A Boss with Benefits Ch. 02


Sharon was a married woman who accepted a position working in the office of Mike a wealthy businessman. She did this despite his declaration during the offer of employment, that at some point he would try to seduce her. She enjoys the work situation and soon becomes erotically interested in her boss as well. They tease each other over the course of several months before Sharon accepts an invitation to join him for a day alone and away from work.

Mike was at the marina early next morning. He was part owner of a large motor yacht, an investment he shared with five other entrepreneurs. He and his partners in the yacht used it to entertain clients and government officials. It was a full time business as they also rented it for private parties. They had engaged the services of a Captain who also acted as Manager of the small corporation. It was not a money making investment but it did provide them prestige and a lot of pleasure.

Mike occasionally entertained ladies on board, the elegance being much more conducive to seduction than a motel. It was a beautiful morning and he was assisting Steve, the Captain, in preparing the boat for a daylong cruise with Sharon.

Mike was a realist. He did not actively seek out women for sex. But he had worked in enough offices to recognize that a relationship between office workers could easily evolve into an intimate encounter. One can spend more of their waking hours with an assistant at the office than with their mates at home. Conditions are ripe for personal involvement.

Mike’s current situation, working from his home in basically a two-person operation, could magnify the pressure and opportunity if the two were compatible. Mike ensured the latter by his hiring procedure. And then he basically allowed nature to take its course, placing the burden on his new associate to initiate the sex. Sharon had done that in spades. Despite informing her at the outset of his most likely attempt to fuck her, he had made no further move until she had become the aggressor.

Sharon was disappointed when she arrived at the office to find that Mike was not around. The phone rang within minutes, it was Mike, “Morning Sharon, are you ready for a picnic?”

Cautious at first, Sharon countered, “A man of mystery, I like that. Whatever is the plan?” She wondered what sort of game he was playing. Her mind had been on sex all night long but getting laid on a blanket in a park had not been one of the fantasies!

Mike said, “There will be a cab there to pick you up in ten minutes. I’ll be waiting for you here.”

Despite not having any idea where ‘here’ was, Sharon managed, “Mike, you have my attention, I can hardly wait.”

Mike met her at the Marina gate and paid the cabby. She looked gorgeous, with her beautiful small voluptuous body, excited eyes and sweet lips. He grabbed her handbag and guided her to the boat. His eyes were glued on her jiggling cheeks as they climbed aboard.

Steve was at the other end of the gangplank, extending his hand with a smile. Sharon cringed a bit; did he know what she and Mike had planned? She suddenly felt like a lady of the night! However, that feeling passed quickly and only thoughts of Mike between her legs remained.

Mike guided her down the stairs to a large bedroom with sliding glass doors opening to a back deck equipped with deck chairs and a large bubbling hot tub. They kissed with intense passion, an automatic continuation of yesterday’s encounter. Mike stripped Sharon down to bra and panties.

But as Sharon prepared to lie down on the bed, Mike smiled; “Not yet baby, change first and we’ll go up top. I have to help Steve cast off and leave the harbor.”

Sharon paused and then reached for her handbag. What’s with this guy? She looked down at his groin area to see his erection bulging down along his pant-leg. His eyes followed her movements as she unhooked her bra. His mouth went dry as her beautiful pink-nippled tits bobbed before his eyes. She smiled coquettishly as she tucked each one into a halter-top. She paused, turned from him and pushed her panties down before pulling on a pair of soft tight jeans. She slowly eased the tight jeans over each cheek.

He could barely keep his hands off of her and she knew it. She moved in against him, thrusting her hip out to rub against his bulge and turned her head up for a kiss. She could not remember ever being so ready for sex in her life. Mike ran his tongue around the inside of her lips and said, “Don’t worry baby, you’re going to see enough of this big boy after we get to sea.”

She joined Captain Steve on the flying bridge and watched Mike hustle around releasing lines and checking for problems as they backed out of their mooring. He rejoined them on the bridge and they toasted each other with champagne as Steve maneuvered the big cruiser out to sea.

Mike bent and kissed her softly and whispered, “Let’s go below Sharon,” his hand guiding her back off the bridge. Sharon’s body was burning in anticipation as çiğli escort he fondled her cheeks; she was ready.

