A virgin pegging, my favorite experience! My friend’s boyfriend, Grant, had never tried anal before, but his curiosity had always made him crave it. My friend Naomi told me about it often, and she even tried brainstorming ways to bring it up. She had a little butt plug that she liked to wear from time to time, and he confessed he’d even used her toys to play wth his ass one day, but he’d never gotten as far as pegging. It was all a series of almosts, maybes, and a LOT of porn videos giving away his true desires. She showed me alllll the videos he’d been jerking off to, and we had a good giggle.
He’d been craving it all for a while. But the spark that lit the fuse was the strap-on first time I had with his girlfriend. He walked right in on it! It was a fun and kinky roleplay at first, letting him watch us like we had planned it all for him, and planned for him to “catch” us. He watched from the doorway for a while, horny and too shocked to intervene as I made his girlfriend cum. And she came hard… I’d even picked the vibrating strap-on for her virgin pegging. But that toy was secretly meant for him. We knew that when he saw it in action, he would jump at the opportunity. After all, if I’d already fucked Naomi with it, he wouldn’t feel weird for asking.
As I slipped my big strap-on out of Naomi, she went over to invite her boyfriend in on the action. She lay him back on the bed, kissing him passionately like she’d been waiting for him all night. As the seconds passed, she slipped out of her lingerie bra and had him kiss her beautiful breasts. And as she made out with him, I whisked away his jeans and pants, joining her as we played with him. She was all about him, and I was all about playing with my strap-on with him. As I lubed up the head a little more, I rubbed it against him, working just the tip in as the first part of his virgin pegging. All the while, Naomi stroked his cock and kissed him, eventually turning around in a 69.
I imagine he was overstimulated with pleasure. His beautiful girlfriend sat on his face, riding it, making him play with her. At the same time, her lips teased and played with his cock. And there I was, letting the vibrating head of my thick strap-on slowly press into him, dripping in lube. His moans slowly grew louder as the minutes passed. She deepthroated him, and I slowly slipped in another inch of my cock. Another, and another. Soon, I let that entire 8″ strap-on settle in his ass, allowing him to stretch around it and get comfortable with his virgin pegging.
The first pump was easy… The next few were slow, steady, and tender for his virgin pegging. His moans started mixing with groans. He had a sexy girl laying over him in a 69, completely using him to her own pleasure. And I stood in front of him, with my beautiful titties bouncing as I pumped that cock toy into him. When Naomi’s lips graced his cock again, he practically exploded, bursting in cum as my big strap-on pounded him. The roller coaster of pleasure had taken him so far… And then the true mischief began. I kept going, as did she. His sensitive cock throbbed desperately through it all as we kept fucking him. He was in for a wild night.
Tell me, baby.. How many inches do you want to take? Call 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.