Hooker for a Night
part of the Anonymous Sex Journal
© 2011 Deist Publishing
Smashwords Edition, License Notes
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She contacted me via email, as most of them do. She was tentative, as most of them are.
We arranged to meet at a Coffee Bean in West LA. Sitting outside, I had a red baseball cap on the table in front of me to signal her. As I sat waiting, I tried to guess what it was she was going to ask for. I’d done this enough to see the patterns, and had gotten pretty good at guessing. Maybe she wouldn’t ask at all. Many back out. I’ve been left waiting a number of times. I could sympathize. It’s not an easy thing to do.
When she walked up, it remained me how bad I was at guessing what someone would look like. Somehow I had pictured her as tall, dark, perhaps ethnic. Instead, she was on the shorter side, thin, with no-nonsense shoulder length hair. She reminded me a bit of the actress Holly Hunter, but younger. I guessed early thirties.
“Brian?” she asked as she stood over me.
“Yes,” I said, motioning toward the empty chair. We didn’t shake hands, and she didn’t offer her name. I had told her not to. She sat, but on the edge of the chair, like she wasn’t sure she was going to stay.
She looked at me a moment, gauging, clutching her purse in her lap. She was quite ordinary looking. Attractive, but not very distinctive. Pretty brown eyes though. Wedding ring. Sensible skirt and blouse. No makeup that I could tell, except lipstick. She looked a bit nervous, but controlled. Determined.
“I’ve read the accounts you write. The journal. I think I’ve read everything.” I nodded. “Are they all true?” She jumps right in.
“Yes,” I said. “I make slight alterations, to make sure identities are concealed. I skip things that are just plain boring, but I don’t make anything up. Do you want some coffee? I’m not in a hurry.”
“No. Do you always write about the encounters? I mean, are there some that you don’t write about?”
“Yes. I don’t write about them if they’re too similar to another one I’ve written about. You’d be surprised how many people have the same secret desire. And they usually think they’re the only one.”
“Why do women trust you?” she shifted, as if asking questions from a predetermined list.
I paused. This was tricky. I almost always get asked some variation of this.
“I think a lot of it is instinct,” I said. “They just sense it. I think the trust is partly developed from my writing. Everyone who contacts me has read at least some of the encounters I’ve written about. One of the reasons women have a hard time expressing their sexual secrets is they fear they’ll be judged. But they know I won’t do that. At all. And they know their secrets are safe with me. Forever.”
She listened intently, tightly focused. “Why do you... I mean, what do you get out of it?” She was very direct. I’d hate be to interrogated by her. I wondered if she was a cop.
“I’m a writer. I get to write about it. And frankly, it excites me.” She kept her steady gaze on me.
“And, as corny as it may seem, I like meeting new people and being a part of their lives,” I continued. “Even briefly. Especially in an intimate way. People fascinate me. Which is probably why I’m a writer.”
“Could I change my mind?” she asked. As I studied her face, I was getting the sense she was a very intelligent woman. The kind of person that’s usually a step ahead of everyone else. Always the smartest one in the room, even if nobody notices.
“It depends. There’s no risk in telling me. You’re not committed to anything. Sometimes just saying it is enough. Expressing it.” She continued to study me. I could tell she was truly conflicted. I expected that whatever it was, it was a secret desire she’d been nurturing for a very long time. She wasn’t going to give it up easily.
She broke eye contact with me for the first time, and looked down at the table. Many women have a secret desire that excites them, something they’d love to have actually happen, but don’t really expect it to. We live in the real world, after all. The hardships and small disappointment of day to day living has taught them that we don’t really get what we want. They may even be more comfortable with their secrets remaining a fantasy, where they are easily controlled, contained, and low risk. Those women don’t usually contact me.
The women that contact me often have a secret desire that is more of a burden. A desire that won’t leave them alone. Something that wakes them up at night, and tugs at them during odd hours of the day. Nibbles away at them. Pops up during meetings, or diving the kids to soccer practice, or standing behind someone in the check-out line. It grows more vivid and detailed as time goes by, as if nurtured. Usually it’s something that goes against how they think of themselves. I was beginning to think her desire fit this description. Likely it was something she was loathe to even articulate, but I was certain it was something that wouldn’t leave her alone, even many years after it first crept into her consciousness.
There are also women who contact me simply because they want to have their secrets written about. Maybe it’s an ego thing, or perhaps they find it titillating. They get to do something exciting, then read the account of it, knowing others are reading it too. She didn’t seem to fit that type.
She looked genuinely troubled. Her face was tight with worry. She glanced around, as if guilty just for talking to me.
“It’s okay,” I said, feeling sympathy for her. “It really is. You can tell me.”
“I know I can. I’m not entirely sure how I know that, but I do.” She sighed, relaxing a bit. She looked around again. There were clusters of others sitting at tables, bent over their laptops, praying to their phones. “But not here,” she said.
“We can go for a walk, if you’d like. Or we can sit in my car. I’m parked right there,” I said, pointing across the street to my car.
She looked into my eyes again. Assessing. One thing this woman wasn’t was shy. She had a quiet quality to her, but she was brave. She seemed to make a decision.
“Lets go sit in your car,” she said.
~ ~ ~
We sat in silence. I wasn’t going to help her. I had told her all she needed to know, now it was up to her to make the leap. Or not.
She sat there looking out the windshield at a group of people crossing the street, trying to control an unruly dog on a leash. Her lips were a tight line, her brow furrowed. She continued looking out as she spoke.
