The Babysitter |

Pete missed Emily dearly. He was older now, and his longtime sitter’s services were no longer needed. Pete had grown close with Emily during their time together. She was always so kind and loving towards him, and she took good care of him.

Now, at eighteen years old, he missed moments that he never appreciated when he was younger. He missed playtime with Emily. He missed being tucked in at night. One thing he thought he’d never miss was being reprimanded when he would get on her nerves. He loved being a good boy for her, and the thought of her being mad at him was devastating back then. Now, he would remember those times fondly. Her rare emotional outbursts were proof she cared deeply for him.

He recalled his dad spanking Emily from time to time when she’d mess up and wondered why that treatment was only reserved for her. He questioned why no one cared about him enough to spank him when he was bad. He felt left out and lonely.

Often, when he was alone in his room, he’d fantasize about his babysitter taking him over her knee for a bare bottom spanking. These repeated thoughts usually led to heavy orgasms. The kind of release that couldn’t be replicated by viewing the popular porn his friends raved about.

He realized early on that his ual desires weren’t normal and kept them hidden from his friends and various partners out of shame. Privately, he’d view spanking videos or read stories, but his best experiences were when it was just him and his mind alone, dreaming up scenarios involving Emily.

As his need increased, it occurred to him that he could probably contact Emily. He was sure her number was still in his dad’s phone. The thought was scary, though. What if she rejected him or was disgusted by what he wanted? Even worse, what if she told his dad? He figured it would be best to leave her alone, and he resolved to fantasize in silence, but the need kept increasing.

One day, he saw his dad’s phone on the counter. A twinge of excitement arose in his chest. He saw his dad engaged in conversation outside with their neighbor, so he quickly grabbed the phone and sent Emily’s contact information to his own phone and deleted the text out of his dad’s message hi. More excitement tingled through his body when he felt his phone buzz in his pocket.

For several days, Pete contemplated texting Emily, often drafting a message before chickening out and deleting it. Over time, his obsession grew as Emily occupied his mind daily. He decided he had to try, because doing nothing was driving him crazy, so he texted her, choosing his words carefully.

“Hi, Emily,

This is Pete. You babysat me for years. I was hoping we could chat.”

Chills ran up and down his spine as he hit send. The text was innocent enough. He didn’t know whether he actually wanted her to reply. If she ignored him, it would at least give him some closure, and he’d know to stop pursuing. If she answered, he’d have to actually tell her why he contacted her, which was the scarier option.

He couldn’t put his phone down the whole day, checking it constantly. He began to think maybe she was ignoring him. Every time his phone received a notification, his excitement was met with a lame email or sports update. He was tilting, regretting sending anything and trying to stifle the rising panic in his chest when his phone buzzed unmistakenly in his pocket. He quickly took it out, and sure enough, there was a text from Emily. Excitedly, he ran to his room to read it in private.

“Hi, Pete, I’d love to chat! 🙂 Would you like to call tonight?”

Pete’s heart was pounding. He didn’t think he’d get this far. He would rather keep texting where he could carefully choose his words, but he wasn’t about to decline her invitation.

“Yes,” he texted.

“How about now?” she asked.

Pete took a deep breath, trying to settle his nerves, and hit call.

“Hello?” Emily answered quickly.

“Hi, Emily,”

“Hi, Pete.” An awkward pause followed as Pete struggled with his words, unsure of how to proceed.

“Is everything okay?” Emily asked with concern.

“Yes, yes. I just miss you a lot, and I’ve been thinking about you lately.”

“Aww, I miss you too, Pete. I loved spending time with you. You were so fun to hang out with.”

“II just wish we could hang out again.”

There was a short pause as Pete waited anxiously for Emily’s reply. “What’s this about, Pete?”

He didn’t know what to say. Panicking, he hung up. “Idiot!” he yelled at himself while putting his face in his hands and pulling at his hair far past the point of pain. His anxiety was on overload as he closed in on another panic attack, which had become more frequent lately.

His frantic state of mind was interrupted by his buzzing phone. It was Emily calling his phone. He answered the call, remaining silent.

“Pete?” Emily questioned softly.

Her voice calmed him down immediately. “Yes?”

“Talk to me, hon. What’s going on? Is everything all right at home?”

“Yes, everything is fine,” Pete answered, realizing it was now or never. “I’ve just been craving something, and I’m too afraid to ask.”

“What is it, hon?”

Pete took a deep breath. “I want a spanking.”

The following silence was deafening. Pete felt the panic returning, but once again, her calming voice centered him.

“Pete, I want to understand what you’re saying. What do you mean you want a spanking? You need to tell me exactly what you want. Don’t hold anything back,” Emily encouraged.

