Mutually Beneficial Arrangement Ch. 02

"Sorry Ms. Lily," I said in a small voice. She was standing just in front of me now, her eyes glittering and a cute, drunken smile on her face. She was having a hard time staying character. I could tell it was working out just the way she planned, and I was so happy and proud that I was giving her what she needed.

"Insubordination will not be tolerated in this sorority," Lily said, licking her lips.

"Punish me, Ms. Lily, I deserve it," I said in the sweetest, most innocent voice that I could muster. Lily almost laughed at my acting, but she held it together. Instead she nodded.

"Bend over the arm of the couch, pledge," she said and she slapped the palm of her hand with the paddle. I nodded, feeling my heart rate rise slightly. That wasn't acting, I didn't have any idea what this was going to feel like. But for some reason, it was a little exciting.

A moment later, I was standing with my hands down on the arm of the couch. I was bent at the waist, thrusting my ass out far into the room. I was up on my toes, to make my legs look nice. I looked back over my shoulder towards Lily. "Please Ms. Lily, I need to be in this sorority," I said.

Lily had hardly been waiting for me to say I was ready. She was totally overwhelmed by her desire now. Her desire for me. I shivered a little, and waited for her.

Lily walked towards me slowly. I heard the paddle tapping softly on her palm. Each soft tap of her skin on the wood made my heart rate jump, made my legs tremble. She moved so slow, really built the anticipation. And that was what it was too, anticipation. I wanted Lily to spank me with that paddle. I looked over my shoulder again, saw that she was directly behind me.

At first, she didn't spank. I felt her gentle warm hand come down on my ass. Her fingers closed on it slightly, just squeezing the flesh a little bit. Then she flattened her palm and gently rubbed my ass, moving her hand around gently over the skin like the barest hint of a touch.

"I think that ten hard spanks is an appropriate punishment for your insolence, what do you think pledge?" She asked.

"Yes Ms. Lily," I said dutifully, and wiggled my ass back and forth.

"You can tell me to stop at any time. But if I stop before ten, you are no getting into this sorority. Do you understand?" Lily said, her fingers slipping off of my ass.

"Yes Ms. Lily," I said again in my sing-song voice.

"Good," Lily said, excitedly. And then I heard it, before I even felt it. A sharp cracking noise. I let out a yelp from the surprise and it melded in a cry of pain. She had really spanked me! I felt my legs tremble. Slowly the sharp pain subsided, leaving only an intense warmth behind. And a dull pain that didn't leave

"Do you want me to stop?" Lily asked.

"No Ms. Lily, I want nine more," I said, and bit my lip. I knew it was coming again, this time it was not a surprise. I knew the harsh cracking sound was coming before I heard it. But if anything it hurt more, when I was expecting it. I yelped loudly and sort of jumped up a bit in the air. Lily's free hand came down and rubbed my ass again. It felt a bit raw. The pain was real! She was really spanking me.

"Well?" she asked.

"Another," I said, biting my tongue and accepting the pain. I knew that some women enjoyed this sensation. But the truth was, I didn't understand the appeal. The feeling of the pain subsiding was nice, I supposed. But only by comparison to the smack. Ah, and there it was again! The sharp sound followed by pain. Deeper this time, like my skin had been weakened or something. I yelled and my legs shook.

"Had enough?" Lily asked seductively. I steeled myself and looked over my shoulder. Lily was standing behind me, her feet spread, the paddle in her hand. She was smiling devilishly. She looked beautiful. And so happy. I smiled at her.

"Again," I said. And as I was watching, I saw the paddle fly forward, slap against my ass. I turned forward again, grimaced and moaned. My legs felt weak and I leaned my elbows down onto the couch in order to hold myself up. I felt hot pin-pricks in the corners of my eyes. I knew I was about to cry.

"Well?" Lily asked. I was almost halfway there. I could get through this for Lily.

"Again," I said. But my voice betrayed me. I had tried to say it in the same sing-songy, playful way that I had before. But I just couldn't. My voice cracked slightly halfway through. I knew that I sounded a bit like I was about to cry. I guess I was. I didn't turn around, tried to play it off like acting.

Instantly, I felt Lily's sexual energy dissipate. Instead of the hard smack of a paddle against my ass, I heard the hollow clatter of Lily's paddle dropping onto the floor. I felt Lily's hand come down gently on my ass, barely putting any pressure on it.

"Lissie, honey, are you okay?" she asked, real concern in her voice. I looked back over my shoulder, felt the tears but couldn't do anything with them. I sort of shrugged and smiled wanly.

