Senior Year Memories Ch. 34

"Oh my god... Ryan, I can feel it, I can feel it, it's coming..." Jennifer moaned.

"Gonna cum?" I asked.

Whimpering, she nodded. My own orgasm was on the precipice and desperately in need of release, and I began to fuck her even harder.

"Just let it happen, let the dam break... fuck you feel so good... cum for me... you cum for me and you'll make me cum... do it... cum for me..." I groaned.

"It's happening... oh god, I can feel it, I'm gonna cum, Ryan! I'm cumming, I'm cumming, Ryan, I'M CUMMING!" Jennifer cried out, her voice rising to a scream. Her body jolted against mine as the most powerful orgasm yet overtook her, her arms closing around me tightly as she held me close, every inch of her shaking and shuddering uncontrollably from the pleasure of it.

I didn't hold back any longer, especially with her pussy squeezing me so tightly it threatened to push me out of her. I buried my thick cock deep within her spasming cunt and unleashed, moaning loudly as pleasure overtook my senses. I pumped a massive load of cum deep inside of her, each shot threatening to flood her tight cunt. Jennifer took it well, moaning well after her orgasm had subsided as her pussy milked every last drop from my cock.

Finally, as both of us came down from our orgasms, I leaned in and kissed her. It was a slow, passionate kiss, one that she returned in kind. We broke it soon, holding each other and panting, but soon continued kissing. These were light, brief kisses, sharing a distinct intimacy that I couldn't deny as we looked into each other's eyes.

"Thank you," Jennifer said, looking up at me dreamily.

"You're welcome," I replied. As I could feel myself softening, I kissed her one final time and pulled out. A torrent of our juices poured out of her and onto my sheets. Once I might have been annoyed by this, but since this year had begun, I'd become quite accustomed to regularly cleaning my bedding.

I lay down beside her, still catching my breath, while she rolled onto her side so she could drape an arm and leg over me and better look at me.

"So, as first times go, how would you say this went?" I asked.

Jennifer laughed. "You know, it's pretty hard to compare it to anything, since you only get to lose your virginity once and all that... but I have to say, that was pretty fucking amazing."

It was interesting seeing her after a few hard cums. She had almost none of the nervousness or meekness that I would have generally associated with Jennifer Cage. Being nice and pleasantly cum drunk suited her well, and for the broadness of the smile on her pretty face, I could tell she rather well agreed with this sentiment too.

Looking down at herself, Jennifer gingerly toyed with her pussy, scooping up some of my cum experimentally. "Wow, you really cum a lot."

"Yeah... I've been told this," I said.

Smiling a little sheepishly, she looked around my room and said, "Can I use your bathroom real quick? I'd like to get a little cleaned up before we really jump into any more."

I grinned back at her. She was interested in doing more; it was very promising to see that she hadn't been scared off by anything.

"Go for it. I've got two girlfriends, so, it's pretty well-stocked with whatever you might need," I said.

"Thanks!" Jennifer said, climbing off of me and walking into my bathroom. There was a little extra confidence and sway in her step as she walked completely and utterly naked into my bathroom, and the way our mixed juices dripped down her inner thighs... well, that certainly started to bring life back to my cock again.

As she closed the door behind her, I rolled over to pick up my phone and saw that I had a new text.

Josie: How's the slut lessons going? She a good student?

I laughed at Josie's forwardness and responded.

Me: Everything so far so good here. She was nervous, but she's having a good time. I am too. She's nice, and hot.

Josie: Cool. Let us know if you want to make an introduction, Brooke and Alice think she's cute too, could be fun.

Me: We'll see. Want to ease her into things. But she's curious.

Josie: Good to know ;)

I sighed, contentedly holding my phone. Feeling nostalgic, I opened up my Senior Year Memories album and scrolled through the pictures, and found myself most taken at the moment by both my oldest and most recent pictures. I looked at Leah and Kaitlyn for a moment, and if Jennifer was going to take a moment, I thought I had the time to shoot out a couple more quick texts.

To Leah, I sent:

Me: Lust spell's working pretty well on my end I think. Hoping you're seeing some great results too :)

I thought a while longer about what I wanted to send to Kaitlyn. The two of us hadn't had a lot of heart to heart time to talk lately, but I was feeling a particular need to touch base with her. I agonized about the exact wording, but finally settled on winging it and hoping for the best.

