Last summer, I came across a post on Reddit by couple seeking a single male for a threesome. They were in their mid-20s and without any experience with group play. Having played with experienced others during a previous relationship, I understood all the feelings flowing at once: excitement, anticipation, and total anxiety. Since I was in their exact shoes just a few prior, I felt it my stately duty to volunteer as their sexual sherpa and guide them up menage mountain.
The next day, I received a reply back with an invitation to message them on kik (the intermediate step just before exchanging phone numbers). A prudent move considering one can never be sure who may be on the other end. Best to dig a digital moat in case things go south. When I shot them a message on kik, they introduced themselves as Sara and Kevin.
At this point, I still hadn’t seen a photo of either. This can be especially problematic if there’s no physical attraction after a promising back and forth. Although the end game is an orgasm, if I wanted to orgasm without regard for the other person, I’d take my chances at the local glory hole.
After a bit more small talk, I suggested we exchange photos. They had already seen me, but I sent a few more for good measure and waited with baited breath for them to return the favor. One by one, by screen lit up with notifications of new messages. I unlocked my phone, opened the app, and audibly gasped. Sara was a gorgeous blonde with petite body. They informed me she was an avid runner. It showed. In addition, Sara had one of the most adorable smiles I’d ever seen. Her almond-shaped brown eyes were perfectly proportioned atop that rosy-cheeked grin. To his credit, Kevin was a handsome guy; bearded, burly, and what many might label a lumber sexual. He was like Nick Offerman if he fit, half his age, and six-foot-three. I was floored that he would be open to sharing a girl who surely turned heads everywhere they went.
But deep down, I also began to wonder if this may have been too good to be true. As mentioned in my [previous story](https://www.reddit.com/r/gonewildstories/comments/5v362c/threesome_turns_foursome_mfmf_group/), catfish are fairly common in the dating pond. Doubly so with swinging. I, myself, have been called out a few times for potentially being fake. I never get upset because anyone who would consider my photos theft-worthy is paying me the highest possible compliment.
Me: Her smile could melt faces.
Sara: Aw, thank you. That’s sweet of you to say. :)
I always assume I’m speaking with the male half of the couple, but I’m pleasantly surprised when it’s not. There have been multiple occasions where I’ve discovered a guy scheming to unwittingly rope his girlfriend into a threesome. Usually it’s a variation of the following: “Yeah, we talked about a threesome a while back. She wants to try it, but I know she’d be freaked out with a stranger. It has to be organic and someone familiar. So let’s meet for drinks, and I’ll tell her you’re an old college friend. After you guys flirt, I’ll bring it up with her, and she’ll definitely be into the idea.”
It’s a major red flag when an interaction hinges on being complicit in deceit. It’s also not something I’ll ever take part in. My philosophy has always been to make sure everyone is on the same page: limits, boundaries, and communication will avoid a vast majority of issues which will inevitably arise. And if he’s willing to lie about how we know each other, what else could he lying about?
Sara and I continued talking, and she asked when I’d be free that week. From my own past experiences, I realize how quickly a group sex fantasy can run hot and cold. They mentioned their schedules were free that night, so I fucking went for it.
Me: Tonight works for me as well. :)
They invited me out to a restaurant near them, and we agreed to meet for drinks a few hours later. But Sara and I kept conversation kept going, and she teased me with even more photos. Each became increasingly more risqué. Fresh out of the shower, she sent me various various bra and panty combinations and requested that I select my favorite. Since I believe in equality, I sent her three options of boxer briefs: black, green, and blue. The blue were a size too small and overly accentuated my package. So naturally, those were her choice.
The restaurant they chose wasn’t in an area with, how shall I say, the most thriving night of life. The town is populated by families and retirees, who have no use for meddling kids like us. I parked on a steep hill adjacent to the restaurant because my car is too shitty, and my wallet too light, to afford valet.
I texted to let them know that I parked and was walking down. Sara replied and informed she was coming outside to meet with me. I was a bit shocked they would send her to greet a perfect stranger in the dark of night. For all they knew, I could’ve been an axe wielding murderer with great taste in underwear.
