Dating a Masseur?

I received the following email and also got his permission to share our conversation with all of you. The names have all been changed.

Hi Jack,

First and foremost, I love your blog, you are a very skilled writer and masseur from what I read ;) I've been looking in the web for a few days now trying to get some "answers" and your site just hit home.

If you don't mind, I would like to share a recent experience with hopes of obtaining your perspective, as someone who performs sensual bodywork, and perhaps gain some peace of mind of my own.

I'm fairly new to sensual/erotic massages (started this year). My first few times were great and limited to just mutual touching, and/or happy ending. After months of curiosity and as recent as this month, I started experimenting with new masseurs in my area, to my surprise some of the sessions have gone beyond the mutual touching and into oral and rimming etc.

My dilemma comes from this one masseur, tall, blonde, fit, eastern European decent, totally my type, claims to be straight. Throughout the session he was very nice, he kept complimenting me, at first it seemed like he was telling me what I wanted to hear but then again, he was pointing out things others had complimented me on before. Overall a very nice guy, though out the end of the session he let me give him a BJ and after we finished he offered to jump in the shower with me, as we are done chatting and washing off our oil, he looks into my eyes gets close to me and we start making out, I asked if he wanted to cum but he said that he had masturbated already, we both get out of the shower, we dress, we chat a bit more and before he leaves, he leaned over to me and made out with me again, then left. He left me thinking there for a bit after he left..

Come the following week, I schedule another appointment, he wont on with his massage, when he asked me turn over,  I pulled him close to me, we start a deep passionate kissing session, this time he also let me rim him and instead of releasing in bed, we just went to the shower to finish off.. This time while he was trying to cum he just held me tight as we continued to make out, it was hot and intense, and the same, as we got dressed he told me that one of these days he was going to pick me up and go out for drinks (he had mentioned that in the first session), he then kissed me goodbye and left. He later sent me a text, which led to us making arrangements to meet up casually later in the week.

The day off, he seemed to be backed up with work, still he took the time to come and meet, it was a bit awkward, there seemed to be a lot in his head and his phone was non-stop with texts, so we just kept conversation general, can't deny I flirted a bit, then we each went our ways, he said he would be in touch but haven’t heard back.

I've had nice repeat hot sessions with other masseurs, and they've also complimented me but they also kept it cool afterwards. No text backs, no social invites and no kissing.

So I'm not sure if he was just playing me into more sessions/creating client "rapport" or if there was a true spark from his side.. and this is where I'm needing another perspective

It's way too soon to be thinking about stuff, its only been 2 sessions, but would love to explore if there is something more..

I feel silly as in my mid 30s, not in high school, and I guess I should know better, but I just cant stop thinking about him!

Thoughts?

p.s. Thank you in advance and apologies for the long email.

I responded back with:

Dear Adam,

I think the big question here is what are you hoping for? Free sex? Dating? A relationship?

Most sensual workers have to deal with very old men all day long. We are always happy to have someone that we could actually be attracted to. It makes our job easier, even enjoyable. We will always treat such clients better because we like them. Personally, I have never gone on a date with a client because I am not looking to date, I have a partner. I have gone out to lunch with a client (he paid) after a session because he really wanted to talk about the session and his life. I did this only once since we have to be careful of clients getting too attached. 

So, are you getting played? Is he just trying to keep a good client? Maybe. He might actually like you. But, remember he has a job to do and bills to pay. So don't expect him to give up his "job" for you. 

If you are just wondering if he will have anal sex with you, sure! If that's his thing.

So what are you wanting out of this?

To which he responds:

Dear Jack,

Quite frankly, I think I was longing for that physical desire/connection and he just happen to push the right buttons. Is too early for me to think relationship, perhaps friends with benefits, he did mention he was straight, but who knows.. I tend to have no expectations as those usually lead to attachment/disappointment. So I guess In the meantime, I'll enjoy the moment, keep things professional and if something happens then great..

What I know for sure, is that I needed to get this off my chest in order to ground myself, get him out of my head (or at least not have him there as often) and move on.

I truly Thank you for taking the time to read and answer my email and in a non-judgmental way, It's definitely something I cant easily talk with anyone else.

Hope you are having great rest of your day and looking forward to more of your posts! ;)

To which I responded:

No problem Adam,

He may claim to be straight, but I doubt it. He is either saying to attract more customers or he is lying to himself.

Friends with benefits may happen, but realize he would be losing money if he loses you as a client. It has happened the masseurs will date a client, but it is rare.

