Caution: This Erotica Sex Story contains strong sexual content, including mt/ft, mt/Fa, mt/mt, Consensual, Heterosexual, Fiction, Incest, Brother, Sister, First, Masturbation, Oral Sex, Safe Sex,
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.
I don’t suppose I am different from most males, having always been obsessed with sex. But even in retirement the preoccupation seems to take up a disproportionate amount of my time. I wonder how many retirees who have reached the point in their life where they can no longer achieve an erection without the aid of Viagra feel the same way about it that I do. But then Pfizer’s introduction of Viagra, the most successful pharmaceutical introduction in the history in the industry, answers my question.
From my earliest memories I have always seen myself in the company of women. That’s natural of course, being with my mother and her female relatives or friends. I can’t tell though whether I had an instinctual awareness of sex at those early ages, or if I have transferred feelings and understandings picked up along the way. But I have always recognized the softness of women, their breasts, the touch of their hands, and the peculiar formation that was so often prominent where their legs joined when they were wearing jeans or shorts. The fact is that I am obsessed with women. It seems that I have always recognized the magnetic effect they have on men, their touching, hand-holding, love pecks and coy looks of adoration.
I was born on the west side of Cleveland, Ohio. It was there where I had my first brush with sex, if I can call it that. I was playing doctor with a girl named Mary who lived down the street. Though I saw very little of her thereafter I remember her pink panties and the marvelously lipped thing between her legs. We were in the basement; my mother was outside hanging up washed clothes. While Mary and I were in the throes of fondling each other’s parts my brother discovered us at play. He was two years older than I and tended to dominate me. When he saw us with nothing on below our shirts he said to me, “If you don’t watch out I’ll tell Mom Toby.” For some reason it never struck me odd that he didn’t want to get in on the act. But he always liked to hold things over my head in the way of blackmail.
In less than a couple weeks the experience came back and bit me in a strange way. My brother and I shared a room. It was in the morning, I was getting clothes from the top drawer of our dresser. Charlie, who had a mean streak, slammed the drawer on my fingers. When I yelped and cried out in pain Mom came charging up the stairs, opened the door and said, “What’s going on in here?”
I cried out in pain, “Charlie slammed my fingers in the drawer!” Mom’s reaction was to cock her arm and start swinging her open hand at his face.
My brother’s reaction was lightning fast, “Oh yeah?” he said, “Toby was fucking Mary!” It was as if he had stopped time. As Mom’s hand was in route to his face it changed direction in mid swing, slapping mine. My crying and the evidence of my bruised finger were trumped by the malicious charge leveled at me by my brother. In an instant I got a clear picture of the seriousness of sex. There was no reaction on my mother’s part to the foul word that had just come from my brother’s young mouth. After that Mary became a nonentity in at our house and I can’t remember ever seeing her again—perhaps my mother had talked with her mother. But I do remember those pink panties and her beautiful, mysterious parts.
When we moved to the suburbs of Cleveland my brother and I shared a bedroom upstairs in the new house, right next to our parents’. My bed was next to the wall that abutted Mom and Dad’s room. It was here where I began detecting unexplainable sounds that came through the uninsulated wall. The sounds and strange words always happened after we had gone to bed when our parents probably thought that we had gone to sleep. They were a total mystery to me until my own member started becoming erect on a regular basis.
With my first erection I experienced both fear and fascination. Our family was dealing with a plague of boils at the time. When my erstwhile benign penis began to swell I thought it might have to do with that. When it filled and stretched to a frightening length and hardness I feared that it might explode. Overcome with natural curiosity I began closely inspecting it. Masturbation soon took over. Indeed it did burst but not in the way I feared. Damaging abuse came next and, like a hiker in new shoes, I got a burning blister on the underside of my penis.
It seemed that within a week or two my peer group, whose aim was to gain some kind of sexual understanding through the liberal application of show and tell. All five boys were anxious to exhibit his new found toy which, when hard were: small to large, three circumcised and two uncut. Three were straight when hard, two were seriously curved, one upward and one to the right. Much later in our lives would learn that Wayne and Tommy had Peyronie’s disease. It became a topic of conversation during the Clinton administration. We showed our hardness with a sense of pride and raced to see who could shoot first, giving style points to the one who could squirt the furthest and/or cum in the most volume. “Jizz” became a much talked about subject.
Back to our bedroom: It was Charlie’s idea to keep a drinking glass on the table in between our beds. Using it as a stethoscope against the wall we would listen to our parents in bed. Charlie said, they were “fucking.” He told me about the connection of male and female organs. When we heard them in the act we would both get hard and “jack off” while we listened. It just seemed like the natural thing to do. Once I understood what the connection of organs was about and the apparent enjoyment my parents had while connecting, I began picturing how my father’s cock was plying Mom’s vagina. Fantasies about my mother and me connecting in the same way began within minutes of learning about it.
