The White Rabbit - Chapter 3

“Can you uh…tell me where the dildos are?” I asked sheepishly. The girl behind the counter looked at me like I was an idiot, gesturing to the giant wall of rubber dicks behind her.

“Do you need…help?” She asked.

“No.” I wanted to say, but I knew Persephone’s answer would be different if she were here. Instead, she just had to listen to my phone recording from my pocket. I cringed a bit when I said the words I knew she’d prefer.  “Yes please.”

Persephone’s task was a simple one: go to a sex store and purchase a dildo. In person. Do not order one online.

To be honest, the wall of dicks was a bit intimidating. There was a vast array of all shapes and sizes. Some were even shaped like dicks that weren’t of the human species. From her name tag, the clerk’s name was Britney. She smirked a bit at my discomfort. I’m sure she’s had 100’s of men walk in and timidly buy a dildo. Hell, they might have had a woman on the other line listening to them do it too. But that probably didn’t make it any less entertaining for Britney. She was very professional though, and was able to mostly hide her amusement as she waved her hand over the array of options.

“Do you want a hard, plastic material? Or more of a realistic, fleshy rubber?” she asked.

“Realistic.” I said before I could stop myself.

Again Britney bit back a smirk, like she already knew that’s what I would choose.

“We have some with balls, and some without. Which would you like?” she asked almost rhetorically, still trying to maintain her professionalism.

I already had an answer prepared. Not only because I knew what would be the more humiliating option, but because Persephone explicitly specified.

“Make sure you get one with balls.” She’d said, “I can’t tell you how many losers we have come into the ER because they shove things up their asses that don’t have a flared base.”

Persephone had all kinds of horror stories from working as a nurse in the Emergency Room. When we weren’t discussing the kinky stuff, and she wasn’t making me feel like a submissive little bitch, we talked about our days. We talked about life, books, our philosophies on religion, metaphysics, and what an asshole Elon Musk was.

“The one with balls please…” I answered Britney.

She led me to the section of realistic dildos complete with a set of rubber testicles, and even a suction cup on the end, another specification I knew I’d need.

“What…size should I get?” I asked, still a bit overwhelmed. The rubber dicks ranged from anywhere between 3 inches, all the way up to 18.

Britney threw her hands up “Hey, man…that’s your decision…” she said. But after seeing me deflate a little, she stepped in again. “I would say 6 if you’re just starting…8 if you’d like to be a little more…adventurous.” She paused again, “Can I ask…where you’ll be using them?”

I thought the answer was obvious, “Uh…at my house?”

“No..no…that’s not what I meant…” Britney laughed, unable to contain it this time, “I mean…which…?”

The realization hit me, and I felt so stupid. “Oh, my…my butt I guess.” I felt so ashamed to say it out loud, but Britney didn’t laugh at that part, just nodded in understanding. So I continued, “Maybe my mouth too…or…both? I don’t really know yet, but why does it matter?”

“It’s just that most…guys…that come in tend to prefer this one with a slight curve for anal. It hits your prostate better, but is harder to get down your throat. Whereas the straight one slides down easier.”

I looked back and forth between the two options. They both looked so realistic. The way the head was shaped, the way the shaft was bulging with veins, even the little indentations on the rubber balls. I found myself having to wipe away some excess saliva from my mouth at that moment.

“I uh…”

“You want them both, don’t you?” Britney smiled knowingly.

I sighed, looking down at the floor. “Yes…yes I do.”

“What size? 6 or 8?”

We both looked at each other, already knowing the answer.

“Eight.” we both said in unison.

“Chocolate? Or Vanilla?” she asked, referring to the color.

Again, it didn’t take much thought. “Both.” I smiled.

I felt more secure now that everything was out in the open. So what if I was a guy buying a bunch of dildos? If I enjoy it, why is that an issue? Britney didn’t see any harm in it, Persephone certainly didn’t and I…wait, did I just admit to enjoying the thought of a bunch of dildos?

After Britney bagged up my new toys, she threw in a complimentary bottle of lube. “Always make sure to use water-based with these, silicon lube will ruin them.” she advised. “Is there anything else I can help you with?”

I glanced over at the lingerie section. I could feel my clitty twitching in my panties at the sight. But instead of imagining a beautiful woman wearing them for me, I couldn’t help but picture how cute I would look in it.

Britney caught my eye, but let me take my time.

“That schoolgirl outfit…” I finally said, “Do you have that in a men’s large?”

******

“You were such a good sissy buying a bunch of dicks to play with!” Persephone’s voice message chimed. “You even got a slutty little outfit to wear!!”

