One unfortunate sex turns into many

Hey my lovely Readers.

I have been going mad trying to think of material for my Blog, I have plenty of sad stories and information but I really need to break it up with some sexy funny stuff.

Since my Blog has been out there in the world for nearly a week it has gotten over 720 views. Now I don’t know if that is good, bad or normal but I can’t help but be a little proud of myself.

So today I am going to post a little “time line” that maps the beginning of my tragic sex life up until Mr Big.

Maybe some of you will relate, maybe you will read this and say to yourself “hey that happened to me too” all I ask is that you enjoy it and tell all your friends and family or any famous connections you might have about my Blog.

I suppose the only logical place to start is at the beginning, my very first time.

It was summer holidays before college and I was 16 years old, my high school boyfriend Matt and I had broken up about two months ago after a eight month relationship (he is still my longest relationship). He had found himself a new girlfriend only a week after we broke up; but it didn't last, she cheated on him after he lost his virginity to her.

So you can imagine that it didn't take long before he was texting me and arranging for us to catch up.

He told me that he still loved me and that he made a mistake having sex with his ex, what ever he did it worked. All throughout our relationship he had tried getting in my pains but I was too nervous, he would make me feel bad by saying things like “if you don’t give me a hand job I’ll break up with you” or “lots of girls at my work flirt with me”.

One day he invited me over to his house to watch a movie (only now do I know when a guy asks you that he always means sex) it wasn't long till we were making out on the sofa.

He kept asking me “is this ok?” witch I would always respond to with “I don’t know” and continue kissing him.

He asked me if I wanted to come upstairs, I again quietly responded with  “I don’t know” so upstairs we went.

We then began ‘the awkward teenage shuffle’ dance he takes off my top and his top while I try to cover myself, then he spends a good one minuet fumbling with my bra while still kissing me.

He gets the bra off but his next challenge is tugging it away from me while I have two hands trying to cover my boobs and my belly like my life depends on it.

“You know I have seen them before” he says while he releases my bra from it's death grip.

I quickly flatten myself against him, ha now he definitely can’t see me. Then I feel something I look down and see his erection through his boxers, oh my goodness i knew about them and knew what to expect but I have never seen one in real life, I wonder what I’m suppose to do with it. Should I grab it? I know that boys like it sucked but that’s icky.

Next thing I know the radio is on and we are on the bed, I’m laying on my back and he is having sex on me (not a type-o)

I felt like I should be doing something more so I grabbed his back "are you ok, is this ok?" He asked  "I don't know I think so" i respond.

He then started to get me to stroke his thing, but i pulled my hand away.

Fifteen minuets in and i was getting board, i remember the radio playing Rihanna please don't stop the music and a few ads telling me to trade my old vacuum and a McDonald's jingle telling me i can add bacon to any burger for only $1.

By that stage i looked like this:

It didn't take long till i made a noise and told him to get off...Ah romance.

After we got dressed i walked him to subway and then i walked home.

When i started college i had strangers warn me not to have sex with him because he made a $20 bet with a friend that he could get me into bed by Easter,  we had sex the day after Valentines day. I still have never spend Valentines day with a guy.

So that was when it started, my next few sexual encounters were not so "long" or memorable.

I had just turned 18 and i was going to a guy friend Jake's 18th birthday, I had a bit of a crush on him and I liked him a bit back in high school.

The party was good, we got drunk and I had a very low cut dress on (which i still have) everything was going swimmingly.

Once the party wound down the 10 boys went to their tent and my best friend Diana and i went to our tent.

About half an hour later Jake came in and lay down next to me, he then started to put his hand under the blanket and drunkenly play with my minge, he then got my hand and put it on his wing wang woodle, i felt around for the remainder of it but only something the size of my thumb could be found. ok this should be easy to wank off, hmm now where are my tweezers?

Diana then got out of the tent and went to the bathroom, I rolled over and straddled him. Why wont he kiss me? i would but he isn't giving me any signs.

Oops! Diana is back.

I moved over to the far corner of the tent and she slid in beside me. 

I think Jake got the hint and he left.

But after that he had tried getting in my pants every time we drank together. But he never kissed me so he never got any.

After Matt there was a bit of a sex gap.

I think i might have had sex in a night club but i don't think it counts, He slipped inside for only a moment and then i chickened out and went to find my sister.

Then when i was 19 i moved away to a new city and started seeing a 25 year old called Harry, he had a baby, and ironically he wanted to wait three months before we had sex.

But at our  two and a half month mark we were making out in bed when next thing i know we were doing the sixty-nine. I had never put a penis in my mouth before let alone seen one so close.

