Tag: High School

The MILF Chronicles – Prologue

This is a first draft. Comments and constructive criticism always welcomed

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The MILF Chronicles

Part One: Prologue

Everyone has a story to tell I guess. Some are more interesting than others, so I will let you be the judge of mine. My story is one of change. Perhaps change is a bit understated. Radical transformation might be a better way to describe it. I want to relate to you my tale of how I evolved from simple, middle-class housewife to a voracious sex crazed Cougar. It all began with a divorce.

I know that most of these stories begin the same. We married young, right out of college. Had our son less than a year later. He went to work climbing the corporate ladder and I stayed at home being the mom.

Our sex life was average. Nothing out of the ordinary. He was an attentive lover, always making sure that I had at least one orgasm, but doggy style was considered adventurous for us. As the years passed and our son grew, sex became less frequent, less passionate, more like going through the motions. Read more »

Cum Inside: A Family Story- How I succumbed to incest with my sister and mom.

It took me a while to understand that my sister was actually an internet sensation. Way longer than everyone else. Mom didn’t want me to know. They all hid it from me. Maybe Mom didn’t want the Christian town we leaved in to know she had raised a pornstar.

When my single mom got frustrated, she would usually go out drinking with her friends on the town and return home all fucked up and spewing secrets. My sister, Sonya, had moved out months earlier before the coronavirus lockdown over an argument that seemed minor to me. On this night, Mom staggered into the house dressed in high heels and a black dress. I helped her upstairs. Before she could pass out, she told me Sonya has an online adult site.

I was shocked and surprised. My older sister had been very vanilla and nice to me that as an eighteen year old now finished up with high school, I never thought she was remotely sexual at all. I didn’t even remember her dating in school. She was 21 and a few years out of school and didn’t want to go to college. I had naturally thought that was why she was having regular fights with Mom. Read more »

Cum for Class- Sister needs brother’s cum for university project.

“There you are! What took you so long?”

My sister was leaning against the wall in the corridor, looking stressed. I guessed it had something to do with her project – the university professors apparently kept their master’s degree students busy. Things were less hectic for us first-years – we could work really hard if we wanted to, but nobody was breathing down our necks like teachers did in high school, to make sure we did our homework. Having been at the university for about four months now, I had found a nice work rhythm that made sure I kept up, while still giving me time for hobbies and relaxation. I think my sister was working quite a lot harder than I was.

“Hey, sis. Got your message…”

“Yeah, that I sent two hours ago. And an hour ago. And half an hour ago. Where were you?”

“I had things to do – am I your servant now?”

“Yes! Well, at least… look, you agreed to help me with my lab project. You know the one that I’m right in the middle of?”

“That explains the ponytail.” Read more »

No panties at the prom. [FM]

Well my hubs still hasn’t realized that I found his Reddit porn account so I’m going to share more stories until he does.

This one’s short and wet.

When I [18] was in high school, I was dating a guy named Kyle [18]. Typical stupid high school teen couple. Except Kyle was a jazz pianist. And a really good one. I still can get wet thinking about how he could play my body like Mozart with those hands. God. Those hands. Long lithe fingers, strong yet light, and capable of infinite levels of pressure and patterns of motion and he could use both at the same time. He made me cum so hard with his hands I discovered squirting. It was embarrassing at first, but we loved it.

Of course I wanted him to touch me nonstop. Once in art class we were working with clay and I got dripping wet watching him shape a pot on the wheel, sliding his index and middle fingers on the wall and roll clay between his thumb and index and between his palms. I told him inasmuch and that evening he was kneading my tits in his palms, rolling my nipples in his fingers, and massaging two fingers along my gspot while delicately torturing my clit with his thumb. My mind exploded with the first orgasm and the rest was vaporized by the second. Jesus I’m wet now. Dammit. Read more »

The transformation 1

This is written as a part 1, but I don’t know when I will get to part 2

I had noticed the start of the changes 4 weeks ago, from the body of a slightly chubby 40 year old man, I was changed. My skin had gotten softer, my body hair was receding and my head hair was regaining old areas. My dick began shrinking and I began devaloping tits.

I don’t know how this happened, or why, but it has. I started calling in sick a week ago, when my breast became so sore that I couldn’t handle it. Thank god my wife was still visiting her family in Ireland.

This morning I woke up with my dick gone, replaced by a pussy that looked very real. I my first instinct to touch it send ripples through my body as I experienced a pleasure so intense that it almost hurt.

I continued touching myself and tried to think of my wife, but I couldn’t, she was not sexually attractive to me anymore. My mind went to Fred over and over again, he was a young coworker, maybe 23 or so, who had started working in the company about 6 weeks ago. He was tall, muscular and had full black hair. Read more »

Dressing Room Blowjob [F18][Public Sex]

Wearing only her bra and thong, Diane stood in front of her closet and starred into the cavernous wooden coffin, packed to the gills with branded fashion. It offered her no solutions to the question she posed the plenum of carefully selected dernier cri.

