Always with the Jerks

Story Info
Hailey always picks the wrong guys.
3.2k words
3.99
11k
1
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Hi guys this is Katie. This is actually my first time doing anything like this, so I really hope you enjoy it!

-------------------------------------

"Hailey Turner."

Looking up and realizing my name was being called I quickly got up and made my way up to the stage. Looking down at the swarm of students who were also graduating with me I realized how surreal this day seemed. It was just four years ago when I started college as a young inexperienced girl. Of course that all changed when I met Travis.

Travis Ellington was the kind of guy who walked in a room and everyone noticed him. He is an amazingly handsome man. He is 6'2, six pack, dark brown hair, and has baby blue eyes. We met at Chris Parkerson's keg party my sophomore year of college. I had spent my first year trapped in the library and come sophomore year I was determined to get out of my cage. I'm still surprised I was the girl who caught his attention. It's not that I'm ugly. Sandy blonde hair, height is 5'5, curves everywhere, and hazel eyes were always noticed by a few men. Not the Travis Ellington's of the world though. After a few drinks with his friends he finally came over to introduce himself.

"Hi, I'm Travis Ellington."

"Um, hi."

"You gotta a name?"

Blushing I quickly responded. "Hailey Turner."

"Well I just thought I come over here and tell you, Hailey Turner, you are by far the most beautiful woman in this room."

He scooted closer to me making me slowly inch my way backwards. I eventually was trapped by the wall. He leaned in close and I thought he was going to kiss me. I closed my eyes and prepared myself. Five seconds later I realized he wasn't hovering over me anymore. I opened my eyes and saw him smirking at me. Getting aggravated I stood up and walked pass him to the punch bowl. After arriving at the punch bowl I looked over my shoulder and saw he was gone. Apart of me was glad he hadn't followed, but another part had been hoping he would have come after me.

"Hi, were you just talking to Travis Ellington?"

I looked behind me to see a very pretty girl with brown curls down to her shoulder and dark midnight blue eyes. "Well, we didn't really talk. He just introduced himself to me."

"You are so lucky. I have had a crush on him since orientation, but he hasn't even glanced my way."

"Oh, I'm sorry." I really didn't know what to say because after his first glance at me he decided to introduce himself.

"Oh it's totally fine! Besides there is this other cutie here and he has totally been giving me the eye. Oh, I'm Tori by the way. Tori Whitson."

"Hailey Turner. I think I have seen you around before."

Tori and I discovered we lived in the same dorm complexes and instantly became best friends after that first keg party.

Walking back down the stage I easily spotted Tori who was in the back jumping up down waving her arms, so I could spot her. I waved back at her and laughed. Quickly scanning the fifth row I spotted Travis who was flashing his gorgeous grin at me and shaking his diploma over his head. Getting back to my seat I felt so excited and happy. I was about to start a new chapter of my life. It made me think about the first time I was with Travis.

I still remember the date. March 23rd. It stands out in my head because it was the first time I lost my virginity. Tori had been dating a guy from one of the fraternities on campus and had begged me to go on a double date with her. I had told her no a million times before, but for some reason I decided to go on this one. Maybe it was because I was sick and tired of her asking, or maybe I was just desperate. Either way I went.

Tori and I gussied ourselves up. We were going to a fancy restaurant, so appearance mattered. I decided to pull my hair up and curl little ringlets to hang around my face. I decided to dress a little sexy too. I wore a dark purple halter dress that clung tightly to the top of my body and flared out at the end right above my knees. Tori and I decided to drive to the restaurant together and meet the guys there. Well, truthfully I wanted Tori to take her car so that if I decided to bail it wouldn't ruin her night with Ben.

We arrived at the restaurant a little early, so we decided to go to the bar to order some drinks. We had two before the guys finally showed up. I had just sipped the last little bit of my drink when I saw my date. I quickly swallowed my drink causing some of it to dribble down my chin. I quickly turned towards the bar tender who saw the drink dribbling off my chin and he handed me a napkin.

