by Joanna Angel
“I know babe,” Rob said. “Don’t worry, I’ll be back . . . and while I’m gone, you have to send me pics and videos from work to keep me entertained. I want lots of fresh material for spank sessions in my bunk!”
While it definitely turned me on to think of Rob playing to a giant crowd of people, then getting off stage and jerking off in a tour bus to my photos somewhere in Albuquerque, it turned me on a lot more to think about him jerking off into my mouth in my bed in Brooklyn. I also felt like stripping just wouldn’t be as fun without coming home to tell him about it. Sending my stories of how I turned people on all day in a text message wouldn’t be the same, without seeing the excitement he’d get on his face . . . and in his pants.
I gave him a kiss and left reluctantly for work. I contemplated taking a day off and spending it with him, but I reasoned that would actually make this whole goodbye a lot harder.
I sat in the dressing room of Club 42, overlining my lips with a lip-liner trick I’d just learned, which made my mouth look more plump. This, combined with lip plumping gloss, gave me the perfect pout. I contoured my face, I highlighted my cheekbones . . . things I never did before I worked here. I’d learned to paint my face to the perfect shade of slut. The daily transformation from Naomi to Indica felt rather zen, now. Smearing different shades of brown on the different parts of my face like war paint, and blending them all together with a beauty blender was my own form of meditation. But today, the blending of my whore paint just didn’t give me the same sense of tranquility it normally did. I couldn’t stop thinking about Rob.
I looked through my selection of outfits, and it made me frustrated. Everything in the bag reminded me of Rob—everything had some kind of sentimental filthy memory. There was only one outfit that didn’t make me think of Rob, and that was the Catholic schoolgirl one. I bought this one at some point because I figured it should be a staple to have in my collection, but the few times I’d pulled it out, he’d laughed and told me to put something else on. He said it was “corny.” He did drop out of high school, so I suppose he had rejected all forms of school at a young age, and he wasn’t going to make an exception for one whose uniforms spelled out “Sexy High” on the emblem.
Rob had an insatiable sex drive. Just the other day, I’d met up with him at a bar wearing an off-the-shoulder oversized T-shirt, and he somehow got turned on by the sight of my shoulder displayed in that particular way, and he’d dragged me to the bathroom and fucked me before we could even order a drink. But for whatever reason, the schoolgirl outfit was where his penis drew the line.
I slipped on the tiny red plaid schoolgirl skirt, along with the matching bra, a miniature clip tie, white knee-highs, and a little white crop top that tied in between my breasts. I put my hair in pigtails and matched this with black Mary Jane stiletto heels. I looked in the mirror, admiring my long legs, my pouty lips, and my “corny” costume, and I thought I looked fucking adorable. A red-headed, large-breasted stripper acquaintance I’d made this summer who went by the name of Melody noticed my get up, and handed me a giant red lollipop.
“Here, take this. It will go with your outfit,” she said.
“Oh my god, thank you! It definitely goes with it. What a good idea!”
“You’re welcome! I always have a stash of candy in my locker. If I keep it in my house, my daughter will eat it when I’m not looking and then keep me up all night on a sugar high,” she laughed.
“Alright well, I’ll remember that if ever I need more candy,” I replied.
“Make sure you use it to”—she used her hand to make quotation marks—“‘sucker’ all the money out of everyone down there.” She laughed at her own play on words. I had no idea she was a mother. That explained why she was so supportive of my enrollment at Sexy High.
I left the dressing room and went out onto the floor, where I sat down next to a customer to see if I could get a few private dances in before I got called to the stage, something I was usually able to do. The guy had dark gelled hair and a scruffy face.
“Hi! I’m Indica! What’s your name, sweetie?” I asked.
“Oh uh . . . hi. I’m Rob.”
What the fuck. Was this some kind of sick joke? Of all the names in the world, did it really have to be Rob?
Hoping to hold back the tears, I presumptuously decided to sit on this Rob’s lap. Before I was able to ask for a dance, or even ask him anything, he pushed me off of him and said, “Sorry I’m waiting for someone else.”
I had now suffered rejection from two different Robs today. It was not a good day at school.
