Cassie's Revenge

Payback for Cassie

Cassie told me to take off my T-shirt and jeans. I asked if I should take off my briefs and socks too. She rolled her eyes and said, "You don't wash light and dark colors together. They can fade and bleed."

"That's not what I meant." I quipped.

"I know," she huffed. She took my clothes to the washer and dumped them into the hamper. She took off her jeans and her blouse, so she could wash them too.

Cassie had a slim body. Her tits were a bit small but fit into her bra nicely. She didn't have any dark squiggly hairs poking above her panty line or at the inside of her thighs. She was either nicely trimmed or shaved bald. She had high cheekbones, small nerdy glasses, and stylish dark hair cropped at her neckline. Cassie was as cute as a girl could get. Somehow her narrow hips and the large bulge in the font of her panties didn't detract from her alluring girliness. Cassie poured in the detergent oblivious that I was peeling away her undergarments in my mind. She fiddled with the settings, pressed hard on start, and the machine whirred to life.

"That was an obnoxious comment," she said crossly. "If I knew you were going to make it, I would have taken my clothes to the laundry mat."

"What comment?"

"The one about you getting naked."

"Sorry," I said.

"Where did it even come from? I mean, we flirt all the time, but you never hit on me before."

"Sorry," I said again. "It's just you're so cute now."

Cassie shook her head. "How long have we known each other, eighteen years? Do you really want to change things up after all this time?"

"No, I guess not."

Cassie sat in the chair opposite the sofa. She lost herself in thought, and her mood seemed to change. She seemed contemplative and less annoyed. "I've been meaning to ask you something." She said.

"Sure."

"Remember that summer before we left for college, right after we both turned eighteen?"

"I guess, but that was a decade ago. What about it?"

"Remember Jerry's older brother gave us a twelve pack of cheap beer, so we snuck out into the woods to drink it."

"Yes, sure. It was you and me and Jerry, and what was his girlfriend's name?"

"Karen."

"That's right Karen. Little miss Christian girl."

"Oh hardly."

"She tried to be Christian."

"Not that night."

"Well, in her own way she was."

"Do you even remember that night?"

"Yes, the moon was nearly full, so we were trying to hide in the shadows so no one else could see us, but we could see each other quite clearly. We just finished the twelve pack, so I guess we had about three beers each. That was more than enough to get us pretty buzzed. Jerry said he had to pee, so he walks over to a tree and unzipped."

"Yeah, and you're like 'check out the big dick on Jerry!'"

"And Karen giggles, and I asked if she knew Jerry had a big dick. Jerry turns around and says, 'of course she does,' and he doesn't even zip up. He just leaves his dick hanging out the front of his jeans. He walks up to Karen and kisses her hard on the lips. They are making out right in front of us, and Jerry's dick is getting really long and hard. He grabs one of Karen's tits, and she reaches down and starts stroking his cock. I was totally shocked. I wasn't expecting the night to turn out that way at all."

"I wasn't either. It totally took me by surprise." Karen smiled. "You remember what happened next."

"Yes, Jerry pops one of Karen's tits out the top of her bra and starts sucking on it. Karen says, 'come on boys, a little privacy please,' so we walk further into the woods where we can't see them."

"But we could still hear them though couldn't we."

"Yes, Jerry says, 'hey let's do it for real this time,' and Karen says, 'no, I want to stay a virgin.' Jerry says, 'look what you do to me, baby! Look how hard it is.' And I could hear them whisper sweet nothings, but I couldn't make out exactly what they were saying. Then I hear zippers taken down and clothes coming off. Jerry says, 'that's my girl. You're mouth is so wet and hot!' And we're just sitting there in the dark, looking at each other, not knowing what to think."

"You remember what happened after that?"

"I hear Jerry say, 'I got to get inside you baby.' Karen says, 'okay, but only in my ass, so I can stay a virgin.' Jerry says, "spread your ass cheeks for me." Then she's like 'Ouch, slow down your hurting me.' He says 'sorry,' and she says 'that's better.' We hear some moaning and obscene slurping noises, and Karen asks, 'how far are you in me?' Jerry says 'not far, just a little past the head.' And Karen says, 'oh my God, you're so big!"

"And after that?"

"Not sure, I think I forgot. I guess Jerry comes in her ass. They get dressed, and we go home."

"Bullshit, you're leaving out a pretty important detail, and I know you still remember because your recollection has been so vivid thus far."

"You really want to do this?"

"Yes."

"But it's been ten years, and we never spoke about it before."

