The Summer Associate
I have to share with the Nifty readers what happened to me this weekend while it's still fresh in my mind. Well, truthfully, telling you is only a small reason I'm writing this. After years of reading Nifty stories, I finally have one to tell.
On Friday night I met up with some buddies at a local hangout. It was Gay Pride weekend, so the streets and bars were bound to be packed. I'm 42 years old and I stopped going out partying regularly years ago. But Gay Pride is always a fun weekend, so I was game. We were having a great time drinking, dancing and checking out all the guys. Then I saw him standing shyly alone, leaning against the wall, drinking a beer. I recognized him immediately because of the mole on his left cheek. I couldn't remember his name at first, but I definitely knew where I had seen him before.
I am the CIO at an international law firm here in Manhattan. Each summer we get a slew of interns, which in the legal community are called summer associates. They're law school students who work at big firms like mine during the summer break. They're the cream of the crop, up and coming legal minds. Firms court them heavily. Our job is to treat them like gods while they're here. I recognized the kid as one of the summer associates. Every year I give an orientation speech to the summer group, telling them how important technology is to their success as lawyers. He was in the crowd. I noticed him because of his handsome face and his pretty bubble butt. I suspected he was gay when I saw him, so I was not too surprised to get confirmation by seeing him in the bar.
What makes this situation exceptional is that he couldn't be further from my type. I have always liked men who were older than me. My skin is perfectly smooth. I have always had youthful athletic looks. My ass has always been the asset I flaunted most. Suffice it to say, I have always played the role of the "boy" in a daddy-boy fantasy. At the age of 42 I recognize I'm no longer seen as a boy to most, but there are still daddies out there who go for me with my smooth skin and my fuckable muscular ass. Anyway, the point is, I don't usually like younger guys. Most especially not guys almost half my age. They've never done anything for me. But for some reason this kid was different.
So back to the bar...
I watched the boy for a while, pondering whether or not I should approach him. I am openly gay at the office, so I wasn't worried about being outed. But, I have a strict policy of no fucking with anyone from work. My position is as high as you could go on the non-legal side. Not worth risking it over a piece of meat, or in this case, a piece of ass. But, I told myself I was only considering talking to him since he looked so alone and uncomfortable. I wouldn't pick him up; I'd just strike up a conversation and make him feel comfortable.
My buddy Rick noticed me looking and elbowed me. "What are you looking at? Surely not that kid?"
My other buddies laughed. They all knew as well as Rick did that muscular older men were my type. There was no way I could be looking at that twink.
I nodded, "Yeah, he works at my firm. I'm not into him or anything, just trying to decide if I should say, "hi".
One of my other friends, Javier, said, "He looks delicious. Introduce me."
I gave him the evil eye. I wasn't about to introduce an innocent summer associate to my lecherous Columbian friend. In my group of friends, Javier is the only one who likes the twink look. "I work with him, Javier. I'm not going to play cupid for him."
Over the next half hour I tried to get the boy's attention, but he spent most of the time looking down at his beer. Javier at one point tried to pick him up, but the boy rebuffed him without even giving him more than a glance. Poor Javier. I suppose at some point I'll break the news to him that I fucked the boy later that evening. But I get ahead of myself.
Soon after Javier's failed attempt at picking the boy up, he finally looked my way. He took a double take and I knew he recognized me. I raised my beer and tilted my head in greeting. He did the same and looked down immediately. For about 15 minutes after that, he shyly looked up at me several times. Each time, I was looking right at him. I can't explain it. I want to blame it on the alcohol, but the truth is that even sober I would have been attracted to him.
I finally decided to chat him up. I was really feeling bad for him, standing there all alone. I approached him and saw the look of terror on his face. Hoping I could put him at ease, I said, "Hi, my name's Peter. I think we work together."
He shook my hand and said, "Yeah, I recognize you. You're the IT guy, right?"
I chuckled. This kid was going to be a typical lawyer, thinking everyone else was beneath him. I said, "Yeah, the IT guy. That's me."
