Caution: This Erotica Sex Story contains strong sexual content, including mt/ft, mt/Fa, mt/mt, Consensual, Heterosexual, Fiction, Incest, Brother, Sister, First, Oral Sex, Masturbation, .
Desc: Erotica Sex Story: Chapter 1 - This is a coming of age story about 14 year old Toby Wakefield who gets a summer job as a maintenance man at a large Catholic Church, caring for the grounds, the rectory and the convent. Toby is taught about life by Mother Superior, Sister Natalie. The story is more about the life of a young teenage boy rather than the Catholic Church, which I have no intention to demean. It is about human beings rather than religions.
1951 was a banner year for Tobias Wakefield of Burlington Hills, Ohio. He had just finished the eighth grade but being isolated thirteen miles from the city of Cleveland he found there was very little he could do with no money for bus fare. There was only one car in the family, his mother didn’t even have a driver’s license. His older brother at 15 was allowed to hitchhike but Toby could only walk or take the bus for which he didn’t have fare for. He asked his father for an allowance for doing chores in the garden and around the house. His father said, “I’ll give you fifty cents a week and all you can eat, but I’ll buy a power lawnmower from Western Auto (it would be his job to mow the lawn anyway) and you can ask the neighbors if they would pay you to do their lawns. At 25 cents an hour from the neighbors he found that he was soon making $3.00 a week.
His largest customer Ed Bevens, who started Toby at 25 cents an hour to cut his lawn was so impressed with the lad’s work ethic that he soon raised it to 75 cents. Bevens was chairman of the maintenance committee at St. Bartholomew’s Catholic Church which was a mile away from the Wakefield residence. It was a big church with a rectory that housed two priests and a convent that domiciled five nuns—the Mother Superior and four sisters—who administered and taught at St. Bartholomew’s pre-school. A month into summer vacation Bevens told Toby that the church had just fired their maintenance man for drunkenness on the job. He told Toby that he recommended him for the job, “as long as you continue mowing my lawn,” but he would have to interview for the job by talking with the new head priest, Father Desmond.
Bevens introduced Toby to Father Desmond. The Mother Superior, Sister Natalie also sat in on the meeting. The priest was businesslike but quite friendly (he was from Ireland). Sister Natalie, on the other hand seemed the direct opposite. During the interview she never smiled and kept stealing glances at Father Desmond as if she were either afraid of him or didn’t trust him.
Though Toby wasn’t Catholic many of his friends were. They talked him into going with them to C.Y.O. (Catholic Youth Organization) at St. Bart’s. There were enough girls there to pique the interest of any healthy young boy. Father Desmond’s predecessor, Father McNamara, ran CYO and was fun to be with. All the girls liked Father Mac a lot, he seemed to be quite a flirt, always smiling and joking with them. Numerous times when he wasn’t aware of his vigilance Toby caught the priest ogling the girls’ rear ends.
The job paid 85 cents an hour, the minimum wage at the time. His responsibilities were to mow the grass, pull weeds in the flower garden areas ... raking leaves in the fall and doing odd jobs in the rectory and convent. The inside of the church was handled by a full time Sexton. With his lawn at home, Ed Bevin’s and his job at St Bart’s Toby dropped his other customers. But he would be making over twelve dollars a week. During the summer of 1951 he discovered the benefits of American Enterprise. Before 1952 he would also discover different secrets and learn the meaning of carnal knowledge.
For the first two weeks Father Des and Sister Natalie asked no more of Toby than mowing the lawn. Once they saw how well he did the job they began having him do other jobs. Soon he was oiling squeaking door hinges, a window pane needed replacing and a loose stair tread was nailed down. He replaced a leaking gasket on the kitchen sink and replaced a couple of light bulbs...
Toby’s dad was pleased with his son for having secured such an “important” job for a young boy. The young Wakefield had watched his father as a “do-it-yourselfer” and was picking up the proclivity quite naturally. His dad told him, “If you need help or advice Son, just ask.” Then, as if in confidence he said, “But whatever you do Toby stay out of the nun’s bedrooms. When the lad asked why, he said, “It’s just a good policy Son.” Raising his eyebrows he continued with a knowing smile, “That’s just about the only spot in a church where a young man can get into trouble.”
Toby was too young to pay attention to the gossip but there was talk in the community, particularly among the Protestants, of “goings on” on at St. Bart’s. There was no public scandal; the Catholic Church worldwide didn’t work that way at the time. If something “questionable” happened the Church handled their problems internally—short of murder. If there might have been scandalous behavior the local parishes kept a lid on anything that might reflect badly on their Church. Completely unbeknownst to Toby these were undercurrents being discussed among adults in the community with a wink of the eye.
In the case of St. Bartholomew’s only higher up local leaders of the church knew what it was about. Father McNamara the previous head priest had been replaced. That didn’t mean anything to Toby, though he knew Father Mac through CYO father Des was his boss. He listened to his Catholic guy-friends talk about the nuns. Some were totally disrespectful but he thought they were just talking BS. At the same time he found the talk both intriguing and titillating, especially since the word “boner” had become a substantial entity in his life. It tickled his interest even more when he remember his father’s comment about staying out of the nuns’ bedrooms. Then he thought about the stern and noncommunicating Mother Superior and laughed as he murmured, “Like that could ever happen.”