“Ever since I can remember, or since I was old enough to understand such things, I’ve wanted to experience what it would be like to be a prostitute. A hooker. Just once. To have someone use my body in exchange for money. To be used like an object. As an object. I don’t condone prostitution, and I don’t know why... well, that doesn’t matter. I don’t know where it comes from.” She shook her head slowly, mystified. Likely she’d spent many hours trying to figure it out and come up empty. “So there it is. That’s the big bad secret that I’ve never told anyone, not even my closest girlfriends. And now here I am telling a stranger in parked car.”
I waited a moment to make sure she was finished. Then I asked. “Is this something you actually want to do, or is it something you wanted to confess.”
She turned and looked at me. “It’s something I actually want to do. It’s something I want very much to do.”
Thoughts quickly ran through my head. “Do you want me to hire you as a prostitute?”
I could sense her breathing getting quicker. “Yes,” she said evenly.
I looked at her carefully. “I need to ask you something,” I said.
“Okay.”
“Are you a cop?”
She looked truly thrown. “What? Oh my God, no! No, I’m a... well, no, I’m not.”
“If you were, you’d have to say so. Legally, you can’t deny it if you’re asked directly.”
She looked panicked, like she might get out of the car and bolt. “I’m not. Good God, no. Honest.”
“Okay. I believe you. I’m sorry, but I had to ask. Because what you’re asking me to do is illegal.”
“No, you wouldn’t need to actually give me money. I mean, I’m not asking you to do that.”
“I see. Okay, give me a second. Let me think about this for a moment.”
She looked down at her lap. Knees together, dressed conservatively, she looked like a lawyer or an accountant. She sat as if waiting to hear what her punishment would be.
My mind was racing, trying to think of everything.
“Okay,” I said, finally. “Here it goes. If we’re going to do this, I’m going to lay out some conditions. You must agree to all of them. After I’ve laid everything out, I want you to leave. If I hear back from you, that means you’ve agreed, and we proceed. If not, all the best. Clear?”
She nodded, not looking at me, perhaps feeling scolded by my harsher tone.
“Being a hooker means being treated like a hooker. Not just sexually, but in all ways. It’s an identity. If you do this, you’re going to have the full experience. And it may not be what you’re expecting.”
I gave her a moment, in case she wanted to leave right then and there. She continued to sit quietly, but she started rubbing her knee with her palm, like an old nervous habit had suddenly surfaced.
“And that starts now. First of all,” I continued, “you will take money. Otherwise, forget it. You will commit a crime. You will break the law. Otherwise, you’re not really a prostitute. And you must convince me you’re worth it. It’s real money, my money, and you’ll need to convince me that your pussy is worth it. That’s the burden of all prostitutes.” With the word pussy, she stopped rubbing her knee. She was still, except I could see her chest moving as she breathed rapidly. “You can do whatever you want with the money, give it to a charity or buy crack, I don’t care, but you must take it.” Again I gave her a moment before continuing.
“When you go home, you’ll need to take pictures of yourself and send them to me. Disguise your identity however you want. I don’t ever need to know your name. Not even a fake one. These pictures should not be subtle. They should make me want to give you my hard earned money to fuck you. And you need to send me information. You must name your price, and you do this by using the term “roses” instead of “dollars”, so you ask for x amount of “roses” for your services. And for how long? One hour? All night? What do I get for this price? Will you give me a blowjob without a condom? Can I fuck you in the ass? I need all this info to make my decision. And if you price yourself too low, I’ll assume you have a disease, or you used to have a dick, or there’s some other reason you’re less valuable. And if you price yourself too high, I’ll be sticking my dick in some other whore. You’re a product, and you need to price and market yourself accordingly. That’s being a prostitute.”
She didn’t move. She didn’t blink. Her lips looked dry.
“And take that fucking wedding ring off. That’s it. Any questions?”
“No.” It was a barely audible whisper.
“Okay. Now leave. Go.”
She got out and crossed the street, quickly disappearing. I sat there, thinking about her. I suspected she lived a normal, middle class family life, probably in an area like Santa Clarita. The only hookers she’d seen were likely on TV. I figured my chances of hearing from her again were very slim. I expected she was one of those that gets enough relief just from confessing her secret. Enough to go back to her safe, predictable life anyway. As I sat there, I saw her pull out of a parking lot next door. I just caught the side of her face. She was driving a mini-van.
~ ~ ~
The next day, I went back and fourth about something. In the end, I decided to email her test results I had just received, indicating I was disease free. I knew I was clean, but it’s good to have something to show. I wanted her to have an authentic experience, but I didn’t want her to feel she might be putting herself or her family in danger by doing so. I figured either way I wasn’t likely to hear back from her, but if she wasn’t going to do it, I wanted it to be for other reasons.
I was wrong. A week later, around the time I’d forgotten about her, I got an email. There were three pictures attached.
The first was her dressed in thigh-high black boots, a short white mini-skirt and a skimpy tank top. She was standing at a half angle, with her ass lifted up and out. She had her foot propped up on something, enough for her skirt to have slid up, revealing a glimpse of bright red panties. Her hair was slicked back and she had on large black sunglasses.
