It had been several weeks since we saw each other and I was lucky enough to have sex with her. Olivia was one of those girls you never forgot, one you wish to be with, and when the opportunity presented itself again, i had to take advantage
I never expected it to happen, but one afternoon when I saw her, I had to look twice. “Was that really her,” I thought?”
Hesitantly, I smiled and then nonchalantly went over to where she was standing. Seeing me coming her way, she looked down but I could see she was smiling and after saying, “Hi,” I simply asked, “How’s it going?”
It was merely to stimulate a conversation, and being I had been thinking about her a lot, I wanted her to know it, in a casual way. It had been several months since I last saw her and it looked as though she was a little taller, a little more mature.
She had on a pair of those distressed looking jeans, you know the kind every girl liked, and a plain black hoodie. I think she was hoping no one would recognize her, but being she only had her hoodie zipped part way, letting it drape off her one shoulder, hanging open seductively, and you could see her thighs through the torn jeans, it immediately brought attention to her.
As I got closer, trying to drink her in, I could see she was wearing a red tank top under her hoodie. Boldly looking down at her chest, straining to see her firm little boobs as they pressed against that tank top, and seeing her nipples pushing against her top too, it was obvious she wasn’t wearing a bra.
Looking up, Olivia casually pulled her hoodie back on her shoulder, covering herself. I felt a little embarrassed, but seeing a sly little smile, I couldn’t help but smile too. I wanted to send a message that I was still very much attracted to her, and that I liked seeing her again, but was it too much.
She had definitely filled out and being I had been thinking about her, obviously fantasizing about being with her again, it was kind of weird she’d show up.
Again, I never thought I’d have another chance, but here she was, and now I hoped in conversation the opportunity to ask her out would some how present itself. However, as Olivia now innocently explained she was just there picking up her little brother, I tried to listen carefully, and pretend to be interested.
I wasn’t sure if she wanted to see me, and I hoped she might signal some how that she’d like to get together, but it didn’t happen.
“Maybe she wasn’t interested,” I thought, “or maybe she wanted me to make a move,” in either case, I Immediately searched for a way to steer the conversation, or get up the nerve to ask her out.
She was so pretty, definitely more grown up and after nervously shaking her hand, she turned and walked away. I was excited to see her and couldn’t help but try to inconspicuously check her out as she headed down the walk.
Continuing to watch her until she turned the corner, I quietly headed back to the side door. I wondered if she had a boyfriend, or if she was still living with grandma, either way, seeing her again made me want to follow her, wanting to be with her again.
Going back up to my classroom, I continued to wonder about Olivia, and as I left work, I decided to drive by her grandma’s house, hoping I might see her. However, as I pulled down the street where she lived, I realized I better not, and nervously turned around, heading home.
As I drove, I felt a little dejected that I hadn’t been more assertive, but eventually came to understand, “It wasn’t meant to be.”
Deep down though, I couldn’t help but think about her, and when I got home, the thought of being with her again was overwhelming as I sat on the couch. Closing my eyes, I found myself masturbating, remembering what we had done, desperately wanting to do it again.
I thought about wanting to cum but eventually stopped, as I contemplated, “What if, she shows up tomorrow afternoon?”
“What if, she too wants to get together again, but like me, doesn’t know how to say it?”
Continuing to think, “What if, what if,” I unexpectedly got a text message.
Quickly going over to get my phone, I thought, “Who could it be?”
Cautiously looking at it, puzzled, I continued to think, “Who’d be sending me a text?”
“Oh, it was just an advertisement,” as I saw the message, but then there was a text message from earlier that I had missed that simply said, “Hi.”
I don’t know why I hadn’t seen it before, but I was curious and thought, “Who could this be?”
Looking at my phone for a minute and then without thinking, I replied back with a simple, “Hi,” of my own.
Not knowing who it could be and wondering if I’d get another text, I set it down, suspiciously waiting. It didn’t take long before I got another message that simply asked, “How are you doing?”
Like I should know who it was, I smiled and replied back asking, “Who is this?”
I didn’t get a message back right away, I felt it was a scam, however as I put my phone down again I got another text. Reading it and seeing who it was from, I thought, “Olivia?!”
I couldn’t believe it, thinking, “Was it really her?”
Continuing to read her message, I couldn’t help but smile to myself. I was excited, but then suddenly became a little nervous, not knowing if I should reply or not.
“What could she want,”I thought, and then nervously asked myself, “Is it really her?”
Needing to be cautious, I didn’t reply, and then after a while, she sent a message saying, “Sorry I’m bothering you.”
