Jimmys College Landlady

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By Firmly2Part INew ArrangementsEven after a month of being diapered at night by his college landlady, Jimmy Larsen could hardly believe this was happening to him, an eighteen year old freshman. Strangely enough, his eagerness to keep secret his bedwetting problem had led him to choose off- campus housing in the first place. After searching for a room to rent, he answered an ad placed by a Mrs. Sylvia Landino who had a room to rent in her home seven blocks from campus. Mrs. Landino was a shapely widow in her late-forties who immediately impressed Jimmy with her warm, maternal manner. When she told him she wanted a young man around the house as much for company as for the rent, Jimmy knew he had found the right place.Once he moved in, he was careful to keep his disposable diapers hidden in a trunk which he used as a table in his bedroom. And on mornings when he woke up wet, he simply put his disposable diaper in a plastic bag which he concealed in his briefcase and discarded in a public trash can on the way to school. When everything went smoothy o relax and focus on other issues, like the difficult transition from high school to college. In a few months, he had gone from being an experienced senior who younger students looked up to and who knew everyone to a young, shy, freshman who didn't know anyone and who was ignored by the older students. It didn't help that almost everyone in his class seemed more mature, experienced, and self- confident. By the end of the second week, he was very glad to be living in a real home with a warm, older woman he could talk to. Mrs. Landino seemed to understand exactly what he was going through and always made lots of time to hear his thoughts and worries at the end of the day. She was one of those persons who naturally drew him out and helped him put things in perspective.In the middle of the third week of class, Jimmy got too drunk at a freshmen bash. By the time he got back to his room around midnight and finished undressing, the walls started to spin. He remembered pulling back the covers and lying down on his bed for a moment, hoping things would settle down. After that, he must have passed out. The next thing he knew, it was morning and his sheets and mattress were soaked. Because the mattress was wet, there was no way he could hide the problem, especially with classes that morning. Had it been a weekend, he could have waited until Mrs. Landino went out shopping and then washed the sheets in the basement. And he could have dried the mattress off with his fan. But with a 9:00 French class and the first test of the semester, he was unable to take care of things before leaving. To make it less obvious, he left the bed unmade with the sheets gathered somewhat to hide the wet spot while allowing air in to dry things out a little. His plan was to return at lunchtime, turn on his fan with the door closed, and at least get the bedding dry.When he returned around 12:30, Mrs. Landino greeted him with a funny little smile and said,"Jimmy, when you drop off your things in your room, could you please come down here? I think we need to have a little talk about something."Jimmy's face flushed but he managed to keep his cool. Perhaps she hadn't found out and just wanted to chat about something else. He nodded to her and quickly headed up to his room. At the top of the stairs, a single glance confirmed his worst fears. His bedroom door was wide open with his stripped mattress lying next to the bed on its side. His fan was on the floor pointing at the mattress. A much larger wet area, now almost dry, indicated Mrs. Landino had already scrubbed the mattress. The wet sheets were nowhere to be seen. Suddenly he noticed the distant hum of the laundry machine.As he entered his room, his first reaction was panic. Then he remembered how much worse it would have been had he been living in a dormitory. At least no one at school had found out. Knowing that Mrs. Landino was waiting downstairs, he tried to collect his thoughts and decide what to say. How would she take it? Should he tell her everything, even about getting drunk? And would she ask him to leave?Finally he faced the inevitable and trudged down to the kitchen. By then, he knew he had to tell her the whole truth. If she caught him lying about anything, he wouuld lose all the sympathy she had showed from the start and he would probably lose the room."Why don't we go in the parlor where we can sit down, Jimmy," Mrs. Landino said as he entered the kitchen. Jimmy swallowed and followed her into the next room. Apparently it was to be a real heart to heart talk since Mrs. Landino sat down on the sofa and patted the cushion next to her. At least she didn't seem angry. As Jimmy sat down, he felt a little like a small child caught doing something wrong who now had to confess.Before she could ask a single question, Jimmy began speaking in a rush of words. Over the next few minutes, he described everything from his longstanding bedwetting problem to his need for nighttime diapers and his reasons for choosing off-campus housing. He was relieved when he saw Mrs. Landino nod and smile reassuringly. If only he could have trusted her before and not hidden anything. His mind flashed back momentarily to his childhood and to the relief he had often felt when confessing a misdeed to his mother. In that instant, Jimmy realized how lucky he was to have found such an understanding, older woman as a landlord. It was as if her sympathy and warmth had made it safe for him to tell her things without fear of embarrassment or humiliation.Mrs. Landino listened patiently until Jimmy finished. After a moment of silence, she began speaking."First of all, young man, I thank you for your candor and honesty. Not many boys your age would be truthful about a problem like this and I want you to know how much I appreciate that. Let me also say that wetting problems are a lot more common than you think. Why do you think the stores sell so many adult diapers? If it makes you feel any better, my son wet the bed on and off into his mid-teens and we took care of the problem the same way you do. So having someone in the house who needs diapers isn't a problem for me.""What is a problem, young man, is the way you damaged a brand new mattress by coming home so drunk that you passed out. That is completely unacceptable behavior for a tenant in my home."Jimmy hung his head, knowing full well she was right."Normally, if a roomer got drunk and damaged my property, I would ask him to leave right away. But since you have been so honest with me and since the damage was not intentional, I am willing to allow you to stay providing we can come to a new agreement.""Oh thank you, Mrs. Landino ... thank you so much ... I just knew you would understand. You don't know how scared I was of living in a dorm and having my classmates find out.""Well, you can be sure I won't divulge your secret to around around here. But before you decide to stay, you had better hear my conditions. I'm well aware there are a lot of drinking parties on campus and that you will probably have too much to drink two or three times a semester. Since you are obviously not responsible enough to control your drinking, you can continue to rent my room providing I take charge of all your diapering. That way, I can ensure my bed and sheets are protected. Another accident like this and I will have to throw out that mattress entirely and buy a new one along. Do you know how much that mattress cost, young man?""No