The Siren Sisters Pt. 03

Teddy was born in Nawlans as he called it, the youngest of 6, he never excelled at academics or sports having just barely graduated high school. After school he worked a number of odd jobs, day labor, waiting tables, he finally ended up in sales. Weather trouble in the area had the real estate market booming. He flipped foreclosed property for a year or two which gave him a nest egg so he could pursue his true passion, women. His big dick and charm ensured he was well equipped for that, and it beat working for a living.

He bedded a series of wealthy widows. Nothing illegal just rent money and gifts of clothes and jewelry. Eventually, one of them took him on a cruise as her companion. He quickly realized that there was fruit to be picked in this environment so after the cruise he left his patron and booked a couple of trips to test the waters. Things went well but his flamboyant personal style drew the attention of management, so reluctantly he had to cool it down a bit.

One day, a representative of the lines asked him if he would be able to accompany a lonely, VIP widow to a ball. Once he signed an NDA and swore to be discreet, things progressed well and his new 'employers' explained the Sirens and told him that they were trying to offer passengers more options. He wasn't too keen on gay for pay but Teddy was nothing if not adaptable and a survivor.

Most of his duties centered on making nice to well-heeled and usually lovely older women. He drew the occasional overweight dowager, but he thoroughly enjoyed the few M-F-M threesomes he had been involved in. Even after the house cut, he was making more than he had been on his own and the accommodations and perks were much nicer.

Sid listened with interest, "Well we have at least two things in common. I started out as a freelancer, Larry and Jade brought me in. Also, we are both whores. I am Bi so my girl on girl gigs are good for me especially when Jade is involved. A word of caution about Jade. She reads people amazingly well, don't ever lie to her or try to bullshit her. She will know."

"Roger that. My place or yours?"

"Mine, let's go!" Sid signed the bill, adding a nice tip for sweet attentive Alice and led Teddy off by the hand.

Alice was surprised at the generous tip and hurried after Sid to thank her with a hug. Sid told her, "Don't mention it, you are good at your job and deserve some recognition."

Sid noticed Ling's door closed and heard her meditation music, so she put her finger over Teddy's lips and led him to her room. She kicked off her shoes. Stripping, she walked into her bathroom to start the spa shower and get it warmed up. She invited Teddy in with a crooked finger and undressed him. She was pleased to see that his above average cock was already hard. She noticed that his eyes were locked onto her shaved pussy as she pulled him into the warm water, and they started a rather spirited make out session. Sid pulled back his foreskin and soaped up his head and shaft, she diverted to his ass crack because he seemed to be enjoying the hand job a little too much. She was trying to pace him. She wanted him in her mouth and pussy.

Teddy groaned, "This is a nice change, I usually have to do all the work."

"Patience. I will be putting you through your paces tonight, enjoy a little pampering while it is on offer."

Teddy returned the intimate washing favor, and they slipped out to dry. Sid fell on her bed, legs spread wide and commanded. "Eat this pussy you stud." Teddy dove in with no warmup. Which prompted Sid to make a mental note. We will need to teach this kid how to tease. He did get the job done and he did get Sid off. Once she came down, she decided to give him the taste test. The copious amount of slime he generated while eating her was very good. Vintage under 30 cock. She then asked. "How many pops can you do?"

"Normally at least 3. For a beauty like you probably 4 maybe 5."

Sid giggled, "We will see about that." For his part, Teddy enjoyed watching his white prick disappear into her cocoa lips. Her lovely plump lips were tightly encircling his cock. As her mouth drew back and plunged back down, he enjoyed how his prick glistened with her saliva. Sid is so much juicier than my normal older partners, everything she does feels good. Is that natural talent or Jade being her mentor he wondered. She went deeper with each stroke and made guttural almost gagging sounds as she took him deep into her throat. While she worked him, he reached down to feel the wetness of her pussy increasing so he could lube up two fingers and insert them deep into her dripping hole. Finding her g-spot he felt her body stiffen at the dual pleasure. Watching his white cock and digits entering the delicious openings in her rich brown body, started to cause his cock to swell and his ball sack to tighten up.

