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 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 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 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.

Cheryl said, “Take me on my knees.”

“You want anal?” I asked. I was so naive since I thought doggy style was only for anal sex.

Cheryl laughed and said, “No honey, I don’t do anal, but I’ll show you how to get in my pussy.”

With that, she got on her knees in the middle of the bed and motioned me to join her. As I got behind her, she held my cock and guided it to her pussy. Once I felt her wetness, I pushed forward, and she pushed back, and I entered her easily. What an amazing feeling, my first time inside a woman. Cheryl lay flat on the bed with her ass in the air as I grabbed her hips and began thrusting in and out. I felt like a porn star.

As I was pumping my cock in and out of this beautiful pussy, I started spanking her ass. I’m not sure why. It just seemed like the right thing to do. Cheryl was moaning and saying, “Oh yes, baby, spank my ass. It feels so good. Don’t stop. Spank me, baby.” I now know that not every woman enjoys being spanked, but what luck that my first woman loved it.

After a few minutes, Cheryl got up on her hands, so I could reach under and grab her tits as I continued to thrust in and out.

I could tell I was going to cum and I told her, “I’m going to cum.”

Cheryl just said, “Cum inside me, baby. Cum for me.”

I soon screamed as I came inside her pussy. Once I stopped spurting, she collapsed on her stomach and I collapsed with her with my cock still inside.

We lay like that for a while, both of us moaning in pleasure. I kissed her cheek and held her tight. I didn’t want to let go. After a few minutes of cuddling, she started to roll over, and I fell out of her pussy and rolled on my back.

She looked at me and said, “That was amazing. Was that your first time?”

I was so embarrassed. It must have been a terrible experience for her that she knew it was my first time. I blushed and told her yes as I looked away. Suddenly, I didn’t feel worthy to have a woman like this.

Cheryl looked at me and said, “Oh, James, I’m so happy I got to be your first. You were great.” As she said that she started to kiss me. She then said, “Let me clean up your cock.” And with that, she turned around and went down to my limp cock. She took my cock in her mouth and started to nibble my head and use her tongue on my shaft. It didn’t take long for me to get hard again.

Once I was hard, she moved on top of me in a 69 position. I saw this amazing pussy in front of me and I just dove in. I had no idea what I was doing, but Cheryl’s moans were telling me I was doing the right things. My cum mixed with her pussy tasted amazing. My first cream pie. I had tasted my cum before, but it was so much better mixed with her pussy juices. Cheryl would pause occasionally to tell me where to lick her pussy and how great it felt.

We kept going for several minutes, and soon I could tell I was going to cum again. I told Cheryl, “I’m going to cum.”

I expected her to take her mouth off me and jerk me off, but she kept going, and soon I was cumming in her mouth. Oh my god, it felt amazing. After I was done cumming, Cheryl turned around and came to me, and started kissing me. As her tongue went into my mouth, she pushed cum into my mouth, and we shared a cum kiss. We kept kissing and sharing my cum, and soon we both swallowed what remained in our mouths.

She asked, “Did you like that?” I just nodded my head and said I loved it. She said, “I didn’t know if you’d like your own cum. That is so hot.” How could I not like it? I’d like anything this amazing woman wanted to do.

We wrapped our arms around each other, cuddling and kissing and just holding each other. It was pure bliss. Cheryl then looked at me and asked, “James, can you make love to me?” I was confused since I thought that’s what we had done, but then she said, “I want you on top, making love to me.”

I wasn’t sure I could get hard again. She rolled on her back and spread her legs. I moved to get on top of her. She spat in her hands to get some lube and then grabbed my limp cock and began to stroke me. As she did this, she started talking to me and saying dirty things to get me hard again.

“Oh baby, I love your big cock. I want you to make love to me. Take me, baby. Make me cum, baby.” Her words and her hands had the right effect, and soon I was growing.

As soon as I was hard, I moved to her pussy and she guided me inside. I then got as close to her as possible and wrapped my hands around her face as I kissed her and began pumping in and out of her pussy. I loved being so close to her. Our bodies were completely together, and we were kissing passionately.

I then elevated myself, so I could better see her as I continued making love to her. Cheryl started massaging her tits and pinching her nipples. I went down, and she fed one of her tits into my mouth. I already knew how sensitive her nipples were.

She continued to moan and encourage me. “Oh, James, suck my tits. I love it when you bite my nipples. Harder James. Harder.”

I kept making love to her. I then took both her nipples in my hand and started to pinch, squeeze, and twist them. She was screaming in pleasure, and soon I felt her pussy tighten around my cock as she finally orgasmed. It was nipple play that she needed to cum. Once I felt her pussy tighten, I went faster, and soon I was cumming too. I again emptied my load inside her. My third orgasm in an hour.

As I collapsed on top of Cheryl, I put my arms around her and held her tight. I never wanted to leave her and never wanted this moment to end. I suddenly felt I was in love. Certainly, I was in love with the feeling of sex with this amazing woman.

After about ten minutes of cuddling, Cheryl said, “You were wonderful. Thank you for making me feel so desirable.”

I told her she was completely desirable, and I had fantasized about her often. She liked that and asked if I thought about her when I masturbated. I just smiled and told her I always thought about her when I masturbated.

Cheryl then said, “You should get going, James. I’m sure you had big plans for tonight.”

I asked her if she would like to go on a date sometime. She told me I was much too young for her to date and that we couldn’t do this again. I was so disappointed.

“You need to date a girl your own age. But we will always have this memory.”

As I got dressed, Cheryl put on a robe. She then walked me to the door and hugged me and kissed me. I did not want to leave. I wanted to spend forever with her. But in the back of my head, I knew she was right about dating someone my own age. I gave her a last hug and kiss and went on my way.

I saw her a few times after that when she picked up her daughter. We never talked about our experiences with each other. I graduated soon after and went on to college. Her daughter went to pre-school, so my mom stopped babysitting for her too. I never saw her again. To this day, I still think about her and masturbate to the amazing night I spent with her. I often think about what she must look like today. I’m sure she is still beautiful.