Senior Year Memories Ch. 17

The fear must have registered on my face, because Rachel looked down at me with concern. "Are you sure you still want to do this? We can stop, anytime, I swear."

"No!" I pleaded. "No, I don't want to stop, I can't stop now, it's just... it's a little overwhelming. I've never... never done anything like this, considered anything like this."

"Take your time," Rachel said, slowly rubbing her soaked pussy lips along my cock. "We're in no hurry."

"Thanks," I said, watching her, feeling her, loving every sensation that came from my cock that threatened to overwhelm me and my better judgment. I wanted this so bad, no matter how wrong I knew it was, but the fight between my mind and my body was stronger than I ever anticipated it could be.

Was I really ready for this? Was this a line I wanted to cross? Was this something I could live with after all the other lines I'd crossed?

Reaching down, I grabbed my cock and lined it up with her entrance. Smiling, Rachel lifted the camera above her head and took a couple quick pictures. It took me a second, but I realized she was recreating almost exactly the first pictures Kaitlyn had ever taken for my Senior Year Memories album, only instead of a slutty mean girl cheerleader, I was being straddled by a sexy redhead covered in tattoos who just happened to be my best friend's sister.

"You ready?" Rachel said, setting my phone aside and teasing my cockhead with a little extra pressure. I felt her lips part around me slightly without accepting me inside, the anticipation excruciating.

"Yeah," I said, nodding.

Rachel nodded in return, gritting her teeth and sitting down on my cock.

"Oh, fuck!" we said in unison as the first few inches of my cock penetrated her. She wasn't kidding about it having been a long time since she'd done anything sexual, as it was a tight squeeze that threatened to make me cum then and there.

"You know," she grunted, shifting a couple more inches inside of her. "I've seen a few big cocks in my day, even been lucky enough to have them inside of me, but if there's one thing I've learned, it's that you never know how big it really is until it's in you. Fuuuuuuuuck."

She said the last word as a long, stretched out groan as she accepted even more of my cock into her beautifully tight pussy. I was more than halfway inside of her already, and with the slightest drop, Rachel dropped entirely onto me. Her eyes went wide with surprise, perhaps shock even, and she threw a hand over her mouth to keep from screaming, but she did well.

We were officially past the point of no return: I was now fucking Rachel McNeil.

"Holy shit," Rachel said, grabbing for my phone again. "I just need to see this, need to know that it's real, need to know..."

She angled the camera for a close up view of my cock spreading her pussy wide open and took a picture. When she looked at it, her eyes went even wider.

"God, fuck, that's so nice, so nice," she said, wiggling her ass on me in a way that drove my cock wild.

"Yeah," I whimpered, pretty far past real, solid words at this point. If I were the one giving Rachel goosebumps before, the roles had been reversed pretty handily as she took over my cock. My entire body was sensitive, every square inch of my skin feeling like it was a bundle of nerves. This wasn't made any easier as Rachel ran her fingers lightly down my rather unimpressive chest. I wanted to return the favor, but found it hard to get my hands higher than her hips.

Silently, her eyes never leaving mine, Rachel began to rock on my cock. She developed a slow, sensual pace, one that never threatened to become the savage fuck that I was so used to these days. This was about us, and our connection with each other, where getting off was a secondary concern even if it was the ultimate goal. We were one together here, and there was nothing in the world that could stop us in this unbelievably hot union.

I held onto her hips, helping her rock back and forth, matching my hips with hers as we worked a few inches of my cock in and out of her pussy. I could tell Rachel loved looking down at me, satisfaction the only emotion her face would betray as she kept fucking me. It felt a little unnerving how she stared into me, and I couldn't keep my eyes from darting around, taking in the rest of her as I worked at trying to believe that this was actually happening.

Seeing my eyes focus on her tits, Rachel smiled silently and leaned down, offering them to my mouth. Almost delirious with pleasure at this point, I couldn't help but lean up and take one of her beautifully puffy nipples in my mouth. I suckled, I licked, I nibbled, living for the sounds that she made, and only when it seemed as if I brought her to the peak of pleasure did I switch and start in on the other nipple.

A certain, desperate urgency had begun to take me over, and I started pumping up into her a little faster than the pace she'd determined demanded.