Recognizing the signs of his impending orgasm, Sid continued to pleasure him but concentrated on her own pleasure, bucking her hips against his hand and relishing the feel of his big, beautiful cock in her mouth, so she could get her own orgasm in before he blew. Teddy sensed what she wanted so he held back a bit on bursting into her mouth and worked his thumb over her clit so he could deliver as promised. Sid moaned around his dick, so he knew he had hit the right buttons on her eager body. She buried his cock all the way into the back of her throat pressing her nose against the base so she could breathe in the maleness exuding from the glands in his erogenous zones. Arching her shoulders and back she shivered and moaned out her orgasm. Not only did her cunt spasm, but her throat did as well. Teddy let go and started shooting ropes of his white jizz down her throat. Sid drained him.

"This takes me back to fond memories. My first time was with a negro preacher's daughter, Pearl. That sweet little bitch fucked my brains out and ran me all over the parish."

"Is that why you sound so dumb, redneck? Because your brains were fucked out by a proud black sister?"

"Whoa. Whoa. Darlin' I meant no offense. Where are you from?"

"Outside Detroit. Sorry to be so touchy, apology accepted. Sid pushed him over on his back and sat on his face while she readied him for the ride of his life, she hoped. "You eat pussy good. That is one of the best apologies I have had from a dumb white boy." Teddy laughed into her pussy. He was hard again by the time she squirted in his face. So, she repositioned and lubed up his spear on her fat juicy lips doing her best stripper slide working him to a frenzy running her wet cleft all up and down the length of his prick while she dripped on him in anticipation.

He made her come in missionary, doggy and gave her a 'Hum job'. While eating her pussy again, he hummed the base riff for a rock song and got her off. To her amazement he didn't seem to mind eating her with his own spunk dripping from her hole. For their final act of their night of debauchery, Sid got him hard one final time with her mouth and once again in doggy commanded "Teddy, get in here and stick it in my dirty fucking asshole."

Teddy bent down for a closer look. "Not dirty at all, smells like coconut. Tastes good." As he rimmed her and then stuck his tongue up her ass. Sid was willing and eager, so Teddy was able to lube his tool in her cunt with a combination of her drippings and his spunk.

He easily slipped his helmet past the guardians of her forbidden hole and once in, Sid confidently slid back on the cock she was learning to love. Once she was halfway down she asked, "Teddy, let me drive for a bit, once I am ready for a good fucking I will let you know. This will require all of your will power but will help me find my rhythm and get off with you."

Teddy grunted his consent and ran his hands along the small of her back giving her a light touch massage instead of grabbing her hips and pounding into her. Sid moaned, "Oh yes that feels so nice, keep doing that. You are pretty sweet for a dumb redneck." As Sid bounced, she rapidly reached the point where she was close, and as things progressed she pushed back deeper and deeper until he was balls deep in her fine black ass. For his part Teddy was visualizing his prick deep in her ass and trying to estimate where in her hips his cock head was getting to. Sid's orgasmic energy built up to the point of bursting and she groaned, "Now's the time. Fuck my ass, cum in my ass, I need it!"

Teddy grabbed her hips and plunged his thick ready cock in and out of her pulling almost out before thrusting back in until his thighs slapped against hers. "Dumb redneck, eh? This dumb redneck is going to make you cum, black girl and fill you again with his white boy goo."

As the exuberant hammering continued, Sid drifted into the euphoria of an intense anal orgasm. She moaned and panted. This feels so good. I love this redneck. Her legs started to twitch, and she shivered as he rammed her ass past the point of no return. One final thrust pushed her out of the plane, and she was in freefall. Her ass spasmed and her pelvic floor muscles started to milk him. Teddy couldn't hold on and dumped his final load into her thirsty butt hole. They both groaned, "Oh, God. Cumming. Cumming."

They collapsed giggling, Sid complimented Teddy. "Well done!" You have my vote." As she totaled up the final score Sid 7 - Teddy 4 she smiled. Sid fell asleep on Teddy, her arm draped across his chest.

Ling.

Ling and Rose stopped at the Spa to pick up some custom padded foam blocks and bolsters. "We use these for some of our bigger breasted clients when they get a massage. I have heard it can be uncomfortable lying on big breasts for too long, we even have a massage table with a breast gap that some women enjoy."

