Spanked by the Landlady!

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Thank you, Mrs. Landino. With six years of babysitting experience, I know how to deal with bad boys. On the other hand, I've never spanked anyone as big as Jimmy. Will he give me any trouble, Mrs. Landino?"

Thus it was that Sally arrived the next Thursday night. Jimmy couldn't decide whether to be embarrassed or to congratulate himself at the propect of a diaper weekend with Sally. It was clear they both liked each other. In fact, Jimmy was extremely attracted to Sally and knew his diaper routines would probably lead to some fun betwen them. At the same time, he couldn't help but feel some embarrassment at the prospect of letting an eighteen-year old woman put him in diapers. Had she already told her girlfriends at her community college about Jimmy? Would word leak out at Jimmy's college? The conversation at dinner was even more embarrassing.

Roleplay Spankings

Janet took the phone gently from Steve's shaking hand. He swayed for a moment, then sat heavily on the floor Janet took the handpiece from him. He usually knows not to put up a fuss at diaper time, Sally, since it means a spanking. Can you reach in my diaper bag and get his pacifier? That always helps when he's fussy."

Now just relax, boy, just like we did before,” said Kim and Mark felt his hole lubed generously. He groaned at the first sensation of penetration into his rear end. Slowly, Kim worked the plug into place until it was properly seated. Mark struggled to keep calm and accept the intruder in his butt. Mark returned to his captive and savoured the sight of the helpless older woman writhing on the bed, helpless and unable to find relief. He drank from his tall glass of ice water and walked to the side of the bed. Looking at the glass he held, he fished out an ice cube and placed it just above one clamped nipple and let the melting water drip onto the engorged member.

Virtual (Phone / Skype)

When Mrs. Landino came out in the skirt, all of the sales ladies came over. One was no more than Jimmy's age and she looked at his diaper area repeatedly with a big grin on her face. Then, in the middle of a conversation with Mrs. Landino about the skirt, the oldest sales lady remarked out of the blue,

Ding-dong.” Just then the front doorbell rang, shattering the silence. I gave out an involuntary whimper, causing Mrs. Fairchild to smile widely as she squeezed my panty. “Wonderful, the ladies are here!! Now I expect little Princess to be on her BEST behavior, Auntie hopes she doesn't have to give snookums a spanking in front of the guests!” I opened my mouth to say something and the Landlady slipped her index finger in, stroking my tongue with its tip. “If Princess wears an extra pretty dress for Auntie, than she can have the WHOLE day off, how does that sound honeybunch? Just nod your head for me sweetheart.” No gloves today Princess, your nails are so pretty!!” the Landlady cooed. “You see darling,” she continued, “you were right. Yesterday's dress was far too grownup for you, this is much more suitable for Auntie's darling little sugarplum!” Yes, he did, Sally. That's because I caught him doing something very naughty." Mrs. Landino said with a wink. Sally immediately understood what she meant.Hush cupcake, Auntie can see that her adorable Princess needs a LOT of help.” Soon I was in nothing but the pink satin panties, which were tenting embarassingly. Mrs. Fairchild reached for them. “My darling girl obviously LOVES her silky panties, doesn't she?” I stood like a statute. Mrs. Fairchild frowned, and yanked the panties down around my ankles. “You just don't learn, do you sweetlips?” She reached for the large purse she had rested on a chair, and removed her stainless steel hairbrush. She then sat on the edge of the bed and crooked her finger for me to approach. He remembered being tied to a pole. Before Kim tied his legs, she pulled off his underwear leaving him completely naked. Almost cocooned in rope, Kim tormented him for an entire afternoon. Billy comments that it must be difficult to stuff an animal like that, but the landlady comments that she stuffs "all of [her] little pets [her]self when they pass away" (643). The landlady offers Billy another cup of tea, and he rejects it because it tastes like bitter almonds. The landlady insists that Billy sign the book, as she tends to forget the names of those that come to her house, and Billy asks if any other people have come through the house in the past 2 or 3 years. She looks at him out of the corners of her eyes with a gentle smile and tells him he is the only one. Yes please Auntie Dear.” Smiling, she reached over and gave my cheek a hard pinch. Then twirling me around, she untied the apron and helped me remove it. She proceeded to help me disrobe completely, dispite my protests that I could do it myself. I remembered to drop a curtsy, and I meekly asked Auntie Dear if she could help me untie my apron. This seemed to please her enormously.

Now cum for mommy, dear boy! I want to feel you cum inside me...NOW!” growled Kim and with that command, Mark shot his load into Kim’s waiting womanhood and she yelped as her own orgasm followed. Tell Auntie that you want to wear pwetty dainty frilly dresses every day cupcake, hmmmmmmmm?” Suddenly her hand was gripping the bulge of my rubber trainers while the other hand worked the pacifier furiously in and out of my wet mouth. As she continued to squeeze my diaper and rubber covered pen-s I could feel another orgasm building inside me. I frantically tried to supress it, but when I couldn't turn away from the beautiful face of the Landlady, her eyes drilling into mine and her lips now parted in a wide smile as her hands worked away. “Hmmmmmmmmmmmmmmmm?” Mrs. Fairchild began to tsk-tsk. I could feel my pen-s, still tightly caught in the vise of her thighs, shriveling. “Now look what my naughty girl has done. We'll have to do something about this, won't we Princess?” I could only shudder, imagining what lay ahead. Kim: “Oh, Mark, I just can’t make an exception. I need to worry about the apartment’s upkeep and I can’t do that without the funds from the rent.”Jimmy groaned silently once he realized Sally was the young woman his age. He was even more embarrassed when Mrs. Landino took him by the hand and said, I also forgot to mention that she would go in and out of my room to “empty the trash” and retrieve a drinking glass if I forgot to bring it downstairs. Apparently there were only 3 glasses, a shitload of mugs, but 3 glasses that could only be used to enjoy cold beverages. My using one threw her glass game off so she would travel through the house like Indiana Jones in a quest to retrieve the only other glass that would allow her to enjoy her frosty beverage kept cool by her ability to keep that refrigerator door firmly closed. I was then dragged by the hand into Mrs. Fairchild's room. A number of articles of clothing were laid out on her bed. She removed my slippers, nightgown and panties and handed me something. Room to let for clean tidy boy, non smoker, must be new student of the university, correct candidate will enjoy welcoming home of experienced landlady My my Princess, you certainly love your new dress! Auntie knew it would be perfect for you the moment she laid eyes on you!” she teased in the condescending tone adults usually reserve for young children. I felt like I was going to die from embarassment. I had to do something!