I try sucking on it and licking it, then he put it deep in my throat and i was nearly sick so then he got me to sit on his face.

I was truly happy he decided to shave his stubble that day. But what he did next is something that will stay with me till I'm a sweet old lady in a home telling grand kids NOT TO USE TEETH!

I want you to imagine for  a moment rapid moving teeth like this:

Now imagine winding up the teeth and putting them against your clit.

Harry and i never did get to the three month mark, I felt a bit cheated after all that.

Then there was Leigh.

He was a cute military guy i met online, by our second date he was telling me he didn't want a relationship and was asking me back to his dorm to "watch a movie" by now i knew what that translated to

The sex was good although I really had nothing to compare it to, I never climaxed and when he was about to cum he would say "where should I put it?"

In other words "I want to cum on you or in your mouth" 

I always chose mouth, It's less messy.

I got pretty good at head with him, I also lied and told him "I'm the best and i love giving head" people only believe what you tell him.

One night while giving head I burped, "umm that felt weird" he said. I looked up at him and wiggled my fingers like tentacles and said "I'm a Kraken From the Sea!"

I think he pretended not to hear me...Thank god.

That wasn't the only time I humiliated myself in front of him.

once we were having sex and he wanted to cum on my chest, i figure his penis is a guest in my body and i need to be a obliging hostess. So i let him.

Big mistake, it went on my face in my hair and in my eye. You have no idea how hard it is to get cum out of your eyebrow. I told my Mum and she called me Jizz eye for a year.

Haha that's the face I made.

Then i was 20.

I picked up in a night club for the first time. I was drunk and he was ok looking. Diana got his friend. we went back to their place and there wasn't really a lot to it.

The wind died quickly no matter how much I sicked and wanked, but we were so drunk i don't think ether of us minded. Then i was sick on the grass outside and my friend and i got in a cab and went home. 

I don't remember his name.

Then near my 21st birthday i had one last hook up with Leigh  It only shows how dumb i am. He tricked me and made me think he loved me and we could be together. 

Then he called me a week later to tell me he can't see me because he will be doing stuff. Wanker.  (story of my life)

A week before i turned 21 i met the love of my 21 year life, the guy i wanted to marry, and the guy I could open up to.

Anyway you don't need to know about that. What you do need to know is that i got my period while having sex with him, we were doing it doggy style and he says "can you smell something metallic?" 

My heart stopped, he turned on the light to reveal blood everywhere.

On his dick his belly his face and all over me and the sheets. 

Well if that isn't bad enough, It happened to me twice. And I'm on the Pill.

Lucky that is so bad it cancels out the fanny burps and cum dripping out of me in the shower or farting on him during sex.

Long story short we were about to move in together and then suddenly he pulls away then after months of me crying and trying to make him come back he tells me he can’t love me anymore. Now he has a new skinny girlfriend.

And that brings me to Mr Big

Here is the link:

http://anawkwardgirlsguide.blogspot.com.au/2013/03/saturday-night-with-mr-big.html

So I hope you got some kind of entertainment out of that, I did in some ways. 

So if you have ever done anything in the bedroom that would make you cringe, it's ok. We have all been there. 

Boy have we.....

All the best 

The Awkward Girl

xoxo

Saturday Night With Mr Big

Hi people.

As promised I will relay my traumatic Saturday night with Mr Big.

I think I will start with my intention of the night.

After my breakup with my ex and the discovery or his new twiggy blond girlfriend I needed to move on and fill the void, and the best way to do that was with a strangers junk.

I planned on going out alone, (a risky move for someone who has been drugged twice in a night club) but I was willing to put that aside in the pursuit of love.

Everything was set; 

• My roommate would be away till Sunday afternoon
• My house was mopped, swept and vacuumed
• I put my new sheets on the bed
• I had spent the last two weeks researching how to pick up men in nightclubs.
• I got a tight red dress and a bra that will take me from a B to a C cup.
• Hair was done - although i did loose a fight with a bottle of toner.
• Fake tan wasn't too blotchy
• And i covered my bleeding shaving rash on my lady bits with Sally Harrison Air Brush Legs (remember that name, one day it will save you)

I looked pretty good, despite the fact i was so bloated i looked four months pregnant, but that went away in good time.

Bow chika bow wow

Yep I was going to be in for a fun filled night.

I first went into town with some friends that were going to an event called sky fire, It was only 6:30pm so i hung about watched the fire works ate too much cheese and chocolate and drank 3 mini bottles of champagne.

