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.
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