My Full First Time

I've not really been looking for this sort of thing, but I haven't closed the door on it either. At 40+, I've got the run of the mill domestic life. A comfortable law practice, spouse, kids.

But I've dabbled.

One day a few months ago I found myself in the middle of an agonizingly boring mediation. I was paired up with another mid-30s attorney named Paul. We represented aligned clients, so the mediator put us in a conference room together. Neither of our out-of-state clients attended in person. Multi-party mediation leaves a ton of free time, as the mediator makes his way between each party.

Paul and I are on really good terms, but we aren't exactly friends. We had drinks in a small group after a bar function a few years ago. He's an Adonis though, without question. A high jumper at a small college, I would put him at 6'3" and around 210. Paul is a black guy, and his dark skin and short hair always made me think of a taller Carl Lewis when I saw him. Paul isn't married, but he does have a six year old. Paul is boisterous, sarcastic, and as genuine as they come. We contrast each other physically, but our personalities are very similar. I stand a few inches taller, but I'm probably walking around at 275 these days. And white. Physically, the only thing I have on him hails from my "glory days" as an athlete at a Power 5 school. I bring that up from time to time when I see him. Paul's a smart guy, he probably always picked up on my insecurity around him.

But on this day we were just two bored guys eager for progress. In mediation I really only have the option to work on other projects, read whatever I can get my hands on, or chat with the other people in the room. After about six hours together, we had collectively exhausted all options. After a brief chat with the mediator Paul and I were faced with 60 minutes or more of downtime and our conversation turned towards sex.

Apparently Paul is bi-sexual, and since leaving college he hasn't kept that completely private. I had no idea. Again, I've dabbled - but I've discussed that with exactly zero people in my life. Discussing that side of me with Paul never crossed my mind, until it did. Spending 6-7 hours in a room with a guy like him disarmed me completely. When I started to share I wasn't looking to initiate anything with Paul. But things can certainly escalate quickly.

I told him about being a teenager and being drawn to erotic literature. Straight at first, but that quickly turned into all manner of gay stories. As the internet expanded that shifted to also watching straight and gay pornography. I held back about always being drawn to bi-racial themes.

I told him about my first experience with a man. Mid-twenties, I was in New Orleans for the wedding of a college roommate. Craigslist was the thing at the time, and I spent the weeks leading up to the trip posting and responding. I was determined to have this experience, and I landed on a very nice gentleman from the area. He was at least 40 and handsome. A principal at a local elementary school. I was staying at the W Hotel a few blocks from Bourbon Street. He was more of a bottom than he led on, but we had a fantastic time. We both came multiple times - he left me with a hug and a kiss, and we were both smiling.

I told Paul about my second experience with a man. Number 2 was probably mid-50s, and a local find on CL. An evening alone resulted in him coming over after I'd offered a blowjob. I was eager to get him over because he had an absolute unit in his pants. After he made himself comfortable on our couch I went to my knees in front of him. Too inexperienced, I didn't come close to taking all of him - but I swallowed his entire load.

I also told Paul about my third and final experience. Business took me to Nashville, alone. Craigslist was in its final days, but I arranged for a married 30-something "dude" to come by my room in the middle of his workday. Basically a repeat of guy #2, but in a decent downtown hotel room. I shot the biggest load of my life, to that point, after swallowing his.

These hookups spanned a decade, so yeah, I considered it dabbling. Somehow, I rationalized these hookups partially by always messing around with married men.

Verbalizing all of that for the first time should have sent my anxiety through the roof, but Paul had completely disarmed me. And then it came - Paul wanted to know if I was attracted to him. Straight and to the point, I responded, "of course."

Now it was his turn to share. Apparently Paul limits this side of him to a very small hook-up group of professionals that he meets quarterly. They all take the day off, get together at a nice hotel, and spend 4-5 hours together. Paul started to tell me about his "partners." KJ is a medical device guy who spends a respectable amount of time in a surgical room with the area's top orthopedic docs. He was a D3 basketball player, but a serious injury early in college led to his line of work. Marcus is an accomplished accountant. Both KJ and Marcus were married with children, and apparently studs that looked very similar to Paul. Paul didn't have to describe their cultural background because I picked up enough to know.

