First time with Trans

After years of curiosity about Trans community, I book a session with a professional black trans in my area. Things don’t quite follow my fantasy

Became very interested in fucking a “sissy” for a long time, and watched a lot of porn about it. The idea of dominating a sissy got me very horny, as I enjoyed dominating women sexually but was blessed and cursed with a rather thick cock. All but one, has said hell no to anal. The one was such a wild and freaky slut,

I chased that sexual high for years. After nothing but flakes and fakes on the Grindr app, I started looking at escorts. There weren’t any sissies, but I did find a few of the trans community. The black trans women, looked the part more than any sissy I had seen. They however were packing some equipment that made even what I was blessed with seem tame.

I eventually decided to let fate decide, found the escort I wanted, and the price for an hour booking. Placed a Sportsbook parlay on $5 that would net the needed amount. If it hit, I would follow through and book appointment. It hit, I woke up to the information and immediately got horny.

I masturbated and never booked, and felt like a coward about it. Messaged them back and inquired about the hour + massage. Repeated the process and the universe forced my hand. I booked the hour and a half. The half hour massage, I felt would give us time to chat. I was so lost in the massage and how amazing her touch was, I opened up about what brought me there.

The massage transitioned to me on my back and soon my cock is being sucked with a desire I’d yet to encounter. I was in bliss, these gorgeous plump lips wrapped around my cock. Large heaving tits that looked and felt so natural. Butttt, and oh my but, hanging between those thighs, was dick longer than mine and flaccid. Just shiny and smooth dangling around my head as she engulfed my cock to the base.

I couldn’t help it, and reached out and gripped it. There was heft and density to this thing. I directed it to my mouth and popped the head between my lips. She let out a moan, with a throat full. This further turned me on, and soon I was working this thick rod into a rock hard problem. She had now began only stroking my drool covered cock, while slowly working on my depth abilities.

I was so lost in the moment, I don’t recall when she stopped touching me and was only cradling my head and fucking my mouth. I remember looking up at her while she guided her dick in my throat. I gagged and coughed and she became so gentle. Removed her cock and straddled my hips and pressed her tits against me and kissed me like I’ve yet to be kissed. After our lips parted, she whispered in my ear, “you won’t soon forget this fantasy whiteboi”

She flipped me over on bed, and pulled me to edge of bed. She began to suck me from behind and prod around my ass with her finger. I tried to object, but while having cock sucked, extremely hard to say no. She told me the lubricant would help numb the pain, I was being prostate milked while sucked from behind.
Then I felt some sort of pressure from something plastic enter me, and a gush of pressure fill me. She gripped my cock very hard at the base and repeated that sensation. I had no clue what had occurred, but felt a lot of pressure.

She let go of my cock, and told me to go relieve the pressure in bathroom and take a fast shower. I was very confused, but felt embarrassed I might have gotten **** on her. So I did as asked and came out to profusely apologize. She immediately put me to my knees and told me to apologize with my mouth the right way. We picked right back up where we started.

When she turned me over this time, I was so eager to be milked, the entry of her tongue almost made me cum. She ate my ass and furiously worked my cock with her hands, driving me absolutely crazy and wanting to cum. She stopped abruptly and asked if I wanted to cum. I told her yes, but she said how bad do I want it?

Do I want to just cum, or do I want to CUM. I matched her intensity and tone and I felt her finger, or fingers slide into me. Alternating her tongue and deep finger thrusts while slowly but firmly working my cock, I thought I was about to CUM like promised when she again stopped. I pleaded no, don’t stop. She was putting something on herself now, but on my belly I could only stare back at her tits and watch her fumble around.

She placed her hand in the small of my back and gently but firmly holds me in place. Then it all made sense, I understood why everything was happening. As I could feel that monster pressing against my licked and finger fucked ass and not putting up the fight I thought it would. I half heartedly mustered out a, I don’t think I’m ready as I feel her hips and mine meet. Maybe 8-9 inches of thick black meat deep in my guts.

The strokes started slow, but once she found and consistently hit my prostate. She became an animal, “oh I knew you would love this dick” hammering away at my hole. I was made to suck it between position changes and got every bit of my hour & 1/2 and then some. She pulled out, removed condom and fucked my mouth til she came on my face.

It was truly a life changer, still love dominating women, but now bring in a dick or two to also experience it.

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