Astor Heights Boy's Academy Ch. 05

Author's note: This story is completely fiction and is bases on a story line supplied by a reader. I took the basic story line and embellished it. This story will contain vaginal, oral, anal, group and bi-sexual sex. All characters are at least 18 years of age. The story got a little long so I will submit it in chapters. In this chapter Chris will discover things about Brad and Paula Penny that he would have never imagined in his wildest dreams. Rick breaks the news to Andy about his mother and Andy looks to Millie for guidance. Benji receives some unexpected pleasures from a couple of other students.

A WEEKEND OF REFLECTIONS

Paula Penny was sitting at the kitchen table enjoying a cup of coffee and reading the morning newspaper while her husband Brad was off playing golf with his regular foursome. Paula's mind began to drift and the events leading up to the marriage to Brad filled Paula's head. It had been four years since Paula then Paul had graduated from Astor Heights Academy. As soon as Paul turned 18 he began having sex with Brad Penny. Just as Brad treated the other gay students with whom he had sex; Brad was never interested in their cocks. He would always be willing to give them a reach around jerk off when he fucked them but that was as far as he would go.

Paul let himself be talked into becoming Paula and Brad's live in partner. It was a four year project to transform Paul into Paula. Paul was sent away to a so called finishing school where he was taught how to be a woman. He was given female hormones to assist with the transformation. Over the course of time Paul developed breasts and his hair got longer. He began to lose his body hair and he truly began to resemble a young woman and a very pretty young woman at that. Paul was pampered at the finishing school and he received many spa treatments consisting of hair styling, pedicures, manicures, body wraps and massages.

The attendants at the finishing school called him Paula and eventually Paul accepted the feminine name. Paula's favorite attendant was a cute young man named Angelo who was Paula's masseuse. Paula loved the way Angelo massaged and caressed his body with a variety of oils. The best part was when Angelo would pay special attention to Paula's ass before he eventually fucked it. Angelo would also stroke and suck Paula's cock until Paula ejaculated.

Another part of the training was culinary school and Paula became an excellent cook. Brad would visit Paula at the finishing school during school breaks and over the summer months until Paula graduated. Brad then arranged for a civil marriage and returned to Astor Heights with his new bride. The rest of the faculty was surprised when Paula arrived and they were impressed with Paula's beauty. None of them knew that Brad was seeing anyone and they were shocked to hear that he married such a knockout. Of course they had no idea it was one of their former students. It took awhile before Paula was comfortable in public as a woman. However the transition had been very easy and Paula was accepted by everyone. Some of the other wives even invited Paula over for tea and to go shopping, invitations that Paula always politely refused. Even at faculty social affairs Paula occasionally a felt a man's hand graze over his shapely ass.

Paula was somewhat content with life today but the one thing Paula did not care for was Brad's infidelity. Paula knew that Brad continued to have sex with gay boys at the academy. Of course Brad always made sure the boys were of legal age but Paula was put out by the indiscretion. Paula had to sit home and do a woman's work while Brad did as he pleased. Paula thought back to Angelo and the good times they had together. Paula would love to have a lover like Angelo. Just then a knock was heard on the front door.

"Who could that be?" Paula thought, "No one ever came around the house."

Paula stood up and tightened the short terry robe around his body and walked to the front door. Paula looked ravishing with the long brown hair draped over the robe and the shapely legs displayed below the short hem. Paula looked through the peephole in the front door and saw a young man standing on the porch wearing a jogging suit. Paula recognized the outfit as an Astor Heights warm-up.

Paula opened the door and stared at the handsome young student on the porch. "Hello can I help you," Paula asked.

"Oh hi, my name is Chris and I'm a student at Astor Heights. I was wondering if Mr. Penny was home," Chris lied as he knew that Brad Penny played golf on Saturdays.

"No he's not home right now. He's playing golf and he won't be home until dinner time. Can I tell him why you stopped by," Paula asked still surprised that the student was so far from campus.

"Oh its okay, I was just out jogging and I thought I would stop by and say hello. Are you Mrs. Penny?" Chris asked already knowing the answer.

Chris just stared at the young Mrs. Penny and wondered how Brad had landed such a beauty and why Brad Penny was fucking gay students at school when he had such a hot wife at home. "Is something wrong?" Paula asked snapping Chris out of his dream state.

