Lucky with Ashley

It was a new school year, one that I was looking forward to and even though I had a full class, there was one particular young lady that I wanted in my class, but unfortunately she was not assigned to me.

Ashley was a thin Latina with long blonde highlighted brown hair, and she was tall for her age. She wore glasses, and even though she still had braces, she had an infectious smile with big lips. Ashley was very young, but she really had a great figure, and looked great in jeans. As the time went on, my feeling for her grew and being that she was kind of tall, I tried to justify my feeling subconsciously for her but, deep down I knew she was too young to pursue.

As I said, she wasn’t in my class, but I was able to pretty much interact with her everyday. She had a friendly outward attitude, big eyes, sexy lips and when she happened to be wearing jeans, I loved watching her from behind, because she really had a great little ass.

Over the next few months, we kidded with each other whenever we talked, and she seemed to become more easy going, even a little flirtatious. I knew I had to be careful because whenever we started to flirt with each other, I had thought of being with her, but I quickly told myself to stop before it became inappropriate. However, I think there was starting to be a mutual attraction that we both felt but we couldn’t pursue our feeling or at least I felt I couldn’t because she was a student and she was so much younger.

More and more, I really started to want to be with her and when Ashley asked if she could start coming in early and I agreed, but then she immediately asked if I could stay late too. I was hesitant at first but of course I agreed wholeheartedly, always hoping something might happen between the two of us, thinking that maybe there was a way to ask her out, but I would always reject the thought telling myself, “Your too old.”

Ashley continued to come in early and stay late so we could work on her assignments, but I felt that her assignments wasn’t the reason she was coming in, because basically her assignments were done and we usually ended up just hanging out and talking. When it finally hit me, I realized she had become infatuated in a away about spending time with me. I was delighted that she found me interesting enough to want to spend time with me, but again I knew I couldn’t pursue her.

I wanted to be with her too but I also felt it was just an infatuation, continuing to tell myself that I needed to be careful, and thought to myself, “What was I going to do if she wanted more.”

I felt that we were in the same boat when it came to actually acting on our feels, and so we were left with spend what time together, thinking about, “What if.”

One afternoon however, while we were working on one of her assignments, time had gotten away from us and when I looked at my watch, I said, “Wow, it’s late, we should probably get going.”

As we both looked at the clock, Ashley smiled at me and said, “Yea,” and after a short pause the opportunity to be with her innocently presented itself, and it would soon become obvious that we wanted to be with each other when Ashley asked, “Can you give me a ride home.”

I was apprehensive, but it was kind of late, and when she said that she would have to walk home because her parents were out of town, I again hesitated, worried, and immediately thought, “What would people think,” but when realizing how far she would have to walk, I felt it was an innocent request, realizing I probably should give her a ride.

She was visible excited and reaching over, she gave me a big hug, thanking me for give her ride. It felt great to feel her and she smelled great too. As we looked at each other, I said we should probably get going. As we headed out of the building, we cut across the blacktop area on our way to the parking lot, and it didn’t look like anyone noticed us leaving together, or at least I hoped no one saw us.

In the car, Ashley seemed a little nervous as we pulled out of the parking lot, but when I asked her which way I need to go, she seemed to snap her out of it. Looking at me, she gave me a few directions on which way to head and trying to keep it easy-going, I tried to make idle chit chat. Everything seemed to being going okay, and after we made a few turns into the nearby neighborhood, Ashley looked over at me and said, “This is it,” as we pulled up front of a small house.

As she undid her seatbelt, I held my hand out to shake hers, but as she turned back, and looked down at my hand briefly, I felt there was something else weighing on her. Ashley immediately looked up at me and asked if I wanted to come in. I was shocked and hesitated as Ashley said, “Do you want to come in? “ reminding me that no one was home.

I was troubled and when I again didn’t say anything right away she seemed almost apologetic when she said, “Maybe you can wait until I go inside.“

I was torn, I wanted to be with her, I wanted to go in but I was having conflicting thought about being alone with her. However, when Ashley reached over and touch my hand, I immediately realized this was the opening I was hoping for and thought, “If I don’t take it, it’ll never be there again.”

She now opened the car door and as she looked at me she said, “Thanks for the ride home.”

Without hesitation I said, “Well maybe I can come in for a little bit.”

Ashley immediately smiled at me and said,”Come on.”

She was as excited as I was nervous, but as we looked at each other, I simply nodded and replied, “Yea, okay.”

Ashley was beaming and as she opened her door she said, “Come on, let’s go.”

I quickly opened my door, but as I got out of the car, I became very paranoid as we headed up the walk. I looked around to see if anyone was watching, and being it was dark, I didn’t noticing anything, but made sure to hurry us into the house.

As we went in the front door, the living room was immediately to the left and the kitchen was further back, and as Ashley asked if I wanted anything to drink, she put her backpack down and walked toward the kitchen. I asked, “What do you have,” as I followed her into the kitchen. Ashley opened the refrigerator door and said, “Well there’s water, Pepsi, and there are a couple beers, if you want one.”

I was hesitant but when I asked her to choose she said, “Let’s share a beer.”

I agreed and as she handed it to me, I opened it and immediately took a big drink, hoping it might calm my nerves. I now passed it to her, and after she too took a drink, we stood there sharing the beer as we talked about stuff. Our conversation wasn’t really about anything that I can remember and as we eventually finished the beer, Ashley asked if I wanted to go watch some TV.

She ushered us into the living room and as we sat down, Ashley scooted close to me, and leaning into me, she kissed me on the cheek. I was shocked and as I looked at her, she was smiling as I asked, “What was that for?”

Ashley quickly replied, “Thanks for the ride home and for wanting to hang out.”

I couldn’t believe it and as I put my hand on her thigh, I told her, ”I always enjoy spending time with you,” which made Ashley put her hand on mine.

As I looked at our hands, Ashley gently squeezed mine, causing me to look up at her. There was a pause as we looked at each other, she leaned into me and hugged me. It felt good to hold her and as I kissed her on the head, she looked at me, and kissed on the lips. It kind of shocked me but it was nice too, and as we continued to look at each other, I put my hand on her waist, and we kissed again.

It didn’t take long before we were French kissing, tongues in each other’s mouths as we started to feel on each other. Ashley‘s body felt so good and as we continued to make out, I reached up, feeling on her boob. Even though I could feel she had on a bra, it was giving me a hard on. Boldly now, Ashley reached down trying to undo my pants. I wanted her to get them off and as she struggled to undo them, we stopped kissing and leaning back, I tried to give her better access, and thought, “Oh my god, is this really going to happen?”

Seeing that she was continuing to have a hard time, I stood up, and as she looked up at me, Ashley asked, “What’s wrong?”

Nothing was wrong and as I got my pants undone for her, she immediately inched them down until they dropped to the floor. She could obviously see the bulge in my boxers, and after looking up at me briefly, she grabbed at it, and as she started to fondle it, she seemed fixated. Ashley was still sitting on the couch but as she moved forward a little, I reached down to adjust my cock.

Ashley looked up at me, as I inched my boxers down, but immediately she grabbed them and pulling them down, I again adjusted my cock, so it wouldn’t hang up as my boxers came down. She suddenly stopped, and as I pulled the top open a little, I pulled my cock out.

It wasn’t fully hard but as it hung right in front of her, she looked up at me briefly for reassurance and as we smiled at each other, her eyes returned back to my cock. Ashley took it in her hand, and immediately started pulling it as she fondled it. It felt so good and as she started to actually rub it as she pulled on it, she again looked up at me for approval asking, “Is that okay?”

It was better than okay, but I simply nodded my head and putting my hand on hers, I tried to show her what to do. It felt so good and I hoped maybe she would want to suck my cock, but when she didn’t really move to do it, I tried to lean forward, push my cock toward her face.

Ashley looked up at me again. She seemed appreciative and a little confused. At first I don’t really think she knew what I wanted, but when she realized I was trying to get her to suck me, or simply let go of my cock. Ashley was obviously scared to do it, but as she continued to look up at me, I reached down,I continued to stroke my cock, which made her look down.

As she watched, I reached down and took her hand and tried to put it back on my cock, she looked at me and I told her not to worry as we rubbed my cock. Ashley again looked down as we continued to rub my cock, but I wanted to see if I could convince her to suck me..

Ashley looked at me hesitantly, but when I asked her to open her mouth, she looked down at my cock, she still looked scared, and when I whispered, “Close your eyes,” she looked up at me.