Sometimes, while lying in bed and hearing expressions of joy wafting through my wall I would hump my pillow, imagining it was Mom. To enhance my pleasure I cut the seam large enough to get my erect cock inside its feathered interior. When I came and pulled it out of my pillow it resembled being tarred and feathered, the sticking medium being white rather than black.
Our house was situated on an acre of ground, most of which was grass that had to be cut each week during the summer. The first two years we lived there my brother and I mowed the grass with a push-type lawnmower. When Dad finally bought a power mower we were able to do it in less than half the time. He made it clear that when we were finished with our lawn we were free to ask neighbors if we could mow their lawns for money. Charlie opted out. He was fifteen and got a regular summer job.
By the time I was fourteen I had eleven customers; they liked the fast and efficient way I worked and were kind enough to recommend me to others. One day my best customer—Mr. Bevens—took me aside and said, “I know of a job that would be good for you Toby. The lawn is bigger than any that you are doing now. They pay well and they need someone to do extra yard work and small handyman stuff. Do you think you might be up to it?”
Ed Bevens was chairman of the maintenance committee at St. Bartholomew’s Catholic Church. It was a big church with a rectory where the two priests stayed and a convent that housed six nuns: the Mother Superior and five sisters who administered and taught at St. Bartholomew’s pre-school.
Mr. Bevens introduced me to the head priest, Father Desmond, and the Mother Superior, Sister Natalie. The priest was businesslike and quite friendly (he was from Ireland). Sister Natalie, who seemed to be the direct opposite of Father Des, treated the interview very seriously. She never smiled. With lowered eyes she also kept glancing at Father Des as if she were either afraid of him or didn’t trust him.
I took the job; it paid me $1.00 an hour, the minimum wage at the time. It mowed the grass, pulled weeds in the flower beds, raked leaves in the fall and did odd jobs in the rectory and convent. The church itself was done by a full time janitor. With my lawn at home, Ed Bevens’ and St Barts’ I dropped my other customers. I was making a lot more money.
For the first two weeks Father Des and Sister Natalie asked no more of me than mowing the lawn. Once they saw how well and efficiently I did the job the work that had been shelved was now being demanded of me—just like with any older structure repairs had to me made: door hinges squeaked, a window pane needed replacing, a loose stair tread needed nailing down, the kitchen sink dripped, light bulbs needed replacing and so forth.
My father was pleased that I had been hired for such an “important” job for a young boy. My comfort level with fixing and repairing was the result of watching him as a do do-it-yourselfer. “If you need help or advice Son,” he told me, “just ask.” Then, in a confidential tone he said, “But whatever you do Toby, stay out of the nun’s rooms. When I asked why he said, “It’s just a good policy.” Raising his eyebrows he continued, “That’s one of the few places where a young man can get himself into trouble.” There was underlying feelings in the community that some unspeakable thing had gone on at St. Bart’s. The local parishioners were tightlipped about anything that might have happened and there was no public scandal. But it didn’t take me long to get the sense of unspoken undercurrents about the previous Head Priest, Father McNamara. A number of my friends were Catholic and belonged to St. Bart’s. Because there were so many girls going to CYO (Catholic Youth Organization) they convinced me to go with CYO with them—this was before I was hired. When I went I noticed how blatantly Father Mac ogled the girl’s butts.
By the end of the summer I had been in both the rectory and convent many times. Father Des, Sister Natalie and the other five nuns were regularly asking me to do chores for them. I had a free rein in both quarters with the exceptions of Father Des’ inner sanctum and the nuns’ bedrooms, “cells” as the called them. I’d seen inside the door of one of the bedrooms once. It was quite small and spare. The nuns in general were friendly and kind to me, offering me milk or tea and cookies during more breaks than I thought were necessary—they would joke with me and make fun of my youthful shyness. It was like I was part of the family, a younger brother that everybody seemed to have fun with. Sister Natalie was still stern with me though, just as she was with the other sisters. But when she thought I wasn’t paying attention I sometimes found her looking at me in a strange way that I didn’t understand. Maybe I reminded her of her brother or something. On rare occasions I would notice her almost staring at me with one of her tight smirks. The pupils of her eyes seemed like they were taking pictures. More often than not I was uncomfortable around her. At the same time I felt strangely attracted to this dour woman of the church.