"Oh sorry, it's just that you are so beautiful. I didn't expect you to be so pretty and it caught me by surprise," Chris replied getting bolder and feeling more confident.

"Really, that's a nice thing to say. Listen, I just made a fresh pot of coffee. Would you like to come in and have a cup," Paula asked knowing that it was a dangerous step to take and Brad would have a fit if he ever found out.

"That would be great. I could use a break from the jog," Chris accepted.

Paula let Chris in the house and then led him toward the kitchen. Chris walked behind Paula and admired the shapely legs and curvy ass. The short robe was tight around Paula's buttocks and Chris could see them undulate beneath the robe. Chris felt his cock stir and he wondered to himself if Mrs. Penny took it in the ass.

While Chris was visiting with Paula Penny, Karen Brown the principal's wife was sitting on the sun porch sipping a cup of coffee deep in thought. As Karen stared out the back window into their wooded lot she thought about the events of the past week. She knew that her husband Dave was banging the school nurse Millie and she knew that he was also fucking that horny slut Renee. But Karen did not resent Dave's extramarital activities as she had a good thing going herself. Once she had found out about her husband's indiscretions she decided to test the water herself. It had been so easy to seduce the young men, Rob and Jimmy, who maintained the grounds and landscaping.

Karen had invited them in for ice tea and the young men stood in her kitchen in their cut off shorts and boots. Karen had a short robe on and her shapely legs caught the boy's eyes. Things moved quickly that day and the two boys kicked their shorts and boots off and then they pulled Karen's robe from her body. Rob was the first to fuck her and she liked having his cock in her. Rob came quickly and flooded Karen's pussy with his seed. Karen felt the jets bounce off her inner walls as her womb was filled with semen. As quickly as he entered her Rob pulled out just as fast and he was immediately replaced by Jimmy. Karen maneuvered her body so that her clit was in contact with Jimmy's cock. Jimmy lasted a little longer than Rob had which allowed Karen to orgasm before he came in her. Jimmy fired a barrage of cum into Karen's pussy as his body jerked like a coiled spring.

Karen was then placed on all fours with cum dripping from her pussy. Rob got in front of her and stuck his cock in her mouth. Karen liked sucking cock as she felt it put her in control of her partner. As she was sucking Rob's cock, Jimmy was playing with her ass. Karen remembered Jimmy using cooking oil as lubricant for her asshole. Up to that moment Karen had never had anything in her ass but she liked the feeling of Jimmy's finger worming around in her rectum. Karen recalled Jimmy's finger leaving her ass and then he applied oil to his cock. When he pushed the head of his cock in her ass, Karen winched with pain and screamed. Most of her scream was muffled by Rob's cock in her mouth as her eyes filled with tears. However Jimmy was persistent and Karen was determined to take his cock in her ass. Before long her ass was numb and she only felt fullness in her bottom. After a few more minutes Jimmy was sliding his cock in and out of Karen's beautiful ass and Karen was able to return to sucking Rob's cock. The two boys were excited beyond expectations as they worked Karen's luscious body.

Rob came first and shot another big load this time into Karen's mouth. Karen swallowed some semen but Rob fired so fast and so much that most of it ran out of her mouth and down her chin. Rob backed away and stroked his cock shooting a stream on Karen's hair. Karen had since put her head down and turned her face to one side as Jimmy continued to ream her ass. "Babe I can't tell you how good you look with my cock in your ass," Jimmy had told her.

Jimmy fucked her with a few more strokes before he pushed his cock all the way in and unleashed his load in her rectum. Karen actually liked the feeling of semen shooting into her ass and the warm liquid seemed to soothe her ravished anal passage. Karen found herself involuntarily clenching and unclenching her sphincter muscles around Jimmy's cock. That drove Jimmy wild and he called out to his friend. "Rob you have got to fuck this ass, she is incredible."

Karen was pleased with herself that she had been able to handle Jimmy's cock in her ass. Minutes later she was straddling Jimmy's cock as it filled her pussy when she felt Rob testing her asshole. Rob then pushed his cock into her ass and this time there was hardly any discomfort. The two boys and Karen figured out a rhythm and soon the three of them were racing toward another round of orgasms. Since the boys had already cum twice they lasted much longer that time, which Karen was pleased about as it let her have multiple orgasms before they came. Karen felt them ejaculate into her pussy and ass and she squeezed their cocks with her vaginal and sphincter muscles. Rob and Jimmy were sexually sated and drained.