"Hey. Sorry we're late. This one here had to take his precious time fixing his hair," Ben said pointing towards Travis.

"Oh it's no problem! Me and Hails had a few drinks and caught up on the latest gossip," said Tori already cuddling up to Ben.

"Well, let's go get our table before they offer it to someone else," Ben said while ushering Tori to the waiter who was waiting for us.

I started to follow, but Travis grabbed my arm facing me towards him.

"Hey, I just wanted to make sure you're okay with me being your date. Walking in I kind of notice you spitting your drink up and I wasn't sure if that was a good or bad sign?"

I realized looking at him that I was actually excited he turned out to be my date. Of course I couldn't let him know that.

"Well, I guess we'll know by the end of the date," I said with a coy smile.

He gave me an amused look and led me to the table where Tori and Ben were already devouring the rolls.

I couldn't believe how much fun we had talking about all the parties that year, especially the one where Ben got drunk and decided to go skinny dipping. Eventually we had covered every subject known to man including the racy topic about sex.

"I think the first time is the worse time," Tori explained while eating dessert," I mean you have no idea what you are doing and it hurts."

"Babe, I think the guy you lost the big V to had no idea what he was doing, so of course it sucked," said Ben.

"Well, Robbie Smith certainly knew what he was doing," laughed Tori who started playful poking Ben in the chest.

"Yeah, let's see whose name you're screaming tonight," Ben said tickling Tori on her side.

"Ben, stop it!" shrieked Tori,"we haven't let Hailey tell us about her worse and best time."

I suddenly notice all three set of eyes looking at me waiting for me to tell them about my sexual encounters. Problem was my experience stopped at making out.

"Um, well, there was this guy my junior year of high school and we did it. It was bad. Then, there was another guy senior year of high school and he was really good," I said unconvincing.

I noticed Tori and Ben seemed satisfied by answer, but then again their hands at that point had disappeared under the table. I did notice Travis giving me this look like he was unsure about something. After dessert, Tori wanted to go back to Ben's place so Travis offered to drive me back to my dorm. About twenty minutes later we arrived in front of my dorm room.

"Thank you for the lovely evening," I said while pulling my key out of my purse," I actually had fun tonight."

"Yeah I did too. Look I'm going to be blunt. Can I come in your room?"

I stared at him startled by his question. That had to be the reason why I opened the door and motioned for him to enter. It was completely against the rules for boys to stay over.

He came in my room and saw that my half of the room was neat and tidy. He saw my pink lace curtains, white trimmed bedspread, and my desk with organized folders and books. The other side of the room had an unmade bed and stuff scattered everywhere.

"You and your roommate must get along very well," Travis said sarcastically.

"Oh yeah, let me tell ya," I said laughing.

"Actually, it's not too bad because she spends most of her nights at her boyfriends," I said while taking off my heels.

Travis followed me and took his shoes off too. Then he decided to flop down on my bed.

"Comfortable?" I asked feeling unsure if I should join him.

"Yeah," he nodded," you should come join me," he said suggestively.

I swear I only got on the bed because I had no where else to sit. And lord knows I was not going to cross into my roommate's uncharted territory. I got on the bed and scooted all the way back so that I was resting against the headboard. Travis sat up next to me.

"So those guys you were talking about tonight, did they have names?" asked Travis.

"What guys?" I asked looking at him and then suddenly remembered my made up boy toys," oh, oh yeah, uh, Jack and um Dave."

Travis gave me that same amused look he had on his face tonight when I suggested we will have to wait and see if my spitting up on myself was a good sign or bad sign.

"Well, I hope Jack and um Dave know how lucky they are to have been with you," said Travis.

Travis suddenly leaned forward and kissed me. His lips delicately touching my mine, but it still sent an electrifying shock through my body.

"What, what are you doing?" I asked breathlessly.

"I'm kissing you. Hopefully better than Jack and Dave," he said returning his mouth to mine.

