tagMatureThe Accidental Gigolo Pt. 01

The Accidental Gigolo Pt. 01


Chapter 1: Accidents Will Happen

I am a genuinely nice guy. To take just one example, I never needed to be reminded that there was a community service requirement we'd have to meet before we graduated; I'd fulfilled it before I got to eleventh grade. Mostly to get out of the house, true, but also because I really enjoyed working with the deaf kids at the public library. My cousin Martha was deaf, and the fact that my mother couldn't be bothered to learn Ameslan made it all the more attractive to me. Martha and I could sit there and "chat" right under my mom's nose. Mom's younger sister Penny knew exactly what we were saying, but she apparently had her own issues with Mom. I saw her biting her lip on more than one occasion to keep from laughing. The kids at the library were just delighted that I knew it, and we had a great time each week.

It's true that I am just a teensy bit accident-prone. And that some of those accidents were at least partially my fault. Although to hear my mother talk about it, you'd think that it was entirely predictable that a truck carrying maple syrup would crash at 4:15 p.m. on a road that I would be driving at 4:17 p.m. I mean, they weren't even going to raise our premiums for that. But no, I'd be riding my bike for the foreseeable future. And I could see where some of our neighbors might have thought, solely as a result of a complete accident, that I wasn't a nice guy. Although I still can't believe that Old Lady Willingham thought I hit her dog on purpose with that baseball; she nursed that grudge even after his cast came off.

Anyway, I think it ought to be understood, right up front, that I am a nice guy. And in that light, you have to believe that blackmail wasn't the first thing I thought of while I was watching the videotape. It wasn't even the second thing. As nice guy as I am, it actually wasn't something I thought of at all. It was an accident. That's right, an accident. If you want to point a finger of blame at somebody, I say let's start with the tape:


My mother, Deirdre Martin, peered at her friends over top of her undersized wire-rim glasses.

"All right, girls," she grinned, "but you have to swear that not a word of this will ever leave this room."

"Swear," Laura Stone gave a hesitant smile.

"Swear," Pamela Lee said.

"Swear," Natalie Winston echoed.

"Good," Mom said as she leaned forward to begin the round of tales. "Well ladies, remember last summer when I treated myself to a weekend at that fancy health spa?"

The other women nodded.

"I think I told you all about the golf and tennis, but I didn't tell you about the tennis instructor I treated myself to," Mom smiled wolfishly. "Twenty four years old, six feet two inches tall, 200 pounds of muscle, and a cock that never got soft."

"How big?" Pam asked, unconsciously licking her lips.

"Big enough," Mom snickered. "It's the only seven inch prick I've ever had."

As Mom poured another round of wine, Laura took a deep breath and began her own story. Since her divorce, she'd dated very little and engaged in sex even less frequently. As her friends gasped, she told them of the evening when her son had been out of town on a camping trip and one of his young friends had dropped by. Before she knew it, the two were upstairs in bed.

"How old was he?" asked a shocked Natalie.

"Seventeen," Laura admitted.

"Well hung?" Pam asked.

"Average," Laura shrugged.

"How'd you finally get rid of him?" Mom asked.

Laura smiled.

"It wasn't really a question of my getting rid of him," she sighed. "I'd have kept doing it the whole rest of the summer. We did it a few more times, and then he pretty much told me he was moving back to younger stuff."

"Speaking of younger stuff," Mom smiled, "Pam?"

"I need to start a little further back," Pam began. "When I was 21, I was a little short of cash. So I posed for a few pictures in a magazine."

"Any magazine we'd know?" Mom asked.

"Not unless your son collects some pretty obscure stuff," Pam chortled. "Anyway, about six years ago, one of my students found the magazine. Scared the shit out of me. Finally, he agreed to give me the magazine, but of course he had a price."

"Drive a hard bargain, did he?" Natalie giggled.

Pam laughed along with the other women.

"Hard?" she grinned. "Yes. Good? No. Big? No. After a while I just couldn't do it without laughing. So I decided to toss him out. By that time, I'd gotten him to give me all the pictures from the magazine, and I'd bought up the only two copies left in the local porn store. Once he didn't have anything on me anymore, I basically threatened to go to the police with his little blackmail."

"You hypocrite," Laura looked a little shocked. "Wasn't it you who tossed your husband out a few years ago cause you caught him doing his secretary?"