As I made my way down the hill, Sara came bounding toward me from the shadows. When we were within in a few feet of each other, she threw her arms around me and gave me a bear hug. She was giddy and tipsy and very handsy. For the briefest of moments, it felt like we might kiss. I resisted the temptation out of respect for Kevin, whom I’d yet to meet at this point.
Sara and I walked the rest of the way making small talk before she grabbed me by the hand and led me into the restaurant. We made a right turn past the host stand and plopped down in a corner booth. Kevin had a massive smile plastered on his face as we exchanged pleasantries and shook hands. Sara situated herself between both of us, a sign of things to come that night.
The server came to our table, and I ordered a vodka club. I could tell they’d already had a few cocktails to help ease the first-time jitters. As we made introductions, I learned that Kevin was attending med school at my alma mater. Sara had likewise just left her job to pursue further schooling and get her JD. I’ve found consistently that the kinkiest people also seem to be the most intelligent. The only satisfactory theory I’ve settled on is that a curious mind in school remains a curious mind in sex.
To ease a bit of the tension and address the kinky elephant in the room, I’d told them the story of my [London threesome.](https://www.reddit.com/r/gonewildstories/comments/5p1cy5/an_american_swinger_in_london_mfm/) I mentioned that although I’d enjoyed myself that night, I definitely preferred something more ongoing.
After a half hour or so, Kevin excused himself to go to the bathroom. When he was just out of view, Sara practically jumped in my lap, and we began making out like middle schoolers on the couch. And then, as though her parents walked into the living room, she immediately stopped when she spotted Kevin. I figured they’d spoken about this, since she was so brazen with her tongue jitsu. I could tell Kevin was trying to maintain a pokerface, but his smirk tipped his hand as to how he was feeling about seeing his girlfriend kiss another man. A little later on, Kevin once again excused himself. And once more, Sara attacked me like I’d just returned from a tour in the military.
I began to wonder what the family at the adjacent table must’ve thought about this whole setup. First, a young couple enters the restaurant together. Then a friend arrives and joins them. Once the first man is out of the sight, the woman furiously begins kissing the second until his return.
Kevin returned to the table and when I finished my vodka club, they asked if I’d like to join them at their place. I told them it sounded fun and since I’d only had one drink, I offered to drive. They gladly accepted. Sara stumbled a bit as we walked up the hill and nearly got clipped by a passing car. Luckily my reflexes were on high alert. I put an arm around her and ushered her to safety.
Sara rode shotgun, and Kevin sat in the backseat next to my duffel bag. Because Sara had an expressed interest in being dominated during our earlier text conversation, I packed a few goodies for later.
As they gave me directions to their apartment, they told me about their crazy downstairs neighbor. Sara chatted him up one day and had mistakenly given out her number in an effort to be friendly. The neighbor misinterpreted this as interest on her part and for the past several months, he would periodically message her with walls of text. Often, they were unintelligible revelations he’d had while taking psychedelics on camping trips. His musings was a far cry from Terrence McKenna. I pulled up to their street and parked a few houses down. The three of us tiptoed by their neighbor’s apartment and up the stairs as not to arouse suspicion.
Once inside, Sara poured me a drink and offered to take me on the official apartment tour. I dropped by bag, and we walked through the dining room and into the living room, until she finally led me to their office. I looked around. Seemed like a typical setup; lamp, desk, carpet. When I spun back toward her, she pushed me into the swivel chair and straddled me. We picked up where we left off in the restaurant and then some. Within less than a minute, she pulled down her dress, and I was sucking on her soft nipples. This intensified faster than I anticipated. Maybe a little too fast because Kevin called for a brief timeout as he watched just outside the office.
Kevin: Can we take a break for a minute?
Sara slipped her dress back on over her shoulders and made her way to the bathroom. Kevin pulled me aside.
Kevin: So this is really exciting for me, but I’m still not sure how comfortable I am yet with it.
