How college debt led me to start working as a private masseuse, part 2 [MF]

Whoa, didn’t expect my last post to get the response it did ! Didn’t mean for it to get that political in the comments either, but I will acknowledge that I’m pretty privileged: I’m in a demographic that’s highly sought after for this type of work, and also could ask my roommate for advice in the beginning, so I’ve gotten to be super choosy with my clients. There’s guys who will pay a lot more than my current ones, but I find them super unpleasant/potentially dangerous so I don’t take them on. And yeah, the whole thing is kind of fucked up and makes it really hard to date because I don’t have much free time of my own anymore – I don’t know if I can ever get married at this point given that I’d want to be upfront with my spouse about what I’ve done (hookups are also tricky because I have to stay clean for my clients). I mainly take it day by day: my living expenses are almost fully covered by this gig, so I can focus on paying down my student loans with my legit job. And thanks to being choosy with my clientele, I actually get to have some pretty good sex on the regular – being frustrated is never a problem haha. It’s a matter of selective focus, and all that.

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.

[MF] Sleeping with and dominated by my former professor

A couple years ago, I got my first and only B in college. Thanks, multivariable calculus. Mostly, I remember sitting in section confused out of my mind as my TA talked about B coordinates and eigenvectors and stuff. The poor grade was partially my fault; living on the opposite end of the campus as lecture meant I did not go to office hours as much as I should have. As a result, while some girls in my class talked about how the professor was attractive enough to make up for the 12 hours of psets we had to do a week, I skipped lecture often enough that I didn’t even know what he looked like until the final exam. By then I was so tired from 10 straight hours of studying that I barely glanced at him before diving into the blue answer booklets.

I’d totally deleted Professor M and his class from my memory, until recently when I split up with the older man who’d taken my virginity and had been breeding me on the regular. He recommended I rebound with a friend of his, and as pissed off at him as I was at the time, well. When I met Professor M again (in the parking lot of a Denny’s of all places), I noticed all the things I hadn’t the first time: how tall he was, how he could definitely hold me down and keep me down, and how the touch of silver at his temples made him quite handsome.

The last time breeding with my daddy [MF]

Whoa, it’s been a while! Life got pretty crazy for the past couple months, but it’s finally settling in, so I thought I’d do a quick update on me and Sam for anyone who’s interested. For a variety of reasons that I won’t get into, we’re no longer seeing each other, but he was nice enough to set me up with a friend of his who has very similar tastes and – unbelievably – was one of my first professors in college. But that’s a story for a different time. Below is from the last time Sam and I hooked up; trying to preserve the good memories from this strange period of my life:

Ever since I got an IUD, Sam and I had been, for lack of a better term, fucking like rabbits in heat. He’s probably had his way with me against every supportive surface in his apartment, and plenty more times on the rug or floor. I couldn’t seem to get enough of him stripping me down, dominating me both physically and mentally as I try to get away, and finally cumming inside me as I beg him not to get me pregnant.

Bred in his bed [MF]

Just a quick update on what Sam and I have been up to this past week! :)

We met up Thursday night – that is, Sam picked me up at my place, and we damn near fucked in his car in his apartment parking lot after he ate me out in the back seat, dress rucked up to my stomach and my office heels grinding into the fogged up window glass. Sam then had me suck his cock for a few minutes, just sloppy, enthusiastic sucks around his cockhead and balls, before pushing me away, zipping himself back into his jeans with some difficulty, and telling me to follow him.

One of his neighbors gave me a dirty look as we caught her exiting her apartment, grocery tote bag in hand. I blushed as I imagined her realizing that not only did I look well-fucked, I was about to be even more so by the much older, obviously aroused man beside me. Then a second later we were inside Sam’s quiet apartment, kissing deeply against the front door, stumbling into his warm bedroom.

Playing at impregnation [MF]

So after reading several reddit comments/insights yesterday, I decided to try and get over my sexual hang-ups by immersing myself in them wholeheartedly. It’s definitely going to be a slow process, but I wanted to get started right away before I chickened out, so I asked Sam whether we could meet again that night. He was surprised since we usually take a day or two’s break after each session, but agreed quickly when I said I wanted to explore the impregnation kink he’d teased me about having after fucking me bare the day before. After exchanging ideas from our favorite porn videos (and NSFW subreddits!), we were ready to start.

Sam first fucked me with a condom to a light orgasm on his couch. That in itself was a lot of fun, as he turned the TV on and we both watched The Office as he took me doggystyle. Then Sam led me naked to his bedroom, where I sprawled between his legs as he reached between mine and worked my vulva over with our Hitachi.

