After crossdressing forever, I finally decided I was going out dressed. Although I had dressed for men before, I had never been out dressed. I had a 4-day weekend coming up, and I had decided that was SarahAnn’s coming-out time. There was a gay/drag club on the beach a few miles from home; that was my target.
Friday came, and I was so excited that I could hardly move. I got up early, made sure my body was hairless, showered twice, douched twice, and chose my outfit. I wanted to be cute, but not slutty. I wore a light and dark blue checked skirt, brown pumps, light blue thigh highs, and light blue French-cut panties with a matching bra, topped off with a button-up light blue blouse, and my long blonde wig.
I waited anxiously for night to fall so I could leave hopefully unobserved. At 9 I left my heart pounding. Driving down the road, having cars pass me was exciting; SarahAnn was in the world finally. When I got to the club, I twice started to leave, then finally checked my makeup for the hundredth time, took a deep breath, grabbed my purse, and headed inside.
Once I got inside, I headed to a stool at the bar close to the window. I ordered a Coke from the bartender, who smiled as he set it in front of me. “You're doing fine, hun,” he said. “I can spot a first-timer a mile away. Nice outfit,” he said as he walked away. That relaxed me somewhat. I turned around to check out the bar; there was a small crowd but a line at the door.
As I scanned the room, I caught sight of a handsome man walking towards the bar who appeared to be looking directly at me. I turned back to the bar and watched him through the mirror as he seated himself at a table directly behind me.
When the first stage show started, I turned around, purposely spreading my legs enough to give him a peek up my skirt, if he was looking. As I watched the show, he came up beside me and gently placed his hand on my knee and pushed them together. I looked at him and smiled. “I’d like to keep that view for myself, not the whole place,” he laughed, and I giggled a bit. Hi. I’m Thomas, and you are? I started to introduce myself, then adjusted to my feminine voice and stammered, “Hi, I’m SsaraahAnnn!” My face felt like it was on fire. He rubbed my knee and said, “Calm down, hun, can I buy you a drink?”
We moved to the table and began to chat about—I don’t remember what, but I was so engulfed in what was happening with me. I had never felt so happy; I was being courted by a handsome man. He asked me to dance, and all I remember is reminding myself, "Don't lead, don’t lead. I was so thrilled with my decision to come tonight, and feeling so girlish, I didn’t want it to ever stop." We danced several times, a couple of slow ones, and a couple of faster ones. When we set down, the bartender came, and Thomas told him we were about to leave and didn’t need anything else. The bartender turned to me and smiled. “Oh, go, girl, nice catch! Thomas said he hoped I’d walk to the beach with him to get some fresh air; I was almost to the door before he finished his comment.
The walk to the beach was only about a block; we crossed the street and went between 2 high-rise condos. When we got to the sand, Thomas said that I’d never make it in those shoes, and he needed to use the restroom. I looked around and said, "I don’t see anyone, and I promise not to peek." He laughed and said, “No no, I mean in my condo,” and he pointed up at the building next to us. “I assumed you wouldn’t mind; I promise I’ll be quick." I nodded and took his hand. “Lead away, kind sir," and we headed for the outside elevator.
When we stepped off the elevator into his condo, I was shocked it was gorgeous; the beachside was all floor-to-ceiling windows. What a view. He went to the bathroom, and I realized that my soda needed to exit me as well. I asked if there was another bathroom and made a beeline for it. When I came out, Thomas was sitting on the couch looking at the ocean. He asked if I was ready for our beach walk, and I pointed to the window as I sat down next to him. “Why walk when we have a view like this? He said he was looking at something prettier and pulled me to him, his lips meeting mine and his tongue plunging deep into my mouth. The kiss was long, soft, and full of passion.
His arms engulfed me and moved up and down my body; mine began to explore his as well. Our lips parted for a moment, then smashed together, our tongues playing tag in my mouth. His hands explored my body, moving from place to place, squeezing, then moving on. I suddenly realized that my hand had found the front of his pants and was rubbing his hardening cock; his had slipped under my skirt and was rubbing between my legs through my panties. We kissed and fondled each other for what seemed like hours, both of us moaning softly.
I made the first move and unzipped his pants and reached in to massage his now hard cock. As I messaged him, I pulled away from his lips and slid down on my knees in front of him, fumbling to undo his belt and release his substantial manhood. Once his pants were opened, I began to kiss him through his underwear, as my boy clitty tingled with excitement, as I pulled the elastic band on his underwear down his cock, literally jumping in my mouth, his manly smell filling my nose, the uncut cock filling my mouth. This was my dream come true.
I sucked, kissed, and licked him through his underwear. I pulled his pants down so I could taste his balls. He kicked his shoes off, and I pulled his pants off. I looked him directly in his eyes as I took his cock as deeply as I could; he pulled me up onto the couch so that he could fondle my ass while I loved on his cock! I moaned loudly when his finger slid into my bussy, first 1 finger, then 2, then a third. My god, he was making me feel things I had never felt before. Then he whispered, “I want to breed you, Sarah; I want to cum so deep in you that it will never come out!” I could only moan against his cock..
He pushed me back on the couch and slipped my panties off and moved between my legs, kissing me deeply. He slowly and gently penetrated me. Very slowly, he pushed deeper as I pressed against his glorious cock. As my body accepted his large manliness, his movements became faster and deeper; he would push, and I would push back. I had never felt like this before; I wanted his cock in me forever! I wanted his hot cum pumping into me! He fucked me for what seemed like hours, kissing and moaning, and then I felt him stiffen, then groan, and drive his cock deep, as it throbbed, spewing his hot cream deep inside me! I realized this was the first time I had been made love to, not just fucked! I vowed to myself this wouldn’t be the last time!
We lay together while his cock went soft inside me, we cleaned up, and we chatted for a while about where our relationship might go, as neither of us wanted it to be a one-night stand. We traded phone numbers, and I headed home before daylight. By the time I reached home, I had three texts from him. Before the day was over, I was already getting ready to head to his place as soon as it was dark out! While dressing, it dawned on me his cum was still inside me; it never did come out of me.
(The next day to be continued)
