Archive | January, 2015

How I lost my virginity

10 Jan


There have been many great failures in American history. Vietnam war, Bush administration and the losing of my virginity. I’m going to shed some light on the disastrous beginning of my sex life.

I was a horny little bastard who started masturbating at 10 (before i could even shoot a load)  I remember doing it by accident but liking it.  Apparently I was going about it the wrong way for years by doing some over the top maneuver.   Eventually I learned not to cum into the palm of my hand.   Grew tired of being known as “sticky fingers”. 

When I turned 15 I was one of the first to get on AOL.  This was heaven in a electronic box for teens everywhere.  We could have dirty chats with strangers even share explicit pictures.   My poor parents thought I was using that Compaq to make something of myself.  Ha!

The good old days of A/S/L/ the universal internet greeting better known as Age? Sex? Location?   I’d always lie because know one really knew what a catfish was back than.  Hell we were all catfishing  each other in 1996.  I’m sure that 18 year old big tits blond who got me off was really some 49 yr old 300 pound bearded trucker named Bob.  Bob sure did know how to cyber, good old Bob.

Now I wasn’t too socially awkward or bad looking that I couldn’t get girls in school.   Its just that girls on AOL (Or Bob) came across as really easy.  I used the chat rooms as a way to explore and get to know females sexually.   Eventually I graduated from cybering and phone sex to wanting to meet chicks in person. 

 Getting laid became my sole purpose in life.  I searched the internet for slutty girls to lose my virginity to. I eventually made an internet girlfriend named Elizabeth from the Bronx.   She was a sweet girl from a good family.   That created a problem she had morals and was a virgin.  Typically a virgin is a prize most guys would want to achieve but being one myself I needed something else.  A damaged hates her dad kind of girl who’ll fuck & suck just to get back at him for walking out on his family. 

 After about a month of dating which felt like an eternity that got me no where but kissing.  I realized her panties were locked tighter than fort Knox so I moved on to plan B.  Elizabeth told me about her slutty cousin “Jessica” who met a few guys off line an fucked them.  So I dumped Elizabeth and befriended her cousin on AOL instant messenger.   After some talking I convinced her to skip school one day and come to my house.  “I’ll have weed and drinks” I said to sound cool and seal the deal.  

My idea of a party at fifteen was some Zimas and my brothers weed.   I stole  a joint from his secret stash.  To this day he still keeps his weed tucked in a box of Newports.   My brothers joints were slim as toothpicks but I was a sophmore with limited resources.  The skinny J with more paper to weed ratio would be enough to impress Jessica.

Jessica was a little older than me and I already had the inside track that she was experienced (Nice way of saying shes a whore).  I bullshitted her and said I’d fucked lots of girls and could make her cum.  I bragged about my large penis which by a teenagers standards still was’nt that big.  See I was born hung for a baby but I out grew my dick quickly so it really was not much to brag about.  Yet I did.  Now I had this hot slutty girl coming over expecting to get the fuck of her life.  I panicked.  

Shit I dont even have condoms.  How the fuck do I get condoms?  Sex ed had scared me into thinking aids was running wild among high schoolers.  I could’nt go to the bodega my parents are friends with the owners.  My parents knew everybody in the neighborhood.  Than I remembered my friend Willy’s dad owned a gas station and they had a condom vending machine.  I asked  Willy for some Jimmys for my Johnson.  Willy obliged and hooked me up with three rubbers.  He also got me a pack of Zimas.

Weed? Check .  Alcohol? Check? Condoms? check.  I was ready! Or so I thought.

We cut school as planned.  She came over to my house and to my delight she was as hot as described on the chat.  I could’nt believe I was about to bang a hot chick.  It was a sure thing she told me so herself she came to fuck.  Of course that was all on the phone and on instant messenger but no one lies on the internet right?

After some smoking and Chinese food I got the courage to make my moves.  Nothing like General Tso’s chicken to make a boys balls grow.   Must be the msg.

