I really started to want to be with her and the more time we spent together I hoped 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.”
There were many years that I had students in my class that I found very attractive. Yea they were a lot younger, and yea I had thoughts of being with them, but never pursued it because I was so much older. This particular semester was no exception, and even though Ashley wasn’t in my class, I saw her in the hallway quite often, and every time I saw her, I wished she was in my class. From the first time I saw her, I had to do a double take, and when she smiled at me in the hallway and said, “Hi,” I was instantly attracted to her.
She was obviously Latina, kind of tall, had long brown hair with blonde highlights, and even though she was thinly built and flat chested, she had a great figure, especially in jeans. She wore glasses that I think added to her allure a little, and even though she still had braces, “What an inviting smile,” I thought.
Ashley had great lips, I think accentuated by her braces and as she walked past me and headed down the hallway with her friends, I couldn’t help but turn to watch. Long legs, nice firm little butt, and as I turned and headed to my classroom, I smiled, wanting to see her again.
Like I said, she wasn’t in my class, but I was able to interact with her pretty much everyday, and as time went on, I became infatuated with her. Her tall thin frame, and her friendly outward attitude, big eyes, and sexy lips, had me subconsciously trying to justify my feelings for her, but deep down I knew she was too young to pursue.
Over the next few months, we kidded with each other whenever we talked, and she seemed to become more easy going, and when I started to be a little flirtatious, I knew I had to be careful. I wanted to be with her, I had thoughts of having sex with her, and not wanting to push her away, I quickly had to tell myself to stop before it became inappropriate.
However, I do think there was a mutual attraction we were feeling, one we both needed to suppress because of our age difference, and with me being a teacher, I knew I couldn’t act on. More and more, I wanted to be with her, but there was no way. Suddenly one day, Ashley suddenly asked if she could start coming in early for extra help. I of course wholeheartedly agreed, naively feeling it was just an innocent request. She seemed excited, I was too, and being able to see her and be with her every morning was nice, but again I had to be careful.
One morning as we finished, Ashley asked if I could stay late. I was hesitant but again naively told her, “Of course.”
I was always hoping something might happen between the two of us, wishing that maybe there was a way to ask her out, or that maybe she’d say something that would signal it would be okay, but again I would tell myself, “There was no way, you’re too old.”
Ashley continued to come in early, and stay late so we could work on her assignments. However, her assignments wasn’t the reason she was coming in, because they were basically done, and we usually ended up just hanging out and talking. When it finally dawned on me that she might have a crush on me and that’s why she wanted to spend time with me, I was thrilled, but nervous too.
Maybe it was because I paid attention to her, or that she felt comfortable joking around with me, in any case, I was delighted that she found me interesting enough to want to spend time with me, however I knew I needed to keep my distance.
I continued to want to be with her, and feeling she was just infatuated, I continued to tell myself that I needed to be careful, and thought to myself, “What was I going to do if she wanted more.”
In a way, I felt that we both wanted to be with each other but didn’t know how to acton our feelings, we were left with spending what little time we had together thinking, “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.”
When we both looked at the clock, Ashley smiled and simply said, “Your right,” and then turning back, we looked at each other.
There was an awkward pause, but then the opportunity to be alone with her innocently presented itself, and it would soon become obvious that she wanted to be with me.
Standing up and walking toward the door to my classroom, Ashley asked, “Think you can give me a ride home?”
I was apprehensive, but being it was kind of late, I told myself it was just an innocent request, especially when she said that she would have to walk home because her parents were out of town. Looking at her, I hesitated, worrying, “What would people think?”
However, when I realized how far she would have to walk and being it was late, I decided I should probably give her a ride. She was visibly excited and reaching over, she gave me a big hug saying, “Thank you.”
I couldn’t help but smile as she hugged me. It felt great to hold her and smelling her faint perfume was nice, and as we looked at each other, I nervously said, “Well, we should probably get going.”
Heading out of the building, it looked like everyone was gone and as we cut across the blacktop area on our way to the parking lot, I could see it was basically empty. Looking around as we moved toward my car, it didn’t look like anyone noticed us leaving together, or at least I hoped no one did.
