Tess looked exactly like something I would like. She had long bright red hair that she would wear straight, in a pony tail, or sometimes in beautiful loose curls. Her skin was creamy and lightly freckled. She was tiny, about 5'2 and thin, probably not 95 lbs. But she wore amazing curves on her small frame. Think size 2 but with a defined waist and perfectly round ass.
She was everything I was attracted to. Except for one thing, she was annoying. It seemed like every time she said something to me I got thoroughly annoyed.
We had been working together for about 2 weeks when the flirting started.It was intense. I was new and just learning my way around. I didn't even really know who the players were yet. And yet, every time I turned around there she was, asking when I worked next, asking if I wanted to hang out, asking if I had plans. Maybe it's because she was a year younger than me. She was about to be a college freshman and I was about to be a sophomore. Maybe it shouldn't have mattered, but it did. Maybe it was because I saw her endless prattle as immature. Maybe it was because she overshared. Whatever it was, I was annoyed every time she was around.
We worked at a restaurant in the mall food court, and as the new guy I was often relegated to trash duty. In truth, it really wasn't that bad. Our trash wasn't particularly dirty and you got a good walk out of it. To get to the compactor you had to walk outside, then it was about 50 yards to the building it was in. You went through a door and pulled the wheeled cans up a ramp to the top and then dumped the trash and wheeled the cans back down. We always went in pairs, especially with the girls. We didn't live in a dangerous area, but it was still a mall parking lot after dark. Tess figured out very quickly how to use this "safety protocol" to her advantage.
"Chris said you have to help me take the trash out."
"OK."
We were about halfway there when she stopped and looked at me.
"What would you do if I just kissed you?"
I was immediately annoyed. I hated stupid girl stuff like that. I turned wry very quickly. I gave it a quick thought. What could I say to shut this down? I was almost aggressive when I responded, "I'd shove my hand down your pants." I intentionally used the word "shove."
We pulled the cans up the ramp and emptied them. She was on the high side of the ramp as I began to move the cans so I could pull them down. Then, she actually did it. She tapped me on the shoulder, and when I turned around, we were almost eye level. She began kissing me. It wasn't a cute, soft easy lips kiss. It was a full send, tongue and all make out kiss.
I actually thought the words, "Well Fuck! I can't bluff this now." So, I did it. I shoved my hand past her belt, and right down the front of her pants. I turned her so she was leaning up against the railing that lined the ramp. I leaned into her. I thought maybe she would back off. Instead, she used her new found height to reach around my head and pull me closer. I felt her panty line. I stopped for a moment. Her kissing continued. I thought if I pushed a little further, she would decide it wasn't a good idea. She had no intention of backing down. I thought to myself, "Fuck! This is actually happening." I kept pushing. When I got to her hairline, she moaned slightly. It was obvious, no one was backing down.
I pushed all the way down into her panties. I cupped her entire pussy in my hand. Like the rest of her, it was tiny. I rubbed it slightly. She moaned a little. I rubbed easily on her clit. She put pressure on my hand and moved her hips slowly in the same rhythm. It was obvious there would be no retreat from either side. I slowly began to work my finger up and down her slit. She softly mumbled, "mm hmm" through the kiss.
I tried to slip my middle finger inside of her. I had to push slightly. It was tight. Then I felt something familiar. It was the soft velvety feeling of a pussy that had been used little. I recognized it because my high school girlfriend and I were both virgins until we weren't. That tight velvety feeling disappeared gradually as we had sex more. I had no idea if she was a virgin and I certainly didn't want to ask. I was feeling mixed emotions. I was excited, intrigued, and even slightly annoyed at the way this was happening.
I moved my finger until it was comfortable inside her. She moved her hips in unison, pressed harder onto my hand, and moved slightly so my finger slid slowly in and out. A couple times I tried to slip a second finger in her. She flinched a little. I moved my hand trying to make more space. The angle was odd with my hand inside her belt. She even tried to help. She spread her legs a little further, trying to make some space. She was really just that tight. Even though I found her annoying, I didn't want to hurt her.
Instead I reached my middle finger into her as far as I could and began to rub behind her clit. She immediately began breathing faster. She grabbed my head with both hands. She pressed her lips hard into mine and her tongue went rigid. I applied a little more pressure, still rubbing her clit from the inside. In less than 2 minutes she was cumming in my hand. Her body had tensed and her pussy had clamped onto my finger. I wriggled it slightly and waited for her body to relax before I removed it slowly.
About halfway back she stopped and looked at me. "I know I owe you one and I intend to pay up." It was the only thing said the rest of the night.
