Bill's Big Boss

"Oh I do love a good cruise, but Annie and Frank both insisted I stay here and treat you to a professional massage this morning," Chloe said. "So no rush, but when you are finished eating, shower and then head over to my studio upstairs. I have you booked for a 90 minute full body massage and I won't take no for an answer."

"That sounds fantastic. I love massages," Bill said. "I would feel a little weird asking you to do one though. You are on vacation too, right?" Bill said hesitantly, not quite believing he would say anything that could jeopardize having this beautiful woman shower him with physical attention for an hour.

"Oh honey, my life is a vacation," Chloe replied. "That Frank lets me practice massage on his friends sometimes is hardly an imposition. Finish up and eat, shower, and then use one of the robes in your room. Walk over to my studio and knock. I'll be ready for you."

Bill couldn't believe his luck. He tried not to seem too eager so he savored his croissant and coffee as best he could before heading upstairs to shower. After he was done, as instructed, he put on only a robe before walking over to Chloe's massage studio on the second floor.

Bill knocked when he reached the door, eliciting a bubbly, "Come in!" from Chloe inside. She was still dressed in her white yoga pants and crop top, which firmly gripped her ample chest and curvy ass without exposing them. The shades were drawn and the room would have been pitch dark but for some scented candles that already had Bill falling asleep and there was soft meditation music playing.

"Here is a towel. I am going to step out for your privacy. Please remove your robe and lay face down on the table with the towel covering your midsection. I'll be back in a minute," Chloe instructed.

Bill waited till Chloe closed the door behind her before he removed his robe, placing it on a hook on the door, and walked naked to the table before lying face down, placing the towel over his butt. He felt a little exposed, but the lighting and music had him relaxed already.

About a minute later Chloe knocked and entered without really waiting for a response. "I am going to be using medium pressure," she said as Bill could already hear her rubbing oil in her hands. "Let me know if you want more or less pressure. Also, you're not allergic to coconut oil are you?"

"No, coconut oil sounds great," Bill replied.

Chloe's hands felt warm, wet, and wonderful as they began to methodically loosen up the muscles on Bill's back. She worked both hands down his spine, starting from his neck, before flaring out and working his lower back muscles just above his butt. Then she used her forearm, again starting at the top of his back, to smooth out his muscles, first working his left side then his right.

Next she worked his neck and shoulders with her hands, taking the time to knead out any knots she found, again working his left side then his right. After his shoulders she moved to the length of the back, again stopping to focus on knots when she found them, again starting with the left and then the right. She had a system. She had done this before. And she was very good at it.

Bill enjoyed Chloe's work on his upper back, then lower back, then feet. Chloe then asked him to turn over, assuring him she would hold his towel to maintain his privacy. Bill felt a little nervous, but Chloe had earned his trust with her professionalism so he dutifully turned over, the towel safely covering his manhood the entire time.

Chloe again worked his neck, lifting it up and stretching it out as her fingers worked his skin. She then lowered his head back on the table and began tracing his face with one finger at a time. She then massaged his temples before giving his full scalp a thorough rub down. Now inundated with coconut oil, his hair was going to need another wash.

Finally, Chloe moved to the other end of the table and started working on his feet, first left then right. She then began working on his hamstrings before announcing, "You feel a little tight here. I am going to get up on the table and stretch you out a bit, is that ok?"

She could have asked for a million dollars and Bill would have said yes, but he did manage to mumble, "Yes please."

Chloe then folded his knee up so that it was bent, and pushed herself up onto the table as she rotated his leg stretching his hamstring muscle but also his inner thigh which on some level Bill knew must have exposed his manhood to her.

But Chloe said nothing, finishing three rotations before replacing his leg back down on the table and moving on to his other leg. When she had done both legs, she moved back behind his head and began massaging Bill's pecs. "You are doing so great," Chloe said. "I can tell you are very relaxed. We are almost done, but I need you to really relax for this next part, OK? Can you do that for me?"

"Anything," Bill murmured in bliss.

Chloe then slowly moved her hands down past his pecs, past his stomach, and under the towel. But she didn't stop there. She continued past his rapidly hardening penis, until she was cupping his balls. He tensed a little, but Chloe softly reassured him, "Buddhist monks often massage their own balls," Chloe explained, as her cupping changed into each of her hands gently massaging his balls. "It is proven to help circulation throughout your body and improve your focus."

