Gregory Gets A Pretty New Babysitter

“I told you, your opinion on this matter is moot,” said Brenda when Gregory begged her to cancel the babysitter she had hired to look after him while she went out for the evening. Brenda had hired Jessica to look after him while she went on a date. Jessica was the daughter of a neighbor and a senior in high school who was willing that evening. Before Gregory could try to reason again with Brenda, the doorbell rang, and she opened the door to the babysitter. Gregory was lovestruck by Jessica’s figure. She had long brown hair, perky boobs, and was very beautiful. While Gregory played in his room, Brenda went over the house rules with Jessica and explained his bedtime routine and how he needed a bath roughly an hour before bed. Brenda and Jessica reached Gregory’s room, and Brenda showed the babysitter where she could find the wipes, diapers, cream, and the onesie for after his shower.
Gregory’s face was as red as a tomato from the embarrassment of being seen wearing a diaper by such a beautiful young lady, and he avoided her eyes the best he could. While Brenda explained the last things to Jessica, Gregory could only take small glances at her, still hoping that Brenda would rethink her choice. The second the door closed behind Brenda, Jessica’s demeanor changed completely. She looked back at him with a mischievous glint that sent shivers running up Gregory’s spine. “Your mommy told me that you had to wear diapers, so I guessed it was, like, a medical issue, but you’ve got a onesie on,” said Jessica, looking down on him. Jessica stepped closer to Gregory, who meekly stood behind her, his eyes on the floor. “Then again, you seem to be a poor excuse for a man. Did you think you’d make a better baby?” Gregory moved his mouth, but words didn’t come out, and Jessica continued to make fun of him. Gregory was so embarrassed that he could feel his heart in his ears, and the second he tried to make eye contact with Jessica, he looked away again.
Jessica loved his weak and embarrassed expression and continued to make fun of him, hoping to see him cry. For Gregory, being belittled so intensely by his babysitter, he felt more than humiliation. Even though he was embarrassed to the point of tears, the more Jessica teased him, the more Gregory felt a burning flame growing stronger inside him. While Jessica showered and put him in a new diaper, she looked down on him and told him his penis was smaller than a child’s and that he needed a diaper. Gregory felt more excited with each insult but tried not to show it. Gregory didn’t even notice when he fell asleep. Only when he heard the front door and Jessica’s gentle voice talking with Brenda did he realize that he had been dreaming Jessica was still mocking him. He overheard them talking, Jessica reassuring Brenda how a good boy he was and how Brenda asked her if she was available to take care of him again next week. Hearing Jessica agree to it made Gregory wish the weekend would arrive fast.

Aunt Brenda

1-888-430-2010