Me: I don't know if I've said this enough, Kaitlyn, but thank you for starting me on this crazy year. I wouldn't have been able to do any of this without you, and I don't think I can ever repay you for that.

Suddenly feeling a little nervous myself at how Kaitlyn might respond to that, I set the phone down just as I heard Jennifer's hand on the bathroom doorknob. She wobbled back into the bedroom a little giggly, looking at me with playful eyes.

"I just had sex!" she declared proudly.

I laughed. "I know, I was there."

"I just couldn't stop looking at myself in the mirror..." Jennifer said. "Because I still look the same, but I don't feel the same, because now, I've had sex."

"Feels good, doesn't it?" I asked.

"Hell yeah," she said. "And I think I even look better too. I don't know if that's possible, because I'm still me, and I haven't really changed, but it's a change... do you mind the glasses and the ponytail? Should I ditch them?"

"You wear whatever's comfortable for you, that's all I care about," I said.

Jennifer beamed at me. "Cool! I think I've watched too many movies where they make a woman hot by removing her glasses and ponytail, keeps putting these stupid questions in my head about what I should and shouldn't be doing, and-"

She tried to take a step and wobbled against the bathroom doorframe, giggling.

"Walking is... difficult," Jennifer said. I got up and took her in my arms, helping her to lie down on the bed before joining her.

"That part gets easier with time," I said. "I mean, I've never done it from your side precisely, and I still get wobbly after some good, solid sex, but it does get easier."

"Good, because I want to have a lot more, and I don't want to feel so messed up from it *every* time," Jennifer said.

I laughed. "I think sex always messes us up a little bit, makes us a little cum drunk, but that's where a lot of the fun comes from. If it's not driving you a little crazy, it's not worth it."

"That an official lesson?" Jennifer asked, leaning in to kiss me.

"Not... not really. You're going to hear a lot about sex from a lot of people, some of it's right, some of it's not, the real challenge is figuring out what works for you. Just keep an open mind, your self-confidence and your self-respect intact, and you'll figure out what works best for you," I said.

Her smile fell slightly, but not completely. "I can see the need for that. My mom... she didn't have the best experiences with guys. My dad left us when I was really little, and the guys she got with since weren't the best for her. I think it kind of warped how she viewed sex, and what she would teach me about it, like she thinks she can make me into a different person from her if she makes me more scared. I'm sorry if it's a problem in anything we do, the way she fucked with my head, but I'm really trying to not let her inform everything. Really. I'm trying to do this for me, and I'm gonna keep trying this for me, but it's going to have its rough spots, I know, and-"

I kissed her. "You did pretty well already."

"Yeah?" Jennifer asked, clearly less because she didn't believe me and more because she needed validation. That was something I was happy to provide.

"Yeah," I confirmed.

She groaned contentedly, melting against me as we made out for a moment. It felt good to press our bodies against one another, our hands gently exploring as we enjoyed the afterglow of some quality sex and the promise of more to come.

Jennifer sighed. "I wish you had some toys."

Raising an eyebrow, I asked, "Oh? Why?"

A little embarrassed, she blushed. "It's nothing, sorry, forget I said anything."

"But you did say something, about something you wanted, and I want to hear it," I said.

Still looking a little sheepish, Jennifer said, "It's... just a whim. I didn't want to say that you weren't awesome or anything, because what we did was awesome, it felt *so* fucking good, but..."

"But what?" I asked, prodding her, hoping I'd be able to better help her communicate her wants.

Jennifer looked at me, biting her lip in consideration for a brief moment before looking up at me with her big brown eyes and saying, "At home, I have a few toys I keep stashed in this small box under my bed. I had to sneak out to get them, but I've made good use of them... and one of them is..."

She trailed off, her voice going very quiet again as she had a difficult time expressing what she needed to express.

"What is it?" I asked, reaching for her and gently squeezing one of her nipples.

Jennifer moaned, closing her eyes and finishing, "...a butt plug."

"A butt plug..." I said, curiously letting the words roll off my tongue.

"Yes..." she admitted, sheepish. "I was nervous to use it at first, I wasn't sure what it would feel like and anal always looked so intense in the videos I've watched, but I gave it a try, and when I did, it was such... wow, it made me cum harder than anything else. I was just wondering what it would be like doing some of the things we've done with one of those."

I thought about this for a moment before politely disentangling myself from Jennifer. "You say you keep your toys in a small box beneath your bed?"

