Dillon's Harem Ch. 01

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Vanilla girlfriend wants to play in front of her roommate.
3.2k words
4.67
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57

Part 1 of the 8 part series

Updated 02/13/2024
Created 11/29/2023
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"So, any big plans for Friday night?"

I startled awake. I had dozed off at my desk again. My new coworker Ava was looking down at me. Ava had quickly become my favorite coworker, and not just because she was one of the most competent people to have cycled through this office in my time. At 26, she was only a couple years younger than me, and she looked like Victoria Justice, but with big blue eyes, which were so iridescent they actually successfully pulled your gaze up from her cleavage, which, granted, was pretty well covered up by her professional attire, but she accentuated well what I estimated to be a 34B chest, which-

"Hello? Dillon? Any big plans tonight?"

"Oh, uh," I tried to pull myself back to the present moment. "Uh yeah, Hannah and her roommate are going to a rave tonight, and they invited me to join them because their other friend got sick."

Ava's eyes somehow got even wider. "Those ARE big plans. I didn't take you for the rave sort."

"No, this'll be my first one. I think it's only Hannah's second or third one too. Brittany goes all the time, and I don't know, it seems like it could be fun! Do you wanna see what the girls are planning to wear? They looped me into a group chat where they've been discussing outfits."

"I'd love to!" Ava was always so positive about everything. She had a very former cheerleader/former sorority sister energy, overlaid with her background in psychology and HR. In my opinion, she was too good for this inside sales role, and I was already preparing myself to lose her at any time.

As I scrolled quickly through my texts, Ava continued making small talk. "You know, I don't think you've shown me a photo of Hannah yet. I'd love to meet her!"

"Yeah, we should set something up." I said absentmindedly. My mind had immediately wandered to the potential of hanging out with Ava outside of the office. "Uh, here's a photo of the two of them together. I think this is more or less their final choices."

"OMG! I love these fits! Wow, Dillon, Hannah's pretty hot. I mean, I figured she would be, obviously, because you're so attractive... I love that leather jacket on her!"

"What?" Had Ava said she thought I was attractive? She said something else too. I gotta try to concentrate. I looked at the photo myself. "Oh, no, Hannah's got the blue hair. That's new. The redhead in the leather jacket is Brittany."

Ava blushed. "Oh, well Hannah is so gorgeous! They're both beautiful. Gonna be a fun night for you!"

She wasn't wrong. I hadn't actually looked at this photo while I was working, but now that we were looking together, the girls were beautiful.

Hannah and I had been dating about two years, and everything was going pretty well. Our sex was rather vanilla, but she was insanely beautiful and exactly my type, so vanilla was still amazing. She was 28 years old (same as me), 5'6", and a slender 115 pounds. She was naturally a very light blonde, and when she wore her hair down, she looked just like Phoebe Bridgers. For the rave, Hannah had gone bold and dyed her hair a vibrant cerulean. She was wearing a navy blue fishnet top, over a royal blue bikini top and white denim short shorts. You could see most of her perky 32B breasts through her outfit, but her nipples were covered.

Next to her in the bathroom mirror, flipping off the camera, was her roommate Brittany. Brittany has gone with a tough, sexy, leather look for tonight, but in reality, she was the kindest, smartest, funnest girl I'd ever met. I was so happy with Hannah, but I'd be lying if I said I hadn't fantasized about hooking up with Brittany, or at times, even pulling off the roommate switch that George Costanza had warned against attempting. It didn't help my fantasies that she was openly bisexual. Brittany was a few years younger than us at 24. She stood tall at 5'10", but had roughly the same weight and boobs as Hannah, so the two often shared clothes. Brittany looked like Karen Gillan, with natural red hair. Her ass was perfect, whether I got to see Brittany in her bikini, or her pajamas, or a towel as she walked from the shared bathroom to her bedroom. For the rave, Brittany had her hair in cute pigtails, which countered the hard look of the black leather jacket, black pasties, and black leather skirt. The jacket covered her arms completely, but didn't have any sort of fasteners and didn't quite reach the bottom of her rib cage, so it left most of her torso exposed.

"Anyway, I hope you have fun tonight! I wanna see more photos on Monday!" Ava walked away from my desk.

I felt bad for not asking what she was doing this weekend...or maybe she had told me while I was zoned out, looking at that photo. Tonight was going to be fun with these two! I decided 2:30 was good enough for a Friday, gathered up my things, and headed straight to Hannah's apartment.

***

I stood in Hannah's bathroom and looked at myself in the mirror. Rather, I tried to look at myself, when I wasn't distracted by the I Spy picture that was Hannah and Brittany's bathroom counter. You couldn't even see the white tile under all the beauty supplies. I understand why they started prepping and pregaming at noon, and why it was overkill for me to arrive a little after 3:00.

