Can’t Have it All – Part 1

The first time I laid my eyes on her, she genuinely took my breath away. I know that sounds cliche but there was truly no other way to describe how I felt. She was walking along the outskirts of campus that led to the train station. She wore a white tank top with blue jeans, ripped at the knees. Coming in at 5 foot 6 inches, she would’ve stood about 4 inches shorter than myself. Throw in the fact that her hair reflects that of a brunette and she doesn’t sound particularly unique, but that’s not what gravitated her to me. It was the way that she carried herself: Confident but not arrogant, with eyes that had a sense of depth to them. I’ll admit that of the two relationships I’ve had in the past, both originating through lust, their shallow personalities were what warded me away in the end; I could already tell that wouldn’t be a problem here.

On the third day of the semester, I walked into my 8 am class with about as much enthusiasm the average person could have concerning Physics 201.

“Can you take my bag and grab me a seat? I’m gonna hit the bathroom before class starts.” My friend Elena asked me.

“Yeah, no problem.” I replied as I grabbed her backpack, taking a brief look at her backside as she ran off. I don’t take pride in sexualizing my female friends but I also won’t blame my occasional moment of weakness, especially this early in the day. And besides, Elena was a bombshell shrouded in a combination of baggy clothes, tomboyish traits, blue highlights to go along with her neck-length hair, and a standoffish gaze that kept any potential partners at a tantalizing distance.

Labeling her as ‘blessed’ wasn’t a huge exaggeration. Although she wasn’t one to advertise, Elena had a body most girls wouldn’t stop bragging about. With an ass to die for on top of 34C breasts (Only knew this because she left a bra on the floor once when I came over to study) sitting high and mighty on her chest, it’s not always easy to avert my eyes when the opportunity to ogle arises. Throw all that on a tall body with a pretty face and it’s a shame most guys can’t get near enough to even have a word with her. If we weren’t childhood friends who had been coincidentally reunited after entering the same major, I doubt I’d even get close enough to be friend-zoned.

As you’ve probably already figured, I’m a pretty lustful guy (I prefer to use a more classier term than “constantly horny”). Entering university really opened the door for me to convert my thoughts into actions, so you won’t ever find me complaining about hookup culture.

As I climbed the lecture hall stairs I found my mind beginning to fill with distracting fantasies of Elena and I, followed by a scolding given from me to myself. I was so engrossed in the battle between me and the horniness that I didn’t even notice the girl until after we had bumped into each other. Considering I was weighing in at roughly 180 lbs, our collision was enough to end with her caught awkwardly kneeling on the stairs while I loomed over her, saved by quickly grabbing the desk with my hand.

“Shit, you okay?” I asked before processing the face of who I was talking to.

“Yeah, thanks.” Replied the brunette I’d been eying as she made her way to the train station on the first day of class.

“I’m going to assume you weren’t trying to purposely bulldoze me.” She said jokingly as a smile flashed in my direction. Now considering my history with girls, I’ve never really had that phase of struggling to strike up conversations. Coming into university and having frequent interactions with a girl like Elena has given me the ability to keep up a conversation even if my mind was more focused on some other part of her. As I was about to reply I realized this was the first time I had seen this girl up close and personal, and wow! Black leggings accentuated her thighs and ass while the thin green top gave my eyes access to the outline of her bra. Her tits weren’t as big as Elena’s but she definitely wasn’t lacking that department.

“Um, yeah. I-I wouldn’t do that. Are you okay?”

“You already asked me that.”

Fuck.

“Hey Aly, all good?” Elena, my saving grace, asked me as she came up the stairs.

“Y-Yes.” I responded, impressed that I could even get that word out.

“Oh hey Elena!” The brunette greeted.

“Hey Lindsey, I didn’t know you were in our class too!” Elena replied as I continued to awkwardly stand between them waiting for my mouth to formulate a single coherent sentence.

