The Amateur Masseur (Patreon)

Contains: Breast Expansion, Sensual Massage

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I

I’ll admit I was pretty nervous reuniting with Alex after so many years. We were practically best friends in high school, but when her dad had to move for work I figured I never see her again. Over the past six years I’d come to realize that what I felt for her all those years ago was a crush. Well, it seems silly to call it a crush now, considering how young we were. But the feeling has never gone away, so maybe ‘crush’ isn’t even a strong enough word.

I wondered what she looked like now. I never had the guts to look her up on social media. It didn’t seem right to chase after that fantasy when I’d likely never see her again. After all, what high school relationships ever last? Besides which, we didn’t even have a real relationship. We were only ever good friends. She probably didn’t even think about me that way.

I’ve never been much of a ladies man. All through school the most I had going for me was my height, just over 6’2. But I’m hopeless at sports and not smart enough to fit in with the nerdy crowd. Anyway, Alex is coming over today. I can’t believe she’s back in town after all these years.

Nothing could have prepared me for my first sight of Alex all grown up. She was taller of course, reaching nearly to my chin. But then, when I’d last seen her we were the same height. Her hair was much longer, the dark brown strands hanging straight and shiny all the way to her lower back. She was still thin but had subtle curves to her hips. And holy shit, her boobs. When I’d last seen Alex we were both in our teens, probably just starting puberty. The adult woman who stood before me looked like she’d been run over by the puberty truck. Her black tank top stretched snug across a pair of melons that would overflow my hands pretty easily.

“Hi…” she said softly.

“Hi!” I blurted. “You –uh– you look really nice, Alex…”

She literally blushed. Had she always been so pretty? No wonder I’ve had a crush on her all these years.

***

It was like no time had passed at all. Alex and I still got along like the proverbial peas in a pod.

“…and then he said some students came to him asking how he could fail them after saying they could skip class!” She was saying.

“Oh my god… idiots!”

“I know, right? Always some morons have to ruin it for the rest of us…”

Alex laughed.

“So what else is new with you? Do you… have a girlfriend?”

My heart skipped a beat. What did it mean that she’d come right out and asked that? I didn’t dare to hope…

I shook my head.

“Nope! Free as a bird.” What was I saying? I sounded like one of my dad’s poker buddies. “How –uh– how ‘bout you?”

Alex looked down, her cheeks turning pink again. How had I ever let a goddess like this slip through my fingers?

“I had a few dates to dances in high school, but nothing since then.”

“That’s surprising.” I said frankly.

“Well… this is so embarrassing…” she began.

“Come on Alex, this is me you’re talking to.”

“I know, I just… I don’t like talking about it. People get real weird.”

“Well I’m already weird, so no worries there.”

She laughed. A lilting, melodious alto that I found unexpectedly alluring.

“Well, I think it’s these things.” She said, nodding down at her chest.”

“What? Your –um– chest?” I managed to squeak out.

“See! Even you’re being weird about it!”

I held my hands out apologetically.

“Sorry, sorry. I won’t be weird, I promise.” I started again, slowly. “So, you think that, what? Guys aren’t attracted to you?”

“Well… yeah.” She said, still looking down.

“Alex, look at me.”

She did. Her eyes were still the same bright blue diamonds I remembered. Full of knowing and ready to smile or laugh at any opportunity.

“You are the prettiest girl I’ve ever seen.” My face felt warm, and I was trembling, but I pressed on. “Any guy who doesn’t see that is an idiot.”

Her reaction surprised me. She didn’t look away or laugh. She kept staring into my eyes as if trying to see into my soul.

“You… you really mean that?”

“I really do.”

In a flash of time that probably only lasted a few seconds, but which felt like ages, I ran through all the pros and cons of what I was about to do. People always agonize about trying to date a friend. The risk of ruining the friendship. The pain of being ‘friend–zoned.’ But really, I told myself, I’d been separated from Alex for over six years, and here we were as close as ever. If she turned me down, we would survive. And if she didn’t, well…

“Would you have dinner with me, Alex?”

Her mouth fell open. “What… like… a date!?”

I nodded.

Alex was silent for several agonizing seconds. Just when I was about to retract my offer, laugh it off as a joke, she finally spoke.