Nodding my head trying to let her know it would be okay, she closed her eyes. I tried to guide my cock into her mouth, but when the head of my cock touched her lips, she pulled way, opening her eyes. I told her to relax and as she briefly looked down at my cock, she closed her eyes again and opened her mouth. I again tried to put it in her mouth and she seemed to wince a little. It felt good but I could tell she was still scared, and when I put my hand on the back of her head, and pulled her closer, she opened her eyes. Leaning forward, I started to move my cock in and out of her mouth, which caused Ashley to again close her eyes.

It did feel good but as I watched, it seemed she was becoming a little more relaxed, even though she kept her eyes closed. Eventually I had her stop saying, “You need to stop,” as I let go of her head and grab her by the shoulders.

She did stop, and as my cock dropped out of her mouth, she grabbed at it, holding it as she looked at me. It felt good, and as I quickly sat next to her on the couch and kissing her, I told her it felt really good, as she continued to grope for my cock. We started making out, and when there was a brief pause, Ashley suggested we go to her bedroom.

I immediately agreed, and as we started to stand up, I grabbed my pants off the floor and after pulling my boxers back up, Ashley took my hand. She headed us down a short hallway, and pointed out a bedroom on the right, a small bathroom on the left, and then her parent’s bedroom was next to that.

We then walked into the bedroom at the end of the hall, across from her parent’s room, and as we went in, Ashley said, “This is my room.”

I followed her into her room as Ashley sat on the bed and laying back, spreading her arm, but I was looking at her legs spread. She now turned onto her side she said, “What do you think.”

I wanted to feel her pussy as she laid there, but as I looked around, her bedroom was rather small, with a small window. Her bed I figured must have been a twin, there was a dresser and matching night stand with a lamp, and as I looked around some more, she had posters on the walls, and a shelf with a few items on it.

I walked around looking at the stuff she had on her dresser and the posters, but I was really looking for a way to hopefully have her ask me to stay. After a pause, Ashley said, “Why don’t you sit down.”

It surprised me at first but as I looked over at her, she was smiling and as I dropped my pants on the floor, I quickly moved over and sat on the edge of her bed, right next to her, and she giggle a little. After I told her how nice her room was, there was another pause and a feeling of nervousness came over me and when I said, “Maybe I should get going.”

She smiled at me and after another short pause, she said, “Why do you want to leave,” as she sat up and scooting closer to me. I really didn’t want to leave and as we looked at each other, she said, “I really appreciate you giving me a ride home,” and as her eyes shyly looked away, I took her hand.

Ashley looked back up at me and when our eyes met, I leaned into her, and we kissed. I wanted to make it happened and I was seriously aroused by the thought of making love with her, but there was a long pause and I worried. I didn’t want to go too far, or too fast and I too was at a lost for words, but as her gaze turned back to me, and she turned to face me, she said, “That was nice, I hope you can stay a little while.”

It was nice, and I knew she was interested in more than just the ride home; I felt she was giving me permission but I continued to think, “Should I really be here.”

I decided to do it and taking her hand, I looked at her and said, “Ashley, you’re really pretty and … ,” but before I could finish she lead over and kissed me on the lips and as I returned the kiss, I grabbing her by the waist, pulling her closer.

We only kissed for a second or two and as we stopped and looking at each other we again smiled at each other. I didn’t know what to do, but didn’t want it to stop, and when we paused, Ashley asked if I was okay.

I quickly said, “Yea, I’m okay, are you okay?”

She nodded, and as we kissed again, I put my hand on her one boob, squeezing it gently. She did gasped, but we kept kissing. I could feel her small little boobs, and even though she was wearing a bra,I could feel her nipples. Ashley’s shyness seemed to fade as she moved her hand down between my legs, feeling on my crotch as we kissed.

Ashley groped to feel my cock as we kissed and when she finally found it, I’m sure she could feel it was hard, because right away she started to rub and squeeze on my cock through my pants.

“Are we really going to do this,” I thought, as I reached around her and quickly undid her bra through her top.

Immediately Ashley covered her chest and when I tried to lift her top over her head, she didn’t stop me, but as her shirt came over her head, she quickly held her bra against her chest with both hands. She was nervous to let me see her body but when I kissed her, she let her bra fall down her arms, eventually let it drop off the bed, but she again covered her boobs with her hands.

