Saturday, February 26, 2011

The most aggravating client.

OK, how to annoy your masseur? By not taking no for an answer, ever.

Actual texts from a client:

Client: morning

Me: morning

Client: Can I ask you a question?

Me: Sure

Client: Will you top me?

Me: No, sorry.

Client: Why not?

Me: I don’t do that with clients.

Client: Do you ever top?

Me: Yes, I am a top, but only with my partner.

Client: So, will you top me?

Me: No.

Client: Can I still get a massage?

Me: Yes, and I hate texting.

He schedules an appointment, he is a repeat client. We will call him Hank. He is a married man in his 30’s, muscular but also a bit over weight, bald, and a successful business owner. When he is on the table, he is a perfect gentleman. As per arranged, I do give him the usual manual release, but I stay dressed. The most he does in reciprocation is to occasionally stroke my leg. He takes an hour massage and tips exceedingly well. No mention is made of sex or the texts, all he talks about is his business and his father.

One week later, it starts again.

Hank: morning

Me: morning

Hank: Can I ask you a question

Me: Sure

Hank: Will you top me?

Me: no

Hank: Why not?

Me: I don’t do that with clients.

Hank: Why not?

Me: I don’t. I think you need a hooker, they are expensive.

Hank: Do you know any?

Me: No. Why do want to be topped?

Hank: I have a buddy who lets me suck him off, he wants to top me.

Me: So let him.

Hank: He has a huge penis, it scares me. Looking for a smaller one to break me in. I’ve never been topped.

(not sure how I should feel about this….)

Me: Ok, I can give you a prostate massage and gently work your anus open so you can take a penis.

Hank: So you won’t top me?

Me: No

Hank: Can I still get a massage?

Me: Yes

And we schedule another session. He only wants an hour, so I give him quick massage to relax him before I start work his ass while he is still lying on his stomach. I start with lots of lube and one finger. He likes the sensation as I work the finger back and forth and rub his prostate. I add another finger and my other hand I stroke his back and legs. He is very tight so we spend a long time with the just the two fingers. He undulates his hips more so I reach under to find his penis (average sized) and it is partially erect. I stroke it and he starts to moan. I withdraw my fingers from his ass and add more lube, I stop stroking his penis as I start to work three fingers into his ass. He tenses and I stop, my knuckles are still outside his ass, if this is going to work, he will need to relax so I just wait. Eventually his sphincter starts to relax and he pushes back onto my fingers, I work them in circles as I gently push forward. My knuckles slip through and all three fingers are into as far as the will go, I pause again to let him adjust to the new feelings. His penis had lost a bit of firmness, so I play gently with the head and it regains its full firmness. I start a rhythmic pumping of my fingers in and out of his hole as I stroke his cock, then his legs, then his back and then back to his cock.

I remove my fingers and tell him to get on all fours. I add lube to my fingers and again insert three, this time with very little hesitation. I add lube to his cock and start milking him while I thrust my fingers in and out of his hole. I remove all three finger and add my pinky as I go back in, he grunts but he takes it. I work his hole around and back and forth, paying close attention to his prostate while I continue to milk his cock, he moans loudly and shoots all over the sheet on the massage table. I stop the thrusting and keep my fingers in as far as they will go in his ass while he shoots.

When he is finished, I withdraw and get a cum towel and start cleaning up my hand and his cock and wiping as much cum as I can off the sheet. I lay a fresh towel on the sheet and tell him to lie on his back. I use the few remaining moment to give the front side of his body a rub down. Other than some moans and groans, he has been silent about the activities, he had talked a bit about his business and his father at the beginning of the session but has not talked in words for some time. “How are you doing Frank?”

“Fine. Good. Thanks.”

“Are you OK with the ass play?”

“Yeah, that was good.”

“OK” I say. “You took 4 fingers which means with a little patience you should be able to take just about any cock. Just let him know to go slow, prep yourself with some finger play and you should be fine. About the only difference is that I stopped when you came, a lot of tops won’t. They want to get off in your ass and will keep going until they do. Also, make sure that he wears a condom and you use plenty of lube. No negotiation on that. Got it?

“Yeah. Thanks.”

A little more chit chat about his work and he leaves, giving me another generous tip.

A week later, the same texts except he now wants to be “topped roughly.” I say no repeatedly and he books a regular massage. He shows up an hour late. Not cool. He apologizes and says he’ll leave if I can’t take him now (I can and frankly I need the money).

So, as we get started I ask him how being topped by his friend went. “We didn’t do it, I chickened out.”

“Sorry to hear that.”

“I am just afraid it will hurt.”

“Did it hurt when I fingered you?”

“No, it was uncomfortable a couple of times.”

“Did you enjoy it?” I ask.

“Yeah.”

“You still want to be fucked though, you asked me again today.”

“Yeah.”

“But not by your friend?”

“Not ready.”

“OK” I say. “You want to be fucked roughly by me so you are ready for him?”

“Yeah, will you?

“No. But I will work your ass pretty damn hard with my fingers again.”

“OK”

So we set off on a similar routine as before, but I go up to four fingers much faster and really shove them in and out hard. I pump his cock as before until he cums but I continue to shove my fingers in and out of his hole until leaps forward off my fingers.

“Are you OK?” I ask.

“Yeah.”

“A bit different feeling after you are done cumming isn’t it?”

“yeah.”

“Sure your OK?”

“yeah.”

I finish the massage in silence and after we are done I tell him that odds are that is what your top might do. “If he does and it is too much, then you just leap off of him like you did with me. The best position for a first timer is generally with both of you lying on your sides with the top behind you. The other option for a first timer is for you to squat over his dick while he is lying on his back, this puts you in control. Doggy style is fine on a bed, but don’t let him pin you up against a wall or a table, you will then have no control whatsoever.”

“Ok”

That was all about a month ago. He still has not let the guy top him. He still texts me every week. I still really hate texting. He still wants me to “top him roughly.” I still say no, he still gets a massage and finger the hell out of his ass and he tips me well. He still wants appointments at the last second and has shown up late and done a no show, all cardinal sins. When he does show, he is generally well behaved and tips well, so that is how he is still my client.

If I knew of a good gay sex therapist or surrogate, I would recommend that he see one. How frustrating it must be for him to know what he wants but be so afraid of it at the same time. I feel sympathy for his situation, I really do. I am just a sensual masseur and not wanting to be anything more in that line of business right now.