Bill could definitely feel the circulation in his penis improving, which had now turned the towel into a tent. He should have been worried that his boss's wife was touching his genitals, but he was already so relaxed and what she was doing felt amazing. Her soft delicate fingers methodically applying pressure to each ball. He was in heaven.

"Almost done," Chloe whispered, as one of her hands went back to cupping both of his balls, while the other pushed away the towel entirely and firmly gripped his cock.

Bill knew this was coming, but he still tensed when he felt her hands wrap around his manhood. "Relax, Bill. Let it happen. This is Frank's gift to you. He wants you to be as happy as possible."

With that assurance, Bill fully relaxed and Chloe began working her hand up and down his shaft. She worked his dick slowly at first, moving her land the full length of Bill's member, all the way down to the base of the shaft and then up so that her top fingers covered the top of his penis.

As Bill began moaning with pleasure, Chloe picked up her pace, shortening the length of her strokes so that the most friction was applied just to the head of his penis. She then lowered her cotton constrained chest onto his forehead. The warmth and weight of her perfect tits resting on his head combined with her perfectly manicured hands working his cock, was too much. Bill's balls tensed and pulled upwards as his first stream of cum shot out.

Chloe slowed her pace but continued to stroke him as rope after rope of cum flowed through his balls up his shaft and out onto his chest. She even continued to stroke him after he stopped cumming, his shaft still twitching in her hands. Not until his manhood began to deflate did she take both hands and begin to massage his own cum into his skin.

"You were a very good boy Bill," Chloe said in her bubbly voice. "The perfect client. Again, Frank won't be mad. He knows. This massage was his gift to you. I am going to step out, you can lay here as long as you want. There is a shower behind that door in the corner to get the oil out of your hair."

Bill's head was swimming. What just happened? His wife's gorgeous boss had just jacked him off. Did he just cheat on his wife? Should she tell her? Would Chloe? Would Frank?

As he tried to compose his thoughts during a long shower, Bill came to the conclusion that neither Chloe or Frank was going to tell Annie about his happy ending. He was starting a new job with Frank. Why would Frank want to make his life difficult? Guilt aside, that was an amazing massage. He felt fantastic. He should relax and go with that feeling.

After he finished showering and dressing, Bill headed downstairs to the kitchen just in time to see Frank and Annie walking in from the dock. Chloe was already outside walking toward them and she greeted Frank with a big hug around his neck, which he turned into a deep kiss leaning her backwards and firmly gripping her ass. Unless he was mistaken, he thought Annie looked a little jealous.

But her mood improved when she saw him and bounded over for her own hug and kiss. "Oh baby Frank's boat is amazing!" she beamed. "It's the biggest sailboat I've ever been on and he even let me drive it."

"Steer the boat," Frank corrected with a smile. "And she's a very fast learner, Bill. She took to it like a natural, tacking and jibing like a pro. I may have to get you both memberships at the yacht club."

"Oh no I don't think I could sail somebody else's boat Fank," Annie cooed. "I'd be too nervous. You were such a good instructor and you made it look so easy," Annie continued, flashing Frank a wink that Bill caught. And then for the first time, Bill noticed that Annie was wearing a swimsuit he had never seen before. It was a bikini! The bottom was high waisted giving her stomach some helpful support, but the top was a halter wrap cross with a tie in the back that, at best, covered half of her ample bosom. She looked very sexy. And even though he had just cum half an hour earlier, his dick got rock hard just looking at her.

"When did you get that new suit? I love it," Bill said.

"Oh this is another gift from Chloe. She bought it for me yesterday. I was embarrassed to try it, but Frank insisted. I'm glad you like it. I don't think I could wear it back home, but I just feel so much more relaxed here," Annie said.

"Well I sure hope I can convince you to wear it back at the neighborhood pool," Bill said. "I'd feel like the luckiest guy there."

"You already are the luckiest guy," Annie winked back, giving him a peck on the cheek.

During lunch, Chloe announced that she was going to take Annie shopping again and Frank offered to let Bill join him for a workout in the gym. Bill had never been a gym rat. It was always too intimidating to know what equipment to use. But Frank offered to show him one of his workout routines.