It sounded like her and I wanted to reply, but continued to worry it might be a trap. However, when I got yet another message asking, “Can I call you?”
I smiled to myself and then sent a smiling emoji with a message saying, “Sure!”
I think she too was a little nervous because it seemed to take forever for her to call, but then suddenly my phone rang.
Clearing my throat, I answered it simply saying, “Hello.”
Waiting to hear her voice, she eventually said, “Hi.l
It made me smile, and not knowing what to say, I waited and when she said, “It’s Olivia,” I thought, “Oh my god,” and then replied, “Olivia from school?”
She said,“Yea,” and after a few seconds she asked, “Are you surprise?”
Of course I was surprised, I would never have expected her to contact me, but then as I searched for what to say, Olivia spoke up telling me, “It was nice to see you earlier.”
Simply agreeing, I replied, “Yea, it was,” and then nervously asked, “How are you doing?“
There was a slight pause, but then she hinted at wanting to see me, saying “Maybe I’ll see you tomorrow.”
I didn’t know what to say, I was so nervous but then before I could say anything, Olivia replied, “I miss being in your class.”
Smiling to myself, I naively said, “I miss having you in class too.”
Listening, she didn’t say anything for a second and then searching for what to say, I boldly suggested, “Do you want to get together sometime?”
She still didn’t say anything, which made me blurt out, “Maybe we can go get something to eat?”
Olivia again hesitated, not saying anything, but then excitedly said, “Sure!”
Smiling to myself, I immediately replied, “Do you want me to come get you?”
She again, didn’t say anything right away, but then said, “Sure, if you want to.”
Of course I wanted to, but worrying it might be a set up, I suggested we meet up at the school. A little confused at first I think, she agreed, and when I told her, “I’ll be there in about a half hour,” she seemed very excited.
I was excited too, but being it was already getting dark as I headed over to that part of town, I was still very nervous. I wanted to be with her again and as the thought of being with her raced through my head, I hurried to get her.
“What could we do, I thought, “where could we go?”
I really wanted to be alone with her and I thought about bringing her back to my house, but “How could I get her to go?”
Any way, as I pulled up front of the school, there she was, and seeing me pull up, she hurried out to my car. As she got close, I reached over the center console, and opening the door, I said, “Hi.”
Quickly getting in and buckling her seatbelt, Olivia looked at me and smiling she also said, “Hi.”
She was still wearing the black hoodie from earlier, and the red tank top too, but she had changed into some white sweatpants. Not wanting to bring any attention to the fact I noticed, even though I really wanted to see her legs, I simply smiled and questioningly asked, “Where do you want to go?”
Olivia was hesitant to answer and as I looked over, I noticed she must have on some make-up. It made me smile, and looking twice, it reminded me of how hot she looked the time she had dressed up as a witch, a sexy witch for Halloween. Catching myself, quickly looking back at the road, she blurted out, “Can we go to your house?”
“Oh yea,” that’s what I wanted but smiling I said, “Don’t you want to go get something to eat?”
It wasn’t apparent right away that she wanted to be alone with me, and seeing her shyly smiling, and not saying anything, I suggested a little place kind of close. Olivia looked over at me and then nodding said, “Yea, that’s good.”
It made me excitedly smile too and then reaching over the console, I patted her thigh.
I was excited to be with her and when we went in and sat down, I felt she wanted to say something. However, our waitress quickly came over and smiling she said “Hi,” and then asked, “What would you like to drink?”
Looking over at Olivia, she ordered a Coke and then as the waitress looked to me, I ordered a margarita, and then I asked, “Could we get some chips and salsa?”
It was nice to be with Olivia and as we talked, I found out that school was going good and when I asked if she had a boyfriend, she hesitated but said, “No, I don’t.”
I still felt there was something weighing on her, but “What could it be?”
As we continued to make idle chit chat, our waitress eventually brought our drinks, and asked if we wanted to order some food. After placing our order, I could see Olivia eying my margarita, and as our waitress left, I smiled knowing she wanted to try it and figuring she had probably drank before, I asked, “Do you want to try it?”
It made her smile and after a nod, I subtly pushed it toward her. Olivia quickly looking around, took a pull off the straw, and then looking over at me, she smiled. Smiling too, I asked, “Do you want another?”
Olivia immediately grabbed it, and after taking another drink, she pushed it back toward me. We had to be discreet but it was obvious she liked it, and after quickly polishing it off, I ordered another.
Our waitress eventually brought our food, which was good, and as we ate, we ended up finishing off yet another margarita. I tried to make sure she ate something, because she was definitely feeling no pain, smiling a lot, and not saying anything.