I'm not a bad looking guy. I'm gonna look like a schlub next to the two bombshells I'm so lucky to be accompanying tonight. But I'm not a bad looking guy. 6'0" give or take a couple inches depending on my posture, a strong jawline, a permanent pompadour that would make Clark Kent jealous. With my shirt off, you could tell I went to the gym a few times a week. Raves were not my usual scene, and I didn't want to spend too much on an outfit I'd only wear once, so I made do with what I had. A black leather jacket without a shirt under it, some tight dark jeans, and some white sneakers. I kinda looked like I matched Brittany more than Hannah, but that's okay. I wasn't supposed to be here at all, until Taylor started getting light-headed yesterday.

I left the bathroom to find my girls in the living room. "Dillon, a couple ground rules for tonight," Brittany started. "1. Don't consume anything that was not handed to you directly by a bartender or one of us. 2. Don't wander off. 3. You're filling in for Taylor tonight, so you're not grinding on Hannah and making me a third wheel. We're all dancing together tonight in a circle. 4. Keep your hands to yourself and/or on us. 5. Come take a shot."

I looked at Hannah with some consternation. ""She's the boss, babe! This is gonna be fun!" Hannah handed me a shot.

'Yeah, I am the Boss Babe. And don't either of you forget it!" We clinked glasses and downed our shots.

***

It took me a few minutes of jiggling to get our front door open. We had sobered up hours ago, but my small motor skills were struggling, between exhaustion and an adrenaline high.

"That was amazing!" Brittany said for the 100th time. "Did you two have fun?"

"So much fun!" Hannah answered, for the 100th time, but with no less enthusiasm.

"I know YOU had fun, Dillon." Brittany smirked at me.

She wasn't wrong. I wouldn't want to do this every weekend, but getting to dance with Hannah AND Brittany, getting to move to the beat in such close contact, getting to squish together in the back on an Uber...I wouldn't mind if Taylor got sick every now and then so I could tag in.

I was ready for bed, but Hannah slumped onto the couch while Brittany went to the kitchen to pour another round of shots and put something modern and instrumental on her vintage record player. I wasn't gonna be the first to call it a night, so I sat next to Hannah.

As Brittany brought us our shots, I zoned out, looking at her chest. I don't know how long Brittany was waiting to hand me my drink, but I was startled back to the present by Hannah's elbow in my side, so I reached for the shot in Brittany's outstretched hand.

"To my best friends!" Brittany toasted. "Cheers!" Hannah and I chorused, and then we all downed our shots.

Brittany maintained eye contact with me as she took her leather jacket off and threw it toward the front door. She was now standing in front of me, in nothing but a tiny black leather skirt, and an "X" made of black electrical tape on each nipple.

I could feel a new sort of tension in the room. I had always lusted over Brittany, but that had always felt very one-sided and unactionable. Tonight, though, as we had danced together, as the crowd had jostled us into errant physicality, as our blood pumped in sync, as we were overwhelmed with adrenaline and euphoria...

"You know, Han. Dillon was such a good sport tonight, and he did such a bang up job filling in for Taylor. It's not fair that we've paraded him all night through a room of hot women in g-strings and lace. Don't you think he deserves to finally see some fully uncovered tits?"

I wanted to look for Hannah's reaction, but I couldn't tear my eyes away from Brittany picking at the corner of her electrical tape.

"Hmm, well I suppose he does deserve some expression of my appreciation." In my peripheral vision, I could see Hannah moving about, and then a flash of blue flew over my head to follow Brittany's jacket.

"Exactly," Brittany purred. "Dillon, care to do the honors?" I could see that each X had the smallest corner peeled up now.

Hannah got on her knees next to me on the couch, put her right hand on my thigh, and whispered in my ear, "Do it. Rip it fast, like a band-aid."

I gingerly reached each hand toward Brittany's homemade pasties, and grabbed the corners firmly between two fingers. I had never been this close to her tits before. I looked up into Brittany's emerald eyes, and she looked down into mine with what I didn't dare mistake for lust. With a deep breath and full eye contact, I ripped the tape off all at once.

Brittany scrunched her eyes shut and sucked air in sharply through her gritted teeth. She looked for a moment like she wanted to scream "FUCK!". Instead, she resumed her lustful eye contact with me and husked, "fuck."

I shivered with my whole body, despite the sweat on my brow. I slowly shifted my gaze down, until I finally saw my crush's fully exposed tits for the first time. They looked remarkably like Hannah's: two round, perky handfuls, so creamy, capped with nickel-sized dark pink nipples. I couldn't stop my eyes from tracing the subtle curve from her collarbone, down her sternum, under the slight crease of her boob against her torso, and up the outline on the other side. Those nipples were burned into my memory forever.

"Aren't they spectacular?" Hannah whispered in my ear. "I've seen them so many times, and the urge to suck on them has never gone away. Maybe one day I actually will take a taste. For now, there's something else I have the urge to suck on."

Hannah started fiddling with my belt. I couldn't believe she was doing this in front of her roommate, who was still standing tall and proud in front of us. Brittany took a few small steps backward and sat down on the coffee table. I guess she was staying for the show.

Hannah finally got my belt and pants undone. She reached her petite hand in and pulled out my throbbing cock. She jerked it a couple times, as she whispered in my ear, "Don't take your eyes off Brittany." Then, she bent over on her knees next to me and took my hard cock in her mouth. I groaned immediately.

