tagMatureThe Accidental Gigolo Pt. 02

The Accidental Gigolo Pt. 02


Chapter 5: The Accidental Dominant, Part Two

I figured that it would take me a little less than an hour to wash and wax my dad's car to my mom's satisfaction. That would still give me five hours or so to get online and learn everything I could about Mrs. Stone's unusual, er, preferences before she arrived.

That was the theory, anyway. Subtracting the time that my mother insisted I spend mowing our lawn so that it looked nice when Mrs. Stone was going to arrive — arrive after dark, mind you — left me with three and a half hours. Minus the weed-eating left me with two and three-quarters hours. Minus the time it took me to prepare dinner left me with two hours. Minus the time we actually spent eating dinner, during which my mother developed a wholly unexpected and very poorly timed interest in my computer programming skills, which might after all be marketable if Pam Lee wanted to use them at her high school, left me with a little over an hour. And then you have to subtract the time I spent doing the dishes, the time I spent tidying up the den, and the time I spent showering, the only activity of the bunch that was my idea.


My mother's voice cut through the bathroom door, the sound of the fan, and the towel with which I was drying my hair. I pulled the door open an inch.

"Yeah, mom?" I yelled back.

"Mrs. Stone is here. We're leaving. We'll probably be quite late. So whenever you can tear yourself away from your shower, maybe you can lower yourself to come down and say hello."

My mother is one of those rare people whose sarcasm loses none of its effectiveness when she screams. Bitch.

"Have a good time!" I yelled.

"I'm serious!" she yelled back.

"Me, too."

That one was more or less a whisper, of course.

I wrapped the towel around my waist and walked down the hallway to the window overlooking the driveway. From there, I watched my father, in his tuxedo, hold the door of the nicely washed and waxed Jaguar open for my mother, dressed in a strapless black gown. The car purred down the driveway, and I went back to the bathroom to finish up. I shaved, I blew my hair dry, and then I tried to decide what to wear. What did the well dressed master wear, anyway? If I had managed to get fifteen damn minutes to myself this afternoon, I'm sure I would have found some sort of website. Jeans? Too informal. Sweats? Too high school. A tux? I actually owned a tux. No, too James Bond. She'd probably just start laughing. She was probably down there laughing anyway, come to think about it. I mean, this was a successful business woman down there. After her divorce, Mrs. Stone had started her own interior decorating firm, and currently employed half a dozen people. She was probably waiting downstairs right now to rip me a new one unless I agreed never to breathe a word of what had happened this afternoon to anyone, ever. Damn it.

I pulled on a pair of humble khaki slacks and a nice, freshly laundered button-down shirt, and I headed downstairs.

When I got to the last step, I just stopped and stared. Laura hadn't heard me approach, and was sitting on the couch. She was dressed in a white shirt and a short, plaid pleated skirt. She was wearing kneesocks and a pair of shiny black patent leather shoes. I couldn't believe she had worn that outfit here. Then I saw a little tote bag in the corner of the room, with a pair of jeans thrust into it. That was what she had worn here. She had changed after she arrived.

Even more unbelievable was what she was doing. Her left hand was holding a magazine. I could tell right away that it wasn't one of our magazines, because it had a centerfold. And if Mom ever found a magazine with a centerfold, Dad and I would both be looking for work as eunuchs. Laura's right hand was underneath her cute little skirt. Her eyes were slightly unfocused as she studied the centerfold, and the tip of her tongue was pressed against her upper lip. My tentative conclusion, from all of the evidence in front of me, was that this successful businesswoman had dressed up like a little school girl and was getting herself off on a Playboy magazine. Holy shit.

And then suddenly she looked up as if she had heard me, thrust the magazine under the couch cushions, and jumped to her feet before turning to look at me.

"Mr. Martin," she said. "I'm sorry, I didn't think you were getting home until later."

Later than what? And when did I become Mr. Martin?

She tried to surreptitiously wipe her hand on the back of her skirt, and offered it to me as I walked into the room. I took it, still slightly sticky, and she eagerly shook my hand.

"I'm Laura, the new babysitter your wife hired," she smiled. "Didn't she come home with you? She said she planned on getting a little tipsy to celebrate your new promotion. So what, she was afraid of ralphin' in the car? Did you just get her a room at the hotel and come back to take care of the boys? You could have just called. I would have been happy to spend the night."

