humiliation sex stories – Page 5 – Page 5

Mrs. Robinson’s Panties

My mother used to send me up the street to help a single mom with chores around the house. At first I hated it. Then I discovered her lingerie in the laundry and started trying it on. She never found out, but I often fantasize that she did. This is one such fantasy. Mrs. Robinson was like a little sister to my mother. I wasn’t even sure how they’d first met, but she was always around when I was growing up. When I was in junior high she’d gotten married and bought a house just up the street from my

September 18, 2024 No Comments

Mother in Law

My wife’s parents and I had been planning a trip for many month to Texas, and when the time came to go, we had some interruptions that worked in my favor. When the time came to leave my Father in law could not fly out with us due to urgent business and my wife had a friend die. I did not know the friend, my wife wanted to show up out of respect, we had reservations, so she said “you and Mom go, we will show up tomorrow”. Trish (Mom) is a bit of a pill to travel with, but

September 18, 2024 No Comments

Mother’s Sexy Clothes

It was a typical Saturday night in our household. I was preparing for another night in front of the television, while my Mother was getting ready for a night on the town. There was only the two of us in the house since my Father left us when I was about four years old. I was eighteen years old, but due to being skinny and boyish looking people took me for being about fifteen. I was also very shy, especially around girls. I longed to have a girlfriend, but I just did not have the confidence to ask anyone out.

September 18, 2024 No Comments

Mrs. Alison Jenkins

Mrs Alison Jenkins part 1 It had only been two weeks since Steve, my husband had gone to work in Australia for a whole year. Already I missed him and hated living on my own. We had only been married for a few months and moved several hundred miles away from my parents because of his stupid job and now I was stuck here alone. To be fair the small village in North Yorkshire was lovely and unlike London where I grew up everyone was very friendly even if they did consider us both to be “posh southerners”. We had

September 18, 2024 No Comments

Milli’s First Lesson

Janice pulled the Lexus into the driveway, and noticed her bedroom light on. She was positive she turned it off before she left this morning. If her wayward Nephew was nosing around in her room there would be hell to pay. She was already extremely ticked off at having to attend a meeting with his Principal this morning. A meeting which ran on too long, causing her to miss her flight to Chicago. Thank goodness she was able to assure the Principal that Bill would be on his best behavior for the next few days, until graduation. Janice closed the

September 18, 2024 No Comments

Modern Health Care? (chapter 2)

I was enormously embarrassed sitting on the exam table in the nude with just a towel wrapped around my waist. My classmate Donna was grinning ear to ear as she watched me sitting there. Dr Lerner turned to my stepmother and announced. “ you can pick up a prescription for antibiotics on your way home. I will need to recheck his wound in a week and would like to to use him to demonstrate an uncircumsed penis to interested hospital personel at that time.” She hit a key on her tablet and said, “Donna will show you where to find

September 18, 2024 No Comments

Modern Health Care? (chapter 3)

The three of us. Donna, Sharon, and myself. lay in a post orgasmic puddle on the floor of Sheila Duffys living room when we heard the phone ringing loudly. Donna rose slowly and picked up the phone. The loud voice of Mrs Duffy was heard yelling heard yelling, “get moving, you have to get Everett ready, Barbara will be picking the three of you up in an hour to drive all of you to the of you to the school. Make sure you get him really clean, make him cum at least twice so he does’nt squirt all over anybody

September 18, 2024 No Comments

Mom and Her Drawers

Part I It was kind of a dull rainy Saturday and Mom announced that she would be going out to do some shopping for the afternoon. She asked if I would like to accompany her but up to that point I found her shopping quite boring – and besides, I had other things in mind. But first some background. I was then about 10 years old and by some crazy fluke had recently discovered a unexplainable fascination with my mother’s lingerie and of all things – her shoes. Mom was in her late 20s and although not beautiful, was a

September 18, 2024 No Comments

Mommy’s Little Pervert

Mommy hates me because she got pregnant with me and she says I ruined her life. I never met my daddy. I also turned out to be a scared, submissive little boy who she says is a little sissy boy. I kinda look like mommy. I have the same black hair as her and she makes me keep it long. People have told her that her daughter looks just like her and that makes her mad. I’m supposed to be a boy, but you can’t always tell by the clothes she buys for me. I get some hand-me-downs from my

September 18, 2024 No Comments

Mom’s Humiliating Catfight

This was absolutely the last straw. The last couple of times Billy got beaten up at his junior high school, there was really not much I could do. Children can be awfully cruel, and aside from advising him to stay out of the troublemakers’ way (and failing that, try to reason with his harassers), I had to accept that this is part of a boy’s growing up experience. The last time, I suggested that we report the incident to the school authorities, but Billy objected, not wanting to come across as some wimp. In a way, he was right