"Just humor me."

"Are you sure?"

"Positive. Tell me what happened next."

I wasn't sure why Cassie wanted to discuss this after all these years, but she was looking at me so intently that I knew it had profoundly affected her.

"Okay," I said, after taking a deep breath. "You ask me if I had a hard-on, and I said I did. I asked you if you were hard and you said 'like a rock.'"

"That's exactly how I remember it. " She agreed. "Then what?"

"You just kept looking at me, staring at me for a while, which I thought was strange. Then you said, 'whip it out.' And I said, 'huh?' and you said, 'seriously, whip it out.'"

"And you said, 'no way, man!' " Cassie interjected. "You didn't speak to me or look me in the eye for the rest of the evening. You didn't call for over a week, and then you just show up at my house with some tools. You fix my Rock 'Em Sock 'Em Robots, and we just pick up where we left off like nothing happened."

"Yes, I agree your account is accurate."

We were silent for a while, and then Cassie said, "So, after all these years, I'm still curious about what you thought about the whole thing?"

"Are you angry?"

"No, just curious. Now that you feel it's okay to hit on me, I want to know why you were so cold back then."

"Gee Cassie, what can I say? We were just kids back then. I had never even kissed a girl, and my best friend wants to see my dick. I didn't know how to handle the situation."

"So it was because I still thought I was a boy?"

"Well, that's certainly part of it. It's not like someone could be gay back home, you still can't. People are so stupid there."

"Including you?"

"Yes, including me, but like I said, that wasn't the entire reason. You were pretty girly back when you were trying to be a boy, and honestly, you were looking pretty good in the moonlight that evening."

"I know. I could tell by the way you were looking at me."

"Cassie, you need to understand I was just a confused kid. I knew nothing about girls. I didn't mean to hurt your feelings, if that's what I did."

This seemed to satisfy Cassie. She was silent for a while, during which she became more relaxed. I, on the other hand, was feeling pretty tense. I found it hard to account for my prior misdeeds.

"You said me being a boy was only part of the reason. What was the rest of it?"

I couldn't help but chuckle. "It's pretty stupid, really. Just the insecurities of an eighteen year old boy."

"I'm listening."

"Okay, like I said, I had no sexual experience before. All I knew about sex I had learned from porn."

"That's understandable. What was the name of that horrible sex ed book we had to read?"

"Something like, 'Thirty-Two Reasons to Wait Until Marriage.'"

"Yeah, that's it. How horrible, and ineffective too. I don't think any of us waited until marriage."

"I think Karen did."

"Her asshole didn't."

"True," I agreed.

"Go on." Cassie commanded. "You were saying."

"Okay, here's the deal. The only dicks I had ever seen before were the big ones in porno movies and Hustler Magazine. And when I saw Jerry's dick, which was the first dick I had seen in the flesh, I figured your average dick was about eight and a half inches long. I was convinced I had the smallest dick in the universe. Honestly, I was afraid that if I showed you my dick, you'd laugh at it and tell everyone in town how tiny it was."

Cassie turned red and buried her face in her hand. "Oh my God. You poor man! Was that the real reason?'

"It was. To me, having a small dick was my deepest darkest secret. Then I went to college, got in a few relationships, learned that I was pretty much normal, and mostly got over it."

"Mostly?" Cassie asked.

"We all have our insecurities." I explained.

"How did you, you know, finally get the courage to show it to a girl."

"I started dating this girl who had a lot of sexual experience. By the time I met her, she had already fucked like ten other guys. I would suck her tits, but I wouldn't do much beyond that. She kept asking if I had sex before, and I told her that I hadn't. She said she really wanted to fuck. One night, I got all her clothes off, but I still had my tighty whities on."

"I hate tighty whities," Cassie said, "They remind me of diapers."

"I don't keep any anymore."

"Yes, I noticed. I've been doing your laundry all day without any help from you at all."

"Sorry."

"Go on."

"Okay, I was kissing her and sucking her tits. I figured I should try to get her to cum so she wouldn't lose interest and dump me, so I was trying to flick her bean--"

"Flick her bean?"

"You know finger her clit."

"That's funny. Flick the bean. I've never heard that before."

"She wasn't getting wet though because I obviously wasn't doing it right. I had no idea where her clit was. I was probably digging my thumb into her pee hole."

"Ouch."