Mrs. Landino, Jimmy replied."Three hundred dollars with the box spring and you can only buy it as part of a set.""I'm sorry, Mrs. Landino. I promise it will never happen again. Really"."You can promise all you like, Jimmy, but the simple fact is there are lots of drinking parties on campus and a young man who comes home drunk can easily forget what he has promised. While it's clear to me you're a good boy overall, you will need adult supervision to make sure you are properly diapered at night. That's my decision and it's final. Of course, you are free to look for another room to rent. Or you can continue to live in my home under my rules. Which do you prefer, Jimmy"?After a long pause, Jimmy managed to say,"I ... I guess ... I guess I'll stay, Mrs. Landino ... but I really think that ...""No buts out of you, young man, is that clear?""Yes ... Mrs. Landino," Jimmy replied, at once infinitely relieved and nervous about what to expect."I think it best if you move your diapers to the bottom drawer of my smaller bedroom dresser. It's empty and that way you can be sure none of your friends ever find them in your room. We wouldn't want that would we?""No Maam.""And that way, I'll be able to take care of any diapering you need while you're staying in my house. If you're wet and need to be changed at night, you'll just have to come and let me know if you want to be changed into dry diapers. Are we clear on the house rules?""Yes, Mrs. Landino.""Good. Now I have to go out for some food shopping. I think I'll swing by the medical supply store and pick up some adult-sized plastic pants so we can make absolutely sure everything stays dry. Diapers leak sometimes, don't they, Jimmy?"Jimmy's only answer was to blush."The sheets should be done in the dryer in about ten minutes. When I get back, I expect to see your bed all remade and your diapers moved to my dresser. Are we agreed?""Yes, Mrs. Landino. Thank you for letting me stay. I don't know what I would have done - I suppose there aren't too many landladies like you.""No, I don't suppose there are, child. I realize this may be a little embarrassing for you at first but try not to think of it that way. If you were in a hospital for some reason and I was the floor nurse, I'd be putting you in diapers and plastic pants every night and changing you in the morning. Since I diapered my son Billy until he was fifteen, I have lots of experience taking care of boys like you. I imagine you'll get used to it in a few weeks."The First NightBy the time Mrs. Landino returned, Jimmy had remade his bed and was halfway through his homework. Nothing was said of their new agreement that night at dinner though Jimmy knew it must have also been on her mind. Afterwards, he did the dishes and retired to his room to finish his homework. At 9:30, he heard a quiet knock on his door."Come in", he called out.Mrs. Landino poked her head in and said,"I'm about ready to go to bed, child. Why don't you go into the bathroom and brush your teeth and get into your pjs and all that so we can get you into your diapers. OK?""OK, Mrs. Landino." Jimmy's heart was racing and already his face was a little flushed. He got out a pair of pyjamas and went out into the hallway to the bathroom. After five minutes, he reemerged, dressed for bed, his dirty clothes dropped off in the bathroom hamper.As he approached his bedroom, he could see Mrs. Landino arranging his diaper things on the night table alongside his bed. His sheets and blankets were turned down and a towel laid out on the bed. She had turned the main room light off so that the only light came from the bedside lamp. Somehow the relative darkness of the room and the warm pool of light on the bed reassured Jimmy as he entered his room. Mrs. Landino seemed to know how to create the right atmosphere of privacy to make an awkward situation less difficult."Are we all ready, young man?""I guess so, Mrs. Landino.""Good. Why don't you just lie back on the towel and relax. Mrs. Landino is going to take good care of you, I promise."Jimmy felt funny stretching out on his bed - a college freshman about to be diapered by his land lady - but he did so without protest. Once he was lying down, he felt a little better. At least someone else was taking care of him ."Let's take these off for now, young man, shall we?," Mrs. Landino said as she unsnapped his pyjamas bottoms and slid them down. Then she sat down on the bed beside him, the little table within easy reach."Keep your hands to your side, Jimmy ... I've seen plenty of boys before, believe me. If you're not too old to wear diapers, I don't think you need to worry about modesty. After all, I'm going to be seeing a lot of you from now on at diaper time. Now be a good little boy and do as I say."As she moved Jimmy's hands firmly to his sides, she gave each one a little slap. Jimmy's face got even redder. What did she mean calling him "good little boy"? The language was disturbing yet somewhat reassuring. Maybe it really would be nice to let his sexy, maternal landlady handle his diapering? Deep down, he knew there was a side of him which enjoyed feeling like a "little boy" - it was something which came at night after he turned out the light and lay there in his diapers or woke up in the morning wet on the inside and dry on the outside.Before he realized what was coming, Mrs. Landino opened a container of Vaseline and scooped out a rather large gob."Be a good boy and bend your legs up .. for Mrs. Landino ... that's it Jimmy ... all the way up.""Mrs. Landino, I don't need anything like that ... really ... it's not necessary.""Nonesense, child, we cannot have you getting a diaper rash, can we?""But Mrs. Landino, I don't get diaper rash normally ... you don't need to use Vaseline.""Not normally, perhaps, but that only shows it does happen from time time. Now bend your legs up, Jimmy, and don't give me any more trouble unless you want me to turn you over and give your bottom something a lot worse than Vaseline. Do you want a spanking, child?"Jimmy blushed deeply, unsure of how to respond and embarrassed by the very nature of the threat."You're ... you're not serious, Mrs. Landino.""Just continue fussing and you'll find out, young man. Now lift up your legs ... that's better. You agreed I would be in charge of this so don't tell me how to do my job. Starting tonight, you're going to be properly diapered and that means a good vaselining first and plastic pants afterwards."Jimmy gave in and let her raise and fold his legs until his knees almost reached his chest. In this fetal position, his bottom was fully exposed. Though he saw what was coming, he still gasped when Mrs. Landino's warm hand began smearing vaseline on his cheeks."It feels a little funny at first, doesn't it Jimmy.""Yes, Mrs. Landino, it sure does." What he didn't tell her was how wonderful it felt, especially when her hand slid deep between his cheeks."Most little boys like it when their mommies rub Vaseline on them, Jimmy. I gather even big boys don't mind this ... do they?"As she said, "little boys", she slid her hand deeply between his cheeks again. Though Jimmy managed to stifle a moan, he was not as successful at suppressing the beginnings of a different kind of reaction which promised to be exceedingly embarrassing. He tried quietly biting his lip and that worked for a while.After she had rubbed a liberal coat of Vaseline on his bottom, Mrs. Landino lowered his feet back onto the bed and spread his thighs. Then she scooped out another dab of Vaseline and began working on Jimmy's front. Once she started there, Jimmy knew the battle