September 18, 2024 No Comments

Lord Malcolm

Let me introduce myself. I’m a robust, fun-loving, healthy, good-looking and mature woman of fifty, and I’ve always had a keen interest in good sex. Some of my most memorable encounters have involved the sexual awakening of a young man, or boy really, largely by *my* skill and intuitive understanding of what arouses these young people. Many lads have received the benefit of what I had to teach them about themselves, but none of them has been as personally rewarding as the fourteen year old scion of the noble and wealthy family with whom I work as nurse/governess. Lord Malcolm,

September 18, 2024 No Comments

Massage Therapist’s Mother

When I was 20 years old, I once went to a normal massage therapist (which was actually in a beauty salon). Not being used to seeing men walk in there, I got the most curious looks as I stepped in to ask about their therapy sessions. The young woman took my name down and gave me an appointment. When I came back the next day for my appointment, I was greeted by the mother of that same lady. I was not too happy because the mother was clearly in her late 40’s early 50’s. I decided to go for it

September 18, 2024 No Comments

Masturbating for Sandra (ch. 1)

Sandra and I have always had a curiously sexual relationship. Not that any physical contact has ever taken place, but sex is never far off the agenda when we converse. My partner is her husband’s sister, so I guess that makes her my sister-in-law; indeed, I met Lesley at one of Sandra’s parties. This is vaguely irrelevant, although it does explain the relationship, e.g., outrageous flirting and general horsing around with somebody I see frequently, although no contact One Sunday afternoon, I had returned home from playing golf, showered and as usual, was intending to spend the rest of the

September 18, 2024 No Comments

Masturbating for Sandra (ch. 2)

About two weeks later, Lesley was out for the evening and I was carrying out her instructions. These were to tidy up the house, sort the laundry, etc while naked and erect. I was to maintain an erection for two hours by masturbating then, after 9pm, it was up to me. I could either continue masturbating or not, but I was not to ejaculate without permission. We often play this game. It is part of the humiliation and exhilaration of being naked and under somebody else’s direction. Of course, I could just strip, wank and get on with stuff, but

September 18, 2024 No Comments

Masturbating for Sandra (ch. 3)

Many months had past since the previous episodes of this short saga, during which time normal relationships were resumed. Sandra and I kept bumping into each other at various family functions and would occasionally speak on the phone, but for some reason my masturbatory efforts on her behalf were never discussed or even referred to. There were highlights of course. At a drinks party for my birthday at a local bar, Sandra came over to the table where I was sat with a beer she had just bought for me. Nothing unusual in that, except that she was wearing a

September 18, 2024 No Comments

Lisa’s Panties

Bob McClintock had got himself into some major trouble. He had had his run-ins with the law before, and even done a couple of thirty-day stints in the county jug, but this time he had really hit the big time. For his part in an arson plan gone wrong he had netted himself four years as a guest of the Feds and, even with remission for good behavior he was going to be doing every day of two and a half years. Things might not have been so bad if his wife, Leona, was still alive, but she had been

September 18, 2024 No Comments

Living With Mrs. Harwood

Justin began reading his journal. His mind wandering back to a few years ago. Monday Journal Entry Well here I am. It has now been six weeks since I moved into Mrs. Harwood’s home. My parents now somewhere on their round the world excursion. I haven’t had any letters from them for a few weeks, so I have no idea where they actually are. But I do know that I won’t be expecting them home for another eleven months, give or take a few weeks. Mrs. Harwood lives just a few streets away from our own home. But with mum

September 18, 2024 No Comments

Life in a Female Household

My dear mother died of grief shortly after my father was killed at the start of the First World War. It was then left to my father’s sister to raise me along with her two daughters. Her husband was also away commanding a regiment of fusiliers somewhere in northern France and, my aunt, far from being enthusiastic about having a thirteen year old boy joining the household, resigned herself to yet further inconvenience of that damnable war and reluctantly allowed me shelter and succour within the bosom of her household provided that my own governess accompanied me and that

September 18, 2024 No Comments

Laundry Day

Chris stood a little back from the wooden fence and watched the children walking to school. Most walked in pairs he noticed. Some carried lunch pails or books. Many had those backpacks slung over one shoulder. He was grateful they were too busy laughing and watching each other to notice the naked man tied to the clothesline in their neighbour’s backyard. The fence with its thick, angled boards worked well to hide him. Chris sheltered behind the fence, knowing he was not invisible. He could feel the blush rise in his cheeks each time one of the kids looked

September 18, 2024 No Comments

Johnny Gets Spanked part 3

John slept little Friday night, lying in bed wondering what was happening to him. When he did fall asleep he had another one of those scary but unbelievibly sexy dreams. He dreamt that Ms. Anderson was the head coach of the Cheerleaders and had decided they needed a mascot. She came to his classroom in the middle of the day dressed in a short cheerleader skirt and tight sweater that emphasised her breasts. She anounced to the whole class that “little Johnny” was to be their new mascot. Everyone, especially the girls, laughed at him and Ms. Anderson grabbed his

September 18, 2024 No Comments

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