Senior Year Memories Ch. 34

Now, I'd never put much thought to Jennifer's body before this moment, mostly because she did a good job of concealing it with those loose shirts and overalls. When she was grinding on top of me, I could definitely feel that she was a girl on the curvier, softer side than a lot of the girls I knew, but seeing her now I could finally take all of her in. Her thighs were on the slightly thicker side, and she had a little extra around the stomach, but when this also meant she had a beautifully thick ass and a pair of succulent-looking DDDs straining her tank top, unbound by a bra and with her firm nipples clearly poking through the fabric... well, when combined with her cute as can be face and huge smile, there was only one thing I could say.

"Wow."

Jennifer's blush escaped her face and flooded down into her upper chest. "I was hoping... I was hoping you would like it. I'm not as tiny as a lot of the girls you go with, but-"

"There's no but about it," I said, pulling down my sweatpants and dropping them to the floor. She looked down at my erection straining against my underwear and smiled at me. I took her hand and pulled her back to me. She straddled my lap once more, and without the roughness of her overalls between us, we really began to make out as she ground against me. With less between us now, I could feel her more distinctly against my cock, the way she insistently ground against me as she sought pleasure.

"You feel very nice against me... your cock..." Jennifer said, hissing through her teeth as she ground more urgently.

"You feel really good too," I said, kissing her, letting my hands drop to her magnificent ass and squeezing her. Jennifer let out long low moans as I did this, grinding with a greater need against me.

I looked into her eyes, trying to read her, but the way she was rubbing against me, I knew that she might cum soon if I didn't do something about it first. Don't get me wrong, I wanted her comfortable and I very much wanted her to cum, but while I was doing this at her speed, I still meant to help lead the way.

Carefully, I wrapped my arms around her and twisted her to the bed so that she landed on her back. Jennifer landed hard, giggling and looking up at me lustily as I was briefly above her.

I didn't stay there long, though, dropping so that I was lying on my side beside Jennifer, staring into her eyes as she looked into mine. There was a silent cloud of powerful lust between us, and watching her massive chest rise and fall under her tank top with each of her heavy breaths... it was truly a luscious sight.

It was also a sight I knew how to make even more exciting.

Slowly, I reached down and grabbed the hem of her tank top. I looked into Jennifer's eyes as I did this, searching for any sign of resistance, and when I found none, I began to pull it upward. I pulled it over her stomach, then up to the base of her massive tits, giving me a tantalizing view of the creamy expanse of her underboob. Finally hooking my fingers under the fabric, I pulled the tank top up over her breasts, bunching the tank top above her tits as I finally got a good look at them bare.

They were every bit as massive as I imagined beneath her top, full and soft, creamy and pale and topped with firm pink nipples. Surrounded by areolas the size of silver dollars and sticking out seemingly as hard as bullets, they just looked like they were begging to be sucked on.

Who was I to give up such an invitation?

I leaned down and took her right nipple into my mouth, slowly licking it over with my tongue before closing my lips around it, licking and suckling and doing everything I could to make this the best sucking I had ever done, because I wanted her first time to be memorable. The way her eyes first widened, then lidded over and her mouth dropped into a pleased O as I applied my talented mouth to her, I knew I had achieved what I set out to do.

"Oh, Ryan... oh, Ryan it feels so good, I've never... oh, wow! Please Ryan, keep going, it feels so good, it feels so amazing, Ryan!" Jennifer cried out, moaning loudly as I slipped over to her other nipple and gave it the same worshipful treatment.

I alternated between her amazing breasts for a good long while, enjoying pleasuring her while easing her in, but soon it felt the right time to begin pushing things forward. Gently, I began to graze my fingertips down her belly and toward the waistband of her panties. I was looking up into her eyes with a mouthful of tit the entire time, taking in her reactions, first as I reached her panties, then as I pressed my fingertips slightly beneath the waistband, gently grazing her trimmed pubes. I looked into her eyes questioningly as she silently took in my intent, her breathing ragged as her mouth stayed open in that pleased O.

Gently, I nibbled at her nipple, making Jennifer moan wantonly.

"Please, Ryan..." she whined.

I took my mouth from her nipple, wanting to hear her say it. "Please, what?"

Her face flush with lust, Jennifer dropped her voice and said, "Please touch me."

I smiled at her. "You got it."

