Shameful, Secluded Ravishment [Anal][Feminization][MM][Humliation] (from a /r/dirtywritingprompts request)

I’d just turned eighteen the day before my flight crashed. Brett, the boy I crashed with, was nineteen. The flight was nearly empty and we’d been the only two in the back of the plane; it had broken free of the rest and we’d somehow glided and crashed in water. There had been a storm. It was deep wilderness. We had no idea where. We walked for seven days without finding the rest of the plane or anyone else. It seemed like we were maybe somewhere in Alaska–mountains and verdant forest stretching across what seemed like the whole world. We survived on water and very little food. On the seventh day we found the cabin. We figured it was some wealthy hunter’s cabin. The place was stocked with food, drinks, fuel, toiletries, a generator. It had pretty much everything you’d need to survive in the wilderness–except a functioning radio, any maps, or a compass. We settled into waiting it out for someone to find us in the cabin.

[ff](mtf), Unexpected Interest [slow build][kink][tender]

Hello, and welcome to my wonderful wall of text. For boarding right to the sexy bits, “***” has been provided for your convenience. If you have the following sensitivities or turn offs, please take advisement that MyPoisonIsReddit is not responsible for any injury or suffering that may occur:

All the consent

D/s, Mistress/Slave

Impact Play

Anal Play

Degradation/humiliation (S*** mentioned)

Biting/Marking

Bondage

The Trans Agenda(TM)

Ironic Catholicism

My horrible sense of humor

This is the story of one of my most recent partners. As a bit of background, I’m a transgender woman. I started hormones a year ago, as soon as possible after my new insurance kicked in and a little after I turned eighteen. I’m tall, average build, and have some gentle curves and perky B cups. My hair and eyes are both a dark brown, and my hair is wavy and shoulder length, with natural red highlights. My genitals are still in their original configuration, although it’s become shorter and plumper, and I have a Midwestern accent that almost never comes out, but my domme tells me it can be sexy when it does.

Marcus with the big dick [MM]

So I’m bi.

I wasn’t always bi. In fact, for most of my life, I considered myself totally straight. In fact, I still consider myself MOSTLY straight. But in my early 20’s, beginning with an unusual attraction toward a good male friend of mine, and culminating in this story, I’ve gradually pushed the boundaries of my sexuality, so that today I’d say I’m equally attracted to attractive men and women, although I find far fewer men attractive than I do women.

I had had two lackluster experiences with Grindr guys before. We didn’t match personality-wise at all. But I was browsing again, bored and horny; and I get a message from this guy named Marcus.

“What’s up man? You’re cute ;)” he says.

I flirt back, and we exchange pictures. I like what I see – nice abs, smooth coffee-colored skin, a really cute firm butt (I don’t know what it is about cute butts but they’re maybe my favorite feature on both sexes). And an above-average-sized penis. It made my mouth water.

My First Jobud Experience [MM]

I only recently found this subreddit, and after reading some of the stories of people’s experiences, I figured I’d add mine to the mix (this was previously posted on r/jobuds). Sorry for this wall of text, but keep in mind, this happened back in The Olden Days. There was no internet porn! Because there was no internet! If you wanted porn, you had to watch the scrambled cable channels in the hope of a couple seconds of boob or find your dad’s single issue of Playboy in the bottom of his dresser drawer under the Hai Karate. Basically, good spank material was hard to come by. I had to make up for it with a good imagination.

Anyhow, my first sexual experience of any kind involved me and my best friend Matt. We had been friends since we were little, going to school together and hanging out on weekends. Sleepovers were common, just the two of us when we were younger, then as groups when we started staying up all night playing Dungeons and Dragons. Yes, we were nerds. Big time. None of our group had ever had girlfriends and most weren’t very athletic. If we weren’t playing D&D, we were quoting Monty Python and talking about the hot girls we knew, but never dated. But nobody every copped to beating off. It just wasn’t discussed back then.

[MF] Laura’s sorority sister kicks it up a notch!

So as I mentioned, after I fucked Laura, I ended up fucking her pledge sister in the sorority. Enjoy!

I met Hiromi when she came by the house asking to borrow a screwdriver (and a guy to use it). Apparently something needed fixing in their sorority, and so being outgoing/cute/friendly, she decided to swing by and ask us for some help. I answered the door, and seeing her, I immediately knew I’d do whatever it was she was going to ask. Hiromi stood about 4’11”, with a tight, firm body but a big ass (for an Asian girl). Her tits were a little bigger than apples, plump and perky on her chest, and her long black hair was slightly curly and she wore it straight down her back, with bangs swept across her forehead. Her almond-shaped eyes were dark brown, and she had a cute button nose, a few freckles, and a sweet, small mouth that seemed to always be smiling. “Can you help me out real quick?” she asked, and I immediately obliged, walking over to her house and helping fix the kitchen table which had somehow lost a leg. As I worked, we chatted about our friends/school/Greek life, and we seemed to really hit it off. When I left, I gave her a quick hug, feeling her small body pressed against mine, and said “Swing by tonight for a drink if you want! Not many guys around, but we can still have a good time!”

