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[MF] Erotic massage freebies and ex-coworkers
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WindJammer27 is a male/female couple
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Throughout my extensive catalog of sexual adventures here in Japan I’ve never actually hooked up with a co-worker. Former student, yeah, ex-coworker, sure, but not someone I’m still actually working with. Part of me doesn’t want to dip my pen in the company ink, but if the stars aligned I wouldn’t object.

Kana is a woman I would have belly flopped into the company ink for. I don’t remember the specifics of how we started talking – maybe/probably a company party and we casually just started chatting and ended up hitting it off. She worked in a different department but sometimes our paths would cross. We’d talk using the work messaging app and end up chatting about all sorts of stuff, which lead to us occasionally hanging out outside of work.

Kana is short, I think a little shorter than Japanese average. The short and stocky but very cute type. She kept her hair dyed a dark auburn brown, with slight curls. I could tell she had a nice, juicy body under her clothes but she never wore anything revealing or tight-fitting to work, so that was all left to the imagination.

At some point I ended up revealing my freaky nature to her. I generally keep my exploits close to the chest, especially with co-workers, but there was something about Kana that prompted me to spill the beans. At this point I wasn’t an erotic massage therapist – that was still many years away – but I did have a lot of hook ups under my belt, not to mention my experiences at swinger bars and what not.

Kana was very interested, and curious. She didn’t prod, but made it clear that she wanted to hear about these stories, and hungrily ate up whatever escapade I told her about. She said that she was insanely curious about these things, but would never have the courage to actually do any of them herself. Kana had a boyfriend, and I myself would often be involved in some way or another, so I considered our friendship to be entirely platonic. I’ll admit to fantasizing about her every now and then, but honestly it never seemed like anything that would actually become a reality.

Well. Never say never, I guess.

Kana would eventually quit her job. I think we hung out maybe once or twice after she did, but she got married and moved to her husband’s area. I would quit as well, and then end up moving to a different part of the country. Kana and I fell out of touch, and to be honest I kind of forgot about her. And that was at least 6 or 7 years ago.

Fast-forward to the present. I have business that put me back in my old stomping grounds, and as I’m walking on the street I notice a familiar woman…it only takes a few seconds for my brain to recognize Kana. She recognizes me and we, surprised as all hell, greet each other. We talked a bit on the street but couldn’t chat for long as she had two young kids in tow. She told me that in the time we’d grown apart she was, obviously, now a mother of two. And she’d come back to this area as part of raising them.

Later that night I was able to find her contact info and shot her a message. She replied back and we agreed that the next time I’m in town again we should meet for lunch. About a month later I did have business in town, and she was able to free up an afternoon, so we met for lunch.

Not long after she quit the company she got married, and kids followed soon after. Her husband travels frequently for work, and is currently on an overseas assignment, leaving her pretty much alone to raise the kids. With her youngest now in elementary school she was able to go back into the workforce, working a job with flexible hours that allows her to do the parent stuff she needs to do.

After catching her up on the mundane stuff in my life, Kana asked wryly, “Okay, now what about the other stuff? The juicy stuff?”

“…What juicy stuff?”

Kana punches my arm playfully. “C’mon, you know, the juicy stuff.”

“I don’t have any juicy stuff, I’m just a boring dude.”

Kana playfully punches me again. “That’s such a lie. There’s no way you haven’t been up to stuff. I know.”

She then reminded me of some of the past stories I’d told her. I actually had forgotten that I’d let Kana in on my secrets. Things felt a little different now though. Back then we were younger…and I wasn’t sure I wanted to jump right in with her, given how much time had passed, and the fact that she was now a mother to two young children. But I saw that same sparkle in her eye, hungry for whatever erotic morsels I could feed her, that shone so brightly 6-7 years ago. It was still there, still hungry.

“All right you got me. To be honest, there is one new thing I’m doing. I do work as an erotic massage therapist for sex services for women.”

Kana’s face lit up at the revelation. She’d heard about the concept but wasn’t familiar with it, so I told her about it – getting appointments, meeting up with women. Giving them an erotic oil massage that ends with me going down on her and giving her a happy ending. And…the variations, such as women who’d be like “I don’t even need the massage.” I also told her about the pussy eating contest in which I placed third.

We talked some more about other things until it was time for her to go pick up her kids from school. We both agreed that it was good to have reconnected and that we should have lunch again if I was in town again.

About two months later I would be in town again, so I reached out to Kana and we made plans for lunch again. After some brief mundane conversation Kana asked about the erotic massage gig. She asked about the kinds of clients I get, and I told her the majority were married women who were dissatisfied with their sex lives. For them, paying for a service didn’t count as cheating.

“So,” Kana asks, “your customers can be anybody?”

“Well, anyone who books me, yeah.”

“So how do you…you know…you can just make out and do sex stuff with anyone?”

This…is such a loaded question from women. My male brain wants to be like – yeah! Don’t worry about your age or your looks, if you want to get down we can get down! But over the years I’ve learned that a lot of women don’t see it the same way. Many women want their partners to choose them specifically, not just because they have a vagina and are willing. Being over-accepting on a guy’s part can be unattractive in a “oh, he’s not interested in me, just my parts” kinda way.

