For Halloween, Oliver wants to be a pretty princess. It’s the only time of the year when crossdressing is encouraged, really. And normally uptight and prudish Oliver came to me with a sweet request to be a slutty princess. Then, he wanted me to give him crossdresser strapon sex at the end of the night. How could I say no to that?
Rather than go for a very poofy ballgown dress, Oliver chooses a little tight black dress and shows off his costume and makeup to me in my bedroom. The makeup is decent. Really, it’s probably applied a little too heavily. But as it’s Oliver’s first time with makeup, I want to instill confidence rather than humiliation. Especially since Oliver came to me with his request. So instead of saying anything about the heavy makeup, I ask him to give me a twirl and show off his outfit.
As he spins, he bends over to show off the black lingerie he’s chosen for himself. There’s a black thong and a flash of a buttplug. Curious, I kiss him as my hands reach around his hips to his asshole. He really does have an anal plug. To be honest, I’m impressed by how dedicated he is to having crossdresser strapon sex tonight.
Oliver falls back onto the bed, opening his legs for me. His dress slides up his hips and over his stomach. The action leaves his “clit” exposed, as his thong has somehow moved to the side. “Come on,” he begs me in a high-pitched voice. Then, he moves his legs up by his head, trying to entice me to fuck him. “I don’t need prep.”
“Because you’re a slut,” I remind him. After a moment, I remember how much he wanted to engage with the crossdresser strapon aspect of our sex. “A slutty princess who prepped herself,” I add.
While I adjust the harness for my strap, Oliver is tugging the anal plug in and out of his greedy asshole. Honestly, watching him play with himself reminds me why I love Halloween. It allows guys like Oliver to break free of their inhibitions, just like Oliver is doing right now. Tonight, he’s not an uptight man. Instead, he’s a slutty princess ready for me to fuck and ruin.
I move between his legs and reach down to pull out his anal plug. Surprisingly, his asshole releases it easily, though it gapes a little. After his hole is empty, it clenches around nothing, desperate to be filled again.
How can I say no to such a pretty crossdresser underneath me? So, I lean down to kiss him. At the same time, I line up my strapon with his entrance to give him the crossdresser strapon sex he craves. As he opens his mouth, I push the head of my dildo inside him. Immediately, his body tenses up at the penetration.
In response, I stop moving and wait for Oliver to relax and adjust to my dildo’s girth. Plus, in order to give him some extra breathing room, I pull back from our kiss. When I do, I notice that his lipstick is smeared over his mouth.
Although it’s messy, for me, his lipstick smear shows how much he’s into our crossdresser strapon session right now.
He takes a moment to breathe before he nods for me to continue. I slowly move my hips back and forth, manipulating the strapon in and out of him. Next, I kiss his neck as I give him the deep anal fuck that he needs right now.
From the corner of my eye, I see his fingers gripping the sheets. At the same time, I feel his cock twitch as it smears precum over my belly. Knowing he’s close, I give him one more kiss. “Pretty princess,” I tell him, trying to engage in that crossdresser strapon sex fantasy of his. Sometimes, a few words are all it takes.
This is also a success. My words are enough to shoot him over the edge. In fact, his body tenses up and he shoots quite a large load between our bellies, cumming hard. As he shakes through his orgasm, I slow, loving the feeling of my crossdresser underneath me.
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Megan is extremely open minded. Plays along with even the most taboo fantasies. Close your eyes and enjoy!
Jamie has gotten insanely popular, so she is often “busy” or “offline,” but a call with her is well worth the wait. Sweet, attentive, and often funny as well as dirty, she has raised my fantasy role-play into something hotter than I ever imagined it could be.
Paris is incredible! She has such a sexy voice and an open mind.
My first call with Dixie was so fantastic! Unbelievable voice! So soft, so sweet, so nurturing, so Southern! Dixie is everything I ever wanted in a Southern lady. Her voice will leave you shaking and breathless as she weaves her Southern charm and teasing into your mind. Dixie is the one I have waited for my whole life! Five big stars for this sweet, classy Southern lady who touched something very deep within me. I LOVE Miss Dixie! The Southern Belle of my dreams!
Brittany is the best! She remembers and always engages. Others sometimes guide the call through a generic script and don’t really listen. Brittany ALWAYS shows up and makes you feel like you’re special and important!
Brittany knows exactly how to get me as turned on as physically possible. She is amazing.
I have been calling PSK for well over 10 years. This was my first call with Skye and she was amazing. She is beautiful and her voice is so sexy. I laid some frame work for a nurse role play and Skye took it from there. I will be back every 2 weeks for my follow up appointments and physical therapy. Thank you, Skye.
I just finished my second call with Skye, and she is such a sweetheart. She’s easy to talk to and made me feel very comfortable. I’m very much looking forward to talking with her again.
Jesse is incredible, a true professional!! I love talking with her.
Yesterday I was honored again to be in Aileen’s presence. What an amazing call. We touched on the 10 tenants of Aileenism that I have written for Her. Call Her and perhaps She will share them with you. I love ❤️ and worship Aileen. As it says in Aileen’s Holy Scripture chapter 13 verse 15: Though She slay me yet will I trust in Her.
Roxy is awesome, especially if you like to roleplay. You will not be disappointed when you call her. Her oral skills are insane. She likes to blow more than your mind.
I can’t say enough good things about Raven. From her sexy voice to her storytelling skills, she’s outstanding. She definitely pays attention and follows along in roleplay. Definitely one of the best.
