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 though 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 I 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 felt 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 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.