Tale of a Sissy Named Janie

5/5 - (1 vote)

Part One – How It All Began Johnny’s father was an inventor who worked covertly with the CIA, but he died tragically in a car accident when Johnny was only six years old. Somehow, Johnny inherited the same love of inventing and tinkering that his dad had, and he was great at installing gadgets around the family home. Johnny’s friends and classmates thought he was great as he would help them fix broke gadgets or help them build projects they were working on. Many people in his neighborhood felt he might become the next Thomas Edison or Elon Musk. But...

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Figuring It Out with Auntie Rosa

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Rosa smiled as she wiped some suspicious white stains off her favorite leather couch, using a chance to leave her yoga class early just to finish a few little tasks, like removing cum from her couch before it was stained for instance. Her nephew had a perfectly natural libido for any young adult… alongside the perfectly natural lack of care on where he worked on himself, were she of a more traditional demeanor she'd have gone straight to him, perhaps even made him clean it up himself, but she liked to think that she was better than that. Sure enough,...

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Mom’s Big Boobs

5/5 - (1 vote)

Mom’s Big Boobs is a follow-up to Sister’s Big Boobs, a story about a little sister who’s insecure about her big tits, and a loving, well-endowed mother who encourages her son to have sex with her to make her feel better about herself. You can read the first part here: Sister’s Big Boobs ***** The next morning, I woke up to the footsteps of Mom moving around the kitchen downstairs. I still felt the ache in my thighs from last night with Sofi, and a certain lightness, like I’d unburdened a part of myself. I took my time getting dressed,...

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Sister’s Big Boobs

5/5 - (1 vote)

“Alex?” Mom knocked on my door. “Can I come in?” “Sure,” I said, spinning my chair around. She slipped inside, wearing a knee-length summer dress. Her chestnut hair spilled over her shoulders. My mother was tall and pretty, a perfect oval shape with almond-shaped eyes. She had a subtle hourglass figure with plenty of curves you just wanted to squeeze, but at the moment, she looked upset, which weighed her down. She sat on the edge of the bed and sighed. “What’s this about?” I asked. “It’s about your little sister, Sofi,” she said. “Ever since her boobs started growing,...

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Mom Taught Me to Fuck with Grandma

5/5 - (1 vote)

My name is Kevin. I’m 12 years old and I’m the only child to a 38-year-old single mom. My mom is single because my dad died 2 years ago when I was 10. I’ve been having regular sex with my grandmother, who is 73 years old. Not only does my mom know, she frequently watches. When I was 8 years old, my dad brought his mom to live with us because she was showing early signs of dementia. At the time I didn’t know my mom couldn’t stand her, but realized that after my father died and her true feelings...

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Helping and Seducing Granny

3/5 - (1 vote)

Every week I go over to my grandmother's house to mow the lawn and generally fix up and clean up her yard. She tells me how much she appreciates the help, now that her husband is gone. One day this summer I learned just exactly how much she appreciated me! I walked into her kitchen that afternoon all sweaty, and drank a glass of lemonade she made for me. She noticed how hot and tired I was and made me sit in the kitchen while she fixed me a snack. I sat and watched my grandmother move around the kitchen,...

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Twisted Tupperware Party

5/5 - (1 vote)

Nick lived a typical lifestyle in a typical medium sized North American city. He had recently celebrated his 16th birthday with his loving parents, Jim and Sandy. Nick was a pretty average kid, normal looks, good grades in school, lots of friends of both gender. However, Nick had always felt at odds with the fact that he had so many close female friends yet none of them ever wanted to move to another level. Why was he so close to them yet unable to date them? It was a question that bothered Nick frequently and caused much stress in his...

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Mommy and her Baby Boy

4/5 - (1 vote)

Jack waited on the corner for the car that picked him up every afternoon. As usual, he was impatient and shifted his weight from one leg to the other. He looked through the chain-link fence into the schoolyard which was empty at that time of day, but suddenly turned his head and smiled when he heard the car pull to the curb. The woman quickly got out of the car and almost ran around it to the curb where she took Jack's bag and gave him a peck on the cheek. She then opened the car door for him and...

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My Widowed Aunt

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Aunt Rita was my mum’s oldest sister and although she lived at the other end of the country she was always very close…. In fact I always thought of her as my second mum… She was married to Harry who was a lovely man and who I was also close to…. A bit like my best friend in fact. When they were sixty uncle Harry died suddenly… I went to the funeral with my mum and we stayed for about a week…. Rita was in bits…. Before we left to come home my mum told Rita that if she wished...

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My Old Grandmother

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When I was young I sometimes went to stay with my grandmother who was in her 70's and who lived with my unmarried Aunt, her daughter. It was a small house and I had to sleep in the same large bed as my grandmother. She would change for bed in the bathroom and wore a very long, modest nightdress buttoned up to her neck and down to her ankles. But I could still clearly see the shape of her body, the swaying of her large saggy breasts and the outline of her nipples as she moved to the bed. One...