Anyway, I am glad that I could help and I hope you remember to keep me posted. 

And about 30 days later he did:

Hi Jack,

It's been a while, wanted to give you an update on my situation and my observations, and I apologize upfront as I certainly don't want to nag you with my stories.

I have continued having sessions with him ever since we last talked, each session continues to be intense: kissing, oral, mutual orgasms etc.

Aside from the sexual stuff though, I am starting to notice that I also simply enjoy spending time with him, he's witty, we share some good laughs, stories about our families and I feel as we have a great connection, he always leaves me feeling great. I wish the time I spend with him would never end but unfortunately it seems to be limited to just a couple of hours a month. He always talks about us going clubbing or working out together but aside from that other time we went out, we really don't communicate in between sessions, there's maybe a small catch up chat when I contact him for an appointment but that's about it, which is perhaps a good idea, based on what I've read about client/therapist boundaries.

To add to my frustration, I learned from social media (I found him online :-)) that he's been going out with this girl! He had talked briefly about her a couple of sessions ago, but it didn't seem as something serious, however social media seems to indicate otherwise, although it looked as if it's one side sided from her, (could be my wishful thinking kicking in) plus, I'm pretty sure she doesn't know about his gig. Either way, can't deny it stung a bit seeing them together.

From what I'm telling you today, does it sound like another case of transference? Here I am speaking about of his relationship with this girl being one sided, yet I wonder if all these feelings I'm having are a result of me reading too much into his actions when in fact I'm just another day at his "job".

I replied:

Dear Adam,

Yes, it does sound like a case of transference. You are seeing what you want to see. He could easily be very much in love with this woman and marry her someday. That has little to do with your relationship with him. Whether he is just being nice to keep a good client or whether he genuinely likes you or more has little to do with his feelings for this woman. Just realize that he most likely will never leave her for you, that almost never happens. ;-)

He responded:

I wish there could be more of this out there on which people could share and discuss these types of experiences without the LMTs getting all worked up and judgmental about it.

As far as your advice, I concur, woman/man, it's not my intent for him to leave anyone for me (still bummer for me), however I now know better to at least hold-off on making any moves. I'm fairly new to sensual/erotic work, so my feelings may be more common than what I think.

Anyway, I literally just finished a session with him this afternoon and all I got to say is, if he's not feeling anything whatsoever towards me, then he's one hell of an actor!

Thanks again,
- Adam

About a week later I received this from him: 

To buy or not to buy, that is the question..

I typically have tons of candles around my place when he comes, a while ago he had mentioned he really liked one of them. I'm going home the Holidays, and I'm thinking of getting him one, for our last session of the year, its a tad pricey. What do you think? Is it tacky/creepy/clingy? I wonder if other clients also feel this way.. lol

p.s. I share my feelings with you, but I haven't mentioned any of this to him of course, up to this point, I've kept things professional in between sessions, I think, not sure if he knows how I feel.. don't want to make a fool of myself.. 

- Adam

My response: 

Hey Adam,

Many of my regular clients give me something around the Holidays. Generally, it is an extra large tip, but other gifts I have received are collectable Christmas ornaments, bottles of wine or other alcohols that they noticed on my bar, live plants and the like. It is better to give an early gift than to come back from vacation with something you bought while you were away because you were thinking of him, that starts getting creepy. Just relax and have fun with the situation, however, keep your eyes open for the real man of your dreams, one who is not taken or "straight."

He replies:

That's valid point, I did think about bringing him something :-p, but I'll just go ahead and get him the early gift instead. You are so right about the relaxing part, I need to remind myself to do that, I'm usually good at keeping things NSA or not even consider "straight" guys, but then there's always that one person/exception to the rule that gets to you.. sigh..

I appreciate you getting back to me, hope your day is going well

About 10 days later I received:

Dear Jack,

I know that you advised me to just relax and enjoy the situation, and to a certain extent I am, however as each session progresses, the feelings of taking things a step further grow, next step being perhaps hanging out socially.

First, there's not much of an age difference between us, we both have pretty active social lives, like similar music and attend similar places (I go to gay bars but tend to hangout more in the straight scene also).