I loved it when I got a chance to hear her real voice. Ever since she first sent that first video of a black screen with her seductive vocals I was hooked.

She would only send me tidbits though. When I asked if we could have phone or skype sessions she refused.

“I can’t have you getting too worked up and excited.” She said.

“But I send you videos of me doing…stuff…all the time!” I’d retort.

“That’s because you’re a pathetic little sissy and you like the humiliation.”

I couldn’t argue that.

So it was only when I did something good, when I needed motivation to do something bad, or when she just felt I needed to be teased that she would reward me with vocal messages. Soundbites. Just enough to get me mewling and desperate to earn the next one. Like an addict looking for his next fix. A part of me worried ‘she’ was using a voice modification software, or one of those A.I. programs. Just the other day I saw a hilarious video just the other day of Joe Biden, Donald Trump, and Barack Obama all playing Rocket League and talking shit to each other. If they could make that sound so real, what was keeping this mysterious person from doing the same? I tried not to think about it too much. Ignorance is bliss afterall.

“How did I know you would get a black one? 😂” she typed, “you even got them with balls!!”

“You told me to get them with balls!! 😫” I reminded her.

“No…I told you to get one with a ‘flared base’, it was your decision to make the base a pair of rubber testicles 😜”

Damn it. She was right. Did I choose them because it was what I thought she wanted, or did I choose it because it was subconsciously what I wanted?

“Well I’m off to bed.” She said. “Sweet dreams, sissy. And try to keep them dry 😉”

That was it? She made me go through all this trouble to buy some rubber dicks and she wasn’t even going to make me use them?? I actually felt more than a little disappointed.

I stared at them in their packaging. I even had them laid out next to my new schoolgirl outfit. She didn’t tell me to buy that either, but I did it anyway.

Why would she make me buy them and not let me use them? Sure, I could just do it myself, I didn’t need her to tell me to use them,  but just the thought of doing it on my own accord made me feel dirty. “Gay” even. I’m mostly straight, so playing with rubber dicks on my own would hurt that image. For some reason, her telling me to do it would make me feel better about it. It’s not gay if it’s ‘forced’, right?

She didn’t even give me tasks the next day, or the day after that. I wore panties to work even though she didn’t tell me to. I figured she would if she could, she was probably just busy.

But that didn’t stop her from talking with me about other stuff.

“You can’t tell me you don’t find Ayn Rand to be at least a little bit pretentious.” She’d said, “Her writing is dripping with this ‘holier than thou’ attitude that unfettered self-interest is good, and any modicum of altruism is destructive.”

It’s not that I didn’t enjoy our intellectual conversations. I very much did. It helped humanize her and make her less of a fembot that only spewed orders and tasks. But at the same time, I kind of wanted her to give me orders and tasks. Something to do with the new dildos I just bought. Because…I didn’t want the money to go to waste…

I wanted to ask her something like “when are you going to make me play with my toys?” But I didn’t want to sound needy. Or, at least, too eager to shove dicks up my holes.

So on the third night of her not mentioning anything about them, I grew impatient.

I’d already taken the dicks out of the packaging the night before. I just wanted to see how they felt…

Turns out they did have a realistic feel to them. Squishy, yet firm, like actual skin.

So that night I decided to go all in. I put my school girl outfit on. It fit really well, actually. I liked how short the skirt was, how it was slightly revealing and made my pantied ass look so cute. I stuffed the blouse with some socks to give myself a little cleavage. It made my chest look a lot better. I even put my hair in little pigtails using some rubber bands. I didn’t have any makeup, I was always scared of buying it on my own.

I examined the two rubber dicks. Attaching the suction cups to the floor so they were pointing straight up. I didn’t really know where to go from there. This is where I wanted direction from Persephone.

I imagined she’d want me to touch them, so I did, wrapping my hand around each one. They felt big in my palms. They were big. I could barely wrap my fingers around them. But I liked the way they felt. I started stroking them, up and down one at a time, then at the same time. I thought about how I like to be stroked. Not that I’ve been stroked by anyone else, but how I imagined I’d like to be stroked. I put more tension on my thumb and forefinger than anything else. Stroking them up and down and circling around the heads. I did this for a few minutes.

I knew what to do next, everyone does. No one wants to get a handjob all day.

“You’re gonna have to suck it.” I imagined Persephone saying, or perhaps it was my own internal dialogue?

I tentatively bent over. The cock seemed much bigger as I got closer. I opened my mouth, taking the head of the black one inside. It tasted like, well, rubber. It took up more of my mouth than I expected. I tried to go down as far as I could, but it wasn’t much at all. I gagged almost as soon as it touched the back of my throat. I stayed there for a bit, sucking and moving my head just a tad, trying to stroke the other one at the same time.