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Grandma, What BIG Tits You Have!

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When my mother called to tell me that my grandmother needed a hand over her house moving things around and storing some of my grandfather’s belongings. I jumped at the chance to see her since I hadn’t visited in a while with her living a few towns over. I just never made the time and this would be a good excuse to catch up since grandpa’s death. I got there about 11 am as she answered the door and I was taken aback at the amazing shape she was in well into her 60’s. Long flowing blond hair that had...

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Mom’s Macromastia Mystery

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It was close to the December vacation and I couldn't wait. I was literally counting the minutes of the clock at work and knowing tomorrow morning, I would be on my way back home. I haven't been home for about 2 years and the thought of warm winter fires, the smell of pine, roast meats, vegetables and laughter just sounded like what I needed. Finally work finished, I left in my car and drove home. Luckily not too much traffic. I picked up a pizza on the way home as I didn't feel like cooking. I finally got home and...

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Bath – a Mother and Son Story

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Carol hadn't had sex since her husband Ray had left more than four years ago. Strange as it sounds, the thing that finally brought her celibacy to an end was her son breaking his leg. *** Mike was 14 and a natural athlete. Whatever sport was in season, he played. He was good at all of them and great at some. It was at a baseball game where an inexperienced player slid into second base, spiking Mike's left leg and breaking it. There was knee damage as well, so Mike was now laid up with a cast almost hip to...

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Roger’s Auntie Becomes His Mummy

5/5 - (1 vote)

I have always been a fairly mild and meek person and would never get involved in any sort of confrontation and for that reason people seem to treat me rather badly. As an 18 year old in his last year at school I had begun to rebel a little and although my parents told me off a lot I tended to ignore them and do what I wanted to anyway. One day just as term was about to finish my mum said that I was going to spend the summer holiday with my auntie Dee. She said that as I...

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Caught My Son Jerking Off into My Panties, and Then…

4/5 - (1 vote)

A few years back, I started to find several pairs of my panties in my son’s hamper when I was going to do laundry. They were obviously used and very messy and I honestly didn't know how to react. This was before we were intimate with each other the way we are now, if you’re at all familiar with my post history. Anyway. In the end I did nothing and hoped that he wouldn't do it again, that it was just sort of a one-time thing, something he did out of curiosity and that I wouldn't need to talk to...

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When I Was Twelve!

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When I was twelve years old, my parents had been divorced for several years. One day, my mother was in the bathroom when she called me to get her a clean towel from the laundry. I got the towel and went over to the bathroom door. It was opened a crack, so I just pushed it the rest of the way open, and stopped with my mouth open. “I’m…I’m sorry, Mom,” I said. She was sitting on the toilet seat with one foot pulled up and polishing her toenails. She was completely naked. I just stood there and stared at...

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My Aunt

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My story begins during that one fateful trip my aunt made to visit my mom and I. I was 19 at the time and my mom and I lived alone in our condo overlooking the water. Our house was nice, a big pool and a hot tub downstairs (my mom had a great job and that left us very well off). I also had a problem. After many years of masturbation I could not make myself reach an orgasm. I thought I came close a couple of times, but the fact that it never happened to me was cause for...

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Stripping for My Nephew

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I slid my hands over my skinny toned stomach as I smoothly put my slinky black bra over my round D cup breasts. My nipples were still erect from my performance. I slid on a white wool sweater and tied my silky blond hair into a loose bun. I pulled out the last of the bills that were stuck in the waistline of my thong and organized them in a neat pile before putting them into my bag. “How’s the crowd tonight Carly?” “Not bad Stacy, a few horny businessmen but I’m afraid I milked them for everything they have...

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Buying Panties with Mom

4/5 - (1 vote)

My mother did it one day. I had no idea it was going to happen until it was already happening, and I had no choice but to go along with it. This is the best I can recall of exactly what happened during that forty-five minutes that in some ways will always stay with me. First off, let me tell you that my mother is a truly sexy woman, and we have been living secretly as husband and wife for years. She's fairly well-off, and she has this thing she likes for us to do, and we do it several...

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Harry Massages His Mother-in-Law

5/5 - (1 vote)

"Did I tell you that my Mother is coming to stay with us?" I shook my head, and then I said, "No." "I thought I did." She hadn't. My Mother-in-law coming to visit, was something I would have definitely remembered. "When, and for how long?" "Just for ten days," then she looked at me and smiled, before adding, "She will be here on Sunday." I smiled back, because I didn't want an argument, but inwardly I groaned. In less than a week, 'The Bitch' would be here. That was my pet name for her, but I called her Helen to...

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