That New Guy

Note: If you haven't already, read the previous chapters of That New Guy, which are prequels to this story.

***

The Monday morning after the sex-filled weekend (or sex-filled Sunday night, in Rachel's case) found both Rachel and Meg lying in bed, rehashing their multiple, highly-satisfying orgasms, prior to their alarms even going off. Finally, Rachel got up and went to Meg's room, sitting naked on the edge of her bed, happy to find that she was already awake.

"I need a quickie orgasm to take the edge off," Rachel said.

"I was thinking the same thing," Meg replied, "climb aboard."

Meg threw back her covers to reveal that she was also naked and Rachel straddled her in a sixty-nine. They each managed to bring the other to another orgasm before Meg's alarm went off then they went about their morning routines, getting ready for work.

Meg and Deb were both conservatively dressed that morning and both only interacted with Jake when he strutted over to each of their workspaces, expecting both of them to still be interested in using him to make the other jealous. He was stumped when both of them were completely indifferent. He called each of his buds, who all feigned ignorance about why the two of them would have completely lost interest after Saturday's festivities; they all knew that their own chances with Deb and Meg were shot if Jake found out why they were no longer interested in him. Deb and Meg had discussed the fact that he still had the flash drive with Meg's photos and Deb's video and wished they had thought to grab it before they'd left his house on Sunday morning. Fortunately, they found out a couple of days later that Chuck had thought to grab it and it was now in his possession. They both promised to reward him for being thoughtful and foresighted. He assumed that they would be rewarding him together but they were so relieved that they decided he needed an even bigger reward than that. When Deb invited him over for her reward, Rachel was already there. Of course Meg's reward was going to be the same sort of set-up.

After Deb, Rachel and Chuck were all thoroughly satisfied and lying in Deb's bed recovering, Deb recalled Meg sharing that there was a story about Chuck and the master bathroom at Jake's house.

"Since I assume you'll need some time to recover from that," Deb said, "I heard there was a story about you and Jake's sister in their parents' shower that sounds like it'd be pretty hot."

"Oh God," Chuck replied, looking embarrassed, "why do you want to hear about that?"

"Well," Deb said, "if you share all of the intimate details, I'll bet we're all ready to go again by the time you're done."

That was all it took and so Chuck began his tale...

It was right after Ashley had finished her freshman year of college and I wasn't even aware that she was back home yet. I was in Jake's neighborhood and tried to give him a call but he didn't answer so I figured maybe he was in the pool and decided I'd just stop by. I came around the back of the house the way you and Meg did on Saturday but, rather than finding Jake, I found Ashley, with her back to me, just shaking her long, brown hair out of her swim cap. She was in a one-piece swimsuit and had obviously just finished a workout in the pool. I stopped in my tracks, staring at her perfect ass, realizing that she was really all grown up now.

She and Jake had never been really that close. She was quiet and smart but not unattractive, just young. To Jake, she was just his annoying little sister. She and I had always gotten along, partly because we were both pretty smart, not that I'm tooting my own horn. You know Jake, though; he's not the sharpest tool in the shed so it was hard for him to relate to how smart she was. I didn't have that problem. But she was still just Jake's little sister until that day I saw her after her workout and I realized that she was a woman now, a desirable woman for sure. With that realization, I managed to not only drop my car keys, but kick them as well. The noise startled her and she turned around suddenly but smiled when she saw that it was me.

"Hey, you!" she said enthusiastically.

"Hey, you," I replied then bent down to pick up my keys as my eyes traveled along the length of her body behind my sunglasses. Like the rest of the family, she had an athletic physique and clearly worked out regularly. Her legs looked a mile long and she appeared to have a substantial rack squished into that one-piece swimsuit.

"How was school?" I continued, "I didn't know you were back."

"It was tough," she replied, making a face, "I'm still recovering from finals. I just got back yesterday."

"That's really saying something," I said, "if it was tough for you."

"Oh shut up," she said, flushing slightly, "I'm afraid Jake isn't here, though. I get home yesterday and he and our parents are gone all day today."

"I tried calling him but he didn't pick up," I told her.