In the next picture she was dressed as a school girl. Her hair was in pigtails and she had on Mary Janes with striped ankle socks and a soft pink sweater. She was against a wall, as if she’d been ordered to stand against it, back to the camera. With one hand she was lifting her argyle skirt and pulling her white cotton underwear aside, her hand just barely hiding her ass. Her other hand was holding a large sucker. Her head was turned to the side just enough to show her tongue out, licking the sucker. There was a backpack and school books strewn about.
The third picture was her in a very skimpy yellow bikini. She was sitting on the ground, back to the wall, elbows casually on her knees and her legs half open. Her body was completely oiled, shiny and slick. She had on bright red lipstick and high heels. She’d put a black stripe over her eyes.
I studied the pictures. She was fit. Yoga, pilates, running fit. I never would have guessed from having met her, but her body, though not very curvy, was tight and toned. And sexy. She knew her best asset was her ass, and she made the most of it. She’d put a lot of thought and effort into the pictures, that was clear. And she’d done a great job. Especially considering she likely had to do them by herself.
I noticed another attachment. Opening it, I saw it was similar to what I’d sent her; a recent clean bill of health from a local medical clinic. She’d blacked out her name and address.
The body of her email had all the details I asked for. 300 roses. For an hour. She had stated very few limits. I booked her for two hours. For five weeks later. I wanted her to have a long time to think about it. Prepare for it. Anticipate it.
~ ~ ~
I had debated about the hotel. I’m sure she would have been more comfortable in a normal chain hotel, like a Best Western or something, but I wanted her to have the full treatment. I settled on a dive hotel in Canoga Park. A dive, but safe. It was in a well lit area away from too much street activity. I emailed her the specifics, telling her what to bring.
I set it up like I was a company man on a short business trip through town. When I got to the hotel, I paid cash. I wondered if I could write it off as a business expense. Not that writers have a lot of expenses. I sent her a text with the room number.
The room was appropriately tacky. Bed, nightstand, table, chair. It had that light smell of disinfectant masking stale smoke. There was generic faded art bolted to the wall. But it appeared clean. Relatively. I arrived at 9:00, an hour early, to clean up and make some adjustments.
The closet had mirrored sliding doors. The bed was the squishy, springy type guaranteed to give you a tortured nights sleep. There were those old, stiff brocade pillows on it, the decorative kind with thick ropy patterns sewn into it. I unmade the bed and slid it over so it was right up against the mirrored closet doors.
I opened my briefcase and laid papers out over the table and generally messed the place up a bit, making it look lived in. The room was warm. There was an AC unit along the floor under the window. I turned it on and it made a humming noise, but no cold air seemed to be coming out.
I put the money in a sealed white envelope and set it on top of the TV.
I went into the bathroom and took a long shower, taking my time shaving. The sink had rust colored stains around it from cigarettes left burning. I dressed in a good suit, keeping the tie loose.
I sat in a chair and propped my feet on the bed, opening a beer I’d brought. I almost never drink, but I swished some in my mouth for effect. I turned on the TV, leaving the sound off, and set my phone out. I waited.
~ ~ ~
At exactly ten o’clock there was a tap at the door. I picked up my phone and began a conversation. I opened the door while pretending to talk on the phone.
“Yeah, tell Eddy he’s fucked if he doesn’t get on board with this...” She was dressed in a stylish overcoat, her hair up, reading glasses on. Except for the bright red lipstick and dark eye shadow, she looked like she could be my business partner. She had a duffel bag over her shoulder. I gave her a once over glance, waiting a beat to make her feel I was deciding, then motioned her to come in.
I nodded toward the TV, still on the phone, and turned my back. I could see her in the closet mirrors as she took the envelope and stuffed it in her bag. I turned back to her, still barking the phone. “I don’t care who he used to work for, I need to know he’s on our team.” I turned to her and gave her a nod as I turned off the TV. She took off her glasses and untied her hair, shaking it out. She unbuttoned her coat and let it drop to the floor. I could see her hand shaking as she did it.
She was wearing the thigh-high boots and short white miniskirt. I could see her red thong underwear through the thin white material. She wore the same white blouse she had on when I met her. I had asked her to. I wanted her to have some direct connection to her normal life. She had it unbuttoned to her stomach and a black lace push-up bra on underneath. She wasn’t busty, but the bra did a lot to accentuate what she had, and I could faintly see her nipples hiding just under the shear lace of the bra. The overall effect was stunning.
I looked her over slowly, in pieces. I wanted her to really feel what it was like to be completely objectified. I stared at her tits. Tilting my head, I held my gaze on her crotch. I still hadn’t even looked at her in the eye.
“Listen Mike, room service just showed up, can you hold a sec? No, I want to finish this, let me just put you on hold a sec. Yeah.” I set the phone down.
“Come here,” I told her. I motioned with my hand for her to turn around. “I want to see your ass.” She turned slowly, obediently, and arched her back a bit, pushing her ass out. “Lift your skirt.” She did, showing me a tight, beautifully toned white butt dissected by the thin stripe of her crimson thong.
“Turn around.” As soon as she did I put a hand behind her head and pulled her in forcefully and gave her a deep kiss, turning my head and opening my mouth, gorging her with my tongue.
She was taken aback, expecting anything but that. I even felt her legs start to give out from under her. Then she steadied herself and tried to kiss me back. Her lips were dry and her tongue a bit rough.
I pulled away and went into the bathroom. I came back with a glass of water, handing it to her. She drank it down and I kissed her again. She was ready now, and really kissed me back, eager to prove herself. I broke the kiss and grabbed her chin roughly and stuck my thumb in her mouth. She looked at me, unsure. Then she closed her mouth and sucked. I could feel her tongue rolling over my thumb.
