tagFirst TimeVirgin Guy's First (What If) Ch. 01

Virgin Guy's First (What If) Ch. 01


A little background first is in order I think just bear with me through the little pitty party please.. or move on.. I am 23 years old, around 6'7 when I stand up straight, typically only about 6'3 because I tend to hunch to try to hide and because I'm shy and my back hurts. I have AP Scoliosis and a Caephosis of The Spine which earned me the nickname "Turtle" my last year of high school before I quit. I have dark brown hair, dark green eyes, wear glasses on occasion though I'm actually supposed to wear them all the time and I weight about 250 pounds with what looks like a beer gut and man boobs but its actually where my stomach is pushed out where my lower back arches backwards really far.. My stomach is actually flush with my ribs.. I was put down all my life from the idiots at school to my own cousins and eventually my sister. My dad was away a lot TDY for the military and would come home to fights that had been raging and end up beating me for even touching my sister after she had been beating me for months.

My so called friend would also use me as they saw fit and even beat me up to try to make themselves more popular if they thought it'd work. I've been used and abused since 5 years old and so now I am very shy and don't know how to make friends and have abandonment and trust issues.. Ok enough of the poor me background..

This is a "what if" basically one of my fantasies about my first time, because at 23 I've only ever been with one girl, didn't even really date her, just met her and then started kissing shortly after because that's what she wanted to do. I was with her off and on for 4 weeks and took care of her needs as much as possible thinking it'd make her want to keep me around or maybe return the favour.. After about 30 orgasms in 5 sessions.. she dumped me without having ever stroked me to orgasm or given me a bj or anything.. I had to beg even to get her to look at me or touch me through my pants... anyways here we go..

One day, I was in Roseville, trying to get a job at the Discovery Store, and was turned down in an on the spot interview. It was the same old story as any other time I tried for a job. "What have you been doing for the past two years since you were laid off from your previous employer? I'm sorry you just don't have enough work experience, come back when you get some and we will see what we can do." After that, I was really down and felt stupid for even trying and for just how nervous I got during the confrontation, so I wasn't watching where I was walking, just the three feet of floor in front of my size fifteen Converse All Stars I wear to interviews. As I was walking out to the parking lot I actually, physically, ran into a woman and knocked her flat on her ass and sent her bags and their contents everywhere. I was so shocked and an emotional wreck anyways that it took me a full minute to realize what happened. By then she was up and seriously pissed as well as slightly hurt. It was the first thing that I noticed, not how she looked or even that it was a she, just that it was someone I had hurt. I immediately apologized, and quickly set about picking up her things while trying not to look at her.

When I was finally at the last bag, she must have had ten bags, I froze, noticing what the contents of her last parcel were... It was a Victoria's Secret bag and I had just stepped on one of her panty sets.. I stood there half bent over, unknowingly giving her a good view of my butt in my slack-like cargo pants.. I just couldn't move, there was no way I could pick up the little frilly materials that made up what I would consider her most intimate items, well next to her collection of sex toys I'm sure she owned.. It was also the first time I realized she was female.. I stood up, shaking like a leaf and not even remotely able to look at her, I just slowly backed away from the bag and tried my best to apologize once again but my voice squeaked and cracked like a pubescent teenage guy, which elicited the cutes giggle I've ever heard from a grown woman.

"Oh come on, it's not like you've never seen a girl's negligee before. You picked up the rest of the things you made me drop, it's only fair you pick that one up too." I heard, she had the most amazing voice I had ever had the pleasure of witnessing and it sent chills down my spine, and oddly enough, for the first time in my life, made my dick start to harden, which only fueled my confusion.

Once again I looked at the skimpy garments on the ground and turned away unable to bring myself to do it. "Ai, Aiee" I squeaked and tried again. "I'm sorry I knocked you down. I wasn't paying attention to who was in front of me, I was just trying to get out of here and to my car as quickly as I could, I just want to go home and forget I even came here." I commented, probably sharing more than I should have, as I have then tendency to do when I'm nervous.

