Big vs. Biggest

A story based of a suggestion from Sirhugs. Thanks for the inspiration.

*

It was early Friday morning. Sean was lying on the couch in his girlfriend's college dorm apartment watching TV in only his boxers, when her roommate, Janelle came in, wearing only a sexy little baby blue nightie.

"Hi, Sean? How's it going?" Janelle greeted him with a smile.

"Hi, Janelle. Just resting up from a busy night before my classes. I'm glad I don't have an early one today." Sean replied, glancing up at Janelle's brief attire.

Janelle was a natural blonde, tall and voluptuous with long tanned legs that seemed especially long and strong today.

"So, is Jane in class?"

"Yes, she's in psychology class now. How was your date last night?"

"What is it with guys and my big boobs. All any of my dates want to do is grab them. I wish I could find a guy that would look at my face when we're talking, one who could think of something besides groping me."

He says, "Yeah, women are the same way about my big cock. I get no respect as a person."

She says " Big cock? I bet. You're just like all the guys, bragging. I bet I've seen bigger."

"You want to bet, huh? I'll bet you it IS the biggest one you've ever seen." Sean challenged.

"Well, this should be easy, 'cause you're gonna lose! I bet it's not the biggest I've ever seen. With these boobs, I've seen some big cocks. So, what do you want to bet?" returned Janelle.

"If mine is the biggest, you have to strip and masturbate, all the way to a climax. OK?"

"And if it's not, you have to masturbate without looking at my breasts. And, no touching, OK?"

"So, show me your little thing. Let's see it."

So he flops it out, semi erect. It is indeed the biggest non-erect cock she's ever seen, but she lies to him, "I've seen bigger, several, in fact." But she wonders how big it gets hard.

"Well, that's not fair. It's not hard," He replied.

"Well, I suppose you are right about that. It might get bigger when it is hard. Why don't you play with it a little and we'll see how big it gets, OK?" She asked.

"Jane and I had a pretty good time last night and I need something to help me get it up.

Why don't you show me those big breasts you're complaining about? Maybe they'll help me get it up." He said, as he began stroking his long member.

"Well, I guess it would be OK to show them to you. You've practically seem them already with me running around here wearing this." She said while using her hands to show that she meant the attire like the nightie she was presently wearing. "But you can't touch them, only look."

She stood across in front on him, several feet away, and slowly lowered the straps of her flimsy garment. He could clearly see the tops of her breasts straining to get out and her nice cleavage. This was going to be good. He had always wanted to see them in the flesh. She pulled one strap over her arm, then the other. Only her breast's sheer size was keeping the thin, silk-like material from falling. Clearly, she wore nothing under it and her large nipples were faintly visible. She pulled the material down and over one breast, and repeated for the other, leaving it bunched at her waist.

Thrusting them out for Sean's approval, she asked, "Well, what do you think? Are they the biggest you've ever seen, at least on a girl my size? I know they're bigger than Jane's 'cause I've seen hers."

Sean's jaw dropped and his mouth hung open at the lovely sight before him. Janelle was much thinner that he had imagined and her breasts were even larger, in relation to her thin body, than he had expected.

"WOW! No wonder all your dates want to grab them. They're beautiful. Hell, I want to grab them myself."

"Unh, unh! No touching. Remember my rules. I've had too many guys grabbing them already, so you can only look. Besides, you're dating my dear roommate and I wouldn't do anything to hurt her."

"You're right. This is only a bet. You think you've seen bigger penises than mine? Well, we'll see. That's really helping, seeing your big breasts. I can feel the blood draining down to my other head. See?"

"Oh, yes. I see all right. It does seem to be getting a little bit bigger, in fact. And it's really kinda nice seeing you stroking it like that."

"Would you mind holding them for me, since I can't touch them. Let me see you touch them, ok?" Asked Sean.

Janelle obliged by hefting them both up in her hands, offering them out for Sean to see. Upon seeing his penis swell even more, she flicked both nipples with her thumbs to make them wake up and stand out nice and firm. It was turning her on seeing this large cock growing right in front of her.

Her action caused an immediate reaction in Sean. His penis had grown so much that he could now use both hands to stroke it. It was getting bigger and harder by the second and would be at its maximum very soon. He wondered if Janelle liked it or was just trying to win a bet.

