Copyright 2017, Jeremy J. Watson
When I was a kid, I watched a movie that featured a butler. Seeing that, I wanted to become a butler also. I don’t know what attracted me at the time, but I think it was something about being quietly elegant. Maybe it was also something about witnessing eccentricities, yet not participating. It was as if the butler is the calm center in a swirling storm, and I liked that.
Later, another notion was added to my desire to become a manservant. It came to my attention that a person has a one-in-a-million chance of becoming great. But as a butler, you have a high likelihood of being near greatness. The butler who serves an industrial or political leader can have surprisingly strong influence in world-changing decisions.
In high school, I took home economics and was the only boy in the class. I was afraid I’d be mocked for that, and I was, but there was an unexpected fringe benefit: All the girls in the class liked me, and it wasn’t long before I was dating some of them. Oh, I suppose it helps that I’m tall and thin, but it was that home ec class that really opened doors.
After high school, I went to England and attended the British Butler Academy, better known as the BBA.
My first job was totally non-glorious. I couldn’t find work as a butler, so had to work for a year as a concierge in a hotel. Whereas a butler gets to see eccentricities and remains discrete, the concierge sees more ordinary carryings-on, and rapidly gets tired of endless guys coming to his counter and asking, “Where can I get laid?” There were a couple of interesting events during that year, however.
Once, I was asked to personally bring an expensive bottle of wine to our presidential suite. When I stepped off the elevator, I found the door to the suite partially open. Announcing “Concierge” loud enough that the guests could hear me even if in the bath, I was met with, “Come on in.”
Stepping into the main room, I immediately felt good for the house staff. With many guests in our top suites, there is junk strewn everywhere, including spilled drinks here and there. Not these guests. They were evidently nice, quiet, respectful people. They were not in the main room, and so I went into the bedroom, where I found them both, a man and a woman, openly naked on top of the bed. They acted as if all was absolutely normal. I was momentarily shocked, but remembering to comport myself as a professional, I simply approached with the wine bucket.
“Oh, thank you,” the man said. He wasn’t half-bad looking, even without clothes. He was hairy, but well-groomed, thin, and had a nice smile. Glancing down at his nether regions, I suddenly saw that he had a big, solid erection. I was standing right there, and yet he seemed just fine with that. The woman was a very pretty Asian with small breasts, which I will admit, I like. I was especially attracted to her round ass. She rolled over, and for a moment, I had a clear view of her dark brown asshole and the lower portion of her pussy. It took me a moment to realize she gave me that shot on purpose.
You’ll never guess what she said: “Won’t you join us?”
As if I wasn’t shocked already!
After a moment’s hesitation, I did what any proper concierge would do, “Oh, thank you so much for the invitation, but I have duties today.” I left them with their wine bucket, and left quickly, thinking about that incident for the rest of the day.
When I got home, I had a good wank remembering what I had seen. I was also kicking myself for days for not taking them up on that invitation. As the hotel’s concierge, I could have easily left a message that I was doing something for some of our guests and would return in a couple hours.
On another occasion, a famous rock star was in our establishment for a few days. I won’t tell you his name because you certainly know of him. He was drunk from the moment he walked into the lobby, until the morning he left. I don’t know how he managed such a state so continually, and felt sad for him. Here was a guy who was on top of the world, and he was ruining it all. Rumor has it that he wasted money, and now that a few years have passed, he’s flat broke and still trying to live like a millionaire.
Anyway, I was called to the top-story hallway where all the best suites are located due to a noise disturbance. I discovered our unfortunate rock star yelling incoherently, and trying unsuccessfully to masturbate his soft penis while standing stark naked in the hallway. Although I was quite disgusted, I approached him kindly, and he pushed me away a couple of times. Being fairly large, I wasn’t worried about a physical confrontation, but was quite put off by his nakedness. I really wanted to keep him at arms length or greater. Finally, seeing no other approach, I tackled him like a football player, carried him to his room, and arranged him, still naked, in his bed. He kept asking me whether I wanted a blowjob. That, I certainly did not want.
The final incident before I got a job as a real butler happened just days after the drunk rock star. To my delight, the same couple who wanted the wine delivered had checked back in. I was hoping. well… I was hoping they might possibly repeat their invitation, because I was convinced if they did, I’d really like to participate this time. But more than likely, I had blown my opportunity by declining the first time. In retrospect, asking the concierge specifically, to bring the wine was because they wanted me, not some random hotel employee was an honor. And I fucked it up by declining!
The first two days of their visit, I didn’t hear a peep out of them. My horniness got the best of me, so late in the morning of the third day, I asked the desk clerk whether they were still in residence, and they were. I couldn’t resist, so I went up and knocked on their door.
The man, fully dressed this time, answered. “Oh, Hello!”
It was an enthusiastic greeting. However, when I asked whether they were enjoying their stay, and whether the hotel could provide ‘anything special’ for them, he thanked me, said they were perfectly happy with the hotel’s provisions, they needed nothing, and that was that. Damn!
Friday morning, I thought they had checked out. Oh, well. I found out they hadn’t, and foolishly got my hopes up. At 11am, I got a call to bring them, personally, another bottle of wine.
My heart racing with anticipation, I put a notice on my desk that I’d be unavailable for a couple of hours. I went to the restaurant, got the bottle, filled out the paperwork, assembled a wine bucket with four glasses, and took the elevator to the presidential suite. As I knocked on the door, I felt a bit light-headed and my knees were weak. I knew I had been horny, but this was ridiculous, and certainly unprofessional.
Well, I knocked on the door, but there was no answer. Unlike last time, the door was locked. Now what?
A full thirty seconds later, the woman was taking a moment to fumble with the lock, and then it opened. There she was, a beautiful, short, skinny, dark-skinned woman, probably from the Philippines or somewhere like that, with long black hair. Hold on a second, I should say, really long black hair, all the way down to the top of her butt. She was as naked as the day she was born, right down to having removed her crotch hair. It was all I could do to avoid fastening my eyes on her delicious, rounded, not-droopy small boobs.
I had forgotten to say anything. She said, “Well, come on in.”