There was little need for foreplay. They stripped quickly and their bodies clapped together as if attracted by magnets. Mike grasped her ass cheeks, squeezing and spreading them. “You have the most delectable ass I have ever seen,” he groaned. “It was the second item that I noticed on you.”

Sharon had taken his stiff cock in hand, pressing the shaft against the inside of her forearm as her fingers worked down the shaft to caress his balls. She moaned, “What was the first thing?”

He surprised her with, “Your eyes and lips.”

Oh God, how sweet she thought, almost crying. His hand went to her breast, caressing it and squeezing a nipple.

“And your tits,” he moaned seriously.

Sharon pushed the long shaft of his cock between her legs, sliding her already slippery slit along the top of it. She could feel it throb between her legs. Sharon whispered in his ear, “That’s going to be a challenge but I want that big thing in me. We can play later; I want you now.” She would not tolerate more delays.

He followed her onto the bed, moving on his knees between her spread legs as she settled her head on the pillow. He caressed her slit with two fingers before hooking them under her pretty reddish bush. Her chest was heaving and her tits jiggling as she reached down to guide his knob back along her slit.

Mike’s body was so taught it was singing like a violin. He had pictured this day for months. He enjoyed the feel of her hand on his shaft, the velvet wetness of her pussy lips on his knob and her hard nipples against his chest as he lowered his body down on her. Her hard clit teased his knob as she rubbed and pushed her body up at him. She was tight, and he allowed her to work his cock inside of her at her own speed.

Sharon was in another world as she gradually forced her pussy around his cock, feeling it pop into her as her lips closed behind the knob. Anxious as they both were, the full entry took some minutes, with Sharon pulling more of his shaft into her pussy, and then Mike fucking her with whatever length was in her. The procedure was repeated several times. She was afraid that she would get off before she had it all.

Suddenly, it seemed as if his cock had pushed aside a barrier in her tunnel, it was all in her and he was leaning down over her on extended arms. He began to stroke her, slowly at first but as she loosened his speed increased. Soon he was down on her, his arms under her back, his hands clutched to her shoulders, chinning himself in her body while she ground her tits hard against his wiry chest. She pulled her knees up and felt his balls slapping against her ass cheeks.

His strokes quickened and Sharon reacted by thrusting her hips up to meet him. It was magic, they were soon in perfect rhythm, his cock pressing from side to side and top to bottom as he stroked her. She was off before him, her heels digging into his back as he thrust madly away inside of her. Her orgasm set him off and he followed with the short hard strokes preceding the explosive jolts of hot cream. Sharon trembled in relief as he lay on her, receiving his cum as her pussy clutched and released convulsively around his cock.

“That was worth waiting for,” Sharon smiled as Mike continued stroking her slowly with a softening cock.

He pushed up on his extended arms and smiled down, “Now for a hot tub to freshen up before I get to pay attention to the rest of you.” He bent and sucked her nipples before pulling his cock out of her.

Sharon lay there and watched his beautiful tight ass cheeks move away. He filled two glasses with champagne. He saluted her with a smile and pointed to the hot tub, just outside the glass sliding doors. He settled down in the bubbling water and gave her his hand as she moved in beside him and accepted her glass. The warm water felt good on her pussy, a little bruised after the pleasant pounding it had just received.

They toasted each other, Mike saying softly, “A beautiful beginning to a long pleasant day.” They kissed and settled down, stretching their legs and submerging their bodies to their chins in the gurgling warm water.

Sharon could not remain silent, always seeming to need to fill a void. “This is beautiful, what a lovely way to spend a morning.” She kissed him and then, “Do you bring all of your assistants for a boat ride?” She said it with a smile, not really expecting an answer.

Mike grinned, “Do you really want to know? Or are you just making conversation? You are one bold lady, but I like that about you. You hide very little.”

Sharon felt a buzz in her body, she felt challenged and decided that she really did want to know. It excited her to think of being one of his hand picked concubines. She moved up over him and planted an open mouthed kiss as her hand slipped under the water and grasped his partly stiff cock. “Yes I want to know. çiğli escort bayan Don’t tell me their names, just how many women have you brought out here.”

“Ah God,” Mike groaned as she stroked his stiffening cock, “Just assistants? Or how many ladies?” He was teasing her, but was seeking to find a reason for her prodding.

