A Gentleman's Companion

(With thanks to Mike for his tireless help with proofing and editing - you know who you are!)

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For university, I attended a well-known college in central London.

Whilst I had been affirmably "gay" during my gap year, I had branched out when I got to university and had had a number of lovers, and one-night stands, both male and female.

I now knew I was bisexual, rather than gay, but for various reasons I was very discreet and had no intention of outing myself as either in the rather conservative college environment.

Whilst I really enjoyed sex with young men of my own age, I also craved the sort of sex with an older man that I had in my relationship with Andrew. (Please see my "Gap Year Experience" stories for more detail.)

It was a little difficult to find such older men in a university environment, unless you were after the faculty and, for the moment, I thought that was a little too close to home.

So, in order to find a more discreet liaison I placed an ad online:

"TDH student seeks older man for friendship and maybe more. Can be somewhat wayward and may be in need of corrective measures."

In addition to the age gap, I was missing the submissive relationship I had had previously with Andrew and wanted to see if I could find someone to fill that role. So, I thought I might as well be as upfront as possible to ensure I was attracting the right sort of interest.

I had quite a few responses to the ad, most of which were from inarticulate perverts. Now I have nothing against perverts, in fact I greatly enjoy the company of certain perverts, but I do need them to be able to string a sentence together.

However, amongst all the chaff there was one response that piqued my interest. Well written, polite, from a man who described himself as Richard, a mature English bachelor, inviting me to lunch. (Now, dear reader, take note, being invited out for lunch in response to a gay hook-up does add a note of distinction, and I was interested. Class!)

He left a number, a mobile, so I gave him a call.

He answered after a couple of rings, with a refined drawl, and I introduced myself.

He said he had been intrigued by my advertisement and would be delighted to take me out to lunch the following day. He proposed a well-known restaurant not far from the college but far enough - and expensive enough - to reduce the risk of running into anyone I knew and having to face awkward questions.

I knew that this particular restaurant probably merited a suit and tie. So, suitably attired, I turned up at the appointed time and, as instructed, asked for him by name at the front desk.

The rather attractive receptionist gave me a once over and a nice smile and then showed me through to the table. I idly wondered whether it would be worth trying to slip her my number on the way out. But I needed to focus on the task at hand.

I was led through to a discreet table in the corner of the dining room, sufficiently far from its neighbours to allow a private conversation. Sitting at it was a distinguished looking grey-haired man, probably in his mid-to-late-fifties, dressed in a lightweight tweed suit and what looked like a club, college or regimental tie, tied in a small tight knot.

He stood to greet me and offered his hand.

"I'm Richard, pleasure to meet you."

"Hello." I responded "Dan. Pleasure to meet you too."

"Do sit down."

"Thank you."

"Would you like a drink? I tend to stick to scotch and soda, but I can recommend the dry martini. They do a very nice job here. Ostensibly a very simple drink; but it's surprising how many apparently reputable establishments cock it up."

"Thank you. That sounds good."

I was secretly amused at the detail and precision he brought to the discussion of aperitifs, and also noted the upper-class vulgarity with which he expressed himself.

The waiter brought the drinks and asked if we were ready to order food. Richard studied the menu, and ordered for us both, without consulting me in any way. I noted that he had chosen a very healthy meal for me. Light, and high in fibre. I was slightly bemused by this but thought my mother would have approved!

I was intrigued that he didn't even acknowledge what he had done.

He simply said, "So, tell me about yourself." in a rather peremptory manner.

Brisk and direct.

"What do you want to know?"

"Where did you go to school? What are you studying? Where and why?"

I told him about my high school and university studies, the details of which are not important to this story, and he seemed satisfied with the answers.

"Good, good."

Nodding.

"Why did you place that advertisement? What are you hoping to achieve?"

His manner was authoritative. That of one used to command. I guessed he was ex-military. It was clear that he was in charge of the conversation.

I answered carefully, and truthfully. That I was looking for a relationship of some sort - which I realize I hadn't fully defined for myself - with a significantly older man.

"Why do you want an older man?"