I followed her to the back bedroom, where her guy, also bare-ass naked, was idly stroking himself, maintaining his beautiful circumcised erection. You’d think when I came in, he’d instantly cover up with a blanket. Instead he just kept going, and said, “Well, hello! I’m Paul. This is Lilly.”
I introduced myself, “Mr. Carter. Ah, call me James. James Carter.”
I should point out that I was born under the name Franklin Kowalski, but thought “James Carter” was so much more butler-like, With my parents’ help, I had it legally changed when I was eighteen.
“Welcome James. How many duties do you have today?” he asked mockingly, but with a big smile.
Actually, I had quite a few things I was supposed to do, but in that instant, I knew they were not going to get done that afternoon!
Lilly, standing behind me, lifted my jacket off. As she was finishing that, without asking, Paul started unfastening my belt. I felt like this was a dream. It couldn’t be real. These things just don’t happen to ordinary people. Ordinary people get married to ordinary mates, have ordinary children, do ordinary work and then have ordinary retirements. That was a major reason I wanted to be a butler. Because it’s not ordinary.
Within moments, they had my clothes off. I’d like to tell you I was erect from the start, but that wasn’t the case. I was soft as a noodle, and instead of thinking how glorious this situation was, all I was thinking is that I should be sporting an erection now. The more I thought about it, the more the stubborn thing stayed soft.
I guess that’s psychology for you. It will thwart you every time!
They seemed fine with my situation. They guided me onto the bed, where I stretched out flat. Paul made some comment about me having a nice body which I barely heard. That’s because Lilly had jumped cross-legged onto the bed, then shifted to laying on her belly with her head hanging over my crotch and put my penis in her mouth. She sucked my dick for a good minute or two, while Paul ran his fingertips over my nipples. That felt particularly good. No one had ever done that before.
Still, I stayed soft. I was starting to freak out about the lack of an erection at that point. Here was the start of what promised to be the best sexual thing that had ever happened to me, and I was soft. Paul came around to the foot of the bed, and did something weird. He pushed my legs up and set my calves on his shoulders. This partially exposed my asshole. While I watched, wondering what he was planning, he licked his index finger, then placed it against my asshole. It felt wonderful.
That was the second thing that I had experienced for the first time in my life. I thought he was going to press it in, which I was very much looking forward to, but no, he just left it, against my anus.
That did the trick. Pulse by pulse, my penis rose to its full glory in Lilly’s mouth. She said, “Ummm!”
Psychology was getting me again, No sooner than I gave up worrying about not getting hard, I had to start worry about ejaculating. If I came right now, I knew it would spoil the mood. Yet, she kept sucking, and it was so nice.
Reluctantly, I pulled out, saying “Thank you so much, but I’m going to cum.”
Lilly came up and kissed me on the mouth. It was very good French kissing, I might add. While that was happening, Paul scrunched up even closer, and did start to press his finger into my ass. It wasn’t going in very well and almost hurting. He pulled back out, reached over to the headboard and came up with a bottle of lube. His finger well coated, he then came back to me, and twisting a little bit, he placed that finger of his fully into my asshole. Again, I was close to cumming, but I think he knew, because a moment later, he pulled out again. He pulled out slowly, and I could have sworn his finger was a foot long. That pre-cum feeling subsided as I was realizing that I had almost ejaculated without my penis being touched. That, too, would have been a new experience.
They had something specific they wanted to do, and guided me into the right position. Lilly got on her hands and knees at the head of the bed. I was also on my hands and knees, right behind her. And I mean right behind. My mouth was situated so I could lick her pussy, and my nose was right against her asshole. You’d think that would be disgusting, but it was delightful. She had a sweet odor, which I later learned is typical of the slight smell secreted by the area around the anus. It is really quite delightful. Of course I started licking her inner labia right away. I also placed my hands against either side of her ass, spreading it as wide as possible, which she seemed to like.
Meanwhile, Paul was doing something behind me. I glanced back for a moment before returning my attention to Lilly’s delicious ass and cunt, I couldn’t quite see, but figured out from the little red packet that he was putting a rubber on his erection. Oh, oh, what was he planning? I wasn’t sure I was ready for that.
I felt his finger against my asshole again. He took his sweet time putting that finger in me, but I cherished every moment. Meanwhile, I had removed my hands from Lilly’s ass. I needed one hand to hold my upper body so I wouldn’t strain to maintain position. With the free hand, I reached around her small right leg, and managed to reach her clit area, which I started gently rubbing. I found her vagina had become quite wet. It was more than just my saliva. She was really very wet.
When I felt the delicious intensity around my ass increase, It dawned on me that Paul had withdrawn his finger, and was now trying to squeeze two fingers in. He took his time, and although I was expecting pain, it was just totally pleasant.
Lilly started shivering, or jittering or something. I don’t quite know what it was, but it was for sure some sort of effect of sexual pleasure. I didn’t want to change anything I was doing so as too keep her in whatever delightful state she was in.
I felt a slightly scratchy feeling, and discovered Paul had withdrawn his fingers, and was running his tongue around the lower portion of my ballsack and the area just before my anus. His neatly trimmed beard was kind of like sandpaper, but nice.
He quit that after a moment, and I was a bit disappointed. That licking treatment was keeping me very erect, yet wasn’t orgasmic. That’s a really good feeling, by the way. Next time you get a chance, try to maintain a situation where you’re quite erect, but not ready to cum. Just enjoy that state for a while.
While Lilly continued to shiver, and emitted a an occasionally high-pitched squeal of delight, Paul had returned, and he was pressing his fingers against my butt again. Oh, but it wasn’t his fingers. It was bigger and blunter. He was pressing his penis against my ass. I wasn’t so into guys, but didn’t find it objectionable. In fact, I was looking forward to him pressing that big thing all the way into me. I thought it would probably hurt, but was alright with that. Somehow, I came to where I really, really wanted that inside me.
But it wasn’t happening. Paul was just kind of pressing against my butt, and I had the fleeting thought that that might be all I was going to get.
He pressed a bit harder and then maintained that pressure for a while.
Suddenly, pop, my anus stretched to accommodate, and he was in me.
He pulled back out. Then with pressure, he popped back in again. OK, that hurt, but just a little tiny bit. He did it a third time, and a fourth, just going in a little bit, but enough to get that stretchy pop. It didn’t hurt in an aching sense, but it had a bit of a sting. I was fine with that. It was almost imperceptible compared to the totally excellent feeling of being man-fucked for the first time in my life.
