Tag: first time

Before The Virgin's Date Night

Phonesex with Felicity 1844-332-2639 x 270

My sweet boy FINALLY nailed a date for this year’s prom! His whole life, he has been shy and reserved. He was more into gaming systems than girls, and for a while, I assumed he was either Asexual or gay. So you can imagine how special it was for me to watch him talk about how she wanted his tux to match her dress and that he was anxious about finding the right corsage to highlight his boutonniere.

He wanted everything to be perfect for his little queen, and that made this Momma’s heart so happy. The afternoon of their special day was more relaxed for us than his little dates. She was running amuck getting her nails, hair, and makeup done. So he said anyway. I was less than surprised when my sweet boy approached me and asked for a favor. He confessed to still being a virgin ( Momma knew) and asked for tips to ensure his date would enjoy their after-party.

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Girls are curious

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Girls can be so curious. Curious and bold. I was at a sleepover as a young adult, one of my first and last, actually. There were three other girls and I. Somehow, the topic of porn came up, and a few of the girls said they’d never watched one before. Now, this was back in the day when you could drive to a movie rental place and pick up a DVD for a few dollars. The apartment we were staying at happened to be across the street from one of those places.

We ran across the street with giddy laughter and bravely showed our IDs to get into “the back room.” There were a few creepy, pot-bellied older men looking at dirty movie covers as we browsed. They seemed less than impressed with our high-pitched squeals and embarrassed chuckles.

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During one of my very first sleepovers, my cock took control over me. I ended up riding my best friend.

My friend Donny and I had stayed up so late playing video games that by the time we crawled into bed, he had passed out hard. I was tired too, but I was also very hard. I’d never shared a bed with another person before, and seeing him lying there, deep in sleep, I don’t know. Something just took over me.

For the longest time, I just watched him and rubbed my cock through my boxers. Yes, this was before I fully embraced my fem-side. He’d fallen asleep on top of the covers in both but a loose-fitting pair of shorts. The only light in the room was the glow of the tv. The soft flicker lights made things feel like a dream. I knew I shouldn’t touch him without his permission. Hell, I knew he’d probably freak out on me, but I wanted nothing more than to roll him over and see what it felt like to ride him.

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I wouldn’t say I’ve always been a slut, but I’ve definitely have always been on the promiscuous side. Theo knew this, and I guess that’s why he came to me. We were in the library studying for yet another final when he closed my book while I was still reading it. It surprised me but got my attention, so I looked up at him. His big hazel eyes looked worried as he stared back at me.

“What’s wrong?” I asked quietly. His hand was still on the cover of my textbook when he let out a heavy sigh.

“Kaykay, I need your help with something. Something I’m scared to ask anyone else and am really embarrassed. Do you think you can help me with this,” He paused and looked behind me. “You know, telling everyone?” I was super curious and nodded eagerly. “Ok. Can you help me lose my virginity?”

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Phonesex with Felicity 1844-332-2639 x 270

It’s challenging to think about, I know the reality of it scares you a lot, but the first time you suck cock for me will be magical. You fantasize about it so much, and in your head, it’s always flawless. The truth is, it’s going to be exciting and uncomfortable. Think about who that man will be.

For sure, he’ll be taller than you. He’ll be more muscular and more masculine. I won’t pick a man who’ll be patient or gentle. He’ll push you down to your knees and yank his cock from his pants. Look up at us while you’re down there. How does it feel? Knowing you’re about to lose your throat’s virginity?

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