It Barely Fit

Author's Preface: All the characters/participants in this story are eighteen years old or older.

We both had limited experience and Valerie was my first...my first on many levels. The relationship had that usual progression of tentative advances...stolen kisses...steamy make-out sessions...groping...second base...a hand in the panties or third base...that kind of thing.

We actually met in high school, since we were both on the track team; Valerie was tomboyish, very cute, with blond, curly hair. I remember we would sometimes talk after meets, but nothing ever transpired because we were both so shy and awkward.

Then college happened...and she was doing two years at junior college, while I headed off to Champaign-Urbana. It was only ninety miles, but sometimes it seemed like an ocean. She chose the junior college route because she got an athletic scholarship; she was a great asset to their program.

We'd talked a few times after she broke up with Jason; I think it was in November, when she got the nerve to invite me to one of her practices. I was struck by how she looked that day; she was definitely feminine, but her whole body was toned and built for speed. Her ass looked amazing in running shorts and, more than once, I admired her perky breasts. They weren't huge and fuckable, but they were definitely suck-able...wet dream fodder. Even with a sports bra, they had that mesmerizing bounce and jiggle. I know it sounds pathetic, but I was horny college guy; I couldn't take my eyes off her tits, especially when she was digging in...or doing hurdles.

After that, I went home to visit a couple times, and we spent a few hot nights, groping and making out in the car...first a handjob...then a blowjob...then another. Whether it was from a curious grope or a handjob, she seemed infatuated after those first encounters. I distinctly remember the first handjob, where she undid my belt, and I unzipped my pants, eagerly helping her to push them down with the underwear. I'm a little surprised I even noticed, but her eyes got big, and she had this awkward grin, "Holy shit, Rob...that's...that's a lot bigger than Jason!"

Then she nodded, "Yep, I got a way better deal...a bigger and better deal!" She giggled, "I could've guessed that, though, because you have big feet...you know what they say 'bout guys with big feet?"

Jason was one of my best friends in high school and in college; we both ended up in Champaign...we were pretty close. Anyway, her remark fell in line with something I remembered him saying, "We barely got past a blowjob...we did it once, but I think she was looking for something more." He shrugged, "Women...I don't know."

Jason had been on the track team, too, but he was a lot more athletic...he was even a star running back in high school. Anyway, after he started college, he grew more interested in this hippy chick that liked to hang out at this club. I stepped in when he broke up with Valerie...it could've been awkward, but he wanted to move on, and even encouraged me to call her.

I was only the second guy she had really been with, but when she found I was bigger, she seemed all curious and turned on. If she was turned-on by something bigger...I was fine with that.

She smiled awkwardly, "Can I...can I touch it?"

I anxiously nodded, pushing it forward, "Please...yeah...yeah, you can touch it!"

She wrapped her fingers around it, and smiled when the fingers wouldn't meet, "Wow...this is fun...you're shaped like a big banana!"

That dainty hand was all my cock needed, swelling and pulsing in her grasp. I watched her explore it, trailing her fingers over the shaft, but then she started stroking it, grinning, "Let's just see what this guy can do."

"Does that feel good?"

I nodded, and she added a second hand...it felt amazing, and I could tell she was into it, as much as I was. I settled back into the seat, watching every move she made. She pulled one hand away and started stroking faster. I was crazy horny, and it didn't take long, before I felt it coming.

My body was tensing up and I moaned, "Ahhhh...ahhhh...I...I'm gonna cum...ahhhh...ahhhh!"

I was out of my mind and thrusting my dick through her hand; I grunted, as a thick stream exploded from the tip and landed on my shirt. She squealed as more pulsed out and drizzled down over her hand.

Smiling, she looked up into my eyes, licking it from her hand, "Mmmm...you needed that didn't you?"

I just nodded, and grinned, but that handjob was one of many; along with a few blowjobs and a few steamy, finger fucks, we became very familiar with each other's needs. I know we both wanted more, but that was what we could do...it was where we were at...you know?

A week or so later, I remember it was the first time meeting her parents and she was wearing a skimpy dress that made my encounter with her mom and dad extremely uncomfortable. We got through dinner just fine, but only lasted a half hour or so into the movie. It was long enough to get through the previews and the popcorn, before we headed back to the car, for more pressing needs.