Pete took a moment to gather his words. “Sometimes, I miss when you would get mad at me and scold me, but you were always too nice to discipline me. I didn’t have anyone to keep me in line with a firm hand. I know my dad spanked you when you were bad; why did no one spank me? I’m sure I behaved badly enough to deserve a spanking.”

“You certainly did sometimes,” Emily responded, deep in thought. “I didn’t know you knew about my spankings.”

“Well, you weren’t exactly quiet,” Pete replied jokingly. He felt like a huge weight was lifted off his chest, having confessed his desire to her.

“Well, Pete, I think you’re right,” she said after another long pause. “Someone needs to teach you a lesson, and I don’t think it’s gonna be your parents. You got away with so many things. It’s time you answered for them. We’ll see how quiet you are when your bottom is being lit up like Christmas.”

Pete’s knees weakened at her words, his hard on pressing outward in his shorts. “Text me an evening you can come to my house. Arrange to stay the night; you won’t want to be driving home when I’m finished with you.” She hung up, her last words ringing in his ear. He texted her that the following weekend would work.

The few days leading up to the weekend were the slowest days of his life. The anticipation and trepidation drove him wild, but the day finally came. All he could feel was wave after wave of excitement.

On the day of, Pete received a text from Emily. “Do you still have your pajamas you used to wear?”

“Yes, I do,” Pete replied.

“I expect you to bring them with you. Also, no boxers. I expect you to wear the same tidy whities you used to wear.”

“Yes, ma’am.”

“Please arrive at 7:00 sharp. Don’t be late.”

Pete drove to the address Emily had given him. He thought about purposely arriving late but decided not to push it. She answered the door, smiling warmly. She was as beautiful as he remembered, wearing her short shorts and comfortable tshirt, her blonde hair falling over her shoulders. She hugged him joyously and pulled him inside.

“I’m so happy to see you, Pete! I’d love to catch up, but we have some business to attend to. The guest room is down the hall. That’s where you’ll be staying tonight. Did you bring your pajamas like I asked?”

“Yes, ma’am,”

“Good boy. Now, go to your room and change into them. I’ll be there in a minute.”

Pete entered the bedroom. It reminded him of his old bedroom growing up. The room was very small, with a twinsize bed in the corner. He changed into his pajamas, which were a bit small for him now, and sat down on the edge of the bed, waiting nervously.

Emily entered a minute later, holding a nastylooking wooden hairbrush. Pete was fully aroused, watching his longtime babysitter brandish the hairbrush. Emily sat down next to him, setting the hairbrush down on the bed. Pete’s eyes were fixed on her long, tan legs.

“Pete, this has been a long time coming. There were many times when I was watching you that you were very naughty. You purposely got on my nerves many times. I should’ve spanked you good and hard then, but no matter, I’ll make up for it all tonight. I’m going to send you to bed tonight with a blistered bottom. Now, stand up.”

Pete obediently stood up in front of her, his erection poking out the front of his tightfitting pajama bottoms. Emily reached up and pulled down his pajama pants, sliding them all the way down to his ankles. His white cotton briefs fit snugly, outlining his arousal in embarrassing fashion. “Bend over my lap.”

Pete obediently positioned himself over her bare thighs. He felt a rush of pleasure as his hard penis pressed into her legs. She put one arm around him and placed her hand on his bottom, positioning him so his top half was supported by the bed with his feet on the floor. His thin underwear was the only layer of material between her palm and his bare bottom. She started spanking him firmly with her hand, one after another.

The impact was hard, but not too painful. Pete enjoyed the smacks while being held close by her. His erection grew stronger against her leg as she spanked his bottom. He felt wonderful, finally getting the punishment he wanted for so long.

After a few minutes, she stopped and lowered his underwear, baring his bottom. He didn’t resist, enjoying the erotic feelings of his underwear coming down at the hands of his beloved babysitter. The cool air washed over his warm bottom. Her soft hand rubbing gently over his cheeks. His hard penis was pinned against her bare leg, adding pleasure with each movement.

She began spanking his bare bottom hard with her hand, landing stinging smacks to his exposed flesh. The pain was higher but still manageable, and Pete quickly fell into a trancelike state, feeling the rhythmic impact to his backside. He could feel an orgasm approaching and did all he could to limit his movements against her leg. He did not want this to ever stop. She continued for several minutes, covering his bottom with sharp spanks until it was glowing red all over.

Emily stopped, examining his red rump in contrast to his white underwear halfway down his thighs. She knew he was enjoying every bit of this. “Go stand in the corner, young man, and face the wall,” she ordered.

