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.

For those of you here who are just horny and want to hear more about my misadventures in being a private masseuse, I gotchu as well. Last weekend was a pretty fun time.

My other client, let’s call him Drew, is a pretty successful entrepreneur but kind of short for a guy, which has hampered his dating prospects somewhat (he’s a hopeless romantic who pays for sex because he’s too paranoid about being “used” to get into a real relationship, which is a whole bundle of issues I’m too well compensated to call him out on at the moment). He’s a pretty typical massage-and-happy-ending kind of guy, pleasantly vanilla – there’s not much else to say about him. I like Drew, especially as a counterpoint to Ken, who’s turning out to have a very intense domination streak to him. I don’t think of myself as submissive in general, but something about Ken always gets me face down, ass up, and slightly feral in ten minutes flat.

His biggest kink at the moment is what he calls “reluctant breeding”, which I’m…surprisingly into? The kinkiest thing I’d done before this whole massage gig was calling an ex-boyfriend “daddy” occasionally, but this weekend Ken took it to a whole new level. As I wrapped up our usual deep-tissue massage, already slightly wet from anticipation, he asked me to take off my clothes and lie on my stomach on the bed.

This was a little surprising. Usually Ken wanted me on my back with my legs thrown over his shoulders or locked around his waist as he pumped me full of cum and played with my tits, or else he’d take me doggystyle, hard and rough and almost careless. The most creative we’d gotten was me riding him while he sat in his enormous home office chair – that had been wild. Struggling as his hands held my hips down and forcefully slid me up and down his cock, rocking every so often so he’d hit my G spot and make me tighten up all over…fuck that was good. I might have even fucked him for free for that experience. But I digress.

On my stomach this time, I felt Ken’s hands moving over my skin, thumbs digging into my lower back before his fingers wandered elsewhere, groping and kneading. Ken is grabby when he really cuts loose. This all was nothing new – he often liked to give me almost a little mini-massage before taking his own pleasure. I wasn’t complaining; being expected to be both an excellent masseuse AND an excellent fuck is physically exhausting sometimes. Even better, he apparently was going to finger me again, which didn’t always happen when he was impatient (hence I’d started stretching myself out a bit before coming over). I sighed and moaned a little as Ken slicked up two fingers and tucked them right inside my cunt, finding my g spot with pinpoint accuracy and massaging it, making me gasp and rock back for more. It felt good. Warm and good. His other hand pressed down on my back, making sure I wasn’t arching up, and I squeezed down appreciatively as a third finger joined the first two. Maybe Ken wanted to fuck hard today, and wanted me open and ready. Or maybe he wanted to go slow, and was just enjoying the foreplay. It turned out to be both.

I’d just shuddered through a light orgasm, sighing and relaxing into the sheets, when Ken’s fingers suddenly pulled out and were replaced by his cock sliding in – and in, and in.

“Oh fuck,” I gasped, trying to adjust to the heat and stretch.

Ken chuckled and gave an experimental thrust. “Say thank you, sweetheart,” he grunted.

I muffled it into a pillow, already halfway to coming again.

If I’d thought doggystyle with Ken felt deep, this blew that out of the water. Something about the new position – laying prone on the bed, his heavy thighs bracketing my hips and pressing them down into the mattress, meant that the head of his cock was hitting me inside just. Right. Every. Time. He thrust. It felt unbelievably good. My whole spine turned liquid and my legs actually started quivering as Ken started to pick up the pace, holding me down and fucking into my pussy using his position of total control. I couldn’t get up, couldn’t change the leverage, could only lie there and take it over and over as his cock punched another orgasm out of me in no time. This time, I moaned out loud before I could help it. Wetness started to leak out to coat my thighs.

Ken liked that. “That’s it, that’s it,” he said, pinning my wrists to the bed as I started to thrash. “Pull your legs together,” he ordered.

Blitzed out, almost drooling, I obeyed.

