A Transformative Encounter
Author's Note: I hope you enjoy this story. You can find my other stories on this site. Please check them out. This is a work of fiction between consenting adults.
I left my dinner meeting and returned to my hotel room. As I often do, I opened my laptop and first responded to the email that had accumulated during dinner. After clearing email, I opened my favorite date site to see if there was anyone around looking to play.
I saw a few interesting posts but the one that caught my eye was this one: “late 20’s gurl who likes to dress up and service older guys who are all-man.”
“Hmmm,” I had never been with a T-Girl. I’d always wanted to but never had the real opportunity. And here was opportunity knocking at my door. So, I said hello and within a few minutes we were talking about what we were looking for. They told me to call them “Katy,” and with that the boy I had been chatting with became all girl. He told me his preferred pronoun was “she” and “her”.
We bantered back and forth. I let on that if we met it would be my first time. She laughed and said, “careful, meeting me won’t just change your life, it will transform you.”
Intrigued, I tried to convince her to come and visit me.
She was hesitant. Despite the listing on the app, she rarely visited men in their hotel rooms. I told her that I understood that and thought it was a safe and practical practice.
I finally convinced her to meet in a neutral place: the bar across the parking lot from my hotel. If our drinks went well, we could adjourn to my room. If not, we both could walk away. She told me to give her 30 minutes.
I took a quick shower, dressed in casual clothes and went over to the bar. I had told her what I would be wearing so that she could spot me when she came into the bar. “That way,” I had explained, “if you don’t like what you see, you can walk out; no harm no foul.”
I was sitting at the bar nursing my drink when a drop-dead gorgeous younger woman sat down beside me. She had long, blonde hair parted in the middle. Her eyes were crystal blue, and she had a soft face and plush lips. Her cheeks were firm and high, as were her breasts, to quote an American poet.
I was about to say “this seat is taken” when I noticed the whimsical smile on her face.
“Hi,” she said. “Hi,” I responded, “I guess this means you liked what you saw.”
She sat down and I ordered drinks. We chatted. I told her a little bit about who I was and what I did for a living. But mostly I got her to talk and tell me about her. She lived in Boys Town, not too far away. She worked at a part-time job that didn’t pay enough and that she didn’t enjoy.
As she talked, I was transfixed by her beautiful face. She had a pert little nose and narrow cheeks. Her lips were naturally red and full. Her little tongue was cute, and I was captured by it every time it slipped between her lips. Her hair framed her features nicely. As we got to the end of our drinks, I felt emboldened to reach out and stroke her cheek. She literally purred as I did so.
I whispered, “come back to my room with me.” She just nodded.
I paid the bill and we walked over to the hotel. Within minutes we were in my room.
I used the bathroom and then she did. While she was in the bathroom, I took off my shoes and socks and sat in the wing chair that was perched in a corner of the room, beside the floor-to-ceiling window. I gazed up Michigan Avenue but my other senses were totally riveted on the bathroom door, willing it to open soon. I could hear her finishing up in the bathroom as I gazed out the window.
The door opened and she stepped out and took my breath away. She was about 5’9” and weighed around 125 pounds. She was dressed in a black one-piece teddy made of lace and silk. Thin straps came across her shoulder and held up the bra cups. They joined in the middle with a swath of lace, about 3 inches wide, then went down past her navel to a G-string that was attached to either side of her luscious looking crotch by a thread of silk.
She posed in the door, bending her left harm at the elbow and placing her palm at the back of her head. My cock was rock hard and pleading to be let loose. She stood for a minute or so. Her hips were thin and ran straight down to two very sexy legs, all the way to the floor, where her bare feet stood.
She walked toward me, her hips swaying back and forth. Her cock was captured in the bikini panties and didn’t move a bit while she walked toward me.
She stood in front of me and smiled. “Do you like what you see?” “Yes,” I whispered, “oh, yes.”
She turned slowly in front of me so that her thin butt was squarely in my face. I reached up and stroked her ass. She purred softly and pushed back at my face. Taking that as a cue, I gently pulled her back toward me, using her hips as handles. The thong ran down between her cheeks. As I drew her closer, I placed my left hand on her lower back, just above her sacral dimples that sat across each cheek. I encouraged her to bend forward and she did. As she did, those lovely mounds opened like a blossoming flower inches away from my nose and mouth. I smelled the lightest fragrance. I couldn’t identify it, but it was faint and sweet and rocked me down to my balls.
