Dillon's Harem

"And that's how my team raised sales numbers in our district by 6% this quarter!"

Polite applause forced me back to the present. I had missed all of Ava's presentation. I was grateful she had cleaned off her face, but I spent the whole 2:00 meeting paranoid that I could see my cum on her collarbone or seeping through parts of her blouse not covered up by her jacket. Luckily, it was one of those meetings I just had to sit and listen to - nothing for me to contribute, really. I couldn't believe how bubbly and unperturbed she could be, standing there in cum-stained clothes, after what we had just done together in my office a few minutes ago. Based on the way my coworkers pushed forward in the meeting without comment, it seemed like they didn't notice anything out of the ordinary. Just Ava being her exceptional, positive, stunningly beautiful self.

As my boss talked about market forecasts, I zoned out again. Ava's blowjob had been phenomenal. I still felt phantom throbbing in my cock. At the same time, I felt incredibly guilty. Hannah had told me not to cum because she had a surprise planned for me tonight. I wondered what Ava's Stress Relief Workshop would actually be like when she conducted it a few weeks from now. Surely, it wouldn't be anything like what she had practiced with me this afternoon... No, I couldn't let this happen again. It was too risky. I vowed to keep Ava's blowjob tucked away in my memories and in the locked folder on my phone. Hannah and Brittany didn't need to know about it. Why was I even considering Brittany? Hannah was the girlfriend I had-

"Hey, it's Friday. If there's not any other new business to discuss, let's cut the meeting a little short today. You all finish up whatever work can't wait until Monday, and then take off for the weekend."

Didn't have to tell me twice. We all shuffled out of the conference room. I hurried to my office, shut down my computer, grabbed my stuff, and made for the exit.

***

Hannah answered her door in pretty casual clothes. I wondered what she had planned for tonight. I took a few steps into her apartment and then stopped in my tracks when I saw her roommate Brittany.

Brittany looked gorgeous as always. The 5'10" redhead was wearing a thigh-length sundress, green with small white and purple flowers, and white heels. I couldn't help but scan every soft inch of her slender arms, shoulders, and cleavage, all exposed by spaghetti straps with no hint of accompanying bra straps.

"Surprise!" Hannah exclaimed. "Your date tonight is with Brittany!"

"What- why-" I tried and failed to form a question.

"Well, we've been talking and, through no fault of her own, Brittany has had a bit of a bad streak of dating bad guys. No offense, Brittany. It's been a while since Brittany has been on a real date with a good guy. That's why I offered to lend you to her! I want you to take her out and show her a good time. Realign her expectations of what a date should look like."

Brittany smiled at me, demurely. "If you want to. I think it could be fun, for the two of us to spend the evening together. We never really get to do that."

"I- well- yeah, I'd love to. Um, I'd love to take you out." I was suddenly very nervous, more nervous than I'd ever been on a first date before, and this one was just a fake date, for practice!

Hannah continued to explain, "I've made dinner reservations and bought movie tickets. Classic. You two should go out, get to know each other, have some fun, and then come back here. I'm gonna go hang out with Zoey for a few hours. I should be back about 11:00."

"Okay, um, sounds great." I was being so awkward. This was a great surprise, but I guess I wish I had prepared differently.

"Yay!" Hannah gave me a hug and a kiss on the cheek. "Thanks, babe! I love you!" She then leaned in and whispered in my ear. "This is why I haven't let you cum all week. I want you all riled up, so that after your date, you can come back here and fuck her senseless. I have a feeling she'll put out on the first date for you. Make sure to cum deep inside her. I want my tongue to have to really hunt for your cum as I lick it out of her." My cock responded immediately.

"What time is the movie?" Brittany seemed anxious to get going?

"7:00, so you two should get going! Dillon, be respectful and show Brittany a good time. Brittany, bring Dillon back in one piece. Oh wait! Let me get a photo of you two kids going on your first date, so cute!"

When Hannah was done playing chaperone, I took Brittany's hand and led her out the door and to my car. I opened her side for her, helped her in, and then turned to take one last look at Hannah in the apartment window. Hannah smiled and waved and then gave me a thumbs up. With a deep breath, I trudged around the front of the car and got into the driver's seat.