As we looked at each other, I gently pushed her hands down, exposing her firm little boobs. Ashley had puffy little nipples, that didn’t seem fully developed but as I felt on them, I immediately wanted to go down to tongue and suck her nipples and so I gradually moved down to suck her neck, and feel her boobs, eventually I made my way down to her boobs, tonguing and sucking her right nipple.

Ashley was so sweet and when she didn’t stop me, I moved my hand down to feel her crotch through her jeans, as I felt on her boobs, eventually tonguing her nipples. She did let out a little gasp but again, she didn’t stop me.

I wanted this and as I moved backup to kiss her, I immediately tried to undo her pants. They unbuttoned easily and as I unzipped them, she reached down grabbing my wrist, making me stop.

She was young and I had a suspicion that she had never been with a guy before and so in acknowledgment, I stopped and leaned up kissing her. As we continued kissing, she seemed to relax a little and when I slid off the bed and started pulling her pants off by the legs, she didn’t stop me, instead she grabbed her panties so they wouldn’t come off too.

Ashley was so pretty, and as I stood there for a minute admiring her, I started to feel nervous about what I was about to do. She was so young, skinny, and laying on her back, she was looked flat chested with only puffy little nipples.

As my eyes returned to hers, Ashley smiled as she adjusted her panties. Immediately, I climbed back on the bed with her and as I put my leg over her legs, we kissed. I spread her legs and pressed my cock against her pussy as we kissed. I now got up on my tiptoes and gradually slipped off my boxers, casting them off the bed and returning to kissing her and pressing my cock against her.

I was there and as I moved down her body, kissing and feeling her, I wanted to see her pussy and eat her if she’ll let me, and it didn’t take long before I was kissing the insides of her legs and her pussy through her panties. I eventually mouthed her pussy through her pantiesand when I pulled them to the side, Ashley put her hand on my head, but again she didn’t stop me. She only had a small amount of hair and I wasn’t sure if she had trimmed it, or if it was because she was so young, in either case I wanted to taste her.

As I looked up at her briefly, I could see her eyes were closed and I thought to myself, that she had never had anyone do this before. Pulling her panties aside a little more, I gently kissed her pussy and pushing my tongue in her slit made her rise up on her elbow. Looking up at her to reassure her, I put my one hand on her stomach and again dipped my tongue in her slit. At first she tensed up, but as I spread her lips, she laid back, and willingly spread her legs. Ashley really was tight, and as I indulged in eating her pussy, all I could think about was getting my cock in her.

Kneeling now I wanted to take her panties off and as I gradually started to pull them off, Ashley again rose up on her elbows. Her panties were damp and as I got them all the way off, she watched as I simply dropped them off the bed. I started to gently massaging her thighs, as I continued to think about fucking her. Ashley smiled at me, which immediately had me lean up to kiss her, and as I did, I let my hard cock pressed against her.

As I knelt in front of her it was quite apparent now just how young Ashley was, and I became a little nervous, and looking up at her, I could tell she was too. She really was skinny and her little tits, puffy little nipples, and tight little pussy had me questioning what I was about to do. However, when Ashley started to reach toward my cock, I smiled realizing she wanted to do it too.

I moved my hands up her thighs until I was feeling her pussy with both hands, and as I spread her pussy and fingered it, I could see Ashley watching. She was wet and I knew she would be tight. As I went back down to eat her pussy again, Ashley laid back as I bent her knees.

Ashley started to wiggle and moaned a little as I ate her pussy, arching her back a few times. I had a feeling she was probably going to cum and when she gently squeezed my head between her legs, I knew she was close.

Suddenly, she put both of her hands on my head and told me to stop, but I kept going, knowing she was going to cum. When Ashley realized I wasn’t going to stop, she let go of my head and laying back, she seemed tense up. She was breathing hard and as she reached down, touching my head she said, “Stop!”

When I stopped, I gradually moved up, kissing her body until I was on top of her, and reaching her lips, I kissed. She was out of breath and being I was still between her legs, I let the head of my cock brush up against her pussy. She pushed me away slightly but as we continued to kiss, she stopped pushing me away.

Ashley was still reeling after coming and as we kissed, I reach down, trying to guide my cock in her, and at first, she didn’t realize what I was doing, but because she was so tight, I found myself pushing kind of hard, which caused her to pull away saying, “Stop!”