"I am fine, let's keep playing!" I said, knowing it wasn't convincing.

"Oh baby, did I actually hurt you?" Lily said, moving around so that she was standing next to my head. I felt her lips coming down my lips, kissing me gently. She moved up, and kissed each of my eyes, kissing away my tears. Her hands ran through my hair, gently.

"It's fine, I am fine. Please don't...I don't want to ruin your game, let's keep playing," I suggested. Lily pulled back, shaking her head.

"No! Oh my god, Lissie, I never ever want to hurt you. I am so sorry. We should have set real rules before we started playing the game, I was just so excited," Lily said, I had never heard her so concerned.

"It just stung a little bit more than I expected. I think it might be because I've never done that before. I wasn't like...ready for it," I said, already feeling better, just knowing that Lily cared for me. "I feel silly, I wasn't trying to make a big deal about it."

"There is nothing silly about this," Lily said, "I made a mistake and I am so sorry."

"It is okay!" I said, leaning forward and kissing Lily, "It is just a little red ass," I tried to joke.

"You're being sweet," Lily said, her eyes looking sad, "But the last thing I ever want to do is hurt your perfect little ass!" And she kissed me again, "I am so sorry, let me..." she started and then she trailed off.

"Lily, I..." I started. But she quickly rose up and walked around behind me again. I was still leaning against the the arm of the couch, my ass sticking out. Lily quickly dropped down onto her knees behind me. I felt her arms wrap around my thighs.

"So red! I am such a..." Lily started, shaking her head. I saw how red her face was, shame and embarrassment. I didn't know what to say. Lily never lost her composure before, not even in the depths of her sexual desire, "Poor little red ass!" Lily said. And then she leaned forward and placed her lips on the warm, inflamed cheek of my ass, kissing it lovingly.

I sighed slightly, it felt nice. Lily's soft, thick lips against my throbbing ass. Lily's hands moved slowly up and down my thighs, gently caressing me. She pulled her head back for a moment, moved to the side and kissed another spot on my ass. I sighed again. Lily moved again, kissing. The sorority game was forgotten, never to be revived.

"That feels nice," I said softly, and it was true. As he lips touched me, it was like they instantly soothed. The throbbing stopped, the heat sort of subsided. As she kissed more and more places, the pain began to sort of evaporate. It flew away. And, I knew it wasn't anything she was doing with her mouth. It was her obvious concern for me. I didn't hurt anymore because of how badly she wanted me not to hurt.

And the more that Lily kissed me, the more she seemed to enjoy herself. She knew that my ass wasn't hurting anymore. And she knew that her lips felt nice against my soft, smooth skin. She started to kiss faster. I felt her tongue slip out slightly, taste me.

"Thank you, Lily, it feels so much better," I cooed. I looked over and saw Lily looking up at me over my ass. Her eyes were sparkling against and I could tell she was smiling as she kissed.

"We girlfriends again?" she asked. I giggled.

"Lily, if you ever wanted to spank my ass until I cried, you just have to ask. I will do anything for you," I said. And I think that we both recognized when I said that that I didn't mean that I would do anything just because she would pay me. But because I wanted to.

"I appreciate that," Lily responded, "But I prefer to do things that make you feel nice. Like this," And with that, she leaned forward again, and pressed her lips against my ass. I arched my back, pressing my ass back into Lily's face. Her hands continued to move up and down my thighs, as her mouth kissed all over my ass, an at the base of my spine,and the tops of my legs. Her mouth was a whirl, moving around me and kissing every inch of my ass.

"You have such soft lips," I groaned. Lily didn't respond, at least not in words. Instead, I felt her hands work their way up my thighs slowly. Her lips moved towards the center of my ass, kissing the cheeks right where they came together. And then her hands moved up to the my ass cheeks. Her fingers sort of splayed out across my ass, grasping them. She pushed into me now, sort of splitting my ass cheeks apart.

Her lips continued to kiss, but more slowly, more deeply. I felt her tongue licking against my skin. I felt her hair in the loose pigtails draping down over me. I felt her warm breath against my ass as she moved closer and closer towards the center of my ass. My breath caught in my throat. I felt my nipples grow hard and my knees grow weak.

I think that in that moment, we both knew what was going to happen next. I think if either of us had said anything about it, that it probably would have stopped. That we both would have grinned sheepishly and done something more vanilla. But I didn't say anything. And neither did Lily.