At this point in my life, I had never heard about role-playing, and I certainly had never given even the smallest consideration to acting out sexual fantasies. With the damage my mother had done to my psyche, I figured that I was lucky just to have the fantasies. So I was completely mystified by her references to my wife and "the boys." Still, there had been a Playboy involved earlier.

"Um, yeah," I slowly answered the last question that I could remember her asking. "The boys."

"Oh, they're fine," she said. "I put Billy to bed right after his bottle, and little Terry Junior went to bed at his normal time. Well, almost his normal time. We had to have a little discussion first. That's a pretty advanced little ten-year-old ya got there, Mr. Martin. If ya know what I mean."

I had no idea what she meant.

"So everything else was, um, okay, Laura?"

"Oh, yeah," she smiled. "I was just sittin' here, like doin' my homework. Oh God, speakin' of homework. Mrs. Martin said you were like a history major. That is just so amazingly weird. 'Cause I got this homework question, and ya know, like, I could go home and get on the 'Net to find out, but then my mother will hear me, and she'll think I'm in one of those lezzie chat rooms again. Oh, it's not like I'm like that, you know, a lezzie, but the girls there are just real nice, ya know? And God, they know so much. Anyway, I didn't know how else to find out, so if I could just ask you, that would be so cool."

She looked at me expectantly, while I tried to figure out which of her statements had been actual questions and which were just regular sentences that she had ended with a question mark. There were lots of girls at my school who talked just like that. In the meantime, I glanced around the room. The living room was full of books, including two different sets of encyclopedias, that my mother had purchased to make us look intellectual.

"Oh, yeah, books," Laura saw my look. "I just can't do books, ya know. Too big, too old, too boring, too much extra crap in 'em, ya know? So anyway, I know, like, George Washington was the first president, and Abraham Lincoln was the second, but who was like the third? At first I thought it was that guy on the twenty — Jackson? — but then I was like, well, maybe it's the guy on the ten. You know, one, five, ten, twenty? But I didn't have any tens. Do you know? It wasn't Kennedy, was it?"

By this point, I was actually biting my tongue to keep from laughing.

"Um, Roosevelt," I said.

"Cool," she gave me a grateful smile. "Let me just write that in."

She walked to the corner of the living room and dropped to her knees in front of her tote bag, thrusting her butt back at me.

"God, where did I put that?" she muttered, tossing her jeans to one side as she rummaged through the bag. "Was that Franklin or Freddy?"

"I'm sorry?" I choked.

"There were two Roosevelts, right? Was it Franklin or Freddy?"

She was still looking through the bag, and a pair of handcuffs came flying back at me as I told her it was Franklin.

"Oh, God," she turned to me with her hand covering her mouth, her eyes wide with surprise. "God, I'm so embarrassed you saw those. They're my mom's."

She crawled toward me to pick up the handcuffs.

"Your mom's?" I asked. "Is she a police woman?"

"God, no," Laura giggled. "She and Daddy use these when they, you know, do it?"

"The handcuffs?"

"Yeah. I drilled a little hole in my closet so I can watch 'em. Anyway, I was takin' 'em to school to show my girlfriends, and I guess I just forgot they were in here. I'm so sorry, Mr. Martin."

"That's, uh, fine, Laura," I said. "You should be more careful, though. Your teachers could see them."

"Oh, God," her eyes grew wide again. "They would like have a shit fit. Oops, I'm sorry. Except Ms. Lee, of course, she's my French teacher. She'd probably soak one of her little thongs if she saw something like this. I swear, she is such a slut."

"Ms. Lee?"

"God, yes. She is such a cocktease. And she is really pretty. Although not much in the boob department, ya know."

She looked down with regret at her own breasts.

"'Course, some of us got a little too much, if ya know what I mean. I guess it all evens out, huh? Anyway, she would go apeshit for these things. Do you want to see 'em? Maybe Mrs. Martin would like to, you know."

"I don't think Mrs. Martin would like to lose that much control," I said. But I took the cuffs from her anyway.

"Oh, well, you can get out of 'em," she eagerly snatched them out of my hands to demonstrate. "See, you just press here, on the outside of the cuffs, at the same time, and they just pop open. So you can actually get 'em off yourself if you have to. 'Course, you're probably right. Mrs. Martin doesn't really look like the type."

"No," I agreed. "Probably not."

"Although she apparently has no trouble bein' on the other end, huh? I mean, spanking little Terry."