“You bastard,” Sharon gritted out, “How many assistants like me.” She plunged her tongue into his mouth and squeezed his cock.

He responded, “Do you want to know how many I brought for a boat ride, or how many have I fucked on board?” He was in the moment with her, the trash talking about sex was turning them both on.

She moved her mouth down his body and he began to lift out of the water realizing that she wanted to go down on him. He sat on the edge of the tub with her body between his legs, she holding his cock like an ice cream cone. She glared up as if angry at him, flicking her tongue at the knob, “How many did you fuck, probably the same number as you brought out here.” As soon as the words were out, she clasped her lips around his great knob and stroked his shaft. She looked up at him and ran her bared teeth over the velvet of his knob.

His knees turned weak at her sudden move, but he continued their little game as if more inspiration was required. “You’re right baby, I have brought five out and fucked all five, and now you are the sixth, and the best.” He grabbed her head and held it still as he slipped a good part of his cock in and out of her mouth.

He bent down and lifted her up, “Pussy time Sharon, want to lick yours.”

She would not give up. “Did you tell them that you would fuck them like you told me?” She wrapped her arms around his waist and rubbed her tits on him, totally turned on.

“No,” he offered, “You were the first one that I tried that on. The last lady quit and walked away when I touched her breast.” They kissed as he spread her with his knee before grasping and squeezing her entire pussy. “She had started coming to work braless and I assumed was teasing me, but I guess she wasn’t,” he grinned. “Let me dry you off.” She stood there, breasts heaving as he urgently toweled them both down.

He guided her to the bed and sat her down on the edge, before dropping to his knees between her legs. She braced herself back on her hands as he licked his way from her knees to her pussy. “Oh God,” she groaned, grabbing his head as his mouth engaged her juicy lips. He was all lips and tongue and fingers, kissing, licking poking and sucking all at once. She had never encountered this intensity of oral sex, “I’ll come, I’ll come,” she squealed, “don’t get me off this way.” But he continued until she fell back jamming her pussy at him, twisting her legs around his neck before losing consciousness as her body convulsed.

Then he was on her, forcing her back on the bed as his cock forged its way between her legs. He jabbed and thrust his cock through her still trembling pussy lips. She could taste her own pussy on his thick tongue. He was all in her in two strokes, humping her like a wild man, his body under the control of some basic human urge. He clamped her two hands in his and pinned them above her head as his other lifted her ass up for a better angle.

Suddenly she was back in the real world, her eyes blazing up at him as he lifted his upper body allowing him to see her eyes and bouncing tits. She grabbed his hips and pulled hard, dug her fingernails into his ass cheeks, encouraging him to pound her, suddenly needing to feel his blast of hot cum. His eyes closed tightly, he bared his teeth as she felt his cock swell even more before he jammed it in her and released his load. He collapsed on her, she raising her knees a bit as he ground away, cum still oozing out of his knob.

“Wow sailor,” she said with shaking voice, “Been at sea a long time?”

He rolled off of her and grinned back, “That one has been building since you first walked into my office. Let’s jump in the tub, dry off and go check the sights.”

She rolled to him, “Will I have to walk much? Not sure I can. This guy’s a brute.”

They dressed after their dip and climbed up to the flying deck where Steve was peering out over the water. Mike said, “Take a break Steve, Sharon and I will take over for a while.

Sharon moved up beside Mike as he sat at the wheel. He was not touching it just staring ahead. “Why don’t you steer?” she asked.

He said, “Oh the course has been set and is being controlled by the GPS, we just have to watch for logs or other things in the water. If you see something, just flick this toggle switch right or left, it will come back on course after a bit.”

She moved up against him. It was if she was living a dream, unreal but perfect in every way. They were cruising a long narrow inlet with no signs of human habitation; she standing and rubbing on this beautiful man, her body was humming. It was not even noon hour and she had been laid twice. It escort çiğli was honeymoon stuff.

He circled her waist with an arm, pulled her tight to his hip and bent to kiss her. Their lips hovered, tongue tips engaging softly, but being careful so as to not lose themselves in sex here on the bridge. It was idyllic and Sharon felt her loins go slack, the thought of him between her legs filling her mind. He slipped his hand down inside the back of her bikini bottom and fingered the crease between her cheeks.

