Author: Dependent-Bit-6653

My luck got even better: I had a hot threesome on vacation with my former prom date Jenn and new girl Kathryn [MFF]

Sorry for the long delay writing this promised follow up to the story of my very fortuitous hookup with my former prom date Jenn: https://www.reddit.com/r/gonewildstories/comments/trr2ui/three_years_later_i_randomly_ran_into_my_prom/

I’ve played around with the narrative structure here a little bit, hope you enjoy! I ended up being with Kathryn for a couple years and I have many, many stories I could tell about her and all the nasty, filthy sex we had if you are interested in hearing more about her.

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Kathryn, completely naked, was across the living room and peering into the doorway of Jenn’s bedroom.

“Jenny? Wanna play with us?” I couldn’t hear Jenn’s response, if there was any, but Kathryn slipped through the doorway. I quickly followed and Kathryn was already climbing under the sheets, hands and feet starting to tangle together with Jenn’s. I came around the other side of the bed and climbed in next to Jenn. Kathryn kissed Jenn, aggressively, her fingers already running through Jenn’s straight brown hair, and I snuggled up behind Jenn, her free hand reaching to grab my arm, welcoming my contact. Holy fuck, this was really happening! Read more »

Three years later, I randomly ran into my prom date Jenn, almost had a threesome with her friend Molly, fucked her, and came on her tits [MFF]

From across the apartment complex parking lot I saw an unmistakably familiar figure walking in the yellow streetlights.

“Jenn?” I called out. She recognized me and waved, then walked across the way to me.

“Hey! How the fuck are you?” I asked. She stood in front of me, tall, somewhat gangly, and girl next door cute, brown eyes, shoulder length brown hair, and a distinctive nose. I think objectively speaking she was average looking, but there was just something amazing about her eyes and her smile – reader, you simply can’t explain any of this to someone didn’t feel the same nervous flutters every time she looked at you.

“I’m great, how are you?” she asked in reply, gesturing to my outfit, which happened to be a colorful pink sheet wrapped around my body, flip flops, and a plastic crown of olive branches.

“Oh, um, toga party,” I explained with a goofy grin.

“I can see that,” she laughed. Read more »

I invited Chaya to visit me – we had a morning full of unbearable teasing and hot, intense sex (long) [MF]

This the story of another date I had with Chaya, who I have written about twice before here:

Two hour fuck and ass play marathon with cute Jewish girl next door Chaya, 26 [MF] from gonewildstories

And here: https://www.reddit.com/r/gonewildstories/comments/sntrc9/jewish_girl_next_door_chaya_and_i_hooked_up_again/

Although this story is mostly about the morning full of sex, we spent the entire day together and it was amazing to get a chance to really connect with her more deeply as a person, especially in a beautiful surrounding. My heart is a little bit guarded, but I’m excited to see what the future might bring for us. Thanks for reading.

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After our last date a couple months ago, I had been keeping in touch with Chaya and finally, I decided to make a move and ask her to come visit me. We were still just getting to know each other and I thought it might be too forward to ask her to stay at my house, so to keep it at least somewhat gentlemanly I bought her a plane ticket and booked her a room at a very peaceful, wooded resort nearby. Reader, the wait to see her was almost unbearable, but somehow I managed to distract myself through the days. I was in a bit of guarded, anxious disbelief until the minute she texted me to say she’d landed and was on the way to the hotel. We planned to meet in the morning and spend the day together. Read more »

Risky fuck at my new girlfriend’s house on Thanksgiving. Did her parents hear me creampie their daughter? [MF]

We arrived at Athena’s parents house for Thanksgiving and set our bags in the doorway. This was our first holiday together as a couple and I was officially meeting the parents and family for the first time. No pressure.

She was Greek, as you might guess from the name, which meant a big, loud family and a lot of introductions.

“Let’s take our bags up to my room,” she offered a few minutes later, giving me a chance to take a break from the commotion and merrymaking. I stuffed a piece of baklava in my mouth, set my wine down, and grabbed our bags.

Following her round ass up the staircase was a treat in and of itself. At the top of the steps, we reached her childhood bedroom. School yearbooks, favorite stuffed animals, pictures of friends, and a violin she used to play once upon a time.

“I’m going to change real quick,” she said as she pulled her sweater off. I immediately got hard admiring her standing there in her bra and jeans, already horny from several hours in the car and half a glass of wine. She had perfect olive skin, Mediterranean brown eyes, shoulder length brown hair, and curves to die for. Read more »

I fucked an old fling and her dirty talk was absolutely on fire [MF]

Sorry for the long delay between stories, but I hope this one is worth the wait. A couple weeks ago I had the chance to hook up again with an old fling who I have previously written about here: https://www.reddit.com/r/gonewildstories/comments/sbn2vp/hot_afternoon_fuck_and_intense_anal_orgasm_for/

It seems like a few things have changed in her life since I last saw her, but from the looks of it she’s doing great, and most importantly: the sex was just as wild and hot as last time.