Finally, Paul pushed all the way in. I felt the pressure, and a slight ache, which went away in a minute, to be replaced with a super-horny feeling. I could tell he was pushing all the way in me, because I could feel his hairy thighs pressed against my ass, yet I felt that not only could I accommodate more length and width. If he had it, I wanted it.
It was just too much, and again without my penis being touched at all, I felt like I was about to cum. Just as I was realizing that, I did cum, ejaculating all over their bed.
Evidently, being an expert in such matters, Paul knew when to gently, slowly pull out of me, leaving me to recover from my orgasm.
As I lay there, Lilly came over to Paul who was now sitting on the edge of the bed, removed his greasy rubber, and started doing something I wouldn’t have suspected was enjoyable. She was firmly massaging his balls through his scrotum. It looked painful to me, but he was loving it.
She then switched to something else. She had put some of the lotion on the palm of her right hand, and grabbed the shaft of his erect cock in her left. She then started rubbing the palm of her hand over the tip of his dick. I had no idea what he was experiencing, but it made him moan, and kind of yell, and squirm all over the bed as if he wanted to get away. But instead of pushing her aside and leaving or anything like that, he just accepted whatever effect she was having on him. Moments later, he ejaculated.
With all the shaking or whatever she had been doing, Lilly hadn’t had an orgasm yet. Both of us men turned our attention to her, As per Paul’s guidance, she laid on her back on the bed while he kissed her and fondled her beautiful little breasts. I was to lick her clitoris, which delighted me. To my surprise, even though it had only been perhaps fifteen minutes since I ejaculated, my member rose to attention again, growing uncomfortably between my belly and the bed. I shifted position, trying to proudly show it off to my two guests. (My, how my shyness had melted away in such a short time.) I continued to lick Lilly’s cunt, and she started squirming and arching her back, as well as that shivering thing. I felt her wetness coating my chin and running down all over the bed. Again, for a fleeting moment, I thought of the house staff, realizing how they’d now have to clean the bedspread and sheets. They’d have no idea that I had contributed to the mess.
She screamed, and had a crashing orgasm as I continued to tongue her. At that time, I wasn’t experienced with women, so didn’t know whether I was supposed to stop and let her calm down, or what. So I stopped. Simultaneously, Paul and Lilly almost yelled, “Keep going!” I resumed, and she had two more orgasms within the space of a couple of minutes. My neck was starting to ache, and my tongue was getting tired, but I would have gladly kept going all day if she hadn’t finally asked me to stop.
We hugged in a big, lazy pile for quite a while. Finally, they thanked me profusely, and sent me on my way, both blowing air kisses and promising to look me up the next time they were in town.
For the next few months, until I got my first real job as a butler, I kept checking the guest lists every day looking for them, but they never returned. I had questions which to this day puzzle me. I wanted to know if they had done this before. Do they travel from town to town, finding concierges or likely candidates and invite these guys to their bed, or was it just me? Do they particularly like three-ways, or are they more versatile? What were their thoughts about all this? I’ll never know.
I got a job as a real valet, and was delighted. Delighted, that is, until I had been on the job a week or so. It was a family. The parents were nice enough, but they expected me to spend most of my time taking care of their two bratty children. Try as I might, I could not tame those kids. Talk about entitled. The boy was 12 and the girl was 16, and they thought they owned the world. They were so impulsive and impolite that taking them shopping or to a kid’s birthday party, or to their dance and tennis lessons was embarrassing. I started to realize, I was a high-priced babysitter. Two weeks into the job, I gave my notice, and even though they hadn’t found a replacement for me by the end of the month, I was out of there.
Two months of unemployment followed, and my money was running out. I started looking in Craigslist for any sort of job. Maybe a minimum wage retail job would be OK. I saw the city had an opening for a garbage truck driver. I seriously considered it.
At the last moment, the agency called with a possible job. It was a guy who’s identity wasn’t to be revealed until I took the job. He had something marked ‘special requirements,’ which I knew as butler-talk for some sort of eccentricity.
These eccentricities that clients can have range from anything such as duck hunting through swamps on cold winter days to performing one’s duties dressed in strange costuming. I was desperate, and pretty much decided in advance I’d accept any requirements even resembling reasonable. I’d even take on another family with horrible children, if necessary. I also knew I was low on the agency’s list. The old, experienced butlers get the cherry jobs, and the young guys, such as myself, get whatever scraps are left, if any. So, this must have been a scrap. I was curious what the ‘special requirements’ might be that everyone else in the agency had turned them down.
I arrived at the interview promptly at 10am Tuesday morning, and was met by my client’s personal assistant, a shorter, balding guy named Frank. The interview went well until he revealed that the family I had worked for dissed me. Damn them! Their children were monsters, but they couldn’t admit that. Instead, they blamed me for mishandling the kids. Their reference was very negative. I did my best to tell the truth about that situation, that the kids were going to grow up and be miserable adults and despite my best efforts, I couldn’t control them. I was sunk and started imagining myself bagging groceries for minimum wage.
Oddly, Frank then went on to describe the work, and the client’s needs. Could it be he found me acceptable anyway? The client, as yet unnamed, was a very wealthy industrial leader. I could tell he was successful from the home. It had twenty rooms or more, including an indoor tennis court, ballroom, theater, and swimming pool. Evidently, the guy was very pressed for time, and was a bit of an efficiency freak. He couldn’t tolerate anything that wasted his time. Then, my duties were discussed. I was to be more of a personal assistant than a valet. I wasn’t so sure I’d be so good at managing appointments, booking air flights, and so on, but I was certainly willing to learn.
I asked Frank why he was leaving. It sounded like a pretty good job to me, forgetting about the ‘special requirements’ for a moment. Surely, that was no big deal, right?
“Well, you have to understand something, and I hope this doesn’t cause you to bolt and run for the hills.”
That certainly got my interest up. What could he possibly be talking about? Did the client work for the Mafia or something?
“OK, so there’s something he likes, and I just can’t… well, I can’t…”
And he paused, composing himself.