Lily's mouth moved directly over the small, pink rosebud of my asshole. I felt her warm breath against my sensitive skin, felt it contract. And then I felt lily's warm mouth press in a chaste kiss, directly on my asshole. I took in a gasping breath. I had been expecting it, but it was so much more intense that I had imagine. So much more sensation!

"Oh fuck!" I groaned. I pushed myself up on the arm of the couch again, so that I was balancing on one hand. The other hand instinctively raised up to my breast, grasping at the flesh and feeling my hard nipple against my palm. I pushed my hips back farther into Lily's face.

"It feels so dense and warm!" Lily responded, her lips still against my ass, I could feel them fluttering against my asshole. I could hear the surprise in her voice. Not just because of what I felt like, but because she as doing it at all. I knew Lily well enough to know that this was not some sort of plan. She had been kissing my ass gently, and had seen me going more excited had smelled my arousal, and she had just rolled with the impulses her body gave her. She might not have ever thought about kissing my asshole before, but now she needed to do it. I understood Lily, because I felt the same way. It was the main reason that, despite all of the reason we shouldn't work, we did.

"Don't stop!" I begged. Lily pressed her face more firmly into my ass. Her warm, wet lips pressed against my anus. She peppered it with kisses, and each one seemed to send a bolt of lightning up my spine. Her hands continued to press into my ass cheeks, massaging my flesh. Her fingers felt gentle but firm.

And then I felt her lips split open. I didn't know that I wanted her to until I felt her soft, wet tongue slip out of her mouth. It pressed flat and silky against my anus. Lily dragged her tongue up my asshole, coating me in her saliva. It felt like her tongue had wrapped around all of my nerves. She kept her tongue soft, dragged it down my asshole, did it again.

"Oh wow, Lily, that's amazing," I gasped. I could no believe how good this felt. If someone had told me even two hours earlier I would be doing this, I would have said it was disgusting. But here, in the moment, I never wanted anything else.

Lily groaned and I felt her lick more forcefully. She buried her face more deeply, which allowed her to pull one of her hands back. I looked over my shoulder, and could only make out little bits of Lily's body, but I could see that that newly freed hand was between her legs, and I knew that she was pleasuring herself. I smiled, knowing that Lily was enjoying herself. Knowing that she, like me, needed more.

"Put it in deeper, taste me inside," I groaned. I didn't even really know what I meant. It was just the dirtiest thing I could think to say. But even if I didn't know, Lily did. Her tongue rubbed up and down my ass once more, soft and wet. Then I felt it get rigid, firm. For a moment, it just settle against my asshole, she wiggled it slightly. It tickled and I laughed and squirmed. But Lily stroked my ass, calmed me.

"Ah!" I said, not even a word but a noise. I some ways, it was just as surprising as the first spank. But instead of a shocking pain, there was just an overwhelming pleasure. Lily's hot, rigid tongue had pressed half an inch inside of my tight asshole. To my surprise, my body just sort of opened for her, letting her slip easily inside of me.

"Oh my fuck, Lily, your tongue is inside my ass!" I gasped, pushing backwards, trying to drive her tongue deeper. I felt the way my asshole squeezed around her tongue, the way she wiggled inside of me. I'd never felt anything like it before. I tried to push myself open, to take more and more of Lily's tongue inside of me.

"More!" I begged. As good as the sensation felt, I needed more of it. It wasn't enough. I felt Lily press more deeply inside of me, felt my asshole squeeze her tongue tighter and tighter. I could felt her spit dripping down my legs. Hell, I could feel my pussy dripping down my leg. She stretched me wider, but soon she couldn't fit anymore inside. Her tongue was as deep inside of me as she could get it. It swirled and tasted inside of me, making my eyes roll back in my head.

"Oh god, more!" I begged, knowing that it wasn't possible, but needing to beg for it anyway. Instead, Lily rapidly gave me less. I felt a delicious little slippery feeling as Lily's tongue pulled out of my anus. That feeling was incredibly nice, but once her tongue was entirely out of me, I groaned a little. I missed it already.

"Whew girl, you taste good!" Lily said, and then she leaned forward and kissed my asshole again. I shivered a little.

"Why'd you stop?" I whined. I looked over my shoulder and saw Lily looking down, fiddling with something in her lap. She leaned forward and kissed my thigh.

"Patience Lissie," she said laughing a little, "you said you wanted more." Before had a chance to ask what that meant, I felt her left hand return to my ass. She sort of spread her fingers apart against me, pulling my ass cheeks apart. I felt the cool air on my wet anus and shivered a little.

