Chapter 6: Old Friends and New Encounters

Samantha looked at her Bulgari Serpenti Tubogas Lady watch, which her next client had paid over $50,000 for as a gift. She was three minutes early, exactly as she had planned. She knocked at the door of room 3419 at the Four Seasons.

Samantha was back in operation full-time again to satisfy the needs of some of her most important clients and keep her escort business from losing long-term clients. The man she was going to see again was one of them. A few seconds later, an old, smaller, white-haired man in an impeccable, expensive suit opened the door.

Harry Bridgewater smiled at what he was seeing. Samantha was dressed in an expensive, black Dolce & Gabbana bustier-style, sheer midi dress that hugged her body and highlighted every curve. Her skin between her neck and breasts was bare except for the thin spaghetti straps. Her stylish black open-toed Jimmy Choo sandals with 4-inch heels lifted her ass and defined her curvy legs to magnify her backside. She was carrying a stylish and extravagant Hermès Birkin handbag to finish the ensemble.

The entire outfit had cost Harry around $100,000 in total. Harry had given her the dress because it was his favorite, and she had worn it for their last few encounters. He loved how it displayed her incredible body. The shoes and bag were two of the many “gifts” he’d given her each time he met her. They were some of the most exclusive handbags, shoes, jewelry, and accessories he had given her over the last nine years. She had dozens of gifts in the third bedroom of her condo, where she stored them, using them so seldom that she would let the other girls borrow them if they needed to display wealth or that “certain look” for a date. Men would usually know little, but women at these affairs instantly recognized the labels and were impressed. The men took notice of the other trophy women primping his girl and her expensive accessories. The client would feel important without knowing why.

“Hello, Harry,” she purred as she stepped inside the suite and gave him a warm, sincere hug, followed by a deep kiss. Her breasts crushed into his chest, causing Harry to breathe shallowly. In the Jimmy Choo heels, she was four inches taller than he, so it was she who bent over so their lips could touch.

“Oh, Samantha, my dear, it is so wonderful to see you again. While I love our phone encounters, there is no substitute for hugging and touching what is before me in living color. Stand back for a moment, and please, just let me soak in your magnificent beauty.” Samantha retreated a step, tipping her head a bit with a sassy smile. His heart melted watching her. Harry was one of the good ones, a client whom she had truly come to like as a friend.

“Do we have all evening and tomorrow morning, dear?” Harry was always a gentleman, never assuming anything was expected. For Samantha, he was one of the men to whom she would give what he wanted, except for marriage. He had already asked her, twice in fact.

“Of course, baby. I’m all yours. Now, do you want to go to dinner or have a quick roll in the hay first?” Her voice was sultry and inquisitive, speaking each word with warmth.

“Let’s go to dinner first. I truly enjoy showing you off to the other restaurant patrons.” Samantha giggled at the comment. She liked to be shown off, too.

Samantha put her bag, containing another change of clothes, her lingerie, her personal items, and a few sex toys Harry appreciated when he desired her to perform wicked acts, down next to the bed. Together, with his hand wrapped around her lower waist, they walked out the door and to the elevator.

Harry was a unique man with an uncommon background. He didn’t like interacting socially if he could help it, even though it was often required in his business world. Ruthie was the love and centerpiece of Harry’s life. They married upon graduating from college, and together they had one daughter. Sadly, she had died tragically when she was 13. The hole in their hearts never completely healed. Harry found his primary comfort in being held by his naked Ruthie while in bed together. What started out as an infrequent thing became a regular occurrence. Harry lived for any time he could get to be alone and enjoy the love of his life, curled up into her loving breasts.

In the early days, Harry was a ruthless businessman and was cursed by many other important people of his era. He hid his reaction to the attacks, but inside, they destroyed his confidence and desire to interact with others. What saved him was going home to Ruthie, where she could soothe his conscience and help rebuild his confidence. After a particularly rough day, Harry would lie naked on the bed with Ruthie and act out his frustrations like a child. He would cry, scream, and pout, curling up into Ruthie’s naked, giant breasts. His head would swirl around into them, begging for forgiveness and mercy. She would mother him, telling him everything would be okay and that he was twice the man of anyone else. Harry often used Ruthie’s sweet boobs to ease his soul, being swaddled into her, providing him the only true safe harbor from the exterior pressures of his complex business life. When the world beat him down, Ruthie provided renewal in her unique, special way.