She clapped both hands over her mouth this time, as if she had said a little too much. And by this time, I was getting a little more comfortable in our little improv.

"How do you know that, Laura?"

"I, um, I..." she let her voice trail off.

"I can find out, Laura. Mrs. Martin had this little security camera system installed."

"Oh, God, please no," she said. "He was just, you know, acting up, so I, you know, spanked him. It was pretty clear he knew the drill. I mean, pullin' his pants down for me and everything."

"So you spanked my son?"

"It's not like he hasn't been spanked before," she protested.

"By my wife," I pointed out. "Did she give you permission to spank him?"

"No," she hung her head.

"Then, um, why did you do it?"

"I, um, God, I'm so embarrassed, Mr. Martin, please don't make me say."

"You have to tell me, Laura. Otherwise I'll have to tell Mrs. Martin, and then she'll end up showing this video to your parents."

"Oh, God, no, please, please," she wrapped her arms around my knees. "Couldn't you just, like, punish me yourself, and then we could just, like, you know, forget the rest?"

"And how should I punish you, Laura?" I asked with a smile.

"You could, like, spank me?" she slowly offered her suggestion.

"You might like being spanked," I said. "In fact, I think you do like being spanked. Do any of your boyfriends spank you, Laura?

"Gawd, they're such babies. Little babies, you know? I mean, Gawd, Terry Junior's bigger than — ohmyGod, I'm sorry."

"Come here, sweetheart," I said. I backed up and took a seat on the couch. She started to get up.

"Stay down, honey," I instructed her. She began crawling towards me. "And bring the cuffs with you."

She crawled back for the cuffs and started to return. Feigning difficulty crawling, she put the cuffs in her mouth and finished the journey, dropping them into my outstretched hand. She remained kneeling between my legs.

"Take off your shirt, Laura."

She sat back on her heels and made a production of unbuttoning her shirt, interrupting her progress every other button with a fearful glance at me. She tossed the shirt aside and reached put both hands behind her back.

"Did I tell you to take off the bra, Laura?"

"No, sir," she yelped.

She jerked her hands back in front.

"Did I tell you to move your hands?"

She quickly put them in back again. I picked up the cuffs and pressed the catches. Laura bowed in front of me, and I cuffed both hands behind her back. Standing up, I yanked her to her feet and pushed her towards the stairs.

"Hold on," I commanded when she was halfway up. From the step beneath her I reached up under her skirt. She had ditched her panties, as well.

"Good girl, Laura."

"Thank you, sir," she whispered.

I escorted her into my bedroom, and stopped just short of the bed.

"Wow! Is this where you and Mrs. Martin...?"

"Where Mrs. Martin and I what, Laura?"

"Fuck?" she whispered.

"Mrs. Martin fucks with me all the time in this room," I answered honestly, suppressing a smile. "And this is where I'm going to fuck you, Laura. Get on the bed."

She crawled onto the bed with some difficulty and finally arranged herself against the headboard, her legs spread. Turning my back on her, I kicked my shoes into the closet. My socks quickly joined them. I took off my shirt, and hung it up. I took off my pants, and hung them up, too. Finally, I turned around, and slipped my fingers into the waistband of my briefs. Laura's eyes were locked on my crotch as I nonchalantly exposed it.

"Oh, fuck, I can't," she hissed.

"Can't what, Laura?" I asked.

"Can't possibly fit that inside me," she snapped her legs together, her face taking on an aspect of panic, her voice starting to tremble. "God, you're fucking enormous, Mr. Martin."

"I think you can handle it, Laura," I said.

"Um, I don't think so," she started to slide toward the left-hand side of the bed as I approached the right. "NO!"

I reached forward and grabbed the handcuffs, jerking her back into the middle of the bed. Her loose, pleated skirt had flown up, over her rear, and she buried her head into my bedspread and scrambled to pull her knees underneath her.

"Please be gentle, Mr. Martin," she whispered.

I clicked open the handcuffs again.

"Put your hands between your legs, Laura."

I cuffed her wrists again.

"You were playing with yourself earlier tonight, weren't you, Laura?"

"Mr. Martin," she whined, tugging just a little at the cuffs I held in one hand.

"Stop squirming, Laura," I gave her a swat with my other hand.

"Sorry," she whimpered.

"Wait here, Laura."

I went downstairs and fetched her magazine from underneath the cushions of the couch. When I returned, Laura was in exactly the same position I had left her. I got up behind her again, and opened the centerfold in front of her.