After a grueling hour with free weights, Frank invited Bill to join him in his sauna. Bill was embarrassed to strip naked, but after Frank entered the sauna in just a towel, Bill followed suit. After sitting down on one of the benches and unwrapping his towel, however, he immediately regretted it.

Frank sat across from him in the small space of the sauna with his colossal cock hanging between his legs. Bill's average package paled in comparison.

"That pain you feel is good," Frank said, as Bill rubbed his sore muscles. "That means your muscles are getting bigger. If you get into a routine and work with weights every day, switching between arms, legs, and core, you'll be amazed at the results," Frank advised. Bill could only nod in response as he admired Frank's chiseled body.

"I know it has been tough providing for everything Annie wants," Frank continued. "She is a beautiful woman. You are very lucky. And trust me I know how much beautiful women desire. You think keeping a woman like Chloe is cheap? And she isn't even a mother."

"But your worries are over now," Frank continued. "This promotion is going to work out great for both of us. You are going to be a great asset for the company, and we are going to compensate you accordingly. Wives have many desires. I imagine that Annie has many desires. A bigger house. A bigger car. More children," Frank said.

"As long as you are with my company, I will make sure Annie's desires are met," Frank said, and Bill could have sworn that Frank motioned to the hefty hose hanging between his legs. "Whatever she wants, I'll make sure she gets it," Frank continued. "If you want me to, of course."

Bill was eager to make Frank happy. Sure he could find another job, but his new promotion afforded him a salary he previously could only dream of. And he desperately wanted to make enough money to keep Annie happy.

"You've given me a great opportunity," Bill said, trying to look Frank in the eyes without gawking at the massive man meat hanging between his legs. "I will absolutely do my best to live up to your expectations."

"That's great to hear Bill. I think this is really going to work out. Chloe tells me you enjoyed your massage this morning," Frank said with a barely concealed grin.

"Uh... yes. Chloe is very good at what she does," Bill stammered. "She is so... professional. Gorgeous and professional. Your gift was very much appreciated," Bill managed.

"Chloe is talented," Frank responded. "She will be pleased to hear you appreciated her massage. All I ask in return is that you also appreciate the gift and truly embrace this relaxing week."

"I will. I will," Bill assured. "It is a gorgeous house, the weather has been great, and Annie and I have had a great time so far. I'm sure it will only get better from here."

"I think it will," Frank said. "I think it will."

That evening after dinner Frank suggested they enjoy a movie in the living room and the ladies said they both wanted to see Titanic. It wasn't Bill's favorite movie, but he relented as Frank didn't seem to object. Annie surprised Bill by wearing a short lace black nighty, but he figured they weren't going out, so she might as well be comfortable, even if she was showing way more skin then she usually did.

"Another gift from Chloe, I presume," Bill asked.

"She is so fun to shop with Bill," Annie said, "and not just because she's buying, although that helps. She just makes me feel sexy again. Like hanging out with the cool kids."

The couples started out sitting next to each other on the luxurious couches, but when Bill complained that his neck was sore from lifting weights, Chloe suggested he move to one of the rooms' swivel chairs so she could work her magic on him. Bill readily agreed.

Bill was in heaven enjoying Chloe's work on his neck when he distinctly heard his wife moan. He ignored the first instance, and the second, but when his wife moaned a third time, he apologized to Chloe and turned the chair.

What he saw shocked and aroused him at the same time. His wife was sitting with her legs across Frank's lap, they were locked in a deep kiss as Frank was fondling her breasts with one hand while his other hand disappeared under the bottom of her nighty. Bill realized that Annie was moaning because Frank was fingering her.

"Relax and enjoy the show," Chloe leaned in and whispered in his ear as she extended the massage from his neck to his shoulders. "She wants this. She needs this. And by looking at your pants I can tell you want it too," she said. And she was right, his dick was fully erect.

"I need to see it," Annie said, pushing away from Frank's embrace. "I want to hold it."

Frank pushed down his satin pajamas, as Annie moved off his lap, revealing an enormous erection which Annie immediately took in her pudgy hands, stroking it vigorously. "It's magnificent," Annie said.