"He probably irritated Mom or Dad playing with his phone and they made him shut it off," she laughed, "You'd think he was still a teenager but I think he just gets distracted by shiny things."

"Well, I don't want to bother you if you're still recovering from your finals," I said, "You're probably going to appreciate the time to yourself."

"Actually, you're more than welcome to hang out," she replied, "I was just planning to go take a shower. You want to join me?"

She asked that question less with confidence and more with hope. I could feel my cock stiffen slightly in my shorts.

"Seriously?" I asked, "I can't even tell you how much I'd love that."

She smiled so broadly that I think my heart may have skipped a beat as it occurred to me how beautiful she was and that I was, at the very least, about to see her naked. We headed into the house and, as we made our way upstairs and she led me to the master bathroom, I tried to position myself slightly behind her when I could to continue admiring her sweet ass. Once we were in the vast bathroom, she stopped and turned back toward me so I slipped my arms around her and kissed her. She responded by wrapping her arms around my neck and slipping her tongue into my mouth. We made out as my cock stiffened against her but, as much as I was enjoying making out with her, I really wanted to get her naked. I brought my hands up and started to slide the shoulder straps of her swimsuit down her arms. She dropped her arms and we parted so I could watch as her succulent tits were revealed.

Of course, compared to yours and Meg's, they weren't really that big but per my standards at that moment they were. As they were freed from the spandex confines of her swimsuit, they sloped down to her large areolas and hard nipples, so I lowered my head to lick and suck her nipples while continuing to slide her swimsuit down. Once her swimsuit was down to her hips, though, I stopped then, after I'd licked and sucked her nipples a bit, I dropped to my knees and continued to slide her swimsuit down. Her dark brown bush was trimmed to a narrow triangle so as not to escape from the edges of her swimsuit. As I gazed at it, my hands were pushing her swimsuit down over her ass, caressing the soft, smooth flesh. My cock was a steel rod at that point but there was something I couldn't resist doing while her pussy was right in my face.

Once she'd stepped out of her swimsuit, I ran my tongue along her slit, tasting her pungent juices and causing her to moan. I ran my hands over her toned ass while I was licking her pussy but, when I brought a hand down to slip a finger into her, she leaned back against the sink and parted her legs a bit for me. Her pussy was nicely snug and quite slippery as I slid my finger in and out while licking and sucking her clit. She moaned louder and longer, which was obviously a good sign, and my goal was definitely to make her cum. I hadn't thought about fucking her before that day and now I wanted to make sure that she experienced enough pleasure that she'd want to get together for sex whenever we had an opportunity. I'd been honing my oral technique for years for exactly that same reason so I just put what I had learned into effect.

I didn't necessarily want her to cum quickly but I also didn't want to draw out the pleasure to the point where I was denying her the relief of an orgasm. Based on how hot and wet her pussy was along with the noises she was making, I was feeling pretty confident that she was building quickly toward an orgasm. I just had to count on my technique also making it a highly pleasurable one. I was certainly enjoying the opportunity to be devouring her hot pussy and wanted to assure that I'd have future opportunities, as well. I knew it could end up being tricky having a sexual relationship with Jake's sister but, feeling and tasting her hot pussy had me pretty certain that it'd be worth the effort. Even that soon after being invited to join her in the shower, I wasn't thinking that I just wanted to fuck her; we had a mutual respect for each other going back a few years so I was immediately thinking that this could be more than just a one-time thing. I wasn't thinking about dating her but I wasn't completely ruling out the possibility of some sort of relationship.

When she started tensing up while holding my head and pulling it against her pussy, it was clear that she was on the verge of cumming. I didn't modify my technique or my pace since both had served me well thus far and it ended up being just a few minutes later when she momentarily held her breath then gasped as her body started shaking. I continued to devour her through her orgasm, which was long and appeared to be highly pleasurable. Only once I was certain that she'd finished cumming did I sit back on my heels while sucking her juices off of my finger. I was admiring her body as I sat there while she was catching her breath and recovering.

"You're really good at that," she finally said, opening her eyes and looking down at me.

"It was my first time," I lied with mock seriousness.

"Bullshit," she said with a smile, calling me out, "It may have been your first time with me but it certainly won't be your last."