The room could sense my insecurity. I tried to mingle with customers, but they all seemed disinterested. I made my rounds, asking several people if they wanted to buy a private dance from me, and they all rejected me, one after another after another. People got up and walked away as soon as I sat down. What was I doing wrong? I sucked on the lollipop and pouted in the corner while all the men spent copious amounts of money on people who weren’t me.
The DJ announced that I was next on stage. I walked over to the small waiting area behind the stage, wiping tears away from my face with the miniature tie around my neck. I walked onto the stage, and the DJ played “Oops! . . . I Did It Again” by Britney Spears. How clever. He must have seen the schoolgirl outfit and thought this would be a good fit. I glanced up at the DJ booth from the stage and gave him a nod of approval. Unlike Rob, this DJ understood the appeal of the schoolgirl.
And just as the beat of the music kicked in, something flipped inside of me. I couldn’t quite explain where it came from. I pranced around the stage and sucked on the lollipop. I channeled my bratty rollercoaster of emotions into this dance. I pouted, I pulled my pigtails, I stomped my feet, I lifted my skirt up and went directly over to the Rob that had just rejected my lap dance, put my ass in his face, took his hand, and made him smack my ass. The customers clapped. I got down on all fours and made some of the other men spank my ass while I sucked on the lollipop. People were showering dollar bills on me, and I felt alive. I slid the skirt off, untied the top, rolled it up, and put it in my mouth like some kind of ball gag, while I smacked my tits and pinched my nipples. I was having fun!
When the song ended, I walked off stage feeling like a million dollars, but actually more like eighty to one hundred dollars, if I had to guess what was in this wad of sweaty bills.
I quickly collected myself backstage and threw my outfit back together. I normally went up to the dressing room after a stage session to reset myself, but today I didn’t want to leave the floor. I had a fire burning in me, and I had to keep going until it went out. I could feel the energy of the room, and I knew it was a good time to ask people for a dance.
I walked out on the floor with my now slightly disheveled schoolgirl costume and a half-eaten lollipop that was getting sticky. Tony stopped me in my tracks as I was heading to the sea of suited men to see who I could get to buy a dance.
“Hey, you’ve got a guy waiting for you up in VIP,” he said.
“What? Really?” I replied.
“Yup. Half hour. Room four. I got his credit card. So go on and get up there.” He motioned to shoo me away with his hands, like I was some mosquito buzzing around his ear. I’d never been to the VIP room before. I seemed to be a one to three lap dance kinda gal here. I hadn’t quite figured out how to charm someone intensely enough that they’d want to whisk me away for a half hour to the land of very important things. Perhaps everyone was waiting for me to get my diploma from Sexy High before letting me back there.
I walked past the bar, turned the corner, and went down the VIP room hallway. There were only four VIP rooms total, so I was in the last one down the hall. They had red lights on top of each door that indicated “in use” or “vacant”—you know, like the bathrooms in the airplane.
The doors in the hallway were all black, with silver handles and a stark number on each door painted in gold. I opened door number four. A handsome guy with tattoos and slicked back long hair, wear
ing black pleated pants, a white collared shirt, and a tie, sat on a plush purple couch next to an ice bucket full of root beer. I did a double take. This mysterious guy was Rob. And not the guy who’d rejected me and then later smacked my ass, the other Rob, who’d fucked my brains out all summer and was leaving tomorrow.
I was in shock. I blinked my eyes a few times to make sure I wasn’t having weird delusions of Rob. I wouldn’t put it past myself in this mental state to hallucinate him. Just the other day, Rob posted a bunch of photos on Facebook from his sister’s wedding, and he’d worn a T-shirt and a leather jacket. Somehow the strip club was the only thing that had the power to make him put on a tie.
“Well, hello Indica! I’ve been waiting for you!” he said.
“Are you fucking kidding me right now!” I whispered, closing the door behind me.
“Excuse me! Miss! I paid top dollar for the VIP experience, and I don’t want to be talked to that way.” He shook his fingers at me in disapproval.
“I can’t believe the one time you came to see me at work, I’m wearing the schoolgirl costume. Do you still think it’s ‘corny?’” I laughed.
