Guided Masturbation Stories
Mrs. Sylvia Bellano
A young college student is very well cared for over the knee and between the bosoms of his landlady. Anonymous, circa 1995
– Part I
Before applying to college in 1963, I spent a number of weekends visiting prospective schools in Ohio and Pennsylvania. I had already heard a lot about Smithson College from my first cousin, Fred who was then in his senior year and full of stories about wild parties, road trips, and other mayhem. As a scholarship kid, he lived inexpensively off campus by renting a room from a widow who worked as a children’s librarian in the public library. In exchange for a modest rent and help around the house and yard, Fred enjoyed the benefits of a normal home. Mrs. Bellano did all the cooking and even took care of his laundry. In contrast to dorm life with its tiny rooms, bad food, and noise at all hours, Fred had it pretty good, especially since Mrs. Bellano was a great cook. The only downside was the need to observe basic household rules. Fred had to be in by 10:30 on weekdays and 12:30 on weekends. He also had to keep his place neat, do his chores on time, and not bring liquor into the house. Though he sometimes missed the freedom of dorm life, he saved a thousand dollars a year over the costs of campus room and board. And since he was a scholarship kid, he didn’t really have much of a choice. Living on campus was simply out of the question.
Though I could never tell Fred, I had a particular interest in hearing about his landlady. It seems she still spanked her fifteen-year old son, Tommy. And on a few occasions when Fred had forgotten to do his chores, Mrs. Bellano had even hinted Fred would have gotten the same treatment had he been her child. The idea that my cousin lived with a woman who spanked her teenage son and believed such discipline was still appropriate for a misbehaving twenty-year old aroused many fantasies in me. For nothing intrigued me more than the idea of a loving, maternal figure who doled out spankings in her home. Such fantasies emerged from years of personal experience in a household where spanking was frequently used to maintain discipline. I had been spanked by my mother right up til puberty which came rather late at the age of sixteen. Even then, I think my mother stopped more because I was getting erections than because I was too old. By then, domestic spanking was central to my sexual fantasies. When I masturbated, I pictured a sexy, older woman spanking me while I wriggled on her lap or bare thighs until orgasm. Sometimes she consoled me afterwards by suckling me at her breasts or by taking me into her bed for passionate lovemaking. In hindsight, such fantasies emerged from my sexual insecurity and extreme shyness around girls. By imagining I would be initiated sexually by an older, experienced woman, I created sexual scenarios which were non-threatening. (Up until college, I had never even dated, much less kissed a girl.) Given this background, it is easy to see why I was so excited and curious to hear that my cousin’s landlady still spanked her fifteen-year old.
I saw Fred a lot during his vacations since he lived four houses away. Needless to say, I always tried to steer the conversation around to whether Mrs. Bellano had spanked Tommy lately without trying to appear too interested. Though Fred was happy to provide some details – Tommy was always spanked on the bare bottom in his room with the door closed – Fred would only go so far before asking why I wanted to know so much. That was my signal to back off and change the subject lest he suspect I had a special interest. Nor did I want Fred to know I had been spanked myself til I was sixteen.
In the summer before my senior year, I made plans to visit prospective colleges including Smithson. Fred asked Mrs Bellano if I could stay with them and she readily agreed. Hoping Fred would be too busy to meet me at the train station in midweek and that Mrs. Bellano would come instead, I arrived on Wednesday and was indeed met by Mrs. Bellano. On the basis of Fred’s descriptions, I had no trouble recognizing her and waved as I stepped off the train. To my wonderment, she was even more beautiful than I had imagined. In her late thirties, she had lustrous black hair which cascaded thickly around her face and over her shoulders and set off her smooth, pearly white skin. Her eyes matched her hair and flashed like dark jewels in her lively face. In a period when voluptuous women were still widely appreciated, Mrs. Bellano had a heart-stopping hourglass figure. Her hips swept out from her relatively narrow waist with large, full curves which rolled sensuously back and forth with each step. As if in musical counterpoint, her lush, tightly sweatered breasts accented these larger movements with their own swaying. No doubt, most people at the train station that day saw only a plump woman greeting a relative or friend and gave it no notice. In contrast, I was almost mesmerized by Mrs Bellano’s ripe, jiggling, womanhood which seemed heightened with every ordinary movement.
Greeting me as if I was a family member, she swept me into her arms for a big hug and a kiss. Though it lasted no more than a few seconds, my head spun as her heavy breasts pressed against my chest and a wave of strong perfume engulfed me. I even began to tremble and wondered if she noticed. As we walked down the platform, I tried to make small talk but my mind was completely absorbed in her wonderful scent and sight. I was particularly fascinated by the regular swishing sound of her nylons rubbing against each other. After reaching the end of the platform, we had to go single file to get up the narrow stairs. By politely inviting her to go first, I took my place directly behind her where I could gaze more openly. Her cotton summer dress clung to her revealing a fat bottom and the lines of a pair of bikini panties which called additional attention to the lush curves they failed to contain. As she climbed the stairs, her heavy bottom cheeks bobbled and wagged with a fleshy life of their own. And with each step came the wonderful silky swishing noise from beneath her dress. By the time we reached the top of the stairs, I had to conceal a throbbing erection by holding my bag in front of me. Already my mind raced with fantasies of attending Smithson and renting Mrs. Bellano’s room.
Though I was off touring the college campus for most of the following three days, I did see a lot of Mrs. Bellano in the evenings. Her cooking was indeed delicious and her manner warm and inviting. By the end of the weekend, it was clear she liked me and I did nothing to conceal my warm feelings toward her (though I tried to keep from staring too much lest she think me vulgar). Only once did I give myself away. It was on my last day – Sunday afternoon – and Fred was outside mowing the grass. Following Mrs Bellano’s instructions, I took three glasses from the kitchen into the living room and placed them on the coffee table while she made lemonade. I then sat on the sofa and waited. After a few minutes, Mrs Bellano came in holding a pitcher full of iced lemonade and sat in a chair across the table from me. Since it was quite hot that day, she was wearing a loose-fitting sun dress which left her shoulders and upper torso bare. And because the coffee table was so low, she had to lean forward and bend way down to pour the lemonade. When she did, I suddenly found myself looking directly at two enormous, pillowy white breasts nestled snugly against each other in a pink brassiere which was so low cut I could only see it primarily where it crossed between and underneath her breasts and along the lacey edges. Even if she hadn’t been preoccupied in pouring lemonade, it would have been hard not to stare.
