I wanted to be with her, but was scared to make a move, feeling it might turn her off, but Olivia was very attractive, and being she was part Native American, she had great features. Yea, she was very young and I of course found myself constantly thinking about her whenever I saw her as I checked her out.
It was a Friday afternoon and being I was excited to leave the building, I hurriedly packed up and left . However, as I passed through the lobby on my way to the parking lot, I saw Olivia sitting out front. Curious, I opened one of the doors and asked, “What’s going on?”
Olivia looked at me and smiling she told me that she was waiting for a friend to pick her up. Olivia was very attractive and being she was part Native American, she had great features. Yea, she was very young and of course I found myself constantly thinking about her whenever I happened to see her and always found myself checking her out. She had a firm little ass that looked great in jeans, and her perky little tits had me constantly looking at them whenever she wore a top that accentuated them. She really had a nice little body, but because she was shy and very self-conscious, she always tried to hide it.
I always remember a time last year when she dressed as a witch for Halloween. She was in all black and had dark makeup, and the first time I saw her like this, I couldn’t help but think about being with her. It was a flowing costume with black lace sleeves and skirt. It was tight against her chest, and even though she didn’t really have anything there, it showed off her tits, and I still remember her firm little legs beneath that lacy skirt, and her little ass shake as she walked … what else can I say, I couldn’t help but stare.
Anyway, I knew she was having to live with grandma along with her two brothers because her mother was either incarcerated or had been, in either case, grandma had custody.
I was much older than Olivia, but whenever I saw her, I couldn’t help think about being with her, even if it was only once. Any way, as I continued to look at her, I asked, “Do you want me to give you a ride home?”
Like I said, “She was very shy,” and as she looked down she shyly said, “I’m okay.”
It was getting late and knowing it was the right thing to do, I said, “Come on,” trying to prompt her to come with me.
Looking over at me smiling, I gestured with my head for her to go with me and as she smiled and grabbed her backpack, she stood up. Heading through the building, toward the parking lot I subtly asked, “Where’s your boyfriend?”
Olivia was a little hesitant but said, “We broke up,” and then said, “It’s a long story.”
I didn’t ask anymore but was definitely curious about what happened and then as we got in the car and buckled up, I turned the key and said,”Okay, which way.”
I wanted to be with her, but was scared to make a move, feeling I might turn her off, and as I listened to her direction, I couldn’t help but glance over smiling.
Her house wasn’t very far away and when we eventually pulled up front, and I didn’t see any lights on, I put the car in park, and looking over at her I asked, “Who’s home?”
Olivia quickly replied that no one was home and explained that her grandma and brothers had gone to visit her aunt that wasn’t doing well. I was kind of shocked that she would be left home alone and seeing she was nervous too, I innocently asked if she wanted me to go inside with her.
Hesitantly, Olivia said, “It’s okay.”
Smiling, I reached over the console and as I touched her hand that was resting on her thigh, I said, “Let me come in with you,” and then said, “Just to make sure everything is okay.”
Olivia briefly looked down at my hand on hers, and then as she looked up at me, she shyly smiled and nodded her head.
Turning off the car, we both climbed out, and as I followed her up the walk, I couldn’t help but look at her butt. She had on a pair of faded and tattered jeans and an oversized black hoodie that conveniently hid her body, but I still couldn’t help but look at her legs and her ass as she went up to the door.
The neighborhood wasn’t the best and her grandma’s house was a small prefab that could have used some work, but was clean. Staying back a little as she put the key in the door and eventually opened it, she turned and asked me in.
Throwing her back pack on the floor by the door, I asked her if she wanted to show me around. Smiling, Olivia said, “Sure,” and as we walked the house, moving from room to room, checking to make sure everything was okay, Olivia pointed out each bedroom.
When we went into her room, I made sure to look in her closet and under her bed. Looking up at her as I stood up, she seemed appreciative that I was there, and after politely saying, “I guess everything is good,” she nodded and smiling we both headed back to the front room.
Following her, I said, “Maybe I should get going.”
This made her turn and as she looked at me, she hesitantly managed to say, “You can stay, if you want. “
Smiling back I asked, “Are you sure?”
Of course I wanted to stay and when she shyly smiled and nodded, I smiled and said, “Okay, maybe for a little bit.”