By the end of the summer he had been in both the rectory and convent numerous times. Father Des and Sister Natalie, along with the other four nuns were more frequently asking him to do more chores. He had never been in any of the bedrooms, “cells” as the nuns called them but he had once seen inside the door of one of them. It was quite small and spare with just a cot a dresser, and a floor lamp.
In general the nuns were quite friendly and kind to Toby. They seemed to enjoy having him around. Like aunts or big sisters they offering him milk or tea and cookies during more breaks than he thought was necessary—as a boy he was a no-nonsense fella. Soon, even though the sisters knew Toby was of the protestant faith they would joke with him and make fun of his youthful shyness. It was like he was part of the family, a younger brother that everybody seemed to have fun with.
Sister Natalie on the other hand (Mother Superior) was quite stern with him, just as she was with the other sisters. But when she thought he wasn’t paying attention Toby would sometimes catch her looking at him in a way he didn’t understand. Maybe I remind her of her brother or something he would think.
Toby worked outside the buildings more than inside but was beginning to spend less time in the rectory and more in the convent, there always seemed to be more odd jobs there. Mother Superior was always in the convent, often alone. The other nuns attended to the preschool. When another nun was by herself in the convent and Mother Superior was there at the same time it wasn’t unusual for Sister Natalie to say to her, “I would like to see you in my cell in ten minutes Sister.” When this happened they were always there for the best part of a half hour. When they came out both Mother Superior and the sister looked like they had just washed their faces. But there was no bathroom in any of the nun’s cells. Toby didn’t know what to make of it.
By the end of October the grass had stopped growing. The leaves had fallen from the trees and were being raked into piles (they burned them back then). With the exception of Mother Superior the five sisters were helping Toby rake them. For some reason leaf raking always brought out the child in people. Maybe it was because winter would soon be upon them and they were anticipated the prison-like atmosphere winter always brought on. The youngest sister, Mary Cecile and the oldest—below Sister Natalie—Sister Marie Celeste, were acting like girls Toby’s age. In their penguin like habits they were jumping and laughing and rolling in the piles of leaves. Whenever two or more people were raking leaves it was always like a party. Toby, having done it with girls his own age would wrestle in the piles of leaves and try to cop a feel from the young girls—all the boys would. When he jumped into the fray of rollicking penguins he felt Mary Cecile’s hand firmly grope him between his legs, copping a feel of her own. With an embarrassed face and voice she said, “Oh excuse me Toby.”
“What happened,” asked Marie Celeste?
“He-he-he, I touched Toby’s privates,” Mary Cecile said. Toby thought she didn’t mean to grope him but was terribly embarrassed at her answer.
“It’s a good thing you didn’t touch his member.” Marie Celeste said, “It would been seventeen Novena’s for causing another scandal.” It was as if the other four sisters had seen a terrible accident. The shock on their faces was ghastly. When Marie Celeste saw their reaction she said, “Oh my,” and crossed herself. To Toby she said, “Not a word of this to Reverend Mother Toby Wakefield, do you understand? Then added PLEASE?”
All of sudden Toby’s confusion began to grow as well as the germ of understanding and the mystery of why everyone seemed to be interested in parts that resided beneath clothing.
Toby had become familiar enough with all of the sisters that he felt totally comfortable with them. Something else was happening though. Those plain women in penguin suits had developed personalities. Being devoid of artificial makeup, he began seeing them as total persons. Though lacking color each had a distinct beauty of her own. Since the day Mary Cecile copped a feel on his balls he began thinking of them as females rather than just nuns.
Whereas he had been fantasizing the usual suspects Toby’s stable of adult women had grown to seven: his mother, his aunt and his four of his five sisters in Christ, the nuns. Fearing that she might have some kind of supernatural powers he never included Mother Superior. Rather than having just one woman stroking his young tool there were six, allowing him a day of rest which he rarely left wank-free. Having cut small a hole in the end seam of his pillow his masturbation had become more sophisticated. Each time he copulated with Mom or Aunt Mary: or Mary Cecile, or Marie Celeste, or Agnes, or Kathleen the feathers that stuck to the lotion-like sperm on his dick began depleting the fluffiness his pillow. His fear kept nagging at him though. Can Sister Natalie read my nasty thoughts and divine my wicked behavior?
It was Saturday after Halloween; Toby only worked Saturdays now until school would be out for the summer. The four sisters had left yesterday afternoon to attend a Catholic elementary school workshop in Columbus, Ohio. Mother Superior was keeping him busy in the pantry in the kitchen. They were reorganizing it. At noon they stopped and had a lunch of sandwiches that Sister Natalie made along with a pot of tea. While they were eating Sister Natalie said, “I am sure you know Toby that the rest of the sisters and I are very happy with your work here, don’t you?”
Toby found that as long as others were around Sister Natalie she played the role of Mother Superior very seriously. But when they were alone, like they were now, she became a kind of buddy as well. “Yes Reverend Mother,” he said. “I am so fortunate to have this job. Not being Catholic I have always been concerned that I might not be accepted here ... that maybe you wouldn’t like that fact that I’m not a member of your faith.”
