Posted 3 of our successful conquest but as most things in life, it's not all good and along the way, we had a couple failures, this being the one we remember most. So it was about two years ago, we had a couple 3 ways under our belt and CL was our go to spot at times. The month was October, so we decided to post a Halloween theme ad, a few hours pass and we get a hit from a fairly sexy first timer, she responded with shy witch in the subject. She was drinking at her place and stumble across our ad, wanting to live out this fantasy, and get DP. I was in bed already, fairly early at 10pm on a Sunday. But we messaged enough to get an invite over, she was a good 30mins from us, but sent pics and voice verified. Anyways, she wanted some Jack Daniels, and for us to be there soon. I pick up my buddy and we head out, now this was the first time a woman had offered to host. We were very nervous at this time, not knowing what to expect, since we heard of robberies and at times murders from online meet ups. We get there, and we noticed an ok area, and her apartment, it seemed safe, but we still had our reservations. She comes out to meet us, my buddy going first, as I parked, we had discussed if who would scout the actual room and give clear, me being in the car in case we needed a quick get away. I know, super paranoid, young and still inexperienced to the online hook ups. He gave the clear, and I went in, we talked and that's when I remember I had forgotten the Jack, kick in the ass for that. We keep talking and she mentions, that there's a liquor right next to the apartments, dumbass us, both of us go, buy the Jack, when she messages us that she is no longer interested. Ugh!!! We tried calling her and knocking, to no success. We kicked ourselves so hard that night and at times still remember the one who got away, even thou we more than made up for it. Too describe her, she was about 5'3 nice moderately fit body, upper 30s, wearing a short skirt, fuck me boots, and a blouse, white girl with autumn hair.
Tag: Fantasy
crossdress fantasy leads to popped cherry [m/m]
As a teenager, I had a grown from admiring and jerking off to hot girls in porn, to slowly becoming jealous of them wanting to BE them, instead of wanting to fuck them. This fantasy grew into some experiments with lipstick, panties, and stockings during my later teens – but never more than that. However – everytime I jerked it to porn- i was picturing myself as a girl on her knees sucking dick and getting fucked.
one summer evening, my little fantasy got the best of me – I was slipped into the lace panties I had hidden in my room and pleasured myself watching a girl get fucked – pretending in my mind I was her.
After my session – I decided to go out to the bar with some buddies and forget about my secret slutty desires. After a few drinks I got bored with bar scene and decided to text a gay guy I had met a few days before.
[M/F] Honeymoon anal. With long back story.
Long time lurker, first time poster. Skip to the honeymoon part for the point of the story and the more detail.
We have been together for six and a half years now, and just recently married. She is 5'4", brunette, lusciously curvy with an ass to die for. I am 5'10" average build, broad shoulders, nothing too wild. We began our relationship her as a virgin with very little experience, and myself who had sex about three times with a past girlfriend.
Throughout the start of our relationship, we began to slowly explore our sexual boundaries. It started as usual with groping, teasing, leading to oral and eventually we did the dirty. This opened up a whole new side of both of us as we were constantly horny and in need of each other. Three, four and five times a day and we had to stop just because we were so sore. We talked about each others fantasies, and mine being the standard for a guy – anal, facial, swallow, etc.; and hers being on the conservative side – back seat of the car, different places in the house, the most elaborate of wanting to be in a tent outside. We started to slowly satisfy each others desires albeit, rather clumsy.
The Four Seasons [MF, oral, exh, fantasy, choose-your-own ending]
So this is a bit of an unusual format for a reddit post, but I'm posting the introduction here, and then each of the four paths will be a separate link in the comments. Hope it's not too confusing, and thanks for reading!
I stood at the cliff’s edge, surveying the majestic scene before me. The sun was just beginning to rise over the snow-tipped mountains in the distance, sunlight scintillating off icicles in the pines’ branches. In the gorge before me ran a wild river, rushing through the landscape. In the middle were Arcadian hills, punctuated with wildflowers emerging from their hibernation. It was beautiful.
I sat down, took out my canvas and paints, and began to attempt to capture the beauty of nature before me. I had come out to the wilderness alone for a weekend camping trip. I had planned to invite my girlfriend, but just before I was going to ask her, she had broken up with me, complaining that I focused too much on painting and nature and not enough on her. I was still devastated, but pouring myself into my work was helping to soothe my troubled soul.
My Halloween toyboy adventure with a [M]il[F] (24/45)
I had been reading this sub for a while, and even though I've done some things worth of being here, I never felt like posting them. I feel like I should say this though: all that's written here happened last Friday, the night before Halloween.
Also, sorry if this is too long, I'm going to write everything I remember, and it's the first time I write about a sexual experience.
No costume yet, but I was still excited about going out, the previous weekend I had managed to get some extremely strong weed, so I just wanted to go out and have fun. I was going out with some friends to meet some fellow redditor at a party, so we shared one joint and headed to the party. It was so strong that we got there pretty high, got a drink each, and started walking around and talking to people, the party was at a bar, not too dark, with loud music that still let you hear other people. There were about 30-40 people in "our group", mostly dressed up, so it seemed like it'd be a good night.