In the car, Ashley seemed a little nervous too as we left, but when I asked her which way I needed to go, she seemed to snap out of it. Looking at me, she pointed which way to head and as I drove, she gave me a few directions. I tried to keep it easy-going, making idle chit chat, and nervously joking around with her.
Everything seemed to be going okay, and after we made a few turns into the nearby neighborhood, Ashley looked over at me and said, “This is it.”
Stopping out front of a small house, she undid her seatbelt, and holding out my hand wanting to shake hers, she turned back, looking down at my hand briefly. Ashley then took my hand, and as we looked at each other, I felt there was something else she wanted to ask. Ashley then shyly looked down and after a pause she blurted out, “Do you want to come in?”
I was shocked, and again hesitated but as I looked at her she said, “It’s okay, no one’s home.”
Troubled I thought, “What should I do?”
And when I didn’t say anything right away she seemed almost apologetic saying, “Maybe you can wait until I get inside?”
I was torn, I wanted to be with her, I wanted to go in but I was having conflicting thoughts about being alone with her. Smiling as we looked at each other I said, “Someone will probably show up soon.”
Ashley then reached over, touching my hand, and as I looked at her, she quietly said, “They’re out of town, visiting my grandparents, it’s okay, you can come in.”
I had forgotten, “There was no one home,” and now after telling me, “They we’re out of town,” and seeing her looking over her glasses smiling, it was obvious she wanted me to come in.
Thinking, “Maybe it was she didn’t want to go inside alone,” and then immediately realizing it was the opening I was looking for, I thought, “If I don’t take it, it’ll never be there again.”
As she opened the car door, she looked at me questioningly and said, “Thanks for the ride.”
Immediately, without hesitation I said, “Well, maybe I can come in for a little bit.”
Ashley looked at me smiling excitedly and said,”Okay, come on!”
She seemed very anxious, which made me nervous but when I saw her beaming as I looked over, I smiled and unbuckled my seatbelt. Quickly getting out of the car and going around to where she was, she looked at me and again said, “Come on,” motioning for me to follow her.
I became very paranoid as we headed up the walk, cautiously looking around to see if anyone was watching, but being it was dark, I didn’t notice anything, but still made sure to hurry 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. Inquisitively I asked, “What do you have,” as I boldly followed her into the kitchen.
Opening the refrigerator door Ashley said, “Well there’s water, Pepsi, and there are a couple beers, if you want one.”
Looking in hesitantly, there was a pause and when I asked her to choose, she said, “How about we share a beer.”
Smiling, I agreed and as she handed it to me, I opened it and immediately took a big drink, hoping it might calm my nerves. Smiling, I passed it over to her, and after taking a drink, and choking it down, she handed it back to me.
I don’t think she really drank but as we stood there sharing the beer, making idle chit chat, we eventually finished it. Ashley now asked, “Wanta go watch some TV?”
Seeing her smiling, I agreed it was a good idea, and when I asked, “Why don’t you grab another beer,” she again smiled and grabbed one from the refrigerator.
Ushering us out to the living room now, and over to the couch, I instinctively sat at one end. Looking up at her, Ashley handed me the beer and as I took it, she sat next to me, and scooted closer. It was nice to be with her and then as I took a drink, she leaned over and suddenly kissed me on the cheek. I was shocked, and as I looked at her I smiled and asked, “What was that for?”
I could see she was blushing and there was a brief pause as we looked at each other, but then Ashley quickly replied, “Thanks for the ride home,” and finished by saying, “and for wanting to hang out.”
I couldn’t believe it and as I looked at her, I casually put my hand on her thigh and told her, ”I always like spending time with you.”
This again made Ashley blush and as she put her hand on mine, and I too looked at our hands, I gently gave it a squeeze. Looking up, Ashley smiled and then as we looked at each other, she leaned into me and gave me a side hug.
Instinctively, I put my arm around her and hugging her back, I gave her a kiss on the head. It felt really good to hold her, but when we leaned away from each other, she seemed to look at me startled. Smiling at each other briefly, I gave her a more serious look, and then leaning toward her, she closed her eyes.