Second, there's been a couple of things he's said and done that lead me to believe there's a mutual interest there but I've taken them with a grain of salt due to the nature of his job and/or because he never seems to follow through in between sessions:

• Constantly bringing up us going for a drink or him picking me up at the gym - he hasn’t followed through on this one as of yet.
• During one of our latest conversations, as we cuddled, we discovered we had a bar in common, which he followed by a “Well.. that’s where we met right?” - I took this as him trying to come up with a story for if we ever hang out together, don’t know
• He has foreign phrase tattooed on one his arm, when I asked him what it meant, he said "Adam is my favorite client" - cliche I know and I rolled my eyes but still thought it was cute ;)
• He also mentioned that if he ever has sex (intercourse) with a man, he would like for me to be the one - also cliche, won't hold my breath but still included it here
• Now the one that threw me of was that during the last session, he mentioned that his roommate was gonna be out for the weekend and that if I wanted, I could come over to his place for a visit, I told him I would let him know  - This one I figured was a bit more elaborate, why would you go through all that hassle of having to deal with someone and offering such a thing if you weren’t interested
• That same day, late evening he sent me a picture of him, just because
• A couple of days later, I sent him good morning text, he actually followed through, we had a nice exchange for a couple of hours, totally unexpected

I'm not sure if I should just sent him a follow up on his offer to meet him as his place, what do you think?

- Adam

My advice:

Adam, 

Sure, if you are interested and he is interested why not have a meet up at his place. You trust him. See if he follows up with it. Still, don't expect love, but friendship and sex may be on the table. If however he does not follow up with any of it, you will have to decide whether you want to continue with things as they are or not. Hope that helps. 
- Jack

Jack,

It does, I guess the point is to go with it and if nothing happens I'll have my answer. 

But the do the things I've mentioned below sound like typical "sales" techniques? Like you personally wouldn't do some of these things with your clients, right?

thanks for responding Jack

- Adam

Dear Adam, 

I would never go that far, quite the contrary, I make it very clear that it is a provider/client relationship. Especially when asked by a client to spend time together outside of massage, I answer that I am flattered, but I keep my personal and professional life very separate. If he is willing to spend a fair amount of time with you, without getting paid for it, then it is legitimate friendship (and who know, maybe more). Always be wary of those that say they are straight, they may have issues that you can not help them with. 
- Jack

Jack,

Yep, Im trying to be extremely careful because of that, I certainly dont wanna get hurt, but I do like him a lot!

He just responded that he wont be able to meet tonight, so I'm not going to make any further efforts and let him make the next move if he's interested..

Adam, 

Let him know that you are available (if you are) for the rest of the weekend and if he wants to get together with you, he just needs to let you know. In other words, make it clear the ball is in his court. 

Jack,

I'm guessing by now, he should have a pretty decent idea that I want to hang out, so if he really wanted to meet, I would expect for him to ask for my availability some other day.. 

- Adam

Dear Adam,

You are most likely correct. It seems that he has a very active social life, between working at massage, having a girlfriend, a roommate and other friends he hangs with. No point in sitting around waiting for him to call, best get out there and have some fun! Best of luck Adam!

Jack,

That's the other thing, he seems to always be available whenever I want a massage, not sure how he does it, he only does out calls, so he drives all over town/burbs.. but you're absolutely right, I'm definitely not sitting around, just a bit frustrated :-/

Thanks for keeping up with me Jack.

So people who read all the way through this, what do you think of the situation that Adam is in? Have you had similar situations? How did they end?  What advice would you have given? What jumps out at you in this exchange? Keep in mind, Adam is a regular reader and will see your responses. Thanks! 

