So I figure this is the best place to put this story. I was a masseuse for a while at a spa that was connected to a hotel in one of the nicer areas of the city. This is one of my experiences with a regular of mine.
I like to call this gentleman Big Tipper. He was a bit older, kind of thicker around the middle, super gregarious, owned a business, and had been married and divorced a couple times.
This day, BT came in for a massage. A coworker was buzzing back and forth between the rooms doing a deep clean and reorganizing, so I gave him a normal massage. You can’t see into the rooms, but with the doors opening and closing around us I think I was too jittery to do anything.
When the massage was over he asked if I would go to his room and spend some more time with him. The number he gave me was BIG. I don’t want to go into it, but even in retrospect it sounds like a lot. I told him I had a couple more clients, and he gave me his room keycard saying “text me when you’re off, no pressure.” He still tipped for the massage and then left.
I ended up at his door pretty much immediately after my last appointment, as I had plenty of time to think it out. (I won’t go into that here, but I organized my private life stuff on the elevator ride up.) He was in a robe and smiled, giving me a big hug and ushering me inside.
We sat down in the living room and he put the cash in front of me. He said that he only had a few requests. No condoms, no boundaries on the acts, no limit to how many times, and I would spend at least the night with him (I could go after he fell asleep, along those lines). I asked him if he was going to ask for any weird stuff, like gross or painful things, and he said ‘no’ and that he just wanted to not have to get confirmation for everything. It didn’t seem crazy, so I let him know I was good to go and he made a hand gesture to tell me I should put the money away.
After I put my purse away I turned back and he had taken off the robe. He told me to get undressed and start sucking him.
He has seen me naked a bunch already, so I just went with the flow and put my stuff in a nice pile on the end table near the door. I then got down on my knees and played with his balls while licking all over his cock, taking my time with everything. He moved and sat down on the couch, letting me bathe him in attention. He groaned more and told me to moan too, saying that he didn’t like how quiet we had to be at the spa. I complied, acting it up and moaning around his cock and trying to sell it.
After a few minutes of that he asked me to ride on top of him. He asked me what I thought about taking his cock without a condom, and I said it was pretty hot. I get creamy when I’m wet, and I was getting into the role so I actually had some good lubrication going when I dropped down onto him. Again he asked I moan and talk some more, so I asked him how it felt to fuck me raw. That sent him over the edge and he came inside me.
When we both calmed down a bit he moved his face towards mine and started kissing me. I realized it was actually the first time we’d ever done that. I moved my hips back and forth a bit, grinding against him and he started getting hard inside me again. When we finally broke away I told him how naughty it was that we just kissed while his cum was sleeping out of me, and that sent him over the edge again.
We stayed like that for a few minutes and he said he wanted to shower and eat. He ordered some room service for us, and we went to shower while we waited.
He told me to try to use the toilet, and gave him a weird look but he just went past me into the shower and pretended like I wasn’t there.
In the shower I soaped him up with my body and he started to get hard again but said he wanted to try something after the shower, so I gently played with him and we got into new robes together. I hid in the room when the food arrived because I didn’t want anyone who worked for the hotel to see me.
After we ate and watched some TV for a bit he grabbed his bag of toys and told me to lay back and play on my phone. Over the course of the next hour he stretched out my asshole with progressively larger toys and a ton of lube. It felt a bit off at first, I didn’t really do butt stuff beyond licking back then, but it wasn’t hurting. Just a backwards fullness.
When he had gotten me to take what felt like a gargantuan dildo in my ass, he pushed another one into my pussy and just had me be ‘full’ for a little bit.
I expected him to pull them both out, but he left the one in my pussy alone and slowly pulled out the one in my ass. I wasn’t empty for long though, and he replaced the dildo with his cock.
He was actually a bit smaller than the last dildo, so instead of it feeling uncomfortable or pushing too hard it felt pretty reasonable. He didn’t need to ask me to moan then, as I was getting into it. As he fucked my ass he curled over my body and sucked each of my nipples in turn. When he thrusted he moved the dildo around in my pussy, and the feeling was intense. I came without realizing it was on the way and he calmed down for me. Orgasming is kind of intense for me, so I usually get kind of weirded out by it.