"You gonna cum soon?" she whispered to me.

"Yes," I whimpered. "You?"

"Gonna take a little more work for me. You need to cum, you just cum, so long as you make sure to help me finish afterward," she said, squeezing my cock with her pussy.

"I can agree with that," I said. At that, she quickened her pace only slightly, working and milking my cock for all it was worth. Waiting this long for release had been exquisite agony, a buildup of pressure that I was at once enjoying and so grateful to see at an end. Soon my balls were swollen, twitching, ready.

"That's it, cum for me, Ryan, cum for me, fill my pussy, do it, cum for me, cum for me," Rachel goaded, smiling as she never once gave up her rhythm.

That was it. That was all I needed. My grip tightening onto her hips, I gave a few last, preparatory thrusts before the floodgates opened. I came and I came hard, wave after wave of cum exiting my cock and filling her pussy, each shot feeling like a miniature orgasm unto itself for how long this had gone. My vision blurred, went dark even, but never once was I unaware of the pleasure in my cock as Rachel continued her slow, deliberate fuck. My breathing took on a rapid, husky tone, my heart beating a mile a minute. I didn't want to pass out, I shouldn't have passed out, not with all the risk that would entail.

Soon my vision was back, and I got to see the glorious sight of a triumphant Rachel McNeil looking down at me.

"Good?" she asked.

"Very," I replied.

"Good," she said, climbing off of me. My oversensitive cock falling from her tight pussy almost made me yelp, but I caught myself, focusing on the river of cum exiting her stretched pussy as a distraction. Rachel lay down next to me, her fingers already hard at work masturbating her cum soaked pussy.

"Well?" she groaned. "Are you gonna help, or aren't you?"

"I'm helping, I'm helping," I said, sliding next to her, getting back to suckling on one of her nipples and gliding my fingers over her sensitive skin while she touched herself. As much as I loved giving pleasure to women, there was a certain joy in watching someone masturbate, completely lost in their own pleasure as they touched themselves in a way only they truly understood. While Rachel may have looked utterly in control and confident only a moment ago, now she was lost in pleasure, her own eyes needy, her breath coming in ragged pants. I didn't interfere with her touching, only helping by stroking, sucking, grabbing her ass when needed, everything I could to help her reach her explosive third orgasm.

For how hard it hit her body, I was amazed that she was able to keep as quiet as she did.

"Thank you," she panted, her body still flush with the afterglow.

"No problem," I replied, licking one of her nipples playfully.

"No, seriously. Most guys don't seem to get that you often need a little help afterward," Rachel said, pulling my face up for a kiss. It was a nice, lingering kiss that I couldn't help feel held the same sadness, confusion, worry and joy as my own kiss, and one both of us knew couldn't last.

"Well, I'm not like other guys," I said.

Rachel rolled her eyes at me. "I can't believe you used the 'I'm not like other guys' line on me."

"Well, it's true, isn't it?"

"Yeah, but that doesn't make it any less cheesy," she said, pulling me in for another kiss.

Reality seemed to reenter the room a little bit at a time, the overpowering drive of lust taken by a more urgent understanding that what we'd done was, again, something that shouldn't have happened.

"We should, ummm, probably get dressed," I muttered.

"Yeah, we should, shouldn't we?" Rachel said, her fingers still trailing over the cum that coated her pussy lips. She played with the fluids, getting them on her fingers and stretching them out in strings, playing with them as if she were nervous or bored.

Sighing, she finally rolled onto her side away from me.

"You okay?" I asked.

"No. Pretty fucking far from okay, really," she said, still turned away from me.

For as nervous as I was for staying in this room, Rachel's tone kept me in place.

"What's wrong?"

"Everybody out there. I had fun with you, but it still doesn't change that they're all out there waiting for me to appear and fuck something up. Would that we could just hang out in here, screwing around all day without needing to worry about any of their shit, right?" Rachel said, a short, sad bark of a laugh punctuating the sentence like a gunshot.

I wanted to tell her that it wasn't that easy, that we weren't in a situation where we had the luxury of taking it easy, but with how much pain she was in I couldn't actually say those words. Hoping to calm her, I rolled into her so I spooned her from behind. When she didn't reject me, I put one arm around so I could hold her close, gently running my other hand through her hair.