“Yeah, we’re sitting just over here if you want to join us.” Lindsey offered as she pointed to the desk nearest her.

I’ll admit that morning was definitely not one of my proudest moments. I sat next to Elena while she was in the middle between Lindsey and I. I tried to get some words into any conversation they were having but my prior embarrassment, on top of the physics jargon being thrown into the room, was stifling my usual charisma. Though, from listening in to their whispers I deduced that my initial impressions of Lindsey were spot on; Definitely not just a looker. Even the way she spoke was enough to encapsulate me, finding myself staring for a couple seconds too long.

“All the more reason to make a good first impression, dumbass.” I mumbled to myself as class neared its end.

“You should consider dating again. Your taste has gotten better since your last relationship, don’t you think?” Elena said as she suddenly steered the attention onto me. I opened my mouth to argue, ready to spiel the same words I say whenever Elena says anything about me dating again until I felt Lindsey’s gaze pierce through my eyes and into my soul, waiting intently for my reply. I realized that my usual counter which discussed how I enjoy being a ‘free bird that can lay in any nest it pleases’ may nip the bud of any chance I may have still had with Lindsey. But then again, maybe that’s exactly what she was looking for.

“Yeah, maybe I’ll start considering it.” I spat out.

“Oh my god, really?”

“I guess.” I said, attempting to keep a casual tone. “I’m not gonna rule it out, but I wouldn’t be against something a bit more casual too.” I added, as if it was an announcement to any and all girls in the area. At the same time the class was dismissed, leading us to go our separate ways.

“You like her don’t you?” Elena poked, with a sly smile forming at her lips.

“Whoa, how’d you know? Was I being that obvious?” I questioned as we sat down together on the train.

“Just two days ago you were talking about that ‘free bird’ bullshit.” She said while making air quotations. “I doubt she noticed anything but you can’t fool me.” Say what you will about Elena but I do have to admit there’s not too many people who can observe the way she does. Though oddly enough I feel like I sensed a hint of sadness in her tone. Was it dissatisfaction? Jealousy?

“Nothing gets past you, huh?”

“Nope!” She said with a big smile, crossing her arms in a way that made her tits jiggle.

“So what do you think, is she a long-term type of girl or is she cool with just some fun?” I said nonchalantly while harnessing 19 years worth of will power to not look at her chest as it bounced.

“Sorry Aly, your horny ass is gonna have to commit if you want a taste. She’s never been the type to hook up just to destress. I wouldn’t say you’re not her type though, unlike me unfortunately.”

“Oh? I didn’t realize you were interested too.”

“Yeah well, She doesn’t swing both ways like I do so not much else to be said. If you want her, don’t hold back. I’ll be cheering you on.” She said with a laugh, placing a hand on my shoulder as if assuring me it wouldn’t bother her.

It’s not often Elena shows this side of her. Considering the way she usually acts in public, vulnerability doesn’t always suit her. The fact that she can feel so comfortable and genuine around me and yet so closed off with others attracts me to her. But, I’d say that Elena’s my best friend and I wouldn’t want to jeopardize what we have. Though I can’t deny how truly gorgeous she is with her deep green eyes and warm smile, her slim waist and curvy hips, her perky tits that are just begging to be squeezed. How it would feel to grab her wrists and pin her onto a wall, grinding myself onto her ass as she –.

“Hello? You in there?” Elena had gotten pretty close to me and was waving her hand to grab my attention, incidentally making one of her tits recoil as her arm moved.

“Uhhh sorry I just zoned out there.” I let out as we started getting up from our seats on the train.

“Yeah I can see that– whoa!” Elena exclaimed suddenly.

“What? Oh!” I yelped while twisting my body, hoping that she hadn’t gotten too good of a look at my semi-hard cock.

“Um. Sorry about that!” I said while quickly walking out of the train.

“It-It’s not a big deal. Wonder what you were thinking about while you were zoned out.” Elena chirped while regaining her composure, though my mishap had seemed to get her a lot more flustered than I would’ve expected.

