Cyndi & Friends Ch. 02: Discoveries

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Later that night, Cyndi gets more help.
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Part 2 of the 4 part series

Updated 04/15/2025
Created 03/26/2025
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Kate's Story

I stared at the ceiling. All of us sleeping together on a futon had seemed like a great idea in the abstract. Now I was wishing for some privacy. 

Jacob and I were in the rec room with Cyndi, like a high school slumber party. It felt a little silly, since we're all nearly 30, but it had been a great evening. Jacob and I met in college and have been together since, and Kate has been our best friend the whole time. The plan was for Jacob to give Cyndi some relief after nearly a year of her unintended abstinence. And he had; I had left them downstairs and her orgasm was audible from the kitchen. But a complication I hadn't considered was how horny it would make me. I had tried to get myself off, but the popcorn was finished too soon. Now she was sleeping beside us and I was the one who needed relief. Jacob and I hadn't discussed anything after I got back with the popcorn, but clearly he had come too, since he was sleeping peacefully on my other side, leaving me stuck in the middle with no way to satisfy myself.

I rolled onto my side and watched Cyndi as she lay on her back, peaceful and lovely in the stark light. Moonlight was streaming through the glass blocks of the high windows, illuminating her in waves. Full moon was on, let's see, the 28th, so, yeah, one day from full. We had picked a good weekend; even the stars were aligned. The moon, anyway.

She looked angelic lying there, round cheeks glowing in the reflected moonlight. I lost myself staring at her long eyelashes and cute nose, the curve of her upper lip, her lips themselves, full and soft and shaped for kissing. Did she kiss Jacob with them earlier? Had she wrapped them around his dick and sucked him? Had he filled her mouth with his cum? I wished I had had time to talk discreetly with him after they had done... whatever they had done. I didn't want to embarrass Cyndi by discussing it in front of her; it was probably enough of a bombshell to know that we were open to sexy times with her. Sex. It was limited, but it was sex. I needed to be honest with myself. Anyway, I didn't know the details of what they had done.

Not that it mattered. She was here, and I was horny. I stared, unsure of what I was feeling. I watched her full breasts rising and falling under the blanket. She's four inches shorter than I am, and adorably rounded. I love my athletic body, but if I were lesbian I'd want to bury myself in her soft curves all night. If I were a lesbian. Which I'm not. I found myself wishing the blanket wasn't hiding her nipples. The way they made their presence known through her thin camisole earlier in the night had been very...

Was I getting turned on by her? My best friend? A woman? I only had sex with boys. Specifically, one boy, for the last however long. Decade? Decade. I didn't even think about women; why was I thinking about her? Our clever plan was turning out to be a can of worms. 

Her eyes opened and she turned toward me. "Oh, hi," she said.

"Hi."

"Can't sleep either?"

"Oh, were you awake?" I asked. I was glad she hadn't seen me staring.

She nodded. "Have you been awake the whole time?"

"Yeah. Thinking about things."

"Same," she replied.

"I thought you were asleep. You looked so peaceful," I said.

"I was hoping I could get to sleep by pretending to."

"Fake it till you make it?"

"Yeah, something like that. It hasn't worked yet." She turned toward me. "But that's what slumber parties are for, right?"

I smiled. "Yeah! Since we can't sleep, might as well stay up whispering."

"Sure," she said. "What should we whisper about?"

Straight sex. We can talk about straight sex. She has plenty of stories about that. "Remember that time I walked in on you and, what was his name? Danny? When you were giving him a blowjob?"

She smiled. "Davy. I think."

"You've forgotten his name too?"

"I only saw him once! And you scared him away!"

"Sorry about that. I didn't know you were--"

"I told you it was okay."

"I can't believe he actually left in the middle of a blowjob just cause I saw you. And then didn't want to see you again!"

"Oh, he wanted to see me." she answered. "He called me for like a week afterwards. I didn't want to see him. He was a jerk. Didn't I tell you?"

"You probably did, I can't remember all your conquests." She stuck her tongue out at me. "Anyway, if he was such a jerk why'd you give him a blowjob?"

"I was hoping once I made him come he'd go away."

"Does that ever work?"

"More often than you'd think. Also I was horny."

"Girl, you're always horny!" I noted. "Especially recently."

"It's been a long year," she sighed. "But you're right, I am." She paused. "Does that bother you?"

"Oh hell no!" I replied. "You're perfect just as you are."

She smiled, then looked thoughtful. "So I've wondered, are you really less horny than me, or do you just not show it as much? Or do you get satisfied better by having Jacob there all the time to satisfy you? That didn't make sense, sorry. I--"

"I get it." I thought a second. "I think I'm probably as, uh, sexually motivated as you. Maybe sometimes more. Like tonight. That's why I can't sleep."