Her milky globes bulged up and out of her brassiere, spilling over generously at the tops into unconstrained patties wobbling gently like mounds of jelly. With my heart pounding and my senses dazed, I forgot about all else and stared shamelessly. Fortunately, Mrs Bellano was absorbed in pouring the lemonade, using a spoon to keep ice cubes from tumbling out of the pitcher and splashing into the glasses. And because she had to pour slowly to avoid spilling or splashing on the antique table, I had about two full minutes to feast on the view she unwittingly presented. Even as she poured, a little voice told me to stop staring before she looked up and caught me but I ignored it, glued to the sight of so much naked, womanly flesh.
By the time I looked up, I found her dark eyes looking directly into mine. Instead of sitting up abruptly in shock or embarrassment, she held her position for a moment as if to use her breasts, now knowingly exposed a few inches below our connected gaze, to remind me of what she had caught me doing. And as she straightened up, a little knowing smile crept into her expression which only heightened my embarrassment. Turning bright red, I mumbled a thanks about the lemonade, looked out the window, and wondered aloud if Fred had finished the mowing. To my great surprise, she only gave me a warmer smile before hoisting her glass and toasting to the success of my college search. Then looking me straight in the eye, she said,
“As you know, Billy, I will be needing a new tenant next fall now that Fred is graduating. You seem like just the kind of polite, young man I am looking for. If you get accepted at Smithson and decide to come, you should consider renting Fred’s room. It’s a lot cheaper than the dormitory and Fred tells me I’m a great cook.”
I could not believe my ears? Here was a woman who had just caught me staring fixedly at her breasts inviting me to be her new tenant. It was as if she were flattered by my attention. With my insides churning even more, I managed to stammer that Fred had really enjoyed renting from her and that I would certainly think about it, especially since I was also looking for ways to reduce costs. After promising to let her know when I heard from the admissions office, I looked up with relief to see Fred entering. An hour later, Mrs. Bellano drove me to the train station and gave me an even longer hug which fueled masturbation sessions for at least he next month.
My senior high school year passed slowly. I counted the days til the college letters went out in the spring. When my acceptance letter came from Smithson, I gave out a loud cry of excitement knowing I would be seeing Mrs Bellano every day for the next four years. And so it was that I found myself moving into her house that August, little more than a year after our first meeting.
On the very first night, after Tommy had finished the dishes and disappeared into his room, she sat me down in the living room to explain the house rules and my chores. I was to do the dishes every other night or set the dinner table on alternate nights (sharing that job with Tommy). My room was to be kept clean as well as the single bathroom which everyone shared. In the summers, I was responsible for weekly mowing. Weekday curfew was 10:00, weekends were 12:30. I was not to bring any alcohol into the house or to come home drunk. She then explained that she used a monthly lease so that she could evict any tenant who failed to follow these rules, something which had happened twice in ten years. I assured her she could count on me and that I would treat her house like my own. In turn, she insisted I call her Aunt Sylvia.
Then Mrs. Bellano introduced the subject I had been waiting for.
“Billy, as you know, I’ve been a widow since Tommy was four. It’s been quite hard raising him all on my own without a father figure in the house. And Tommy’s a rather head-strong boy, still quite immature for his age. I don’t know if Fred told you or not but in this household, I use spanking to keep Tommy in line. I’ve been spanking Tommy ever since third grade and don’t intend to stop now just because he’s a teenager. If anything, a bare-bottomed session over my knee is more effective in reminding him how to behave now as he enters his teen years. I’ve tried other things like grounding and cutting off his allowance but nothing works as well as a spanking. Tommy’s even admitted as such himself. Though he hates getting spanked, he does prefer to get his punishment out of the way quickly. Of course, at fifteen, he’s rather old for such methods but that only makes them more effective. If he wants to avoid spankings, all he has to do is mind me. Despite his best efforts, he seems to get into trouble sooner or later regardless of how old they are and Tommy is certainly no exception. I often tell him he can expect to be spanked as long as he misbehaves under my roof. Of course, the older he gets, the more embarrassing his spankings are and the more he hates them. But the choice is his.
For example, he didn’t make his bed yesterday and today he forgot to put the trash out so that we’ll have twice the amount in the garage for the next week. He knows he’s earned a spanking before bedtime tonight which is why he went to his room early. Since it’s somewhat unusual to spank a youngster his age, I thought I should give you some advance notice and offer an explanation so you aren’t surprised. You’ll find that Tommy earns a spanking about once every eight to ten days. That may seem like a lot for his age but it’s half what he needed up until two years ago. This change alone shows the value of my methods. Now if you’ll excuse me, I have a naughty boy to attend to and I know you probably have some studying to do.”
With that she disappeared up the stairs and into Tommy’s room. Immediately I rushed into my room, closed the door and began to masturbate as I listened to the sound of Mrs. Bellano scolding interspersed with Tommy’s pleas for mercy followed at last by the sharp, distinct noise of a hand slapping a bare bottom. This sweet music lasted a full five minutes, during which I achieved two climaxes accompanied by thoughts of Mrs Bellano spanking me. Afterwards as I lay in bed, I could not believe I was going to be spending the next four years living with this incredibly nice, sexy lady in a house which resounded periodically with spankings.
