Dillon's Harem Ch. 08

"It really couldn't have gone any worse, is all I'm saying."

"Hmm?" I had to stop to catch my breath, and Kelsey stopped with me. "What couldn't have gone worse?"

"The orgy! Dillon, weren't you listening at all?" Kelsey asked.

"I... well, I was! But then... I must've gotten distracted." I answered sheepishly. I still wasn't sure why Kelsey had texted me to go on this run with her - I would've assumed she'd take Hannah's side in the break up - but I was glad she did. I liked this girl, and not just because she had gotten naked and stroked my dick a couple weeks ago. The memory of her nude body was getting me distracted again, as I looked my ex-girlfriend's friend up and down. Kelsey had such toned legs from her active lifestyle. Her tiny blue running shorts complemented her Georges Seurat-inspired leg sleeve tattoo, and her tight red sports bra complemented the flush in her heaving 36D tits. Her abs had a delectable thin sheen of sweat that I wished I had caused. I couldn't tear my eyes away from her expansive cleavage, as I remembered her confession that nipple play alone could make her-

"It was fun, obviously," Kelsey explained. "I tried a bunch of new things that I loved (although my sister tried to make me try a few things I didn't love). It changed my relationship with my roommate in a pretty constantly horny way. But I mean the way we handled you and Hannah couldn't have gone worse. I just feel like if we had included her, if we had at least talked to her about it, idk, if we had just done things differently, then maybe you two wouldn't have broken up afterwards."

"Yeah... yeah, I wonder the same thing sometimes," I replied glumly.

"Listen, we all really like you, Dillon. We think you and Hannah are a good match, we like hanging out with you, and we like having naked fun with you." Kelsey reassured me. "We want 2 or preferably 3 of those things to happen again. So, would it be alright if I called Hannah and plead your case for you?"

"You would do that!?" I was incredulous. "That would be amazing!!"

"Okay, great! I'll call her this afternoon. In the meantime... I see you staring at my tits! Does exercise make you horny?"

"Well, YOU make me horny," I said pointedly.

"That's a good answer," Kelsey smiled. "Exercise does make ME horny. So in the meantime, while you're technically broken up... how about some of that naked fun?"

This day just kept getting better. "Right here? Right now?"

"Why not? I mean, it must be weeks since a girl has made you cum," Kelsey speculated. I decided this was a good time to keep my mouth shut about Ava and Acadia. "Do you really wanna wait any longer?"

"Nope!" I looked around. I'd never done anything in public before, but the trail was empty. It had been hours since we had seen anybody else.

"Good! Then take your fucking shorts off."

I did as I was told, and Kelsey held out her hand for my shorts. She took them and laid them on the path in front of me, so she'd have a relatively soft place to kneel. Of all Hannah's friends, I had thought Kelsey was the most ambivalent toward me. Not so, I realized, as Kelsey took a broad lick of her palm and then grasped my quickly hardening dick. Kelsey proved again the assessment I had made during our orgy: she gave the best handjobs of any girl I'd ever known - ever heard of, even. I don't know how she did it, but her hand felt as good on my cock as a mouth or a pussy. It was warm and tight, but simultaneously soft and luscious. She gripped her fingers individually and crooked each knuckle independently, so that her hand perfectly conformed to the size and shape of my cock. As she stroked me up and down, each square centimeter of her hand constantly reformed around me so that my erection was always perfectly enveloped. Kelsey also seemed to know exactly how fast to stroke me, how to bring me right to the edge without letting me cum, and how to perfectly massage my balls. She put just the tip between her lips and pushed her tongue out to swipe back and forth along my frenulum, while both hands stroked my shaft.

"Do you like that, Dillon? Huh? You like the way I stroke your big cock? Look how, even with two hands, there's still room to stroke you up and down. Hmm, I bet you wish I'd stick this cock down my throat or in my little 23 year old pussy, don't you? But no, I just like giving handjobs! Maybe you wish there was another girl down here who would be more willing to blow you? Like maybe my black goddess of a roommate, Zoey? You know that ever since our little orgy, I've been making her suck my strap-on? She seems to be into it, and it turns me on like crazy. Maybe we'll let you watch again sometime... Are you ready to cum, Dillon? Are you? Wait, hold on!" Kelsey let go of me all at once and staved off my orgasm. "I have one more treat for you." Kelsey stood and shimmied off her shorts, giving me an up close and personal look at her pussy and her landing strip. "Sit down!" she commanded.

