I got a visit from one of my all time favorite customers. This is a guy who’s been coming here for years. And let me start off by saying he’s one of the sweetest, nicest clients I’ve ever had. He used to come in every couple of months, but I haven’t seen him in a while.
Anyway, “Tony” as I call him, always comes in looking the same – a short, clean-cut middle aged guy in standard business shirt, tie and slacks. I guess you’d say he looks like an insurance salesman, which is funny because he is an insurance salesman! LOL
I practically jumped out of my seat when I saw him today. I gave him a big hug and we exchanged some quick gossip before I led him into my session room. His routine is pretty much ritual after all these years, so I don’t even need to ask him what he wants. I tell him to get comfortable, then I leave the room. As I’m leaving, I check my watch and note that I don’t need to return for 20 minutes. So I take my time booking him in and just sort of dawdle around till it’s OK for me to return.
Exactly 20 minutes later, I knock on the door and he tells me to enter. I walk in and Tony is gone. Standing before me is “Tina.” Tina is a flawlessly made up woman – complete with makeup, black high heels, thigh-high stockings, garter, short red skirt, conservative white blouse, black bra and panties, and a long expensive wig of dark brown hair.
“Hi Tina!” I said. “I’ve missed you!”
Tina smiles back, “I missed you too! It’s been so long.”
“The usual?” I ask.
“Oh, of course,” she answers. Tina’s voice is slightly higher in pitch than Tony’s. Now let me explain here that Tony is not gay. And I think his wife would agree! He’s definitely only attracted to women, but his thing is that he really gets off when he’s dressed like a woman. I think they call that a transvestite – correct me if I’m wrong. Anyway, he says that he feels “soft” when he’s all dolled up and that he feels like he can better relate to women that way.
Tina’s sessions are unique (to say the least). He always gets the mutual massage, so I tell him to lie down on his back and relax (I’m just going to call Tina “him” from now on since it gets confusing switching back and forth). I take my Gap T-shirt off, then my jeans, but I leave my Victoria’s Secret G-string and bra on. With him on his back, I start running my hands up and down his arms.
“You look so pretty today Tina. I love your new blouse.”
“Thanks CJ. I got it on sale at Macys.”
One of the things I have to do is tell Tina all during the session how pretty he is. That really turns him on. Now I have to tell him that he’s “pretty” and not “hot.” He prefers to keep the talk very sweet and sincere. I guess you could say Tina is a lady and not a tramp. LOL
I always start off each session by slowly taking his blouse off while I’m laying on the flattery. When I’ve unbuttoned it completely, he sits up and helps me remove it. Then I start to gently massage his “tits” through the black bra (it’s always black). The bra isn’t padded or anything, so he actually gets a decent massage of his pectorals. I should note too, that he doesn’t touch me during this. He just lies there and softly moans every now and then.
Next the high heels, stockings and skirt come off and he flips over onto his stomach. I work his back and legs in more or less a therapeutic kind of way, but I’m still complimenting him on his looks the entire time. When I finish the legs, I tell him it’s my turn and we switch places.
I take off my bra, but leave the G-string on. He likes to start off with a quick, but thorough massage of my back and legs, but I know he can’t wait for me to flip over. His massages are always very gentle and sensual – especially when it comes to my breasts. He’ll sometimes spend a good portion of his session just on them!
So I roll over on to my back, and he climbs up on the table and straddles my hips while he’s still in panties and bra. He puts some warm oil on his hands and starts to slowly massage my tits, running his hands in large, gentle circles around each of them. I have to confess that I love this part. This is one of the few decent perks of my job – the occasional, fabulous, relaxing breast massage. Most guys just want to squeeze them and pinch the nipples (Gawd I hate that). Anyway, for what felt like an eternity (yet still too short in my opinion), he caressed me very gently – first one way; then the other. I'm loving it – I just have to lie there and throw in the occasional “… you’re soooo pretty…” every now and then.
I’m not even looking at the clock at this point. I don’t have to – he ends my massage by cupping each one of my breasts with his warm oily hands and says with a smile “I think we’re almost done.” This is my cue that it’s time for his happy ending. We always finish with a breast release, and it’s done in a very specific way. I stay on my back and he moves up and straddles my stomach. With the panties still on, he pulls out his already hard cock through the sides of the panties (it’s usually hard and poking out during the breast massage anyway). He adds more hot oil to his hands and lubes himself up, then he places his dick right between my already oily tits.
Let me explain now that in all the years he’s been coming to me, I have never touched his cock. Not once. It’s part of his kink I guess. Tony once told me that he has a group of friends that share his fetish. Every once in a while, they’ll all get together at one of their houses and hire a stripper. They’ll dress up in their finest women’s clothing and sit around in a circle with the stripper in the middle. Then they’ll watch her dance while jerking themselves off.
So Tony’s cock is now resting between my oiled up breasts. I make it a point to keep my hands dry for a breast release since it provides me with more control over The Girls. I can now hold them up and push them slightly together to gently wrap his cock. Tony starts to slowly pump in and out of my oily cleavage. With my hands dry, I can control the tightness that I’m wrapped around him. His cock is big enough to stay in there and not slip out. When my hands get all oily, the best I can manage is to just push The Girls together, let the guy do all the work, and hope for the best.
“How pretty am I?” Tony manages between moans. His eyes are closed and I can tell he’s getting close.
“You’re the prettiest girl Tina… I love how pretty you are…”
He always gives out this little grunt before he cums, so I have enough time to sit up slightly and release his cock from the warm folds of my cleavage. He grabs his cock with one hand and jerks himself off onto my left breast. I let him catch his breath and enjoy the view of his little mess before I ask if I can clean myself up (guys just love to marvel over anything they cum on, so I try to indulge them). He gives me a throaty “Thank you!” before un-straddling me. I wipe myself up with the table sheet, then hop down.
Since I don’t have to clean him up too, I just wipe up with a soapy towel. He won’t change his clothes in front of me, so I quickly throw mine back on and tell him to take his time. Then I make my way outside and leave him alone in the room. About 15 minutes (and 1 cigarette) later, “Tony” walks out of the room – a short, well dressed insurance salesman with a gray shirt and red tie. “Tina” is now carefully packed away inside a small leather brief case. I give him another hug and tell him not to be a stranger. He says “Thanks again!” and leaves. It’s a shame Tina can’t come out and play more often. Oh well.