Written with help from Dean.
*
Well Tommy's social life was extremely busy between sex with the principal, Dorothy Baxter, his neighbour, Jennifer and his teacher, Juliet Baker. Each one of them was obsessed for his cock. Having several beautiful older women chasing after caused Tommy's confidence to skyrocket. Tom was having sex with each of them at least once and many times twice per week. His confidence during sex was improving and becoming highly confident. Tommy heard his mother yelling to get ready for school.
Waking up was difficult this morning because he had an extended sex session with his neighbour, who rode his cock until it would not get hard again. Trying to wake up he remembered last night and his cock started getting hard from the erotic thoughts. "Tommy Tyler get out of bed and prepare for school" Tommy's mother Stacey said as she burst into the room. Unfortunately, she stopped in her tracks when she saw the massive tent.
Mom looked shock and placed her hand over her mouth. Turning away from Tommy (unable to make eye contact), she said, "Tommy get up and get ready for school. I will not write you another late slip." Jenny quickly turned around and left the room quickly but Tommy could see the blush in her cheeks. Tommy smiled as he realized his effect on his mother.
Wanting to follow his mother's instructions, Tommy quickly got out of bed and took a shower. As he soaped his body, Tommy thought about leaving a cum deposit in the shower but his neighbour had drained his balls enough that it was not necessary this morning. "Bye Mom. Have a nice day today. I'm leaving for school now." Tommy yelled as he closed the front door. Tommy started his car and drove to school.
Tommy placed his backpack in his locker and moved toward his home room class. As he moved past the administration offices, Tommy saw Dot unlocking her door before seeing him. "Tommy, can I talk to you after home room?" asked Dot.
A quick right turn and I was looking into the principal's eyes with a 'yes Dot, what do you want?' look. "Tommy, I would like to see you after home room. Come in my office and I'll give you a permissions slip for your first class," responded Dot. With a permission slip in hand, Tommy proceeded to his home room.
Following home room, Tommy went to his first class and handed the teacher the principal permission slip. The teacher told him to move quickly or the principal will get upset. As Tommy left the class, a smirk appeared on Tommy's face, knowing she will not be upset with him because he planned to be satisfying her carnal urges. After all, Tommy was the only one who called the principal Dot because he drew out the principal's hot sexy "alter ego" from the formerly icy principal.
Standing in front of the principal's door, Tommy opened the door after a quick knock. Tommy saw an empty office because the school's administrative assistant had not arrived to work yet. Tommy moved through the room and knocked on the inner office door. A husky "Come in" was heard, which reignited the blood flow to his groin. Opening the door, Tommy entered the room and saw the principal sitting on the couch.
Dot stood and Tommy could plainly see she made some wardrobe changes since their earlier encounter. Tommy could see that she did not wear a bra because those "G" cup breasts were rolling loosely. The pressed white blouse had all the buttons undone, which allowed a mile of cleavage exposure. The principal's skirt was gone, leaving expensive stockings and a tiny black lace panties.
"Well Ms.Baxter, you are looking sexy this morning. Is hubby leaving you unfulfilled?" Tom said with a huskiness in his voice.
"My limp dick husband wouldn't fulfill my needs even if he tried. I need a real man to give me satisfaction. Know anyone who could fulfil that role Mr.Tyler?" asked Dot oozing with sexiness.
Tom moved in front of the principal spread apart the loose shirt exposing her full and very firm breasts. Tommy said, "Ms.Baxter, Have I unleashed this slutty persona? I remember the nice, faithful Dorothy Baxter who was a dedicated principal and wife. Now, you throw off the educational rules and your marriage for a big dicked student. Have you changed that much?"
"Absolutely, Tom! I've stripped off the good girl persona and the slutty college girl Dot and she wants your big fucking cock to fill her cunt. And Tommy, we only have an hour before your next class, so we do not have time for small talk" growled the half-naked principal. Kicking into high gear, Tommy stripped off the white dress shirt. He picked up the lust principal and set her on the desk.
Dot was squealing and giggling, loving the big dicked stud newfound sexual confidence. Tommy began devouring the "G" cup breasts in front of him. Sucking, licking and nipping them to Dot's delight. With his left hand, he rips the flimsy and thoroughly soaked panties from her body. He placed it over his nose to inhale her scent as he devoured the firm full breasts.
"Tommy - You have become such a stud since I took your cherry. You exude sexual confidence, which is turning me on" squealed Dot. Tom was getting turned on like never before. While still feasting on Dot's massive mammaries, he began unzipping and taking off his pants.
"Good Boy stud. Show me that big fat cock," squealed the totally enraptured principal. It was fully erect and a deep purple head. When the pants were off, Tommy lifted his head and said, "Has hubby been giving you the high hard one?"
"He tried but I couldn't feel him anymore," groaned Dot.
"Well, you are going to get reacquainted in 15 seconds" growled Tom. He quickly lined his cock and fully penetrated the principal's pussy.
"Holy FUCK TOM!!!" screamed Dot.
"You are a sexual god, you fucking stud. How does my cunt feel? I bet it feels tight because your huge cock is spreading my cunt and rearranging my insides to accommodate your huge cock." groaned Dot. Tommy looked his principal in her eyes and started to power fuck the educational professional.
