Chapter 8

Two down, four to go, it was going to be a long night. I walked down the hallway and back down the stairs. I stood in the entrance way to the leaving you and peaked around the corner. Next was Emily which I wasn’t sure I was comfortable with doing things with her. She was a fairly innocent and shy looking girl, it just felt wrong time be her first, which I knew I would be. However, she did agree, which either she wanted to partake in these events or she had been forced in by peer pressure. In the end, I knew I would be the bad guy if it was peer pressure, and in the end regretted it.

I stood in the entrance way watching Emily as she sat on the couch. She had that innocent look on her face like she always does. Her knees were closed, and her hands were folded over her legs while she twiddled her thumbs. She seemed nervous from what I could tell, but she looked calm, just waiting patiently. At this point, I wish I had my pants, which I had left upstairs in the bathroom with Abby. It would have at least made approaching her a little bit easier. By some miracle my erection was gone, so my member laid in a half limp phase between my legs which made it a little less awkward. I didn’t want to waste any more time, so I went ahead and let my presence be known. I cleared my throat.

“Oh, hi there.” She faced me, a light smile was present on her face. Nothing in her tone of voice, nor look on her face, showed any awkwardness about me being naked. Her eyes skimmed over my exposed body in a way that revealed her curious, despite being so innocent. When her eyes meet mine, she noticed that I had been watching her, a light blush covered her cheeks in a cute embarrassed way.

“Hey,” I said in an awkward manner, which was weird. I didn’t expect to be the awkward one in the situation.

“Can I come and sit?” I was still trying to respect her personal space, unaware how she felt about the situation.

She looked at me and glanced at the couch. “Oh yes, of course, of course, you can!” She blushed a little harder and patted the seat next to her. I still couldn’t tell how she was feeling.

I approached the couch slowly, as if not to scare off a beautiful bird perched on a branch. I was just an observer, trying to observe the nature up close, without spooking it. I didn’t want to frighten her, this wasn’t even about sex anymore. I just wanted her to feel comfortable, let her know that she didn’t have to do anything she didn’t want to.

“So um ... are you comfortable wi...” I didn’t pause on purpose, no, I was surprised. Emily leaned in on me and planted a small kiss onto my lips. We both looked into each other’s eyes with light blushes on our face.

“Did I do it right?” She looked down at her legs, the blush was still present on her face.

That’s when I realized that she did actually agree on her own free will. I wasn’t sure how long it took her to make up her mind on the situation but she was content with her decision and wanted to move forward. I smiled lightly as I noticed how mature she had become. Sure I had always looked at her body as slightly mature, but this was the first time I really noticed her personality grow.

“Oh I don’t know, it was a little fast, maybe you should do it again, just a little bit slower this time.” I said with a playful smirk as I placed one of my hands on her thigh.

To my surprise, she actually took me seriously. She leaned in once more and placed a sweet kiss onto my lips. It was passionate, very passionate. I felt warm inside and my little friend began to poke his head up. She pulled her head away slightly after we kissed for a few moments. Her eyes were closed, but I had kept mine open to observe her.

“I’m pretty sure you got it, one more time to be absolutely positive.” I whispered the words before she could say anything or even open her eyes.

Once again, she leaned in and placed her lips against mine. It was a slow start, just multiple slow kisses back to back. My hand beginning to stroke up and down her thigh lightly as we sped up. The kiss started becoming deeper and our heads twisted from side to side. I could tell it was her first time, but it was still natural to her as she caught on quickly.

As the kiss broke apart we both sat breathing heavily, our faces mere inches apart. I had opened my eyes and stared at her cute face. Her eyes stay closed for a few moments before opening to meet my gaze. Her eyes were a beautiful blue color that matched her dark brown hair. As our eyes connected, she blushed and looked down to avoid the eye contact.

I know I mention her being cute and innocent a lot, but that is who she was. It’s hard to imagine her in that situation because of how she normally acted. This was a whole new Emily to me, and I was watching my steps. Trying not to scare her off.

“I’m umm...” She started but paused before finishing. She looked up into my eyes and took a deep breath before exhaling. I could see the nervous confidence in her eyes.

“Here’s the thing, I’m really nervous about this, but I still want to do it. I wasn’t pressured into this, the other girls even tried to talk me out of it, but I’m ready. I’ve just never done this before so I don’t know what to do.” She rambled everything out in one breath and kept eye contact the whole time.

