A Dinner Party Ends Unexpectedly

I like to write about events as they occurred, and not all go according to plan. This is one of those times.

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This story starts like so many others, on an online dating app. It was my late 30's, oh so close to 40, and I found myself single.

Being nearly 40 and single is far different than being single in your 20's and 30's. You begin to slow down, and want more meaningful relationships, rather than the wild times of the last 20 years.

Leo and I met on Ok Cupid. An app for people looking for relationships more than quick hookups. Leo must have liked my profile, as he messaged me with a brief introduction. "Hi, your profile caught my eye. I see you like to travel. Where is your favorite place to go?"

I clicked on the small picture of Leo next to his message. Opening his profile I was taken aback. Leo was a gorgeous man. He was 10 years older than me, and I have to admit older men have always been weakness of mine.

The profile stated he was 6' 2", hard to judge from a picture, but if accurate he would tower over my 5"8" frame. He had a full head of wild hair, a brownish color, and a slightly receding hairline. What struck me most was his build.

Leo was not overly muscular, but you could tell he kept in great shape. He looked like a football player, with a slight belly. I could only imagine his powerful arms pinning me down as he had his way with me.

His interests aligned with mine well, I noticed he had played rugby in college. I thought to myself that's where he gets his muscular physique. Feeling a twitch in my cock, I messaged him back.

I replied that Vegas was my favorite destination. I travelled there frequently, usually once a month. Leo responded to my message that he enjoyed Vegas as well, but had only been a couple of times. Maybe I could show him around sometime.

I was hooked, I would love to show this gorgeous man Vegas, starting with the hotel room. We began talking back and forth, each message becoming more flirtatious than the last.

After a day or two of messaging, Leo asked me for my phone number. I happily responded, and later that day we talked for the first time. Leo had a deep voice that just oozed masculinity. We spent some time getting to know each other, with some flirty undertones thrown in.

Leo told me he was having a get together on Friday. Him and two other couples. He asked if I wanted to come over and join him to round out the numbers, and maybe afterwards spend the night.

Heart racing I accepted, although I was a little nervous to meet so many new faces. Friday arrived and I raced home from work to get cleaned up, and pack a few things in case his offer of spending the night was legit.

Leo lived on the second floor of a two story condo complex. His condo was a corner unit with two bedrooms, and a small balcony. I knocked on the door and Leo greeted me warmly. Another couple had already arrived, and one more was on the way.

Leo introduced me to the couple that arrived early. They were both late twenties or early thirties based on their appearance. One was tall and thin, and the other just slightly shorter with a more muscular appearance. Apparently they knew Leo from a mentorship program they participated in.

Within a few minutes the other couple arrived. A tall muscular man wearing a t-shirt, and tight jeans that showcased his bulge. With him was a petite brunette woman in her mid twenties that he introduced as his girlfriend. That took the wind out of my sails, as I had hoped to see more of that bulge at some point.

Leo had planned an entertaining evening of dinner and games. Dinner consisted of a chicken dish that Leo had prepared himself. Following dinner we cleared the table and sat down to play Cards Against Humanity. I had never played before, but it was apparently a favorite of this group.

I picked the game up quickly, and we played several rounds late into the night. As the evening grew late, the other two couples took their leave, thanking their host for the enjoyable evening.

Leo and I were the only two left. He asked if I enjoyed the evening, to which I replied I had so far. He said he knew what could make it more enjoyable. I smiled as he took a step towards me.

Leo wrapped his arms around my neck and leaned in slowly. He kissed me deeply, his lips gently pressed against mine. He took my hand in his and guided me into the bedroom.

He led me to the foot of the bed. He reached down and pulled my shirt over my head leaving my chest exposed. He placed his hand on my chest, rubbing his thick fingers along my nipples causing them to become erect.

My hands moved towards his chest, tracing the contours of his muscled body. Slowly I began to unbutton his shirt. Marveling at his chest as I worked my way downwards toward the last button. His chest was well defined with wisps of the same brownish hair, but touched with speckles of grey.

Leo continued to work my nipples during this time, twisting and pulling sending waves of pleasure through me. I could feel my pants tightening, my cock ready to break free.

