Learning Myself Through Jeff

I first met Jeff some 15 years ago while on an overnight sport-fishing trip out of San Diego. Living and working in Orange County at the time, I had originally planned to drive down that evening with one of my co-workers, but he cancelled out on me at the last minute, so, rather than waste the tickets, I ended up going alone.

As I boarded the boat, I saw that there were only about a dozen other anglers -- most of whom were older men who appeared to have opted for a cold night of fishing and drinking to staying at home watching last season's re-runs, or worse, getting stuck listening to the wife drone on about the latest crisis involving the neighbor's cat.

Jeff was somewhat of a stand-out from the beginning. He was tall, looked to be in good physical shape and was very well spoken, which I gathered based on the group's informal round of introductions. After meeting our shipmates and hearing the captain's safety instructions, we each retreated to what we felt would be our lucky deck spots and began to set up our rigs. Jeff took up a station about eight feet from mine.

Unfortunately, we had picked a bad night to go out. Not only was it damp, but the wind seemed to drive the cold right through you. To make matters worse, the fish seemed to be anywhere else in the Pacific except where we were anchored. No one was getting any action. In our boredom, Jeff and I sparked up a bit of a conversation -- mostly just small talk about work and the weather. He told me that he was a mortgage broker and I explained that I worked as a rep for an advertising agency.

As the evening wore on, and with the beer evaporating from the cooler, we somehow got on the subject of women. Being about 15 years older than me, Jeff told me he was twice divorced and single. I confided that I was between girlfriends at the time too.

"It sucks being without someone to suck your dick every night, doesn't it?" he said laughing. "Amen, I'll drink to that," I replied. "Especially on a cold night like this one. And this beer isn't keeping me warm either. I've got a bottle of JD in my bag if you're interested," I said.

"That would be awesome," he said. "I usually bring a bottle on these trips too, but I was running late and forgot. I owe you one!"

We continued joking and sharing small talk until the boat captain came around to poll everyone to see if we wanted to head in early. It was practically unanimous, so we reeled in our rigs while the crew pulled anchor. What a fucking waste of time and money, I thought, as the boat chugged back to the dock.

Just as we headed in past the breakwater, Jeff held out his hand. "Here's my card," he said. "The next time you're down this way, give me a call. Maybe we can get together for a beer or grab a bite to eat or something -- on me. Oh yeah, and don't forget to call me if you're ever in the market for a mortgage."

I took his card and told him thanks, and gave him one of mine in return. "Same here, next time you're up in the OC, give me a call."

I never really expected to ever hear from him again. Happily, though, I was wrong. What I didn't know was that night had marked the beginning of a special friendship -- and turning point -- in what otherwise might have been just another ordinary life.

Less than two weeks later, I was sitting in my office getting my chops busted by my boss about my expense report when our bubble-headed receptionist popped in. "I hope I'm not interrupting anything important, but Mike, you have a call on line three."

"Ok..." I said, waiting. "...And do we know who it is?" I asked in somewhat of a snarky tone. "I think his name was Jeff something... Oh yeah, and I think he said he was with a mortgage company? I'm sorry, I didn't want to interrupt, but I thought it might be important," she finished apologetically.

"Ohhhh, that Jeff," I said sarcastically. "Yes. It is important. Do me a favor and tell him I'll be right with him."

Jeff's timing couldn't have been better. I told my boss it was a personal matter and asked him to give me a minute. Then I quickly closed the door behind him.

I answered the phone. "Hi Jeff, Mike speaking."

"Hi Mike, thanks for taking my call. I wasn't sure if you'd remember me..."

"Absolutely," I said. "What can I do for you, Jeff?"

"Listen, we're having our annual open house party at our office tomorrow evening and we're reaching out to invite prospective customers. I know this is super short notice so, if you can't make it, I totally understand. I was just going through my wallet and found your card and thought you might be interested in coming down. We're starting the party right at close-of-business, but these things usually last well into the evening. If nothing else, I thought it would be a good networking opportunity for you -- and there will be plenty of eye candy," he laughed.

"That actually sounds great," I said. "I had planned on taking tomorrow off anyway, so that works out perfect. Hey, thanks for the invite!"

"My pleasure," Jeff said. "It's nothing fancy -- business casual -- but we usually have a great time."