Pam simply gave the older woman a smug smile.

The women turned to Natalie, finding it hard to believe that the youngster had already cheated on her husband after only three years. She hadn't. But on the morning before the wedding, while her prospective groom was sleeping off his hangover, the prospective bride was having her fun with the prospective best man.

"Nothing since then?" Mom asked.

"Nope," Natalie said as the phone in the kitchen began ringing.

"Excuse me," Mom said as she rose from the table.

"Although not because I'm really satisfied at home," Natalie muttered after a healthy gulp of wine.

"Oh, come on," Pam growled. "You're married. You can have it any time you want."

"Tell you what," Natalie said. "You find me someone who can really do it well, and you can have him any time you want."

Pam smiled and leaned forward.

"Yeah, I know what you're going to ask, you slut," Natalie giggled. "It's a little above average. The problem is it comes too fast and it ends too soon."

"Well, you can keep him then," Pam said. "Laura?"

"Yeah, right," laughed the brunette. "Who'd wanna screw a 39-year-old divorcee with a college age kid and a size 12 ass?"

"Someone who likes that Double-D rack!" Natalie offered cheerfully.

"Oh, sure, I can probably get some boy to come over," Laura said. "But not the kind of man I want."

"Somebody man enough to keep that ass in line, huh?" Pam said bluntly as Laura flushed a deep crimson.

"Anyway what do you care, Pam?" Laura interjected. "I wouldn't think you'd have any trouble getting laid!"

"My husband may have been a bastard," Pam said with toss of her hair, "but after his seven-inch cock, anything smaller doesn't even seem like fucking."

"I wonder how good Deirdre's son is," Natalie said, raising her eyebrows. "He's turned into quite the little muscle boy."

"Terry? He is cute," Laura agreed. "But I'll bet momma has him a little too "whipped," if you get my meaning. All that 'yes, ma'am,' and 'no, ma'am' stuff."

Pam smiled.

"And I'll bet we know who'd like to be whipped instead," she said, making Laura blush again. "But she's right, I think you're out of luck, Nat. He's in my French class this year, and I doubt he's any different than the rest. At least when it comes to size."

"And how would you know?" Laura asked slyly.

"At least once a week, I wear one of those tight little dresses that produce a hard-on in every boy in that class," Pam gloated. "And I haven't had a good look at Terry's bulge, but this year's jocks are a pitiful little bunch. Hell, as long as it's been since I've been laid, if I thought any of 'em even had a good thick six inches I'd be conjugating all the verbs he wanted for him after school."

"Hey, you're the quantity queen," Natalie giggled. "I just want quality."

Mom breezed back in the room just then.

"Well, ladies, I'm afraid we have to call it quits," she said. "That was my office. They just made an arrest in that forgery case I've been working on and I've got to go downtown."

Mom walked out of the room behind her guests, a faint smile playing across her lips.


I shut off the videotape and my first thought, I swear to God, was that I couldn't believe my mom was such a bitch. I mean, I could, because she was, but really, taping her friends talking about sex? After she'd steered the conversation in that direction? What a fucking bitch! My second thought? Did Laura Stone really think I was cute? I mean, I'd heard her say it, but did she really think that? I reminded myself of Rudolph the Red-Nosed Reindeer ("She things I'm cuuuuute!"), not for the first time.

I'd returned to an empty house just a few minutes after Mom and her friends had left. Almost by reflex, I'd begun to clean up the table where they'd been sitting, when I noticed that something in the room was out of place. It took me a while to identify the video camera sitting on the bookcase, pointed directly at the table. Moving closer, I noticed black tape over the red light that glowed to signal that the camera was on. And sure enough, the camera was on. I turned it off and ejected the tape. Obviously, Mom had been taping her friends, and didn't want them to know it. But why? On second thought, who the hell cared why? I had a tape of three of my mother's beautiful friends, three women who'd starred in more of my fantasies, waking and sleeping, than all the other women in the world combined.

It wasn't like I had a huge database of fantasies. I mean, it's not like I did it every night or something. Maybe every other night, but not every night. And there were girls at school that I liked, and actresses, of course. Hell, that chick on the Today Show looked real good some days. The one that read the news, not so much the one that took Katie's job. But these three women — Laura Stone, Natalie Winston, and Pamela Lee — were the stars. I dug through the cassettes on the shelves and found a defective tape that I'd unsuccessfully tried to use a few weeks ago. I slipped it in the camera and put the camera back where I'd found it. Then I turned it back on in the "record" mode, so that Mom would simply assume that she'd put a bad tape in the camera. By the time she returned late that afternoon, I had already downloaded the tape onto my PC and hidden the video file in a very safe folder in my hard drive. Erasing the tape was even easier.