Nonchalantly, he asked if I would be interested in joining them - pending their approval. My previously non-existent anxiety turned into stammering and a red face.

"Oh yes, yes, I would love that."

"Alright, I'll shoot them a text now."

As Paul started to type the mediator appeared out of what seemed like nowhere. I'm not sure how well I composed myself, but we got through it together. Hour 8 of the mediation produced a resolution to the legal matter, and also a response from the group - I was welcomed.

"Can you get free Thursday afternoon? Everything is already set up"

Man, this was going to happen in two days?!

"Almost nothing could keep me away."

Looking at Paul in the eye, dressed to the nines in a tailored suit, all I could think of was sex. I would have parted ways with a hug, a kiss, and/or a blowjob, but a simple handshake was all I got. Now I was faced with nearly 48 hours of my own thoughts, fantasies, and plans.

I bumped into Paul the next morning. I was down to what, 30 more hours! We found ourselves in a quiet corner of the courthouse, with adequate privacy. Our whispering didn't draw any attention.

"Hey bud, still up for tomorrow? KJ and Marcus are still down, but they've only got a couple of hours"

"Paul, you can't imagine how excited I am for this. A little nervous, but wildly excited. The only thing - can I set a few ground rules?"

"Done. Tell me what you want."

"Ok, you know my history. I'm down with all the touching, kissing, and oral we can squeeze in. And I can't wait to watch everybody go at it, but if it goes further I only want that with you."

I didn't have to verbalize it, Paul knew. Even at my age I was untouched there. I had a cherry that could be taken. I'm not sure if that's partially what got me in the door, but it didn't matter.

"Done. I'll let the guys know before you get there. And you don't need to bring a thing, or worry about any details.

Perfect. The wait until the next afternoon was a mixture of ecstasy and anxiety.

I hardly slept that night, but kept with my normal routine in the morning. I went to the gym around 6:00, and followed that with a few hours in the office. Late that morning I ran by the house to trim as much as I reasonably could, shower, and clean myself out.

The hotel was perfect - brand new and in a secluded part of town. Paul gave me the room number - 814 - and the nerves definitely crept back in on the elevator ride up. Paul greeted me at the door and welcomed me in. I went around the suite and got a name and a handshake from everyone. If this were the setup for a video shoot the title would undoubtedly have white guy ganbang somewhere in there - but the atmosphere was the opposite of that. We were all professional guys, and the feeling was more of congeniality - very relaxed and more like a board meeting. Paul was as always in a perfect suit, but his tie was loosened a bit. Marcus and KJ wore tailored khakis, pressed button-ups, and Patagonia vests with their employers' logos on them.

Almost immediately I observed that Paul wasn't lying, they all looked very similar. The average height had to be 6'3", and only Marcus stood out physically. He looked like he might be an amateur body-builder in a few years, with muscles making his shoulders and chest bulge more than the others. I chuckled to myself, reminded that I was the most accomplished athlete in the room (again, "glory days"), but there was no doubt I was in the midst of studs.

There was no rush to anything, despite the forewarning that Marcus and KJ only had a few hours. I was excited and hoped that 2 hours really meant 3, but the situation dictated that I too could be patient. It had been 8-9 years since I had been with a man, but the promise of quarterly meetings was on the horizon. Room service, or one of the guys, had brought up a six pack. It was on ice and Paul had us all grab one. He toasted "to new friends" as we all sat back down.

The only difference was Marcus and KJ both sat on the couch. We were in the "living room" part of the suite. Before, only Marcus had been on the couch. But nothing happened. They didn't so much as bump knees together as we continued to drink. After being in the suite for 20 minutes or so I excused myself to go to the bathroom. I'd caught a glimpse of the massive space when I came in, but the door was mostly closed. As I walked in I stopped dead in my tracks when I saw it. Sitting neatly in a medium sized toiletry bag were condoms and plenty of lube. I'm certain they heard the slight but audible gasp. I shut the door and finished my business (through a semi-erect dick).

After cold water on my hands and face I walked back out into the suite. The scene had shifted slightly - Marcus had his arm around KJ, and Paul did a slow gaze from my feet to my eyes. He had taken his jacket off and loosened his tie a bit more. At first I blushed, but then I went to him.