“I want you craving my bare cock,” he said as I counted out three intense, white-out orgasms in quick succession. “This is just gonna make you nice and tight for me. You’re not satisfied yet, are you?”

[MF] Got carried away and let myself get barebacked by a married man

So originally I thought this would be a super quick, fun update about my sexual relationship with a married man and the kinky stuff we usually get up to:forced orgasms, fucking machines, the works. However, things got a little out of control during a sex marathon we planned to pass the bitter cold today. My head is still spinning with thoughts about what it means. My body is less confused. I’ve been alternating between enjoying the memory and burning up in shame, so hopefully this will help me work through my thoughts.

By this time Sam and I have had our arrangement for nearly three years. My parents ask why I never seem to have a long-lasting relationship with the good, solid Asian boys they “introduce” me to. In truth, it’s because after our dates, I rush as soon as possible to Sam’s apartment to let him take me apart like I really need. On his part, his wife knows that he’s seeing SOMEBODY, but as long as he keeps up appearances for his family’s sake, she actually prefers to know less. She’d probably be accepting if she knew he was tying up a girl young enough to be his daughter several times a week to be machine-fucked and deep throat him, but I’m grateful she doesn’t ask too many questions.

My [F] forced orgasm experience with a married man (part 6) (end)

“No more,” I sobbed after a particularly brutal orgasm that left the sybian soaked and my stomach cramping. I was no longer sitting on the sybian but slumped on it, too exhausted to do anything but take the mechanical cock still churning me open.

“One more,” Sam promised. And another, and another, until I’d forgotten the discomfort and that I’d ever been anything but right here, riding the perfect cock for my next vaginal, full-body orgasm

“I want you to get addicted to being fucked,” Sam admitted as he moved in front of me. The sybian was now on its third-highest setting and I was sweating out another orgasm in agonized pleasure, weakly moaning a combination of “Yes daddy” and “No more daddy.” “I want you to put yourself to work earning your orgasm,” Sam continued, moving to stand in front of me. He fed me his cock inch by inch, and I sucked at it eagerly, filled up at both ends as I rocked my hips with the sybian cock. Sam had overloaded me with sensation, and he talked about how well I took to being fucked and how I really should have done this sooner. I didn’t care about being a virgin anymore. I didn’t care that Sam had a family while I had his cock down my throat. All I cared about was that I was still coming in leg-shaking waves as the sybian cock rotated lazily through my vaginal walls, like some kind of slutty nymphomaniac. Nothing else mattered besides the dildo relentlessly fucking a space for itself into my pussy.

My [F] forced orgasm experience with a married man (part 5)

“I want you really wet for this,” Sam said as I lowered myself onto the machine, spreading my pussy across the little nubby pad that Sam assured me would prepare me to take in the cock attachments he’d yet to put on the machine. I was shaking from nervousness and arousal and shame – not only was today the day I would lose my virginity, but I was losing it to a BDSM machine operated by married man, who’d already done countless filthy things to my body. Moreover, I’d agreed to do this in his apartment that he stayed in on nights that things with his wife got really bad, and the tiny quarters made everything we did feel even more illicit.

Then Sam turned on the Sybian, and it was like he’d flipped a switch in me from ‘remorseful’ to ‘begging for it’.

“Describe how it feels,” Sam said as I writhed over the rumbling machine, feeling its powerful vibrations shake my legs and stimulate my whole pussy.

“It feels like it’s going IN me,” I moaned as the Sybian’s vibrations rolled over my whole lower half, and embarrassingly, two minutes later, I started to chant, “Gonna come gonna come please let me come daddy.”

My [F] forced orgasm experience with a married man (part 4)

That’s how our next few sessions went as well. We’d meet in his hotel room after he was done with work, maybe have a drink or two while complaining about our respective days, and then Sam would force orgasm after orgasm out of me with a new clit toy of the month before making me suck his cock or give him a thighjob. It’s weird to think back on all the stuff we did without outright penetration – Sam pressing me into walls, his cock furiously rubbing between my pussy folds as he fucked my legs and groped my breasts; taking a shower together, which ended with me deep throating him for the first time and choking on his come; him laying down on the bed and me sliding my pussy over and over his cockhead until he came. We’d both decided to stop using condoms at that point since we’d gotten tested. This was rapidly becoming all too comfortable, even though I was still feeling guilty over helping Sam cheat and then guilty over liking the sex with him so much. He’d indulged my fantasy while introducing me to new ones: sensory deprivation, 69-ing, exhibitionism (sucking him off by the glass balcony door), and daddy-daughter role playing.