Paying Off the Gambling Debt

My wife, Jessie, and I like to place bets on sports events. It has never made a lot of sense to either one of us the bet money since we share it anyway. Therefore, we usually place bets for "favors." I won the last bet, and with it, I won an evening during which Jessie would do whatever I asked.

I picked a Saturday night for the adventure. We went out to eat. I had Jessie dress for the occasion by wearing a button down shirt with a see-through bra underneath and a loose, short skirt that ended about halfway between her waist and her knees. Jessie is nearly 5 feet 8 inches tall and weighs approximately 140 pounds. Her 36 C breasts and rounded bottom look great in virtually anything. Her shoulder-length brown hair and dark brown eyes and full lips give her a sensual appearance that I adore. Looking at her as she got ready, I could hardly wait, knowing what I had planned.

We were seated at a table toward the back of the room. Our waiter was a young man named Kyle. I told Jessie to position herself so that if Kyle stood in the right place, he would be able to see down her shirt. It didn't seem to take Kyle long to realize the opportunity as he slid a bit to his right while taking our drink order.

I told Jessie to unbutton one extra button before he came back with the drinks. Her shirt was open nearly to her breasts, and I suspect you would be able to make out her nipples if she leaned forward so that the shirt fell away from her a bit. When Kyle returned, she did just that. Kyle leaned down and over her shoulder a bit as he gave Jessie her drink. His eyes were clearly looking down into her shirt as he placed the drink on the table. He blushed when he saw I had caught him staring down my wife's shirt.

By this time, Jessie was getting into the spirit of the evening. She started flirting just a bit with Kyle as he explained the specials to us.

While he was taking our order, Jessie "accidentally" dropped her spoon on the floor. Kyle quickly knelt down to pick it up, and was hidden from my view by the table. Jessie told me that he was looking at her thighs as he stood back up. She didn't give him a glimpse under her skirt at that point, but enjoyed the attention enough that I thought she might as the evening wore on.

Nothing further happened until Kyle asked if we wanted an after dinner drink. We ordered and he quickly returned. As he placed the drinks on the table, Jessie again "accidentally" dropped something. This time a tube of lip gloss that she had just used. Kyle again knelt down in front of her. I could not see what was going on, but Nicole told me she opened her knees a few inches. Her skirt was short and she said she was certain that Kyle had looked directly up her skirt. He must have, because when he stood up his ears and face were red as a beet.

When Kyle returned with the check, I noticed that he had written on the back, "Thank you for coming in. I Truly enjoyed serving you." We weren't sure if that was his normal signature or not, but I suspect that he did enjoy serving us--or at least serving Jessie.

From the restaurant, we went to a club that has live music every Saturday night. It is typically crowded and the crowd is a bit rowdy. It is also full of people looking for love. Jessie was worked up from the restaurant. She told me how excited she was from having flashed Kyle. I was glad that she enjoyed it, and told her to continue doing anything she thought she would enjoy once we got to the club.

When we got there I let Jessie go in first. I waited a few minutes, and then went in. As we had arranged, Jessie had already found a seat at the bar. I had told Jessie that I wanted her to act like she was to meet a guy at the bar and the guy stood her up. I watched from the other end of the bar as Jessie sipped a drink while looking around the club as if for somebody. She noticed me sitting at the other end of the bar and winked as she continued to scan the club.

After a few minutes, she was approached be a young man. He was around 6 feet tall and seemed to be pretty muscular, with nearly black hair. I would guess he was in his late 20s, like Jessie. I could not hear what they were saying from where I sat, but after a few minutes, the conversation appeared to get friendlier. The man called the bartender over and ordered a drink for Jessie and himself. When the drinks arrived, Jessie followed the man to a table between where I was and the dance floor where Jessie took a seat between the man who bought her a drink and another guy. The second guy was thinner and blond. He was shorter than the first, perhaps 1 or 2 inches taller than Jessie.

The three of them had another round of drinks. Jessie would occasionally touch one or the other of the men on the arm, letting her hand linger a bit when she did. Every once in a while, she would lean into one or the other as she laughed. After the second round, Jessie stood up and made her way to the ladies room. The men leaned together and spoke briefly. It appeared that they were enjoying her company.

