had many similar scenarios as my first at age 23, but now a decade later and I'm not sure I have.

I was living in DC for the summer, studying for the LSAT and working as an intern at a prestigious DC Law Firm. Although it was technically just an internship, the goal was to get a job offer before I hopefully headed off to a top 10 Law School.

The work at my internship was arduous. I usually got to the office around 7:30am and didn't leave till around 10:30 or 11pm. I worked my tail off that summer, but to be honest I always felt at my best mentally when I was working hard. I was previously a D1 Tennis Player and had always been the fittest guy on tour. At 5'10 I wasn't the tallest, big-serving hulk out there, my my lean muscular frame certainly could do some damage, and I ultimately had a very successful collegiate career.

Although I was, and still am, inherently competitive and hard-working, I am also quite shy. Both of my parents were corporate workhorses, and my two brothers and I were raised by live-in Nannies. Bereft of the warm and fuzzy household I craved, I always aimed to please. At the same time, and it was likely because I was closeted and dealing with deeply internalized homophobia, mature alpha men intimidated me. And there were plenty of extremely big egos at this firm....

Phil Pratt was arguably the most intimidating. He was about 6'3 and probably close to 270 lbs. You could tell at one point he was a collegiate football player, but now closer to 60, he was a beefy, barrel-chested man with big legs and a gut. Even still, you knew Phil was a jock. His forearms were thick and hairy, and just about every intern was both afraid and envious of Phil at the same time.

Phil intimated the shit out of me. Definitely not on purpose, but whenever I had to work on something for him, I anxiously knew we'd have to have a one-to-one meeting for me to present my findings. Often in these meetings my anxiety would kick in. Phil would kick back in his chair listening to my voice quiver while my dry mouth didn't help. As my own worst critic, it was at these points where I felt like a hopeless pussy who could never be a partner working at a firm with men like Phil. With my throat tightening and my voice quivering, I just imagined what Phil thought of me...what a scared little boy...how had I even had the balls to get this internship?

By early August, despite the "exposure therapy" of presenting my findings to Phil on numerous occasions, I was still finding myself at peak anxiety when I had to meet with him in his office one-on-one. It drained me every time...and after meeting I felt defeated and worthless. The blows to what little ego I had were gut wrenching. When it got really bad, I almost felt like Phil felt bad for me...but this was a comforting feeling...I was harsh on myself, my own delusions of unworthiness.

It was a Thursday night and I was hunched over my laptop trying to finish my last email before I could catch the last subway and hopefully fall into my bed by midnight. I had no girlfriend to get back to...only my roommate Eddy who was on my collegiate tennis team with me.

I was furiously typing away, over in the corner of the office designated for interns. There was one other intern, Sarah, who I had gotten to know and was still up late with me. As a partner, Phil's lavish private office was way on the other end of the floor, and I hadn't seen him until he was literally half-leaning on the desk next to me.

"Hey Tom" Phil said. I startlingly flinched and my voice cracked as it knotted up when I tried to say "Hey Phil" back to him. I was ashamed but Phil confidently smiled and said "have a sec?" I had no choice. I was able to lower my voice by an octave and mutter "sure" back to him...immediately regretting how I sounded like a prepubescent boy. "Come on over to my office, I want to chat," Phil commanded as we both walked over.

My anxiety being alone with Phil was through the roof. I knew I would freeze up back at his office and it would be the end of me. I thought I was going to slip out of the office, but not tonight.

"Shut the door and take a seat," Phil gruffly ordered. "You seem stressed Tom," Phil commented. "You been getting laid?" he asked. "A handsome jock like you must have all the ladies, right?" he asked...trying to sound rhetorical. "I...I do alright," I stumbled, swallowing my words as my throat tightened. I could feel my face becoming red and Phil chuckled "relax Tom...do you find me scary?" he asked smiling.

I tried my best to reassure Phil I was just another "bull pen bro" by muttering "No" but Phil didn't buy it. Before I knew it, Phil was behind me with his giant paws on my shoulders. His hands were massive, strong and beefy like the rest of him. "Wow!" Phil exclaimed, "these are some of the tightest shoulders I have ever felt...all that lean muscle from college tennis now hunched over that laptop for 14 hrs a day...and this is the result."

