Not So Casual Encounter

We both agreed it would be just casual. No strings. Little did we both know that it turned out the way it had.

The text finally came in. He was waiting downstairs for me. Craigslist was perfect for those lonely moments where you need to let loose. We didn’t exchange pictures. Set it up that way so we wouldn’t have to worry about getting too attached. Instead we treated this like a one-night stand. Only problem, my best friend had not left like he promised. Kevin didn’t know who this person was coming over. I was too embarrassed to let him know my intentions. We aren’t the type of friends to keep things from each other. But I have not ever done anything like this. I was as he called, “a good girl prude.” By no means am I a virgin. I just preferred to have dated a guy a few months before letting it get that far. To be honest I haven’t had sex for two years. Had relationships that failed before we made it to the bedroom. Suffice to say I was more than willing to throw my morals away for fifteen minutes of pleasure.

“Jess?” Kevin looks to me curiously as I get up and go to the door. I can hear his concern. All I can do is just look at the door.

“My…boyfriend is waiting downstairs. Please don’t embarrass me Kev. I want this one to work.” I plea my lie. I was desperate for him not to question it.

“No wonder you wanted me out. You think I’m going to fuck this up. Look Jess…I’ll play you up.” I don’t say anything and leave. In the elevator I use the heel of my palm to hit my forehead over and over. I don’t know what is worse. Lying or the fact I have to get this guy to pretend to be my boyfriend to hide my shame. I play it over and over in mind as I leave the elevator and see him standing outside the doors. I stop, staring at him. I didn’t expect him to be good-looking. I mean he’s more attractive than my best friend and that is saying something. I open the door for him with a big goofy smile.

“Hi welcome. Um what’s your name?” I ask. We never exchanged names either. The realization was a bit unnerving. I had to remind myself that this was just a casual encounter.

“Kevin.” He answers smiling. God, he has a great smile. And the same name as my best friend. This awkward. “You?”

“I’m Jess…um…” I bite down on my lower lip and run my fingers through my hair. I’m not in his league. I know because I am overweight and my self-esteem isn’t very great. I was expecting someone ugly. So passing him off as my boyfriend will be challenging. I lead him to the elevator and we get in when the doors open. “Look Kevin…my best friend is still home. He lives with me. And I told him you are my boyfriend because I didn’t have the guts to say you are just a one time encounter.” I look down, staring at my shoes knowing he’d want to cut out. He probably wanted to when he figured it was me coming to get him. To my surprise he takes my hand. A little rough, very warm and it felt calming. I look up to him and he’s smiling at me.

“Sure I’ll pretend. It’ll be okay.” His words were sweet but deep down I feel like he is just as desperate to get laid. He wouldn’t do this if we were actually trying to date. I unlock my door without letting go of his hand. We walk in and find my best friend in the kitchen pouring himself some soda. He looks up and gives a look. I know that look. I give it to him every time he brings home a girl way too beautiful for him.

“Hey Jess this must be the boyfriend. Hey dude, I’m Kevin.” He holds out his hand to Kevin. This is going to be weird.

“We actually all call him Mutt. Mutt this is Kevin.” I introduce and let go of Kevin’s hand and go into the living room and sit down against the wall. My living room is bare, apart from the blanket bed in the corner I sleep on. My room, the only one in the apartment, is shared by a couple who never paid me a lick of rent even though they have money. You guessed it, apart from being an insecure, overweight woman I am also a pushover. Thankfully they are not here. All I need is more people to witness this charade.

“Nice to meet you Mutt. So your Jess’ best friend?”

“Yup, have known her since we were kids. I was twelve she was thirteen when we met online. We didn’t meet till she was like sixteen and moved to Texas. She ended up at my school. It’s actually a really funny story.”

“Mutt please don’t…” I interject. Most my relations, friendships or otherwise almost always started online. So yes, when I sought out a sexual encounter I of course turned to the internet.

“I’d like to hear this babe. Jess never talks about herself.” I look to them when Kevin says that and holds my breath. He called me babe and he wants to hear something personal? He’s breaking my rules! They both leave the kitchen and sit down. Mutt sat a foot away from me and Kevin sat next to me and put an arm around me. This is so weird! My heart is pounding.

“You need to be patient with Jess. I’m her best friend and she still doesn’t fully let me in. But when she does, little by little you can’t help but love her.” I smile. That would have to be the nicest thing Mutt ever said about me. He's usually a dick. “Okay back to how we met. Jess and I lost contact a few months before. Last I heard she was in foster care and that she wasn’t allowed on the internet in the group home unless for school. I thought I lost my best friend. Then I met this girl who, well, didn’t see a fat, clumsy tub of lard like everyone else.”

“Wait you were fat?” Kevin asks. I laugh. It is hard to believe Mutt was ever fat.

“Yeah, true story Kevin. Back in high school Jess was the hot one. She was cheer captain, class president, track star. Everyone loved her. But she didn’t hang out with the popular kids. She hung out with me and Natasha. You should of seen how weird it looked. This beautiful girl with a killer body!”

“Mutt stop! Just tell the story.” When Mutt talks about what I use to look like, it makes me more self-conscious.

“Okay, okay. Well one day Jess is talking to Natasha and Natasha is pissing her off. Then Jess says "ie condosa." It clicked. I only knew one person in the world that said that. She said it to me hundreds of time online. So I grabbed her and said "your JessStarryNights!" I couldn’t believe my best friend has been her for the past month. I mean, Jess dropped a QB for putting splatter paint in my locker. She always stuck up for me. She is the most incredible person I ever met." Mutt gets up looking at his watch than to me. I am blushing pretty bad. He has never put me in such a light before. Normally he's just an asshole. “I got to go Jess. Have fun.” He waves and leaves me alone with Kevin.