We had planned to leave my car at the station and go back to my place to study for the rest of the day. As we entered the car, I turned on the music as fast as I could in an attempt to ease the awkwardness of the situation. As I began driving and things started settling down, I realized the song playing was The Weeknd’s Or Nah. Although both Elena and I love the song, it obviously wasn’t going to help our situation so I decided it would be best to change it. That is, until it became evident that if I skipped the song it would admit that I felt uncomfortable, which would imply I was feeling some sort of sexual tension. Was I overthinking this? Possibly, but I put my foot down and I focused on the road.

I continued taking brief glances in Elena’s direction to see if I could figure out if she was feeling uncomfortable. She seemed pretty normal but her face was no longer soft and vulnerable like she usually is with me. She seemed hard-pressed and serious, as if attempting to hide her emotions.

“Can you lick the tip then throat the dick or nah? Can you let me stretch that pussy out or nah?” The song played.

All of a sudden I noticed red flushing on her cheeks. At the same time, we made eye contact which she broke with unnatural haste, as if feeling some sort of shame.

“Are you okay?” I hadn’t ever seen her this flustered before. Her chest heaved up and down as she parted her blackish-blue hair.

“I don’t think I can keep this in anymore.” She responded quietly, as if hoping I wouldn’t hear.

“We should talk about this. If you have something to say then just let it out Elena.” I said, concerned. It was very worrying to see her like this, and if it was about what she saw back on the train then I thought it was best for us to just lay out our feelings and talk it out.

“We’ve been friends for so long. Are you sure you want to hear this?”

“Yes I’m sure, just tell me how you feel.” I urged. There was no getting out of this conversation now, no matter how awkward it may get. But, from my perspective it was better to just get this over with.

“I-I need you.”

“What?”

Elena moved swiftly, pressing her lips into the slide of my lips. She placed her hands on my right arm and thigh. If there were any cars around me I may have crashed. She continued kissing me, moving down through my chin to my neck. She unbuckled her seatbelt, getting nice and close to me. Her breasts rubbed into my arm as she attacked me hungrily with her lips.

“Elena.”

She looked up at me and it was as if her thoughts were painted in the pupils of her eyes.

“I’m all yours.” She didn’t say it, but I know she meant it.

Every thought about controlling my lust, about not acting upon my thoughts of Elena, about not ruining our friendship, about driving, about Lindsey; They were all gone.

Elena moved her hands so one gently held my neck while the other edged deeper and deeper into dangerous territory. When she finally embraced me, she didn’t hold back. She began passionately rubbing my cock, applying pressure to stimulate me even more than I already was. The embarrassed, flustered Elena was completely unrecognizable compared to who was touching me right now.

“I couldn’t stop.” She whispered into my ears, as if admitting her sins.

“I couldn’t stop looking at it, and you tried to hide it from me, but the image had already burned itself into my mind. I needed it. I needed to touch it.” She panted needily.

“Oh, Elena.” I moaned softly. “Keep rubbing me, it feels incredible.”

“I can do you one better.” She said seductively, a fiery look in her eyes.

She began to unzip my pants, freeing my erection like her life depended on it. I didn’t live far from the station but I hadn’t felt so horny in all my life. I started accelerating, attempting to keep my focus on the road as the lioness feasted on the meat of her prey. Elena took my rock-hard shaft into her soft hands and began stroking it with a yearning. As she massaged my member, I took one of her breasts into my hand, kneading into it. She looked up into my eyes and gave me that look once again, as if offering herself to me. Then, while keeping eye contact, she took the tip into her mouth.

“Fuck, Elena!”

“Mmmmm.” I felt my cock vibrate with the sound of her voice, amplified by the swishing of her tongue around the head. She began slowly lowering her head up and down my cock, sucking deeply. She placed one hand at the shaft, stroking and rotating as she bobbed. The other hand found its way down to where her inner thighs met.