I responded with a tiny moan letting him know he was much, much better. He started kissing me with more intense desire. I allowed him access into my mouth so his tongue could find mine. He kissed me while stroking my tongue with his tongue. He used one hand to grab the clip out of my hair causing my hair to plummet down. He laid me down on the bed giving me a few more kisses and then decided to move his lips toward my ear. He nibbled at it making me feel very hot like someone had started a fire in the room. He moved his way down to my throat giving it tiny kissing. He leaned me up a bit to undo the tie that holds my dress up. After it was untied he slowly pulled my dress down to expose my breasts.

"Wow," he said while slowly gripping and rubbing his hand over one of my breast," you have an incredible chest."

He leaned in and started kissing around my nipple making it get hard. He then put his mouth right on my nipple and started to suck.

I started moaning and felt a tingling sensation below. Moving over to my other breast he did the exact same thing.

I realized during this time I was about to have sex for the first time and started to feel a little scared. It felt so good and I really liked Travis, but could I actually go through losing my virginity.

"Hey, where'd you go?' Travis said looking concerned.

I realized staring in his eyes how much I wanted him and decided to just go for it. No more doubts.

"I was waiting my turn," I said grabbing him and flipping him under me.

He was shocked so he didn't try to stop me. I think he wanted to see what I was going to do. I unbuttoned his shirt and had him slide his arms out of it. I started kissing him on his chest. Big wet kisses circling his nipples like he had done to me. I put my mouth over one and started to suck hoping he was enjoying it. His low grunts gave me my answer. I switch to the other giving it the same treatment; a kiss with a bit of tonguing.

I sat up and started to unbutton his pants sliding them off and throwing them on the floor. I could see through his boxers how excited he had become due to my kisses. I pulled his boxers off to reveal his penis. The first penis I have ever seen. It was huge. I just sat there and thought to myself that there is no way that thing is going inside of me.

"Hailey you are kind of freaking me out and making me feel self conscious with your staring," Travis said looking at me again with concern.

"I'm sorry," I said looking at him," it's just that you are really big. I don't think you will be able to stick that thing in me."

Travis started laughing and he sat up on his elbows and said, "Hails don't worry about it not fitting. It will be fine." He stroked my face with his hand and I knew everything would be okay. I pushed him backed down on the bed and he gave me a questioning look. I answered him by putting his dick in my mouth.

I started by sucking the rim, so I could make him harder for me. He obliged and started growing in my mouth. I started taking more of him in my mouth and started going up and down. He started moaning and letting me know how good it felt. I eventually got a mouthful of cum in my mouth, and one finally grunt from Travis. I sat up wiping away the mess he made on my face, and I was suddenly thrown down against the bed. Travis pulled my dress completely off and started rubbing his fingers around my breast getting my hot again. Then, he suddenly started to rub downwards until he got to my thigh. He made me open up my legs, so he could rub his hands back up to my crotch. He started to massage my clit with his thumb causing my knees to shake. He then stuck his index finger into me causing me to gasp for air. He kept massaging me and I felt this energy being built up and I knew he was going to make me explode. Suddenly, he stopped and placed both of hands on my thighs to keep them spread apart. All of the sudden I felt this tongue sweeping over my clit causing me to lose control. My first organism hit me so fast. I cried out in pleasure and shook uncontrollable in Travis's hands.

Travis pulled himself up to level his face with mine. "Baby you taste so sweet," and he started kissing me so I could taste. He got up off the bed and went over to his pants and pulled out his wallet to retrieve his condoms. He crawled back over the bed.

"You wanna put it on?" I shook my head no.

After putting it on he leaned over and positioned himself on top of me. He grabbed my legs and had them laid on his forearms. As he was about to entered I stopped him by pushing my hands against his chest.

"What's wrong? Do you not want to do this?" Travis asked with disappointment in his eyes.

"No, I want to really badly," I said with pleading eyes," it's just, well, there was no Jack or Dave," I blurted out and hoped he would understand. He looked at me then I saw the click in his eyes.

"You're a virgin?"

"Yeah," I said self consciously.

He laughed and I looked up and realized he was smiling at me.

