More people than you would expect

Rachel and Deedee’s eyes rolled at the same time while Trent stared in open mouth shock at the forwardness of his longtime crush, Jessica. Their server Tony maintained his professionalism and simply laughed in his deep baritone voice, a bright smile on his lips. “We do everything a la carte here ma’am. So it is made to order. We find that that means that we can manage to satisfy everyone’s cravings. Now, how about we get a bottle of wine started for the table?”

Rachel nodded at the wine, pointing to a cabernet sauvignon on the menu. “Yes, let's start with a bottle of this, four glasses.” Rachel’s voice seemed to bring Jessica back down to earth as she went back to reading the menu, but still snuck glimpses of the tall, dark, and handsome waiter.

“I’ll be right back with that. Is there anything else I can get started for you?” With a few shakes of her head, Rachel sent the waiter away before she turned back to look at Jessica.

“Honey, didn’t we come to spend time with our friends tonight? I know you want to run off and show him your little tattoo, but that is not our plan tonight. Now, if you are good, maybe I’ll let you have dessert.” Rachel’s words caused a shiver of anticipation from Jessica as she grinned in agreement. Turning back to look across the table towards Deedee, Rachel raised an eyebrow quizzically. “Now then, tell me more about you two? All I know about this one is that Tiffany just moved in with you? Oh and something about your son disappearing recently? Sounds like you two have had a busy weekend already.” The regal blonde slipped her arm around Jessica’s shoulder and pulled the bouncy woman into a tight cuddle as they sat and waited for a response.

Turning to look over at Tiffany, Deedee grinned. “Do you want me to tell the story or do you want to lay it all out, Tiff honey?” Trent’s eyes shot open as the implied threat of having him disclose the truth of the situation sat unanswered. His breath shot through his nose as he shook his head in the negative, attempting to get Deedee to tell some made up story.

Saved by the arrival of the wine, Deedee watched Trent as the four glasses were poured for them by a different young server. Rachel motioned to the woman who was busy pouring the drinks and spoke. “Tell Tony to just bring us out the chef’s choice tasting courses please. We are keeping it light this evening.”

As the server pouring the drinks left the table, Jessica and Rachel shared a look. Turning back to look deep into Deedee’s eyes, Jessica revealed her opinion. “I think we should tell her.”

Trent’s confusion was short lived as his mind was suddenly occupied with a new and more physical feeling. A soft delicate foot was rubbing against his calf. Looking around the table, he surmised that it could only be one person. Locking eyes with Jessica, he was surprised to see her wink at him as the foot slid up and toyed with the edge of his skirt. Deedee and Rachel took the exchange in quietly as they both sipped their wine. Breaking the silence, Deedee turned to Rachel. “I’m not sure it is a good idea.”

Jessica’s eye roll was almost audible as she sighed in annoyance. Rachel, sensing the disorder at the table, smiled towards her date. “Let me tell you a story.” Trent tried to pay attention to the older blonde but it took all of his concentration not to stare at Jessica as her foot slid along his soft legs, prying between his knees. Trying to escape the encroaching appendage, he pushed back against the booth, only for his plug to be pushed deeper inside of him. A soft moan and closed eyes briefly was the only response he gave to the feeling of the toy inside him prodding him in ways he was not used to.

Deedee’s hand reached out to pat Tiffany’s knee and ended up contacting something else. Chuckling as she realized what Jessica was up to, she slid her hand to its originally intended location and gave her son’s soft knee a pat. Looking back to Rachel, she decided to see where the enigmatic woman would take this. “We would love to hear a story.”

Rachel’s hand scooped Jessica’s hand up and entwined her fingers around her date’s. “So, about 10 years ago, I had this guy come work for me. He was nice enough. Worked very hard to keep people around him happy. Had a beautiful girlfriend who treated him like garbage, but he loved her. Heaven only knows why.” Rachel’s smile took on a nostalgic look. “She would come to company parties and flirt with other people or just belittle him. It was a bit depressing really.” Shrugging, she went on. “One night, he and I went out to a bar. We had just solved an emergency and I wanted to reward him for his work.”

Taking another sip of her wine she smiled wistfully. At the same time, Jessica’s foot was worming its way between Trent’s bare thighs. Her manicured toes pried at the soft skin as she stared him down and chewed on her lip sexily. Done with her drink of wine, Rachel continued. “After more than a few drinks, he confessed that his depression was starting to get the better of him. Constant mental **** by his girlfriend was driving him lower and lower. He told me all about these problems they had in the bedroom. How her frustrations at him kept coming out in public.” Trent’s mind was having a difficult time keeping up with the story, even more so because he had no idea why it was being told. Finally, he felt Jessica’s foot tap against the hard plastic of his cage. He could feel her toes gripping the pink prison and just moving it around as she stared across the table at him.

