I actually met Wino just before PhD and I were officially separated. Meeting and being attracted to him is what actually prompted me to tell PhD I wanted to see other people, basically since I knew in my gut he was cheating on me, but wouldn’t admit it.
6′, 29 (now 31…now 37 and married!), born in Kansas to a privileged family, went to school for film but ended up consulting in Chicago and then selling high end wine for a winery his parents bought in to, plenty of wine, 420 and immaturity, thin, big nose, cute mole on his face, ridiculously wide smile, goofy dance moves, perfectly groomed dark hairy chest that makes me want to curl up on it and touch it for days.
He was the first guy I slept with after 16 years of monogamy.
I met him at the dive bar in town. He was well dressed in a white button-down shirt and dark jeans. He looked like the typical Napa tourist.
That night a culinary classmate and I had recently arrived there after dinner at a restaurant around the corner. It was Thursday night and we had no class the next morning, so it was already the weekend. I had enough to drink at the restaurant that I don’t remember how Wino and his older, Iranian companion struck up the conversation with us.
Early on, the Iranian turned to her and made a wild guess saying she was 23 with a long-distance boyfriend. Pretty spot on since she was 24 and had a long-distance boyfriend. He then turned to me and, with a strong gaze, told me I was 27 and available. I laughed and agreed. I was 38 at the time with a long-term boyfriend I was about to separate from.
He moved closer to me and whispered in my ear, “Why don’t we go back to my house for a glass of wine?” I laughed out loud uncontrollably and told him there was not a chance in hell that I would go home with a stranger. He told me he didn’t want to have sex with me, and I replied positively that he wasn’t going to get to.
An older man got up to karaoke “New York, New York” and I grabbed Wino by the hand and dragged him to the dance floor to get away. The physical closeness of my chest and stomach touching his caught me unaware and made me feel excited and weak at the same time.
I hadn’t felt so sexually attractive in months, maybe years. On several occasions throughout the night, he grabbed the belt buckle on my jeans. I wanted to grab him and run the one block back to my apartment and fuck his brains out.
My girlfriend left around 11:30PM, but I didn’t want the night with Wino to end. We yelled at each other over the bad karaoke going on behind us. At one point he just stared at me and started to move in for a kiss. I certainly wasn’t going to have a first kiss with anyone in a dive bar, but more importantly it was full of classmates and restaurant workers that knew I had a boyfriend.
He leaned in to ask me if he could take me to dinner some time. My mouth said yes before my brain spent any time thinking about it. I gave him my phone number and he sent me a quick ‘hi’ text.
Fast forward three weeks (and separated with PhD) and on the second drinks date with Wino we went to Yountville for a bite. I was nursing a hang-over, but decided tonight was the night so I put on the flirty blue dress I bought it New Orleans. It had an angled, frilly line from the mid-thigh to the knee across with a rectangle cut breast line that let my small boobs be their perky selves.
After dinner, he invited me back to the small apartment he was staying in on a fancy wine “compound.” It was dark, but the grounds were immaculate. Bungalows all around the property with a pool, tennis court and main house in the center. He gave me a tour and all I could think about was all the places I wanted him to fuck me.
When we settled back in his place on the big leather couch, he opened a bottle of wine from one of the many boxes covering the living room floor.
We talked, only briefly, before he leaned in, grabbed the back of my head, and opened my mouth with his. He moved his hand down my back and pressed me into him. I slid on top to straddle him and felt his hard cock pressing against my panties. When they clung to my lips, I knew I was already soaked underneath. I pulled in closer, rubbing my pussy along his cock repeatedly.
He got up, grabbed my hand and took me into the bedroom. I wanted this so bad. I wanted to be fucked again. To feel sexy. To feel a cock inside me. To feel hands on me. Lips on me. Skin on me.
We both undressed quickly. As soon as I was naked, he turned me over on my stomach.
He reached his right arm around me and pressed his warm, soft-haired chest tight against my back and he thrust deep inside me. I felt his hard lower abdomen push up against my ass and spread my cheeks slightly. I put my hand against the head board and pushed back so he was as deep as he could possibly get inside me. I arched my head back so that my hair and cheek brushed his face.
We rode together like that for several minutes – both breathing heavy. I felt close to him – something I hadn’t felt in a long time.
He pulled out and asked, “Can I come on your back?” I nodded, and he began to rub his long, slender cock against my left ass cheek close to the crack. With his hands on each side of my hips, he thrusted keeping his body close to mine. I could hear the mounting excitement in his breathing and moaning. He came quickly and quietly before jumping up to grab a towel.
While I lay there for those few moments alone, I felt removed from my body like I was in a dream watching someone else in bed with this barely 30 year old man. I had never thought I would be in someone else’s bed again. It felt new and exciting. I felt sexy and attractive again. I didn’t want to leave this new place in my head.