Looking at the youth with a dour smile Sister Natalie rolled her eyes and said, “Of course we would prefer that you were Catholic young man. I pray every day for your soul.” She crossed herself, looked at him and said, “When you interviewed for the job Toby and told me what faith you were it bothered me that you weren’t Catholic. But, after we let Josh Larkman go you came too highly recommended not to hire you. I’ve forgotten what faith you told us you are. Could you refresh my memory?”
“Quaker,” Toby answered.
Uncharacteristically the usually dour nun formed her mouth into a crooked smile and asked, “Do you mean you use “thee” and “thou,” when you worship?”
“Oh no Mother, they did that in the old days but not anymore. Other than our belief in non-violence and non-discrimination we are like many of the other Protestant faiths ... Oh, except for the fact that much of our worship is silent, like meditating.”
Looking at Toby as if she were taking his whole body into her eyes she said, “Interesting.” She cleared her throat and said, “I’ve forgotten how old you are Toby.”
The way the oldest of the nuns was looking at him was making him feel peculiar. He wasn’t uncomfortable, it was just strange, like the hair on the back of his neck was trying to stand up. “I’m fourteen Mother; I’ll be fifteen in May.”
Smiling she said, “Then you’re a Gemini.” Her eyes sparkled, “Father McNamara was a Gemini (he was the one who Father Des replaced).” She chuckled and said, “I’m accustomed to a person with a split personality.”
“I don’t understand Mother.”
“Gemini is a sign of the zodiac Toby. Its astrology, everybody is born under a sign of the zodiac. You’re a Gemini. I’m a Taurus. My birthday is in late April. A Gemini is a split personality, both serious and funny. Taurus the Bull is always constant. They say that Gemini and Taurus are perfect matches in a marriage.” She smiled at the discovery. “I always thought you were a Gemini Toby.” This was the first time she had given this particular kind of smile, full and warm, and open.
“Father McNamara was a Gemini too. But I already said that.” She appeared embarrassed. “He and I got along um ... famously.” She lowered her voice almost to a whisper at the last word. What she said next was too faint for the boy to hear, “I really miss him Toby.”
“What did you say Mother?”
“No matter Toby, I want to talk with you about something else.” She cocked her head and looked at him with an almost parental smile of concern and asked, “Do you have a girlfriend Toby?”
“I’ve never been out with a girl Reverend Mother. I’m only fourteen.”
Reaching over and patting his hand she said, “Then you’ve never ... I mean.” Though he had never been alone with a girl he thought he had an idea what she might have meant but wasn’t sure. Sandwiching Toby’s hand between hers she looked longingly into his eyes and said, “You have to be very careful with girls Toby. A boy like you, a Gemini, could get into serious trouble with ... um ... you know.” She looked away as if she were experiencing some kind of reverie.
“I don’t understand Reverend Mother.”
It was almost an aggressive act when her head snapped back and she stared at the boy in a way he had never seen a woman looking at him before. “Toby,” she said, “You’ve never been allowed in our cells; no man ever is. Nor has any boy your age. But since you are such a trustworthy young man I need to ask you to do something for me.”
His father’s words echoed in his ears, ‘Stay out of the nuns’ bedrooms.’ Swallowing hard he asked, “What kind of work are you talking about Reverend Mother?”
“They haven’t been painted in ages Toby. I’d like to start with Sister Kathleen’s; it’s the furthest one back. Give me about ten minutes and come meet me there.” It was a command. When he started getting up she said, “No Toby, finish your sandwich first. Ten minutes.” She rose and, the way all nun’s in habits walked she floated out of the kitchen. He thought she had to go to the bathroom.
Watching the clock on the wall moving ten minutes was agonizing. At nine minutes, walking slowly back to the wing with the cells Toby went to the last one and knocked on the closed door. “Come in Toby,” was Reverend Mother’s muted invitation.
Shy and tentative Toby opened the door. The room was dimly lit and tiny. Blinking to clear his eyes he opened them wider. The uncharacteristic way Sister Natalie was smiling at him was not the only reason that made him think can I be dreaming? He could see no painting materials and the room still looked pretty fresh. What he was looking at couldn’t be the sister Natalie he had come to know. Since working in the convent the only outwardly human parts he had seen of any of the sisters were hands and faces. Everything else was completely shrouded by their habit. Each face was cocooned by a wimple and veil. They were creatures of black and white, penguins. Everybody joked about it including all of the sisters except Mother Superior. Toby was stunned by what he was seeing but the Reverend Mother seemed to be enjoying his discomfort. Had anybody asked if this vision would have been possible Toby Wakefield, like Vizzini in The Princess Bride would have said, “IN CONCEIVABLE.”
The mirth on Sister Natalie’s face was like she had just told a “knock-knock” joke. As she eyed the gawky youth she giggled at the comic look on his face then shook in waves of laughter. Finally coming down she said, “Oh Toby, I’m sorry,” trying to catch her breath. “But you have just reminded me of Laurence.” At the question mark on Toby’s face she clarified, “Laurence is my younger brother. He’s two years younger than I am Toby. But I only get to see him once a year.” Her voice trailed off as she said, “And since he got married...” Leaving it up in the air her aura visibly saddened. Her stare intensified. It was as if she seemed hopeful that the boy would understand what she was trying to explain. Her smile softened, causing Toby to feel the beat of his heart on his eardrums. His stomach sank and his knees grew week as he ask himself, “can this really mean... ?” His ears buzzed like he had fallen on the hard floor and hit his head.
