A Sissy Boy is Made

"Oops." Was all Jaclyn said.

Hoping to gain approval Gregory quickly responded awkwardly, "Ah ... don't ... don't worry Ma'am I'll get them."

Smiling again, Jaclyn patted Gregory on the head as she said condescendingly, "Oh, sweetie, I'm not worried at all." Then she abruptly turned on her heel and left the room with Gregory still on his knees. Jaclyn couldn't help but giggle to herself as she exited the file room, knowing that Gregory was smitten with her, and how he had almost apologized to her when she had been the one to spill the papers all over the floor. She intended to take full advantage of this situation.

Over the next few days, Gregory found any excuse he could find to be in the presence of Jaclyn, and this didn't go unnoticed by her. She took every opportunity to tease and otherwise embarrass Gregory. She would often tease him a bit by leaning forward to give him a look down her top. She even rubbed her big round bottom up against him a few times when they happened to be in tight quarters. Jaclyn's playful verbal jabs gave him hope that maybe he could have a relationship with her, but he was too shy to actually ask out such a powerful woman. Jaclyn thought nothing of her teasing, but Gregory lived for those little exchanges.

One evening, after a really good month at the brokerage, Jaclyn invited the whole office to a local bar for drinks and appetizers. The drinks flowed and everybody got loose and was soon having a great time. Jaclyn teased Gregory mercilessly over and over right in front of the entire group.. Time after time Jaclyn sent Gregory to the bar to retrieve yet another round of drinks for the table. Jaclyn took great delight in using Gregory as her own personal waitress. Gregory understood the demeaning position he was being put in, and how everyone in the office would now view him. However, he couldn't deny her or the sexual excitement that stiffened his male rod as he did everything she asked.

By 10 P.