"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.
"The girl was on top," I told her.
"The girl? Not your ex-wife? What about her?" She asked as her lips traced all over me.
"I was on top with my ex-wife," I said as I grabbed her butt with my hands and started to grind her groin on top of mine.
"How about Jessica and Kourtney?" She asked.
"Jessica was doggy-style in a hot tub. Kourtney rode me for our first time," I said, barely finishing the last word before Hannah's lips were back on mine and she was slipping her tongue into my mouth. As we kissed, she took over, moving her groin on top of mine, and I moved my hands in between us and started to undo the buttons on her shirt. When enough were undone, I slipped one of my hands inside her shirt and started to squeeze her breasts through the bra she had on.
She moaned into my mouth as she felt my cock growing big in my jeans and pressing against her groin. I finished undoing her shirt, and she helped to slip it down her shoulders and off her arms, tossing it behind us. We briefly stopped kissing so she could pull off my shirt, and I started to kiss her chest and neck as she moaned at my touch.
I was rubbing her lower back with my hands, and I slowly worked them up until I was touching her bra. It was plain and black, and I quickly unhooked it. She slid it down her arms, and it joined our shirts on the floor. I glazed down at her C-cup-sized breasts, studied her nipples, and slowly moved my hands up to cup both of them.
Hannah moaned as I squeezed her breasts and moved my fingers over to her nipples. I used my thumb and index finger to rub them before I moved my head forward. I stuck out my tongue and licked all over and around both of her nipples before sucking them into my mouth one at a time.
"Oh yes," Hannah moaned as I sucked one nipple into my mouth while pinching the other one, going back and forth between the two. I continued to suck, lick, and squeeze her nipples while Hannah unwrapped her arms from around my neck, moved them down between them, and scooted back just enough that she could unbutton my jeans.
I breathed a sign of relief as she pulled my hard, thick, six-inch-long cock out of my boxers and wrapped her hand around it. Pulling away from her breasts, I asked her, "Should we move to the bedroom?"
Hannah looked down at my cock, then glanced backwards towards my room. I said, "There is still time to back out."
Instead of answering, she stood up off me, letting go of my cock as she did so. I stood up behind her, shook off my pants and boxers so I was completely naked, and followed Hannah as she walked into my room.
Once there, I wrapped my arms around her waist again and pulled her close. I kissed her lips before I kneeled down on the floor in front of her. I kissed her stomach as I started to undo the snaps on her jeans and pull them down. I had been curious what kind of underwear she had on and smiled when I saw a pair of plain white panties. As I hooked my fingers into them to slide them off, she said, "Sorry, it's nothing fancy or sexy like Jessica wears."
"That's OK," I said as I lifted up her feet to get them off. "It took Jessica a while to start wearing thongs. Maybe we'll have to buy you one."
"Oh gosh," Hannah moaned as I started to kiss her inner thighs and softly lick around her vagina. I had never seen her vagina, only touching it inside her pants, but it felt like she had shaved off most of her hair, as she only had a thin little strip right above it.
I helped her lay down on the bed, climbing on it to join her, but staying in between her legs. I kissed all around her thighs again, then ran my tongue up the moist slit of her vagina. Hannah moaned as I pushed my tongue past her lips and darted it in and out of her pussy. At the same time, I brought one of my hands up and started to rub the outside of her pussy, uncovered her clit, and started to rub it.