I played the video the next weekend, when both of my parents were at work. It started out as an ordinary card game, with the four women still just chatting, but I'd already pulled down my pants and begun stroking my cock. Mom had deliberately taken the seat — almost pushing Natalie out of it when she tried to sit there — with her back to the camera. That was good for two reasons. The first was that I had a good view of the other women. The second was that I didn't have to look at my mother.

Because, believe me, the last thing I wanted was to find myself jerking off to pictures of my mom. My friends would have paid good money for a video like that; they had all confided to me, at one time or another, that my mother was the first one they thought about when they were doing it. Like I really needed to know that. Some of them, the little pervs, had even thought of her when they were fucking their girlfriends. I really wish that they hadn't told me that part. But it explained why my house was one of the more popular hangout places. At family get-togethers at Grandma's house, where you didn't actually have to be friends with anyone because you were gonna get invited back next year no matter how much you pissed 'em off, Mom was fond of boasting that she had the same figure that she had had in college. And her face hadn't changed much, either. The only difference was that the long blonde hair she'd had then was now styled into a short professional look that suited her job as an Assistant District Attorney. She knew perfectly well the effect she had on my friends, and lapped it up like a cat, teasing them with shorts that were too short and tops that weren't quite top enough. They just ate it up and came back for more.

On her left in the video was Mrs. Stone, my "Aunt Laura." Laura Stone had been Mom's best friend ever since she'd invited Mom, as a young college sophomore, to share a suite of rooms that Laura and two other senior girls had snagged. She was now 39, the oldest of the four women who had sat down around the table, ostensibly to play hearts. She was the shortest of the three women and perhaps the heaviest (although by no more than 10 pounds), but her chest was easily the biggest of the bunch. A few years ago I'd peeked into Mrs. Stone's closet when I took a break from mowing her lawn and went into the house for a drink while she was out grocery shopping. There it was, a 38-D bra in her hamper. Maybe she swelled to a Double-D in the fall, like Natalie said; was that possible? In any event, I was very pleased to see her in profile on the tape. And because it was still only the end of September, with unusually warm temperatures, Mrs. Stone was wearing a very tight cotton T-shirt. Awesome.

I turned my attention next to Natalie Winston, sitting on the right of my mother. Ms. Winston — "oh, please call me Natalie," she was always saying — had moved in next door, with her husband, about eighteen months ago. She was 28 or so, a number I'd arrived at by piecing together some clues she'd tossed off about her college days. With her bouncy auburn hair and beautiful blue eyes, I just knew that she'd been a cheerleader then, and she'd been the main subject of my jack-off sessions over the past summer, when she started visiting our pool. In the tape, she had on pair of much-too-long shorts as well as a pink sleeveless shirt. Natalie also had a very nice chest.

The final woman, Pam Lee, had been the subject of my fantasies for most of the last school year. She'd taught French at the high school for the last five years, and the locker room scuttlebutt put her age at 31. I'd first seen her when I was an eleventh grader last year, when my French teacher had been the gruesome Mrs. Lee. And I'd spent many afternoons last year daydreaming about her long black hair, long legs, and dark complexion. She was the tallest of the three women, and the least endowed. But she was exotically beautiful. I couldn't believe it when she and my mom became friends over the summer, and I couldn't believe it when I found out she was my new French teacher this fall. I was salivating at the prospect of seeing those fashionable suits and short skirts every day. Boy, talk about mistakes. She might be a goddess, but in class she certainly earned the nickname passed down in the boys' locker room over the past few years: la garce Française. The French bitch never missed an opportunity to put down the boys in her class, particularly those involved in sports, and I hadn't been spared just because my mom was a friend of the teacher. A month into the semester, I was wondering how quickly I could pick up Spanish.

I shot my load ten minutes after I started the tape, but I kept the tape running. There might be some even better views to use next time. At that point, they were still just playing cards, gossiping about the woman across the street who had gotten herself pregnant in spite of her husband's vasectomy. Then I watched in amazement as my mother deliberately steered the conversation to sex, and my mouth fell open as each of the women — including my mother — admitted to their past indiscretions. My cock was already starting to rise again.

