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My First Time With A Woman

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I had lost my virginity to my best friend Jayson but maintained that I was still straight. Now I was going to be with a woman. A real woman!

When I was 16 I lost my virginity to my best friend Jayson. We had fooled around for years. From just watching each other masturbate, to working up the courage to give each other oral sex. Eventually we made it as far as anal sex.

It was about a year after Jayson and I had started having anal sex together. It was an on and off type of thing. Jayson had moved to a different school a few towns away and we hung out less and less.

I was 17 and beginning my senior year of high school. I had never had a real girlfriend yet. I had made out with a few girls here and there but never made it past that.

I lived in a duplex, we lived in the downstairs unit and in the upstairs unit, another family. A mother and her two kids. The mothers name was Kim, and her two kids were Julie and Klint. Klint was 2 years younger than I was, and we hung out from time to time, mainly because I was in love with his sister. Julie was in the same grade as I was and I had been in love with her from the moment I met her when I moved into the neighborhood 9 years earlier.

Julie was thin, had black hair, pale skin, and had developed rather nicely. For a girl that probably didn’t weigh more than 100 pounds, she had a nice set of breasts. She was somewhat nice to me. I’d sleep over at their house sometimes and she’s have a friend sleepover as well and we’d always hang out and even play truth or dare. It’d always come to a screeching halt when someone dared someone else to kiss one another.

One night after Jayson and I had finished having sex, we laid in bed talking. He asked if there were any hot girls I liked at school this year. When I shrugged off the questions he had, he realized that I was still hung up on the pipe dream of dating Julie. He urged me to just ask her out.

“If she says no, at least you’ll know and you won’t have to think about it anymore.” He told me.

For some reason I had never thought of it like that. It still didn’t help with the fear I had of her.

Fall was starting to wrap up and winter was coming but we had an unseasonably warm November day and Julie had decided to lay out in our backyard and get some sun. She did this regularly in the summer and I always got a fantastic view from my bedroom! I’m not going to lie, I masturbated while staring at her in her bikini hundreds of times.

Something about this particular day, I had had enough! I was just going to go outside and ask her out. I was going to be confident and assertive. I opened the back door and approached her. She lifted her head and pulled up her sunglasses. My heart was pounding so hard I couldn’t hear myself think. I chickened out.

A week passed and I was hell bent on trying again though. I worked up the courage on a Saturday afternoon to knock on their front door.

“C’mon in!” The voice from the other side yelled. “Oh, hey! Klint is hunting with his dad this weekend.” Kim said as she noticed it was me.

“Oh.. um.. I was actually looking for Julie.” I said awkwardly

“Oh my God! Are you…” she asked

“What?! No! No, I’m just needing help with some homework.” I said staring at my feet.

“You don’t have any books with you.” She said laughing. “C’mon in. I could use your help with something.” She added.

I entered and closed the door behind me. She told me Julie was at the movies with another guy, but she was wondering if I’d help her with a few chores around the house. I was really bummed about Julie but I reluctantly agreed to help Kim with her chores. It was nothing big, I helped her move some furniture around so she could vacuum and not much more.

When we finished, she offered me a Coke and we sat on the couch. Kim, was a 44 year old version of Julie. Thin, black hair, pale skin, albeit kind of weathered. At the time I thought she looked old, but now that I’m almost 44, I realize that she looked normal for a woman in her mid 40’s.

“You’ve had a crush on Julie for a long time haven’t you?” She asked. “You don’t have to answer, I and everyone already knows.. including Julie.” She added after I didn’t answer her original question.

We talked for about 15 minutes while I drank my Coke. She asked about the football season and how school was going. Very basic on the surface questions. Then she got up and went to her room for a moment. When she returned, she was wearing just her bra and underwear. I was so unbelievably taken back by it, that I dropped my can of Coke on the floor.

“Sorry!” I yelled out

“No, I’m sorry. It’s laundry day and my clothes were filthy and I caught you a little off guard I imagine.” She said laughing a bit.