was lost. He could only shut his eyes to reduce his embarrassment. Fortunately, Mrs. Landino made it a lot easier by saying,"Oh ... don't worry about that, Jimmy ... that almost always happens at diaper time, especially with bigger boys. You needn't be embarrassed ... in fact I'd say you ought to be proud."That last remark made Jimmy blush even more. At the same time, he was flattered and excited by her compliment and it helped relax him a little. So did the incredible sensations of her hand. Finally, she finished his vaselining and wiped her hand on the towel. Though Jimmy was still too embarrassed to open his eyes, he presumed she was reaching for his diaper. And when he heard the loud rustling noise they made as she unfolded it, he breathed a sigh of relief. Immediately he resumed the fetal position so she could tip him further back and slip the diaper under his bottom. She then lowered him onto the soft fabric, spread his legs again, and pulled the front of the diaper between his legs until it covered his erection. She then stopped for a moment, tickled his chin, and said,"You can open your eyes, Jimmy. We're all covered up now. You shouldn't be embarrassed when you look so adorable in diapers. I can't decide whether you're the most handsome young man I've ever seen or the cutest baby I've ever changed."Jimmy blushed again but managed to open his eyes. He was beginning to like this, especially all her compliments."Let's get these diapers taped on snugly up, shall we?""Yes, Mrs. Landino".She bent back over his loins and taped the diaper snugly into place on eather side. When all that was done, she took the new plastic pants from the bedside table, shook them out."Be a good boy, Jimmy, and lift up your legs so Mommy Landino can get your baby pants on. I think I might as well call myself Mommy Landino at diaper time since I might as well be your mommy. I hope my little boy doesn't mind, does he?"Jimmy blushed again and said nothing as Mrs. Landino ruffled his hair again before tucking his feet through the leg openings and sliding the plastic pants all the way up his legs and thighs. Putting one arm under his thighs, she rocked him backwards a little more and slid the pants over his diapered bottom before pulling them up over his front. Just before lowering him back onto the table, she gave his padded bottom a few playful spanks and told him again how cute he looked. Even with diapers and plastic pants, Jimmy noticed his erection was still visible.After making sure the diaper material was tucked in all around, she put his pyjamas bottoms back on. With that finished, she closed up the jar of vaseline and asked Jimmy if he was all ready for bed. When he nodded, she pulled the covers over him, kissed him goodnight, and turned out the light."I'm locking the upstairs bathroom for the night just so you don't try to sneak in there and pee. If you have to make wee wee, that's what your diapers are for. If you need to go potty in the middle of the night, you can knock on my door and come through my room to use my bathroom. That way, I'll know you aren't trying to get out of your diapers once I put you to bed for the night. Do you understand, Jimmy?""Yes, Mrs. Landino.""Good boy. Now nightie night, sweet Jimmy."As soon as she closed the door behind her, Jimmy began masturbating through his diaper to relieve the tremendous arousal which had built up through the whole process. With minutes, he had a big orgasm and fell into a deep sleep.In the morning, he awoke to the usual sensation of wet diapers. Only after lying there a while did he remember the previous night's activity. It hit hit like jolt. As he began replaying those events slowly, the door opened and a cheerful Mrs. Landino entered wearing a pink, silk bathrobe. Tightly belted at the waist, it strongly emphasized her large, jostling breasts and full hips. She carried a small plastic bag and a little washbasin with a damp cloth. Putting these down on the bedside table, she sat on the bed, kissed his forehead, and asked in a teasing voice,"How's Mommy's diaper boy this morning, Jimmy?"Jimmy blushed immediately but managed to say, ""Fine, Mrs. Landino.""Splendid. Mommy's going to check to see if we're wet this morning."Drawing down the bed covers, she sat down and unsnapped his pyjama bottoms."Lift up, please, sweetheart."Jimmy raised his hips so she could slide his pyjamas bottoms off."That's it. ... Now lift up again so Mommy can take your baby pants off."Jimmy lifted his hips as his plastic pants came down with a loud crackling sound. Mrs. Landino then tucked a finger under his disposable diaper at the crotch area."We certainly are wet, aren't we. I'm glad I got you these plastic pants. I was afraid you might be a heavy wetter."As she sat down, her breasts swayed freely through the clinging silk and Jimmy tried not to stare. Unfortunately it was impossible to ignore them once she pulled his legs into a fetal position. As she bent forward to begin untaping his diaper, her bosom rubbed repeatedly against his knees.Once the diaper was carefully untaped on both sides, Mrs. Landino pulled the front section down between his legs. Jimmy helped her by lifting his hips again so she could slide the wet diaper out and drop it into her plastic bag. Fortunately, he was not aroused that morning and the experience wasn't as embarrassing as it could have been. He even enjoyed the sensation of the warm washcloth as she gently cleaned his diaper area. When that was done, she gave him another kiss, and said,"See, now that wasn't so bad, was it, Jimmy?"He shook his head."I told you Mommy Landino had lots of experience changing diapers. Now off you go to your shower. I'll have breakfast downstairs in fifteen minutes. And I'll see you again here tonight at bedtime."Part IIThus went Jimmy's first night being diapered by his landlady. At first, he was terribly embarrassed when she called him "little boy" or referred to herself as "Mommy Landino". Yet even that was done in such a loving and teasing manner that Jimmy soon got used to it, especially since no one else ever heard her talk that way. It was a special language she used only at diaper time.Their routine continued like that every night for the rest of the semester with a few minor variations. After a few weeks, Mrs. Landino began diapering him around 8:00 so she wouldn't have to interrupt her own routine of reading in bed for an hour before turning out the lights. Since his nighttime diaper came off only if it was wet or when the morning came, he always made sure to go to the bathroom before she diapered him for the evening. At that period, he was still more embarrassed than aroused by the whole thing. The last thing he wanted was to wet before bedtime and need another change.Of course, with an earlier diapering time, it didn't always work out that way. Six or seven days after she began diapering him at 8:00, Jimmy decided that he didn't need to pee beforehand. As it turned out, he was wrong. By 9:30, things were bad enough that he knocked on her door and asked if he could use the bathroom. As usual, Mrs. Landino was in bed reading, dressed in her silk robe."Jimmy, you know once Mommy Landino diapers you for the evening your diapers only come off for number two or if you need changing. You should have made wee wee earlier when you had a chance, young man. Now you'll just have to use your diapers. Maybe you'll remember to use the bathroom first in the future. If you wet before you go to bed, just come and get Mommy and she'll change you."Since there was nothing he could do, Jimmy returned to