Ling ran a warm bath with scented oil added and they soaked while enjoying another drink and some relaxing meditation music. While in the tub Ling massaged Rose's temples and examined her flaming red hair with great interest. "Tell me about your home and your life."

Rose grew up in Fort William, a small city in north Scotland in the shadow of Ben Nevis, the tallest mountain in the British Isles. She was an only child but had a few cousins to play with when she was young. Her parents wanted more and her interest in sex cemented as she listened to her parents practicing, trying to give her a sibling. She had more than her fair share of the local lads before moving to London to study acting and avoid being dubbed the village bicycle. Small stage roles and a few TV commercials came her way, London was like a candy store for her, and her tits were a currency that few men could resist.

As she continued her tale, she slipped under the water, so her breasts were free floating. Ling's fingers were drawn from Rose's temples to the lovely smooth orbs with swollen grapes at the tips that were floating invitingly in front of her. As she matured into her 20s Rose's sexual and sensual appetites grew, almost beyond her control. But something was missing, being an only child, she was rather selfish and had never learned to share. She shared her body but only to an extent. Her longest relationship only spanned months, at best a half a year. She had to admit to her therapist that she was a shallow and selfish bitch. Her therapist suggested that she needed to work on empathy, love isn't selfish. Love must be given.

Her father had died years before. When her mother got cancer, she moved back home to care for her. After all, her mother had no one else, no other children, no living siblings. At first it was difficult, why was she giving up her life for her mother? The easy answer was she was the woman who gave her life. But... she still struggled. She made a few friends at the hospice. One woman her age, Lily was there with her dad almost every day, they became fast friends.

One morning Lily asked Rose to look in on her dad later in the day, I have a date this afternoon, after all a girl must pay rent. "A date pays the rent?" Rose asked, wanting to know more.

"It does if you are a high-priced call girl." Rose did as her friend asked. In fact, she enjoyed it. When she went to his room to see him, Lily's dad Sam broke into a huge smile. Hello Rosie, you are so sweet to visit an old sod like me. For the first time in her life Rose understood the old adage 'it is better to give than to receive'. The next morning, she visited her mother but snuck a peek around the doorframe first, her mother was obviously in pain and uncomfortable. Rose cleared her throat and her mother looked over, the mask of pain falling away from her face to be replaced by a look of pure joy. "Rose?"

"I am here Mommy, are you alright?"

"Can you get the nurse? My head hurts so bad I can hardly see." These two small incidents changed the selfish, shallow girl forever. Once mom was feeling better, she went to see Sam, not because she wanted anything other than to see him smile. Lily was there and she thanked Rose for looking in on Sam.

Rose asked Lily if she could talk about her work. "We can talk here, Daddy knows."

They talked about what it was like to have sex for money. Why men would pay a woman for sex. About how sometimes it was more about time or a human connection and other needs. Lily took on Rose as her protege. Rose excelled at the job, after all she was an actress. Even though she was compensated well financially Rose loved her new career for many reasons.

While Rose was reminiscing, Ling was softly talking her through breathing exercises. In. Out. In. Out and synching up her own breathing with Rose. Ling gently massaged Rose's breasts. Sides, nipples. Ling's fingertips were like magic wands in a Harry Potter story, gently teasing out the deep memories. Rose sighed contentedly.

After both their parents died, Rose made the hard decision to leave Lily and return to London. Once she was back, she tried out for acting roles, but it is a fickle business, and a girl needs to eat and pay rent, so she continued escorting. A man named Dirk arranged a date with her via e-mail. One of her old lovers and biggest regrets had been named Dirk.

Rose agreed to meet this Dirk. She shared a small sparsely furnished flat with another escort who she occasionally did doubles with and that was where they were meeting on a Thursday morning. When she opened the door, she gasped, it was the Dirk she had known. Her Dirk. He was in the movie business, and they had dated for 6 months the year before her mother got sick. She had hoped for more but at that time she was her old selfish woman. They had talked about the future, but he couldn't commit largely because she was too selfish, and he worried about disaster down the road. Eventually, he moved on and then she did too.

