Paying for a Lost Bet

This is a story about a bet resulting form a near platonic office romance. Somehow the loser ends up feeling like a winner anyway when he pays his debt.

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Jim knew should never have agreed to this bet. Yes, he had lost fair and scare and he never reneged on a promise. But now here he was, sitting on a chair in her living room, blindfolded! Who knew what was going to happen next because there was nobody else home. Even her husband was away visiting his mother in Ottawa with their two kids.

When she opened the door after he rang the bell he was struck immediately by her traditional but somewhat scantily looking outfit. Her midriff was bare and there was ample cleavage showing in a loose top that was tied just under her chest. The top had tassels on its sleeves that ended just below her elbows in lace fringes. She also wore a beautiful long necklace and a white silk scarf that highlighted her lovely golden- brown skin. Her colorful skirt was short and loose showing off her long slender legs.

She gave him a big smile and a hug with the words "Assume you are here to pay up Jim!"

All he could do was nod while he gave her his coat and jacket and then took off his shoes as requested. Preceding him into the house he could not help but admire her tight ass that moved so lovely over those long legs. She was barefoot with only a thin golden bracelet on her left ankle.

It had been a silly challenge between the two of them at the office party. He had been so sure he would win. The gleam in her dark brown eyes had made him daring, helped by a few too many drinks. They both had promised with a laugh and giggle that the looser would have to do whatever the winner wanted for a few hours. It would happen in private and no humiliation or pain was allowed. They had joked about doing dishes, cleaning the house, or writing a difficult report.

In retrospect he had to admit that at that time he had very different ideas in mind, but he lost. The upside of the arrangement was that if he made it through without saying "stop, no more" she would do the same for him. And that would likely temper whatever she made him do.

Arriving in the living room she told him to sit down in a large straight-backed chair with leather cushions.

"I'll blindfold you now. Just don't move and follow all my instructions. Ok?"

"What are you going to do?"

She head a naughty gleam in her gorgeous large brown eyes, he noticed. Her luscious raven black hair was tied back in a ponytail making her cheek bones more pronounced. She smiled seductively when she pulled a silken blindfold from somewhere from her colorful skirt. The smile made her mouth very inviting and her teeth looked extra white against her golden-brown skin and full dark-red lips.

"Trust me, you will like it."

And with that she slipped the blindfold over his eyes and left the room. His last glimpse of her had been a peek down her blouse when she bent over him to put the blindfold on. She had lovely breasts in spite of having two children. When his gaze followed their shape he realised they were loose inside the blouse, that that there was no bra. He almost saw her nipples, but not quite, as the cloth was pulled over his eyes and the view disappeared.

His heart jumped in his chest and his mind spun with wild thoughts for a while but as the minutes went by he calmed down. Being blindfolded heightened his other senses, he could still smell the traces of her perfume mixed with a hint of tea tree oil.

In in his minds eye he could conjure up her image almost at will. She was a gorgeous creature, early thirties, petite, jet black hair, large glowing brown eyes with a mischievous glint, lovely light brown skin, and legs that made your heart skip a beat. He hoped she would come back without a bra.

There had been a chemistry between them right from the start. She liked his jokes and listened to his stories over coffee or lunch breaks at the office. She had twirled a few times for him when she walked into his office, behind the door so nobody could see. When her loose skirt had risen high up her thighs it had given him an instant painful erection.

Her background fascinated him, India was a county of many great stories, and lovely women. She was a woman with ambition and was an expert on office gossip. On the odd occasions their hands or bodies had touched, first by coincidence and later sometimes on purpose, it had always been electrifying. Standing or sitting close to her always made his heartbeat faster as if their auras touched and sparked. Although neither really wanted to complicate their lives they both had become aware of their strong mutual attraction. Somehow they both knew how to get the other person's attention even in a crowded office. The few times they went for a walk during lunchtime it had taken effort to not end up holding hands.

Only once had she allowed him an intimate touch. It happened when they were reviewing a test report she had brought into his office. As she stood beside him while he sat at his desk he had dropped his hand as if by accident and touched the back of her knee. When there was no reaction he had made the touch deliberate. Her reaction had been to move ever so slightly closer to him.

While both pretended to read the report, you never knew who would walk by the open door, he had started to move his hand up and down and more to the inside of her leg. A quick glance at her face showed him a slight smile followed by a quick nod, while she kept discussing the report as if nothing was happening.