his bedroom and read for another thirty minutes before giving up and flooding his diaper. A few minutes later, he went back down the hall and kocked on Mrs. Landino's half-open door."What is it, Jimmy?""I wet myself, Mrs Landino""That's OK sweetheart, Mommy will change you as soon as soon as she gets a diaper. Just wait there a second."He watched her get up from the bed, staring openly at the way the silk clung to her swaying body as she fetched a clean diaper from her dresser. If she noticed him looking at her, she certainly wasn't annoyed. On the contrary, she smiled as she took him by the hand and led him back to his bedroom. That was the first time she changed him at night wearing her silk bathrobe. That was his favorite thing about morning changes - the sight of her breasts jostling freely against the thin silk. Tonight, she looked even more lovely and she seemed to have on more rose and lavender perfume than usual. Even before his pjs came off, Jimmy was quite hard. When she undid the tape and pulled his diaper down, she drew in her breath just enough for Jimmy to notice. .Since she was in her bathrobe, he was not about to close his eyes. There was just too much swaying, perfumed, female flesh a few inches away. And this time she seemed to spend more time applying Vaseline to his penis as if recognizing the extra attention it needed. She even added an extra compliment in the middle of his Vaselining."You are certainly a very big boy in some ways, Jimmy. You going to make your first girlfriend very happy someday ... did you know that."Once again, Jimmy blushed and said nothing. But inwardly, he was proud. It wasn't long after that before Jimmy began wetting two or three times a week around 10:00 just so Mrs. Landino would give him an extra change while wearing that silk bathrobe. By then, the whole experience for Jimmy had shifted from embarrassment to pleasure and sensuality. On a number of occasions, he almost climaxed in her hand during his Vaselining. By mentally fighting his arousal, he avoided this escalation. It would have been a little too much, too fast and he was afraid of how she would respond...New Developments at Diaper TimeAs could have been expected, the experience of being diapered every night and changed every morning by Mrs. Landino had its own dynamic and gradually transformed the experience for both of them. By the fourth week, Jimmy looked forward to his nightly diapering. In fact, it had become the highlight of every day and he was even comfortable with his erections. In fact, he was secretly proud of them and allowed himself to smile at Mrs. Landino's litle compliments.Mrs Landino sensed his growing acceptance and was pleased. She even encouraged it by showering him with extra affection around the house. Whenever he came home from school, she welcomed him with a hug and a kiss. And she always gave him a big kiss at bedtime and in the mornings. She also began to smack him on the bottom around the house when he passed by. This rapidly turned into a game where he tried to dodge her hand at the last second. And when she connected, they both giggled.After noticing how much he appreciated her silk bathrobem, Mrs. Landino made a point of changing into it earlier in the evening so she always had it on for his nightime changes. She also spent more time applying vaseline. She could tell Jimmy was inexperienced sexually and shy in that department. Yet she also saw how he was slowly accepting the pleasures of his own body as long as they stayed within the safe context of his diapering.To test the waters further, Mrs. Landino began arriving at diaper time with her robe belted less tightly so that it opened a little in front when she leaned forward. She was careful not to do anything too obvious or scary, allowing Jimmy to think he was simply enjoying accidental glimpses of her cleavage. But there was nothing accidental about it. And judging from the fact that he was often erect in his pyjamas even before she applied his nightime Vaseline, her little displays seemed very much appreciated.One night in later October, she put on a transparent white chiffon negligee beneath her bathrobe instead of the usual cotton nightie and left her robe tied a little more loosely. She also put on some extra perfume. When she sat down on his bed and pulled off his pyjamas, her robe fell open somewhat, giving Jimmy an eyeful. This time she spent a full five minutes Vaselining him, working his bottom thoroughly before tending to his front. In her exertions, her robe opened a little more, though not beyond what seemed accidental. Keeping her gaze fixed on her task as if she didn't notice, she continued his Vaselining.Jimmy couldn't believe his luck. As Mrs. Landino's massaged him, her robe had opened enough so that he could see her breasts dancing beneath a transluscent chiffon nightie he had never seen before. On and on his Vaselining went, each movement of her hand stimulating both Jimmy's penis and adding to shimmering movements of her breasts. Before either of them knew it, Jimmy's hips began to jerk uncontrollably and jets of semen shot from his penis onto his chest.Fortunately, Mrs Landino knew just how to respond. Rather than showing any surprise, she continued her massage as if nothing were amiss and even complimented Jimmy."My, my .. you certainly are Mommy's little man tonight aren't you, Jimmy. Don't be embarrassed, child. This is the most healthy, natural thing in the world for a boy your age and it was bound to happen sooner or later. I'm just glad Mommy is here to give you the relief you need. You're Mommy's special little boy tonight, aren't you ... yes you are"While Jimmy was initially embarrassed by his climax, he was also secretly thrilled to see she wasn't upset. A new element had been added to his diapering and he knew it would happen again, probably in the near future. As fate would have it, Jimmy did climax again, the very next night, and indeed, on most nights after that during his vaselining. And Mrs. Landino in turn continued to leave her bathrobe more loosely belted to give tantalizing glimpses of her bosom during his diaper changes. After a while, Jimmy realized it was probably deliberate but by then he was too excited by the whole experience to care. In fact, the thought that Mrs. Landino was aroused by his diapering created an increasingly charged, sensual atmosphere which he eagerly awaited each night and morning.Jimmy's First SpankingOne day in early December, Mrs. Landino came into Jimmy's room around 8:30 and caught him masturbating on his bed. He had already climaxed when she diapered him a half hour earlier but the whole experience had only left him more keyed up than ever. His pyjamas bottoms were down around his knees and his diapers and plastic pants were pushed down below his hips as he lay back in the fetal position and worked on himself. His horror gave way to relief when she used the teasing voice she always used at diaper time."Don't you dare pull those diapers up, child ... you just stay right there without moving an inch. You know Mommy told you not to do that. What did I say was going to happen if I caught you playing with yourself again? You remember. Mommy said she would put you over her lap and give you a good spanking, that's what. And then she would put you to bed early. Stand up, you naughty little thing ... stay there while I sit down ... we'd better get this robe out of the way so it doesn't get wrinkled .. now come here over my knees ... that's a good boy ... ... Maybe a good lesson from Mommy will teach you to behave yourself