“He has a requirement most evenings that I would like to fulfill for him. Oh, I tried to be willing to do it, but I just can’t go there. I’m happily married, you see.”
Holy fuck! What was this guy trying to tell me? I sat politely waiting for him to spit it out.
“He wants, well,… He wants handjobs.”
I laughed. I know I shouldn’t have. This was quite painful to Frank. But to me it would be a breeze. Not that I’m gay or anything, but that experience with Paul and Lilly taught me that I’m not afraid of guys. You know, satisfying guys.”
Seeing the pained expression on Frank, I stopped laughing, and apologized, explaining that I had expected something worse.
It was his turn to laugh, “What could possibly be worse?”
We both laughed, and the tension was broken. Suddenly, the PA and I were like co-conspirators. Without me so much as saying so, Frank knew I was willing to take the job. Without him so much as saying so, he was glad I was willing to take the job.
It seemed he was stuck being the personal assistant for his client until he could find his replacement. No, he had never actually given his client a handjob, but they were no longer getting along well. He explained that he felt his employer had felt embarrassed about asking and being turned down. His employer felt he couldn’t continue to have a PA that wasn’t on his wavelength, as he called it.
Several men, and then some women had been interviewed, but when they heard the special requirement, one after another had politely declined.
My next interview was with the client himself, the man who was, hopefully, to become my employer. When he came down to the little office off the kitchen, I smiled inwardly to myself. I knew it was somebody wealthy, but I had no idea it was going to be Justin Cableson. Last I heard, he was the third richest man in America. He looks as good in person as he does in the media. Tall, clean-shaven, longish hair, graying temples, sleek build, and a self-assured walk as if he knows everything will go his way. I liked him immediately, special requirement and all.
He seemed like a straight-shooter to me. In his interviews he always got right to the point, and wasn’t afraid to state the truth. I decided to respond in kind.
After brief introductions, I came right out and said, “I heard about your special request, and would be delighted to provide that service.”
“We’re talking about handjobs, right?”
Boy, he was a straight-shooter.
“Yes, I had a former client who liked similar sexual activities, and I was not only happy to comply, but my client was happy with it too.”
I didn’t go on to say that this ‘client’ was actually just Paul and Lilly and it was a one-time thing.
“Oh, and who was that?”
Ah, he was testing me. “You know I could never tell you that, right?”
I passed his first test.
“Can you take shorthand?”
“No, I’m trained as a butler, not a personal assistant, but I’d be happy to learn anything you need.”
“No. I was just asking. Can you work a cellphone?”
“Big-time. For instance, I’d have no trouble installing apps to do things like a sophisticated sound recorder for dictation.”
“Dude, I like your can-do attitude.”
“Will $110,000 annual salary and your own room here in the house be OK?”
“Will I have to wake up at all hours for ‘special requirements’ or anything else?”
“Whereas the occasional emergency could happen, it’s not likely. I’m kind of a weirdo. I don’t drink or do drugs, therefore I don’t get drunk. I like to go to bed at 9:30 and get up at 5:30. Can you handle that?”
“My favorite hours! Sir, I’m so happy to hear that you don’t do drugs or drink. A man after my own heart. You don’t smoke, do you?”
“I used to, but you’ll be pleased to know I’m never going back.” Oh, and please don’t call me ‘Sir.’ I’m Justin.”
Realizing that he did seem to prefer an informal attitude, I answered in a very unbutler-like way, “You got it Justin! How about $120,000?”
“How about $115?”
He laughed. “I would have paid 120.”
I laughed. “I would have accepted 110.”
We both laughed.
My work started the next day. I was happy about that, because my money was all gone, and I was starting to dig into my credit cards. The only disappointment was that all my life I had wanted to be a butler, and it was turning out that I’d be more of a personal assistant. I could deal with that. The handjob thing didn’t bother me at all. Perhaps it should have. Strangely, I was actually looking forward to that part of the job.
Frank, the former PA was happy too, since after a single day of training, he could get on with his life. The training day went nicely. It turns out Justin liked the idea that I was formally trained as a butler and decided he might like to take advantage of some of the things I could offer that a plain old personal assistant would be unable to provide.
That first day found me at Justin’s mansion at 7am, with a car full of belongings. Frank showed me to my room, and I quickly unpacked, meeting Justin, Frank, and some other guy in the little office off the kitchen. That was to become my office. I was given the password to the computer, and shown where to find important phone numbers and things like that. The other guy was Duane, the cook, and he had a somewhat larger office next to mine.
At 8am, I rode with Frank and Justin to his office, where I shadowed them, learning what’s what, and meeting so many of Justin’s employees that I couldn’t keep track.
At lunch, I assumed Justin would go one way, and we’d go the other, but he invited us to the best restaurant in town, and to my relief, he treated. I thought he’d talk about business, but he spoke mostly of his past, telling us rather humorous stories of getting into trouble in his teenage years. I almost came out and asked why he wasn’t married, but held my tongue. I could imagine that might be a sore point.
In the afternoon, I met more employees. His headquarters is a 210,000 square foot, four-story building. There’s no way I’d know everyone, or what they all do. It seems most are either programmers or graphic designers.
At 5pm, almost on the dot, Frank thanked Justin and was on his way. I felt a momentary stab of fear. Suddenly, everything about taking care of Justin was in my hands. What if I didn’t know how to handle travel plans, or didn’t realize a certain person had a special need or something? In a few minutes, I got over it.
I drove Justin home in the car in which we had arrived. It was my first time driving the car, and I rather liked it. It was unconventional, much like I came to find out Justin can be. It was a Ford, F-350, six-wheel one-ton diesel crew cab pickup truck with a Lance camper on the back. Weird choice for a billionaire, don’t you think? The thing had a six-speed manual transmission, which I tried my best to shift smoothly, as Justin sat next to me, fiddling with his cellphone.
The only thing he said on the five-mile trip was, “They say ‘don’t text while driving,’ but I think it’s OK if I text while you drive, right?” followed by a brief laugh.
I pulled into the driveway, nearly plowing over a lamp post on the way in. Justin just giggled.
As we walked in a back door leading to the kitchen, he said, “Would you mind coming by around 7pm?”
“Come by where?”
“Oh, right. My bedroom.” That’s on the west side, along the hall just in front of the swimming pool.”
