The Making of a Sex Story for this sub.. Need help (Hope this is allowed)

A group of our friends made a poker bet (both male and female) where the winner would get to choose what the loser has to do and post it to this sub. A woman won and a man lost. She is making the loser dress in full drag, and walk down a low traffic path in the woods asking passer by's (mostly men) if they would like to play a game.

The game consists of the "participant" picking a random sealed envelope. They open it up and whatever is on the card inside, the "crossdresser" will have to do. And then take a pic/video of the act and post it in the main thread (which I will make) once he/she is out in the woods this weekend.

We need ideas for the cards. And also the crossdresser will be in an extremely slutty outfit. We did a test run of what she will look like and may post the pic if this blows up enough. He/she actually is quite passable….

Here are some we have come up with so far, just about nothing is off limits. The more embarrassing the better. The participant reads the cards to the CD.

[m]y first time meeting a girl with an oral [f]ixation

Meeting Ally was completely unexpected. It was a few years ago, and I was new at my current place of employment. My staff team was asked to give a tour of our facility, and Ally was one of the many people who came through. I was caught off guard to hear her ask me if I was [insert my name here]. She was extremely friendly and smiled the whole time. She explained that she knew a good friend of mine, who had mentioned me a few times, and she recognized me based on his description of me. She was really smiley, told me that my friend had said great things about me, and gave me a hug, saying that we'd have to get together and meet properly sometime. I agreed and she went to continue the tour.

Ally was short and bubbly with dirty blonde hair. She's a good 5 years older than I am. She is also one of the more extroverted people I've known, and is always happy to meet new people. I didn't get even the slightest hint of a sexual vibe from her – not in a bad way, she just didn't broadcast in that direction. Physically, she was tiny. She had enough flesh to let you know she was attractive and female, but was definitely on the lean side. Her skin was thoroughly tan from spending a lot of time outdoors, and she was almost always smiling or laughing about something.

The Slut Chronicles-The Threesome (FMM)

If you haven't read my other story, a little back story. My name is Olivia and I'm in my mid-20's with long darkish hair, green eyes, pale, big ass and C cup boobs. I met Shane at my first job out of college and we still work together in an office. He's tall with blonde hair, brown eyes, and a great smile (and a perfect dick.) We always used to talk about what turned us on, bukkake, gang bangs, rough sex, messy blow jobs, the works. Shane started texting me asking how much I would enjoy being cum on by two guys. It turned me on so much. I wanted to make this happen. I wanted to be a good little slut and sit on my knees as two guys jerk off into orgasm all over my begging face. I was determined. I had a fuck-buddy that I knew I could trust. I had a friend named Rob. Rob and I had been friends for years and just recently became blow job buddies. He is tan with dark curly hair and the build of a body guard. He would come over often and I would give him sloppy blow jobs and he would tell me what a good slut I was. It was the perfect relationship. I told Shane that I thought Rob might be interested in fulfilling our fantasy of having a BJ three-some. We arranged the date and the day came I was so excited. The thought of sitting on my knees while 2 guys jerk off onto my face left me unable to focus on anything else. I got home and immediately changed into lacy panties and a matching bra. I waited by the window wondering who would get there first. Shane pulled up and came inside. He took of my bra and panties and started to pull my nipples and used them to force me on my knees. I stared up at his cock as he took off his belt and took out his cock. I slowly took his hard cock into my mouth pushing it between my lips as I took more and more of his cock into my mouth I pinched my own nipples. Suddenly he stopped me and made me stare at his perfect cock. He took the back of my head and forced his cock down my throat as I pinched my own nipples harder. Then he knelt down behind me spreading my legs apart revealing my wet pussy. He fingered my clit hard as he put his hand over my mouth to muffle my moans. He pushed his finger into my pussy as he continued to rub my clit and I fell into his arms shaking with my first orgasm. He stood up and grabbed his belt, he put it around my neck and pulled it tight as his cock forced its way into my mouth. I deep throated his throbbing cock as he used the belt to guide my head. He kept pushing his cock harder into my throat as he pulled the belt tighter. My pussy was so wet. He let go of the belt and took it off from around my neck and walked over to the couch. Shane sat on the couch as I knelt in front of him. He wouldn't let me suck his cock just stare at it. He held it and hit my cheeks with his cock as I opened my mouth and moaned. I started to tease his head with my tongue. Circling around his head as I looked up at him and took his entire cock into his mouth. We heard the door open and Rob came up. "Look at this good little slut" Shane said as Rob took of his shoes and pants. Then Rob came up behind me as I was sucking Shane's cock. "What a good slut you're being," Rob said as he pushed a finger into my pussy. I moaned with Shane's cock in my mouth as I fucked him with my mouth. Rob pushed another finger into my dripping wet cunt and fucked me hard. I kept sucking Shane's cock as I moaned harder and suddenly felt an orgasm wash over my body. Rob took his fingers out of my pussy and made me suck them clean. Tasting my own cum turns me on so much, I moaned as he swirled his fingers around my mouth. They both stood up in front of me, their cocks hard. The stroked their cocks gently as I scooted over to Rob and started to lick his cock. I licked from his balls to his head then circled my tongue around his head looking up at him then looking over at Shane who was stroking his cock staring at me. I put more and more of Rob's cock into my mouth as I reached over for Shane's. I started to jerk Shane off and fuck Rob's hard cock with my mouth. I then went back over to Shane and started to fuck his cock with my mouth now stroking Rob's cock softly. Shane took his cock out of my mouth and hit my face with it, I heard Rob moan. I then went over to Rob and he hit my wet face with his cock. I kept alternating blow jobs and hand jobs as my pussy got wetter and wetter. Shane took my hair and shoved my face onto Rob's cock as he slapped my nipples. He kept slapping my erect nipples as he stroked his cock with the other hand. I sucked on Rob's head taking more of his cock into my mouth continuing to use my tongue to stroke his cock inside my mouth. Shane took my head then shoved his cock into my mouth grabbing a handful of my hair and fucking my mouth with his cock. I stayed still with my mouth wide open as he pulled my hair and kept using me as his fuck toy. I could hear him moaning and getting closer then he took his cock out of my mouth and as I looked up at him stroked his cock until ropes of hot cum came out of his cock and onto my face. As he came onto my face Rob pulled me by my hair over to him and came all over my face, moaning loud as his cum covered the areas that Shane's couldn't. I moaned as I laid down on the ground, loving the feeling of cum of two men all over my face. A few minutes after Shane left, Rob stayed. I started to get ready to leave the house and Rob threw me on the bed on my stomach and ripped off my pants. He then shoved his cock into my pussy hard and fucked me until his cum filled my pussy. He then told me to put on my pants and we both left. We all want to do it again, but with more guys next time.