in the future."Had she not been using such a teasing, sensual voice, Jimmy never would have allowed her to put him over her knee like child. But she chose her words and tone carefully, all but hypnotizing Jimmy. To encourage him further, she pulled up her robe and bared her lush, waiting thighs while steering him forward by holding his penis. As extra encouragement, she smacked his bare bottom with her right hand.When he was finally positioned over her knees, his diapers and plastic pants tangled at his knees and his bare bottom sticking up helplessly in the air, Jimmy felt completely vulnerable and childlike. Yet he also felt secure, safe and protected ... like he did when she vaselined and diapered him. At the same time the sensation of his throbbing penis against her bare thighs was incredible, especially as she began palming and spanking his vaselined bottom in a playful way.Right away, Jimmy realized she was just going to give him a sensual spanking. Jimmy responded accordingly as his penis found a space between her thighs. Before long, he was quietly thrusting in time to her smacks. As she spanked the aroused child, Mrs. Landino continued to lure him on with her wonderful teasing, scolding voice. And she met each of his little thrusts by opening her thighs slightly only to tighten them around his Vaselined penis as he pulled back. He had become her little toy and he loved every sensation she offered. Within five minutes, it all came to a head. Jimmy began crying out loudly as he exploded between her soft thighs. Ever the attentive Mommy, Mrs. Landino continued to spank him gently through his orgasm and for another few minutes until he regained his composure."Now, that's we've taken care of that, young man, it's time for the real spanking I promised."With that announcement, Mrs. Landino began to spank Jimmy more briskly, all the time watching him carefully so as not to push things too far. Thus she paused for breaks and extra scolding when necessary. And throughout the process, she explained exactly what she was doing and why."Young man, while you may not think you have done anything bad, I'm going to give you the real spanking I promised if I ever caught you playing with yourself again. I can understand the frequent impulse to masturbate. You're hardly the first college-age boy renting from me with that problem. But you are going to learn some self-control as long as you live in my home. Do you understand? Mommy doesn't mind if you have a climax when she's putting on your Vaseline. That's a perfectly normal reaction from a boy your age. I'm also well aware that a boy your age needs a reasonable amount of relief. What I won't stand in my home is a child who masturbates frequently, whenever he is left alone, without any sense of measure or reason. You've already had one climax this evening and that should have been enough. Do you hear me, Jimmy? I expect you to control yourself much better in the future. ""Yes, Mommy, I'm listening ... please don't spank me any more ... I promise I won't play with myself again.""Do you expect me to believe that, child? I already asked you once. And I told you exactly what would happen if you disobeyed me again, didn't I?"Jimmy had nothing to say in his defense."I think it's time you learned a good, old-fashioned lesson which all little boys need to learn from time to time. I believe that the punishment should always fit the crime. Since this isn't the worst thing you could do and since I have only warned you once about excessive masturbation, I will go easy on you this time. It's also your first spanking. Thus I'm only going to give you a taste of what will happen if Mommy catches you masturbating like this again.""Mommy, please noooo ... please no more spanking," Jimmy cried as the vigor of her spanks began to make a real impression on his fanny."We're just getting started, you naughty thing. This may not be a severe punishment but you are going to learn a good lesson before we're through. Just to let you know what a really sound spanking from me feels like, here are twenty five hard spanks. As I give them to you, keep in mind that you will get a hundred such spanks followed by fifteen minutes of corner time and another hundred if I ever catch you doing this again after you've just been relieved."Mrs. Landino started in on the hard spanks which immediately brought a real cries of protest from Jimmy."One ... two ... three ... four ... five ... six".She spanked more slowly now, alternating from one red, bouncing cheek to the other, raising her hand two feet above Jimmy's cheeks and flicking her wrist at the last moment. She was obviously a very experienced disciplinarian."Seven ... eight ... nine ... I thought a real spanking might get your attention, you naughty child ... ten ... eleven ... twelve ... It is my experience that any boy who is not too old to wear diapers is definitely not too old to be well spanked over the lap of an older woman whenever he misbehaves ... thirteen ... fourteen ... fifteen ... I hope you're listening because Mommy is going to start using spankings to make sure you mind her ... sixteen ... seventeen ... eighteen. As I think you are beginning to see, I am a very capable woman when it comes to giving out spankings, even for big boys like you. ... Nineteen ... twenty ... twenty-one ... Sooner or later, every boy who rents this room and disobeys me learns that. You may be the first wetter I've had, Jimmy, but you are certainly not the first boy I've caught masturbating who went over my knee. Twenty-two ... twenty-three ... twenty- four ... twenty five. There ... now just remember ... that's only a taste of what a hard spanking would be like. If Mommy was giving you one of those, you would be crying your eyes out now."For a moment, JImmy thought his punishment was over. But when Mrs. Landino resumed spanking his red bottom with more moderate smacks, the desperate child wailed,"Please no more spanking Mommy ... please ... I won't play with myself anymore ... I promise.""I'm sorry young man but we're just past the beginning of your paddling. Though I'm not going to spank you that hard anymore, I am a firm believer in long, slow spankings. I four age learn a much better lesson if they spend a a good fifteen minutes over Mommy's lap. There's something about a long spanking that gets a child's attention and allows him to have a real talk with me about his behavior. A short spanking doesn't correct problems very well at your age. With a prolonged lesson, you can think about what you did wrong and what will happen if you misbehave again. A longer spanking also helps most older boys admit that they needed their punishment. Short spankings often leave a youngster bitter and more rebellious. After a long spanking, a child knows he's been well punished and usually feels better afterwards. Especially when Mommy takes him on her lap for a hug and a kiss and tells him that his punishment is over.""Only when a boy your age gets to the point where he can admit he deserved to be punished does he reap the full benefit of a spanking. That's why cuddles afterwards are important. They help older boys understand how spankings are a sign of maternal love which they still need in many ways, even in college. Believe me ... no boy who went over my knee didn't deserve and need the spanking he got even if he couldn't admit that right away. That's where long spankings help so much. Something different seems to happen. By the time I'm finished, most naughty boys your age can admit they still someone to set firm limits for them. Of course, a