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Back in New York City for the first time in quite a while, I shot my girl River a note asking if she’d like to hang out. Much to my delight she was free for the evening, and yes, she’d love to catch up over a drink. I waited to meet her outside my hotel after dinner and she arrived bundled up against the cold – hard to recognize – but her striking icy blue eyes were unmistakable peering out from under her knit toque and over the warm collar of her coat. Read more »

I fucked and creampied my college ex in the bed and in the shower before her boyfriend came over [MF]

I knew I shouldn’t be going over to Elise’s apartment, but here I was. We had been on-and-off since freshman year, currently off, and interesting development: she now had a boyfriend. Boyfriend or not, she needed help with her chemistry homework, and among my many charming qualities I had gotten straight As in four semesters of O-chem and finished most of a chemistry major. Who better for the job? He would understand.

I knocked on the door to her walkup apartment and she answered in a v neck t shirt and pink sweatpants. She was tall, with straight brown hair pulled into a ponytail, a slender body, and perfect Ds under her t shirt. I could not help but notice her nipples poking at the fabric.

“Hi,” she said, inviting me inside. I gave her a hug and I reached down to say hello to her cat, Felix, who was rubbing against my leg.

She walked me to the bedroom and hopped onto the bed with her notes and textbook. I started explaining resonance electrons to her and working through the homework questions with her. Getting into the subject material, she scooted close to me attentively. Read more »

Summer Love – monthly contest submission [MF]

I remember her flashing a fake ID to the bartender and bragging about it. We were young and dumb.
Platinum highlights in her hair, green eyes, sun-freckled cheeks, a toned, tan beach body, a perfect pair of double Ds under a crop top, and a denim skirt leaving little to the imagination.
We stole a kiss over two shitty margaritas. Back to my place.
Her skirt and bra on the floor of the bathroom, she herself waiting on my bed in her top and thong.
Touching, kissing, tasting, our bodies in motion and sweat on our skin in the warm Florida air, her jasmine and vanilla scent more intoxicating than the cheap tequila.
Her necklace dangling between her tits as she sucked my cock, looking up at me with those green eyes, spit dripping down her chin and the butterfly charm bouncing off her chest.
“Fuck me, bad boy,” she whispered in my ear.
I answered with my hands, my fingers running over her hard nipples, slipping down her panties and between the wet lips of her shaved pussy.
Her thighs spread, my hard cock pushing inside her, her moans, my moans, the summer song of ecstasy in the night.
Her on top, fingernails sharp on the skin of my chest, riding as if it was the only way to get through the dark of the night.
Faster and faster, the heat rising to a boil, pulling her tightly to me as I came inside her. Crying out, her body pulsing in rhythm with mine as we shared the moment of climax.
We kissed in the darkness, dizzy in the afterglow. Feeling every emotion, it was summer love.

Jewish girl next door Chaya and I hooked up again. Mind blowing fuck – and – she wanted to try anal. [MF]

I’m very happy to say that I recently got another chance to see Chaya, who I have previously written about here: [https://www.reddit.com/r/gonewildstories/comments/rqs0f0/two_hour_fuck_and_ass_play_marathon_with_cute/](https://www.reddit.com/r/gonewildstories/comments/rqs0f0/two_hour_fuck_and_ass_play_marathon_with_cute/)

Who knows where this tête-à-tête will go, dear readers, but for now I am enjoying the wild sex and incredible chemistry.

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It was late on a Monday afternoon in my office and I got just the email I had been waiting on for a couple months. I grabbed my phone:

“Chaya – great news. I have a meeting in town next Wednesday. Any chance you want to get together?” I knew what the answer would probably be, but almost immediately her response came:

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“This is the best news!! Did you want to get together before, after, or both?” That’s my girl.

“As much fun as it would be to go to a meeting with dirty secrets and a huge smile on my face 😈 I don’t think there would be time.”

“Well, ok, what time is the meeting, so I can content myself with sending you naughty texts during? 😈” Read more »

I fucked a total stranger in front of the hotel windows in Vegas [MF]

This story has been on my long list of adventures to write about but I was inspired by this very excellent recent post to put it on the top of my list: https://www.reddit.com/r/gonewildstories/comments/ruhz6h/so_all_of_vegas_can_see_mf/

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This happened in January 2020 just before COVID. Also note that this Rylee is not the same Riley I have written about before (and God I hope I write about her again).

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Finally, seriously be careful about going to random strangers’ rooms in Vegas, trust your judgement and don’t carry any money or valuables.

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It was a chilly January Saturday evening in Las Vegas and I had been flipping through Tinder after dinner. I was at the Cosmo sipping on a Manhattan and got a match very nearby. A few texts back and forth and I invited her to meet for a drink but somewhat to my surprise she invited me to her room next door at the Vdara. I am always game so I agreed, dropped my wallet and watch off in my room upstairs (gentlemen, never carry anything you don’t want stolen from you when going to someone’s room in Vegas), and walked across the short walkway to the Vdara lobby. Read more »

Latina single mom with huge tits swallows my cum at lunchtime between meetings [MF]

I knocked on the door of Kayla’s duplex and she let me in, greeting me with a hug. I noticed, and appreciated, the low cut shirt she had put on for me as she pressed up against me. I stepped inside and her lazy yellow Lab arose from his seat at the foot of the living room couch to give my hand a sniff and a lick, and seeming to approve, laid back down.

“Hi dear, how are you?” I asked.

“Fine – wrapping up this meeting. Go help yourself to a drink, baby.” She unmuted and returned to the last couple minutes of her Zoom – I wondered exactly how she had the camera angled given her choice of top – and I set a white envelope containing a few hundred dollars on the corner of her living room pandemic work from home desk as I walked past to the kitchen. Read more »