Up until that point, my sexual experience had been limited; if Natalie Winston was hoping I'd be good, she'd be well advised to wait until I got out of this place. Because basically since I was old enough to talk, my mother had taken advantage of every opening to remind me what she'd given up to raise me, that she had stood first in her law school class when she'd become pregnant, and that she would have been able to earn even more than my father earned if she hadn't had to suspend her education to take care of my baby, and that I owed her. In truth, she seemed to enjoy her work, especially her occasional appearances in the newspapers and TV news as she prosecuted yet another of the city's sex crimes. But she would never admit it to me or even my dad. In fact, she would sometimes remind my dad of her former class standing as a subtle put-down, although his large paycheck meant that she couldn't treat him like she did me.

Hell, Laura was right. I was whipped. My mom had left me with the self-esteem of a rabbit. The first couple of girls I'd gotten up enough nerve to ask out had practically fled the house giggling when I brought 'em over, as ordered, to meet Mom and Dad. They'd been treated to my baby pictures first, and then to a discourse on how sickly I'd been when I was growing up. I had finally grown into my tall, gangly body, thank God, sporting what I thought of as a decent set of muscles honed by my daily swimming practice. But I still saw myself, through my mother's calculating eyes, as a perennial weenie.

Since then, I'd manage to sneak out with a girl once or twice. But the girl with whom I'd gotten the farthest had taken one look at my cock and drawn the line at a hand job. Although I knew I had the biggest cock on the swim team, it was apparently one of the biggest in the school, and she wanted nothing to do with it. Maybe Ms. Lee wanted some, though, huh? I grinned as I recalled her remark about her need for a big cock. Hey, you want some of this, bitch? Well, maybe not, but I was entitled to dream. I rewound the tape to a point where Ms. Lee had stretched across the table for a misdealt card, giving the camera a tantalizing peek down her low-cut blouse, and froze it. I was surprised I could come again that quickly, too.

It took me two weeks to find the magazine. The problem was that if you just put "Pam Lee" into Google, you got Pam Anderson. "Pamela Lee" was even worse. And "Pam Lee" with "nude," with "naked," and with "posing" weren't (obviously) any better. "Pam Lee" and "coed" — that turned out to be the answer. And oh my God, that particular issue was still available from the publisher. Of course I ordered it. I invariably picked up the mail, even on weekends, because Dad got home late and Mom couldn't be bothered. The magazine was a bit pricey at this point, being ten years old, but ya gotta do what ya gotta do.

And it wasn't until I got it that I realized that I had a problem. My mom, the bitch, was constantly searching my room, looking for signs of the steroids that she was convinced that I must be using in order to develop muscles. Nobody on my father's side had muscles like that, she pointed out. And it was obvious that I hadn't inherited anything worthwhile from her side of the family. So obviously I was taking steroids, and she scoured the place every other week. And it's not like she even pretended to do it while she was putting away the laundry. Hell, I did the laundry in the house. I was the one who made sure her 36-C underwires got hung up to dry instead of going in the dryer and her size 4 panties were nice and fluffy soft. Yeah, I know. Fuck off.

Keeping it at school was a similarly bad idea. By order of the School Board, prodded and supported, I suspected, by crusading Assistant District Attorney Deirdre Martin, we were subject to completely random locker searches at the whim of the principal, the assistant principal, and the head of the art department, who was a reformed drug addict who was assumed to have special insight into the hiding places that we secretive druggies used. The three of them had a lot of whiMs. So my locker was another poor storage place.

I finally just said the hell with it and threw the magazine out. Oh, of course, I kept the pictures. I'm whipped, I'm not stupid. Once again, I scanned 'em onto my hard drive, where they were hidden in a file that you'd have to be a computer genius to find. Occasionally, though, I'd download one to my cell phone, where I could easily hide it from view with the press of a button, and where two other buttons would permanently erase it. Until I downloaded another one. In retrospect, of course, that wasn't the brightest thing to do. I will accept responsibility for that. But I'm not going to beat myself up over it. After all, I was probably the most wildly successful accidental blackmailer in history.

Report Story

byMarshAlien© 55 comments/ 484086 views/ 272 favorites

Share the love

Report a Bug

5 Pages:123

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: