FFM – sex, drugs, and my first threesome

A few years ago I was dating a very lovely young lady, for the sake of this story we will call her Carolyn. Carolyn was my ex-girlfriend’s best friend, and we had been good friends throughout my relationship with my ex, but when that relationship ended Carolyn swooped in and claimed me for her own. I wasn’t complaining, Carolyn was 5’2″, 95lbs with 28H breasts and the tightest, tiniest pussy I’ve ever experienced. She was a goddess, and little did I know she was a freak too.

Once during my relationship with my ex, she told me about a time her and Carolyn got drunk together in the hot tub and Carolyn started asking weird questions like “don’t you think girl’s bodies are so sexy?” and “have you ever considered being with a girl?.” After some more of these questions, my ex was getting a little nervous and then suddenly she felt a hand on her inner thigh. She didn’t know what to do, so she started talking about something trivial. As she talked, the hand moved up her thigh and under her swimsuit and began rubbing her clit. My ex freaked out, got up, and left, and her and Carolyn never spoke of it again.

[M/F] Cheating Wife from Craigslist in Austin, Texas

I’m not particularly proud of this story, but it was hot and so much fun. I have one of those problems that most of the readers in this subreddit do. High libido, but to the point where you can’t think straight unless you get some kind of sexual release.

 

I had been super into facial abuse videos and was looking for a willing partner. So, naturally, I posted an ad on Craigslist to try to find a woman willing to let me destroy her throat and make her mascara runny. Yeah it’s impossible. Anyway, after posting my ad, I noticed a post from a girl that was 26 years old that was into kinky rough fun. 99% of ads on Craigslist are fake. If you’re there long enough (read 10 minutes), you know how to spot them. Her’s was legit, and I messaged her telling her about my own facial abuse ad. She read my kink list and said “YES Please”.

 