I sat quickly and my hopes soared that maybe I'd get to fuck another of my ex-girlfriend's friends.

Kelsey sat in my lap reverse cowgirl style, with my cock pointed up in the air between us. She reached down and thumped my cock against her pussy hair a few times. "This is where I want you to cum," Kelsey instructed me. "Right here on my thin little bush."

As Kelsey resumed stroking me, I reached up and pulled her tits free from her sports bra. I started tweaking her nipples and massaging her massive boobs. Over her shoulder, I saw a jogger approaching down the trail, but I was too deep to care now. Kelsey said she could cum from nipple play alone, and I wanted to add that notch to my figurative bedpost. Exercise must really get Kelsey horny, like she claimed, because I soon started recognizing the signs of orgasm in her. When the jogger was close enough that Kelsey could hear his footsteps, she turned and looked over her shoulder sharply in a panic. I took the opportunity to surprise her by pinching her nipples and pulling slightly. The excitement of what we were doing, combined with the thrill of being caught pushed Kelsey abruptly over the edge and she came violently in my lap. Her orgasm triggered mine, and I came hard and heavy, shooting six or seven thick loads into her pussy hair. The jogger sped up as he passed us and hurried down the trail.

"Give me your phone," Kelsey said once she'd caught her breath. I unlocked my phone and handed it to her. Kelsey pointed the camera down from her POV, toward my still mostly erect cock and her pussy covered in thick ropes of my cum. She took a few photos from slightly different angles until she was satisfied. "Don't let Hannah see those," she warned me.

***

***

***

"So, how long are you gonna be at your parents' house?" Kelsey asked.

I probably should've been mad at her for her part in the orgy with my now ex-boyfriend, but I mostly blamed Dillon for that. Plus, I needed the support of my friends right then.

"Oh, I don't know. Probably another couple of weeks. I can work remote, so there's no rush for me to come home." I told Kelsey.

"Makes sense... Are you still mad at Dillon?"

"Of course I am! He cheated on me!"

"True, true. If it's any consolation, I don't think Dillon was TRYING to cheat on you... He really seemed to think that you would be okay with blowjobs. And then at the end, Brittany blindfolded him so that he wouldn't know which of us was putting him in which hole. He looked genuinely relieved when he found out he hadn't fucked any of us, just Brittany." Kelsey explained.

"I guess that helps a little... I'm still not ready to forgive him though." I determined.

"I didn't think you would be! Maybe you shouldn't be. Go have some rebound sex! That'll make you feel better!"

I laughed. Maybe I did need to get fucked. Even things up a little.

"It was a weird night too..." Kelsey continued. "I thought it would be weird to see my step-sister slutting around, but I was actually fine with that, which was weird by itself. What got me though is that Taylor kept giving me these weird looks. And at the end of the night, we were all watching Brittany ride Dillon... I sat in the big chair first, and then Taylor insisted on squeezing in next to me! I kept trying to tell her to get her own chair, but she wanted her naked body pressed up against mine while we both masturbated. Even worse, the hand that wasn't on her clit, she used to stroke my thigh! I don't know, it just felt like she was coming on to me..."

"Hmm, that is weird." I agreed. "I mean, Taylor has always been a bit of a flirt, but- oh, hold on. Victoria is calling me. We're going out to dinner tonight. We'll have to talk about this more later. Thanks for calling to check in on me!"

***

After dinner, I spent the night at Victoria's place. She had her own apartment, of course, and it was nice to get out of my parent's house for a bit.

"It's been so great catching up with you!" I gushed. "I know we text pretty regularly, but we haven't had a hang like this since, what, high school?"

"I'm having so much fun!" Victoria agreed. "I'm glad to see you liven up too. You need it after what Dillon put you through!"

