Alice’s Wonderland: Pegged Pegger


I had woken up extra early. The little research I did on the usage of enemas, had taught me that the preparation, execution, the wait after the execution, and the aftermath, would take a considerable amount of time. Not something one should do when in a rush. Thankfully, the simple mixture of water and salt that I had mixed up, made for an easy and effective homemade enema. All-in-all, the procedure took up about an hour, giving me some extra time to mentally prepare for today’s training.

Suddenly, the phone lit up. “Hey babe!” the notification read. It was Laura. I quickly unlocked my phone to open our chat. A follow-up message appeared,  “What have you been up to? You’ve been so quiet! When I told you to surprise me for Valentine’s Day, I did not mean for you to ghost me!”

I quickly typed back, “Sorry, love. Working on your surprise took more effort than I thought it would! But it’ll be done soon and then I can show you! I think you’d be surprised to learn what I did for you!”

“I’ll let you get back to it then! Looking forward to finding out!” Laura’s message read.

Well… At least I did get a chastity cage, which was the surprise I originally wanted to get for her, but I still didn’t have much of an actual excuse as to why I hadn’t talked to her for a few days. Hopefully, Alice would soon teach me something that would actually help me please Laura, like she said she would. Then at least I could claim I’d been training on that for so long…


Alice met me at Wonderland’s door and hurried me inside. “Come on, we don’t have all day!” she said. “Employees’ room. Get naked, and wait for me there.” Her cryptic explanation was cause for concern, but I had learned not to question Alice anymore, so I went into the employees’ room and got myself ready as instructed.

“Been doing workouts?” Alice asked as she walked into the room and saw me naked.

“Besides the ones you’re giving me?” I replied with a hint of sarcasm.

“Don’t get coy with me, doll. You know the punishment for being a wise ass.” Alice said, her hands reaching for her necklace.

“I’m sorry, Alice,” I quickly replied. “I meant that I haven’t done any ‘additional’ workouts.”

“Well, your body seems to have taken on some curves!” Alice concluded. “Not too noticeable when you’re clothed, but like this, I can definitely see you’ve changed.”

“Is that a good or bad thing?” I asked, a little concerned.

“For me and Tyler, definitely a good thing. I’m not one hundred percent sure about Laura, but I’m sure she’ll think you’ve become a lot more visually appealing too,” she said. “Besides, every girl loves a guy with a nice ass, so don’t worry about it.”

“If you say so…” I said with hesitation.

“So, I’m guessing you probably already figured out today’s training, given the enema assignment,” Alice said. “I take it all went well?”

“Yeah,” I sighed.

“But?” Alice probed.

“Laura texted me,” I continued. “She got suspicious of my absence and I told her I was working on her Valentine’s Day surprise… but, besides the cage, I don’t really have much to show for.”

“Oh,” Alice said and chuckled. “Then today’s lesson is for her too!” She grabbed a hold of the bulge in her jeans, stretching from her crotch to just past the bottom of her right pocket. “No machines today, because today I’m going to personally teach you how to take a pounding, using my strap-on,” Alice said. “Now that’s a skill you can show Laura! I bet she’d enjoy tearing your ass apart now that it’s getting into shape.”

“Laura never mentioned having any desire for trying out pegging, so I’m not so sure about that,” I said.

“You mean you didn’t peg her for a pegger?” Alice laughed. Taksim escort “Sorry, you practically handed that one to me.” She took a moment to recollect herself. “She probably never mentioned it because you were lacking the ‘assets’ to awaken that desire within her. But now you’ve got a booty that’s just begging for it! Trust me, she’ll want a piece of this ass,” Alice said as she slapped my ass.

Alice had a point. Thinking back on it all, it made sense that Laura wouldn’t feel any desire towards pegging if the visualization didn’t look all that exciting to begin with. On the other hand, telling Laura that I hadn’t contacted her for days because I was too busy working on shaping up my ass and training myself for receiving anal penetration, just so she could peg me, would also be a very awkward reveal… I had to come up with something else… but what?

“First things first,” Alice said, interrupting my trail of thoughts. “Because it’s your first time, I want to be on the safe side. So I brought water-based lube, muscle relaxants, and even some healing cream just in case something does happen.” Alice walked over to the table in the center of the room. She grabbed a familiar pill and a glass of water, handed them to me, and said, “Here’s another painkiller, like the one I gave you after I dolled you up the other day. It’s best to take it in advance, so when we start you’ll already be in less pain if the muscle relaxants aren’t potent enough to subdue your anxiety.”