I liked being with her, and felt the longer I was there, the better my chances were to maybe make out with her and maybe even, we’ll you know, but knew that it was probably far fetched.
Standing there waiting, Olivia finally said, “Wanta watch some TV?”
I really didn’t care what we did and as we sat on the couch, I looked around as she turned on the TV. Her grandma’s house was modestly decorated and realizing there was a lull in our conversation I casually asked to use the bathroom. Olivia glanced back and looking down the hall she said, “Yea, it’s down there.”
Pointing down the hall she then stood up and said, “Let me show you.”
Olivia was definitely starting to feel a little more at ease and as she showed me where the bathroom was, I made sure to brush against her, in an attempt to flirt with her as I moved past. Smiling at her, I could see it embarrassed her a little and as she headed back to the living room, I quickly ducked in to pee.
When I went back out to the living room, Olivia was looking my way and as I deliberately sat right next to her, she nervously scooted over a little. Again scooting closer to her, we looked at each other, and smiling I asked, “What are we watching?”
She had picked a scary movie and as we continued to look at each other Olivia asked, “Do you want something to drink?”
Olivia stood up and pausing the movie, she headed toward the kitchen. I immediately stood up, which made her look back and smiled when see saw me following her.In the kitchen, Olivia opened the refrigerator, and as we both leaned down to look in. Casually putting my hand on her back, she quickly stood up. I’m sure it made her a little nervous but when I saw there were a couple sodas I said, “How about those?”
Smiling, Olivia grabbed them and after handing me one, she turned to face me and let the door close. Moving away a little she asked, “Do you want some popcorn?”
It sounded good and after grabbing some out of the cabinet, she opened the microwave and put it in. Olivia closed the door and facing the microwave as she set the timer, I couldn’t help but step closer and flirtatiously grab her hips. Again, it surprised her I think and not wanting her to be scared, I let go and stepped back.
Olivia looked back at me smiling shyly and seeing she was blushing, I took a drink from my soda, smiling. I knew she was nervous and after the timer went off, Olivia grabbed a bowl out of the cabinet and dumped the popcorn in the bowl. As we both sauntered back out to watch the movie, and we both sat down, I again deliberately moved closer, sitting right next to her. She again nervously scooted over just a little, and as we ate popcorn and drank our sodas, subtly reached over and putting my hand on her thigh. I didn’t want her to be nervous, but I wanted her to know I was interested, and when I gave her leg a little squeeze, she looked at me, smiling.
There was a slight pause but as we looked at each other I casually asked, “So, what happened with your boyfriend?”
Cautiously smiling, Olivia shook her head and then said, “My grandma made me break up with him.”
“Really,” I said, and then asked, “Why?”
Looking down, Olivia shook her head and then said, “She caught us making out.”
Smiling, I asked, “Where, In your bedroom?”
Olivia looked at me and after a second said, “”No, right here.”
Looking down at the couch I asked, “What did she catch you doing?”
Shaking her head no, she seemed embarrassed to tell me, but after some more prompting she said, “We were making out.”
Smiling, I pressed her and asked, “What do you mean?”
I felt I knew what she was trying to tell me and when she said, “We were watching a movie and we had a blanket over us.”
She was still a little embarrassed to tell me but then said, “Well, we had the lights off and we were, kissing,” and pausing she looked at me said, “and you know.”
Smiling I asked, “Know, what?”
Shyly looking down she again shook her head. Gently squeezing her leg I said, “You don’t have to tell me,” and then said, “I understand.”
Looking over at me, Olivia blurted out, “He had undone my pants and had his hand up my shirt and when my grandma came down, we obviously looked guilty.”
“Really,” I said, “what happened then? “
She was mad and knew what were we doing, and angry she told him he had better leave.
Thinking about wanting to do the same thing, I started to get a hard on and when I saw her looking down at my hand on her thigh I said, “I’m sure grandma was pissed.”
Olivia looked up at me now and smiling she said, “Yea, she wouldn’t let me see him anymore.”
Scooting closer, I put my arm around her and giving her a hug I said, “You’re really pretty Olivia, and …”
Olivia now leaned against me and said, “And what?”
Holding her away from me and looking at her I said, “I know I’m a lot older but,” and before I could finish saying something that would have revealed my true feeling she smiled and putting her arms around my neck said, “You’re not old.”