At this point in my life the farthest I’d gone was some finger banging.  I wasn’t even good at that. My hand was like Christopher Columbus discovering America.  I explored had no idea where I was going but accidentally found some land.   Much like the Native Americans she regrets my invasion.

After some intense making out and taking all her clothes off.  There she was a sexy naked girl on my moms couch.  I thought about fucking her right there but even though my mom was old school and wrapped her couches in a condom of its own with plastic I didnt think it would be right.  So I lead her to my room in all her naked glory.  The first of what I’d hope would be many conquest in my lair.  

I laid her on my bed and we made out again.  I was still in my t-shirt, Jordache jeans, and sneakers.  I was self concious all of a sudden I thought about my lies…

I was’nt a 6 ft 180 fit 17 yr old sexually experienced stud with an 8 inch dick like I made myself out to be on AOL.  I was a chubby 5’9 virgin and well if I fucked her twice I technically would be giving her 8 inches of dick just not all at once.  I froze had no idea what to do.  Think, think.  So that I did.  I took a moment and thought back at all my years of porn watching to that point.  I reenacted my favorite porn scene so I did what Peter North would do.  Call me Pedro South cause I went down.

I dont know what I did with my mouth but Jessica sure seemed to like it.  I think I was naturally good at this from eating lots of mangos.  I ate her for awhile until she leaned up and started kissing me than said “put it in.”  Hmmm what is this “it” she speaks of? My not 8 inch dick? Fuck!  Okay I figured if she didnt stop when she noticed I”m about 3 inches shorter in height than I claimed to be she may not notice my penis is three inches short either.  

I grabbed the condom and ripped it open.  Pulled it out and thought I have no idea how to put this thing on.  Why the hell didnt I pay closer attention in sex ed? What am I supposed to do with this rolled up plastic sock? Ok I’ll do what I do with laundry and unroll it yeah thats it.  So i unrolled the sock I mean condom and I unrolled it way too far thinking I’m the mandigo I claimed I was.   I start sliding it on and as I pushed down I kept filling it with air.

I was making balloon animals with my condom this was becoming a nightmare.  Not only do I not know how to fuck I dont know how to put this on.  She asked if everything was ok.  “yeah I’m good just this condoms broke”.  I pulled out another.  This time I rolled it out to a length more suitable for my sausage.  This was less of a chorizo length and more fitting for a vienna sausage.   I put it on with less balloon animals this time.  Finally got it to where I think I could get it in.  Now how do i do this? 

I fiddled around down there for a bit still in my t-shirt and knee high socks hovering over this sexy seventeen year old.  I lied about my height, weight and dick size I can tell by the look on her face she was expecting by now for me to be lying about how good I’d fuck her.  Still she didnt stop me she was nice enough to lend me a guiding hand on where she wanted me to go in.  And go I did!  I gave this girl the five best strokes of my life than poooooof.  A magical eruption happened filling my balloon giraffe condom up.

“You didnt finish did you?”  She asked with a horrified look on her face.  “No were just getting started. I think I hear someone at the door hold on let me check.   I made my escape to the living room to recover.  I took out my last condom took the other cum filled condom and put it in my jordache jeans back pocket.  I dont know why I did that I had a garbage can ten feet away.  Guess I was saving it as a memory so one day I could pass on the used condom to my son.

I went back in the  room and hoped I could do a better job the second time around.  Afterall this girl just deflowered me and shes been a good sport.  I tried to do something not sure what but the second time I lasted longer so much longer that I was thinking she might think I’m gay if I dont finish soon.  Eventually she got tired of my fat sweaty body crushing her and moved me over.  She got on top and showed me exactly how experienced she was.  

It was great the kind of sex you only dream of or watch in a movie.   This girl put it on me and I’ll remember Jessica forever. 

We hung out and hooked up a few times after but than I got a new girlfriend in high school and that was the end of that.  Years later I ran into her again and found out shes cousins with one of my friends.  I told her the truth that she was my first and she felt honored about taking my virginity.  I also told her the one thing I didnt lie about was giving her 8 inches of dick that day.