That had been months ago and now Karen would have sex with Rob and Jimmy at least once a week. Sometimes it was just one of them and sometimes it would be both of them. Rob suggested adding another guy but Karen hadn't agreed to that yet. She was deep in thought when Dave entered the sun room with a cup of coffee in his hand. "A penny for your thoughts," Dave said cheerfully.

"Good morning, I was just day dreaming looking out into the yard. How did you sleep?" Karen replied.

"Good, I always sleep well after great sex with you," Dave answered and then leaned in to kiss his pretty wife.

"How are things going at the academy with all the changes?" Karen inquired.

"Oh you mean the staff, alright I guess. Things have settled down over the first couple of months," Dave responded.

They were both referring to the addition of three female teachers to the staff. Actually one was a replacement for the English professor who took a sabbatical. The other two were French and Music teachers. The Board had decided to add French as another language and to add Music as a minor subject to the curriculum. Dave had resisted the hiring of female teachers as the academy had never had a female faculty member. The Board however had decided that it was time for some diversity and Dave had to accept their decision.

THE NEW FACULTY MEMBERS

Beatrice Hollander was an accomplished English teacher with excellent credentials. She had been unemployed for awhile but she explained to the board that it was her decision to take some time off. Beatrice had taught at several school including private ones and it was at one of the private schools were she met her demise. The school had covered up the incident so that there was no trail of any negative reports. Beatrice was old school and she believed in discipline. There had been many a time when she used her wooden pointer on a bare fanny both boys and girls alike.

Beatrice actually enjoyed having 18 year old girls bent over the desk with their skirts flipped up and their panties down around their knees while she spanked their bare bottoms. The same was for 18 year old boys with their knickers and underwear down around their knees. One day the boy students revolted and the tables were turned on Beatrice. The boys held her down bent over the desk with her full length skirt pulled up over her back. Her panties were pulled down as far as they would go restricted by the garter belt. Beatrice was spanked with her own pointer and then the boys fucked her repeatedly. For hours Beatrice had 18 year old cocks in her mouth, ass and pussy. She was filled with youthful cum and she had also orgasmed multiple times.

It was an act that Beatrice never forgot and she had loved every minute of it. After that day she had sex with 18 year old boys frequently which is what led to her eventual termination. Now Beatrice would be teaching again at a boy's private school. She could hardly control her emotions and conceal her excitement when she arrived on campus. The year ahead would prove to be challenging for 45 year old Beatrice in many ways.

The French teacher was pure French and she was thrilled to get the job at Astor Heights Academy. Claire had moved to the states just two years ago and it was her first job in America. Claire taught English for four years in France before moving to the states. The 28 year old French beauty was a sight for sore eyes at the academy. Claire was not worried about it being so male dominated as she would not be distracted by their presence. Claire had left her lover and former teacher, Monique, behind in France but she had been able to find discreet lovers in the states. Claire was sure that she would be able to maintain her professional image and meet discreet lesbian lovers while at Astor Heights. Claire was in for a pleasant surprise when she would spend one Saturday shopping with Jill the school secretary.

Doreen had taught music at a divinity school prior to her divorce and termination from the school. Her husband, a minister and head of the school, caught her with three 18 year old boys in bed together. For years Doreen had had sex with 18 year old boys without being discovered. Usually the sex was at the school in the music department but occasionally she let boys into her bed at home when her husband was away. As with Beatrice there was no trace of indiscretions in Doreen's career and in fact she got a glowing reference from the divinity school. Doreen was like a kid in a candy store at Astor Academy but she knew that she had to be discreet. At least this time she had her own apartment and she did not have to worry about a spouse.

PAULA AND CHRIS

Chris became enamored with Paula as they sat at the kitchen table and chatted over coffee. Paula knew that Chris was ripe for the taking but Paula was unsure how Chris would react to a wife with a cock. Paula refilled the coffee cups for both of them and that's when Chris decided to make his move. Chris made up his mind to hit on Paula and since Paula never changed out of the short terry robe, Chris was certain that Paula would be receptive to his advances. Chris stood up and walked up behind Paula and put his arms around the pretty young wife.