He let go of my hand and looked down at his beer, "Sorry, didn't mean to say it that way. I hope you didn't take offense."
I assured him I was not offended at all and that I was just glad he remembered who I was, otherwise I was going to feel real foolish for having approached him. He looked up at me and smiled. I had broken the ice.
We talked and drank for about an hour. I peppered him with questions about his life. At first it was just talk about his aspirations as a lawyer. But, as he got more comfortable with me, he spoke more about his private life. He grew up in a small town in Michigan. He is the youngest of 6 sons; his mother is a good Irish Catholic - no birth control. He is closeted to his family, only having realized he was gay when he was in undergraduate school. As we got drunker, he revealed even more details. He had only been intimate with two guys, though he had frequented the cruisy men's rooms on campus. The guys he had tried to date just didn't do it for him. He said he was pretty much uncomfortable with the whole scene.
My heart really ached for the kid, whose name turns out to be Conner. Officially Conrad, but he hates the sound of that. I tried saying encouraging uplifting things in a futile attempt to be the one who finally showed him how to be comfortable with who he is. I did everything I could to keep the conversation friendly and not sexual. Even though I wanted to rape him right there, looking at his handsome young face, framed by his slightly wavy black hair. He has grey eyes, like a wolf, light skin and that mole on his left cheek. His body, though not muscular like I usually like, is well defined. I don't imagine he has ever set foot in a gym, but he apparently eats well enough to stay in decent shape. Then there's that ass. It is truly the piece de resistance. He was wearing painter shorts that night and, even though they were loose fitting, his ass cheeks still pushed the fabric out in a curve. I wanted this kid and I wanted him bad. But I maintained a perfectly professional demeanor. That is until...
During an uncomfortable silence when I couldn't think of anything else to ask, without sounding like I was forcing the conversation, we were both watching the crowd on the dance floor. Conner placed his hand on my shoulder and leaned up to my ear. At 5'10", I'm not the tallest guy around, but Conner is shorter, probably 5'8". So, he was touching my shoulder and leaning into my ear and said, "Peter, please don't take this the wrong way, but I've thought you were hot ever since you made your presentation to us."
I was speechless for a second, but recovered quickly. I turned to speak into his ear, "Ummm...I'm not sure how to take that the wrong way. I sure hope I've taken it the right way. The feeling is mutual."
He rubbed his cheek gently against mine. My cock stirred. I wanted to reach down and cup his ass. I glanced over at my friends. They were doing shots, apparently unaware of what was going on with me and the "kid".
Conner placed his hand on my waist. As much as I wanted to start making out with him right there, I was stupidly self-conscious of doing so in plain view of my friends. Yeah, I have no idea why it is so important to me, but I didn't want my friends to know I was about to fuck a 23 year old.
I asked him, "Let's go somewhere quieter."
After he shyly said, "OK. I'll hit the men's room real quick", I told him I'd say goodbye to my friends and would be right back.
I told my friends that I was going to escort the kid to a cab, since he was too drunk to get out on his own. Then I'd be heading home myself. Only Rick doubted the sincerity of my story. He gave me a meaningful look and I said, "Aw come on! Since when am I the daddy??" That was enough to convince him that my story was on the up and up.
I retrieved Conner and we headed out the door.
We strolled through the neighborhood, talking more easily now that the pounding dance music was far behind. I was beginning to chicken out, reminding myself not to mix business with pleasure. But then he blurted out. "I want you to fuck me."
Yeah, right there on the street with dozens of Gay Pride celebrants milling about. I was in the middle of describing to him how Chelsea had changed through the years and he just blurted that out. I was stunned into silence as I stopped dead in my tracks. He turned to face me and wrapped his arms around my waist. He looked me directly in the eye and said, "Now."
I stared back, not sure what to say. I stammered something unintelligible, then he gave me a kiss and said, "I have always fantasized about being fucked in public. Follow me." I followed like a lap dog.