“I… I’d like that.”

***

My hands shook as I pressed the doorbell button at Alex’s apartment. I hoped I was appropriately dressed. I’d dug a nice pair of khakis out of my closet and wore a button down plaid shirt. A few moments later the door swung open to reveal a woman slightly shorter than Alex, her little sister Allie, who I estimated was about nineteen now.

“Oh hey, it really is you! You clean up pretty good for such a tall freak.”

“Allie!” I heard Alex’s voice from several rooms away.

“Loverboy’s here Alex!” Allie called back. To me she added in a quieter voice. “Make sure you wear a condom, big guy.”

I felt like a bucket of cold water had been dumped over me.

“What!? I… I’m not…”

Allie erupted in laughter, doubling over. It was like Alex’s laugh pitched up an octave.

“Oh man, you should see your face! ’I, uh, erm…’ That’s too good!”

Alex’s voice made me look up, breath catching in my throat.

“Will you knock it off you little fungus!”

She wore a simple black dress with a tiny flower print. The skirt hung just past her knees, and the top had two wide straps over her shoulders that framed her big breasts gloriously. I must have been staring, because Alex turned shy again, looking toward her feet. I wondered if she could even see her feet.

“I think you broke him, sis.”

“Sorry… is it… too much? I can go change!” Alex started to turn, but I waved a hand to stop her.

“No no, sorry. You look amazing.”

Alex pulled a few strands of hair off one shoulder, twisting them in her fingers. “Really?”

“Beautiful.”

“T–thanks…”

“D’aww, aren’t you two adorable.” Allie said in a perfect imitation of a sweet old grandma.

“You have fun tonight. And remember what I said before!” She pointed at me accusingly as she stepped behind her sister.

“Don’t wake me up if you decide to come back here, and if you do get lucky, make sure you take care of these!”

Allie reached around her sister’s torso to grip a plump breast in each hand. Cleavage poured out of Alex’s dress and wobbled as Allie’s fingers squeezed and pressed.

“She loves a good massage, don’t you sis?”

Alex writhed and swatted her sister’s hands away. “Will you knock that off, you creep!”

Alex took my hand and led me out the door. Allie’s voice followed after us.

“You’ll thank me later!”

I wasn’t sure at the time which of us she meant.

II

My relationship with Alex progressed surprisingly fast. I guess it shouldn’t really have surprised me— we knew each other so well that we were able to fast–forward past that whole awkward early phase. By our third date she came back to my apartment and we made out on the couch.

I held and gripped Alex’s waist as our tongues danced. I was careful to avoid touching her beautiful breasts. We separated and she met my eyes, both of us breathing hard. She was wearing jean shorts, and a simple tank top. It wasn’t as revealing as that first dress had been, but her shape was unmistakable through the tight shirt.

“You can feel them if you want…” She said shyly. “I don’t mind… since it’s you.”

I let my hands drift slowly up Alex’s body, feeling the soft round shapes filling her massive bra. Watching for her reaction I pressed in slightly, feeling the weight of them push back against the tips of my fingers.

“Well?” Alex asked with a faint moan.

“Amazing…” I breathed.

“Really?” She asked, arching her back slightly to press herself even more into my hands.

“They’re perfect, Alex.”

“You –hmm– don’t think they’re too big?”

“What do you think ‘perfect’ means, babe? I love them because they’re yours. No more and no less.”

I leaned in to peck a kiss on the tops of each pale bosom in my hands. Our lips met again and my hands didn’t leave Alex’s breasts for at least another half hour.

***

“You know…” Alex began.

We were in bed together for the fourth time in as many weeks. Our bodies moved in a perfect rhythmic dance. I was propped up on my elbows above her, and my fingers worked the beautiful flesh of her breasts and held them in place as her body moved up and down. Periodically my lips left Alex’s mouth to tease and stimulate her nipples, but I did most of my work with my hands.

“If I had known you were such a ‘boob man’ –ahn– I would have tried to seduce you a long time ago…” She continued.

I met her eyes with a wry grin. “Is that what you did, ‘seduced’ me?”

Alex kissed me again, grabbing my hair in her hands the way I liked.

“Who do you think that ‘first date’ dress was for? I hadn’t worn it in years and was practically spilling out of the thing.”

