Secretary Sandwich Pt. 02

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The threesome picks up a fourth on a business trip.
15.1k words
4.75
39.6k
43

Part 2 of the 4 part series

Updated 06/09/2023
Created 12/26/2019
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dpingjessie
dpingjessie
1,153 Followers

A couple months had passed since business partners Jason and Shane began double-teaming Jason's secretary, Abby. The first couple weeks were a blur, during which the 25-year-old blonde was treated to about as much dick as she had in the rest of her life combined aided by the fact that she was almost always taking two simultaneously. None of the three of them ever actually shared with any coworkers what was going on, yet it was inevitable that some people were starting to notice the interesting dynamic among the three. People minded their own business for the most part, though, because Jason, Shane and Abby were all doing blameless work for the company, which was bringing in a lot of money. Rumors spread, but if things remained relatively professional at work, anything anyone said was only harmless office gossip.

Of course, when it came time for the company's annual convention in the middle of that winter, some eyes were rolled when Jason, the director of the department, selected Abby and Shane to accompany him. Though Shane was a new addition, it was hard to argue against his case, since there was a noticeable uptick in profitability since his arrival right around Christmas. Abby, on the other hand, was a secretary, and while it was justifiable that the two men needed someone to keep them organized and on track during the several days they would be away, it only fueled the rumor that Abby was sleeping with both men. Of course, she was. What people didn't know is that often she was sleeping with both at the same time.

There were plenty of other people who would have liked to have been picked to go on a business trip to Florida in the middle of the cold winter. Jason would never have admitted it to anyone else, but Abby was being brought along for strictly personal reasons when it came down to it. If he and Shane were going to be away from town for several days together, they needed Abby with (under, on top of, between) them. It was an opportunity Jason wouldn't pass up no matter how suspicious it might seem to some. And so the three boarded an airplane to Tampa at the start of the first full week in March.

The three of them had been talking up this trip for the days and weeks leading up to it, and that buildup continued right through the flight and up to their arrival at the hotel. By the time they were in the room, they simply left their suitcases by the door, and Jason and Shane were undressing Abby before the door had fully shut behind them. No one even thought to close the curtains in the spacious hotel room as Abby was stripped down while they trio made its way toward the closer of the two king-sized beds in the room.

Abby was completely naked when her thin, 5'4" frame was tossed playfully on the bed by the young men, who took their turns to disrobe and then join the lady. They had just a little more than an hour to be in the conference room downstairs for the first seminar, and all three of them needed to shower and change into nicer clothes before heading down. They didn't have the luxury of a drawn-out escapade and got right to it. After several weeks put into this type of activity, the three had well mastered the art of the devil's threesome.

As soon as the boys were on either side of her, Abby grasped a cock in each hand a beat them off furiously, ensuring they were rock hard for her. It was a formality, of course, since both Jason and Shane had been ready to go since their bags hit the floor a moment ago. Seeing those athletic men ready to ravish her with their big hard cocks had Abby's pussy dripping wet in no time, so all that was left to do was get into position. Shane directed Abby onto her hands and knees as he set up behind her, allowing Jason to kneel in front of the secretary and enjoy a blowjob while Shane guided his prick into Abby's tight pussy. As Shane slid in, he held onto Abby's waist and moaned, goings balls-deep inside her while the girl held the base of another man's cock and skillfully sucked the rest of its length.

The men pumped in and out of either end of Abby for a few minutes and then switched. Abby was now sucking her juices off Shane's cock while Jason pounded her from behind, leaning forward and squeezing her tits as he fucked her while his business partner pulled gently on those blond strands of hair and slid his penis up and down Abby's throat. Several minutes into the throes of intercourse, and none of them had yet realized that the curtains were still wide open and that they were on clear display to more than a few rooms across the hotel's courtyard.