Interestingly, my room was very close by.
I arrived at seven on the dot. Butlers are very careful about timing. I was expecting him to get right down to this handjob business. He didn’t.
“I’d like to start taking advantage of your services. In this closet, are most of my clothes. In those drawers, you’ll find T-shirts. Over there, the ties, and there, pointing to yet another closet, are the clothes I don’t like. Your job, if you don’t mind, will be to set out one set of clothes every day, so I don’t have to figure out what’s what. You’d be surprised how many minutes I waste looking for the right things to wear.”
“Ah, interesting. I understand.”
I efficiently picked out a set of clothing, underwear, shoes and all, and arranged the items around a chair near his bed.
“That’s it. Now treat yourself to a swim in the pool, or a hot tub, or watch some TV in your room, or the theater, if you’d like.”
“Thank you, Justin. I don’t really watch much TV.”
“Really! Neither do I!”
I could so tell I was going to like working for this guy. I was also surprised that he didn’t get right to his ‘special requirement.’
The next day, Thursday, was much the same. To the office at 8, I did a few PA things, but nothing important, really, mostly looking for ways to be useful. Justin had a business meeting which I didn’t attend, eating lunch with nothing for company but an ebook on my phone at a nearby diner. I filled the afternoon acquainting myself with an office that had been set up for me in the building. We went home at five, again with Justin texting on his phone the whole way. I started to get the idea that much of his business is conducted by texting. Later, I found he can log into his server farm, update software, and all sorts of cool things right from that little phone of his. Mostly, his employees do all that, but he likes to stay on top of everything.
Friday was mostly a repeat of Thursday. I was starting to worry that my duties as a PA were nearly non-existent, and was trying to find some way to be useful during the day. I had thought the former PA had lots to do. I couldn’t quite tell, but it seemed Justin had other people handling his email, setting appointments, and all that. I didn’t understand. Perhaps I’d need training which was to come later.
Justin wanted to go the the office again on Saturday, so we drove on over at 8am again. He introduced me to a guy I hadn’t seen before. This was Rodney. He was to be the new PA. My heart sank. Had Justin decided I wouldn’t work out? Seeing my expression, he quickly added, “I’ve decided, James, that I should take advantage of your special skills, and utilize you entirely as my butler.” I went from great fear and disappointment to joy in approximately five seconds flat.
“By the way, James, it’s the weekend. Do whatever you want. Stay in the mansion, go somewhere, whatever you’d like. Take the Ford truck if you want. Do you like camping?”
As we arranged, I took the truck home, and left Justin in the office. Taking my time to study the mansion, I realized it was a fucking mess. There were piles of dirt and dust here and there, the hot tub area was actually moldy, even the multiple-acre yard could be better kept. There was a staff of six other people who were supposed to be taking care of those things, but they obviously weren’t being done right. I decided this is where I could fit in.
I worked the whole weekend by myself, physically emptying wastebaskets, cleaning toilets, whatever needed to be done. I decided I’d mostly lead by example. My role in life wasn’t to chagrin people into doing their jobs. My job was to inspire them to do their jobs. We learned about household management at BBA. Often the butler is head of household, in charge of everyone in the kitchen, the home, and the grounds.
Sunday afternoon, I texted Justin, to find out whether if he agreed with my thoughts. He did. I asked whether he’d mind making an official announcement to the staff that my role was to take charge of the house. He didn’t mind. He also never made the announcement.
It took months to bring them all in line and doing their jobs properly, especially since I couldn’t get Justin to specifically tell them that I was their manager. I did it entirely without embarrassing anyone, leading by example, and encouragement. You know what? It worked. There was one young fellow who was kind of lazy and toxic, telling the other staff that I was a slave-driver and all sorts of things like that, but somehow, even he came around. I think the unifying factor was Justin. Everyone found him likable. I did to, but I have to admit his management style was lackadaisical, giving everyone too much autonomy. On the other hand, he was managing a multi-billion-dollar company just fine.
Within the first couple of months, Justin never really wanted anything personal from me besides laying out his clothes.
He never requested the ‘special requirements’ and I soon forgot all about that.
He didn’t ask, but I discovered he had a habit of taking a quick shower at 7:30pm most nights, jumping in the hot tub for a few minutes, then finishing with another shower. I realized the second shower was to rinse off the chemicals. I suggested that we update the hot tub to chemical-free. He had an ultra-violet filter installed, and then asked me to celebrate with him.
At 7:30, I met him in the tub room next to the pool. Up until then, I had never seen him use the pool, and never seen him actually use the tub either. I had only seen his towel-clad form going to or from the tub.
I came in, and he was unabashedly stark naked. That was the first time I had seen him that way. It was natural enough. We both jumped in the tub, me having removed all my clothes also, and talked about life in general for fifteen minutes. He also thanked me for the chemical-free idea. He then stepped out and wrapped back up in his towel. I couldn’t tell for sure, but he seemed to have a semi-erection.
He went his way, I went to my room. I hadn’t been with anyone in a while, and seeing him that way did something to my brain. Now, I’m mostly interested in women, you know. But still, I felt the need to jerk off, and I did, with visions of Justin for some reason.
A few days later, I came in to arrange his clothes. I had forgotten it was Saturday night. Well, I didn’t totally forget. I was going to lay out Sunday clothes: Jeans, T-shirt, and sandals, but had forgotten that James doesn’t generally go to the office on Sundays and that changes his Saturday evening routine. I didn’t really know what hed did on Saturday evenings, but he’s never in his room at that time on weekdays. So I just came right in, and found him there, jerking off in the recliner next to his bed. He didn’t have a chance to hide, although he quickly tried to pick a shirt up off the floor and cover his erection.
“Nothing to be sorry for. My apologies for barging in.”
“It’s to be expected. You’re my butler, after all. I shouldn’t have any secrets from you anyway.” And with that, he threw the shirt back on the floor. His erection was subsiding.
I felt badly for wrecking his private moment. It also brought back to my mind the long-forgotten ‘special requirements.’ Without thinking it through, I blurted out, “Remember when you first hired me?”
Now at this point, I knew I was making a mistake, but I was committed. Plus, Justin has often said he is a fan of communication. Whenever any sort of situation arises, he feels it is best to communicate it fully.
