Caution: This Sex Story contains strong sexual content, including Mother, Son, .
Desc: Sex Story: Chapter 1 - Sunny Rollins lived up to the name Sunny - - she was open, cheerful and quick to smile. She played piano and sang at the famed Carlyle Hotel. She also merrily entertained guests upstairs in her room. Her young son, Bobby, became her manager, booking her after-work appointments. He loved everything about his mother. Sunny's voice, her sexy good looks, her gusto when making love with her clients. Bobby shared his mother's friendly disposition. And appreciation for the sexier things in life.
(Jimmy, and I are continuing with our alternate chapter experiment. If you see my name, or Jimmy's name, in front of a section, that's who wrote the sappy prose which follows.)
"There's no people like show people..."
Sunny Rollins knew from an early age that she would have to make it on her own. Her mother, while nice enough when she wasn't high, wasn't very responsible when it came to basics. Like rent, food, clothing.
So at the age of 8, Sunny started singing. In public. For money. On weekends. Grand Central Terminal and Times Square were her two most lucrative gigs. Crowds, especially from out of town, were charmed by her youth. The tiny face, haloed by flaming red hair.
And her voice! Without any formal training, Sunny could flat nail it. Even jaded New Yorkers were impressed. She easily brought home over $100 a day. More when she worked both locations.
As she grew older, she was booked into an occasional slot downtown. Singing and playing piano on a small stage. An actual stage! Late one night she was discovered belting it out in an East Village dive bar by a Cafe Carlyle regular who was slumming downtown one night.
He was a valued Carlyle customer. And a generous tipper. So the assistant hotel manager arranged for Sunny to audition -- 5 minutes only -- in front of the legendary Bobby Short. Sunny was 14 when the Carlyle hired her to work the Cafe one night a week. She was that talented. And they knew her youth would be a novelty draw.
She named her son after Bobby Short out of appreciation for the audition. He didn't have anything to do with Sunny's pregnancy, but seemed amused when she told him about it.
Long used to being appraised by men, Sunny talked her way into the assistant manager's bed. A different kind of audition. After an hour, he was half in love with the little girl. Sunny parlayed that into what she later told her son, Bobby, "It was the smartest move of my life. Give Mr. Bennet some pussy for a free room. At the Carlyle!"
Bobby, around12 at the time, smiled in appreciation of his mother's wisdom.
Sunny went on, "Then word started spreading in the audience about how much I love fucking, simply adore it."
Bobby knew the Tip Jar story was coming. He loved hearing it no matter how many times Sunny told it.
"Then one night there was a $100 bill with a phone number written on it. Can you imagine, $100! Of course that was then."
Bobby heard the next familiar words before his mother said them, "These days I wouldn't even suck a cock for just $100."
This, Bobby knew full well. He kept the family books as well as managing his mother's appointments. They both loved the money, but also appreciated the goods and services they bartered for.
A doctor, dentist and attorney. Although the lawyer was more 'just in case' than actually needed. This was the third Carlyle hotel room they'd lived in. And the largest. The assistant manager, Mr. Bennet, had moved a baby grand piano from storage to Sunny's room.
"Let's go on with the show..."
She taught Bobby piano and they loved practicing her acts together.
It was still just one room plus a large bath, but as Sunny frequently told her son, "It's the fucking Carlyle!" Just one bed, but that was fine. Bobby had slept with his mother every night of his life.
Bobby was a true son of the city. Sunny taught him the easiest stations to slip into subways without over-burdening the turnstiles with tokens, then Metro cards. He roamed all over Manhattan from the Harlem River Ship Canal down to Battery Park.
When he was 12, one of his mother's clients -- a dean at NYU -- got him admitted to the School of Performing Arts. The red-headed boy was younger and smaller than his classmates, but his musical abilities let him fit in pretty well.
"Next day on your dressing room they've hung a star..."
Sunny's career, while limited to the Carlyle, blossomed. She had her one night in the Café and now two to four nights a week at the piano in Bemelmans Bar with Ludwig's famed murals. She could sing the lyrics to almost any requested song.
When she first started performing in the Bar, Sunny told Bobby, "Buy a bigger notebook, kiddo. A whole new room to work. You'll be booking me more clients than ever."
"That's terrific, Sunny."
Because him mother was in the entertainment business, Bobby got to meet others who played the Carlyle. Everyone from Debby Harry to Woody Allen.
Sunny and Bobby also knew everyone who worked in the hotel. Managers, concierges, cooks, maids, bellmen. Everyone. They were both blessed with an uncanny ability to remember names. It was Mr. Wallace, Mrs. Simpson, Miss Evert. Sunny and Bobby were unfailing polite to everyone from the top brass down to the lowest dishwashers.
The kitchen called up to Bobby frequently, offering breakfast, dinner for two, a new dessert. It was the opposite of room service. And it was free.
Every day after his mother had entertained a guest or two, Bobby handed his favorite desk clerk, Miss Rogers, a sealed envelope. Miss Rogers, a trim gray-haired 62-year old knew exactly what was in the envelope that she placed in the hotel safe -- cash.