Interrupting Rachel’s story, the first courses arrived. A number of finger foods were placed on the table. Selections of meat and cheese, dips and chips, and various breads were set out before all four of them. “Alright ladies, I’ll let you get to it. Let me know if I can be of any more service.” Tony’s deep smooth voice only increased the pressure that Jessica was putting into her soft **** of Trent’s caged cock and his smooth balls. The worst part about it for Trent was that this was the first time in days that anyone had touched him there. Since he had woken up with the cage on, he had been trying to ignore it. Deedee’s attentions had certainly caused arousal but had been focused elsewhere.

Trent’s heartbeat sped up as Jessica continued to toy with him, all while staring deep into his eyes. She grinned before slipping a breadstick between her pink lips. Before he could get too lost in the sensations Rachel went back to her story. “Now, I actually really liked this guy. He was sweet, caring, and giving. The biggest issue? He had no backbone at all. Or a better way to put it was that any hard resistance he put forth was so small that it didn’t matter.” Jessica’s giggling fit interrupted the reminiscing as she gripped the cage between her toes and moved it up and down almost like she was jacking Trent off with it.

Rachel ignored the byplay and simply moved on with her story. “Thankfully, due to our success in handling the issue, the higher ups threw our department a party. Wives, girlfriends, boyfriends were all invited. It was a cute little thing where the company rented out a bar for us.” Trent’s hands were at his sides clenched in white knuckled fists, or at least as much of a fist as he could make with the nail extensions. Staring back into Jessica’s eyes, he was torn between begging her to stop and praying she would find a way to yank the infernal thing off of him. Of course the manipulations of his most private area by his crush certainly made the cage’s fit even tighter than normal as he swelled within it.

“Knowing that this man’s girlfriend was going to show, I decided it was time for me to get involved. It was easy enough to separate them. Using her outfit as an excuse we made our way to a private area in the bar and chatted. What I learned was less than surprising. My employee was letting this woman walk all over him. She didn’t work, she would let her friends speak ill of him constantly. Their relationship was a trainwreck. It was simple enough to get her to keep going as I plied her with drink after drink. By the end of the night she was more than a little drunk, and I was driving all three of us back to their apartment.” Grinning at the memory, Rachel took a bite of some of the meat at the table before a swallow of the dry red wine chased it down.

“So we get back there and this guy is going nuts of course. Never in his life had he imagined his abusive girlfriend would give him a threesome with his boss. Of course that was never going to happen, but he didn’t need to know that.” Rachel pulled Jessica’s hand up to her lips and placed a gentle kiss against it. “I had no plans on sleeping with my employee that night, or ever really.”

Jessica’s voice cut in as her foot found its way under the elastic of Trent’s panties and slowly **** his thighs even more open. “Oh, I think deep down he knew it hun. He was more self aware than anyone gave him credit for. Just too weak willed to do anything about it.”

Seeing the byplay going on, Deedee leaned and brought her lips to Tiffany’s ear. “Are you enjoying the cute little footjob hun?” Her own hand slipped down to spread his legs out wide, pulling one up over her lap. “Listen to the story baby. It would be rude to our friends if you ignored it.”

The haze in Trent’s mind as Deedee and Jessica toyed with him grew and all he could do was nod. Tearing his eyes from Jessica he looked to Rachel and took a deep breath before asking her to continue. Nodding, she went on again. “Typically in polite company I would spare the delicate details, but I think tonight they are really the crux of the story” A second foot joined the first as Trent’s lower body was assaulted by both of Jessica’s appendages. While the first foot toyed with his cage, Jessica’s second foot began to worm its way lower towards a different prize.

“The three of us end up on their couch together. This woman and I were doing our steady best to ignore my friend. Everyone in that room knew he wasn’t going to be a part of that evening. Still, I felt bad. So I decided to involve him, to a lesser degree. Telling him to strip his girlfriend for me was a lot of fun. His hands trembled as he pulled her little black dress off. By the time he had slipped off her heels, panties, and bra, I could see a tiny little bump in the front of his slacks. Telling him to strip afterwards confused both of them.” Rachel paused her story to lean over and kiss her date squarely on the lips. Trent sat staring at the two gorgeous blondes making out in front of him as one of them shoved her feet under his skirt. He could feel the dampness gathering around Jessica’s toes as it leaked out of his cage. All while Deedee sat there and nibbled on his ear, holding him in place.

With Deedee on one side of him, a wall on the other side, Jessica’s feet shoved into his crotch, and the back of the seat behind him, Trent was pinned in place on all sides. It was at that moment that the big toe of Jessica’s second foot found what it had been searching for. The plug bounced within him as her toe pushed on it. Trent’s breath caught in his throat as Jessica began to slowly push it into him, then wait for his body to push it out. Part of Trent wanted to scream out how he was being abused, but a growing part of him loved the attention. His mind used the excuse that it was the attention of his long time crush driving him to these heights. That thought helped him ignore the growing feeling that spread from the plug slowly fucking him as it was pushed it in and out of his ass.

Pulling back from the kiss Rachel continued her story after another sip of wine. “It was so cute how he stood there naked while I pulled his wife onto my lap. I could tell why she was always so brutal with him. Laying there between his thighs was the smallest little dicklette I had ever seen! There was no way he could have ever made his wife feel good with it. His wife could see me staring at it and she told me all about how he had never made her cum without his tongue or a vibrator. The hurt look on his face as she revealed all the times she had faked it for him was really sad. Can you imagine that?”