“Well… Whatever happened to the handjob thing? It seemed at the time that was important to you.”
“You’ve always been so proper James, that I thought it might not be right. Might bring you down or something. Besides, when I first thought of it, I used it more as a tactic for getting rid of Frank, which worked nicely, don’t you think?” With that, he smiled big.
“Really?! I mean that you thought it would bother me?”
Well, you’ve been so good at running the house and everything. You’ve even gotten the cook to use less sugar. I didn’t want to risk wrecking a good thing.”
“Well, thank you, and I’m honored. But I would have. Still will, if you want.”
“I wouldn’t know how to proceed. I’ve always been asexual I think. Or, I guess the term is ‘solo-sexual.’ I’ve been too focused on business, not enough on my social side. I dated a girl only once, and it was a disaster.”
“What do you mean?”
“I’m probably on the spectrum. You know, kind of Asperger-like.”
Justin, you’re as from that as anyone I’ve ever met,” I laughed.
“Well, something’s wrong, and I’ve been quite lonely. About as far as I go with sexual things is this woman in town. She’s a massage practitioner.”
“So you just get massages?”
“Well…” and he hesitated, “She gives me happy endings.”
“Sounds fun. You’ve never wanted to date one of your employees, for instance?”
“That wouldn’t be right.”
“What if it was?”
“There is this one red-headed woman, a programmer…”
“Would you like me to arrange an introduction?”
“No, that wouldn’t be right.”
Another long pause.
“But, could you? That would be so excellent.”
“It might be a bit weird, what with you owning the company and all, but I think I could arrange so that if she is interested, you two could get together.”
“Have someone send me her contact info, and I’ll take it from there.”
“Dude, you’re such a friend!”
“It’s just part of the job, what a butler does.”
“What about you, James? I mean, if it’s OK to ask. What about your social life?”
I realized I had been absent-mindedly staring at his now-soft penis, and quickly looked away.
“What about your social life? It it something you can talk about?”
“Ah, well, yes. Come to think of it, I’ve been kind of solo-sexual like you. All my life I’ve wanted to be a butler, and have been focused on that. Oh, I have had some sexual experiences, some of which were quite weird…”
“Weird?” he interrupted.
“Oh, like this one couple I met when I was working as a concierge. At that point, I told him the whole story about Lilly and Paul, without revealing their names or exact descriptions, of course.
We’d been talking a good hour, and I found myself sitting on the edge of his bed, very unbutler-like, while he remained unclothed in his recliner. Again, I found myself staring at his penis. As I had been relating more details than I probably should have about exactly what Paul, Lilly and I did, his penis had started to rise again. Now, it was a six or seven-inch tower sticking straight up at a 90-degree angle to his body, and pulsing.
Now, if it were me sitting there, I believe I’d ask my butler do come help me out with it. But he didn’t. He was too shy, too polite.
I decided I had to take matters into my hands, quite literally, even if the situation might turn weird. I was pretty sure it couldn’t get too out of control. I knew I wouldn’t lose my job, no matter what.
I stood up, to a slightly puzzled look in Justin’s eyes. I came over, and knelt by the side of the recliner. I slowly, hesitantly, reached out, and touched, not his penis, but his scrotum. I thought that would be less personal, somehow. Like a better place to test the waters.
He could have done anything. He could have pulled away and yelled, “What the fuck?” I’m sure some guys would. I was also sure Justin wouldn’t. I was right. Instead, he scooted forward in the chair, spreading his legs a bit, so I could have better access.
I touched his scrotum more boldly. I could see his balls pull up a little bit at my touch. It also felt intriguing. My own scrot is covered with hair. His was soft and silky smooth. I think it might be naturally that way. He’s less hairy overall than I am. I started touching his scrotum more boldly, eventually working up to feeling the balls within with the thumb and first two fingers of both hands. I know that guys, including myself, can have sensitive balls, so I was quite gentle.
“That’s so excellent, I can’t even tell you! Can you go ahead and squeeze a bit firmer?”
I continued to massage his balls, noticing that his penis was rock-hard, sticking straight up, and again pulsing a bit. I noticed my own penis was starting to feel constrained in my pants.
“Yes, it feels great.”
So, I continued to massage his balls. At one point, the right one slipped from my grasp and jumped, like a wet bar of soap, to another position in his scrotum. He flinched.
“No, it all feels great. In fact, if you don’t mind, squish them both around like that some more.”
I was rather surprised, because I thought this would hurt him, but he seemed to be loving it.
My back was starting to tweak, so I had him move to the bed, where I pulled up a small rolling chair, then continued the ball massage a bit longer.
After a while, I decided it was time to go for the main attraction. Leaving his balls alone, I then wrapped one hand around the shaft of his warm, firm penis, and just started pulling the skin up and down a little bit.
He immediately ejaculated, with warm cum flowing over the top of my hand, and onto his stomach. I didn’t expect it to happen so soon. Knowing how I feel immediately after orgasm, I let him down very slowly. I stopped stroking right away, of course, but didn’t let go of his penis for about 30 seconds, until I saw that he had calmed down.
For a moment, no words passed between us.
“Thank you so much James! That was a dream come true. I had dreamed about, and hoped for this for so long, I can’t tell you!” Cool, because I hadn’t been entirely sure if it was just a way to get rid of Frank, or if he really wanted this, or just what.
The next day we did the same thing, and the next and the next. It became a regular service I performed for my employer most evenings. Even though he usually took much longer to ejaculate than that first time, I enjoyed giving the service very much.
Soon after finishing with Justin and laying out his clothes for the next day, I’d retire to my own room, and jerk off, almost always with images of Justin’s penis being foremost in my mind.
Almost from the start, Justin offered to reciprocate, but I declined. I had this silly notion in my mind that I’m the butler, and he’s the client. It had to be a one-way street.
One time in his room, something came over me. His penis had been close to my face. I leaned down a little more, and the next thing I knew, the head of his penis was in my mouth.
“Oh, my god!”
I paid no attention, just drew his penis further in. He came in my mouth quite quickly. I’d have thought I’d be grossed out, but I rather liked the taste and texture, swallowing the whole load.