“Eat me,” Katy moaned. “Please, eat me.”
I did not need to be asked a second time because as she first uttered the words “eat me” my mouth was already diving into the space between her cheeks, and my tongue was licking its way across the inner walls to get to the bare, pink rosebud that sat at the center of her ass.
I reached it and kissed it, pulling her cheeks apart. Her hole opened around my tongue and my little whirling dervish was inside of her making love to her sweet canal. Her legs were shaking. I reached up and stroked her package through the silk and the lace. She ground her crotch against me.
I was a man possessed. My face was buried in Katy’s backside with my tongue going in and out of the slick, wet tunnel. The sweet smell of perfume had now been replaced with a sexy and pungent aroma that was one part perfume to five parts sexual funk. I loved it and lapped up the juices that were flowing from my mouth, making sure to reapply them to this wonderful hole with my tongue.
She stood up, letting her cheeks close around my face. I groaned and leaned back in my chair. “Well, hell,” she said, “that’s one way to welcome someone into your room.” We both laughed as she dropped her hands to find my arms and gently urged me upward and out of my seat.
“Let’s not get too far ahead of ourselves,” she whispered. Then she started to unbutton my shirt. When I raised my hands to help, she batted them away. She leaned in and lightly kissed me on my mouth as her hands undid the buttons on my shirt. Still kissing me, she opened my shirt and rolled it down and off each arm. She tossed it aside. I was now bare chested.
She pulled away to look at my chest. She purred again, like a little kitten, as she moved in to suck my nipples. Her lips fastened to my left tit as her hands found my buckle, undid my belt and pulled my zipper down. I reached down to help her take my pants off. She once again batted my hands away. I groaned as she lightly bit my nipple to reinforce her command. I groaned and let her push my pants down below my knees. She then took her hands and pulled my left leg up and out of my pantleg and her left hand followed.
I was now standing with this gorgeous young gurl affixed to my breast, clad only in my boxer briefs. My 6” cut cock stuck straight out. She kissed her way down to my belly. I then felt her lips around my cloth-covered cock. She licked and sucked my cock through my undies. Her hands circled around my backside and stroked my ass.
I ground into her mouth and groaned loudly. I looked down. All I could see was the top of her pretty little head. I stroked her hair. She tugged my boxer briefs down and I stepped out of them.
Once freed, my cock sprang at her mouth and demanded to be let in. I felt that cute little tongue lick the underside of my cock. She held my balls in one hand and my cock in the other and proceeded to kiss and lick my shaft up and down. She sucked on my balls, each one separately and then together. She took my cock in her mouth and proceeded to take me down her throat. Her tongue and mouth muscles squeezed me like a virgin pussy.
My knees were shaking. I was bucking in and out of her mouth at a nice pace. She slowly stopped me, pulled back and stood up. We kissed. I sucked on her cute little tongue as if it were a little penis, milking it and enjoying its rich texture.
“Fuck me,” she moaned.
She didn’t have to ask twice. I gloved up while she prepared herself on the bed. She was on her knees, with her ass facing me. I leaned in and spit on her hole, taking time to lick her deeply. Then I got up behind her and slowly pushed forward.
Slow was not in her vocabulary, however. She pushed back and suddenly I was deep inside the tightest boi pussy I’d ever had. I could feel her ass muscles constricting around me as I pushed in and pulled out. She was bent forward and I was on my knees behind her, fucking her long, deep and continuously. I stroked in and out, my balls slapping against her as I plunged deep. Her boi pussy grabbing me on the backstroke, trying to keep me in as deep as possible.
I reached under and grabbed her cock and balls. She was rock hard. She felt small, maybe about 3 to 4 inches hard. I stroked her and played with her balls as I pushed my cock in and out of her. Her cock felt nice in my hand. I made a quick, mental note to suck it later.
But for now, I was fully engaged in fucking this beautiful little boi gurl. I pushed in and her cunt muscles grabbed me, drawing me in deeper. I started to move quickly in and out, my balls slapping against her thighs. I groaned and exploded, shooting volley after volley of cum. When I was done cumming, I let my flaccid cock slide out of her.
She groaned and flipped over on her back, stretched out in front of me. Her cute little cock, was rock hard and beckoning my mouth. I noted, with pleasure, that she was not bald. She was neatly trimmed. I knew that soon I would be nuzzling my face in that public hair as I sucked the cum from that petite-sized cock….
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