As often happens with freshmen, I went somewhat wild my first semester away from home in the unregulated atmosphere of college. Never had I had so much freedom and I found myself coming home a little late on some weeknights due to parties. Mrs. Bellano even warned me about following her rules on two separate occasions. One night in early October, I told Mrs. Bellano I was off to the library to study. And I really was. Unfortunately, I ran into my best friend who persuaded me to blow off the evening by going to a party he’d heard about in someone else’s room. I then five or six glasses of a vodka fruit punch which doesn’t taste at all like alcohol and by 8:30 I was drunk. By 9:30, I was so soused, I completely lost track of the time. When I finally looked at my watch, it was 10:30 and I knew I would be in trouble with Mrs. Bellano. I staggered home, arriving just before 11:00. Unfortunately Mrs Bellano was still up reading in the living room and there was nothing I could do to hide my inebriation when she began questioning me. But instead of scolding me, Mrs Bellano simply said,
– Part II
“Young man, you are in no state to discuss anything with me tonight. You should go straight to bed for now and we can talk in the morning after Tommy goes to school.”
The dreaded moment finally came the next morning when Tommy departed around 8:20. Though somewhat hung over, I was more upset than anything else about letting Mrs. Bellano down and jeopardizing my position as a tenant. After sitting me down on the sofa, Mrs. Bellano seated herself in a nearby chair and began.
“Young man, when you signed the lease here, you agreed to follow certain simple rules which are probably no less restrictive than the ones your mother applies in your own home. You’ve had a warning last week and now I find you coming back after your curfew and staggering in drunk on a weekday. And on top of it all, you lied to me by saying you were off to the library. I consider dishonesty far worse than lateness or drunkenness which one can expect from someone your age from time to time. But there is no excuse for dishonesty nor can I have any tenant living in this house whom I cannot trust. Since you’ve already had one chance, I really don’t see any other choice than to ask you to find another apartment.”
“Please, Mrs. Bellano,” I responded, “I know I was a great disappointment to you last night. You’ll probably never believe me but I really was going to the library until I ran into a good friend who invited me to a party. I know I shouldn’t have gone partying on a weeknight and I made things worse than ever by drinking so much, but I swear I wasn’t lying when I said I was heading for the library. That really was my plan.” Then, with my heart pounding, I found myself adding,
“I know I’ve messed up big. But isn’t there anything else you can do instead of making me leave? I really like it here and want to stay more than anything.” Mrs. Bellano paused for a few moments, looking at me thoughtfully. Finally she spoke,
“Billy, if you were my son, I would have other ways of controlling you but you’re not. The only way I can handle a college age tenant living under my roof is through a system of trust and basic rules. And you have proved yourself untrustworthy.”
“I know I have, Mrs. Bellano, and I really regret it. There’s no question I deserve to be evicted but I beg you to find some other way to deal with me.”
“What would your mother do if you pulled a stunt like this,” Mrs. Bellano asked. I hung my head childishly and replied,
“She would punish me. Mrs. Bellano”.
“And how would she punish you?” Mrs Bellano replied?
“She’d probably ground me for two or three weekends”.
“Well, Billy, I really don’t think that would work very well. You’re much too old to be acting this way and I doubt a grounding would have any long lasting effect. I know what I would do if Tommy ever acted this way, even if he were your age. What did your mother do when grounding didn’t work?”
Though my mouth went completely dry, I managed to stammer, “Well, actually, Mrs. Bellano, up until two years ago, my mother sometimes … well you know … she sometimes handled me … um … you know … the same way as you handle Tommy. And besides … um … if I want to stay on … in … you know …. in your home, I suppose I don’t really have much … have much choice, do I.”
With her eyes widening and a smile playing about her lips, Mrs Bellano paused again as if weighing certain possibilities.
“So, your mother brought you up the same way I raise Tommy, did she? Well, I’m glad to hear I’m not the only one who believes in old fashioned methods. I don’t know, Billy, I just don’t know. What am I going to do with you? My best judgment tells me I should look for a more reliable tenant. On the other hand, it might work if you were willing to let me treat you as my own child. I suppose I could consider trying a temporary arrangement … a kind of probation period … let’s say for two or three months. You would have to be in earlier, perhaps by 9;00 on weeknights and 10:30 on weekends. Any lapses, late chores, or other problems would result in punishment from me. If things worked out for the whole two or three months, you could go back to your original curfew but I would still punish you when you got out of line. Without some long-term, effective means of maintaining discipline in my home, I just don’t see how it could work. I think you should think carefully about my proposal, Billy? You know what happens to Tommy when he misbehaves, don’t you?”
“Yes ma’am, I do,” I said with my head still hung down.
“Look at me when I’m speaking to you, young man, and call me Aunt Sylvia, please. Do you think you would like to try this proposal of mine?”
“Yes, Aunt Sylvia, if you think it would work.”
“Well then, what do you think you have coming for your behavior last night and for that matter, from now on whenever you act up?”
“A … a … a sp … spanking, Aunt Sylvia?” I asked.
“Yes, young man. A sound spanking on your bare bottom. Actually, since you missed your curfew, got drunk, and probably lied on top of it all, you’ve earned two spankings, one in a few minutes, the second at bedtime tonight since Tommy will be sleeping over at his friend, Johnny’s house tonight. Judging from your behavior, I suspect it won’t be the last time I have to put you over my knee. I never thought I’d have two naughty boys living in my home who needed spankings but that’s exactly what I have now, isn’t it Billy?”
“Yes Aunt Sylvia.”
“When is the last time your mother spanked you Billy?”
“Last April, Aunt Sylvia, after I stayed out til midnight without telling anyone where I was.”
“Why … that means you haven’t been spanked in six months. No wonder you’re acting up so much. Six months … I’d say you’re badly in need of the spanking you’re about to get.”
“Oh… please … Aunt Sylvia … please don’t spank me now .. please,” I begged, fighting back a tear.
“Nonsense, young man. A sound spanking is just what you’ve been asking for with your recent behavior. Now give me your hand, child, and come upstairs with me. You’re long overdue for this lesson and I’m going to make sure it’s a good one.”
