As he became more relaxed, some of their queries became more personal.
“How long since you had sex? I mean, used him?”
He found himself being open. “Last Friday, but a lot has happened since then. It feels like months already.”
Another man seemed to stare at the lock as others conversed. Then asked, “Does it hurt?”
Richard certainly had an answer for this. “Sometimes. But what surprised me, is that it is almost comforting, like a security blanket.”
They stared back at him like he was crazy.
“If you squeeze yourself in your hand really firmly, or have your wife do it, that is how it feels. The harder you try to get, the tighter it feels. I’m desperate to get out and cum. But it also can feel good.”
Later, in another department, a young woman asked, “Are you angry about being locked up and humiliated like this?”
He knew he was not angry, but had to think about his answer, so was quiet for some time.
“No, no I don’t feel any anger. I mean, think about what I’ve been doing. I think I deserve any torment Jenny decides upon, don’t you?”
The young woman grinned. “Yes. It’s good to know you do too, though.” She leaned forward, exposing her cleavage to him, and her eyes lit up as she saw the bulge in his pants bob.
Richard made it back to his office after three hours of interactions. All of the talk about his situation, the glimpses of flesh, and flirtatious females had him almost apoplectic. His shaft was straining against it’s prison, and he had a wet spot on the front of his jeans.
He had waited as long as he could. But now his bladder and his bowels made it obvious he should not have forgone his morning sabbatical. He made his way the short distance to David’s office.
He was standing with his legs crossed, but David was on the phone and held up his hand for Richard to wait. He was really struggling at this point; afraid he might mess himself.
After five minutes, David finished his call, “Sorry, Dick, that was important. What’s up?”
“I umm, I need to go to the bathroom.”
David stood, “Okay, let’s go.”
Richard started walking quickly to the men’s room, “Uh, you have to go with me?”
“Your wife was quite clear. She said if you were not supervised, you most certainly would jack off. So yeah, I have to go with you.”
In the bathroom, David used his key to unlock the padlock. He had Richard lower his pants, then reattached the lock.
“We can’t just take it off for me to pee?”
David chuckled. “I ain’t tryin’ to get your hard-on back in that little cage. Mrs. L said you could piss with it on.”
Richard went into a stall. David leaned against the row of sinks to wait. When Richard was done, they reversed the process so that the lock was visible again.
Before they walked back out, David calmly admonished, “I am not thrilled about taking a grown man to the bathroom either, but do not wait so long next time. It is what it is, so make the best of it.”
David seemingly went everywhere with Richard. This was not really that unusual. As executive assistant, Katrina had done the same. While Richard would be talking to someone, David would be taking notes regarding memos that needed to be sent, phone calls made, directives written as a result of the discussions. Supervising his “boss” was just a fortunate side effect.
As Jennifer and Richard walked past security on the way out of the building that afternoon, he noticed the “Dick’s Dickless Oral” box was in place. It had a graphic of a man on his knees with his head buried between a seated woman’s legs on it, along with instructions.
In the short time they were in the lobby, Richard observed half a dozen women stop on their way out for the day and drop in their business cards.
That evening at home, Richard was reminded to strip as soon as they walked in the door. Maria had dinner ready and ate at the table with them. A new norm had been set. After dinner, she began to clear the table.
Jennifer stopped her, “Dickie will get the dishes tonight. Let’s go in the living room and relax with some wine.”
After he had finished the dishes, Richard joined them.
Jennifer asked him how his first day back at work was and how he was doing with the chastity. He explained how he had been surprised by the staff’s attitude towards him, that it was mostly positive.
“And how is little Dickie doing?”
Richard hesitated to gather his thoughts and decide how honest to be. “Every little thing arouses me. He is trying to get hard almost constantly, and seeping pre-cum. It’s been leaving wet spots on my jeans.”
Maria, affected by the wine, began giggling uncontrollably. After she had gone on for nearly a minute, laughing more each time she looked at Richard, Jennifer, also laughing now, asked, “What? What is it?”