“I’m sorry,” She managed to escape from her mouth. “I’m sorry I made a mess in your car. It just kept leaking out of me and onto the seat.” She pleaded. “I think I need to be punished, daddy.”

Holy fuck.

I had never been called that before. It’s not that I didn’t want to be, I just didn’t realize I wanted to until she said it. I’m not particularly quiet during sex, oral or otherwise, but what came out of me right then was purely primal.

I took the hand that was groping her breasts and placed it on her head, pushing her down onto my cock. The sounds of choking and gagging filled the car. Just as I was starting to get close, we arrived at my house. I cursed myself for driving too fast but considering no one was home, I knew the fun was just getting started.

“Let’s continue inside, no ones home.” But Elena just kept sucking and stroking, as if she hadn’t heard me. I grabbed her by her hair and pulled her up, spit trailing from my cock to her mouth shimmering in the sunlight. I pulled her face up to mine and kissed her passionately, our tongues dancing and our salvia mixing.

I grabbed her hand and escorted her through my front door and into the kitchen. I had planned to take her straight to my room but we weren’t able to get that far.

“Mmmm, kiss me.” Elena moaned as I leaned her onto the kitchen counter, our mouths eating away at each other.

Wanting us to put us at the same height, I grabbed her waist and pulled her up onto the counter as she let out a gasp of surprise and excitement. Pulling her body so it was right up against my groin, I began grinding myself into her with a rhythm of an ocean; Wave after wave, crashing down upon her. I don’t know what it was, maybe the fabrics of my jeans chafing back and forth on her cargos, but the feeling was driving me insane. Letting myself get high off this feeling, along with heat forming between us, I let out a deep, animalistic groan. A sudden rush of embarrassment flooded my cheeks but Elena didn’t seem to notice, matching my energy as she let out beautiful sounds of pleasure.

I let my hands roam free and explore the curves of her body, having wanted to experience this feeling for so long I found it difficult to hold myself back. I drifted my hands from her breasts down through her stomach, stopping at the end of her shirt. She moved her arms accordingly as I began lifting it up and off, revealing the cute, black bra that held her incredible tits. I let my lips travel quickly but thoroughly down to my prize, leaving licks and kisses as I went down my path. I moved my hands to her back and fiddled with her bra, (praying my experience wouldn’t fail me right now) and took it off as we continued our lustful embrace.

While I put my full attention into her breasts, taking careful swirls of my thumb around her nipple, Elena grabbed my other hand and placed my thumb on the opening of her lips. As I let my mouth accept her hardening teat, gently sucking and kissing, she let my finger enter her. She let her tongue flow along the underside, controlling my hand to push and pull my finger as I returned the favor. With my left hand holding up the breast I was suckling on, I began inching my hand down from her mouth, letting it trail down her neck all the way to the lower abdomen as she watched with longing.

I let our lips reunite as the outercourse took place down below. I let my hand make its way to her snatch but kept venturing further to her thighs, squeezing them firmly. I undid her zipper and slipped my hand under her panties. As I brought my hand to the source of her wetness, I stayed for only a brief moment. My fingers coursed lightly along the outskirts of her lips as Elena let out a moan of discordance in conjunction with my teasing.

“Oh, please.” She managed to let out. “Touch me.”

Finding it too difficult to resist the pleads for the fulfillment of her bliss, I took my index and middle finger and began sliding them up and down along her opening, making sure to include her now-swelling bud. Her wetness continued to build up, creating a small mess on the surface of the counter. I then left my two fingers directly on her clit, letting them spiral softly along as she let out a groan of pure satisfaction. I then moved my fingers around so my thumb was playing with her clit while my middle finger yearnfully teased her opening.