Sunny's tax attorney, no fees charged of course, had her declare 75% of the Tip Jar money. The clients she entertained up in her room tipped her a minimum of $500, sometimes a lot more. Not bad for an hour or so's pleasure.
The attorney also negotiated a formal living arrangement with the hotel. Her compensation for performing at the Cafe and Bar was the room -- ILOS. In lieu of salary. He told Sunny and Bobby, "Don't fuck with the IRS. Declare the room."
He smiled at Bobby, "The rest of the cash -- nobody knows from nuttin' right?"
The attorney told them, "Now that you have your room included in the contract, you don't have to worry about management changes. You're set."
Bobby smiled as his mother slipped out of her robe and unbuckled Mr. Granger's belt. Bobby understood that their attorney had time for only a blow job during the day. He'd be back for more one night soon.
Bobby loved watching his beautiful mother making love. When he was much younger, he didn't understand the strange new yearnings he was feeling. Now at 14 he understood them completely.
Sunny had started Bobby out singing in public too. He was slight for his age and looked younger than 8 when he first started belting out songs in Grand Central and Times Square. That worked to his advantage, Bobby too cleared over $100 a pop.
He didn't quite have his mother's voice, not many did. Sunny had gone from an 'achingly pure' Joan Baez soprano to a huskier Diana Krall contralto. Sunny's voice, singing and speaking, radiated sex.
"Let's go on with the show..."
Sunny had always been open with her son. Even if she had had the luxury of a two bedroom suite, she would have still slept with him and told him everything. They had that kind of relationship.
She explained her second career to Bobby, "I like sex. Men love to fuck me. They pay to hear me sing, no reason not to pay for my pussy."
Bobby smiled up adoringly to his mother, "Very smart, Sunny."
Even before he started booking her clients, Bobby could tell whether his mother was expecting company when she got off work. He'd hang her gown up carefully. Place her panties in the laundry, which the hotel picked up every Monday. No charge, but Bobby always gave the bellboy a $20.
He'd follow his mother into the bathroom. If she ran a bubble bath, no visitors that particular night. A shower meant company was on the way.
When her son was younger Sunny was reluctant to send him away while she entertained visitors. She was pleasantly surprised that many of her clients, including some of the few women who wanted her for a change of pace, didn't mind if the polite little boy watched. In fact some of them got off on it.
For the ones who were uncomfortable with an audience, Bobby would take a long bath. Out of courtesy he turned a radio up so the clients wouldn't think he was eavesdropping.
Before she caught on at the Carlyle, Sunny had worked part time giving happy ending massages. She still kept her portable massage table in a closet. As a youngster Bobby didn't have the muscles to knead as deeply as Sunny liked. But he grew stronger, if not that much larger.
Since he now managed his mother's schedule, Bobby knew when there was time to give her an after-work massage. It was impossible to tell which one of them loved it more, mother or son.
Bobby would have the table set up, crisp sheet, candles lit. Sunny would walk out of the shower, a faint scent of fresh flowers, smiling her sexy smile. Only 5' 2" but her erect posture made her seem taller. That and her presence, honed by a lifetime of performing.
Bobby was as proud of his mother's taut body as she was. Small boobs, 34, but full. Pinched waist, curvy little butt, great legs. And that lustrous mane of flaming red hair topping it all. One of the Carlyle accountants, Ruth, trimmed Sunny's red pubic thatch into different shapes: a diamond, an arrow, a heart.
Sunny told Bobby, "My pussy is my best asset, even over my boobs."
Bobby smiled at his mother, "Your pussy belongs on a little girl, Sunny."
He had heard more than one man tell her that and Bobby knew his mother loved hearing it. And he supposed it was true. The few women that he'd seen in bed with Sunny seemed to have comparatively large, even huge pussy lips. His mother had just a whisper of a little slit.
Bobby gave his mother one of two kinds of massage. If a client were scheduled, Sunny would whisper, "Just to the edge, baby, leave me on the brink."
Over the years Bobby had gotten to know his mother's body as well as his own. He became quite skillful at teasing Sunny's clit, using just one finger inside her pussy, taking her to the verge of orgasm.
Depending on who the client was, Bobby would leave to roam the city for a couple of hours. He was just as comfortable at 4 in the morning as 4 in the afternoon. He knew every doorman up and down Fifth and Park and Madison Avenues.
If a client didn't mind an audience, or even requested that he stay, both Sunny and Bobby loved it. Sunny had taught him which clients wanted him to stroke their cocks, or suck them before he guided them into his mother.
They tipped more, those clients.
The second type of massage was when Bobby had Sunny all to himself after she got off work. These were languid, sexy sessions that they both loved. Bobby would finish by licking his mother, something they both could relish for hours.
Bobby didn't have a girlfriend yet, but Sunny knew it was only a matter of time. She sucked her son off once or twice a day. Sunny told him, "I'd like to fuck you, baby, but that would be incest and I'm just not sure I'm ready for that. Yet."
