A Night on the Town

Alice’s night on the town

Recently I went out for a night on the town and found two new friends and a memorable experience. I’ve been dressing as a female since I was 10, but until two years ago hadn’t made the transformation. When I did, I was left wondering why I didn’t do so sooner. I’m not a movie star but I don’t cause small children to run screaming either.  Having said that though, my friend that does my makeup is a magician. She makes a rather plain me into movie star gorgeous. This night I was scheduled for a 3-hour session and the end result was nothing short of spectacular. My long blond/brown hair was perfect as were my nails and of course my makeup. That night I chose a form fitting rose colored top that hugged my D cup breasts and moved as they jiggled. My pants were black leather so snug they looked painted on. When I walked into the club, many eyes, male and female tracked me. Perhaps wondering which movie star I was and sure they’d seen me, but unsure where.

I walked across the club with my butt swaying suggestively in those tight leather pants. I settled myself at the bar and ordered one of my favorite micro brews. I proceeded to people watch. In this club there were a lot of watching to be done too.  I found myself swaying in place to the music’s hypnotic beat.  Eventually a truly stunning lady sat down next to me at the bar. I am bisexual and submissive by nature. The lady, Paula, was blond, very shapely, but less endowed than me. She nestled a bare thigh to mine. Her short micro skirt hardly hiding her lower body and it was clear she wore no panties. She leaned across to me and nibbled my ear as she whispered into my ear, “I want you”.  Her perfume was an intoxicating cloud around us as she placed a hand on my breast and teased my nipple into full erectness. She had my full attention as a brunette settled on the other side of me and whispered into my other ear, “Hi, I’m Lilly”. She like Paula brought my other nipple to full erectness. Lilly it turned out was a translady. This was clearly demonstrated to me as she took my hand and placed it in her crotch. She didn’t feel like the largest I’d ever met, but she was by no means small. I was becoming increasingly distracted by the attention that both Lilly and Paula were giving me. Paula by now was kissing me up and down my neck and Lilly was busy giving my own crotch her attention. 

It didn’t take too much of this attention for me to be led away hand-in-hand with Paula leading and Lilly and I in a close embrace. A long dark limousine pulled to the curb as if conjured. The door sprang open and Paula pulled Lilly and I inside. The door closed and we were off.  Paula guided my face to her pussy and I got to work. Her clitoris was huge. Almost like a small penis. Paula was wet, ready and making small moaning sounds at the back of her pretty throat as I got to work. I gave her clit my attention, sucking on it and licking it from tip to base. I inserted three fingers into her and she was so wet and slick that her pussy swallowed my entire hand. She began to fuck herself on my hand. I could feel Paula’s vaginal muscles contract around my hand like a hand gripping mine. Only this hand was warm, slick and wet. With each time she drove herself down on my hand I could feel the tip of my middle finger touch her uterus. Then all at once my middle finger slid into her uterus and Paula began screaming her ecstasy. Over and over, “Don’t stop, Don’t Stop, OH GOD!”.  Paula had peeled down her top and was massaging her magnificent breasts topped with erect nipples an inch long. She was indeed a stunning woman.  With all this going on you might have though I’d be distracted enough to miss what was going on behind me, I was… almost.

Lilly had managed to work my leather pants down to give her access to my ass. What I thought was Lilly lovingly stroking my bare ass was actually her getting me really lubed up.  Now I’m not a size queen and some dicks are simply too big to fit in me comfortably, but Lilly was like Goldilocks, not too big, not too small. Just right. She gently settled into me balls deep. I had this wonderful sensation of being filled just right, no pain, just a lot of pleasure.  It took a couple of cycles to get us all in sync, but soon Paula would drive herself onto my hand and Lilly drove herself into me giving a little extra boost to Paula. I felt my middle finger slip all the way to its base into Paula’s uterus as Lilly drove deeply into me.  I felt Lilly grow inside me and my anal muscles gripped her tightly as though my body wanted to keep her deep inside me and not let her go. Soon it was my turn and I was screaming my ecstasy in counter point to Paula’s.  I’m not certain how long this went on it seemed like forever, but I’m sure it wasn’t. But Paula’s vaginal muscles contracted so tightly around my hand, I couldn’t move it and I found myself being covered in vaginal fluids as Paula pushed my hand out. Paula was a squirter, and she came like a fire hose. Almost at the same time, I felt Lilly twitch inside me and another fire hose was going off inside me. Warm seed flooded me.  Slowly as we all caught our breath, we became aware that the car was not moving any more.  We rearranged our clothes and as I did so, noted that there was a goodly amount of cum dripping from me. Lilly triggered the door and we stepped out. This was obviously a private garage someplace; in all the lust I had no idea where we were. The confusion must have shown on my face.  Lilly smiled and took my hand. We are at our place. Lilly led me to a private elevator and we all faced the door. Paula took out a key card, I can’t for the life of me figure out where she stashed it. Inserted it in the control and it pinged green. A rather longish ride and the doors opened on a lush garden. The place over looked the downtown and the view was breathtaking. Still holding my hand Lilly led me over to what must have been a king sized lounger next to a pool.  Lilly began undressing me as Paula undressed Lilly. When we were both nude, we both undressed Paula. Paula lay back on the lounger her hair spread out underneath her.  Lilly began lubing up Paula’s ass much as she’d done for me. Paula sighed as Lilly entered her. Paula tugged on my legs indicating she wanted to 69. She immediately sucked my dick into her mouth. Now unlike all those porno flicks, hormones prevent me from becoming erect, but Paula had amazing technique and I was in heaven once again. I lowered my head to Paula’s pussy and went to work.  Paula began bucking her hips in rhythm with Lilly’s thrusts. Lilly thrust a large glass dildo into my hands and I eased that into Paula’s pussy. Almost at the same time, I felt Paula insert a similar dildo into my ass. Lilly and Paula came at almost the same time too. I was showered with pussy juice and hot shemale seed.  We rested a bit and Paula offered me a strap-on.  Lilly stepped behind me and pulled it tight on me. While my dick doesn’t get hard, there was a place in the strap-on for my dick. It all fit as though made for me. Paula took up a modified doggie position with her hands on the lounger, giving me a perfect view of her wonderful ass.  With Lilly under Paula we filled her from both sides and established a rhythm that soon had Paula bucking under me.  Paula came with a scream and Lilly pulled out and showered me with her cum.  By now it was starting to become light we’d been busy most of the night. We went inside and collapsed into a huge bed. What we did when we woke up is another story.