Mailboys Uncaged Ch. 03

Mailboys Fear The Paddle

Mistress M loved to spank naked mailgirls and mailboys. There was something deep inside her that was triggered by having attractive young women and men willingly present their bare asses to her by bending over her spanking bench to be punished with the paddle. It hurt, a lot. Even knowing that, the woman or man assumed the position for punishment and stayed there until she finished. The financial consequences of disobedience were so unthinkably bad that obedience was the only reasonable option.

The wooden paddle had a dozen small holes in it to reduce air resistance. That wasn't a factor for the broad swing of the paddle but it did come into play in the last quarter inch before wood hits skin. The sting of contact was stronger because the air had places to escape. Some paddle strokes were delivered to one cheek or the other. When both cheeks were hit with the same stroke, there were actually two impacts, one on each cheek. Mistress M was not sadistic enough to do permanent damage, but her punishments left a lasting impression on the skin and in the minds of those she punished.

Known and feared by the mailboys and mailgirls, Mistress M was actually two people. Mairi and Morag were twin sisters from Scotland, and expert in the use of the tawse from their homeland. This eighteen-inch-long, two-inch-wide piece of thick leather was cut into two tails. When slapped against unprotected human flesh, the sting was immediate and the burning sensation was long lasting. They always carried a tawse clipped to their belt for on-the-spot punishment or encouragement. The mailboy/mailgirl app on their smartphones gave them the location of all their naked employees and continuously updated demerit totals.

Most of the people at D-Flowco thought it was just one person, if they've thought about it at all, because the two of them looked alike, dressed alike in black and were almost never seen together. The mailgirls and mailboys considered them to be equally bad. The sisters each worked four fourteen-hour shifts then four days off so one of them was always available during the hours that the mailgirl/mailboy program was active.

Early mornings were the busiest times. Collars must be locked into place and all the mailgirls and mailboys must be inspected to make sure their 'uniforms' met grooming standards, including shaving their genital area. Mairi and Morag lived downtown, but stayed in a small, basement apartment in the D-Flowco building on workday overnights.

These athletic, dominant fitness instructors were recruited by Naomi Oyama, manager of the mailgirl/mailboy program, from an upscale, kinky, BDSM weight-loss clinic with stationary bikes, treadmills and other exercise equipment. Clients were weighed in the nude once a week, and if they failed by being overweight, got a spanking and would do that day's workout in an ass-baring 'red thong of shame' which signalled to all they'd failed to reach their target weight. It was a more powerful incentive to skip dessert or a second glass of wine, than traditional weight management programs.

****

Mailboy for the Day, T7, was nearing the twenty-five-demerit threshold. It was approaching 7:00pm when his shift would end. Ross started later than the others because of the time it took for his manscaping to remove all the hair from below his neck for his day as a mailboy.

Mistress M found him attractive and wanted to paddle him. She also thought he was too soft on the mailgirls he encountered in his usual job. It undermined her authority to have D-Flowco managers treat her mailgirls in a too-friendly manner. She wanted him to stand before her and obey, as she showed him the paddle and ordered him over the bench. She wanted to teach him a lesson.

T7 knew he had only a few minutes left. He started the afternoon at sixteen demerits, and had received a few more here and there. Sure, he knew his way around the building, but he didn't necessarily know the fastest way between any two offices the way experienced mailgirls do. Should he run up the stairs to the third floor and then across, or should he go across first and then up the stairs? All deliveries were timed based on the shortest times, and he was not meeting that standard.

As his afternoon as a mailboy continued, he was just a little bit late for several deliveries and his demerit total slowly grew. One resulted from a pickup from CEO Melanie Jenssen. There was no receptionist in sight, and he didn't really want to walk into her office naked and unannounced, but when his MMU beeped to tell him he was late he knocked on her door. She called him inside and moved in very close to transfer a message to his MMU. He could feel her eyes on his butt as he walked away.

When he got the twenty-fourth demerit, late in his shift, he really started to sweat. Getting twenty-five would earn him a paddling he did not want. He'd seen the mailgirls and mailboys get punished, and he knew it was a most unpleasant experience.

