by Joanna Angel
I grabbed the lollipop off the root beer bottle, got back on my knees, and put it close to his cock.
“Cum on my special sucker!” I said. I had to pat myself on the back for how naturally the slutty schoolgirl thing came to me. I guess all that time in school had paid off in some way. He smiled and took control of his own cock. It was hard for me to properly hand job him and hold the lollipop at the same time. With my knees on the ground, a lollipop in my hand, and a giant smile on my face, I patiently waited for cum. I mean, I wasn’t lying when I said I was a good girl.
To go back and see Naomi and Rob have anal sex, turn to page 292.
To continue with Naomi in this fantasy, turn to page 299.
Oh wow. I was not expecting him to say anal. Rob and I hadn’t had anal sex before, and I had very little experience with the act in general. I wondered if doing this for the first time with Indica would be cheating on me with other me?
But of course I would give Rob my asshole. I would give him any hole, anytime, anywhere, and I firmly believed that all attendees of Sexy High took it in the ass, anyway. He sat there with his legs and arms crossed, waiting for an answer.
“Of course, I’d be happy to offer the full service to such a sexy VIP customer.” I winked.
“And, how much will that be?” he asked. Was he really going to pay it? I suppose he did already pay to get into the VIP room. How much was he willing to spend on the fake me? Last night we went dutch when we ordered pizza. Naomi was really getting the raw end of the deal here. I honestly had no idea what to charge or what the standard rate was for this type of thing, and I still didn’t know if this was a trick question, or if I was on an episode of Punk’d, right now. Was the real Rob in dirty jeans and flannel going to come out from behind a curtain?
“One thousand dollars,” I said. It sounded like a good round number for anal. I mean, I was a “student” after all, so the money obviously would go into my education.
He folded his hands. “Let me see your ass. I need a better look at my merchandise first.”
The amount of dedication he put into this role-play was sexy, scary, and admirable all at once. His demeanor in here felt like a mob boss, but I was happy to submit to this handsome client no matter his “business.”
I turned around and lifted my miniature skirt up, showing off the tiny thong stuck inside my ass crack. I sucked on the lollipop for good measure—it made sense in this particular pose. I arched my ass and showed it off, and he scoped it out like he’d never seen it before. I couldn’t imagine what I would do if I was rejected in this roleplaying scenario—that would lead to a unique relationship issue between me and Rob that I didn’t think I could begin to explain to my friends, or a therapist for that matter. From the serious way he considered my ass, I feared there was a chance of that rejection actually happening.
I can’t lie. This panicked feeling turned me on. I wanted to be the best filthy little slut for him that he’d ever had . . . and I also didn’t want to think about how many he’d had. I pulled my thong to the side and I spread my ass checks open for him.
“Come on, Daddy, it’s ready for you!” I said. Rob smiled on the couch, and he rubbed his thighs. He reached inside his pocket and took out ten hundred-dollar bills, putting them on a small table next to the couch. I knew he’d just gotten some kind of tour advance, and I felt privileged to know that he chose to spend it on my asshole instead of extra phone chargers and mouthwash.
“Thank you.” I smiled coyly. So many mixed emotions swarmed inside of me. The blurring of what was real and what wasn’t made me nervous, and excited, and confused . . . and wet. This was my first time escorting, but not really. This was me and Rob having sex, but not really.
I had no idea if this was allowed or not. I spotted what looked like a security camera in the corner of the room on the ceiling. Would I get fired if I was caught? The thrill of all the uncertainty, the way Rob looked in that god damn sexy suit, and the sheer filthiness of this little plaid skirt that just barely covered my ass crack made me so fucking hot. Rob had such a big cock, and I had very little experience with anal—that went for both of my personalities— but in this moment, I wanted him to hurt me. That’s just how dirty I felt.
