Regretting the Path Not Taken

In college, I was good friends with a girl named Ivy. We roomed together our junior year, we did theater and choir together, and we hung out a lot with our group of music friends. But we rarely spent time one on one. I was a little intimidated by her bold and outgoing personality, and a LOT intimidated by the lust she ignited in me. At that time I was deep in denial about my bisexuality and could not begin to consider that I might not be totally straight. But Ivy was absolutely gorgeous. I could get lost in her big blue eyes, her loud laughter, the sight of her body in revealing clothes. In contrast to my curviness, she was slight and slim, with hips as narrow as a boy's, small breasts that were rarely confined in a bra. I used to zone out sometimes staring at those gorgeous breasts barely out of sight beneath a low neckline, just big enough to cup in my hand, wondering what her nipples looked like, felt like, tasted like. But whenever we changed in front of each other in our dorm or in the theater dressing room, I always looked away, terrified of my feelings.

In our senior year, Ivy moved out of the dorms and into an apartment with her new boyfriend, Chad. Our entire friend group loathed him. Chad was brilliant but pompous and condescending, and now spending time with Ivy involved spending time with Chad too, watching her drape herself all over him. But I didn't want to lose her friendship, so I swallowed my dislike and toughed it out.

One night I went to their apartment to hang out, but Ivy wasn't home from her part-time bartending job yet. I sat in their small living room across from Chad, sipping a beer, nodding at whatever nonsense he was pontificating about. The conversation took an abrupt turn when he suddenly said, "So Ivy and I wanted to ask if you'd be interested in having sex with us."

I stared at him in shock at the unexpected proposition. It gave me an aching feeling in my chest to have the chance to fulfill a secret desire, but with the awful caveat of including Chad in the deal. I tried to imagine what he'd be like in bed -- probably as obnoxious and pushy and self-centered as he was in daily life. I was too young and dumb and shy to realize I could have negotiated, told him he could watch but not touch. I didn't know what else to do but decline. "Um, that's really nice of you to offer, but I...I don't want to...do anything that'll ruin my friendship with Ivy."

Chad nodded. "Fair enough. Would you be interested in having sex with me? She doesn't have to know."

I felt so awkward. I stammered out another polite decline, and my loathing of him grew to see how easily he would have cheated on her. He didn't seem too bothered by my rejections, and the conversation moved on. I guzzled the rest of my beer to drown out my anxiety.

Mercifully, Ivy arrived home from the bar soon after. We all kept drinking, me more than my usual amount, and then smoking. We ended up back in the living room, her and me on the small sofa together. I was too drunk and stoned to remember how we ended up watching porn. We giggled and cracked jokes at the low-budget production, critiquing its stupid script, all three of us pretending we weren't turned by the scene.

Ivy's leg moved first, pressing her thigh against mine. Next it was her shoulder leaning in to me, the slight weight of her hot against my side. Finally it was her hand. Her fingers moved light as a breeze across my bare thigh, up to the hem of my shorts, her touches slow and tentative.

My whole body was on fire. I closed my eyes and held my breath. A frisson of pleasure trilled up my spine, spreading goosebumps across my skin, hardening my nipples so fast they hurt. My whole consciousness centered on the spot she was touching, the nerve endings firing as if she was electrifying them. My limbs felt tingly and limp as everything in my bloodstream flooded to my pussy. The arousal hit so hard it took my breath away.

Somewhere in my hazy substance-addled brain, I had just enough presence of mind to wish I had more presence of mind. But it was all I could do to remember how to breathe. Her fingers traveled higher, up the leg of my shorts, and traced against the crotch of my panties. I know she could feel my pussy lips swelling, the heat building, the wetness just beginning to seep through. She traced her fingers down over the length of my slit, then up again to the spot where my clit throbbed. Gently she rubbed in slow circles, her touch only light enough to be an agonizing tease over my underwear. 

I closed my eyes as she slid her fingers into the leghole of my panties, finally making contact. Her finger slipped easily past my swollen lips, into the hot wetness of my cunt. My head dropped back against the sofa cushion, and I exhaled a quiet whimper. Then she pulled her hand away.

The loss of contact left my pussy aching. I opened my eyes. There stood Chad next to Ivy, staring down at us, a hard bulge in his jeans. She rubbed her hand over his hard-on. Her smile was sly, her eyes filled with a challenge -- your move, sugarcane.

I wanted so badly to pull her close to me, away from her asshole boyfriend, and give her the kiss I'd been trying not to imagine for years. I wanted to strip her bartending uniform shirt off button by button, to finally run my tongue over those beautiful small breasts, to take her nipple into my mouth, kiss and suck and gently bite while she writhed beneath me. I wanted her hand back between my legs, stroking between my wet folds, rubbing my clit that was throbbing from her teasing, hard and needy and desperate for her touch. But sitting there under Chad's leering smirk, I couldn't do it.

I mumbled something about needing to go home. They protested, eventually convinced me to sleep on their couch and not walk back to the college alone in my inebriated state. So that was how I ended up lying in the dark in their tiny living room, the room spinning slightly around me, regret boiling inside me, listening to the noises of sex wafting from the bedroom.

They'd left the bedroom door cracked open. At first their sounds were quiet, all whispers and rustling. Then they got louder. Ivy made the most exquisite moans of pleasure, her voice sending arousal throbbing through me. "Fuck yes," she moaned. "Lick this pussy. God yes. Like that. Right there. Right there." I imagined her lovely body draped naked across the bed, her legs spread wide for him, as he kneeled between her thighs where I wanted to be. Or was she sitting up and straddling his face, bucking and grinding against his tongue, her juices flowing freely down his cheeks and chin as he licked and sucked her to ecstasy? I shoved my hand down my shorts and into my soaked panties. The sound of squeaking bedsprings started up, and I rubbed myself in sync with their rhythm. I imagined her beautiful pussy stretched around his cock as he fucked her. I wanted to fuck her like that, to fill her up and plow into her as hard as she wanted. I imagined myself with a strap-on, equipped with a dildo bigger and more amazing than whatever Chad had, giving her the fucking of her life. 

The bedsprings' squeaking grew faster, and so did my fingers rubbing my clit. My hips started squirming as I got closer. I imagined looking down and seeing her face between my legs, those gorgeous big blue eyes staring up at me as she suckled my twitching clit. That image sent me over the top, and I arched my back as the orgasm rose up and crashed through me. Wave after wave of contractions pounded through my cunt, sending stars into my vision. I tried to keep quiet but I know I moaned. As I sunk back into the sofa and caught my breath, Chad's obnoxious voice started up in the bedroom, announcing he was cumming. I listened to the bed's squeaks slow and then stop. The regret at my lost chance eclipsed the last twinges of pleasure in my pussy. I rolled over and fell asleep for a few hours, then woke in the early morning and disappeared while they still slept so I wouldn't have to face them. For the rest of the school year I hoped so hard they would break up so I could go back and take my missed opportunity without Chad in the picture, but they stayed together and got married after we graduated. I wish I could go back in time and redo my entire college experience with all the knowledge and courage I have now. I'm so annoyed at the shy and meek girl I used to be! But at least my memories of gorgeous Ivy have left me some excellent material for masturbation fantasies today.