Practice Makes Perfect

“Can I stop now?” I asked. Gasping for breath.

“Did I say you could stop?” She snapped, barely looking up from her phone. Swiveling around in her chair.

“My cheeks burn and my jaw hurts!” I whined.

“Then you’re not keeping it wet enough, and you’re not relaxing your jaw, or you’re relaxing too much. You should be drooling like a dumb bimbo. And make sure you hum. They like that. It vibrates and makes them think you’re into it...even if you’re not.”

I opened my mouth to argue, but felt her heel on the back of my head. Forcing it back onto the big rubber cock suction cupped to the wall. The same one I'd been sucking on for the past hour and a half.

“You need to get better at deepthroating.” She said, forcing me further and further with her leg until all 10 inches were down my throat and I was sputtering and squirming.

Right when I thought I was gonna pass out, she released. Allowing the python to slide out of my gullet. I gulped for air.

“You really...gasp...think...gasp...someone is gonna last this long?” I asked between breaths. Drool, tears, and spittle leaking from my face.

“If you do it right they won’t last 2 minutes.” She said, finally looking up from her phone. “But you never know how many will be waiting in line. And I can't have a bitch that quits early! Balls.”

I started lapping at the fake rubber testicles. Licking and sucking them and feeling like such a fucking freak as I was forced to “play” with my toy in front of her.

“You really fink it’ll be thatt manyf?” I asked with the rubber sack still in my mouth.

“There’s no telling.” She said, “your Instagram’s taking off, you get dick pics on KiK every 5 minutes, and your Tumblr account has over 2k followers. Every time i post a pic of your slutty butt we get messages from all kinds of guys ready to fuck it. Speaking of...”

She snapped her fingers. Twirling them around, apparently intending for me to do the same.

I pivoted on all fours so that my ass was facing the cock.

“Do I get lube?” I asked inquisitively.

She thought for a second then shook her head. “No, you should have kept it wet enough while sucking it. You never know when some guy will just flip you around the same way.”

I shivered at the thought. But didn’t want to argue and make matters worse.

I reached back and grabbed the shaft, feeling the head flop around my cheeks until I got it between them, and pressed it against my hole.

The first few inches always feel like they’ll tear me open, but I’ve finally learned to spend a couple seconds there, allowing my sphincter to relax. Though I doubt I'd have that much time with a real one.

I started rocking back and forth. Slowly working it more and more inside of me. Wincing at the pain.

“You really...think...we’ll...find someone?” I asked in between grunts.

“Oh I know we will.” She said, tapping at her phone again, “if I started you a Grindr account I could have 5 guys here by the end of the hour!”

The reality of her words hit me like a hammer. It was something I'd fantasized about for years: being used by a guy, but the possible transition from fantasy to reality petrified me.

She tapped away on her phone while I tapped my ass against the cock. Now that I’d worked it most of the way in it was becoming less painful and more pleasurable.

“Do you think...you’ll...fuck other guys too?” I asked. Keeping my eyes down on the floor as I grunted and twerked.

She simply shrugged. “Probably.”

She seemed so nonchalant about it. But it made my insides shift. It was ironic, most of our conversations revolved around me getting fucked by other guys, yet for some reason I never thought that she might get the same treatment.

I started blubbering pathetically, “b-b-but i don’t want y-you t-to f-fuck—“

“Turn around and put it back in your mouth.” She said, cutting me off. Either not caring about what I had to say, or wanting to shut me up before I could get out what she already knew I would say.

“But it’s been in my...”

“Ass. Yes. It’s called ‘ass-to-mouth’. All the little sluts do it. So you will too. And if you’ve been douching and cleaning like I've been telling you to, it shouldn’t be a problem, should it?!”

“N-no ma’am...” I said, defeated. I turned around and cringed as I took the cock back in my mouth.

She always did this, any time things got remotely intimate she would change the subject or make me do something depraved. It was like she had attachment issues and this was some kind of coping mechanism for her.

That was actually how we met. Apparently one of her boyfriend’s was getting too attached and she needed relief. A quick post on Fetlife and the next thing I knew I was at her apartment getting my ass lit up by her hair brush.

But maybe I’m the one with attachment issues? We’ve never said we’re boyfriend and girlfriend. Sure, we’ve been on ‘dates’. But that was mostly her finding ways to publicly humiliate me. Like taking me to the park or the mall in a diaper, and then changing me when there was sure to be people around.

We’ve never even had sex. Of course, that would be difficult with the cage she makes me wear...

“You’re leaking.” She said.

I looked down, dick still in my mouth, only to see strings of precum dripping out of the chastity cage between my legs and onto the floor.

“Spin back around and put it in your ass while you lick up your mess.” She barked.

I did so obediently, lapping up my sticky juices off the wood floor.

“When do you think I'll get to...cum again?” I asked apprehensively. Worried it might set her off. But she finally stopped swiveling in her chair and looked up. Contemplating.

“Hmmm...how ‘bout now?” She asked.

“Really?!” I was so taken aback. It wasn’t the answer I thought I'd get.

