I got home earlier than usual, clutching the nondescript shopping bag close to me. I immediately headed to my room.
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Had the past few hours really happened? Shame ran through me like a river, currents of embarrassment and disgust battering and turning me around. I wasn't gay. I had nothing wrong with people who were gay, of course, but I'd always dated women. I always masturbated to women.
However, I couldn't deny what had occurred.
I dumped the bag onto my bed.
As I did, even though nobody was around me, I blushed. Clara hadn't been stingy. Inside was a whole dildo training set with varying sizes, several butt plugs, a large bottle of anal safe lubricant, a cellophane package of frilly women's underwear, and what she had called an "enema bulb."
Another pack of bubblegum fell out next to it. A sticky note on it said "For Jessi." I pocketed the pack, happy to replenish my stash, which was running dangerously low.
Finally, a huge and realistic black dildo, complete with wrinkled silicone testicles, flopped onto my sheets.
I originally opened the bag Clara's in her room, but my brain had refused to fully understand. I felt like I was in a fugue state.
This whole time I had known her, Clara had been referring to me as a "good girl" and a "sissy." It was only now that the full weight of what she wanted from me fell onto my shoulders.
She didn't just want me to just make minor changes if I was going to date her. She wanted to fundamentally transform me.
I should've been horrified. I should have cut everything right there and never contacted her again.
Instead, I felt more aroused than I had ever before.
I buried my face in my hands.
Even still, I felt my body burning, craving stimulation, completely out of my control.
With shaky fingers, I lowered my hands and touched the realistic plastic cock, comparing it to the one I just cleaned with my mouth. It was much softer, with an ample amount of give and flexibility.
It was also just a touch longer than Cameron's, but it was certainly less thick. After swallowing his over and over, I was sure that even with my bruised throat, I would have been able to take the majority of this one.
What was I saying? instead of running away as fast as I could, I was comparing a fake dick to a real one I had just let deflower my esophagus?
I dejectedly grabbed the enema bulb and went to the bathroom.
"You need to wash yourself out good," she said. "Women have to take dick all the time and are expected to never complain. If I'm ever going to date someone long-term, I need them to understand how much work that is."
Part of that work was the preparation, apparently.
I took the bulb and filled it with water from the sink, Inserting it into my ass. I squeezed, sending lukewarm water shooting into me. I shivered. I never had to do something so clinical to myself.
I did this repeatedly, filling myself with water and emptying until it ran clean, following the instructions Clara had given me.
Finally, I was done, and I stood.
I looked in the mirror. I could see my aching, purple balls hang from my body, and my dick, forced into a two inch long cage, had a distinct sheen of pre-cum on its head.
Why couldn't I stop leaking?
It was only after the enema I could shower. As I scrubbed soap over my body, I paid special attention to my ass.
Maybe Clara was right. Men never realized how much work women had to go through to get ready for these kinds of things. The anxiety in me ebbed a bit. Maybe that's all this was. She was trying to show me how narrowminded I would've been without a real life experience.
I finished showering and headed to the bedroom.
I looked at my phone. Clara had sent me the new link.
She had said this one was something to watch instead of listen to, and I wondered what it would be.
I opened the link and it automatically set itself to full screen. Holy shit. It was two hours!
The screen was black with a faint pink spiral spinning in the background. Faint shadows and shapes danced across the screen, playing tricks on my eyes.
A steady, even drone started to sound. A feminine robotic voice filled the air.
“Your brain is tired.”
I jumped, not having my headphones in. I paused, put on my headphones, sat in bed, restarted the video, and I pressed play again.
“Your brain is tired.”
I sighed. I was tired, that was true.
“Your body is tired too.”
I felt myself relax. I had been working on overdrive, and I suddenly felt it hit me like a train.
“Close your eyes and imagine a bubble bubblegum inflating around you with every breath.”
I followed the instructions, breathing out and thinking about a large pink bubble growing larger and larger. It was thick, wet, and sticky, with granules of sweet sugar melting.
“Let the bubble float, sinking delicately down through the air.”
I felt my body, still and heavy, become nearly weightless in my bubble. It really was like I was floating down, slowly descending.
Sink deeper in your bubble.” Fingers snapped.
My brain quieted.
“Float down.”
I floated in my bubblegum bubble.
“Sleep, sissy.”
I heard the sound of snapping fingers.
I blinked bleariness out of my eyes. It was dark outside. I looked at my screen—the video had just finished and was closing out.
Jesus. I guess I must have slept almost through the whole thing. It seemed like a relaxation or guided meditation video.