I worked outside the buildings more than inside, spent less time in the rectory and more in the convent. Mother Superior (Sister Natalie) was always in the convent, often alone. The other nuns were attending to the preschool. When another nun was in the convent 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 at least a half an hour. When they came out both Mother Superior and the Sister would usually look more relaxed than when they went in. They even looked like they had just washed their faces. But there was no bathroom in any of the nun’s cells. I didn’t know what to make of it.
By the end of October the grass had stopped growing and we were raking the last of the leaves (we burned them back then). With the exception of Mother Superior the five sisters were helping me rake and pile them. It was fun. The youngest sister, Mary Cecile and the oldest below Sister Natalie, Sister Marie Celeste, were acting like girls my age. In their penguin-like habits they were jumping and laughing, rolling in the piles of leaves. When I raked leaves with girls my own age it was always a kind of party. As we wrestled in the leaves the boys would try to cop a feel from of young girls. At St. Bart’s when I jumped into the fray of rollicking penguins, I felt Mary Cecile’s hand firmly grasping my package, copping a feel of her own. Embarrassed she said, “Oh excuse me Toby.”
“What happened,” asked Marie Celeste?
“He-he-he, I touched Toby’s privates,” Mary Cecile said.
I was terribly embarrassed at such a public answer.
“It’s a good thing you didn’t touch his Toby.” Marie Celeste said, “It would been seventeen Novena’s for causing another scandal.” When the other four sisters scowled at her accusingly Marie Celeste said, “Oh my,” and crossed herself. To me she said, “Not a word of this to Reverend Mother Toby Wakefield, do you understand?”
At that moment I began understanding volumes.
I became familiar enough with all of the sisters that I felt comfortable with them; I could have been a brother or nephew of theirs. Something else had happened since I started almost six months before; those plain women in the penguin suits had developed personalities. While they were devoid of any makeup I began seeing them as total persons and discerned that each, though lacking color, had a distinct beauty of their own. Since the day Mary Cecile grabbed my balls I began thinking of them as sexual beings, rather than just nuns. My father’s admonition, “Don’t go into the nun’s bedrooms” developed greater meaning.
My stable of adult fantasy women had grown to seven: My mother and my six “sisters.” Rather than having just one woman stroking my dick under my covers at night there were seven. Now my surrogate pillow served as seven women. But each time I “copulated” with Mom: Mary Cecile, Marie Celeste, Agnes or the other two “brides of Christ,” the feathers that stuck to the sperm on my dick depleted the stuffing of my pillow just a little more. My real fear was, can Sister Natalie read my nasty thoughts and understand my pillow-fucked behavior?
It was Saturday after Halloween—I only worked Saturdays until school was out for the summer. The five sisters had Friday afternoon to attend a Catholic elementary school workshop in Columbus, Ohio. The convent was eerily quiet. Sister Natalie was keeping me busy in the pantry in the kitchen where we were reorganizing it. At noon we stopped and had a lunch of sandwiches that she made and a pot of tea. “I am sure you know Toby that the rest of the sisters and I are very happy with your work, don’t you?” she said.
“Yes Mother,” I said. “I am so fortunate to have this job. Not being Catholic I was concerned that I might not be welcome here or that maybe you wouldn’t like that fact that I wasn’t a member of your faith.”
Looking at me with a wry smile she rolled her eyes and said, “We would of course prefer that you were a member of the faith young man. I pray every day for your soul.” She crossed herself, looked sternly at me and said, “You told me when you interviewed for the job what faith you were but I have forgotten. Could you tell me again?”
“Quaker,” I said.
Uncharacteristically she formed her mouth into a crooked smile and asked, “Do you mean you use “thee” and “thou,” when you worship?”
“No Mother, they did in the old days but we don’t now. Other than our belief in non-violence and non-discrimination we’re like many of the other Protestant faiths ... Oh, except for the fact that much of our worship is silent, like meditating.”
“Interesting,” she said,” looking at me as if she were taking my whole body into her eyes. Clearing her throat, she asked, “How old are you Toby?”
I couldn’t make out why she was looking at me so completely, it was making me uncomfortable. At the same time I could almost feel the hair stand up on the back of my neck. “I’m fourteen Mother; I’ll be fifteen in May.”
Smiling she said, “You’re a Gemini.” Her eyes sparkled, “Father McNamara was a Gemini.” She chuckled and said, “I’m accustomed to your split personality.”
“I don’t understand Mother.”
“Gemini is a zodiac sign 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. They say that Gemini and Taurus are perfect matches in a marriage. I always thought you were a Gemini Toby.” This was the first time she gave me a full, warm smile. “Father McNamara was a Gemini too. But I already said that.” She seemed embarrassed by what she had just said. “We got along famously.” What she said next was almost too faint for me to hear, “I miss him.”
“Pardon me Mother?”