"Those boobs are so big that I bet you could suck your own nipples. Can you?"

"Yes, I can, you naughty, horny little boy. I suppose you want to see, right?

"Oh, yes. Please show me how you can lick them. I've never seen a girl kiss her own breasts."

Right now, she wanted to kiss them anyway, since she was getting so turned on watching her roommate's boyfriend stroke his big cock. She obliged by sticking out her tongue and lifting one up to meet it. She licked all around it before taking it into her mouth to suck it hard for several seconds before releasing it. Never taking her eyes off his cock, she licked and sucked the other one too.

"Well, I think this is as big as it's gonna get. What do you think? Have you ever seen a bigger one, or do I have to keep masturbating until I cum?" Sean quizzed.

"You're gonna have to keep masturbating. You lose. I have to see you make it cum now." Replied Janelle.

"You're kidding! OK, but tell me, who have you seen with a bigger one? Name one guy and I'll believe you."

"OK, Well there's, uh, what's his name. Oh yeah, and... Oh, shit! I can't lie any longer. No, there's no guy bigger than you. That's the longest and biggest cock that I've ever seen. No wonder Jane screams so much when you two are making love!"

"I knew it! You were lying to me. You lose, so start masturbating for me now. You have to pay your bet. And, yeah, Jane likes it pretty much, but we have to take it easy when I put it inside her so I don't hurt her. At least she doesn't scream and run away like some girls have. It's really frustrating when that happens, you know? And by the way, the screams, they are usually loudest when I'm eating her, not when I am inside her."

"OMG, I can't hide it any longer. I'll masturbate for you. Besides, I would have to go do it in my room anyway after seeing what you are doing there. That thing is huge. I wish I could play with it too, but I know I can't, so I'll just imagine it tearing me apart."

"OK, so get started. I have classes soon."

Janelle stripped the rest of her nightie off and stood there in only her little blue lace hipster panties. Stripping them off hurriedly, she sat down in the chair opposite Sean and raised her legs and placed them over the sides. Her wet, shaved pussy was open for Sean to see. Never taking her eyes from his cock, she massaged her breasts with one hand, licking her nipples and biting them. This time, it was for herself as much as it was for Sean. Her other hand dropped to her pussy and rubbed down and up, wetting her fingers before flicking them quickly over her small clit.

"Please keep doing that to yourself, OK? I know I lost the bet and you don't have to masturbate if you don't want to, but I really like seeing you doing that. Oh, my, it is so huge!" Moaned Janelle while rubbing herself firmly.

"Oh, I don't mind doing this. I'm enjoying this too. And, truth be told, if we had made the bet about your breasts, I probably would have lost and had to do this anyway. You have the biggest breasts I've ever seen on such a little girl. And seeing you doing that to yourself is very hot!" said Sean.

Suddenly, the door flew open and Jane came storming in, stopping dead in her tracks at the sight before her.

"WHAT THE FUCK?! WHAT THE HELL'S GOING ON HERE?" She demanded.

"It's not what you think, dear. Calm down and we'll tell you." Said Sean.

"CALM DOWN? MY roommate and boyfriend naked together in my apartment and I'm supposed to calm down?" Jane yelled.

"Oh, Jane. It's true. It's not what you think. I just lost a bet and now I'm paying it off. I would never mess around with your boyfriend." Explained Janelle.

"It's true, and I wouldn't cheat on you either, dear. She was complaining that all her dates want to do is grope her big breasts, and I said that I knew what it was like with my big cock and all, and she said, sure, all the guys say that and that she'd seen bigger. So, I made a bet that she had never seen a bigger one than mine, and if she had, she would have to masturbate to orgasm in front on me. So, she's paying off."

"And we made a rule that we couldn't touch each other, only watch. And he DOES have the biggest cock I've ever seen and I didn't mind paying off my debt as long as he kept playing with it." Added Janelle.

"Well, you weren't touching each other. And, I guess if you were cheating on me you wouldn't do it here, would you? He DOES have the nicest cock, doesn't he?" Asked Jane.

"I'm sorry. I would never hurt you. I guess we'll stop now." Said Janelle.