I texted Clara as I unwrapped a piece of gum and started chewing it, salivating as it filled my mouth with sugar.
- “Hey! I finished the video.”
My phone buzzed.
- “Good. 🙂 What did you think?”
I decided to be transparent.
- “Honestly? Slept through the whole thing.
She texted back again.
- “That's okay! Try this one out. It's shorter!”
She texted me again. This one was a video link.
Just like the last, it automatically brought itself to full screen.
Only this one wasn't a spiral.
It was Clara, her hair tied back with black ribbon and wearing a baggy, black sweater with a spiderweb pattern. She was sitting on the left side of the screen, a faint smile curling just the corners of her black lips.
"Hey there, baby."
Had Clara made this video just for me?
"I know that I gave you a bunch of new toys to play with," she said through the screen, "but I thought you could use a little help getting used to them."
I felt my stomach dropped. I had known that something like this was coming, but after having gone completely blank the last two hours, had almost forgotten. I stared at the various plugs and toys strewn across the bed.
As I did, I felt something different from before. Previously, when I looked at them, I had felt fear and aversion. I still felt those things, but now, intertwined along with them was an intense curiosity.
The way that Clara had explained it when I was at her apartment was that all men have a kind of G-spot of their own.
"I'm going to help you find that little cum button inside of you," Clara said through the video.
It was like she always knew what I was going to think next, even during a recording.
"So I want you to float down," she said. She snapped her fingers.
My body relaxed, and my mind became fuzzy. That meditation video had really done a number on me. Just at the sound of her snapping, I felt something shift. I continued to stare as I chewed my gum, feeling my eyes get glassy.
"We're going to start nice and small," she said, reaching off screen and pulling out one of the trainer dildos that she had purchased for me. It was maybe five inches long and thinner than the others, meant for someone's first time.
I reached out my own hand and followed suit, Grabbing the same dildo. It was made of hard glass, so it was smooth and cool to the touch.
"Vaginas get to make their own lube for the most part, but unless you want to use your spit, you're going to want plenty of this for your first time," Clara said. She grabbed the bottle of jelly lube and squeezed it out onto the dildo, putting down the bottle and using her free hand to spread it along its whole surface, as if she were stroking a cock.
I swallowed and tried to mirror her, adding lubricant and running my hand up and down it's glass shaft. There were gentle ridges and bumps along, meant for extra stimulation. As I felt them run along my palm, I wondered how it would feel inside of me, touching parts of me that had never been touched.
"You also have to add plenty of lube to your asshole," she said. "I'm not opposed to causing you pain, But I want to make sure that pleasure comes first."
She took her already lubricant-covered hand and added more to just her pointer finger, swirling and stirring it through the air as she slowly moved it up, clearly indicating for me to push the lubricant into my body.
I hesitated. Was this really who I was?
Once again, it almost felt like Clara was directly responding to me. "If you ever want to understand your feminine side and date me, you need to do this."
Even though she couldn't see me, I shyly nodded
"So just sink deeper," she said, and she snapped.
I melted back on my bed, leaning the phone against a pillow so I had both hands free and bringing my lube-soaked finger to my ass. The cold, viscous liquid touched my skin, and I gasped.
After using the enema bulb on myself, I thought that I knew how it would feel to have something in me. Now, though, as I prodded at my puckering asshole with a single finger, I felt like there was a vacuum inside of my body. The sensitivity in my ass skyrocketed, and even as I pushed in to my first knuckle, I felt my whole quickly relax, hungry for more.
"You're going to need to push the lube is deep as possible," Clara said, smirking. "The more you get inside of yourself now, the better you'll feel later."
I steadily pushed the lube into myself, feeling something growing steadily inside of me.
The cock I had sucked earlier that day flashed through my brain. If this was how good a single finger felt, what would it be like to have that monster rearranging my insides? Would he take it slow with me like he had with Clara? Or would he piston in and out of my ass like I was just a toy? How would it feel to be used by him?
Oh, fuck. I was imagining being fucked by a guy.
"Good girl," Clara said, interrupting my thoughts. "Now, after you get used to just your finger, we're going to move onto your first fake cock." She held up the first glass dildo again. I want you to work the tip in, not pushing yourself too hard.
I apprehensively pulled my finger from my ass, lining up the lubricated dildo in its place. I go. This dildo, while not nearly as large as some of the other ones Clara had included for me, was still significantly more substantial than a finger.
The worst part was that most of my nervousness was eclipsed by excitement.
I applied even and steady pressure, relaxing and flexing my ass muscles to accept the foreign item into my body.
