We all know one – a really nerdy chick. She’s young and single, surely virginal because she’s kind of weird and not much to look at… but she does have this one feature that, along with a couple beers, would make you aaaaalmost wonder what it would be like to hook up with her. Besides, every nerdy girl has a hot friend.
The nerdy girl I know is Kathryn. She’s kind of awkward socially, but has always been nice to me personally, and when she says or does things that would get on some people’s nerves, I don’t hold it against her. She’s super smart, one of those people who, whenever she says something that sounds weird or might insult certain groups of people, everyone assumes she just knows more than they do and lets it go without a challenge. She’s not mean… she just doesn’t have much of a filter and likes to inform people, many times of random stuff, to the point that I can see it when people cast her as a know-it-all.
The one feature of hers that has made me, when I have a bit of a buzz, wonder about hooking up … well, it’s two features, a pair of features: her tits. I know, you’re thinking I’m the typical perverted guy who just likes a well-endowed chick for her big tits, but actually no, it’s not like that. Hers are just the way I like them… maybe B cups if that, they stay put when she moves, and become perky firm mounds when she stretches her arms over her head. She wears old t-shirts a lot of the time, ones she’s probably owned from before she, ummm, filled out (even though she’s pretty lanky and skinny, and may not be considered “filled out” even now), so they’re often a size too small, and thin enough that if I stare, which I admit I do occasionally, I can make out the material of a textured bra underneath, even some nipple.
Kathryn has kind of frizzy hair, actually does wear nerdy glasses, has a complexion that’s far from smooth, and even tough her tops are snug, she wears mostly pants that are baggy on her skinny hips and flat butt. Not ugly, but nothing to make anyone take a second look. Except those tits.
Besides, she has that friend, Nikki, who’s smoking hot. five-foot-nine or more, swishy reddish-blonde hair that she likes to pull in front of one shoulder, green eyes, full tits that must be at least a C cup, a thin, toned core and curvy ass and hips. She dresses very nicely, businessy-attractive with heels just high enough, skirts and dresses just short enough, pants just tight enough, and tops just low enough that get the guys’ imaginations stirring. A while back, I had taken to fantasizing about her, and have tried to make myself believe that she was eyeing me as well. Hanging out with Kathryn has given me more opportunities to be around Nikki, and even though hooking up with her is very unlikely, a guy can dream, right?
Not long ago, Kathryn got on a kick of trying to create social situations for herself, asking anyone and everyone to do stuff with her. She’s nice enough, so she wasn’t facing rejection enough to make me feel sorry for her, but it was a little weird. Even more weird was when she invited me over to her place one weekend when she knew my girlfriend would be out of town. Others were invited too, including Nikki, so I was interested enough. Kathryn said she’d make dinner and we could all watch a movie or something. And hey, it was free dinner and I might learn something about comic book characters or sci-fi, so, why not.
I arrived late, but found out that I was the first one. The conversation was indeed awkward – there are the normal pleasantries, like thanks for inviting me, thanks for coming, and the customary tour of each room of her place. It was kind of messy, but just cluttered and not dirty… kind of fit her personality. As she exchanged some texts with the others, it became apparent they wouldn’t be coming.
“Well, I do have dinner going, and since you’re here already, we can hang out.” I guessed she just didn’t realize it’s inappropriate to be alone with someone who’s attached. But, if I would have gone home, I’m sure I would have just spent the evening jerking off to thoughts of Nikki, imagining me unbuttoning her silky blouse and unzipping her mini skirt to reveal an exciting lacy stocking, garter belt, thong panty, and push-up bra ensemble.
I thought that actually relating to another human rather than dreaming about something that would surely never happen would be the better choice… so I decided to stay. Kathryn is pretty cool, and I didn’t want to be a jerk and leave her with no one she went to the trouble of cooking dinner for.
“Well, it sure smells good in here,” I told her. And I wasn’t lying or just trying to make her feel good – the aroma of whatever was cooking was making me glad I went.