He pulled back a bit, smiled at her and whispered, “We better keep our eyes ahead. Do you want me to call Steve back up? I want you naked again, I can’t seem to get enough of you.”

She rubbed his fully erect cock as she melted her body against him, “Call Steve.”

It was a week later and Sharon and Dot were in bed, naked. They were sitting up with their backs against the headboard and a sheet covering legs and hips, leaving their breasts exposed. They were nicely intoxicated, both from gin and sex talk.

They made a striking pair. The small reddish blond and the black haired olive skinned woman, holding hands while sipping martinis. Dot rolled towards Sharon until one of her tits brushed Sharon’s arm as she kissed Sharon’s neck.

They had slept together in college when they had been roommates and had enjoyed the warm soft feel of each other’s bodies, had kissed a bit, but had never engaged in full sex. Now, twenty or more years later, they knew more about life and were quite relaxed in a return to that period of their lives. Sharon had recounted the events of the day on the boat with her boss, leaving no detail unspoken.

“I’m hot baby, tell me what happened next,” Dot whispered while cupping a freckled milk white tit in her hand. They kissed a woman’s kiss, slow and gentle but intense. Dot pushed the blanket down to expose their bare legs, stretched out below them. Dot’s thick black bush covered her rounded mound in vivid contrast to Sharon’s trimmed reddish orange V.

Sharon continued, “He was insatiable. I was with him about 8 hours that day and he was erect for at least seven of them. I was worn out. But his fingers were magic and his cock irresistible, just looking at it made me hot, and he kept it out all the time we were alone. We returned to the bedroom as Steve turned the boat for our return voyage, probably a two-hour run down the coast. The sun was bright and warm and he suggested we stretch out naked on the back deck sheltered from the wind.”

Dot’s fingers edged down Sharon’s belly to the V of her legs, sorted through her pussy hairs, and then slowly ventured between her legs. Sharon’s hand went down to cover Dot’s. “Oh God Dot, if you want to hear the end of my tale, you better remove those fingers.” They kissed again, a much more intense though still tender exploration of tongues and lips.

Dot pulled her fingers back out after hooking two of them inside Sharon’s pussy, “Go on babe, we have all night together.” She circled Sharon’s nipples with her damp fingertips, and then licked each pink nipple.

Sharon continued, “We lay down on a mattress in the sun on the back deck, side by side, warming ourselves. It was so peaceful with the only sounds being the hum of the motor and the seas surging around the hull. He had a big bone on again, pointing straight up at the heavens. I was a little sore and quite frankly not looking forward to another session. But his body told me that was what was coming my way. I decided that maybe a hand job might serve us both well. I rolled towards him and began stroking his cock, while kissing his chest and sucking his nipples. He groaned, ‘beautiful baby, don’t stop’.”

Dot rolled partly on top of Sharon, pushing her knee between her legs and then lifting it up to rub against Sharon’s pussy. “Ah damn,” she cried, “I want some of that, you lucky bitch.” Sharon ground her pussy against Dot’s upper thigh, their tits now tangled together as she continued in a strangled voice, “I told him that I wanted to jerk him off and watch him cum. He said, ‘go for it’.”

The women rubbed wildly together for a minute, and then giggled and lay back from each other. Dot said, “I want to see where this goes with us sweetie, but also want to hear the ending. How about we just play with each other’s pussy while you provide the final details of your hand job.”

Sharon laughed and agreed, “Let’s continue but take it slower, my plan did take a turn of sorts.” They separated a bit on their sides, their legs parted and then they reached for the other’s pussy. Sharon enjoyed the gentle exploration of Dot’s fingers, to the same degree that she loved a man’s larger and more aggressive probing approach. It was more soothing and yet equally erotic.

“I didn’t know if I could get him off with my hand only, but was prepared to go down on him if it was called for. What I did not foresee was what would happen to my own body. I became more and more excited as I felt his passion build, he arching his back up, his hand clasped around mine as if fucking my fist, along with his groans and demands for more and more. My pussy began to ache, demanding to feel that monster in me again. He was very close to coming when I suddenly mounted him, knees each side of his body and lowered my pussy down.”

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