Annie then threw one leg over Frank's lap, straddling him and aligning her womanhood with his manhood. She then slowly lowered herself onto his giant cock. Bill could not see her face as Frank's member entered his wife's pussy, but he heard her cry out, "Oh my god, it is so big."

Annie rocked her pussy back and forth on the first inch of Frank's dick for a few strokes before taking another inch and then another. "Oh god it feels so good," she moaned, as Frank greedily began sucking her breasts,

Annie then leaned in to lock her lips with Frank and slammed the length of his girth into her womb. She briefly shuddered as his entire length took her. "It's so full," Annie stammered, releasing Frank from their kiss. "I feel... so full." She sat there, motionless, impaled by his cock for at least a minute before she started slowly grinding her clit into his pubic bone.

Frank let Annie do all the work, except that he went back to suckling on Annie's bulging tits. It wasn't long before the stimulation was too much for her. "I'm cuming. Oh god I'm cuming," Annie cried, as she ground into Frank with increased ferocity. "Oh...Oh...ughnn," Annie moaned as Bill watched her butt and leg muscles contract. Wave after wave of pleasure was spreading through Annie's body and at the epicenter of that joy was a vagina stuffed with a hard cock that was hitting nerve endings she never existed.

Annie's moans and convulsions slowly grew softer and less violent until she was still. At that point Frank lovingly stroked her hair and whispered in her ear, "Was it everything you hoped for?"

"Better," was all Annie could muster in response. "It was better than I ever imagined."

"We're not done yet," Frank said, subtly guiding her off his cock, there was an audible "pop" when it finally came out. He placed her on her hands and knees facing her husband. It was a deep couch, as wide as a single bed, so there was plenty of room for Annie to be on all fours.

God she was sexy in the doggy position, Bill thought, her ample tits hanging like tear drops beneath her and her big bubble butt exposed and vulnerable behind her. Bill would have loved to fuck Annie in this position but his dick could barely get past his wife's abundant cushion and even when he did poke through, he never lasted very long.

"Please put it back in," Annie pleaded, her pussy aching to be filled again. "Don't tease me. I feel empty without it."

"Do you promise to be a good girl and do as your told?" Frank asked, cunningly running the head of his member along her sopping wet folds.

"Yes, yes, I'll do anything, just please put it back in," she pleaded.

Frank had no intention of torturing her with anticipation, and he drove his shaft deep inside her with one smooth stroke. Annie's body straightened in delight and for the first time since the movie started, she was now staring directly into her husband's eyes.

"Oh baby, he just feels so good," she tried to explain. She had been so overcome with lust for Frank's cock she had totally forgotten her husband was in the room. "Please don't be mad at me baby," she whimpered, as Frank began to pump in and out of her. "I'll make it up to you, I promise. Just please, let him finish. He feels so good."

"Tell her it's ok," Chloe whispered into his ear, pausing her massage for a moment. "Tell her you love her."

"It's ok," Bill said, "I love you so much. I just want you to be happy."

Frank had picked up his pace as Annie and Bill spoke to each other. Soon everyone could hear his heavy balls slamming into Annie's clit with each thrust. Her breasts were now swinging in circles colliding into each other as she matched each of Frank's thrusts pushing her needy vagina back onto his cock.

"Do you like getting fucked like this Annie?" Frank interjected. "Does your husband fuck you like this?"

Annie broke eye contact with Bill, turning her head sideways to answer him. "Oh god I love it Frank. Please don't stop."

"Does your husband fuck you like this?" Frank asked again.

"No. No. I'm sorry Bill. But no he doesn't. He's not big like you. He can't take me like this... oh god it feels so good," Annie replied.

"Look at your husband Annie. Tell him how much you love my dick. Tell him that you need it," Frank ordered.

Annie turned her head back so she was looking straight into Bill's eyes. "I love Frank's cock honey. I need it."

"Whose pussy is this, Annie?" Frank asked. "Is this your husband's pussy or is it mine?" Frank asked.

"It's yours. It's your pussy Frank. Just don't stop fucking me," Annie said.

And with that Frank picked up his pace and lowered his upper body over hers so that he could kiss her mouth, his tongue eagerly invading her, and her tongue welcomingly intertwining with his. Frank then moved his hand from holding Annie's hips and began fondling her swinging tits. First holding them firm before using his fingers to play with her nipples.