Chelsea Ch. 01

Story Info
Friendship turns erotic.
4k words
4.18
18.3k
2
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

"We're the directors—our hands will hold steady. I'll be John Cassavettes—let me know when you're ready. Man, we make our own movies. Man, we make our own movies. Man, we make our own movies. Man, we make our own movies." – The Hold Steady "Slapped Actress"

Does your life ever seem like a movie? You know what I'm talking about? Sometimes you're just sitting there living your life and if you think about it from a detached perspective, you can almost hear the bad soundtrack in the background and the people in the audience asking themselves how that character got into that situation. That's where I was at. How did I get there? Good question.

************************************

I showed up to work one night incredibly hung over. When I found out that I was going to be training a new server I was not excited by the prospects. The last thing that I needed was to answer someone's questions all night while my head reminded me of the bad decisions I had made the night before...then I saw her. She had beautiful wavy brown hair, and the biggest, most beautiful brown eyes I had ever seen. Her smile was electric and I was immediately smitten. It didn't hurt that she was tall, with incredibly long legs and what looked like beautiful breasts.

"Are you Jake," she asked.

"I am," I replied.

"My names Chelsea. I think you're supposed to train me tonight."

Suddenly my headache was starting to dissipate and I was forgetting about the 5 shots of Wild Turkey from the night before.


"Cool," I said. "Follow me and we'll get started."

For the rest of the night I showed her what to do and talked to her. I found out that in addition to being beautiful she was smart, funny and more than a little sassy. I love the sassy. As the night went on the conversation between us became more and more natural. After our shift ended we had a drink or two with some of our co-workers and went our separate ways. I was so happy as I walked home that it was a little frightening. This was six months after a long-term relationship had ended. That relationship had died for a number of reasons, but a big part of it was that I just wasn't able to communicate very effectively. After the break-up I made a pact with myself that I wasn't going to do that again. The next time I had an opportunity with a woman I was going to be honest and up front with her, no matter the eventual consequences.

***********************************

That night had been about a month ago. As the days went on Chelsea and I got closer and closer. We saw each other a lot at work and went out all the time with friends. She was very flirty with me, constantly touching me on the arm or shoulder when we were talking, making suggestive comments, the usual. She laughed at me all of the time. I'm funny, but not that funny. After a while, I knew that I wanted to be with her. And that gets us caught up to how I ended up in my own little "movie".

I had gotten up the nerve to ask her out and she said yes. I guess I had assumed that she understood I meant it to be a romantic date, but I wanted to make sure. So using my new life rule to be honest and up front I told her how I felt. I started some long speech about how I thought she was beautiful and smart and funny and that every night when I went home I thought about when I would be able to see her again. It was good, really good.

I was ready for her to admit her feelings about me when she said, "Can you sit down?"

We were walking to the movie on a snowy February night. The only place to sit was the front porch of some random house. I sat down and instantly realized that in addition to what was undoubtedly going to be a crushing denial from Chelsea, I now had a wet ass. "Sure," I said.

"That is about the nicest thing that anyone has ever said to me," she said. "And I've had so much fun with you over the past month, but I just can't do that right now. You're a friend, and I want you to stay that way, but I don't want a relationship with you."

I listened to what she was saying, and the only thing that entered my mind was, "this sucks." She had recently ended a relationship too, so I was ready for her to say that it was too soon, but that's not what she said. She said, "I don't want a relationship with you." Combine that with a wet ass and the night wasn't exactly going as planned.

"Jake?" she said.

"Yeah?"

"You haven't said anything," she answered. "I still really want to go to the movie with you."

Spending two hours in a movie theater with a woman who just rejected me was about the last thing that I wanted to do. At the same time, I didn't want to let her know that I was totally hurt and act like a child taking their ball and going home. So while I was planning on kissing her tonight, and maybe exploring that sexy body a bit, I was instead going to go to a movie with my "friend".