I got down on all fours. The floors in the VIP room were significantly nicer than the floors in the rest of the strip club. I supposed there was some routine vacuuming done in here, just in case someone had to get ass-fucked on the floor. My skirt hiked up to my chest. I put my hands behind me and pulled my thong down to my ankles, though my cropped white top, my bra, and my minitie were still completely intact. Fully exposing my asshole to him without any kind of foreplay, and without even showing him my tits, made me feel like such an ultimate little fuck doll. I really was a bad schoolgirl.
“Use me,” I said. “Use my holes, Daddy.” My face was on the ground, my ass in the air, and the god damn lollipop was in my hand.
I had to find something to do with this lollipop. I should have put it on the table before I got down on my hands and knees, but it was an essential part of my outfit, my act, and maybe my entire existence at the moment. I didn’t want to throw it down on the ground because, as I said before, this was a very clean ground, and I didn’t want to mess things up for the next girl who got fucked on the floor. If I got back up, I’d ruin the whole “use my holes, Daddy” vibe I’d so proudly created. For the price I was charging here, I shouldn’t mess up any moments.
I stuck the lollipop back in my mouth, but it was admittedly awkward to suck on a lollipop with my face on the ground. Then I had an idea.
I took the lollipop and stuck it in my ass, with a big smile on my face. This wasn’t a cheap lollipop with a small white paper stem, this was a fancy lollipop, and the ball of sugar was connected to a plastic tube with rainbow-colored glitter bling inside of it. My asshole was now literally sweet as candy, with a tube of glitter and a ball of sugar sticking out of it. I couldn’t stop giggling as I waited for this sucker in my ass to be replaced with cock.
I could see Rob’s dress shoes walking step by step in my direction. He crouched down, lifted my head off the floor, and grabbed my cheeks. “Oh, you’re really in for it today,” he said softly, but sternly. He unzipped his pants but left the top button closed. He pulled his hard cock out of the zipper, remaining fully clothed with just a hard cock sticking out.
He then removed a skinny leather belt from his pants. He folded it and made it into a kind of loop. He slowly walked behind me and . . . whack. He smacked my left ass cheek with his belt. It stung in the most incredible way. I wanted more. I let out a painful and pleasurable moan. Whack! He did it again, even harder, on my right cheek. Now my cheeks felt unevenly punished.
“More! I want more!” I cried, and I spoke from the heart. Obliging, he smacked me on my right, then my left, then my right, then my left, all while the lollipop remained stationary inside my asshole.
“You want one more?” he said.
“YES!” I cried. He unexpectedly swung his belt at a different angle and managed to whack underneath me, smacking my pussy.
“FUCK!” I screamed. This hurt, but it was a good hurt. Tears came out of my eyes, but I truly felt like I was about to cum, and he hadn’t even touched me.
“Give me your cock,” I moaned. This feeling of submission and desperation was so intense—it was a place in my brain that I’d never visited before. I never really liked anyone telling me what to do, but my issues with authority seemed to disappear when there was a lollipop in my ass and a belt on my pussy.
I could hear him fidgeting around with something behind me, like he was ripping something open. I waited patiently, crying and begging, with my head on the floor. I felt the lollipop come out of me. I wasn’t sure where he was going to put it, but that wasn’t my concern at the moment. He spread my ass cheeks open, and I felt a warm splash of lube. I could feel it drip down to my pussy, which was already incredibly wet.
“Give me your ass,” he grunted. He grabbed my hi
ps, and slowly but firmly pushed me down his cock. It felt . . . smooth. I lifted my head and looked back at his cock, which was inching into my ass, and I could see that he had a condom on.
This was the first time I’d seen a condom on his cock. Yes, I will admit . . . we were mere strangers when we first met, with a completely irresponsible trust in each other’s body parts. After the first few irresponsible sessions, we both went to get a full panel of STI testing, and we both came back negative . . . at which point we joyfully cheered and returned to our irresponsible fucking. I didn’t know if there had been any other Indicas in his life (or on his cock) since I met him, but it was nice to know that if there was, he’d use a condom.
While the friction of a condom isn’t ever as good as bare skin inside of you, the role-play of me being a complete stranger whose asshole couldn’t be trusted without protection made me so fucking hot that the rubbery texture going in and out of me didn’t bother me at all. It turned me on even more.
