A Work Day with Miss Deb Pt. 02

This is the second part of a multi part story following our heroin, the 50 year old Miss Deb, also known as the Handjob Queen, through a normal work day supplying relief to her clients.

Her next client was due at 10 a.m. so she had a bit of time to kill. Cole was gone before 9, so she had another cup of coffee and watched TV for a bit. Her next client was another of her "Good Boy" crew, the younger members of her client list. His name was Jack, and oddly enough it was his mother, and friend of Debs who had set him up for his first appointment with her two years prior.

Jack is a bit of an enigma. A tall young man of 22, he still lives with his divorced mom while attending a local university. Painfully shy, he came off a little nerdish on first meeting, but the boy had a body men would pay for. Washboard abs, large muscles bulging throughout, and a very long dick. His normal attire and glasses triggered the nerd vibe, almost like a Clark Kent look. When his high school flame broke up with him after graduation, he became more introverted and depressed which is what led his mom to set him up with her friend Deb. His mother knew that the best way to get a man out of a funk was to supply some sexual relief, but there was no way she was going to do it for her own son! Luckily, she was close enough with Deb that she knew what her friend did for a living.

At this point in their working relationship Deb was convinced that Jack would do anything for her, and she was probably right. But rather than keep the status quo she had used their appointments to help the kid with his self-esteem as well as give him advice to help with relationships, of which he has had a few she was happy to report. In fact, he had a pretty good dating life now but still kept a monthly appointment with Deb. She was sure that the main reason was because he was loyal to the woman who had helped him, plus it was an easy way to get a nut that his momma was paying for!

Deb really enjoyed Jacks visits. She never even asked him what he wanted to do, she just guided him into whatever scene she had in mind. Because of this Jack generally got a little more "attention" than the other regular clients. Today would be no different.

Jack pulled in right on time and walked straight over to give his "mentor" a bear hug with those lovely biceps. Deb hugged him right back.

"How are you doing my young stud?" she asked.

"I'm great Deb. Just started an evening job for some extra money and still dating Mary who I told you about last month," Jack told her.

"Is she putting out for my man?"

"Yes she is! She has a little problem because she says I'm a little to big for her, but we work around it," he laughed.

"I'm sure you are bottoming out in her with that long tool of yours. That can be painful, and I trust you do pay attention to make sure she's comfortable?"

"Oh yes ma'am," he said. "We try different positions to make it better for her."

"You are a good boy Jack," she said. "Now get those pants off."

He quickly did as he was told, standing in the kitchen with that beautiful hard cock pointing straight in front of him. It had a slight upward curve and was just a marvel to look at.

"Go ahead and strip down so I can get my eye candy for the day as well," Deb told him.

Again, he followed her direction and was quickly nude. She walked around him, stroking and petting him all over. Across his hard stomach, up his chest, and around to grab his ass. She pulled off her shirt and rubbed her large titties into his back while reaching around to grab his cock with both hands. He wasn't super thick or veiny either for that matter but was long enough that when hand over hand the head was still showing. She squeezed. He moaned.

She slowly slid around to his front keeping her breasts in contact with his body while doing so. She grabbed a pad off the kitchen chair and tossed it down in front of him. As she lowered herself to her knees in front of him, she made sure to let her tits drag across his cock. Again, she grabbed his meat with both hands, then placed the head into her mouth, sucking lightly. This was going to earn her a spanking when Jim got home, so she figured she probably ought to make it worthwhile. Her panties were definitely getting damp by the time she dropped one hand to his balls and started sucking the young man's cock. With her right hand around the base of his penis she could just get the rest of it into her mouth without gagging. She pulled down on his nuts with her left hand while stroking and sucking him.

Yes, this was quite a bit more then most clients get. Especially without paying extra. But she had feelings for this boy that she had helped along. And she was horny. There was that.

She kept constant tension on his balls while she sucked his cock. He was lightly thrusting in time with her, one hand hanging to his side and the other lightly holding her ponytail as they worked together. He could feel the tingle of his pending orgasm start and his balls pulled up against her gentle pull on them.

She stopped sucking long enough to ask, "Are you going to cum on my tits or in my mouth, good boy?"

"Mouth please," he groaned. "Please!"

"I could have guessed as much," she laughed, then resumed sucking and stroking his member. His balls pulled up tight against him so she reached through his legs with her left hand and started to ever so lightly run her index finger along his ass crack. When her finger got to his hole she lingered there, rubbing circles around it. Again, he moaned but louder. He was starting to lose control and she knew it. He was respectfully face fucking her basically. When he started cumming she applied pressure to his back door. Not entering, but steady pressure pushing forward as the thrust into her fist and mouth. She lost quite a bit of his semen, so he ended up both cumming in her mouth AND on her tits. When he had settled and started to soften, HE was the one that went to retrieve the towel. Yes, she had taught him well.

He hurried back with the warm towel and cleaned her off as she stood in front of him. Only then did he clean himself.

"Thank you so much Miss Deb."

"You are so welcome Jack," she said running her hands over his pectoral muscles on last time before he got dressed. Her damn panties were now wet. Not damp, but wet. But that would come in handy for the next client she thought.

As usual, small talk was made as Jack got dressed and Deb put her shirt back on. He was nearly skipping back to his car as he headed out. She smiled and waved from the door.

Now she has over an hour until the next client. Her pussy is tingling, and she thinks this would be a good time to text her husband an update of how her day is going. If she's sitting here horny, he should be as well.

After she'd told him how she'd sucked off her young client his text read: "Darling, you know you will be reddened up for that when I return. And I'm hard as a rock right now at work, so you'll be getting some punishment for that as well. I miss you sexy."