As I said in my last post, I work a side job as an erotic massage therapist here in Japan. There's a lot of other stories I want to tell about that, but this just happened this past weekend and I gotta talk about it lol.

While I have the side hustle, I do have my own personal hook ups as well. Last Friday night I spent the night at one FWB's place, with plans to visit another Saturday afternoon. Me and FWB1 woke up early Saturday morning, which gave us plenty of time to fool around. We had sex twice - I'm not a morning person and had kind of a hangover from the previous night, so I went down on her plenty to compensate for not being as energetic as I ordinarily would have been.

Having cum twice already I made my way to FWB2's place in the afternoon. I wasn't sure how much I'd be able to give her, but I managed sex twice with her as well, also giving her plenty of oral to kind of balance things out. I don't mind at all, as I love eating pussy (I mean, being an erotic massage therapist...I damn well better lol). I ended up leaving her place a bit later than I'd planned for, but quite satisfied with four orgasms with two different women before nightfall.

So feeling like my day was complete, I buy some alcohol to enjoy on the train ride back home, thinking my day is more or less complete. I'm only on the train for maybe five minutes when I get a message from my erotic massage shop - I have a new customer who wants to meet me, tonight. I was actually kind of far away from Tokyo, so I explain that while I'm heading back, it'll take a while, I'll arrive around 11 pm. The shop coordinates with the customer and she's fine with that, and books me for 3 hours. This means I won't be able to make my last train home, and I would have to go straight to the appointment, even though I didn't have any of my tools with me. ...My tools being massage oil, and a small vibrator the shop gave me. I figured I could buy massage oil somewhere along the way, and the vibrator...well, hopefully either the customer wouldn't want vibe play, or whatever hotel we ended up going to would have one. I spent the majority of the train ride back thinking about this new customer - three hours is a good chunk of time, how was I going to use it? What kind of service did she want?

Eventually I finally meet up with her - she's tall and slim. I would guesstimate she's in her mid 40s. Big, round eyes, and a soft, innocent smile. She's wearing a white blouse and light blue pants. The name she gives me is Rumi - not her real name of course, but it's not like I'm using my real name either.

Rumi and I met up in Shinjuku Kabukicho, which is more or less the nightlife center of all of Japan. I'd hoped to buy massage oil, but the nearby variety shop was packed with people, so I abandoned that plan. I found out that Rumi hadn't booked a hotel, which meant that we'd have to go looking for an open one, in the middle of the nightlife capital at 11 pm. I didn't like our chances, and I was thinking of possible contingency options, but as luck would have it the very first place we tried had a few open rooms left, so we took one and off we went.

Upon entering the hotel I got paid (money up front), and we took some time to small talk while she filled out the counseling sheet. Her answers boiled down to - "I'll leave it to you". The hotel didn't have a vibrator so we'd have to forgo that, but they did have a cheap bottle of massage oil. Not ideal, but better than nothing.

We showered separately - her first, and then I took mine. She'd come out of the shower wrapped up in her towel, but when I finished and it was time to start things, she disrobed and began to lay down on the bed, giving me my first look at her body. She wasn't just slim, she was extremely toned - not an ounce of body fat on her. Despite her slim frame, she had a bolted-on pair of at least C-cup implant tits. No sooner than I'd had time to look at them, she said "Don't mind my tits. I got these done for when I did video work a long time ago, but you can touch them no problem."

Oh, video work. ...Wait, what?

"Video work...do you mean porn?"

"Ah, yeah. I used to be a porn actress, but that was a long time ago." She elaborates - "I did porn videos maybe around 20 years ago. I really enjoyed it! But I aged out. No one wants to see an old woman on camera." I assure her that if she made a porn today, I'd watch it. Not even joking there.

But I do have to take a moment to appreciate that the third woman I'm going to be sexually involved with today, is a former porn actress who is paying me to service her. ...I know, that doesn't seem real, I wouldn't believe it either if I hadn't lived it. Sometimes I still doubt myself.

We start the massage. We chat for a bit, but as I do her legs, back, and shoulders, she becomes relaxed so I just shut up and do my thing. After about 40 minutes of working her back, I have her flip over and lay on her back. I notice that her pussy is completely shaved. I work her legs and thighs again, and as I work my way up her thighs she starts to moan slightly and squirm. Okay, here we go. I work my way up her inner thighs, and massage the area between her pussy and her legs. Use both hands to squeeze her folds together, and work my hands upwards to indirectly stimulate her clit. More moaning and squirming from her.

