I was back on Grindr. As a shy young twink, I was not yet brave enough for gay bars, so I would spend my nights scrolling through profiles. While I had racked up a decent amount of hookups at this point, most of the time nothing happened. I would message a few guys and trade some pics, but I would usually decide that it's not worth the hassle and jack off instead.
This time, however, I was able to catch the eye of a beautiful trans woman. So beautiful, in fact, that I thought for a while the profile was fake. Yet the way she messaged seemed real enough and she gave me her snapchat username. We exchanged a few pictures on snapchat and she had a bunch of selfies and videos posted on her snapchat story. Seeing all of this was enough to convince me she was real.
From her pictures I could tell that she was tall. Her body was fit and strong. Then she sent me videos of her stroking her dick. That made me so horny I felt like I was going to go insane. I had to use all the restraint within me to avoid straight up begging her to fuck me. Instead, we simply agreed to meet at her place later that night.
Unfortunately, I didn't have a car at the time, so I had to take an uber. The driver liked to chit chat, so I made up some story about visiting a friend. Yada yada. All while having a backpack full of my "gear": lube, condoms, dildos, butt plugs, anal douche, etc.
When I got there, she was even taller and more muscular than I expected. I found this to be incredibly sexy, but it slightly intimidated me. She was only dressed in a robe. I had barely stepped inside when she asked me to take off all of my clothes. She said we would take it slow, but that she wanted to see what she was working with tonight. I hesitated. She flashed what was under the robe, revealing a hard body and thick dick. I think I might have actually drooled. She covered herself with her robe and politely asked again for me to get completely naked. I dropped my backpack and took off all of my clothes.
"Wow, you are so sexy," she said. I felt embarrassed and turned on at the same time. She told me to spin around, bend over, and such. I felt silly but I did what I was asked to do. I suppose she was testing my submissiveness and obedience. She then approached me and ran her hands all over my body. I really felt her height then, as my eyes were barely at her chest. After she was done exploring my body with her fingers, she gave my butt a hard slap and told me to sit down on the couch.
She left the room for a few moments, leaving me feeling awkward and exposed. She came back with two drinks in her hand, offering me either one.
"Rum and coke? Or gin and tonic?" she asked. I opted for the gin and tonic. As I sipped, she kept going on about how sexy I was and said that she wished I could see it for myself. I confess her constant compliments were making me feel happy and confident.
After we finished our drinks, she said, "here, lie like this." She directed me to lie in a certain way on the couch. It felt a little uncomfortable as she twisted me so both my face and my butt were facing toward her.
"Great, hold that pose," she said. Then she backed away from the couch. She disrobed, leaned against the wall, and started to stroke herself. At that moment, it felt like my entire body was turning bright red with heat. My dick became stiff, and I started breathing heavily. Seeing such a hot woman stroke herself to me was melting my brain. Then, without warning, she got out her phone and snapped some pictures.
If I had my head on straight, I would have protested. But at that moment, my brain was overheated and there was little capacity left for rational thought.
She then went to my pants that were lying on the floor, got out my phone, and gave it to me. I had three snapchats from her. I opened them, to see myself, lying naked on her couch. She was right. I looked sexy. The way she had me pose made my butt look big and my waist look small. I looked extremely fuckable and could not wait to be fucked.
"See," she said, "so sexy." She then took my phone away and kissed me. Hard. Forcefully. Pinning me to the couch. I emitted small moans, reinforcing my submissiveness to her.
But this initial makeout session was just a tease. She pulled away and directed me to her bathroom. She told me to shower and get ready for her. I asked to go grab my backpack and did so. I hastily cleaned out my ass and took a quick shower. Our little preamble made me desperate to be fucked.
When I exited, I heard music coming from the bedroom, so I wandered my way in there. She was on her phone when I walked in, but set it down and handed me another gin and tonic. I drank it eagerly, wanting to have a little buzz on when we finally got to fucking. When I was done with my drink, she surprised me by picking me up and carrying me to the bed.
She laid me down on the bed, then crawled on top of me. She paused for a moment, lingering over me, emphasizing the size difference between us. Then she kissed me hard. She pinned my arms against the bed. She then started pressing her dick against mine, emphasizing another size difference between us.
She then stopped and adjusted herself so that her legs were pinning my arms in place and her hard dick was right in my face. She teased me with it at first, slapping my face and rubbing the tip against my lips. I stuck out my tongue. She smacked her cock against it a few times, then slowly slid it into my mouth. She only gave me a few seconds to get acquainted with it before she started ramming it down my throat. She would pull out for brief moments and I would desperately try to catch my breath. Then she would ram it back down, harder and longer. She started grabbing my hair to keep my head in place and forced her entire shaft down my throat. Over and over. I was a complete mess of saliva and tears, but this just seemed to egg her on even more. Finally, she pulled out and actually let me recover.
Knock, knock. Someone was at her apartment door.
"Perfect timing," she said, and she hopped off the bed. I didn't know what to do, so at first, I just laid there in her bedroom. I could hear her talking to someone, but she didn't seem like she was in a rush to get back to me. So I went into her bathroom to clean myself up.
When I got out of the bathroom she was back in the bedroom. With a friend. A big friend. A big, naked friend. A large, black, muscular man with an enormous dick between his legs.
"See," she said, talking to her friend, "I told you he is cute. I already used his throat, but I saved his ass for you." Her friend didn't say anything. He just stared at me. With hunger in his eyes. And started slowly stroking himself.
Desire and eagerness sparked within me seeing that huge dick, but the suddenness of the situation was too much for me. I walked out of the bedroom. Neither of them tried to stop me, but the woman followed me out. I walked to the apartment door, but I couldn't find my clothes.
"You are free to leave," she said. "But I seem to have misplaced your clothes." Fuck, I thought. For a brief second, I considered leaving. Running out the door. But I had no clothes, no phone, no money, and was miles away from my apartment. It was cold out. Shit, shit, shit.
"I'm kidding!" she said. She must have seen the panic on my face. "I'm kidding. Here." She went over to a cubby next to the door and pulled out my clothes. She must have folded and stored them when I was in the shower.