As she was on her hands and knees cleaning up my mess, I couldn’t take my eyes off her. Suddenly she went from Mom next door that was just kind of good looking to, holy shit my cock is rock hard mom next door.

My cock did just that too. I was instantly rock hard and I adjusted myself when I thought she wasn’t looking. She caught a glimpse of it out of the corner of her eye and looked up at me. She smiled as she sat back on her heels and placed the towel on the table. We stared at each other for what seemed like 20 minutes but in reality was only about 5 seconds.

Kim reached her hands behind her back and unhooked her bra and threw it on the floor. She had small little A cups but for a 44 year old woman, they were outstanding! Her nipples were tiny and dark, and they looked as hard as my cock felt. My jaw was wide open and I was speechless. As sat there staring at her, she crawled toward me and began unbuttoning my pants.

“Are you still a virgin?” She asked as she unzipped my pants and reached inside.

A shockwave of ecstasy shot thru my body as her cold hand wrapped around my warm cock.

“Kind of…” I mumbled in response unable to focus on anything beyond her cold hand.

“Sit back and relax.” She said placing her hand on my chest and pushing back into the couch.

She then pulled my pants down to my ankles, and crawled back between my legs. Once again her hand wrapped around my shaft. Her lips and tongue hit the tip of my cock and I almost came right then and there! I couldn’t believe what was happening!

Jayson and I had been exchanging blow jobs with each other for a couple years now and he wasn’t good at it at first but had gotten pretty good at it over time, but he had nothing on Kim. She was a professional cock sucker! I couldn’t believe it!

After 2 or 3 minutes of her sucking my cock, she stood up and pulled her panties down and kicked them at me. They landed on my chest and I picked them up and smelled them. She laughed as she she began to straddle me. Looking back I’m surprised she didn’t end it right then and there.

She reached down and grabbed my shaft and placed it against her pussy. She was so wet that I slid inside her effortlessly. She sat down on my lap and my cock went balls deep inside her.

“Holy shit! You got a thick cock!” She moaned out as she began to grind.

My hands reached around and grabbed her tiny little ass. It felt like I had two apples, one in each hand.

“Smack it!” She demanded

I did as she ordered. I smacked her ass once, then twice.

“What kind of pussy are you? Smack my ass!” She said much more assertively.

This time I smacked it much harder.

She put her little tit right in front of my face and demanded that I bite her nipple while I smacked her ass. Her hand then reached around to the back of my head and grabbed my hair. Her other hand was digging into my shoulder. She had very long nails and she left some serious marks.

“Oh god! Oh! Oh, harder! Harder!” She screamed out “ I’m gonna cum!”

She began yelling out so loud. Her body was shaking and her toes had curled. She was out of breath.

“Oh my god, I haven’t had an orgasm like that in a good long while!” She said trying to catch her breath. “How do you wanna fuck me?” She asked

“What do you mean?” I asked back

“Do you want me doggystyle, on my back? Don’t you want to cum?” She asked

“I came when you were cumming.” I said back

“Haha, I didn’t notice.” She laughed

“You were screaming pretty loud.” I responded

She climbed off me and sat next to me. My cock was soaked! It was covered in my cum and her juices.

“You made quite the mess.” She said laughing

“This is your mess.. mostly.” I responded

“You caused it.” She said

She stood up, picked up her bra and headed toward her room. She turned back and asked where her panties were. I picked them up and handed them to her.

“You know what? Since you like them so much, you can keep them. As a way to remember this.” She said walking back to her room.

I thought: how could I ever forget this? I pulled up my pants and sat back down waiting for her to return. When she came back, she was just wearing a bathrobe and carrying a towel. She seemed surprised I was still there. Suddenly it was awkward again.

“I’m gonna go take a shower. Thanks for everything.” She said kissing me on the cheek.

I left and was quite pleased with myself.

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