- Jack

Hot time, with a young priest

In my line of business, we meet all types of people and that is really cool. However, we have to be careful since there are a lot of freaks in the world as well, which is why, when I get a request from someone new, I tend to do at least cursory search on any info I have on them. Depending on the means of contact, I can do a quick search on line to see if any flags go up. The biggest flag of all is if nothing shows up at all, that makes me worry. Some guys in the business keep on line lists of bad clients information that remain free and searchable so other workers can avoid them. The best search results show something personal about the client which usually means they have nothing to hide, like if I find a Facebook listing for them or a Linkedin listing, anything that lets me know just a smidgen of who they are. I get the use of fake names and blocked numbers and anonymous email addresses, you don't want to be blackmailed and are scared. Put yourself in my shoes though and you realize that I have a lot more to be worried about than you.
So, the other day I get a call from a new number and a guy wants to set up an appointment for later that afternoon, the time is available so I set up the appointment and give him my info. I then check the phone number quickly on the net and it looks like it belongs to a priest. Now this is not the first time this has happened and I am sure it will not be the last that I get someone from the clergy. Past experience says that there is a 50/50 chance he won't actually show and if he does, he will be over 60.
When the time arrives, he is a minute or two late, but he showed! I open the door and try to hide my surprise. Standing before me is a very attractive man in his mid-30's, reddish hair, 6', slim, well dressed in black slacks and a button down shirt (no priest collar).
He tells me name is Trent. I welcome him and show him to the room, do the usual check in with possible aches and pains and places he may not want touched, everything seems fine. He seems friendly, a little nervous and not overly chatty. I let him know that he should undress and lay face down on the table and hold up the towel that he can use to cover himself if he so desires. I leave the room to wash my hands and to give him time to undress. When I enter again, he lying on his stomach, uncovered. His skin is extremely pale, his legs are very hairy, almost satyr like. His ass is round and plump. He is indeed quite thin, but his legs are well defined. I check to make sure he is comfortable and then go to work on his shoulders (I remain clothed as I do for all new clients). His shoulders are tight and I drape his arm over my leg as I sit on the edge of the table to lift the shoulder blade and out me in a better position to work the trapezius muscle. His hand finds itself next to my calf muscle and his fingers slowly start stroking my leg is soft little circles. I switch sides and there is a repeat performance of the light stroking, nothing more, just soft little circles.
I get up to work the rest of his back, there are not a lot of issues so the strokes are more long and flowing than and deep tissue work,  I think that I hear the occasional soft moan, but it is so soft, I am not sure. I finish the back with a very light touch with just my finger tips. His glutes become covered with goose flesh, his back arches slightly, possibly another of those soft moans is heard.
I move to his feet and start working my way up to his ass. Those solid hairy legs require a bit deeper work, but he can take it. The hair on his legs stop about a 1/4 of the way up his very round ass, then they are completely smooth. A small bit of hair peeks from the crack. I start working his glutes with earnest and his hand is now next to my crotch, he ever so lightly explores the mound in my shorts with his fingers, finding the tip of my cock through the fabric and starts making lazy circles around it. I stroke up and down the crack of his ass, separating the cheeks and teasing his puckered hole, now his ass starts to rise and fall, as his hole begs for more attention. I switch sides and repeat the process, his hand becoming bolder and actually gripping my cock through the fabric. I lube up my thumb and center in on his hole, rubbing him with the lazy circles he seems so fond of, he raises his ass higher trying to impale himself on my thumb. I tease for a little longer then let him have it. Now a real moan escapes his lips as my thumb explores his inner most regions. I back off but only for a moment as I lubricate two fingers and slip them into his hole so very slowly, vibrating my hand as I do so. His hips start bucking back against my hand, forcing my fingers deeper inside, bouncing off his prostate. I slowly fuck him with my fingers while he moans appreciatively, my hand slides under his hips to find his throbbing cock. I play with it lightly until the pre-cum is leaking out in a slow steady stream.
Removing my fingers from his ass and cock, I give him a light rub down with a towel and light strokes along his entire backside with my finger tips before I tell him to turn over. I let him drink some water while I check out his stiff cock, it is not overly long but it is quite thick, nestled in a nest of neatly trimmed red pubes.It looks almost angry as it jerks and continues to leak pre-cum.
He lays down on his back and I move to his head to work his chest, accidentally grazing his head with my erection. He reaches back over his head and grabs my shorts, pulling them down, my cock springs up and hits him in the side of the face. He turns his head and reaches out with his tongue to taste my cock. I let him lick it for a bit before moving around so I can feed him the entire length. He takes it greedily down his throat, moaning as he does so. I slowly fuck his mouth for a time as he looks up at my face. I pull out, he says nothing but never takes his eyes off of me. Moving to the side of the table, I start massaging his cock. He moans and thrusts into the air. I play with his balls and he rolls his head from side to side, his hand has found my cock and is beating it frantically. I move my left hand down between his thighs and stick three fingers up his ass. He humps on them and it is all I can do to keep from jumping on the table and throwing his ankle up to his ears and fuck the living daylights out of him. But alas, I let frig my cock while I frig his while leaving him to hump my three fingers up his ass. He comes rather quickly after that.
Now that he has come, he is looking directly into my face again. I continue with the massage and stretches, but his eyes continue to follow me as I work. His hand will occasionally stroke my cock when it is near. When I finish, I ask him how he feels and if there are any places I missed. He states that when he has sex he doesn't want it to end until the both parties have come. I smile and say this is all about you, not me.
After he leaves, I look him up on line and finally find a picture of him in his Priest outfit. Next time....;-)
- Jack