Phil worked my shoulders with his massive hands as I winced in pain. I even let out little murmurs of pain as Phil kneaded his masculine paws into my shoulders. Standing behind me, he then tilted my head back and began massaging my tightened neck. I could tell Phil was actually enjoying it deeply, and before I knew it, I was in a trance...a sober high the likes I'll never experience again. I had surrendered to Phil and he wasn't judging me but rather caressing me.

With my head tilted back, it was pressing into his big girthy waist. I thought I had died and gone to heaven as Phil worked through the kinks in my neck...I moaned in both pain and pleasure.

Phil was still massaging me from behind when I felt a growing bulge pressing into the back of my head. I felt lightheaded and couldn't control my own erection. "Look at me Phil reassuringly ordered." I swiveled around in my chair. "No. I want eye contact Tom." Phil ordered. I met Phil's confident stare with a submissive gaze back up at him. It was then that he untucked and subsequently unbuttoned his shirt. He then smiled as he unzipped his fly, knowing full well that this was my first homoerotic experience.

Phil's cock was absolutely gorgeous. At 8.5in semi-hard, I could only imagine what it could grow to. It was a beefy uncut alpha cock. As a "straight" man, Phil had a big bush and humungous balls. His hairy chest and belly ultimately culminating around a big bush designed to keep his two massive balls warm.

Instinctively I knew what I had to do. I had never tasted a cock but had subconsciously fantasized about it since puberty. With his big sausage fingers, Phil guided his semi-hard cock into my mouth. I'll never forget that first experience. Phil's uncut cock head was only just appearing, and I remember the sweaty, musky taste of his dick that had been wrapped up in his briefs for the past 12 hours.

Although my mouth was originally dry from the excitement, as Phil guided his cock deeper into my throat, everything seemed to naturally lubricate. "How is that Tom?" Phil asked. I moaned in pleasure and tried to take even more of Phil's now 9.5 in cock down my throat. With his big strong hands, Phil massaged my head, neck and ears...which only further motivated me to please my big, mature, alpha savior. "See Tom? There's no reason to be afraid...you're a good boy and I'm one of the good guys."

By now I was working over Phil's cock using everything I could muster with only my mouth and throat. Phil's massive, bloated cock head kept hitting the back of my throat. I tried pushing swallowing further but every time my jock body seized as I gagged. My now we were both naked and this 6'3, 270 lbs, 60 yr old hunk was having his way with me. "Look up at me," Phil barked and I obeyed. His man meat was logged down my throat and my eyes were tearing up from gagging. "Awww," Phil gently murmured as he felt along my throat, massaging and feeling his own cock pushing its way down past my Adam's apple.

I put everything I had into that moment...not knowing if or when I'd ever get another chance. I sucked with such enthusiasm that my lean muscular body writhed every time I gagged. I had tears in my eyes trying to force Phil's cock down my throat. "Relax Tom," Phil chuckled, "it'll go down easier." Sure enough, as I focused on relaxing, and Phil gently but firmly pressing the back of my head, I noticed I was suddenly taking most of Phil's cock. My forehead was now pressing against his belly as he gently thrust his cock further down my throat. "Ahhh what a nice, good young man you are," Phil deeply and passionately mumbled. "You ready for the big treat?" He chucked.

I moaned in accordance, and before I knew it, Phil was shooting thick ropes of semen down my throat and spilling into my mouth. I remembered my first taste of semen...a truly unique flavor that I'm still not sure about to this day. That said, being as attracted to Phil as I was, just the thought of his Precum still sends me into a tizzy.

Phil tilted my chin up to look at me from above. He smiled, instantly knowing he had just tamed his anxious, stressed puppy. He slapped his daddy cock on my forehead and mopped his cum-covered dick all over my face, carefully and gently avoiding my eyes.

We had both gotten exactly what we needed. For me it was building a connection with the most intimidating alpha man at firm...one I used to tense up in fear just thinking about. For Phil it was fun but I could tell from that day forward he actually cared.

By the end of august, and several blowjobs later, I had accepted my offer to the firm. My confidence had increased to a level I had not thought possible. To this day I have been at the firm. Phil purposefully made sure I wasn't his associate, while also serving as the best mentor I'll ever have.