few boys have trouble admitting that even after many spankings. The one thing they do agree on, though, is how effective spankings are as a method of punishment, especially at your age.""Once a child your age admits that he both deserved that first spanking and learned a good lesson, he knows exactly what to expect if he misbehaves again. It also helps at that point to go over all the house rules again while he's still over my knee so he knows all the things which will lead to more spankings. You'd be surprised at how well behaved most of boys are the second time they have to go over my knee, especially if its something I already warned them about."What's even more surprising is how quickly most boys test my resolve by misbehaving in some way or another within a few days. I suppose they just can't believe I actually took their pants down. One boy even left his door slightly open so I would catch him masturbating just to see if I meant what I said. Of course, he wished he hadn't.""You might also be surprised at how many college students renting this room seem to need regular discipline once they get their first punishment. One roomer four years ago earned about two or three spankings a week, usually for trying to peep on me in the shower. He also got drunk with a friend who was staying over for the weekend. He later told me his friend didn't believe I spanked him and wanted to visit to see what I was like. After catching them red-handed in this room, I marched the friend to the corner and gave that boy a good spanking right then and there with his friend watching. Judging by the expression on the friend's face, I think he knew he was next. He was. I finished with the first boy and put him in another corner. Then I took the friend out from his corner and brought him over to the bed and took his pants down. Boy was he embarrassed when I saw how excited he was. Of course, that didn't last very long once his spanking began. He was the cockier of the two but he cried even more once he went over my knee.""As you now know, I believe in giving spankings right away for some things such as masturbation. For most offenses, however, I prefer to keep what I call a "bad boy" book where I write down any misbehavior on a daily basis. Starting today, I'm going to start a "bad boy" book for you and keep it in my top dresser drawer. On Sunday night, before I put you in diapers, I want you to come to my bedroom exactly at 7:30 and fetch your "bad boy" book from my dresser. You will then add up any spanks I've marked down for that week and tell me the number. After that, I expect you to apologize for being so naughty and ask Mommy to put you over her knee for a good spanking. Do you think you can do that, Jimmy?"As Mrs. Landino posed the question, she delivered three extra hard spanks to Jimmy's scarlet bottom which elicited immediate assurances from the tearful eighteen-year old."That's Mommy's good boy," she said, as she returned to the less severe spanks. In your case, Jimmy, I intend to punish you with more than just spankings. If you earn more than one hundred spanks per week, you will be grounded for the weekend and wear diapers round the clock unless you have to go potty. That includes if we have to go out anywhere. Do you understand?"Jimmy nodded and began crying. Since the crying stage was in some ways the most important stage of a good spanking, especially for an older boy, Mrs. Landino continued spanking Jimmy for another five minutes. It was only when an older boy allowed himself to break down and cry that he truly experienced his childish dependency and need for guidance and discipline from an adult. A teenager who cried during a spanking was much more likely to understand why he still needed traditional punishment. He was also much more likely to be free of any resentment afterwards. Just to make sure Jimmy understand all this and that she had no hard feelings, Mrs. Landino thought of offsetting the first spanking with a little reward later if Jimmy seemed receptive.Finally, Jimmy's punishment ended. It had been a long spanking, as promised, but both of them knew it had not been overly severe. The fact thaty Jimmy stopped crying fairly quickly showed it was more of an important psychological release than anything else. And when Mrs. Landino stood him on his feet and gave him a long hug, he hugged back and promised to be good. Instead of being angry, he all but clung to her as she held him closely and rubbed his sore bottom. She then took the clinging youngster on her lap and rocked him in her arms for five minutes and told him how well he had taken his first spanking. Only then did Mrs. Landino pull his diapers and plastic pants back up and put Jimmy to bed early. Just before closing the door, she turned and said,"Young man, if I ever catch you playing with yourself again, you're going to go right back over my lap, you know that don't you?"Jimmy nodded from the bed."And next time Mommy's going to give you a sound spanking, Do you understand? Plus day diapers the next weekend. Now you try to go to sleep, angel, even though it's a little early. I'll stop back in around 10:30 to check on you. Goodnight, child.""Good night, Mommy."That spanking was the first time he had ever called her Mommy. Somehow the tingling warmth of his bottom and the after glow of his earlier orgasm all added up to new feelings of love and security for Jimmy and he wanted her to know that. He hadn't planned on calling her Mommy - it had just slipped out earlier during the spanking and now it sounded right in a new way. As he lay in bed, his bottom still tingling warmly in the soft confinement of his diapers, he felt closer to Mrs. Landino than ever before.An hour later, Jimmy was just drifting off into a sound sleep when Mrs. Landino returned, dressed only in her silk robe and carrying a clean diaper. It was completely dark except for Jimmy's nightlight. After checking his diaper and finding him dry, she placed the clean diaper on the side table and carefully stretched out alongside Jimmy but higher up on the mattress so that her full bosom was near his face. He stirred and snuggled directly into her breasts. Was he beginning to wake up? She couldn't tell. What was clear was the way his face had pushed a little deeper into her bosom. Working slowly so as not to awaken him further, she drew back slightly, opened her robe and move forward so that her bare breasts enfolded Jimmy's face. He murmured slightly and snuggled into her some more. It didn't take long for his lips to part as he instinctively found a nipple and began sucking gently. For the next twenty minutes, Mrs. Landino lay there while he nursed, both of them utterly content. What Jimmy didn't know was how sensitive Mrs. Landino's breasts and nipples were and how much she loved such oral attention. When she gradually noticed a new urgency to his suckling, she whispered,"Angel, are you awake?"Jimmy stopped nursing long enough to say,"Yes, Mommy.""Would you like to come sleep in Mommy's bed tonight, darling? That might help you feel better after your first spanking.""Yes, Mommy"."That's my sweet child. Mommy will help you get up ... that's right ... You'll sleep better in Mommy's bed, won't you.""Yes, Mommy, Jimmy murmured, still half-asleep."That was the first of many nights when Mrs. Landino came to fetch Jimmy from his bed around bedtime. She usually left all the lights out and wore just her chiffon nightie which opened completely in front. Sitting on his bed, she would cradle his head in her lap and open her nightie. After fifteen or twenty minutes