After some initial struggling, I felt the first inch of the dildo slide inside of me. I gasped as it did, my stretched hole responding with pain. I let it sit in the same spot for a moment.
"you are such a good princess,” Clara said from my screen.
Then an embedded video popped up to the right of her. It was a of a cock that had just started to enter an asshole. I could see the shaved thighs and wide hips of the recipient, and a caged cock hung between their legs.
"So we're going to play a game," Clara said. "You're going to follow along, fucking with the metronome that I play, going as deep as I say to."
My eyes widened. I knew that there would be instructions during this video, but to hear that I had to push this cock into myself with every beat caused a flutter in my heart. I wasn't going to have control over the speed or intensity. Clara was. My cage tightened at the idea of once again being at her mercy.
"One more thing," she said, her smile being replaced with a stern expression. "Don't you dare fucking cum."
Cum? From a dildo?
My brain felt like mush. I knew this was wrong, but I couldn't stop.
"We're going to start off easy," she said, her smile returning, "so just go with the first few inches for now."
An electronic metronome started to sound, click, click, clicking slowly. Its beat matched the rhythm of the couple in the video, just like Clara said, and I saw the thick pink cock start to tease the bottom's hole, only entering a few inches before pulling back each time.
I steeled my nerves, and I started to move my own dildo, looking between Clara's face and the tight asshole being gently fucked.
My body tingled as I did, and with just the first few inches inside me, I felt discomfort starting to fade. With dread, I realized that my asshole was already getting accustomed to being filled.
I pulsated the dildo in and out of me with the metronome, and I stifled in involuntary groan.
"Deeper now, sissy," Clara said, "I want you to know what being fucked is like."
The video changed, and it was now of a chubby femboy in a miniskirt and stockings. His cock was uncaged and erected, but still, it only stuck 3 inches into the air. He held a dildo that was lodged in his ass, and he was taking almost the full length. The metronome changed subtly to match his rhythm.
I took a deep breath and dove deeper, taking all five inches of the slim glass cock to its base.
I almost gasped as I did. It felt like someone was stroking my cock from the inside, and after a week of no orgasms, I could feel my balls swell in response. I angled the dildo up slightly, finding the sweet spot that made me leak most. lubricant ran down my ass crack and stained my bedsheets, but I didn't care. I just wanted to keep feeling this.
Why was I so sensitive? Was it because of the videos from Clara?
I felt a warm wave of pleasure lapping over me, and my concerns felt like they were pulled away from me.
I watched Clara nod into the camera, encouraging me to give in.
I unconsciously imagined the bubblegum blowing up around me again, consuming me and surrounding me as I explored deeper and deeper into my tight asshole.
"Good slut," Clara said, Sending another ripple of pleasure through me with her praise. "Now don't you want something bigger?"
She put the first training dildo down, and she grabbed one two sizes up. It was just a little over 6 inches long and thicker than the first. The metronome stopped, and the video next to her faded.
I looked over at the same dildo laying on my blankets. Its glass twinkled up at me. The cock I had in my ass now felt amazing, but wouldn't it feel better to be even more stretched? Wouldn't it feel better to be fuck deeper?
She was right… I did want more. I was horrified at this realization, but my body moved on its own.
I licked my lips, and I removed the first dildo from me, quickly grabbing the next one. I immediately felt the vacuum inside of me, and I craved to be filled again.
I scrambled to apply lubricant, working my hand up and down the shaft excitedly. God, it felt different from a real cock. A real cock was warm and soft in my hands, and it made thick cum…
Jesus Christ. I pushed these thoughts from my mind.
"I am not gay," I muttered to myself as I lined up the next dildo to fuck my asshole
"start slow again now," Clara said, but you can still go deep."
Another video appeared next to her. This one was a lithe white twink in panties. He was tied by each limb face down to a bed so that he was spread eagle. A muscular olive-skinned man walked into frame and slapped his ass hard, causing the twink to squeal.
Then there was a jump cut, and the metronome started as I saw the muscular man on top of the twink, the panties now torn off and thrown to the side. The muscular man's thick, juicy cock was steadily invading the white twink's asshole. Unable to form words except for a high pitched moan, the twink writhed under the larger man's weight. I felt my mouth water, watching the balls of the olive-skinned man slap against the twink, trapped in bondage, and I moved my dildo to match their pace.
Oh, fuck. I had imagined that the larger dildo would satisfy me, but as I continued, I realized that I was already pushing down on it as I took it to the hilt, craving just another inch or two. I still needed more.
I continued like that for a while, training my ass as Clara told me how fast and how deep to go through the recording. The video would switch every so often, speeding up or slowing down to teach me how to take dick at different tempos.
