Massive Ass Play with a Friend [MF]

Shortly after graduating college, I moved to a new town where I didn’t have many friends close by. This led to me cruising facebook a lot to find old acquaintances that lived in or near my town. During this time I reconnected with an old high school friend named Amanda. She had always had a crush on me, and I always thought she was cute, but we never dated. She was still adorable. She was 5’6” 140 lbs with curly brown hair and lots of freckles (which I love). She was not well-endowed up top with just A cup tits, but her booty was wide and plump… just the way I like them.

Now for the bad news… she lived 4 hours from where I was currently living. Bummer. But that didn’t stop us from messaging constantly on facebook. At first our messages were innocent and rehashing old memories. Then I got flirtatious by teasing her about her crush on me and saying how it was too bad we didn’t live closer. She shot back that I wouldn’t be able to handle her as she had gotten a bit more wild since high school. This piqued my interest. Just how wild?

Post trip fuck, part 2 (M/F, encouragement, detailed, Anal creampie)

You’re sultry words of all of the things you desire and enjoy fill my ear as you whisper your fantasies. My cock has lost a bit of its rigidity since cumming inside of you, leaving enough room for our combined mixture of pleasures to leak out of you around me.

“Don’t let your dick get soft now baby, that was just rubbing the easy one out.” You flick my ear with your tongue. “I wanna feel that long, thick, cock stretching my tight little pussy some more.” You can feel your encouragement working inside of you as I stiffen to fill you. “That’s it,” you breathe heavily into my neck. “I’m your little fuck toy. Use me, abuse me, fuck me…” you’re last words trail off as you start to suck on my neck.

Fully revived and hard as a rock, I start to pound you again, using my own cum as lube to ease your insane grip on me enough to not tear you open. I see you leaning forward enough to watch yourself getting stuffed and your pussy lips being pulled out with my strokes outward. You feel the drag on the walls of your snatch as you grip me, my now shorter and faster strokes only shallowly inside of you but sending explosions of sensation through you as I brush your G spot.