I picked up the phone. “Yeah Mike, I’m back. Meatloaf. Okay, well we’ll have to get him on board.” Cradling the phone, and undid my belt. My thumb still in her mouth, I pulled her down, then pushed on the top of her head. “He seemed enthusiastic enough when I met with him last week. What changed his mind?”
She got on her knees and undid my belt, then unbuttoned my trousers. Her hands were shaking terribly. I pretended not to notice. She pulled my zipper down, then slid my pants and underwear off my hips, letting them fall to the floor. My shirt tails hung over my dick.
“Tell him he can have the same percentage they were going to give him.” She parted my shirt tails.
I looked down at her as she stared at my dick. Her black boots jutted out behind her. She looked up at me, mouth partly open, lipstick smeared. I was growing bigger. I nodded to her
She reached up and cradled my balls, holding them softly. She opened wide and put my dick all the way in her mouth. My eyes closed as the wet, electric pleasure rolled through me. I wasn’t completely hard yet, so she was able to take me all in, her nose pressed to my pubes as her hand held my balls.
I reached for the top of her head, my fingers gripping her hair. I pulled my dick out of her mouth. Look at me, I mouthed to her. Open your mouth, I said silently, then put my tongue out flat. She did the same, her mouth open, head tilted back, tongue out flat.
“Okay, I’ll give him a call in a little bit. Hay, how’s Linda? She over that nasty cold?” My dick was now completely hard. I grabbed it at the base and traced her lips and tongue with the tip of it. I slapped her flat tongue with the head. I brushed my cock against her cheeks, then over and above her eyes, my balls sliding over her open mouth. She began to lick and suck my nuts.
“Good, glad to hear it. Yeah, don’t want it to get cold. Right, see you next week.” I tossed the phone on the table, impressed with my improvisational skills.
There was a slurping sound coming from her as she tongued my balls, pressing her face into the soft sack, now wet with her saliva. I disengaged and took a step back, stepping out of my pile of pants. She looked up at me, on her knees, spittle dripping off her chin. I slowly unbuttoned my shirt and slipped my socks off. I started stroking myself. My cock was fully engorged, the head straining up.
I stepped forward, holding my dick at the base. I grabbed her by the hair and pushed my cock into her mouth.
“Lets see how good you are at suckin’ dick. That’s it, suck that cock.” She gently stroked the shaft with one hand and carefully licked and sucked the head, kissing around the crown.
“Harder. Suck it, don’t make love to it for fuck’s sake. Smoke that cock.” She got rougher, putting her hands around my ass and pressing me in as far as she could. She started bobbing her head, looking up at me, as if seeking approval, my dick sliding in and out of her mouth.
“That’s it. Take it deep. Suck it like a fuckin’ whore.” She gagged lightly and pulled off, quickly going low and hungrily sucked my balls again, now jerking my wet dick. Her small hand barely fit all the way around. She came off my balls and went back to sucking me, now trying to push me deeper. I think she had watched some porn and was trying to emulate the pros, and was quickly getting an appreciation for their skills.
I expect her normal sex life was boring and predictable. A product of a boring and predictable life in general. She probably had an out of shape husband that thought he was doing her a big favor by going down on her once a year. I imagine she married young, was devoted to her children, and only had an orgasm when she could sneak some time to herself. Like sneaking a smoke. I doubt she’d felt what it was like to be really fucked since college. Maybe not even then.
She had loosened up and was getting the hang of it, really working my dick over. She was trying to get it all the way down her throat, but couldn’t quite get it past her gag reflex. I could feel the wave of an orgasm building, getting closer. I pulled my dick out of her mouth and told her to stand up. She was still fully dressed.
“Get on the bed. On your back.” She crawled on the bed, not easy to do gracefully with thigh-high boots on. She lay there, legs pointed toward me, her head propped on a pillow. “Spread your legs.” She did. Her short mini slid up around her waist. Her red thong panties barely covered her snatch. I could see a dark wet spot on them. “Spread ‘em wider.” I stood over her and reached down, grabbing her panties at her hip where they were thinnest, and yanked hard, tearing them off her. I held them to my face, feeling the wet spot against my nose. They smelled like wet, clean metal.
I stood at the foot of the bed and reached down, grabbing her shiny boots at the ankle, yanking them up. The leather felt cool and slick. I spread her legs slowly, looking at her crotch. I could tell her thighs were wet. Her pussy was shaved clean, neat and glistening.
I pulled her down the bed toward me, then lifted her legs and pushed them all the way back, almost flipping her backward. “I said spread your legs. Lemme look at your cunt.” She hooked her arms under her knees and held her legs up and back, her knees all the way up by her head, completely exposed. Her small puckered asshole looked out, exposed for the first time, as if making it’s debut. “Open your pussy for me.” She slid both hands down under her ass and pulled her pussy apart, spreading the lips wide, exposing her gash. “That’s it. Stay like that. Just like that. I want to admire you.” I wedged one of the firm brocade pillows under her lower back so she could maintain the position.
Then I pulled the chair to the foot of the bed and sat, about two feet from her open pussy. She couldn’t see me from my angle.
“Ummm, that’s some good looking cunt.” I leaned closer and blew on her wet crotch. I could look across her body and could see her chest rising and dropping quickly with her breathing.