I swallowed the pill down with some water and handed the glass back to Alice.

“These are alkyl nitrites, or ‘poppers’, as they’re more commonly called,” Alice said, showing me a small bottle filled with some liquid substance. “Essentially, it is both a muscle relaxant and aphrodisiac. It intensifies sexual pleasure and it loosens up muscles like your anal sphincter, making it the perfect aid for anal sex!” Alice explained. “Just make sure only to inhale a whiff of it. Trust me, you don’t want this stuff to actually touch your skin.” She mimicked inhaling it through her nose with the closed bottle before handing it to me. “Go on, try it!” she said encouragingly.

I took the bottle, twisted the cap off, and took a quick sniff of the vapors before closing the bottle again and giving it back to Alice.

“Perfect,” Alice said, as she unbuttoned her jeans and took them off. “For now, we’re still training you for Tyler, though, and he might use you anywhere he sees fit. So I’m going to pick…” Alice looked around the room. “The table!” she said. “Knees on the edge of the tabletop, bend over with your back arched, stretch your hands in front of you, and rest them on the tabletop. I want to see that ‘face down, ass up’ position! That will be your pose for today’s training.”

The poppers had shifted my somewhat nervous anxiety into a slight excitement. I realized I had prepared for this. I took an enema, Alice had me take medication, she brought lube, and she even brought a cream if something did go wrong. It was all planned out to take my concerns away and put my mind at ease. And so it did. I felt my mind and body relax.

“This might feel a little cold, but don’t worry, it’s just temporary,” Alice said. She squirted some lube on her fingers and rubbed them against my sphincter. The initial cold touch of the lube dissipated as it slowly warmed up to my body temperature. Alice applied a little more lube and gently inserted her fingers inside me, coating my internal sphincter. My body provided no resistance, as my muscles fully relaxed to the sensation of her fingers probing me, along with the sensation of the cool lube being applied to my internals.

“That should do it,” Alice said as she pulled her fingers out one last time. She Taksim escort bayan reached for the lube again and spurted a glob of lube onto her strap-on. “Are you ready for Tyler to fuck you, doll?” Alice teased, as she stroked her strap-on, spreading the lube across the head and the entire length of the shaft. She walked up to the front of the table. “Actually,” she said. “Why don’t you give it a kiss for good luck first?” Alice clearly enjoyed seeing me in that position. “You look so perfectly submissive like that,” she continued.

I raised my head so my lips could meet her strap-on. As I leaned in to kiss it on its tip, Alice grabbed my head with both hands, forcing my lips to stay centered on the head. I was half expecting her to either apply pressure with her hips or attempt to pull my head down on it, but she just kept it in place and remained motionless.

“Go on,” Alice said. “Give it a good, long kiss. Close your eyes, pucker up, and make some noise! I’ll even remove my hands from your head, so you won’t have to worry about ‘surprise blowjobs’. As long as you keep kissing it until I say you can stop!”

I closed my eyes and puckered up my lips. The ‘kissing suction’ noise that escaped my lips, lasted so long, that I thought I was going to run out of air. As I was about to give up and take a breather, I heard a single ‘click’.

“Aw, ain’t she a beauty? I’m framing this one!” Alice said as she showed me the photo. I should have known that when Alice promises the absence of a specific surprise, it means it’s not without surprises entirely. Now Alice had a picture of me, duck-faced, kissing the head of her skin-colored strap-on. With her body out of frame, someone could easily think I was ‘head-to-head’ with a real cock.

“Alright, that’s enough fun for one day,” Alice said, slowly walking to my side. “Don’t worry, dolly. As long as you keep behaving properly, this will remain our secret! Nothing to worry about! Just some good fun between friends.” Her hand brushed my ass as she reached my backside. I shivered from the unexpected touch, which made me make my body and ass wiggle. “Hm, yeah girl, shake that ass!” Alice chuckled and gave my ass a firm slap.

“Ah!” a moan escaped my lips. My face went red.

“Looks like the poppers still have you excited, good!” Alice concluded. “Then let’s begin before they wear off.” She placed the tip of her strap-on against my sphincter. “Ready or not,” Alice started, placing her hands on my hips.” Here… I… Come!” She thrust forwards while applying pulling pressure on my hips to make sure I wouldn’t get pushed forwards.

