A Transformative Night Out: Embracing Change

FINALLY I GOT LAID!
Occasionally as a kid I'd play with my step sisters sexy panties. I chocked it up to normal prepuberty curiosity. Later in my 30's the urge returned to dress up like a slutty hooker. It nagged at me almost daily. I gave into my urges and started practicing how fast I could dress up, apply makeup and a wig, and look fuckable. Over the course of several months I was able to perfect going from man to woman while consuming 3 beers. Being a fast drinker, I was able to pull off hunk to hottie in just over 30 minutes. While perfecting my transition, I always wondered what it would be like to get laid like a woman.
Often I would cum while applying makeup after getting dressed up. Dressing was the easy part and usually took only 10 minutes. I realized that while getting dressed the only thing I thought about was not tearing or destroying the delicate lacy lingerie. So I switched to applying makeup first thinking that would solve the issue. The issue I soon realized was that I really wanted to get laid. One day I posted on CL, and yes if you are wondering I shot cum everywhere while writing my post. About a week later I got a reply from a nice looking guy. He was sexy to say the least. I responded laying down my law asking if he was man enough to follow my rules. He claimed and promised he would respect my rules to the letter. So he and I set a date and time. The evening finally arrived, I was jittery with excitement about how the evening would go. Arriving at his place as just a normal dude, I gathered the balls to ring the door bell. He answered the door looking me up and down. I just stood there holding a large paper sack with heavy duty string handles." Can I help you?, he said..I didn't order any takeout food." I snickered, " I'm not a food delivery guy, I'm your gal for tonight." He gasped for air, then stated, "I sure hope you know what you're doing!" "Common in!" As I entered his apartment, I said, " fooled you too! I got this! Anyone noticing me probably thinks I'm a friend of yours bringing food and came to watch the fight." Iron Mike is on pay per view in 10 minutes put on and turn the volume up." So he did just that, then asked me if I wanted a drink. "A full glass of Cabernet, if you have it." I replied. He scurried off toward the kitchen leaving me in the living room. When he returned with my wine I tried to not let on that I was surveying the place looking for red flags like photos or anything telling that he was not in fact single or that we could possibly be interrupted by a roommate or significant other. No red flags, time for action. He handed me the wine, nodding over his left shoulder, "bathrooms over there. If you need anything just holler." I looked him in the eye and said, " you all good with this, once I come out of the bathroom there's no turning back?" "Yeah sure". He replied. Silently I turned and went and closed the door behind me. I was nervous as hell all of a sudden. I slugged down the wine and began applying makeup which took about 10 minutes. He yelled down the hall, "want another drink?" In a soft womanly time I said, " yes my little sex kitten". I heard him chuckle a bit. I began dressing. Then he knock on the door and said, ""its on the small corner table." "You good in there?" He asked. I replied as slutty sounding as could be, "Are you ready to give up some dick?" The pause before his reply and his voice told me I caught him off guard cuz I really sounded like a woman. " "Ohh.. yeah" he answered.
I finished up confident I looked as hot as humanly possible with my fake boobs , wig, makeup, and slutty outfit. I walked down the hall into the living room to find him naked. I knelt down, sucked his hard cock til he came. He carried me to his room threw me down & fucked me for 3 hours. Laying sweaty, & satisfied, my only thought was,"I finally got laid." We met 3 weekends in row after that night, each better than the one before!