All I ever did in real life was drive her home a couple times. I wish the rest had actually happened. Only the fucking is fantasy.....
I was working as a bagger at my local grocery store when I was on high school. I eventually made cashier, but right before they promoted me, I was senior bagger and got the 6 am to noon shifts on both Saturday and Sunday. I liked it fine. I didn't mind getting up early and I'd still have most of my day left when I'd get off work. Another reason I liked it was Dawn, a cashier who was in her 30s and still pretty hot, worked the same shift. I'd try to bag for her as often as I could. She wore her smock that covered her body most of the time, but I'd seen her in street clothes a few times. She was 5' 8" or so and had blonde hair and big blue eyes. Her boobs were pretty big and she had a nice ass. At 16, she was really nice to look at. She was also a flirt, not just with me, but with most of the guys there.
One day after our shift, I was leaving and heard someone call me....it was Dawn. She asked me for a ride home. She didn't live far and I wanted to show off my car...a 1977 Olds Cutlass Supreme. It was my pride and joy. I'd only had it for a few months and babied it. I opened her door and let her in the car. "Nice car. My old boyfriend had one like this. The back seat is kinda small though" she said with a teasing tone as I drove. "Yeah, it looks like it" I managed. I figured this was par for the course....her flirting with me and loving the tease. As we got close to her house, she offered to make me lunch to thank me for the ride. I was starving, so I agreed.
At her place, she made us grilled cheese sandwiches. I could hardly taste them as my imagination was starting to get the better of me. Where was this going? Was I gonna walk out of here with blue balls or what? I really had no idea what might happen. We finished eating and she looked at me and licked her fingers. "How was your sandwich?" she asked. "Filling. Thanks." I was stunned as she moved over to me, grabbed my hand and licked my fingers like she did hers.
Her mouth was so hot that I almost lost my load right there. She withdrew my fingers and asked me if I had a girlfriend. I didn't, but was ashamed to admit it to this lady who was driving me crazy. "I'm surprised....you're very attractive. All those girls at work and you're not dating anyone?" I stammered something about all the ones I was interested in were involved with other guys.
"What about me? I'm single. Maybe we can't date, but we could have other kinds of fun. Don't think I'm a child molester, but I love young guys who want to learn. Would you like to learn some things?" I couldn't even answer her. I guess she took that as a yes.
She led me to her couch and said we could start slow. She told me to relax and let her handle things. She knelt in front of me and undid my pants and slid them down. My cock was hard enough to cut steel by that time. She grasped me firmly and told me she was going to give me a hand job, then we'd work up to other things, but first I needed to learn to control me releases. She started stroking me slowly, telling me how to try and hold back. It was excruciating, but I managed not to come right away. She picked up the pace a bit and made it a bit tougher, but I managed to hold back. I was moaning and whimpering as she stroked me until she told me it was okay to let go.
I didn't care about making a mess on her or her couch or carpet....I just wanted to let it go. My cock twitched like mad as I came. The first 3 or 4 strings landed on her still-clothed chest. The rest she caught with her hand, then licked clean. As I recovered, she got up and said that the lesson had ended and every time I gave her a ride home, she'd give me another. Needless to say, I was glad we were both scheduled the next day.
I couldn't wait for noon on Sunday. As the clock ticked, I kept sneaking peeks at her. She'd smile a bit, but I'm sure she was concerned about hiding her feelings. We got in my car after work and I went damn near 100 mph to her place. She offered to make lunch, but I wasn't interested. She took me to the couch for my next lesson. "Today, I'm going to give you a blow job. It's like a hand job, but I'll be using my mouth." I knew what it was, but hearing her say it was a turn-on itself.
She lowered my pants again and opened her mouth. Unfortunately, I was not able to hold back as easily as I did with the hand job. After maybe 15 seconds, I couldn't hold back and came in her mouth. She choked down my cum and said, "That won't do. You need to try again when you're ready. Until then, I want to show you how to finger a woman, okay?" I was up for anything.
She undid her pants and removed them and her panties. I had never seen a real pussy and my cock sprang back to attention. She smiled and said, "Ready again I see. But we need to stick with the lesson plan." She spread her legs and showed me what a clit was, how to stroke it and how to gently insert a finger until she got wet. As I stroked her clit, she put her head back and started to moan softly. Her hips began to rock and I knew something was going to happen, but wasn't sure how a woman got off, but I was going to find out.