The movie ended up being fine. I walked her back to her apartment and she invited me in to see the pictures from her semester abroad. I looked through the pictures with her, all the while feeling the sting of the rejection. She was acting like nothing had happened, and while I tried to do the same inside I was screaming. We spent the next month or so going through the same motions we had established in our friendship.

We would see each other at work, have some drinks with our coworkers and have flirtatious conversations again and again. It was getting to the point that I couldn't take it anymore. Something had to change. Either we were going to see where the relationship could go, or we had to spend less time together. The present situation was horrible for me and I needed to do something. I decided that I was going to give it one more shot, with a different strategy.

***********************************************

There was a group of us going out for the night. Everyone was meeting at the bar we worked at and we were going to go out from there. My friend Mike saw me as I walked in.

"What's up?" he asked.

"Nothing," I said. "Is Chelsea here yet?"

He rolled his eyes at me. Mike was my closest friend and had gotten pretty protective of me. He had made it pretty clear that he thought Chelsea was being a bitch about the whole situation.

"Why are you doing this?" he asked. "She loves all the attention that you give her but she is never going to give you what you need. She's fucked up, man."

"I can't help it," I said. "I know that something needs to change though. I'm going to give it another shot and if it doesn't work, that's it."

"Christ," Mike said. "What are you going to do? You don't have another long speech planned, do you?" He chuckled as he said it. I had told him about my first attempt to win Chelsea's heart and how it failed. Somehow, he saw humor in it that escaped my imagination.

"No more speeches," I said. "I've been thinking about it and I think I figured it out. I know that she likes me, but something is holding her back. I'm just going to change the dynamic a bit and see what happens."

"Whatever," he said. "Just let me know when you're about to start. I want to make sure I have a front row seat. And don't be nervous, at least it isn't snowing tonight."

I didn't hear the last part of what he said because I was watching Chelsea walk across the room towards us with Molly and Courtney, a couple of our friends. She looked incredible. She was wearing an incredibly tight pair of jeans that showed off her legs and ass. Her little black top was trying to contain her chest, but the cleavage it allowed caused my imagination to go into overdrive. She was smiling her electric smile when she came up to me.

"Hey Jake, are we ready to go," she asked.

I nodded, grabbed Mike and the five of us headed out the door. We walked in a group to the destination for the night, another bar on campus where we knew the bartenders. Mike was walking up ahead with Molly and Courtney. The three of them were laughing about something, more than likely the fact that I was going to give it another shot with Chelsea tonight. Chelsea and I were talking about classes and work, but I was only half paying attention to the conversation. The bar that we were going to was underground, and just as we were descending the stairs I leaned over to Chelsea and whispered, "I'm going to seduce you tonight by the time they make last call."

"Really," she said, starting to giggle. "We'll see about that."

For the next few hours I didn't say a thing to her. I didn't talk to her or sit by her. Occasionally I would look over and smile, but that was it. I was having a blast with my friends. The vodka was good and cold and the buzz was outstanding. It was one of those nights that you imagine when you think about college. You always hear that you'll have the time of your life, and this was one of the nights they were talking about. As the night went on, Chelsea started to get a little jealous. I wasn't talking to another girl, I just wasn't talking to her. At about 1am, 30 minutes before last call, she came over to me.

"You haven't talked to me all night," she said.

"I know," I replied.

"How are you going to seduce me if you aren't going to talk to me," she asked.

"I still have half an hour, right?"

"I guess so," she said. "But you better use it wisely."

With that, she winked at me and walked away. I knew then and there that my plan had worked. At last call I ordered to drinks and brought one of them over to Chelsea.

"Here you go sweetie," I said. "Do you wanna go to the afterbar with me?"

"Sounds good," she said.

We finished our drinks and left the bar with Mike, Courtney and Molly. As we were walking out Mike asked how things had gone.

"Perfect," I said.

"Dude, you didn't talk to her all night," he said.

"I know," I said. "And it worked perfectly."

Chelsea and I were walking just behind Mike, Courtney and Molly on the way to a friend's house for the afterbar. We didn't really say anything, just walked. About halfway to the house, she reached over and grabbed my hand. The feeling when she took my hand was electric. Her skin was so soft that I didn't want to ever let go. I looked over at her and she smiled.