M/F – Valentine’s Day Surprise

I’m a hopeless romantic. I think, even with all things considered, I’ll always be one. Maybe I’ll have a reason again to be hopeful. Stuff like Valentine’s Day always makes me hopeful. Call it corny, but that, random acts of kindness/love, and pretty much any romantic comedy gets my heart a pounding, in the best ways. Cute girls do that too.
So a wicked cocktail of inspiration found its way in front of me on Valentine’s Day 2013. Leah and I had been dating since the beginning of that school year. Was it love? I don’t know, we whispered to each other after we fucked. The way I pulsed in her was slow and sensual. And she’d lightly dig her nails into my back as she whimpered into my ear, and her breathes would pick up as she’d start to tighten around my tan cock. And before long I’d be erupting onto her stomach, kissing her cheek, and spooning her.
Her pale skin and red hair fit so well with the little black dress she wore that night. Her meek smile was something I had gotten used too. Leah always had a worry…always had something her mind, even when we were together in our most intimate moments. So as we started to dig into appetizers at a swanky hotel restaurant a couple hours away from our college town, I didn’t put much thought into her slightly less than excited demeanor.
You know, I think when you’re truly focused and in love with someone, every extraneous noise sort of becomes all muddled. Like you’re underwater. And that person you’re focused on his your clarity. Clear as day. Valentine’s Day was about surprises. And I had delivered mine. A four star hotel room, that amazing dinner…and hopefully I’d be delivering a weekend of lovemaking. But Leah had her surprises too.
And it’s crazy how fast she sank into the deep end with me too.
“Did you hear me?” I had to have paused too long, “I cheated on you.”
Her voice was static. It was fuzz. Her transgression had happened when she went home over Thanksgiving break. And again Christmas break. Some old ex. Some emotionally manipulative asshole. Her words. Not mine.
“So what do you think about that?” she leaned back and bit her lip. A helluva Valentine’s Day surprise. And I got hot. I got furious.
“Why?” I finally breathed, digging my nails into my palm.
“He fucked me like he hates me. He always did. You just couldn’t ever go there with me.”
That stung. I’ll admit it. Especially because it’s not what I fucking meant.
“No,” I growled, “why are you telling me this now?”
“Because you’re too good. You’re too nice,” she shook her head, locking her green eyes with my browns, “I don’t deserve all of this. This dinner. This room. I just deserve to be punished in my loneliness.”
She poked at her food as I felt my heart throb in the most painful of ways.
“You’re probably right,” I muttered as I shoved back in my chair. I wasn’t so much furious as I was numb, as my mind was racing with any possible ideas of how to get through the rest of the night without drinking myself to death. Shaking my head, I pulled a couple of bills from my wallet and threw it on the table.
“Wait, what are you doing?” she asked genuinely as I paced off in the direction of the elevator.
“Fuck you,” I breathed. A flash of hurt crept across her face, as she stood to try and follow me. Leah was pretty petite, so my angry and long strides hastily beat her to the elevator. I waited for the door to open as she padded up to me, quickly sliding in as she continued her approach. Things might have been different if I would have just mashed the “close door” button, but she slipped in at the last second.
The room was a few floors up, but thankfully there wasn’t any elevator music. Come to think of it, maybe it would have been better for my wandering mind. We stood in the back corners of the vessel, I’m sure both debating about what our future held. Not even as a couple. I’m pretty sure that was over. But I almost started having second thoughts as I stole glances at her.
She stared forward, that meek smirk back at home. Her pale neck sloped down, and her small, pert chest rose and fell ever so slightly. Her ass was pretty small, but hey, it fit the figure fine, and as the black dress hugged it and hovered over her ivory thighs, I just fucking pounced.
Pressing her up against her corner, my palms found its way harshly against her stomach, as my lips kissed her hungry mouth. She let out a moan as her hand fell to my wrist, and she pressed her body up against me. Leah bit my lip as she pulled my hand up level with her neck, and I closed my fist around it. I bit back. Harder. We roughly made out, pausing only when the bell dinged and the doors open.
Her smile was wider as she looked up at me, and I glared down at her. My hand coasted down her collarbone, and I roughly squeezed on her tits, before I dug my fingers into her shoulder and pushed her in front of me. In seconds I was pressed up against her from behind, and she was stifling moans against the door to our room. I slid my keycard into the door and slowly opened it, before grounding my hips into her from behind. When we were slightly out of the sight lines of the hallway, I roughly grabbed her ass cheek through her dress. Leah cussed in affirmation, as I pulled up the material to squeeze her globes. No panties. Fucking bitch.
I pulled my hand back and rapped it down hard as she yelped. I shoved her and the door forward even more, pulling her out of the way by her wrist to slam the door behind me. And I shoved her back against it.
“Hold your fucking dress,” I commanded, as I started slapping her small ass again. On. And off. I railed against her ass, as she wiggled it for me. After five or six spanks, I slid my fingers down and spread her thighs open. She was gushing.
“Fucking drenched? Just from that?” I whispered into her ear, before biting at her neck.
“Mhmm fuck, I told you I like it rough,” she happily laughed out.
But this wasn’t even about her.
I dug my fingernails into her side and shoved her in the direction of the bed. She crawled around on all fours as I started to unbutton my dress shirt. Tossing her legs over the edge, she dipped a hand between her thighs as I approached, but almost dutifully started to focus on my belt and slacks. As I shimmied out of my dress shirt, she pulled my throbbing tan cock out and jacked it off as she smiled up at me.
When I pulled off my white v neck, she dived onto my length, slurping fast and hard. She was so fucking eager. Slutty red lips grinned around my cockhead, painting my tan manhood. And as I buried her hair in my fist, I face fucked her. But after a couple of minutes, I couldn’t even look at her.
So I forced her off my cock, slapping her cheek as she closed her eyes and moaned. My hand found her neck again, as I moved her back on the bed, where she eagerly spread her legs. Dancing out of my boxers and slacks, I shook my head and jacked my dick.
“Turn,” I said simply, and she followed orders well. Sashaying that ass, she was so fucking ready. And I was too. I was ready for one last memory. Spanking her one more time, I pushed the bottom of her dress up before sinking my full length into her tight little pussy.
“Mhmmm fuck,” she cried out, almost surprised. My hands gripped the globes of her behind, as I pumped in and out, groaning out under the duress of her gates. I spanked her every once in a while but for the most part I just channeled my anger into her.
Leah looked back every so often, biting her lip. And I knew that face. But I had come to hate it. I balled her hair in my hand and pressed her down into the bed, spanking her even harder as I picked up speed. When she resigned herself to that place, I tore the straps of her dress down so I could squeeze her little tits, nipples capping under my dominance.
She moaned against the bed spread, cussing as she bounced her ass on my cock. I pulled back and spanked her, before sinking in again, feeling her cunt gush all over my thickness. And I felt so fucking close. I badly wanted to press my whole body weight against her, and cum deep inside. But all things considered, that was probably an awful idea.
Still, I picked up speed, digging nails into her ass cheeks, pumping in and out as I felt cum start to rumble in my balls. And right as I was a few strokes away, I slipped out and quickly wrapped my hand around my dick, slickly sliding up and down my shaft.
“Mhmm fuck….fuck you Leah,” I growled, blasting cum all over her lower back, and painting the material of her dress. I fell back into a sitting position as she warily looked back over her shoulder.
“I need to shower,” I said simply, “I want you out of here by the time I’m done.”

