Emily’s Dare by mdb5056

A literotic sexstories: Emily’s Dare by mdb5056
It had been a messy breakup with my ex Amanda. I had caught her in bed with another guy. It had been months of long, painful and lonely nights alone cuddling my pillow. Then I found Emily.

She had been a high school friend of mine and several years younger than me. As we re-connected, I discovered I had been her high-school crush but she was much too shy to say anything. She was going to school a couple of hours away from where I was living at the time, but it was always an exciting prospect to make a trip down the road to see her.

Emily has shoulder length very curly light brown hair. Constantly running her fingers through those curls, tempting me at all turns to press her up against something and have my way with her. She constantly wore very tight jeans (that left little to the imagination) with some variation of t-shirt that only accentuated her ample breasts. For being several inches shorter than me, she definitely had a pair of tits and an ass that would knock any guys socks clean off.

She lived in on-campus housing as a “RA” (Resident Assistant) in the dormitories with a whole floor of freshman girls. Basically she was in charge of overseeing activities for the freshman girls who lived on her floor. I never paid much attention to anyone else on the floor, except when Emily wanted to introduce me to someone or they were going out for dinner or something. If memory serves, there were about 20 rooms on this floor with 2 girls to room.

The massive benefit to this job she had been, not including her room and board was paid for, and she had a room all to herself. This made it all but impossible to keep our hands off one another at night when she’d invite me back up to her room.

It had become a weekly event to drive up on a Friday and stay till late Sunday. She had events and games planned for her residents and sometimes I’d help…but the nights were always ours. We soon discovered it was getting harder and harder for us to wait till we got back to her room. It started with make-out sessions on public transportation, then proceeded to fondling on park benches and pretty soon I was groping her just about everywhere. Needless to say, her freshmen residents were very aware of how crazy we both were about each other.

One Friday, as I was making my weekly trip up to see her, I received a text message from her. “Hey sexy. I can’t wait to see you. Hurry to me! I want to cum all over your dick. :-9” She has a pretty good habit of riding my dick, digging her nails into my chest, cumming forcefully and licking it up afterwards. I don’t think I have ever driven that fast before.

When I arrived to her floor, I noticed right off that there was some big commotion at Emily’s door. Just about every girl living on this floor (and some of the guys from the floor below) was standing in and around her doorway. Slightly concerned, mostly confused and a touch frightened I hastened toward the middle of the hallway where her room was. My appearance must have been greatly anticipated because as soon as someone noticed me approaching all the girls exploded in shrieks and uncontrollable giggles.

A hole opened in the mass of bodies crowding the doorway and I stepped into the room. There, surrounded by some now naked freshman girls I had been introduced to earlier in the semester, was Emily: Fully naked, on her back facing me, laying on her bed, held by several girls spread eagle in front of me with a gigantic smile on her face and a huge vibrating dildo sticking out of her ass. The dildo was humming away and Emily was shaking from the vibrations. Sweat clung to her body like many of the curls of her hair. She was apparently unable to make words anymore, the only things I heard from her were groans and moans of passion. It was clear as soon as I laid eyes on her that her freshman floor mates had talked her into this, that she held no objections and that she had been cumming on this vibrator for some time now.

As I stared at her I could only read her lips. No sound came out, but the message was not lost in translation. She mouthed the words: “Fuck” “Me”. Her eyes were rolling up in the back of her head as she said this.

At least two girls had a hold of both her legs and several more here running their hands over her chest and down her sides and through her hair and across her face. All she needed was my (now) rock hard cock and she would explode in several passionate but equally violent orgasms in front of everyone.

In one amazing seemingly endless moment, I looked around the room at all the girls and guys (at this time they were fondling each other but looking on at both Emily and I, as if looking for inspiration or a sign) who here eager to see my reaction to this. Almost everyone in the room was either naked or mostly so, except for me. My one and only reaction was apparently so simple and so perfect everyone reacted simultaneously and in a fury. I smiled.

I smiled and that was it. Some of the girls surrounding me took to tearing off my clothes and rubbing my already hard dick, getting me ready for the pounding Emily was about to receive. As my clothes left my body I caught Emily clawing the bed sheets she was laying on as she succumbed to another muscle clenching orgasm. That vibrating dildo was unrelenting and it was clear she loved ever second of this.