Kissing her on the lips, I nervously looked for a reaction. I had wanted this and when she seemed to kiss me back, I felt she was okay with it too. Leaning away, I patted her on the thigh, and as she opened her eyes and she saw me looking at her, she smiled and gave me a hug.
After hugging for a little, we sat back and held hands as we gathered our thoughts. Looking over at her, I subtly said, “That was nice,” which made her smile bashfully. Grabbing the beer off the table, I casually took a drink from the beer and then handing it to her, she took a drink too.
Seeing it was almost empty or maybe needing to gather her composure, Ashley asked, “Do you want me to get another?”
Nodding, I said, “Sure, if you want to.”
Ashley quickly stood up and hurried into the kitchen to get another, and as I sat there waiting, I knew I had a big smile. Sitting there impatiently waiting, I heard her open it, and then as she came back into the living room, I watched as she took a drink. Smiling at her as she moved closer, she handed it to me, and then as she sat down, I too took a big drink. Setting it down, we scooted closer and then as I nervously looked at her, I casually put my one hand on her leg. Ashley immediately leaned against me, and as I pulled her closer, she looked up at me and we ended up kissing.
Passionately kissing, I started to worry, realizing what was happening, and not sure I should be there, I held her away. As we looked at each other I asked, “Are you okay with this?”
I was super nervous but when she smiled and leaned into me again, and said, “Yea,” I found myself smiling.
Pulling her close and holding her, it didn’t take us long before we were kissing again, letting our tongues explore each other’s mouths. As Ashley started feeling on my back, I slid my hand up her leg until it was on her crotch. It took a moment, but when she felt what I was doing, she quickly brought her hand around, and pushing it away she said, “No, don’t.”
We were still kissing, but I sensed some nervousness, and not wanting to go too fast, I simply moved my hand back down her thigh. Looking at each other now, I eventually put my hand on her waist, and when I gave her side a little squeeze, she smiled.
Even though Ashley had a slight frame, her body felt so good and as we started to make out again, I gradually moved my hand up to her chest, until it was right under her left boob. Ashley drew in a breath as we continued to kiss, and then as I moved my hand up to feel on her boob, she opened her eyes and put her hand on mine, stopping me. I could feel she had on a bra, but again she was very flat chested, so her bra was very small. Continuing to gently feel on her little tits as we looked at each other, I could feel her erect nipples pushing against her top.
Ashley instinctively looked down now at my hand as I felt on her tits, and then looking back up, we again kissed. I could feel Ashley was smiling as we kissed, and then as she playfully bit my lip, I smiled too. It was so hot, I couldn’t believe it, and wanting more, I slowly and awkwardly moved my hand to her crotch again.
Feeling on her pussy through her pants, I reached my other hand down to my crotch and as I adjusted my cock, she looked down too. I already had a hard on and when she realized what I was doing, she now curiously groped for my cock through my pants. When Ashley felt how hard I was, she suddenly stopped and pulled her hand away.
Looking at each other there was a pause and when I asked, “Are you okay,” she again looked down and smiled mischievously.
Ashley then reached down and boldly tried to undo my pants, which made me look down too. I hoped she’d get them off, but seeing her struggle, I leaned back trying to give her better access. Eventually, I had to help her and as we looked at each other, I smiled and thought, “Oh my god, is this really going to happen?”
Adjusting my pants, she looked at me a little confused, and asked, “What’s wrong?”
Nothing was wrong and as she continued to look at me for reassurance, I smiled and then reached down, quickly unbuttoning my pants. Ashley immediately looked down, and anxiously watching as I got them umzipped and gradually inch them down. Eventually, I wiggled a little, letting them drop to the floor, and when she looked up at me again apprehensively, I smiled.
Ashley immediately looked back down, because it had to be obvious that I had a hard on, and seeing my boxers bulging, she was definitely curious. Catching herself, she looked up at me smiling, and then hastily reached out, she grabbed at it.
I was still worried but as she eventually took hold of my cock through my boxers, and squeezed it, she again looked up at me. She was smiling but seemed to be somewhat fixated on it, and when I reached down and put my hand on hers, gradually having her start to rub it, she turned a little on the couch.
