Second Thoughts and Sloppy Seconds

The more Penny thought about this the more excited she was getting. She had really really enjoyed ravishing her Mom and displaying her sexual superiority in front of her 'husband', but with those two it just wasn't right. They weren't into it. They were just into each other. Now here was a couple of friends who shared the same kink. She could show off and cuckold Teddy to her heart's content. Oh this would be fun!!!

The more Teddy thought about this the more excited he was getting. At first he hadn't believed Jennifer when she had told him that her roommate Penelope had 'equipment' downstairs, but she had been SO adamant he had come around. And not just some weird post op tranny or something either. A real, all natural, futanari packing both sets of organs. A real futanari! In the flesh! His deepest desire come true. On top of it Penny was fucking hot, way out of Teddy's league on his best day.

The more Jennifer thought about this the more excited she was getting. She'd only ever been with Teddy and was curious how another lover would feel. Sure Penny looked big, but Jen assumed she wasn't much of a grower. Her flaccid member being bigger than Ted at full mast, it surely couldn't get that much larger. Also, while she was completely embarrassed and overwhelmed by this whole situation, she was secretly overjoyed to be taking place in something so wild and uninhibited.

They all just look at each other a moment, unsure of how to start this thing. Penny decides to take the lead.

"Okay Ted. Tonight we'll just be bedding our beautiful Jennifer here, okay?" Penny states. Ted was an unknown factor right now, she wanted to see how he performed before agreeing to anything more with him.

Jen says nervously. "No backdoor stuff! Yuck! And I'm sorry, no mouth stuff either. Just one at a time please." She didn't want to have to worry about one in her mouth during sex. She was pretty bad at oral plus she wanted to focus on one partner at a time.

Penny nods. "You bet Jen, whatever you want. Although you should really reconsider the mouth stuff, it's pretty great." She laughs excitedly. "Oh man, we're gonna have fun! You're not going to regret this."

Ted just sat there, in utter disbelief that this was really happening to him. He couldn't wait to get started! He clears his throat. "Ladies first."

Penny winks at him. "Sure Ted, I'll bed her first but..." She looks at them sitting on the bed fully clothed. "...you guys show me yours and I'll show you mine." She goes and makes sure the door was locked.

In unison they nod and begin undressing. They were an odd couple to be sure. Ted was overly skinny while Jen was overly portly. Both were pale and in poor physical condition, though both young and healthy still. Teddy had stick limbs and thick knobby joints, his hands and feet seemed a bit too big for his body. Jen for her part did not wear her weight well. Her midsection bulged past her hips and as she removed her bra Penny saw her roommate's smallish uneven breasts sort of merged with the fat of her upper torso and arm pits. Neither had an ass to speak of, both flat and dimply. No two ways around it, these two were pretty ugly. Penny didn't care though, this was just some fun sex with friends. Besides, they sort of suited one another.

Finally they both peel out of their underwear. Jen had a wild unkempt wiry red bush, the curtains definitely matched the drapes. Ted's aching boner pops out, stretching skyward. He had an average slab of man meat, a shade under six inches and like the rest of his body a bit too much on the thin side. He was uncircumcised, his dark knob peaking out from its hood. Penny cocks an eyebrow approvingly, Teddy might be a candidate for her pussy after all.

Teddy notices her staring admiringly at his manhood, he stands up tall and proud. He says. "Your turn."

Penny smiles and nods. She unties her robe and shrugs it off, the soft cotton blend slipping off of her shoulders and falling to the floor. Both Jen and Teddy stand agape at the flawless specimen of humanity before them.

For Jen it was Penny's body. Wide hips, thin tight six pack midsection, large perfect symetrical breasts; the idea hourglass shape. Her skin was healthy and smooth. This body combined with her long blonde hair and sparkling blue eyes. Her face was angular but gorgeous. She was a knockout. Jen suddenly felt very self conscious about her own flabby body.

For Teddy it was all about the cock. He just gawked at it. Not only had he not been prepared for a big one, he had actually been expecting a small runty one. He had, for some reason, assumed her mutation would produce a little stunted half developed penis. Instead she was hung like a prize stallion! She utterly overshadowed what he had always felt was a pretty good sized package. The worst part was that she wasn't even fully hard yet.

Both of them began having major second thoughts. Penny, misreading their jealous gazes for lust, forges ahead. Time to give Teddy what he was after.