This time it was Ken’s turn to curse. “Fucking tight,” he panted, and I hissed in agreement. It felt like being stretched to my limit, physically and mentally, being used this like. “You like that?

“Too deep,” I wailed, even though another involuntary squeeze of my cunt around his cock and my toes curling in ecstasy gave me away. “Too deep, too deep sir!”

“I think it’s just right. Hungry little cunt like yours, you don’t even know what deep feels like yet.”

“Don’t cum inside me,” I begged. “I don’t want to get pregnant, sir, don’t cum inside me please.”

Ken loved it when I struggled a bit, and I felt him grow even harder, thrusting more enthusiastically than before. “I don’t care,” he growled. The sound traveled straight down to my neglected clit, which I frantically reached down to rub and relieve. In no time, I’d cum again around Ken’s cock, almost crying this time from the overload of sensation. My head was somewhere else, floating high above and drunk on orgasms and being dominated so thoroughly, while my body was a feral, sweaty, wanton mess, fucked-out and still begging for more.

“My turn now,” I heard Ken whisper into my ear after I came down from the high of shaking apart underneath him.

I whimpered as he started to turn me over, still speared on his cock. The friction and stretch was veering wildly between too good and too much. This was always the hardest, most intense part: looking him in the eyes like he wanted as he bred me full. Ken made sure both my ankles were locked around his neck before he started thrusting again, hands grasping at my breasts while sucking hickeys all around my collarbone and neck as I sobbed.

“I’m gonna come inside you,” he warned as his balls slapped faster against my ass. “I’m gonna cum inside your pussy, how do you feel about that?”

“I don’t want to get pregnant-”

“But doesn’t this feel so good? You don’t like how good I make you feel?”

Ken pinched my clit between his fingers and gave it a good hard roll as he pumped in once, twice, harder. I bit down on my tongue to keep from screaming at how amazing it felt.

“Please don’t cum inside me,” I begged again. “You can cum anywhere else, just don’t- not inside my pussy.”

“Tell me it feels good.”

“Yes, it’s good, it’s good, it feels so good,” I chanted. “But I don’t think I can-”

“I don’t care.”

I whimpered and covered my face. “But I’m not on birth control, sir.”

It was all pretend, of course, but in that moment I actually felt the zing of the fantasy, that this man might actually manage to knock me up if I didn’t resist, cum flooding up against my walls and trickling through my cervix, fertilizing me.

“I don’t care,” Ken repeated, kissing me deeply before grabbing my left ankle and tugging my leg straighter as he shoved in harder, faster, more primal. “I’m gonna cum inside you.”

“*Nooo-*”

“Gimme a baby, sweetheart.”

“I can’t, oh please don’t, oh FUCK,” I moaned as Ken thrust one final time, gasping and face screwing up in pleasure as his cock started to pulse inside me, wet heat flooding my cunt and even trickling out as it coated my walls in hot spurts.

I’m not sure how long we stayed like that, both coming down from the intensity of the experience. I do remember whimpering when Ken finally pulled out and the way our skin stuck together. He was nice enough to clean me up while I lay there like a wobbly, fucked-out starfish, laughing when I whimpered as he wiped over my oversensitized mound. I felt woozy, but good, and took it happily when Ken slipped his fingers back inside me to feel his cum and push it deeper. Of course, one thing led to another and I ended up sucking him off one last time while he fingerfucked a final, muscle-cramping orgasm out of me, but the tip was more extravagant than usual so no complaints there.

So yeah, when it’s good, it’s really good. Next week we’re planning on experimenting with restraints, and Ken’s been dropping hints about being interested in spitroasting me with a friend of his, but I’m not quite there yet. Maybe someday. For now, I’m pretty happy to give massages, get my clients off, and paid well for it, and even sometimes get fucked out of my mind as a side perk. It could be worse.

Source: reddit.com/r/gonewildstories/comments/c7j4gr/how_college_debt_led_me_to_start_working_as_a