The Truth About Wine and Hot Nerds

Back in my mid 20's I was dating a VERY conservative Christian girl in her late 20's. Once I came out as an Atheist, our dating really cooled off from hand holding and snuggling while watching movies at my place to... meeting in public more and more with her female roommate.

Let's call the christian girl I was dating Madison, and let's call Madison's nerdy roommate Evie. Both of these women were modestly curvy brunettes, maybe 5' 6". Madison had absurd, Disney princess prettiness, and was one increment thinner than Evie. Evie was always dressed a bit frumpy, like she deliberately bought clothes two sizes too big

Evie and Madison had been friends for most of their lives, and I was pretty sure Evie was used to Madison being "the pretty one" which was a gross underestimate of her charms. She was a very attractive girl, but she had no fashion sense, a dumpy haircut, and coke-bottle glasses. And as I think more and more about it- you should imagine Evie as a slightly taller Velma in baggy clothes? And now I wonder if she was going for that look on purpose.

One night I was cooking at Madison's place. I was nice and dressed up, date-ready. Madison was... wearing basically a sweatshirt and gym shorts. She wasn't wearing makeup and had her hair in a bun. I got the vibe that the magic was gone. Especially when right as I was plating dinner, Evie came through the door. This was planned. Her roommate was there as a buffer. Yeap. I was all the way out. I hid my heartbreak pretty well, and we had some great food to eat, so my night wasn't a complete wash. I set the table for three, and I made jokes and smalltalk.

Evie told me I looked really nice. We saw each other all the time at work, so I was a bit more dressy than usual. I returned the compliment as Evie was basically in her work clothes, which weren't TOO baggy today. Madison didn't seem to mind the lack of attention on her ensemble. We finished dinner and shared a bottle of wine between the three of us. Somehow the conversation turned to how we look at work, how we look on a date, and how we look online.

"Madison is one of those lucky people that looks great everywhere" said Evie admiring her across the table. I couldn't help but agree. Even in a no-effort way, she looked amazing. Like some heavenly visitor gracing we petty humans with her presence. Evie also found the opportunity to make a self-deprecating comment about her looks

"Me, I look like a goblin every where I go" she said

"That's not true! You're both very pretty. I was super intimidated approaching Madison, I always thought you two were twins, or at least sisters." This was my honest first impression of the two.

"Really!?" They both guffawed"

"Gods' honest truth. Now, me, I look great in person. I'm easily an 8/10." This was a bit of an exaggeration, but I went on with the boldness of wine

"Adrian Brody snozz, handsome, classic Frenchman features, maybe a bit gangly- but in pictures, I look like a bridge troll!"

Evie perked up "Ooh! lemme see you in pictures!"

"Sure! Just lemme make sure you don't see any of my naked pictures, those are true atrocities!" I joked.

Without hesitation- Evie leaned in even closer "I bet you look great naked too..." with her face that close, and the implications of that sentence, my heart skipped a beat, and I could feel a rush of blood to my cock.

"umm... well... let's just get you these pictures." Evie scooted her chair right next to mine. Madison, seemed completely disinterested, and excused herself to open another bottle of wine and refill everyone's drinks. Evie and I flipped through a few pictures of me in junky clothes I'd wear out to bars, or hanging out with friends, some of my snazzier selfies, and I started to pull the phone away when I knew we were starting to sneak up on some... "artistic nudes" of myself. I thought I was in kind of a weird situation, where the roommate of my soon-to-be-ex was ogling my dick, and it'd be DOUBLY weird since we all work at the same place.

I didn't want to become "that guy with the big dick" at the office. But I think Evie read the hesitation, read the tension in the moment, and flicked to the next few pictures.

And there I was, in black and white, erect cock out, and in a few of them stroking. I had the good sense to leave my face out of my nudes, and try to anonymize it a bit with black and white... but my hand wrapped around my dick was definitely the same as the one holding the phone.

Evie let out an ecstatic gasp. "What!? There's no way that's you..." she said barely over a whisper. But as she leaned for a closer look, she put her hand on my thigh. I leaned into her touch unconsciously, hoping to perhaps brush against her hand. My cock was swelling inside my slacks at her proximity, and the obvious excitement she had of seeing me naked. I could smell her perfume on her neck, and my head was getting empty with horniness.

Madison had downed another glass of wine and was on her smartphone pecking away at a clicker game or something.

"Hey... you like Zelda, right?" Evie said, reading that Madison was completely ejected from the conversation.

"Who doesn't!?"

"Why don't you help me out with a spot I'm having trouble with."

"Sure!" I picked up on what was going on, but I was so goobery-wine-buzzed and horny that I told Madison "we're gonna play Nintendo!." She barely answered with a grunt.

We both, breathlessly went to Evie's room and shut the door behind us. She let out a suppressed squeal

"Oh my god! Is that real? I've never seen one so big!" she said in a frantic stream of giggles.

