An Interesting Proposition

It was on a slow Friday afternoon after I had ran out of motivation to work, about an hour before quitting time. I spent the last hour of work on a dating website, swiping mostly left. I was looking for something to do for the weekend. After 45 minutes or so I came across something different. She was a fairly attractive redhead with a good figure and a pretty smile. In fact she was beautiful, in a fiery sort of way. The biggest issue I had with the picture was the guy with his arms wrapped around her in a very familiar sort of way. He was tall and lean and he looked to be in his early 40's with a touch of grey in his dark hair and beard. I decided to investigate further before I picked a direction to swipe. This is what her profile looked like.

Hello! My name is Haley, and I have a different sort of proposition for you. The guy in the picture happens to be my husband, he also happens to be top. We are looking for a cool guy to go have a nice dinner with and if we hit it off some drinks afterward. Here's the catch though he wants to date you, I don't. Now I know this ad isn't for anyone, its for the few of you that are bi-curious but have never tried anything yet. I know you guys are out there, even though you won't admit it to anyone (or even yourself) and we want you! We promise we will be as discreet as possible, my husband prefer no one else knows too. Here's how it will go, we meet at a restaurant and pretend we're old friends. You have dinner on us and if everything goes well we will go for a few drinks afterward. You can go as slow as you want and only as far as you feel comfortable. And here's the best part! If you decide that you weren't as curious as you thought you were, just say the word and I will step in and we can pick up where my husband left off. If you decide that you enjoyed my husband, then we could possibly work out a long term arrangement. Some things to note.

You must be:

Actually bi-curious and not bi-experienced

At least average attractiveness

Be sane and fun to hang out with

If it goes this far:

Be a complete bottom (he will not bottom and at best he might stroke you off)

Be at least somewhat submissive (he will not force anything but he will take the lead)

Be ABSOLUTELY STD free!!

Understand that this may only be a one night stand

I read and then re-read the profile, my eyes occasionally flitting back to the photo. I was curious, both sexually and about this proposition. It really was a great way to finally try something that I had always wondered about. I had before considered trying to find a couple to try it in a three-some but as much as I had fantasized about it, I had always held back because I wasn't sure I was going to enjoy it. I swiped right and thought to myself I doubt they will respond anyway. The clock hit 5:00 and I left my office. Before I made it home, I felt my phone buzz in my pocket. I waited until I walked through my door to check it. It was a notification, I dropped everything on the counter and unlocked my phone. Nick and Haley had liked me back and had sent me a message. I quickly read it then replied and before I finished making dinner (frozen dinners take forever in the oven) we had set up a date for tomorrow night. I ate dinner then took a long shower, thinking about Nick more than I should have.

The next day passed slowly and I put off getting ready until an hour before the date. I never understood what took women so long to get ready, it take me 15 minutes to shower and another 15 to be ready to head out the door. When the time came I showered quickly to avoid a repeat of what happened last time I took a long shower. I got ready and then spent the next 30 minutes watching mindless You-tube videos till time to leave. I pulled up to the restaurant and headed inside, I immediately saw them as I reached the Please Wait to be Seated sign, I continued passed the sign without slowing. My heart was beating like a drum and I felt that if I stopped that I might decide to turn and run.

They both turned at the same time as I approached the table, they flashed smiles in recognition and I returned a nervous one back. They gestured towards the empty seat across from Haley and sharing an adjacent corner with Nick. I sat quickly and they introduced themselves. We quickly fell into easy conversation, Haley was upbeat and always smiling and Nick was engaging and funny as he relaxed back in his chair. By time we finished dinner we were laughing and joking like we actually were old friends. Nick downed the last of his third scotch, set down his glass and let his hand fall down to land in his lab. He said something funny and I turned to smile at him, he smiled back and his eyes glanced down at my lap and then back to me. Our eyes locked and I understood what he was asking and in response I brought my knee over right next to his. His hand casually slid across his legs and drug his fingernails across and up my thigh until he let it drop slightly above mid thigh. My jeans crotch tightened in response and I quickly took a drink to hide my sudden blush. It wasn't long and Haley was ready to head to the bar so Nick pulled out his wallet and dropped a 100 on the table, Haley stood up after him and I followed suit.