Me: Hey, no worries. We’ll go at your pace. We can stop anytime you want.
Kevin: So I’m thinking you can just play with her through her clothes but her panties stay on tonight.
Me: Perfect. Works for me.
Sara exited the bathroom and coyly asked what we were planning.
Kevin: Why don’t you try on your lingerie and have him choose something he likes?
Sara: Oooh. That sounds fun.
I followed Sara into the room, and she sat me on the edge of the bed.
Sara: Cover your eyes.
I did as I was told. After a moment, I heard rustling from inside their walk-in closet.
Sara: Open ‘em.
I opened my eyes to see her modeling a sheer babydoll with matching blue panties. With my jaw on the ground, I twirled a finger to have her spin around for me. I wanted to get a look at the full package. Her ass was even better in person.
Me: Hm, I like this one but what else ya got?
Sara: Close ‘em again.
After a moment, she caught me peeking through my fingers.
Sara: Hey, no cheating.
I had to try. When I opened them back up, she was in a black teddy with a plunging neckline. She sauntered over to me and put her perky b-cups dangerously close to my face. I put my arms around her waist, and she put hers around my neck. For a fourth time, we were engaged in a heated makeout session. She mounted me on the bed but true to my word, I left her clothes on.
Sara had other plans.
She untied the straps behind her neck and leaned down so her nipples were brushing against my shirt. I felt Kevin’s gaze on us and looked over to the door. He was enjoying the show and nodded in approval this time. My hands roamed all over Sara’s body, but I couldn’t get enough of her ass. I caressed at first then began to give it little spanks. Each time, she would yelp with subdued delight and smile. I bit her lower lip, kissed her neck, then moved up to hear ear.
Me: You are so fucking naughty, you know that?
Sara began grinding her pussy into me. And when she felt my cock begin to stiffen, she grabbed my hand and brought to the crotch of her teddy. Even through the fabric, I could tell how turned on she was. Sara pulled them to the side, so I could get a better feel. I looked over to Kevin once more, but he’d taken a step back from the door at this point. From this angle, he could see us, but we couldn’t see him. He peeked his head in for a moment.
Kevin: It’s OK!
Earlier Kevin had expressed a fantasy of being a voyeur while Sara and I played, and we were all too happy to fulfill it. Sara pulled her teddy off then moved onto my jeans. She’d shaven a perfect landing strip into it during her shower, since I told her it was my favorite. Seeing it sent me over the edge. All of the available blood in my body rushed straight into my cock. When she climbed back on top only the thin fabric of my boxers, the very ones she’d picked out, separated me from her dripping wet pussy.
At this point, Kevin had seen enough. He entered the room, walked over to the side of the bed, and pulled down his boxers. While still straddling me, Sara leaned over and began to suck his thick cock. I laid back and enjoyed the show while using my thumb to rub circles around her clit. After a bit, Sara had also had enough. She climbed off me and got on all fours with her ass facing Kevin. He entered her from behind, and without warning, she pulled out my cock and put it in her mouth. For the first time, Sara was being filled from both ends at once.
I got up on my knees on the bed to give her an easier angle. With each thrust, Kevin forced her mouth farther and father down my shaft. After a bit, we found an even rhythm, gently pushing her back and forth between us. Sara was getting close, but she didn’t want to cum just yet. She turned around and positioned Kevin against the head board then bent over and licked her cum off his cock. Sara’s amazing ass and perfect pink lips were absolutely torturing me as I watched them. I wanted to take her right then, but I figured sex was most likely out of the question and didn’t want to push it. So I had to do the next best thing.
I walked into the front of the apartment where I’d dropped my duffel bag and returned with my riding crop. I teased Sara with love taps up and down the back of her thighs, calves, and the bottoms of her feet. Soon I graduated to stinging each of her cheeks.
THWACK.
THWACK.
Sara: AhhhhMmmmm.
It was difficult to hear her moan with his cock filling her mouth. I continued giving her red marks until the mere anticipation of not touching her drove her wild. Though it was dimly lit in the room, I could see she was dripping.
