Author’s note: All characters depicted in this story are completely fictional and all are over the age of 18.
Editor’s note: story contains gay male scenarios.
“Couple Looking for Adventurous Male Playmate,” the subject line read. “Bi-Curious Newcomers Encouraged.”
There was something about the headline or maybe the large breasted faceless woman in lingerie in the poster’s profile picture that made me take interest in this headline over the many other singles and couples looking for playmates.
Two years earlier, my ten year marriage to my wife had dissolved. We got married too young and were too dedicated to our own freedom to keep the union steady over time. Early in the relationship, we explored every straight laced sexual fantasy we could come up with. We used toys and tied each other up. We sent naughty pictures from work bathrooms or hotel elevators. Eventually, that wasn’t enough so we sought out other couples with whom to explore other boundaries.
There were always rules, though, to keep one of us from becoming “jealous”. She didn’t like for me to kiss other women and we always had to be in the same room even if we weren’t both participating. One time, after she begged for months, we had a threesome with a man in which the other man and I exchanged brief handjobs. I did it for her, having little attraction to other men in that way. We put on a good show just as she and other women had put on a good show for me or the other woman’s husband. It seemed like the women were into it, and I watched my ex-wife orgasm thanks to another woman’s hand or tongue on many occasions. It all felt like a weird dream, though, and we eventually lost interested in sharing intimate moments with other couples and then, finally, each other as we drifted apart.
Now freed of the bonds of marriage, I had spent a year just traveling and trying to reconnect with old friends or missed female connections. In that first year, I had sex with my share of partners, mostly old female friends who also found themselves divorced and in their thirties. When I shared the story about exchanging handjobs with another man with one of those friends, she mentioned she that she had the same fantasy for years. What she and her ex-husband found was that he liked to fool around with other men as long as she was present. He had never pursued a man before she came along, nor did he ever find them attractive if he was just on the street or in a bar, but something about a no holds barred approach to sex with partners took their sexual play to another level.
The idea stuck with me, for some reason. I didn’t ever think of other men in a sexual way but, I guess after you see enough porn or watch enough straight sex in person, your mind starts to wander. When I would watch gangbangs or double penetration porn scenes with multiple men, I’d find my eyes drifting to watching the men enjoying jacking off while they watched the woman at the center of the action. With some help from some anonymous internet posts, soon my attention drifted to heteroflexible porn, where men enjoyed when a woman took both their cocks in her mouth at the same time or rubbed their erections together at the moment of ejaculation.
Suddenly, I found myself intrigued by the possibility of a sexual relationship with other couples with less rules. There was no wife to get jealous or judge me, so I thought, “Fuck it. What’s it going to hurt if I just see what happens?”
When I stumbled on the post by “CocklynCple”, I instantly connected that to Brooklyn and figured they weren’t far from me and the worst they could do was say no. From my time spent sharing my ex-wife with other couples, I learned that other couples liked my muscular but not too intimidating frame and that my dick was big enough to draw some stares but not so intimidating that it made other men jealous. The profile picture was taken from a side profile and it really showed off the woman’s curves. She had big full breasts and nicely rounded ass. My ex-wife had dropped a ton of weight in college and, ever since, was skinny as a rail. I think it was why I started drifting toward curvy, but just short of voluptuous, women as we started swapping with other couples. I liked burying my face in their tits and feeling my pelvis bounce against their ass.
“Saw your post and thought I’d reach out to you. I’m an athletically built guy in his early-ish thirties. Divorced. Swapped partners a few times when I was married but never hooked up with a couple on my own. Just looking to connect with adventurous couples and thought your profile picture looked stunning.”
Before I attached a photo to my message, I made sure to do a few push ups and crunches. I posed for a selfie in my mirror so I could catch what I thought was a fair representation of my body from my neck down to the top of my pubic area. I fired off the message with the headless and cockless photo and waited.
I spent the next day at work kind of a worried mess. “What if I’ve messaged one of my ankara dansöz escortlar coworkers?” I worried. “How awkward would that be?”
I at least made sure to register the account I sent the message from under an alternative email address I created for just such an occasion. That meant I also had to wait until I got home to check that email account. I didn’t want an IT guy snooping on me to discover what I was up to, even if I knew my company would consider that information confidential – confidential to the IT team and HR, at least.