“Thanks,” she says. “It’s-” and then she said about 10 syllables, none of which I could understand. A favorite local dish of some place in the world which I’d be embarrassed to admit I have no idea where it is. “I looked up the perfect wine to pair with it,” she said, and described some characteristics that bring out and compliment the such-and-such flavors of the dish. Yep, she’s nerdy. She poured us each a half a glass, and we sipped it while we chatted.
“It’s going to be a few minutes before it’s done, and then it has to rest for a while,” she said, tipping her glass up to swallow a big mouthful of her wine. “So… do you want to have sex?”
I almost dropped my glass, staring at her. She’s joking, right? She looked serious, but she has such a dry sense of humor, so I wasn’t sure. “Ummm… whaaaat?” I was stalling, trying to read her.
“I think we should. It’ll be fun,” she said.
“Well, sex is fun,” I agreed, “but…you know I have a girlfriend, right?” I didn’t really consider Kathryn fuckable, so I tried the excuse that wouldn’t exactly let her down. If was going to cheat on my girlfriend, I would hold out for someone like Nikki… I wouldn’t go for a nerdy chick like Kathryn. Would I?
”I know, dumb-shit,” she said. I feel like a dumb-shit for asking. “And that’s a weak excuse anyway. Like you’re putting it on me to back off rather than saying no out of a sense of… fidelity or something.”
I figured, hey, she may just be serious. But if I did agree and it turned out she was kidding I’d feel like a big doofus.
“Well…” I said, nervously, now actually wondering whether I’d consider it or not. “You caught me off guard. You are pretty… forward. If you’re serious.”
“Sure I’m serious. I’ve never done it before, but I want to, and we’re here alone together. What better opportunity? Besides, I see the way you look at my boobs, and Nikki has mentioned it too.”
Shit – she’s caught me ogling her tits? And others have noticed? I needed to change the subject fast.
“Wait… you’ve never done it before?”
“Seriously, are you really surprised?” It’s almost like she was telling me that nerdy girls don’t get laid. Well, maybe they don’t, but I wasn’t going to agree with her, about her.
“I mean, I wouldn’t think you… I don’t think I’m, like….“ Shit… if she really was a prude, she’d be offended if I thought she was too slutty, but if she had wanted to get laid but been unable to, I’d be risking making her feel bad for being undesirable… so I just stopped talking.
She had set her wine glass down and was leaning back on the couch, arms behind her head. Was she doing this on purpose, trying to get me to look at her tits? I tried to retain eye contact, or look somewhere else, but I noticed them alright. Hell, I found myself actually considering doing her. Was I really attracted? I mean, she was willing, assuming she wasn’t playing me, and those tits…. But was I thinking of a sympathy fuck, giving her some dick because I didn’t think she could get any otherwise?
After an awkward silence, she grabbed me by the hand. “So… if that’s a ‘yes’… and if you want to get some of these,” she said, cupping her pert titties. She started leading me out of the living room… toward the bedroom, I assumed.
I wasn’t saying “no.” I found myself being coerced into going through with this. Well, not even coerced, but thinking, why the hell not?
Yep, we arrived in the bedroom. Standing next to the bed, we smiled hesitantly at each other while I took another drink of my wine and she tipped her glass up to finish hers. She made the next move, leaning her face into mine and giving me a kiss. Not an awkward nerdy virgin never-done-it-before kiss, but a nice soft lingering one. I reciprocated, and after a few more, she separated and smiled big. “Mmmm, that’s nice,” she told me, and leaned in for more.
“Ummm, yeah,” I agreed. My dick responded, stirring in my pants, notifying my brain that it didn’t give a shit that this chick is nerdy. Sitting on the bed, Kathryn patted the spot next to her, and I joined her as we set our wine glasses down. After a couple minutes of making out, she was pretty obvious about pushing her tit into my forearm, so I slowly moved my hand to cover it. As my tongue swirled in her wine-flavored mouth, my fingers felt the contours of her bra and definitely a stiff nipple through her shirt. When we separated, we were lying on our sides facing each other, my growing boner telling my pants to set it free.