"Don't stop on my account. I've seen both of you naked before. And, a bet's a bet. So, if you lost, you have to pay up. It's only fair. Do you mind if I watch too?" Jane asked.

"OK, I guess not. I was so turned on that I was about to cum when you walked in. Now, I'll have to start over again." Groaned Janelle, not wanting the sight of Sean's cock to end.

"Don't mind me. Take up wherever you left off and maybe I can do something to help." Informed Jane as she sat down beside Sean and kissed him.

Janelle took up more or less where she left off, only playing with herself more slowly. It wasn't so bad masturbating in front of a guy, but it was a little awkward doing this in front of her roommate. However, she was so turned on by Sean's massive cock that she easily fell into the fantasy of thinking about it inside her, and quickly restored the rhythm she had before.

The scene excited Jane also. She reached over and replaced one of Sean's hands with her own, wanting to feel it for herself, and stroked it in harmony with his strokes. Janelle liked this, she could tell, as she stroked herself even faster. Jane's hand accentuated the massive size if the cock she was holding. One of her hands crept up under her shirt to play with her own nipple, sending shivers all the way down to her clit.

They all enjoyed the sights and sounds of lust permeating the small room as they stroked and watched. Not wanting to waste the moment, Jane dropped to her knees at Sean's side and moved her face near his cock. Glancing over at Janelle for approval, she sucked the head of his cock into her stretched lips.

"Oh, yes, such him off. That's so sexy. Suck him good for me. It's so hot seeing that."

Moaned Janelle.

Jane sucked as much of him as she could, which was less than half of it. It filled her so fully that there wasn't much room left to use her tongue. They both still had their hands of the bottom half, continuing to stroke it. It grew even larger, filling with blood and cum getting ready to explode. Sean was very turned on with the sight of Janelle, with her monster tits, rubbing herself to orgasm in front of him. And with Jane helping, he wouldn't last long now.

Janelle crammed 3 fingers into her pussy while continuing to furiously frig her clit, which had enlarged considerably from her ministrations. She shuddered inside as the first wave started inside her. She was cumming, and fingered herself as hard as she could until the next wave shook her even more than the first.

"Look, look, She's cumming!" Sean said to Jane so she could see too.

"I see. Let's show her how much you cum. Let me do it, OK?" Said Jane, removing his hand and taking over control of his cock. She stroked it hard and long, licking it all over, watching the reaction Janelle was having at the sight.

Janelle certainly had a reaction to it. She started cumming over and over, not able to stop, not wanting to either. Seeing her friend sucking that big cock and stroking it was too much for her. She wanted to see it cum too, see it shoot, imagining it was shooting deep inside her as she came and came, over and over. Jane had stopped sucking it and was stroking it long and hard while licking up and down it long length. She knew she would see it shoot soon, if she didn't pass out first.

Sean suddenly tensed up his whole body, pressing his cock up in the air searching for relief. Jane squeezed it hard and pumped it as fast as she could, waiting for the warm sperm to unload itself from deep within him. Then, one load shot far up in the air, landing on his stomach.

Watching him shoot caused Janelle to cum so hard that she almost passed out. Her pussy squeezed her fingers and she gushed out a warm torrent of wetness over them.

Jane pumped Sean's cock hard and readied herself for the next shot. This time, she caught it in her mouth as he came again. She swallowed and waited for the next one, trying to catch every drop in the air and not let it go to waste. He came several times, shooting less and less each time, until it was barely coming out. Jane lowered her dead to meet the wads and wound up sucking his head to get the last few squirts. She cleaned him off with her tongue and stopped stroking as he started shrinking down to normal again, his breath gasping for air.

Glancing over at Janelle, they saw that she had one hand squeezing her big boob and the other tightly clasped between her legs. She was breathing hard and had a look of lust and satisfaction on her face. They had done their job. The bet was paid.

After they all recovered and freshened up, Jane told Janelle, "Hey, any time you want to see Sean's cock, just tell me and I'll show it to you. Maybe we could both enjoy it sometime. It's certainly big enough to share! Next time, I might say it's ok to touch!"

I hope you enjoyed this little story. It was fun to write. Please vote and leave a comment. Any suggestions or ideas for improvement are welcome.

Thanks, HornyHenry