Crossdresser Strapon Sex: Pegging Oliver for Halloween

Oliver confessed he wanted crossdresser strapon sex for Halloween.

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.

He must have wanted this fantasy for a while now.

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.

And I should reward my slutty crossdresser with my strapon.

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.

Oliver gasps as I push as deep as possible during our crossdresser strapon sex.

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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