I spent Thanksgiving at my brother's house. Besides my brother, his darling wife, and me, the festivities included our parents, another brother, two sisters, everybody's spouse, and rugrats all around. I was the only one single and childless. I always preferred it that way, but this year I was a little envious of them and their broods.
When I got back to the city, I called Susan Worthington. Susan and I go back a long way, nine years to be exact. We met when I was a sophomore stud and she was a bright new frosh. On our first date, we went to my dorm room and fucked until we both were sated. We've dated ever since. Nothing steady. We both play the field, but we are friends. In fact, she is the best friend I have.
"Hi, Susan," I said when she answered the phone.
"Well, hi, Santa. How are those big Christmas balls hanging?"
"They need polishing, sweet cakes."
"That's not my fault. I polish them every chance I get."
"How about dinner tonight?" I said.
"Just dinner? I was hoping for a sleepover."
That was one of the things I liked about Susan. She never complained about what I did when I wasn't with her or what I did for a living when most women would complain loudly. She just wanted me.
"A sleepover is what I had in mind," I replied.
"What time?" she asked.
"Better make it seven. I've got the first of the Christmas parties tonight."
"Seven it is. Have fun at your party, Santa."
I'm an unlikely Santa Claus. I'm only twenty-eight, which is far from the right age of three hundred and something. I'm six six, which is about a foot-maybe a foot and a half-taller than the jolly old elf. I weigh two hundred fifty pounds, which is about the right weight for Santa, but mine is all muscle. I keep it that way with regular hard workouts.
I do have a thick beard that extends half way down my chest. I started it in high school as a joke, but Molly Swingmore thought it was a turn-on. I kept the beard even after I dumped Molly because I liked it. The women love it or hate it, and some who thought they'd hate it end up loving it. They like it better white, so I keep it that way year round. My hair is longish, wavy, and coal black. In the Christmas season I color it white.
I went to college on a football scholarship, blew out my knee when I was a junior, and was told my football days were over. Fate plays strange tricks sometimes. After my surgery, the hospital was overflowing with a flu epidemic so I shared a semi-private room. Cecil, the guy next to me, had a knee replacement. He was in his sixties, rich as hell, and an alum of the school I attended. He was a football nut so we got along well.
A woman about thirty-five and classy in a slutty way, if you know what I mean, came in to see Cecil. Her clothes and jewelry were expensive, but the clothes were skimpy and tight and the jewelry was gaudy, and she wore a little too much makeup. Cecil introduced her as Pearl, his wife. Pearl whispered in Cecil's ear.
"Well, ask him," Cecil said.
She stared at me like a starving dog looks at a steak. "Can I see your cock?" she asked.
I stared at Cecil. "Don't worry, Eddie. Pearl plays around. I know it and I don't care. Sometimes I watch and sometimes I join in for a threesome."
I flipped back the covers, pulled my jockeys down, and let my cock free.
"Oh, God, that's soooo nice," she whimpered. She dragged her nails down the shaft, wrapped her fingers around it, and gave it a hard squeeze. "I want to fuck you," she said.
"All right," I replied. "But I'm immobile. You'll have to do it."
Pearl locked the door, stripped off her pantyhose, crawled on the bed, and prepared to mount up.
"Personal foul. Unsportsmanlike conduct," Cecil snapped. We both stared at him. "That's not fair, Pearl," he said softly. "The kid's football career is over and he's going to need money. Offer to pay him."
"I'll give you two hundred dollars if you'll fuck me," Pearl said to me.
"All right," I said.
"Not so fast, Eddie," Cecil said. "You need an agent to help you negotiate the contracts. Let me handle this. Pearl, he's a whole lot better looking and has a much bigger cock than that black guy you're paying to fuck you. Eddie deserves a least double what that guy gets."
"Leroy's a woman pleaser," Pearl said. There was a steely look in her eye. "Maybe Eddie is one of those assholes who doesn't care about the woman."
"Good point. I'll tell you what we'll do. He'll fuck you now for free. If he's good and you're pleased, his fee is a thousand a date, twenty-five hundred for a weekend, and that's one girl only."
"Agreed," Pearl answered greedily. I could feel her pussy dripping on my thigh.