Tess lived with her grand parents. I had no idea why. I did know they were super strict and wanted no part of letting her ride in cars with boys. Several times she had tried to get me to give her a ride home. They always shut it down. I found this pretty amusing. First, it frustrated her. And, second, I would have given anyone a ride that asked for one. We all looked out for one another. It's just the way that industry worked.
One Thursday, she asked me again. "Can I get a ride home tomorrow?"
"Yep." It seemed like a safe bet. I calculated the odds somewhere slightly less than winning the lottery.
After we finished closing, I ducked into the bathroom. I was planning to go hang out with my buddies, so I changed into my typical shorts, tee, and flip flops. When I emerged, there she was.
"Ready to go?"
"UUUhhhh Yeah." I was completely shocked.
We walked to my car, a decent hand-me-down SUV that had belonged to my parents. My buddies and I were always packing it full of stuff, so the rear seat was almost always folded down.
She lived about 20 minutes away, no interstate necessary. She began giving me directions. She prattled on in between directions. I was about 50 % tuned out. "Make a left. I really liked what you did to me." All of a sudden I was tuned in. I hadn't expected that.
"Turn down this drive way and go to the very end. I've only done it once."
I was caught off guard. I didn't need to ask any questions, she immediately began to fill me in.
"It was the guy I went to prom with. We weren't even dating or whatever. He brought a condom, so I figured we'd try it. He was so nervous, he almost came putting the condom on. Then, he hardly got any of it in me before he pulled it out really fast and came in the condom."
I actually laughed.
She laughed a little. " I guess it is funny now."
"That is exactly some shit that would happen to you." She laughed again.
We reached "the end." There was nothing there- No house, no drive, nothing. We were in a stand of trees. "Where are we?"
"The other side of my uncle's farm."
I had already learned that all farms, for some reason, have "another side." It's a place that is not reachable from the main area of the farm and requires you to drive around, usually on country roads, to enter from a different direction. I sarcastically thought to myself, "This is great."
"Where is the house?"
"About a mile that way." She pointed.
"Where is your grandparents' house?"
"Right across the street from his. She looked at the clock on the dash. I told them we had a team meeting, and Carrie was bringing me home. We have about 30 minutes."
She didn't wait for me to respond. She pulled her polo, t shirt, and bra off in one motion and climbed between the seats to the back. "C'mon! We don't have that long."
I was way too big to be climbing between seats. In the time it took me to open the front door, get out, close it quietly and open the back door, she had taken off her hat, and she was slipping her panties over her ankles. She leaned back diagonally, her head behind the passenger seat, her feet toward the back driver door. Then as she leaned back, two things happened that changed everything. As she leaned back she just opened her legs. She hadn't said anything, She wasn't waiting. She just spread her legs, feet on the floor, knees wide. There she was, completely open. I was truthfully stunned for a moment. I took in her pink nipples against small, round creamy breasts, and a tuft of shimmering red hair at the top of her mound. The inner lips of her pussy were slightly opened and the same pale pink as her nipples. She was the most beautiful thing I had ever seen.
"Well, C'mon. Take them off. We don't have too much time." My shorts fell to the ground. I stepped out of my flip flops and removed my shirt in one motion. I climbed in.
"Those too." She pointed at my boxers. I slipped them off. Then the second thing happened that changed things. She immediately grabbed me and pulled my naked body directly on top of hers, between her legs. She adjusted her hips slightly, placing my now incredibly hard cock directly on her pussy. Her legs stayed wide. "They won't let me go on birth control. But..." She paused, and her voice got soft. "You can cum ON me anywhere you want." She looked into my eyes."I won't mind."
She hadn't said "I don't mind," as if it was some common and current occurrence. She had said, "I won't mind." It was something that was going to happen in the future and she was OK with it.
"Now, put it in."
I actually leaned in and kissed her as I began sliding my tip up and down her slit. She was already wet. I pushed the head in slowly. It was incredibly tight. She both moaned in pleasure and winced slightly. I pulled the head out and slipped it back in. She moaned, but didn't wince this time. I slipped it out then back in 4 or 5 times, just fucking the very beginning of her opening with the head of my cock. The opening had loosened slightly. Somehow, I had managed to end up with an inordinate number of virgins. Normally I could tell. I couldn't tell if she had a cherry or not. I could only feel that she was tight.
"More," she said softly. "More." I applied pressure and pushed a little deeper. I slowly worked into her until l was about half way. I pulled back and fucked her easy. Her opening was still tight around my shaft as I slid slowly in and out of her.
"All the way," she said. "Put it all the way in."