Slowly rubbing her soft skin he moved is hand up higher and higher to where the skin was really soft and sweet. The only tell had been the color on her face and the lower timbre of her voice. There was also a sharp intake of breath when he moved his hand back and forth just under her core. Her leg had started to vibrate a bit when his hand reached so high it could go no further, where the fabric of her panties was damp, quite damp. When he slid his index finger into her slit and rubbed it back and forth she had to lean on him to catch her breath.

"Oh, you make me so wet" she murmured into his ear as she bent a bit forward, her leg vibrating faster.

"Close the door and come and sit on my lap" he whispered.

But right then his boss walked by yelling "Urgent meeting in the boardroom, right now!"

And that had been three weeks ago. They both had been more careful and kept a bit of distance, acknowledging that they were playing with fire. Until the party. And now here he was, at her house, in her living room, sitting on a comfortable chair, blindfolded.

She had left about 10 minutes ago, keeping him waiting with anticipation. Soft music was playing, while he wondered what was going to happen. Would she make him do the dishes, and cut the grass, or kiss him and ravish him? Or something completely weird, like paint his body?

He suddenly heard her enter the room without saying anything, but he could hear she was moving, dancing around him. Every once and a while she passed so close by him she would lightly brush his legs or back. All the while he felt the air movement and smelled her perfume.

Suddenly she sat on his lap, put her hands behind his head, and kissed him. It was tentative at first but when he respond she increased her intensity and open her mouth. Her tongue quickly entered between his lips looking for his. He felled like she was still dressed the same, as he tentatively moved his hands up to her hips. While kissing him she slowly moved forward, until she rubbed against his suddenly almost painfully hard member which she no doubt could feel through his thin pants. As the kiss intensified so did the movement of her hips and the rest of her body. Her tongue went deeper into his mouth and she moved sensually against him with her whole body. It started to feel like heaven.

After a few minutes she broke the kiss and got up.

"Stand up and take of your clothes, please"

"Are you sure?"

"Yes, I am very sure!"

Jim hesitated a second but then stood up and stripped of all his clothes. When he pulled off his underwear as the last item his erection stood out clearly from his body and sitting down again it stood defiantly erect from his lap.

She sat back on his lap again, still fully dressed, and started kissing him again. But when she moved her hips forward he suddenly felt she was naked under her dress. When she pressed herself against his erect penis he felt first a tuft of pubic hair, and then the wetness of her nether lips.

Slowly she kissed him with greater intensity and started moving her lower body against the root of his penis in a very sensual manner. He could feel her heat as her lips must have parted against the base of his cock. As the kissing went on and on her movements became more heated. Jim had the greatest difficulty in keeping his hands by his sides as instructed. Grabbing her and inserting himself became a very tempting thought.

"Nod your head if you like this."

Dumbfounded he nodded. The last thing he wanted was for her to stop. But how far would she go?

"Don't you dare to move" she instructed him and the returned to the deep kissing with him.

Bracing herself with her arms around his neck she slowly rubbed herself up and down his penis as her breath became more and more ragged. He realized she was working herself to a climax rubbing longer and higher along the length of his dick. Her breath turned into a pant when she started rubbing her clitoris against the sensitive top of his prick. As she neared her climax, she rose even higher until the tip of his prick was between her labia and he could feel her wetness dripping down his shaft.

"Don't dare to come until I tell you!"

And then she quickly lowered herself onto him for a few centimetres. It was all he had dreamed off, feeling her heavenly heat slide over the bulb of his member. With a few quick movements of her hips she impaled herself halfway down onto his pole and then climaxed with a shudder. He could feel her contracting around the embedded part. She was quite tight, surprisingly. It was almost too much for him but by making two fists he succeeded in controlling his ejaculation, although he was sure some pre-cum must have escaped.

After the major waves of her orgasm passed and her contractions subsided she finally relaxed somewhat. She put her head against his chest, and as she relaxed gravity kicked in. Ever so slowly she slid down onto his pole until her bum kissed his thighs. She sheathed him and the sensation of having her fully impaled on his member was out of this world.

Gently she rocked back and forth as if they were going to continue with a real fuck. Jim really needed some release, in spite of the glorious feeling of being so deeply embedded inside this woman he had wanted to take since that office episode at his desk. After a minute or so she lifted her head.

"You fit, but just barely!"

Jim sighed and slowly tried to move out and in.

"Don't move. And don't come. I want to try something I have never done before."

Slowly she rose and when his wet penis popped out it suddenly felt cool. When she was standing he heard the rustle of her clothing just before she planted a kiss on the tip of his penis.

"Don't move" she repeated and left him sitting there. Slowly his breathing calmed down, but his penis remained rock hard. Suddenly he felt her behind him.