The idea of joining his buddies in a putting contest to support charity was great. He did not expect to lose. Even as he did naked deliveries for the first time, he thought he could do it as well as anyone else. In this moment, he wondered whether a little bit of arrogance was going to get him in a lot of pain.

Mistress M had been tracking T7 on her smartphone. Now that he was close to finishing, she hoped he arrived at the shower room without earning twenty-five. She wanted him to arrive with a sense of relief, and to think he had escaped her paddle. That's when she'd order him to toes position for an inspection which she would fail him on and issue one or more demerits to make his feared paddling a reality.

Bashir, Scott and Dean were all waiting for Ross to shower, get dressed and join them for a beer. They watched through the one-way glass, as he entered the shower room. They saw his relaxed expression change as Mistress M ordered him into toes position and change again as his MMU flashed red when Mistress M issued a demerit. They could not hear anything, but they watched in disbelief, as Mistress M pointed her paddle toward the bench. For each of ten strokes of the paddle, they imagined how much it must have hurt and how lucky they were to be watching instead of being paddled.

Iris, from his office, was watching, too, but not with the group of managers. She let out a sob when Ross jerked from the first impact of the paddle and thought it was all her fault because of the demerit she had caused him to get that morning. She had no way of knowing that Mistress M would have issued several demerits, if that's what was necessary to push T7 over the twenty-five-demerit threshold.

Ross showered and emerged from the change room a few minutes later. He walked awkwardly because of his sore ass, but was relieved that his one-day ordeal was finally over. His buddies greeted him warmly, praised him for his performance and his bravery, and said they'd all stand up in the bar together with him tonight because Ross obviously wouldn't be sitting for a while.

****

Mailboy 22 was a favourite of many of the women at D-Flowco. An informal group met for coffee on Monday mornings to talk about what they'd been doing on the weekend. The time on Monday was flexible because it was based on 22's schedule which was posted online. They met for coffee at his scheduled morning break because that's when they could watch him in the shower washing off the sweat from a couple of hours of delivering packages, envelopes and electronic messages.

The women were experienced managers. They had worked through the controversial start of the mailgirl program when several of their co-workers quit and urged them to also quit as a protest against naked mailgirls running around the office. They were all pretty and in good physical shape and they knew that made them vulnerable to being coerced into becoming mailgirls. They liked their jobs and the pay was good, so they worked hard, earned excellent performance scores and were careful not to make mistakes.

For 22, getting sweaty was inevitable because all of the deliveries were timed, and being late earned demerits that could result in him getting bent over the spanking bench and paddled. He was in great physical condition, and his dark Latino looks were very attractive.

Another thing that could earn him a lot of demerits was getting an erection. That was forbidden, and mailboys either took the anti-erection pill or were locked into a metal cock cage. Speed-walking naked around the office making pickups and deliveries was arousing, but the pill he took every morning when he arrived at the change room, protected 22 from erections all day long. He did not, however, like taking the pill every day. "I don't really need this pill," he said to himself, one morning on the way to work. "I've been on nude beaches a lot. I got a little bit erect the first couple of times, but that was years ago and I've learned to control it." That morning he bit the pill in half and only swallowed half.

The women's group watching him in the shower every week, had speculated about what his cock looked like when it was stiff. On that same day, three of them decided to have a little contest to see who could get 22 hard. A photo would prove success. He showered and did yoga with beautiful nude women every morning, so how could women in office attire cause his cock to swell? If he was the man they imagined he was, seeing a forbidden glimpse of a woman underneath the revealing clothing she was wearing, might turn him on.

Touching a mailboy or a mailgirl was prohibited, but they discussed unbuttoning two more buttons on their blouses or accidentally brushing past him, as he stood waiting for a pickup. Carla, the more senior manager, had access to summon a specific mailboy, so she offered to coordinate the plan that afternoon. She would schedule 22 to their three offices one after another.