[MF][FM] Being an old man’s college-girl fucktoy

“I should probably go grab my laundry,” he said, which was her cue to get dressed. He threw on a pair of Vans and washed out Levis that were perfectly fitting for his grown-up-angsty-boy persona. She stood at the door, dressed, with her purse on her shoulder, awaiting a romantic salutation. “Come ‘ere” he said, holding out both of his arms to embrace her. “Are you fucking kidding me, another hug?” she thought to herself, disappointed. Wanting to maintain her status as the “chill-younger-girl-he-likes-to-fuck,” she went along, showing no sign of disappointment. “See you soon!” “See ya.” he barked. She walked toward the elevator after leaving his one-bedroom apartment downtown. “What the fuck was I thinking? ‘See you soon?’ What kind of clingy weirdo am I?!?.” She left the building and approached the sidewalk outside as she had many times before. The walk home often occupied her mind with racing thoughts. The first time, she wondered why she hadn’t asked for his name. She only knew him by his Fetlife handle, brattamer_1981_. His name was an afterthought compared the feeling of his hot breath against her neck as he learned the landscape of her body from behind for the first time. She had practically forgotten that he had a name by the time her forehead was cradled into his shoulder as they recovered from their first romantic romp. Not used to having men cuddle her after sex, she suspected that he might want more. Afterall, he had kissed her during sex and cuddled her in his bed after. “Maybe he actually likes me?” she questioned. The second time, she asked what he went by. “Mickey, and you?” “Ana. Just Ana. Only one syllable, doesn’t really warrant a nickname.” God, that sounded nerdy. “Why am I like, this?” she thought. That night he told her that she was beautiful, and though she suspected that he might have just said it because he was getting off, she couldn’t help but feel that it had more meaning. No man had ever told her that she was beautiful during sex, as all of her prior experience had been casual. Not knowing if he was just different or this meant something, she remained hopeful. A seed had been planted, and she was wet enough to grow it into a complicated, confused flower. The third time…oh, that third time. He texted her late, and she happened to be out, downtown. “U free tonight?” “Yeah, but not for another half an hour.” “Fine. You down to eat my ass?” “Of course. See you around 11?” She spread herself wide open to let the insects in She leaves a trail of honey to show me where she’s been She has the blood of reptile just underneath her skin Seeds from a thousand others drip down from within That night he was playing Nine Inch Nails like the man child that he was. But she loved it. It made her feel mature and dirty, just like him. “Say ‘thank you, daddy,’ you fucking slut ” “Thannnnkkkkk you, daaaddyyyy” she cried. Oh, my beautiful liar Oh, my precious whore My disease, my infection I am so impure This third time she wanted to nestle into his chest post-sex and ask him whether he preferred Kirk to Picard, how he got the scar below his left temple, when he got the bike in his hallway, and whether he wanted to go for a ride the following weekend. Instead, she wiped the cum off her chest and asked him if he typically dated younger woman. “I mean, my girlfriend is 24, so yeah.” The internal rolodex of prospective questions within her came to abrupt stop. What did he mean he had a girlfriend? She knew this was casual, but she didn’t know he was that unavailable. Just after midnight, he lifted his arm up from around her shoulder and walked his naked body over to the spot on the floor where he had dropped his clothes. He began to dress, and she knew this was her cue. “You gonna grab an Uber?!” “Nah, I’ll just walk.” “Good for you!” She had hoped that he would offer to buy her an Uber home and not praise her like an alcoholic stepdad, but her ideal expectations were long gone at this point. “Thanks, take care,” she replied, trying not to show the disgust and disappointment that was bleeding from within. “This is okay, I’m still getting what I want” she told herself over and over again on the third evening walk home. She knew from his FetLife bio that he was seeking “casual play partners” But part of her wondered if the possibility for more existed. Maybe after fucking her he’d want more. Maybe a post-sex conversation about The Police and Talking Heads would turn into something more meaningful. Maybe he’d tell her a story that turned into two, or seven, and she’d have no choice but to fall asleep on his chest and wake up on his cock. Maybe she’d have the courage to kiss him. But now, that possibility seemed like a pipe-dream. Despite this, she wasn’t ready to give up. After all, she was getting fucked by an experienced, dominant, older man. That itself was milk and honey. Who was she to ask for a cream? The fourth time she wanted to present herself differently. She wanted to be seen differently. If she was to be taken seriously as a potential romantic partner, she’d have to act like it. She put on the only push-up bra she owned with a tight-fitting turtleneck that showed her young feminine figure. A bonafide tomboy often mistaken for a butch lesbian, she applied eye makeup with the confidence of a drag queen and the skill of seventh grade girl trying to fit in. She wore her hair down for the first time in years and applied her 7-year-old perfume from her first communion to the back of her neck and cleavage. “Fake it till you make it” she repeated after crudely applying dried-out red liquid lipstick before turning off the bathroom light. She walked up the three-step staircase after getting buzzed in. The odor of the building was evident with the slightest crack of the entry door and was overwhelming. The smell of marijuana, mildew, and hurried, likely-paid-for sex penetrated the Section 8 building from the lobby all the way up to the 13th floor, where she frequented her unrequited lover. She stepped in the elevator and looked at her phone. “Still in shower, doors unlocked.” “Come in and get naked and start rubbing urself” She walked to the end of the hall and entered as she always had. With the sound of the shower water running in the background, she started to undress. She was irritated that the presentation she had worked so hard on would now go to waste. Ugh. The plan was foiled. Why couldn’t he have just been ready and undressed her once she arrived? He wasn’t going to get to see how hard she had worked just to look good for him, or how well her supple breasts cradled the lace-lined push-up bra. As she folded her button-fly jeans and turtleneck from off her young body, she noticed a rose-colored Post-It Note adorned with a message. “Thanks for letting me spend the night baby. Luv u <3 -Ami” Ami must have been his girlfriend. Ugh, why did she have to read that. It’s not like it changed anything, at least she didn’t think so. Her overly-analytical mind started to spin. “If I knew he had a girlfriend before, seeing her note and therefore confirming her existence and relation to him means nothing. I’m here, and he’s going to fuck ME. There’s nothing wrong with that. I’m okay with that.” She spent these moments alone with herself consumed with both thirst and anguish. She began touching herself on his couch, hoping that if she could get turned on, she could get out of her head for the few minutes it would take her to cum. On top of the end table between the couch and bed laid a Trojan Ultra Thin condom, lube, and a rose quartz butt plug. Fuck. What did this sadistic son-of-a-bitch have in mind? The sound of the water stopped abruptly. “There’s my little fucktoy.” Here we go again. “Get on your knees.” She leisurely took her fingers out of herself and began to dismount. “GET ON YOUR FUCKING KNEES.” She dropped immediately and took him in. She looked up at him, hoping for approval and maybe, just maybe, some praise. “Goooood girrrrl.” Yes. She was pleasing him. Maybe he’d want to get used to this. “Look at that pretty eye makeup. I LIKE that.” “He noticed that I tried!” she thought. “It looks really good, but I also want to make you cry it off.” Before she could soak in the compliment, he grabbed a handful of her overly-processed bottle blonde hair and forced her onto him, as she tried to sneak a breath in the midst of gagging on his cock and her saliva. Fucking him was simultaneously the best and worst thing that could happen to her. She was jerked around, called miserable names, and asked to do things for which she had little interest. But it was the only time that she felt at peace within herself, and the anxiety that typically consumed her would vanish. Do you know how far this has gone? Just how damaged have I become? When I think I can overcome It runs even deeper She loved everything about the way he fucked. The way he felt inside of her. The way he slandered her ruthlessly, but carressed her face sweetly. The way her face stung after well-deserved discipline had been administered. The way his salty warm cum mixed with seas of her spit to fill her mouth and leak out of the corners onto her erect, pierced nipples. She didn’t feel anything except the pain and shame. It was welcomed compared to the typical anxiety and depression that typically plagued her. And in a dream I’m a different me With a perfect you We fit perfectly And for once in my life I feel complete “Ahhhhhhh. That was fun. Fuck. I didn’t you know you were such an anal slut.” “In more ways than one,” she quipped, partially hoping he’d laugh at the double entendre. “You gonna catch an Uber?” “No, I think I’ll just walk. “Good for you, Hannah. Have a good rest of your night.”