***

"That movie was so bad!" Brittany shrieked with laughter. "Did you see the special effects when that car exploded? It looked like they were holding a bic lighter behind a matchbox car!" Brittany laughed some more.

"Oh, and the lead's accent? What country was she even supposed to be from? She kept flipping between Japanese and Jamaican!" I had really had such a wonderful time tonight, and getting to laugh together on the drive home felt magical.

"How did it end? Did they ever find the macguffin?" Brittany asked.

"Oh, what, were you having trouble following the plot for some reason?"

Brittany smiled at me slyly. "You know I got bored in the middle! And when I get bored, my hands get fidgety."

"Oh, is that why you started giving me a handjob, right there in the back row?"

"No one saw us! And yes, that's the only reason why. Just boredom. Not because your penis is one of the most glorious things I've ever held in my hands. So yes, I got a bit distracted and I missed the end of the movie. How did it end?"

"Umm, I also got a bit distracted," I smiled.

"You were supposed to keep watching! At least you were still facing forward!"

"Well, when you turned toward me to start jacking me off, I noticed that I could see right down your dress, and that you weren't wearing anything under. Once I saw nipple, the movie was pretty much over for me." I explained.

"Babe! Now, if Hannah asks about the movie, she's gonna know we weren't paying attention."

"I don't think she'll care too much about that," I advised. "At least we can tell her how nice dinner was. You kept your hands to yourself there."

"Ugh!" Brittany feigned indignation. "Of course I did! That was a fancy restaurant!"

"It was really nice getting to just sit and talk, just the two of us."

"It really was," Brittany agreed. "I genuinely had such a wonderful time tonight. I had no idea we had so much in common."

"I really feel like our personalities just meshed so well together. I feel so close to you." The car was silent for a moment, but not an awkward silence - a content silence, as we enjoyed each other's simple presence. "You know, I wouldn't mind doing this again some time... I mean, if Hannah is okay with it. It doesn't even have to be a formal date. It would just be cool to hang out with you."

"I would too," Brittany smiled at me. "If Hannah's busy or just isn't interested in what we wanna do, it would be nice for just us to go." There was another moment of content silence. Then, "Okay, I can't wait any longer. I need that dick in my mouth. Keep your eyes in front of you this time, babe."

That was the second time on this car ride that Brittany had called me 'babe,' like Hannah usually did. I liked it.

Brittany turned sideways in her seat, like she had at the movie theater. She was probably flashing her ass out the passenger window, but there weren't many cars on the road tonight. She fiddled with my pants and extracted my cock. She stroked it a few times to get it hard. "You know, that mold we made of your cock is so accurate. It really looks and feels just like this. Thanks for letting me use you as a model. I've been practicing with Little Dillon pretty much every night. I can't wait to get the real thing inside me." The image of Brittany using a me-shaped dildo sure helped me get hard!

Unfortunately, that's when I pulled into the parking lot of our apartment complex. Brittany still had her hands working my shaft and balls, but she hadn't got her mouth on it yet. "We're here," I announced.

"Ugh! Not yet!" Brittany complained. "Just give me a minute." Even though I had parked, Brittany still pressed forward. She took my head into her mouth and started sucking.

I looked around. In the distance, I could see a couple sitting on a park bench. To the right, there were a couple women lounging by the pool. It was dark and no one was looking our way. I'm not sure I would've cared if they were. All I cared about was Brittany's mouth, bobbing up and down on my shaft. I let out a moan of sexual satisfaction. Brittany took me all the way to the base and then hummed as she slowly pulled off. My cock sprung from her mouth with a small popping sound.

"Alright, let's take this inside." Brittany growled at me.

The next thing I knew, we were making out in the hallway, while Brittany tried to get her keys out of her bag. She finally handed me the keys, so I could struggle with the lock, while she threw both arms around my neck and both legs around my waist. We continued making out as I lumbered into the apartment, carrying my little redheaded sex pistol like a koala. She dropped from me and ran to her record player.

Seconds later, I heard Theory of a Deadman's "Bad Girlfriend" and I saw my pseudo girlfriend running toward me at full speed. Her embrace pushed me up against the wall, as she resumed making out with me and unbuttoning my shirt. "I've been waiting too long for this," Brittany informed me.

