"Oh yes," I heard Jessica moan as she rode me. It was early Saturday morning, and we had woken up before the sun came up, our hands instantly reaching out for each other and our fingers exploring our bodies as we pulled each other close and started to kiss.
We quickly had our pajamas off, and Jessica straddled my lap, sliding my thick, six-inch-long cock into her wet pussy. Her hips had been rolling back and forth on me as I reached up with my hands and squeezed her C-cup-sized breasts.
"God, you feel so good," she said with a look of pure pleasure on her face. "Are you excited for tonight?"
After a few weeks of planning, I was going to take Hannah, Jessica's sister, out on a date that night and take her virginity afterwards.
"Yes, I am," I told the brown-haired woman as I put my hands on her hips and helped to guide her up and down my cock.
"Show me what you're going to do to her," Jessica said.
I pushed her off me and helped her lay down on the bed. I climbed between her legs, laying my thick cock on her pussy, as I leaned down and passionately kissed her. I reached between us and guided the tip of my cock into her waiting vagina, ending the kiss as I slowly pushed all the way inside her. I helped myself still for a few moments before I started to pull back out and started to thrust in and out of her.
"Oh, yes, Danny, baby, that feels so good," Jessica moaned. "Hannah is in for a night. I'm kind of jealous."
"Why is that?" I asked her as I slammed into her over and over.
"Because the first cock she'll ever feel inside her is you," Jessica said.
I started to think about what being inside Hannah would feel like, how tight she hopefully was, and what her moans would be like. I pushed myself above Jessica, thrusting in and out of her, going harder and faster, until I felt my orgasm building up, and I pushed deep into her as cum erupted out of my cock and shot deep into her.
Jessica rolled her hips under me, pumping my cock as she felt the cum inside her. She grabbed my face, her lips meeting mine in another passionate embrace. When we ended the kiss, our foreheads touched as my cock went limp and slipped out of her.
"I can't wait to hear all about it, and I really can't wait to ride you tomorrow," she said as I rolled off her and got up out of bed.
Part of what took me and Hannah a few weeks to plan was where this all would take place. She didn't want to get a hotel room just for it, and she was in between apartments, living at her parents house, and it was definitely out. The only option left was mine and Jessica's apartment, but we had to convince Jessica to leave it for a few hours. So, as Jessica left that night with her son Liam, planning on taking him to visit his grandparents, take them out to dinner, and go to a movie, I left at the same time, meeting Hannah at her favorite restaurant.
When I arrived at the restaurant, Hannah was already waiting for me, and I rushed inside to find her in the waiting area. She gave me a quick, nervous hug before the hostess called our names, and we followed her to our table. Hannah had chosen to wear a tight pair of blue jeans that night, and I admired her butt as she walked in front of me. Her brown hair was down and loose, ending around the middle of her back, and I kind of was hoping that she had a hair tie to pull it back in a few hours. The restaurant had a western-style theme, and Hannah had put on a checkered blue and white button-down shirt and brown cowboy boots to finish off her outfit.
As we sat down at our table, styled like an old stagecoach that the restaurant was famous for, Hannah laughed and said, "I never know if I'm underdressed or overdressed when I come here."
I laughed too, looking around at the other people in the restaurant. It was a good mixture of people in business suits and families out for a dinner night. We both browsed the menu, talking about different options before we both settled on a steak and shrimp meal. We ordered when the waitress came with our drinks, and sat back as we waited.
"Is it just me, or is this weird?" She asked me.
"My whole life for the last two years has been weird," I said with a laugh. "What makes it weird to you?"
"I don't know, being on a date with my sister's boyfriend, knowing what we're going to do tonight, and knowing that I've somehow convinced myself that it's all OK," she told me.
"We don't have to do anything if you don't want to," I reminded her. "We can just enjoy this night out between two almost family members."
"I know. But I still want to. Jessica thinks that I should give you a blowjob first to make you last longer. What do you think?" Hannah asked, lowering her voice so she wasn't heard in the restaurant.
"I don't know. If we had all night, maybe. But it might be best for your first time if it doesn't last super long," I told her.
"Yeah, that makes sense," Hannah replied back as our food was brought out to us. We ate our meal while we talked, paid at the end, and walked out of the restaurant holding each other's hands.
I walked her over to her car and wrapped my arm around her waist, pulling her in close as she wrapped her arms around my neck and laid her head down on my shoulder. "Thank you for dinner," she said. "It was good."
"Of course," I told her. She turned her head towards mine, and our lips met for the first time that night. We kissed for a few seconds before she pulled away, and I asked if she was OK.
Hannah nodded her head and said, "Yes. I think so. Just nervous."
"We really don't have to do anything if you don't want to. Nobody is forcing you, and nobody will think less of you. I'm totally OK with just ending the night here," I reminded her.
"I know. I'll see you at your place, OK?" She turned to get into her car, and I shut the door behind her. I jogged over to my car and jumped into it, following her as she drove out of the parking lot. On our way back to my apartment, I was stopped by a red light. Hannah made it through and I arrived a few minutes after she did.
I parked my car next to hers and glanced over at her, still sitting in her car. She smiled at me before taking a deep breath and getting out of her car. "Here we go," she said as we walked over to my apartment, and I let her inside. She pulled off her cowboy boots right inside the door before turning back to me as I shut the door behind us.
She wrapped her arms around my neck again as we leaned together and began to kiss more. I wrapped my arms around her waist, pulling her close to me, as we walked towards the couch. I fell backwards onto it, sitting down, as Hannah climbed onto my lap. She stopped kissing my lips, instead kissing my face, neck, and anywhere else she could reach.
"What position did you lose your virginity in?" She asked me.