“No matter, I want to talk with you about something else Toby.” She cocked her head and looked at me with and 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 my hand she said, “Then you’ve never ... I mean...”
I thought I knew what she might have been getting at but couldn’t really believe she was suggesting it. Sandwiching my hand between hers she looked longingly into my eyes and said, “You have to be careful with girls Toby. A boy like you, a Gemini, could get into serious trouble with girls.” 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 me in a way I’ve never seen a woman looking at me before. “Toby,” she said, “You’ve never been allowed in our cells (the nuns’ rooms), no man has. But since you are such a trustworthy young man I need to ask you to do something for me.”
Remembering my father saying, ‘Stay out of the nuns’ bedrooms, ‘ I swallowed kind of hard and asked, “What is it you want me to do Reverend Mother?”
“The rooms 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 I started getting up she said, “No Toby, finish your sandwich first, ten minutes.” She rose and floated out of the kitchen, the way all of the nun’s habits made them appear when they walked.
Looking up at the clock I saw that I had a little more than one minute to go. Sister Natalie was obsessive about time. I had learned early on that when I had lingered and was late I got a harsh scolding. Walking slowly back to the wing with the cells I went to the last one and knocked on the closed door. “Come in Toby,” wafted through the door. Opening the door I was shy and tentative. The room was tiny and dimly lit. Blinking to clear my eyes I opened them wider. Mother Superior was smiling at me in such an uncharacteristic way for her that I thought, can I be dreaming? Surely what I was looking at couldn’t be the sister Natalie I had come to know. For me, since working in the convent the only outwardly human parts of the nuns that showed were hands and faces. Everything else was so tightly covered by the habit; their faces were cocooned in their wimples and veils. Everybody thought of nuns as penguins (the sisters even joked about it); truly these women were creatures of black and white.
While I was stunned the Reverend Mother seemed to be enjoying my discomfort. Had anyone asked if it were possible I would have said, “Inconceivable.”
The mirth on Sister Natalie’s face was like she had just told a joke. As she looked at me she giggled at the look on my face. Then she shook in rolls 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.” Too astounded to reply I guess my face was a total question mark. “Laurence is my younger brother. He’s two years younger than I am Toby. But I only get to see him once a year. And since he got married...” Trailing off her entire aura saddened. As her staring intensified she seemed hopeful that I would understand what she was trying to explain. Her smile softened, causing my heart to beat. But that wasn’t all that was beating. My ears seemed to be buzzing. It was like I had fallen and hit it on the hard floor, nearly knocking myself out. What I was looking at seemed fuzzy in an aura of light. I had seen something like it in an old copy of Playboy that my father kept hidden away. It was a picture of a naked Marilyn Monroe.
Sister Natalie was no Marilyn Monroe but to my stunned and staring eyes it finally dawned on me that what I was seeing was true. The once sour and stern nun was now a beautiful naked woman. Her body was long and slender, probably about five feet seven inches. Her legs were shapely; her hips full, starkly punctuated where her legs came together by a full, unruly thatch of curly, dark brown hair. Her breasts were small for her size, probably a B cup, and her nipples, centered in tiny areolae, looked like mahogany colored Spanish peanuts. Her skin was white and seemed delicately transparent. Her long dark hair was elegantly parting over her shoulder and splaying over her back and breast.
‘I’m sorry Toby,” she said, “I’ve thought about it for long time. This is the best way I could think of to bring our relationship to this point. Would you like to sit beside me on the bed?”
My reeling mind shouted would I but my legs weren’t moving and butterflies filled my stomach. This I did know though, the lump in my throat felt like it was going to strangle me and the bulge in my crotch felt like it would explode.
In a more dominant voice Reverend Mother commanded, “Come sit by me on the bed Toby.”
It was the kind of fantasy that was easy for me to create in my mind. But I was still having trouble convincing myself that it was actually happening, if indeed it truly was. As I got nearer she reached out her long arm causing more of her long hair to fall over her breast and said in a sultry, siren-like voice, “You’re not dreaming Toby, this is actually happening.” She tenderly touched my cheek with her fingers and said, “I want you to call me Cassie; that was my name before I took my orders. When we are alone like this ... just Cassie, do you understand?” Like a zombie I repeated the name. She tugged my hand and I sat on the edge of the mattress of the narrow single bed.
Giggling she 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. Sitting up beside me and swinging her legs to the floor she guided me to sit just in front of her breasts and shoulders. With her right arm over my shoulders she coaxed my face toward hers and kissed my cheek. My immediate thought was of how soft her lips were. Funny I thought I always imagined they would be hard. -Not taking time out for commentary she kissed each of my eyelids and the tip of my nose saying, “You’re such a sweet boy Toby. Every sister thinks you’re delicious.” Her lips pressing on mine were like warm, soft pillows.