The fuzzy image he saw of Sister Natalie began to clarify. Having seen something like it in an old copy of Playboy that his father kept hidden away, it was a picture of Marilyn Monroe. She was lying on a bed, naked. Sister Natalie was no Marilyn Monroe. But to the fourteen year old boy’s stunned and staring eyes she was exquisite. The once dour and stern nun was now a beautiful woman. Her body was long and slender, probably about five feet seven inches. Her legs were shapely, her hips full. Where her legs came together a full, bushy thatch of curly, dark brown hair etched itself on his eyes. Her breasts were small for her size—petite. Her nipples were centered in tiny areolae that looked like mahogany colored Spanish peanuts. Her skin was so white that it seemed almost ghostly and her long dark hair that was parting over her shoulders was elegant, splaying over her back and breasts.
“Toby, Toby,” she said patting her hand on the bed, “Come sit beside me.”
His reeling mind shouted YES but his legs weren’t moving. He struggled with a lump in his throat that felt like was going to strangle him. And the bulge in his crotch had swollen near to the point of bursting.
In a more dominant voice Reverend Mother commanded, “TOBY, come sit by me on the bed.” It was the kind of fantasy that was easy for the boy to create in his mind. But he was having trouble convincing himself that it was actually happening. As he got nearer to the bed the commanding nun reached out her long arm. More of her long hair fell over her breast. While she had done this with priests before she had never seduced a person outside of the faith, particularly a young boy. For the wild side of Sister Natalie the wickedness of a person so steeped in religious order was almost more titillating than she could bear. In a sultry, siren-like voice she declared, “You’re not dreaming Toby Wakefield, this is actually happening. Now, come sit beside me on the bed.”
Tenderly she touched his cheek with her fingers and said, “I want you to call me Cassie, Toby. Cassie was my name before I took my orders.” she puckered her lips in a sexy moue. “When we are alone like this just call me Cassie, Ok?” Tugging at Toby’s hand she caused him to plunk his bottom on the edge of narrow mattress of the cot-like bed.
Like a zombie Toby repeated “Cassie.”
Giggling she stroked his head and said, “But you don’t have to be so serious about it darling.” She had been lying on the bed with her elbow on the pillow, supporting her chin with her hand. As she guided him to sit just in front of her breasts and shoulders she sat up beside the stupefied teen and swung her legs to the floor, her naked body now sitting to the right of him. With her right arm over his shoulders she coaxed the boy’s face toward hers and kissed his cheek.
In his confusion Toby’s immediate thought was of how soft her lips were. Funny he thought I’ve always thought they would be hard.
Not taking time out for commentary Cassie kissed each of his eyelids and the tip of his nose. “You’re such a sweet boy Toby,” she cooed. “Every one of us thinks you’re delicious.” Her lips pressing on his were like warm, soft pillows.
The only time Toby had kissed a girl was at party while playing Spin the Bottle. French kissing was something totally foreign. When Cassie opened his lips with her tongue he stiffened his body, thinking he was going to come in his pants. When he opened his mouth and accepted her tongue her breathing became wild and he almost let go. But for some reason he clutched the hidden sphincter inside him.
Breaking the kiss she said, “I know this is all new to you darling. Try to hold back your urge to ejaculate as long as you can. But when you do come don’t be embarrassed, I’ll understand.” With an sympathetic smile she chuckled, scrunched her nose like a rabbit and formed her mouth into an understanding moue. “Besides, you’re young and you’ll have another erection quickly enough he-he-he.” Everything she was doing and saying was conspiring to separate the boy from his male essence.
Taking a break Cassie said, “Let’s start getting your clothes off of you Toby.” As she pulled up the hem of his sweatshirt he raised his arms to help. “ ... and your t-shirt sweetie,” peeling that off as well. “Mm,” she sighed as she smoothed her hands over his naked skin, “You’re so smooth and muscular, still a boy’s muscles though.”
Taking hold of Toby’s shoulders she pulled on his right and pushed on his left, turning him to face her. She sandwiched his face between her hands and kissed his lips, opening her mouth. The second French kiss was easier for him to understand and he dutifully put his tongue inside. “Mm-hmm,” she approved and snaked hers into the boy’s mouth, wriggling it and wrestling against his. Her hands slid down his back and she pulled his chest against her breasts. “Oh sweetie,” she sighed, “touching another human’s body this way, particularly a male’s,” is heavenly.”
It was like she was talking to the future when she said, “One day we won’t have to separate ourselves like this. We won’t have to dress like penguins. We won’t have to lock ourselves up in cells.” What came next sounded strange coming from Mother Superior. “Hug me baby.” Still unable to completely come to grips with his fantasy role the young teen was slowly disconnecting from Sister Natalie and joining Cassie who said, “Put your arms around Cassie and tell her that you love me.”
Being a fourteen year old having just gone through puberty there was no way he was going stop a seduction in progress, molestation or whatever you wanted to call the “perverted” action that was working such wonderful magic on his virginity. In league with this soft, wet and surprising woman he believed that he was going to learn mysteries that only a woman could teach him. But he couldn’t stop thinking how did Sister Natalie turn out this way?