“Hiya, handsome!” The subject line of the couple’s response read. My heart was pounding as I slammed my mouse button to open the message.
“Honestly we were looking for a total newbie, but we I liked your picture so much that my hubs agreed to go for it. When you say ‘swapped partners a few times…’ did that mean you hooked up with guys, too, or just the other women?”
And there it was. The moment of truth was upon me. How could I hook this couple without offending them or misleading them? I didn’t want to really “hook up” with a guy. I just thought it might be hot if the woman in the threesome was totally uninhibited and that, in turn, could lead to some sexual boundaries being pushed. I had no real idea how far I’d go, so I decided to undersell with the potential to overdeliver for them.
“Awesome to hear back from you. Sorry if this reply comes too quickly or too late – I don’t know the usual protocol. I never hooked up with other guys, but I’m game to see what happens. Hopefully we would all just click and we could have a great time together?”
I took a deep breath and fired off the new message. To my surprise, the response came back within the hour.
“Hey sexy – Yeah, we just want to have a great time. No set expectation but we look forward to bringing you back to the dark side. Lol. Here’s a little more of me to tantalize your further. Can you text us to let us know your serious about meeting up and we’ll set something up?
-Alice and Tom”
I noticed the website’s messaging system had an attachment. I opened it it to find I was looking down into the eyes of a very attractive brunette woman who looked just a few years older than me. She had a nice round face and thick wavy shoulder length brown hair that matched her eyes. She was on her knees looking up into the camera, with her hand around a thick partially erect penis and her breasts were bared. I looked down at her melon shaped cleavage that fell low on her chest. Her oval-shaped areola ran vertically on the tips of her breasts with small dark brown nipples at the center. My cock jumped a little as I looked at the photo with this perspective that made it look like she was holding my cock, or at least a stunt cock, and had trouble preventing myself from jerking off before I could get to my phone.
“Here’s my number. Thanks for the lovely pic. Here’s my beautiful smiling face so at least we’re almost even. When do you want to get together?
My fingers flew across my phone screen and then I took several selfies of just my face until I found one I was happy with. I’m certainly not George Clooney but a few lines on my face have actually helped frame up my face a little better as I’ve aged and I’ve always been told I have a nice smile. Braces as a kid really worked for me and I learned how to show off how perfect they turned out without being too toothy.
“Awesome. Sounds like we’re neighbors in Bklyn but we don’t like running into ‘real’ friends on play nights so can you meet us at the hotel below in Queens? Tomorrow at 9 ok? We’ll bring booze.”
“Queens? The fuck?” I thought. I understood, though. I wouldn’t have wanted some of my college friends prying into my adventures with my ex-wife, for fear of too many questions or because I just thought they were hideous monsters and didn’t want them pushing in on our sexcapades.
“Sounds great. See you two there. Remember to txt me the room # when you check in?”
Short and sweet, just as I hoped. The second the meetup was agreed to I felt myself getting hard again. The image of Alice’s tits wouldn’t leave my mind. I wanted to stick my cock between them and rub until I nutted all over her cleavage. I pulled my shorts down and rapidly pumped until I came in my palm. Normally I could last quite a while by edging and changing speeds, but I felt like I needed the relief. Maybe I wouldn’t nut immediately upon entering the room if I got a little of the fantasy out of the way now, I thought.
The following night, after work, I showered and spent some time cleaning up my manscaping so my shaft and balls were nice and clean but maintained a short layer of hair in other areas so I didn’t look like a child. I liked the feeling of the cool air in the bathroom on my cleanly shaved genitals as I walked out and gave myself just a couple strokes to enjoy myself before I moved on. Outfit after outfit went on my body and then off before I realized I needed to get the hell to ankara saatlik veren escortlar the subway before I ended up late for our first “date”. In the end, I kept it simple with a black t-shirt, jeans and a pair of Timberlands that made me look a little taller and tougher than I actually am. I threw a few condoms, a tube of lube, and a bottle of mid-shelf whiskey into a small duffle bag and darted for the door.