When we got to the house we went in to get a beer. After one sip, Chelsea looked at me and asked if we could go sit on the porch. The second we got outside she turned and kissed me. The kiss was passionate and deep and long and incredible. It was one of those kisses where the chemistry is there right away. There are some kisses where you know right away that the person is right or wrong for you. I knew right away that it worked. As we kissed our tongues gently explored each other. She tasted like cinnamon and it was truly delightful. After what seemed like only seconds she pulled away and looked at me.

"I'm tired," she said. "Can you walk me home?"

"Of course," I replied. "Let's go."

It was about a 10 minute walk back to her apartment. We stopped every block or so and just started kissing. Leaning against trees or buildings we were just exploring each other's mouths, feeling the euphoria that comes with new lust. With each successive kissing session I started exploring her body with my hands more and more. Her tight jeans allowed me to feel every inch of her legs and ass as though there was nothing there. Each time we started kissing the urgency would build, with the gasps and moans of pleasure getting louder and louder.

After half an hour we finally made it back to her apartment. We called for her roommate when we entered but no one answered. She smiled at the knowledge that we had the place to ourselves, grabbed my hand and led me back to her bedroom. The second we got in her room she shut the door and faced me with a mischievous grin on her face. I approached her and pressed her up against the door, holding the back of her head with my hand and pulling her into another kiss. She lifted a leg up and wrapped it partially around my body. With a little moan and giggle I knew that she could feel my stiff cock pressing against her.

I lifted her up and carried her over to the bed, her lithe body feeling weightless in my arms. I sat down and she straddled me, both of us sitting up and continuing our passionate kissing. I could feel her incredible breasts pressed against my chest and I started to caress her back under her top. Her skin was impossibly soft, and being this close to her reminded me just how intoxicating her scent was. As we kissed, she reached down and pulled her top over her head, leaving her in a very sexy black lace bra. I unfastened her bra and finally saw the breasts I had been fantasizing about. They were beautifully large and round without the pull of gravity that comes with age.

She ran her fingers through my hair and pulled my mouth down to her chest. I hungrily kissed, licked, sucked and nibbled every inch of her breasts. The feeling of her nipples hardening in my mouth only intensified my desire to please her. She was whimpering as I alternated back and forth, exploring not just her nipples, but the sides of her breasts and the valley between them.

She stood up and looked at me. "Do you want to see my ass Jake," she asked. "I know that you've been dreaming about it. I've seen the way you watch me. I've seen your eyes linger on my ass as I walk by."

As she said this she turned around and unfastened the button on her jeans. She started to slowly shimmy them down her legs, looking over her shoulder to gauge my reaction. I was transfixed by just how sexy and erotic she was. As her jeans made their way past her beautiful ass I saw that she was wearing a tiny black thong. Her ass was round and curvy but tight and muscular all at the same time. Once her jeans were off, she approached me once again.

Rather than allow her to straddle me again I stood up and held her in my arms. She was naked save for the thong she was wearing and my hands wandered around her body as we kissed, caressing her and enjoying her soft, curvy body. I laid her back on the bed and started to kiss her jaw line while I caressed her sides and stomach. I kissed my way down to her shoulders and neck, enjoying the soft moans of pleasure escaping her lips. I continued my exploration of her breasts, savoring the taste and marveling at how incredibly her body smelled. As I kissed down her stomach I could feel the heat radiating from her pussy through the thin little thong. I could feel her starting to thrust her hips up at me, anticipating my arrival at her center.

I kissed all around her hips and her upper thighs as she spread her legs for me. Her thong was unable to fully cover her and I could see the outer edges of her pussy and smell the intoxicating scent of her arousal. She was silently pleading for me to stop teasing her and focus on her pussy but I ignored her. I kissed my way down each thigh, exploring the legs I had been ogling for months. Her thighs and calves were incredibly sculpted and my exploration of her body was causing my cock to strain against my pants, begging for freedom.