We walked out of the restaurant and up to a white Benz. Nick hit the unlock button on his keys but instead of grabbing the driver's door, he grabbed the handle to the backseat and swung the door open. Haley walked up to him, gave him a deep long kiss and took the keys out of his hands and turned towards the drivers seat. Nick flashed a smile at me, climbed into the back and slid over to the middle seat. He gave the seat next to him a pat and after a moments hesitation I started towards the car. I climbed into the backseat of the GLE 550 and looked over at Nick, he had both arms spread across the backrest of the seat. I slowly sat back until his arm was gently pressed against my back. I could feel the heat of his arm soaking through my button up shirt. I shut the door and Haley put the vehicle in drive and started pulling out of the parking lot.

Nick turned to me and started telling about the bar we were heading to I watched his lips closely but wasn't paying attention to his words. He noticed where my eyes were and slid his hand up my neck from my shoulder and onto the back of my head. His fingers tightened on my hair as he held my head immobile. I closed my eyes as his head started moving forward and I felt a warmth on my lips that I knew was from his. My head reeled as he kissed me and instinctively I started kissing back. He parted his lips and sent his tongue to explore my mouth, the scruff of his beard tickled my cheek. Instantly my blood flashed to boiling and I had to place my hands on his broad chest to keep my balance. He kissed my deeply with one hand tangled in my hair tilting my head to compliment his, I felt his hand brush my leg and then his fingertips on my inner thigh.

I barely noticed the low moan that escaped my lips. He took the sound as encouragement and he started stroking up and down my thigh, my legs spread wide for him of their own volition but he did not take advantage of the additional access. Instead he grabbed a hold of my leg right above the knee and used it to turn me to face him more directly, pulling it over his knee and dropping it so that my leg was hooked over his. Then his hand starting back up my leg, this time on the outside until his hand slid up and cupped my tight ass. He slid forward on the seat taking my body with his until I left the seat entirely and my thigh slid down across his. He dropped his hand out of my hair and grabbed my other cheek and pulled me in tighter until my crotch was nestled up tight against his thigh.

He continued to kiss me deeply as he played with my ass. Pulling me closer and relaxing, forcing me to grind back and forth on his leg until I was breathing heavily. He let go with one hand and grabbed my right hand that was still clutching his chest. He started inching it down across his pecs and onto his abs. I got the idea and he let go as my hand continued its downward journey. I let my hand drop until it was full of the bulge that was in his pants and when I started to stroke across the material of his chinos, he let out a low moan and redoubled his efforts to dominate my mouth.

He let me continue to tease him through his pants for a few minutes until I had him unbuttoning and as he started to unzip, my hand greedily dipped inside. I brought out his throbbing cock and began to slowly stroke it. I heard a muffled gasp from the drivers seat and remembered his wife was still in the SUV with us. I hadn't noticed until then that we had parked. I hesitated for a second but he quickly brought me back to him when he stopped kissing my mouth and moved his mouth down to my throat. I closed my eyes and tilted my head back as he buried his head into the curve where my neck met his shoulders. He stopped playing with my ass for a few seconds and undid the button of my jeans before his hand returned, dipping down inside of my underwear this time. The heat of his hands over my body made me to start stoking his hard cock faster, he brought his fingertips down following along my crack until they brushed my asshole. I moaned and shivered simultaneously and with his other hand he grabbed the back of my head again and brought my eyes back down to his. He paused for a second as his fingertips traced circles around my anus and then I closed my eyes and parted my lips and started to lean forward to kiss him again. His fingers in my hair brought me up short and instead he tilted my head even further until I was staring at his huge cock. His hand met little resistance as he pushed my head down towards his masculinity and I slid off of his leg and back onto the seat. I let go of his cock and moved my hands to his thighs for support. My lips parted to accept his cock and he slipped his hand out of my pants and up my back to the back of my head. The added pressure pushed my head down until the tip of his cock was spreading my mouth wide.