"Mmhhm," I agreed. I sipped my wine and looked over my best friend. She was a year younger than me, about the same 5'6" I was, with shoulder-length brown hair, and brown eyes. Her boobs were a little bigger than mine, as I knew she was about a 34B to my 32B, but not enough bigger for me to be envious. People often compared her to Jewel Staite. When we had got back to her place, she had changed into her pajamas: a matching short-sleeve snap-up shirt and shorts, both made of a turquoise silk with a small floral pattern. She'd lent me a similar all-black set for tonight.

"By the way, I LOVE the hair! That fiery metallic red? Very sexy villian-era of you. Have you done anything else rebellious in your rebound?"

I appraised my friend in a new light. I'd always thought she was cute. I don't know if it was the rebound or the wine or my recent experiences with Brittany... but I started to get a bad idea.

"You know," I began, "not really. I'm itching to though. I wanna get back at him for cheating on me. I wanna do something wild. I'm horny as hell... what do you suggest?"

"Well, obviously you need to find some random guy that'll just fuck you senseless!" Victoria giggled. "Hey, you're in your hometown. Any old crushes you wanna text for a booty call?"

"Hmm, maybe... I don't know if that's wild enough though... What's the craziest thing you've done sexually?" I asked.

Victoria blushed lightly, but grinned at me conspiratorially. "Have you... ever done anal?" she asked me.

"No! But that's perfect!" I felt like I had hooked Victoria and now just had to reel her in.

Victoria hesitated for a second, but then dove under her bed and came back with a shoe box. "You should try it! It makes you feel so good and full and it makes the guy cum so hard." Victoria then started showing me her toy collection. "See I use these more slender dildos when I play with my asshole. And see how these butt plugs get progressively bigger? That's how you train yourself to take a dick up there."

"Wow, this is a lot. It's a little intimidating, actually, to think of putting something up there... do you think, well, do you think you could help me?"

Victoria froze. "Wouldn't you want a guy to- well or by yourself you could start small and-"

"You just seem so experienced, and I trust you so much because you're my best friend. I'd really feel safe and comfortable if you would help."

"Well... I suppose I could...yeah, yeah, I could. It wouldn't be weird. We've seen each other naked before." Victoria gradually agreed.

"Right! Just a few minutes ago even!" I started taking off the black pajama shorts she had lent me.

"Oh my heavens!" Victoria exclaimed. "I didn't see your bush earlier. You dyed it red too? That's hilarious... and hot."

"How should I start?" I asked Victoria, whose neck had started to flush.

"Um, get in like a doggy-style position," she instructed me. "And then lube up your finger."

With my face turned away from hers, I smirked to myself. I lubed up my finger and reached back, but I pretended like I couldn't quite get a good angle. "This feels so awkward! I'm just kind of poking at the hole, but I can't really get inside."

"Well, try putting your arm under you and reaching between-"

"Could you try for me? Please?" I interrupted.

"Try what?" Victoria asked nervously.

"You know! Could you lube up your finger and-"

"Ahh, I don't knowwww," Victoria hesitated. "That's a really private area and I've only ever put my finger inside my own and-"

"Pleeeeease? I just need to do something crazy to get back at Dillon, and I need your help!"

"Well... well, I guess... What are friends for?" Victoria took the lube from me.

I felt a little bad about manipulating my friend, but a darker side of me was very turned on.

Victoria stared at my asshole for a couple of minutes as she talked herself into this. "It's just a finger," she finally said to herself. She put her left hand on my ass cheek for stability and pressed her index finger against my virgin asshole. "Take a deep breath," she told me and she pushed the tip of her finger through my tight little ring.

She was right. It did feel good. Strange, but good.

"Are you okay?" she asked.

"I'm great," I answered. "Go deeper!"

Victoria slid her finger very slowly, deeper and deeper into my ass.

"Oh my God, I feel so full! Is that all of it?" I asked.

"You're like halfway there," Victoria informed me. I could hear her grin as she spoke.

"Holy shit. Okay, keep going." I realized everything was clenched down there, so I tried to relax my muscles. Her finger felt so deep in me and I'd never felt so full.

"Okay we're most of the way in now," Victoria announced. "How do you feel? Good? Good! The next step then is to pump a little to open you up more."

"What do you mean pump- ohhhhhhhhhhh," I moaned. Victoria was fucking me with her finger, and fireworks started going off in my brain. I think I said holy shit again, but I could just as easily have gone nonverbal.

