Jamie was your typical high school jock, with one exception. He had already turned eighteen and was starting his Senior year at a brand new school. After getting caught dating his math teacher and the gossip that followed, his parents thought it best that he get his priorities in order. Being one of the best pitchers in the area and a lefty to boot, Saint Mary's, a Catholic school two towns over, came calling with an offer of free tuition and a spot on the baseball team. He started making some new friends, even going out a few times, but after last year, he was keeping his head down and staying out of harms way.

Harm's way for Jamie had always come in the form of girls, particularly redheaded and built for sin. With that in mind, masturbation filled the need for relief in between a date when the urge struck. Being 6'1" with what the girls called fuck me brown eyes to go with his athletic build, offers were not hard to find. It was the second and third dates that slowed when the girls realized he was serious about staying in the good graces of everyone while he finished the year. He would gladly share a kiss or two, rarely allowing things to go much past that point for fear of ruining a good girl's reputation. These "nice" girls pushed for more, wanting to see if all the rumors were true, so Jamie getting discouraged concentrated more on his studies and the scouts in the stands watching his every pitch.

It was now April with the weather turning warm. Being a Senior, he wasn't expected to wear the school uniform and on Friday's was free to wear what he wanted within limits. Today, he was in white khaki shorts and a black tank top showing off a well developed upper body after years of weight lifting to keep in shape. He was sporting a golden brown tan after hours outside at practice, which made his killer smile that much whiter. With his brown hair feathered and parted in the middle, it was a package few did not take a second glance at when he passed them in the halls. 

With lunch period starting, he decided to enjoy the nice weather instead of the cafeteria and headed for the outside tables. Not knowing the rules, Jamie removed his shirt to get a little sun before he had to get back to class. As he was laying there on the picnic table with his eyes closed, he started to think on Ms. Mason his former teacher and the fantastic tits he got to play with on a regular basis until they got careless and got caught fucking in the nurse's office late one afternoon by the principal. Not realizing how turned on he was getting, his cock grew and started poking out the bottom of his shorts. Startled by girls walking by, they started to giggle and move quickly away; that's when he realized what had happened and quickly covered himself. Looking around and seeing nobody else in the area, he quickly composed himself praying that only a few saw his indiscretion. Sitting in biology class, Jamie was startled to suddenly hear his name being called over the P.A. system asking him to come to the office.

"Maybe something is wrong at home",Jamie mumbled to himself as he gathered his books heading to the first-floor housing administration.

Greeting Sister Mary Agnus with his best smile, he said, "Hi I am Jamie Dodd, and was told to come to the office."

"Ms. Evans will be right with you Jamie."

"Who is Ms. Evans Sister?"

"She is the new Guidance Counselor, replacing Sister Mary Elizabeth."

As Jamie sat waiting, he saw the girl who was outside at lunch when he had his cock mishap. He couldn't help but notice she was dressed better than most girls, wearing a blue blouse and black pencil skirt showing off a well-developed ass and legs holding up one sexy package.

"Jamie?"

"Here Ms."

"I am Ms.

Evans, won't you please come in and shut the door"

At twenty four, taking her first school assignment, Grace Evans never expected to still find younger guys attractive. Now here sat eighteen-year-old Jamie Dodd, and she was getting wet just looking at him. Well, that wasn't entirely true, her panties started getting moist after seeing his beautiful cock spring to life as she was walking back to her office after lunch. She was in so much lust, she took a detour to the ladies room using her fingers to get herself off. " He is hot, I need to focus," Grace thought as she took her seat to chat. 

"Jamie, I am Ms. Evans your new advisor and wanted to take this time to get acquainted"

"Thank you, Ms. Evans, I never met an advisor before and I am not really sure what you do?"

"First, please call me Grace as I believe in an informal atmosphere in this office. Second, my job is to take you in my hands and watch you grow to your full length, excuse me, I meant potential."

Jamie couldn't help but notice that as Grace was talking, she was tracing a circle with her pen around her magnificent tits making it very hard for him to pay attention.

"I am sorry Grace, what did you ask me?"

Jamie looked up from her breasts to look at her as he asked this and her eyes had a very familiar look in them. A look he had seen before, one that his old teacher had just before they made the choice of lust over common sense.

Grace knew her teasing was turning him on, she could see the outline of her efforts pushing against his shorts.

" I asked if you had the tools needed to succeed? I would very much like to give you 100% of my attention."

Grace knew she was sending out a signal, her mind was telling her she was making a huge mistake. Her desire was winning the internal struggle as she knew this was going to end only one way. With the momentary silence, Jamie also knew what was happening, already skating on thin ice after his last MILF quest was doing his best to keep it in his pants.

"I believe my tools are up to the task, would you like me to hammer home that point for you?"

Grace came around her and took the chair next to him.

"Jamie, I think we need to make sure you can handle anything that pops up and I would love to give you my full attention."

" I would love that Grace, but I have made this mistake before and it ended with disaster."

Writing down her number and address for Jamie, she handed it to him with the promise of no regrets leaning in giving him a long soulful kiss.

"This will be a fun ride Jamie, take it with me?"

With that she reached under his shorts and gave his cock a squeeze, telling Jamie to call her as she sent him back to class with a major erection and a lot to think about.

Grace stood with the door closed opening her desk drawer pull out her Nun's habit.

"What am I doing, two more weeks until I take my final vows and become cloistered with the Little Sisters of the Poor.
I have to scratch this one last itch or I may regret it someday."

Jamie, on the other side of the door, was lost in his own thoughts as well.

"School is almost done, I will be in college or playing baseball somewhere. Why can't I ever start making choices with my big head and not the monster?"

With that, Jamie took her number and shoved it in his pocket knowing he would be calling her very soon.