Trent’s eyes bugged out as Jessica toyed with his cage. Jessica spoke up interrupting Rachel’s story. “Oh, I think Tiffany here gets it. Don’t you babes? She has probably dealt with tiny dicked guys who couldn’t get a woman off her whole life.” Wiggling her eyebrows up and down she manipulated his caged cock with her manicured toes. Trent’s mind was under **** from the insinuations as he thought back to all the times he had fucked Brittany. Whatever the truth had been, his hazy mind conjured images of her unsatisfied at his tiny cock. The thought entered his mind that Deedee would certainly have been able to satisfy her.

Rachel laughed at Jessica’s words and went on with her story. “So there I sat making out with her, but he just looked so lonely, so ****. Figuring it would be better if he covered up, I told him to get dressed again. But we both knew he wasn’t a real man, so I made him wear his wife’s clothes.” Turning to look Trent in the eyes, Rachel smiled and went on. “You should have seen his face as he did it without question. Slipping her thong up his legs, pulling on her bra. It was so cute. The best was when he kept going without being told. I had figured he could stand there in just her thong and bra, but no he even slipped into her heels. I couldn’t believe they fit him. Come to think of it, they were these cute black stilettos, almost like the pair you are wearing Tiffany.”

Jessica’s **** on his plug and his cage continued as Deedee spoke up. “Tiffany picked those out for herself tonight. In fact she picked out her whole outfit. I’m very proud of how good my girlfriend looks tonight.” Trent felt an odd sense of pride fill himself as Deedee supported the choices he had made. “It sounds like Tiffany and this coworker of yours both dressed themselves up in all black to please someone.”

“I was impressed at how he handled her clothes. Later he told me it was the first time he dressed up. I’m still not sure I believe him though.” Jessica’s giggle at the statement coincided with her toe pushing against his plug again. “So I spent the rest of the night pleasing her. It turns out she just needed someone to really take control of her. To show her who was boss. After doing that once or twice she turned into the perfect little submissive slut.”

“The next day she was breaking up with him. I think she thought that her and I would hook up. Instead, I mentored him even more closely. He quickly turned from a pathetic excuse for a man into the perfect little employee. To this day he is still one of my greatest success stories.”

Rachel’s focus changed to the food before them, clearly having finished her story. The end of the story brought about an end to the ministrations of Jessica as well. Even Deedee placed his leg back down onto the seat as she too began to nibble off the food in earnest. The sudden change of pace and odd ending of the story left Trent reeling. None of it made sense. Questions about why Jessica had done that while in front of Rachel circled his mind. Around those rotated questions about if the story had somehow been about him. Confused, he looked around the table and spoke his mind. “Like, I don’t get it.”

The trio around him laughed good naturedly as he sat there glancing around trying to figure out why he didn’t understand the joke. Rachel’s eyes linked up with Trent’s and she quirked a smile. “Jessica hun, why don’t you take Tiffany here and go see if you can find some dessert? Maybe explain the story? I think Deedee and I need to chat.”

All three women moved to step out of the booth and make way for Jessica and Tiffany. Linking her hand around his, Jessica began to pull Tiffany back towards the bathroom. “Let’s freshen up first.”

Trent looked back at Deedee with fear in his eyes as he realized that Jessica was going to lead him back into the women’s room. Realizing that this was the first time he would cross that threshold in public, his eyes pleaded with Deedee to save him. Her slightly predatory smile gave him no respite. “Don’t forget to redo your lipstick Tiffany dear.”

So it was that Trent was pulled into the small women’s restroom behind Jessica. As her fingers flicked the lock on the door closed, he turned to her to ask why he needed to be here. The words never made it out of his mouth before his dream girl crushed their lips together. The pair molded into each other as Trent became overwhelmed by need. Their hands were all over each other as they moaned into each other’s mouths.

Jessica’s hands slipped down to Trent’s round skirt covered ass and slipped her hands under the soft material to grasp his bouncy bubble butt. Trent’s hands slipped to the place he had forever dreamed of and grasped at her breasts through the leather dress. A moan from Jessica came as she pulled back to stare into his eyes. “God I’ve wanted to do this to you for so long.” Her fingers worked their way to his plug and he moaned as she played with the sparkling gem.

Jessica’s voice was full of lust as she leaned in and licked his ear. “Play with my pussy baby. Hurry, we don’t have long.” Not needing any more directions, Trent’s hands slipped down her body to slide up under her skirt. The pair stared at each other as Trent’s hands slipped up to search for her moist slit. The grin on Jessica’s face grew wider as she began to tug on his plug with more ****. The warmth of Jessica’s groin almost felt like it burned Trent’s hand as it slipped up against a hard plastic cage.

“No honey, my pussy is in the back like yours.” The blonde giggled. “Didn’t you know I was the employee Rachel was talking about.”