Twenty minutes into my trip, I got a friendly message with a hotel room number. In another twenty minutes, I was standing outside the room, hand trembling a little as I paused mid-knock. I didn’t know what I was scared of: I had seen couples fuck in front of me before and had let people watch while I fucked my ex-wife but, somehow, this felt different. It sounded like some upbeat top 40 song was playing behind the door. I heard a woman laugh and then swallowed hard and rapped on the door a couple times.
When the door swung open the brunette from the anonymous messages I was standing in front of me. She was wearing a white tank top that did little to hold back her filled out mammories or hide her dark pointy nipples. Her right arm stretched up the inside of the door and her left hand held a tumbler with brown liquor.
“Here he is!” Alice announced in a chesty friendly voice.
“Nice to meet you, too?” I shyly replied.
“Get on in here!” she said, hugging her free arm around my waist and ushering me into the hotel room.
They had picked out a mid-range hotel, nothing too swanky but certainly better than an hourly rate motel. The room comfortably fit a king sized bed, a chest of drawers with a tv on top, and a couple small armchairs next to a little round table on the far wall.
I spotted a tall middle aged man, probably in his mid-forties, with dark brown, almost black, hair and a slightly broader frame than my own standing near the little table. His hair parted naturally to the side and he had a sharp jawline that met a square jaw at the bottom. His long sleeved collared shirt hung on the chair with a nice pair of loafers under it and he was dressed in a tight white undershirt and a pair of black dress slacks.
“You must be Tom,” I said and extended a hand.
“Great to meet you, Bobby. Thanks for meeting up with us.” He spoke in a distinctly upper class New York gravely tone as we shook. “Got anything special in there?”
“Just the usual I said,” feeling a little embarrassed about dragging my give-away duffle bag into the room.”
“I’ll just tuck it under here, then,” Tom replied as took my bag and placed it under the small table. “Let me know if there’s anything in here you find we don’t have. Need a drink?”
I looked at the very expensive bottle of small batch whiskey on the table and decided not to mention the mid-range bottle in my bag. “Sounds great.”
As we sipped on the whisky they poured Alice danced around the floor in time with the music. She was wearing a short pair of khaki shorts that hugged her thick bottom tightly. Her breasts jiggled and swayed as she moved and Tom and I both took time to appreciate her curves as they passed between us. I sat on the edge of the bed while Tom found a home in one of the chairs. We made small talk about the music or movies we’d recently seen. I was glad they gave me a minute to decompress from the commute and drink a little liquid courage.
“OK, no more talk. Night’s wasting,” Alice playfully nagged.
As the music shifted to a sultry R&B track, Alice sashayed over to Tom, placed her hands on his shoulders and then leaned down to plant a slow passionate kiss on his lips. She gyrated her hips in front of him. It was pretty hot to watch her ass sway back and forth at my eye level from just a couple feet away. She turned around and used the arms of the chair to lower her ass into Tom’s crotch, locking eye contact with me while she shifted her butt in his lap.
“You like what you see, Bobby?” She asked.
“Definitely,” I cooly replied.
“Come over here,” she said.
I stood and crossed the short gap between the bed and the chair. It took a little effort but I managed to kick off my ankle high boots without embarrassing myself. I stood straight up in front of the chair, letting Alice appreciate my full size standing over her and then set my glass down on the table. She was looking up at me and Tom was watching her take measure of my body.
Alice ran a hand up my crotch and to the bottom of my t-shirt which she pulled upward with the stroke of her hand. She kissed the skin just below my belly button with an open mouth, taking time to suck on it for a moment. I could feel a shift in my pants just from watching this sultry woman work.
“Come up here, Tom,” Alice said as she rose from the chair and took his hand.
I backed up toward the bed to make room for the couple on the floor. She turned to face Tom, wrapping her arm around his neck and standing on her tiptoes to reach her mouth to his. I felt a hand groping at my waist and ankara azeri escortlar Alice found my hand and pulled me toward her back.
It was now or never, I thought, and I slipped one hand into her back pocket and used my palm to cup her ass cheek while her hips continued to sway. That didn’t meat Alice’s expectations, as it turned out, and she pulled my hand from her pocket and then guided it into the top of her waistline.