Fucked a teen Slut and i eventually fucked her mom, but first the daughter!

A little background first, this story happened 10 years ago, I was 20. I was living in this shit hole of a shared house, in a not great area of my home town , I was in great shape through my job as an Electrician and hitting the gym regular, I was making good money so was out every weekend just generally getting into trouble which is how this story came to be.

It's the middle of the summer late at night an I'm on my way home from a friends place, we been drinking and smoking a bunch of weed so I'm pretty buzzed , as I round the corner to my place there's a girl leaning against the wall trying to light a cig. Now this girl is not my type at all, she is what I'd call a skally, wearing jogging bottoms hair tied back tight an too much gold jewellery, a pretty common sight around here. But my god the tits on this girl were amazing some of the biggest and perkiest I have ever seen an they were just bursting out of her crop top. I offer a light and introduce myself, her name is Jenny and she's been doing the same as me tonight a few beers an some smoke so we're on the same level. We chat about general shit, our night our an whatever, I can't keep my eyes off her an I catch her doing the same. Jen was just 18 an had an amazing body she is quite short maybe 5,6 to my 6,2. Tidy body with a peach of an ass. Long brown hair cute face an as I said beautiful boobs.

Tinder scare

Ok so i should preface this that it was my first time using Tinder and for along time it was gonna be my last since it lead to the worse sexual situation of my life.

I decided to download it and see what the hype was and within 24 hours i get matched with a good amount of people one was a 34 year old women that looked pretty hot in a black and white photo who was immediately keen to meet and arranged to meet at her place 3 days later which i was dumb and 19 years old so i did without anymore pics being sent. On my way there on the train she leaves me some texts telling me if i want coffee i'll need to buy some milk and bring it to her place and not to be surprised by the lack of furniture, I responded with a bad joke because i was kinda confused with 'Lol it's fine as long as there's a bed' which got no response. I had my phone on silent and realized i got a voicemail from her as i was walking to her place which was just saying 'how far away are you' but the voice was a lot different from what i pictured.

Bastille Day, 2011 [MM/F]

She stood, legs apart, arms extended to support her weight against the sink in the bathroom. The stranger who stood behind her had his cock inside her cunt. The stranger who stood at her side snaked his hand between her legs to touch her clitoris. Loud moans escaped her lips. She tilted her ass fractionally up and wriggled backward. She squeezed her pussy about the shaft, consciously at first, then reveled in the sensation as it contracted involuntarily in orgasm.

She was wet inside: gushing, in fact. The fact of her coming made the anonymous cock that was fucking her climax as well. The semen shot into the condom. She clutched the porcelain. Her knuckles whitened.

After he had released, she extricated herself from the softening penis and went to her knees and sucked the next man's offering. Her throat loosened. Cords of spit dripped from the wide shaft. Extracting a condom from the box on the ground, she covered him.