One such room was occupied by a woman in her early 30s named Lisa who was in Tampa for a very different reason. She was a 5'3" Filipino girl with dark skin, dark hair, dark eyes and, like Abby, a gorgeous, innocent smile. Her name was Lisa. What most people didn't know about Lisa was that she had a wild side. While her marriage to her husband of four years seemed completely wholesome, she was married to a man who a couple years into the marriage admitted to hotwife fantasies, and Lisa, after being initially shocked, was more than intrigued. The result over the past couple years were several hookups with other men where Lisa would take a picture or video and send it to her husband and even a couple threesomes which had both involved her husband. Since Lisa and her husband had a reputation to maintain, she rarely hooked up with men from their hometown. However, whenever she was out of town, her goal was clear. In this instance, it was the first time Lisa was taking a vacation by herself with the sole purpose of sending her husband evidence of her with another man.

Lisa had been in Tampa for a couple days already without a lot of luck. She had generated a lot of attention, of course, at the bars and beaches she had been to but hadn't found any guys who really got her motor running. That was until this afternoon when something caught her eye out her hotel window, which, of course, was two athletic guys who looked like they were using a cute blond girl as a Chinese finger trap for their cocks.

Lisa sat down on her bed while her mind ran wild with the idea of herself being the next girl to be treated that way by those guys. She wished she had a way to connect with them. What a surprise it would be for her husband! For now, she just decided to relax and enjoy the show. It was very apparent to Lisa that all three of them were having a great time, and those boys were giving it to that girl really good. Lisa's pussy was so wet as she watched that she couldn't help but masturbate as the entertainment continued. The more wrapped up in she got in the porn, the more she felt attraction toward not just the men but the girl in the middle as well.

For the next few moments, the men took turns fucking the girl in different positions, including on her back, doggystyle and missionary. Sometimes the other guy was having his dick sucked or stroked, and sometimes he was just watching. Lisa wasn't sure, but it looked like they each took a turn in the girl's ass too, something Lisa had never done. She very definitely hadn't tried what they finished with, which was double penetration with the girl on her hands and knees between the two men. They must have done it before, because all three of them moved like a well-oiled machine and seemed to be having a blast. It was during the sex sandwich that Lisa came from her fingering herself. She would want to give that a try if she were lucky enough to cross paths with these hot guys.

Meanwhile, unaware that they were entertaining at least one onlooker, Shane and Jason were ready to burst (literally) from the pleasure of double-penetrating their sexy secretary, who was soon in the midst of her own crushing orgasm. Shane was on the bottom, plugging the blond girl's tight pussy while her lovely tits jiggled in his face, and Jason was behind Abby plowing her ass in sync with Shane's thrusts into her so that they were sawing in and out of her perfectly. As Lisa had observed, the men really had the double-stuffing down after all their weeks of doing it. As Abby came down from a screeching climax, Jason announced that he was ready to plaster the sweet girl with his load, so he pulled out. Shane gently pushed Abby off him so that she was on her back, and the two boys knelt on either side of her, moaning loudly as they jacked off until they took turns cumming on her pretty, grinning face. Jason erupted first, spurting semen across his secretary's eyes, nose and mouth. Once he finished, Shane took his shot, creaming Abby's cheek and forehead while getting a little bit in her hair and around her eyes.

As soon as everyone was done cumming, Jason realized they had taken a little longer than expected, so Abby hurried into the shower while cum streamed down her face and neck. Jason picked up the room, and Shane hopped in the shower for a few minutes with Abby but only to get clean - this time. There would be time later during this convention for shower sex. As Jason piled clothes up, he finally noticed that the curtains had been drawn back the whole time and he wondered if anyone had seen them. It didn't matter to him if they did. In that case, he hoped they had put on a good show.

Next, the trio of Jason, Shane and Abby attended the first seminar of the week long convention. While they were obviously there to put in hard work, in the back of their minds they were all looking forward to the week long debauchery that was in front of them. Abby was looking to push the limits of the group sex that she was having with Jason and Shane, if that was even possible. She was hoping to add a third cock to the mix this week, maybe pick up a guy at a bar or something so she could be properly gang-banged. She wasn't ruling out the possibility of fooling around with another women, also. In fact, back in college she had fooled around with some of the sisters of her sorority. To Abby there was just something special about another women eating her pussy as opposed to a man. Jason and Shane had done a wonderful job at eating her out but another women would just knew how to pleasure another women.