“You don’t know what I like. You don’t know anything about me! I’m just a customer who saw you out there, and I liked what I saw . . . so I got a VIP room.” He smiled a sinister smile. The depths of Rob’s kinkiness never ceased to amaze me, and the fact that I always enjoyed going right there with him amazed me even more.
So, Rob got a VIP room with Indica, not Naomi. I had to leave Naomi out of this, but if Naomi didn’t exist, then Rob wouldn’t have ever come in here. Or would he? I suppose that didn’t matter. Indica had different personalities on different days, and sometimes her personality changed by the hour if she felt like changing outfits between shows. But right now, Indica was a bratty attendee of Sexy High. The type of student who specifically got herself into trouble because she enjoyed the punishment. I sucked on my lollipop in an exaggerated way. Rob grabbed his crotch.
“Your management told me that ‘extras’ could be available here, but that would be up to you,” he said. “Are you a bad girl? Do you offer extra services here for a VIP customer?”
Did I? Was this a trick question? Normally, if I was confused about something at the strip club I’d call Rob and ask him what to do, but I couldn’t exactly do that right now. “Yes, I am a very bad girl,” I replied. “And I’d be happy to be your little whore in any way you want me to be for the next half hour—as long as you pay the price,” I said in between taking very long licks of lollipop. I raised my voice to a higher pitch, about an octave higher than my usual tone, and I giggled in between my words.
“So what will it be, Daddy?” I said. “What do you want?”
To see Naomi give Rob a hand job, turn to page 286.
To see Naomi and Rob have anal sex, turn to page 292.
A hand job! This was . . . exciting. Much more exciting than the usual over-the-pants rubbing that went on in here.
“Just a hand job? How about I replace this sucker with your cock?” I suggested.
“You bad girl . . . No Indica, it’s not safe to put a stranger’s cock in your mouth.” He gave me another “tisk tisk” motion. I forgot—in this fantasy I was an untrustworthy stranger, and giving a hand job was the “cleanest” way to interact with a stranger’s penis.
“How much?” he said. He was dedicated to this role-play fantasy, and part of me was turned on while part of me was incredibly flustered. I wanted to carry it out properly—I’d never been to the VIP room, and I’d never done any extras here in the strip club. It had never been offered to me, and had it been, I would have politely declined because it felt like doing extras would be cheating. But in this instance, Rob was cheating on me . . . well, um . . . on Naomi. With Indica. Luckily Indica strictly adhered to client confidentiality. She didn’t even know Naomi. This split personality existential crisis was definitely veering away from the sexy and “safe” hand job I had to begin.
“Um, $500!” I replied. I truthfully had no idea what to charge. Five hundred seemed like a nice round number.
“Well that’s a lot more expensive than the other girls,” he replied.
I got frustrated. Was he comparing me to the other girls in other strip clubs that he got hand jobs from? Is that what he was planning to do on tour? Go from club to club getting less than $500 hand jobs, while I cried and sent him sexy text messages? I didn’t know how I felt about that. But that was Naomi’s problem.
“Well, I’m better than the other girls,” I replied, with the perfect bratty inflection in my voice, if I do say so myself. He seemed impressed with my answer. He nodded in approval.
“Alright, well let’s see what you can do,” he said. He took out five hundred-dollar bills and placed them on the small end table next to the couch. He did tell me at one point he got some kind of advance before he went on tour, for whatever supplies he might need for the road. I felt a bizarre sense of pride knowing that this money was being spent on me, and not socks and toothpaste.
I put the lollipop down and balanced it on top of a bottle of root beer. I got down on my hands and knees and I crawled toward Rob, who was sitting on the couch with his arms folded and a smirk on his face. I truly got off on this challenge to see if I could be his perfect little prostitute.
I felt the bulge of his cock under his dress pants. I could tell he wasn’t wearing any underwear beneath them—it was just a thin layer of whatever blended fabric this was. He’d never seen me in a schoolgirl outfit, and I’d never seen him in suit pants. We were truly two different people. The gel in his hair gave him an entirely different scent. His tattoos just barely peeked over his shirt collar, leaving so much to the imagination. He looked so dark and mysterious, like Keanu Reeves in The Matrix, and admittedly also kinda like Christian Bale in American Psycho. There was something so dangerous about his dominance in a suit, and I wanted to take every risk imaginable with him.