I don't want to think about the calories, but i told myself the many hours of dancing ahead of me will work it off.

Finally it was 9:30pm and i gave my friend my jacket and booz and walked to the Uni Pub.

It was about half full in there, plenty of good looking guys but the night was so young it would have died at birth.

So i had one drink and moved on to a popular bar/club called Moose Head, i thought this would be a perfect time to get my stamp and they were having a St Patrick's day party.

 *sigh* i should have stayed at the Uni Pub, this place is deader than Lindsay Lohan's career.

I moved on. What i really needed to find was a bar where people go before the action, and it needs to be full enough so i don't look like a pathetic girl all alone in a dark bar.

People already think i have a sad face; i don't need to be pathetic too.

I felt exposed in the middle of the cobble stone square, people were looking at me. i pull my shoulders back and attempt to walk with confidence, i tell myself they are only looking because you're so hot and you're the only girl in a red dress I've seen all night.

I find a semi crowded place called Hippo Bar filled with middle aged men in suits and the odd younger one. Perfect!

I ordered a disgusting overpriced glass of champagne and placed myself on a seat on the balcony and fiddled with my phone in the hopes that people will think I’m texting all my friends and arranging a meeting.

It clearly didn't work.

I looked up and saw a girl in her late 20s early 30s smiling at me. Let’s call her Ms Hippo Bar)

She asked me why such a pretty girl was sitting alone.

I raised an eyebrow at her "do you really want to know?"

"Yeah, I think so" Ms Hippo Bar said after a long pause.

So that’s what i did, i told her of my intentions and of my extensive research and that i have even taken the time to vacuum my house.

She was impressed with my commitment to the cause, clearly i had put a lot of thought into this.

She then called over her husband (Mr Hippo Bar)

She tells him what I'm up to and that I'm nervous and she asks him how i should proceed.

Mr Hippo Bar tells me that a girl as stunning as me and in THAT dress has the luxury where i can stand in any room in any given well lit spot and the men will come to me like flies on honey.

All it takes is a smile and a touch to the arm.

He also pointed out that i look sexy and not trashy because I’m not showing any cleavage and i had flat shoes on.

Mr and Ms Hippo Bar then started to point out 30 something year old men i might like, so that was my queue to head to TnG (a popular pre-night club spot with some live music)

As i walked the short distance to TnG i went past a few cafes and restaurants, there were business men sitting outside drinking coffee and ending their night.

As i got closer the one facing me looked up and his associate followed his gaze, in perfect timing their heads turned as i walked past. It reminded me of a cartoon.

It took everything i had not to smile to myself and to keep walking till i got to the bar.

But that was just what i needed, I truly felt like i could command the attention of any room. This must be what self esteem feels like.

So i payed the $5 entree fee and i went straight to the bathroom.

Its so annoying how quickly alcohol passes through me, its not as bad as coke but pretty close. 

I am also happy to report that i also pooped while i was there and that made me feel a bit lighter.

I could hear some girls in the bathroom talking about drunken sex, immediately my ears perked up.

Now these are some woman i can talk to.

i came out and washed my hands and waited for them to come to the sinks.

"Like OMG! I like so love drunken sex!"

"OMG Meeee Tooo. It is like so amazing"

One looked at me and saw me smiling.

"You know what I’m talking about gurllll?"

I laughed at her and admitted that i have never had drunken sex.

"Well you gotta be gettin out there and have some"

The drunk girls left the bathroom and i counted to ten and followed. I think i hoped that they would include me in whatever fun time they were going to have.

I saw Bathroom girl at the bar and stood next to her pretending to order a drink, then i let out a silent yet deadly fart.

Bathroom girl suddenly looked around and said "Omg what is that? arg it's disgusting!"

I took this as a opportunity and pretended to notice too "Yeah your right, eww someone must of done a walk by fart"

I then tried to start something up "hey you’re the girl from the bathroom" 

She looks at me a moment "oh yeah! Hey! Go and have drunk sex! See ya"

Damn it. opportunity gone.

There was nothing more for me at T'n'G so i made my way back to Moose Head hoping that things had picked up there.

As i was making my way a random guy lost his shit and went crazy over my dress "OMG! Holy Shit! You look so good you should be in L.A!!"

"umm thanks random"

Well Moose Head had improved.

People were dancing and drinking, i made my way up to the dance floor and i saw a friend of a friend (Tights as Pants)

We exchanges niceties and i got up on the higher part of the stage to check out the meat market.

I was dancing for only a few moments when (Mr Big) started to dance with me. He was everything my ex wasn't.