He chose to stretch out on the dirty floor. His hand held the erection upright for her to mount. She lowered over the prick and bounced herself on top of him. Her hand reached behind to finger his balls.

my[m21] roommate[f22] who liked eating cum

I don't have a long story like the ones recently on the front page of /r/gonewildstories. But whatevs. Here it goes.
Just after college, I got a job in Chicago. Des Plaines was the closest place I could afford even with three other roommates. It was me, a dude named Kevin, and two girls Lanie and Chris. Everybody thought Lanie and Chris were a lesbian couple. They weren't butch or anything. They were both actually pretty cute. They just always hung out with each other and never had guys around. They weren't lesbians though. Chris was dating some dude who went to Truman, and Lanie liked to fuck me.
One night after Chris and Kevin had gone to sleep, I was rooting around in the fridge for a beer. Lanie walked in wearing just a t-shirt that only came down far enough to hide half her ass. She asked me to pass her a beer, sat down on the couch across from me, chris cross applesauce so I could see right up her crotch, and asked if I wanted to fuck. I said yes. We went at it for about 15 minutes or so, but after she came she pushed me off of her and said "I don't want to get pregnant. Let me get you off with a handjob." Then she jacked me off until I shot my come into her other hand. Then instead of wiping it on a towel or something she licked her hand clean. That was a little weird for a first date, but who was I to complain, right?
After that, it was a regular thing. About two or three times a week, Lanie would just ask if I wanted to fuck and then drag me into her room or mine. It didn't matter if there were people around either. She'd do PIV and even anal if I asked for it, but she didn't want me to come inside of her even though I always had a condom on after that first night. And she absolutely refused to suck my cock. Wouldn't even let it get near her lips. She swallowed every drop of come, though. She usually brought me off into her cupped hand, but now and then she'd make me jizz into a shot glass and swallow it. Or if we were having a party, she'd get me to come into a wine glass before the people arrived. Then later on she would pour wine into it and tease me by sipping it while everyone was around us. Facials, jacking me off so I shot directly into her mouth, jizzing on food and making her eat it. Anything and everything was cool as long as I didn't come inside her pussy or ass or get my cock anywhere near her lips. No sleepovers or cuddles, either. I never asked why. I just assumed she had a good reason and didn't want to make her bring up whatever fucked-up shit caused her to feel that way.
I lived there for two years and then moved away to take a job in Minneapolis. When I told Lanie, she almost looked as though she might start crying. But then she shrugged and said "that's cool" and asked if I wanted to fuck. We screwed, she jacked me off onto her tits, and then I watched her scrape my come off and eat it bit by bit. We fucked and she swallowed every night for the next two weeks until I moved out. And that is the story of my ex-roommate Lanie who never gave a blowjob but finished the job as good as any porn starlette could have.

a cute girl [f]rom college and a cabin bathroo[m] blowjob

I was in my first year of undergrad when I met the crowd that Sara hung out with. They knew how to have a good time without getting stupid and trashing the entire neighborhood, so I was always up for a night with them. The guys were a laugh riot and the girls were great-looking–add booze and some lax RAs to the mix and we had a recipe for a lot of dorm fun.

My eyes were initially drawn to Jay–she was 5'8" with dark brown hair, a pretty face, and some amazing hips. What really had me distracted, though, were her breasts. She never wore anything revealing, but her chest was too big to hide, and the shape…needless to say, I was a bit preoccupied. So much so that I failed to notice Sara properly the first few times we hung out.

Sara was an adorable short brunette with gorgeous pale skin. Her breasts weren't huge–B cups–but they had a great shape to them and her perfect skin only made them better. She tended to wear fairly revealing tops, and I snuck a few glances when I thought she wasn't looking.

[m]y grad school [f]wb again, and the first time I had my cum swallowed

Chelsea and I remained good friends after our fling. We hung out regularly for the next year, up to and after graduation. That summer, she had decided that she would be moving back to her home (several states away). I was really sad to see her go, as we had become very close friends. She had at least one brief fling with a neighbor guy from her apartment complex, and I was really happy for her, but he seemed to lose interest after a time. One of the last times we hung out before she moved, we were both unattached again, and had enjoyed raucous laughter with several beers, wine glasses, and some great movies in the living room of her apartment. It was around 1am, her roommates were gone, and we were winding down. We joked playfully about demanding sexual payment for various favors owed to us by friends (we routinely made dirty jokes). The beer in my system reminded me that she had made remarks long ago about the fact that she enjoyed giving head, although she knew she wasn't very good. I was exceptionally horny, having gone without for a few months. I also still found her very alluring, and my physical desire for her had grown strong again after over a year without fucking her. I had also spent the entire evening checking her out, and particularly enjoyed her ass in her jeans as she would go to the kitchen to get another drink. As we sat on the couch, I figured I’d take a shot at some fun. Being the brazen jackass that I am, I locked eyes with her and said, "I'm seriously craving head. Will you give me a blowjob?" She immediately chuckled, and gave me a playful smile. "Sure."