Standing like a model in the center of the room Penny looks to Ted. "Like what you see?" She begins stroking her long fat cock. Mouth wide Teddy just nods, she was so much hotter than anyone he'd seen in the flesh. A pang of jealousy flares up in Jennifer, she did not care for this stare Ted was giving her roommate.

Penny is grinning at him. "My goodness, mine is so much bigger than yours isn't it Teddy-boy?"

Ted just laughs nervously, at a loss as to what to say to that. It was an obviously true statement, getting more true by the second as she strokes it to life. Only then does it hit him that she was about to take his girlfriend with that monster. He is still over the moon with arousal, Penny was everything and more he had ever dreamed of seeing. But the green eyed monster suddenly came to life within him. He didn't know what to do though, what to say, they were already into it now. Instead he just giggles nervously once more, social awkwardness and depraved curiosity keeping him from saying anything.

Jen had had enough of Ted ogling Penny's perfect futa body and giggling like a school boy. She finds their lube on her headboard and starts wetting her hairy puss. She says, with more than a bit of an edge to it. "Come on Penny, let's give him what he wanted!"

Ted looks at Jennifer stunned. He realizes she knew about how big Penny was and she had agreed to this without telling him. Now she was hurrying it along! She was humiliating him on purpose! Oh yes, the misunderstandings were flying around thick and fast now. Despite it all Ted was transfixed.

"That's the spirit Jen!" Penny cheers. "You can feel a real cock for once."

Penny studies Ted's reaction to that. His eyes widen and he looks down, mentally comparing their members once more. Penny is feeling good. Oh yeah, he liked it alright. Kinky little Ted.

Penny grabs her roomie and flips her over, she positions her so that her legs hang down from the bed and her body is perpendicular across the mattress. Like being bent over a table. Penny grabs her shaft and begins to play with Jen's slit with the head of her cock. Jen gasps.

If anything Jen had over-lubed her pussy, wanting to be double sure she was well prepared for Penny. A sickly squishing squelching sound accompanies as Penny presses in.

"OHHH! OW!" Jen cries. Penny felt easily twice as wide as Teddy. "God, you're splitting me open! Fuck!"

"Shhh." Penny says. Too loud and they would draw attention from their neighbors. She was concerned though. "Want me to stop Jen?"

Jen growls, she reaches back with both hands and grabs her bottom buttocks and spreads herself wide. "No...don't stop...just be gentle....you're stretching me out Penny...oooo...."

Penny is happy not to have to stop. She slows down and takes some time to really let Jennifer adjust and open up. She takes some time just holding still, but exploring Jen's body with her hands. Then she begins with slow shallow strokes, pressing in just a bit deeper each time, and holding it there just a bit longer each time. She encourages Jen, telling her how good she felt, asking her for feedback. For now she was fucking her with a feminine touch. By contrast Teddy generally just jammed in and started thrusting.

Penny looks over to Ted, he was still hard as ever but it seemed like it was time to get him involved. Time to really scratch that cuckold itch.

"Oh my Teddy, she's taking it so good. She is tight, tight, tight." Penny motions downward. "Check it out. Deeper than you'll ever be and I've got room to spare." She gives Jen's flabby ass a light spank. "Tell Teddy how it feels Jen."

Jennifer starts by letting out a long throaty growl. "Guhhhhhhrrrr....so full..so full..so full...she's so fucking big Ted...so fucking big..."

Penny laughs. "Oh boy, I think she likes it Ted!" Pulling back she takes a few shallow strokes. "We can share this part Ted..." Then she pushes into Jennifer hard, plunging deeper than ever. "...but this part is all mine."

Jennifer screams into her blankets as she is filled to bursting. Both she and Penny feel as she butts against the cervix.

Ted almost felt sick as he watched his girlfriend struggle to take the monstrous cock...and then succeed at it! And the cherry on top, she was starting to enjoy it.

Jen pulls her face out of the blankets. "Oh my god! I...I...I fucking love it. God you feel good Penny..."

"Whose do you like better Jen?" Penny asks.

Without hesitation. "Yours! Yours, yours, yours, yours. No comparison!" She is panting as her orgasm begins to build. Her whole body suddenly shudders and tightens as she buries her face in the blankets once more to scream. Ted had never gotten a climax like that from her, nor would he.

"Ha! No comparison Teddy. You're getting cucked by a girl dude." She laughs. He blushes furiously. If this wasn't getting him going nothing would!