Kathryn noticed, smiling at it, and moving her hand down there. I didn’t move, letting her fingers nudge and prod my stiffening shaft. She said she’d never “done it” before – by the way she kissed, I couldn’t imagine she’d never done that before, but I wondered if she’d ever seen a dick, or touched one, maybe given a hand job, or blow job, or dry humped without penetration.
“Do you have a condom?” she asked.
Oh, shit! Here I was actually about to agree to have sex with her, my dick getting hard in anticipation, and now it was going to get shut down before it even got started. “Ummm, no.” I tried to make light of the situation. “I know this is will be hard to believe, but… I really didn’t think I’d need to be prepared tonight… for… you know….”
She snickered and got up from the bed. “That’s okay,” she said, opening the drawer of her nightstand and picking up a small box from inside. “We can use mine.” Handing it to me, she said, “I hoped these would come in handy someday.”
I looked at the box – a 10 pack of lubricated condoms – good ones, not latex, but the ‘real feel’ material. “Ooooo… super thin for super sensitivity,” I said, reading the box out loud.
“Yeah, but they’re strong.” I looked at her funny, because… how would she know? The box wasn’t opened, and she said she’d never had sex before. “Like 30 percent stronger than a couple other brands I looked at. They have great reviews, and labs have pressure and stress-tested them. But latex is a problem for some people, so, I didn’t want latex for sure. Plus, these are really thin so people say they to feel a lot better than others.”
“Sounds like you did your research.”
“Always.” Listening to a nerdy girl talk about condoms was… actually kind of hot. I wondered what it would be like for her to describe sex toys. Her voice was actually pleasant now that I thought about it… I began to smile at the thought of her doing phone sex or being the voice talent for some erotic sex story audio.
Kathryn pulled her shirt off and dumped it on the floor. Unbuttoning and unzipping her pants, she pushed them down to her thighs, revealing her bony hips, then turned around to sit her skinny ass on the bed. After untying her shoes and letting them drop, and pulling her socks off, she recovered from her rookie mistake and pushed her pants the rest of the way off. She looked a little nervous, but surprisingly not shy, leaning over to me for a kiss while she pulled at my shirt. I wrenched my shoes and socks off and stood in front of her, pulling my shirt off too. She smiled and gave me an “oooo”, as I began to undo my pants.
In a moment, we were both in just our underwear, and she was eyeing my crotch, where my hardening dick was making a pronounced tent in my boxers. I looked down at her in her fairly plain peach-colored little panties and the matching bra that her small tits weren’t able to fill out. Not nerdy, whatever “nerdy” bras and panties look like, but certainly not overly ‘sexy’… she’s nothing special, but there’s nothing that was a real turn off. Since a willing chick getting naked in front of me, wanting my dick in her, doesn’t happen nearly as frequently as I’d like, this was an opportunity I decided I wasn’t going to pass up. Plus, backing out now would make me even more of an asshole than if I just wouldn’t have started. Was I going to do this for her, or for me?
Kathryn unhooked her bra in the front, the cups falling away to expose her titties, which definitely didn’t disappoint. By the way her puffy areolae were tipped by stiff, perky, protruding nipples, it’s a wonder that they hadn’t been even more obvious through her shirts before.
When I pulled down my boxers and my mostly-hard cock sprang free, Kathryn gasped and laughed. That was an excited laugh, not a derisive laugh – right? She was smiling big, and it was the first time I’d really noticed how pretty and straight her teeth are. Now I’m sure she was one of those homely girls in middle school or high school whose braces made her even less attractive, but they were sure paying off now.
I figured she liked what she saw well enough, because she pushed her panties down and kicked them off her feet. She removed her bra completely and lay back naked in front of me, immodestly displaying her pubic hair. which was kind of sparse but covering an area that seemed fairly large surrounded by her skinny legs and bony hips. Simple stud earrings, a cheap plastic watch, two rings, and her glasses were all that she had on at this point. She was ready.