And with that, Mrs Bellano crossed the room and took me firmly in hand as if I were a little boy. Pulling me to my feet, she marched me upstairs to my bedroom smacking me on the bottom to make sure I kept moving in the right direction. Closing the door behind us, she escorted me to my bed, sat down and with one tug pulled me over her lap. Before I knew it, my right hand was tucked up into my back, my pyjamas pants and briefs were lowered to my knees, and my spanking had begun. I was surprised at how hard Mrs Bellano spanked – much harder than my mother – and soon I was begging to be let off. But Mrs Bellano just tightened her grip on me and continued walloping me, alternating between one cheek and the other.
“Oh … oh … Aunt Sylvia, it hurts so. Please, no more, oh no, please”
“It’s supposed to hurt, you naughty thing, it’s a spanking. You should be grateful I don’t believe in using the hairbrush. You can beg me to stop all you want but I promise you it won’t have any effect. We’re just getting started here and you’re going to be a lot more sorry before I’m through. I find all bad boys act pretty much the same once they’re bare-bottomed across my knees. They might be eight, twelve, sixteen, or eighteen, but long before I finish with them, their fannies are bright red and they’re sobbing like little children. That tells me they are learning a good lesson. And believe me, young man, before I’m finished with you, you will be taught a very, very sound lesson. It’s time you found out exactly what to expect every time you misbehave in my house. Do you understand me, Billy? You can whine and beg for mercy all you want now but you’re not going anywhere until I see a very well spanked, crying little boy over my knee.”
At my age, I could easily have escaped but it would have meant finding another room to rent. By agreeing to Mrs Bellano’s arrangement, I had given her a kind of invisible power over me, as if I really was a naughty child who could be easily held in place for a sound spanking. It was clear I was allowed to kick and cry out like any youngster but I had to stay put until Mrs Bellano deemed my spanking was finished. And true to her word, she taught me a good, very long lesson. On and on she spanked. After a three or four minutes, she settled into a slow, steady pace moving back and forth from cheek to cheek. As I kicked and pleaded, it suddenly struck me that I had indeed behaved terribly and that I fully deserved the childish punishment I was now getting and would continue to get in the future. Without fully understanding what was happening, I began to sniffle and cry in a childish tone while giving up the worst of my struggles. It was a turning point for both of us and marked the moment when I sank into a certain acceptance of my punishment. Here, at last, was the loving guidance I missed so much since my mother had stopped spanking me two years before. Through my tears, I realized Aunt Sylvia had been right. After a good five minutes over her knee, I had indeed become a crying little boy who had broken an important rule and needed to have some firm correction to make everything right again at home. Whatever else was happening right then, I knew I was safe in a loving household with a woman who cared enough to make sure I got the discipline I needed.
I know that first spanking from Aunt Sylvia lasted fifteen minutes because I could see the bedside clock the whole time. It would have gone on longer but the phone suddenly rang in the next room and Mrs Bellano had to get up to get the phone. But instead of leaving me on my bed, she quickly stood me up and marched me to the corner.
“You are to stay here, young man, until I return. If you think I’ve finished with you, think again. You still have some more medicine coming and you can spend the next few minutes thinking about that while I see who is on the phone.”
After she left, I looked down in dismay at my bottom which was completely scarlet from one side to the other and from the tops of my cheeks to the base. The thought of more spanking to come was hard to believe yet as Aunt Sylvia chatted on in the next room, the stinging gradually subsided into a warm, comforting glow. As I thought about what was coming, I found myself getting an erection. Horrified, I squeezed my penis hoping to abate the problem but it only made things worse. By the time Mrs Bellano returned, I was hugging the corner to hide what was now a very stiff penis curving all the way up to my navel. (Though late to puberty and completely inexperienced in anything sexual, I was nonetheless rather well endowed.) Crossing over to the bed and sitting down, Mrs. Bellano smoothed her skirt and announced,
“All right, little boy. I think we’re ready to finish your spanking and get you off to school. Get your naughty bottom over here.”
Instead of doing as I was told, I remained frozen with embarrassment, hiding myself in the corner. When Mrs Bellano threatened to postpone the rest of my spanking til Tommy came home from school and carry it out in the living room, I turned reluctantly and hobbled towards her doing my best to cover myself with my hands. Of course this was quite impossible. My face turned even redder at Mrs. Bellano’s comments.
“Goodness, we are well equipped, aren’t we, young man! And I see you approve of my discipline methods, Billy. Hmmm … it looks like you’re going to need more spankings than I first thought. Now wait one minute while I get my new skirt out of the way. We can’t have you ruining it with an accident, can we? With that she raised her skirt almost to her waist, revealing plump thighs sheathed in pink stockings and garter belts and a glimpse of pink panties. I tried not to stare but it was impossible.
Taking my hands away, she looked with evident approval at my now throbbing penis before tugging me once again over her lap. I gasped as I felt myself pressing into her soft, warm thighs but more was to come. For Mrs Bellano carefully opened and closed her thighs, trapping my penis in a firm, velvety grip which brought from me an audible moan. Immediately she began spanking me. Though her thigh-grip anchored me even more firmly over her lap, it also transformed every little twist and turn of mine into a gentle frigging sensation. After a few minutes I completely lost control of myself as my struggles on her lap gradually turned into little pelvic thrusts. My cheeks descended with each spank before arching up to meet the next one. In response, Mrs Bellano began spanking me with an even slower, gentler pace which was more of a slapping caress. And suddenly I found myself saying things I had only been able to think secretly up until then.
“I know I’ve been naughty, Aunt Sylvia. I’m sorry for being such a bad boy. Oooohh …. ooooohhh … I’ve learned a good lesson, I really have. I promise I’ll be good … I promise. Oooooh … Noooooo. Don’t spank my fanny any more this morning, Aunt Sylvia. Please let me have the rest tonight.”
“Don’t worry about that, young man. You’re going to be spending at least thirty minutes over Aunt Sylvia’s lap when she puts you to bed tonight. Now do you understand what I meant when I said how I was going to handle you? Are you sure you want to stay on in my home?”
Ooooh yes, Aunt Sylvia. Please let me stay on even if you have to spank me when I’m bad. Are you going to spank me every week like Tommy, Aunt Sylvia?”
