Virgin No More
I remember my first time like it was yesterday. Everything leading up to it. It is as vivid as having breakfast just this morning. His name was Sean. He was Irish, quite nearly off the boat fresh with a thick accent and a smile that melted my heart. At 6'4’’ and 220 lbs, he was a built gentle giant. I had started a profile on a gay chat app just a few days prior to our meeting. My profile stated simply that I was a virgin and scared but curious. Sean was the first to message me saying “I will be patient”. I had cross-dressed privately many times since I was 15 but now I was trying to have my first meeting fully dressed with another man. Time to go where I had never been before. I agreed to meet Sean at his house in Montauk, NY for dinner. He asked what my favorite meal was (chicken Alfredo) and he promised to prepare an immaculate dish. The afternoon of our meet, I put on a brand new pair of tight jeans with a long sleeve henley top with a black leather jacket and matching bra and panties and I drove out to the address he gave me. It was a small bungalow house with a meticulously kept yard and garden. The winter air stung my face as I stood outside the front door debating whether I should ring the doorbell or runaway out of fear. I took a deep breath and rang. The door opened and the same smile from his pictures greeted me as he welcomed me in. “You look amazing, Jesse” he said, seating me at his dining room table. “Thank you, I bought this outfit just for this date” I replied sheepishly. “I don’t know if you are a drinker but I grabbed some wine for dinner, I figured a little buzz might take the edge off for both of us. May I pour you a glass?” he asked confidently, holding up the bottle. “Wonderful, yes please, I’d love some”. How thoughtful, right? He brought dinner in from the kitchen. It was a large bowl of wonderful chicken Alfredo. We began eating, stealing glances and smiles, our silverware clinking lightly against the plates. Finally after some silence, I decided to take a leap of faith and jump into conversation. “I love your accent. Irish, right?” I began, taking a long sip of wine. “Yes, that’s right. Been here for three years on a work visa. Working for an oil company” he replied, leaning in towards me. “That’s hard work, dangerous stuff, you gotta be careful in that line of work” I said, trying to breath, eat and act casual simultaneously. “It can be” he answered. He refilled my glass and sat back down. “Tell me about you. When did you begin crossdressing, becoming interested in men, et cetera?” I told him how I had started dressing as a teen in my sisters clothing and how this was the first time I had even gone on a date with a guy. “A virgin?” he exclaimed. I nodded shyly. “Well we can go as far as you want to, whatever you’re comfortable with. I am really enjoying this date and would like to see something regular come out of this”. We finished dinner in a much more relaxed state than its beginning. He took the dishes into the kitchen. As he was cleaning, I took off my boots and sat on the couch. The heat from the radiator and the half bottle of wine began to encompass me and I began feeling my primal urges boiling inside of me. I knew that this was it. I was going to give my virginity to this man. I was going to take his seed inside of me, wishing that it’d turn me into a woman of his dreams. “Alright there, Jesse” Sean’s voice snapped into my head. “Yes, um, was just thinking” I stammered. He gave me a long look as he dried his hands. He tossed the towel onto the table and stepped up close to me. His burly hands wrapped around my waist and gently squeezed my butt cheeks. A sly moan escaped my pursed lips and my arms instinctively wrapped themselves around his neck. “Be gentle, but don’t stop. I can’t back down now. Don’t let me” I whispered. He led me into his bedroom. He went into the bathroom, shutting the door behind him. I immediately removed my top and jeans and socks. In a black and pink laced matching bra and panty set, I laid out on his bed. Moments later he came out of the bathroom, naked, his stocky sunkissed body glowing amber in the soft lighting. He stared longingly at my body and I could see his dick twitch in anticipation. I remember thinking, this is what it feels like to be desired, to be wanted. I gave him a little wiggle of my bum and he crawled into bed on top of me. I could feel his hammer rubbing against my panties, so I grinded my hips back against him and he began kissing my neck, my back down to my hips and thighs. He gently tugged down the panties, dropping them on the floor against the bed. The alcohol was taking full affect now and my inhibitions had vanished. “Do it” I whispered. He obliged, pushing his body down on me, his manhood slipping deep inside my ass. I groaned loudly. My vision was stars, my body lost all strength and went limp. He slowly pushed deeper inside me as a loud gasp of pain and relief escaped me. “Are you ready?” he looked at me. I nodded. We melted into a tangled mess of body parts, sweat glistening our bodies and the windows fogging against the bitter night. For the next two hours, our hands and tongues explored each others bodies. Then the time came. I could feel his balls twitching, ready to explode and he began to pull off of me. On my back, I locked my legs around his, holding his body against me. “I’m going to cum” he gasped. I smiled and nodded and he released thick loads of hot man seed deep inside me. His eyes rolled back in his head as he collapsed on the bed next to me. It was a little after 9:30 at night by this point. Knowing I had work the next day, I rolled over on top of him, looking deep into his eyes and giving him a soft kiss. “Thank you, Sean” I said, brushing his hair out of his face. “For?” he replied. “For being patient and understanding. Everything tonight, my favorite food, the wine to calm my nerves, it all meant so much. To be honest, I knew I was going to give myself to you before dinner was even over” we both laughed. “Jesse, you are beautiful and sexy and amazing in bed and a wonderful date and I want to make sure it continues” he begged. I began to put my clothes back on. “Don’t you worry about that, Sean. You made a great first impression. I will definitely be back”. We chatted a bit more, he wrapped up the leftovers and helped me out to my car. As I drove away, I could see him in the rearview mirror, staring after my taillights driving away. What a magical night. I’ll never regret losing my virginity to the day I die.