I felt like such a slut. Sucking and stroking two dicks at a time, bent over in a schoolgirl outfit. I was a bit ashamed at how painfully hard my cock was inside my panties.

I switched my mouth, sucking the white one now, trying to keep them both pleased.

“Mmmphh!!” I heard myself moan, a bit too loudly with the cock in my mouth. Why was this making me so horny??

I pressed my head down as far as I could, trying to deepthroat. I barely even got halfway down before I choked so hard I could taste a bit of bile rising from my stomach. I smacked my tongue to clear the taste, then got back on it. Trying to focus on keeping my teeth from accidentally scraping along the shaft. The dicks were getting wet from me drooling all over them, it made it easier to stroke. I licked the balls the way I saw pornstars do, licking back up the shaft.

Soon, my jaw started to ache. Turns out holding your mouth open for a while makes the muscles around it get fatigued. I took a break, continuing to stroke both.

Again, I knew what the next step was. “Lick it before you stick it,” they always say.

But these dicks were already pretty big for my mouth, I couldn’t imagine fitting one of them in my ass. Maybe I should wait for Persephone, I thought. But another part of me was saying I was already dressed up and horny, what better time than now?

I knew enough about anal sex to know that I couldn’t just shove it in. I had to get my hole ready. I slipped a finger into my mouth to get it wet with my saliva. Reaching back, I pulled my panties aside and pressed it in between my cheeks.

I gasped as it entered. Persephone had made me do this a few times while I was rubbing my clitty.

“Eventually I'm just gonna have you finger yourself and cum just from that.” She’d said.

I still wasn’t quite used to having something in there, but I must have been more relaxed today because it went in easier than usual. I stayed there on all fours, using one hand to finger myself, the other to stroke a fake cock, with the other one in my mouth. I was kind of proud of myself for multitasking so well.

After getting my entire finger inside, I got out the lube Britney had recommended to me at the sex store. I squirted a very generous amount onto my hand, and coated between my crack. My finger slipped in much easier now, so I added a second, and eventually even a third.

“You can never use too much lube.” Britney had said, and I took that to heart, squeezing a large dollop onto the head of the black penis.

It was the moment of truth. Again, the cock seemed to be much bigger now that it was about to go inside my asshole. I brought it around behind me, trying to hold it upward so the lube didn’t slide off. The gel felt cold against my hole, and the head felt ginormous. I took a deep breath, biting my bottom lip, and pressed it inward.

Even going slow, it felt like I was getting stretched open. With only the head entering my rectum, I felt like my sphincter was gonna tear at any moment, every muscle inside was trying to keep it from going inside. I pulled it out, sighing as the pressure released. Then gathered my breath, and tried again.

It took several attempts of going back and forth to finally get it in a few inches. I still felt like I was getting split open, but less so the more I worked it. Over time, my ass seemed to relax and I was able to give it a small in and out motion.

There was a certain spot where it felt really good when I pressed against it. I tried to focus on that, but it also gave me the feeling that I needed to pee.

The position was too awkward to fuck myself and suck the cock in front of me, so I decided to take advantage of the suction cup. I stuck the black dick to the wall, hiked up my skirt, and backed my ass up onto it. I put my hands between my legs to guide it, brushing by my wet and sticky panties as I did so. It was as if there was a constant stream of precum escaping my clitty at all times. I put the other dick under me, able to focus all my forward attention on it.

It was hard not to imagine being used this way. Some big black man behind me, fucking my ass while I sucked off another. My cock was throbbing again while I rocked back and forth on the rubber ones. I was able to take more in both holes now. My gag reflex seemed to have almost disappeared, and I had to have the black dick at least halfway up my ass. It was starting to feel good. Like, really good. I caught myself moaning again, even groaning when the cock accidentally slid out and my ass was left empty. I’d eagerly reach between my legs and aim it back in again.

My panties were sopping. I was incredibly horny. Looking sexy as fuck in my dirty fucking schoolgirl outfit while I fucked myself like a sissy whore. I was pleasing dicks. Two dicks. BIG dicks! Persephone would be so proud of me. I was proud of me.

My thoughts were spinning. My head was spinning. I was in this circular haze of desire and submission. It all felt so wrong, but also so right.

I wanted to cum. I needed to cum. And I wanted it to be while I was spit-roasting myself in the middle of my apartment.

I rubbed the front of my panties the way Persephone always told me. The way I'd made myself cum the last 20 or so times this week. But this was different, I was a slut. I was a whore. I was a sissy.