"Yeah?" Jennifer asked, curiously looking at me as I reached beneath the bed.

I grabbed the large box from beneath my bed and pulled it out, dropping it onto the bed at her feet. "Then you should really get a load of *my* toybox."

Jennifer sat up and looked at the large plastic tub I kept beneath the bed. I grinned at her curiosity and opened it up, revealing my impressive collection of dildos, vibrators, bondage gear and other toys I had accumulated.

I explained as I rooted through the box, "For Christmas this year, a bunch of my friends got together and got me one hell of a collection of sex toys. I got a lot of good stuff in here, but it was Josie who got me..."

I grabbed a selection of the toys I was looking for and spread them out at the top of the box for Jennifer to better see. "...a truly epic collection of butt plugs."

Jennifer's eyes went wide as she leaned in over the box and took in the collection of toys.

"Wow," she said.

"Good stuff, right?" I asked.

"That's... one way of putting it," she replied, shifting around uncomfortably on the bed as she took in the collection. "And all of these... fit?"

I laughed, picking up the biggest of the plugs. "They're meant to fit, but whether they actually can I think is up for debate. Brooke and Josie are really into filling their asses, but even they can't fit the biggest of the collection here. Brooke got really close, but even she couldn't fit it."

"I can imagine that being a problem," Jennifer said, her eyes wide as she reached out and touched the big plug I was holding. I saw her shiver slightly at the contact, her eyes fluttering, but she soon withdrew.

No, no matter how much experience she might have had with her own plugs, this was something she knew better than to get too adventurous with right away.

Briefly, she sorted through the box before finding a medium-sized black rubber plug that seemed to catch her interest. For her level of experience, it was a little bigger than I would have expected.

"That's the one you want?" I asked.

"Uh huh," she nodded, smiling brightly.

"You sure? I mean, that one's not exactly small," I said.

"It's only slightly bigger than the one I have back at home. I think I can take it, if you have enough lubrication, that is," Jennifer said.

I shifted the contents of my toybox to reveal the Costco-sized container of KY Jelly that Nadia had gotten me for Christmas. While I had gone through some of it already, there was quite a bit to go.

"Ah, wow, yes, that is a lot of lube," Jennifer said.

"It's come in handy," I said, grinning. "So..."

She licked her lips, nodding. "Yeah. Yeah, I'd like to do this."

I kissed her. "Cool."

Jennifer asked, "So, how should I do this? I mean, I've done it before, but it gets a bit awkward, and I don't want to mess anything up..."

I said, "It's not that hard. Getting on your knees is a good start; I've been with some girls who had the easiest time going face-down, ass up, but however you feel most comfortable, I'm good for."

"Face down, ass up sounds good," Jennifer said, enthusiastic. She smiled at me sweetly, leaning in for a quick kiss before turning around and getting up on her knees. She bent down toward the head of the bed, resting her head on her arms as she stuck her delicious-looking, round ass out towards me.

I looked at her ass for a good, long moment, taking in her soft curves and the view this angle gave of both her inviting pussy and sweet, pink asshole between her cheeks. With the plug in my hand and the lube not far away, I knew what I should have done, but she just looked so inviting...

I leaned in, kissing her asshole, running my tongue around her puckered bud. Jennifer first yelped at the unexpected attention, but then groaned.

"Oh... that feels sooooo goooood, Ryan..." she moaned.

I could have done this for a while, given her a truly intense rimming, but I wasn't going to deny her need to be filled by the plug. Well, not for long anyway. I did stay there a little bit longer, kissing and licking and probing her asshole with my tongue before leaning back, giving her a kiss on one of her glorious, round cheeks, then finally doing what I'd set out to do with the plug.

Squeezing a generous amount of lube on the conical plug, I made sure to get it nice and slippery before lining it up with her tightest hole.

"I'm not going to lie, this is going to be fun, but will also get pretty intense once we get to the end," I said.

Jennifer looked back at me, smiling. "I've had a butt plug in me before, Ryan."

Smiling, I pushed it forward, sliding the toy into her ass a little bit at a time. "I just wanted to be sure you knew what you were getting into. Or, more appropriately, what's getting into you."

She hissed, dropping her head to the bed and moaning. "Oh, fuck, that feels so good..."

"Only got about an inch in... let's see if you can fit more," I said, pushing it deeper into her asshole.