"That doesn't change anything, you still knocked me down, hurt my ass, and made my shit go everywhere, and look! You ruined this pair of panties! Those were my favourite ones, and the only pair they had my size! What are you going to do to repay me for them? See these? Look at me when I'm talking to you.. LOOK!" she shoved the panties right in my face, forcing me to acknowledge her and the panties in question, and making me blush and harden even more. "What's the big deal? It's not like you haven...." She trailed off looking me right in the face as I looked off into nothingness off my right shoulder. I don't know why but when I get nervous I always turn to the right, I guess its to try to shield my good ear (I have over 60% hearing loss in my left ear)

"Oh... my... fucking... god... No fucking way... Are you serious?!"

I looked at her for the first time, right in her face and saw the questioning look, but in a split second I also saw just how unbelievably gorgeous this woman was. Long dark hair, ice blue eyes that I have to admit weren't too appealing at that moment, and the most perfect compaction that I could only dream of having.. To put it simply, even only looking at her face, I knew this woman was way beyond my league, not that I was actually thinking about trying to ask her out or anything, it was jus the automatic guy thought I guess.. No that's not true, most guys wouldn't be in that situation, they'd be trying to pick her up and making some rude comments about her undies by then.

I was awakened from my seemingly momentary but actually couple minutes of thought by her, "hello, Earth to big guy, you in there? I'm the one that got knocked on my ass and you are spacing off like you had a concussion."

"Wha? Huh? Oh yeah, I'm sorry, what were you saying?" came my reply, I truly was out of it. Cute giggle again, "You really were spacing off weren't you?"

In a very rare completely subconscious moment where the stars aligned and I said the right thing I replied "No I wasn't spacing out, I was just thinking how your eyes rival the bluest of skies and how anyone would be so very lucky to get to gaze into them everyday of his or her life."

Now it was her turn to blush and be speechless, as well as my own because I couldn't believe I actually said that. We stood there for what felt like hours but really was all of thirty seconds before. "Wow! So, there is some suave, romantic, poetic features hiding in the overly shy, tall, incredibly cute guy, that's afraid to even pick up a girls underwear. Speaking of which, what are we going to do about these.. I could have you pay for them.." she trailed off seemingly trying to think of the best way to make the situation out to her benefit.

"I really am sorry I ran into you, and I'm sorry for ruining your, um, panties, but I can't pay you for them. I don't have any money, I was here trying to get a job and they rejected me again and..." I stared down once more hurting again, tears starting to well up once more, "I'm sorry, I need to go." So I turned and left but before I could get anywhere, "Hey wait up big guy, I'm sorry, I didn't mean to be such a bitch, I just get really aggressive when I hurt."

"I know the feeling. I've actually punched brick walls when I got hurt. I am sorry, are you ok? I didn't hurt you too badly did I? How's your... *gulp" I stammered, staring at her amazingly cute round ass for the first time, innocent by intent, but now meaning something far different as I subconsciously wondered what it'd feel like in my hands or naked in my lap or... I snapped to feeling the sudden moisture in my pants and the now painfull, and painfully obvious, hard-on pushing the front of my pants out. I quickly tugged down the front of my shirt trying to cover it but she ad already noticed and her hormones were now firing on all cylinders and making her se me in another light as well.

"You know what, forget it, it doesn't matter, its just a flimsy, overpriced, piece of material anyways.. I'm Diane." She offered her hand to me out of the blue making me look up from her ass that I was still staring at even though I meant to look away. I slowly looked up, checking her out, though once again not meaning to, noticing her fit body, amazing though not overly large breasts, and the fact that I could actually look at her eyes and her mine without me bending over or her craning to look at me. The thought went through my head but.. "Wow, she's tall"

"Excuse me?" she said looking me in the eyes.

"What? Oh, um." I blushed "I was just thinking that you are pretty tall, I'm not used to being able to look women in the eyes without really looking down on them.. You must be, what, 5, 10?"

"Hehe, 5 11 actually, I know the feeling, typically guys are only as tall as me or shorter, and all my girl friends are way shorter at like 5 foot.. it sucks. It must be hard for you to date girls that are so much shorter. Always having to sit down, bend over, or pick them up if you want to kiss them.. Guess it'd be great for bj's though, you'd just have to stand there and let them do it." With that she looked up and noticed just how uncomfortable I was which reminded her of her earlier observation and thought, before my bulge distracted her.. "Oh hey, you never did say answer me about why you were so shy, and you didn't tell me what your name was when I introduced myself and that's just rude."