Nancy was first. She had changed into her yoga clothing after lunch, and was standing when 22 arrived. Turning her back to him she bent forward to tie her shoelaces, giving him a full view of her ass through thin tights. She wore nothing underneath, and 22 could surely see the curve of her butt and outline of her labia. Turning her head to look behind her before she stood up, she stared at his cock, but there was no reaction. With an unhappy look on her face, she bumped her phone against his MMU to transfer the message to Francine and then 22 left.

Francine was second. In the privacy of her office, she took off her jacket, blouse and bra. She pulled her scoop-necked blouse back on again and let her 38D breasts push against the thin fabric. Her erect nipples made it obvious that she was braless. When 22 arrived at her office, she leaned forward giving him a full view of her large breasts, while she bumped her smartphone against his MMU to receive one message and transfer another message. He couldn't help himself. He looked right at her breasts, then realized how obvious he was being and looked away. "You don't have to look away, Felipe," Francine said. "I bet you'd like to hold them in your big, warm hands and kiss them."

He stood up straight, and looked at the wall behind her desk. "Regulations require that all mailboys be addressed only by their number," he said. "This mailboy will hurry to deliver your message ma'am." She looked at his cock which was still, disappointingly, small. He turned away and headed for the next destination which was Carla's office.

Mailboy 22 knew he was in trouble. His penis had not obviously started to swell, but he felt the telltale tingling in his balls and knew an erection was starting to build. Nancy had a great ass and he loved the look of Francine's tits. She was right. He would love to suck on her nipples. He had admired both women before, and they had been friendly and flirty with him, but never like this. "What can I do?" he asked himself. There was no time to ejaculate, even if he could find a private place to sneak into for a couple of minutes. A cold shower or ice cubes might help, but that was also impossible. There was just not enough time and he didn't want demerits for being late. He continued walking quickly to Carla's office, willed his penis to stay small, and hoped for the best.

When he knocked on the doorframe and walked into Carla's office, he knew he was in deep trouble. She had closed the blinds and stood before him with most of the buttons on her blouse unbuttoned. Her black bra was on display. A faint hint of the perfume she wore was in the air. She held her phone in front of her, recording video of him standing in her office. "Toes 22," she said, and closed the door.

He felt his penis start to swell, as soon as he stood naked before her in the inspection position. Then it popped right up. He dropped to his knees and covered himself with both hands.

"I'm sorry. I'm sorry. I'm sorry. I mean no disrespect ma'am. Please don't report me. I'll get the paddle again and the last time I was sore for a week. I'll do anything you want," he said.

"Anything?" Carla said in reply.

"Yes, I'll do whatever you want."

"Okay. That works for me." She shut off her phone camera. "I have video of your unauthorized erection, so don't even think of changing your mind." She opened her mailboy app and booked 22 on hold in her office. "You have ten minutes to get rid of it. Do you want some ice from the break room?"

"Yes, please, some ice," he replied, so she opened her door, leaving him kneeling on the floor. She returned in a moment with a coffee cup full of ice cubes which he immediately held against his balls. He was relieved when his cock started to shrink.

"To pay off this debt, you will come to my home this Saturday night at 6:30pm. I'm having some women friends over for dinner. You will greet them at the door, serve drinks and then serve the meal. You will, of course, be in your mailboy uniform.

"What's your phone number? I'll text my address. Don't be late," she added.

The ice cubes worked, to his great relief, and his cock returned to its normal size. Carla dismissed him, and he walked away to wait on a nearby mailgirl/mailboy mat, wondering what would happen on Saturday night.

Carla told Nancy and Francine the result of the contest. "My blouse was unbuttoned when he arrived. I put him in inspection position and his erection popped up before I did anything. I was going to blow on his cock, careful not to actually touch him, but I didn't have to.

"He begged me not to give him multiple demerits so he's agreed to serve drinks and dinner at my place on Saturday night. Please come for dinner. I'm inviting a couple of other friends who I'm sure will like being served by Felipe with his clothes off."

It was 6:30pm when 22 selected Carla's suite number on the intercom. He took the elevator to the tenth floor and tapped on her door. She greeted him with a big smile. "Leave your clothes in the guest room down the hall on the left," she said. "You can wear what I left on the bed."