He led me to a quiet block, then down a short staircase leading to the basement of a building. It was tucked away so no one on the street above could see us, not even if they were walking right toward us. I saw a couple used condoms and wrappers on the ground. This was clearly a popular spot for quickies.
I was nervous. I am no prude. I have had my share of sleazy encounters through the years, like sucking a guy off on the subway platform, getting fucked in the steam room at the gym, getting passed around at sexy parties, etc. So, the sleazy aspect of the situation didn't concern me. But I was out of my element by being the top. And, I was still unsure about doing it at all with him. I wanted to slide my cock into his ass. I wanted to feel the muscular globes bang against my groin. I wanted to use his hole for my pleasure. All very normal desires, but so unusual for me.
Conner, who had been shy and uncomfortable in the bar, was now assertive and confident. While I was lost in contemplation over what to do, he took matters into his own hands. He got onto his knees and unzipped my shorts. My 7.5" cock was hard - it had been hard for the last several minutes. He deftly pulled it free from my underwear until the shaft was sticking out my fly. He gave it a few tender licks, then took it into his mouth. He was good. His years of experience at the glory holes in the university had made him a good cocksucker. I hissed as I dropped my head back, succumbing to the pleasure. Conner's young mouth was wet, warm, and talented. He swirled his tongue on the underside, nibbled on the head, then swallowed it all down his throat without gagging. After holding it deep in his throat for a few seconds, he pulled off with a slurping sound and a deep intake of breath. He then proceeded to repeat this several times.
As much as I enjoyed his oral skills, I had to get at that ass. And, although we were safely out of view of the public, I felt an urgency to get this going before we were caught. I reluctantly pulled him off my pole and into a standing position. I wrapped my arms around him and brought him into a deep tongue- dueling kiss. His breath tasted of beer and Listerine mints. His lips were full and edible. His tongue strong and insistent.
With my arms around him, my hands didn't hesitate to lower until they were cupping his bubble cheeks. Normally at this point I'd be unzipping the guy's pants, trying to fish out his cock. But I hadn't even thought about Connor's meat. I was, for the first time in my life, completely focused on my partner's ass. I was squeezing it gently through his shorts, then he reached around and guided my hands up and under the waist band. I felt his smooth skin immediately and wondered if he was wearing a jock strap or if he was going commando. Either way, I enjoyed the easy access and, within seconds, found he puckered rosebud. As soon as I touched it he moaned into my mouth and nodded, "Uh huh".
For the next couple of minutes I played with his hole as much as I could with the shorts limiting my movement. I had a finger knuckle deep and with the other hand I was pulling a cheek away, giving my finger more access. The hole felt tight and moist. Had he been sweating? Had he pre-lubed? Had he put spit on it while he was sucking me? Whatever the source, his hole was moist and my finger slipped in easily.
He stroked my steel hard cock with one hand while he fumbled with his shorts with the other. The next thing I knew, his shorts fell to the ground, giving my hands freedom to explore his ass without constraint. But he wasn't interested in finger play. He turned around and pressed his butt cheeks against my cock. He twisted around so he could kiss me again then said, "I'm so glad you were at the bar tonight. I've wanted this for so long but could never find someone I trusted enough to do it."
He then bent over and spread his cheeks. I knew he wanted me to penetrate him right then, but I wanted to eat his hole. So, I squatted down, not wanting to kneel on the dirty concrete, and I got my first taste of his young hole. I immediately realized the moisture on his hole was lube. I'm not sure when he applied it, but the taste was unmistakable. The idea that this kid was as much of a slut bottom as I had been at his age made me leak precum. I don't remember ever pre-lubing my hole before going out. But I always carried packets of lube with me everywhere I went. I loved getting fucked and I was always prepared. The boy scout in me, I suppose. Conner must have been one too.
For several minutes I ate his hole. Alternating between fucking it with my tongue and sucking and nibbling on the rosebud. I also enjoyed kissing and licking his completely smooth cheeks. They were as beautiful and enticing as I had imagined. This kid was gifted by the gods with the perfect fuckable ass.