I thought to myself, so, I’m really going to do this, huh? Kathryn isn’t anything that fantasies are made of, but hey, nerd pussy is still pussy, right?
I climbed onto Kathryn as she scooted back on the bed, our naked bodies pressed together, my hard dick lodged against her hip. The two of us groped each other while we made out, and I could taste the wine on her mouth. She let me grab her perky little tits, and I glided my hand down her leg, and up, all the way to her ass. She reached for the box of condoms, and I knelt over her, one leg between hers and one leg on the outside.
She opened the box and separated one condom package, handing it to me. “Here, time for this.” I tore the package open and lay on my back for a moment while I rolled the condom down my dick shaft, then got back on top. She touched the floppy end with her fingers and pulled on it gently, then pulled her leg out from under me and swung it to the outside, so now I was between her legs. I took a good look at her lewdly-splayed naked crotch, a generous but not unsightly bush of dark pubic hair, thin enough that I could make out her meaty pussy lips.
My cock was aching to get inside, but I knew I needed to take it easy with this one. I started kissing her tits, barely sucking in a nipple before she put her arms under my armpits and around my back, holding me tight and actually pulling me up her body. So I collapsed above her, trying to keep most of my weight off, and let her attack my mouth with hers, a little awkward at first with her open mouth and tongue, but kind of nerdy-hot with pronounced “mmmm” sounds. She dug the fingers of one hand into my hair, while the other made its way in between us and found my dick, guiding it into her crotch. I broke from her and knelt between her legs, angling my cock down and pushing the tip into her pubic hair, gently rubbing up and down to find her slit.
“My vagina is wet,” she announced. “You can put it in.”
“Uh, yeah, that’s nice, but we need to go slow.”
“No, just put it in. You’re not going to break anything.”
Ummm, a hymen, maybe? “Well, I don’t want it to hurt…”
“It won’t.” She scooted into me a bit and reached a hand around to grab my ass. I leaned forward and pushed, my cock meeting some resistance initially and then penetrating inside. “Mmmmm,” she hummed, “yessss, put it in.” So I gave her half of it, in and out with sawing motions to get her used to the feeling. She pulled me down and arched her hips up, her pussy encasing pretty much my whole dick. I decided to give her as much as she wanted, collapsing more fully onto her, surprised that I was buried all the way in to my balls right away. It was a snug fit, but much easier than I expected.
“Oooo, yessss…” she whimpered.
“That’s okay?” I asked, withdrawing some and pushing back in. I didn’t want to go too hard with her… not because I’m a gentleman so much as because I was actually getting into fucking her now, and didn’t want her to tell me to stop.
“Oh yeah. Just because I’ve never done it with a guy before, doesn’t mean I haven’t, well… had practice.”
I assumed she meant masturbation, and not just the rubbing kind, but the penetrative kind too. Huh, she did say “with a guy,” so maybe… she and her nerdy girlfriends had gotten bored during D&D night one time and started fingering each other? Or, if she had popped her own cherry and gotten herself ready for dick, that’s no problem for me. But then I got concerned… maybe she had fucked herself with a huge dildo and thought all cocks were that big and I was turning out to be a disappointment?
These thoughts flashed through my mind, but were displaced by my thoughts of how to control what was going on between her legs. I was enjoying this a little too much, her warm snug cunt providing some firm pressure all along the length of my cock, so I had to think about how to pace myself. Kathryn kissed me deeply, grunting slightly but never backing off while she wrapped her legs around me and gyrated.
“You can do it harder,” she said, grabbing my ass, a little more lust in the brown eyes peeking out from below her crooked glasses. “It’s good.”
“All right…” I drove into her deeply, excited that I was giving her a good time her first time. Grabbing a tit instinctively and burying my face in her neck, I was really fucking her now, not just wiggling my dick around in her. I did her deep with full strokes, my own lust making it difficult to hold back.