After about ten minutes of kissing and hugging that introduced him to the pleasure of fondling her breasts she said, “Stand up Hun.” Kissing, hugging and tit play was so new to the boy if he didn’t have to struggle to hold his jism back he could have done it all day. Cassie was ready to move on. With a wry smile she said, “Let’s take a look at what you’ve got in your pants you beautiful boy.” Unbuckling Toby’s belt she undid the button and zipped down his fly. The way she licked her lips made her appear like she was getting ready for the feast of her life. Pushing her hand under the elastic of his BVDs she grasped his cock and assessed it with her fingers. “My, my Toby you feel much larger than I expected.”
The sensation of her hand on the fourteen year old’s cock made him cramp the muscles in his ass to keep from coming—he had done it before when he was trying to shoot longer streams. But now his young ego inflated at the compliment which made his effort even more desperate. For some reason he felt that it was important for him to hold back. That’s right he remembered she asked me to hold back so he flexed his glutes harder still.
When Cassie grabbed hold of his underwear and pants together and pushed them down the head of his cock caught in the waistband and it snapped back, slapping against his stomach. “Teenage boys,” she said with glee, “you’re erection is slanting up at an angle (Father Mac’s had become a downward arc).” Toby wondered how many boys his age Sister Natalie might have seduced. With her index finger she pressed down on his glans until his penis slipped from her hand and slapped again against his belly. “Amazing,” she marveled.
Assessing his size she said, “My, my, my Toby Wakefield, you certainly have something to be proud of,” giving him a smile of surprised which was pleasing confirmation. Holding it in her hand she inspected it further, assessing its general size and contours. Lifting it up she studied the cleft under his knob, the ring of his circumcision scar behind his glans and his seeping slit. “There are men, Toby, who would love to be able to boast that theirs are the same size as yours. When you get older young man you’re going to make some woman quite happy. I hope we know each other long enough for me to find out.” She noticed something else, his scrotum hung down like a bull’s and it was quite full with its two man-sized testicles. Laughing she said, “I’m pleased with you Toby, REAL pleased.”
The look on her face was like; perhaps a mother bird’s would be when her young chick was perched on the rim of the nest for its first flight. He doesn’t know where to begin. It’s precious. The way she was initiating this young man made her feel like a woman of purpose. Cuddling him to her brought out maternal instincts. With a wink she said, “I know you want to be inside my um ... cunny sweetie and I want you there too. But when you go inside me I want you to stay hard for a while.” Uncharacteristically she winked again. “I’m going to make you cum now honey, I’ll do it with my mouth ... and you’re going to do it real fast. Then we’ll get you hard again and you’ll be able to stay hard longer for Cassie’s pleasure.”
In all of his fantasies he never thought of a woman putting his penis in her mouth. He had always come with her jacking him off, or inside his pillow as if he was fucking her. He was glad she said it would be alright to cum, the cheeks of his ass felt like they were going to start cramping. Biting his lip he held on and wondered how she was going to put it in her mouth.
Grasping the boy’s substantial cock Cassie bent forward and took the lavender, helmet-shaped head into her mouth. Easing her lips just behind his flange she bobbed slowly on it for a few short strokes then took him deep inside her mouth. He struggled not to come but on her eighth thrust he couldn’t help himself. “CASSIE” he warned, wondering if it really was alright for a boy to come in a woman’s mouth.
As what felt like a mile of sperm shooting inside her mouth he saw Cassie looking up with thankfulness in her eyes. “CASSIE, he called out with his first shot then “CASSIE, CASSIE, CASSIE.” He was not only overwhelmed that she grunted and sighed at each shot but that she swallowed each one as well. With her lips and tongue she milked him until every trace of his jism had been cleaned from his softening member. The sensation of her continued suckling was so intense that it felt like the head of his penis was on fire.
“Come to Cassie,” she coaxed then snuggled him to a long hug. As she kissed him her lips seemed softer and her tongue probed more delicately. He wondered if she really liked swallowing his nasty jizz and for a few moments thought if it was alright to kiss the mouth he had just shot such slimy stuff into. But, as her incredibly soft lips caressed his, her hands fondled him with light touches that raised goose bumps all over his body. While caressing his bottom Cassie found his balls and cradled them like Captain Queeg in The Caine Mutiny rolling his worry balls. To Toby’s shock and pleasure she even rimmed the tight moue of his anus. He didn’t know what to think of that but it made him feel good.
After cuddling for short time Cassie chortled and said in a sing-song way, “Oh goody, I feel it moving down there.” She pushed his body to shift his weight then stood over him. “Lie flat on your back sweetie,” she said. When he complied she placed her knee on the edge of the mattress, threw her right leg over his body then positioned herself just above his emerging erection. She stroked him into further hardness and said, “It seems boys are harder than men he-he-he, and so quick to recover.” With a joyful giggle of surprise she added, “I almost have to pry your cock back young man to make it point straight up.”