Then Elena did something I didn’t expect. She grabbed my right hand and pulled it into her, forcing my finger to penetrate her slit. My middle finger plunged within her, and she looked deep into my eyes as an inaudible ‘oh’ failed to get past her lips. I let her take control of the pace, guiding my hand to get herself off. Feeling how soaked she was, I inserted a second finger.

“Oh fuck, Aly!” She moaned.

“You like that? You like fucking yourself with my hand?” I panted.

“Yes daddy I love it!” There it was again, and god did it make me go crazy. Elena then adjusted herself to make my fingers go deeper inside, letting me take the reins as she held one hand on my chin and the other on the small of my back. She began rocking her hips to the rhythm of my hand, letting out a long moan as the sounds of her pussy splattering filled the kitchen.

“Oh keep finger fucking my pussy. Ohhhh it’s so good.”

A smile couldn’t help but form across my face hearing that. As I obliged and kept up my act, I watched as her breasts bounced to the movement of her hips, her hair swinging into her face, her eyes not able to look away as my fingers continuously disappeared inside of her. Wow, she was beautiful.

I needed to take her. And I needed to take her now.

I took my fingers out of her, and placed my hands on her butt. As she let out a needy whimper, I picked her up and started towards the stairs. She caught on and wrapped her hands and legs around me, showering my neck with kisses and bites as we climbed the stairs; A bra and a pool of discharge forgotten in the heat of the moment.

I couldn’t resist squeezing her ass as we made out. I placed her onto my sheets and removed my shirt and pants, my boner piercing through my underwear. I noticed her eyes start to roam, a devious look in her eyes.

Having worked out for the last 3 or so years, I was proud of my body and enjoyed the attention she was giving me.

As I positioned myself above her, she gripped a hand onto my boner.

“I felt you twitching in my mouth right as we made it to the house.” She admitted with a sly smile. “I know how bad you want that sweet release.”

She moved herself onto her knees and pressed her lips onto the outline of my cock. Looking up at me, she began licking from my balls all the way to the head, holding eye contact. Once at the top of my boxers, she used her teeth to release my fully erect cock.

“Where are your condoms?”

Uh oh.

“Um, well.”

“You do have condoms, right?”

“Uh, I just ran out.” I admitted.

“Way to fuck this up.” I mentally scolded myself. All this teasing and foreplay just to miss out on the real thing?

“Well, I’ve never taken raw cock before but I know you’re careful with other girls so I trust you. Just make sure you pull out.”

It took everything in me to not start jumping up and down.

“Yeah okay, deal.” I said, trying to sound as nonchalant as possible.

Elena started taking off her pants while I took off my underwear. When I looked up she sat there, completely naked.

“God, you’re gorgeous.” I let out, as Elena immediately blushed a light red.

“Thanks, you’re not so bad yourself.” She replied while staring directly at my throbbing member.

I once again positioned myself over her, my penis resting just under her belly button. I had known Elena long enough now that I knew she preferred rougher sex, and that was perfectly fine with me. I knew she trusted me, which is why I didn’t hesitate to take my fingers and force them into her mouth. As she lay there with both hands on my chest, I continued perforating until my fingers were dripping in saliva. I then took one of her nipples and placed it between them, giving it a nice pinch until moving on to the other one.

“Please fuck me.” She moaned. “I can’t wait any more!”

“Beg.”

“What?”

“Beg me.”

She hesitated.

“Well I– ohhh.” She let out softly after feeling my cock move up and down her pussy.

“Beg.” She knew I wouldn’t yield.

“Please daddy, please fuck my pussy. I’ll be good for you, daddy. I’ll be a good s-slut for you.”

Whoa.

I could tell she didn’t realize what she was saying until she said it, but there was no way I could resist myself after hearing that. I let the head of my dick enter her as we locked eyes. As I went in to kiss her, I let the rest of my shaft slide its way in.

“Ohhhh.” We both moaned in unison as our lips met.

I started thrusting into her rhythmically, as her hands held my shoulders and her legs wrapped around me.