“At least once a week, Billy. It’s now clear to me you are one of those teenagers who is still very immature and very much in need of firm guidance, especially regular, bare-bottom spankings. Fortunately, I know exactly how to handle a boy with your needs and I will do my best to see they are met. Do you remember the Mother Goose nursery rhyme about the “The Old Woman Who Lived in the Shoe who had so many children, she didn’t know what to do? Well, she gave them hot soup and lot of bread and spanked them every night before putting them to bed. That seems to be the kind of routine you might need. Don’t you agree?”
“If you think so, Aunt Sylvia.” At this point I would have agreed to anything since I was seconds from orgasm.
“I’m glad to hear that, Billy, since you’re going to be spending a fair amount of time over my lap. Why you’re obviously … Oh my! … Oh my goodness! You dear boy! You dear, dear boy!
At that moment my hips began uncontrollably jerking as I moaned audibly and began to shoot jets of semen between her soft, welcoming thighs.
“Oh my goodness, you certainly are excited, young man. I suppose it’s a normal reaction for an eighteen year old when he’s bare bottomed across a grown woman’s lap.”
As I continued to pump my loins up and down, Mrs Bellano spanked away with the same gentle pace while squeezing me with her thighs. My semen had moistened things sufficiently so that I could thrust deeply between them. After a dozen such thrusts, I collapsed limply across her lap and she began fondling and caressing my sore cheeks as if to soothe them. And instead of scolding, she commented on how cute and spankable my fanny was and how well she knew we were going to get along. Finally, she stood me up and left me to take my shower after reminding me I had another spanking coming at bedtime.
– Part III
All during school that day, my mind dwelled on the events of the morning and the impending second spanking. Dinner with Mrs Bellano was excruciating if only because she made no mention of the change in our relationship, asking me only about my classes and telling me about her day at the library. After I had finished the dishes, I retired to my room to do my homework while she read the newspaper in the den. It was only then that I noticed an illustrated copy of Mother Goose rhymes from the library which she had placed on my bedside table. Opening it to the page on “The Old Woman Who Lived in a Shoe”, I saw a full- page, color illustration of a long line of bare-bottomed children waiting to go over the old woman’s lap or crying and rubbing their bottoms after their spankings. Within seconds, I was stroking a hard penis through my clothes with thoughts of what Aunt Sylvia had said earlier about how I needed regular discipline. At about 9:30, she poked her head in and said,
“Billy, I see you’re enjoying your Mother Goose Rhymes. I’m going to run myself a bath right now. I want you to get into your pjs now before I go in to take my bath. I’ll be back in three minutes to check on you.”
I blushed at being caught with the book open to the large illustration of “The Old Woman who Lived in the Shoe” and closed it quickly. Hurriedly I changed into my pyjamas as I heard her start the bathwater in the nearby bathroom. I then sat on the bed, wondering why she wanted me to check on me before taking her bath. After a few minutes, she came back in wearing just a pink terry cloth bathrobe.
“Good boy, Billy. I’m glad you know how to mind Aunt Sylvia. Now come on, stand up … that’s it … come over to the corner with me … that’s my good boy … Aunt Sylvia wants you to stay right here in this corner while I take my bath. Do you understand? You can think about why you need to be put over my knee for another good spanking and what’s going to happen to you every time you misbehave in my home. Do you understand?”
Just in case I didn’t, she planted four good spanks on my pyjama bottoms.
“Remember, I don’t want to catch you out of this corner when I come back after my bath. Do you understand me, sweetheart?”
“Yes, Aunt Sylvia … I guess so.”
“That’s a good boy, Billy. I’ll be back to take care of you a little later. Here, I’ll move your book to the desk here so you can see it from the table.”
After opening the book of nursery rhymes to the page I had been examining and placing it next to me on my desk, she left my room and returned to the bathroom where she closed the door. In a flash, I was out in the hall and down to the door which had a big, old-fashioned keyhole. I looked through just in time to see Aunt Sylvia take of her pink bathrobe and show her gorgeous heavy tits and bottom before she stepped into the tub and disappeared from sight. With my heart pounding, I returned to my room and began playing with myself on my bed, careful not to erupt and make a mess. Eventually, I heard the water begin draining from the tub and I got back into the corner well before she finished her bath and opened the bathroom door.
Five minutes later Aunt Sylvia came in wearing the same pink robe over a lacy white nightie which peeked out flimsily at her neck. The robe was tied at the waist in a way which moulded her full hips below and the freely undulating mounds of breast above. I was pleasantly surprised at how much cleavage was showing. A wave of bath oil and perfume made her seem even more sensual. Sitting down on my bed, she let the lower half of her robe part, revealing bare flesh all the way up to mid thigh. It was then that I realized she must have been wearing a baby doll nightie.
“Turn around, young man. Have you been thinking about why you need to learn another lesson from me today? As that book shows, bedtime is the best time of all for putting a naughty child over a maternal lap for a good spanking. Especially early bedtime like 8:30. As you’ve heard, I use bedtime discipline frequently with Johnny. Although you could probably benefit from a bedtime spanking every night, Aunt Sylvia will spare you the embarrassment of warming your bottom when Johnny is in the house. I imagine you wouldn’t want him telling all his friends in the neighborhood. But whenever he is staying over at a friend’s house or is out for the evening, I want you to be in your jammies by 8:00. Do you understand?”
“But Aunt Sylvia, Johnny’s out almost every Friday and Saturday night and he has choir practice on Monday and Wednesday nights. Surely you don’t mean I’ll have to stay home on the weekends and got to bed early?”
“That’s precisely what I mean, Billy. You are going to be out to bed early after a good bottom warming whenever Johnny is out for the evening. Just like tonight. And starting next year when Johnny goes away to college, I might start putting you to bed early every night, say at 10:00 so you have time to do your homework properly. Besides, it looks like you are looking forward to what you’re about to get from me. Why don’t you be a good boy and come over here.”