"Ok, sounds fun! I'll see you tomorrow," I said and hung up. Cool, I thought. Downtown San Diego on a warm Friday evening with plenty of free, high-dollar wine and beautiful ladies! Now all I had to do was break the news to my already-pissed-off boss that I wouldn't be in the next day.

I made the most of the next morning. With a fresh haircut and new shirt and coat, I knew I'd have to leave early to beat the weekend traffic down the coast. I was glad I did. As it was, I didn't make it to Jeff's office until a little before 6.

I was actually kind of surprised that, with it being a Friday evening, so many people showed up. But the company was having a great turnout. It was a virtual "Who's Who" of the San Diego real estate scene, or as I call it, the "Pretty People of Professional Real Estate."

I was chatting up a very petite and attractive brunette residential agent when Jeff made his way over. "Mike! Hey, it's great that you could make it. I see you're already getting to know some of our guests..."

The way he spoke, you would have thought we had been friends forever.

"Yeah, this is a great party," I said. "Thanks for inviting me. By the way Jeff, this is my new friend Leona."

"Oh, yes. Hi Leona, did you ever get that couple closed on their Gaslamp District condo?" he asked. (Obviously, he and Leona knew and had worked together before.)

"Nope, never did. I was so bummed. Would you believe that two weeks into their escrow, they went out and bought a $40,000 car? Blew the escrow right out of the water!"

"Unbelievable! Well.. It's not the first time that kind of thing has happened and probably won't be the last. Listen, I hate to leave you two alone, but I've got to make some more rounds." Jeff said. "You look great, by the way," he said as he leaned over and gave her a kiss on the cheek. "You look great too, Mike," he added with a chuckle. "I'll catch up with you guys a little later."

"So, Mike, how long have you known Jeff?" Leona asked, turning her attention back to me.

"Actually, we just me a week ago. On a fishing trip of all places."

"Really? Wow," she said. "He really seems to like you."

"Well, what's not to like?" I said in a lame attempt to flirt.

"Then good for you," she said, patting my hand. "I hear he's quite the catch -- if you know what I mean?"

'Whoa, whoa, I didn't mean it like that."

"Well, if you did, you probably wouldn't be disappointed. I hear he's pretty big and hmmmmmmm quite popular, so I'm just saying..." she whispered as she took a sip of her drink. "Now, if you'll excuse me, I have to find to the little girl's room. It was very nice meeting you Mike!"

"Likewise," I said, taking a gulp from my glass. That's just great, I thought! Now she probably thinks I'm gay and is in the ladies room telling all of her friends. Then it dawned me... was Jeff gay? Not that it really mattered, but he sure didn't seem that way.

As the evening began to wind down, I found Jeff holding court with a small group next to the roll-in bar. I walked over and stood there for a while, waiting for an opening in their conversation to thank him and say goodbye.

"You're not leaving already are you?" Jeff said, stepping to the side for a moment. "Can you wait just a minute? I have something I want to talk to you about."

"Sure," I said, curious. "I guess I'll get another drink."

"Ok, atta-boy," he said. "I'll find you in a minute."

True to his word, a few minutes later Jeff made his way over to where I was standing.

"Hey Mike, I'm sorry I didn't have a chance to talk with you much this evening, but it's been kinda busy. I don't know what your plans are for later, but we're thinking about changing up some of our advertising and I wanted to know if you think you're firm would be interested in giving it a shot?"

"Absolutely," I said.

"Great, I'm getting ready to get out of here. How would you like to come by my place and we could talk? I don't live too far from here and it would be on your way back up the coast."

"Yeah, that would be great," I said.

"Good. Here's my address in case we get separated leaving here. Give me just a few more minutes to wrap things up. If you like, maybe we can sit out by the pool and discuss it over cigars and Scotch."

"You got it. That sounds great," I said. "Take your time."

Now my mind was really spinning. Was he serious about possibly moving some of their ad business to our firm, or was he just blowing smoke up my ass in order to get me alone at his place? While it would be awesome to walk into Old Man Peterson's office on Monday morning with a big fat new account, I was concerned about what I might be expected to do to earn it!