[F]irst time anal with [M]y crush with his friends over (Third Story :)

A quick link to the first story:

[F]ucking [M]y high school crush at our reunion from gonewildstories

And the second :

[F]ucking [M]y crush in a movie theater for our first date [Public] (Second Story) from gonewildstories

Real quick, I wanna thank all of you so much for reading and commenting, it means a lot to see so many people intereted in my wild sex life :). I love you guys asking questions and rooting for me, it’s really sweet :) so lets jump into it!

After our little date and Porter telling me he jerked off thinking about fucking my ass, I knew my night was going to get wild. So I decided to prepare a little bit, because even though I’ve always thought anal was hot and sexy, I’d never actually done it before. Thankfully, I live in the wonderful city of Portland and went to a 24 hour sex shop to buy a butt plug, oil, condoms, and pester the two sweet men at the counter about tips and tricks for first timers. After getting the supplies and thanking the kind gentlemen, I headed home to get some sleep before work. As soon as I woke up, I lubed up the butt plug, and start to tease my asshole. Little by little, my asshole began to stretch and take the full girth and length of the plug before pushing it all the way in to leave for the day. I got dressed in what I planned to go to Porter’s in; tight Zelda themed yoga pants, pink lace bra, and the lucky Carolina Panthers shirt.

The Business Professional’s repeat exhibition performance [MF] Long

This takes place directly after my previous story [[part 2](https://www.reddit.com/r/gonewildstories/comments/bmxbe4/mf_business_professional_has_a_breathtaking_view/)]. However, it’s written so that the previous stories are not a required read. This is version 2 of this post because I wasn’t happy with my original writing. I skipped over some parts, taking certain liberties here and there with indulgences. But, the dialogue and events are as true as I can recall. Yes, even the end.

***

Katie was texting me throughout the morning on how amazingly awesome last night was. She was playfully begging me to play hooky from work.  No, not distracting at all. But I got through the day by some miracle without getting fired for pitching an 8-hour trouser tent. 

I made a pit-stop at my place to shower, picked up an extra change of clothes and grabbed my bedroom fun bag. The way she was going in the texts, we would be needing to kink things up a bit.  The traffic was insane heading back to her Hotel but I was making headway even though it was a Friday evening. Katie alerted me that she finished with another day of booth duties at her conference and was now headed back to her Hotel. I was well over half way there myself and would arrive earlier than expected.