"Cause... really?" She sounded nervous.

"Yeah. After all I'm the only one who hasn't come tonight."

She froze. "What do you mean?"

"You did come, right? When I was upstairs?"

"I... Oh my god, you heard? No, I... I mean..." She was tearing up.

"Cyndi, what's wrong?"

"I'm sorry," she said in a shaky voice. "Oh Kate I'm sorry!"

Love and confusion welled in my chest. "Sorry for what?" A sudden realization struck me. "Oh shit. He didn't tell you, did he?"

"Tell... tell me what?" she asked between sobs.

"That this... that we wanted to do that."

She looked at me. "What? No, but I--"

"We wanted to give you some relief. Some, y'know, sexual relief. If you wanted it." I was tearing up. "You thought... Aw shit, we fucked it up, didn't we? Oh Cyndi, I'm so sorry."

"You don't understand," she repeated. "I led him on."

"That was our whole plan though. We'd go where you led. Oh fuck, we should have told you to start with."

She regained some control of her breath. "Cause you know I'm a slut?" she asked, half laughingly.

"No, silly!" I wiped a tear off her cheek. "Cause of your year of sex exile. Your sexile," I added, hoping to lift the mood with some humor. It didn't work. Her tears started again.

"I'm sorry Cyn! What did I say?" I asked.

"You... you two are so perfect for each other and I've messed it all up!" she blubbered. "I was leading him on. Petting his leg, touching him. What if you hadn't planned for it? How could I do that to you?"

"Hey now!" I interrupted. "Like, what if we had all been playing five-dimensional Plutonian steam hockey?"

"Five-what?" She laugh-cried. 

"It's from Gödel E... It's from a book, you probably haven't read it," I answered. "It's about counterfactuals, how you can't change just one thing and ask what would have happened."

She looked confused. "Sorry. Whoosh!"

"Okay, bad analogy." I tried to explain more clearly. "Yes, you were leading him. Did he follow your lead or discourage you?"

"I mean... Followed, I guess."

"That's what I'm saying. If he hadn't wanted it, if we hadn't wanted it, he would have moved your hand off him or something. Would you have kept going then?"

"No," she sniffled.

"See? You didn't do anything wrong. We're the ones who fucked up."

I was silent, contemplating how completely we had failed our own beliefs about consent. I felt like a complete ass and couldn't think of anything to say. After a minute she wiped her eyes and said, "When I told him it wasn't my first rodeo he said blowdeo. And you just said texti... What did you say? Sexile. You guys are the perfect pair of nerds! I never want to hurt you."

"Thank you, yes we are," I agreed. "And we know it. That's why we decided it was okay to have you over. To have you come over!" I said. This time she laughed.

I looked at her with love. "I'm sorry we didn't tell you first. I mean, ask you first. That was stupid," I said. 

A moment passed.

"I'm still going to kill that bastard for not telling you afterwards though," I added.

She giggled. "God, is he still asleep? With us making all this noise?"

"He can sleep through anything," I answered. "It's his stupor-power."

She laughed out loud, then quickly covered her mouth and giggled quietly. "Don't actually kill him, please? But if you want to punish him, maybe I can help." Her impish cheer was coming back. After a short silence, she added, "So you knew the whole time? What we were doing? Even while you were right there? And it's okay?"

I almost laughed. "Not exactly what you were doing, but the overall gist was pretty obvious. I could hear squishy sounds, and the sofa was moving. And I could smell your excitement."

"Oh god. I thought we were being so subtle."

"This isn't some porno where a guy has sex while his girlfriend sits obliviously next to him!"

She laughed. "Still, I can't believe you knew and just... Sorry, it's all a little hard to take in. Even for a slut like me."

"You're my favorite slut, you know that right? But yeah no, I get it. We're not some guy you just met. Or girl. Can you ever forgive me?" I asked.

"Of course." No hesitation. "Can you forgive me?"

"C'mere," I said, holding up my arm and sliding the other under her head. She snuggled up to me with her head under my chin. "Nothing to forgive, I told you."

We lay there, her head against my chest, our arms around each other. I stroked her hair, my heart filled with warmth and tenderness. I wanted to hold her and love her forever. "This is nice," she said after a minute. "Thank you."

"For making you cry?" I still felt like a shit.

"For wanting to make me... come. For caring. For holding me like this."

"Sorry my chest isn't nicely cushioned like yours." Why was I thinking about her boobs again?

"It's okay," she said. "Not everybody needs a bosom for a pillow."

I pulled back and looked at her. "Thanks for that song." 

