I didn’t want her to feel self-conscious, she was so pretty, and when she said, “Sorry they’re not very big,” I smiled and told her, “It’s okay,” and then said, “I like it.”
This made her look at me and seeing her smile, made me smile too. I didn’t want her to worry, because right now the size of her boobs really didn’t matter. I wanted to fuck her, and when I went to move her arm, and I looked at her, Cassie smile too, but nervously.
As she dropped her arm, exposing her chest, I moved my hand to feel on her budding little boobs. It was very apparent she was probably younger than 18, and when she suddenly blurted out, “I’ve never done this before,” I looked up at her.
I figured she hadn’t, and trying to put her at ease, I smiled and said, “Cassie, your beautiful.”
This comment made her look down and seeing she was blushing, I put my hand under her chin and then lifting her head I said, “Don’t worry,” as I gave her a kiss.
She smiled, and then as I continued to feel on her little breasts, I moved down, eventually tonguing and sucking her nipples. Cassie again took a deep breath, as I mouthed her nipples and took most of her boob into my mouth. Stopping, I laid her back now, and then climbing on top of her, I looked at her and said, “If you want me to stop, tell me, okay.”
Cassie nodded, which made me smile, and after giving her another little kiss, I kissed her neck, eventually making my way down her chest and stomach. I could smell her faint perfume or maybe it was a body wash, in either case, I wanted to taste her.
Putting my hand on her mound again, I looked up at her, and seeing she had her eyes closed, I got between her legs. Cassie quickly leaned up on her elbows and looking up at her, I smiled and then dropped my head between her legs. She now reached her hand down, touching my head and as my tongue dipped in her slit, she laid back again.
Eating her pussy, Cassie arched up a little, and as I put my hand on her chest, trying to steady her, I closed my eyes as I licked and tongued her little pussy. I wanted to try to get her off, but then Cassie suddenly reached down, grabbing my head saying, “Stop.”
I didn’t want to stop, but looking up at her and seeing a concerned look I asked, “Are you okay?”
Cassie nodded, and seeing her smiling guardedly, I smiled too and moved back up, casually wiping my mouth. Kissing her, I grabbed her sides and giving them a little squeeze I said, “Don’t worry.”
Smiling at each other, I again explained, “If you want to stop, just tell me.”
Cassie again nodded, but it was obvious she was nervous, and seeing this I kissed her again. Looking at me and smiling she told, “Just go slow.”
Telling her okay, I kissed her again, and then out of nowhere I subtly asked, “Are you on the pill?”
This made us both pause and then smiling Cassie said, “Yea, my mom put me on it.”
Giving a more serious look I smiled and said, “That’s a good thing.”
Cassie smiled too and then nodding shyly, we again kissed. Leaning off her a little, I grabbed my cock, and as I guided it toward her little opening, I stopped and asked, “Do you want me to use a condom?”
I didn’t really want to, and when she didn’t say anything I said, “I’ll be careful,” she unknowingly nodded.
Seeing she was a little apprehensive, I said, “Just relax.”
Cassie now laid back and as I moved up, I brushed the head of my cock against her pussy and then gently pushed into her. “Oh my god,” I thought, “she’s so tight,” and as I moved my cock up and down her slit and pushed a little harder, Cassie grabbed the covers, clinching them.
I knew it must have hurt, but I wanted to be in her and then as I pushed into her more, the head of my cock suddenly slipped in. Cassie immediately raised up and quickly pulling away, she exclaiming, “Ow!” which made me lifting off her, letting my cock slip out.
I knew it was uncomfortable and seeing a somewhat distraught look I asked, “Are you okay?”
Looking at each other, I could see Cassie was concerned, but then after taking a deep breath she said, “Just go slow.“
Smiling, I felt Cassie wanted to do it, and then as she put her hands on my waist, I looked at her and said, “Try to relax.”
Nervously nodding, she laid back again, and seeing she was really trying to relax, I again tried to push into her. Right away I struggled to get my cock in her even a little, and thought, “Oh my god, don’t let it hurt.”
Again, she was so tight, it was frustrating and when she felt me take in a deep breath, she asked, “What’s wrong?”
Desperately wanting to be in her, I didn’t say anything but then as I said, “You’re really tight,” she smiled and laying back Cassie told me, “It’s okay.”
Again, I didn’t want it to hurt but I knew I had to just push into her. Trying to go slow as I leaned into her, I hoped she’d relax enough to let me in. Looking at her, she put her arms around my neck, smiling and as I pushed into her a little, she wiggled and then holding me, I asked, “Are you okay?“
Cassie nodded, and seeing her continuing to smile, I kissed her and then hurriedly pushed into her. Immediately, Cassie let go of my neck and pushing me, exclaimed, “Ow!” as the head of my cock slipped in.