Paul stood and met me as I approached his chair. His hands went to my tie and jacket, as he started to speak.

"Those two will start out together. I want to ease into things with you before anything gets too crazy."

While Paul spoke to me he started to unbutton my dress shirt. Methodically he worked his way down. In no time he was placing my cufflinks on the bar. Next, he untucked my undershirt and removed my belt.

"Let's sit down for a bit and watch."

We sat on a loveseat opposite from the other two. We were close, like a new couple pressed together at a movie. Not wanting to go too far, but to participate myself, I went to one knee -- first removing Paul's shoes and socks, then my own -- before quickly returning to the cuddle. Marcus and KJ were playfully kissing each other, along with some heavy petting. They weren't oblivious of us, occasionally sending playful glances our way. I turned towards Paul and intentionally inhaled deeply. As my lust for him began to build I wanted to take him in with every sense.

The first change in Paul was a hand on my thigh. He didn't move straight in for my crotch, but given the situation it was a pretty modest placement. I mirrored Paul's movement and moved my hand to his thigh as well. I immediately realized I hadn't chosen nearly as modestly. The edge of my outer palm had most definitely landed on the bulbous head of his penis. We locked our eyes for a moment, before I set my sight towards his thigh. The outline of a significant member ran down the thigh of the leg closest to me. I rubbed my hand up the length of it until I was cupping his balls. Paul closed his eyes and breathed in deeply. When he opened them he nodded towards the other two. Somehow they had advanced their action and were going at it pretty heavy and I had missed them disrobing to their boxers. I think Paul redirected my attention to gauge my comfort level.

My lust for Paul only intensified. We pulled the remaining tops off each other as we started to make out.

"Still good?" Paul asked.

"1000%"

We continued to kiss, but my hands went to his belt and then he lifted his hips so I could pull off his pants. Paul was just in his boxer briefs and my hands went straight for his crotch. Now it was me inhaling deeply -- Paul's cock hadn't reached full rock-hard erection, but it was definitely massive. My eyes went wide and Paul just nodded and smiled. At this point I was ready to establish my role and come out as submissive. I put my hands on his waistband and asked, "may I?" Paul's hand went to the back of my head as he again lifted his hips. He pulled me in for a passionate kiss as I finished disrobing him. As the kiss finished, I leaned back from him. I wanted to see all of him, and I got my wish. Paul was the peak of the male physical form. Strong jaw line, muscles all over, beautiful smile, wonderful eyes, freaking ABS, and a damn hammer for a cock. I was transfixed by the cock on this man. Very closely trimmed from the bush all the way to his hole. He had slightly spread his legs so I could see all of it -- clearly aware the affect he was having on a guy like me. A thick vein ran up the long shaft, and the mushroom head was perfect -- bigger now than when I first brushed up against it. The length, several inches more than I had, was staggering, but the girth was manageable -- I could get my hand around at least. It must have been eight inches or more. Again, he was sporting an absolute hammer. I wanted to go straight to my knees, but Paul had other ideas and his words brought me out of my daze.

"You're going to use your hands, both of them. This cock is more than you know what to do with. Wrap both hands around my shaft."

I obeyed - no other thought was possible. There were other people in the room, but they could have been a million miles away -- for now.

"You want to use your mouth, but not yet. Touch every inch. Daddy likes to be stroked."

I was still in my boxers, my dick hadn't been touched, and I almost came with that one word, daddy.

Paul leaned back slightly more, and his legs got a little bit wider. His huge cock had to be fully erect now, right? I marveled at its perfection. I indeed touched every inch. The foreskin of his cut cock slightly rolled back and forth perfectly in my left hand. I used my right hand to explore his balls. They were perfectly proportional to the rest of his cock -- enormous. Everything in his crotch made me salivate, envious, and raging with lust. His skin was perfect and supple, from his shaft to his taint. I took my time to explore his taint, lightly around his hole, and then with both thumbs to spread open the slit at the top. Bringing out his sighs, soft moans, and smiles turned me on even more -- and the bead of precum gave me the reassurance I craved. Daddy was getting what he wanted, but his words once again brought me out of my daze.