She helped me up then switched places with me, so I was leaning against the sink as she dropped to her knees and went to work opening my shorts. Since we'd be showering and she was fully naked already, I went ahead and stripped off my shirt as she got my shorts down, followed by my briefs. My rigid cock popped out in her face but she helped me to step out of my shorts and underwear before gripping it and pumping it gently then guiding it into her mouth. I moaned as she inhaled it, sliding her lips down my shaft as she pumped the base. She immediately started to enthusiastically suck me off and I knew it wouldn't take much of that before I was spewing down her throat. Admittedly, it was not the best blowjob I'd ever received but, as they say, a blowjob is like pizza: even when it's bad, it's still pretty good...and it wasn't a bad blowjob by any means.

Honestly, I was kind of glad that it wasn't the best blowjob I'd ever received because then I'd have been wondering how many cocks had been in Ashley's mouth before mine. I preferred to maintain the image of her as unsullied, whether it was accurate or not. Just the fact that it was Ashley, Jake's little sister, made it an even more enjoyable blowjob but the fact that I now considered her a hottie as well further amplified the pleasure. So, bottom line, I had no complaints about this blowjob and didn't hesitate to encourage her and let her know how good it felt. I ran one hand through her thick, dark brown hair but didn't push my cock any deeper into her mouth, leaving the pace and depth entirely in her control. My orgasm was slowly building and I was relishing the pleasure that I was feeling as a result of her cocksucking.

As my cock started to swell even more with the approach of my orgasm, she maintained her pace and the pleasure continued to build. I did warn her when I was getting close, just in case, but she didn't pause or hesitate. When I exploded into her mouth with a moan, she swallowed my load without any apparent issues and continued to suck me off until I was completely spent. When she released my cock, she sat back on her heels and looked up at me.

"That was outstanding," I said, reaching down to help her up.

"That's very nice of you to say," she said, "but I'm not sure that it was that good."

"Trust me, I'd be happy to experience that every day," I replied, "In fact, if you're not feeling confident about it, I volunteer to let you practice on me whenever you want."

That made her smile so I took her in my arms and our naked bodies pressed together then I kissed her. We made out a little bit before finally heading into the shower. She grabbed a hair thing and put her long hair up then adjusted the water and wet herself down as I admired her naked body. When we traded places and, as I was wetting myself down, she grabbed a bottle then we each took a handful of the body wash it contained. We each lathered up the body wash then started to lather up each other. Of course I started with her tits and she started with my cock and balls but we did end up thoroughly washing each other while getting ourselves all worked up again in the process. When we finished up and were drying each other off, I was fully rigid again and ready to slip my cock into her snug pussy. We headed to her bedroom first, bringing our clothes and towels along with us.

I'd never really been in her room before; I'd only held brief conversations from the doorway. It was big, as was her bed, and had a desk and an armchair among other furniture. She went to her nightstand and dug around in a drawer as I stared at her bare ass then she extracted a condom that looked like the kind we used to get from our Resident Advisors in the dorms back in college.

"You don't mind, do you?" she asked as she handed it to me.

"Of course not," I replied, tearing it open and rolling it on.

"I don't have a lot of experience," she said, almost apologetically.

"Then you should be on top," I replied, "so you can be in control."

I got onto her bed and lay in the middle with my sheathed cock standing straight up then watched as she climbed on, her tits swinging and bouncing. She straddled me as I continued to admire her physique then I guided my rigid cock toward her pussy and she eased herself down onto it. We both moaned as her snug pussy engulfed my throbbing cock and I was happy to see a smile on her face rather than a grimace. She sat on my cock for a moment before beginning to move slowly up and down. I moved my hands up her thighs to her waist then reached further up to fondle her tits, caressing the soft, smooth flesh and running my palms over her hard nipples. She gradually increased the pace at which she was riding my cock and her pussy felt amazing even through the condom.