I caught the hint and extended my hand down the back of her shorts, kneading and caressing the meaty flesh inside. She was either wearing a thong or no underwear at all, as I was caressing bare skin. My cock was rising just a little more and I pressed my crotch into the middle of her thick cheeks so she could feel my excitement. With my left hand, I reached around and underneath her tank top. She sighed as my hand cupped the underside of her heavy breast and I found Tom already had a hand on top. I pulled away for a moment after I made contact with Tom’s hand but he pulled it back toward his wife’s breast.
“There’s plenty to go around,” he whispered without breaking his exploration of Alice’s breasts.
After a few minutes of Alice and Tom making out while we fondled her breasts, Alice dropped her hands to her waist and I watched her arms shuffle as she unbuttoned her shorts. With a flip of her hands, her shorts dropped to the carpet and I had a direct view of her bubble butt below me. My question was answered as she wore black thong panties with just a single thread cutting between her thick cheeks.
Next came the sound of a belt jangling, then a zipper opened and Tom’s slacks joined Alice’s shorts on the floor. I watched over her tan freckled shoulder as Alice slipped a hand inside the fly on Tom’s tight black briefs and then the hand emerged holding his stiff pink cock. It was circumcised like mine and looked like it matched my impressive length with just a little more girth.
With one hand, Alice stroked Tom’s cock and, with the other, she reached back and fumbled for my belt buckle. I reached down to give her a hand but she pushed my hand away and then found her mark. She opened the buckle, slipped the belt out of the way and then found my zipper and pulled it to its base. With my fly wide open, her hand slipped over my waistband and down to my thickening shaft.
“Oh, that feels great,” I whispered.
Alice turned her body to the side, so we could watch while she stroked Tom’s shaft in her left hand and my growing member in her right.
“Two big cocks, just for me,” Alice bragged.
The busty woman lowered to her knees and pulled Tom and I closer together. Her mouth encircled the tip of Tom’s’ penis head, and then she bobbed on his shaft a few times before sliding her lips across the bottom of his flesh until her lips found my mushroom shaped head just inches away. Her hands reached up next to her face and pulled at our cocks until Tom and I straddled up to each other so his penis head sat on top of mine. Alice took the two heads with her lips and sucked at our merged flesh. After a moment of popping her lips on the tips, Alice stood up.
“Carry on,” she encouraged with a wave of her small hands.
“Do you mind?” Tom asked as his fingers reached for the penis tips in the middle of the semicircle.
“Not at all,” I whispered as I felt my heart began to race. I couldn’t’ believe how turned on I was at the sight of a strange man reaching for my cock, but I think what really turned me on was the thrill I got doing it in front of this insatiable woman with those big luscious tits.
I continued to stare down at the hand rubbing back and forth from my cock to his with the occasional glances to Alice. She was caressing her erect nipples under her tank top and then lowered a hand into the front of her panties were she rubbed herself beneath the black lacy fabric.
“Guys, this is so hot, but I don’t want you to forget I’m here,” Alice said.
“As if we ever could, Tom replied, dropping his hold on our pricks and reaching for Alice’s breast before locking his lips onto hers again.
My hand carefully reached forward and I returned the favor, slipping my fingers around the base of Tom’s meaty shaft and sliding my hand from the base of his dick all the way to the base of mine and back again. His penis was still extended between the fly on his briefs so I could only get so far before reaching the thick fabric.
“Oh, God!” Tom exclaimed as he buried his cheek into Alice’s thick chest.
“Now that is awesome,” Alice said with a smile while she watched me sharing a jerk with her husband. His erection was a little softer than mine when I started but stiffened up quickly with help from my grip.
“Don’t waste him, yet,” Alice said after clutching Tom to her breasts and watching my hand for a couple minutes.
Alice took Tom by the hand and led him to the bed. She bent over and pulled her thong to her ankles before climbing up on the bed. Tom circled around to the side of the bed, dropped his briefs to the floor, revealing a bare set of plum sized balls, and then offered his cock to the side of her face. I dropped my pants and boxers and stood there, stroking my cock while I watched Alice’s fleshy yet toned butt cheeks jiggle while she began pumping her mouth on Tom’s hard shaft.