He retrieved a packet of lube from his shorts while I continued to eat him. Then he straightened up, and said, "Fuck me now."
I stood back up, and his hand was instantly on my hard cock. He spread lube liberally on it, answering one question that had been in the back of my mind from the very beginning of this encounter. He wanted it raw. And I was glad to give it to him.
He arched his back so his ass pressed against my lubed cock. I grabbed his two perfect cheeks and spread them. I quickly found his hole and pressed in. It was tight. Very tight. He recoiled from my first try. But pressed back. Good bottom. Insistent, despite the pain. As I slowly entered his young hole, he used his hands to press back and keep me from going too quickly. If he only knew how understanding I am to the needs of a bottom. I considered reassuring him that I knew what it was like to be in his position, but I decided not to. Let him think I was a selfish top who needed to be tamed.
My head exploded with the pleasure of his tight warm velvety hole. As his tunnel swallowed up each inch of my cock, I shivered in excitement. The situation of being just feet away from the people strolling down the street combined with the incredible feeling of his young ass was overwhelming. I had to concentrate on not cumming as soon as I bottomed out. When my balls hit his cheeks, I paused to take a breath and to enjoy the sensation. I also knew that Conner would enjoy the feeling of fullness you experience when a cock is balls deep inside you.
But, Conner had something else on his mind. He maneuvered so he was once again able to kiss me and said, "Breed me, Daddy."
How many times had I been the one to say that to guys plowing my hole? I never thought I'd hear it being said to me. I had mixed emotions at that point. On the one hand, I really didn't like the idea that I was old enough now to be considered a daddy to guys Conner's age. It was a little bit of a rude awakening. On the other hand, I was so turned on by being dominant and fucking such a beautiful young ass that I didn't care. I simply had the animalistic need to deposit my seed deep inside him.
I gave him a quick kiss, then pressed him forward, so his back was arched again, giving me the best angle to drill his hole. I pulled almost all the way out, then slowly slid back in. Conner did not like the slow pace and started fucking back. I got the hint. He wanted it fast and hard. So, I complied. I grabbed his hips and fucked his boy-hole hard.
I came close to cumming almost immediately, but we were interrupted by the sound of a police car driving down the block. We both stood perfectly frozen in place, fearful that we were about to get caught. But they passed by without noticing us.
With the imminent danger of being caught at the forefront of my mind, I went right back to work. After about a dozen strokes, I hit the point of no return. I felt the cum travel the length of my dick and exit through the head. I was proud that I was giving Conner what he wanted...no, needed. I shot four or five times, then I nearly collapsed on top of him. Conner pressed with a finger the spot between my balls and my anus. Damn! He was trying to get every drop inside of his hole. Understanding what he wanted, I pulled out, squeezed my cock to milk out the last load, then pushed right back inside him to plant it there.
Then it was over. Conner pulled off me and, in a quick motion, pulled up his shorts. As he fastened them he gave me a quick kiss and said, "Thanks. I needed that. But I have to run now."
I cleaned the lube and cum off my cock with the end of my t-shirt, then shoved it into my pants. We then headed up to the street together. We walked in complete silence, my mind still processing the entire encounter, and I have no idea what he was thinking. At the corner he said, "I'm hailing a taxi from here. See you at the office." With that, we parted ways.
It's now Monday morning and I'm about to head to the office. I have no idea what's going to happen. Honestly, I'd really like to fuck that beautiful ass of his again. Though I suspect the encounter with Conner was a one-time thing for him, which is good because it will help me keep to my rule of no playing with colleagues from the office. But, the more important thing is how that encounter has changed me. He awakened something in me this weekend; I'm now obsessed with the asses of 20-somethings. I loved being on top that night. I think after all these years of being a complete bottom, I've finally graduated to being truly versatile.
I'm going to enjoy exploring this new side of my sexuality. And I owe it to an awkwardly shy summer associate.