"Not so fast," Cecil said. "We want you to introduce him to your friends. He'll need a stable to live well."
"If I introduce him to my friends, I want some freebies," she said.
"Once a month free," Cecil said.
"Once a week," she countered.
"Twice a month."
"Damnnit, Cecil. I'm your wife. It's your money I'll be paying him."
"Once a week is fine with me," I said.
"Okay. Once a week it is. Do we have a deal?"
"Deal," Pearl said and I echoed her. Pearl clambered onto my bed and promptly impaled herself on my cock as Cecil watched happily.
That's the way I became a gigolo, which was my primary source of income as I finished college and earned a masters. And that income allowed me to start and build my business. Thanks to Pearl I soon had a cadre of willing wealthy women who paid me for sex. I became a Santa Claus because one of the ladies I serviced thought it was cute. I soon came to love the season for all the right, and the wrong, reasons. And I charged an arm and a leg to work the Christmas parties.
Christmas season is hectic. Fortunately, my stable of ladies who pay are usually involved with their own families and social events so I can focus on the Christmas parties. I have different costumes for my different "roles" as Santa. There's the standard suit and padding for the kids parties and something a little sexier for the teens or the adults who aren't sure what kind of party they want. For office parties, I wear a lycra spandex suit without padding. And for certain special occasions, I wear red leotard bottoms and nothing else.
I like company parties best of all. Women who are the epitome of decorum all year long lose their inhibitions and want to spread their legs for sweet old Santa. Maybe it's a payback for all those presents over the years. I usually end up with a pocket full of names and phone numbers. The ones I like, I call. For some reason things were different this year. I didn't see as many that I liked.
On December 17, I was working a company party in a major office building. It was the standard rowdy crowd and I collected an average numbers of names and received an average number of gropes. One darling little number caught my eye. I knew immediately who she was and I wondered if she remembered me. She tried to be discrete as she stood in line to sit on my lap, but her eyes never left me for long.
"Hi, Santa," she said softly when she sat on my lap, her big blue eyes locked onto me.
"Hi, Cindy. How are you?"
"I knew you'd remember me," she beamed.
"I could never forget you, Cindy."
"Eddie, I'd like to talk to you in private."
"I'm through here at four. Why don't you have dinner with me?"
"Oh, I couldn't, but we can talk for an hour or so."
Her name had been Cindy Durwood and we had sat next to each other in freshman biology because of the alphabet. As fate would have it, we had a class together our sophomore year. There we chose to sit together.
Cindy was a living doll, and I wanted to treat her that way. You know-undress her, lay her back, and play with her. She was not quite five feet tall and probably weighed a hundred pounds. She had raven hair she wore short, porcelain skin, a bee-stung lower lip, and huge blue eyes. The effect was the sexiest wood nymph you ever saw, but Cindy didn't act like a nymph. She was modest and demure from her clothes to her actions.
There were damn few girls I wanted that I didn't bed and Cindy was top of the list.
She was waiting when my Santa shift was over and followed me to my car. We sat in the front seat of my Porsche and talked. She'd married Robert Kenyon, who was the love of her life, the only boy she ever had, and all that. I remembered the name. He was the reason she wouldn't date me in college.
I could tell she was ready to talk about what she really wanted to talk about. She was quivering when she said, "One of the girls at the office told me you're a gigolo." I admitted it was true. "Good," she said with a smile. "I'd like to hire you to have sex with me."
"You what?" blurted out of me.
She giggled, reddened, and covered her mouth with her hands, but in seconds her hands fell away as she openly laughed. "Oh, Eddie. I wish I had a picture of your face." She leaned forward conspiratorially. "I knew how much you wanted me, Eddie. It was fun having the biggest stud on campus chasing after me. I'll admit I led you on, and I loved flirting with you, but I never, ever, would have cheated."
"I know," I said.
"Do you want to know why I want to have sex with you?"
"Not really. I just want to do it."
"Why I'm doing it is all important," she said seriously. "Bobby wants me to have sex with another man while he watches. He's been after me for three years to do it and I've always said no. He even had an affair and told me about it, hoping anger would make me have someone else."
.... There is more of this story ...