Here I have to decide how dedicated I want to be to the whole massage portion. This time I decide - not very. After working her pelvic area for a bit - still not having directly made contact with her pussy - I work my way up her stomach and to her shoulders. I put my hands under her back and massage upwards, bringing her body closer to mine. For Rumi, this seems to be a combination of feeling good physically, and feeling good sexually. She almost unconsciously raises her arms to embrace me. I lay her back down and straddle her while kneading her shoulders from the front. Ordinarily I would move down from here and start massaging her breasts, but I was super-aware of her implants, as they were kinda stiff and I wasn't sure that would be pleasurable for her. I rested my head on her breast, letting the warm breath from my mouth caress her nipple. Rumi lets out the biggest moan yet - okay, so her nipples are sensitive. I move my head to let my lips and breath trace her areola and tease her nipple. She's got very cute nipples, small yet pert and aching for more attention. After a bit of teasing I finally start licking and Rumi responds very loudly.

While licking her nipples I slid my hand down between her legs. She was already wet, but only moderately so. I lightly fingered her clit, sometimes letting my finger slide down and tease the entrance to her pussy. Eventually I hit my limit, and slid my body down, positioning my head between her legs. I wasted no time diving into her shaven pussy, starting off with slowly licking her clit. I started off slow, and would gradually increase speed and intensity while gauging Rumi's reactions. She was already loving the slow licks, but her moans only got louder as the intensity increased. She would build and build and build, but never seemed to get past the hump and orgasm. While licking I slid a finger in and began fingering her. This definitely increased the pleasure for her...but still couldn't get over the hump.

After a while I decided to come back up, to give her a break. We cuddled and kissed passionately, our tongues intertwining like actual lovers and not two people who met for the first time an hour or two ago. As we kissed her hand slid down and began to lightly stroke my cock over my boxers. Despite having cum four times already this day, I did have a modest erection. Rumi stopped kissing for a minute in order to ask - "May I?" Of course you may! I slid my boxers off so that she could touch my cock directly. She stroked it while returning to kissing me, and after a few minutes she slid down and took me into her mouth. She was all over it, taking all of it into her mouth, licking up and down my shaft, aggressively working the head. Technique befitting a former pornstar. She started off sitting between my legs, but starting to position herself to the side, so that I could reach her with my hands. Taking the hint, I reached out and fingered her while she continued to suck my cock like, well...you know. This lead to us 69ing each other. With her positioned on top of me I penetrated her pussy with my tongue and tongue-fucked her.

We stopped 69ing, and she came back for more cuddles and kisses. I asked what I could do to bring her to orgasm. She said she liked being fingered with two fingers while being licked, so I slid down again, began licking her clit, and this time fingered her using two fingers. Again she responded very well to this, lots of build up and build up...but still never getting over the hump. To mix things up occasionally I'd stop licking her clit, and with my fingers still inside of her shift my body forward so that we can make out. I'd move my body together with my fingers as if we were having penetrative intercourse. And a few times I let my cock rub up against her pussy without my fingers inside. ...Since intercourse isn't officially offered I can't and won't offer to do it, but if she asked that would be a different story. With me rubbing my cock against her she seemed to enjoy it, and it felt like she would be receptive to penetration...but she didn't ask, so I didn't try. Ultimately I would slide back down and continue to lick her pussy. Instead of trying to force her to orgasm, I decided to just enjoy licking her pussy. Taking it slow, savoring her taste and her wetness, sometimes picking up the pace when I felt her getting into it. Just enjoying eating pussy, which I do enjoy, and giving her as much pleasure as possible without getting hung up on orgasm. It is not an exaggeration when I say I was licking her for around an hour. ...I had to keep my eye on the clock to make sure everything was within the reservation time.

Unfortunately that time ran out, and I never did get her off. I came up and cuddled with her, and apologized for not being able to bring her to orgasm. She said it was no problem at all - "It all felt really, really good. I was so horny this past week I could have pounced on someone, but I finally feel relieved and satisfied." I have to take her word for this. Of the 3-hour reservation time, I'm pretty sure I spent at least 90 minutes of it with my head between her legs. ...Time well spent.

She showered and we both got dressed. I asked Rumi what name she went by when she was a porn actress, but she didn't tell me, saying it was embarrassing. When I went home I did try to search for her with what little I knew of her, but this is literally looking for a needle in a haystack, so no choice but to give up. Despite not getting off I do hope Rumi enjoyed our session, and I certainly hope to see her again in the future.