I knew it hurt and when she tried to pull away, I tried to hold her still. Telling her to relax, Cassie twisted and grabbing a handful of the covers she said, “Stop!”
Pulling out, I hoped she’d relax, but seeing it was obviously hurting and feeling Cassie arching her back, attempting to get me to stop, I slid down a little kissing her chest. Frustrated as I continued to hold her, I let it slip all the way out of her. Cassie then took a deep breath, noticeably relieved and then seeing her smile, I asked, “Are you okay?”
She had her eyes closed tight, but nodding and smiling she again wrapped her arms around my neck. I hoped she was okay, and I hoped she let me try again, and after giving her a kiss, I asked, “Do you want me to stop?”
It made her pause for a second, but then opening her eyes and looking at me, Cassie simply said, “It hurts,” and then said, “I don’t know.”
Immediately I asked, “Maybe we should stop.”
Again, I really didn’t want to stop and hoped she’d let me keep trying, and seeing her apprehensively smile and not say anything I said, “Let’s try it again.”
Looking at me, Cassie smiled, and then nodding, she took another a deep breath. Smiling too, I said, “Try to relax,” which made her shifting a little, as she laid back.
I knew she was trying to get comfortable, and then as I slowly pushed into her a little and then took it back out, I hoped she’d relax. I wanted it to work and then as I gently wiggled the head of my cock in her wet little slit, and I felt her relax, I pushed into her. “Mmm,” I was in her, but as I guided my cock into her, every now and then, Cassie wanting to wiggle free.
Again, telling her to relax, I slowly tried to move my cock in and out of her, Cassie again grabbed a handful of the covers, continuing to squirm. It did feel good to be in her and I hoped it wasn’t hurting to much.
“Mmm,” I thought as I continued to push into her.
I wanted to cum, and as I started to fuck her, moving my cock in and out, I knew it wasn’t going to take long before was going to cum.
Holding her and kissing her, trying to fuck her, I continually tried to reassure her by softly asking, “Are you okay?”
Cassie again nodded saying, “Just be careful.”
Right now, I didn’t want her to worry, I wanted her to know everything would be okay, because there was no doubt I was going to cum, that’s if, she didn’t stop me. Trying to be as careful as possible, continuing to move my cock in and out of her, I wanted to cum. Bucking my hips into her a little faster and a little deeper, holding her and kissed her, I felt it.
“Oh my god,” I thought, “I’m going to cum,” and as I held her close, giving a couple deliberate pushes into her, my cock started to jerk inside her.
I was out of breath and when I stopped briefly and said, “Oh shit!” she raised up and asked, “Are you okay.”
“Oh yea, I was okay,” and then as my cock faintly buck and cum drained inside her, I again slowly moved in and out of her.
Stopping and holding her I kissed her cheek and said, “Yea, I’m good.”
Continuing to lean up, sensing something was wrong, Cassie pushed on me hastily asking, “What are you doing?”
Continuing to hold her, not saying anything Cassie said, “Don’t cum in me!”
Leaning up and quickly pulling out I thought, “Oh my god!” as I moved down.
It was too late, and seeing she was distraught as she pushed me to get off her, I grabbed my cock and knelt in front of her. It felt good to have cum, but as Cassie sat up and saw me inconspicuously squeeze the last little bit out, she hastily reached down to her crotch.
Watching her and seeing her reaction as she felt the sticky slippery cum that was oozing out of her, I moved to lay next to her. Bringing her hand up and looking at her fingers, it was obvious she was upset, and then showing me she said, “I didn’t want you to cum in me.”
Not knowing how to respond I simply smiled and said, “Sorry.”
Looking down as she frantically fingered her pussy, trying to get it out, I could see cum had spilled out onto her bed. Wanting to reassure her it would be okay, I put my hand on her leg, and then patting her thigh I said, “It’ll be okay.”
She was definitely upset and after a pause, Cassie quickly rolled off the bed, and hurried into the bathroom, closing the door behind her. “My god,” I thought, “what if she’s not actually on the pill.”
Worrying as I lay there, thinking why she didn’t say something sooner, I asked myself, “Why didn’t I thought about it too.”
Eventually, I heard the bathroom door open and as she came back in the bedroom, I tried to smile. She had a towel wrapped around her, making sure it covered her and then without looking at me she wistfully said, “I think you should probably go.”
I understood what she was feeling and not saying anything, I got off the bed and started getting dressed.
Pulling up my shorts and putting on my shirt, I tried to reassure her by asking, “You’re on the pill, right?”
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