With everything being fully lubed up, the poppers, and the foreplay, Alice managed to fully insert her strap-on inside me on the first thrust. If my arms weren’t already flat on the table, Alice’a thrust, and the shock of stimuli that followed shortly after, would surely have made me lose my balance.

Reaching full insertion, Alice gave me a moment to collect myself. “That went well! Looks like I don’t even need to stretch you out!” Alice said. “Lucky doll, that means today’s session will be a rather short one.”

And with that, Alice started slowly retracting her strap-on. I could feel its movements every inch of the way. The sensation was very strange, but not painful. A mixture of pleasure and slight discomfort. Thankfully, the enema I took in the morning had already done its job of emptying me. It saved me from an awkward response to this strange new feeling.

Having just the tip left inside, Alice started pushing again, slowly. Retracting at full insertion, and pushing again. Slowly at first, but gradually picking up the pace. “I’m sure Tyler wouldn’t be this gentle with you,” Alice said. “So, try to enjoy it.” Escort taksim A few more thrusts followed before she reached a regular tempo, similar to that of the fucking machine.

With the strap-on repeatedly prodding against my prostate, I found myself starting to release short breaths of air. Alice took notice and picked up the pace. “Panting like a bitch in heat, are we?” she said. “Just don’t let Tyler catch you making those cute little sounds.” Her speed increased, and so did my volume. Short, quick breaths turned to moans as Alice got rougher with me.

Alice could tell I was nearing climax, and in response, she slowed down, nearly coming to a full halt. She leaned in closer to me as she ever so slowly moved her hips. “Can this cute little panting doggie do tricks too?” she asked, almost whispering. Her seductive, sultry tone sent shivers down my spine. Before I even had the time to reply, she continued, “Can this cute little doggie cum on command?” I whined in response.

“10…” she started counting down. “9…” her pace started building up again. “8…” she pushed a little extra hard near the end to make sure she went as deep as she could possibly go. “7…” Alice’s hand started wandering around my body. “6…” her hand had found its way to my caged genitals.

“5…” once again my exposed balls were gently massaged. “4…” my moaning tensed up. “3…” Alice quietly joined my moaning. “2…” her pace became fast and irregular, as if approaching climax herself. “1…” Alice moaned louder and she squeezed her strap-on. “Cum for me, doggie!” Alice exclaimed. I felt her strap-on had released a lukewarm liquid inside of me. Her command along with the feeling of something flowing inside of me triggered an orgasm of my own.

“Before you ask, yes. I did use a special strap-on with a hidden liquid container.” Alice said. “And also, yes, it was real cum I just deposited inside your cute little butt. Consider it your hazing. You are now a fully-fledged doll and ready for your first real dick.”

Real cum? But how? Alice didn’t have a boyfriend, did she?

“Judging by your quietness, you likely have another question,” Alice continued. “No, I will not disclose where I acquired this cum. A girl has got to have her secrets!” She giggled defiantly. Pulling out her strap-on, Alice said, “Give me your left hand.”

I obediently reached behind me with my hand, and Alice grabbed it. She extended one of my fingers and pressed it against my sphincter. “Make sure to keep this from leaking!” she commanded. “I’ll be right back.” Alice walked off.

After a minute of waiting, Alice came back. “I brought you a gift!” she happily said. “You can remove your finger now.” I did as she asked and as soon as I removed it, Alice forced something inside again. “There we go, all plugged up. Now it won’t leak out when you walk!” Alice said.

“Walk?” I asked, confused and tensed up.

“Yeah! This place has no showers, dummy!” Alice replied. “And I did promise you a shower, so I’m bringing you to my place to get you all cleaned up.” She squeezed my butt cheek. “Doesn’t mean the fun has to stop here, though,” she said. “So you’re going to carry that load all the way back home with me.”

“Is it far?” I managed to ask.

“Only twenty minutes away,” She replied. “Though, given your predicament…” she eyed my butt plug and mimicked taking small steps. “More likely about thirty-five or so,” she said and laughed. “Come one and get dressed.”

“But what about the store?” I asked as we walked out of the employees’ room.

“I’ll close early,” Alice replied nonchalantly. “You may have noticed the store is practically dead. It’s more of a warehouse, really. I’ll just close up now and fill out the online orders first thing tomorrow morning.”

“And your boss?” I hesitantly asked.

“He owns fifteen stores just like this all across the country,” she said. “He’s not scheduled to be in my region anytime soon. He wouldn’t notice, trust me.”

And so we set out for Alice’s home…

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