Asking her if everything was okay, she looked at me and after a nod, I leaned down to give her a kiss. I hoped that she would try to pull my boxers down, and after a little bit, I knew I needed to help her. Reaching down with both hands, trying to inch them down, Ashley suddenly grabbed the bottom of the leg holes, which made me smile as she slowly pulled them down.
Again adjusting my cock, so it wouldn’t hang up as she pulled them down, she suddenly stopped. I didn’t want her to stop and so I reached down, continuing to pull them down. It was obvious she was apprehensive but I think she wanted to see it too, and when my cock suddenly flopped out, she leaned away. Smiling, I took hold of it and even though I wasn't fully hard, she watched as I pulled on it.
Looking at her, all I could think about was wanting to fuck her and when I let go, letting my cock hang, she nervously looked up at me smiling. When she saw I was smiling too, her eyes went back to my cock.
Ashley seemed cautious, but still seemed curious too. I’m sure she was thinking, “ What should I do,” and then as she timidly looked up again for guidance I smiled.y told her, “Go ahead,” trying to convince her it would be okay to hold it.
As she looked down again, I reached out and taking her hand, I casually placed her little hand around my cock. Ashley was unsure, and pulling away scared, she again looked at me. Leaning over, I gave her a kiss and when I said, “Don’t worry,” she smiled.
She had small hands, and as I again moved her one hand toward my crotch and placed it around my cock, Ashley looked down, watching. As I slowly moved her move her hand up and down the length, she hesitantly looked up at me again, which had me ask, “Are you okay?”
Ashley sheepishly smiled and as she again look down as she stroked my cock, she asked, “Is this right?”
It was better than okay, and when I smiled and nodded, she looked down again and continued to stroke it. I hoped she might want to go down on me, but I didn’t want to press my luck. Instead, I reached my one down, and as I tried helping her, she looked up at me.
I think she suddenly got a little nervous, because she was now rubbing my cock at arm’s length. Grabbing her chin so she would look at me, I smiled and the. gave her a reassuring kiss. Ashley, suddenly let go and quickly putting her arms around my neck, she gave me a big hug. It startled me but I immediately thought, “How nice it was to be able to feel her body next to mine.“
Making out with her now, I wanted to see more of her, I wanted to see her little tits and when I again brought my hand up, and briefly felt on them, I hastily tried to lift her shirt up over her head. Bringing her hands up to her chest, stopping me, I looked at her. Ashley was smiling and then as we looked at each other she suggested, “Wanta go to my bedroom?”
Smiling, I immediately agreed, and as we started to stand up, I pulled my boxers back up and quickly leaned forward grabbing my pants off the floor.
Ashley smiled and then taking my hand, she led us down a short hallway. I was nervously excited as we headed toward her room, but along the way she enthusiastically pointed out a bedroom on the right, a small bathroom on the left, and then a door to her parent’s bedroom next to that.
After briefly looking in, she pulled me into the bedroom at the end of the hall, across from her parent’s room. As we went in, Ashley said, “This is my room.”
As I followed her in, she quickly went over and sat on the bed. She then laid back, and smiling, she spread her arms over her head. It was hard to not stare at her body as she laid there with her legs spread, and even though I couldn’t see anything, I desperately wanted too.
Ashley now turned onto her side and leaning on her elbow she said, “What do you think.”
Moving over, I wanted to reach out and grab her as she laid there, but instead I sat down on the bed next to her. Ashley’s bedroom was rather small, but as I looked around, she had a window that faced the street, and her room was decorated nicely. Her bed, I figured must have been a twin, with a dresser and a matching nightstand that had a lamp. Continuing to look around some more, she had a couple posters on the walls, and a shelf with a few items on it.
Eventually, I nervously stood up and walked around looking at the knick knacks and posters, and when I looked back at her laying there, she was still leaning on her elbow, smiling and watching me. Smiling back, I hoped she would ask me to stay, and after a pause I said, “You have a great room.”
Ashley continued to smile and then said, “Why don’t you sit back down,” as she reach her hand out patting the bed.
Looking over at her I thought, “I’m in deep now,” and as I dropped my pants on the floor, I quickly moved over to sit next to her.