Paula tensed up briefly when Chris put his arms around him and held him tightly. Chris nuzzled Paula's neck and then let his hands slip inside the robe to find Paula's medium sized form breasts. Chris fondled the breasts and tweaked the nipples causing Paula to groan. Chris then opened the belt on the robe and when the robe parted, Paula's erect 6' cock peeked through.

"What the????" Chris yelled when he saw Paula's cock.

Chris backed away as he was stunned momentarily. "I'm sorry Chris, I should have told you. Actually I should not have let you in. Please sit down and I'll explain," Paula spoke.

Chris sat back down in the kitchen chair. Paula brought over the two cups of coffee and sat down at the table. Then Paula explained everything to Chris and obtaining Chris's agreement to keep the secret. When Paula finished explaining the situation Chris was more relaxed and then he felt obligated to tell Paula about his own bisexuality. Chris explained his relationship with his roommate Benji to Paula who was pleased to hear the story.

"Chris if you are still attracted to me I would love for you to fuck me just like you fuck Benji," Paula said in the sexiest tone he could muster.

"I would love to fuck you," Chris accepted.

Paula then led Chris into the bedroom and dropped the robe to the floor. Chris stared at Paula's naked form and then asked, "What do they call you?"

Paula smiled and replied "There are lot's of names for people like me. Transsexual or tranny for short, ladyboys is another and of course there are a few not as flattering," Paula explained.

"I think that I like ladyboy," Chris said.

"Good, now let's get those clothes off of you," Paula said as she approached Chris.

Paula undressed Chris ever so slowly and by the time his underwear was peeled down his legs, Chris was rock hard. Paula stared at the 8' cock in front of him and then lowered his mouth on the shaft and began to slowly sucked Chris's dick. As Paula sucked Chris's cock, Paula wondered how it would feel in his ass. It would be the biggest cock that Paula ever had in the ass and the prospect of it excited him but frightened him as well. Chris was incredibly turned on and without warning he ejaculated into Paula's mouth. Paula was caught off guard by the volume and force of Chris's ejaculation but Paula recovered quickly and managed to swallow Chris's entire load. It had been awhile since anyone had cum that much in Paula's mouth.

Paula stood up and patted Chris gently on his balls. "I know that there is plenty more where that came from," Paula said as he licked his lips and then added, "Now I want you to fuck me but first we have to grease up that ass buster of yours."

Paula took out a tube of lubricant and applied it to Chris's cock. Chris stayed hard the entire time as Paula stroked the impressive young shaft. "I like playing with your cock. I bet I could do this all day but I do want you to fuck me first," Paula cooed.

Then Paula got on the bed on all fours and handed the lube to Chris. "Get my ass ready for your big cock," Paula whispered.

Chris took the lube and squirted a gob right on Paula's anus and then pushed it in. Chris worked first one finger and then a second In Paula's asshole. Paula put his head down on the bed and arched his back further emphasizing the shape of his curvy ass. Chris was still amazed how much Paula resembled a girl and it served to turn him on even more. Chris caressed Paula's lovely ass as he lubricated his asshole. Chris then left his fingers drift over Paula's scrotum and tickled his perineum. Paula's cock twitched when Chris's finger ran over the perineum and again when Chris caressed the tight ball sac. Satisfied that Paula's ass was ready, Chris knelt behind him and eased his cock into Paula's ass.

Paula placed his hand on Chris thigh as if to guide the penetration. "Nice and slow, let me stretch out for you slowly," Paula gasped as his ass was spread wider than ever.

"Oh my, you really know you have someone in you when you're there," Paula gasped.

"God you are really tight," Chris echoed.

Chris took his time slowly feeding his cock into Paula's ass and then withdrawing it slightly. Each time Chris would go a little deeper and then stop to allow Paula to adjust. Paula wondered if Brad would be able to tell the difference once Paula's ass was stretched by Chris. Then Paula felt Chris's pubic hairs tickle his buttocks and he knew that Chris was buried to the hilt. Chris began a slow methodical fucking of Paula's ass and he relished every second he was in the beautiful derriere. Chris reached around Paula as he leaned over and his hands brushed against Paula's tits. Chris had momentarily forgotten that Paula had tits but now he held the tits and caressed them teasing the nipples as well. At that moment Chris truly felt like he was fucking a girl in the ass.