As I pushed a little harder, I could feel it moving deeper. Then it was like something let go and I slid in almost all the way to the base. She let out a multi pitched, "Ooooooohhhhhhaaannnnhhhh!" I couldn't tell if it was pleasure or pain. I pulled back and ever so slowly went back in as far as I could go until I could tell she was uncomfortable. I let it sit there. I also somehow remembered how annoying she was. I gave a quick little soft thrust. She let out a loud "UUUUnnnnhhhh!" I secretly snickered inside.Even though I had given her that little grunt, I really wanted her to be enjoying it.
I found a stroke and a rhythm that seemed to work for her. When she was ready for more, she would lift her hips to meet me. If it kept feeling good, I kept going. If she winced I would back off a little. Eventually I worked it more or less all the way in. It was still tight, but sliding in and out.
"I want to try top."
"Are you sure?"
I knew if she was on top, it would be on her to control pace and depth.
"I want to know what its like to ride you."
I rolled off her. "Before you get on, I want to see it."
"See what?"
"The opening I made in you."
She opened her legs wide, exposing her pink pussy and the opening I had made in it.
"What does it look like?"
"It looks amazing. I stretched you out. Are you glad?"
"I can't believe how good it is."
She climbed on me and never reached for my cock. Instead she lined herself up and just sat down on it. That took her deeper than she realized. Her body tensed and she landed with a fairly loud, "Oonnnwwwhhhh." I placed the back of my hands on my thighs and pushed my fingers up so it lifted her off of me slightly. Her body relaxed and she began to move.
At first, she bounced up and down. Eventually she realized she could move in a more circular motion and slide me in and out while controlling the depth. Her breathing had quickened. She was making little moans every time she went down on me.
I asked, "Are you gonna cum?"
"I think so."
"You're really good."
She actually replied, "mmmmmmm."
I got a little cheekier. "Your pussy is good."
"Oh yes." Her breathing got faster yet.
I went further. "Do you like being a good fuck?"
"God yes. Oh yes."
I went full send with the dirty talk. "Do you like being a good piece of ass? Do you like using your pussy? You know you're gonna to make my cock cum. Your pussy is so good I'm gonna have to cum."
"OH MY GOD!!! IM GONNA CUMM!!!"
I slid my hands out from under her and rubbed her clit with my thumb. She began to cum immediately. She arched her back. Her beautiful hair streamed down. In the middle of her orgasm she came down too hard and screamed. She never stopped, though.
"Oh my God. I didn't know that would happen. I didn't expect that. I feel you got harder. Am I really gonna make you cum?" I nodded.
"Will you get under me and spread your legs again?"
Her answer was obvious. She rolled off of me and onto her back. Her legs opened again.
I couldn't wait to be back in her. I pushed in. It was still tight, but I slid to the back. I found a rhythm sliding in and out of her. Occasionally I would go a little deep or hit the wrong angle and she would let a small squeak.
After a minute or so, I could feel the pressure. "You're gonna make me cum! Your pussy is gonna make me cum."
"Really?"
"YES! Fucking you is gonna make me cum."
All of a sudden I wanted to see it. I lifted off her and looked down at my cock buried in her. She was stretched. Her red tuft pushed against me. I pulled back and saw the pale pink of her inner pussy. It was all I could take. I slammed into her. She screamed. I did it twice more, as deep as I could. She screamed each time.
She replaced the screams with words. "Cuuummmm! Do it! Oh God! Cuuummmm. Please! I owe you! Cuuummmmm!!"
I pulled out fast and laid my shaft in her slit, my balls pushed against her opening. I pushed on her slit once then as hard as I could.
It began to rope out of me. The first shot landed on her left tit, side, and in her hair. She went complete freak. "GOODDD YESSSSS! KEEEP Cuummiing! Don't Stop! Put it all on me! I waaannnt it all! Don't stop cumming! Please don't stop. Please keep cumming. Make sure I get it all!" She kept screaming as long as it squirted out of me.
I collapsed on top of her exhausted. I kissed her and was glad to do it. Our chests heaved. I replayed it in my mind. She hadn't complained one time. She hadn't tried to pull away. She hadn't told me it hurt. She had opened her legs to me and took me in and out of her body for almost 30 minutes.
It was like she was in my head for the conversation I was having with myself. "I was glad to do that. I wanted you in me."
"Did it hurt?"
"Sometimes."
"You never tried to stop."
"I wanted it for you."
"I would have been easier if you had asked."
"I wanted you to have me. I wanted to owe you and then pay you."
"How does your pussy feel?"
"Good. It hurts a little. It feels fucked."
I looked down at her. She was covered. She had me all over her, her chest, stomach, hair, arms.
I reached for the towel in my overnight bag.
"No! Don't clean me off." She got back in the front seat and put her t shirt on directly over the mess I had made on her. She folded her hair up including the sticky part my first shot had landed on and put her hat over it.
I only drove part way down her drive way. She reached up and kissed me on the cheek, then got out.