“Yes!” I shouted, pushing my ass back on his cock as far as it could go. “I want it all the way inside me!” I said. He continued to thrust toward me with his wrapped gift of cock. I could feel the curve of him slowly push through me. I could feel my asshole stretching, his cock growing. One more little thrust from him, and I felt my pussy against his suit pants. He was all the way in.
“Good girl!” he said, and he pushed my head back down onto the ground. And then, there was no mercy. Now that he’d slowly pushed his way in and knew I could take it, there was no looking back. I mean, literally, my head was back on the ground, so there was no looking back. He spread my ass cheeks and fucked me hard. I moaned and yelled in ecstasy. I had never felt like such a filthy whore in my life. I’d been having sex with Rob all month, and this was unlike anything we’d done before. I was his purchased fuck toy in here, and he was a mysterious sexy stranger. The fantasy and the reality of this scenario pushed me mentally and physically in ways I’d never been pushed.
Just keep fucking me. Keep pounding my ass. Keep using me. Keep taking me.
He smacked my cheeks and pounded my asshole, switching off between calling me a good girl and a bad girl, depending on the thrust. He smacked me harder, he fucked me harder. I felt nerves inside my ass that I’d never felt before. He lifted my head up toward his head, so I was arched all the way backward, while he continued to rail my ass. He put his arm around my neck and fucked me with abandon. My eyes teared up again—I could barely breathe . . . and then . . . I came. I came so fucking hard from my ass. He released his arm from my neck, and my head dropped to the ground. I gasped for air and my whole body shook. I felt myself get tighter and tighter, and I felt his cock bulging inside me.
“Did Daddy make that asshole cum?” he asked me. I mean, it was a rhetorical question. He knew.
“Yes! Yes, yes,” I wept.
“Stay right there, I’m gonna fucking cum,” he said, holding me still, pounding away at my tight, sore asshole, using me for his pleasure. I obediently stayed in place, only going where his hands told my hips to go. He thrust a few more times before he pulled out of me, walked around me, and brought his cock close to my face . . . with the lollipop in hand. I smiled. It was time for my treat.
To go back and see Naomi give Rob a hand job, turn to page 286.
To continue with Naomi in this fantasy, turn to page 299.
“Alright, tell me what you want!” he said.
“I want your cum. Give me your cum,” I kept repeating. And then a giant load of semen spewed from his cock directly onto the lollipop. I took the lollipop and stuck the whole thing in my mouth, sucking it eagerly. His jizz mixed with sugar was such a tasty snack.
He breathlessly patted me on the head. “Good girl,” he said.
“Yeah, I know!” I giggled. He zipped his pants back up, and then there was a knock on the door, and Tony entered.
“Hello! Sir, are you interested in getting another half hour?” Tony asked, barely sparing a glance for me on the floor.
“No that’s all I’ll be getting today! Thank you,” he replied politely. Rob really was the ultimate classy gentleman when it came to the process of getting extras from a stranger.
“How did she do?” Tony said to Rob, as if I wasn’t sitting right there, naked with a jizz covered lollipop in my mouth.
“Great! She’s great.” Rob smiled at me, and then Tony gave me a thumbs up.
“Alright, you guys take a few minutes to collect yourselves, then, get the fuck out,” Tony said, laughing at his own joke, which wasn’t really a joke.
I swallowed. “Got it!” I said.
Rob winked at me and said, “Your money is on the table.” Something I certainly never thought I’d hear from someone I was madly in love with.
I attempted to count my money in the cab ride home from work. I stopped after $1,800, and there were still stray singles that needed to be counted. After my VIP room stint with Rob, it was like the customers could smell my happiness, and the requests for private dances kept coming in. My stage shows were a nonstop barrage of dollar bills, payment for my slick and seductive moves, and my witty, campy interactions with all the customers by the stage. I pulled people’s ties, I deep throated their root beer bottles, and at one point, I took off a man’s eyeglasses and rubbed them on my pussy. It’s fascinating how different the same room feels, depending on how many people reject you.
