It’s summertime, and I am taking my boyfriend, Chris, to Vegas, baby! It’s going to be an epic trip, and I will finally be able to help Chris explore his trans curiosity.
A few months ago I was at Chris’ place and I needed to borrow his tablet to watch a video while I was trying my phone. When I opened his browser, I saw that he has been watching a lot of trans porn.
When Chris came home from work that night. I told him about what I found. Chris’ face turned red as he hung his head down and admitted that he is trans curious. When Chris looked up at me, his expression looked like he was expecting me to slap him. Instead, I took him by the hand, and told him that I want to know more.
The idea of having a trans curious boyfriend was such a turn on to for me. Starting that night, we started watching trans porn together. Chris and I would have some of the best sex of our relationship as he ate my pussy and told him that I wanted to see him on his knees with a beautiful woman’s cock in his mouth.
Over the next few months Chris and I experimented with his trans curiosity as best we could through pegging. And I love how hot he looks with my strap-on cock in his mouth, but I know pegging and a strap-on is no substitute for the real thing. That is when I decided to plan this Vegas trip. It’s Vegas baby, anything can happen.
I knew that to move Chris’ trans curiosity into reality I would need some help. That is when I called my friend Grace. I’ve been friends with Grace since college. She is one of the most beautiful trans women that I have ever met.
Grace is tall and statuesque. With deep cocoa skin, and soulful dark brown eyes. She has stunning a set of C cups, and the best I have ever seen on a living human.
Grace and I have been friends since college. We even hooked up a few times back in the day. So yes, I’m very familiar with what that dick do, as the kids say. Which made Grace the perfect person to help make Chris’ trans fantasies a reality.
While Chris was at work, I called Grace. I gave her a quick snapshot of Chris being trans curious and asked if she would be willing to meet us in Vegas to make it all happen. Because she is one of the best people in life, Grace agreed to help with my plan. So I started making arrangements for our trip to Vegas, baby!
It’s our first night in Vegas, baby! Chris and I spent the day doing some shopping, having a sumptuous lunch followed by a relaxing massage. Now it’s time to get ready to hit the club.
Tonight, I’m wearing a slinky little black dress with a pair of fuck-me pumps to die for. Chris slipped into his oxblood suit with a light pink shirt and a deep crimson tie. He knows I melt every time he wears those colors. Against his fair, pink complexion, they make him look ridiculously handsome instead of washing him out.
As I helped Chris with his tie, he asked me what kind of club that we were going to. I told him that we were going to a club that was welcoming to everyone, but is especially popular with the dolls.
A bit of flush rose in Chris’ cheeks. Before he opened his mouth, I knew that he was wondering about the odds of having a trans curious experience. I finished with his tie, and gave him a butterfly kiss on the cheek. I took Chris by the hand as we walked out of the room saying “It’s Vegas, baby, anything can happen.”
When Chris and I got to the club, it was every bit as epic as I wanted it to be. The VIP booths were luxurious. The music was fantastic. The dance floor was full, and there were dolls for as far as the eye can see. I gave the hostess my name for our VIP reservation. The hostess was a beautiful blonde doll with legs for days and an ass that you can bounce a quarter off of. I could almost feel Chris’ eyes laser focused on her ass as she took us to our VIP booth.
As Chris and I sat in our VIP booth sipping top-shelf whiskey, Grace walked into the club. The music was pumping, but it seemed as though everything stopped when she crossed the threshold. Her silver shift dress looked like liquid metal against her chocolate skin. The laser lights sweeping across the club made her deep brown eyes seem alive with fire. Her bright red lips promised mischief while making it clear she chose her company carefully.
Even though I knew Grace was going to be here tonight, my eyes followed her to the bar. Watching her perfect ass swaying to the music as she leaned over the bar to order a drink.
Grace got her drink and waded into the crowd for a while. I don’t know how long I had lost track of her, but when she appeared at our VIP booth she was beautiful. Grace didn’t say a word. She reached her hand out to me me and lead me to the private VIP dance floor above the crowd.
I could feel Chris watching us on the dance floor. Smiling, I motioned for him to join us. I pulled Chris close to me and kissed him as we danced. Grace stood behind Chris grinding against him to the beat of the music.
As Chris gabbed my around my waist his eyes got wide. I know that it was the moment realized that Grace is trans. The three of made out on the dance floor what felt like a magical eternity. While Chris was kissing me on the neck, Grace gave me the signal that it was time to take this party back to our hotel room.
Back in the room, the make out session continued. Grace and I made Chris sit in a chair at the foot of the bed and let him watch me make out with Grace.
I laid Grace back on the bed and straddled her. Grace grabbed my hips and slowly pushed her long, thick, black cock into my pussy. Grace wanted Chris to see me take every inch of her cock. As hot as it was, the way Grace spread my pussy out took me by surprise because I had forgotten how good it felt when Grace stretched me out.
Grace fucked me until I squirted all over her cock. I slid off of Grace’s cock to catch my breath. Grace sat up in bed with her cock in her hand, looked Chris in the eyes and asked “Do you want to taste it?”
Slowly, Chris got out of his chair and got on his knees in front of Grace. She pulled Chris’ head back and slid her cock into his mouth. I slid out of the bed and got on my knees behind Chris. I pressed my tits against his back and reached around and started stroking his cock.
As Grace fucked his throat I whispered to Chris how fucking hot he looks with a big black cock in his mouth. Grace pulled he cock out of his mouth just long enough for Chris to catch his breath. Chris took a breath and smiled saying “I can’t believe that this is really happening!” I kissed him deeply. Loving the taste of my pussy and Grace’s cock on his lips. As Grace slid her cock back into Chris’ mouth and I said, “It’s Vegas, baby. Anything can happen.”
Vegas may be behind you, but your journey is just beginning. If Chris’s adventure has you wondering what it takes to embrace your feminine side with confidence, don’t stop here. My Sissy Training Guide is packed with beginner-friendly tips, confidence boosters, and inspiration to help you explore your transformation one step at a time. Then give me a call and let me guide you thought your journey.
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