As the last article of clothing left my body (oddly enough my socks), I was gently pushed forward. The door closed shortly thereafter, and it made me think for exactly a tenth of a second how 50+ people could fit in a room designed for 2.

Just as I was about to reach out and grab hold of Emily, one of her freshman floor mates slid in between us. After a split second, I remembered her name. Amber smiled a sly and very telling smile. She had orchestrated this. She had been the one to invite all these onlookers and get my girlfriend impaled on this vibrating dick and begging for my cock. I could have kissed her for all that.

The room hushed. Amber let me know that earlier in the night a couple of the girls had played truth or dare with Emily. The way they play the game is with a deck of cards. Red cards are truth cards and black cards are dare cards. The last card drawn of both colors has to be something super embarrassing or risky. The apparent ultimate dare was what was unfolding before my eyes.

Amber, giggling along with several other girls, continued by saying that she had drawn the last red card. Amber’s ultimate truth was she had never sucked a guy’s dick before. As she spoke she kept sneaking glances down toward my throbbing dick. I guess it should have been obvious to me what was going to happen next.

Amber dropped to her knees in front of me and engulfed my cock with her mouth. The warm, wet and smooth insides of her mouth caused me to gasp in both surprise and pleasure. “Hot damn, she is a natural” I thought to myself. I looked up toward Emily, still clenching the bed and gasping for air. She never lost that intoxicating smile and she watched in her own sense of pleasure as this tiny freshman girl choked herself on my dick.

A few moments later, Amber stood back up, wiped her mouth and kissed me. Just enough to tell me thank you for letting her experience something that she had always wanted to do. She then whispered into my ear to fuck the shit out of Emily.

As Amber slid off to my left, Emily in the same exposed position tried to lock eyes with me. Still smiling she mouthed those words again. Only this time, she added another at the end. “Fuck.” “Me”. “Please.” Damn, I love it when she says please.

In one smooth motion I wrapped my arms around her thighs and positioned my dick right on top of her clit. She bit down on her lip and was threatening to draw blood at any second. The girls surrounding us craned their necks to catch glimpses of our shared moment.

I locked eyes with Emily again, but this time I spoke. The first words from me this entire episode. My message was simple too, and despite saying it loud enough for everyone in the room to hear, it was meant for just her. “I Love You Emily”.

As I finished saying her name I impaled her with every solid inch of me. Despite having a total of seven girls holding her down and grabbing a hold of her, she nearly broke completely free as she gasped a full breath of passion. Her body shuttered, her legs trembled and she came. She came all over me in one solid instant. The vibrator had subsequently shot off like a rocket across the floor, banging into a couple of people and the mini-frig in the corner.

Her nails found my back and immediately dug into me. Using my arms locked up under her legs, I gently lifted her off the bed and gently let her rise and fall on my dick. With every movement up or down she tightened her grip on my back. At some point she was also biting my neck, but I don’t remember quite when that started.

As the night progressed I caught glimpses of everyone else in the room sucking and fucking and fingering and smothering. Only glimpses though, because I was consumed by Emily and how she clung to me. As I stood, erect in the middle of this fuck-fest, with Emily still shaking on my dick, I let her cum several more times. I did not speed up my motion at any point, often allowing myself to slowdown to a thrust every couple of seconds. As she clung to me she took every thrust and climbed steadily closer to another eruption.

Finally, after what was, as close as I could tell, to an hour, I was approaching my own climax. Emily, being very aware of my signs and signals, told me to sit her on the floor. I let her back rest up against the side of her bed and she looked up at me. I expected exhaustion from her, but I was shocked with the enthusiasm as she grabbed my cock and started to suck it dry from all her cum.

As I approached my ecstasy, I felt pairs of hands running over me. It was at this point that Emily and I realized the rest of the room had taken note of our situation and wanted to lend a helping hand. Hands ran over my ass, legs, arms, chest, back, sides, hair, neck and face. Emily found herself in the exact same position as she continued to take my dick in her mouth.

It soon became too much and I let out my own groan of pleasure and felt myself unload all down Emily’s throat. She swallowed and continued to suck as I all but collapsed in front of her. It was her turn to torment me with passion.

We collapsed in a heap on the floor and caressed each other softly. Her floor mates took the hint apparently and let us lie in our own puddle of ecstasy. The door closed again and we felt each other drift off.

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