My First Rodeo

My First Rodeo

By HeadBincharge

I was barely out of my twenties when we met during a business trip to Chicago. We were both travelling with our original spouses. It was an industry type trip that both men were invited to with attendees from across the country. We were on a shuttle taking us from the airport to the hotel. I remember watching him walking down the center aisle towards us when he stopped in front of our row and introduced himself as Steve. We all came from the same area, and the men did business together but had not met in person before. The four of us ended up hanging out those few days. Nothing from that trip stands out other than I ended up with a new job working as Steve's assistant to help him expand his business. I had no idea just how much my life was about to change.

On my first day of work, Steve was 3 hours late. He nonchalantly walked in and realized I had been sitting there waiting for him to show up. That was the last time I had nothing to do. I shared a shitty little office with 2 other employees and on the other side of the wall was the President's office. We were all too close for comfort in that space and it could be intimidating at times. There was plenty of mind fuckery going on but building rapport with Steve came easy and we clicked early on. He could be rough when communicating and had an edge that made a lot of people afraid to approach him. It didn't take much to set him off. He got so worked up one day that I jokingly called him "cowboy" to diffuse the situation. That apparently stuck with him and weeks later during a heated meeting, he suddenly called me "cowgirl" to get my attention. It stopped me in my tracks and we both laughed.

Because of the tight space we worked in, there were times when Steve and I came too close to each other. At the start I was not at all attracted to him physically but that changed from a single touch. I was standing behind his desk updating a calendar he had on a bulletin board as I had been doing since I began working for him. That day, like many other days, I was wearing a short skirt and high black heels. Suddenly, I felt his full hand on my calf that rose up to the back of my thigh. He held just long enough for me to notice it wasn't by mistake. Steve was leaning back in his chair and talking on the phone. We made eye contact and he mischievously smiled at me. I walked away, not sure what had just gone down. But I knew I wanted it to happen again. Steve is tall and lean, with plump lips, big masculine hands and from what I could tell, a massive cock. So big that he had to adjust his huge bulge every time he sat down. I found myself mesmerized by that and wanted to unzip him. I'm petite with huge breasts and a small ass which were now on his radar. But he was my boss and we were both married.

I remember thinking this new attraction to Steve was a very bad idea. I had been married for seven years at the time, and the sex was great with my husband. He always got me off first, so I wasn't out looking for another man to satisfy me. I have a very a-type personality, and my husband was random about pretty much everything. Maybe that was the attraction originally. But Steve was different. Complicated and charismatic with an aggressive mean streak but sexy in a mid-western WASP kind of way. We laughed and yelled a lot. At one point, he was about to walk by me in the office hallway and stopped to run his long fingers across my chest, softly touching me. I was wearing a low-cut silk blouse and both of my huge nipples responded by immediately getting hard. He laughed and leaned in closer to whisper "don't fight this" and continued down the hall. He was baiting me and I was hooked. The sight of him now made my pussy tremble.

Our work schedule was hectic, many days requiring long hours, so the pull towards him was impossible to ignore. Being near him drove me crazy and when we very close to each other, I could smell Irish Spring on his skin. It was becoming more apparent that our attraction to each other was a fierce sexual tension that I hadn't known before him. Then, Steve called me over Memorial Day weekend from a local hotel where he was "relaxing" and asked me to come hang out. My husband was away for a few days, which Steve knew, and I had too much time on my hands. I tried to say no but he was relentless. The next thing I remember is being in the hotel elevator headed up to his suite. The door was slightly ajar and when I walked into that room he jumped up to meet me at the door hugging me very tightly against him. I felt him get hard. When he sat back down on the couch, he patted the cushion next to him for me to sit. I did as I was asked. He moved over to be even closer. "Just kiss me", he said.

I hesitated but gave in after his third request, which had become more of a demand. Steve was used to getting what he wanted. I could see the outline of his hard on and wanted to touch him. Our lips coming together for the first time was insanely delicious. He held the back of my head when we kissed and having his tongue in my mouth shook me to my center. We kissed and touched each other for hours. I was laying on top of him with his very hard dick between my legs as I squeezed and pressed myself into him. I knew I was much wetter than normal. My safety was that he still had jeans on with only the top button open. I kept my clothes on, but my thong was soaked through to my shorts. I wanted to fuck him so badly but held out that day and was naively proud of my resistance. But the idea of having him inside me was all too consuming. I would use him when I needed to cum on my own and now thought of him when I fucked my husband.