Ashley shyly giggled a little as I sat next to her on the edge of the bed, and when I instinctively put my hand on hers, we looked at each other. I wanted to kiss her but a sudden feeling of concern came over me. I was worried about what we were about to do and looking away I nervously said, “Maybe I should get going.”
Ashley looked at me concerned and as she put her hand on my back, there was another short pause. Scooting closer to me, I looked over at her and she said, “Why do you want to leave?”
I really didn’t want to and as we looked at each other, she said, “I want you to stay if you can.”
Ashley’s eyes shyly looked away now, but when I took her hand, she looked back up at me. I knew I wasn’t going to leave and when our eyes met, I turned to face her more and gave her a kiss. Closing our eyes as we kissed, I eventually pushed my tongue into her mouth. It startled her at first, making her pull back, but she didn’t stop, instead she tilted her head slightly. I wanted to make it happened and I was seriously aroused by the thought of making love with her, but I was also nervous knowing it was her first time.
Continuing to kiss, I moved my one hand up under her boob again, and as I gently cupped it, she again gasped and we stopped kissing. Ashley then glanced down as I put my hand on her boob, and giving it a gentle squeeze she looked at me. I worried, but seeing her smile, I realized she was okay with it.
Looking at each other now, I was at a lost for words, but as she sat up on the bed until she was kneeling, I stood up. Smiling at me, I quickly climbed on the bed with her and when I smiled back at her I said, “This is nice.”
Kneeling in front of her, Ashley put her arms around my neck and as we again kissed I thought, “This is so nice.”
I knew she was interested and 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 leaned over and kissed me on the lips.
Quickly returning the kiss, I grabbed her by the waist, and pulled her closer. We only kissed for a second or two and as we stopped and looked at each other again, I worried, I didn’t know what to do, but didn’t want it to stop, and after a paus, Ashley asked, “Are you okay.
Looking at her for a second, I quickly said, “Yea, I’m okay, and then inadvertently asked, “Are you sure you wanta do this?”
She seemed confused, but I needed to know and when she said, “Yea, don’t you,” I smiled and gave her a hug. As I held her by the waist, I looked at her and after a pause I smiled and said, “I’ve thought about being with you for a long time, Ashley.”
This made her shyly smile, and then leaning toward her, we again hugged and I gave her a kiss. This really felt good and as I gave her another kiss, I moved my hand up until it was on her one boob. Gently feeling on it, giving it a sublte squeeze, she gasped as we kept kissing. Feeling on both of her boobs now, I could feel her little nipples were getting hard.
Ashley’s shyness seemed to be fading a little, and again I thought, “Are we really going to do this?”
Reaching around her, feeling for her bra strap, quickly unhooking it through her top, Ashley immediately leaned away, covering her chest as her bra dropped off her shoulders.
Looking at her, I immediately tried to lift her top over her head. Smiling, Ashley eventually lifted her arms up, letting me quickly slipped it over her head. Casting it off the bed and turning to look at her, she was blushing as she held her bra against her chest with both hands.
She was obviously nervous to let me see her body but when I again kissed her, she inadvertently let her bra straps fall down her arms. Telling her, “It’s okay,” she smiled, letting me take it off.
Tossing it aside too, she again covered her chest, crossing her arms. As we looked at each other, I gently pushed her hands down, exposing her firm little boobs. She really was so pretty and seeing her firm little tits and hard little nipples, I instinctively reached up, to feel on them as we looked at each other.
She didn’t stop me and after a simple little kiss on the lips, I moved to kiss her neck and then kissed my way down her chest. Closing my eyes as I started kissing and sucking her right nipple, she exhaled in anticipation. Ashley was so sweet and when she didn’t stop me, I moved my hand down to feel on her crotch. Continuing to tongue and suck her nipples, as I tried to fel on her pussy. Yea she still had on her jeans, but when she casually spread her legs a little, giving me better access as I felt on her pussy, she took a deep breath.