I was beginning to understand the situation a lot better now. Emily was the youngest of the group, the “baby” if you will. She probably felt like the out one, like she was behind everyone. She wanted to prove to her friends that she was mature enough to do what they did. She wanted to fit into the group.

“I understand, then let me lead.” I gave a small smile and leaned in hard and placed a kiss on her soft lips. I laid her on her back slowly, the whole time our lips were connected.

We kissed for a moment, with her on her back and me hovering over her. The kiss broke and we panted in each other’s face, her eyes looking up into mine. I started slow, placing my hand on her waist and slowly sliding it up. My hand slipped under the bottom of her shirt and made contact with her bare skin. She blushed and sucked in her stomach out of surprise.

She didn’t fight me, not least did she resist or look nervous. She had this confident look as she kept eye contact with me. She squirmed a little and scooted down on the couch to get in a more comfortable position, her head was rested on the arm.

“Just be gentle please.” She whispered and closed her eyes as she kissed me one last time before giving up control to me.

“I’ll be gentle, I promise.” My hand continued up her body and her breathing stumbled a few times. Her breathing had deepened and her body squirmed under me.

Finally, my hand went over her breast and I grabbed it with a light grip. She groaned lightly and wiggled a little, but didn’t open her eyes or speak. I placed my lips against hers once again, and she responded with a light kiss. My free hand went for her jeans and skimmed the rim before unbuttoning them. Next, her zipper came down slowly, the whole time I kept our lips connected.

“Here, let me help.” She smiled up at me and opened her eyes.

Her arms went down and her thumbs slipped into the waistline of her pants. She lifted her butt off the couch and tugged down, I helped pull them off of her legs while she pushed down. We managed to pull off just her pants, leaving her panties hiding her sweet spot. She looked up at me with a blush color faced and I groaned lightly.

I leaned down and once again placed my lips against hers. The only difference was the type of kiss. I kissed her deeply, filled with my lust and passion. Surprisingly she responded by pressing back into me. Her arms going up and wrapping around my neck to pull me close. My hands wandered, and slipped down onto her pink lacey panties. I didn’t go in then, but I did threaten so by pulling back at the elastic and letting it pop back into place lightly. My hand continued to travel down until it felt a wet spot in the cloth. Her body squirmed as she laid under me, but she kept eye contact the whole time. I pressed my fingers into the wet spot and she groaned lightly.

“I’m really enjoying the foreplay and all, but we only have fifteen minutes left. Maybe one day when we have more time we can continue the sensual play. Right now, I want you to take me.” She broke eye contact and her face turned a dark red.

“I understand, then lets to it.” I smiled and kissed her neck lightly, which stifled a moan put of her.

I pulled her pink lace underwear down her legs and she pulled her right leg through, leaving them to hang on her left. I was surprised to see that she wasn’t completely shaven below. Instead, she had a nice trimmed bush that covered her mons. From my view inside her legs, she was a bright pink color and very wet, a dark spot had started to appear below her ass.

“Are you sure you’re ready?” I asked one last time to make sure she didn’t want to back out now. She didn’t speak, she simply nodded at me and closed her eyes, once again she wrapped her arms around my neck to pull me closer.

I grabbed my member and rubbed it against her opening lightly, which caused her to squirm. After lining myself up, I began to lightly press into the slit. She groaned and dug her nails into my back. I went in slowly and she never told me to stop, so I didn’t stop until I was completely buried inside of her.

“Ashley was right, it doesn’t hurt ... I’m just full. The stretching is uncomfortable, but it’s not too bad.” She smiled and kissed me, her eyes locked with mine. I didn’t respond, but I did smile and return the kiss.

My hand slipped under her shirt once again found her breast which I fondled. I was letting her get used to the thickness before I began moving. Emily was really verbal and told me how it felt good for me to touch her breast and play with it like I did. So I decided she had adjusted and was ready for me to move.

I pulled my member out her opening slowly and pressed in the same. I found that pattern to stroke with and she went crazy. She didn’t scream loud, nor did she curse. She simply moaned and her body wiggled and squirmed under me.

“This ... this feels really ... really good.” She panted to me as my body rocked against hers. Her eyes were open so we watched each other’s facial expressions. Every now and then, I would groan at how tight she wrapped around me, how good it felt.