It was fun to be with her, and she did seem to be more relaxed, but not wanting her drunk I said, “Wanta leave?“
She smiled and nodding excitedly said, “Yea, if you want to.”
Leaving and getting in my car, Olivia questioningly asked, “Can we go to your house?”
Looking at her suspiciously, I smiled and then asked, “Are you sure?”
Olivia, smiling, almost blushing said, “Yea.”
“Well,” I thought, feeling we had gotten through the social awkwardness I said, “Yea, okay.”
I so wanted to take advantage of her, which immediately had me thinking, “How can I get her in bed again?”
I wanted to do it with her, but continued to worry as I drove. Finally, pulling into the driveway and playfully grabbing her waist as we hurried inside, she giggled as we went through the door. Feeling I had a chance, I turned her and as we looked at each other I remarked, “You’re really pretty,” and then without hesitation said, “I’ve been thinking a lot about you.”
It left her speechless, and then blushing she eventually said, “Me too.”
Seeing her looking down and smile, I again grabbed her by the waist, which made her cautiously look up. Leaning toward her, we hugged and I gave her a kiss on the head.
Continuing to hold her, I boldly said, “I’ve missed you,” which made her look at me, and then getting on her top toes we ended up kissing.
Taking her hand and leading her over to the couch, it still felt very fun and trying to avoid awkwardness as we sat down, I asked, “Do you want anything to drink?”
Shaking her head and saying, “No,” I smiled and again reached over taking her hand.
Olivia looked at our hands briefly, and then looking up smiling shyly, she leaned toward me, casually giving me a kiss on the cheek. We ended up hugging and then almost immediately, we started to mess around on the couch, tickling and grabbing at each other.
Laughing, I let it slip, “I’ve really missed this.”
Looking at me smiling, Olivia leaned on me, gave me a little hug, and we again kissed. Thinking, “Oh yea,” as we let our tongues now dance in each other’s mouth, I slid my hands up to feel on her chest.
I wanted more and as I tried to subtly unzip her hoodie, we stopped kissing. Looking at each other, I thought she’d make me stop, however, seeing her smile and then kissing me again, I casually slid it off her shoulder.
Olivia now looked down, and then helped to unzip it the rest of the way. Smiling, I pulled it off her shoulders, and then tossing it to a nearby chair, I instinctively found myself staring at Olivia’s chest.
She really had nice firm little tits, and yea, maybe they were small and a little underdeveloped but right now it didn’t matter. However, as she adjusted her tank top and I saw her little nipples pushing against it, I couldn’t help but reach out, grabbing her by the waist. Looking up, Olivia smiled and when we kissed, and she closed her eyes, I so wanted to feel on them.
Closing my eyes too, I let my one hand casually reach up until I was feeling on her one boob. At first, as I cupped it, she didn’t notice, but then startled a little, we stopped kissing. Olivia now shyly looked down at my hand as I started to feel on her tit. Looking down too, I moved my other hand up so I was now feeling on both of them, which made Olivia look up smiling as she put her hands on mine.
Looking at each other, not wanting her to stop me I said, “You’re so pretty.”
This made Olivia lean toward me, and as we hugged each other, and I gently gave her a kiss on the head, she said, “It nice being with you.”
Again, we looked at each other and then as we kissed, Olivia daringly let her hand move to my crotch. I knew what she wanted, and so spreading my legs slightly as she groped, she found it. I couldn’t help but smile to myself and as we kissed, Olivia smiled too.
Sliding my hand to her waist, we stopped kissing, and I jokingly asked, “What are you doing?”
She didn’t say anything, but instead embarrassingly she moved her hand to my leg. It was obvious she could tell I had a hard on, even though it was through my pants. I didn’t want her to stop and when we again kissed, and as she again closed her eyes, I let my hand slide down between her legs.
Olivia now turned her head slightly, and feeling her open her mouth as we kissed, I slipped my tongue in and immediately felt for her pussy through her sweatpants. “Oh my god,“ I thought, “she isn’t wearing any panties!”
Shocked, I stopped kissing her and as we looked at each other, Olivia smiled and asked, “What?”
Smiling slyly, and giving her a subtle little kiss, I so wanted to fuck her and wanting to get her in bed, I eventually asked, “Do you want to go to my bedroom?”
She was hesitant, but as I stood up, and she looked up at me, I took her hand and gently pulled her to her feet. Giving her a hug as she stood up, I tried to reassure her as I took her hand and led us toward my bedroom.
As we went through the door, it was for the most part dark, which I felt was okay and when I turned to face her and we kissed, I casually reached down to again feel on her pussy. Smiling, I asked, “Do you not have on underwear?”