She ran her hands all over my cock, looking almost hungry. She savored the soft, almost silky skin, covering the shaft, trailed her fingers over the wrinkly, stretched sac and caressed the thick, spongy head.

When she saw the first clear bead, she looked into my eyes and licked it from the tip, probing with her tongue. I remember moaning something like, "There's way more where that came from...but I guess you know that."

She nodded and took it into her mouth, swirling her tongue all over the head, tracing the ridge and savoring its pulsing girth.

She was exuberant, and excited to explore, with her lips, her tongue and her eyes. It was like the best cock she'd ever seen. You could see it in her face, when her eyes rolled back; she yearned to take it all, filling her mouth with as much as she could get.

Her efforts quickly overwhelmed my senses, and I dug my fingers into her curls, encouraging her to take it deeper. Looking back, it seemed crazy because I remembered her giving her mom and dad a little peck on the cheek before we headed out...and now those same lips were wrapped around my dick...and doing crazy, nasty things to me.

"Ohhhh...Val...rie...that feels so good...yeah...yeah...yeahhhhh!"

It was always amazing to have my dick in her mouth, because she always seemed to want what I wanted. She bobbed her lips up and down my dick and I shuddered, knowing I was close. I tried to push things back, but I knew that wasn't working, and groaned, "I'm close, Val...you want...you want me to cum'n...cum'n your mouth?"

That's when I felt her lips tighten, and I let it go; it was a big load, and she swallowed every last drop. It's more than sexy when she swallowed it, but she loved having you fill her mouth...and flood her tongue. I couldn't help but think Jason was a dumbass for letting her go, but I was walking on air, with a big ass grin.

It's like she knew what I was thinking, and I remember she looked up, "You know...he was half as big...you have a man's dick!" She giggled, "I guess I've moved up from a boy's dick to a man's dick!"

That was pretty brutal, but it made me feel confident and manly...she knew what she wanted, and what she needed.

I felt good about things, and thought everything was headed in the right direction, but it made me crazy, too. All I could think about was spreading her legs and fucking her brains out. Having my way with her, was the goal was, but looking back, I was witnessing the birth of a size queen, before I even knew what that was about.

************************************************************

Our first try was at her house. Her parents were gone for the weekend, and we were out on the deck. It was a beautiful night with a warm autumn breeze. Sitting in my lap and buck naked, with her legs tight around my waist, Valerie was definitely committed to home plate...we were both ready. I remember we were all hot and horny, making out like a scene from a movie...my dick was rock hard, upright and pressing against her ass.

I got the condom on...I had practiced at home, because I knew I'd be nervous as hell. When I tried to push inside and she squealed, "Stop...it's toooooo...bigggggg...so big!" I stopped and apologized, but anxiously tried again. I got it wedged between her pussy lips, but the condom tore, and she squealed again, "Ohhhhhhhhh...that's big...it stings...take it back out!"

I went to put on another condom, but it tore, before I got the damn thing on. I had to look frustrated, because I was...I even practiced putting on the damned condoms...but I remember Valerie looking super disappointed, "Do you have any left?"

"Three," reaching for my pants, and holding them up, "I got three more!"

She got the sexiest smile, "Let's try again!"

I was super careful, rolling it on, down over the shaft; I got about as far as before but it still wouldn't fit...and she looked at me, "This's not working, Rob...I'm too tight...and you're big...I'm sorry...I'm so sorry."

Not knowing what to say, I apologized, too, "Sorry...I didn't hurt you...did I?"

She was almost in tears, but I think that inspired tenacity and she shook her head, "You didn't cause any damage...you're just bigger, and it's really tight, down there." Then she grinned, "I just need practice...we just need practice...you know?"

I was more than willing to practice and anxiously nodded, but then she looked down, "Wow...you're so horny, and you came with five condoms...let me make it up to you?"

That night, I got an amazing blowjob and vividly recall that lusty look...or cock-lust...it was just like Jason described, but I was determined to go beyond the blowjob stage. Her tongue swirled over the ridge, up over the very tip and then down the shaft, going all the way to my balls. She took my load, as usual, and it didn't take very long...I was so fuckin' horny.