I wanted this and when she didn’t stop me, I moved backup to kiss her. Immediately I tried to undo her pants, and when they unbuttoned easily and I started to unzip them, she reached down grabbing my wrist, making me stop. I didn’t want to, but knew I should. Ashley was so young and my suspicion of her never having been with a guy before had to be true, but for some reason I felt that right now she wanted to be with me.
Acknowledging her, I stopped and moving my hand to her side, I kissed her. Continuing to kiss, she seemed to relax a little and as I laid her back and pulled her pants down, she gave me a concerned look.
Smiling, I grabbed her pants by the legs and as I started to pull them off, she giggled and then lifting up, I pulled them down. Throwing them to the floor, Ashley quickly grabbed her panties, and as I watched her adjust them so they would come off too, I smiled seeing her pussy through her powder blue panties.
Ashley was so pretty, and even though she was rather skinny and flat chested, I couldn’t help but admiring her, thinking how I wanted to be in her. However, when she saw I was staring, I think it made her a little self-conscious because she again tried to cover her chest.
Looking up and smiling at her as she lay there, I could seeing a concerned look on her face, which made me became a little nervous. However, when our eyes met, and I saw her smile, I immediately slid on top of her. Ashley scooted back a little, and as I moved to lay next to her, putting my leg over hers, I gave her a kiss.
Eventually, I climbed back on top of her, and spreading her legs, I made sure to press my cock against her pussy. Trying to keep my weight off her, I reached down, gradually slipped off my boxers. Smiling at her as I struggled to get them off, I eventually went to kissing her after casting them off the bed. Again making sure to press my cock against her, I slowly moved down kissing her neck and then kissing down her chest, feeling her little titties. I wanted to see her little pussy and I wanted to eat her, “If she’ll let me,” I thought.
It didn’t take long before I inched my way down until I was kissing the insides of her legs. Looking up at her briefly and see that she was laying back, I immediately started mouthing her pussy through her panties. Running my tongue in her slit, she grabbed the covers. She was definitely wet and smelling her wet little pussy, I pulled her panties to the side. Ashley leaned forward and as I put my tongue into her slit, she put her hand on my head. Lightly licking pussy, she brought her knees up.
Indulging in eating her pussy, making sure to flick her clit, Ashley arched her back and spread her legs a little more. Realizing she had probably never done this before, I looked up at her briefly. She had her eyes closed and smiling, I pull her panties aside a little more. Looking down at her pussy and spreading her lips a little with my finger, I again plunged my tongue in her slit. Ashley suddenly rose up on her elbows, and when I looked up at her again, I put my one hand on her stomach, trying to steady her.
Moving up and kneeling in front of her now, I slipping my fingers under the band of her panties. Looking at each other and smiling slyly, I gradually started trying to take them off. Her panties were definitely damp and as I continued to look up at her as I pulled them down, Ashley instinctively reached down to cover her pussy.
Getting her panties over her feet, she seemed to smile, which made me look away and smile too as I dropped them off the bed. Quickly climbing back on top of her, I kissed her and then kneeling in front of her, I started to gently massage her thighs. She only had a small amount of pubic hair, but it looked like she must trim it, and when I started to finger her, she smiled and laid back.
I wanted to fuck her and as I laid on top of her again, and pressed my cock against her, Ashley grinned, which made me lean forward and give her a kiss. I’m sure it was obvious that I wanted to fuck her, but I needed her to know it was okay.
Kissing her neck, I eventually moved my way back down tonguing and sucking her nipples briefly before moving down further until I was between her legs. At first she tensed up as I got between her legs and gently spread her soft little pussy lips with my fingers. Ashley again laid back, and as she willingly spreading her legs, I moved in the eat her pussy. She really was tight, and after licking and tonguing her slit, I pushed my tongue into her, eating her pussy. Ashley did reach down, touching my head with one hand, but didn’t stop me.
I desperately wanted to be in her, but I wanted to try to get her off first. She smelled so good and as I continued to plunge my tongue into her and flick at her clit, Ashley started to wiggle and moan a little. I felt she was probably going to cum and when she started squeezing my head between her legs and arch her back, I knew she was close.