Her contented sigh was a good sign.

"But we can't do that, can we?" she asked.

"No. We can't," I said.

"It's a nice dream, anyway," she said, with a slight chuckle.

"What's the laugh for?" I asked.

"Well, we could still have some fun, mess with the others a little if you'd like," Rachel said.

"How?" I asked, skeptical. Though Rachel was on a definite path to recovery from the bitch she used to be, that didn't mean I wasn't still on the lookout for trouble.

"See if there really is a betting pool with actual cash on the line about what happened to me back at school. I tell you what happened, you win the pool, we split the cash right down the middle," Rachel proposed.

It was an interesting proposition, even if there likely wasn't that much money on the line, though I was more interested in finally finding out what had happened to her. She'd been purposefully vague and mysterious about why she wasn't at school this month, and I'd be lying if I said I wasn't interested in finding out what had happened.

"Sounds like an interesting plan. You'll really tell me what happened?" I asked.

She shrugged against me. "There's not a lot to tell, but if you promise not to share it until we're ready to claim some cash, I'll tell you."

"Of course. If you want to share, I mean," I said.

"There's not much to share, really. It's a short, simple story where I didn't actually do anything that wrong for a change," Rachel said.

"Oh, now I really gotta hear it," I said.

She elbowed me in the stomach, not too hard, but enough to get her point across. I amended, "Sorry!"

"You know I don't have to tell the story," she said.

"No, seriously, I want to know."

"Really?"

"Really."

"Because this isn't easy to share." She said this somewhere between completely serious and a joke, and in response I dipped my fingers down into her pussy, massaging it gently. Rachel groaned appreciatively, especially when I kissed the back of her head.

"Please, share."

"Well, when you put it like that..." she purred, nuzzling back against me. "My roommate was having sex with one of our professors, standard college shit, but when she tried to break it off with him, the prof tried blackmailing her into a sex for grades thing."

I stopped rubbing her. "Asshole."

"That's what I called him," Rachel said, taking my hand in hers. I thought for a moment that she'd take me back to her pussy, but she just held on as if holding on to me were all that kept her on this world. "She didn't want to do anything because she didn't think there was anything she could do. I disagreed. So, I hacked his phone and brought the proof of his blackmail to the administration. The prof was fired and my roomie was free of him. However, the prof had enough friends around school to expel me, run my name through the mud and get my roommate to hate me. How's that for gratitude?"

"That's bullshit!" I exclaimed, stopping myself only when I heard my voice going too high.

"It is and it isn't. Hacking his phone was illegal as fuck, so in a lot of ways I'm really lucky all I got was expelled. And, it isn't all bad news," Rachel admitted.

"It's not?"

"No. My faculty advisor, she saw what I did and was impressed and sympathetic, pulled some strings with friends of hers to get me a job with a pretty bitchin' cybersecurity company up in Portland; I'm supposed to head on up next week. It's not much to start, but once I finish my online classes and get my degree, it'll be a pretty nice job. It's definitely something I can do," Rachel said.

I didn't know why this stung me as much as it did. That Rachel would be leaving definitely hurt, but probably would have been best overall. That all she did was try to save her friend and wound up having her life run through the mud for it?

"Why haven't you told your mom? Or Tori? Why don't they know what happened?" I asked.

"Because they wouldn't believe me. Mom, Dad, Tori, they got this image of me they can't change, and if I'm being honest, it's one I did everything to earn. I really do want to make things right by them, no matter how long it takes. I want them to know... I want them to know that I'm sorry. That I'm not just some fuckup anymore," she said.

"Well, you won me over, and a few weeks ago I hated you. They don't hate you, so you've already got a head start on them," I said.

"Yeah, thanks for that, I don't think I can get them the same way I got you," Rachel said, provocatively rubbing her ass against my cock, squeezing me with her cheeks. Despite the seriousness of the conversation, it was hard not to harden at her touch.

"You didn't win me over because you were hot. You won me over because you helped me when I needed help, even when I didn't know I needed it. Open yourself up to them, let them know that you'd be willing to do the same and then actually help them when they need it, and you might start repairing some of those bridges," I said.

"That... might actually work," Rachel admitted.