As such, I try to answer this question as delicately as possible. “Well, it’s not just anyone. I really like women who are sexual and enjoy sex, there are a lot of women out there who aren’t. And if she picks me, trusts me with her time and her body and her sexuality, I consider that to be an honor. So at that point she’s not just someone, she’s someone I have some common threads with, a connection at least.”

Kana seems satisfied with my answer. But I can see something churning behind those big, gorgeous eyes of hers. “Still, it’s amazing that these women can do those things with a stranger. I don’t think I could.” She paused, staring out the window of the restaurant we were having lunch at. “But, I am curious. You know…my husband is away from home a lot.”

“Well, if you are curious, I know all the resources and what not, I could help you through the process…”

“Oh no,” she says somewhat sheepishly, “I could never do something like that with a complete stranger.”

In my younger days I probably would have missed the loaded implications of that sentence. Fortunately with age comes experience, so I was able to do the math almost instantly. She’s curious about it, but doesn’t want to do it with a total stranger. She knows me, and I’m an erotic massage therapist, so…

Even still, as the realization hit me I froze. I couldn’t find any words to say. All I could do was look into those gorgeous eyes of hers, as a rush of emotions came flooding back. Fantasies from years past, stuffed into the “that’ll never happen” box now rushing out, becoming so palpable that I could literally taste it. Kana had always been a beautiful woman, but now being a hardworking mother made her even more attractive.

After what felt like an eternity, Kana broke the silence. “How do you make a reservation?”

“Ah…no. I can’t take money from you…”

“But if you’re doing this as a job, you can’t do it for free, right?”

Again, my experience helped to save me, as I realized what she was thinking. There’s a world of difference between cheating on your husband with your friend, and utilizing a service to take care of your needs.

“Well you know,” I said, “there is something called “monitor”. Basically the customer gets a free session in exchange for providing feedback.”

“I see. Do you do this “monitor” stuff?”

“Well, I am always open to finding new practice partners. I need to stay on top of my game.”

“Then…maybe I can help you practice?” She spoke so softly that if there had been any sort of somewhat loud noise within 50 km I wouldn’t have heard her. Fortunately I did.

We very quickly finished lunch. While Kana phoned her kids school to let them know she might be a little late in picking them up, I quickly searched for a love hotel in the area. Fortunately there was one – something old and basic – but it would do.

We arrived at the hotel, and I explained that normally, we take separate showers and then get started with the massage. I let Kana take her shower first, then I took mine. All the while my heart was racing, pounding, my mind in disbelief at where I was, with who, and at what was about to happen.

After her shower Kana had been wearing a bathrobe. I instructed her to lay face-down on the bed…and to remove the bathrobe. I held up my towel in front of her as she disrobed, and laid it on top of her from her back to just covering her butt. I could see her legs for the first time…good, thick legs. Looking up a little further I could just see…but we would save that for later.

I started my massage at her feet and worked my way up her calves. I didn’t bring any of my massage oils, but the hotel did have some lotion on hand. It wasn’t great, but it would have to do. …For the most part, women utilizing erotic massage don’t care all that much about the massage part of it. But I always feel like if you’re going to do something do it right, and I happen to take a lot of pride in my massage.

Kana and I continued to chat a bit while I worked her legs, but as I moved up to her thighs the conversation fell silent. She had her legs closed, so I gently parted them so I could work my hands up her inner thighs. As I did, I could see a sliver of wetness streak between her legs. To say that Kana was wet would be like saying the Pacific Ocean is slightly damp. Holy fuck she was soaked. This was “fuck foreplay and fuck me now!” wetness. My cock was rock hard and every fucking fiber of my being wanted to. …I have no idea how I didn’t. I continued the massage.

Eventually I moved up, massaging her back. I was straddling her butt as I worked, sometimes bending over her depending on the massage technique. I usually keep my boxers on during a session – it’s a sign to the woman that this is her time, not mine, and penis does not have to be involved in any way. Despite that mine was poking out of my shorts, and every time it made contact wit her thighs it felt like I could easily glide inside of her.

I finished working Kana’s back and asked her to roll over. I held the towel up so that I wouldn’t see her as she did, and placed it back on top, covering from her tits to just below her pussy. I could tell that Kana was still feeling nervous, a lot of clients still feel bashful at this point.

“Nervous?” I asked her.

Kana smiled sheepishly. “Yeah, a little. I mean, we are friends and it’s not like we’ve ever been naked in front of each other before…”

Without hesitation I reached down and took off my boxers, tossing them aside. “There. Now you’ve seen my penis, and right now I’m more exposed than you are.”

Kana laughed. “I guess that’s true.”

I went back down to massage Kana’s inner thighs. The towel was moved up slightly, revealing a slightly hairy bush.

“Sorry,” Kana said, “it’s been a while since…”

“What? There’s nothing to apologize for.”

“Don’t most foreigners like it shaved?”

“I don’t particularly care either way.”

I worked Kana’s thighs a bit more. …God, her pussy was so wet. I wanted nothing more than to finger it, lick it, fuck it. And I’ll admit, I wasn’t giving the massage portion the time I usually do. May have been speed running things a bit.