“I wish we– mmm – fucked sooner.”

“Now that we’re doing this, I’ll admit I used to take glances at your tits whenever you weren’t looking.” I told her as we continued making love. She let out a laugh.

“Yeah I noticed.”

“Wait, what?”

“C’mon, it was obvious but I didn’t mind. I should’ve confronted you about it. We could have been fucking for the last year!”

“Looks like we need to make up for lost time.” I announced as I grabbed her hips and flipped her onto her stomach, re-inserting my full length in one go.

“Oh fuck.” She let out. I couldn’t see her face but I knew she was smiling.

I pulled up her hips to put us in doggystyle, keeping up my pace as I pounded into her. I grabbed a fist-full of hair and pulled her head back while keeping my eyes on her ass while it bounced, and wow it was some view! Elena slipped a hand down to her pussy, touching herself. Removing my hand from her hair, I groped her bubble butt before giving her a light spank.

“Harder.”

Oh my god. This girl was driving me crazy.

I spanked her, hard. She gave a yelp and I knew she was loving it. I continued slapping her ass, letting it turn a fiery red before giving her a rest.

“No, don’t stop. Please keep spanking me!” She begged. “I’m so close.”

“You’re going to cum for me?” I asked, a sadistic tone in my voice.

“Yes I’m going to cum for you, Daddy. Please–OH.” I cut her off with a hard spank. As I beat her already-ruby red cheeks, I felt her body start to spasm. She took a pillow and covered her mouth with it.

“Mmmmmm.” Muffled moans escaped as Elena hit her peak, the walls of her vagina contracting around my cock.

As her orgasm subsided, I flipped Elena onto her back and kissed her deeply.

“Are you close?” She asked.

“Very. It was a good thing you came when you did.”

Elena flashed me a smile before sitting up and pushing me down onto my back.

“I haven’t cum like that in a long time, so I’ll make sure to finish you off like a good slut.” She said as she made her way down to my tool. Without warning she took me into her mouth, going straight down the shaft and letting out a gag. Using the same technique as in the car, she expertly sucked me off. She kept her eyes right on mine, watching my reaction to her prowess.

“Oh Elena, how are you so good at this!”

She continued slobbering on my cock, letting off to breathe but still stroking me. She then spat on it, spreading the saliva until it was practically submerged.

“I think that’s enough.” She decided with a smile on her face.

“For what?” But before I could get an answer, Elena’s tits were being squeezed on my member.

“Oh my god.”

“I know how much you love my big, perky tits.”

As Elena used her breasts to get me off, I couldn’t help but to watch in awe. Whenever it felt like there was a bit of friction, she’d spit on my cock to negate it.

“Elena. I-I’m close.”

“Where would you like to cum, daddy?” I could barely even think, but I managed to come to a decision.

“On your face.”

I quickly sat up while Elena obediently adjusted herself to her hands and knees. She placed her mouth on just the tip of my dick while stroking the shaft vigorously, waiting for her reward.

“Oh, oh fuck! Elena!”

As she took her mouth off my cock and stuck out her tongue, I involuntarily jolted my head upwards. Line after line of white, hot, sticky semen poured out of me, painting Elena’s face. I couldn’t take my eyes off of her. As if she couldn’t have done anything sluttier, she grabbed my still-semi-hard cock and slapped it repeatedly onto her face, letting it pick up some cum before taking it back into her mouth and sucking it dry.

“Wow.”

“Has your slut satisfied you, daddy?”

“Fuck yes you have.” I blurted, half laughing. Elena joined me in the laughter.

“Let’s get you cleaned up, huh? I’ll grab a rag.”

“Actually, why don’t I take a shower.”

“Yeah that works too.”

“I might need some assistance making sure all the cum gets off, you wouldn’t mind joining me would you?

I think my cock twitched.

“Not a problem. I’ll make sure you’re nice and clean.”

She couldn’t help but giggle as we made our way to the shower.