It was slightly unsettling to be interrogated so directly. In my experience, people skate around topics like that. Possibly to avoid embarrassment, or possibly for fear of the truth.

I thought I might as well be as direct as I could in return.

"I find older men more interesting. And I like to be taken care of. Told what to do. Maybe dominated a little (by which I actually meant "a lot"!)" as I looked him in the eye and held his gaze.

Rather disappointingly his response was simply "Hmm. Very interesting." Which left me feeling rather exposed. Unclear as to whether I had said the right thing.

However, he seemed satisfied, and he moved the conversation on. We ranged broadly over a number of topics. Some mundane and some quite in-depth.

As we talked, I realized that he was skillfully ascertaining my sexual biases (bisexual) and current relationship status (nothing serious but a few FWBs, both male and female).

He seemed really to want to get to know me. He wasn't giving much away about himself, though he was clearly a wealthy man, with the autonomy to take a long, liquid, lunch, in the middle of the week, on a whim.

Finally, at the end of the meal, we relaxed over a glass of rather good brandy he set out his stall and came to the point.

"I am a very busy man. Not so much with work, but with a range of activities across business and leisure. Many of which intersect. I also have fairly specialist, niche, sexual interests.

"Whilst I am bisexual, and do engage sexually with women,"

(I noted the rather prim language with amusement.)

"my primary interest is in young men. In particular, young men who are sexually submissive and enjoy - or at least tolerate - being physically punished on a regular basis.

"I am too busy to go out and look for such men in local bars and clubs, and I don't have the emotional energy - or frankly interest - to have a relationship with a whiny young man who is always demanding attention or feeling neglected, or wants some money for something, or doesn't feel like sex tonight. I simply do not have the time for all that nonsense."

I smiled inwardly at this - not to put too fine a point on it - rant, but externally I just nodded and looked serious.

He smiled.

"If I had been born a two or three thousand years ago, in Greece or Rome, I suspect I would simply have purchased a stable of handsome young slaves. Or, only a couple of hundred years ago, in the British Empire, I could have employed a nubile young houseboy to keep me warm at night.

"Or perhaps hired a young man from one or other of the universities as a 'secretary' who would have had a range of duties, not all related to note-taking or letter writing! Read between the lines of the biographies of some of the 'great men of history' and you will see them."

I nodded, intrigued.

"I did actually read a biography of Cecil Rhodes once, which started me wondering along those lines."

He smiled again.

"Yes. Well, you have some idea what I mean then."

And then, more ruefully.

"Sadly, none of these is an option today - although that is probably a jolly good thing - so I have decided I need something with a more modern-day twist. I want a young man who, in exchange for a monthly stipend, becomes my 'companion'."

He looked at me. Holding my gaze.

"That is an interesting idea." I said, genuinely intrigued. "Like full-time, live-in companion?"

"No," he smiled "not full time! I have other things to do! No, I am thinking perhaps a few days and nights per month, as well as accompanying me on occasional trips."

"What sort of trips?"

"Mostly pleasure. Occasionally there will be some with a 'business' element, but most of my business tends to be conducted in quite nice places. What that really means is helping me to entertain friends and business associates now and then. Book restaurants, order wine, set up meetings, arrange business papers. That sort of thing.

"But of course, that would only - or at least primarily - be for the sake of external appearances. You would also have more intimate duties. You would sleep with me overnight - I hate waking up in an empty bed - and we will, not to put too fine a point on it, have sex regularly."

I nodded.

"I will also punish you on a regular basis."

I looked him in the eye, eyebrow raised, lips slightly parted, questioning.

"Don't worry, I am not a psychopath! I will be reasonable - and I promise you won't suffer any long-term damage!"

And I believed him. I had a sense that he was genuinely a pretty straight-down-the-line sort of man. One who knew what he wanted, and was determined to get it, but also one with empathy, and one who would keep his word. How did I know? I just did!

But I wanted to tease him little, to flirt...

"Tell me more..."

But he moved off-topic, to safer ground.

"The point is, as you will surmise, that as well as being sexually available, and able to take - and even enjoy - some punishment, I need such a young man to be of certain appearance and cultural standard."