It made her blush and not saying anything, Olivia too reached down and then said, “No,” as she smiled and again grope for my cock.
Quickly finding it, she started to rub it through my pants. Yea, I was hard and even though I didn’t want her to stop, I reached down and undid them. Smiling, Olivia anxiously helped inch them down and as my pants fell to the floor, and I kicked them aside, we looked at each other.
After adjusting my boxers, she again gave me a sly smile as she moved both her hands down to my crotch. Looking at each other as she felt for my cock through my boxers, I hoped she might go down on me. Backing her toward the bed, and then giving her a kiss, as she started feeling on it, I stopped her asking, “Are you sure you wanta do this?”
Olivia hesitated but then smiling, she leaned up and giving me a kiss, I felt it must be okay. I wanted to see if she might go down on me and as I put my hands on her shoulders, pushing her to her knees, she looked up at me cautiously, but eventually went down.
Looking at each other as I fumbled to get my cock out through the little flap, she looked down, watching. However, as I got it out, and she saw it, Olivia nervously looked up. I hoped she might want to try sucking it, but knowing she had probably never done it, I had to be careful. Seeing her apprehension, I said, “It’s okay,” and as I held it out, I then told to her, “Not to worry.”
Seeing her smile sheepishly, I asked, “Do you want to try it?”
Olivia now looked down at my cock, but I could tell she was scared. Moving closer, trying to get her to take it in her mouth, she looked up. Smiling at her as I continued to stroke it, I said, “Close your eyes.”
She smiled, but I could see she was scared. However, she did close her eyes and when I told her, “Open your mouth,” Olivia open her eyes and nervously looked up at me.
Again, telling her, “It’s okay,” trying to put her at ease, she again looked down at my cock.
Olivia seemed to smile, and when I again said, “Close your eyes for me,” and continued by saying, “Open your mouth,” she timidly closed her eyes, but grimaced as she opened her mouth.
I didn’t want her to worry and as I moved closer, and tried to guide my cock toward her awaiting mouth, I asked her to open it more. I tried to be as careful as possible, but when the head of my cock unintentionally touched her lip, Olivia immediately opened her eyes and pulling away, she looked up at me, scared.
I knew it wasn’t going to happen, not this time and not wanting to ruin my chance to fuck her, I reached down and pulling her to her feet, Olivia said, “Sorry.”
Not wanting her to worry or feel sorry, I kissed her and said, “Don’t worry.”
Kissing her again, and giving her a reassuring smile, I eagerly reached up to feel on her tits again. It made her smile and feeling things were good, I lifted her onto the bed. Olivia let out a little giggle, and as I moved between her legs, as they hung over the edge, I leaned toward her, giving her a kiss.
Looking at each other, I tried to lift her tank top up, however Olivia stopped me jokingly saying, “You first.”
Smiling, Olivia now inched my shirt up and after quickly helping her and dropping it to the floor, I again tried to take off her top. Getting it over her boobs just enough, I smiled at her and then moving down, I started sucking one of her pouty little boobs and tonguing her nipple.
Olivia didn’t stop me, but instead took a deep breath and as she laid back, I climbed on the bed with her, quickly moving on top of her. Smiling and then kissing her, trying to keep my weight off her, I again moved down to tongue and suck her nipples.
Closing my eyes, relishing the moment, letting my hand drift down to her crotch, I started fingering her pussy through her sweats. Creasing her slit, I looked up at her briefly, giving her a smile, before moving down even more. I wanted this so bad and when started to mouth her pussy through her sweatpants, Olivia reached down softly touching my head.
Stopping and moving to kneel in front of her, I grabbed the band of her sweats, and as I pulled them down, she stopped me. I didn’t know why, but thinking she was just a little apprehensive or maybe nervous, I smiled and then looking at her, I tried to let her know not to worry. She didn’t stop me, but instead laid back as I pulled her sweats down, and then lifted her ass up, letting me get them off.
Dropping them off the edge of the bed, and moving up to kiss her, not wanting her to feel self conscious now that she was naked, I quickly reached down and pulled off my boxers. Olivia, up on her elbows now, obviously curious, wanting to see my cock, but being it was dark and I was on top of her, it made it difficult.
Kissing her and then moving down to suck her neck, I let my hand again drift down to her pussy. Feeling her fleshy little mound, I scooted down to first kiss and suck her little tits. Kissing her stomach now, quickly moving my way down, positioning myself between her legs, spread her pussy with my one hand.