[MF][minor Trans] Wormtongue

This is the story of the the time I had a tongue in my prostate.

I met Kyla at a dance club in Bucharest. We hit it off and ended up back at her place. She was slim, about 170 cm tall, jet black hair, and had on a tight black dress. She had full lips, soft skin, and brown eyes. Her apartment was in a very old building, at least several hundred years, but was beautiful with large spaces and high ceilings. Despite its age it was fully modernized and quite luxurious.

She was quick to kiss me as soon as the door shut behind us. The intensity caught me off guard as her tongue explored my mouth urgently. In the embrace we groped like a couple of teenagers and I was lead quickly to her bedroom.

Now just in her panties my eyes were treated to two spectacular breasts being highlighted by the ambient lighting. As she pulled me closer she reached into my pants and started stroking my already hard cock. She whispered to me that she wanted to put it in her mouth and proceeded to fully undress me until I was standing there naked with her kneeling in front of me.

That time i met Amy, the facefucking MILF of Montreal. [MF] [shower sex] [MILF]

When I was growing up, I lived beside a Ms. Loris Bachman, a stay at home mother of 2. She was the definitive embodiment of a MILF. Red vivid hair to her waist, legs for miles, an ass as big as her tits. It was like finding Jessica rabbit had settled down in your neighborhood, had two kids and you would see her at PTA meetings or community events offer cookies and a smile. I remember fondly of seeing her reading poetry out loud on her back porch at her book clubs, drinking English breakfast tea. Every so often I was awake early and i would see her come home from her morning run in her tight Lycra running shorts and low cut running top, pale skin glistening with morning sweat. Soft spoken but with a mother’s firmness, she would tenderly dote on you one moment and whip your ass when you got out of line the next. She would wear these very conservative but skin tight clothes that could not hide a body made for sin. 

 

[MF,fm] Julie and the kids [not much sex, but voy., mast. and ‘sextortion’] Part 3

I ordered the smoke detectors with integrated wifi spy cameras the next day. It’s something I had seen online before, but never had a use for…until now. I ended up getting four of them, one each for my bedroom, the guestroom where all three were staying, as well as the bathroom, plus one extra in case I found another use for it.

I paid the extra $29 for express shipping, even though I might not have time to install them until the weekend. Things at work were pretty busy, not leaving me much free time during the day to start installing these things.

We got into somewhat of a routine over the next two days. Julie got the kids ready for school, and we all went in my car to drop them off, and later to pick them up. She and I were home during the day, but because I was busy with actual work, she just loafed around watching TV with nothing else to do.

Julie’s did get called in for one shift in the evening. The kids would be home with me “babysitting” them. I said it was fine, that she needed the money. I even let her use my car that night so she wouldn’t have to figure out how to get back at midnight via cab or bus.

A Brief Night’s Disruption

I wake up from the sensation of a snake coiling itself around my right wrist. It slowly circles once, then twice, and begins to constrict. I panic and reach out with my left arm to grab it, but find my arm restrained. I can feel something wrapped around my wrist, and whatever it is, it is firmly anchored to what I can only assume is the bedpost.

In my moment of confusion, my right wrist is yanked, hard, and bound. Now both my arms are restrained.

From in the dark, at the foot of the bed, I can hear something shifting. There is the light snapping sound of elastic hitting skin. The bedsheet is slowly pulled from my body, exposing my chest, my abdomen, my groin.

Something begins to crawl onto the bed and up my legs and settles just above my penis. Heavy breathes blow hot air on me, causing me to quickly engorge.

First there is a light flick, a quick darting of something wet and warm against the tip. Then I am engulfed, hot saliva against my fully erect penis sending shivers along my body, heating me.

First [t]i[m]e with a ladyboy…

So a little background… I’ve had some fantasized of hooking up with couples and participating for several years now. I had started to think it would be hot to participate with both, sucking a cock with fresh kissy juice dripping off and seeing what it would feel like to take a dick in my mouth.

Sad to say this hasn’t happened and I never thought I would find myself one on one with a cock until I visited Thailand. Those girls had me so intrigued with the beauty paired with a nice cock and I saw my fantasies widening to include some of these beautiful trannies you find in Asia.. I live in SE asia and travelled to Bangkok several times and my curiosity grew.

Fast forward to last week and I was on my way through Tokyo and had some free time and scrolled through local wechat and found a good looking girl with a very nice cock and we exchanged messages. I was hesitant and told her as much since it was my first time and she told me she would be gentle and was reassuring.