I don't know how long Victoria worked her finger in and out of my asshole, as I was drowning in ecstasy, but at some point I came, screaming into her comforter.

"Wow," Victoria said. "That was so hot. I've never made a girl cum before. I've actually never seen a girl orgasm, except in porn... That was... that was just so hot..."

I could hear the arousal in her voice. She didn't know it yet, but I'd be returning the favor before this night was over.

"While you're all loosened up down there, we should do one more thing," Victoria explained as she lubed up her smallest butt plug. "This one is just a little bigger than my finger. You should wear this for a little while to see what that's like. If you wanted to keep going down this path, you'd trade it out for incrementally bigger ones."

I was barely listening, as my libido and my brain dealt with the toy Victoria was pushing into my asshole. I took a couple deep breaths and concentrated until Victoria told me it was fully inside. I collapsed onto my side, and looked at my best friend of the past 20 years. Her hand was idly teasing her inner thigh. Her nipples were poking through her pajama top. Her face and her clavicle were flushed a deep red. Her eyes had a glimmer of lust to them.

I crawled toward her. "Thank you for helping me rebound," I said as I stared into her eyes.

I continued to crawl toward her and on top of her. She laid on her back, and I stood on all fours over her, with one hand on each side of her shoulders and one knee on each side of her thighs. I leaned down and kissed her on the lips. Victoria's lips parted to accept this soft kiss from her best friend.

"I have another idea for more rebounding," I told her.

I started to make out with Victoria, and after just a moment's hesitation, she engaged with me. As our tongues fought to explore each other's mouths, I let my hands roam up and down her body. Without breaking contact between our lips, I grabbed her shirt with both hands and ripped the snaps open all at once. Victoria gasped, and I took the interruption in our make out session as an opportunity to start kissing down her chin, down her neck, and to her chest. I looked up into her golden brown eyes as I sucked one of her nipples into my mouth. Her back arched as she moaned quietly. I couldn't wait to taste my friend, so I impatiently continued my path down her tight belly. I pulled her shorts off, revealing her shaved pussy. Her lips were flapped open and glistening. It looked so delicious, so I leaned down-

"Wait! Wait!" Victoria stopped me.

Uh oh. Did I move too fast? Was my seduction coming to an end before I could get my prize? I prepared myself to apologize.

"Can we-" Victoria began, but stopped short. "I think I'd be too wound up in my own head if all I had to focus on was you eating me out. I'd be too self-conscious to have you looking up into my face while I tried to cum. So... could we sixty-nine instead? I think I'd enjoy it more if I were a more active participant."

Even better, I thought to myself. I grinned as I sat upright. I crossed my arms and pulled my shirt over my head. I crawled around until I could deposit my pussy on my straight friend's mouth.

"Ok," Victoria breathed heavily. I've never done this before so..."

"You'll do great," I assured her. "Just do what you would want done to you. What I AM doing to you."

Together, we bent our heads toward each other's pussies. I took a broad, slow lick with a flattened tongue all the way up her slit. Half a second later, I felt her do the same to my slit. Without any words, I taught Victoria everything Brittany and Zoey had taught me. Victoria was timid, but she was a quick learner. It was almost like licking a voodoo doll of myself, as everything I did with my mouth, I felt on my pussy a couple moments later. I went down on her until I made her (and thereby myself) cum. Victoria didn't let up. I think feeling my body convulse in pleasure on top of her gave her a new confidence. She stopped following me step by step, and instead started mixing and matching what she had learned and experimenting with new licks and nibbles and sucks. I was surprised when she made me cum a second time before I had gotten her off again.

I quickly returned the favor, focusing my attention on her little clit, making the girl I grew up with undulate under me. I heard her moan and I felt her pant between my legs. It was so hot knowing I was the first girl to ever make her feel like this. I think I had always wondered what my friends' sounded like when they came. Victoria let out short little bursts of high-pitched whimpers, almost like she was chirping.

When we were both satisfied, I rolled off Victoria to lay side by side on our backs on her bed. She sounded blissfully bewildered as she asked, "Oh God, is this what all pussy tastes like??"