Hooker Strap-On

I've easily seen more than 200 escorts. 90 percent of the time I'm in to straight sex but occasionally I'll get fucked by a shemale or take a pegging from an escort. This most recent time a couple of days ago I went for a pegging. Because of covid I wanted a girl that was cool with wearing a mask. For a day or 2 I browsed ads and called a couple. I only really like to see someone that answers the phone or at least texts very quickly back and fourth. The one I saw on Saturday answered the phone. She was a very cute Latina, short and thick where she needed it. She had face pictures in the ad and seemed verified. I had called her before but this time was the first that she picked up. She agreed to fuck me with a strap-on for $260 for the half hour. It always turns me on to ask them about services over the phone so I tried to get as much info as possible. She said no to taking video but yes to watching porn. We agreed to meet at her condo at around noon. Since I had a bit of time to kill, I stopped at a sex shop downtown. I brought my own dildo and strap but I wanted to see if there was something slutty I could wear. While I was browsing I settled on a school girls skirt and black and red leggings. I actually had my heart set on something more like a cheerleader but this was good enough. While I was asking the girl that worked there about sizes and styles I was starting to get turned on. I kept saying little asides like "ooh I would look really slutty in that..." and I was almost tempted to start asking if she knew much about pegging just to test the waters. I had about 10 minutes until my ass-fucking session and I could barley contain my arousal. I arrived outside her building. She had me wait because she was expecting a delivery guy and she would let us in at the same time. I usually don't like delays like this, sometimes they seem suspicious but I had seen her ad up so often I was sure she was legit. Finally she told me to just come in with someone and take the elevator to her floor. When I got to her place she took a little long to answer the door (I swear they do this to fuck with us lol). She came to the door in some lingerie booty shorts and bra. She was wearing a mask but I could tell she looked just like the add. She was really bubbly and friendly, even if it seems a bit fake sometimes it's still better than when they act disinterested. She offered me a shower which I gladly took. I brought my dildo into the shower and loosened up my asshole a bit. I squirted out a bit of lube from earlier in the morning when I fucked myself a bit to get in the mood. When I finished in the shower I dried off with my own towel and got dressed into my new slut uniform. When I exited the bathroom I saw that she had laid out a bunch of toys on the kitchen island. A 7.5 inch dildo looked fucking amazing and I asked if we could strap that on her. I got on all fours on the bed and pulled up my skirt. I played a porn video on my phone. It's a compilation of girls taking cocks in their asses and saying the filthiest things possible. She rubbed lube around my freshly shaved asshole and balls. She told me that I was her fuck-whore and I was going to beg for her fat cock. After several minutes of teasing and rubbing my asshole (she declined to rim lol) she inserted a small blue butt plug. After she took that out she was gearing up to fuck me with the strap for the main event. I shot up to my knees from the doggy position and put my hands down to catch all my cum. This was actually the first time I think I cummed without something touching my dick. She apologized for some reason and asked if I wanted to keep going. I said I did and got down on all fours about to lick my cum and let her fuck me but honestly I wasn't feeling it. I got back up and just told her I changed my mind and could I shower again. I got cleaned up and told her how much I loved the session, even if it didn't last long. I'm glad I got to see how good she was and I can't wait to have a more thorough sissification next time.