Two minutes later he stood in front of the mirror to adjust the white collar, black bowtie and white cuffs. He had not worn a stripper kit before, and he thought he looked very good. Carla also expressed her appreciation when he joined her in the stylish, modern kitchen. It had white cabinets, white countertops and stainless steel appliances. His cock was limp and Carla was more business-like than flirty. He was used to being naked in public and he wasn't particularly turned on.

"The oven is on to keep the hot food hot. There's room in the fridge for the salads," she added. "Stay out of sight when the food is delivered in a few minutes. Tonight's not the night for a naked pizza dare."

The intercom buzzed and the food arrived as planned at 6:45pm. They opened the packages, transferred the food to warm or cool serving dishes, and put it away.

Just before 7:00pm, Carla said, "The red wine is already open to breathe. You can open and pour the Prosecco into the tall flutes as soon as the intercom buzzes. Please greet my guests at the door, take their coats to the closet, and offer them a drink. There's white wine, as well as the Prosecco, if anyone asks.

"There will be five women at the dining room table for dinner. Once you've served us you can snack on dinner in the kitchen, but check with me frequently and be alert, in case any of the wine glasses need to be refilled."

The first two women to arrive were Francine and Nancy. They were delighted to be greeted by their favourite mailboy wearing a bowtie and cuffs. Francine was wearing a short wraparound dress, and clearly had decided against wearing a bra that night. Nancy wore a classic little black dress and tasteful jewellery. They each accepted a glass of Prosecco and stood in the living room, while they admired the view. A couple of minutes later, the intercom buzzed, and they turned to watch the front door. They were not disappointed when Mandy and Suki saw 22 for the first time.

Their eyes opened wide, their jaws dropped, their mouths hung open, as they stood there speechless at their first sight of a gorgeous naked mailboy in the flesh. Suki almost dropped the flowers she brought as a gift for Carla. "Please come in," 22 said. "May this mailboy take your coats?"

There were many appreciative comments as 22 served drinks and then dinner. Being careful not to make him spill food or drink, all five women's fingerprints were on his ass before the meal was complete. His cock got some attention too, and was up and down several times. The women liked that a lot. The conversation before and during dinner was full of laughter. The two women who did not work at D-Flowco had many questions about how Carla had arranged tonight's entertainment, but she was not willing to provide specifics.

Around 10:30pm, the other two women left together, so only the people from D-Flowco remained. "Felipe," Carla said, "let's drop the mailboy thing. You can get dressed now. You can use our first names, too."

When he returned from the guest room, she said, "I'm sure you figured out this was a setup. We all like watching you in the shower and wondered how your penis looked when it was full sized. I'm the only one who saw that at work and I gave a very positive report to the others, who have now seen it erect, too. We've had a lot of fun tonight and hope you've enjoyed being here.

"I haven't saved the video from my office anywhere but on my phone, and I'll delete it now that your work is complete."

"Let me give you a hug," Nancy said. "I enjoyed squeezing your ass and you can squeeze my ass, too." Felipe was quick to accept her offer. His hand slid down from her waist to her ass and to the bare thigh below. He lifted her skirt hem, as his hand slid back up again. With a nice handful of bare ass, he gave her muscular left cheek a good squeeze, while she gave him a kiss on the cheek.

"I'd like a hug, too," Francine said, opening the front of her wraparound dress. She was completely naked underneath. "I teased you with my breasts so you're welcome to kiss them. Holding one large breast in each hand, he gave each nipple a kiss with lots of suction. They were already erect and they got bigger in response to the touch of his lips and tongue. She pressed her body against him, as they hugged.

Carla opened her arms wide. Philipe moved in for a hug from her, too, enjoying the feel of her breasts against his chest. "I can call an Uber on my account to drive you home," she said. "There's wine left over, so you're welcome to take home a bottle of whichever one you like.

"We're going to continue to watch you in the shower," Francine said. "It's a turn-on for me, and helps me work all day with a smile on my face and a tingle in my pussy. I hope you think of us when you're rubbing soap all over your body in the shower, but don't focus your thoughts on my breasts too much. We don't want you to get into erection trouble again."