He pistoned in and out of the now thoroughly sloppy pussy. Dot closed her eyes and placed her head in the crook of Tom's neck. When the stimulation got to intense, she dug her fingernails in his back and bit into neck and shoulder flesh.
"Fuck Tommy I can never get enough of your cock" Dot screamed. "If my cock is rearranging your insides, let's take it one step further. Lets create a baby together! Are you on birth control? Let me claim your body for our offspring!" Tom screamed. He continued his assault on her juicy pussy and he could see her completely taken to sexual high she's never experienced.
"Yes, Yes I haven't been on birth control since our first encounter. My inner slut wanted you to claim my body for your progeny. Claim me as your woman and I'll claim it's my husband's child. When I divorce him, he will pay child support for your child," cackled Dot.
"You are an evil woman Dot. Your slutty persona would force your soon to be ex-husband to pay for another man's child. Well let's begin planting seeds in your garden." said Tommy. The fuck session got faster and more powerful with long powerful strokes.
Suddenly, Dot screamed, "Holy shit, I'm going to cum so hard!" Tom drove a couple of powerful strokes and pulled out. A stream of pussy juice arced into the air landing on the carpet and Dot screamed out an incoherent string of words. When she stopped squirting, Tom reinserted his huge cock into her inflamed pussy and drove it fully into her pussy.By now his cock was slamming into her cervix.
"Here it comes. I'm planting my seeds into your garden Mommy!" growled Tommy. "Yes, Yes Daddy make me a mommy!" screamed Dot. Tommy howled and unleashed 6 or 7 streams of thick creamy cum. The two lovers were breathing heavily trying to come down from the sexual highs they achieved.
Suddenly, the door opened, Emily Jones entered saying, "Sorry for being late for work Ms.Baxter. Oh My God!" Tommy and Dot were unable to respond because of their altered state. Tommy began pulling his still rigid cock from the principal's pussy. Emily still standing frozen in the doorway, watched the student's big, wet and fat cock becoming disengaged from its resting place.
"Ms.Jones -- please come in and close the door," Tommy requested. As if controlled by someone else, Emily did as instructed. "Do you like my cock, Ms.Jones?" questioned Tommy.
Ms, Jones nodded blankly.
"Ms.Baxter -- would you like to see your assistant clean up my cock and your pussy?" questioned Tommy.
"I think you have an excellent idea, Mr. Tyler." responded the finally coherent principal. The aide moved slowly as if hypnotized toward the visibly sloppy cock. When she stood in front of the well-endowed student, Tommy put his hands on her shoulders and gently pushed her to her knees. Tommy wrapped a hand through her red hair and gently pushed and pulled her head onto his cock.
Looking down Tommy saw she wore a provocative top exposing her pale white breasts which were not as big as her boss. Tom estimated them to be an "E" cup. Tommy reached inside her top and pulled out her right breast and squeezed it. Emily began moaning and groaning from these new sensations.
After about 10 minutes polishing Tom's flesh hitching post, the student pulled the young aide off his cock. "Ms. Jones -- you cleaned my cock very well. Now, you need to do the same to Mrs Baxter's pussy. I need to get to my next class," informed the student.
Emily dutifully began cleaning out the principal's sloppy pussy. Tommy dressed went over to the principal and gave her a smoldering kiss. He whispered into her ear "Gotta run to class, Mommy."
Dot whispered huskily "See you soon Daddy." All the while, Emily continue to lick her boss's pussy. As Tom left the office, he heard the principal groan and squeal.
Tommy went to his second class, which was Juliet Baker's class. The teacher was dressed professionally but provocatively. Wearing a mid-thigh leather skirt, a light blue shirt with 4 buttons opened and 4 inch spiked heels. Tommy took his typical seat near Chandra and Ronnie. One look at the teacher's outfit and he started getting hard (even though he just finished an intense coupling with the principal).
Tommy was able to focus on the classroom lessons to learn the topic. When the class ended, Tommy, Ronnie & Chandra began walking out. Juliet, who was seated at her desk, looked up and said, "Tommy can I talk to you?" Tommy apologized to his friends and turned toward the smoking hot teacher.
"Hi Ms.Baker, you look very nice today" commented the student.
"Thank you, Tommy," replied the MILF teacher. As Tommy closed the door and sat in the chair closest to the desk, he said, "What do you need Juliet?"
The teacher looked him in the eyes and said, "Tommy, I need you to relieve my stress. My husband has been incorrigible lately and has been withholding sex. Please Tommy, I need you bad! I thought we could go back to my place at lunch and have 4 or 5 hours together. I can give you a pass to get out of classes. I'll say it's a school project."
"Wow, that's an interesting offer. You must be really stressed to need 4 or 5 hours of stress relief," Tommy said with a little chuckle. Juliet scribbled something on a paper and handed it to the student. "Meet me in the parking lot at 12 pm and you can follow me home," replied the studly student as he glared at the luscious cleavage.
"See you at noon" said a smiling Tommy. He grabbed her arms and pulled the MILF teacher to her feet. He pulled her into a tight hug and gave her a passionate kiss while feeling the teacher's world class ass and breasts.
Tommy released her and left her staggered and she whispered, "Wow Tommy."