I remember feeling indebted and emotional, saying, "This's been frustrating for both of us...you need one, too." Not completely confident, I asked, "Do you want me to finger you?" But then I threw it out there, "or maybe lick you, down there?"

She was more than eager, when I shoved my face between her legs and started eating her out...she was the first for that, too. It was a little awkward but, with a little coaching, I got her what she needed, and learned the finer points of Eating Pussy 101.

It was wet, and I couldn't resist the urge to push my tongue inside. Savoring the taste of arousal, I slurped and pumped my tongue deeper, into the tiny gap.

As I probed and licked her out, she was clearly enjoying it, moaning louder and louder; sort of grunting, she directed me to go higher up, "Do my clit."

Yeah, that was the spot...it was the spot that always made her shudder and moan louder. When I felt her hands, guiding and pushing me into that spot, I felt confident that I should focus everything on her clit.

I was startled at first, when she started bucking and grinding, but then I felt very accomplished, when I realized it was an orgasm.

She was moaning, "Ohhhh...ohhhh...Rob...Rob...Rob...yessss...yessss...oh my...god...yesssss...oh my god...wwwow!" She was breathing heavy, but relaxed and smiling, "Wow...that was amazing...Jason never did that for me! You are the first man to ever make me cum like that, but then you're the first man to ever go down on me!"

Despite feeling proud of what I just did, I didn't really know what to say, so I just held her in my arms.

I remember kissing her cheek, but then she asked, almost begging, "Things didn't go the way we thought, but I want you stay...can you still stay here...please? It's the first time that I've spent the night with a guy...please?"

I certainly wasn't driving back to Champaign, and I don't really know where she got the idea that I might stay at my parents'. Of course, I hadn't told them that I was even in town, or back from school...there was no way I was passing on the opportunity to spend the night with my girlfriend. I quickly nodded, with a big grin, "Yeah...I wanna spend the night...and it's a first time for me, too."

She gave me a big hug and kissed me, before laying her head, back on my chest, "What you did for me was amazing, and please don't think the attempt was your fault or anything...because I'm not done with you."

That night, Valerie fell asleep in my arms; it seemed like she fell asleep in two seconds. My mind was spinning some but snuggling with her seemed to calm me down. We both yearned for something more, but I wasn't far behind her, in falling asleep. I gently caressed her hip and cupped a butt cheek, thinking about the skimpy running shorts she runs in, and what it was like to have that bare bottom in my hand. Now that I'd experienced this, those damn shorts were going to send me over the edge...thought I might have to wrap my crotch to control my dick.

Knowing my girlfriend was determined to try again, I fell asleep that night, dreaming of burying my face between her thighs, again...getting past the blowjob.

*****************************************************

That week I went out and got new condoms, only to discover there were bigger sizes. Maybe the ones in my wallet were old, but they were definitely too small. I guess I thought they were one size fits all...and hadn't really given it any thought.

Valerie talked to a girlfriend (or girlfriends), and I think that's where the word got out about my attributes. It did wonders for my reputation among her group of friends, but my focus was on Valerie, and I wasn't really planning to hook up with her friends. Anyway, her friend Lisa told her about KY, and helped her at the drugstore. Valerie called me with the news and told me she'd even practiced...of course, I had to hear the full story. She started out by fingering herself and followed up with the handle of kitchen utensil (I remember it was a whisk that she hid in the back of her closet).

With new condoms, the lube and some practice, we were ready for another try; we just needed to find another opportunity where we could get together...a break from her training or just a weekend. I didn't want it to be in the car or in a motel, but then we caught another break. This time it was my parents that were leaving town, and they were taking my brother...score! I could head home and have the place to myself.

There was little foreplay, before the panties came off. We were making out and I gazed into her eyes, as if to get her approval, before gently lifting her leg up and pushing it off to the side. Spreading her legs open like that, exposed her freshly, trimmed pussy; I trailed my fingers through the little muff, cupping the mound, and gently pressing my fingers over her lips.

Teasing the tight folds, I opened her with my fingers, and she was moist...which I thought was a good sign. I smeared the lube over her pussy lips, slowly inserting one finger then a second...she was tight as fuck and groaning. Because I didn't want to hurt her, I was hesitant to spread her open more, but then I felt her relax some, and I whispered, "Doin' okay?"

"Yeah...I think so...it feels good...you know...but maybe put some more in there."