He found it strange that this officious nun who was always so severe in her everyday life could be giggling like a teenager. Her use of the word “cock” was both strange and exciting for him as well. The beautiful thing for this uninitiated boy was that he could satisfy his curiosity about penetrating a woman while watching exactly what she was doing. Hovering over his rigid penis she grasped it and directed it between her legs. Seeing his suck- reddened phallus being held in her hand Toby was overwhelmed as it appeared, just below the luxuriant brown thicket of her pubic hair, to be connected to the warm, soft slipperiness of Cassie’s quim. She mopped his peckerhead in the sopping groove of her vagina then found her opening with it. He winced with pleasure before crying out “Ooh, ooh Cassie as he felt his knob being taken by the mysterious warm pudding of her womanhood.
The many times he had humped his pillow he had wondered what a woman’s glistening labia felt like. Were they just wet kisses? And he couldn’t even imagine what being inside a woman would be like. As she fitted his head to her accepting opening she dipped in mini-bobs like she was fitting a finger into a tight glove. The feeling was exquisite beyond description as he felt his swollen knob pop inside her sexual O-ring. Then, as she began an indescribable descent on his throbbing boner, he watched as her mouth formed a perfect oval and, like a caroler singing “Joy to The World, then matching the length of her downward slide with a perfectly metered “O-O-O-O-OH.”
For a fourteen year old boy whose cock had never experienced the inside of a vagina there was no explanation. It was wet, warm and spongy. It was a silky kind of pudding with a grip. It stroked his erection yet moved as if his maleness and her female pocket were a mold of his sculptured penis. Since experiencing his first erection Toby’s cock had become the center of his universe. Now his universe was lost in the galaxy of Cassie’s indescribable pussy.
He was waking up from this extraordinary dream about being with Mother Superior in such an unbelievable way. Yet he was hearing Sister Natalie’s voice—her real voice saying: “I’m amazed Toby that we have been fucking for so long.”
Geez oh man, he thought, I’m actually FUCKING the MOTHER SUPERIOR. Fucking he thought, running the word through his brain, surprised that a bride of Christ would be using such profanity. But she actually was and was humping the hell out of his cock.
Almost completely out of breath she gulped, “I’m surprised and pleased Toby that you have stayed hard for so long. She lurched upward, his phallus coming out of her pussy with a wet sounding “Shlook” and said, “Look at the clock Toby, PHEW, it’s been almost fifteen minutes. I have to stop and rest for bit.”
When her pussy had made its first slide on Toby’s cock he felt like he had to come. With a heroic clutch of his ass-cheeks he was able to stem the tide. His balls hurt at first from his first orgasm but when he worked through this urge he showed a natural penchant for long rides in the saddle. Instead of popping his wad he felt the thrilling ambiance of an experienced cunt-wrangler. It was beyond Cassie’s expectation. Her ball-deflating blowjob had defused the second round eruption. Settling on his stiff phallus Cassie let her breasts cushion her weight on the boy’s chest. With a delighted sigh she gave him an open mouth kiss and murmured, “You’re all I could have hoped for my little man.”
With a frisson of disappointment Toby said, “I-I thought you said I was big.”
Realizing that she had somewhat bruised the young man’s ego she smiled and said, “Aww, I wasn’t putting you down baby, you ARE big.” She touched the tip of his nose like a power button. “And you’re so damned cute. Not only do you have a large penis Toby, you can go as long as any man I’ve ever been with. She gave him a conciliatory kiss and continued; “Now this is Cassie talking, not Sister Natalie and certainly not the Mother Superior. But most men I’ve been with baby can’t fuck nearly as long as you.” With a big smile she added, “And who would have ever thought that it is the first time you have ever done it.”
These compliments coming from such an unlikely woman canceled the growing feeling of inadequacy. They would set the tone that would turn this boy into an incredibly confident man. After resting for a few more minutes what Cassie said next came from so far out of the blue that he couldn’t believe his ears. “Have you ever seen dogs having sex Toby?”
He couldn’t even imagine what Cassie was getting but he answered, “Yes Cassie, I’ve seen them do it with the male over the female’s back.”
“EXACTLY Toby, we can do it just like that, he-he-he and it’s SO much fun.” She pushed herself up on her elbow again and said, “Now that I know how long my li ... um ... young man can last we can do it that way. It’s a lot less tiring for both of us.” She pushed on his shoulders and Straitened up as she said, “Let’s get that magnificent cock of yours out of my pussy honey then get off the bed. Then I’ll get on all fours, just like a female dog and you can fuck me from behind just like you told me.” Not waiting for an answer she continued, “Okay Toby, up, up, up now.”
As she stood up the inexperienced young man’s eyes poured over the attractive nun’s body. The total absence of sun on her body made her skin white and transparent like fine, bone china. And it was so incredibly smooth. Though she had a small lace of crows’ feet at the corners of her eyes the rest of her body looked like an alabaster statue. He grinned as he looked at the luxuriant but whimsically unruly patch of dark hair that covered Mother Superior’s mound. He had the urge to rest his face on it and get his nose closer to the smell that was emanating from the mysterious slit which he had not yet eyed. She kneeled on the edge of the bed, her heart shaped bottom becoming prominent as she leaned her muscular back forward and laid her head sideways on her crossed arms. It was like she was making an act of supplication. He thought of Sister Natalie dressed in her black and white penguin habit that was hanging on the hook on the door. He thought of the stern and efficient Mother Superior and reminded himself she’s Cassie.