My tongue flicked of its own volition to taste the pre-cum already leaking from his cock as my lips consumed the head of his cock, he let out another moan and slowly pushed my head further down, my mouth quickly filled up with his thick cock and I had to stretch my jaw open wide to give him full access. About halfway down his shaft, the tip of his cock was pressing against the curve where the roof of my mouth met my throat. He pushed a little harder, wanting me to take all of him but I couldn't and when I convulsed from gagging, he let up pressure. I explored along his shaft with my tongue and I began to make small movements up and down. His fingers tightened in my hair again and he took over, first pulling me up by the hair until the tip passed back over my lips and then pushing me back down. I let him guide me as I did my best to tease his cock.

Once I got into the proper rhythm dictated by his hand, he let go with his other hand. It touched back down at my waistline and he slipped it back into my pants, this time heading straight down the center until I felt a cool, wet sensation across my hole. I wasn't sure I was ready to be violated so I let go of one of his legs to reach back and move his hand but before I could get there, he slowly but firmly pushed his finger inside of me. My hand froze and the mixture of pleasure and pain caused another moan to rip from my throat, this time muffled by a mouth full of hot throbbing cock, prompting him to push even deeper inside. My hand quickly dropped back to his leg to brace myself as I was roughly penetrated and squeezed tightly. Once his finger was all the way inside of my I could relax my grip, my mouth still doing its best to please him.

Ripples of pleasure emanated from his finger as he started to slowly move it up and down but not quite enough to break the grip my anus had on his knuckle. He uttered a breathy whisper "Your ass is so tight..." and in reply I slid my hand to his balls and started to fondle them. I could hear whimpering coming from the front seat so I stole a glance to the front of the vehicle. I could see two eyes in the rear view mirror watching me go down on her husband and Haley's shoulder moving back and forth as she played with herself. He moaned again loudly and my eyes returned to the job at hand and then tilted further to look up at him. His head was thrown back against the headrest and his mouth was open, his breaths coming sharp and fast.

I realized he was about to cum and I wasn't so sure I wanted him to cum in my mouth, I began pulling back away but his fingers seized my hair even tighter and he forcefully pushed my head back down on his cock. When the head of his cock was tight against the back of my throat, his whole body stiffened up and instead I did my best to try to accept his load. He pulled his finger nearly out of my ass, went completely still for a second before suddenly shoving it back in with the first convulsion of his orgasm.

On his second convulsion, hot semen hit the back of my throat and I desperately tried to swallow to keep from choking before he mercifully let my head go. I quickly went to work bobbing up and down as he shot load after load into my mouth and down my throat. I did my best to swallow it all but a little escaped out of the corner of my mouth. I slowed to a stop as his body relaxed back into his seat. His finger slowly slid out of me and I dared to look up at him in embarrassment. He stared down at me and when our eyes met he smiled and let his hand drop out of my hair and down onto my back. His eyes held mine and I smiled in return, cum still running down from the corner of my mouth. His hands brought me back up to a sitting position before moving up and cradling my head. His index finger brushed up from my chin along the path his semen left, he gently pushed down on my chin to open my mouth and slipped his finger in. I stared back at him as my lips closed around it of their own volition and I flicked my tongue against it to clean his cum off of it. He pulled his finger out and I obediently swallowed. He kissed me again, softly this time and only on the lips. He probably didn't want to taste himself but he tasted so good to me. Haley put the SUV in drive and started driving us back to my car.

As I kissed him I wondered if this was the end of the date. It gave me a mixture of disappointment and relief, I didn't know what I wanted to do. He stopped kissing me when we arrived back at my car, I looked around for the first time since we left the restaurant. I was a little disappointed as he told me goodnight and kissed me again beside my vehicle, his hands on my ass again. I told him goodbye and climbed wondering if he wanted to go out again. He must have sensed my question and asked me if I wanted to do this again next Friday. I told him yes and he nodded in affirmation, he said goodnight and closed my door. I put my car in drive and headed home, the musky taste of Nick's cum still strong in my mouth.