"I take my mouth off her tit and lick her the inside of the thigh right where her bush hairs start. Instantly, her pussy gets wet, and I go down on her. I didn't know much about technique back then. I just licked up and down her slit, but she was totally getting into it. She was moaning, and arching her back, and pinching her nipples. I'm doing this for about ten minutes, and she starts reaching down the font of my tighty whities and pulling at my cock. I'm glad it's hard because it's tiny when it's limp."

"So you have a grower?"

"Totally. Anyway, she says, 'I can't take it anymore, fuck me already,' but I say 'I don't know, are you sure?' She says 'stick your cock in me you faggot!' Somehow my tighty whities came down. I don't even remember how we got them off. We didn't put on a condom or nothing, which was pretty foolish. I slide my cock into her dripping pink slit, and I push hard forward. My cock totally disappears into her giant dark bush and she says, 'I'm cumming already! I'm cumming!' And that was pretty much it. A few more thrusts and I'm blowing my load into her juicy warm pussy."

"So that's how you got over having a small dick?"

"Yeah, I gained a lot of confidence by making her cum my first try. A few days later we're getting ready to fuck again and she's putting a condom on my dick. I never wore one before, and I thought it was going to be all baggy and slide off, but it seemed to fit okay. After I cum I ask her if I have a small dick and she's like, 'I don't know, maybe it's a little small. I don't care too much about that.' She told me she had this boyfriend before who had a really big dick."

"How big?"

"Over nine inches."

"That's big!"

"She said they always had to take things slow and that he couldn't put it in all the way. She said the guy didn't really like having a big dick and wanted to be smaller. I didn't believe her at first, but I do now. At the time I thought she was just trying to make me feel better. We had sex a lot, and we both really liked it. Me thinking I had a small dick kind of became an inside joke, and she'd always tease me about it. You know, say things like 'stick your little dick in me right now.' Or 'fuck me with your little dick.' It became a major turn on because she liked me the way I was."

"So you two kind of got into the small penis humiliation thing?"

"Yes," I agreed. "I guess it gave me more control of my insecurity."

"She seems like a pretty good person, at least as far as sex goes." Cassie said. "What happened to you guys? Why did you break up?"

"We kind of just drifted apart as we got older. We remained friends until graduation. She told her friends I had a smallish dick, but that I fucked pretty well with it. After graduation we lost touch. Last I heard she was a lesbian, which would explain why she likes getting her button licked so much and doesn't care that much about dick size."

"That's kind of a cool story," Cassie said.

"Are you still mad at me, for being weird all those years ago?"

"No. Not anymore. I know what its like not to feel at home in your own body."

"Well, you have a really nice one now."

"Are you hitting on me again?" She asked crossly.

"No, of course not. You're way out of my league."

"Damn right I am."

Cassie got up and poured herself a glass of water. She stood against the kitchen counter, looking at me, not saying anything, just looking at me.

"So you think I'm pretty now?"

"Very."

"You didn't turn out so bad yourself. You were so scrawny when we were eighteen. I'm glad you filled out."

"Thanks," I said, which was greeted by silence. Cassie seemed to study me.

"Whip it out." Cassie ordered.

"Ha, ha, that's funny. Just like you said ten years ago."

"No seriously, whip it out. I want to see it." She put the glass down and moved closer.

"Really?"

"Yes, most of the guys I've been with have big cocks. I haven't seen too many small ones."

"No," I said.

"Why not? You owe me after all these years."

"What were you going to do ten years ago if I took my dick out? "

"I was hoping we'd jack off together. I think I also wanted to suck you."

"You want to do that now?"

"No."

"Then why do you want to see it?"

"Closure."

"Seriously, closure?"

"It was humiliating getting rejected sexually the first time I ever made an advance."

"Sorry, " I said.

"It's okay, but you should show it to me."

"Okay but only if you show me your tits."

"No."

"Why not?"

"My tits are weird."

"I'm sure they're not."

"They are. They're ugly."

"Come on, you've got to take your bra off to wash it anyway."

"Okay, I'll show them to you, but you have to be nice, and then you have to show me your cock."

"Agreed," I said.

Cassie reached behind her and undid the clasp. She slowly pushed her straps down, but paused right before the cups came off her tits "If you laugh, I'll kick you in the nuts."

Cassie's tits were definitely different. They were narrower than I was used to and tapered on the way down. They were nearly conical, each ending at the largest puffiest nipple I had ever seen. They weren't pretty in the traditional sense, but they were hot as hell.

"You're tits are totally hot." I said.

"You think so?" she said, smiling.

"Can I touch them?"

"You should kiss me first."