A flash of light crossed my brain and I froze. A moment later I started moving again, getting our rhythm back.

“Do you mean you… grew?” I asked shakily.

Alex laughed. “Man, you really are obsessed. We’re –haa– twenty–three now, I’m pretty sure I’m –hmm– done growing. I just meant it was an old dress.”

I nibbled on one nipple, making Alex cry out.

“Gods, how are you so good at this?”

I kissed each of her nipples and met her eyes again.

“Like you said babe, I’m obsessed.” I grinned.

“Oh yeah?” She smirked. “Had a lot of –mmm– practice?”

“I promise you Alex, yours are the first I’ve ever touched.”

“–Hmm– lucky me then. All those poor girls out there –ahn– are missing out.”

“I’m the lucky one.” I insisted, leaning down to kiss her deeply.

***

After we’d been dating about six months, I asked Alex to move in with me. She agreed instantly, and though Allie put up a bit of a stink at having to find a roommate, I could tell she was happy for us.

Over time I found myself sometimes torn between the two new loves of my life— Alex’s breasts, and the woman herself. Really it was a false dichotomy, the two were intertwined so tightly that there was really no separating them in my mind. Luckily for me despite her initial shyness, my affection for Alex’s breasts seemed to have freed her from her negative self–image to the point that she began to love them too.

In the bedroom my hands rarely left Alex’s chest regardless of the positions we tried. I even once tried laying on my side so I could go down her while still massaging her tits. The experiment went so poorly we both collapsed into giggles before I went back to my more practical position, even though it meant taking a break from her perfect breasts.

Outside the bedroom I found myself just as obsessed. Alex usually got off work before I did, so I would often surprise her with a hug from behind that segued right into a good long groping. She rarely minded, and often would lean against me, eventually grinding her perfect ass into my lower half once my massaging got her frisky enough.

Sometimes one of us would join the other in the shower. It was a tight squeeze, but Alex joked that her breasts never got quite as clean as they did when I cleaned them for her. I would spend ages staring at the way the water coursed down her chest and into her cleavage, squeezing them together until a pool of water collected in the soft chasm between them and then pulling them apart to let it all splash down between our feet.

And every once in a while, if Alex was in just the right mood, we’d sit together and watch movies at night. To clarify, she’d sit on my lap. We watched TV together most nights, but these nights were my favorite. We somehow got the position just right so my legs didn’t fall asleep, and with her laying back against my chest I could easily see over her head. And the best part, was that I could slip my hands under her arms, take one perfect breast in each hand, and slowly play with them for hours. The first few times we tried this very quickly escalated to sexy times, but eventually I got a feel for just how much I could stimulate her flawless orbs without getting her too worked up.

I frequently found myself amazed at how large they were. So full and fat, like two plump firm fruits in my hands. Some evenings I could even swear they were bigger than I remembered, but I always told myself it was my imagination. After all, we were much too old for her breasts to still be developing.

***

I undid the buttons on Alex’s work shirt and stared in awe — as I always did — at her bra–clad beauties.

“Is this new?” I asked, fingering the lace edge of her baby blue bra.

Alex nodded. “I um… broke one of the old ones.”

My eyebrows raised questioningly.

“Not like that you weirdo! It just wore out. I’m pretty hard on bras, you know…”

“Well, let’s let this one rest awhile then…” I teased, reaching behind her to undo the hooks.

As Alex drifted off to sleep in the afterglow, I got up to use the restroom. I saw her new bra laying on the floor where I’d tossed it earlier, so I bent to pick it up so it wouldn’t get stepped on. I happened to see the tag sticking out.

“30H”

Now, I don’t know the first thing about bra sizes. Or at least, I didn’t before I started dating Alex. But she’d explained to me that she wore a 30DDD, which was the same as an F–cup. For a moment I thought maybe she’d grown even bigger, but then I remembered what she’d said about ‘sister sizes’ and figured it must just be that. I of course was forgetting that sister sizes usually included a change of band size, and H is two sizes up from F, not one. In retrospect I chalk my oversight up to the hazy state of my post–coital brain.

***

My suspicions were confirmed when Allie invited us over for lunch. On my way back from the bathroom I overheard them in the kitchen talking.