I stood and went to the restroom as well. Jessie was coming out as I walked past the ladies room. We were hidden from the table where she had been, and she asked my how I was enjoying the show. I told her that I was and asked her if she was. She told me it had her excited and horny. Jessie asked how far she should take the evening, and I told her to do anything she was comfortable with. I would enjoy watching unless she signaled me to step in. With a smile she turned on her heels and went back to the table.

After relieving myself, I made my way back to the bar just in time to see Jessie making her way to the dance floor with the dark haired man. He had his hand in the small of her back as he followed her through the tables to the floor. The floor was crowded and I could not always see them; although, Jessie always seemed to work her way back to the near edge of the floor. Due to the crowd, they had to dance closely, even to the fast songs. There was no doubt in my mind that they were dancing close because they wanted to as well, though.

At one point during the second or third song, Jessie turned her back to the dark haired stranger and backed into him. He took the hint and placed his hands on her hips and began to press into her backside. His hands began to move to her stomach and up toward her chest before she wrapped her arms over his and leaned back into his chest, holding his hands in place. Shortly, she turned to face her partner and they danced one more song before returning to their table where another round waited.

After the drinks were finished, Jessie went to dance with the shorter gentleman. They also stayed close, with plenty of flirtatious touching. After a couple of songs, a slow song came on. I'm not sure why, but I half expected Jessie to return to the table. Instead she put her arms around the blond man's neck and moved in close. After a minute or so, I noticed that one of the blond man's hands was working its way down Jessie's back to her butt. He began to slowly trace his fingers across her skirt. Jessie tilted her head up and kissed him on the neck, letting him know she approved. The dance floor was still crowded, so I could not see everything that was happening, but occasionally I would catch a glimpse of this man's hand on Jessie's butt, feeling her contours through her skirt.

After the song ended, Jessie went to the ladies room again. As I had earlier, I met her when she came out. She asked if I thought it would be OK if she invited her new friends back to our house. She said she had told them she came alone in a cab, and was not with anyone else since she had been stood up. We decided that I would follow them most of the way home, but then she would take them a round-a-bout way into the neighborhood, allowing me time to get into the house and hidden before they came in. I made my way out to the car to make sure I was ready when they left.

After a couple of minutes they came out of the club with their arms around each other as if they were old friends. They made their way to a car and the taller, dark haired gentleman drove. All three sat in the front seat, with Jessie in the middle. At stop lights she would turn from one side to the other, kissing her suitors.

Soon we approached our neighborhood. Jessie had her driver turn as I proceeded straight so I could get to the house first. I was making my way upstairs when I heard the front door open. Jessie was telling the guys she was with that she was actually married, but her husband traveled a lot and was out of town. She had been planning to meet a co-worker at the bar but had been stood up. She then told them how lucky she considered herself to meet two handsome gentlemen who offered graciously to give her a ride home.

Jessie showed the guys, she was calling them Brad and Garrett, the alcohol and asked them to make her a drink while she went to the restroom. She came upstairs and nearly attacked me when she found me in the bedroom. She was obviously as turned on by her antics as I was. Jessie asked me if I just wanted her to flirt some more or if she could take it farther. I told her to go as far as she liked, as long as she did it somewhere that I could watch.

She went back downstairs to the kitchen, grabbed her drink and led the way into the living room to turn on some music. I crept partway down the stairs. The stairs in our house open into a hallway which has its back wall covered in mirrors. From the dark stairway, I was able to look into the mirrors to see everything that was happening in the living room. As Jessie bent over to turn on the stereo, Brad, the dark haired man, came up behind her and grabbed her hips. Jessie stood up and leaned back into him as the slow music began playing. Brad leaned down and kissed Jessie's neck. As he did so, his hands began to move to her stomach, and then up to her breasts. This time, Jessie did not stop him. Instead, she lifted her arms and reached back around his neck. Brad took the hint and brought his hands up to caress Jessie's chest.

He slowly began to undo the rest of Jessie's buttons and reach inside her shirt. Garrett was sitting on the couch enjoying the show as Brad and Jessie began to sway together. Brad slid Jessie's shirt off her shoulder's, leaving her in here bra and skirt. Jessie turned into Brad, put her arms around his neck and held him close. Garrett left his place on the couch and came up behind Jessie, lifting her skirt.