I moved up and, with the towel still covering her breasts, massaged her shoulders. Kana closed her eyes and seemed to let her body just enjoy the sensations. I moved down from her shoulders and massaged the side of her breasts. The towel fell, revealing her full breasts and delicious brown nipples. I massaged her whole breast, careful to tease her nipples with my fingers without actually touching them. Kana’s body squirmed, and I could feel the literal heat coming from her pussy.

I had restrained myself long enough. I couldn’t take it anymore. I bent over and took Kana’s left breast into my mouth, running my tongue all over her pert nipple. Kana let out a gasp of both pleasure and anticipation finally fulfilled. I licked both left and right, fondling the other with my hand. Kana moaned in pleasure but kept elevating her pelvis and twisting her legs. I knew what she really wanted. I wanted it too.

I slid down and almost immediately pressed my tongue into her pussy. Kana’s body exploded with pleasure again. The entire lower half of my face was almost instantly covered with her juices. I licked up as much as I could, softly pushing my tongue inside of her, then licking up and working her clit. I found the way she liked to be licked and dedicated time to licking her. She built up to her first orgasm, screaming in pleasure as her body bucked. I grabbed her ass with both my hands, softly resting my tongue on her clit until she calmed down, then slowly started licking again, building up to her desired intensity, coaxing another orgasm out of her. I did this several times, bringing Kana to several powerful orgasms.

After the third or fourth I came from between her legs and slid up to lay next to her. I put my hand on her stomach, and she put her hand on top of mine.

“Well,” I asked, “how would you rate my performance?”

Kana stared at the ceiling. “I now understand why women pay for that. Your services must be in high demand.”

“Well, I do okay for myself, but I wouldn’t say high demand.”

“You should be in high demand.”

We both shared a chuckle at that.

Kana then asked the question I often get asked from clients. “So, you’re not allowed to have sex, right?”

Legally, we erotic massage therapists are not allowed to offer penetrative sex as a part of our services. I told Kana as much.

“…However,” I said, “I didn’t tell my shop about this meeting, and it’s not like I’ve taken money for this either, so I’d consider this to be pretty off-the-books.”

Kana’s gaze never left my face and she reached down and took my engorged cock into her hands. I…could not hold back any longer. I couldn’t let her stroke it either, I might not have lasted even ten seconds. I got on top of her, gently parted her legs, and slid inside of her. It was as smooth as I had imagined it to be, and her pussy was so warm and welcoming.

I bent over and, believe it or not, Kana and I kissed for the first time. I felt her soft lips upon mine briefly before she had her tongue in my mouth. I thrust at a moderate pace while we tongue kissed, but eventually I had to straighten myself out. I looked down to see Kana, a good friend and someone I had fantasized about but never entertained the reality of anything more, naked, sweaty, fucking soaked at the crotch with my cock inside of her.

Dreams do come true.

I played with angles and speeds, finding the combination that did it for her. I worked that, and watched as Kana’s face contorted with pleasure, leading up to another body-bucking orgasm. I set out to do it again, but I was getting a bit too close to exploding myself, and I didn’t want things to end just yet. I went back to bending over and kissing her, because honestly the visuals of what was happening was far too much.

Kana I think sensed the battle I was waging. “Are you close to cumming? You can if you want.”

“No, not yet. I want to enjoy this a little more.” More tongue kissing and slower, sensual thrusting to help me cool down a bit, and then when I had reset enough I straightened myself again and went back to the rhythm that she liked. It didn’t take long for Kana to cum again. Her pussy tightened around my cock as I felt some kind of juices spilling out of her. One more…I fucked her to one more orgasm after that, but now I was really approaching my limit.

Kana knew. “You can cum.” She said in a sweet yet lustful voice.

“Where do you want me to cum?” I asked.

Kana knows that I’m snipped and test regularly, which is probably why she said what she said. “Cum inside of me. Please.”

Hnnnnngh. If there is such a thing as an orgasm button, she fucking smashed it. The words alone almost caused me to bust. So it only took a few more strokes for me to absolutely unload inside of her. I’m surprised the force of it didn’t send her flying.

I stayed inside of her for a moment before rolling off and laying next to her. Kana reached down and began to play with the mixture of her and my juices that were now spilling out of her.

“It’s been a long time since someone has cum in my pussy” she said, almost matter-of-factly.

“…I did not expect today to go in this direction” I admitted. “I hope you enjoyed?”

“Oh god yes, very much.” Kana turned into me and nuzzled her head into my chest.

We laid there together for a bit, but we both had our lives to get back to. Specifically, Kana had to go pick up her kids from school. As we got dressed she said “so that’s what erotic massage is all about, interesting”, treating it as her experiencing my services more than anything else. I think that helps her deal with any awkward feelings she might have about it.

That was a few months ago. Kana and I are still in regular contact, and like before, we agreed to meet up again for lunch the next time I’m in town. …I have no idea if it will just be lunch, or if she’s satisfied with that as a one-time thing. Certainly I’ve love to experience her again, but honestly, once a man’s had his dream fulfilled, what more can you ask for?

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