Two; or, the prequel to a threesome. [MF] [second person] I may be persuaded to include pictures.
I waited for you in the restaurant; sure, I was early, but you were also late. I wore a navy blue dress and thigh-high brown boots. Dinner was awkward. I was shy, you seemed nervous. We chatted, getting to know each other. The details weren’t very significant—we talked about work and school and the restaurant. I barely remember them now, which does make me somewhat sad.
We drove to the hotel and stood around somewhat awkwardly again. Finally, we agreed it was time for me to change. I disappeared into the bathroom and quickly slipped into a lacy black bra, pink lacy underwear, and my skintight, black dress (the one that’s too short and too low-cut for me to wear in public—if it were one or the other, I could get away with it). I looked in the mirror, fluffed my hair a little, adjusted my bra so my breasts were just starting to pop out of the v in the otherwise round neckline of my dress. I stepped into my nude heels, took a breath, and opened the bathroom door. I left my hand on the door frame and took a step out, leaning my torso ahead of my legs. I shyly stepped the rest of the way into the room. You turned and stared at me while I stood, one leg extended slightly behind me, toes against the floor, heel swaying in the air. My hand is still on the door, the other hanging by my side.
Halloween in Wonderland (F/M)
Halloween always offers a good excuse for me to go out dressed up in cosplay, but on the downside it always comes soon after a major convention that I go to so I usually don't have the time or money to spend on doing anything spectacular, and haven't even bothered at all in recent years. However, this time around a number of my friends were insistent upon a night out, and feeling uninspired and a little lazy I decided that the most fitting thing I had to wear was my Alice in Wonderland outfit which I hadn't worn in quite a while. So, come Halloween evening I pulled on the blue and white dress and white thigh-high stockings with lace tops that allowed just a little flesh to show between their tops and the bottom of the dress.
All prepared, I headed off – first to a friend's house, then onwards to a nearby club. I didn't expect to get much attention given some of the far more revealing outfits on show all around, but I did get plenty of shouted comments over the blaring music, mostly asking whether I was as innocent as I looked. To start with I simply smiled at these questions, but as the alcohol flowed my responses got a little braver – a "maybe not" here, a grin and a wink there, and to be honest the attention was getting me a little excited.
Halloween oral sex & 69 with [m]y girl[f]riend.
Some years ago, my then girlfriend and I were invited to a Halloween party at the home of one of her best friends. Every year since, on Halloween, I relive the memories of that night. This year, I thought I'd write it down.
We weren't particularly inspired by costume ideas that year, so she dressed as a sexy cheerleader and I threw on a football jersey. So the night started with me already a bit more turned on that usual, since as part of the cheerleader outfit, she did her makeup in a really pretty way, with (foreshadowing) red lipstick. She very rarely wore makeup, so she was looking really good: 5'7", brunette, a slim frame proportionate to her body with the perky C-cup breasts that make mid-twenties girls so beautiful.
As we were getting ready earlier in the evening, she made a point of not letting me see her naked while also dropping a few subtle reminders that she'd had her legs waxed the previous day. This left me tantalized that maybe she'd had them extend that waxing to her pussy, which she had never had completely bald but which she knew was a fantasy of mine.
Closer (mostly buildup, M/F, F/F teasing, continuing an earlier thread)
It's been a while since this fantasy, and things have … progressed is probably too strong of a word, but the fantasy has solidified. My wife and Vicky went out of town for a night for a girls' weekend kind of thing not too long ago. Before that happened, I told my wife that if any situation were to arise with Vicky that she might want to participate in, I expected a phone call asking for permission. I told her that details and photos wouldn't hurt either.
I received a handful of texted photos ranging from the typical selfie at a bar to one of my wife doing her makeup in the mirror with Vicky in a towel in the background. Enough to pique my imagination, but not enough resolution for useful details. Basically, a whole lot of teasing.
However, one photo stood apart from the others. It was an upskirt pic with the other person's hand on the inner thigh, pointing. This was torture. I couldn't tell who I was looking at, who was pointing, and due to the shadows, whether or not the person was even wearing panties! I texted my wife and asked what I was seeing and if she needed permission for anything.
Walker [MFf] [Fantasy] [mdom] [bdsm] [dark]
It was a cool, autumn evening. The sky was overcast, and the rain beat off his leather duster as he walked in the park. Not many people were out, except the few dedicated runners in their rain jackets, breath puffing from their hoods.
Walkers boots crunched on the gravel path as he moved to stand by the lake. This was his place in the town to relax. He stood in the edge of the water, back to a small tree his lean form fit behind, and drank from the bottle. The burn of 80% alcohol was a pleasant sensation, even if his body burned it quicker than he could drink it. The metal plates in his boots directed the large amounts of heat he produced into the ground.
As his mind wandered the skies, touching upon the birds and even the invisible entities past the atmosphere, a tingle brought him back. Stepping away from his body, still sipping the liquid fire, he roamed the park, following the trail. The electric buzz in the air was a trail easily followed. She was arrogant with her power. Uncaring for what found her. Or it was a trap. Again. Watching. Waiting. His anticipation grew.