Then I came, and I felt like a fucking loser.

The post-nut clarity hit hard. After having one of the best orgasms of my life, I snapped back into reality with giant rubber dicks in both of my holes. My drool and ass juices were all over them. My own juices were all over my panties and my new outfit. The dicks suddenly didn’t have the same appeal.  The blouse suddenly felt binding. Everything about me just felt…gross. Used. Even though I basically just used myself.

I slid the dick out of my ass, stood up, and looked in the mirror. I really did look like a cheap slut. Outfit and hair all disheveled, I was sweaty, and I had juices leaking everywhere.

I cleaned myself and everything else up while I tried to erase what I just did from my mind.

******

I didn’t tell Persephone about what I did. I was too ashamed, too embarrassed that I let myself get to that point. What did it say about me that I couldn’t resist a pair of rubber dicks?

As the day went by and my libido built back up, I started finding ways to justify it: you spent a lot of money on them, you might as well use them. It’s not gay if they’re not real. It was just one time, what could it hurt?

But it wasn’t just one time. Two days later when I was in the throes of horniness, I did it again. The next day I put one of them higher on the wall and practiced servicing it while I was on my knees.

Persephone’s tasks had been too simple. “Lick the cum from your panties when you’re done playing with your clitty,” or “go to the restroom at work and shove your finger up your ass.”

It left me wanting more. Needing more. I found myself thinking about how much better the rubber dick felt up my butt instead of my thumb.

It was like I wasn’t getting enough from her, but I didn’t know how to ask for more without it looking like I was a gay little whore.

“I’m going to ask you something and I need you to answer honestly.” She said one day.

It always made me nervous when she started a conversation that way. Like when she asked me what my real name was (Alan), where I was from (Lousiana) and if I was a virgin (obviously. Unless you count my schoolgirl escapades…). I probably should have lied about those things, but I was growing to trust her more and more each day.

“Sure.” I sent. “You can ask me anything…”

I always felt a little tension as the Persephone is typing… indicator came up. It seemed to take forever. Or maybe my anxiety just made it seem that way. Finally, her message bubble popped up:

“Have you used one of your dildos already?”

I gulped, a fresh flood of shame filling me. What should I say? Should I tell her I used them without her permission? Would she be mad? Did I even need her permission?

I could just deny it. She had no way of knowing if I was lying. She might even get a little upset and angrily make me use them in order to ‘punish’ me.

I didn’t want to have to tell her that I used them on my own, but this relationship—whatever it was—wouldn’t work if I wasn’t honest.

“Yes Goddess,” I sent, “ I did. I’m sorry 😔”

I cringed from the humiliation, knowing what I did and not knowing how she’d take it.

“Did I say you could use them?”

“No Goddess…”

“But you did it anyway??”

“Yes Goddess…😣”

I braced myself for her wrath. Her reaction and resolution, but instead I got:

“Bahahaha!! How did I KNOW you would??”

I didn’t know what to say to that. The fact that I did it to myself was humiliating enough, but to know that she expected it…

“I’m gonna need you to tell me everything. And i mean *everything*! I want every single detail from how it tasted, how it felt, and how it made you feel.”

And so I did, I typed out every single detail of my adventures with the rubber dicks over the week since I bought them. I was hot with embarrassment the whole time, but I had that submissive chill as well.

“The fact that you fucking spitroasted yourself is just so damn funny to me 😂” she said.

“So you’re not mad?” I asked.

“Mad? Of course I’m not mad! I always expect sissy baby girls to play with their toys! And I find it sooo much more hilarious when I leave them to their own devices, and they end up doing it without me even telling them 😈”

I smacked my face with my palm. She did it intentionally. She purposefully didn’t give me tasks with the dildos because she knew I would play with them on my own, and I played right into her hand.

“This should go without saying,” she typed, “but from now on, you are not allowed to cum unless there’s a dick in your ass or mouth…or both. Unless I say otherwise. You need to learn to associate your pleasure with the pleasing of someone else at the same time.”

It seemed reasonable. I had already been following that particular guideline the last few days anyway. I didn’t have a single orgasm without at least one of those dicks inside me.

“How will you know if I'm following that rule?” I asked.

“I won’t.” She said, “But let’s just say…I trust you will have no problem acquiescing my request 😉”

Damn it, I hated when she was right, and so far she’d been right about pretty much everything.

“Now, because you decided to be a little whore all by yourself, I think it’s time you send me another video, holding up your toys, and using your sissy voice to remind me exactly what a little slut for cock you are…”

To Be Continued...