I stood back up and I picked up my beer, looking down at her, stroking my dick and taking a swig. She looked up at me from between her knees. She had a mix of expressions playing across her face. I knew she was very excited, her body couldn’t mask that. But she was also nervous, and embarrassed, and even scared. I doubt she’d ever cheated on her husband, and I doubt she ever thought, despite her fantasies, that she’d ever actually do this. Even when she imagined her hooker-for-a-night fantasy, I doubt she pictured it as explicit as this. Her bravery was likely shocking even to her.
It was getting warmer in the room. The AC unit wasn’t doing much and she had a light sheen of sweat forming on her face, making it shiny. I doubt her boots breathed very well. She gamely held her position. I reached over into my briefcase and pulled out a condom, tearing it open with my teeth. I put down my beer and rolled the condom over my dick, making sure she saw it.
I moved onto the bed, kneeling before her open pussy. She was still spreading herself wide. She looked down and watched as I pressed the tip of my dick against her opening. The head disappeared. Then I pushed all the way in and held it there. I slid out, then slowly stabbed her again. I looked at her. The tendons in her neck were tight. By gently bouncing the springy bed with my knees, I was able to move in and out of her without touching her in any other way. My dick was the only contact. I bounced harder, getting a light rhythm going. Then I slid out and rubbed the head of my dick over her pussy, pushing it against the top of her opening. It was getting hotter in the room, her face was getting shinier.
I pulled out and slipped the pillow out from under her. I moved on top of her. As I did, I noticed a light cesarean scar across her lower abdomen. It looked like she’d tried to cover it with makeup, which had partly come off from sweat. I pulled her legs back down to a more comfortable position around my waist. She was so much shorter than me that her face was barely higher than my chest. Her hands went up around the back of my neck, likely an old habit with her husband. Her leather boots felt cool wrapped around my hips. I could feel one of her heals dig at the center of my back.
I unbuttoned the last two buttons on her blouse, then reached behind her. She arched her back as I unhooked her bra. I pulled her blouse off and slid her bra straps off her shoulder and tossed them both aside. I had to pull out briefly in order to move down her body, licking her nipples and massaging her tits, sliding a hand back around and down her back. Though her breast were not large, her nipples were swollen and pointy. I moved up to her neck, then her ear, biting, licking, sucking. I reached down and slid back into her as I kissed her. She tilted her head back to meet my mouth. I started moving in a slow, deep thrusting pattern.
She clamped onto me, lifting her ass and meeting my thrusts as I pushed deeper. We were built up speed fast, then fell into a steady, hard fucking, the bed bouncing frantically up and down. I was pushing off my toes get the most penetration into her, pressing the weight of my body into her. The sweat between our bodies was making me slide forward and back with each thrust. Rivulets of sweat rolled down her neck. She was breathing hard under me, her eyes rolling back, grabbing my hair in balled-up fists. When I was close to the point of no return, I stopped. Abruptly. And rolled off her.
We were both panting. I got off the bed and stood there, pulling the condom off my dick and tossing it aside. I went into the bathroom, drank a glass a water, and put a towel around my waist. My dick was still hard, angry at being denied. I came back out.
“Go in the bathroom and change,” I said, still catching my breath. She looked unsure, laying there with her legs still open, her pussy wet and swollen. “Go!” I pointed to the bathroom. She got off the bed and grabbed her bag and went into the bathroom.
I sat in the chair and waited.
~ ~ ~
A short while later she came out, dressed as a school girl.
She had on everything from her picture; argyle skirt, light pink fuzzy sweater, Mary Janes and striped ankle socks. Her hair was in pigtails. Glossy pink lipstick. She held some schoolbooks sweetly in front of her. Her legs had chaff marks just below her skirt from the leather boots. I sat there sprawled in my towel, swigging my beer as she stood there twisting her ankles and twirling a pigtail, looking at the ground. Though I’m sure she was at least thirty, her small stature, smooth skin and fit body, combined with the outfit, really made her look like a living sex fantasy. My dick was screaming for release under the towel.
“Who’s been a very bad girl?” I said gravely. She put out a pouty lower lip and rocked side to side. “Who’s been disobeying the teacher and needs to be punished?”
With a meek voice she said, “I have. I’ve been a bad girl.”
“That’s right. You’ve been a very bad girl. What do you have to say for yourself?”
“I’m sorry.”
“I’m afraid that won’t cut it. I think you need to be punished. Do you agree?”
“Yes.”
“What’s that?”
“Yes. Yes, I deserve to be punished.”
“What do you suggest?”
“Maybe, um... maybe I need a spanking?”
“Humm. That may not be enough, but it’s a start. Okay, let’s get this over with. Come here.” I slid forward on the chair and reached up, grabbing her by the shoulder and pulling her face down across my lap. She grabbed the edge of the table, books falling to the floor. I slid her over, positioning her over my lap, her ass over my right thigh. I lifted her plaid skirt, revealing her loose fitting white cotton underpants with pale blue bunny rabbits printed on it. My cock was pushing so hard against the towel I squirmed to relieve some of the pressure.
I slowly gathered her underwear in the center, admiring her beautiful butt. I was dying to pull her undies all the way to the side and spread her ass cheeks and get to her asshole and pussy, but I refrained. I gathered her underwear at the top in one hand so they ran in a bunched line up her butt crack. Her small butt was perfectly formed, toned and youthfully soft. The towel was bunched up on my leg, under her crotch. I adjusted her position so the folds of the towel would press against her pussy. I parted her legs slightly to get better contact against her snatch.