The Cum Collecting Buttslut [str8][fm][anal][slut]

She walks around in a mini-skirt and a tight top. She sees a tall, dark-haired boy she fancies. “Hey, handsome,” she says seductively, playing with her hair. She lifts up her skirt, shows her butt and spreads it. She displays her butthole slowly expanding into a wide gape. “Looks like it’s quite empty in here, you wanna help me with that?,” she says in a baiting way. He’s immediately drawn to her, as if hypnotized, his large dick growing hard in an instant. He proceeds to grab her butt and insert his dick in her already slippery ass. “Ooh, you’re such a large boy. You couldn’t resist me, huh?” she says with her high-pitched voice, faking being impressed. He starts fucking her ass as hard as he can, completely mesmerized by her. She’s roughly rocked back and forth, but still unimpressed and rolls her eyes. “That’s all you can do big boy? Why don’t you fuck me harder?” she says innocently. And he goes as hard as he can fucking her ass. “That’s… nice,” she says, unfazed, looking at him, batting her innocent eyes. He’s unable to hold it in anymore. He moans loudly and fills her ass up with cum for a few good seconds, and lets out a sigh. “Heehee,” she snickers. “That’s what I thought.” She gets a large buttplug out of her purse, and inserts it into her rectum, as to keep the cum inside. She kisses his cheek. “Thanks,” she says, leaving with her purse in hand, going on to collect some more cum.

[M]y mother in law [F] seduced me while watching TV

So it was my MIL’s birthday (50) and we had drinks and so we decided to spend the night. My wife is an early sleeper and likes to sleep, so she went up in the guest room to sleep while I stayed downstairs with my MIL.
For a 50 yr old Ive always thought she was gorgeous. Chubby but really nice breasts and ass. She would often wear loose shirts and whenever she’d bend over I always got an eyeful.

So we’re watching tv, and she gets up, and tells me she’s going to get ready for bed and off she goes, leaving me to watch tv.

A couple minutes go by and I hear her coming back, she is in normal(ish) PJs, a pair of shorts with an undershirt and no bra, I immediately gaze down a little to see her nipples poking through. I start feeling blood rush down to my cock and it starts pulsing and rising, I tried to ignore it and continue watching tv, but I can’t stop thinking about her and what she’d look like without her clothes.

[F]ucking [M]y crush in a movie theater for our first date [Public] (Second Story)

Link to the original story if you haven’t read it: https://www.reddit.com/r/gonewildstories/comments/bo0w61/fucking_my_high_school_crush_at_our_reunion

I’d like to open this story with a quick thank you to the people in the comments who told me to get it together and ask Porter out again, I would be kicking myself for not taking advantage of this oppurtunity given to me, so THANK YOU!!

Anyway, so it had been two days since me and Porter had hooked up and we had been texting a little back and forth. I took the advice of you guys and Baylee and said fuck it and asked him out to see a movie with me. I was really nervous about being rejected, I’ve got a bad past with men, but to my suprise he said he’d love to meet up with me. We agreed to meet up later and I chose a theater I knew would be less crowed and chose to see Long Shot because I knew most people would see Pikachu or Endgame. I wanted him alone in a public place where there was the danger of maybe an usher coming in but not too many people. Also, and more importantly, I got to actually wear something attractive unlike the last time. It was pretty easy to up my game. I wore some hot pink thigh high socks because I knew those and that color turned him on. A flowery skirt that came just above the knees, a white lace bra that you could easily see through, and a light pink shirt that draped over one of my shoulders and exposed the other as well as the starp of my bra, and most importantly, no panties. I realized i might have gone overboard on the pink but it was too late for that and I headed out.

Friends with Benefits have wild drunken sex [MF] [ORAL] [ANAL]

THIS IS A TRUE STORY [MF] [ORAL] [ANAL]

I was probably 5 or 6 years older (28) than most of the guys in the limo, guys I’d worked with for a couple years at a big TV store and I’m a bit of an odd duck but they knew I liked to have a good time so they invited me to their bachelor party. I figured I may want to cut out at one point because they might go to some places with a lot of young folks that I just wasn’t interested in so I drove myself down and met them at the strip club and we took the limo from their.

I cheated on my date with a girl I didn’t even know: Part 3 [M/F, str8, public, cheating]

Morning came with the chirping of birds, and the faint sparkle of sunshine breaking through the curtains. I found myself lying against her back, pressed up against her. My left arm was under me and pushed straight out. Her head was resting on it, and I could hear her soft breathing. She was still asleep. My right arm was wrapped around her stomach, with her arm wrapped over it and her hand clasping mine.

As the sunshine began to peek through the curtains, I lay there, listening to the rhythm of her breath. Her naked flesh was so warm and so soft against my body. I couldn’t bring myself to move for fear of waking her. Instead, I lay there, still as could be, my eyes admiring every curve of her form, every tiny hair glowing in the beams of sunlight. Wondering if this was the beginning of something wonderful or just a dream unlike any before.