I kissed back up her inner thighs and finally started to plant soft, gentle kisses on the thong-covered outline of her pussy. Her moan was loud and beautiful, a sound I had been dreaming about. I hooked my thumbs in the waist of her thong and pulled it down her legs. Once uncovered, her pussy was an incredible sight. She had a small, rectangular patch of hair trimmed very short above her pussy. Because of her current level of arousal she had already opened up to me, and her clit was peeking out from its hood.

With the tip of my tongue I traced the outline of her pussy. Her moaning intensified and she pulled my face deeper into her pussy. Her taste was amazing and I wanted nothing more than to drink her juices for the rest of the night. As I circled her clit with my tongue I slid a finger inside her. Her body stiffened as she moaned at my intrusion of her pussy. She started thrusting her hips up at me while I started flicking her clit with my tongue. I curled my finger and started to massage her G spot while I licked her clit. I was reaching up and pinching her nipples and caressing her body while I explored her pussy. Her moaning got louder and louder.

"Fuck me with your tongue Jake," she moaned. "Don't stop baby. You're going to make me cum. Don't stop, please don't stop."

I continued to lick and suck on her clit, occasionally tracing the outline of her pussy with my tongue while I rubbed her G spot. Her body stiffened as she thrust her hips into me, feeling the release she was looking for. After she relaxed I removed my finger from her pussy and just kissed around her hips and inner thighs. After a minute she rolled me over and got on top of me, kissing me with urgency and intensity.

"I love tasting my pussy on your lips," she said.

The only reply I could think of was, "me too."

She slid down my body and unfastened my belt. As she unbuttoned my pants she smiled at my hardness, loving that she had me so aroused. She pulled my pants and boxers down my legs, giving me an incredibly erotic look as she took my cock in her hand. The feeling was indescribable. The girl I had been dreaming about was holding my cock and looking into my eyes while she licked her lips. She reached out with her tongue and licked the underside of my cock. I shuddered at how marvelous it felt.

She circled the head of my cock with her tongue, stroking its length while she licked. She looked up into my eyes and took my cock into her mouth, swallowing about half of its seven inches. Her mouth moved up and down on my cock as she massaged my balls with her hand. I ran my fingers through her hair and pulled her mouth onto my cock, reveling in the intense feelings she was giving me. She would alternate between taking my cock down her throat and giving my cock and balls a bath with her tongue. Chelsea was the kind of girl who sucked cock because she enjoyed giving pleasure, not because she felt obligated, and it showed.

After a few more minutes of her oral assault I lifted her up and pulled her on top of me on her bed. She straddled my hips and pressed her pussy against my cock. She was sliding her pussy back and forth on my cock, using it to stimulate her clit with each pass. I could feel her wetness spreading all over my cock and it aroused me even more. After a few minutes of kissing and grinding she reached down and took hold of my cock, pressing my head against her opening. She sat down on my cock and both of us moaned at the feeling of her pussy enveloping me for the first time. As she started to ride my cock I allowed my hands to roam all over her back and ass, gripping her hips as she rocked back and forth on me.

"Jesus, Jake, your cock feels so good inside me," she said.

"Your pussy feels incredible baby," I responded.

From there, it was a blur of moans and gasps and kisses and licks as she rocked back and forth on my cock. I was holding her hips and caressing her soft skin. I could feel the urgency build from within as my orgasm came nearer and nearer.

"Chelsea, I'm going to cum if you don't slow down," I said.

She looked deep into my eyes and said, "cum inside me baby. I've been waiting for this for a long time."

She started riding my cock faster and faster, squeezing me with her muscles. I couldn't take it any longer and started kissing her as my cum exploded from my cock. She stayed on top of me, my cock inside of her as we came down from the high of our coupling. After a minute or two we started playfully kissing and exploring each other's bodies with our hands. After a while she rolled onto her side with her head on my chest and we fell asleep holding each other.

*****************************************

"Is this sort of some old summer fling
And this thing we have
Will it mean anything
When October rolls around
Will you sober up and let me down

12