Continuing to smile for a moment, she suddenly looked down. Smiling to myself, I shift so I was facing her more and with her arms still around my neck, I lifted her chin. Looking at each other, I leaned toward her and as she closed her eyes, I kissed her. Olivia again shyly looked down and as I tried to make eye contact I again lifted her chin and asked, “Are you okay.”
Nodding her head, not saying anything, she smiled and leaned over giving me a hug. I wanted this and as we looked at each other, Olivia instinctively said, “I’m not sure we should do this.”
I knew what she meant, but immediately ask, “Do what?”
I felt she was looking to see my reaction, and when I shifted a little on the couch and said, “Maybe I should leave,” Olivia looked at me hesitantly but then immediately said, “No!”
It was obvious that she was having conflicting thoughts but as I again pulled her close and gave her a hug, I instinctively kissed her on the head. Looking at me, I moved my hands to her waist and when she leaned toward me and closed her eyes, we again kissed. Immediately, I tried to push my tongue in her mouth, which I think startled her a little, but as our tongues met, I reached my one hand up to feel on her chest.
Being she was kind of young, Olivia wasn’t big breasted and as I felt on her little titties, I could feel that she did have something there, but wasn’t very well developed at all. Gently cupping her one breast, I moved to casually pull her hoodie up over her head. Olivia smiled and then as I got it over her head, she quickly pulled at her top, adjusting it. Tossing her hoodie on a nearby chair, I looked down at her chest and then immediately reached down and tried to undo the top button on her jeans. Looking up at her to see her reaction as I fumbled to unzip them, she reached down stopping me.
Moving my hand away, I leaned up and after giving her a kiss, I laid her back. Smiling as she laid against the pillow at the one end of the couch, I couldn’t help but look down. Her top had inched up a little, exposing her poochie little stomach but as Olivia shifted and as she pulled her top down, trying to cover her stomach, my gaze shifted to her pants as they lay open. Slyly trying to reach into her pants, I looked up at her smiling. However, as soon as my fingers slipped under the band of her panties, Olivia immediately reached down and grabbing my wrist, she said, “No, don’t.”
Smiling at her and moving my hand to her waist again, I sat back, took a deep breath, and patted her on the thigh. Olivia now raised up on her elbows and looking at me she said, “I’m sorry.”
Not wanting her to worry, I smiled and said, “It’s okay,” as I gently rubbed her thigh.
This made Olivia smile and then leaning up, she put her arms around my neck, giving me a hug. Putting my arms around her and hugging her back, Olivia let it slip saying, “I’m just scared.”
Moving my hands to her waist and giving her a little squeeze, I smiling said, “Don’t worry.”
Olivia nodded and after a kiss, I asked her if she wanted me to stop. Blushing a little, Olivia kissed me again and as I casually slid my hand behind her back, I felt for her bra strap. I wanted to undo it but when I didn’t feel any hooks, I realized there must be a clasp in the front. Smiling, I leaned back and as we looked at each other, Olivia asked, “What’s wrong?”
It made me smile, and as I stood up, and took her hand, I tugged at her, prompting her to stand up too.
I wanted us to go to her bedroom and as she stood up and I pulled her to follow me, Olivia asked, “Where are we going?”
Smiling at her, she hesitantly smiled back and as she grabbed her pants not letting them fall down, I led her down the hall. Glancing back as we headed toward her bedroom, I could see she was nervous; I was nervous too, but as we went through her bedroom door, and I turned to face her, I put my hands on her waist and gave her a kiss.
Even though there was a little light coming in from down the hall, it was kind of dark, but as my eyes adjusted, I turned her to face the bed. Hugging her from behind, letting my hands move up to her chest, I leaned down, kissing and sucking her neck, eventually feeling on her tits.
Olivia then turn and facing me, she smiled. Holding her by the waist, I backed her against her bed, and lifted her up, sitting her on the edge. As we looked at each other, and I pushed her back a little, I could see her pants had inched down just enough to where I could see the band of her panties. Moving between her legs, Olivia smiled and then as she nervously put her arms around my neck, I felt I had a chance.
Looking at each other as I held her by her waist, we kissed and again moved my hands up to feel on her tits. I had a hard on thinking about wanting to fuck her, but knew I needed to be cautious, because I felt she had never done it before.