"Do you like her, Laura?"

Her body twitched but she just stared at the centerfold.


It was more a cry of surprise than of pain. My little swat hadn't been hard enough to hurt, just to bring her attention back to me.


"Yes, I like her. Yes, I was playing with myself. Please, Mr. Martin, this is so humiliating."

"Is it? More humiliating than it was for Terry Junior to have to pull his pants down in front of you so you could take a good look at him?


"Well, you little bitch?"

"OW! I didn't mean to. He just turned around when he was pulling them back up. I never touched him, I swear. OW!"

"Like I give a fuck, you little slut. Now let's see you play with yourself some more. Come on, isn't she pretty? Imagine having her do this."

I drew a finger up her exposed slit. Laura moaned.

"Or imagine a nice big dick in here," I added, pushing two fingers inside of her.

"Yessss," Laura whispered.

"I don't care what you imagine, honey," I leaned down to whisper in her ear. "But you better start doing it."

I pulled back and pulled her cuffed hands between her thighs. Her fingers quickly replaced mine, and I sat back on my thighs to watch this beautiful lady pleasuring herself for the second, no, the third, time that day. God, was it really still the same day? Eight hours ago I had showed up at Mrs. Stone's house hoping for a payday of thirty bucks or so. Now here she was at my house. She could keep the thirty dollars.

"Ummmmm," she moaned, driving two fingers in and out of herself. "OW!"

She dropped her hands to the bed when I spanked her, and I lifted them again.

"Did I tell you to stop?"

"No, but you..."

"Punished you?"

"Yes, sir."

"Should I add an extra punishment for stopping?"

"No, sir, I promise, I'll be good."

Her hands were working furiously again, and when I delivered the next smack on her upturned cheeks, she didn't break stride once. If anything, she started to expect it, and to incorporate it into her little self-service session. So I changed the tempo, waiting a little longer to deliver the next one, and then adding two short swats in quick succession. It didn't take her long to reclaim the state, just on the precipice of satisfaction, that I had left her in when my mother had cut us off a few hours earlier.

"Oh, fuck, Terry, I'm coming. Oh, God, I'm —"


"Terry," she whined.

I yanked her hands down, watching the way her whole body quivered, whether in expectation of another blow or because I had denied her fulfillment I couldn't tell. I knelt behind her, determined to finally bring that deferment to an end.

"Hands behind your neck, honey," I ordered. She obeyed immediately.

"Oh, fuck, Terry," she moaned as I thrust forward.

I pulled back.

"Terry?" she wiggled her butt at me.

"Terry?" I asked coldly.

"OW! I'm sorry, Mr. Martin. Please, Mr. Martin, ooooh, yes."

After a minute or so, Laura decided that it was too hard to remember to say "Mr. Martin" on each stroke forward, and simply settled on "sir." After another minute, it became "oh, sir," and then "fuck, sir," and then she dropped the "sir" entirely and just groaned the word "fuck" every time I buried myself deep inside her. And then finally I picked up the pace to the point that she could only manage to grunt. I didn't last long, of course. After our afternoon foreplay, I was probably even more eager than she was. But I did last long enough to hear her muffled scream of "Yessss!" as her muscles contracted around me, which was certainly more than enough to cause me to lose it inside her. I added a few groans of my own as I passed through an extraordinarily extended version of that delicious sensation that occurs just before ejaculation, and then I held her hips in place until I was completely drained.

I reached forward and realized suddenly that this woman had actually tired me out. Me, a high school athlete. And her, my mother's 39-year-old college roommate. I grabbed hold of her bra strap and yanked her upright. She waited as I opened the cuffs, and briefly rubbed her wrists before turning back to me with a big smile.

"You know, I have to tell you that you were even better than I thought you would be," she smiled at me.

"Well, then I have to tell you that the whole thing fell a little short of what I had always imagined," I told her.

I watched her face fall. In a few seconds, her chin would start to quiver, and then a small tear would appear in the corner of one of her eyes. She would take a deep breath, and tell herself that she couldn't expect any more than that, and then she would smile at me and say that she hoped I had enjoyed it a little, at any rate.

"Yeah," I said before she had a chance to start. "If you had told me that I would fulfill my dream of doing Laura Stone without ever having had a chance to enjoy those amazing tits, I would have found that very, very difficult to believe."

A whole range of emotions played across her face, the disappointment ultimately being replaced by an almost child-like delight.

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