I followed Jeff to his house, which was on the bluffs overlooking the Bay. It must have easily been a $5 million home. Once inside, he told me to make myself comfortable. "There's beer in the fridge over there under the bar and several brands of Scotch and whatever else you might want to drink. Take your pick. Also, there's a bathroom down the hall to your left. I'll be right back -- I'm going to change into something a little more comfortable."

From what I could see, the house was impeccably decorated. I took my jacket off, laid it across the arm of the couch and poured myself a glass of Johnny Walker. Jeff came back wearing a pair of swimming trunks, sandals and a Tommy Bahama shirt.

"So what do you think of my place?"

"It's beautiful," I said. "The mortgage business must be treating you pretty well!"

"I can't complain. It pays the bills. But, actually, I inherited this house from my parents. My dad was an admiral. If you can believe it, they bought this place over 40 years ago for just under a hundred thousand. Now some of these homes now go for $10 mil and up, which is well above my pay grade. When I first got it, I had it redecorated and added the pool. You want to sit outside?"

"Sure," I said. I was starting to feel a little bit more at ease that this was actually a legitimate business meeting.

We started our conversation seated in front of the fire pit, sipping Scotch. He wanted to know all about our firm and what my role in it was. He also had a lot of questions about me personally. Where was I from, did I have family, was I seeing anyone? He had an exceptionally calm demeanor about him.

After a while, he got up and turned on the Jacuzzi. "I don't know about you, but I'm getting kind of cold," he said. "Feel free to join me. If you're shy, there's are some extra trunks over there in that chest. And just like that he stripped naked and eased himself down into the water.

One thing was certain. Leona had been right. I couldn't help but notice that Jeff was very well endowed. I glanced over at the plastic pool chest for a moment, and thought better of it. I did go inside to get undressed though. I didn't want to leave my pants and shirt wadded up on the tile next to the pool. As I made my way back out toward the Jacuzzi, it occurred to me how small my cock must have looked compared to his. I quickly sat my glass down and climbed in.

I took another drink, leaned my head back and closed my eyes, still unclear and a little uneasy sitting there in a Jacuzzi naked with another man -- and an almost complete stranger at that. That's when he began THE conversation...

"Hey Mike... have you ever had sex with another man?" Before I could answer, he added, "I'm not judging, just asking."

"Uh, no. I haven't," I said in a slightly questioning tone. (Actually, I hadn't unless you counted the time my friend and I got really drunk in high school and jerked each other off to see what it would feel like to have someone else jack you. I wasn't going to bring that up though.)

"Are you seriously telling me that you've never wondered or fantasized about it?" he asked.

"No, I guess I can't say as I...

"B.S.," he said laughing. "B-u-l-l-s-h-i-t."

My defenses immediately went up. "Look, Jeff, I'm not gay -- I'm not even bi if that's what you're getting at. But I'm guessing you are?"

"I don't like using labels," he said. "I just like having amazing sex."

"So you do go with men and women. That's cool. I think a lot of people do. It's just not my preference. Guys aren't my thing."

"How do you know if you've never tried it?"

"Probably because I've never had the desire."

"You say it like it's a bad thing, but you really don't know do you? Let me ask you this... you like getting blowjobs don't you?"

"Yes, but not from men."

"Honestly, what difference does it make if it's a woman or a man pleasuring you? Ok, have you ever had anal sex -- I mean with a woman?"

"Yes."

"Did you enjoy it? C'mon, be honest."

"Yes, of course I enjoyed it."

"I bet you came harder in her ass than you ever did in her pussy, or probably any other pussy for that matter."

Well, Jeff did have me there. I'd only had anal sex twice in my life, but both times were completely mind-blowing. "Ok, that's true, but..."

"Now think about it. Why was it better?"

"I don't know. It was just hot. And she had a great looking ass!"

"I'm sure that's all true, but think about it. One of the reasons it was so hot was because anal is simply that anal is more physically pleasurable... Tighter hole, more direct stimulation, etc. Secondly, it's more psychologically stimulating -- for both partners. The submissive receiver or bottom (whether woman or man) gets off knowing that she/he is offering up a part of her/his body for the extreme pleasure of her/his lover. For the giver, or the top, it's exciting because he knows that he is physically dominating and pleasuring his bottom."

"I guess that makes sense," I said.

"Now, leaving gender out of the equation for a second and remove all of the labels, it's just sex. It's just two people giving each other pleasure."