"Two things, firstly you never actually asked me why I was shy, you just went off about "no way, oh my fucking god, you cant be serious.." however you did it. Secondly, My name is Justin, though everyone calls me Otis, don't ask it's a long story, but I do go by Otis, and yes, I know, "like the cute little puppy in that movie." So don't go there." I snickered..

"Hell no, pugs are ugly, but you are cute so I don't see the connection other than the name." she laughed and I noticed her very slowly checking out my entir body and saw her bite her lower lip, for the first time I could see a woman actually was interested in me and attracted to me..

"You really think I'm cute? I'm sorry to say but I think you hit your head and not just your ass. Nurse, I think she needs a checkup from the neck-up ASAP, ding, Doctor to surgery please, doctor to surgery.." She lost it and started laughing her ass off.

In a fit of giggles, "what the hell was that? That was the funniest thing I've heard in a long time, where did it come from?"

"Sorry, my parents and sister call me Batty sometimes." I offered.

"Batty? Why the hell would they call you Batty other than your minds probably got a bunch of bats in it..?"

"Oh its for Batty Koda, you know, Robin Williams' character in Fern Gully. Remember, bzzt wrong channel.. Where he was always on the wrong channel and his mind wouldn't work right, it's also where I got the checkup from the neck-up thing." I explained seeing the connection that no-one else could, as usual.

"Oh yeah, I remember that movie, I think I have it on VHS somewhere still. That was his element, he was right at home in that movie, total improv, well kind of. Hey I just had an idea, I know how you can pay me back for the panties, and you won't even have to pay at all, no money. All you have to do is come with me, *giggle* and just hang out with me for a while and keep me company, I will even let you pick where we go. How's that? Sound good to you?"

She had this mischievous look on her face that I could se she was trying to hide, and what was with that giggle? No way could she be trying to get me to fuck her, no way would a chick like her want me.. "Ok sure, I guess, where do you want to go, what do you want to do?"

"Nope, I said you get to chose, and not just home to get laid either. haha.. ( followed by a really quiet "mmmm" so quiet I thought I imagined it) So where to?"

"What kind of things do you like to do?" I asked really not sure what to do, thinking to myself, is she asking me out or is this really just to pay off the panties?

"Like I said, its up to you to pick, I'm up (quick glance to my crotch) for anything, you name it. except for sex." With that she gave me what can only be described as a shit eating grin.

"Well, there is one thing Id really like to do, as long as I don't make too much of an ass of myself, but I can't afford it, and I can't go home to get the clothes for it.." I thought out loud again.. I really need to stop doing that..

"What do you need for it? If its not too expensive I will pay for it, you will just owe me more time with me to pay me back, hmm and maybe a nice backrub too.. I bet your big hands would be great for giving a backrub, nice and strong but probably gentle too.." She really surprised me with that one and once again I was dumbfounded and wondering if I was just too dense and she really was trying to tell me the only thing she really wanted was me inside of her. I crossed that out of my mind. A 5'11 probably large C, small D cup, beauty like her (no clue really I just know they look nice and fit her body perfectly) couldn't possibly want that from a big ogre like me.

"How about we go Ice Skating, its cold, but I've only been once and I love hockey, I've always wanted to skate since I first saw the Mighty Ducks as a kid, it's why the Ducks are my favorite NHL Team. Hence why I said wed need the right clothes and stuff, and I'm not sure they'd have size 15 skates to rent."

"Wow! Ice skating! That'd be so fun! I've never been ice skating on a date before, this will be a first. I haven't skated in years, I hope I don't fall on my ass too much though, you already made is sore, yeah lets go buy some warm clothes and see if we can buy some skates, I am not wearing rentals.. eww gross." I had to laugh at her, now that she was relaxing, and not being so proper she was really showing she was a normal girl, a very beautiful one, but still normal and a bit of a dork. I could seriously fall for a woman like this. Completely not realizing she said it was a date..

An hour and a half later we were in a local shop, we had already went and bought sweat pants, hoodies, gloves, extra socks, a beany for her, which she looked amazingly cute and innocent in, and an overcoat for me. I couldn't believe it, she had to have spent close to two hundred dollars on me and 200 on her, she must be made of money, and now, she just bought her own ice skates to the tune of 250 dollars and was encouraging me to get my own pair of hockey skates hat are over 400 dollars.. Well after some arguments and some issues with sizing I finally decided to give in and let her buy me whatever she wanted. So I got a black pair of size 15 skates, black and blue hockey "shooters" gloves and a warm jersey that was devoid of any team affiliation, just black. Twenty minutes later we were in the rink both trying not to make asses of ourselves while little five year olds zoomed around like they were flying. We both had to laugh when one decided to skate between my legs, which is quite a feat seeings how I only have a 30 inch inseam.