Laying her back, I said, “Move back,” as I grabbed her hips and pushed her a little.
Grabbing the legs of her pants and immediately tugging at them, Olivia let out a little giggle and then lifted her ass off the bed, trying to help. Smiling at her as I continued to pull them down, Olivia suddenly grabbed at her panties when she felt them starting to slip off too.
Getting her pants all the way down, I tossed them aside and as I looked back up, Olivia was cautiously smiling. Looking back down as she continued to adjust her panties, I found myself looking at her firm little thighs, and when I caught myself staring at her pussy as it pushed against her faded, powder blue panties, I hastily looked up.
Nervously smiling at her, I could see she seemed a little apprehensive, and not wanting to miss a beat, I reached down and undid my pants. Olivia again leaned up on her elbows to watch and after wiggling a little and letting them fall to the floor, I quickly adjusted my boxers and then climbed on the bed. As I positioned myself on top of her, holding myself up off her, I gave he a kiss.
Moving between her legs and pressing my cock against her crotch, she opened her eyes. It was obvious that she felt how hard I was and as I leaned up and knelt between her legs, Olivia curiously looked down, wanting to see. Looking down myself and seeing that my cock was bulging to get out, I smiled and adjusted it, trying to hide it.
As we looked at each other, I smiled and then reached up to feel on her small little titties. Yea, they were small but very firm and as I moved her shirt up a little and put my hand up under her shirt and unhooked her bra clasp, Olivia instinctively reached up, holding her bra against her chest.
Taking my hand out from under her shirt, we looked at each other and as I gently moved her hands away, I gave her a kiss.
Looking at her I asked, “Are you on the pill?”
Hesitantly, Olivia smiled and nodding she said, “ Yea,” and then continued by explaining, “ever since she caught me making out with my old boyfriend.”
Smiling, I hugged her and as I tried to lift her shirt up over her head, Olivia hesitantly lifted her hands over her head as I took off her top. Olivia, being a little embarrassed, immediately held her little bra against her chest and asked, “Do you think we should do this? “
Smiling, I laid her back again, and told her, “If you want to stop,” but before I could finish she said, “it’s okay.”
Moving her hands and pulling the two sides of her little bra aside I thought to myself, “Oh my god,” as I looked at her boobs.
Helping her get her arm out of the one side of her bra, I then pulled on the other side, trying to slip it out from under her. Casually dropping it off the edge of the bed, I leaned up and after giving her a kiss, I again knelt in front of her and tried to get her panties off. Olivia, nervous, eventually helped me get them off and after she cast them off the bed, we looked at each other.
Trying to be as inconspicuous as possible, I looked down at her crotch. She had only a little hair and as I put my hand on it and started to gently rub it, she too put her hand on mine. Looking up at her, I smiled and then after moving her hands to her sides, I put my hand back on her mound.
Smiling as we looked at each other, I again massaged her little pussy, and making sure to try to spread it, all I could think about was wanting to fuck her. Looking down and putting my finger and thumb on the fleshy part of her pussy, Olivia seemed to tense up a little.
It was so hot, I couldn’t believe it and when I pushed down, spreading her pussy lips, making her little clit push out, I immediately looked up at her. Olivia was watching and after a subtle smile, I went down and kissed her pussy.
Quickly getting into a better position and bending her legs at the knees, I dropped down and closing my eyes, I dipped my tongue into her slit.
Olivia now laid back and as I started to lick her pussy, she squirmed a little. Grabbing her thighs and spreading her lips as I pulled her closer, I tried to push my tongue as deep into her as I could, burying my face.
Trying to steady her, I reached my hand up on her chest, feeling for her tits. She was so wet and the musky smell of her pussy was such a turn on, I didn’t want to stop. However, as I leaned up to catch my breath, I looked up at her.
Gently caressing her little boobs, she looked down at me and then seeing her smile, I leaned to one side and reaching down, I tried pulling my boxers off. Olivia smiled and then as I eventually pushed them down and kicked them to the floor, I reached down and stroked my cock briefly.
Olivia strained to look down and when she happened to see it, she smiled and laid back. Moving up, letting my cock brush against her crotch, I kissed her and asked, “Are you okay?”