Garrett undid the clasp on Jessie's bra while Garrett knelt down behind her. He began to lick and kiss the cheeks of her ass while brushing his fingertips along the back and outside of her legs. Jessie arched her back and stuck her butt out to Garrett, who in turn began to lick slowly down Jessie's butt crack, across her pucker, to her pussy. When he first made contact, Jessie could barely stand. After a few seconds, she got down on all fours, wearing just her skirt, while Garrett continued to eat her ass and pussy from behind. Jessie was so turned on from the night the she came very quickly.

She then told Brad and Garrett to sit naked, side by side on the edge of the sofa while she knelt in front of them. As they stripped, I could see that Jessie would be getting the fucking of her life tonight. Brad's cock was thick and looked to be almost seven inches long. Garrett's was every bit as thick as Brad's, but much longer—perhaps eight or nine inches long. Jessie, to my knowledge, had never experienced anything that large, but she looked like she was more than ready to try. She alternated giving them blowjobs until they both orgasmed into her mouth. Garrett went to make more drinks while Jessie pulled Brad off the couch onto her. They fucked in the missionary position until Garrett came back. Jessie then move into a reverse cowgirl so that she could continue to suck Garrett's monster while getting fucked from below. I was so turned on by watching my wife that I could barely keep from touching myself.

After Brad came, Jessie got on all fours again, inviting Garrett to enter her from behind. Garrett must have realized the power of his tool, because her took it very slowly. As he worked his rod into Jessie she started telling him how great it felt and that she had never felt so full in her life. After several slow, gentle thrusts, Jessie raised her head sending her long brown hair flying and pushed back until Garrett was buried inside her. Jessie began to ride his cock. She had a look of sheer pleasure on her face. I slowly began to stroke myself through my pants in time to my wife's partner.

Jessie began to swing her hair from side to side and hump back into Garrett as if she was possessed. Softly, a moan began to build in her throat. It increased in volume as her movements increased with force. Jessie let out a scream as her orgasm exploded through her. I could tell from Garrett's reaction that Jessie was contracting her vaginal muscles and milking his rod for all it was worth. Garrett them tensed and blew his load deep into my wife. After they had calmed down caught their breath, Jessie told the two men she needed a few minutes alone upstairs to freshen up.

I quickly went into our bedroom to wait for her. She came in a few seconds later and came over to me and kissed me. She then told me to lay on the bed with my head over the edge. Jessie straddled my face and pushed her cunt to my mouth, telling me that she had done everything I asked of her tonight, so I had to do this one thing for her. As I licked Jessie's pussy clean, she undid my pants and began to stroke my cock. I was so hard and so turned on by her that it only took a few seconds for me to blow my load. After a couple of minutes, Jessie washed up and went back downstairs. Before she left, she told me to be sure to see here encore, because she wasn't done yet.

Before returning to the stairway, I cleaned myself up. By the time I made my way back to the mirrors, Jessie had Garrett lying on his back and was straddling him. This time, however, Brad had lubed his cock and was pressing it into Jessie's ass. Jessie had never been into anal sex before. I had probed her anus with both fingers and tongue, but she would never let anything bigger or harder in there. Brad seemed to know what he was doing, and Jessie would tell him when she was ready for more, or when to stop and wait for her to grow accustomed.

After ten minutes passed, Brad was all the way inside Jessie's ass. Brad and Garrett then began to slowly pump Jessie's holes. Garrett was sucking Jessie's nipples while Brad reached under her to rub her clit. After several minutes, the stimulation overwhelmed Jessie. She again began to orgasm. Within seconds, Brad did too. Garrett followed suit shortly after. They collapsed together in a heap.

After several minutes passed, they began to collect their wits. Brad and Garrett began to dress while Jessie collected her clothes. She walked them to the door and gave them each a goodnight kiss. She even gave Garrett her phone number so that he could call her, telling him that if I answered to tell me he was selling windows or siding. With that, her gentleman callers left for the night.

Jessie came upstairs, tired, but very satisfied. She came over and kissed me, then asked me if I like her "encore." I told her that I did very much and she promised that I would be the next person to penetrate her ass. Then she told me that I had to help clean her up again. Jessie crawled onto the bed on all fours. I knelt at the edge of the bed to lick her ass and pussy clean. When I was done, Jessie crawled into bed naked and fell asleep.