"Marcus"

A name and a slight wave brought me back to earth. I was still in my boxers but the other two weren't. As I explored, they had shed all clothing. As I explored, they kissed and touched, but mostly watched as I got to know Paul's body. Marcus rose from his seat, his fingers getting another touch of KJ's shaft as he made his way over. Marcus had the darkest complexion of the group, and he was glistening as he approached me. Getting my first look at ALL of him, I found myself speechless. He didn't have all of Paul's length, but the girth was remarkable. A khaki wearing accountant may have been approaching, but it felt like a tall-boy can was headed right for me like a missile. Paul spoke again, as Marcus looked down at me.

"Go ahead and get on your knees." I obliged.

"Run your tongue along his shaft, then take the head into your mouth." Once again, without hesitation.

As I did what I was told Paul put his hand on my back. Almost immediately KJ came over and kneeled in front of Paul. The pecking order was clear here, Paul, Marcus, KJ, then me -- Jay. I had plenty of saliva in my mouth, and I went to work on the head of Marcus's cock. In turn, KJ focused on Paul's balls, taint and hole.

Having gotten unspoken permission from Paul, I turned my complete focus on Marcus. I came for Paul, but I wanted to experience everyone. Still on my knees, I explored around his cock with my mouth and tongue. I brought my hands up to his shaft -- together they could wrap completely around him. As I kissed down to the base the shaft seemed to completely cover one side of my face. With a slight swaying of his hips the missile slapped my check playfully. Having found something I obviously instantly loved, Marcus used his fingers to bump his cock all around my face. When it came to rest right in front of my mouth I didn't hesitate, I dove right in and enveloped the head with my lips. With the head completely inside my mouth I brought my hands up to the shaft and worked it with fervor. The girth stretched my mouth to its limits and I bobbed on his member as much as I could. I desperately wanted this man's cock in the back of my throat, but I couldn't get it there yet. Marcus gave me some reassurance.

"Nobody can. You're doing perfect, don't stop." All I could think was, "I may never stop, sir."

After a considerable effort I came up for air. Glancing to my left I got an update on the other two. I never let my right hand leave Marcus's shaft as I watched KJ completely swallow Paul. KJ had his left hand on top of Paul's thigh, with his other hand aggressively massaging his balls and stroking his inner thigh. I was transfixed on Marcus when he approached me earlier, so this was the first chance I got to really assess the rest of KJ. Like the others, he was wonderfully endowed. Great shaft with nice girth. I briefly reached over to fondle him and quickly realized he too was packing more than me. Perfect. I have an average dick myself, that I'm completely comfortable with, but in that moment I found that I had a desire to be the smallest.

I ran my hand down the length of Paul's thigh before returning to fully focus on Marcus. I went back to bobbing on the first few inches of his meat. I strained my mouth around him, eager for more. My tongue swirled as my hands gripped his shaft like a baseball bat. Marcus wasn't forceful with his hips, content to let me work. His rock hard cock, precum, and grunts told me everything I needed to know in the moment. He kept his hands busy - running them through my hair and giving me occasional squeezes on my neck and shoulders. When I came up for air again he nodded approval at my work. He stepped forward a bit towards me - still on my knees and his cock pointed towards the sky, his balls were right there for me as he pressed them into my face. As I took each in my mouth I knew I read the right cues from him when he ran his fingers through my hair and kept them on the back of my head. Giving this stud head, on my knees, felt very natural.

Some non-verbal communication must have happened between Paul and Marcus, because Marcus stepped around me and sat on the loveseat. I had been worshiping this monster long enough that my mouth and jaw were taxed, so I didn't mind a small break. Both on our knees, KJ and I turned to each other to kiss. Our tongues danced aggressively and our cocks brushed together (somewhere I had lost all my clothes). KJ and I swapped partners. Marcus pulled one knee back with his hand, apparently now wanting pleasure at his hole, and KJ quickly obliged. Now on my knees in front of Paul I was free to use more than my hands on him. First the head and then onto the shaft, I swallowed what I could. Three then four inches went into my mouth. I was on my knees to deliver pleasure to him, but I controlled the pace -- and I loved every second. I was aggressive and pushing my limits. My hands were on his thighs as I focused on fucking his cock with my mouth. I found my rhythm as I pressed more of him towards the back of my throat. After several minutes Paul stopped me. He lightly pulled my hair back, and began to speak.