"I suppose you have a point," I said. "But even so, I'm still not sure I could do it with a guy."

"But you are curious. I can tell."

"What makes you say that," I laughed.

"First of all, I saw the way you were staring at my cock earlier."

"So what? You're hung like a horse. Who wouldn't notice it?"

"Who wouldn't notice it? Or who wouldn't want it? Stand up," he commanded. "Stand up and show me your dick. Don't worry, I already know how big it is, I just want to see if it's hard or not. If it's not, I'll shut the hell up right now and we will both pretend this conversation never happened? But if it is, no questions asked, you suck my dick and nobody is ever going to be the wiser. Deal?"

I was at a total loss at that point. He had me. It was game over. Checkmate. For reasons I didn't understand at the time, my cock was hard. As I looked back on it, I must have been subconsciously fantasizing about his cock. Maybe not sucking it myself, but surly what it would be like to watch one of his lovers milk the cum from that monster.

Slowly I stood up to reveal my raging hard-on.

And just to prove his point further, he leaned over and without hesitation, took my cock in his hot mouth and easily swallowed me to the base. After just a couple of seconds, he stopped and raised up in front of me.

"See? It's only sex. Why don't we get dried off and go inside where it's warm and we can be more comfortable," he said.

Without saying another word, Jeff climbed out of the Jacuzzi. I followed right behind him with his massive cock, balls and firm ass just inches from my face. I could have just gotten dressed and went home at that point, but I didn't. Instead, I just stared dazed-like at his manhood while we dried ourselves, knowing that in just a few minutes, it would be my turn to go down on him.

I was virtually shaking with anticipation and excitement as we refreshed our drinks and made our way back toward his bedroom. This was literally virgin territory for me. I watched with eagerness as Jeff sat his drink on the nightstand. Then, laying sideways his bed, he adjusted his cock and balls for my easy access.

I took a big drink of whisky and sat my glass beside his. My cock was still at full staff as I positioned my body alongside his, placing my head at the same level of his crotch. "Go ahead," he said.

I leaned in and, and for the first time, took the head of another man's cock into my mouth, just as so many of my girlfriends had done with me in the past.

Although I could detect the scent of chlorine, his cock really had no discernable taste. That would come later, beginning with the sweet flavor of his pre-cum and ultimately the salty/sweet and slightly bitter taste of his full load.

His large head felt velvety and spongy against my tongue. I was fully committed at that point and I tried my best to get as much of his shaft into my mouth as I could. Several times I went a little too far, which caused me to gag, but as blowjobs go, I must have been doing something right because Jeff was moaning and moving his hips in rhythm with my bobs.

I was shocked by how much I was enjoying myself. I would pull him out of my mouth and lick and nibble him along his shaft. I especially enjoyed running my tongue along his slit to lap-up his pre-cum, which was flowing steadily. Every few minutes, Jeff would tell me to suck his balls, which I did gladly.

I was at that point where I couldn't wait to be rewarded with which what I was sure would be a massive load of cum. After all, I knew what I was capable of producing when aroused enough, and since his balls were nearly twice the size of mine, I readied myself for what would surely be a deluge. I would have to swallow as fast as I could if I stood a chance of eating his entire load.

As Jeff inched closer to orgasm, he sat up. I slid off the bed, positioned my head between his legs and began sucking him with every bit of suction I could muster.

"Oh, fuck yeah," he said. "Suck that cock! Suck harder! You know you want that cum. I want you to swallow every drop. Once you've drank my seed, I'm going to fuck that tight little ass of yours. You want to feel my big dick up your ass, don't you cocksucker!"

I was so turned on, I was nodding to everything he said.

"Tell me you want my dick in your ass! Tell me how much you want my cum," he said again. I looked up and paused. "Yes, I want your cock in my ass," I said.

I had barely finished speaking and had eagerly gone back to work on his cock when the first blast of his semen spewed into my mouth. That's when he grabbed my head with both hands, and for a brief second, forced his cock all of the way into my mouth and down my throat. Even though I was choking and gasping for air, I still found myself trying to swallow as much of his seed as I could. Looking back on it now, it was in that exact moment that I had been transformed from a normal, average guy, to a cum-loving cocksucker.