This last remark was directed at the large bulge pressing against the thin cotton of my pjs and made me blush. Seeing her crooked finger beckoning me, I came out of the corner and over to where she sat on my bed. With a sly smile, she unsnapped my pyjama bottoms and lowered them. Then to my delight and surprise, she grasped my penis with her left hand and pulled me across her lap while squeezing me rhythmically the whole time.
“You took your first spanking so well this morning, Billy, I think I’ll let you off more easily tonight. I can see you going to need a very special bedtime spanking,” emphasizing the word “special” with a squeeze. And with that, she began a gentle spanking similar to that given after the morning phone interruption. This time she rested her hand warmly in place after each spank. And with every spank, she squeezed me down below with her other hand. Within a few minutes, I called out,
“Oh Aunt Sylvia … oh Aunt Sylvia” and climaxed into her hand.
“You dear boy … oh my … you dear, dear boy. I can see you like your spankings from Aunt Sylvia’s don’t you.”
For my part, I continued to repeat,
“Oh Aunt Sylvia, yes I do … Oh yes, Aunt Sylvia.”
“You’re going to need more bedtime spankings, aren’t you, Billy?”
By then, I would have agree to anything and I did so readily.
“Oh yes … Aunt Sylvia, yesss … more bedtime spankings … yes oohhhh….. oooooohhh.” As I agreed with her every suggestion, I thrust myself in and out of her hand which was now slippery with semen and had formed a wet sheath. At that point, I was lost in a dream-like state of exhaustion, pleasure, warmth, security, and love. I lost track of time and drifted in a slippery, sensual, thrusting state while she continued to masturbate and spank me gently. The next thing I remember was the gradual sensation of another erection returning in response to her continued squeezes.
“My, you are a sweet boy. I’d give you another special spanking now but it’s really getting late. Why look … it’s almost 10:30. I think we’d better get you under the covers so you can get some sleep, OK Billy?”
With that, Aunt Sylvia raised me off her lap, gave me a big hug, and stood up so she could fold back the covers. She then pulled my pyjama bottoms up and snapped them and helped me into the bed. Finally, she leaned over to pull the covers up. In spanking me, her bathrobe had come loose at the top. And as she leaned over to tuck me in, the robe fell open even further, showing me two of the most luscious pair of breasts I had ever seen swaying freely against the gauzy nylon. Her whole torso was still pink from the hot bath and looked all the more appetizing. Because of my angle of vision, I could see everything as she worked to arrange my blankets, even her aureoles crowned with stiff nipples. It seemed every moment of her body transmitted itself directly to her breasts where it was magnified into a jiggling dance. Announcing that my pillow needed attention, Aunt Sylvia bent directly over my face and began to fluff my pillow behind my head. This brought her pendulous breasts directly over my face so that the nylon-covered globes even brushed me a few times. Completely overcome, I fastened my mouth around the nearest nipple with a groan and began sucking for dear life. Instead of pulling away, Aunt Sylvia began softly moaning herself and sat down beside me, lowering herself further against me so her breasts enfolded my face.
“Oh you dear, sweet boy … you dear, sweet boy. You need your Aunt Sylvia’s warm, maternal breasts don’t you? And she needs you too … yes she does. Wait a second … let’s move this nightie.”
With that, she pulled a wispy sting at her neck and let the filmy garment fall to her waist. In an instant, I buried my face directly in her naked, warm, breast flesh, my hungry mouth darting from one nipple to another while she encouraged me with a steady stream of endearments and soft moans. The more I pressed my face into her breasts, the more she stroked my hair and held my head gently but firmly in place as if I were a nursing child. For my part, I made little whimpering noises of pure pleasure, conscious that I sounded like a two year old but all the happier for being free to respond this way to her. Suddenly I let out a little cry as I felt her other hand steal beneath the covers and under my pyjamas to grasp my stiff penis.
Time stood still once again as I closed my eyes and escaped into a dream of breast suckling and masturbation. At some point. Aunt Sylvia turned off the bedside light so the room was dark and pulled back the covers to climb on top of me. At first I thought this was to allow me even better access to her breasts but as I came up for air, I found a warm, wet mouth kissing me passionately, her tongue hotly exploring my lips. Using my hands to continue giving her breasts the attention they deserved, I enjoyed the sensation of French kissing which was new to me. After ten or fifteen minutes of this, Aunt Sylvia shifted up a little on me and guided my penis into the most warm, slippery, heavenly place it had ever encountered. Completely overcome, I lay back and let Aunt Sylvia expertly ride me, holding on to her full hips for life and letting her breasts slap me repeatedly on the face as I captured her nipples in my mouth. As I approached my second orgasm of the night and began shaking and thrusting wildly beneath her, I cried repeatedly,
“Oh Aunt Sylvia, I love you … I love you, Aunt Sylvia.”
“I love you too, you dear, dear boy. I love you too. And I’m going to make sure you are well loved and well spanked and well nursed as long as you are living here with me.”
Guiding a fat breast back into my mouth, she lay down against my side, stroked my face, and continued,
“It’s clear you are still very much a little boy at heart and if there’s one thing little boys like you need, it’s regular bare bottom spankings. Starting tomorrow, I am going to begin a weekly demerit book. Tommy is away most Saturday afternoons with Little League in the spring and summer, basketball in the fall, and hockey in the winter. I want to see you here in your room every Saturday after lunch at 1:30 so we can have go over your demerit book and settle things for the week. Do you understand me”?
I nodded into her breasts without interrupting my eager suckling. As I contemplated the prospect of a weekly spanking hour, Aunt Sylvia went on to describe additional plans for me.
“Saturday afternoons will be a real disciplinary spanking just so you don’t think this is all just fun and games. I’ll start out with a hand spanking and switch over to my paddle. A boy your age can learn a much better lesson when he feels a good paddle on his naughty bottom. And we will have early bedtimes whenever Tommy is away as I said before. There’s one more thing. Since little boys are not allowed to play with themselves, I expect you to behave yourself on that score. And to be sure, I will come in every morning at 8:00 after Tommy goes off to school and make an inspection. If I see any signs of self-abuse, you will get a separate spanking right then and there. Do you understand me, young man?”