Tall about 6'4, handsome, buff like a god and an amazing kisser. No tongue and pure passion.

It wasn’t long till he whipped out his phone and showed me his "modelling picture"

After our night he was kind enough to send it to me, so now i can share it with you. For his privacy i have cut off Mr Bigg's head

Oh and FYI he is a Rugby player (Note the ball)

After a while I offered to get him a drink, he was very shocked by this and he liked it. He said a lot of girls expect the guy to get a drink for the girls.

(Ladies take note, if you want to stand out try getting HIM a drink)

Then he got me a drink witch I reluctantly drank, we went to the bathroom and met back on the dance floor.

A few more moments and he were asking me if I wanted to get out of here.

I couldn't believe it, it worked I did it, I picked up.

A short $35 cab ride later we were back at my place; this was the part I was unsure about.

I took him to my bedroom and unzipped my dress. But he was talking about something I was only half hearing. So I kissed him and pulled off his shirt, he was so confident in his body, and I really don’t blame him. (If you need a reminder please look at the image above)

We went down onto the bed and kissed, it was slow and sweet. Then he started to work on my bra, one hook then some struggling.

I should really help him, this is a new bra and he will be there all night.

“Do you want me to get it? I won’t think any less of you”

But Mr Big’s will was strong and in the end he got it.

Then suddenly he flips me onto my back. It was unexpected but no more than when he sticks his tongue in my love cave, he starts licking and sicking and then he shoves two of his massive fingers inside me, OK ouch but I can handle it.

This carried on for a while until he rams his fingers up so far I gasp, and then he starts to move them against something hard. I don’t like it and the clit sucking is getting old and a bit unconformable.

I just want him to finish and we can sleep.

“Hey…..HEY! You better stop or I'll cum.”

“That’s the idea” he says.

Ok… I pull away and roll him on his back, two can play that game.

I tug down his pants and undies and they fall to the floor. Suddenly I’m in shock, it was like a fist.

I decided to try anyway. I attempt to wrap my lips around his knob but I couldn't get my mouth wide enough. So then I decided to wank at his foreskin and lick the tip, that kind of worked but he wanted more.

So I pulled out a condom and attempted to slide it on, it didn't budge. At first I was thinking I had it on the wrong way but I didn't  With a little more rolling I got it on half way.

I started off on top, with all our kissing and then he eating me out I was pretty wet. I lined myself up and eased it to the entrance. Omg it won’t go in.

I gave it a bit more back and forth and I got the head in, but it felt like I was going to break.

After some rocking back and forth we try with him on the top, Worse! And his hips were wider than mine so it felt like my hip joints were going to pop out.

Then came the new pain. Turns out he likes to bite ears.

You See what I'm talking about.

And he rubbed my clit like a genie was going to come out of my vagina and grant him wishes.

And while he was trying to ram his penis into my now dry minge he started to pinch my nipples like he was expecting them to come off. He only stopped for a second when I said “ouch!”

This went on for an hour and a half, I then reached a point where I had to just say stop, but it took a while to get the hint. At first he then held down my arms and preceded to finger fuck me.

Eventually we went to sleep, after an extra half hour of him softly tickling my skin and trailing his fingers back down under, I then had to grab his hand like a child about to touch a hot stove.

The Next day he started back up again with the tickling. I knew there would be only one way to be rid of him.

“You wanna have sex again?”

I hated myself for asking, I was in so much pain from last night but I just wanted him to cum and go.

So I attempted to put a condom on him again, and then I lay through an extremely painful ten minuets of him licking my bruised clit until I had to get him to stop.

I looked for my lube but couldn't find it. Damn it!

Then he tried to force himself in me again, I was dry and tender but by god was I going to get him to cum.

I got on top of Mr Big my body screamed in protest, then I rode him, it was tricky and I had to nearly slap his hands away when he went for my nipples, after a hour I couldn't take any more.

“Are you close? You got to tell me if you’re close”

No response and I was done.

“what? But I was close” Mr Big said

“Really?!”

I climbed back on and rode him like a bunny fighting through the pain all over my body, and the chafing between my legs.

But in the end he came and I was relived even if it was all over my new sheets.

I made him coffee he had a shower and then soon after he was out the door and in a cab, and I was sitting on frozen peas and calling my best friend.

I hope you liked my first real blog entry, the others won't be as long as this one only happened on Saturday night, so its all still fresh in my mind and my hips are still hurting.

You know i never did get to dance off all that cheese but i think i should get a  merit badge for attempting Mr Big.

oxox The Awkward Girl