Cassie lips were wet. She was a good kisser. I grabbed one of her tits and squeezed gently. The areola swelled and her nipple stiffened dramatically. Fully agitated, it appeared as if someone had put a scoop of strawberry ice cream at the wrong end of a sugar cone. Cassie pulled down at the front of my briefs.

"Take your dick out now," she commanded.

"Okay," I said, slipping off my underwear.

"Oh my God," Cassie laughed. "Your dick is so tiny."

"It get's bigger," I said defensively, "It's a grower."

"Sure it is!" Cassie snarked.

I moved in to kiss Cassie on the mouth but she ducked out of the way. "Uh uh," she said. "Suck my weird tits."

I fit Cassie's puffy swollen nipple deep into my mouth and slurped loudly.

"That's good," Cassie said. She pulled her tit out of my mouth and thrust her other one into my face. "Now, suck the other one."

This time I licked it like an ice cream cone, and nibbled lightly at the end.

"Oh gently," she said, "it's very sensitive."

I reached down and groped at the bulge at the front of her pink panties. It felt massive in my hand.

"Do you want to see my girl dick?" Cassie asked.

"Yes, I do."

"Okay," Cassie said, slipping off her underwear.

Cassie was shaved bald. Her cock was thick and hung low. I could barely make out the contours of a small sack peaking around the girth of her fat salami.

"It's huge!" I said.

"No, it just seems that way because you're so tiny." She began rubbing the purple mushroom head of her she-cock against my little knob. She had to get up onto her toes because I was taller than her and my dick didn't hang much. "Here," she said, let's compare."

Cassie's cock began to stiffen and straighten out. The gentle friction of Cassie's girl dick got my own blood flowing. Slowly, my head peaked out, like a frightened turtle coming out of its shell. Cassie clutched it and pulled. "Here we go, finally," she said. "I guess you could call that a dick."

Our cocks touching, Cassie stroked us both. She was dual wielding. We were sword fighting, snake charming, frotting. It was thrilling. After a short while, we were both rock hard.

"Did you ever measure it?" Cassie asked.

"I think all guys do."

"Trans girls too." Cassie said. "How big is it?"

"Five inches."

"Mine is seven and a half."

"That's big."

"No, that's only above average."

"No, I read a scientific study. It's big."

"Only a guy with a small dick would bother to read such a thing."

"I know."

"You must be incredibly insecure."

"I am."

She studied our hard cocks some more. The disparity in our sizes could not be overlooked. Mine was a scale model of Casssie's, as if hers had been cloned, hit by a shrink ray, and then somehow attached to myself.

"Wow, if you're only five and I'm seven and a half, I have fifty percent more cock than you do."

"Uh huh."

She moved her cock so it was on top of mine. Mine completely disappeared from view, hidden completely underneath her girly girth."

"Actually, I have considerably more girth than you do."

"Uh huh," I said, transfixed if not completely hypnotized by the sight and feel of Cassie's she phallus.

"So, I probably have twice as much cock as you do."

"Uh huh," I said again feebly.

"Put your hand around my big girl cock." She commended. I complied. My thumb barely met the end of my finger as I held her in my fist.

"Stroke it." She said.

I had to loosen my grip to slide my hand up and down Cassie's long cock. I was amazed at how far I had to move my hand and arm to stroke her entire length. The reach actually made my shoulder ache. Cassie gripped my own cock. Her thumb overlapped onto the knuckles of her opposing fingers. She began to rub me, making short strokes.

"Oh this won't do." Cassie said. "My hand is starting to cramp up. I guess I haven't held something this small in a while." She shifted her grip so that she held my little cock with just the tips of her thumb and two fingers. "That's better." She said. "Is that how you jerk your own self off?"

"Uh huh," I said feebly.

"God that's pathetic!" Cassie said. "Small dick men are so useless." Suddenly she let go of my dick. She swung her own hard cock violently so the undersurface smacked my little pinhead with a loud thud.

"Ouch, Cassie!" I whined. My own dick went limp. The end had turned purple and was swollen.

"Hey it looks like you got a little more girth." Cassie said, "but it's still tiny and pathetic!"

"Cassie that hurt!" I protested rubbing my little dick head to take away the sting.

Cassie plopped herself back into the couch. Still hard, she began stroking herself with two hands.

"Like I said, small dick losers are so pathetic. I was going to let you fuck my ass, but I probably wouldn't even feel it. I'm probably better off just sitting here and jerking off. Why don't you finish up the laundry while I take care of myself."