French kissing was something totally foreign to me. When Natalie, I mean Cassie opened my lips with her tongue I stiffened, thinking I was going to come in my pants. When I opened my mouth and accepted her tongue her breathing accelerated. She broke the kiss and said, “I know this is all new to you Toby. Try to hold back your need to ejaculate as long as you can.” When I asked what ejaculate meant she smiled and said, “Cum,” and giggled and clarified, “I guess you boys say ‘shoot.” But when you shoot don’t be embarrassed, I’ll understand.” Chucking she went on, “Besides, you’re young and you’ll get hard again quickly enough.” She smiled and scrunched her nose like a rabbit and formed her mouth into an understanding pucker.
Everything she was doing and saying was conspiring to separate me from my male essence. Let’s get that sweatshirt off you Toby,” she said, pulled up the hem of my shirt. I raised my arms and she stripped it off, “ ... and your t-shirt too dear.” She peeled that off as well.
She pulled on my left shoulder and pushed on my right, turning me to face her as she faced me. She sandwiched my face between her hands and kissed my lips, opening her mouth. When I felt her tongue in my mouth it only seemed natural for me to explore her open mouth with my tongue. “Mm-hmm,” she approved as she snaked hers around mine. Her hands slid down my back as she pulled my chest against her breasts. “Oh sweetie,” she said, “touching another human body like this 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 this fantasy role, I was beginning develop disconnect from Sister Natalie to Cassie who said, “Put your arms around me and tell Cassie that you love her.”
Two things: Being a fourteen year old still going through puberty there was no way I was not going to let myself be seduced, molested or whatever perverted action it took for me to put my virgin penis into this live, wet, soft and featherless nun. And I was going to learn everything that she could teach me. But I couldn’t stop thinking how did she get this way anyway?
After about ten to fifteen minutes of kissing and hugging which gave me the pleasure of fondling her breasts, she said, “Stand up Hun.” Kissing, hugging and tit play was so new to me that I could have done it all day. With a wry smile Cassie said, “Let’s take a look at what you’ve got Toby.”
She unbuckled my belt, undid the button and zipped down my fly. The way she licked her lips made her appear hungry. Pushing her hand under the elastic of my BVDs she grasped my boner and assessed it with her fingers. “Mmm Toby you feel much bigger than I expected.” The feeling of her hand on my pecker made me cramp the muscles in my ass to keep from coming. At the same time my ego swelled at the compliment, which made my effort even more desperate. For some reason I felt that it was important for me to hold back, that’s right, she asked me to hold back. Pushing my pants and underwear down together the head of my cock caught in the waistband and snapped back, slapping against my stomach. With a knowing chuckle she said, “Young teens all get hard at an upward angle.” I wondered how many boys my age she had seduced. With her index finger she pressed down on my glans until my penis slipped from her hand and slapped back again on my belly.
“My, my, my Toby,” she said, “you have something to be proud of. (When I became fully grown my erection was just under eight inches and rather thick. At fourteen I was six inches and normally thick, just about the standard size of most grown men’s cocks). Holding it in her hand she inspected me, assessing its general size and contours. Lifting it up she studied the cleft of my knob, my circumcision scar and my seeping pee hole. “There are men Toby who would love to be your size. When you get older you’re going to make some women quite happy. I hope we know each other long enough for me to find out. Tsk, and I think your balls are going to hang like a bulls.” She laughed and said, “I’m PLEASED sweetie, REAL pleased.”
She seemed to be taken with my condition of being completely lost and not knowing where to begin. “I know you want to put it inside me.” She winked and clarified, “My cunny. But when you get inside me I want you to stay hard for as long as you can.” Uncharacteristically she winked. “But that’s not going to happen yet so let’s get this out of the way so it will get better.” Grasping my cock she bent forward and took me into her mouth, first just her lips around the back of my glans, licking the bottom cleft. Then she took me deep inside her mouth and bobbed. I struggled not to come but on her eighth thrust I couldn’t help myself as I cried out, “CASSIE.”
Looking up she thanked me with her eyes for calling her Cassie. With each of my four shots she made a sighing noise. “Mm-hm, mm-hm, mm-hm.” Then she kept milking me with her mouth until any hint of sperm was cleaned from my penis. The sensation became so intense (pleasure and pain) that I felt like asking her to stop.