Then, Clara put the dildo away, and the metronome stopped. It was sudden, and I felt myself whimper as I stopped my own dildo. I hated to admit it, but I had been getting close to an orgasm.
Instead, Clara reached off screen again, pulling out the massive, veiny, and realistic black cock. I felt my face go pale. I've been able to make small jumps in size, but as I imagined that beast sneaking through me, I felt unsure.
Again, it was like Clara knew every corner of my brain. "I know it's scary, honey," she said, "but ladies are expected to take this and a lot more. I want you to understand every part of me if we're going to be together, and that includes this."
I swallowed, and with shaky hands, I grabbed the plastic penis. It was heavy, and compared to the glass dildos I had been holding before, the silicone was soft and warm.
"Just start with the lube," Clara said, squirting more into her hand to apply to the long shaft in front of her. She slowly ran her tattooed fingers across the ridges and veins, and I could hear it squelch in her hands as she did. I felt like I was in a trance, putting lube into my own hand and copying her movements. As I touched the dildo, I could feel my heart beating in my chest. This thing would stretch me until I was nothing more than a sleeve for it to fit into. Still, I didn't stop.
The bubble filled up more.
Once it was covered in a thick layer of jelly, Clara made a tight "O" with her thumb and forefinger, placing the head of the fat cock against it. I brought the cockhead to my own entrance.
"Just relax, honey," she said. "It's going to be okay."
I tried my best to believe her.
She gently pushed the dildo, simulating a tight asshole with her opposite hand. I applied the same pressure, feeling the bulbous head try to enter me.
With the training I had done so far and the muscles I had newly learned to relax, I shouldn't have been surprised to feel the tip of the massive dick pop into my ass. Still, the unexpected sharp pain took my breath away for a few beats.
"You're such a good girl," Clara said encouragingly. "You're doing so well, honey. "
I groaned, relaxing my hole as much as possible.
"Even if it hurts a bit," she said, "just start moving with this video for me, sweetie."
Another video popped up on the right side of the screen. However, this one wasn't of just men. It was of Clara with a stranger. He was black, lean, tall, and nude, and his face was just offscreen.
The shock of the video distracted me from my pain. The man hadn't started to fuck Clara yet, so I could see the entirety of his dick as he slapped it on her bare ass. She wiggled her hips to tease him.
As he lined up his cock to her asshole, I realized something. The penis on my screen was of an incredibly similar shape and size as the one I had inside of me.
It wasn't just similar, in fact. It was identical. She must have taken a cast and made an exact replica of the cock that was pushing into her ass in the video, and she had given it to me just for this moment.
I was going to fuck myself with this stranger’s dick as he filled Clara.
The metronome started again as the massive dick teased Clara's hole. She moaned loudly, and I could see the same pain that I was feeling right now flash across her face. She had said that if I really wanted to understand her, part of that was knowing how she felt.
I just hadn't imagined that that would have meant fucking myself in sync to a video of her and another man.
This was all going too far, and I felt like I was losing control. I tried to remove the dildo from my ass.
My arm wouldn't move. The aura of pink I'd imagined around me grew thicker, and once again, my body felt weightless. Instead of pulling the dildo out of me, I watched as my hand pushed it deeper.
It wasn't just that I felt like I couldn't control myself. I felt like I couldn't control the craving. My ass was crying for more, and it was denying my attempts to take away what it had. I'd become fully compliant to anything Clara asked of me, digital or no.
As the dildo steadily slid into me, I felt it grind against my prostate. A stream of pre-cum dribbled out from my cage, landing on the shaft as it continued to split me open.
I cried out, half in pain and half in pleasure as the soft plastic cock went deeper than either of the previous dildos had explored. I could feel it slide through my guts, and I swore that I could feel each individual ridge as it bottomed out inside of me.
Click went the metronome.
Just one thrust, and I already felt my brain turning to mush. A stream of bubblegum-flavored drool fell from my lips and hit my chest.
In the video, Clara had also taken the full length of the massive cock in her ass for the first time, and just like me, her eyes were glazed over and her lips were parted. Her chestnut brown cheeks were flushed, and her eyes fluttered as the dick slowly pulled out until only the head was left inside of her. I felt the fake dick inside of me slide out to the same position as my arm unconsciously followed her.
Then, holding her hips tight, the stranger drove into her again carefully, but with purpose. The metronome sounded, and I felt the dildo bottom out in my asshole again, rubbing against my prostate as it did. Each time it plunged into my ass, it felt like it was reaching farther into me.
I was thankful that whoever the stranger in the video was, he was being gentle for now, taking it at a manageable clip.