Nothing could substitute for the haven Ruthie provided him throughout their married life. This simple pattern of internal renewal gave Harry the strength and focus to become extremely rich. Over time, he owned multiple businesses that made him millions, then tens of millions, and now hundreds of millions each year.

After Ruthie died from cancer, Harry turned inward and kept his sorrow to himself. Friends and associates tried to get him out and about again, often setting him up with smart, beautiful, successful ladies, usually middle-aged but frequently 10 to 20 years younger than his 60 years. No matter how hard he tried, from a church woman to a gold digger to an escort, he could never find a woman with whom he could recreate that feeling he had with his Ruthie.

A bit over a year after Ruthie passed, Harry called an escort service to find some feminine companionship as a change of pace. After talking with other well-to-do friends, he got a referral from one of them. He instantly contacted Samantha’s Escort Service to set an appointment. He found it was impossible for a new client to simply date an escort from SES. Early that evening, the first step of being tested happened with a visit from Sharon, who expedited the results so Harry could schedule his date the next morning. After reviewing the videos of each girl, the appointment was set with Harry’s choice after seeing all the girls.

That was Taylor. The blonde Aussie with a beautiful smile and massive tits fascinated him. Her accent was intoxicating to him. Taylor’s video screamed of being all-woman, unlike some immature girls in their early twenties, who had great hard bodies and beautiful faces but no people skills or, seemingly, knowledge of life. Harry much preferred brains to blowjobs at his age. Although a naked blowjob was always pretty great.

A few hours before the date, Taylor had an emergency and had to cancel with Harry. Samantha was finished for the evening, having already had two dates that afternoon and early evening, so after a heads-up from DJ, she took Harry on at the last minute. Harry and Samantha weren’t even supposed to ever meet. The flukish turn of events said otherwise.

Harry was different from most men Sam was used to. He was kind and wise, not pushy, but not a prude, either.

Sam was different from most women Harry was used to. She was kind and personable and intelligent, warm and inviting, and had a naughty streak, too. Oh, and her breasts had the same size, shape, and softness as his dear Ruthie’s.

That first interaction was memorable and set the stage for their future relationship. When Samantha arrived at the upscale hotel and met Harry in the lobby for the first time, she gave him her standard tit-crushing hug. Harry not only liked it, but it jarred some memories from long ago. He couldn’t figure out exactly what it was, but it was infinitely pleasant.

Harry suddenly lost his appetite, or at least for eating food. Skipping dinner and going straight to the suite, he wanted to be with this new, beautiful, blue-eyed brunette as soon as possible.

They were nude and lying on the bed, kissing and fondling each other in less than 15 minutes. Harry hadn’t experienced such warm, inviting breasts since his sweet Ruthie passed nearly a year before. Sam realized Harry liked to be pulled up and his head held between large breasts, and she was happy to oblige him in his desire.

“There, there, Harry, you’re safe now. Everything is going to be alright. Let me hold you. Just nuzzle in and enjoy the warmth of my bosom,” Samantha purred as she stroked his temple. Harry’s mind took him back in time, to when life was perfect and Ruthie was his safety zone, his process of renewal. With Samantha, his safety zone was back.

Samantha understood Harry’s fetish and provided a solution for his unique needs. In Harry’s mind, Samantha, for a few short hours, was Ruthie. And now, for over nine years, their relationship has remained the cornerstone of Harry’s life.

Samantha, having freshened up in the suite bathroom before they went to dinner, walked out and into Harry’s arms. Together, they walked out through the suite’s door and into the elevator. Arriving at the restaurant, they met the impeccably dressed hostess who knew the white-haired regular guest and his date from frequent stays. In addition to having a great bar, Goldfitch’s was a destination restaurant, run by a world-class chef. Every ingredient was organically produced and locally sourced. The seafood dishes were both simple, as in the case of grilled fresh king salmon flown in from Alaska, or complex and delicate, like the Kumamoto oysters from Northern California or the Pacific Dungeness Crab Louis salad.