She rolled the chair over to the box and rummaged through until she pulled out another dildo. A white one this time, with big veiny details. She leaned over, the key to my cage dangling from her neck, and plopped the dildo on the floor in front of me.

“Sit.” She commanded.

I looked at her for more information but it never came. She just went back to her phone. I didn’t want to disturb her, fearing it may make her change her mind. So I spit on the cock and spread my cheeks. Lowering myself onto it.

“A-are you going to unlock me...?” I asked hesitantly.

“Why would I do that?” She said to her phone.

“W-well how am I supposed to cum with the cage on?”

“From fucking your asshole?” She retorted. Eyebrows raised like I'd asked the stupidest question imaginable.

“I-is that possible...?”

“Have you never heard of a sissygasm?”

“N-no?”

“Jesus, with how much porn you watch you’ve never seen a faggot like you cum from getting fucked up the ass?!” she tapped on her phone again, this time scrolling through and flipping it around to show me when she found what she was looking for.

It was a sissy hiking up her skirt and bouncing up and down on a dildo with her tiny clitty in a cage. Basically mirroring my current state. But after a couple of minutes with her pathetic moans and cage flopping around, her moans became more breathey, more high-pitched. Until finally ropes and ropes of cum starting spewing through the tiny hole of the chastity device. She showed me 3 more videos just like it.

“Y-you want me to cum like that…?” I asked incredulously.

“It’s the only way you’ll get to cum from now on.” She said, shrugging, taking back her phone so she could go back to whatever else it was she was doing.

I bit my lip. Not really knowing where to start, but I figured bouncing was as good a place as any.

I hated this position. It made my legs burn and my calves ache. But there was no denying it hit a certain spot in my rectum that I didn’t usually stimulate.

My cage flopped up and down. Clinking and clanking from the dangling lock striking the hard plastic.

She must have gotten bored or something, because after about 10 minutes of me whimpering on top of the cock as I squatted up and down on it, she got up and left the room.

I was a bit taken aback. Usually during my “training sessions” she would watch me. Well...more like “supervise” me as she sat and did whatever on her phone.

I didn’t know what to do, so I decided to just continue what I was doing, searching for any hints of building to this mysterious “sissygasm”.

After about 30 minutes, she finally came back with Chinese take out.

“Still haven’t done it?” she asked with a mouth full of Chow Mein.

I shook my head in frustration. I was hot, hungry, sweating, and not the least bit turned on.

“I don’t think this is gonna happen…” I whined, “Can I stop?”

She shrugged. “Up to you I guess. It’s not my balls that need emptying…”

I groaned as I realized she was leaving it up to me. Did I really want to keep doing this? Not really. But did I want to ruin my chance at getting to cum? Definitely not. It had been at least 3 months since my last orgasm. I needed to get some sort of relief.

I took a deep breath and started going again with renewed vigor. Putting weight on my hands so I could maneuver my hips around and try to find a spot that worked.

There.

A small little button right behind where my penis was. If I hit that I got the most sensation. Even little tremors through my legs. I decided to focus on that.

I leaned back so that the cock was pointed straight at that spot. Driving my hips downward and trying to grind to get as much stimulation as possible.

It gave me this weird feeling like I wanted to pee. I hoped to god I didn’t piss myself right there. She probably wouldn’t ever let me wear anything other than a diaper from now on.

As the rubber dick pressed behind my own dick, I could feel the pressure building. But repeated jabbing of it did nothing but make me feel like I was pushing up against a wall that I couldn’t break through.

So I left it there. Right up against what I assumed was my prostate, and started clenching. Kegeling. Like I'd heard girls do. To my surprise, it worked!

I could feel the pressure building more. I must have been making noises, because she looked up from her dinner and set down her phone.

It was like I was scratching an itch. An itch I’d had for over 3 months. My legs started shaking. Quaking. My entire midsection felt like it was tingling. Was this it? Was it happening?

Finally I broke through whatever barrier was there, and felt warm goo oozing through my cage and down my balls. Her eyes and smile grew wide as she watched.

But there was no pleasure. It wasn’t like an orgasm. Sure it felt good building it up, but the “climax” was as uneventful as a Stephen King novel. I didn’t even lose my horniness. My balls were just slightly less achey.

“W-was that it?” I asked disappointedly.

“I think so!” she smiled. Though the ‘sissygasm’ was a letdown. It felt good for her to show signs of some approval.

“That was...not as good as I thought it would be.”

“Aww...well that’s too bad.” she said without the slightest hint of empathy. “You can try again if you want. But clean up your mess first.”

Dutifully I leaned forward and licked my mess up off the floor. Despite not having much of an exciting ending, I sure did leave a lot of sticky credits on the floor.

“Go ahead and let yourself out.” she said after noting I was done and defeated. She took off her top without caring that I could see her gorgeous breasts. Changed into her pajamas, and climbed into bed.

I gathered up my dildos and other belongings as I took my walk of shame out of her room.

“By the way…” she said just before I closed the door, “You have a date tomorrow with a guy named Marco. I’m sure if you make those sissy squirties he’ll keep having you back!”

Her wicked laughter rang in my ears as I clicked the door shut.

THE END