She kissed his neck which made him shiver with anticipation. Slowly her hands moved down his chest, while she nibbled on his ear, and both side of his neck. She rubbed his nipples, and then lowered her hands until they reached his penis which she stroked while moaning in his ear. It took him a few seconds to realise she was mouthing dirty words about him coming inside her, in every hole. She then reached up, and took his blindfold off, and stepped in front of him.

She was almost naked, her skirt was gone, and her blouse was open. When she twirled in front of him her buttocks looked good enough to eat. Her pussy was bare, except for a tuft of hair above her lovely looking slit. She was gorgeous, lustful, with desire burning in her eyes.

"Are you up for an experiment" she asked.

He could only nod. She reached down and picked up a tube of ultra glide.

"I just want to know what it feels like when you are in my anus. I have never done that but I would like to try. "

Jim nodded. Anything she wanted was hers to command based on that bet.

"Later we can finish the regular way, I have dreamed of you filling me up that way ever since you touched me in the office" she said somewhat shyly.

This time he succeeded in murmuring "OK".

"And I want to see your face as we do this" she added.

She bent forward and started to apply the ultra glide liberally to his penis, after which she rubbed a gob between her ass cheeks. She put the tube down and sat facing him on his thighs.

"Don't move" she said when his hands came up to reach for her hips.

To pacify him she rose up slightly and let him nibble her nipples of her lovely firm breasts for a minute, while her hands massaged his prick, which must have felt like an iron bar to her. He was so distracted that it took him a few seconds to realise she had moved forward and placed the head of his penis against her back door.

She rubbed it a few times back and forth and then slowly lowered herself a bit so he could feel himself enter very slightly. He looked up and saw her face had a big smile on it. Slowly she lowered herself a bit, and started to move up and down, holding on to his shaft to keep it in the place she wanted it. He felt the pressure build, and the suddenly he was past the entrance and inside her with the head of his dick. He was in wonder of her lovely face that remained smiling after a small wince. Slowly she lowered herself, all the while moving up and down, until she had to remove her hand, and her face was level with his.

She looked into his eyes and said "Thank you. This is amazing".

She then closed her eyes and kissed him deeply as she lowered herself the last centimetre or two until she sat on his lap. He felt her anal constriction around the base of his penis and knew himself to be completely buried in her back side. The strong grip felt almost painful, the sensation was overwhelming. His balls contracted and only with the strongest concentration could he prevent himself from coming.

The taste of her tongue in his mouth, the movement of her lips on his, the musky smell of her pussy, was the most wonderful combination of sensations and feelings he ever experienced. It was exhilarating and serene at the same time, as if you combined skydiving with lying on a warm white sandy beach.

Suddenly she broke the kiss, raised her knees, and put her feet beside his hips. When he looked down he could see her cunt, wet and open like a blooming flower. Right behind that was her stretched anus pulsing around the base of his dick. Slowly she started to move back and forth slightly so he slid a tiny bit in and out. The sensation was amazing, it was so tight and so warm. She moaned a bit and the tiny movements seemed to be enough for her to start to build another major orgasm.

She opened her eyes, smiled her lovely smile, and looked at him with love in her face.

"Can you come again in an hour" she asked.

He just nodded.

"Then hold me, and kiss me, and come when I come. We will do my pussy in an hour or so" she instructed.

All Jim could do was put his arms around her to kiss her as deeply as he could. Her hand slid down to her clit as she started to move. She did not need to strum it much; they were both ready to explode. The strokes out and in became a bit longer but remained shallow. From the frequency and rhythm of her contractions he could feel her orgasm was close.

When she went over the top she broke the kiss and with a groan slammed herself down on him and then danced back and forth on his dick, suddenly fucking him fiercely. As soon as Jim felt the wave of contractions in her tight rear channel he let go with a roar and shot load after load deep into her backside, following her movements, fucking her right back with every bounce. Her breasts danced in his face as she gyrated on his dick as he orgasmed deep into ass.

It took them both a while to finish and calm down.

Finally she opened her eyes and looked at him smiling.

"Wow, that was amazing! And I still have another two hours with you."

Jim gently nudged himself in and out of her bum.

"Indeed! You are the boss, but if you order me to do the front as well I will not object."

She smiled.

"Consider the order given. But first we need to take a shower. And then we will and try my bed."

Ever so slowly she got up and Jim felt how he gently slid out of her. Taking his hand she led him to the bathroom where she stripped and wiped away the traces of their first lovemaking before joining him in the shower.