Stretching out flat on the bed she moved as close to the wall as she could, held out her arms and said, “Come to Cassie Toby.” I lay down beside her and we kissed and snuggled. During this time her lips seemed softer, her tongue more probing and her hands caressing me in such a tender way. I had goose bumps all over my body. While caressing my ass she found my balls and fondled them. To my surprise, shock and pleasure she even rimmed my anus with her middle finger. I didn’t know what to think of that but I liked it. After several minutes of cuddling Cassie broke the silence with a chortle and said in a sing-song way, Toby rises again,” capping it off with, “Oh GOODY.” Then she said, “Let’s do it this way Toby,” The way she was including me in the sexual play made me feel good, like I was a member of the team, “I’ll get off the bed.” Sitting up she threw her legs over the edge of the bed and got up. “You lie flat on your back,” which I did.
Placing her knee on the edge of the mattress she threw her right leg over my body then positioned herself just above my throbbing erection. “You’re so hard,” she said with a joyful lilt. I have to almost pry you cock back to make it point straight up, he-he.” I found it strange that a nun who was always so severe in her everyday life could be acting like so silly, not to mention the fact that she had just used a word like “cock.” I was nervously happy and it felt good to be helping to make the Reverend Mother happy.
I found it strangely beautiful for me to be satisfying my curiosity by watching exactly what she was doing. Hovering over my extending penis with her hand directing it between her legs my purplish head disappeared between her legs and I felt the wetness of her cunny collecting on it. I was taken with the smoothness of her pale skin that was so contrasted by the dark thatch of her pubic hair. As she carefully slid my knob in her bubbling trough in search of her hole it made a sound similar to someone putting lotion on their hands and rubbing it. In concentration her eyes narrowed until the tip of my pecker was in place then, as she began lowering herself and taking half of my boner inside her body they widened as she captured a piece of her lower lip with her teeth.
I felt my knob settle in the indentation of her hole then become centered. I watched as I felt Cassie’s hole open over my hardness and tighten on me just beyond the rim of my pecker head. As she moved in mini-bobs it was like she was fitting her fingers into a glove. I could never have imagined the unexplainable feeling of the inside of her wet, warm and clinging vagina as it moved its wonder on “cock” as she had said. Then, as she began an indescribable descent on my pulsing penis, her mouth formed a perfect oval, like a chorister humming background music. And as her body dropped the matched the length of her downward slide with a satisfied, “OOOOOH.”
For a fourteen year old boy whose cock on his virgin journey inside of a vagina the experience was indescribable. It was wet and warm and spongy. At the same time it clenched my hardness as if it were a fist. I couldn’t explain what the inside of her body was doing to me. All can say is, if my cock were the most important thing in the world the Mother Superior’s pussy was the reason for its existence. To me my erect penis was the center of my world and, as that forty some odd year old woman rode me the way she did, I would have sold my soul to the devil just for five more minutes inside her.
To my surprise she bobbed up and down for longer than five minutes then said, “I’m amazed Toby that we’ve been fucking for so long,” So was I. I was equally surprised, even shocked that a Mother Superior would use a word such as “fucking” with such ease and enjoyment. It hadn’t happened without a supreme effort on my part though as I had been clenching the cheeks of my ass to keep from exploding inside her. When her pussy had made its first slide on my cock I felt like I had to come. But with a heroic clutch I clamped the cheeks of my ass together which made my balls ache. She had made it clear to me that she wanted me to stay hard inside her for a long time. When she had sucked my cock she did it for the purpose of desensitizing me (I later learned that she adored sucking cock). After I came she kept sucking me, tantalizing the ultra-sensitive glans which ached incredibly. But I was determined to let her keep fucking me. I just didn’t know how hard I would have to work at it.
As it turned out she was tired as well from her constant carousel ride. “Let’s take a break Toby,” she said. With my hard cock still inside her she lowered her breasts which flattened on my chest as she braced herself on top of me with her elbows on the mattress. Playfully rubbing her nose on mine she kissed my lip, then did that rabbit nose thing again and said, “You’re more of a joy than I could have ever imagined Toby. You’re an unusual boy, caring and willing to learn. Besides that, he-he-he, you’ve got a nice big cock.” She pecked my nose and with a puckery smile said, “I know how hard you have been working to control your urge to cum so I could enjoy it. In short, my sweet boy, you’re WONDERFUL.” Flattening herself against my body in a covering hug she clutched and wiggled her penetrated vagina that was still so full of me. It struck me how, though I loved to cum, I equally loved being inside a woman like this for such a long time. Knowing that she liked it made me feel like a grown man—a real man.
After resting for about three more minutes she said, “Toby, have you ever seen dogs having sex?” It came from so far out of the blue that I was nearly blown away.
In fact I had a couple of times. “Yes.” I remembered how the male dog mounted the bitch and entered her from behind. “I’ve seen them do it a couple of times.”