Raising up slightly, I look at her and could see a look of concern as our eyes met. There was a pause as we continued to look at each other, but finally I asked, “Do you want me to stop?”

Ashley didn’t say anything right away, and when I asked, “Are you on the pill,” she seemed a little confused, or maybe she didn’t hear me, or maybe she didn’t know what I meant, but I felt she had to be on some kind of birth control.

I smiled and leaning forward I kissed her and said, “Just tell me if you want me to stop, Okay.”

She nodded her head and eventually said, “Don’t cum in me okay, Go slow.”

I nodded, kissed her and as she laid back, I pushed a finger in her, trying to loosen her up a little. She was tight but really wet, and after fingering her briefly, Ashley seemed to relax a little. I again tried to guide my cock into her with my hand and when the head of my cock touched her pussy, I could hear her take a deep breath, holding it as I pushed into her.

It was so tight and I could see she was in some pain, wincing and pushing on me a little, I knew I had to go slow as I kept trying to get my cock in her. every now and then, I pulled it out slightly and as I pushed it back in her, I was trying to slowly loosen her up, hoping she’d eventually relax.

I was in her but not quite all the way and as I continued to work my cock in and out of her, it felt so good, and as I tried to start fucking her, Ashley pushed on saying, ”Go slow.” I leaned forward kissing her with her eyes closed, which made her smile but I know started to move my cock in and out of her little faster. I wanted to cum and it didn’t take long before I was close, and when I said, “I’m going to cum,” she immediately pushed on me a little harder and said, “Don’t cumin me.”

I was breathing hard but pausing briefly I said, “I won’t.”

I didn’t want to stop, I knew I had to pull out but I really tried to focus on coming as I continued to pump her. It felt so good and I was breathing hard as I fucked her. I wanted to wait to pull out until I was ready to cum, and it did feel so good, but I ended up waiting to long.

I wanted one last push, but before I grabbed my cock and pulled out, I felt it jump while I was still in her. I quickly tried to pulled out, but it jumped again before I could get off her. I tried to hold my cock, stopping it from cumming as I pulled myself off her. Knowing I was going to cumming, Ashley rose up on her elbows,, as I let cum shoot against her pussy, finishing on her stomach, but when she saw me cum she said, “You didn’t cum in me, did you.”

I worried that maybe I had cum in her, but I wasn’t sure. Ashley’s eyes looked down now, and seeing that I had cum on her stomach, and then seeing cum on her pussy, she freaked out, thinking I had cum in her.

Ashley quickly reached down, and feeling cum on her pussy she started to cry a little saying, “You came in me didn’t you,” thinking I had cum in her.

Like I said, I wasn’t sure if I had or not but I need to try to reassure her that I hadn’t. I quickly knelt in front of her and told her, “See, it’s only on the outside,” as she wiped cum off her pussy lips with the bed covers.

I really hoped that I hadn’t cum in her and as I continued to watch her wipe the cum off her pussy, I thought I saw some cum seeping out of her slightly, but she said she was on the pill, or was she.

”Oh no,” I though, “what should I do?”

I immediately tried to convince myself that it was only on the outside, but I was scared, and I think she was worrying too, because all of a sudden Ashley reached down and as she put her fingered in her pussy, I couldn’t believe it and quickly blurted out, “No Don’t,” which instantly made her stop.

I continued by saying, “You shouldn’t put your fingers in you after touch my cum, I don’t want you to get pregnant.”

Ashley looked at her fingers and seeing cum on them, she realized what she had done. I suggested that she should go into the bathroom and clean up, suggesting she should take a shower and try to clean herself out a little. She nodded and quickly got off the bed and scurried into the bathroom in the hall. As she left the room, I decided it was probably time to go and as I got dressed, I heard the door to the bathroom open.

As Ashley returned to the bedroom she said, what’s wrong. She was holding a towel around her and as I stood up I finished pulling up my pants and said, “I think I should get going.”

She looked disappointed but as we looked at each other, Ashley nodded her head and then gave me a hug with one of her arms as she held the towel against her. I kissed her on the head and as we separated she said, “Yea, it’s getting late.”

We continued to work together on her assignments, but this soon became few and far between. She wasn’t pregnant, which was a relief because it could have gone terrible wrong.

Even though we saw each other a lot that year, we never did spend time with each other again. I continue to miss it and wish we could do it again.

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