"Everybody needs a bosom for a pillow/Everybody needs a bosom," we sang together. Quietly.

"Careful," I said. "No belting, or we will wake him up!"

She looked so vulnerable and beautiful in the moonlight, her face inches from mine, eyes still puffy from crying, hair tumbling over her forehead. I wished so much for a redo of the evening. To save her the pain. Dammit, how could we have been so selfish? I brushed her hair out of the way and kissed her forehead before drawing her back to my chest. My mouth was right by her ear. I wanted to nibble it. What was happening to me?

"Hey," I whispered instead. "Girl Talk?"

"Girl Talk," she answered. She had told me about many of her escapades during Girl Talk, back when she was having regular escapades. And she knew a lot more about Jacob than he realized.

"So," I ventured, "How was it? While I was upstairs."

"Oh god. My orgasm, or the... or his? I can't believe we're talking about this!"

"Girl Talk," I reminded her. The rules of Girl Talk are strict: absolute honesty. "And you can say blowjob. You blew Jacob. It's okay." For once I was the confident one talking about sex. It felt good. "Just tell me about it like any other sex you've had."

She shuddered when I said that, but pushed through. "It's not the same at all. But I'll try. Which first, my orgasm or the blowjob?"

"Orgasm first. Yours, I mean."

She paused a moment, pulled away so she could look me in the eyes, took a breath. "Kate, it might be the best I've ever had."

My eyes filled with tears again, of love. "I'm so glad!"

She relaxed. "I couldn't stop coming! He kept... The way he fingered me inside and out. It was amazing."

I smiled. "He has the best fingers, doesn't he?"

"Oh my god, he touched me like a woman! But his fingers are longer than any woman I've had. Well, maybe Edwina." I remembered the stories of Edwina. High praise indeed. She put her hand against mine. "Your fingers are that long," she added slyly. I blushed, grateful for the darkness.  "Could you really hear me from upstairs?"

"Oh yeah. Even the popcorn maker wasn't loud enough to cover you," I laughed.

"Told you I'm loud!" 

"You weren't lying. I'm glad it was as good as it sounded. Now tell me about the blowjob."

"You're sure?"

"Girl Talk," I reminded her with a stern smile.

"Hokay. I wasn't planning to, you know. I was gonna use my hands. But there it was right there in front of me. His cock, all hard and hot and real, and I had to taste it."

"Real?" I asked with a grin. "Like it was imaginary before? Have you been fantasizing about my boyfriend's cock?"

"Maybe." She looked into my eyes. "Yes."

"So? How was it for real?"

"Better than imagining it!"

"And the blowjob?"

"It was... I think he liked it."

"He usually does. I need details!"

She was silent. "Come on, Cyn. Pretend it's someone I don't know," I said, trying to let my enthusiasm show.

She looked at me for a moment, took a breath. "He came so much!"

"I told you he comes a lot!"

"I guess you did. I wasn't really thinking about anything you'd told me. I was kind of caught up in the moment."

"Good!" I said. "More details."

"Okay, so. Well, there aren't many details. He came as fast as I did. I started with my hands--"

"Both hands?"

"Of course!" That was the Cyndi I knew. "One on his balls, one at the tip, touching with my fingertips."

"Your tips on his tip?" I giggled.

"Yeah, and he was super wet. It was all slippery and shiny and, well you know how much I love precum. That's when I had to put him in my mouth."

"And...?"

"And about 10 seconds later he blew his load. It was so much! Every time I sucked he squirted again. I felt like I could keep drinking him all night."

"Sorry he comes so much," I said. "Did you swallow it all?"

"Hell yeah," she replied. I made a face. 

She laughed. "You remember that I like jizz, right? Especially licking off the extra bits that dribble out afterwards." I think she was teasing me. "Squeezing the last drops out the end with my lips, slurping it in and rolling it around on my tongue before I swallow it all down." Yes. Definitely teasing.

"Well, I'm glad you enjoyed it," was all I could say.

"Sorry you don't like cum," she said.

"Yeah, it's too bad, cause I love everything else about sucking him. The feel of his cock in my mouth, the size and warmth. Especially when he starts soft and I suck him hard. And I love making him come. I just don't like the taste."

"Maybe I should finish him off next time you give him a blowjob," she suggested with a twinkle in her eye.

"Maybe you should!" I answered.

She smiled, then saw the look on my face. "Wait, are you serious?"

"I... Let's think about that later. We're talking about you." I returned to the subject of their earlier adventure. "So, you had a good time? Feel better now?"

She sighed. "Yes, I do. Thank you."

I looked at her and was overcome with emotion. "I'm so glad, and sorry we did it wrong. I love you, Cyn."