I took her nipple back into my mouth, then pressed my hand under her panties. My fingers traced a path through her trimmed bush, until I found a moist warmth that might well have been wetter than I had ever felt a girl. Jennifer looked down at me, practically squealing with pleasure at my first tentative grazes of her outer lips, but sensing her need and wanting to deliver a pleasurable experience, I wasn't going to wait like this much longer.

I pressed two fingers into her steaming folds, tentatively exploring, looking up into her eyes to see what she liked and how she liked it as she looked down at me. Her moans guided me, her quickened breathing inspired me, and when I could see that I had pushed her to a place that she had not expected, I gently pressed my two fingers inside of her, twisting my hand oh so slightly for better purchase... and so I could thumb her clit.

Yeah, you could say that got her attention.

Jennifer's eyes flew open as I gave this attention to her pussy. "Oh my god, oh my god, RYAN!"

I smiled, letting her nipple go. "Good?"

"Just... don't stop, please, Ryan, please don't stop, please keep doing that..." she moaned in greatest desperation.

I was just being tentative, now, and already loving how it made her react; I couldn't wait to see what she was like when I found her g-spot. Which, with any luck, would only be a matter of seconds from now.

"HOLY FUCK, RYAN!"

Ah, there it was.

She might have been vocal before, but now she was simply loud, writhing and shuddering as I massaged her g-spot and clit simultaneously. I looked her straight in the eyes as I continued to do this, pushing her toward that edge. She'd already become quite experienced with her body, but I was going to show her how much fun it could be with a partner. Her juices soon coated my fingers as I continued to pleasure her, her breathing becoming quick and ragged as I brought her to the precipice.

"Do it... cum for me Jennifer... just let go, just let go and cum for me..." I grunted as I fingered her harder and harder.

She looked down at me, a look of uncertain desperation on her face as low, whimpering sounds of unbridled pleasure came from her mouth.

"Oh god, Ryan, you're gonna do it, you're gonna make me cum, please make me cum, Ryan, please, please, please, do it, please... RYAN, I'M CUMMING! GOD, YES, RYAN!" Jennifer cried out. Her body jerked violently against me as I massaged her sex, but I held her close, slowly yet forcefully coaxing her through her powerful orgasm. Her moans had long since lost all form and became something like a pleasurable wailing, though the moment it passed, she collapsed beside me. Breathing heavily, she looked down at me through half-lidded eyes.

"Oh... wow... wow, wow, wow..." Jennifer groaned.

Without taking my hand from beneath her panties, I leaned up and kissed her, enjoying her enthusiasm as she kissed me back.

"That was... that was amazing... thank you, Ryan," Jennifer said, kissing me again.

"It was my pleasure," I said, looking her up and down hungrily. "You are so wet."

She looked away from me, smiling and a little embarrassed. "I'm sorry, I kinda... gush, I guess."

"Nothing to be sorry for," I said, turning her face to mine and kissing her. "It tells me I'm doing a good job."

"I can tell you that. That was a very, *very* good job," Jennifer replied, blushing and looking at me dreamily.

"That was the first time. Just a warmup. The next ones will be even better," I said.

She laughed. "Even better? How could it get better than- OH GOD!"

I began to finger her again before she could finish her sentence, thinking that this was one of those moments where the "show, don't tell" principle applied. With her beside me like this, I fingered Jennifer through three more orgasms, each of them stronger than the last as I helped acclimate her to being with me. Between each of them, I would give her a moment to catch her breath, only just, before moving into the next one, and by the time we were finished, you would have thought the world was ending for the way she was screaming.

She was right about being a gusher, though; by the time I had finished giving her her fourth orgasm, Jennifer's juices covered my hand and soaked through both her panties and left a good-sized wet spot on my sheets. She soon put her hands on my shoulders, gently pushing me away.

"No more... please, no more, I need... holy fuck... I need a moment, Ryan... fuck that's so good, that was amazing..." Jennifer breathed, kissing me messily. It seemed as if every inch of her pale, smooth skin was now flush with pink and lightly sheened with sweat, a look that I had to say was certainly becoming for her.

I pulled my hand from under her panties and licked her juices, finding her to taste quite sweet.

When she looked at me curiously, I asked, "You want some?"

"I've... never done that before," Jennifer admitted.

"Well, today is a day for doing things you've never done before, isn't it?" I said.

She smirked. "You know what, you're right."