"I am not obviously homosexual, and you will never see me acting in any way other than that of a straight man. I do have a small circle of acquaintances who have known me for many years who do know the other side of me, but this is a select and discreet group."

"The young man I am looking for must be able to socialise with me and travel with me without raising questions or attracting attention. He must fit in with the circles I inhabit, socially and professionally. This might sound snobbish, and objectively it probably is. But that is my life, and that is how I choose to live it."

"This lunch may have seemed like an extravagant way to meet you for the first time, but it was partly designed as a test to see how you would blend in."

I must have again raised an enquiring eyebrow, as he continued.

"I am pleased to say that you have done very well!"

He smiled, and like a lot of habitually stern people, when he smiled his whole face lit up.

"In summary, I am a sodomite and a flagellant, who is looking for a catamite!" He chuckled quietly.

I was intrigued, and a bit taken aback by his offer. It had never occurred to me that I might be paid for having sex - which fundamentally was what he was suggesting, even wrapped up in something more akin to a relationship, or a job with wide-ranging duties - and despite my sexually explorative nature, I was also a little taken aback. The idea of being a prostitute - a rent boy - was jarring to my solid middle-class upbringing.

But I had to admit, as an impoverished student, the idea did have some merit. It was also somewhat arousing. It turned me on. There was a power play. A power exchange here, that I hadn't previously explored, and it had an enticing whiff of taboo about it.

I did my best to play it cool. I thought I would tease him a little.

"I was in bed with my catamite when the archbishop called." I said, and smiled.

He threw his head back and laughed.

"Earthly Powers!" Actually, it was more like 'when Ali announced the archbishop had come to see me' but not bad!"

I smiled at that. "I stand corrected!"

He laughed again, delightedly. He seemed to be relaxing.

It was all a bit pretentious, in a middlebrow kind of way, but we were gently establishing our credentials. He wanted a handsome young boyfriend whom he could introduce to his smart friends in the knowledge that he would fit in and not embarrass him. I made, and make, no claim to be a literary sophisticate, but I had read enough to get away with it in a superficial examination, and that was enough for him. He wasn't going to take me to a literary seminar. Just the odd dinner party and - judging by his outfit - shooting weekend.

"So, what do you think about becoming this sodomite, flagellant's catamite?" he said, looking archly at me over his brandy glass.

I laughed at that. "I think that is an intriguing idea." I was by now slightly emboldened by the martini, wine and brandy and said, "Tell me a bit more about the 'flagellant' part."

I thought it best to get a bit more clarity as to what I was getting myself into.

"What exactly do you have in mind?"

"A fair question."

He leant back in his chair and looked me in the eye.

"I like to cane young men. Preferably naked young men. Stretched over my desk, or bending down to touch their toes, or strapped to a flogging bench. I also like to spank them over my knee, or even hang them by their wrists from the ceiling and whip them. And then I like to fuck them. Sometimes I like to fuck them gently and romantically, and sometimes brutally and aggressively."

He paused to gauge my reaction. There was quite a lot to unpack there, but none of it outside of my predilections, and - candidly - my experience. I felt a familiar twitching in my groin as the ideas percolated.

I also guessed that he was getting a sexual thrill from saying these things - wildly inappropriate things - straight out to me, in a restaurant.

I nodded and raised an eyebrow, indicating he should continue.

"But importantly, as well as being willing - ideally eager - to take a beating, I need to be able to talk to them afterwards. I think I like talking with you. I suspect I would like fucking you also. After beating you."

I looked him in the eye.

"I think I would enjoy fucking you too."

A pause.

"And I am perfectly happy to talk afterwards." I smiled.

He chuckled.

"And being beaten?"

"Oh yes. And being beaten! Definitely being beaten."

He grinned. Relaxed now. The hard part over.

"Well, this is a two-part interview, and I am pleased to tell you have passed the first part with flying colours. Would you like to come back to my house for part two?"

"What are the two parts" I asked guilelessly.

"Well, part one was the talking part..."

"Shall we go?" I smiled.

He paid the bill efficiently and we went out into the street, where he quickly found a taxi.