"Cool, because I was just making that up as I went along. I do think it'll work, though," I said.

Rachel laughed, this time for real. She squeezed my now fully hard cock with her ass again.

"Thanks for listening," Rachel said.

"Any time," I replied.

"But, you should totally use that answer to get in on and win the betting pool. I'll even make a good scene of the revelation, get some tearful indignation in there, maybe even raise my voice and air out some long-held family secrets if the opportunity arises. Standard impressively awkward Thanksgiving conversation," she said.

I laughed back. "I wouldn't miss that for the world."

She continued rubbing her ass against my cock. "Seems like there's something else you wouldn't want to miss, either. Still think we should get dressed in a hurry?"

We honestly should have, but she felt so damn good that my better sense was easy to ignore.

"I've got a quickie in me if you do," I said.

"I was hoping you'd say something like that," Rachel purred, parting her legs. She reached between and pulled my cock up to her pussy lips. They welcomed me warmly, our mutual juices making an easy, slick entrance into her pussy. It only took a single thrust to bury myself completely within her, my hand over her mouth the only thing keeping her quiet as I bottomed out.

In the weeks that followed, there came many occasions where I'd Monday morning quarterback this exact moment, trying to figure out if there was anything at all I could've done different that would've prevented the horrible ending I should've known to be inevitable. If I'd just stopped and gotten dressed, I'd have probably pissed of Rachel, but the rest of the heartbreak to follow could've been prevented. If I'd just kept my ears open, maybe we could've continued but avoided getting caught.

I dreamed of all of these outcomes, but nothing could change the fact that they were nothing more than fantasies that couldn't change the fact that I didn't stop, and I didn't listen. I was lost to fucking Rachel McNeil, our second coupling having all of the tenderness of our earlier sex yet with a greater urgency that made it easier to ignore the real world. The first time out she'd set a slow, deliberate pace, but now I was only powered by overwhelming want. I knew then that this would probably be the last time Rachel and I would ever have sex, and I didn't want to let her go without once properly fucking her. I pounded into her, giving her almost the entire length with each stroke, forcing her cries to go higher and higher as they disappeared into my hand.

In a comfortable position, my body pressed against hers, it was easy to just keep fucking her and lose all track of time. I mean, who'd want to keep track of time when they were with a tattooed goddess like her?

Maybe we were at it for a few minutes, maybe even half an hour, it's hard to say when memories of such things become hazy to time, but the rhythmic thumping of our bodies, the way my cock slid so easily and pleasurably into her pussy, her low soft groans matching my own grunts, I knew that she'd be cumming soon and that I meant to join her. I could time this right...

If I hadn't been so focused on this, I would've noticed the light knocking at the door, the sound of Tori's amused, hushed whisper as she checked to see if I was still in the bedroom and if she could join me for another shot of whiskey. Rachel and I were quiet enough that there was no way she could hear us, but that arguably might've made things worse.

"Cumming soon, cumming soon," I whispered. Rachel nodded at me emphatically, her whole body going rigid as her own orgasm stacked up.

"Fuck!" I grunted softly, thrusting into Rachel once, twice, three times before I came, my orgasm coinciding with her own shaking, shuddering cum. I hadn't had time to build up a proper load, but I still fired what felt like an impressive amount into her, leaving me, and her, collapsing drained onto the bed.

This would've been something close to a perfect moment if Tori hadn't exclaimed, "Fuck, Ryan! Did you just cum in my sister?"

If I were in worse shape, this would be the point in the story where you'd have read about me having a heart attack.

Tori stood in the room's doorway, no longer wearing her overalls but a rather nice set of jeans and a blouse she had to have borrowed from her mother that must've been her compromise for not wearing a dress in front of family. Her face was at once pale and wild, angry and disgusted and terrified. Her lips quivered, her mouth lolling open and closed as she tried to put words together.

Rachel and I were silent, our faces probably looking akin to those of deer caught in headlights.

This was about as close to a worst case scenario as we could get, I wagered, unaware that the worst case scenario was hiding just a few minutes away, waiting to explode.

Words found me slowly, even as my cock still lay buried in Tori's sister. "Tori, I-"

The sound of my voice snapped her out of it, forcing her to storm from the room.