I felt the pain subside as I followed along, taking care to not miss a single thrust.
In no time, Clara and this man sped up, and I was now shoving the plastic cock into my own asshole at a pace I wouldn't have thought possible before. My caged dick dribbled uselessly as it bounced with every thrust.
I felt something rising from deep inside of me, and my asshole started to convulse on the dildo as I watched Clara push back on the man in the video.
Then her words from earlier echoed in my brain: "don't you dare fucking cum."
Just like that, I was stuck on the edge. I moaned, squirming in the puddle of lube that had accumulated below me and trying to coax an orgasm out of myself, but all I got was precum.
No matter how hard I pushed, I couldn't force it out of me. Instead, I was trapped on the brink. I whimpered and spread my asscheek with my free hand, trying to fit just one more inch into myself.
As I cried out, the stranger in the video slowed, and I saw him stay in one position as he shuddered and grunted. He was cumming in Clara's asshole, shooting deep into her. Before all of this, I would think about how it would feel to be him.
Now? I wanted to feel his hot cum paint my insides.
What had I become?
The metronome faded, and it was soon just Clara. I didn't take the dildo out of my ass.
"You did so good, sissy," she said from the screen as she faded.
"Thank you," I gasped as if she could hear me.
I wiped off my lubed hand on my chest, and I grabbed my phone, exiting from the video.
I texted Clara after catching my breath..
- “Wow. Second vid was… crazy.”
My phone buzzed.
- “Glad you liked it. Plug up all of tomorrow and wear a pair of those panties I got you, but don't touch yourself besides that, okay, Jessi?”
I looked down between my legs. The huge dildo was still balls deep inside of me. All I had to do was take it out and plug up tomorrow. That should have been easy.
I looked at the collection of buttplugs. They were much smaller, the largest looking like a metallic egg with a handle and jewel at the end.
My brain was fucked. The only thing I could think was that I wished the plugs were bigger.
The next day, I did as Clara said, and I cleaned and plugged myself first thing in the morning, sliding on a pair of lacy fuschia panties once I was done. I started chewing that enticing gum immediately. I had some in my mouth at almost all times now, and I kept blowing bigger and bigger bubbles as I did chores. Its flavor reminded me of something, but I couldn't name what
I didn't have class till later, so I started with laundry. I washed my sheets and told myself to put a towel down next time.
"Next time…"
Was I already planning what my next session with a dildo would be like?
I shifted uncomfortably as I moved the sheets from the washer to the dryer. The butt plug inside of me was just big enough to remind me that it was there, but was only a shadow of what had been inside of me yesterday.
I did my best to distract myself. It was the day before my and Clara's date, and since the instruction yesterday to stay plugged and wear those underwear, I hadn't heard from her. I tried to go out my day without getting too distracted. Thinking about tomorrow wasn't going to make it get here any faster.
However, it wasn't easy to get my situation out of my mind when I had a cage around my dick and thick buttplug up my ass, and what's more, the frilly underwear Clara had bought me kept bringing my attention back to my ass and crotch. It was a subtle feeling, but when I would sit down or stand up, I could feel the smooth satin rub on my hips. I even wore tight skinny jeans, trying to hold them in place.
I swore that I could see an outline of the lace through my pants… I hoped that mind was starting to play tricks on me.
I chose a pink T-shirt to pair with it. I couldn't explain why, but every shirt that wasn't that color just felt too boring.
By the time I got to one of my workshop classes, I felt like I had barely gotten anything done during the day. That was how I felt about all of my classes recently. It was like being around Clara was slowly draining my focus away, and as the teacher held up a graduated cylinder, all I could think about was how it looked like that silicone dildo I had at home.
"Jesse!"
I blinked hard, pushing away the thoughts of dildos, cocks, bubblegum, buttplugs, and panties that swirled in my brain.
My professor had asked me a question, and the whole class had turned to look at me.
I felt my cheeks redden. "Uh–um" I stammered, "can you ask the question again?"
I was summarily kicked out of class.
I floated through my day, feeling like my very brain was replaced with the bubblegum I was chewing. It was mushy, stretched out, and bright pink.
After dinner, I returned to my apartment. Today had been a wash, and I felt like I once again got a taste of what life was like without Clara in it.
When my phone buzzed at eight, I was online shopping. I wish I could say that it was for a new video game or basketball jersey, but no. I was looking at giant silicone cocks, exploring various manufacturers and reviews.
It was Clara. Immediately, my whole world got brighter.
- “Want to come over and spend the night?”
My thumbs trembled as I typed.
- “God, yes.”
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