Chapter 16

The weekend seemed to have flown by way too fast. Jessie was a blast to fuck. She was true to her word, letting Sandy lick Alan’s cum from her twat. It happened more than once too. Sandy seemed to really enjoy being able to. And as much as Alan wanted to push for something more to happen between the three of them, that was the extent of it. Of course neither left the house after that first night. So if Marian and her son moved on to putting on a show involving Kyle taking his mother anally, Alan and Jessie never saw it.

Alan took the woman home with the promise to call her. He has no intention of doing so, but who knows? He keeps all the women’s numbers that he fucks, and on occasion has called up one or two for a revisit. Sometimes it was better than the first time, sometimes the same. Sometimes it was easier than going out to pick someone new up.

With the weekend out of the way, he is happy to head into work to see Judy again. He arrives to find the woman already at her desk wearing a sleeveless sweater, a black mini shirt and matching knee length, black boots. Alan only gives her a wink and says, “Good morning.” He slips past her and walks into his office. Just because they seem to finally be getting closer doesn’t mean they need to break their morning ritual.

After a few minutes he calls her in. Judy goes in and finds him standing behind the desk. She sees the big, black dildo that she stuck in his drawer this morning. “I guess you have something different in mind for today,” he says grinning at her. “It’s awfully big. I wonder if it’s going to fit.”

“It’s a favorite of mine and Victoria’s,” Judy informs him. “How else do you think I can take you, let alone hide the fact that I’ve been fucking you?”

The grin on his face turns upward into a smile. “Come here.”

Judy saunters over behind the desk. Alan turns her away to face the door with her waist slightly bent over and him now sitting behind her. She is so excited to amp it up a little. She is also scared because this could be going too far. She is in love with Victoria, not Alan. What she and Alan are doing is just something different and exciting. While she has never had a thing for real cocks, she does his, but she still likes pussy more. She still enjoys a soft, feminine woman more than a strong, masculine man. Besides, if she is going to get paid more because she sucks his cock, why not do a little more for the pay. Plus, he may just give her a raise. She starts to get wet thinking about the raise, the new game they are about to play and the big, black dildo she had planted in his desk.

“How are you after a long weekend without seeing me?” he asks softly.

“I’m fine,” she manages to say without stuttering. She really is because she was distracted with her girlfriend all weekend and didn’t think once about Alan. But coming to work with a plan and then seeing the man...

Without warning, he slides a finger in her pussy. “It seems you have started without me. You seem more than fine too.” He chuckles, reaching for the massive toy on the desk.

Excitement begins to run through the woman. She loves dildos. She especially loves this one. They are wonderful little toys, probably one of the best inventions man has ever created. And while Judy likes them in all sizes, really likes them big, textured and shaped like real cocks so that her pussy can have a good grip at it. Victoria likes them too, but she prefers the one on the smaller side. She isn’t as big on being split open wide like Judy is. What she likes the most about this one is that like Alan it is long and big. Well ... longer and bigger. Plus it’s smooth and cold! A warm cock is nice, but nothing beats one that is almost as cold as ice.

Alan rises back up from his chair and sandwiches his secretary between the desk and his body. He runs the dildo up in between her legs. His free hand sneaks under her sweater roughly to squeeze her breast. He fingers the swollen nub while at the same time begins to ever so slowly insert the toy into her pussy. Judy knew how it would go down. She knows the man too well, so she purposely didn’t wear any panties to work today. She whimpers and willingly accepts his assault on her.

When the dildo is all the way in, he turns her around and looks her right in the eye. “I know just how wet you can get with my dick, so I wonder how wet you get with this.” He grabs her hand and maneuvers it to the toy to take control and he smiles. “Why don’t you show me how you play with it?”

Judy wiggles her ass up and over the edge of the desk to give her a little leverage and to give her boss the show he wants. She pulls the toy out and runs it from her ass to her pussy. Already her cunt is gaping form the brief intrusion of the toy, just like it is after he fucks her. She is wet ... not she is soaked! She slips the fake phallus back in and is already squeezing her pussy muscles, trying to savor the sensation.

“You know, I’ve changed my mind,” Alan says. He reaches in a drawer and pulls out a pair of panties. “You left these the other day. They can be useful now.”

Judy’s eyes go wide. This has just turned from kinky to extremely kinky. She isn’t certain what the man has on her mind, but she is curious and willing to go the extra mile.

“I want you to put these on,” he begins. “Make sure that it stays in you. You’re not to remove it or come in here to suck my dick or even ask me to fuck you. Got it?”

While Alan can be authoritarian, this is the first time he has been to since she began working for him. It kind of arouses her about as much as the thought of having to do her work duties with it in her. “I got it,” she says.

Judy leaves the man to his own devices. She now has a mission. This is a bit more wild than anything she and Victoria have ventured to do. It is actually the edge she and her girlfriend need in their relationship. They have a strong bond with no signs of it breaking, but something more to add just that hint of flair wouldn’t hurt. When she sits down back at her desk, she is surprised by how the dildo nudges her cervix ever so slightly and it only happens when she is sitting in a certain position.

Usually Alan’s door remains closed, but today he insists on leaving it open so that he has a view of her at all times. It isn’t so that he can ensure that she has the toy in her, but so that he can watch her torture of having it in her at all times. Judy knows this and so two can play this game. She walks to the row of cabinets and sees him raise an eyebrow. It is the first time that she tries to actually walk around, with the exception of leaving his office and going to her desk earlier. She opens a low drawer and walks to its side so that he can see her backside. She bends forward to show him the dildo still lodged in her pussy and takes her time in selecting the documents that she wants. After she finishes, Judy leisurely closes the drawer and steals a glance at him.