On meeting again, they fell into each other's arms, like the old lovers that they were and kissed passionately. Dirk looked great and his smell got her wet. She caressed his cheek and helped him off with his coat.

"Rose, it's great to see you. How have you been? How is your mom?"

"Mom passed about 6 months ago, that was about the time I started escorting. A friend of mine showed me the ropes. Since I was always too selfish to sustain a long-term relationship this was an excellent distraction. Now I have the skills to pass any casting couch test."

"So sorry about our mom. I wish I had known. I would have reached out sooner maybe reconnected before you took this path." He handed her a plain white envelope that held her fee.

"Reconnect. Yes. We are together now. It's never too late they say." Dirk frowned as he reached up to fondle her breasts. I wonder how many other men have fondled these and been in her. How many sweaty little toads.

Rose saw a change in his eyes and then said, "Right then, Let's get down to business." She took Dirk on a tour of her body and new skills. Pampering him like no one ever had before.

Dirk resisted any pillow talk and at the end of the hour he dressed and left. On his way out the door he suggested that maybe they could do this again sometime. Rose was crushed. She had been almost elated when she first saw him, maybe... But his change in attitude shattered any dreams she might have had about becoming a wife and maybe a mother. She was a slut, a slag. Only good for a quick fuck. Her fears solidified when Dirk texted her a few days later. "I loved you once. But now that you are a Prostitute, I can't. I just can't. Not with a whore." Rose wept and drank to kill the pain. She went on a weeklong bender and missed an important audition for a role that would have been perfect for her. Tears were running down Rose's cheeks as she shared this with Ling.

That was 2 months ago. Once she sobered up, she threw herself into auditions, escorting, some volunteer work at a local hospice, anything to keep busy. The role that she had wanted was already cast but she auditioned for others. One of her regular clients was a Scandinavian businessman, he was in town trying to find solutions to the chaos he feared Brexit would bring. His second visit with her in a week was a 3-hour lazy afternoon.

Their last 30 minutes was pillow talk that Rose loved but usually didn't get. "Sven, I am glad you booked so much time. It had been so nice spending time with a gentleman who appreciates a woman. I have bad news though. I may be leaving London soon." Rose said sadly.

"Why? Is there anything wrong?"

"Yes." Openly weeping as she was now doing with Ling, she told him about Dirk. She wasn't going to give up her escorting. It wouldn't make a difference if she did, she was damaged goods. Besides, her regulars treated her well and she was a woman and needed the closeness she got from working. It was too painful to remain in London as her acting career seemed to have stalled and she ran the risk of running into too many people she knew from her old life. Maybe she would go back to Scotland or try settling in Manchester."

Sven looked concerned. "Maybe you would consider another option that would provide you with a better situation. Don't do anything rash. I have a friend who owns a cruise line. They offer courtesan services for VIP clients. Lars treats his employees like family. Is that something you might consider? If you got a position, I would know where to find you when I wanted you."

A couple days later she got a call from Kat. "Is this redhead Rose? Sven asked me to speak to you. We are currently hiring, and he thought you might be interested in a position with us. Can we fly you out for an interview? All expenses paid of course."

"That would be lovely. Sven is such a dear. My schedule is very flexible. How soon do you want to see me?

"If you don't mind, I can fly you into Havana on Wednesday the 11th, put you up in a nice hotel overnight and we can pick you up when we dock the next day. It would be great if you could give us a week to fully evaluate you and make sure you are good fit."

"That works, my cycle should be ending on the 10th and I start my pills on the 11th."

Kat said cheerily, can I have your full name, DL number, email address, etc.? We will send you an e-ticket, itinerary and any other info you need."

And with a sigh Rose said, "So here I am." Brushing away her tears.

Ling had been gently stroking the sides of Rose's massive mammaries as they floated in the water, and occasionally brushing a nipple.

Ling said, "Let's dry off and I will give you a sensual massage. On her in-room massage table Ling built a small platform for Rose's torso about 2.5 inches tall out of a bed pillow and a bolster. Another bolster just below the face hole would support her collar bone. When Rose lay face down, her tits fit into the space between the bolsters. They bulged out the sides, but they were not badly squashed. With the addition of a folded towel to elevate Rose's forehead her spine was relatively straight, and she was comfortable.