Exploring Cheryl – My First Time

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My senior year of high school was a year of sexual awakening for me. This story happened soon after I turned eighteen. It’s about my first time, which was with a beautiful young woman who happens to be a mom. Nowadays, she would be called a MILF. Back then, we didn’t know the term, or certainly, it wasn’t used where I lived.My mom babysat for a few kids to earn extra money. One of the kids she babysat was about three years old, and her parents were divorced. Her mom was Cheryl and she was gorgeous. She reminded me of the famous porn star at the time, Marilyn Chambers. They both had similar hairstyles and similar bodies, including their perfect size tits. Cheryl had blonder hair, through. Both had no problem making me hard. Cheryl probably was about twenty-six to twenty-eight years old.Cheryl would usually pick her daughter up around 5:00 pm. Sometimes my mom had left to do errands, so I got to talk with her as her daughter got ready to go. Just simple talk that I don’t even remember, but it was nice to be close to her. Her face was so pretty with amazing green eyes and her perfume was always intoxicating. Afterward, I’d go to my room and fantasize about having sex with her as I jacked off.One Friday night, I was getting ready to go meet my friends. The plan was to hang out at the mall and then head to the university campus to drink beer and hopefully meet some college girls. It was pretty easy to get beer back then, even if we were underage. My mom asked me if I could stop by Cheryl’s house to drop off a toy. Her daughter had forgotten her favorite doll when she was picked up earlier. Cheryl had called my mom frantically looking for the doll. Seems her daughter was spending the weekend with her dad and was very sad without her doll. Of course, I said yes. At the time, I wasn’t even thinking about the escort beylikdüzü fact that I was going to Cheryl’s house alone on a Friday night. I was only thinking about quickly getting the doll dropped off, so I could meet up with my friends.I got to Cheryl’s house about 6:30 pm and rang the bell. My mouth hit the ground when Cheryl opened the door. She was on the phone (cordless phones back then) and quickly waved me inside. She was wearing my fantasy clothes for a woman; a beautiful black dress, black stockings, and black heels. Her dress was perfect as it was tight and really showed off her curves. Her tits weren’t huge, but the tight low-cut dress really accentuated them. I was hard and just staring at her as she was finishing her call. From the tone of the conversation, I could tell it wasn’t going well. I thought it must be her ex-husband since she had slight tears in her eyes.She finished the call only a few minutes after I arrived. As soon as she hung up she yelled, “God, I hate men. Why are all of you so stupid?”I must have just stared at her with my mouth open unsure of what to say. She looked at me and smiled and said, “I’m sorry, James. I didn’t mean you.”“Was that your ex-husband?”She said, “No, it was supposed to be my date tonight, but he just called and canceled. My first date in months and he cancels at the last minute.”“Why would he cancel?”She said, “Seems like he’d rather hang out with his friends than enjoy this,” as she motioned with her arms up and down, meaning he was missing out on enjoying her gorgeous body.I wasn’t even thinking and just said, “Well, that was stupid.”Cheryl smiled at me and then saw the doll in my hand. She came closer, taking the doll from my hands, and saying, “Thank you for bringing Patty’s doll back. I’ll drop it off at escort akbatı her dad’s later.” She set the doll on the table next to the couch and then asked, “Could you help me with my dress? This thing is so tight it’s nearly impossible to unzip myself.” As she said it, she turned her back to me and lifted her hair, so I had access to the zipper.Holy shit, I could not believe this. Here was this gorgeous woman in front of me, asking me to unzip her dress, alone together in her house. I’m not sure that I was even breathing. I actually was not thinking that anything would happen, but I was thinking what an amazing memory I’d jack off to later that night.Moving towards Cheryl to unzip her dress, I was careful not to get too close or she’d easily feel my erection through my jeans. She probably saw it earlier if she looked, since my jeans were tight. As I reached for her zipper, I kept thinking, I want to remember this forever. Her smell was incredible. Her beauty was incredible. I slowly began to unzip her dress. It wasn’t easy since it was so tight. The first few inches went easy, but then the zipper began to stick. I had to place my hand on her shoulder to get more leverage on the zipper. As I did that, she backed into me and felt my erection. I don’t think it was on purpose. It was just part of the natural movement to help with the zipper.I heard her gasp slightly as she felt my cock through my jeans. I kept tugging on the zipper, and finally, it came unstuck and then went quickly all the way down to her hips where the zipper started. The two halves of her dress now were slightly separated, and I could see her amazing skin. So soft. I could see the black bra she was wearing. I imagined she was also wearing black panties. Clearly, she dressed to make an impression for her date escort beylikdüzü that he would never forget. He truly was stupid to cancel on her.My hand was still on Cheryl’s back and the zipper as she turned around. My mouth must have been open as I was just in awe of what I was looking at. Cheryl said, “Thank you.”She then gave me a peck on the cheek and then a peck on the lips. Oh my god, this gorgeous older woman just kissed me. I opened my mouth and went to kiss her back, and soon our tongues were entwined. After about twenty seconds of kissing, she broke away, didn’t say a word and took me by the hand, and led me to her bedroom. I was in a dreamland, following her as I knew what was going to happen, but I couldn’t believe it.Once we were in her room, she dropped my hand, turned around, and slowly slid her dress off her shoulders and down past her hips. She then dropped it to the floor and stepped out of it. She then took off her heels and looked at me. There in front of me was this beautiful older woman in a black bra, black panties, and black stockings. My cock was so hard.“You are gorgeous,” I said.Cheryl smiled and pulled me to her bed. As she fell back on the bed, she pulled me on top of her, and we began kissing again. My right hand cupped her tits through her bra as we were kissing, and I began to pinch her nipples as I massaged her tits. Cheryl was moaning, so I could tell I was doing what she wanted. She then unclipped her bra from the front and pulled her bra off. She said, “Suck my tits, James. Bite my nipples.” I quickly obliged and started sucking on her. Her nipples got so hard in my mouth. Cheryl was just moaning and encouraging me more as she slid her panties off. With her panties off, my hand went to her pussy as I continued to suck her tits. She was so wet.Cheryl then stopped me and told me it was time for me to get naked. I stood up and started to take off my clothes. As I was taking off my clothes, I watched Cheryl rubbing her pussy with one hand and pinching her nipple with the other hand. I was now standing in front of her with my cock at attention.

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