It was like she had to stop and pay me the compliment, “Everything about you Toby: the way you work, your caring for me and the sisters, your respectful attitude, the way you are working so hard to make me feel good right now, fills me with a sense of surprise.” She wiggled, “He-he-he, and the way you’re filling me right now.”
I was wondering what that had to do with dogs. “Anyway,” she went on, “people can do it the same way dogs do ... and it is fun, he-he-he. Why don’t you pull yourself out of Cassie’s pussy Honey?” I really didn’t want to. I wanted to fuck her fast and hard and cum inside her. “Then I’ll get on all fours, just like a female dog and you can fuck me from behind.” She didn’t wait for an answer. “Okay Toby, up, up, up now.”
When she stood my eyes poured over her body. As I mentioned before her skin was very pale. It seemed almost transparent like porcelain china. Apparently, her body having been covered so completely for so long kept her skin in perfect condition. And it was so incredibly smooth. Though she had a small lace of crow’s-feet at the corners of her eyes the rest of her body looked like an alabaster statue. And her luxuriant patch of curly dark hair that covered her mound seemed whimsically unruly. I wanted to rest my face on it and get my nose closer to the smell that was wafting from her slit, something which I was eager to see. As I watched her naked body knelt 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 appeared that she was making an act of supplication. Cassie I thought as I turned my head and spied her habit hanging from the hook on the door, trying to make sense of her change from Mother Superior, Sister Natalie.
Then my eyes became glued to the spot I had not yet seen, her pussy. It was hidden inside the thick, curly thatch of dark brown hair. She looked back at me and chuckled, then leaned forward as she reached back and placed her hands on the cheeks of her butt.With a wet click the hair parted and opened, exposing the bubbling, pink entrance to her insides. I was looking at the “holy of holies” which almost caused me to lose my battle with premature ejaculation.
Her voice came as if muted by the position of her head, “Toby?”
She chuckled and said, “Once again you’re such a fast learner. Thank you for remembering my name.” 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?” I saw that she was touching a spot at the top of her slit.”
“Mm, I want you to touch the same spot with me, ok?” I put my finger next to hers. She took hold of my finger and placed the tip on what felt like a node. She wiggled in a quick response at my touch. “This is my clitoris Toby. It’s a spot in a woman that is quite similar to the head of a man’s penis, and is even more sensitive. “Rub it gently for me please, ok?”
I rubbed. She writhed, her ass wiggling and her shoulders twisting. “Mm, a little harder dear.” I rubbed harder and her writhing increased. “Keep rubbing.” I did and she tensed and exclaimed, “YES” and relaxed. “Thank you Toby, you’ve given me my first orgasm today. I didn’t know what an orgasm was but got an idea that it made her feel good.
“Now sweetie, put your hands on my bottom, a hand on each cheek. That’s it. Now spread me open.” I watched as the pinkness of her slick groove became exposed and a dark, bubbling hole in the middle of it opened. It looked like it would be pretty slippery. “Put your finger inside.”
When I did it I was once again overwhelmed at the indescribable feeling of this new experience. But I had to fight off a new need to cum. Sliding my finger in and out, I said, “Like this Cassie?”
“Kind of Toby. But as you move your finger in and out press your fingertip kind of hard against the front wall of my vaginal tunnel.” I did and the wiggling and moaning happened again. “Put in two fingers Honey. Yes that’s it.” The wriggling increased and her moans became louder. “Now, as you fuck me with your fingers put your thumb on my clitoris and rub.” Moving wildly she soon had and even larger orgasm. I felt proud of myself.
As she was still taking deep breaths from her exertion she said, “Whew, that was good Toby, it triggered a magnificent orgasm for me.I just wanted you to know how Cassie’s pussy works. Now dear, are you ready to put your COCK inside Cassie’s PUSSY?”
I was surprise when I put my fingers inside Cassie’s pussy at how much it felt like the inside of my mouth. Just like my mouth it was wet, slick and warm. But it molded around my fingers like their size and shape were designed specifically for that mysterious, inner space. And it was tighter. As a matter of fact Cassie made it tight, I could feel her doing it, squeezing her insides that way. At the same time it was softer than the inside of my mouth. It’s so hard to explain these things, other than the fact that I loved it.
I think she understood why I didn’t answer her question. She just laid her face on the backs of her hands again and pushed her ass up a little higher. Taking in her nakedness with my eyes again and thinking about what we were doing, I felt like pinching myself to prove that I wasn’t dreaming. I hesitated for a moment to hold my fingers that had been inside Cassie’s pussy close to my nose so I could smell them. Again, I couldn’t explain the smell other than to say that I wished Cassie’s entire body could smell like that.