“Okay you can take your arm off. No need for the show.” I move trying to shake off his arm only for him to use his other to grab hold of me.

“You try to play it off like your some heartless control freak. Even when we texted you were guarded. Now I see why. But if you don’t want to have sex because things turned out this way. I’ll go. Just don’t pretend to be someone else.” Kevin’s words made me look away. Why is he so nice? I did everything possible for it to not end up like this way. I like him now.

“Things are different now. If we do anything…it’ll mean something now. So I think it’s best you leave now. Cause I don’t want to get hurt.”

“You complicate everything don’t you? Haven’t you ever just let yourself feel good?” His question made me feel worse. Then my whole body tingles. His lips are on my shoulder and moving towards my neck. This small action was enough to cause me to cum. My panties wet with fresh desire. At this point I wouldn’t care if I saw him again. Yeah I’ll hurt when he’s gone, but right now I want to feel good. His hands move down to my breasts. “You were right, you do have huge breasts.” I bite down on my lower lip moving myself away only for him to pull me back. He imprisons my mouth. I feel his tongue push in and play with mine. I have never kissed like this before. The tongue is new to me. He’s holding me so tightly I have no choice but to move with him. Next thing I know he has maneuvered us to my blanket bed. Laying me down gently. He pulls off my top and to my surprise my bra was already unhooked. When did he do that? He takes my bra as well and undoes my jeans. Pulling them off along with my panties. I’m laying there completely naked looking up at him as he pulls off his shirt. I notice the muscle definition. He actually has a six pack.

“Whoa…what kind of a job do you do?” I ask as I gently move my fingertips over his muscles.

“I’m in the army.” His answer surprises me. A soldier? I don’t know really what to think because as I am contemplating him, he opens my legs and shoves his face into my very wet pussy. My back arches and I squeeze my legs around his head. He pry’s them open and holds them open as he licks at the folds of my pussy. No man has ever. 21 years old and I have not experienced this till now. I don’t want him to stop. My inner thighs quiver to his mouth devouring mercilessly. He lifts his head grinning at me. He stands undoing his pants and I watch hungrily. Not sure what to except. He removes his pants and underwear. I see a very thick, erect penis. And he looks down at it then at me. “I know, it’s not very big.” My head tilts to that. Big? What? It’s not small!

“Are you kidding me? Anything under four inches is small. You…you are above expectation.” He snickers at that as I feel the head of his penis penetrating my opening. I reach up and grab hold of his shoulders as he attempts to enter me.

“How is someone as wet as you is this difficult to enter? Not that I mind the challenge.” He whispers in my ear as he continues to attempt. After a few minutes he manage to get all the way in. Huffing hard as he looks down to me with an exhausted smile.

“If men only knew what they were missing with you. Damn. I can feel you squeezing at me. Either your body wants me to work hard for this or it doesn’t like foreign objects.” I giggle at that. Now I understand why my boyfriends hardly wanted to sleep with me. They never told me this. My legs wraps tightly around his waist as he continues. Every bit of him in me felt so amazing. I moan loudly and so much it turns into a whimper. A whimper that sounds like an animal. I quickly cover my mouth to seize the sound. Kevin chuckles at me. He pulls out rolling me on top of him. Another new thing for him. He reaches up playing it my breasts as I attempt to ride his penis only to have it slip out six times in less than a minute. I cover my face frustrated. Instead of letting me feel bad he rolls back on top of me and then flips me over onto my stomach. I quickly realized what he was doing but the euphoria was too much for me to resist him. He pulls my butt up and successfully slides himself all the way in. I can feel the friction of him fighting against my pussy. I hold myself firm against the floor feeling myself begin to pant from it all. Realizing this was longer than fifteen minutes of pleasure. He definitely has stamina. He stops breathing hard and I slowly get to my feet.

“I need water.” My mouth is dry and I feel a bit light-headed. I’m guessing it has to do with the sex. I grab a cup filling it and I lean against the counter drinking it slowly. Kevin gets up and comes up behind me. He reaches around taking the glass and drinking down about a third before giving it back to me. I’m taking a drink when I feel him enter me again. My knees weakened. I didn’t expect him to go again. I can still feel the hot and sticky cum inside me. I brace myself against the counter letting it happen. I didn’t care the edge of the counter was cutting into my breasts. I feel too much pleasure to care. He stops again and I feel even more of his cum explode inside me. This time I felt it. Wondering why I didn’t feel it the first time. I turn reaching up to wrap my arms around his neck. Staring into his eyes. Noticing they looked a greyish-blue. He smiles. I lean in resting my forehead against his. Our naked, sweaty bodies seem glued together. Our hearts both pounding. This moment is almost perfect. Only thing is that he is not mine. I won’t see him again after this. His hand touches my cheek and I look back into his eyes. He leans in kissing my forehead for what seems like ages.

“I have to go. I’m already late.” He says and I hold onto him tighter. If this moment continues forever I could not ask for more

“You just got here.” I whisper.

“Jess I’ve been here almost six hours.” When he said that I look over his shoulder to the stove clock. No way! That’s not possible. “I have to go home and get my weekend bag. I have training. I wish I could stay longer.” I reluctantly let him go. I just stand there looking at my bare feet. He comes back to me. He lifts my chin and places a soft kiss on my lips. “I will call you Jess. This…is not over.” My breath catches and I watch him leave my apartment.

He was right. Seven years later we’re the best of friends with the most "fun benefits." I don’t know what I’d do without him. He can flip from being the most generous, kind and attentive lover to being the most dearest friend. He keeps me from going down toxic paths. Always gives me the strength to move on from places and people who only uses me. I can depend on him for anything. I am so thankful that our casual encounter didn’t become just that.