I had been on a high, and I slowly came down in the leather back seat of a black car. I told Rob to meet me at my apartment for one last goodbye. Were we going to address what had happened? Or would that ruin the fantasy? Perhaps I could keep it going . . . by one day, in a moment of suspicion, going through his credit card statements and seeing that he spent his last day before leaving for a tour in a VIP room at a strip club. I could start a whole fight about it, and scream at him about his excessive spending and infidelity with a stripper.
I got home, and Rob was there waiting for me on my doorstep, smoking a joint in his ripped black jeans and a flannel cuffed up to his elbow. His hair was back to its greasy, free-flowing form, and his tattoos were fully visible through the opened buttons on his chest and the lower part of his arm. It was bittersweet to see him sitting there, so handsome. Happy to see him, but devastated that this would be the last time I saw that sexy, stoned man on my doorstep for the next few months.
I got out of the car, and he took my duffel bag stuffed with stripper clothes and cash, which had mostly come from him. He finished his joint and we went inside. We sat on my couch in silence and loaded up my roommate’s bong with more marijuana. He sucked a giant hit, coughed, and then we began to talk.
“I don’t really want to say some epic goodbye. I don’t want to cry and shit. Let’s just go grab a beer and hang out like it’s any other night, and I’ll say goodbye when you leave,” I suggested.
“Well, I had an idea,” he said, exhaling another large puff of smoke. I wasn’t sure where this was going. Since he was getting stoned, I assumed the idea would have something to do with getting ice cream instead of a beer.
“Okay. Hear me out. I think . . . you should come with me!” he said.
“Um . . . what? Come with you on tour?” I replied.
“Yeah!” he said. I was stunned. I did want to jump in his arms and say yes, but logic and logistics quickly entered my brain.
“Rob, I don’t have time to find someone to sublet my apartment in the next few hours . . . I mean, I did make a decent amount of money today, but it’s not enough to cover me and bills and rent and everything for the next three months!” I was trying to do the math in my head of how much I had and how much I would need, and I was coming up with an impossible answer.
“No, hear me out. When I was at the club today, I snuck in a few minutes of filming your stage show,” he said.
“Wait, YOU were at the club today? I had no idea!”
He rolled his eyes and continued. “Yes, yes I was. I was way in the back, by the bar, when you were on stage, and I filmed
some of it on my phone. I got in touch with a few of the club owners I know across the country . . . I sent them your video and . . . they all said they’d have you dance there when you’re in their city.”
“Wait . . . really?” I replied. I shifted my position on the couch so I could face him. We sat in a moment of absolute silence, which says a lot, because it was never silent in this apartment. His eyes were shifting around the room, his hands fidgeting in his lap. It was like he’d just proposed to me, but instead of crying and jumping in his arms, I’d hesitated.
“Really,” he said, breaking the silence. “You’d be on your own tour while I’m on tour. And your tour sounds like a lot more fun. Maybe I’ll ditch my tour and hop on yours, you know, if you need a bass player while you strip. Ha!” He laughed at his own joke and exhaled clouds of smoke. And then I laughed at the image in my head— me stripping and him playing bass behind me, naked of course. Could I really do this? Follow him across the country?
To see what happens if Naomi decides to go on tour, turn to page 303.
To see what happens if Naomi decides not to go on tour, turn to page 306.
“YES!” I blurted out, without even giving myself any time to think about it. Traveling the US, stripping in different cities, and touring the country with Rob sounded too good to be true. But it was actually going to happen. I imagined myself spreading my legs open on a stage somewhere in the middle of Oklahoma, while Rob serenaded a stadium full of people somewhere nearby. And then we’d meet up after our respective shifts of entertaining and share a giant plate of pork ribs, and we’d have sex in a truck stop somewhere, and snuggle up in a bunk bed on a tour bus. This sounded like a real modern romance. Like a movie. Which . . . gave me an idea.