As his eyes glued themselves to the spot he had not yet seen it was a renewed shock that further hardened the up-tilt of his erection when he saw her pink and moist pussy. It was the first time he had seen one from a “going in” angle. He had seen the little girl’s that he had played with as a child, the bald mound and the outline of her lips. But Cassie’s was surrounded by hair, and lots of it. As if she knew what he was looking at she rocked backward, stretched her arms back and pulled her cheeks apart. With a wet click the hairy lips parted and opened slightly, exposing the pink exposure of the place his cock had been fucking. It was his first vision of the “holy of holies” that nearly caused him to pop and lose his load to premature ejaculation.
Cassie’s voice came as if muted from the position of her head, “Toby?”
“Um ... yes Cassie.”
She chuckled and said, “Thank you for remembering my name baby; you’re such a fast learner.” It was said as if others might not have remembered. How many have there been? Her body moved and she extended her right arm backward. “Do you see where my finger is touching?” He saw that she was touching a spot at the top of her slit.” In a way it looked like a tiny penis.
“Do you see what my middle finger is touching?” He saw that it was diddling the tiny dick at the convergence of her pussy lips. “Touch that spot with me sweetie, ok?” He put his finger next to hers which rubbed her slippery essence over his. Taking hold of his finger she placed the tip on the glistening node and at his touch she wiggled in a quick response.
“Feel the bump Honey... yes that’s it ... rub it, but not too hard.” He was tentative. “A little harder Honey, yes, that’s it, ooh, YES.” Talking through her excitement she said, “This is my clitoris Toby. It’s a spot in a woman that is quite similar to the head of your ... um... penis. Ooh YES ... and it’s even more sensitive. “Rub it gently please.”
She writhed as her ass wiggled and her shoulders twisted. “Mm, that’s good sweetie but a little harder dear.” He rubbed harder and her wriggling increased. “Keep rubbing.” He did and she tensed and exclaimed, “YES,” quivering and collapsing. “Thank you Toby, what you’ve done is given me a delicious orgasm—that’s such a wonderful feeling for a woman.” He didn’t know what an orgasm was but got the idea that she liked it a lot.
“Now sweetie,” she went on, “put your hands on my bottom, one hand on each cheek. That’s it. Now spread me open.” He was astounded as he watched the pinkness of her slick groove become exposed as the hole in the middle of her ring of hair it opened wide. The inside seemed to be bubbling with juices. “Put your finger inside love.”
As he complied he was once again overwhelmed at the indescribable feeling of this new experience. A new wave of excitement brought another urge to ejaculate. Sliding his finger in and out he asked “Like this Cassie?”
“Kind of Toby, but um ... as you move your finger in and out press the tip of it kind of hard against the front wall of my um vagina.” The wiggling and moaning happened again. “Put in two fingers Honey. YES that’s it.” The wriggling intensified and her moans became louder. “Now, as you fuck me with your fingers put your thumb on my clitoris and rub at the same time.” The way she went wild, this time with an even larger orgasm, made Toby feel proud of himself.
After resting for a bit in her “doggie” position her voice became sultry and relaxed as she said, “Everything about you Toby: the way you work, your caring for Mother Superior (talking in the second tense) and the sisters, your respectful attitude, the way you are working so hard to make me, Cassie, feel good right now, has filled me with such a sense of satisfaction.” She sat up and hugged Toby, kissed him both respectfully then passionately. “You’ve given me another orgasm Honey. And you’re just a boy.” She smiled, “and WHAT a boy!” She kissed him again, tensed and shuddered. “Whew Toby that was so wonderful, you’ve just given me my third orgasm. And it wasn’t just a little thing. Do you understand the ways you can get a woman off baby?” It seemed like she was as excited as a young girl at a clothing sale. “I just wanted you to become familiar with my body today but you made it work the first time. You’re amazing. Oh Toby, Toby, TOBY.”
With a broad smile she said, “Now dear, are you ready to put your magnificent COCK inside Cassie’s hot PUSSY?” She didn’t want to minimize the basis of his ego again.
He was still surprise how when he had fucked Cassie’s pussy with his fingers it felt like the inside of his mouth. Just like his the insides of his cheeks it was wet, slick and warm. But it molded around his fingers like their size and shape were designed specifically for that mysterious sexual space. And it got tighter as he felt Cassie making it tighter. At the same time it was softer than the inside of his mouth. It was so hard to get these things straight in his mind. But he loved trying to figure it all out.
She understood his perplexity when he didn’t answer her question ... and was thankful that he just kept doing what he was doing. This sweet child is actually trying to please me. Laying her face on the backs of her hands again she pushed her ass up a little higher. Taking in her nakedness with his eyes he considered what He and Cassie were doing and felt like pinching himself to prove that he wasn’t dreaming. Hesitating for a moment he held the fingers that had just been inside Cassie’s pussy just below his nose so he could savor the scent. He couldn’t explain the smell other than to wish that Cassie’s entire body could smell like that ... that he could smell like that too.
“Time’s a wasting Baby” Cassie said in her playful sing-songy voice.” It brought Toby back to his purpose. Spreading Cassie’s alabaster colored ass to open the threshold of her pussy, he eyed the inviting pinkness. Holding his cock like a baseball bat he pointed the tip at the hole. Leaning forward while Cassie pushed her ass back against it, he pranged her welcoming pudenda and pushed deeply inside her.