“Oh, yes,” Kathryn cried out, fucking back up at me. I was actually close to cumming already.
“Wow,” I told her, “this is nice… I’m close already.”
“Great!” She squeezed tighter. “Do it.”
“Whaaaaa? No… I…”
“Yes, you can finish now. We can do it again later.”
“Oh, wow, I have to stop,” I told her, trying to pull out, but unable to because she was clenched around me. Either she was strong for someone without any meat on her, or I just didn’t want to separate.
“No, don’t,” she hissed, bouncing under me.
“But really… I’m about to… I can’t hold it.”
“Don’t hold it. Do it,” she told me.
“But…” I protested. It was no use, though.
“We can do it again later. Go ahead.”
Later? What? I couldn’t even prepare myself. I was cumming already.
“Ohhhh, yyeeeaaa…” I grumbled, tensing up with my final thrusts.
“Yes, do it,” Kathryn encouraged, fingers gripping my ass and bony hips bucking under me. “Finish inside of me.” I was spewing anyway, but it was good to know that she was on board. I rammed my cock hard and steady deep into Kathryn’s nerdy cunt, flooding the condom inside of her. “Uuuggghhh,” I grunted, powerful orgasm subsiding as I clenched her shoulders. “Uuuuugghhhh…Kathryn, yeeaaahhhssss…”
After my trembling stopped, I kept stuffing my dick inside her, over and over, grunting, holding it deep each time, trying to get a sense if she was trying to get to her own climax, but her lack of movement told me that she was fine with me just doing her and wasn’t trying to get off herself, So when I was satisfied that I was completely empty, I pulled out and rolled off her. “Whoa…that was…”
“Nice.” she finished my thought.
“That does feel really, really good.”
I was proud of myself for not making her first time a bad experience. Well, kind of. “So… it’s really not supposed to be… well, over that fast.” I almost felt bad about cumming so quickly. “But… you were okay with it?”
“Well, it’s usually, you know, the stereotype… the girl complains that the guy finishes too fast.”
“Oh, so you get to have sex, and you’re complaining now?”
“No, no… I’m not saying that. I’m not complaining… I mean, I could have stopped if I wanted.”
“Yeah, right.” She smiled, calling your bullshit. “I’m just messing with you. I know you’re not complaining. I wanted to just do it and not hold back. To get the feeling. I guess I have the rest of my life to experiment and try other things. Don’t have to do everything the first time. And now I know I can.”
“What do you mean?”
“Well, I know I’m nerdy and not that pretty, not like Nikki or anything. I’ve felt like I might never do it. But I guess what I read is right – if I come on to a guy and tell him I want to get some, chances are he’ll give it to me.”
She sat up and looked down at my half-wilted dick. She had only seen it hard up till then, so I hoped she wouldn’t be disappointed now that it had shrunk. “Here, give me that,” she instructed me. I stood up and detached the condom, being careful to squish my cum from my shaft down inside. I handed it over, and she held it up, inspecting it closely, evidently admiring the deposit of thick fluid inside. Pushing her glasses up her nose, she let the full condom dangle in front of her face, grinning, almost giggling, flicking it to make it swing like a pendulum.
She got up and walked into the bathroom, taking her condom with her – nothing nerdy about those cute perky naked jiggling tits. I lay back on her bed, face up, my mind racing while I heard water running. Did I really just fuck nerdy Kathryn? Yes, I did. And because of the way I’m lying face up, my mind is imagining her riding me, her broken-in pussy grinding into me while I pinch those perky bouncing titties… I guess I’d do it again. What did she say about “later”?
The water stopped running, and moments later she returned with two damp washcloths and a hand towel. I wiped my dick and balls with mine while she dug hers into her crotch, and after drying with the towel, she started to put her clothes back on.
“Thank you for that,” Kathryn said, kind of nonchalantly as if I had just helped her carry a box to her car or something. “Ready for dinner?”