“You need to learn to obey me.”
“Yes sir, I’m sorry sir.”
“Sorry’s not good enough. Now take your punishment like a good girl.”
Her butt cheeks practically glowed in front of me, pale white and luminous, split by the white roll of her underwear barely covering her asshole.
Giving her underwear another firm tug and grinding my leg up hard into her crotch, I hauled back and slapped her ass with the open palm of my hand, creating a loud cracking sound.
She let out a loud, forceful “Ahhh!” sound, not in the small voice of the school girl, but a woman shocked. In my excitement I had hit her much harder than I planned. There was an irritated red blotch spreading on her butt cheek where my hand had struck.
I was afraid I’d gone too far. I was pushing this woman far beyond any boundaries she knew. She had asked for this, but in trying to actualize her secret desire I had crossed a line. I was so sexually excited it was clouding my judgment. I waited a moment, staring at the angry red mark on her ass, half afraid she’d get up and run for the door.
“Thank you, sir. I’ve been a very bad girl. I think you should spank me again.” She lifted her ass up off my thigh, presenting it for another smack.
I did. I spanked her again. Not as hard, but close. “Bad girl,” was all I could say in my excited state. Twack, I smacked her again. This time, when my hand came down, I held it on her ass, and pushed down, grinding her crotch against my thigh. Then again, crack!
I could feel my dick springing against the towel with each hit, angry, wanting to be part of what was going on. Her body twitched. She was breathing rapidly again.
“Again -- please. Please. Punish. Me.” Her voice was husky and breathy. It was hard to tell if it was her voice, or if she was still trying to talk like a school girl.
Two more hard smacks. They were loud. “Urghhh!” she called out. She started squirming on my lap, pressing into my thigh. She was gripping the table so hard I thought the wood would splinter. Her butt was burning crimson now, the red spreading all over her cheeks.
I grabbed her ass and rolled it back and fourth over my leg. My dick was pushing against her lower belly, searching for relief. Her legs started to kick out as if trying to run as she tried to stifle desperate sounds. Once more I haled back and let down a hard smack. She cried out again in real pain.
“Get up,” I commanded. She half rolled over to look at me. Her face was flush with excitement, her hairline wet with sweat. “Get up!” I nearly screamed. “You’re a bad girl. You will do what I say!”
“Yes sir. I’m sorry sir.” She scrambled up, gangly and unsure.
“Pick up your books.”
“Yes, sir.”
“Put them on the table. Now, go stand in the corner.” She went unsteadily to the corner of the room and stood there, looking at me.
“Turn around. Face the corner.” She did.
I went to her and stood behind her. “You’re a very bad girl.”
“Yes sir. I know sir.”
“Are you being smart with me?”
“No, sir.”
I crouched down and put my hands up her skirt and pulled her underwear down so they were in a bunch around her ankles.
“Give me your hands.” I took her hands and pulled them roughly behind her. I pulled her skirt up and put her hands on her butt cheeks, down low. I then pushed her hands up and out, spreading her ass open. Her beautiful pink puckered asshole peaked out.
I gently pushed on her lower back. She leaned forward, her head resting in the corner crease of the wall, butt sticking out. She lifted her ass up and out enough for her pussy to be complexly open to me, her hands still pulling herself wide open.
I stood close behind her, but not touching. “Do you promise to be a good girl from now on?” I reached down and very lightly, almost imperceptibly, tickled my fingertips over her pussy lips. Her asshole immediacy puckered, gathering and releasing as she let out a breathy sound.
“Do you? Do you promise to be good?”
“No. Yes.”
“Well, which is it?”
I tickled her pussy again, .
“I... I... uh, uhhh.” She was whimpering.
I took the towel off from around my waist. My dick sprung forward, pissed off and demanding immediate attention.
I moved my finger tips lightly over the outside of her pussy. I could feel the small, tough nub of her clit. Then, without touching anything else, I flicked it, like you’d flick a piece of lint, the tip of my fingernail snapping it. She let out a loud “ah!”
“Bad girl. You’re being punished.”
“I know. I am. I’m... I’m bad. I’m so bad. Please. Oh God, please. Anything.”
I flicked her again. She almost screamed, then tried to thrust herself back against my hand, her forehead hitting the wall.
“Oh, you’re so bad.” Turn around. She did. Her face was strained, wincing. She stood, bent knees together, as if having to go to the bathroom.
“You let me down.”
“I know. I’m sorry,” she said, frowning. She glanced down at my screaming hard dick.
“Did you just look at my penis?”
“No. Yes. No.”
“That again. Okay, you need to learn a lesson. Sit,” I demanded, pointing to the edge of the bed near the mirrored closet doors.
She sat, looking up at me, straightening her skirt and trying to look composed. I stood in front of her, my erect cock springing in her face.
“Are you looking at my penis?”
“No.”
“You are, you little whore.” I stroked my dick. With the first touch I could feel I was already close to exploding. Pre-cum oozed over the head, dribbling off the tip in a glistening string that dripped down, landing on her folded hands.
“You bad girl. You are looking at my penis.” She looked up at me, a pleading look on her face. She opened her mouth, just inches from my dick. My cock was straining forward, like it could smell her mouth. She tried to lean forward but I pulled back.
“I don’t think you’ve learned your lesson.”
She started to squirm. She reached up for my dick.