"I understand Sunny."
His mother did get him some pussy. Ruth, the hotel accountant, when she had time after touching up Sunny's pussy. One of the two maids who made up their room every day. Sunny tried to tip her, but she wouldn't hear of it. Bobby was fascinated by her cocoa skin Caribbean accent.
Bobby's favorite was one of Sunny's clients, Madge. Sunny would eat Madge first. Then Madge fucked Bobby. The session ended with Sunny licking her son's semen out of Madge's pussy. Once in a while the idea of Sunny tasting her son's cum got Madge's motor revving so much that she went for another round.
Sunny told her son not to worry about having just 5 inches. She said, "You're not even 5' tall yet. You have plenty of growing to do. Besides, it's nice and fat, I prefer that to length."
Many of Sunny's clients were in their 60s and 70s. Still plenty of desire, but not that much stamina. But Sunny and Bobby were so welcoming, so pleasant, that the older men kept coming back.
Sunny told Bobby, "It doesn't matter if they last just 5 or 10 minutes. $500 or $1,000 is pocket change to them."
Two types of men had shown as much interest in Bobby as Sunny. The older ones, ones who were a little jaded and were looking for something a little different. And the youngest ones who had come of age in a more open environment.
It made up only a small percentage of Sunny's clients but a few men in both age groups like to pull out of Sunny at the last minute and cum in Bobby's mouth. He lay with his head on his mother's tummy to be ready at the right moment.
Sunny told her son, "I can't decide whether to let them fuck you. In a way you'd be a kind of competition for me. But our tips would go up."
"Whatever you think best, Sunny."
Sunny spread the word among her favorite clients to send their sons, or grandsons, to see her. When they were old enough. She told them that the pussy would be on the house for the kid's first time.
And Sunny was guileless when she discussed it with her clients, "If the kid likes me, he may grow up to be a regular client. Expand my base, that's what I'm trying to do."
For those first-timers, the virgins, Bobby always left the hotel, roaming around until his mother called with an all clear. Bobby carried two iPhones, one personal and the other to schedule appointments for Sunny. All of her regular clients had his number. They appreciated his efficiency too. Bobby never got the time and date wrong and he never overbooked Sunny.
Two appointment per day, that was the max. Sunny told Bobby, "I could handle 5 or 6, but the longer they have to wait for an appointment, the more they want me."
"Very smart, Sunny."
The hotel security team knew exactly what Sunny did in her off hours. They ignored it and Bobby always put something extra in their Christmas cards. Everyone who worked at the Carlyle received a generous annual bonus with a handwritten note from Sunny and Bobby. Well, not the top executives, they just got a card and a note.
Sunny told her son, "Some of them probably make as much as I do. No need to give them our hard earned money."
"You're right Sunny."
Bobby actually knew how much his mother made better than she did. He kept meticulous records for Mr. Granger to use when he did Sunny's taxes each year. Sunny rarely earned less than $1,000 a day in cash, and often a lot more.
That, plus her tip jar and the money Bobby earned singing in public, came to a pretty tidy sum. Other than Sunny's clothes, they didn't have much in the way of expenses. No rent, no utilities. A lot of free meals, thanks to the Carlyle kitchen.
But Sunny and Bobby did eat out a lot. It seemed like half the residents of the Upper East Side knew Sunny from her Carlyle performances. She and Bobby often ran into one of Sunny's clients and were unfailing discrete.
Bobby loved being seen with his mother, a real head turner.
Bobby took his booking responsibilities seriously. He learned which clients needed daytime appointments and which preferred to visit after Sunny got off work.
Bobby tried to keep his mother's mornings free, that's when she caught up on her sleep. One client in the afternoon, one after work, that was the best.
Sunny had roamed all over the city starting when she was 8 or so. So both she and her son knew it well. They loved having lunch around 3 at new places. They took the train to hipster Brooklyn, the Ferry to conservative Staten Island. Another boat to Long Island City. Car service to The Bronx.
Sunny and Bobby avoided touristy places like Arthur Avenue in the Bronx, Times Square, Midtown in general.
Because of her dual careers, they couldn't go out much at night. Even when she wasn't singing, Bobby would usually have her booked to entertain a guest. Or two.
Sunny told her son, "More than two, ask me ahead of time. I like an occasional gang bang, but I need to psych myself up. No, make it three. If it's more than three, ask me."
"Okay Sunny. You do real well with three, I don't know how you can concentrate on that many."
Sunny smiled, "I am good at that. My pussy's on automatic. I concentrate on flexing my butt and sucking cock."
"So it's more like two clients. Mentally."
She smiled wider, "Mentally, yes. But not financially."
Sunny and Bobby had learned that many men were happy to pay more when multiple partners were involved. The same was true when it was a husband and wife.
Sunny and Bobby loved their private time with each other. Roaming the city they loved, holding hands, finding new restaurants. Bobby was so pleased to be seen with his mother.