[m][bi][inc] How I became a sissy

It all started when I was in school, I was a skinny, quiet boy still waiting for puberty to hit. I had just discovered masturbation when I would take a day off school to watch porn and play with myself until my parents came home. At first I was normal enough, playing Hentai games and watching videos and climaxing over and over and over until one day I saw a pair of my Mothers panties on the landing out for the wash. I only noticed them because the night before she had been fucked by my Dad, I know this because I was listening in and playing with myself. I kept the panties. I would rub them on my cock and sniff the creamy spot and it would send me into a frenzy until one day I decided that I would try them on, The feeling of my mums panties against my cock was like nothing id felt before, I went week and just lost myself. on my knees in my room leaning back and stroking my cock until I came all over myself. At that moment I think was when I became Melissa. I would wear them to school with the lace pulled up into my ass and my skin pulled back so every movement could be felt. Fast forward to when I was older, I had already started photographing myself and playing with older men on Omegle and just being a lewd teenage sissy when I decided I would complete the image. I would play in my mothers panties often so why not her bras and heels as well? I was truly a sissy and it only got worse from there. When I was 18 I started roaming the streets at night looking for trash bags that people would throw out with clothes in, the ones with Lingerie and underwear in I would take and the rest I would leave. I found skips and lingerie sets most of which you can see in my albums on imgur. It wasn’t until I turned 20 that I started posting them places. I got my first job and with my first pay check I bought a wig and some anal trainers which turned out to be way to big for my tight little hole but they were fun none the less. Every day I become Melissa more and more and I just need to serve someone, A sissy, another woman, anyone I have so much exploration to do and I hope I can find someone to finish the transformation which started all those years ago.

[M]y [F]irst Experience with a Married Woman (long)

When I went to orientation for my first year of teaching, I met Lisa, a fellow English teacher who taught strictly seniors courses, whereas I taught mostly behavior disorder and learning disordered junior and senior high students. We became fast friends due to the fact we both had the exact same taste in music. We would talk about all of the concerts we had been to the past summer, and turns out we went to a lot of the same festivals, just at different locations. Since she had just relocated from Michigan, her husband still hadn’t found a teaching job in our area, so they were living about 8 hours apart.

At first, I was oblivious to her intentions with me, since in my mind, she was married and there was about a 10 year age difference between us. We went to 6 concerts together the entire school year, and each time I’d drop her off home, it’d be extremely late, but she’d still invite me inside of a night cap. I declined each time, mostly due to the fact that I was usually feeling pretty tired after the shows and would have to work my second job on the weekends. It wasn’t until I went to my friend’s band’s concert that I realized she was interested in more than friendship.

My Discipline – Part 2 [M/f] [Spanking] [Humiliation]

I masturbated many times to the thought of my spanking and to other girls getting spanked in porn. As the bruises from my spanking faded, so did the sharp memories of every sensation and detail about my first spanking. The hormones in my 15 year old brain began to take over and I was craving another spanking. It had been three weeks since I first felt my dad’s belt across my ass, and despite me recent good behaviour I felt compelled to break the rules and get punished again.

That Friday night I went to the high school football game. It finished in plenty of time for me to make it home before curfew. When I started my walk home however, I went right instead of left. It was the long way home. After about 15 minutes into walking the long way I was past the point of no return. Even if I turned back and took the short way, I’d still be late. I did this so I wouldn’t chicken out. Despite how horny it made me to reminisce about my spanking, it still hurt like hell. I had been noticeably sore for several days after. So my rational self wanted to avoid the pain, but by hormones and arousal overrode my rational self because of how intense my post-spanking orgasm had been. I felt like a junkie seeking a fix.

Milk [Mf] [incest] [daddy-daughter] [cum] [lactation] [weirdest thing I have ever written]

“Oh, honey, did I tell you that Emily got her tests back?”

Brent flipped a flapjack in the pan as his wife, Lisa, spoke to him. As he cooked up Saturday morning pancakes, Lisa and their daughter Emily sat at the table, eating them as they came off the heat.

“No, you didn’t. They’re good, I hope.” He replied.

Lisa looked to her daughter, who had her head down as she quietly ate. “Do you want to tell him, sweetie?”

