How college debt led me to start working as a private masseuse [MF]

I’ve held a variety of gigs over the years as a broke college student, and then later as a debt-riddled college graduate working a barely above minimum wage job: grocery store stocker, private tutor, barista, dorm cleaner, uber driver, lyft driver, private tutor again, occasional plasma donor. Still, nothing has paid well as my time as a “masseuse”.

I first got into the job through, as these things tend to happen, a friend. I’d moved to a new city after graduation and thanks to the terrible housing market, was splitting rent for a tiny apartment with a childhood friend. We’d both grown up in the same tough neighborhood; she was now the executive assistant for some big hotshot corporate lawyer. On the weekends and some evenings, however, she had a second job downtown at her family’s “business”, working for her aunt. I assumed as a waitress or something, since she seemed to be paid in cash tips.

Over time, however, I began to notice that things didn’t add up. The envelopes of cash she was bringing back were fatter and fatter, the bills $20s and sometimes even $100 bills instead of $1s and $5s. There aren’t any restaurants downtown that seemed like they could generate that kind of income, so I tentatively asked her if she was doing anything illegal, suspecting something like selling drugs, which I wanted no part of. She hemmed and hawed but eventually caved when I said I’d move out if she didn’t come clean. She told me that she was working as a private masseuse in her spare time.

Now, I’m not an idiot. I knew vaguely what that meant – certainly not that she’d somehow gotten her massage therapist license in the past few months. Intrigued (to be honest, mostly by the money) I asked my roommate what it involved. She wouldn’t go into much detail, but invited me to come along to her next gig and “just watch”.

I watched. I asked her some more questions afterward. I told her I would think about it while telling myself that while the whole thing seemed glamorous and surprisingly fun, ultimately I wasn’t the type of person to get involved in that type of thing.

To make a long and somewhat cliche story short, 14 months later I found myself getting dicked down by a man 25 years older than myself in the bedroom of an apartment overlooking the bay, clothes strewn across the floor, muffling moans into a pillow as the room echoed with the slap of our oil-slick bodies.

Ken was a friend of one of my roommate’s clients. We’d met during my “training”, when he graciously allowed me to practice some actual massage techniques on him. He described his job as sitting in a chair all day and yelling at people, and nodded wryly when I ranted about my job while elbowing his trapezius, and was on surprisingly good terms of 2 out of his 3 ex wives. Over the next few weeks, I became more and more comfortable around him, so when my training was finally done, I barely hesitated before responding yes when he jokingly texted me about doing my “final assessment” on him.

We met at his apartment, as usual, and I gave him an actual massage, as usual. Still, I was a little jittery with adrenaline and anticipation, cunt clenching involuntarily every time I kneaded the plane of his back underneath my hands. Ken was pretty well built, for a man in his 50s, and more importantly I hadn’t had sex in a while: it was only natural to wonder what it would feel like to be underneath that solid weight instead of above it, especially now, when the unspoken understanding was hanging thick and delicious in the air, heightened for the both of us by the folder of cash sitting on the dresser. We’d never slept together before, though there had been that time he sucked both my nipples pink and raw after a session until I was sopping, breathless, before sending me home in furiously wound up daze.

As the massage wrapped up, I tried to remember what my plan had been. It was a laughably clinical checklist. Let my hand drift higher and higher, “accidentally” brush his cock, and let things unfold from there. Before I could execute this extremely seductive maneuver, however, Ken flipped over, raised one eyebrow, and said, “You call that a massage?”

I experienced a moment of actual terror before seeing the hint in his eyes. Gulping, I picked up what he was putting down and said, “I’m very sorry sir, I’m new at this.”

“Clearly. But as a regular customer, I was expecting something a little more. You’ve been holding out on me.”

“I- um.”

“Get on the table.”

“But you’re the client-”

“Don’t make me repeat myself.”