So there I stood, or skated at a new height of probably six foot eleven thanks to the padded, strapped jacket Diane insisted I get o help protect me back WHEN I fell, and it turns out, when she pulled me down when she fell. I was amazed, once I got over my initial cold issues, and fear of being see and laughed at, I was great at skating and within thirty minutes on the ice, I was skating literal circles and figure 8s around her and getting more confident by the second, that is until Id get too close, she'd grab me and it was like Jack and Jill without the hill and we were on frozen water..

We really didn't talk much while on the ice, just laughed and I just enjoyed myself, honestly forgetting about her and just doing sprints up and down the ice at one point and doing Norwegian circles and everything else I could think of. Before I knew it, 5 hours had passed and she slowly skated up to me and told me it was time to go, it was dark and she was hungry.

"How the hell did you skate like that? I thought you said you only skated once, cant stand on blades, and the last time you skated was for seconds in middle school?" she was a little perturbed with my sudden talent.

"I don't know, once I got comfortable, it just was natural.. Maybe it's partly because I'm part Norse, it could be in my blood, who knows. All I know is I love skating and just wish I had a stick, puck, goal, and space to shoot without hurting those kids.. They were fun, challenging me to races and loops and stuff, one even called me big brother, it was so cute." I relived, the little girl that called me "Big Bwother" actually about made me cry and made me want to pick her up and hug her for it, it was so sweet.

Diane saw the look on my face and decided to tease me a bit. "Oh big bwother, you alweady have a stick to play wif, all guys do. 'Cept its more fun to have a cute little girl like me play wif it.. Do you want me to play with your big hard stick big bwother? It is hard isn't it big bwother? Oh wow, that must hurt big bwother, can I kiss it and make you feel better?" She really got to me, and she rubbed me up and down through my three layers of clothes while sitting on the bench next to the lockers with kids running around and I was so hard it seriously did hurt and I was leaking precum like crazy.

"Enough of the "big bwother" its not right, and I thought you said you didn't want sex, that you were hungry and wanted a back rub." I gasped as she gave me a squeeze.

"Big bwother is so hard, he needs his cute little sister to give it a kis and make the pain go away." She teased "Enough of the big bwother shi... Oh fuck!" She moved her hand inside my pants and inside my boxer briefs and it was cold as ice, yet it only made me harder..

"I said I was hungry but I didn't say for food, I'm thirsty too and by the feel of it you've got more than enough meat to satisfy my hunger and more than enough liquid to satisfy my thirst. Come on, lets get out of here. You owe me for all the shit I bought you and seeing you skate around with so much confidence and hearing all the women talking about how sexy and tall you are and how they'd love to suck your cock while you skated and then have you fuck them till they can't stand has my little kitty (she said little kitty with that same innocent little girl voice as big bwother) absolutely drenched and dying to be stuffed.. Now lets get out of here so I can give you head in the car." With that she pulled her now soaked hand out of my pants, looked at it, then me, then while looking me in the eyes licked her palm clean of my juices and said "like going without water for a week and then only having a cup, that only made my thirst grow.. lets go NOW!"

I went to leave like I was but she got an evil smile and said I could only wear one pair of pants out, that it was too hot outside and Id die dressed as warm as I would.. I knew she just wanted my bulge o be visible to all the women but I had no choice so I stripped down to just one pair of sweats, put everything in my bag, put on my shoes and tried to head out as quickly as I could with my sports bag leading the way to hide me. She wouldn't have it though and pulled the bag behind me in effect cutting off the use of my left arm as a shield as well, and then latched onto my right arm and walked me out like a prisoner to a cop car, allowing everyone to look as long as they wanted, and me to get so red it wasn't even funny.. Especially when one little girl asked her mommy what I was hiding in my pants and her mommy said the greatest meat on earth.. which her daughter had to ask why I had meat in my pants but luckily we got out the door before I could be forced to explain..

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