It took Emily a moment before she looked up. “Oh, um, yeah. The doctor said my swelling has gone down a bit.” Her delivery wasn’t exactly enthusiastic.

“He was so surprised, Brent. And to think, he wanted to put you on all kinds of pills or recommend you for some kind of surgery. It’s a good thing that girl at the health food store just recommended a diet change. Much cheaper and much healthier.” Lisa gestured toward her daughter with her fork.

My Discipline – Part 1 [M/f] [Spanking] [Humiliation]

This is a fictional story about teen girl, and never actually happened.

My name is Heather and I have a very interesting story to tell you. You see, from the outside I seem like a very normal and typical 15 year old girl. I go to school, I am on the junior varsity volleyball team, and I get decent grades. All my teachers, neighbors, and acquaintances think I’m a model young lady. Most of the time I am, well except at home.

I am forgetful about my chores, I am terrible getting home by curfew, I give me parents sass, and fight with my younger brother Timmy more often than not. According to my parents my behavior issues didn’t really start until I was 13. They attributed the change to teenaged hormones. They were probably right. The year I turned 13 I spent an average of three weeks out of four being grounded. I had no phone, no tv, no computer. Even with as strict as it was, it didn’t really compel me to do my chores or be nicer to my brother. Since I couldn’t leave the house though, at least I wasn’t late for curfew.

A night to remember Part 3 [MMFFF]

Part 2:

A night to remember Part 2 [MMFFF] from eroticliterature

I sat beside Alex and watched as Lisa slid her hands around Tricia’s back, to rub her hands over her belly. Julia stood in front of her, her hands rubbing her neck, shoulders, and breasts. Water sluiced over all three of them, the dual shower heads in the standing shower of our bathroom spraying warm water over them. Tricia had her head tilted back, her lips parted slightly in pleasure, as the two women rubbed their hands over her body. I’d pulled the standing doors off the shower to open it up, and water pelted out, but we’d covered the toilet and floor in towels to absorb the water. Tricia moaned lightly as Lisa’s hands found their way between her legs, rubbing back and forth across her thighs, and slowly began to move down as she crouched. Julia’s hands continued to wander her upper body, her motions smooth and delicate, barely touching, roaming her hands down Tricia’s arms, then back up to her chest and neck.

A night to remember [MMFFF]

I’ve been writing stories like these for a while now, at least a few years. I’d only ever sent them to my wife, kind of a way to help with foreplay and get her motor running, but this was the exception. While TDY for a few months back in 2013, I wrote this over the span of a night. It’s turned into one of my wife’s favorites, and I’ve shared it with a few close friends since. While certain aspects of this story comes from past experiences my wife and I have had with a few friends, the story itself is original. All the names have been changed. Let me know what you think!

Sometimes you dream of a fantasy, and wake excited, the thoughts, images, and sometimes feelings transitioning between dream and reality. Sometimes it feels so real, you wake hard, or wet, wanting nothing more than for someone to relieve the pressure building between your legs. Sometimes these fantasies are things you have done, or things you’ve imagined doing. Maybe you’ve seen it in a film, or read it in a book, maybe seen it in a porno. For most, fantasies that you dream of will rarely come true, unless you actively pursue them, set things up to work out the dream. Sometimes things just naturally work out, and something you never expected to happen falls into your lap, and you just go with the flow. For a rare few, they have friends or a significant other that are open to helping them fulfil fantasy, to make a dream a reality.