She had stripped off her shirt and bra by this point and was totally naked while I fingered her. Her body was very nice for a mid-30's woman. She'd never had a kid and was still pretty firm all over. My cock was ready to pop again, but I didn't want to fail another lesson. Her breathing got really heavy all of a sudden, her hips pulsed and she cried out in pleasure. Her pussy was spasming around the two fingers I had slipped inside her. As she was coming, I started getting ready to lose my virginity. I stood up and got ready to get between her legs, but she stopped me. "You still need to pass your lesson before you can advance." She then took me back into her mouth and blew me very slowly to keep me from coming so fast again.
This time, maybe because I had come once already, I was able to hold off a bit longer. As I hit the point of no return, she looked up at me with an approving look. I let loose into her mouth for the second time in roughly 20 minutes. She slurped and gulped and swallowed every drop yet again. I felt dizzy and had to sit down. She got me a drink of water and told me the lessons were over for today.
The week went by slow as hell. She wasn't scheduled with me until Saturday and Sunday again and it was torture. I must have jerked off 5 times that week both in anticipation and in retrospect about what happened. Finally, the weekend rolled around.
Saturday's shift was like the week...slow and torturous. I couldn't wait for the clock to hit noon. Dawn managed to whisper to me that she had a special lesson for me. I almost had to go rub one out in the bathroom after she told me this. Finally, we made it back to her place.
"You did well last week, but there is more than one way to get a woman off. Your finger simply won't do all the time. You need to learn how to lick pussy. Are you open to that? I shaved my pussy to make it easy on you." I was kinda hesitant, but figured she wouldn't let me fuck her until she thought I was ready. This time, we went to her bedroom, as she said we needed the room if we were going to do things right.
We stripped naked and got into bed. As she laid back, she gave me the same instructions as she did before the finger lesson...go slow, pay attention to the clit, be gentle until you sense the need to pick up the pace. I did as she said and was soon rewarded with soft moans of pleasure and approval. I licked her pussy lips and tried to alternate licks on her clit. Once I got into a rhythm, she did as well. Her pussy tasted better than I thought it would...it was also hot and wet. As she got close, she told me to start licking her clit harder and harder. I switched gears into overdrive and let her have it. If I thought her orgasm from my finger was strong, this one was like a hurricane. She ground her cunt into my face with such fury that I couldn't breathe for a few seconds.
She screamed and screamed and bucked and moaned and writhed and came. Her eyes rolled into their sockets and she had ahold of my head. After she finished, she said I was ready to start my final lesson.
She showed me how to get into position for man-on-top. I knelt between her knees, holding my cock and staring at her dripping pussy. She pulled me down closer and guided me to her. As the head of my cock pressed against her pussy lips, I gasped....this was the moment of truth. I slid inside her and she gasped in surprise. "Oh my, you feel so good. So big and so thick. Go slow at first, try to hold back like you did in my mouth." It was tough not to just start pounding, but I could see how slow built into fast and hard eventually.
As I slid gently in and out of her, I could feel her pussy grasp my cock. I didn't expect that and smiled as she did it. Slowly, she told me to go a bit faster and harder. She had to slow me down once or twice, but I soon got the hang of it. Pretty soon, her breathing got that familiar sound...she was going to come. I wasn't sure what to do and asked her. "FUCK ME HARD...NOW" she screamed at me.
I spread her legs as far as they would go and hammered her soaking wet cunt. I knew I was hurting her a bit, but I didn't care. As she started to spasm, my balls felt that tingle and I tried to hold off. She knew that look and said,"I want us to come together. Let yourself go when I...." She never finished the thought because her orgasm roared thru her like a runaway train. I figured I knew what she was going to say and let myself go inside her. As we came together, I felt something gush out of her pussy. Later, she told me it was her own cum. I had no idea women could do that.
We lay there sweating and panting and barely able to catch out breath. "Did I do good, Dawn?" I asked. She smiled and said that I got an A so far, but we needed to cover a few more things. We covered doggy-style, her on top, both of us on our sides with me entering from behind. She even let me go up her ass once for a minute, but made me stop....I was too big for her to take.
The next day was Sunday and we covered those lessons over and over. Soon after that, I was promoted to cashier and my shift changed. I only saw her in passing once in a while, but started dating one of the girls I had my eye on at the store. Dawn's lessons really paid off....the girl was amazed that I knew how to fuck so well at such a young age. All I could say was, "Practice makes perfect!"