of nursing, she would get him up and lead him to her bedroom where he usually fell asleep breastfeeding some more. In the mornings, he always suckled again, sometimes waking her up slowly with the pleasure of his mouth. Over the next few months, Jimmy learned a lot more about "pleasing Mommy". And on the first weekend of December, when it was obvious he was very ready and eager, Mrs. Landino finally made a man of him.By the end of the first school year, Jimmy had become a much more self-confident and experienced youing man while living out his deepest little boy dreams at the same time. He also had a terrible crush on Mrs. Landino and did anything she asked. In May, he even allowed her to hire him a baby sitter when she went away for a weekend.Part IIIDiaper Day at the MallThe sitter was someone they had met at the mall the previous November. One Saturday back when they were planning a shopping trip to the mall (which was ten miles away), Mrs. Landino caught Jimmy playing with himself. As punishment, she gave him a fairly sound spanking with about one hundred hard spanks. And she immediately put him into day diapers for the rest of the weekend. For Jimmy, of course, this meant he would have to wear diapers to the mall. Fortunately he had on baggy jogging pants which hid his diapered condition fairly well (though a tell tale rustling was fairly audible). The worst part was the diaper bag slung over Mrs. Landino's shoulder. He hoped no one would connect it to him. And he was glad that the mall was so far away from the college.When they got to the mall, they first shopped for a new sports coat for Jimmy. It took quite a while to find the right one which fit perfectly. He kept wondering if the saleslady noticed anything, especially when she smiled a few timwes at him and Mrs. Landino for no apparent reason. After that, they some cookies at one of the food outlets. By then, Jimmy needed to go pee and asked for permission to find a restroom. Mrs. Landino smiled at him and said quietly,"Little boys in diapers don't need bathrooms, do they Jimmy? You know what to do if you need to pee. Please finish up your Coke so Mommy can do her shopping."Mrs. Landino had a lot of clothes shopping to do and it took almost two hours. Long before they finished, Jimmy had soaked his diaper. Little did he know, it sagged noticeably in back so that the saleswomen all winked at Mrs. Landino when Jimmy followed her up and down the aisles of three women's clothing stores. He tried not to notice the rustling noise of his disposable diaper or the fact that the disposable diapers poking out of the diaper bag were much too big for a real baby. At one point, when Mrs. Landino was talking to a young sales woman, Jimmy began shifting back and forth in his wet diapers. Finally Mrs Landino turned somewhat impatiently and said in a whisper loud enough for the sales lady to hear,"Jimmy, stop that right now. If you need to be changed, you'll just have to wait until Mommy buys this blouse. I'll change you when we get back to the car."Jimmy blushed beet red at the reference to his changing, especially after the sales lady looked down directly at his diaper area and giggled. When Mrs. Landino disappeared into the dressing room to try on a skirt, the sales lady went over to the register where two other sales ladies were and began whispering and giggling some more while looking over at Jimmy. He could tell they were talking about his diapers but there was nothing he could do about it.When Mrs. Landino came out in the skirt, all of the sales ladies came over. One was no more than Jimmy's age and she looked at his diaper area repeatedly with a big grin on her face. Then, in the middle of a conversation with Mrs. Landino about the skirt, the oldest sales lady remarked out of the blue,"Babies seem to get bigger and bigger, these days, don't they?""They sure do," Mrs. Landino responded, with a meaningful glance at Jimmy."It's must be hard to find places to change a big baby when you're out shopping.""You can say that again. He's been wet for at least a half hour but he's got to wait until Mommy gets him back to the car.""Why don't you use our back room over there, Maam. You would have all the privacy you need. There's even a good sturdy counter which will work as a good changing table"."Really ... you wouldn't mind?""Not at all. Sally, please take this nice lady and her boy into the back room and show them the counter. There's no customers here now and we won't need you up front for a while."Jimmy groaned silently once he realized Sally was the young woman his age. He was even more embarrassed when Mrs. Landino took him by the hand and said,"Come along, Jimmy. Mommy's going to change you now after all. Thank you so much for your trouble, Sally. I'm Sylvia Landino and this, as you already know, is Jimmy.""Pleased to meet you, Mrs. Landino. It's really no trouble at all. Besides, it looks like Jimmy really needs to get out of those wet diapers. Does he need to wear them all the time?""Not all the time, Sally ... usually just at night time. He's wearing day diapers as punishment today for misbehaving."Jimmy was so grateful that Sally didn't inquire about his misbehavior that he almost got over his embarrassment at her finding out about his diapers. The three of them went through a swinging door into a large back room piled with boxes of clothing. Turning around a corner, they neared a large counter with packing materials which Sally quickly pushed off to the side. She then set a little low stool alongside the counter so Tommy could climb up."Do you mind, if I stay, Mrs. Landino? I've never see such a cute big baby before?""Not at all, Sally. I'm probably going to need your help anyway."Jimmy turned even more red at that and shut his eyes. Mrs. Landino then pulled out a dry disposable diaper and a plastic garbage bag from the diaper bag, set it on the table, and slipped Jimmy's jogging pants completely off."Where did you find such big plastic pants, Mrs. Landino?"Why at a medical supply store, Sally. Believe me, there are a lot more big babies out there then you might think. This one's fortunate to have a Mommy to take care of him. Of course I'm not his real Mommy, just his landlady, but Jimmy doesn't seem to mind, does he?"Again Jimmy blushed and said nothing. Once his baby pants were removed, Mrs. Landino set them aside on the counter."He's awfully cute in his wet didees, Sally observed""He certainly is, Sally".Finally, Jimmy's wet diaper was untaped and removed. Instinctively, his hands came up to cover himself."Young man, put your hands to the side unless you want Mommy to give you another spanking right here."Jimmy groaned audibly and complied. He felt completely helpless and vunerable, just like a litle toddler."He usually knows not to put up a fuss at diaper time, Sally, since it means a spanking. Can you reach in my diaper bag and get his pacifier? That always helps when he's fussy."Sally was only too eager to comply and brought over Jimmy's blue pacifier."You can give it to him ... he won't mind."Of course, Jimmy minded quite a bit but there was nothing he could do but open his mouth and begin sucking quietly."Sally, we're going to need some wet paper towels to clean him off. Do you have anything like that around here?""We sure do, Mrs. Landino. I'll be right back."In a flash Sally disappeared into an employee restroom. Jimmy could hear some running water and then she returned with some wet paper towels which she handed to Mrs. Landino."It would be easier if you got his legs for me, Sally.""Sure, Mrs. Landino."Sally