Shaking with anticipation, I obediently switched places with Ken, feeling a shiver of pleasure run down my spine as I saw his cock bob, already half-hard, as he stood to lean over me and demonstrate the proper technique. Off came my tank top, my bra, my shorts and panties. Large, rough hands smoothed over my back, my legs, ankles, arms, the cleft of my ass. It wasn’t really a massage, more like gentle groping, my breaths coming faster and shorter as Ken’s fingers found their way between my breasts and the massage table and started rolling my nipples, which sent a straight line of heat down to my pussy. I moaned.

“Been thinking about this for ages,” Ken muttered. “You look like such a good girl, you know that. I knew it the first time I saw you. I’m gonna make a mess of you.”

In no time, he had. Ken’s broad, exploratory touches become more focused, hungry, and soon I was on my back and bucking my hips, thrusting onto his fingers as they plunged into my pussy at a steady, maddeningly unhurried face, twisting and curling until Ken had found the spot that made my skin break out into goosebumps and involuntary moans rip their way out of my throat. I felt warm, flushed, and embarrassingly wet. When his thumb rubbed steady circles around my clit, I felt my whole cunt light up and clench down in pleasure. It had been a really long time since I’d been touched like this by someone else, despite all the touching I’d been doing to Ken on the regular.

Everything was heightened by the fact that this whole time, I was trying my best to suck Ken’s cock as he fingered me ever closer to what promised to be an intense orgasm. Between his thick, hot weight sliding between my lips and the orgasm unfurling inside my core, I was well on my way to being the mess Ken wanted. When I finally came, shuddering, crying, it was with his balls heavy in my mouth and my hair knotted in his fist as I squeezed down hard around four fingers.

I’m not sure how exactly we got from the massage table in Ken’s living room to his bedroom, but after coming hard enough to take out my kneecaps, I wasn’t going to complain when he put me on my back, casually knocked my legs apart wide, and slide his spit-wet still-hard cock into the trembling aftershocks of my pussy.

“Fuck,” Ken muttered as he rocked into me, “how the fuck are you still so fucking tight?”

I didn’t bother answering, eyes too busy rolling into the back of my head as the head of his dick brushed my well-used g spot a few times.

“Clearly you need this massage more than I do,” Ken continued. He thrust again, slower, harder, and grinned when I cried out, legs shaking. “You like that? You want it? Getting massaged inside out? Are you paying attention?”

“Yes. Yes sir.”

“Good. Because you’re gonna earn every dollar in that envelope over there. We clear?”

There were $500 in that envelope – I knew that because that was the rate we’d agreed upon.

I’m not sure how long we fucked. I’d insisted on Ken using a condom our first time, despite both our tests coming back clean, without knowing then that he could last ages with one on. The massage oil I’d applied over his body was all over mine now, and magnified every dirty, depraved sound our bodies made as he slid in again and again. I came one more time, a weak little rolling hiccup after he’d sucked on my nipples hard, but mostly I was too overwhelmed to do anything but take the sensations, clinging to Ken’s back when he wanted to fuck face to face, and fisting the sheets when he took me from behind. By the time he spilled into the condom with a satisfied groan, I was wrung out and putty-soft and sore in the hips.

I left with $500, plus a $100 tip. I joked that I felt like I should give him a cut for the two orgasms I had. Ken told me not to worry about it, but told me that he’d like to renegotiate the terms of our arrangement. Currently, we’re meeting three times a week. It’s pretty straightforward: a little chat, then the massage for an hour, followed by fucking bareback. Recently Ken seems to have developed a bit of a fetish for coming inside me, which I’m happy to oblige thanks to the good ol IUD. At this point, I’m probably earning about ⅓ of my income from this gig if you count another client I recently took on. The roommate and I have since moved to our own studio apartments. It’s not what I imagined I’d end up doing all those years of washing dishes and teaching kids how to take the SAT, but I sure wish I’d started sooner.

Source: reddit.com/r/gonewildstories/comments/c6ghts/how_college_debt_led_me_to_start_working_as_a