A Hot Threesome to Pop His Anal Virginity

It All Begins with a Sexy Little Wish

I have a boyfriend who has been so curious about butt stuff for years. But he’s always felt too shy to try it out. He knows I love getting fucked in the ass, and has picked my brain about it for the past few months. What it feels like… how to relax into it and let it feel good… And now he craves to loose his anal virginity already. I have a trans girlfriend who is coming over for a hot threesome with us, and he is finally going to get his cherry popped from behind tonight!

Teasing Away Any Anal Virginity Anxiety

My girlfriend Jenny shows up in a lacy red dress that hugs her waist perfectly. I know my boyfriend is nervous, we can both see it on his face. So I take control, as he’s always secretly hoped I would, and guide him onto the bed. He’s on his back, head propped up on the pillows, and I kneel beside him, kissing him until he melts. I can already feel his cock pressing hard against me. This isn’t like impulsive car sex, I take my time to loosen him up and get him so turned on he just leans fully into the pleasure of losing his anal virginity.

Jenny and I steer him onto his stomach and knead his lower back, circling thumbs lower and lower, coaxing him with small talk and silly pet names until the tension in his hips melts. He’s so responsive and shy, trembling when I trail a fingertip just past the base of his spine. I tell him how cute his little noises are, how much I love that he’s letting us do this. He laughs into the sheets, face turned, and I see the tips of his ears flushed dark red.

I’m Ready to Make That Dream a Reality

Despite his nerves, he is getting obviously turned on, so it’s time to kick it up a notch. Jenny deserves some love and attention too, of course. I let him lie back and watch, as I crook a finger into Jenny’s bra straps and tug her toward me. Our lips meet, tongues exploring each other’s mouths. As I feel her cock making a tent under her dress, I hike the hem up her thighs until I can wrap my hands around her length. I hear my boyfriend moan softly, already twitching to loose his anal virginity to her gorgeous erection. He is such an eager audience, as I suck her off to get her nice and hard for him.

“God, that’s so fucking hot,” he whispers.

Time to Loose His Anal Virginity

We both turn to look at him. His fingers are already lubed up and pumping inside of his asshole. Jenny grins, winks at him, and pushes her dress down so her tits spill out, nipples flushed and hard. I suck her off a little more, working slow and deep, and then I pull back, using my thumb to smear spit all along her shaft.

“Looks like it’s your turn,” I say to him, my eyes trailing from his face, down to him finger fucking himself. His face goes crimson but he nods. He’s so eager to give over his anal virginity I can’t help but grin from ear to ear. He shuffles to the edge of the bed, lying between Jenny’s legs. I lean down to kiss him while Jenny positions herself with the tip of his cock right at the edge of his eager hole. My hand trails down his chest, over his belly button, and gently grips his cock. Jenny slowly slides her cock into him. He gasps, his head lolling back onto my shoulder as he finally loses his anal virginity in a hot threesome.

It’s always easier to do something new when you have someone like a sexy Goddess of phone sex guiding the way for you. What kind of tantalizing fantasies have you been wanting to explore lately? I’d love to hear all about them…

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