“Jesus Alex, what happened to you?”

“What are you talking about?”

“Don’t play dumb with me. Your tits are huge!”

“Keep your voice down! They’ve always been big…” Alex whispered loudly.

I was so startled by the conversation that I stopped just around the corner and kept listening.

“They weren’t that big when you moved out… are you pregnant or something??”

“No!” Alex gasped. “We’re always super careful… They probably just seem big because you haven’t seen me in a while.”

“Bullshit. Let me see…”

“Hey!”

“Yeah, they’re definitely bigger. What size bra is this?”

“Get your hands off me! It’s none of your business!”

“30 H, holy shit! That’s two cup sizes in like five months. What has loverboy been feeding you?”

“I still eat perfectly healthy thank you very much! Are you saying I look fat?”

Allie clicked her tongue. “No. You’re just as skinny as ever, except for these monsters…”

“I said stop that!”

“Wait… your face is all red. Don’t tell me it’s true?”

“What?”

“Don’t ‘what’ me! All those times you let me play with them and I said the stimulation would help you grow. That was just a prank! Don’t tell me it’s really true!?”

“I think it might be…”

“Fuck me, I bet that pervert can’t keep his hands off them… does he just spend every waking moment groping your tits??”

“Be quiet, he’ll hear you!”

“Ah yes, keeping secrets from your boyfriend, the rock–solid foundation of every good relationship…”

“Shut it.”

“Fine, fine. But damn… I can’t believe it really works. Maybe I should find a nice girl to give me massages day and night to see if I can catch up with you. Maybe it’s genetic?”

“Will you quit it?”

I realized to my shame that I’d been eavesdropping, and made intentionally noisy steps down the hall.

“Hey, what are you two gabbing about?”

“Oh, you know, girl stuff.” Allie said with a wicked smile.

“Hey babe, do you know any nice girls we could set Allie up with?” Alex asked, slipping her arm around my back as I stepped up beside her.

“All the nice girls I know are right here.” I said, leaning down to peck a kiss on Alex’s lips.

“Gross! I’m right here you sickos!”

III

I can’t say for sure whether I started massaging Alex’s breasts even more after Allie’s bombshell revelation. I was doing it so much already that it probably was about the same amount. The only real difference now was that I was paying even closer attention to how they felt. As always they were full and firm, sometimes gravity–defying in the way they held their shape.

In an amusing similarity to Allie’s accusation, I very nearly spent every possible waking moment with my hands on Alex’s breasts, as much as she would let me. Once in a while she’d swat my hands away, if she was cooking or otherwise occupied. But in bed, in the shower, and on the couch, I squeezed and kneaded and fondled the days away.

Allie was right of course, Alex was growing. Not in the way I sometimes read about back in the dark days before I reunited with Alex, those ridiculous stories about busting buttons and tits swelling like water balloons. But week after week I could tell my baby’s babies were getting even bigger.

I wondered if she noticed it too. She must have, since she was the one buying bigger bras. One by one I spotted the new ones when she put them on or I took them off. I’m not proud of this, but I always checked the tags when she was asleep or not at home, and they all were 30H. Then one day I spotted a new one as she was getting dressed. It was a little more utilitarian than the rest of her collection, a dark beige fabric with just a little lace.

“Is that another new bra, babe?” I asked with what I hoped was a nonchalant tone.

“Mmhmm,” she nodded, “it’s not as pretty as my other ones, but it’s super comfortable.”

“Nice.”

“Don’t get any ideas, mister. I’m already gonna be late for work. If you’re good I’ll let you take it off tonight.”

“Double nice.”

Alex rolled her eyes, kissed me, and left for work.

***

“Babe…” Alex began slowly one evening.

We were eating dinner on the couch, she’d paused the TV between episodes.

“Hmm?”

“I think we need to… cut back… on the breast massaging.”

“What? Why? Are you okay?”

“I’m fine, they’re just… a little tender sometimes.”

“Oh, I’m sorry hon. Why didn’t you say something sooner?”

“It’s not that bad, really.” She said reassuringly. “Let’s just uh, keep it strictly to the bedroom, okay?”

“Of course baby, I’m sorry.”

“It’s really fine, don’t feel bad.”