"Too long tonight, or too long ever?" I asked cheekily as I took my shirt off.

"Both," Brittany husked. I took her hand and stepped toward her room, but Brittany's feet were planted. I felt the tug of her resistance behind me, so I turned back toward her. Her eyes burned with a passion I hadn't seen before - there was a concentric ring of another even brighter green inlaid within her emerald irises.

"Bend me over something," she directed me pointedly.

I spun her around and pushed her up against the kitchen counter. She bent at the waist and pulled her dress up to reveal her toned ass to me. I quickly unbelted and unfastened my pants, grabbed her hips, and lined myself up. I could feel my heartbeat pulse in the head of my cock, resting against her pussy lips. I breathed in deep, held my breath, and entered my girlfriend's roommate for the first time.

Brittany moaned with relief, as if I had scratched an itch she couldn't reach. Her pussy felt like home to me - so warm and soft, like she was giving my penis a hug. On my second thrust, I slipped all the way into Brittany's wet pussy, until my pelvis bumped against her ass. Brittany cooed as my cock found a perfect fit inside her. I began thrusting in and out, and Brittany whimpered every time I bottomed out. Faster and faster I pumped my hips, and Brittany's whimpers became lighter and breathier. My fingertips dug into her hips as I pounded Brittany from behind. A hard smacking sound echoed throughout the apartment, coupled with my grunting. Brittany tried to articulate through the pleasure, "I'm- I'm g- na- c-" Suddenly, her back arched, forcing her whole torso upward, and her hands slammed palms down on the counter. "CUUUUUUMMMMMM," she screamed so loud the neighbors surely heard her. Her body spasmed in front of me for almost a minute with the aftershocks of her orgasm. Now I was actually glad Ava had blown me a few hours ago, or else I never would've been able to hold on long enough to get Brittany here.

As Brittany came down from her orgasm, she slipped away from me. She turned and pressed her butt against the kitchen counter. She crossed her arms, pinched her dress in two places, and pulled her only item of clothing off over her head. Then, she leaned back with her arms supporting her weight from behind. I took in her statuesque beauty in full. Her strong cheekbones, her flushed chest, her perfect boobs, her defined abs, her red bush. I couldn't believe I was standing in front of such absolute beauty-

"Fuck me face-to-face now," she commanded.

Who was I to argue? I shook my pants off my ankles as I stepped toward her. I placed one hand on the small of her back and the other hand on the back of her neck. I leaned in to kiss her on the lips, as I pushed my cock into her folds once again. I could feel Brittany smile into our kiss as I worked my cock slowly, passionately, in and out of her. Breaking our kiss, I finally got to cup her perfect 32B boobs, just slightly bigger than a handful.

"This is really lovely," she said to me. "I haven't cum so hard in a while."

"This has been some of the best sex of my life," I agreed.

"And we're not done yet!" Brittany smirked at me. She placed her fingertips on my chest and gently but firmly pushed me back a step, until my cock slipped out of her. She pulled out one of the backless stools from the kitchen counter and silently directed me to sit on it. Brittany bent 90 degrees at the waist and took my cock into her mouth again. She bobbed up and down a few times, while fondling my balls in her hand. Standing up straight again, she looked me in the eye to say, "Yummm, I love tasting myself on you. But I need you back inside me."

Brittany hopped her slender 5'10" body up into my lap, facing me. She used my shoulders as leverage to lift herself up and position my cock at the entrance of her pussy once more, and then she sank down onto it in one motion. She wrapped her arms around my neck and her legs around my waist and began to grind. Her hard nipples pressed into my bare chest as she rocked her hips. I was amazed at the amount of control she had over every muscle in her body. It felt like the full length of my shaft exited and reentered her pussy with each gesture of her hips. "Oh, God, right there, holy fuck, your cock feels so good inside me! This is even better than I imagined when I used your dildo on myself. Fuck! Ugh, I need this cock in my life! I wanna ride you like this every night! Fuck - fuck - FUCK! You're hitting my g-spot and I'm gonna- I'm gonna-"

With a scream, Brittany crested into her second orgasm of the night. Her knees pinned more tightly around my waist, and her arms wrapped more tightly around my shoulders, as her entire body shuddered half a dozen times. It took all my willpower to hold off from cumming myself. As I was once again mentally thanking Ava, Brittany's limbs loosened around me. I felt her go limp and start to sway away from me, so I grabbed her sides more supportively. Her face sank into my shoulder and we rested there together for a moment, with my cock still inside her.