Harry smiled as he saw the other patrons stare at his gorgeous companion. The hostess knew from past visits that Harry liked to show off his woman. So she decided to lead them to their table slowly and deliberately, stopping for a second or two to continue their conversation while pointing out a unique aspect of their restaurant so others had the opportunity to stare at the beautiful brunette up close. The hostess led them on the most indirect path so more diners could witness the beauty walking with him. Most wondered if the gorgeous, cobalt-blue-eyed brunette was his daughter or his latest trophy wife. Nobody thought she was his because of the money he paid her. She looked too classy and sophisticated. Harry smiled as he watched the other patrons stop eating once they saw her and stare. This was the reaction he sought. It was exactly what he wanted, to show off his beauty.

After the long walk across the room was complete and they arrived at their table, the hostess extended her arm. “Will this be acceptable, sir?” she queried.

“Perfect, my dear. Thank you.”

The hostess pulled out her chair, and after Sam sat down, Harry took over and helped her push it in. He sat across from her and looked into her eyes.

“God, I love showing you off,” he quietly murmured.

Samantha giggled, the glance of her deep-blue eyes locked into his. The waiter poured their first glasses of expensive champagne, witnessing their intense feelings toward each other.

“Of course you do. Truth be known, Harry, I like it when you do. I put a lot of work into keeping this body looking the way it does and showing it off to strangers when you are at my side. It thrills me to no end.” Her comment was sincere, as sincere as a whore could be.

The couple enjoyed their incredible food as the evening progressed. Samantha, having been Harry’s paid paramour for over nine years, knew what he wanted and what didn’t interest him. She laughed at his jokes, staring into his eyes with deep interest when he described an event he had experienced. As she cleared their plates, the waitress asked if they wanted dessert or an after-dinner drink. Sam, knowing the answer, responded for both of them, and after bringing their tab and Harry signing it to be charged to his room, waited for Harry to pull her chair so they could go arm-in-arm to the elevators. Both laughed as the remaining patrons stared at them as plainly as when they entered.

Harry held his key card to the keypad, and the sound beeped as the light turned green. He opened the door and waved his lover into the suite. He spun her around with more force than Samantha expected and pulled her into him, kissing her deeply. Immediately, he turned emotional.

“You are the light in my day, Samantha. It’s so much more than your incredible feminine beauty and grace. It’s that warm, loving smile, that heart-melting giggle of yours. Yes, I love to see you nude and make love to you if my flesh allows me, but even hearing your voice or seeing you on FaceTime if I can’t be physically with you gives me a similar feeling, as limiting as it is. We’ve been doing too much of that lately, and I am so happy that now we are together in the flesh. You are so enchanting when you lie there nude as we talk about anything and everything. I so love it when you masturbate and suck me off to an amazing climax, finishing off after one of your spellbinding stripteases.”

Samantha reached in and gave Harry a slow, smoldering kiss. She put her entire body into it, touching her naked skin with his. It was a contrast in age, sex, and health. It was the diminutive, white-haired man who was the centerpiece of her attention. Harry gave Samantha nothing but love and respect, which, until then, he had saved only for his late wife, Ruthie.

“Your body is perfect, and the aura around you is even better. When I am with you, Sam, I feel younger. I feel alive, unlike any other time or place. It’s you, dear. You are singular on this entire planet. Yes, you are truly one of a kind. Your power to understand and heal me is rare and beautiful. I am so grateful you allow me to be one of your special clients. I live to just converse with you, to be in your presence. It’s the only time I feel like I did when my dear Ruthie was still alive, over ten years ago. To be able to have you as part of my life is the main thing this old man lives for.”

Samantha had had trouble getting Harry hard for the last year or so, but she felt that this night could be special. Being taller than him, it was easy to pull him into her maternal breasts, giving him warmth and a sense of shelter. As she pulled him into her, he snuggled his head between her globes and relaxed, like he was home in his nest. Sam stroked his scalp, whispering sweet nothings into his ear. Harry’s eyes closed as if he were being hypnotized, enjoying the sweet love Sam was feeding him.

While stroking his temple with one hand, she quietly guided her other hand down to his dick and started to gently fondle it.