[f] Saturday, came and gone

First part: https://www.reddit.com/r/gonewildstories/comments/51qm70/sitting_in_class_f/?st=isz27ckp&sh=ad1aa93d

Second part: https://www.reddit.com/r/gonewildstories/comments/51xny5/thursday_night_f/?st=isz27apb&sh=077e83c0

*Sorry for posting a bit later than Saturday, it was a long weekend of train rides, marathon sex, drugs and techno. Extremely memorable yet blurry. I’ve decided to write down snippets of the best. Hope you enjoy!*

I was standing at the station after hours of traveling, in another country, with my dildo firmly stuffed up my pussy, meeting someone who’s controlled my orgasm for the last four days, for the very first time.

After some nerve racking pacing, he appeared a few meters away. I took off my sunglasses mouthing hi. He was almost charging at me and stopped just a few centimetres/ inches short, apologised for being a little late, went for a kiss-bite and reached for my pussy. “I actually do have a dildo in me.” I whispered into his ear. He checked within two sentences if I was wet, just as promised.

The second my tight jeans came off, he started pumping me hard and deep with the dildo, I lost control immediately and started bucking and moaning loudly. It was a very sensual button. He then stopped abruptly, hovered over me, staring into my eyes with a smirk, “hello.” I was melting. I reached for his belt, but was denied, “not yet, I’m gonna be teasing you for a lonnnng time.”

[Group] What a birthday surprise to remember!!

So let me just say this from the start. Im a 24 years old trans girl. This story takes place when I was just a crossdresser. It was my 21 birthday and my best friend and I, Her name is Demi, same age as me and best friends since high school. She is a normal girl, born a girl at birth. We drove 4-6 hours to LA. I dont want to give specific locations because I dont want to plug anything. So the thing you have to know about Demi is that shes quite the out there person. Shes very vocal and loud but very fun and just an amazing person but very out there. So we got a hotel room and we did fun things all day and night. So after we finished all of that we were back at the hotel room around 9pm. She said the days not yet over and said follow her. So i did and we drove for 20 minutes to this house. I asked what was going on, and she said remember a few weeks ago when you went to the doctors? I said yes and part of the doctors checkup looks for STD and i was clean. Turns out she when the same day and she was clean and sent the results off to the owners of this home so we can get in. we get to the front and people awneser the door, and what i seen I will never forget. It was an orgy of people, like 20 or so, doing sexual things! Ive never been a huge sexual person but it was really hot!!! So we went in and the orgy was full of real girls and either trans or crossdresser, I couldn’t tell. I sat down on the couch and demi just said relax and have fun, as she started to suck my cock. I knew her for many years at this point and she never once did anything sexual to me. As shes doing this somebody comes over and i suck their cock while im getting mine sucked. This went on for like 2 hours. Sucking cocks, Licking pussy and tits, getting my cock sucked by two people at once. I never had sex with anybody that night but a few people licked my butthole, but no fingers. I was to shy for that to happen!! Demi only sucked my cock, i never did anything to her, but i seen other people having sex with her. Also got alot of cum on myself that night!! Me and Demi are still friends today and we talk and see eachother very often, 3 years after that experience. We never did anything sexual to each other after that day and weve never been back again, well atleast i haven’t!! I wont do it ever agian but im glad it happened!! What a surprise to remember!!