Jennifer took my hand in hers and brought it to her lips, tentatively swiping at it with her tongue. Once she got her first taste of her juices, I saw her eyes open slightly with surprise, and she began to lick more enthusiastically.

"That's really tasty!" Jennifer giggled. "*I'm* really tasty!"

"You are. One of the many reasons I love eating pussy," I admitted.

She laughed. "Please, give me a little while before you do that..."

"No problem," I said. I sat up and pulled off my shirt, enjoying her appreciative eying of my modestly muscled frame.

Jennifer reached up, running her hand over my lean muscles and groaning, softly. "So nice..."

I smiled. "I got something nicer than that."

With that, I arched my back and pulled off my underwear, leaving me naked on the bed beside her. Jennifer's eyes went wide as she took in all ten inches of my thick cock, head already beading with precum.

Jennifer whispered, "Holy..."

"Do you want to touch it?" I asked.

Silently, Jennifer nodded. I took her hand in mine, guiding it toward my cock. I wrapped her fingers around the head gently.

"Now, you want to stroke me firmly and gently; I'll let you know if it's too much or not enough. Try spreading the precum around evenly, and don't forget to give attention to the head, that's where it's most sensitive," I said.

"I understand," she agreed, slowly stroking me. It was a tentative gesture as she got used to the feel of my cock and precum, but it didn't take her long to start spreading it up and down the length of my cock. When I began to groan pleasurably when she would gently rub her thumb over the head, she would do this more vigorously, picking up her pace as she jerked me off. I didn't have to instruct her much, sometimes telling her to slow down or that she was squeezing too hard, but she adjusted easily to my instructions and gave a pretty solid handjob.

Soon Jennifer was feeling bold, jacking me more energetically, even reaching over with her other hand to gently play with my balls. While she was hardly an expert, she was learning fast, and I was feeling pretty good. If this kept up much longer, she would have had me cumming in no time.

"Okay, okay, that's good... you can stop now..." I said.

Jennifer whined a little, almost as if she were upset that a new toy was being taken away, but while she stopped jacking me, she did continue to gently hold onto my cock.

I looked down at her with lust and great need, leaning down and kissing her.

"Fuck, you're beautiful," I said.

Jennifer blushed. "Thank you."

Licking my lips nervously, I asked, "Are you... ready?"

Her eyes went wide on catching my meaning, but soon she quickly leaned up and kissed me. "Yes. I am."

Silently, I smiled, kneeling next to her and peeling her soaked panties down her legs and tossing them aside. For her part, Jennifer nervously removed her tank top until she too was naked. I spread her legs and crawled between them, kissing my way up her thighs, planting a firm kiss on her clitoris that drove her wild, before kissing my way up her stomach, to her breasts and to her neck. My cock rested against her inner thigh, throbbing and waiting, needing her.

Jennifer looked up at me with this look between great longing and fear, but her breathing hadn't changed much since the lustiest moments of when I fingered her to orgasm.

Still, I wasn't going to take this next step without her.

"I'll need your help guiding me in," I said, smiling sheepishly.

Nervously, Jennifer nodded again, reaching down and taking hold of my cock. Her hand was shaking, but she took me firmly in hand, running the head against her clit for a moment before pressing me against her folds. Her entrance felt quite tight, and for all the training she had done, I knew this would take some effort.

Nonetheless, I pushed forward and began to penetrate her.

Jennifer looked down as my cock began to slowly press inside of her. "Oh, wow, Ryan, wow... keep doing that Ryan, keep doing that, please, keep doing that, get inside me, please, fuck me, get inside of me, do it, do it, do it, fuck me, please, fuck me... fuck me, do it, do it, do it..."

Then, almost all at once, I felt her muscles invite me in, as the head and first few inches of my cock entered Jennifer Cage's virgin pussy.

Her eyes popped open and her mouth dropped into a familiar O shape briefly at this invasion, but soon after she said two words so quietly I think they barely counted as a whisper.

"Oh god."

My lips found hers as I pushed deeper into her impossibly tight cunt. Jennifer moaned against me as I continued to press into her, sliding inch after inch into her at an agonizing pace. Thank god she was as wet as she was, because at this tightness I might not have been able to enter her otherwise. Nonetheless, she was inviting, urging me forward with her soft words and clutching pussy muscles. Soon more than half of my cock was in her, then three quarters.

Then I was all the way inside of her, my balls resting against her ass.