I didn't waste a second, before scooping up more lube. This time, I pumped my fingers inside, like I was fucking her, and she groaned, "That...that feels good, Rob...do that and wiggle your fingers around...try to stretch it...wider...maybe."

"Still doin' okay?"

"Yeah...yeah, that feels better...a lot better...go slow but try three...three fingers...maybe."

I was glad she was telling me what to do, because rubbing the walls of a pussy was uncharted water, but it felt amazing...and I was beyond horny. Seriously, I think I could have driven nails with my cock.

I rolled the condom on and smeared it with lube, especially the business end. I added a little more to her pussy's tiny slit, confident that it was enough, and giving her a gentle peck, "Sure you're ready for this?"

She seemed more excited than nervous, smiling, "Yeah...more than ready."

I guided it to the entrance, while she spread her legs and opened a little gap with her fingers. It was a given that I wasn't going to slide right in, and I held it tight, pressing the tip against the opening.

She didn't scream when I pushed inside, but she gasped, "Whhoaaaaa...that still feels big...stop there and let me...ahhhh...ahhhh...get used to it!"

Crazy with lust, I was the one that almost screamed; I was exuberant that my dick was in a pussy for the first time, and finally, I was about to fuck my girlfriend. The sensation was incredible...Valerie was tight as hell...it was moist and hot...it was fucking insane...she was my first, and I was no longer a virgin!

They say you always remember your first time...it's true. I felt like I was gonna fucking explode, but I kept it there till she gave me a nod, "Go ahead...give me more, but slow...go slow." To this day, I think it was that slow, gentle pace that helped me to keep my shit together.

"Oh shit, Rob...Rob...oh Rob, it hurts a little, but not much...keep going...it'll get better."

"There's just a little bit more...you sure?"

"Yeah...yeah, keep going...I can take it!"

I went super slow, gently pumping deeper, till it was all in. It felt a little like a blowjob, but over my whole cock...I'd never had a girl that could take it all in her mouth, but it was all inside her pussy. Her hot, velvety insides were tight around the shaft, almost like it was being sucked or squeezed.

I felt more at ease, when she grinned, "Oh my god...it's all in me," and high-fived me! "Mmmm...just hold it there...feels like a baseball bat, but in a good way...it's my first big one...a man's cock!"

Still a bit nervous, I gripped her waist, and got ready to fuck her...but I was prepared to pull out, if it started hurting too much. A little time passed, before she whispered, "Go for it...fuck me...but go slow."

Clearly, things were going good...it was almost miraculous when I felt her push against me, and start talking, "Rob...oh god, Rob...we're doing it...we're finally doing it! Sweetie, it feels good...it makes me feel good...it's still big...but it's perfect...absolutely perfect!"

Overwhelmed with all the sensations, I could barely grunt...or put words together, "Yeah...yeah...it's perfect...yeah!" Still amazed that I was actually fucking my girlfriend, I watched the shaft drag her pussy lips in and out, with each thrust.

Totally surrendering to the pleasure, Valerie grabbed her knees and opened them wider for me. Losing my inhibitions, I took the cue, pressing my hands over hers to hold her legs back...and thrusting harder.

I watched her start rubbing her clit; it was obvious she knew what she was doing, and she smiled "I want to cum on your cock, and Lisa told me this's a good way...ahhhh...ahhhh...ahhhh...and she was right...it feels even better!"

I inched her legs a little wider, gripping her thighs, and thinking they looked even better closeup, than they did out on the track. They were muscular, and toned, but still feminine in the way they met her body and sensuously formed a beautiful ass; it also looked amazing on the track, and better closeup.

My relentless thrusts had her whole body bouncing over the bed, and she was loving it, wildly rubbing her clit and grinding against me. "Rob...Rob...ahhhh...ahhhh...ahhhh...fuck...fuck me...fuck me hard...fuck me hard!"

It was amazing to hear her say those words, and I did exactly what she wanted. I fucked hard, but I was totally overwhelmed, when her orgasm started. I nearly stopped to watch, because it rocked her entire body; she was shuddering and thrashing against me. I was fascinated to feel her pussy clench my cock, but of course it was all new to me. It was the first time I had a woman orgasm on my dick like that...but it was a first for her, too.