“Oh, James, you didn’t need to do that, but I did really enjoy it!”
“My pleasure!” and I meant it.
Pretty soon, there were three things that I mixed in varying quantities to our sessions. Testicle massage, ordinary handjob, and blow job. I also got some books on massage, and learned to give a proper massage, especially back, neck and shoulder rubs. They weren’t sexual, per se, but he liked the massages very much also.
Over the weeks, he kept asking about reciprocating, and I kept declining, resolutely thinking it wasn’t proper.
One day, while I was dusting some items on a fireplace mantle, I was running a little exercise we had learned at BBA through my head. The idea is to put yourself in your client’s position, so you can better understand how your services will best suit what your client wants.
Holy fuck! Suddenly it occurred to me that if I was Justin, I’d want, actually want, to give the butler some attention. I’d want to fondle the butler’s dick.
So that night, I sheepishly asked Justin if he wanted me to participate in some way. with sparkly eyes, he said, “I’ve been waiting for this!”
I quickly stepped out of all my clothing. That in itself was a delight. I had been keeping his room warm so he would be comfortable naked, but it had been a bit of a burden on me, causing me to sweat under my clothing.
It felt strangely revealing after all this time. Oh, I had seen him in the hot tub, and he had seen me naked, too. But on this evening, I was feeling a whole combination of things as I pulled off my last bit of clothing, my boxers, in front of Justin. I was simultaneously a bit scared, as if I was about to do something naughty which would land me in the principal’s office, proud, and relieved. Oh, and surprisingly horny, too. The minute my clothes came off, I was sporting a major boner in front of Justin.
He gasped, and that made me jump. We both laughed.
Suddenly, he was me, instructing me to lay on his bed. He started right in with a blowjob. No ceremony, no touching, and I came right away. Way too soon. I regretted it, just in case we wouldn’t ever do this again. I had wanted to last much longer.
I then ‘did’ him, and we were both happy.
I had done some research on the girl in the office, the programmer, and approached her in a very round-about way, letting her know the boss was interested in having lunch with her some time. She declined. Nothing more was said about it.
In the meantime, Justin and I continued our activities. The usual scenario changed a bit. I always entered his room naked now. Whereas he seemed quite satisfied overall, I thought it would be a good idea to learn new techniques and mix them in to keep things fresh and fun. I read up on the Internet, and discovered some things that I tried. Some worked well, some not so much. Some guys like things pressed into their peeholes. They call it sounding, and they can get quite serious about it, putting long flexible tubes all they way into their bladders. I tried it on Justin, going in only about four inches. While he didn’t hate it, he didn’t seem to like all the preparations, and the safety issue. You see, one has to be careful not to introduce bacteria. He also said it stung to pee for a couple of days afterward. I felt bad about that experiment, wishing I hadn’t troubled him with it.
Just to put that to bed, I had him do it to me. He had purchased a kit of things called rosebud sounds. By the time they arrived, he had decided he didn’t want to use them. Being in a different economic class, I don’t like to see anything wasted, so I decided it might be fun to try them on me. He was all for it. By now, he was getting as much a kick out of seeing me with an erect cock getting sexual pleasure as I was enjoying doing things to him.
So one night, he slathered the things in alcohol, let it dry, then applied some sterile lube to a sound, and the tip of my dick.
Now, these rosebud sounds are quite long, like fifteen inches, and come in a set of sizes, with tips ranging from small like a grain of rice, up to about a half-inch in diameter. The long portion of the sound is thinner, so it is like having a rounded little bullet pushed into your urethra.
My peehole is wider than his, and so he started with a medium size sound. He pushed it against my erect cock, and nothing happened. He pressed gently, but a little harder, and I felt a pop as it suddenly slipped through the opening. He felt it pop too, and it must have alarmed him a bit, because quickly withdrew it. Going in, it felt good. Coming out, it stung just a little bit.
I asked him to do it again, and after a minute, it popped back in. He ever so gently tried pushing more, but it felt like there wasn’t enough lube, so he took it back out. He pressed the lube right onto my peehole and squeezed the tube. It wasn’t quite right against my peehole, so nothing came out. He readjusted a bit, and squeezed too hard. I suddenly felt the lube rushing in and inflating my urethra. Boy, did that feel interesting! I almost ejaculated right then and there.
Then he reintroduced the sound, and sure enough, it started falling in of its own weight, with just the slightest guidance from him. He held my dick up at approximately the right angle so that the sound would have a clear path as deep as it wanted to go. Soon, it was in way deep, much farther than I had expected it would go. It went just a bit more, and pressed against something deep in my body that was amazing. I felt a great feeling building up as he held the sound there. It was sort of like a gotta-pee feeling, but enough different to be very interesting. Evidently the sound was against a sphincter. I had read that there are two sphincters. As he pushed through the first one, the pee feeling subsided, and I was almost disappointed. Not for long, though, since he pushed it on through the second sphincter, and on into my bladder where it slid freely in a couple of inches. That was great!
He just left it here for a moment, while holding my erect cock with his other hand. I was not intending to cum, and didn’t think I was close, but I came. I was concerned that the sound would block the cum, and didn’t know whether that could be a problem, but the cum just flowed out around the sound.
As he slowly pulled the sound out, it stung a bit.
For the next three days, urinating became quite a problem. It really, really stung! I decided that while sounding was fun, I was done with it. I’m told that your urethra strengthens or something so that you no longer have stinging, but I was also afraid of infection.
A milder trick I had learned, which Justin and I both loved was a simple matter of holding or sort of pinching the frenulum. That’s the little fold of skin below the head. By lifting the penis by the frenulum, and just holding for a while, you can get a guy very pre-orgasmic, and eventually, without stroking, he can cum.
Next we discovered a Japanese technique called glans blame, also known as apple polishing in America. I read about it, and decided to try it on Justin. I had seen it once, long ago, when Lilly did it to Paul. The idea is you coat the palm of one hand with lube, and rub it over the head of the other guy’s dick, the glans. It’s supposed to be intense.
I grabbed his dick in my left hand, with just the top sticking out of my fist, and started rubbing with my right palm. He yelled and I immediately stopped. Evidently it was much more intense than I was led to believe.