"You haven't cum yet?" she asked faintly. "Then use me until you do."

Looking around, I decided how I wanted to finish. I carried Brittany across the living room and laid her on her back on the couch, with her ass hanging over the edge of the armrest. At this point, my abs and my legs were tired, but my need to cum was stronger. I stood at the end of the couch, put Brittany's legs over my shoulders, and began fucking her to one last orgasm. I placed my right palm on her pelvis, and rubbed her clit with my thumb, while I pumped my cock in and out. Suddenly, we heard keys sawing into the lock of the front door. I was too lost in the moment, so I kept sawing my cock in and out of my girlfriend's roommate, as my girlfriend entered the apartment.

"Hey guys! Sorry I'm home a little early. I got a little impatient. No, no, please, continue!" Hannah approached the back of the couch and looked down at Brittany. "Damn, that's hot..." She walked around the couch, pulled the coffee table away, and knelt with her face near the joining of my pelvis to Brittany's. "Mmm, mind if I get a front row seat to this action?"

All the while, I kept thrusting in and out of Brittany. I think it turned her on to have an audience, especially when the audience was my actual girlfriend. As soon as Hannah got home, Brittany's sounds became more impassioned and her hips ground into me more. I was well beyond my limit from so much time in Brittany's perfect pussy, and Hannah's encouragement quickly pushed me over the edge.

"Mmm, cum babe. Cum deep inside her. Fill my smokeshow of a roommate with your cum!"

With a grunt, I finally started shooting my load. The flexing of my cock inside Brittany caused her to cum a third time too. Her pussy contracted and milked my cock of every micromilliliter of cum I had left in my body. I'd never felt anything as amazing as sharing a simultaneous orgasm with Brittany.

We each breathed deeply for a few moments, and then Brittany said, "Hannah, I can't thank-"

Brittany was interrupted by Hannah grabbing her hips and swiveling her around until Brittany's legs were draped over Hannah's shoulders.

"Oh, yes, Han, please eat me out! Scoop all Dillon's cum out with your dirty little tongue, you dirty little slut. You know my favorite place to have cum? You know, we've talked about this."

Hannah seemed to nod, as she ground her face into Brittany's pussy. She was voracious as she dug deep into her roommate with her tongue. When she felt like she had gathered up enough of my cum, she propped herself up, leaned close to Brittany, and spit a mouthful of my cum on Brittany's face from point blank range.

Brittany shuddered. "Ugh, fuck yes, you know exactly how to get me going again, roomie. I love having cum all over my face."

"I'm gonna do more than just get you going. Zoey gave me some pointers about carpet munching. We're gonna see who gets you off better, Dillon or me!" With that, Hannah dove back into Brittany's pussy. I watched as my girlfriend's beautiful face pressed up against her roommate's beautiful pussy, which I had been fucking all night. Hannah's nose was buried in curly red bush. Her blue eyes were opened wide and directed up to watch Brittany's reactions. Her mouth was suctioned so tightly to Brittany's sex, but every now and then there'd be a slight separation and I'd see a flick of Hannah's tongue against-

"Hey babe," Brittany got my attention. "Think you got one more in you? Go fuck your girlfriend. Thank her for the evening she gave us."

I was too exhausted to do much more than mechanically push into and out of Hannah from behind, while she licked her roommate's pussy. Hannah was a fresh ball of energy and enthusiastically ate Brittany to her fourth orgasm of the night. Seeing Brittany's cum-covered face scream out in ecstasy was enough to push me over the edge into my second orgasm of the night (third of the day).

Brittany lay draped halfway off the couch. Hannah sat back on her heels. I laid back on the carpet.

Hannah asked the darkness, "So, how was the date? Think you'll ever go out again?"