Olivia, even though she was really young she kept her pussy neatly trimmed, and as I continued to look, I smiled and then went down, pushing my tongue into her as I spread her lips. She really was so tight and closing my eyes, I wanted to hopefully get her off. Licking and tonguing her little clit, fingering her occasionally, I wrapped my arms up around her legs and pulling her close, she seemed to squeeze my head between her legs.
She was going to cum, I could tell and then suddenly exclaiming for me to stop, as she straighten out her legs, I moved on top of her. Wiping my mouth, I could feel her body quake slightly, and trying to kiss her, Olivia again told me to stop.
Laying on top of her, not stopping, wanting to fuck her, I took hold of my cock and tried to guide it into her. She was wet, and really tight however, as I pushed into her and she again told me to stop, I did.
She was out of breath and seeing her smiling I said, “Let me get a condom okay?”
Olivia nodded and then smiling, she pushed me to get off her, but as I moved to get off the bed, she stopped me saying, “It’s okay,” and then with a labored voice she said, “I’m on the pill.”
Giving her a concerned look I asked, “Are you sure?”
Smiling, Olivia remarked, “Yea, my grandma let me.”
“Oh my god,” I thought, “really?”
I was shocked, not knowing what to say, I blurted out, “Okay, I’ll be careful.”
It did make her smile and I couldn’t believe she was going to let me do it, but as we again kissed and I laid her back, I quickly positioning myself between her legs. Leaning up and kissing her, I curled my hands under her arms, and pressing my hard cock against her pussy, I so wanted to be in her.
However, for some reason, I again stopped and politely asked, “Are you sure?”
It again made her nod but seeing an unsure smile, I kissed her and trying to reassure her I started to say, “Maybe we …,” but before I could finish she said, “Its okay.”
Not saying anything, trusting it was okay, wanting to fuck her, wanting to feel inside her, I pushed into her. Olivia, pushing on my chest and telling me to go slow, I kissed her, slowly continuing to press into her. Moving it in and out of her tight little slit, desperately trying to get it in, she wrapped her arms around my neck.
Holding her, continuing to gradually buck my hips, thinking to myself, “She’s really tight,” as I tried to not hurt her, I again stopped and asked, “Are you okay?”
Taking a deep breath and nodding she told me, “Yea,” and then told me, “Go slow.”
Smiling and giving her a kiss, again getting my hands under her arms, I pressed into her. I was basically all the way in her now and as I started to thrust in and out of her, I knew it wouldn’t take long. I was close almost immediately. She was so tight and when I stopped and told her in an out of breath voice, “I’m going to cum, she pulled me close and bracing herself said, “Cum for me,” and then whispered, “I wanta feel it.”
Smiling to myself, pulling her close too, trying to concentrate, wanting to cum as I repeatedly bucked into, I felt it. Pushing deep into her a couple times, and trying to hold her I again said, “I’m gonna cum.”
Olivia put her hands on my ass, quietly telling me, “Go ahead,” as she pushed on my ass, wanting me to keep moving in and out of her.
Stopping and trying to hold her still, as my cock jerked, I told her, “Stop!”
It felt so good to cum and feeling it was pumping deep inside her, I told her, “Oh, yea.”
Hearing this, Olivia asked, “What?”
Trying to ignore her, I held her as my cock continued to jerk inside her. I was done but as I again slowly tried to move my cock in and out, it seemed Olivia was a little shaken. Leaning up and looking at her, I asked, “Are you okay?”
There as a pause, but then smiling and hugging me Olivia said, “I’m okay.”
Sensing that she might be feeling a little uncomfortable about what we had done, I pulled out and kneeling in front of her, I put my hands on her thighs. Looking at her, she did smile, but it was very reserved and looking down, I could see cum had started to flow out of her, which I’m sure she felt.
I think she was suddenly feeling concerned about letting me fuck her and more importantly letting me cum in her. I didn’t know what to say and like before, it wasn’t long before I was taking her home. Yea, she used the bathroom and cleaned up before we left, but I really had hoped she’d want to spend the night.
Taking her home and again stopping to drop her off a couple houses away, we shared an awkward kiss.
She didn’t say anything, but when I asked if I could see her again, Olivia smiled saying, “I don’t know.”
Taking her hand, I smiled, trying to acknowledge her reply, and as she got out and headed toward her house, I turned my car around and left for home.
Olivia was great and I think we had a connection, at least I hope we did, but I also feel it was just a one night stand, or maybe it was an obsession being I was the one that took her virginity.
I think about her a lot, and look for her to show up everyday, but as of now, we haven’t run into each other. I do however, feel there is a chance we’ll get together again, mainly because I was her first and being I think about her all the time, I’m sure she thinks about me too.