He didn’t finish then, but took the dildo out of my pussy and rolled us over to spooning and held me for a while as I got my breathing under control. I told him he could keep going after a little and he slipped in easily. He gripped one of my tits while wrapped around me and then said he wanted to get some air.
He grabbed a cup of water for us and went out the balcony door. I followed him outside, staying naked. The cool air was really nice on my skin, and I enjoyed the view of the city at night.
He got behind me and had me lean on the railing so he could get back into my ass. At this point I was pretty used to it and feeling almost loose, so I just relaxed while he pulled himself into my hips. He came again, this one less strong than the previous two, and kind of slowly penetrated me while staying a little hard.
He stopped again after a bit, saying he wanted to rinse and get another massage. I laid him out on the bed after getting most of the lube and cum off of myself. I was getting kinda tired at this point, but still did my best to give him a good foot massage. When I yawned he told me to take a nap and I hopped into the bed and started nodding off pretty fast. He turned off the light and told me to not freak out, as he might wake me up with his cock.
Sure enough, it was still dark and I was on my back when I felt my legs being moved and him entering me again. In my sleepy haze I started saying how much of a naughty guy he was, filling me with his cock and toys and cum. I don’t know where it came from, but I told him I wanted to taste me on him. Maybe because the lights were all off and I felt like I could get away with saying anything. He was quick to comply and I sucked the tip of his cock and fingered him. The taste wasn’t great, but it felt extremely erotic. I told him to get a toy and fuck me while I sucked his cock.
I could feel him fumbling around in the dark before the tip of one of the toys slid into me easily. He kept the pace up while letting me fully engulf him in my mouth. I didn’t have to try to moan anymore, and just enjoyed the moment with him. I didn’t finish, but I had a good time.
He warned me that he was going to finish and I told him to do it in my mouth. It almost seemed like he was in pain but I couldn’t stop jerking him as those last few spasms went off.
He went to get the lights and help me clean up one last time (my skin was so dry by then, my god). We joked a bit about how at the end I was making him do stuff when I was supposed to be the obedient one.
He asked that I help him get comfortable with the pillows and then run my fingers through his hair while he went to sleep. It was a surprisingly tender action considering everything we’d done up until then.
He dozed off and I made my way home.
For anyone curious, the worst part of it all was really just putting back on my dirty clothes.
Source: reddit.com/r/gonewildstories/comments/u24qq0/fm_i_used_to_be_a_masseuse
That’s so hot and the details are top notch
How does one know to approach a RMT with that kind of thing?
You’d think it happens often, but I get the impression it’s rare as the RMT can lose their career basically if things got out.
well that got me hard wish it was me
Captivating…. I like how you tell your story
Hot!
So he had seen you naked a lot by then? Was he the first regular that you fucked at the spa?
I had an encounter with a masseuse once. She came for an incall for neck pain I’d been having after a game I played the previous week.
This was easily the best massage I’ve ever received, and it got me feeling a sort of way. I acknowledged that and was talking to her about it. I knew what I wanted but was very nervous about the power dynamic of her being in my house and not wanting her to feel pressured. I approached the subject delicately and gave clear outs and asked for consent with anything. What comes next skips over most of that, for story flow.
Essentially, towards the end of the massage, I’d already talked about the faux intimacy it creates and how I was feeling. She was massaging my arm, and my hand was pinned against her side. I asked if she minded if I let my hands wander. With her go-ahead, I was feeling her ass and legs, with occasional squeezes of her inner thigh.
When the hour was up, I started to get dressed, she was in the restroom washing her hands, but then I told her I’d love to add on another half hour, even if just a massage, because it was that good. She said my chest felt tight, so she could work on it some more. It wasn’t long into starting up again that she was leaning into my hand, letting out soft moans. I invited her to get up on the table, and as she did, I slid her pants down and let her ride my face. I told her it was my way of thanking her, so she didn’t have to do anything else. Aside from a little making out after, that was pretty much it. She didn’t charge for the last half hour, but I tipped well for the initial massage.
In hindsight, I came on a little strong on her way out about meeting up in a different context (a date). But even though she wasn’t interested, we had a good time.