took hold of Jimmy's ankles and raised them high in the air to allow Mrs. Landino to gently wash his bottom which was still quite red from his spanking."It looks like Jimmy got quite a good spanking," Sally said."Yes, he did, Sally. That's because I caught him doing something very naughty." Mrs. Landino said with a wink. Sally immediately understood what she meant."Is Jimmy naughty a lot, Mrs. Landino?""Probably not more than a lot of boys his age. The main difference is that he still gets spanked when he's bad. Of course, one normally doesn't need to spank someone Jimmy's age but that's exactly why spankings are so effective with him. He's almost always good as gold for two or three days after a spanking. Sally, will you fetch me the vaseline from Jimmy's diaper bag?"With Sally watching intently, Mrs. Landino applied a little more vaseline. Fortunately Jimmy stayed limp. Only then was his clean diaper slipped on and taped snugly in place. By then, Jimmy's whole body seemed to be blushing. Finally, Mrs. Landino pulled his baby pants back on, followed by his jogging pants. Now that it really mattered much anymore since Sally had seen everything."Feel free to bring Jimmy back here whenever you come shopping here, Mrs. Landino. Next time we'll have the counter all cleared off for you.""Thank you, Sally. That's very thoughtful of you. Jimmy and I come here once a month and we'll definitely keep you in mind ... won't we Jimmy."Over the next six months, Mrs. Landino and Jimmy returned to the mall once or twice a month. Each time the trip was well announced in advance, in part to see if Jimmy would misbehave and earn daytime diapers. Much to Mrs. Landono's delight, Jimmy did commit some fairly minor infractions on the day before each trip so that he earned a daytime diaper punishment. It seemed at some level he enjoyed having other women see him in his diapaered state, especially a pretty young woman his age like Sally.Thus each time they returned to the mall, Jimmy went well diapered with plastic pants. Of course, it was no longer necessary to change Jimmy in the back of the car at some quiet rest stop now that they had a much better place in the mall. By the end of his freshman year, both of the other sales ladies at that store had escorted Jimmy and Mrs. Landino into the back room and helped change his diapers. But Sally took the most initiative. On each occasion, she ended up coming back as well, either to watch or to help Mrs. Landino. She also asked a lot of questions about Jimmy's diaper routines at home and if he had been spanked recently. By mid-May, Sally asked if she could change Jimmy herself. Happy to have found someone Jimmy's age who was so interested in him, Mrs. Landino immediately agreed. It was during that trip when Jimmy lay bare bottomed on the counter as Sally unfolded a clean diaper that Mrs. Landino suddenly got a great idea."Sally, you wouldn't be interested in a baby sitting job would you? I'm going away for next weekend and I don't want to leave Jimmy alone. Since you already know how to take care of him and since you both get along so well, I wonder if you would consider sitting for Jimmy next weekend.""Really, Mrs. Landino? Why I'd be delighted.""Splendid. Why don't you drive over some night this week so I can show you his routine. It's really quite simple.""Great, Mrs. Landino. What about Thursday night?""Perfect. Wht not come for dinner at 6:00. Here's the address and phone. It's just two blocks from the college on Main St. You know where that is, don't you?""Of course, Mrs. Landino. I won't have any problem finding it."Thus it was that Sally arrived the next Thursday night. Jimmy couldn't decide whether to be embarrassed or to congratulate himself at the propect of a diaper weekend with Sally. It was clear they both liked each other. In fact, Jimmy was extremely attracted to Sally and knew his diaper routines would probably lead to some fun betwen them. At the same time, he couldn't help but feel some embarrassment at the prospect of letting an eighteen-year old woman put him in diapers. Had she already told her girlfriends at her community college about Jimmy? Would word leak out at Jimmy's college? The conversation at dinner was even more embarrassing."Sally, I usually change Jimmy into his nighttime diapers around 8:00. On nights like tonight, it's too hot for Jimmy to sleep in pyjamas. So make sure the blinds upstairs are drawn before you change him. He can play in his room in his diapers and plastic pants or watch TV in my room until his bedtime which is at 10:00. You'll need to check him at 10:00 and change him if he's wet. Be sure to use extra Vaseline if necessary.""After that, it's lights out. If you catch him up after bedtime or misbehaving in any other way, just put it down in his "bad boy" book and I'll take care of that as soon as I return on Sunday.""What about if I catch him playing with himself, Mrs. Landino?""Well, as you know, I always punish him right away when that happens but I'll leave that to your discretion. You can mark it down in his book if you want or you can handle it yourself.""Thank you, Mrs. Landino. With six years of babysitting experience, I know how to deal with bad boys. On the other hand, I've never spanked anyone as big as Jimmy. Will he give me any trouble, Mrs. Landino?""If he does, just mark it down in his book and I'll double the number of spanks on Sunday. Jimmy, I want you to do everything Sally asks you, is that clear, young man? If I hear you didn't obey her, I will ask her to give you your Sunday spanking." Jimmy flushed even more when he saw Mrs. Landino wink at Sally."Yes, Mommy", he said without quite realizing what he had called Mrs. Landino "Mommy" in front of Sally."That's my good boy. I can tell you will be in very good hands this weekend.""Do you mind if I have a girlfriend over for company on Saturday night, Mrs. Landino?""Not at all, Sally, as long as your friend doesn't tell anyone about Jimmy's little secret.""Oh I'm sure she won't tell anyone. She already promised me she wouldn't.""Fine ... just make sure you don't mess things up. I expect to come home to a neat household.""Don't worry, Mrs. Landino ... I'll make sure everything is nice and tidy"."Splendid, Sally. After dinner I thought we could take Jimmy upstairs and change him into his diapers a little early tonight. You've already seen how we do things at the mall and you've helped me quite a bit there. Are you ready to try handling his diapers on your own. That way, I'll be sure you know where everything is.""No problem, Mrs. Landino. I'll be happy to do that."After dinner, Mrs. Landino took Sally into her bedroom and showed her Jimmy's "diaper drawer" and his "bad boy" book. Sally noted Jimmy had already earned about fifty spanks that week."Sally, if you're wondering when I'll be home on Sunday, I expect to return by 8:30. Since that is an hour after Jimmy's normal spanking time, I hope you won't mind waiting while I take care of that first.""Not at all, Mrs. Landino.""Since Jimmy often tries to cover up his fanny with his hands during a spanking, would you mind helping me out by holding them in front of him?""Of course not, Mrs. Landino," Sally said, knowing full well Jimmy could hear everything from his bedroom.After going over Jimmy's diaper things, they returned to his room where he was sitting on the bed. After getting him to lie down, Sally began by putting a pacifier in Jimmy's mouth."This is to make sure you don't fuss, Jimmy." As she watched from the side, Mrs. Landino knew she had found just the right young woman for Jimmy.