"Oh my god, Ryan!" Jennifer exclaimed, looking down the valley of her cleavage to her pussy being obscenely penetrated by my cock. "Holy fuck... holy fuck, wow..."

I smiled down at her, kissing her. "Not so bad, right?"

She kissed me back. "This is... this is a lot... but so good... fantastic!"

Briefly, my eyes drifted to the bedside table, and seeing her phone on it I was struck by an inspiration.

I grabbed the phone, handing it to her. "Can you unlock this?"

Jennifer did, and though she was a little confused, it didn't seem like she was in the mood to turn down much of anything as she handed the phone back to me. "Why?"

I was taken to a time that now felt so long ago that felt very familiar all of a sudden. It had been in this bed, with me in Jennifer's position, and I couldn't not embrace the moment for all it was worth. Now if only I could remember all that was said...

Kaitlyn's words came to me, but now in my own voice. "I thought a picture would be best to commemorate such an important occasion."

I angled the camera down and took a picture of my cock in her pussy, making sure I got just the right angle, just the right shot for her to remember this by, before putting the phone aside.

"Some things..." I grunted, slowly sliding out and thrusting back inside of her, "...you want to remember."

Jennifer groaned as I began to slowly fuck in and out of her. "I've got a pretty good memory..."

"So do I, but the more adventures you have, the more jumbled they can get," I responded, continuing my achingly slow fuck. "Pictures, they can help make sure things don't get confused."

"Good to..." she whimpered, eyes rolling back as I thrust back home inside of her. "...good to knoOOOOOOOOOOOOOW!"

I pumped in and out of her slightly faster, wanting to make this fuck last, but she felt so good I couldn't help but quicken my pace. Her body against mine, her eagerness, the way she looked up at me with such pride and need... it drove me wild. She may have had a lot to learn, but I was more than happy to help her on her way.

"It's so good... so fucking good, Ryan... keep fucking me, please keep fucking me..." Jennifer moaned, wrapping her arms around me and holding me close.

"I couldn't stop if I tried... you're so fucking hot, you feel so good... we're going to have fun, you and I..." I said.

"Yeah? You want to keep doing this?" she asked, moaning and looking up at me with some doubt. "You want to keep doing this with me?"

"God, yes..." I groaned, leaning down to kiss her. "You're fucking amazing, of course I want to keep doing this with you..."

"Good, fuuuuuuuck," Jennifer groaned, kissing me long and deep as I increased the pace of our fuck slightly. "Because... none of this changes what I wanted... I want it more, now... I want to do everything, to feel everything, to know everything..."

I reached a hand up to squeeze her tits while I fucked into her, giving her something new to squeal about. I couldn't stop looking down at her, taking in her first time as it happened. I could see her grimacing sometimes, getting used to the size of my cock, but she never asked me to stop, and when I slowed down to make sure I wasn't hurting her, she would only push me to go faster again. Her pussy gripped me like a vise, squeezing and massaging my cock tightly as I thrust in and out of her. It felt amazing, and was nearly enough to push me over the edge.

It was, actually, getting me quite close.

"I'm... I'm getting ready to cum... feels so good," I said.

"Gooooood," she groaned with pride. "That's... that's very good..."

"Where do you want it?" I asked, thrusting into her slightly faster.

"You can cum wherever... cum in me... I want to know what that feels like... I want to feel your cum, Ryan..." Jennifer said.

Alright, that was one question answered, but I had another important one that needed addressing immediately.

"How are you? Are you close to cumming?" I asked, grunting and thrusting into her slightly harder.

She looked up at me, almost a little embarrassed. "It's... I'm not there yet, I'm sorry. It feels so good, but-"

I kissed her. "There's nothing to be sorry for, penetration alone doesn't do it for a lot of girls. Why don't you try reaching down and playing with your clit? A lot of girls I know have done that."

Jennifer groaned, then looked at me uncertainly. "That's not a problem?"

"You not getting off would be a problem," I said with a smile, kissing her passionately again. "Go on, touch yourself... cum for me and make me cum... do it..."

This low, grunted command spurred her into action, and with both hands, Jennifer reached down between her legs to finger her clit. Her eyes went wider and her breathing got much more ragged as she did this, and I could tell the suggestion was quite welcomed. Her moans became louder, her eyes more fluttery and her mouth taking on that telltale O-shape that she seemed to favor when losing control. I still wasn't fucking her nearly as hard as I would many other girls I knew, but I increased my pace to help both of us build toward our orgasms.