Suddenly, she leaned up putting both of her hands on my head, telling me to stop as she tried to pull me up. Not stopping, wanting her to cum, wanting her to get off, I kept eating her. Ashley continued to squeeze my head between her legs, grinding as she lay back. Desperately trying to tongue her clit, she let her legs drop and again reached down, grabbing my head, saying, “Stop!”
Feeling her legs quiver a little, I looked up at her, and after wiping my mouth, I gradually moved up, kissing her body until I was on top of her. She was out of breath but smiling and as I leaned up and kissed her, I made sure the head of my cock brushed up against her pussy. It startled her a little I think, because she pushed me away saying, “No,” under her breath as we continued to kiss.
Moving down a little, making sure my cock wasn’t touching her, she stopped pushing me away. Ashley was still reeling a little and as we kissed, I again moved up and reaching down, I tried to guide my cock in her.
Whispering, “Relax,” Ashley wrapped her arms around my neck as my cock pressed against her pussy. At first, she didn’t realize what I was doing, but eventually said, “Stop!”
She really was so tight, and raising up slightly and looking at her, I could see she was worried. As we pause and looked at each other, I finally asked, “Do you want me to stop?”
Ashley didn’t say anything right away, but as she reached her one hand down to her pussy, blocking me, I asked, “Are you okay?”
She seemed scared, unsure, and as I tried to tell her it would be okay, Ashley looked down saying, “I’m not on birth control.”
I should have realized, but after a brief pause she smiled at me and asked, “Do you have anything?”
“Oh my god,” I thought. I knew I should have been carrying at least one condom, but as we continued to look at each other I sadly said, “No, I forgot to bring one.”
She was definitely worried but as she looked at me, Ashley suddenly said, “You can’t cum in me, Okay?”
Smiling back at her I nodded and asked,”Are you sure?”
Nodding her head, it was obvious that she was nervous. Smiling, wanting to reassure her that it would be okay. Moving up and kissing her as I positioned myself on top of her, she again said, “Remember, don’t cum in me.”
Leaning forward, I kissed her and said, “I promise, and then said, “I won’t.”
I couldn’t believe it, she was going to let me fuck her, but I knew I had to be careful and as we looked at each other I said, “Just tell me if you want me to stop.”
Ashley smiled sheepishly and nodding her head she again said, “Just go slow, okay?”
Nodding and kissing her again, she laid back, putting her hand on my hips. Moving my hand down, grabbing my cock, I slowly tried to push into her. Ashley tensed up a little, which made me tell her to relax.
She was wet but still so tight. I needed to try to loosen her up a little and as we continued to kiss as I moved my cock up and down her slit. It must have felt good, because she did seem to relax a little, and as the head of my cock touched her pussy, she took a deep breath.
I wanted to be in her and as I tried to guide my cock into her, Ashley grabbed my waist as I slowly pushed into her. She was so tight, I didn’t want it to hurt, and seeing her wincing a little, I knew I had to go slow.
Ashley now moved her hands to my chest, and as she pushed on me a little, I stopped, pulling out a little. I wanted to be in her, and kissing her, I again worked my cock up and down her slit. I didn’t want her to stop me, and as I pushed into her again, I hoped she’d eventually relax enough, letting my cock in her.
“Oh yea,” I thought as the head of my cock slip into her, and when I gave her a kiss, she smiled.
I was in her but not all the way and as I slowly worked my cock in and out of her, it really felt good. Leaning up and stopping, I asked, “Are you okay?”
She nodded but I could see it was still a little uncomfortable, and as I continued to try to fuck her, Ashley again pushed on my chest saying, ”Go slow.”
Leaning forward and kissing her, she kept her eyes closed, but seeing her smile, as I started to move my cock in and out of her.
Hunching over her, with my hands under her shoulder, kissing her neck, thinking about how good it felt, I wanted to cum. Pushing deeper into her, continuing to move my cock in and out, it didn’t take long before I was close.
Moving my cock in and out of her faster now, and breathing harder, I simply said, “I’m going to cum.”
Hearing this, it freaked her out and immediately pushed on me saying, “Don’t cum in me!”
Looking at her, I could see she concerned and as she continued to push on me I smiled and said, “I won’t.”
