My connection with shemales started with the Internet. During my teenage years, I used to watch a lot of porn. I watched a little bit of everything and discovered the most diverse categories of adult videos over time, until I came across shemales, which completely fascinated me. But despite that, I had never actually tried having sex with a trans woman, even after years of curiosity. I never considered myself homosexual; I had my girlfriends, and they always turned me on. Even so, the curiosity was always there.
Recently, I started browsing through escort ads on the Internet and discovered that there were many gorgeous shemales just a phone call or a WhatsApp message away. So, I started chatting with them on WhatsApp, asking silly questions like: "Where do you host?" "How much do you charge?" and so on. But in the end, I would always make up an excuse not to meet them, and then I'd delete all the messages so no one would see. Without even realizing what I was doing, I repeated this routine a few times over the course of a couple of days. Some of them sent me videos and said they wanted to see me sucking them off or things like that. It made me hesitate, but the fantasy was taking over.
One fine day, I decided I wanted to get laid. Since I was alone, I went back to the escort sites to pick a call girl. I wanted a woman, but I took a look at some shemales too. I opened several tabs in my browser to decide who to choose later. There were so many options, and it was hard to pick just one among so many hotties.
Finally, I made up my mind and sent a message: "When can we meet today?" and quickly received a reply: "SO YOU FINALLY DECIDED. Anytime, my love." I thought that was a bit intriguing. What did she mean by "finally decided"? But I soon stopped questioning it and booked a time at a nearby motel, got dressed, hopped in the car, and left. I arrived before her and waited anxiously. Soon, the intercom rang: "Your company has arrived," said the receptionist. I waited until she finally walked in.
She was a gorgeous girl, tall, blond, with striking blue eyes. She looked like a doll and greeted me with a sweet, very feminine voice. She was carrying a large purse, which she placed on a small table near the door, and right away we started French kissing. It was amazing. I began by unbuttoning her blouse and taking off her bra. Her breasts were fantastic, just the right size, and I immediately started sucking on them. She seemed to be loving it, making horny little moans and telling me: "I'm dying to see you sucking me down there, hmmm!!"
So I started working my way down, kissing everything in my path until I reached her belt buckle. There I was, on my knees in front of her, undoing her pants without knowing what was hidden down there. As soon as I unbuttoned and unzipped them, I started pulling her pants down slowly, and she gave a little shimmy to help me. That's when I noticed something strange in those panties. My eyes widened, and I leaned back a bit, suddenly feeling overwhelmed by the reality of the situation.
“Well? What are you waiting for to take off my panties?”
I looked up at her and said, my voice choking up, “I... I think I’m getting cold feet!”
She stared down at me with an authoritative smirk. “Excuse me?”
I stood up nervously, “I didn't realize... I mean, you look so feminine, but I'm not sure if I can go through with this!”
Suddenly, her sweet demeanor turned into fierce dominance. She laughed mockingly.
“YOU SENT ME A TON OF WHATSAPP MESSAGES THIS WEEK SAYING YOU WANTED THIS, AND NOW THAT YOU'RE HERE YOU WANT TO PLAY SHY?!!!”
“I’m nervous, I...”
“I CAME ALL THE WAY OUT HERE TO SEE YOU! AND NOW YOU'RE GOING TO OWN UP TO YOUR DESIRES!”
“Look, I can pay you anyway...”
“IT’S NOT JUST ABOUT THE MONEY, IT’S ABOUT YOU STOPPING THE EXCUSES! NOW GET ON THAT BED AND STOP PLAYING INNOCENT!”
“Or what?”
“Don't play coy with me! I know exactly who you are; I looked at your WhatsApp profile, look.”
She held her phone out to show me. It was true! It was my profile.
“Now you're going to own up to what you wanted, or do you want me to remind you of everything you said in those chats? Like that message where you said you were dying to taste my milk!”
I was completely captivated and helpless under her dominant gaze.
“GET ON THAT BED, NOW!”
I hesitated for a second, so she reached into her purse, pulled out a short leather whip, and cracked it hard against the floor.
“GET DOWN...”
She gave a sharp slap with the whip against the side of my thigh—a stinging bite of discipline that ignited an intense wave of heat through my body. The shock of her dominant command melted away my hesitation. Realizing how much I actually wanted to surrender control, I quickly lay down on the bed. Shockingly, despite my pounding heart, my cock was rock hard. I was completely captivated by her power over me.
As soon as I lay down, I watched her strip off her panties until she was completely naked in front of me. Her body was truly stunning, the kind that would make most girls die of jealousy. Her face, though visibly intense and commanding, was perfectly feminine. But when my eyes wandered lower, I swallowed hard. Her cock was huge and incredibly virile.