Pete obeyed, shuffling his way to the corner. His underwear fell down to his ankles to meet his bottoms. Pete didn’t bother picking them up.

“Hands on your head,” Emily ordered.

Pete was thankful to have a break, not only because of the pain, but he had been extremely close to an orgasm for an extended amount of time. His penis ached for a release, still standing at attention. He stared at the wall, listening to his babysitter scold him.

“This is far from over. You’ve been a very naughty boy. All those times I took care of you, and you talked back to me like an entitled little brat. You were so frustrating, and I’m going to take out all of that frustration on your bare bottom tonight. It is very red, but not quite red enough. My hairbrush will ensure your bottom is fully punished before the evening is done.”

Her scolding only made his penis ache more. He had to stand there, unable to touch it with his red bottom on display.

“That’s long enough. Come here,” Emily demanded after several long minutes. Pete turned and shuffled back to her. She stood up, facing him, and gently helped him out of his shirt. “Step out of your pants,” she instructed. Pete obeyed and stood naked in front of her. She sat back down and picked up the hairbrush.

She pushed down on his erection with the hairbrush. “I don’t think you’re going to enjoy the rest of this, young man. I said I would blister your bottom, and I fully intend to follow through. Now get back over my knee.”

Knowing he was willingly about to endure pain he wasn’t sure he was ready for, he laid his naked body over her bare legs, fitting his penis between them. She clamped her legs together around his member and promptly delivered stinging spanks to his bare bottom with the hard wooden hairbrush.

His body immediately curled up in defense, but she maintained a strong grip, holding him in place while smashing the brush into his unprotected bottom. He cried out, pushing against her to escape. Despite his efforts, her determination unwavered. She held him tightly and forcefully brought the hairbrush down over and over again.

His cries turned to howls as the unrelenting onslaught continued. His movements became more animated, and Emily was forced to hold his legs down with her leg. With him held tightly, she worked the brush up and down his cheeks.

“No more! It hurts! It hurts!” Pete cried, struggling against her grip.

“No, Pete. You asked for this. Remember?” she said, not letting up. “You asked for a spanking. I’ve never known a spanking not to hurt,” she continued, landing spank after spank. His crying continued. “It’s hard to stay quiet when you’re being dealt with properly, isn’t it?” The heavy hairbrush was working to perfection, coloring his bottom deep red.

Pete reached back, trying to catch her wrist to minimize the damage. She expertly pinned his wrist down without slowing down. “Why do you insist on being a naughty little boy while I have the hairbrush, and you’re pinned down between my legs with your bottom bared? You must not have learned your lesson yet.”

She pounded his bottom with the brush, the loud smacks ricocheting off the walls of the tiny bedroom. “You will learn to respect and obey your babysitter,” she said, emphasizing each word with a powerful spank. His crying continued, his breath laboring.

She stopped and set the hairbrush down. “Back to the corner, young man,” she commanded. Still crying and sniffling, Pete climbed off her leg and walked to the corner. “Nose in the corner,” she directed. Pete placed his nose into the corner, his shoulders moving up and down as he cried. His bottom burned the whole time as he stood naked and displayed.

“Stay put,” Emily directed as she left the room. “I’ll be right back.” Pete couldn’t help himself. As soon as she left, he reached back to his sore bottom, feeling the heat radiating off it, his hand cool to the touch.

Emily returned shortly with some skin cream. She sat down and called Pete back over her lap. Pete gratefully obeyed, returning to his favorite place over her lap. She gently caressed his sore bottom, inspecting every inch. He relaxed under her soft touch, and his arousal returned. She applied the cold cream, rubbing the lotion into his hot skin. He moaned as her fingers worked it in, massaging his cheeks. The cream burned in a good way. Pete felt fully disciplined and completely taken care of.

“On your feet,” Emily directed. She stood up with him and hugged him tightly. Pete melted in her arms, not wanting to leave. “Ok, hon. It’s time for bed. Bad boys get put to bed early.” She helped him put his pajamas back on and held the covers up so he could slide his body under them. She tucked the covers in tightly around him and sat down, brushing his hair with her hand.

“Go to sleep now. My hairbrush will be within arm’s length if you choose to disobey. Do you understand?”

Pete smiled up at her, completely in love. “Yes, ma’am. I’ll obey.”

“Good boy. Goodnight now. I’ll see you in the morning,” she said sweetly. She kissed his forehead, turned out the light, and exited, closing the door behind her.

In the darkness and privacy of the room, Pete experienced the most satisfying orgasm of his life.

He woke up to the smell of bacon wafting through the house. He remembered he was still at his babysitter’s house and reached back to feel his bottom, which was sore to the touch. He recalled last night’s events. His babysitter had given him the spanking of his life with her wicked hairbrush. The thought of being over her knee and getting his bare ass spanked stirred up his arousal again.