Without looking up, she nodded and when I said, “I’ll be careful,” she smiled and wrapped her arms around my neck, holding on.
I didn’t want it to hurt, but knew it was going to, and as I reached down and carefully ran the head of my hard cock up and down her wet little slit, I hoped she’d relax enough to let me push in. It was obvious that Olivia was scared and when I tried to push into her tight little pussy, she immediately tensed up and pulled away.
Continuing to worry about it hurting, knowing the minute I pushed into her it would, I kissed her and told her to relax. With her eyes closed, Olivia smiled, and then as I tried to position the head of my cock in the right spot to push into her, she took a deep breath. Leaning into her, trying to push my cock into as gently as possible, I could see Olivia had grabbed a handful of sheets.
It was definitely uncomfortable for her and after a couple failed attempts, I finally realized I just needed to do it if I was ever going to get in her. Telling her to relax, I took hold of my cock and as I pulled her close and forcibly pushed into her, she opened her eyes and said, “Ouch!”
Olivia hastily moved her hands to my thighs, and pushing me to stop, she tried to pull away.
Knowing it hurt, I Instinctively pulled out and as I tried to hold her still, I said “Sorry.”
I wanted to be in her, I didn’t want it to hurt, but she was so tight, and as I looked at her, I could see she was scared. Olivia smiled sheepishly and after taking a deep breath, I asked, “Are you okay?”
I knew I needed to try to calm her a little if I was going to have a chance and so leaning forward, I give her a kiss and asked if she was okay. I didn’t know if I should stop or not; I didn’t want to and when I asked her if she wanted me to stop, she shook her head and said, “No.”
Kissing her again I said, “if you want to stop, we can.”
Olivia shook her head and after another kiss, I told I’d be careful. Smiling, Olivia again put her arms around my neck and as I pushed into her I though, “Oh yea,” but I could still see she was in some pain.
Gradually, I started moving my cock in and out, which seemed to work and seeing she had started to relax a little, I pushed into her a little more until I was all the way in. Fucking her now, I hunched over her, and putting my hands under her shoulders, I bucked my hips into her.
I wanted to cum, I hoped she wouldn’t stop me and as I continued to fuck her, I was soon close. Out of breath, I said, “I’m going to cum,” as I tried to keep pumping in and out of her.
Olivia immediately moved her hands down and pushing on my chest she said, “Don’t cum in me!”
Quickly leaning up, I hastily reached down and grabbing my cock, I pulled out. Olivia was up on her elbows and as I held my cock and stroke it, I leaned forward making sure cum shot out onto her stomach. Olivia instinctively pulled away a little when the first big shot of cum hit her stomach. Leaning forward a little more, I told her to stop.
It felt so good and when I saw her smile, I felt she was okay. I was done and as the last little bit of cum dribbled out, inadvertently dripped down on her pussy, Olivia pulled away again.
She was awesome and as I lay next to her and held her, I realized she wasn’t holding me with the same intensity. I hoped we might be able to do it again, but I sensed Olivia was a little uneasy about what we had done and figured she was having second thoughts about it. Immediately, I needed to try to clean her off a little, and as I raced into the bathroom she asked, “Where are you going?”
Holding up a finger as I scooted onto the bathroom, I quickly grabbed a towel and heading back. Smiling, I wiped the cum off her stomach and smiling as I looked at her, I felt I needed to give her a little space, a little time.
I’m not sure if it was because I was so much older or if it was the fact that she let me fuck her, in any case, as I held her away from me and we looked at each other, I could see she was obviously nervous about something. Smiling I said, “I think I should get going,” but she was hesitant.
She definitely seemed to be having conflicting thoughts, unsure if she wanted to be alone, but as she pulled the sheet up, covering herself, she nodded. I felt bad that she was feeling scared and after another hug, I got off the bed, got dressed, and gave her a kiss on the head just before I left.
We of course saw each other at school and I wanted to be with her again, and all the time hoping she’d come talk to me, but Olivia tended to stay just out of reach. I knew she was thinking about what we had done, how could she not, and being she was shy and maybe a little self conscious she was unsure how to come talk to me. Eventually we did talk, but it was very superficial. I hoped she might suggest we get together, but she never even hinted at it. I liked her a lot, and think about her to this day, and every time I see her, I look for a way to talk to her.