Maria held up her hand as if to say “hold on” then ran into the bathroom off of the kitchen. She returned a few minutes later holding something behind her back, bursting into another giggle fit upon seeing Richard.
After regaining her composure somewhat, she showed them what she had. Using medical tape, she had fashioned a little hat out of a feminine hygiene pad. She placed it over the shaft portion of his cage.
Both women erupted into fits of laughter again. Jennifer finally caught her breath, “There, problem solved! Anything else?”
Blushing furiously, Richard’s cock pulsed, visibly bouncing. The humiliation was a tremendous turn on, he had discovered.
Against his better judgment, he blurted out, “Please…. PLEASE, I NEED to cum so bad! I haven’t gone this long since I became an adult…I can’t take it, please….”
Both women looked at each other silently for a moment, then laughed again.
Jennifer took a sip of wine, “You can beg all you want, in fact I encourage it. It is satisfying to know our little program is working. It isn’t that I don’t care. I am sympathetic. But this IS happening. You will not have an orgasm until I have more notches than you.”
She sipped her wine some more. “Does engaging in sex acts make it worse? Or better?”
He looked down. “Both. It feels really good to have an outlet by making you cum. But at the same time it’s like every-time I see or feel someone else get off, it ratchets up the arousal another notch. You know how a ratchet works…until there is a release, it just keeps getting higher and higher and higher. I did not know I could be this horny.”
More wine. “Awww. Poor baby. Well, buckle up. We have to get you trained up for the weekly raffle. It is time for more cunnilingus practice. I think since she helped you out, Maria should get to go first tonight. Then I’ll take you to bed for mine.”
Maria smiled happily and wriggled out of her shorts and panties. She had gotten over her shyness now. She edged her butt forward on her seat and spread her legs open to expose her already moist, hairy muff in invitation.
His shaft throbbed as he dropped to his knees and dove in hungrily, like a man possessed.
He jacked up the ratchet six notches before she pushed him away. He wondered which would explode first, his cock or his balls.
His wife felt she had to have at least as many orgasms as the housekeeper, so she enjoyed seven, giving him occasional direction. She felt he was getting better…he was probably ready. But she did not plan to tell him that for at least another week.
On Wednesday he was in his office when David leaned in. “Kat called. Your wife would like you to come by and see her office. Apparently, the decorating is finished.”
When they arrived they found Katrina sitting at a nice desk in an outer office. There was a couch against one wall. David sat on the leather couch and chatted with his wife while Jennifer showed off her office to Richard.
When Richard stepped back into the room with Katrina and David, he was visibly nervous about carrying out the instructions Jennifer had given him.
David let him off the hook to an extent. “It’s okay. Jenny already asked us about it. You better get to it. We have a meeting in two hours.”
Katrina turned her leather office chair to reveal she had pulled her dress up and wore no panties. “Jenny told me I needed to experience that tongue on my G-spot. I feel privileged that Jenny wants me to help with your training.”
She glanced downward, indicating he should get to work. He looked sheepishly at David, who shrugged as if to say, may as well get to it.
When he knelt down between her legs, she gently guided him to crawl under her desk so she could continue to work at her computer or talk on the phone. Then she scooted forward in her chair and spread her legs enough for him to gain access to her sex.
Richard began slowly, kissing and nibbling on the flesh of her thighs, occasionally caressing her with his tongue. OMG, she smelled amazing. He recalled her scent from the times he had fucked her. It had always aroused him, but he had never been this close before. His heart raced, and he had to focus to calm himself.
Being in this position brought back memories. Amazingly erotic memories. Of all the women he’d had other than Jenny, Katrina had been the most…fuckable. Her sex was full, with puffy lips, and tight. She must do Kegel exercises or something, he thought. And she had all the right moves and rhythms. He also recalled her talents as a fellatrix. He could never admit it openly, but there was a reason he had coaxed her under HIS desk so frequently. She could draw the finish out for as long as she wished, keeping her prey on the edge the entire time.
All of these memories filled his mind in a rush. Coupled with her scent and her flesh surrounding him, it overwhelmed him.
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