She walked over to me and positioned her massive meat right against my cheek. Instinctively, I raised my hands to touch her, and she snapped, “DON’T TOUCH UNLESS I SAY SO!!” She whipped the air right next to me, making a sharp crack. “Now suck it good, and get it real wet with your spit, because I'm taking your ass right after.”
I looked up at my dominant mistress, completely under her spell, as she cracked the whip through the air once more, “Make it shine, move it!”
I opened my mouth, and she slid it in. It was a massive cock, barely fitting inside my mouth. She wanted to push it deep, and the intensity made me gasp, but her commanding presence made me want to please her even more. “Suck it good! Don't forget I'm shoving this up your ass later, and it needs to be dripping wet!”
I kept sucking eagerly until I noticed she was breathing heavily. “Keep going, I didn't tell you to stop!” Thrilled by my submission, I kept going until she grabbed my head with both hands and said, “Now swallow it all...”
Instantly, I felt that blast of thick, hot, salty liquid shooting into my mouth. I eagerly swallowed every bit as another jet came, and another, and another. It was so much milk! When it finally ended, she looked down at me with a sly, dominant smile and said, “Now clean it up real good, I want to see my cock shining.” I stayed there, licking up every last drop that was left. Then she stood up and said, “Now my balls.” I sucked them exactly how my mistress ordered. In my mind, this complete surrender of control was mind-blowing, and my own cock was throbbing hard.
She stood up and stared at herself in the mirror for a while. Then she sat down in a chair next to a table and ordered, “I’m thirsty. Get up and grab a drink from that minibar over there.” But by that point, I was still dazed from the intense pleasure of serving her. She grabbed the whip and cracked it across the mattress. “HURRY UP! Don't keep your Mistress waiting.”
I got up, eager to obey, and went to open the fridge. “What drink does Mistress want?”
She chose champagne. I poured her a glass with complete devotion. She drank it calmly while checking messages on her phone. I stood there before her, completely at her disposal, until she finally ran her hand over her penis and found it ready for round two.
Immediately, she grabbed the whip, cracked it in the air, and said loud and clear, “NOW ON YOUR FOURS, QUICK!”
I rushed to the bed and got into position. She ordered me to stick my ass up and bury my face in the pillow, which I did immediately. I heard the sound of her ripping open a condom wrapper. She gave my ass a firm, satisfying slap, and then I felt some lube on her fingers. Without hesitation, she pushed a finger deep into my ass. I let out a loud moan. “Relax,” she commanded, working her finger inside to open me up before pulling it out. I could feel the bed sinking behind me under her weight. This was it! She grabbed my hips firmly and slammed all the way inside me!!
I lifted my head and gasped at the intense stretch, and she gently but firmly pressed my head back into the pillow. “This is what happens when you play games with a real woman. Next time you book me, you better be ready for the ride!!” I tried to speak, but my breath was taken away by the sheer intensity of it. My cock was rock hard, throbbing against the sheets. The sharp boundary between pain and overwhelming pleasure blurred completely. Gradually, the pleasure started to overpower everything, and I was right on the verge of coming. She gave my ass a few more hard, rhythmic slaps. I could feel her balls slapping against mine when suddenly, the intense stimulation pushed me over the edge, and I blew my load, painting the sheets!
She kept up her relentless, fast rhythm, driving me insane with pleasure. I turned my head to the side and moaned, “It’s so intense, I’m so sensitive!!”
She smirked down at me, “Hold on tight, because I’m taking mine now!” and kept pounding away until she finally hit her climax.
She pulled her cock out of my ass and told me to flip over and face her. It was a breathtaking sight. This beautiful woman with a fully erect penis sitting in front of me. My ass was burning with that amazing post-anal sensation, and my chest was heaving. The bedsheet was covered in my cum.
She looked at me with a satisfied smile and said, “Go to the bathroom and get some paper to clean us up.” I got up, feeling delightfully sore, and brought the paper. I carefully wrapped the paper around her cock and pulled off the condom. I went back to the bathroom and threw it in the trash while she lay on the bed, relaxing.
“Now I want a shower,” she said. “Turn it on, and when the water is warm, call me.”
Right after, she came in and ordered me to soap her body. I washed her thoroughly, dried her off, and helped her get dressed. She packed her whip back into her purse after I paid her fee with a generous tip. She opened the door, gave me a wink, and reminded me to do a proper prep next time. She smiled, closed the door, and left.
After everything, once I was back home, I sent her a message thanking her and apologizing for my initial panic. She replied that she thoroughly enjoyed taking control and that I could book a session with my new Mistress whenever I wanted.
