This past week I visited Chicago on vacation. I would highly recommend it if you haven’t been…so many fun things to do and beautiful scenery, but I had no idea how amazing my favorite tourist attraction would be.
I’m a bi guy who lives a pretty typical “straight” life. You could talk with me all day and never get the slightest inclination that I’m attracted to guys, but secretly I fantasize about what my life would be like if I became a sissy or even a trans woman. The thought drives me crazy, and I often find myself spending my alone time dressed in lingerie with my panties pulled to the side as I feverishly fuck myself with toys. I’ve sucked dick on more than one occasion and love the feeling of making a man cum as I greedily swallow every drop, but I had never been truly fucked like I’ve wanted to so badly.
A few days into my trip I decided to sign into grindr to see what kind of fun might be hiding around my hotel. Scrolling through the users I came across an absolutely gorgeous ebony ts woman who was looking to top. She was slim but curvy, with a nice round ass and what looked like C-cups. Her profile said she was visiting as well, and noted “thick asses to the front, and be able to take dick”. I sent her a picture of my ass spread open that I had taken, and shortly after she replied with a couple pics of her own…her cock was amazing! 6-7 inches and THICK…exactly like my favorite toys. We chatted for a little while and decided to meet. She was staying at another hotel a few blocks away, so I walked over to her hotel where she had the door cracked open for me to walk in with the lights dimmed. I stripped down and went to work immediately on that beautiful cock, sucking and licking like a depraved slut. She wrapped her legs around my head and rested her feet on my back, and clutched my head in place as she started to fuck my mouth as I gagged. I was in heaven already when i finally heard her say “come up here and bend that fat ass over for me”.
I was more than ready. She spanked me and grabbed at my ass while she squirted lube on my hole, and I gasped as she forcefully pushed her cock inside me. She felt me jump forward a little in surprise at how mercilessly she was entering me and laughed a little as she said “sorry baby, but I meant it when I told you that you had to be able to take dick”. The challenge only made me crave her more, and I quickly responded by pushing myself back on her cock. Before I knew it she was balls deep and thrusting hard, and I swear I felt her in my stomach as she pounded me and the sound of her pelvis hitting my ass started drowning out my moans. She fucked me for 10-15 minutes of pure bliss before she groaned that she was about to cum. I couldn’t think of anything else as I moaned and begged for her to own my hole like a slut and fill me with cum. She thrusted a few more times before tensing up, and pushed her cock deep inside me as she came. After we finished, we made out for a few minutes before I got dressed and made my way back to my own hotel with my cock covered in my own cum and her cum dripping out of my ass and down my leg. I’ve never felt so turned on, and couldn’t have imagined a better way to remember my trip to the windy city.
Source: reddit.com/r/gonewildstories/comments/bhikyh/my_favorite_tourist_attraction