I got a little bashful. My back was to the door "umm... do you want to see it?"

"Yes!" Evie said before I finished my question. I was getting increasingly flushed and bashful. I always get this way about my cock. Not that I have anything to be ashamed of. Let's use the term "bigger than average." I slowly unzipped my slacks, pressed my butt and back to the door with Evie staring right at my crotch.

I gave myself a firm grip around the base, and pulled myself out of my boxers, and gave about six, long, full strokes. It was all I needed from chub to full with this gorgeous nerd gawking at me.

"Holy shit! That really was you!."

I couldn't meet her gaze, I was trying to look away from my member, and away from her at the same time but I was fairly cornered. Evie... remembering why we came in here- turned on her TV, and put a Zelda game on for background noise... she came back agog at me.

.".. is it... does it hurt?"

"Not since I pulled it out, but... yeah, maybe a little"

"what do you do when that happens?.".. I realized this was very informative for Evie. She must have been a virgin, and this was very likely her first live cock in person.

"Ummm... I stroke it?" She got down on her knees, and scooted a couple inches closer to me.

.".. do you want to?"

My brain was completely empty at this point and I just let out a gasp, and started furiously masturbating inches from Evie's face. I knew my head and butt were thumping against her door, but I didn't give a single fuck. I noticed Evie's hand move between her closely held together thighs. She was Caressing her legs and squeezing her hand as it got close to her pussy.

"Do you want to help?" I asked through a haze of horniness. She only nodded, I could tell she was extremely nervous. I slowed down my pace, and put my hand down at the base as she reached for the top half. I spit down onto her fingers, and she rubbed my spit onto my cock.

"I like how rough you are with yourself... is this good?" she asked as she pumped my spit lubed dick with her right hand.

"try rolling your fingers over the tip, and rub your thumb- yeah, like that!" she was a fast learner and an enthusiastic student. I set the pace by stroking the bottom half, and pushing her hand up and down with it. I was starting to melt down the side of the door... my legs were going out, but Evie had her left hand all the way down her pants, with the zipper to her fly undone. She had lilac, frilly panties on. Her gaze was fixed hypnotically on her hand bouncing on my cock, or she'd occasionally lock eyes with me as I moaned and squirmed.

"Can we... move to the bed, my legs are getting wobbly!" I said through a half-gasp, half chuckle. We took a 10 second break, and I plopped onto the edge of her bed. She stayed on her knees and scooted over to me.

"Do you want to take your pants off?" I asked as I got fully nude and tossed my clothes in a pile. She didn't answer, but she dropped to her side, and kicked her pants off, leaving her oversized blousey-sweatery thing on. She slid a pair of fairly damp lilac frilly panties off as well revealing a sprawling full dark bush. Somehow, the spontaneity and nerdy lack of trimming made this moment a bit hotter. I gave a bit of a groan at the glimpse of her, bottomless, and we resumed stroking my cock as a team, and she began to touch herself uninhibited.

After a short while I was really starting to lose it, my hips were rolling, and my head was back when I wasn't watching her touch herself, but magical words floated in over the sound of the Zelda soundtrack playing on loop

"Can you... teach me how to suck cock?" Evie asked sheepishly. I could lie, and tell you we went step by step, that I was very patient and very instructive, but I was so far gone, that when I said "yes" and she wrapped her warm, wet mouth around my cock, I stopped being a sentient, thinking being.

She was by no means "a natural" but I gently grabbed the back of her head and bobbed her up and down on my throbbing hard erection. I told her to clench her lips around me as hard as she can, and to press her tongue hard against the underside of my cock. That was all the coaching she needed. She kept one hand wrapped around the base to keep me from unintentionally throat fucking her, and to pace herself.

I could tell from her lusty, greedy moans and the heavy, quick circles she was making on her clit that she was an expert masturbater. I wanted to watch her cum before I did. So I tried to pace myself.

I pulled her face back, and gently guided her mouth free of me, and directed her eyes upward

"Look at me when you cum." I said as she continued to pump my cock with one hand, and rub her pussy with the other. Apparently all she needed was a bit of encouragement, and permission, because she came with a whimper, and strong, trembling leg shakes. But with direct eye contact and a cut off gasp. I could tell she was used to orgasming very quietly, as her room was right next to Madison's.

I very shortly resumed fucking her mouth. I had that very familiar feeling of being right on the edge of cumming, but I had the foresight to ask a question first

"Where do you want me to cum?"

No response, just enthusiastic slurping, and sucking, and stroking

"Evie- where do you wa-" she sped up, her lips locked around me, her stroking hand matching the beat of her head bobs.

"oh fuck, I'm gonna cum!" I said in a shaky whisper. Evie only let out a deeply satisfied moan as I filled her mouth with a thick load. She swallowed with a gulp, and a heavy gasp to follow.

"When can we do that again?" she asked between deep breaths.