I touched his cock over his pants. I bit my bottom lip. I could feel the outline of his shaft and balls getting bigger and bigger.
“Mmmmhmm. It feels like such a big cock! I want to play with it!” I said, continuing with this schoolgirl fantasy, but with someone less than two years older than me.
Like most suit pants, this pair had a button, a zipper, and a little metal hook on a flap that covered the button. I dove between his legs and unhooked the flap with my teeth, and I growled, kind of like a cat, but mostly like a really horny human. I thought of trying to unbutton the entire thing with my teeth, but quickly realized that would be time consuming and most likely wouldn’t even work. So I unbuttoned the button, and I unzipped the zipper.
I pulled down the pants to his knees, revealing his growing cock. I saw a small bottle of lube fall out of his pocket, and I giggled. He really came prepared! I picked it up off the ground and squirted a bunch in my hand, and then squirted a dab on the tip of his cock. I knew he was extra sensitive at the tip. Maybe getting inside information from Naomi wasn’t fair in this game of role-play, but Indica the overpriced hand job giver would instantly know her way around any cock.
I spread the lube around the tip of his cock in a small circle, slowly, around and around and around. He nodded and groaned. I took my lubed-up hands and began to stroke his cock, up and down the shaft, slowly. I worked up a healthy amount of moisture in my mouth and spit on his cock. It took some skill to have it land on the tip of his dick without actually touching his dick with my mouth. A little bit of spit mixed with lube makes everything so much more wet.
I stroked his cock, and it was so sloppy, if someone overheard us they would think I was giving him a bath or something. He unbuttoned his shirt, revealing his toned abs and his soft, un-groomed happy trail. I felt like a lucky stranger, admiring his tattoos and his pecs as if for the first time. His dick was rock hard in my hand, and I felt it pulsate like a beating heart. It was as if I’d sculpted a tall, beautiful cock statue right in front of me. I could see his eyes getting wide
r and hear his breaths getting deeper.
“How am I doing, Daddy? You like your messy hand job?” I stared up at him with pouty lips and puppy dog eyes.
“Oh yeah. Good girl. Keep stroking Daddy’s cock,” he said. I fully intended to do that!
I untied the impractical white crop top from my chest and threw it on the ground. I attempted to unhook my bra, but my fingers were too greasy with lube and I couldn’t. Fuck it. I took the straps down off my shoulders and just pushed the bra down my stomach. The important thing was that my tits came out.
I leaned closer into him and pushed his cock in-between my tits. I put my hand over his cock and over my tits, like I was making some type of boob bridge with my hand. I moved up and down on his cock, with my hand in place. This was how I was still able to get some friction on his cock.
“Push your fucking tits together,” he commanded, and I obliged. He leaned back and thrust his cock toward me, in-between my breasts, as I held them together. Lube dripped down my chest, and I spit on my tits and his cock to keep it flowing. My bra and my skirt were beginning to get drips of lubey grease on them, and I didn’t care. I’d replay this filthy hot memory of escorting for my own boyfriend whenever I touched myself for the next few months while he was gone.
After a while of some intense titty fucking, I got on the couch next to him, spread his legs open further, and leaned over his chest to stroke his cock. I felt the heat of his body against my hardworking arm. The mere touch of his skin brushing up against mine made me shiver. I stroked him with pressure, going faster and harder, pointing his cock at me like it was a loaded gun. I could see his dick bulging, so I licked his ear and nibbled on his muscular neck.
“Lemme see that pussy,” he panted. I slid my panties off and spread my legs open next to him on the couch. I could see him staring at my pussy with hungry eyes, and I felt his cock get harder in my hands. I took my left hand off his cock but continued to stroke with the right hand. I had a good steady grip on it. I spread my pussy lips open with my left hand, giving him the perfect view of my open vagina, without allowing him to touch it. I stuck my fingers inside of me and gathered up the accumulating moisture. I mixed it with some more spit and then placed my hand back on his cock. I was pumping faster and faster, and I could see that he was getting close. I had an idea.