In front of me, the object of my directive was getting herself into position. She scooted herself back further onto the coffee table. She shimmied her leather skirt up above her belly button, exposing her pussy to me! The realization that she hadn't been wearing anything under that skirt all night, including when she ground on me at the rave, hit me like a ton of bricks. I shuddered, accidentally thrusting myself a little deeper into Hannah's throat. Brittany had a thick, curly, red bush. It covered as much of her pelvis as it could without being exposed in average bikini bottoms. Brittany spread her legs and put each foot up on the table next to her, so I had a wide open view of her lovely lower lips. I watched as Brittany took two fingers into her mouth, sucked them for a minute, and then touched them to her clit.

All the while, Hannah was worshiping my cock. She'd lick it from the base to the tip, take it into her mouth, and then bob down on it until her nose touched my pelvis. Everything she did was slow and languishing, as if she were just keeping me warm while I watched Brittany's show.

And Brittany sure put on a show. Her fingers ground into her clit to a rhythm that seemed to consume her whole body. Her chest flushed until it matched her hair. Her breathing got shallower and shallower. She brought her knees together a little as she stuck her middle two fingers deep inside herself and then flexed her legs back apart. Her pelvis pushed out toward me as she ground the palm of her hand into her clit while curling her fingers to touch her g spot. Her eyes closed firmly and her mouth opened loosely. I could see the strain in her other hand behind her, trying to support all her weight from falling off the back of the table. Brittany stopped breathing altogether for a full minute, and her body seemed frozen in time, spring-loaded for when the world started turning again. Suddenly, she convulsed forward, with a burst of exhalation! Her abs shuddered repeatedly like she was doing crunches while sitting upright, and she gasped and grunted as her lungs fought for air against the motivations of her libido. As her orgasm subsided, Brittany leaned forward, her two feet slipping to the floor, her left hand finding support on her left knee, and her right hand finding support on my left knee. She caught her breath, hunched over in front of me, and the feeling of her hand on my leg while I was getting a blowjob nearly ended me.

When she got her wits back, she leaned back on the coffee table again, breaking her physical contact with me, but not her emotional contact with me (at least, that's how it felt to me).

Hannah came up for air and said, "It's my turn for one of those!" She stood up from the couch and removed her white shorts and her blue bikini bottoms all in one motion. She was now fully naked in front of me and her roommate. Hannah also maintained a curly bush, which I found incredibly sexy - you don't see blonde bushes that often. To my surprise, Hannah had dyed her bush the same vibrant cerulean as her hair!

My cock was streaming pre-cum and I could see Hannah's pussy glistening with her own sexual fluids. She stood up on the couch, with one foot on either side of my lap, putting her pussy right in front of my face. I leaned in and gave it a few deep licks. I don't know what it is, but Hannah has the most delicious pussy of any girl I've ever known. I started to suck on her clit, savoring her juices and the thrill of our exhibition to her roommate. All too soon, Hannah pushed my head back - I guess she was too amped up for much more foreplay.

Keeping her feet flat on the sofa on either side of my hips, Hannah squatted down until her ass was on my thighs. She leaned back and put her hands on each of Brittany's knees for support. Brittany still had her feet on the floor and was leaning back in parallel to Hannah, with her hands on the coffee table behind her. Hannah lifted her hips and shifted forward toward me, so I grabbed my cock in one hand and aimed it at her wet pussy. It slid right in like a hot knife into warm butter. Hannah started rolling her hips, massaging my cock inside her, and thrusting her blue bush toward me. I reached forward to rub her clit with my thumb. Meanwhile, Brittany's body was eclipsed from me by Hannah's, but by the sounds I was hearing, I could tell she was going for round two of her own.

None of us were going to last much longer, and we all knew it. Hannah paused to turn herself around. She and I both love finishing with me behind her. She kneeled over my lap, lined up her pussy with my cock, and sank down onto it again. Then, Hannah leaned forward and put her hands on the edge of the coffee table on either side of Brittany's legs. She started slamming her hips up and down, working us both very quickly to our climax. I was shocked and so incredibly turned on, when Hannah lifted her head to find one of Brittany's nipples inches from her face, so she stretched out a little further and started sucking her roommate's nipple while fucking me.

I could tell Brittany was shocked and turned on too because her eyes sprung open. Most of her body was still hiding behind Hannah's, but with Hannah bent over so far, I could see Brittany's face as she masturbated on the other side of my girlfriend. We made eye contact. Brittany licked her lips slowly. I don't know when it happened, but I idly noticed that there was no sound in the room - there was just Brittany's eyes, looking into mine. My consciousness hung suspended in that moment for what could have been an eternity, but just as easily could've been half a second.

Sound returned sharply, as Hannah squealed, Brittany gasped, and I grunted out our simultaneous orgasms. I pumped the largest load of my life into Hannah's pussy. Brittany collapsed onto her back with her head hanging off the far side of the coffee table. Hannah collapsed forward with her face resting on Brittany's knee. I collapsed backward, my head sinking into the couch behind me. I closed my eyes and promptly passed out.

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SirKevinSirKevinabout 1 month ago

Abrupt ending, but an excellent chapter 1.

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