I knew I had to pull out, but it really felt good, she was so tight, and when I again hunched over her shoulder, and started fucking her, I desperately wanted to cum before she stopped me. Breathing hard, I was close, I wanted it to last, I wanted to wait to pull out until I was about to cum.
Suddenly, as I pushed deep into her one more time, I suddenly felt my cock jerk inside her a little. In a panic, I quickly tried to lift up off her, and as I reached down grabbing my cock, it jerked inside her again.
Desperately squeezing my cock, hoping I hadn’t cum in her, I hurriedly lifted off her and kneeling between her legs, I leaned forward and let it go.
Ashley now leaned up on her elbows and watched as cum initially shot out on her stomach. However, when my cum inadvertently dribbled on her pussy, she pulled away, scared.
It felt so good but as I looked at her and squeezed the last little bit of cum out on her thigh she said, “You didn’t cum in me, did you?”
I worried that maybe I had, but I wasn’t sure, and when she saw me smile, she reached down, touching the cum on her stomach. Watching her as she looked down and ran her fingers though the cum on her stomach, I could see Ashley smiling.
Sitting back, out of breath, Ashley reached down to her pussy. Suddenly, feeling cum on her pussy, she became concerned that I had cum in her. Looking at me, almost hyperventilate a little, Ashley was freaked out, and thinking the worst she hastily said, “You came in me, didn’t you!”
I didn’t know what to say and like I said, I wasn’t sure if I had or not, but as I looked at her, I felt she might start to cry. I needed to try to reassure her that I hadn’t and quickly I leaned up and said, “It’s only on the outside.”
Grabbing the sheets, she immediately started to frantically wiping the cum off her stomach and then her crotch. I really hoped that I hadn’t cum in her and as I watched, she bent her knees slightly, I thought I saw cum trickle out of her pussy. Taking a second look, I thought, “Oh no, what should I do?”
Instinctively looking up at her, I reached over and as I rubbed her legs, I tried to convince myself that it was only on the outside. Yea, I was scared and I’m sure she was worried too, but then Ashley all of a sudden reached down, putting her fingers in her pussy. I couldn’t believe what I was seeing, and quickly blurted out, “No don’t!”
Ashley instantly stopped and looking at me I said, “You shouldn’t put your fingers in you after touching my cum, and after a moment I said, “I don’t want you to get pregnant.”
Looking at her fingers and seeing cum on them, she hastily wiped her fingers on the covers, realizing what she had done. Ashley now nervously looked at me, which made me suggest, “Maybe you should go into the bathroom and clean up.
Nodding, she got off the bed and immediately headed toward the bathroom. I tried to follow her, but Ashley quickly turned and looking at me said, “No, I’ll do it,” which made me back away and say, “You might want to take a shower.”
Ashley smiled and then quickly scurrying into the bathroom, she closed the door. I could hear her turn on the water and as I sat there, continuing to worry about what I should do, I decided I should probably get going.
She was only in there for a short time, and as I started to get dressed, I heard the water shut off. Pulling up my pants and quickly put my shirt on, the bathroom door suddenly opened. Looking over as Ashley came back into the bedroom, she was smiling but when she saw me getting dressed she said, “What’s wrong, and then asked, “What are you doing?”
She looked concerned as she stood there holding the towel around her and when I stood up and buttoned my pants I said, “I think I should get going.”
At first, she looked disappointed, but as she stood there and we looked at each other, Ashley nodded her head. Giving her a hug and kissing her on the head she said, “Yea, it’s getting late.”
I continued to worry about her getting pregnant, and when I didn’t see her for a while, I didn’t know what to do. However, she did eventually show up, which was a relief and when she approached me, I asked, “How are you doing?”
Ashley simply nodded and smiling she asked, “Can you help me later with some of my assignments.”
Smiling, I was glad everything was good between us and more importantly, she wasn’t pregnant. What a huge weight off my shoulder that was, because it could have gone terribly wrong. As time went by, working with her became fewer and fewer and even though we did see each other a lot, and we did occasionally flirt with each other, we never spent time together again.
Even though Ashley moved on to another school, she continues to be on my mind, and when I think about the time we spent together, I wish we could do it just one more time.
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