“Time’s a wastin,” Cassie said in her playful sing-songy voice. It brought me back to my purpose. Spreading her smooth, pale ass to open the threshold of her pussy I eyed the inviting pinkness. Holding my cock like a baseball bat I pointed the tip at the hole. Leaning forward I felt her ass push back against it and forced my cock deep inside her.
What happened to my body was like instant climate change. My pecker was warm and loved having it inside her form-fitting pussy. Yet my body became so chilled that it felt like I had gone from one hundred degree sunshine into a deep freezer. I shuddered for a few seconds before heat started rising from my feet: quickly moving to my knees, my thighs, my groin, my chest and finally tickled the rims of my nostrils. I just had to come. But I had made a commitment to Cassie and redoubled my efforts to keep from exploding. My contractions set off opposing actions, the need to spurt my semen and the cramping of my muscles. Squeezing my ass tighter I beat off the threat once again.
The words from Cassie’s mouth were different this time, “Fuck my nasty CUNT Toby, slam my ASS, drive this sinful sister back into a state of GRACE.” Holding her hips I slammed and pulled back, jamming my hips forward and pulling back, making a clapping noise that sounded like applause.
Cassie’s head was now up, her back was arched and she was bucking against me and writhing with all her might. He head waggled wildly, tossing her hair like a wheat field in the wind. She was making so many different sounds that it sounded like she was speaking in tongues. I 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 sounded like gibberish.
“Pinch my NIPPLES Toby, PINCH them. Afraid to hurt her I reached under and pinched her nipples. “I said PINCH my fucking nipples Toby, HURT me.” I pinched harder and her body seized in a spasm which caused her to pause for about ten seconds. “Rub my CLITORIS baby and fuck me HARD.” I slammed against her body and rubbing her swollen node.
Both of our bodies glistened with beads of perspiration and our skin was slipping against each other’s when Cassie said, “Cum INSIDE me Toby, cum in my CUNT.”
My aching balls were swinging up against Cassie’s wild pubic thatch and I was more than ready. Slamming her three more times I was grunting like an animal. Unable to stop my words I said, “Oh my FUCKING God.”
Cassie seemed to hesitate for a second then resumed her climax. When she fell forward her pussy came off my dick and held forth with a long, whooshing pussy fart. Chuckling she joked, “We do make some interesting noises in our sex don’t we young man.” She lay back down with her back close to the wall. Opening her arms she said, “Snuggle with me Toby.” I put my arm under her side and we both hugged, our damp bodies nestling together. We kissed though not as passionately as we began, just coming down and back to life peacefully.
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 very soul.” I listened. I too wanted this to happen over and over again. “You must never forget that I am a bride of Christ, the Son of God. And as such I can’t allow you to blaspheme the name of God.”
Having heard so much about blasphemy at church I knew what she meant and said, “I apologize, Reverend Mother. It will never happen again.”
Lying with this naked woman was strange and wonderful, so mysterious. She was a devoted woman of the church yet she was such a wild, sexual being whom indeed was cheating on what she perceived as her husband. I was just a boy having the good fortune to sow his wild oats in a woman who was willing to teach him every aspect of sex. I didn’t feel guilty at all but I felt guilty for her. At the same time I wondered what kind of world God had created where one of his most treasured creations, a holy woman, was tortured by her need to express herself so desperately that she was doing it with a fourteen year old boy.
“I hope you don’t think ill of my nasty behavior Toby. God is my judge. And I know He will always forgive me.” She smiled in such a blessed way. “We have both sinned you know. I will be forgiven through confession. But I worry about you.” She heaved a heavy sigh and said, “We must get dressed now my sweet boy.”
I was able to pull both my shorts and pants on at the same time. I put on my t-shirt, my socks and shoes. I felt like a voyeur watching Sister Natalie cover herself with her wimple, her gown and her veil, again resembling the penguin that we often joked about. Before we left she asked me, “Will you pray with me Toby?”
At this point in my life, having just been taken to the Promised Land, I in no way would have denied my sexual Angel anything. She took my hand and with both went down on our knees. “I will pray,” she said. “And if you can copy my words.” With that she began her first Novena. By the time she had finished her third I was up to speed on the words and recited the prayer with her until she finished at seventeen. I don’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 you and continues to betray you. Thank you Lord for understanding me. For me 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 Lord, so he can receive Your bountiful forgiveness...”
From my perspective, as she prayed I felt the presence of her penitence. At the same time I wondered when I would enjoy my next sexual lesson. Deep down I was overwhelmed that Mother Superior had chosen me to do this with her. I was quite happy that I was this penguin’s personal preference.