A few days went by, and it became apparent that we were absolutely going to fuck. I caught him staring at me, undressing me with his gaze. I was so turned on. The following Saturday he rented another suite. This time, I walked through the door and into his arms. He was already bare ass naked with a massive hard on to greet me. He pulled my clothes off and we stood mashed together with our lips and tangled tongues fiercely engulfing each other. The world stopped. Kissing became our gateway drug. He begged me to get on the bed. All I remember is saying "fuck it" and that was it. We spent hours in and out of each other's bodies. His mouth in my pussy was next level, and my hands were in his hair holding his head while his tongue explored me, teasing my clit. I wanted all of what he offered, and he knew what I needed. My clit was so engorged, and he kept flicking it with his tongue and put two fingers inside me. I stopped breathing. He ran his other hand over my body stroking my nipples until they throbbed. My slit was slick with juice running onto my thigh that he licked off and then came up to kiss me. Tasting myself on his mouth pushed me over the edge and there was no going back.

My hand wrapped around his swollen erection, stroking him and sucking his tip. His cock stood straight up, ready for me. I finally got to taste him when that first drop of cum came to the surface. I licked it off and ran my tongue around the rim until he moaned and pulled me up on top of him, perfectly positioning me to ride him. When he entered my pussy for the first time he kissed me hard. I had to suck in my breath from his massive size. His cock was thick and long and now deep inside of me. I was so wet that I sucked him in deeper pulsing around him and he grew even bigger. I screamed "fuck me harder" and Steve obeyed. The friction was unbearable. My pussy gushed with his every plunge further into me.

I slid up and down his shaft while his big hands held my ass in place as he started to push further inside me with a need that came from his core. I met him thrust for thrust and together we settled into an intense rhythm. I could tell Steve was about to cum, so I pulled off to control him to wait. He roared in my ear and was wild looking with lust. To retaliate, he flipped me over onto my belly and without hesitation, he entered me with force from behind. I screamed with pleasure. I pushed up onto my knees and he had no mercy. He held a handful of my long hair at the back of my neck, pulling me closer into his base. There was no room between us. He would pull out just to run his cock up to my clit and then slam back into me. I wanted him to split me in half.

At some point he turned me around into a 69 and worked on me softly while my body trembled under his touch. I sucked him down my throat and he moaned. Suddenly, and without warning, I fell apart and came so hard on Steves face with his tongue still inside my tight and very wet pussy. I gushed and soaked the sheets. At that point, he was so hard and extended that I couldn't keep his cock in my mouth while I finished climaxing. Without hesitation, he put me on my back and kissed me passionately while he slid back inside me. Long, deep thrusts at a slow pace. I wrapped my legs around him, drawing him closer. His breathing was getting heavier and I could feel his cock taking up all the space inside me. He made a deep guttural growl and that was what I needed to hear to know he was so close to letting go. I lifted my hips to meet him and with a few more strokes he exploded inside me. Steve lost control. Hearing him cum so hard pushed me into another orgasm with our bodies entwined in sheer pleasure. After what seemed like forever, we both lay back holding each other, glossy with sweat and cum. He kissed me sweetly and said, "we need to do that again and again, cowgirl". As spent as we were, his cock stayed hard. He was lying behind me now holding my hip while his cock was nestled in the lips of my pussy. It was easy for him to enter me again. I was full of cum and he slipped easily back inside me and murmured "mmmmmm". We lost track of time and were fuck-locked like that for hours.

After that day we became even more reckless and sucked and fucked like animals, anywhere and everywhere. During a surprise party for his wife at the time, we stained the living carpet with cum. I left that room with rug burns on both my knees while the party was in full swing on the beach below. We fucked in cars, a luxury resort pool with other people swimming around us, on a desk in a furniture showroom, a truck in the middle of a field, the parking lot of a restaurant before we had dinner, bent over the counter in his office kitchen, standing up in the shower in his office bathroom, empty buildings we were renovating, more hotels, motels, and even his home. We don't work together anymore but even after all these years later we maintain a close friendship with fierce sexual chemistry and continue to hook up when we can. Recently we met at a hotel and were getting it on in the elevator that hadn't moved from the lobby level since neither of us hit the floor button.

It's no longer my first rodeo and I am naked in seconds heading towards the bed waiting for him to take me. But that first time was the best ride, ever.