So much for that idea, or so I thought. In a moment, he asked me to try it again, but more gently. I did, and he didn’t stop me this time. Instead, he squirmed and wiggled as if he had to get away, but he didn’t actually leave. He just took it, whatever it was. I had no idea what he was feeling, but he seemed to be liking its intensity.
I kept going for at least a full minute, and he settled down. After another minute, he told me that it was a unique new sensation that I’d have to experience for myself. Having seen him squirm all around like that, I wasn’t so sure.
On the other hand, I was intrigued, so I switched positions with him on the bed, and let him try. Sitting in his small rolling chair next to the bed, he now clasped my dick in his left hand while simultaneously holding back my foreskin. He just touched the tip with his palm, and I jumped. That was intense! Like him, after a moment, I wanted more. He rubbed gently, and I tried to hold on. It was just too much, and I had to stop him. Oh, it was such a crazy feeling! It made me twist up like a pretzel.
I learned later that uncircumcised guys have a much more sensitive glans.
One day, I got a text that I knew would delight Justin. The programmer woman had reconsidered my offer. Andrea was open to a lunch with Justin, as long as I would come along. I hadn’t met her personally, but the research I did by asking her fellow employees and looking up personnel records indicated that she had no police record, a strong resume, a good work history, and was liked by her co-workers. Her picture was really something, but I assumed it was taken several years ago. The pictured revealed a very light strawberry blond girl with high cheekbones, a small nose, and very light eyebrows. I’m not used to seeing blond eyebrows, and so to me, she looked a bit goofy, but appealing at the same time.
The three of us met for lunch and to surprise, she looked just like her picture, but even better. She was a bit nervous. After all, this was Justin Cableson sitting with her. He was her boss like ten levels up, and a billionaire. We both encouraged her to relax, which probably only made her more tense.
To my astonishment, Justin, too, was nervous. I don’t know whether she detected that or not, but I sure did. He wasn’t saying much, and so it was part of my duty, I decided, to help move the conversation along.
I asked her whether she enjoys her work. She did. I asked her why, and it took her a moment to get rolling, but that sort of broke the ice as she talked about the notion of working quietly on a big project, the satisfaction of sorting out problems, and how programming was like playing a never-ending video game.
Justin sparked to life. After all, he had started as a programmer. He knew just what she meant, and they got to talking about it. I excused myself and went to the bathroom for a very long time. Actually, after the bathroom, I went outside and read an ebook for a while. When I returned to the restaurant, things were going grandly.
Justin started dating Andrea, and they did hit it off. I was almost jealous. She was more my type than I cared to admit. She was medium height, kind of thin, and had small breasts. I’m particularly attracted to small breasts. She kept her long, reddish-blond hair in braids most of the time, and tended to wear men’s style flannel shirts that gave me little shivers of sexuality. But she was Justin’s girl, and there’s no way I’d interfere with that.
What my research didn’t tell me about her is that she had a sister. Two years younger, she was quite similar in appearance, right down to a liking of flannel shirts. Fiona worked as a schoolteacher. I asked Andrea about introductions, and she was delighted. She thought I was just the guy for Fiona, who had recently had her heart broken.
Within a week, I had a date with Fiona, and we hit it off right away. She spent quite a bit of time telling me about her former boyfriend, and I listened eagerly. Anything about her background interested me.
It turns out the guy suddenly decided he was gay and left her. She thought they had fallen in love, but evidently, he had been faking it to ‘fit in.’ She was still recovering, and I seemed to be exactly what she needed. I was hoping it wasn’t a rebound situation.
I knew when Justin and Andrea started having sex, because he told me during one of our sessions. You’d think I might be jealous or something, but how could I be? As of recently, Fiona and I had been doing all sorts of sexual things too. She particularly liked being butt-fucked doggy style, and I have to say, I enjoyed it every bit as much as she did.
Justin and I continued our sessions from time to time, but way less often. When we did play, we still totally enjoyed it. We usually talked about our women, probably way too intimately, while we did things to each other.
One night, when I told Justin about butt fucking Fiona, he got big eyes, and shocked me by asking, “Why have we never done that?”
“Woah, you mean you and I? Hmm, interesting!”
I loved the idea of fucking him, but wasn’t so keen on getting fucked. We talked it over, and the next thing you know, he was on his hands and knees on the bed, and I was behind him, with my rock-hard, condom-clad penis deep in his butt. He said it was kind of “ouchy,” but he seemed to enjoy the whole process.
Oddly, the part he liked best was before the actual fucking. I thought that I should warm him up by placing one, then two fingers in his butt. He was on his hands and knees for that, and I proceeded slowly. He was quite in exstacy when I did that finger business. I was excited to see drops of pre-cum falling onto his sheet from the end of his erect rod. I pressed forward, curling my two fingers so they’d be massaging his prostate. He found that quite interesting. As I did it, it seemed to make some cum that was stored in his prostate gland squeeze out through his urethra, and drip onto the sheet, joining the pre-cum that was already there. I could tell it wasn’t just more pre-cum, because it was white, not clear.
A week or so later, because he wanted to butt fuck me so badly, saying that Andrea wasn’t into that, and with me being the servant and all, I let him. I was expecting the worst, but I rather enjoyed it, just like I had so long ago with Paul.
Somehow, Justin, the doofus, happened to let it slip to Andrea what he and I had been doing in the evenings. She immediately told Fiona, and our jig was up.
Whereas I was scared to death about what Fiona would say to me, it took a weird twist that I did not see coming. She wanted to watch! Furthermore, her sister wanted to watch.
At that moment, I had no idea how Justin might take it, but I was both freaked out, and delighted. I’m a modest guy, and to have an audience, that was just plain weird. Then again, I was probably also a closed exhibitionist, because I was hoping against hope that she was serious and such a thing might actually happen.
It did! A couple of days later, us two guys, and the extremely beautiful teacher and programmer were all naked in Justin’s big bed. We started with just the two guys giving each other handjobs and blowjobs. Seeing that made the sisters incredibly horny. They started licking each others pussies, and gave each other crashing orgasms. You could tell they had done it before. Then we all played every which way. Andrea even let Justin butt fuck her while Fiona and I watched.
I could say it ended with a double wedding, but actually, the that’s just the beginning.