“Sit on your hands. Do it! Sit on your hands.” She did.
Sitting on the edge of the bed, her hands tucked under her, she looked up at me with her mouth in an open o. I couldn’t take any more.
“Are you ready for your punishment?” I asked her in a shaky voice.
She started bouncing on her hands, her pigtails springing. “I am. Yes sir. I’m ready,” she said.
“Sit still.” I was so excited I was light headed. She stopped bouncing and opened her mouth wider.
I stepped forward and stuck my dick in her mouth. I held it at the base and rammed it in, hitting the back of her throat. She let out a muffled mumpt sound, retching slightly, her eyes wide. Rather than backing off, I thrust harder, hitting the back of her throat again.
She took a few rapid breaths through her nose, then relaxed and pushed forward, allowing my dick to slide down her throat. She turned her head slightly and pushed further, her nose pressed into me, holding herself there. I could then feel her constrict and relax her throat, like a swallow. It was as if an electric shock rolled through me. Had she practiced doing this? This was not something an ordinary suburban mom could do. She looked up at me, impaled by my dick, and shook her head slightly, making her pigtail bounce.
I took the clue, grabbing her pigtails. Using them for leverage, I pulled out slightly, then slid back in her mouth and down her throat again. She stayed relaxed, able to take it. She kept her eyes on me and nodded very slightly. A vein on her forehead was so swollen I could see it pulsing. I grabbed her pigtails closer to her head, gripping them firmly, and thrust harder. She let out a hummm sound, a kind of malevolent moan. I started doing full thrusts in and out, the head of my dick coming almost all the way out of her mouth, then stabbing back in.
An uncontrollable urge was rushing though me, moving at lightening speed. I pushed all the way in again, holding it there, and she swallowed again, her neck muscles shifting, sweat rolling off her forehead.
The orgasm hit me so hard I was wasn’t prepared. I was in such a heady state of excitement it just took over, barreling right through me. I let out a cry and, with my dick all the way down her, started to spasm. I convulsed, my dick spurting cum down her throat. She let out a kind of high pitched whine. I pulled back and blasted cum at the back of her mouth. Though her mouth was firmly wrapped around my dick, some cum escaped the corner of her mouth in a forceful burst, sliding down the side of her face and running down her neck.
I let go of her pigtails and grabbed the back of her hair with one hand, pulling her head back as I pulled my spasming dick out. Cum was spewing out in jets as she kept her mouth open, looking up at me, wide eyed. I could see sperm shooting on her tongue, around her mouth, on her lips. I set the head of my dick on her lower lip and two spurts of cum shot out in ropes over her cheeks and forehead.
My body continued to convulse, my hips thrusting. She reached up and squeezed my balls and put her other hand on my dick, gently milking me. She let the last bits of cum coat the tip of her tongue, tracing the head of my dick around her lips. She then slid my cock carefully back in her mouth, about half way.
My body was still doing light spasms. Looking down at her, I touched her cheek and turned her face to the side, toward the mirror. We both looked at her reflection.
There she was, dressed as a school girl, with a big wet cock in her mouth. Her face was glazed with sperm. Cum dripped off her chin. It was on her hands. There was messy splats of cum dripping down her soft pink sweater and some on her argyle skirt.
She was a long ways away from her normal life.
She took a moment to take in the site, burning it into her mind for future reference. As she watched herself, she licked and kissed my cock, reveling in the mess, watching herself tongue and swallow and play with my dick like the nastiest of sluts. She started squirming.
“Okay, go take a shower and get cleaned up and then get your ass back out here. In the other outfit.” She looked up at me, reluctant to let go of her hard won prize. “Go! You’re still on the clock, whore.”
~ ~ ~
She grabbed her bag and went into the bathroom. I put the towel back around my waist and collapsed into the chair, a sweaty mess. It was hard to believe I thought I could actually do more. I felt like every bit of energy and every ounce of fluid left me with the orgasm. I was spent.
I could hear the shower running. I suddenly realized how hot it had gotten in the room. Dense and stuffy, heavy with the smell of sex. I went to the AC unit. It continued to chug worthlessly away. I opened the window above it. Then I opened the front door. I doubted anyone was going to walk by. Besides, it was that kind of hotel, so fuck it. Cool air flowed in like a cool drink of water.
I sat back down and held the beer to my forehead. Warm. I took a long drink and let out a satisfying belch. I never liked the taste of beer, but this tasted like heaven.
I slowly drank the rest of the beer, vainly hoping it would replenish me. The water had stopped running awhile ago. What was she doing?
Then she stepped out. She was wearing the bikini, with tall high-strap heels, and dark red lipstick. It’s like she walked right out of her photo. She’d left her hair wet and messy, giving her a slutty look. Wow. She had come prepared.
I got up and closed the front door, then turned to admire her again. I walked a full circle around her.
“Okay, your job now is to get my dick hard again. Think you can? How are you going to do that?” I went to the chair and slumped back down in it, looking up at her, beer in hand.
She came over to me and straddled my lap, still standing. Good God she really did have a body. Smooth as porcelain, with long graceful muscles and tendons rolling and tucking. Shaved, plucked and coifed smooth. How many other women who look so plain on the street are hiding this underneath their conservative clothes and boring appearance? I wouldn’t recognize her as the woman I met at the Coffee Bean. Her bikini was yellow, tied at the hip. It was too small for her, meant more for an occasion like this than to actually hang out at the pool. Her bottoms strained to cover her crotch. I could see the tight folds of her pussy confined under it. Her top didn’t make it to the bottom of her tits. They pushed out, pale bulges straining under their confinement. Her nipples were clearly visible under the sheer material, embarrassingly provocative, like you’d imagine on a mannequin in a sex shop.