Jennifer moaned and hissed, looking back at me as I pressed more and more of the plug into her ass. She quieted as her asshole stretched to accommodate the toy, and by the time I'd nearly reached its widest point, she was whimpering from equal parts pleasure and pain. Nonetheless, I kept slowly but firmly pushing it inside of her until her hole took the widest point, and the toy settled deliciously inside of her.

"Fuuuuuuuuuuuuuuuuck..." Jennifer groaned. "I'm so full..."

"That's a good thing?" I asked.

"Very," she replied.

"Good," I said, playfully grabbing her by the hips and rolling her over onto her back. It took her by surprise, and with some adjustment at the toy inside of her, but as she looked up at me with her big eyes and pretty smile and utterly inviting body... I felt rather inspired.

"I'm going to eat your pussy now," I said.

Jennifer shivered, her luscious body breaking out in goosebumps as I saw a flush of arousal pass through her.

"Good," she said, simply.

Licking my lips, I crawled between her legs until my face was only inches away from her pussy. I looked up at her through the valley of her cleavage in anticipation, first at pleasuring her and inviting her into this world of beautiful carnality, and secondly because her pussy looked fucking delicious.

I probably should have eased her in, teasing and exploring her engorged, dripping folds, but I needed to taste her properly, and after the fingering I'd already given her, I thought we were well past the point of teasing.

So, I dove in, licking and suckling at her pussy, worshipping her clit while my fingers and tongue gave the rest of her pussy all due attention. Between this, and the plug in her ass, Jennifer had taken on a bit of a different tone than before.

"HOLY SHIT, FUCK!" she cried out, her hands finding my hair and forcing me into her pussy. "Keep doing that, Ryan, holy fuck! Holy shit, Ryan, I can't... that's amazing, that's, wow, fuck, fucking wow, so good, fucking shit, do it, fuck, keep doing that, fuck... motherfucker! Keep it up, do it, do it! Keep eating my fucking pussy, Ryan!"

I didn't need the command to continue doing this, but I welcomed it. Seeing her become less shy the hornier she got was a delightful development, as I knew well how to help Jennifer along that path. I didn't know quite the course we would be taking with her as my apprentice, but I was willing to find out if it meant we did a lot more of this.

I curled my fingers inside of her in that way that worked so well, focusing my lips and tongue on her clit as I rediscovered her G-spot and set her off once more. She was louder than before, her body jolting as if she were struck by lightning. Her wonderfully thick thighs clamped down around my head and neck so hard I thought I might be in trouble for a moment, but that didn't stop me from the worshipful treatment of her pussy as she gushed all over my face.

When she loosened her grip on me, Jennifer gently pushed me away.

"That was... amazing... but if you lick me anymore, I feel like I might pass out..." Jennifer gasped.

I smiled. "So, you never want me to eat your pussy again?"

"NO!" she shouted. "I'd never say that, just... give me some time now..."

"You got it," I said, crawling up beside her and kissing her. "I just wanted to make sure, because you taste really good."

Licking some of her juices from my face, Jennifer said, "I know. Do all girls taste this good?"

I shrugged. "I've heard it varies, but I've generally had good experiences. You do taste exceptionally good, I will say that."

"Thanks. I really do, don't I?" she said, licking more of her from my face and kissing me deeply.

Seeing where her curiosity was leading, I asked, "So... you might be into girls too?"

Jennifer scrunched up her face, uncertainly. "I *think* so? I mean, I've always thought girls were really pretty, and I've gotten off to a lot of girl-girl porn recently too, so I think so? But, I don't know... I'm just discovering how much I really like cock, and I don't know where that puts me. Why?"

I held her close, stroking her side with my fingertips. "I'm not judging or anything, I was just curious, because if you want to find out, I can make some introductions to some girls who'd be more than happy to help you find out."

Her eyes brightened. "You mean it?"

"Of course I do," I said. "In fact, Josie and Brooke are over at Alice's house next door. I'd be happy to introduce you to the three of them later if you want, see if that does anything for you."

Jennifer looked toward the curtain-covered window, thoughtful. "They *are* pretty. Sure. Yes, let's do that. Maybe. I think. I'm pretty sure?"

"Good. They're really nice," I said. I wanted to say that the three of them were also pretty insatiable and would fuck nearly anything that moved given the right circumstances, but I didn't want to scare Jennifer off or anything.