Kevin didn’t last much longer before he pulled out and covered her chest. I later learned Sara wasn’t into swallowing, but she absolutely loved cum on her face, tits, and especially having it rubbed into her skin.
After Kevin finished, Sara flipped on her belly. She had one of the more unique ways to reach orgasm, one that I hadn’t encountered before or since. Like most women, she required heavy clit stimulation. But rather than rubbing her clit directly, she climaxed from direct pressure applied to the entire area. Kevin inserted his thumb into her pussy and used his palm to apply said pressure. While Kevin worked his technique, I watched with fascination until he looked over at me.
Kevin: Hey, do you want to finger her with me?
This was brand new territory. I’d always had a double-penetration fantasy, but it usually didn’t involve fingers. I didn’t see why this should be any stranger, so I leaned over and slid my middle finger inside Sara above Kevin’s thumb. Sara’s pussy was soaked, and after a few minutes, Kevin nodded toward her ass.
Kevin: Touch her back. Feel how warm it gets.
I placed my palm above her ass. Sure enough, it felt as though she’d just removed a heating pad from it. She was getting closer and her little whimpers turned into full moaning. Sara pushed her ass high into the air and came with such force that her body, and the bed, began to shake. It was beautiful and sexy and naughty all at once.
Sara flipped over on her back and cheeks were flushed red. A smile tattooed to her face. Once her orgasm amnesia wore off and she form full sentences, Sara informed me that I was the only one who hadn’t cum yet. And she intended to fix that. Being the unselfish lover she is, Sara brought me to the side of the bed and got back on all fours. Soon after Sara whipped my cock back into playing shape, Kevin was ready for round two. He got onto his knees and entered her from behind. This time Kevin helped establish a rhythm by pushing the back of her head farther onto my cock. Sara would later tell me over text this moment was a personal highlight for her.
A few minutes aboard the fuck and suck express, Kevin pulled out and came on her back. Right after, she looked up at me and said the four most beautiful words in the English language.
Sara: Cum on my face.
I pulled out and edged myself until I was ready. Kevin got into a better position to watch. He had seen her take many facials, but this was undoubtedly an angle he’d never seen before. I gave her a two second warning before I shot rope after sticky rope on, around, and over her face. Some landed on the intended target, most ended up on the bedsheets. But worst of all, a portion hit the corner of her eye. Sara rushed into the bathroom to wash off, and I felt like a monster.
I dressed, cleaned up, and packed my things while Kevin and I reflected on a (mostly) successful night. I’ve never found the post-coital conversation to be awkward. After seeing someone naked and at their most vulnerable, small talk is the easiest of hurdles to jump. Sara emerged from the shower minutes later, right eye bloodshot, and I apologized for the mishap once more.
Sara: Don’t worry, it’s not the first time, and I did kind of ask for it…
To her credit, Sara had a great attitude to go along with her great ass. We wrapped up the night and hugged one another goodbye. They handed me a bottle of water for the road, and I snuck past the neighbor’s window, wondering if he had any idea what had just occurred in the unit above his. I was sure he would send a wall of text to Sara if he had.
The next day I received a long apology text from Kevin. In his excitement, he had snapped a few photos and a short video of Sara and I. He felt awful for not telling me, and the guilt had forced him to reach out. He promised none contained our faces and he got a little too into the role of voyeur. I thanked Kevin for his honesty and told him it was fine under one condition: he had to share the photos with me. Kevin agreed and promptly sent them over. Though the three of us have taken many pictures together since, to this day they remain some of my all-time favorites. Kevin and Sara became the first couple I saw regularly as a single male, and that night would be the first of many more to come.
Source: reddit.com/r/gonewildstories/comments/5xflue/free_drinks_facials_mfm_group_light_bdsm
Hot story, well written, and sounds good that you’ve hit it off well enough to stay in touch (and rather more than just touch ;) ) since. :)
Cheers for sharing!
Care to share the pictures? ?