“What do you wear to meet a man who left you before you were even born?” Diane asked her clothes a second time.

“Running shoes?” Devyn posed.

“HAHAHAHAHA! Oh my God! That was… brutal!” Diane gassed.

“Wear whatever you want, Diane. You are in charge. You decide how much you want to let him into your life. You can decide you never want to see him again, if that’s what you want,” Devyn reassured.

“You’re right!” Diane agreed and pulled out a drawer and selected a pair of Rag and Bone jeans that she particularly liked, a conservative, but fun, button-up blouse that looked fantastic on her and showed zero cleavage. Then, sitting in her desk chair, she laced up her new favorite chunky Simon Miller platform boots that her mother angrily called her about when she saw the six-hundred-dollar charge on her credit card statement. Read more »

[M]y Ex + Public [F]ellatio w/ side of Anal.

I was over dressed for a Thursday night, but I was young and didn’t think twice about blacking out on a weekday. It was my friend’s 22nd birthday, and I was heading to his girlfriend’s house for the pregame. I sat nervously in my roommate’s car, fidgeting as we got closer to our destination. I didn’t know what the night would bring… But I knew that copious amounts of alcohol would be consumed. I knew my ex would be there. I knew that I was falling for someone else and didn’t want to screw it up. But I also knew that I was a sucker for a blonde.

We pull up to the house and there were two maybe three cars parked out front. We got there early, but that was okay, I had been friends with the birthday boy and his girlfriend since high school. My ex would be there too, she was roommates with the birthday boy’s girlfriend. We had dated for a good portion of college, and had broken up months prior. It seemed like yesterday when I was helping this girl move into a swanky apartment in one of the biggest cities in the world. She was embarking on a new journey, while she continued her education at a private school back East. We didn’t think long distance would work, and the last time I saw her, she was crying in front of her new big city apartment. Read more »

I’m a [F] 19 y/o Escort.

I sit in the half-full cafe as the jingle of cups and saucers surround me. The cute barista that offhandedly flirts with me when I get a coffee here is looking over at my empty table. I try not to let her know I notice her. I’m waiting for my date. Well, actually my client. My Sugar Daddy.

The newest one. The others are a story for another day but this is the Daddy I want to write about today. He’s very average. I know that doesn’t sound sexy but if you want the truth? Most Sugar Daddies are not Christan Grey. They are Michael Scott but less attractive (I dunno what that says about my Steve Carrel fetish) They are emotionally stunted civil engineers. The newly divorced middle-aged high school teacher or in Daniel’s case, just a well-off businesses owner with very mundane looks and awkward social skills. Daniel doesn’t pay as well as my other Daddies did. But he’s easy. He’s consistent and I can get him to buy me a coffee and cum in me within a couple of hours of counting the wad of cash he hands me as he takes a seat and sips his Earl Grey. Read more »

In the opinion of this [m], 50% of 69 outweighs 100% [f]ellatio any day.

I preface this post by stating that this is less a specific ‘gonewildstory’ than a general observation I have made in assessing the many ‘gone wild’ experiences I was lucky enough to have in my single days.

Though it’s probably obvious from my earlier posts, I absolutely love 69-ing. As much as I love having intercourse, it retains a special place in my (sexual) heart. I don’t know that I’d say I like it more than intercourse, itself, but I can not say that I like it any less. The two are tied, shall we say.
Like any guy, I’ve also enjoyed getting blow jobs from females. But here’s the thing. I vastly prefer the head I’ve gotten while giving a woman head over passively receiving a blow job. I found that I am more attuned to the sounds of fellatio (like gagging, messy slurping) which are not always the biggest turn-ons for me. When I’m 69-ing, I am concentrating on giving the woman pleasure and enjoying the exploration of her vagina with my mouth, nose, and fingers. Often, instead of listening to slurping or gagging, it would be her moaning from my cunnilingus that I would hear. And though it can be quite a thrill to see a woman ‘go down’ on me, in the typical woman-on-top 69 position I would use, it was always far more aesthetic seeing a (usually hairy) pussy up close and personal. Read more »

Throat Problems? [MF]

In college, I had a best friend, a roomie, a sister almost, Adele. No we were never lovers, but we were as close as we could be and not take our clothes off. There was only one thing we did not share, that was boyfriends. Just before graduation, she met this guy, Gary, nice guy, a bit shy and he really did connect with her. I must admit I felt a bit left out, a bit of jealousy she preferred his company but this too is a bit of growing up.

After graduation, we promised to keep in touch as she went to her home on the West Coast and I went to work for the State Department. My father was an oil worker and by the time I had finished high school, I spoke five languages and at times, English seemed my second language. The State Department seemed a natural fit. I was posted immediately to the Middle East and spent some time reconnecting with childhood friends, and their now husbands if they were important. This opened some doors at times, so I was considered valuable. This personal connection diplomacy is often just as important as official policy, an idea that seemed to have been lost in recent times. I was transferred home and the Covid thing hit. Read more »