“How, huh? How are you going to get my dick hard?” It may have been a rhetorical question at that point.
She shook her hair, light droplets hitting me. Then she surprised me. She slowly lowered herself onto my lap, and holding my face in both hands, gave me a lovely, tender kiss. Sweet and sensuous, she kissed me like someone she missed. She cradled my face and kissed my mouth, my eyes, my cheeks. She traced my lips with her tongue, then passionately explored my mouth.
I wrapped my arms around her and lost myself in her kiss. She pressed down on me, pushing her weigh against me, her breasts pushing against my chest. My dick started to stir under the towel. She kissed me more passionately, grabbing my chin and sticking two fingers in my mouth as she kissed and licked me, then pulling my hair back and biting my neck. She kissed and licked my ear. My cock continued to grow restless.
“That all you got?” I said weakly.
I put both hands on the side of her face as we locked in another deep kiss. I slipped my hands down her shoulders and along her side. Moving around to her front, I rubbed the flat of my thumbs against her nipples, knobby and heavy, letting the thin yellow material rub over her nipples. Then I cupped both breasts in my large hands and massaged them. I traced my finger tips around the edges of her bikini top, then slipped my hands around her back and untied her top, pulling the string and watching it fall away. Her beautifully heavy nipples were puckered out, reaching forward. I slipped my hand under her ass to lift her up so I could lick her breasts. I put her right nipple in my mouth, squeezing the other one with my fingers. I licked and sucked, using my tongue to flick and play with it, then alternated to the other.
It was smothering hot again, and I could taste the salty sweat on her skin.
I put my other hand under her, so I had both hands under her ass, and lifted her higher. She was light, and sitting made it easier to leverage her. I lifted her so her crotch was level with my face. She reached down and untied both sides of her bikini at once, the knot magically slipping away. Her bikini bottom dropped to the floor, her naked pussy in front of my face. I lifted her higher, pulling her legs apart further. Her cunt was shinny wet, the slick folds of her hairless snatch neatly folding around each other.
She put one foot on the table, hooking her heal on the ledge, relieving some of the weight from my hands. I moved her closer and kissed her cesarean scar, running my tongue along the length of it. I pulled her wider with my hands and watched her wet opening gently pull apart, her inviting hole spreading open. She was wet and swollen with excitement, and a bit red from the earlier pounding. She pulled her other leg up and rested her knee on the top of the chair, then reached up behind me. There was a picture bolted to the wall and she grabbed the top of it, now completely holding herself up. She pushed her crotch closer to my face. Using her other hand, she reached down and spread herself, pulling her lips up and out.
She moved her fingers, adjusting, then spread her fingers wide apart. Her clit pushed out, proclaiming itself boldly. It was very large, engorged, as if neglected for far too long. She pushed closer so it was right at my mouth. Her clit poked out so far I was able to touch it with just the tip of my tongue. As I pushed against it, I heard her yelp, her hips jerking. She slipped her hand away, moving it to behind my head as she pressed into my face, straddling my head. I used my tongue to pull her clit all the way onto my mouth. As my face slid into her crotch, I could feel how wet she really was. She was soaked, and my face became instantly drenched as she pushed hard into me, pulling at the back of my head.
It was like her body was lit up from within. As I sucked her, I could feel the heavy heat coming off her, like a fever. The smell, the texture, the taste, sucking the very heart of her sex. It was intoxicating. My whole face was slippery wet, sliding over her pussy, tonguing her clit and gliding lower, gorging at her opening. My dick was so hard now it was painful. I had to lift up my hips and pull the towel out.
I worked her clit, swirling it with my tongue and giving it hard sucks, then pulling it with my lips and licking all around it. Gripping my hair in a fist, she ground into me, controlling the angle and pressure. There was a certain desperation to her movements as she gyrated against me. She was making breathy, grunting sounds, like she was straining. I was expecting her to orgasm quickly. Her body was keyed up, torquing and twisting. With my hands under her ass, I could feel her muscles flexing as her body went though it’s contortions.
It didn’t happen. She had increased her motion until she was fucking my face in a frenzy, nearly smothering me. But she couldn’t quite catch the wave that was trying to move though her. Somehow she wasn’t able to grab onto it as it rolled beneath her, just ahead of her grasp.
I realized I had been wrong about her. Earlier I had figured she only had the occasional orgasm, when she had a moment to slip away by herself. But now I realized it was something different. Orgasms just weren’t part of her life, and probably hadn’t been for a very long time. Somehow that aspect of her had gotten buried, neglected, ignored, and the years slipped by without it happening. Perhaps it was easy to ignore, the invisible need that could be put aside for more pressing matters. She’d learned to do without.
But now her body was paying a heavy price. It wasn’t going to be denied, but she was caught. Having come this far, her body wasn’t going to be stifled into submission. Her healthy, vibrant, beautiful body was ready, bursting and spilling over with lust and desire, but her head couldn’t seem to get it. Her brain was stuck. Some part of her just wouldn’t give in, and she was becoming desperately frustrated. I could hear her, whimpering now in hiccups as she continued to wildly grind my face.
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