“I’ll have to find something else to do while we watch movies I guess.” I joked.

Alex rolled her eyes. “Why don’t I make us some popcorn, massage boy?”

“Deal.”

I hadn’t realized just how much time I spent with my hands overflowing with Alex’s breasts until I was denied that pleasure. Even when we made love, I made an effort to put my hands elsewhere on her body. My showers weren’t nearly as fun, and I had to consciously resist the urge to cup her bloated beauties from behind when I greeted her each night.

About a month after this new restriction, I was startled awake in the middle of the night. The whole front of my body felt cold for the absence of Alex’s form cuddled against me. I blinked open my bleary eyes to see her sitting up in bed, shifted slightly away. She had her arms crossed over her chest, but I could see her soft breasts pressing out between her thin arms under her oversized sleep tee.

“Hmmm, what’s wrong babe?” I mumbled.

“Were you… massaging me in your sleep?”

I was fully awake now.

“Huh… what? Was I?”

“You were.”

“Oh I’m sorry Alex. Maybe I’m –er– going through withdrawals?”

My face must have looked profoundly pathetic, because Alex’s expression softened. She crawled over to me and rolled me onto my back, lifting one knee to straddle my body, siting on my stomach. She took both my hands in hers and guided them under her shirt, where they reflexively found the fat teardrops of her breasts and started kneading her pliable flesh.

“You’re hopeless, you know that?” Alex said as she bent down to kiss me. My hands never stopped moving, and with that my prohibition was lifted.

***

One night we were watching a movie. Alex was one again in my favorite spot— comfortably on my lap while I softly massaged her breasts.

“Hey babe, do you feel a little swollen?” I asked cautiously.

To my surprise Alex simply said “Not really. They probably just grew again.”

I froze. Even my hands and fingers stopped moving. Alex paused the movie then slid out of my grasp to turn and sit across from me on the ottoman.

“W-what?” I asked dumbly.

“Are we finally doing this?” She asked.

“Doing what?”

“–tsk– I’m surprised it took you this long to notice, with your hands on them night and day. Maybe you hold them so much you didn’t notice the gradual change.”

“What are you saying?” I felt a mild panic. I couldn’t read Alex’s expression, but I assumed she was mad. After all, she’d hated how big her breasts were when we started dating, and now they were getting even bigger.

“You’re cute when you try to play dumb, you know that?”

I opened my mouth but no words came out.

“Yes. My boobs are getting bigger. Allie has this theory—“

“I know.”

“You what?”

“I overheard some of your conversation that day at her place.”

“You were listening in on us??”

“No!” I lied. “I just, was on my way back from the bathroom and overheard the last bit.”

“You’re a terrible liar. Well, whatever, I probably should have told you a long time ago, since it turns out she was right.”

The silence stretched.

“So um… how… –er– how…”

“How big are they?” She demanded.

I nodded.

“Well… remember that flesh tone bra I bought last month?”

I nodded again.

“It’s a 30K.”

My mind tried to do the math, but failed. Alex wasn’t wearing the bra in question, and her braless breasts jiggled every time she spoke. I could see her nipples pressing through her shirt.

“I can tell you’re too distracted to do the math, so I’ll help you out.”

Alex slowly crawled from the ottoman onto the couch, still facing me.

“On our first date I was wearing a triple-D.”

She startled my legs and moved closer.

“That’s an F cup.”

She propped herself with one arm beside my head to lean against the back of the couch, and held up one hand to count on her fingers.

“G H I J K, that’s five cup sizes.”

Alex put her other hand beside my head and rose up on her knees until her glorious, perfect breasts were inches from my face.

“In ten months. That’s an extra inch every other month, more or less.”

She pressed her body into mine, and my hands reached up automatically to press into the sides of her breasts as I breathed in her wondrous scent.

“And also,” she continued, breathing a little harder, “that 30K is starting to get tight already.”

I pulled my hands away as if burned. Alex sat back on my knees.

“You can keep going, on one condition.”

“Wha–“ My voice cracked and I swallowed. “What’s that?”

“You have to pay for the next one. At this size they’re getting really expensive.”

There was no mistaking her expression now.

“Deal.”

“Good.” She whispered. “Now get those hands back up here.”