It was still early of the week of the convention. Abby, Jason and Shane knew that they were going to have to pace themselves. They had to be up early in the morning for meetings and seminars throughout the day and they all decided to skip a group session they would often partake in at night. Abby liked to sleep in the nude and her two lovers always joined her naked in bed. Jason and Shane picked a side of Abby and the three of them went into a pleasant slumber.

The next morning the three of them quickly got ready for their meetings and left the hotel room. On the other side of the hotel Lisa was not having as good a time. Lisa had decided to check out a new night club at the recommendation of the concierge at the hotel. It was a complete bust. Lisa had done everything she thought possible to pick up a guy at the bar. She had worn just enough makeup to look natural and worn the skimpiest dress that she had brought with her, but somehow Lisa had struck out at the bar. She was now thinking of cutting her trip short and return home to her husband. She thought back to yesterday of the threesome that she was lucky to witness. Up to this point of the trip that had been the highlight. The lone bright spot of the trip was that she was able to bring her self to orgasm after masturbating. Lisa still couldn't believe how much she had been turned from watching another women get fucked by two athletic guys. She had been lucky enough to participate in a couple of devils threesomes herself with her husband but what she had witnessed yesterday was just different. Lisa had been extremely turned on when she saw what she thought was anal penetration and the ensuing double penetration. She decided to head out for lunch and afterwards go to a sex shop to buy some toys.

A few hours later Lisa returned to her hotel room with bags in hand. Inside the bags were a couple of toys that she thought she might like trying. Perhaps she would get lucky and get to see another sex show put on by the same people yesterday. Lisa was happy to use her fingers to get herself off but nothing could replace a nice firm cock to get the job done. She opened her bag of toys and brought out each of them. She had bought two small dildos and a 12" double-ended dildo. Lisa didn't really care for the double-ended dildo. The person working at the sex shop wouldn't stop talking so Lisa bought it just to so the person would shut up. Lisa couldn't imagine using it on herself so she put it back in the bag.

Lisa walked toward her window hoping to see act two of the sexcapades from yesterday. Her prayers were answered as she saw two of the same three people from yesterday. The blonde women was on her knees giving the guy head. Lisa pulled a seat up close to the window and grabbed the two small dildos that she had just bought.

In the other hotel room Shane was thoroughly enjoying the blowjob he was receiving from Abby. Shane and Abby had gotten out of their seminar early and were free for the rest of the day. Jason was still occupied with meetings and wouldn't be back for a couple of hours. Shane and Abby didn't see any reason not to have a little fun while Jason was away. Abby was bobbing up and down on Shane's cock while massaging his balls. This time, Abby had made sure the curtains were open while her and Shane fucked the afternoon away. Jason had mentioned to Abby earlier in the morning that the curtains were open yesterday during their first threesome of the trip, and Abby felt extra sexy knowing it was possible that someone could be watching. Shane was moaning from the oral treatment that he was receiving. He could feel his orgasm coming on but he didn't want to waste his load spraying it on Abby or forcing it down her throat. While Jason liked to paint Abby's face with cum, Shane preferred to cum in Abby's pussy or ass if he could. Since Jason wasn't around, Shane was going to give Abby a creampie. Abby was on birth control and loved the fact that each of her lover's had preferences where they liked to cum. As long as the orgasms kept coming she was happy to let her lovers plaster her face or load up her holes.

By now Abby had gotten of her knees and turned around. She was only wearing a pair of red high heels. It had become second nature now that she almost always wore a pair of high heels when she was getting fucked by Shane and Jason. Her tits were now pressed up against the window. Shane lined up his cock with Abby's pussy and slowly pushed until he was balls-deep inside. Shane started to pump in and out of Abby's center of sin. They started to build a rhythm, as Abby matched Shane's thrusts with her hips. Shane had his right arm wrapped under Abby's arm as he cupped and massaged one of her tits. His other hand was holding onto Abby's waist for support. Shane nestled his face in Abby's blonde hair, and the two were now rocking back and forth together. The scent of sex was in the air, and Abby and Shane were moaning uncontrollably. Abby opened her eyes to scan the rest of the hotel to see if that any viewers. After a moment she noticed something she was not expecting. There was dark skinned women masturbating with a dildo a floor below their floor. The women had eyes closed and it looked like she was close to climaxing. Abby slightly turned her head to see if Shane had noticed the same thing but he was too busy enjoying Abby's pussy to notice anything else. Shane and Abby could feel each other's orgasms were close approaching, so Shane whispered in Abby's ear that he was cumming. As Shane's white hot cum flooded Abby's pussy, Abby's orgasm crashed through her body. Once again Abby was completely satisfied. Shane pulled out, and cum slowly oozed out of Abby's pussy. Shane crashed on the closest king size bed and fell asleep.