He got up out of bed and followed the delicious smell to the kitchen where Emily was making breakfast. “Hi, honey,” she said brightly when she noticed him. “It looks like you slept well last night,” she said as she smoothed out his hair that was sticking out every which way. She gave him a quick hug. “Breakfast is almost ready,” she continued cheerfully.

Pete poured himself a cup of orange juice and sat at her little breakfast table. They chatted innocently as Emily finished up. She served him a plate of bacon and eggs, and Pete dug in without skipping a beat. “I’m going to get some laundry going; I’ll be back in a sec,” Emily said, disappearing from the kitchen.

Pete continued eating, completely preoccupied. A couple of minutes later, Emily’s voice yelled out from his bedroom, making his heart stop. “What is this!?”

Panicked, Pete ran to his room to see what she was talking about. In her arms were his covers, and displayed on the bed was an ugly stain from his private time the night before. He had been so worked up from his spanking that he hadn’t bothered to hide his ejaculation. There it was, displayed for all to see, and it was so much more than he remembered expelling.

“Didn’t I tell you to go right to sleep last night?”

Pete stood frozen.

“Well?” Emily asked angrily, raising her eyebrows.

“I’m sorry, I had to. I couldn’t sleep,” Pete protested frantically.

“No, you didn’t have to. You chose to disobey. I can’t believe you!”

“I’m really sorry,” Pete pleaded.

“Sorry isn’t going to cut it. I can’t believe I have to teach you this lesson again,” Emily said sternly.

“No, please,” Pete said earnestly, putting his hands together. My bottom still hurts.

“Oh, it’s going to hurt a lot more in two seconds,” Emily said furiously as she marched towards the door to go find her hairbrush. Pete tried to block her path, but she was too strong, pushing her way through. Pete panicked, knowing his sore bottom was about to be lit back up.

Emily returned, hairbrush in hand and a determined look pasted on her face. “Pants and underwear down, now!” Pete fearfully obeyed, baring all once again for her. She grabbed his arm and, in one smooth motion, sat down on the bed, pulling him over her lap. She knew now to lock his legs in place right away. She held her forearm to his back, pressing him down, and started spanking his stillred bottom hard with her hairbrush.

He immediately began crying out and squirming around, trying to escape her grasp. She held him firmly and delivered blow after excruciating blow to his bare bottom. Pete’s cries continued loudly but didn’t dampen Emily’s determination.

“You naughty naughty little boy! I told you what would happen if you disobeyed, and you couldn’t help yourself,” Emily scolded sternly as she continued spanking him. “You couldn’t keep your dirty little hands to yourself. I will continue to spank you senseless until you learn some selfcontrol.”

Pete was a mess, tears flowing freely. The brush crashed constantly into his bare backside, and he could do nothing to stop it. She was angry, and justifiably so. While he protested heavily, he knew in the back of his mind that he deserved every painful spank.

She spent the next minute solely on his sit spot, hitting the same spot on each lower cheek repeatedly until she painted deep, dark red circles. Pete howled, tossing and turning, straining against her hold. “Stop struggling,” she ordered. “You’re only making it worse for yourself.”

“Pleeease,” he cried, but she ignored him and kept beating his ass with the hard wood. Pete, choking on his tears, held on for dear life until finally, after what seemed an eternity, she stopped. She set the brush down and let him lie for several minutes over her knee. She waited for his breath to return to normal, then stood him up and pulled his pants and underwear back up.

“Next time I tell you to do something, you do it. Do you understand me!?”

“Yes, ma’am,” Pete cried through his tears.

“Good, now, go finish your breakfast,” she ordered.

Pete hurried back to the kitchen table to eat the rest of his eggs and bacon. As soon as his bottom touched the hard wooden seat of the chair, he jumped back up in pain and proceeded to eat his food, standing up. When Emily came back, she corrected him. “Sit down and eat like a grownup.”

“But it hurts!” Pete protested.

“Excuse me? Did I put my hairbrush away too soon?” she warned with her hands on her hips.

“No, ma’am,” Pete answered, quickly taking his seat, wincing through the pain.

Emily sighed. “What am I going to do with you, boy?”

Pete finished his breakfast. They hugged, and Emily sent him home with a throbbing bottom and a message ringing in his ear. “If you ever find yourself in trouble again, dear. You know where to find me.”

Those words stayed in his head, taunting him. As the pain dissipated, the warmth and appreciation he felt toward Emily grew. He replayed his spanking during countless masturbatory sessions, and it wasn’t long before he began feeling desperate for another visit with Emily and her hairbrush.