What happened to his youthful virgin body was like instant climate change. As his cock was totally enveloped by Cassie’s warm, soft, wet and form-fitting pussy his body became so chilled that it felt like he had gone from one hundred degree sunshine into a deep freezer. He shuddered for a few seconds before heat started rising from his feet, quickly moved to his knees then his thighs, groin, and chest then. It was a kind of metamorphosis that finally tickled the rims of his rims of his ears and nostrils and brought him back from the rapture.
The words coming from Cassie’s mouth were different this time: “FUCK my nasty CUNT Toby Wakefield, SLAM my ASS, drive this SINFUL SISTER back into a state of grace.” Holding her hips he slammed and withdrew, jamming his hips forward and pulling back, their slamming bodies making clapping noises that sounded like applause for an outstanding performance.
Cassie’s head was up like a breast stoker, her back was arched and she made sounds like she was speaking in tongues. He could make out, “Yes, yes, yes. Fuck me Toby, fuck my dripping pussy, and cram your cock into my hot cunt,” But the other words were gibberish.
His balls were aching and he needed to come but having made the commitment to Cassie he had redoubled his efforts to keep from ejaculating. His attempts to hold off set off opposing actions, the need to spurt his semen and the cramping of his muscles. Squeezing his ass tighter he once again defeated his adversary.
“Pinch my nipples Toby, PINCH them!” He was afraid to hurt her but, at her command, Toby reached under and pinched Cassie’s nipples. “I said PINCH my fucking nipples Toby, HURT me!” He didn’t understand why she wanted pain but he pinched harder. Her body tensed then seized in another spasm which seemed like a ten second paroxysm. “Rub my clitoris baby and fuck me HARD.” He laid into it, slamming against her body and rubbing her swollen node. Both of their bodies glistened with beads of sweat as their skin was sliding against each other’s. “Cum inside me Toby,” Cassie commanded. Cum in my CUNT.” His aching balls swung and thumped against Cassie’s wild pubic thatch. Nothing would stop his jism now. Slamming three more times he trumpeted like a rutting elephant. Unable to stop his words he said, “Oh my FUCKING God.”
Cassie seemed to hesitate for a second then resumed her climax. When she fell forward her pussy came off his dick and she held forth with a long, whooshy pussy fart. Chuckling she joked, “We do make some interesting noises in our sex don’t we young man?”
Laying with her back to the wall she opened her arms and implored, “Snuggle with me Toby, love me.” He put his arm under her side and they both hugged, their damp bodies nestling together. They kissed, though not as passionately as before, just coming down and peacefully back to life.
After about five minutes Cassie said, “Toby, we must get something straight if we are going to continue doing this, something I want to the core of my soul. Though I am Cassie in bed you must never forget that I am a bride of Christ, the Son of God. I can’t allow you to blaspheme the name of God.”
Toby wanted what had just happened to happen over and over again. Having heard so much about blasphemy from his own religious experiences he knew what she meant. “I apologize Reverend Mother,” he said (She didn’t suggest that he call her Cassie). “It will never happen again.”
It was strange lying with this naked woman ... the most seminal event of Toby’s young life. Sister Natalie was a devoted woman of the church. At the same time she was a wild sexual being. Toby was just a boy having the good fortune to sow his wild oats in a woman who was willing to teach him about the mysteries of sex. He didn’t feel guilty at all. But he felt guilty for the Mother Superior. She was a bride of Christ who was cheating on her ethereal husband. At the same time he wondered what kind of world God has created where one of his most treasured creations, a holy woman, is tortured by her need to express herself so desperately that she is doing it with a fourteen year old boy.
“I hope you don’t think ill of my nasty behavior Toby,” Sister Natalie said. “God is my judge. And I know He will always forgive me.” Looking askance she continued, “We have both sinned you know. I will be forgiven through confession, but I worry about your soul, my young friend.” Heaving a heavy sigh she said, “We must get dressed my sweet boy.”
He pulled both his shorts and pants on at the same time then put on his t-shirt, socks and shoes. Feeling like a voyeur he watched Sister Natalie cover herself with her wimple, her gown and her veil, again resembling the penguin that everyone joked about. Before leaving she asked, “Will you pray with me Toby?”
At this point in his life, having just been taken to the Promised Land, he in no way would have denied his sexual Angel anything. She took his hand and as she kneeled Toby went down with her.
“I can pray,” she said. “And if you care to you can copy my words.” With that she began her first Novena. By the time she had finished her third Toby was up to speed on the words and his knees hurt from the hard floor. He felt a bit silly but he recited the prayer with her until she finished the string of rosaries ... at seventeen. He didn’t know why seventeen but that’s the way she did it.
Her final prayer was, “Be merciful to me a sinner Lord, one who has betrayed and continues to betray you. Thank you, Lord for your understanding.” For Toby Wakefield she simply prayed “Please be with this young sinner, he has been led into iniquity by your disgraceful servant. I ask You to help me lead Toby to the path of the true faith so he can receive Your bountiful forgiveness...”
From the fortunate Toby Wakefield’s perspective as she prayed, he felt the presence of her penitence. At the same time he wondered when he would enjoy his next sexual tutorial. Deep down, he was overwhelmed that Mother Superior had chosen him. As far as he was concerned he was quite happy to be this penguin’s preference...