As if to reinforce her question, Aunt Sylvia gently frigged my soft penis with her hand. Again I nodded into a heavy breast, surprised to find another stream of blood beginning to flow into my penis in response to her expert hand.
“If I turn back the covers and find you are stiff, as often happpens to young men in the morning, I will take care of the situation since I don’t want you playing with yourself. There are many ways to milk a naughty boy while spanking him, believe me. If fact, I think you’re going to need another milking right now, judging by the look of things. Billy, why don’t you stand up by the side of the bed so I can show you what to expect. Any young man in this condition needs release but it’s not something he should ever do himself, is it?”
I shook my head and stood up beside the bed while Aunt Sylvia sat on the edge and guided me between her thighs. The whole time she kept one hand on my penis, still frigging me, while palming my warm bottom with the other. All shame had long since vanished and I just stood there, thrusting gently into her hand with my eyes closed and murmuring,
“Oh Aunt Sylvia … ooohhhh … that feels so good.”
– Part IV
Suddenly a thought struck me and I opened my eyes and looked down at my landlady.
“Aunt Sylvia, what if I’m like this every morning when you inspect?”
“Then I will make sure you to milk you thoroughly every morning, young man. My usual method goes like this.”
As she spoke, she began gently spanking me fairly mildly with her right hand while continuing to frig me with her left. SPANK … FRIG … SPANK … FRIG. On and on she went until a circling warmth spread throughout my loins, front and back, dissolving everything into a single tingling, surging, squeezing, smacking, bouncing, thrusting sensation.
“Of course, there may be times when a young man has trouble producing any milk. Fortunately, there are other ways to take care of that problem when it arises. For example, I think you’ll find this method usually works.”
Turning me slightly toward her, Aunt Sylvia bent down and before I knew it steered my hard penis into her warm, wet mouth without interrupting her steady spanks.
As her mouth licked and sucked up and down the full length of me, all I could say was,
“Oh my God …. Oh my God … oohhhh”. So this was it felt like! I quickly felt myself nearing the point of no return and began tensing up. But before anything could happen, Aunt Sylvia straightened back up, gave the head of my penis a hard squeeze which stopped me in my tracks, and said,
“You see what I mean, Billy. There are many ways to milk a young man, even when he has trouble producing. Somehow, I don’t think I’ll ever have any problem giving you the release you need when you get like this in the morning.”
Since I was still in a daze, all I could do was shake my head in agreement, my mind absorbed in the sensations of my penis pulsing in her warm hand.
“There are other options as well, Billy. I can sit beside you on the bed and nurse you while milking you with a baby oil massage. Or I can give you a nice, hot soapy bath and milk you in the tub while you’re being washed. I can also put you inside me and spank you at the same time, like this.”
Aunt Sylvia rolled back on the bed, opening her plump thighs around my loins and pulling me on top of her as she went. Reaching down with one hand, she steered my penis to the entrance of her pussy. Though it was a snug fit, she was sopping wet and I entered at a single thrust. Immediately, she reached around me with both hands and began spanking both of my cheeks as I thrust in and out. Between her own moans, she managed to tell me,
“It’s important … oohhhh … for a young man not to release himself …. ohhhh … when he gets this way. That’s going to be my job from now on. … ooohhhh yyeeeess, that’s it, Billy …. You’re going to learn to associate a climax with obedience to an older, more experienced woman. … ooohhh … Don’t worry about not having enough attention from me, I understand a young man like you needs to have release four or five times a week and I’ll make sure you’re well looked after. Just like this … oohhhh yess, Billy .. like this …. You’re going to be milked and spanked at the same time so you understand to leave these things to Aunt Sylvia. You’re also going to learn everything there is to know about how to please a woman. And perhaps in your senior year, we can find you a girlfriend who is a few years older than you and who understands how to handle big “little boys” who needs lots of special looking after. I think I know someone in my church group who might be just right for you. Would you like that?”
By then, I couldn’t respond. For the combined sensation of thrusting into the soft wetness of Aunt Sylvia and the steady stream of spanks on my bare fanny had sent me over the edge again. All I could manage was a series of sharp cries as I shot hot jets of semen into her and my brain merged, momentarily, with the long, white, liquid heat of that eruption. I then collapsed on top of her soft, warm, pillowy body, barely half conscious. As I felt her guide a nipple against my lips, I managed to open my mouth and begin suckling quietly. Her spanks had now given way to a series of soft, circling caresses which somehow enfolded my whole being through my bottom. With her other hand, she stroked my face and told me what a good boy I was and how she planned to milk me three or four times a week.
“You promise, Aunt Syvlia?”
“I promise, you sweet child”.
“Judging by your immaturity, I think you might need a baby sitter over the Christmas holiday when I take Johnny to Florida to visit his cousins for two weeks. And I have just the right woman for the job. I think you know my good friend, Laura Baxter, who lives two houses down. She raised two boys on her own and spanked them when they were naughty all the way through high school. She’ll know exactly how to handle you if you get into any trouble. So if I were you, young man, I’d behave myself for the rest of the week. Or else Mrs Baxter may find a naughty boy getting a spanked in the downstairs den when she stops by for coffee Saturday morning. And that will just be your warm up session. You’ll be put in the corner while Mrs. Baxter and I have coffee. And then I’ll have her finish the rest of your punishment.
Sure enough, Aunt Sylvia was right. Mrs. Baxter did arrive in the middle of a spanking that Saturday morning. I was terribly embarrassed to hear the bell ring not long after Mrs Bellano had put me over her knee. And I was even more red in the face when Mrs Bellano just called out in a loud voice,
“Come in, Laura, we’re back in the den” without even a pause in my spanking. There I was – a college freshman – lying with my pants and underpants tangled at my ankles over the lap of my landlady crying my way through a sound spanking with a very red fanny.
It was even more embarrassing when Laura Baxter poked her head in and greeted Mrs Bellano as if nothing was amiss. Judging by her reaction, they must have already spoken about my situation.