Her eyes were shining. "It's okay. Bart Simpson at-least-you-tried meme."

I laughed.

She hit me with her beautiful big smile. "Anyway, first time is always awkward. And I love you too. You and Jacob." She grinned like she'd just caught a mouse under her paw. "I love you two too!"

"Tutu? You're wearing a tutu?" I snickered, pulling the blanket off us and rolling her onto her back. "I don't see any tutu!" 

What I did see made my heart flutter. Her hair shone in the dim light. The tiny satin camisole draped softly over her chest had ridden up, exposing the lower curves of her breasts. In the middle of each beautiful mound, a magnificent nipple stood erect beneath the thin fabric. Further down, the moonlight glanced off her bare skin, illuminating the fine downy fuzz on her belly. My gaze moved to her adorable belly-button, and onward to the more tempting areas still concealed by the blanket. She was so beguiling lying there, I wanted her to swallow me up and live in her body the rest of the night.

I realized I had been staring for a minute when she interrupted my musing. "What are you thinking?" I think she knew what I was thinking.

"Oh sorry," I replied. "I was... Do you know how amazing your nipples are?"

"Oh. Thanks? Yes, I do. Thanks."

"You're welcome." I brushed her cheek with the back of my hand.

"You didn't say what you're thinking," she insisted. "Were you thinking about my nipples?"

I hesitated. Did Girl Talk extend to my own feelings? Yes, it did. "I'm just contemplating how I feel about... About my sexuality."

"Hmm." She paused. "Am I..." She continued in a coquettish tone, "Are you getting turned on looking at me?" She was such a vixen.

My turn to pause. Finally: "Yes."

I couldn't tell what she was thinking. Did she want to...? Did I? I knew she'd had sex with plenty of women, but this was me. Her best friend. Whatever happened next I was glad I had been honest.

She looked into my eyes. "Have you ever kissed a girl?" she asked.

Cyndi's Story

I was feeling so guilty I couldn't sleep. Kate was lying next to me on the floor and all I could think of was how I had sucked her boyfriend while she was out of the room. It had been so good when I was swallowing everything his hard cock pumped into my mouth. After a year without any sex at all, it was sweet release. Gushes of his delicious jizz, then spurts, then dribbles, and I drank it all, licking off the final drops that oozed out after he was done. After we were done. It wasn't just him. I had been encouraging him the whole time. Not only had I sucked him, he had put his fingers in me and made me come as hard as I ever had. How could I ignore all that and go to sleep, with Kate so close we were almost touching? I could feel her presence beside me. I kept my eyes closed, calmed my breath, concentrated on the futon beneath my back, and tried to will myself to sleep. It didn't work.

With a sigh, I opened my eyes and turned toward Kate. Her eyes were open. "Oh, hi," I said. I guess she couldn't sleep either. We started to chat, quietly so as to not wake Jacob. I don't remember what we started talking about, but it ended up at sex. It always does. Talking about blowing someone other than Jacob took my mind off my guilt for a while.

Until Kate said she was the only one of us who hadn't come tonight. Suddenly I realized: She knew! She knew I had had sex with Jacob. She must have heard us, oh why am I so loud? The pit of my stomach dropped out and I knew I had fucked up our relationship. I love them so much, and was terrified that I was going to lose them, all for a single night. Even the best orgasm in the world wasn't worth blowing up this friendship. And what about their relationship? What if I had blown them apart?

I must have blubbered for 5 minutes before we figured out that I was the only one who didn't know they had been planning it the whole time. Embarrassing and relieving at the same time.

And then she called Girl Talk. I knew what she was going to ask. I told her honestly he had given me my best orgasm. I teased her about not liking cum, and offered to finish him off whenever she wanted me to. I think she was serious when she said maybe that was a good idea. That helped calm my thoughts. Or anyway, move them to a better place.

Then she threw off the blanket and we were laughing again. She was okay with what had happened. I had been lusting after her boyfriend for months, he had made me come hard with his fingers, and I had sucked him dry and swallowed it all, and she was smiling like she didn't care. Or like she did, and it was making her hot. I suddenly wanted her too. Tall and lithe and fit, lying beside me with the moonlight on her face, her athletic body inches from mine. I could feel her breath, and see the twinkle in her pretty blue eyes. Earlier, watching her peel off her bra and shorts getting into bed, I had felt a new warmth. And here she was in front of me, magnificently naked and inviting, not even the blanket covering her chest. Her nipples were erect on her small boobs, calling to me. My pussy took over from my brain. They had invited me here for sex. I'd already done her boyfriend; it was time to seduce Kate.