[MM] Midwest business trip

So I last week I went to a midwestern US city for work. I was on my own and had my own hotel room for a few nights. So before I left I put up a craigslist ad saying I was looking to suck cock and bottom in my hotel room and if interested to please send a body shot. I’m 25 btw, tall, fairly good looking. So I get a reply from an older guy which is a huge plus. He sends a pic and he is in great shape for a guy in his 50s. Flaccid cock in the pic but he said it was 8.5 in so I figured he was a grower like me. So we swapped some emails and pics and I told him I’d email him when I checked in. So I check in around 4pm and send him a note. He leaves work early. I’m wearing pale green lacy panties and edging to sissy hypno porn when he knocks on my door. I am blown away at how good looking this guy is. Tanned, great shape and wearing his wedding ring. We shake hands and I start tugging at his belt. He drops his pants and I go to work. Sucking and slurping his soft cock. After about a minute he tells me to stand up and we both strip and hop in bed. He lays back and I start sucking again. I come up for air and we look at each other. Now I don’t kiss dudes, never have. Really not even attracted to guys as much as I am cock. But damn if he didn’t make me want to kiss him. And I did. Next thing you know we are wrapped up passionately tounge kissing. I’m panting with pleasure like a bitch and feverishly flushed. I’m calling him Daddy and he’s calling me Nickie and Bitch. He’s on top kissing me now and he sits back with my ass on his lap. He starts letting strings on spit drop down into my ass. That’s when I notice how hard and big he’s gotten. It stuck straight out with a crook at the base. I’d only fucked 2 cocks bigger. I ripped open a condom and he rolled it on and pressed his thick head against the rim on my asshole. He shoved the head in. I’m gasping and just groaning with pleasure. Now the whole cock slides in. Jesus fucking Christ, he was thick. I wrapped my legs around him and threw my arms around his neck. He started thrusting. I was completely filled. He fucked me like that for a good 4 minutes. Then he threw my legs to the side putting me in the fetal position all while banging aways. I twisted around and propped myself up a little so we could french some more. Then he shoved his thumb in my mouth and ordered me to suck which I gladly did. After a bit I pushed him off and got on all fours. He entered me that way but quickly pushed me down into a prone bone. At this point I was shouting. I hoped somone in the other room would hear. I just felt like such a whore and I loved it. You could tell he loved it. I was arching my back and pushing into his thrusts. That was too much for him. He grabbed my ass cheeks and with a roar gave 3 big pumps and flopped over. Holy fuck that was hot. We were both sweaty and tired. He left for the bathroom and came back sans condom. I should have asked he make me eat his cum out of it or dump it on my but I was in such a dizzy fog I just lay there till he came back. He let me kiss and suck his giant cock head free of cum. Then we kissed some more and made small talk while he got dressed. Just a super chill good looking dude. Which trust me, is kind of rare to find with Craigslist. So yeah, that’s my story. I masturbated 3 times after he left and came buckets each time. We plan on doing it again next time I’m up there.

MySexualConfessions[F] – my real sex scenes.

I decided I will group my confessions from now on just to keep track on them.

[[ For who doesn’t know, I made an account yesterday just to write down all my real and untold sexual experiences. I’ve been through a lot of kinky/messy/embarassing/sexy moments and I could never share them with anyone. I decided to better write them down in here and share them with strangers because I will never talk about it in real life.

Stories will not necessarily be related to each other. They can be different sex miments from different times. Each partner that I had will be named – I will be using initials for their names if necessary. Nothing is fake, they are all my real stories – otherwise I wouldn’t waste time to type imaginary things-the internet is full of fake stories. Thank you for reading this. ]]

Note: I am writing now from my phone so mistakes be forgiven.

Note 2: I will identify myself as A, my ex as J. Other people will be named through the story if necessary.

Unintended sexual escalation [MF]

So a few weeks ago, I [wrote about my wife and I turning a routine visit from a friend into our first threesome.](https://www.reddit.com/r/gonewildstories/comments/6rnpfu/and_the_guest_makes_three_mff/?utm_content=title&utm_medium=user&utm_source=reddit&utm_name=frontpage) I had a few people PM me for a few more details and encouraged me to tell a few stories from my single college days.

I thought back on if I actually had any worthwhile stories to tell, and a couple came to mind. I suppose I’ll write them and let the upvotes/downvotes do the telling.

My freshman year of college, I made one of my best friends of my life. Samantha and I hit it off from the start. I admit I had an outstanding crush on her initially, but her having the whole “boyfriend from back home” really friendzoned me quick. Which I reluctantly accepted.

We remained friends and did tons together; partying, studying, concerts, etc. She became a great friend of my entire friend group, or I guess it really turned into our friend group by our junior year. We had an apartment just off of campus, and she lived in one on the other side of town. Often she’d crash on our couch after long nights or if she had an early class. She really just morphed into the fourth roommate.