Meanwhile, Abby was more interested in her audience. The dark skinned women was still furiously fucking her pussy with a small dildo. Abby paid close attention and noticed that the dark-skinned women was also using a second dildo in her ass. She was double-penetrating herself! Abby thought it was extremely sexy that this women may have been watching her getting DP'd the other day, which would explain this woman's inspiration to double-stuff herself. Abby's pussy tingled a bit as she thought about it. It had been awhile since she had been with another women but she did want to have even more fun while on this business vacation.

The whole time the other women didn't notice Abby watching from one floor above. Abby didn't want to be noticed so she joined Shane in bed where they took a nap. Abby made a mental note of the other women and approximately where her hotel room was. Perhaps Abby could have some fun and surprise the boys later in the week.

Shane and Abby woke up to sound of the hotel door opening when Jason walked in after a long day of seminars. Jason noticed that Shane and Abby were naked in bed and commented that the two must have had a fun afternoon. A devilish smile came across Abby's sexy lips, and Shane just nodded in response. Shane was sporting a half hard-on as he got out of bed and considered proposing a quickie right there, but the three of them had planned to go for dinner that evening and return to the room for a night of debauchery then.

Around 8:30 that night in the hotel's restaurant, Lisa was having dinner by herself. Again, her only highlight so far this day was her self-induced orgasm, as wonderful as it was, especially considering she had done so by probing her ass and pussy simultaneously with separate dildos. That was the first time Lisa had ever had something other than a finger tip in her ass. Her husband had tried numerous times to engage Lisa in anal sex but Lisa was never comfortable enough to try. It was also the first time she had ever been double-penetrated in any sense. Lisa was very happy but she yearned for more. She remembered from yesterday those two men fucking that blonde women. Lisa longed to be the women in the middle of those two men. At this point of her trip it was a long shot that she would even see them again. Lisa looked into her empty wine glass and looked around the restaurant for a waiter to get a refill. As she scanned the room, her heart skipped a beat as she saw three familiar people walk into the lobby of the restaurant. There was no doubt about it. The blonde women was easily identifiable. Her 5'4 petite frame was showcased in a beautiful dress. Lisa was positive these were the same three people she had watched two times previously having sex. The trio were guided by a waiter right past Lisa's table. As the trio passed Lisa's table she got a closer look at both of the men. They were young and gorgeous. That blonde women was also more beautiful up close. Lisa's pussy once again started to get moist.

Abby, Jason and Shane sat down for dinner. As the three of them walked through the restaurant Abby couldn't help but notice the young dark haired women from earlier this afternoon, which made her heart skip a beat. She made sure not to make eye contact with the stranger however. Abby got a much better look while they sat at separate tables. Both Shane and Jason were to busy chatting to notice Abby looking up the eye candy that was only two tables away. Abby's brain went into overdrive as thoughts went through her brain of the things she wanted to do to the stranger. The woman appeared to be of Southeast Asian descent judging by the complexion of her skin. Abby's best guess was that the women was Filipino (which was correct). The lady was about 5'2, had a bit of red in her black hair and her tits and ass were were even more full than Abby's. The women sported a very tone body, which made Abby both aroused and jealous. Thoughts of eating out the Asian women's pussy flooded Abby's thoughts. Jason had to call Abby's name a few times to get her out of a trance. Abby returned to reality and ordered dinner along side her two lovers. Abby was now determined to meet this women but didn't quite know how to do it. The Asian women had no idea Abby knew that she had been spying on them having sex. After a few moments, Abby excused herself from the dinner table and headed to the washroom.

dpingjessie
dpingjessie
1,153 Followers