I unbuttoned my pants to provide some breathing room. Leo noticed and quickly moved his hands downwards sending my pants to my ankles. I was now exposed with only a pair of boxers remaining.

Leo ran his hands along my boxers, causing my cock to twitch. With a yank he removed those as well, my cock getting caught and bouncing back into my stomach dribbling a stream of pre-cum.

Leo traced his finger along the tip of my penis, taking the pre-cum onto his finger, which he then pressed between my lips. I greedily sucked on his finger causing a slight gasp from Leo.

Leo took a step back and said "Let's see how you do on something bigger" at which point he unbuttoned his pants and removed them to unleash one of the nicest cocks I had ever seen.

Leo kept his pubes trimmed, so his cock looked bigger than it probably was. It was long and thick, at least six inches thick semi hard. I wondered how big it got fully grown.

I did not have to wait long to find out. Leo placed his hands on my shoulders, nudging me downwards. I dropped to my knees, his cock just in front of my face. I reached out with my right hand, gripping the base of his shaft as I traced the mushroom head with my lips.

Moving my hand to his balls, I worked my tongue down the shaft of his penis, and back up again. I did this several times coating his entire member in my saliva. Returning my grip to is shaft I positioned my eagerly awaiting mouth above the tip and plunged it deeply into my mouth.

Leo moaned and his cock twitched in my mouth. His hand came down to my head encouraging me to go deeper. I sucked until his cock gagged me causing my to pull back a bit. Taking a breath I lunged my throat down on his cock once again as far as I could go. Leo's moans intensified and asked that I stop, he was not ready to cum just yet.

Leo stood me up and pushed my onto the bed. I lay on my back as he climbed onto the bed and rested his body on mine. As our cocks rubbed against each other, he leaned in to kiss me deeply, his tongue finding it's way into my mouth.

Leo rolled off of my and opened his nightstand drawer. From it we withdrew a small bottle of lube which he vigorously applied to his cock, and my waiting ass. Laying back Leo asked if I could ride him, to which I agreed.

I climbed on top and placed my knees on either side of his body. I placed my hands on his chest for balance and positioned my hole over the tip of his throbbing cock. I lowered my self gently onto him as his cock slid into me. A feeling of ecstasy spread through me, his cock filling me up completely.

I began moving up and down, gripping his dick inside of me. He began to move his hips downwards as I moved up, and then quickly upwards as I cam down to slam his penis into me deeper and harder. We quickly fell into a rhythm, our bodies in sync, each movement ending in him deep inside of me. A groan escaping my lips with each thrust.

After a minute or two we lost our rhythm. Perhaps one of us was too enthusiastic, or our timing was off. But on the last movement his penis slipped out and I came down hard on his cock. He doubled over in pain, an ache that only men will ever know reverberated through his body. The hardness disappeared from his dick, and out night of fun seemingly came to an end.

Unable to regain hardness, we agreed we would call it a night and cleaned up and climbed into bed. We talked a bit and drifted off to sleep.

The next morning we awoke and began getting ready for our day. In the bathroom I slipped on a jockstrap I had brought in my bag. I had hoped to continue what we started the night before. Emerging from the bathroom in just my jock I saw Leo standing near the door to the room.

He was wearing pajama bottoms, but nothing else. He moved towards me and kissed me, his morning stubble feeling wonderful against my skin. Placing his leg behind me he threw me to the ground. He dropped down on top of me, pinning me down with my back flat against the carpet.

I could feel the bulge growing in his pants, he leaned in to kiss me again. Our lips connecting and sparks flying. He began to lift me up towards him. I believe to move me towards the bed, but our weight shifted and I feel backwards, my head slamming against the ground.

The back of my head felt tender, the mood once again was killed. Leo apologized profusely. I said it was an accident and not to worry. As I had to be home later I continued to dress and Leo and I parted with a kiss. Leo said he wanted to see my again and I agreed. I said we could talk later, and I made my way home.

As the day progresses my head continued to pound. I later found that my overnight stay ended with a mild concussion, the first of my life.

Leo and I did talk later, and we did eventually finish what we started, but that's a story for another day.