“It looks like you a very naughty boy on your hands this morning, Sylvia. May I come in?”
“Of course, Laura. Since you’ll be sitting for Tommy for two weeks in December, you need to see how to handle him when he misbehaves. Tommy, are you going to give Mrs Baxter any trouble if she has to discipline you? Are you?” SPANK SPANK SPANK
I was too busy crying and kicking to do anything but agree.
“Just to be on the safe side, I think I’ll stop here and put in the corner while we have coffee and let Mrs Baxter give you the rest of your spanking afterwards.”
Though I protested, I was marched to the corner, smacked again and told to stay there with my hands on my head. The two women then settled down for coffee and began discussing my need for a babysitter whenever Sylvia was away. They both agreed Mrs. Baxter would be just right. The discussion then moved on to the problem of self-abuse and the need to check me every morning for signs of masturbation. Mrs Baxter agreed with Mrs Bellano that I would need to be milked regularly to make sure I was not tempted to play with myself. She also suggested a bedtime spanking every night since Johnny would be away and there would be no problem with evening spankings.
“An excellent suggestion, Laura. You’ll be interested to know I gave Billy a bedtime spanking this past week when Johnny was staying over at a friend’s house.” She then whispered something in Mrs Baster’s ear and added in a louder voice,
“I think you’ll find he’s still a big baby in many ways.”
“Perhaps I should take him upstairs to his room and put him to bed for a nap after the rest of his spanking today,” Mrs Baxter said with a wink.
“Perhaps you should,” Mrs Bellano responded, her eyes twinkling.
On and on they chatted about the effectiveness of spankings for boys of all ages. After another fifteen minutes, Mrs Baxter turned to me and said,
“Billy, why don’t you come out of that corner and march over here right now so I can show you how I handle naughty little boys like you.”
Only when I turned was I able to get a good look at her. Laura Baxter was wearing a heart- stopping low-cut sundress which showed a great deal of cleavage even from across the room. And if anything, she was bigger in the bust and hips than Mrs Bellano.
Not surprisingly, I was stiff after listening to all that talk about how to discipline me and did my best to cover myself with my hands. As soon as I came within range, Mrs Baxter swatted my bottom three times and ordered me to keep my hands at my sides or on my head at all times. As I obeyed, she commented,
“It looks like your Billy needs a good milking right now, Sylvia,” Mrs Baxter said.
“He certainly does, Peggy. Why don’t we milk and spank him at the same time?”
“Good idea, Sylvia.
“Why don’t I handle the milking since I have some hand lotion right here. I suggest you stand him between your legs so you can hold him there more easily.”
“Perfect. But let me get this dress out of the way first.” Mrs Baxter drew her skirts up to the tops of her thighs and pulled me in before squeezing them shut, imprisoning me with my bottom sticking out one side, my penis jutting out the other. Standing directly alongside her and looking down, I could see most of Mrs Baster’s breasts jostling about in her sun-dress with a frilly, low-cut pink bra holding them up. Not that I had very long to enjoy the view. She wasted no time in spanking me while Mrs Bellano applied a large dose of lotion to her hands and began rubbing it all over my throbbing penis. Within a few minutes, I went into a series of spasms and shot jets of sperm into a little hand towel Mrs Bellano magically produced from thin air. Apparently the milking had been well planned. I was then put over Mrs Baxter’s left knee, still imprisoned between her thighs, and given the rest of my spanking until my fanny was beet red and I was crying like a baby.
Afterwards, Mrs Baxter soothed me by rubbing more lotion into my burning cheeks while telling me how well I had taken my first spanking from her. She then told Mrs Bellano she thought it would do me some good if she took me upstairs and put me into bed to rest for an hour or so. Not having any choice in the matter and curious as to what she had in mind, I allowed myself to be led upstairs.
Once in my room, Mrs Baxter apologized for spanking me so hard but pointed out that it was for my own good and that I was obviously one of those boys who still needed lots of firm maternal discipline. After tucking me in, she sat down on the bed beside me and took my head in her lap, stroking my cheeks and cuddling me against her bosom.
“Is there anything else Billy needs from his Mommy Baxter? Mommy Baxter can be very nice to her little boy after a good spanking. Would you like to be nursed before taking your nap, Billy? Would Mommy’s little boy like a nice nursing to help him fall asleep?”
The question was rhetorical since I was already nuzzling into her breasts through the thin fabric of her cotton dress. All she had to do was unbutton four buttons in front and her lush breasts practically fell out of her bra into my face. Like Aunt Sylvia, Mrs Baxter always seemed to wear bras with clasps in the front. My mouth quickly found a nipple and I suckled contentedly there for the next half hour while she milked me once more with her hand “just to be sure”.
When I awoke from my nap, Mrs Baxter was gone and Aunt Sylvia asked me how I had enjoyed her visit. When I agreed that she would make an excellent sitter for the winter break, Aunt Sylvia promised to use her whenever she was going out for the evening with Johnny. That night, after putting Johnny to bed, Aunt Sylvia came into my room around 11 PM. I fell asleep lying beside her sucking contentedly on a warm nipple.
The next morning, I lay in bed while Johnny got his breakfast and departed on the school bus. Sure enough, I then heard Mrs Bellano’s footsteps on the stairs and I turned and pretended to be asleep as she came into the room. I had been hard as a rock since waking up and lay there on my back, knowing full well my erection was making quite a tent under the covers. I felt Mrs Bellano draw the covers back. And then I felt her hand lightly stroking my cock. When she saw me stir, she whispered
“Lie still, young man. Let your Aunt Sylvia take care of you. Seconds later I felt her wet mouth take me in and all but swallow me up completely. The pleasure was almost too much to bear and I made half-hearted efforts to push her away. But she kept to it until once again I began to writhe and cry out helplessly. The feeling of shooting hot sperm into her wet mouth was beyond anything imaginable. But as I was to discover, it was only the beginning of four years of college life filled with regular spankings and milkings using a variety of techniques.