"I'm happy you told me otherwise your first time would have been torture. Don't get me wrong it will still hurt, but now I know to be gentle," he said stroking his hand in my hair.

He placed both hands on my hips and leaned forward. I felt his penis rubbing over my clit making me feel hot and aroused again. I could feel him stiffen up like before. He slowly started to enter and I finally understood why girls complain about their first time. He kept pushing in and I kept taking deep steady breaths. After what seemed like forever Travis finally whispered," I'm completely in."

I looked down and the first thing that crossed my mind was how weird this look from my angle. He moved his right hand to my breast and start pinching my nipple. It sent electrifying bolts through my body. He started to slide backwards but halfway out he decided to come back in. It hurt, but I could feel myself widening and knew the pain would eventually stop. He slid backwards this time and came all the way back, and then he retreated right back in. It was starting to feel really good and I was feeling more pleasure than pain. A couple of more times in and I asked him to go faster. He started moving up and down more making both of us moan. I could that energy building up more and more with every thrust he made. I started hungering for more control, so I grab his shoulders.

"I want on top," I told Travis trying to get him to roll on bottom. He obliged and I gained control.

I grabbed his dick and angled myself over him. I moved my hand up and down making Travis moan. I slowly started to enter it into me. I eventually got all the way down on to his dick. I push my hands into his chest and started to thrust my hips.

"Ohh baby fuck me. Make me fuckin cum," Travis said squeezing my hips.

I started feeling that tingle again and I knew it was coming. My second organism resulted in making Travis cum. I was gasping for air so I decided to lie down on Travis's chest. I had a total of four organisms by the time Travis left that morning.

Looking back now I'm thankfully that it was Travis I lost my virginity too. It was nice that there wasn't a Jack or Dave in the picture.

The announcer had finally called everyone up by now and had us stand up and throw our caps in the air. I watched mine go up at an incredibly high distance. It floated right back down to me.

I felt a tap on my shoulder and whirl around to see Travis there. He looked at me with his amused smirk, but then he gently kissed me.

"Travis, I love-," but I was cut off by his sudden movement to the ground. He was position on one knee almost as if...

"Hailey, will you marry me?" Travis asked with an open ring box revealing a beautiful diamond ring.

-----------------------------------

So if you have gotten this far, yay! Don't worry Hailey's story is still not over. We haven't even gotten to the drama yet. Please, please leave your comments if you have any. And please vote! I can't wait to hear from you!

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
7 Comments
AnonymousAnonymousalmost 11 years ago
Big Like

Sequel please! loves it but you can make it longer :)

AnonymousAnonymousabout 13 years ago
Maybe

four organisms refers to sperm. Or maybe he is an alien with four, uh, you know. Or maybe her experience was so psychodelic that she was at a loss for words and forgot how to say the big O!

ZombieQueenZombieQueenabout 13 years ago
good start

the title doesn't have any connection to the story that I can see. But "I had four organisms" made my night. Sometimes typos are just too great to fix.

AnonymousAnonymousabout 13 years ago
Gave it a four...

It's great, but... You had a few mistakes. "Organism" when you clearly met orgasm.

and " It stands out in my head because it was the first time I lost my virginity." You can only lose your virginity once right? I mean, not getting technical where some people say oral, vaginal, and anal, but usually it's just the one time when referred to it in a general way.

But otherwise it's fantastic and I'm definitely looking forward to the second chapter. =]

AnonymousAnonymousabout 13 years ago
Awsome

Great storie but if u want 2 stop it nd break my heart go rite ahead lol naw jkin cant wait til the nex one but please make it soon

Show More
Share this Story

Similar Stories

Ransom Kailee fights for her independence.in NonConsent/Reluctance
Scheherazade and the King A mysterious girl falls into the hands of a troubled king.in NonConsent/Reluctance
A Gilded Cage Ch. 01 She still belongs to him whether she likes it or not.in NonConsent/Reluctance
Endgame A fine lie exists between love and hate.in NonConsent/Reluctance
More Stories