Although my gaze alternated from her tits to her trim bush and up to her face, it seemed like it kept going back to her face, not only because she was so pretty but also because I felt like I had to keep confirming that it was actually her. She had her eyes closed but the big smile remained as she was riding me harder and faster. We got a good rhythm going and I was pushing up into her each time she came down, wanting to give her maximum penetration. Her bed remained silent even as her pace increased but, as her tits started bouncing more, I ended up taking my hands away from them so that I could watch. I brought them back down to her waist then reached around to caress her toned ass. She wasn't shy about expressing herself verbally so it was obvious when she was getting close to cumming. In addition to her vocalizations, I could feel through the condom that her pussy was becoming even hotter and wetter. I think the condom was helping my staying power even though it seemed like no sensitivity was being sacrificed.

Although I knew she was right on the verge, it took me by surprise when she dropped down and suddenly started shaking as she let out a cry. She didn't move up again, remaining seated on my cock as her orgasm coursed through her. Since her tits had stopped bouncing, I brought my hands around to fondle them again as she was cumming. Her orgasm appeared to be another long and intensely pleasurable one so I was pleased to have helped her achieve that. When she'd finished cumming, she remained seated on my cock for a moment as she caught her breath then she opened her eyes.

"I've never had an orgasm during sex before," she revealed before leaning forward to kiss me. We made out for a moment as I went back to caressing her ass while slowly sliding my cock in and out of her again.

"Can we try something different?" she asked when she pulled my mouth from mine, "I've never had a boy in my room before and all of my experience thus far has been sort of fumbling around, usually in the dark."

"And you want to take advantage of the opportunity?" I asked.

"Yes!" she exclaimed, "I don't know if we'll ever have this kind of freedom here again so we should take advantage and I shouldn't assume you'd even want to come back."

"Hey," I said, taking her face in my hands, "I want to come back. In fact, I don't think I want to leave but I agree that we should take advantage of this opportunity then we can figure out what happens next."

She kissed me again then climbed off of my still rigid tool, kneeling on the bed as I sat up. I had an idea so I hopped off of the bed and led her to the armchair then had her kneel on it facing away from me as I stood behind her. While she braced herself on the back of the chair, I guided my cock into her from behind and held her hips as I pushed it all the way in. We both moaned as my hips pressed against her sweet ass then I started to slowly slide my cock in and out of her. She was immediately pushing back and, once we had a rhythm going, I not only moved my hands up to cup her tits but I also suggested that she massage her clit as I was fucking her. She dropped a hand down and her moaning continued. I was hefting her soft, smooth tits while feeling her hard nipples against my palms as I was sliding my cock in and out of her pussy once again.

While I was savoring the feel of her pussy, I was already plotting our next move. Aside from fucking on the floor, which was not the most appealing option, the majority of the furniture didn't lend itself to being an accessory to fucking. I had a couple of ideas, though, but wanted to be sure that the act of fucking itself didn't get overshadowed by any acrobatics. While Ashely wanted to try some new things and I wanted to indulge her, I really was just content with the opportunity to be naked with her and enjoying her snug, slippery pussy. Even though I didn't have as enjoyable a view fucking her from behind, I could still admire her sweet ass and cupping her tits with her hard nipples against my palms was definitely something I was thoroughly enjoying.

Once again, she was setting the pace and it picked up pretty quickly. Each time she pushed backwards, I'd give a thrust but she was otherwise in total control. I think the hand that was taking care of her clit was definitely helping to push her toward another orgasm though I wouldn't have said that she might as well have been masturbating; hopefully my cock was contributing significantly to her pleasure. Based on the noises she was making and how hard she was impaling herself on my cock, I was pretty confident that she was receiving a significant amount of pleasure from me fucking her. I could feel the distant stirring of my own orgasm but, although I was absolutely enjoying the feel of her snug, slippery pussy, the condom was definitely helping to keep me from cumming too quickly.

I was impressed that, as hard as she was pushing back against my thrusts right before she came, her ass did not jiggle even a bit. It was still fun to watch, and listen to the smacking sounds along with her longer, louder moans, right up until she gave that one last push backwards. She held herself motionless for a brief moment, and may have been holding her breath as well, then let out a cry as her body started shaking. I continued to fondle her tits as she was cumming but did not thrust into her, not wanting to throw anything off. Her orgasm appeared to be yet another long and intensely pleasurable one, which I was confident that we both appreciated. I was definitely feeling that a return invitation was by this point a foregone conclusion.