As we sat in the cab on the short trip to his house, he rested his hand on my thigh and then my crotch. He could clearly feel the extent of my arousal. He took my hand and placed it on his lap and I likewise could feel his swelling erection.

I could see the cab driver looking at us in his rear-view mirror. Trying to guess our relationship. I think he was guessing pretty accurately and I raised an eyebrow at him. He saw me and looked away to concentrate on his driving.

When we arrived at his house Richard paid the driver. As we turned to go inside, I lagged behind slightly and the driver said to me.

"By the way, if you need a ride home later here is my number," handing me a printed card.

It was a slightly odd thing to do, as London cabbies don't normally hand out cards. And this one was also odd because it had no details. Just a name and a mobile phone number. "I might give you a discount." Holding my gaze just long enough for me to realize that he was offering me more than simply a ride home.

"Thank you. I'll let you know."

As I took the card, I let my fingers brush against his unnecessarily. I chastised myself for being a total slut, but then refocused on the job at hand.

Richard was unlocking his front door, oblivious to my discreet flirtation with the taxi driver.

The house was one of those imposing white stucco townhouses common to that part of London, and reaffirmed my belief that Richard was a man of considerable financial means.

"Come in. After you," he said, as he opened the door to usher me inside.

I stepped over the threshold, conscious that I was unsure exactly what I was getting myself into, but simultaneously excited and aroused at the prospect of impending sexual (mis)adventure.

The interior of the house was large and airy, and as traditionally furnished as one might guess from Richard's demeanor and dress. This was the house of a wealthy upper middle-class, middle-aged English bachelor.

The furniture was solid and masculine. The artwork on the walls was of high quality and almost exclusively traditional and figurative. The carpet thick and expensive.

"So, young man, are you ready for this?"

"For what?" I responded, a little cheekily.

"For part two of your interview."

He paused and looked at me, searchingly, before continuing.

"As I explained, outside the house, in public, I am 'straight acting'. In private I am not."

He pulled me into him, so our crotches touched. I could feel his erection through the tweed of his suit, and I imagined he could feel mine.

He pulled my head into his and kissed me full on the mouth. I opened my lips, and he pushed his tongue in. He was a good kisser, and I responded. I enjoyed the feeling of being dominated by this older man as he took control of the situation.

"You kiss well." he said, approvingly.

"So do you." I replied.

He smiled.

"Take off your clothes, I want to see what I am buying."

I could sense that the word "buying" had an erotic implication for him. Probably a power play. The eroticism of my being bought and owned by him. I didn't mind. In fact, that word, and the peremptory manner of his instruction, had a similar effect on me.

I took off my suit jacket and instinctively looked around for somewhere to put it.

He realised my conundrum and said, "Just a moment," and went into the hallway, returning with a wooden coat hanger. I stifled a laugh as he hung my jacket up. It was such an incongruous gesture of formality and decorum juxtaposed against the activities that I imagined we were about to get up to.

His upbringing was such that, while instructing a young soon-to-be rent boy to strip naked for him, prior, presumably, to some rather deviant sex, he felt compelled to pause proceedings in order to find me a hanger for my jacket. I found it funny, but bizarrely I also found it rather erotic. The hint of repression, about to be ungirdled. The incongruity also highlighted to me the taboo nature of our relationship. He, much older. Well-bred. Patrician. A different generation. Proposing to pay me for an 'arrangement'.

And I knew, as I removed the rest of my clothes, that very shortly I would be kneeling in front of him, naked, taking his well-bred patrician cock in my mouth. And that was truly a turn-on for me.

Finally, I stood naked in front of him He looked me up and down, nodding with approval.

"Very nice. Very nice. Turn around please."

Again, polite, but without the slightest question that I might not do his bidding. It just wouldn't occur to him. I did as I was told.

People talk about "the male gaze". I like the male gaze. I like being gazed at with approval. I like to be objectified. I liked this.

He came up behind me and I felt the rough tweed of his suit on my naked back and buttocks. He reached around and put his hand under my chin and, grasping it firmly, pulled my head back and around to face him so that he could kiss me on the mouth. His tongue reached inside my mouth, owning it. Owning me.