Then it wasn't cold anymore. I felt the tip of Lily's finger press gently against my asshole. No pressure, just a gentle touch. She circled her finger around on my anus, her fingers tickling over the folded denseness of my skin. Her finger felt slick, and I realized that she had put some lube on her finger. The bottle must've been in the pocket of her cardigan. She kept swirling, and I moaned a little. The nerves were so sensitive, it felt so nice.

"Fuck Lily, what're you waiting for?" I moaned.

"I am not making that mistake again, you tell me what you want," Lily said, but she wasn't teasing. Her voice was thick with desire. Which I thought was a little exciting. She had never mentioned wanting to do...anything to my ass before. And now she was almost drooling at the thought of it.

"Put your finger in my ass. All the way," I groaned and Lily giggled excitedly. She applied a slight pressure with her finger, then stopped.

"If they could see me at work!" she said and sort of shook her head a little.

This is what sex was always like with Lily. Always, at the most wild, exploratory moments, her mind would go back to work. I don't even think that she noticed it. But we she said something about work, it always made me wonder if she would be willing to indulge every whim if we are able to be just like...normal girlfriends. If she wasn't always thinking that everything we did together was sort of wrong in some way. It was like... every body hides certain pieces of themselves. Lily was letting one of her little secret desires out, and all of the other ones just came spilling out after it. I wondered if I sort of felt way too. Or maybe I was just a whore through and through.

Whatever, I didn't dwell on it. Lily didn't give me any time. As soon as she finished talking about work, she was all play. I felt the pressure of her finger increase on my asshole. It didn't hurt, I was very wet from Lily's tongue, and so was Lily's finger from the lube. But it was just sort of...tight.

"It's okay baby, just relax," Lily said, and she leaned forward and kissed my ass cheek. I let out a little breath and felt the tension lessen. I trusted Lily. I groaned a little as I felt the tip of her wet finger slip inside of me, felt my asshole squeeze her tight. I hear her spit on my asshole, felt the warm liquid dripping down around her finger.

"That feels nice," I said and wiggled my butt back and forth, "But more!" I begged again and Lily laughed. But she increased the pressure with her finger. She was so wet, and I was so ready for her, the pressure was gone now. Her slender finger slipped slowly inside of me. Very quickly, she was much deeper than her tongue had ever been. She didn't rush, but she never slowed down either. It was just a sort of constant, gentle push, until I felt Lily's knuckles brushing against my ass. And just like that, Lily's entire index finger was inside of me. Deep in my ass.

"How does it feel?" Lily asked, moving her finger inside of me, just a little bit. It was like every nerve in the lower half of my body was directly attached to Lily's finger. She moved one knuckle, and every little nerve twitched. I groaned and arched my back.

"Oh Lily, I can't believe how nice that feels," I moaned as she kept wiggling. Then she pulled her finger back slightly, I felt my asshole trying to hold her in. The feeling of leaving was almost as good as going in. Soon, just the one knuckle remained.

"Give it back!" I begged and Lily actually threw her head back to laugh. But she pressed her finger back inside of me. A little faster than last time. It was even easier this time. She just slipped inside of me. Lily curled her slender finger inside of me. Not hard, not fast, but just to sort of massage my insides. I groaned, unable to think or say anything else.

Her finger moved out of me again and then back in. Once inside, she curled her fingers inside of me, then slipped it out again slowly. She kept a steady, rhythmic pace. And each moment pushed the tension higher and higher inside of me. My knees were literally shaking and I could feel my pussy dripping down my leg. I could actually smell how aroused I was. Lily could smell it too. I could hear her breathing in deeply through her nose.

I was so focused on the beautiful feeling of Lily's finger inside of me, that I didn't even notice that she had moved. Lily had kept her finger moving, but she had rocked back a little bit on her hips, dropping her head down. Instinctively, I spread my legs slightly slightly. I felt Lily's hair tickling the inside of my leg. And then I felt her lips press into my sopping wet pussy.

Lily's lips rested on mine, drenching her pretty face. Her tongue poured out of her mouth, tasting my juices and swirling her tongue around on me. I heard her moan, and I knew that she was swallowing my flavor. But soon, her neck bent back, her chin slipped a little bit further between my legs. And her soft, warm lips wrap around my clit. I felt her tongue probe at it, soft and thick. Just like she'd been licking my asshole a few minutes before.