Penny allows Jen to ride out her orgasm. Penny loosens her shoulders and cricks her neck, time to go to work.

When the powerful Penny starts up again she absolutely unleashes herself on the unprepared Jennifer. She fucks her faster, deeper, stronger, and better than any partner Jen would ever meet.

Ted just sat there feeling like a fool. As Penny fucked his woman for a long long time he sat and watched politely. Sex would never be the same with Jen after this, after he had been so completely outclassed by this freakish dynamo. The knowledge of being a distant second best would always be in his mind, and surely Jen's as well. Despite it all he is hard as ever, watching futanari Penny in action was something else!

During their sex Penny experiments with a few different positions. She is able to grab her roommate in her powerful arms and just move her around as she wants, putty in her hands. Not a small feat considering Jen's size. In the few bits of reflection for Jennifer she marvels at Penny. It's not just the size and incredible hardness, it's the strength and stamina more than anything. She felt helpless as a baby in her arms.

Jennifer cums almost a dozen times, the last few hard on top of one another, before the end. By the end she is completely worn out, there was no more pleasure to be wrung from her exhausted body. She just lay there, holding on for the finish. She grunts like an animal at each pistoning impact.

Penny has Jen on her side across the bed while she stands on the floor. She holds Jen's left leg up, pointing to the ceiling, hugging the leg to drive in with greater power. Penny lets out a controlled wail, so as not to make too much noise, and dumps her herculean load deep deep inside the overwhelmed red head. Ted watches her balls and shaft constrict and pulse like a heartbeat as she pumps wad after heavy wad into his girlfriend.

Penny wipes her brow with a smile. "Whooooweee! You're turn Teddy-boy, show us what you got." She pulls out with a beefy plop and backs off, going to rest on her own bed to watch the action. Her cock glistening with lube and cum and Jen's pussy juice.

While he didn't really want to he felt he had **** at this stage. He had begged for this to happen after all. His girl friend lay there splayed out catching her breath and moaning. Her gaping vag wide open and leaking creamy nut butter. Her eyes were sort of unfocused and staring at the ceiling. Grabbing his aching wood he slips it into Jen's stretched cunt. It is the sloppiest of sloppy seconds imaginable. She barely reacts as he sheaths himself as deep as he could. She wants to react, to encourage him, but she just can't. She is done, she is so done. She continues to stare up at the ceiling.

Penny, proud of her handiwork and hoping to help get Teddy off, pipes up. "Uh oh Teddy, you better try harder than that." She teases him. "Come on Ted, show her what a man you are! Surely a girl can't fuck your woman better than you. Fuck her! Fuck her hard Teddy-boy!"

Ignoring her he begins pounding into his girlfriend. The copious amounts of jizz and lube making it all the worse. A crude slurping farting sound accompanies each thrust, his cock is damn near rattling around in her ruined tunnel. To make matters worse, he keeps slipping out. With near zero friction holding him in he keeps springing loose on the backstroke. And Jen just lays there, staring blankly. It was pretty shitty for him too, he barely felt a thing.

Penny lays on her bunk watching the sad display, Ted was obviously having troubles getting off. She was going to mock him some more to help him over the edge but it seemed overkill at this point. She finally decides there would be no harm in letting him do her, he couldn't hold a candle to her Daddy anyways. And she was horny as hell!

She spreads out. "Want to try my tight little futanari pussy Teddy?"

Ted nods enthusiastically, anything would be better than this and he was **** to get off after waiting for so long. Pulling out he leaves Jennifer's bed for Penny's. Jen just lay there, still recovering. She turns her head to silently watch the other two.

As Ted enters her tight wet slit Penny lets out a little sigh of delight. After all this fucking her lady parts were fired up like a furnace. "Ohhh....oh Teddy...go slow...ohhhh..."

Teddy lets out a long low moan as he penetrates her. She was so naturally wet and so naturally tight, she felt better than anything he had ever experienced.

In a moment of passion he says. "Oh my god Penny. You are so fucking tight, you feel so fucking good! Ohhhh god!"

Her fit gorgeous body arched under him as she sighed again, thrusting her tits upward. He cups one of her big soft perfect breasts and leans down to lick and suck it. She responds to his every touch. "Ohh Ted!" To top it all off that semi-erect cock attached to this incredible package...this finally was that dream come true for Teddy. He had to go through hell to get to heaven, but heaven was finally here!

Jen lay on her bed watching this spectacle. She was beyond jealousy at this point, she was just numb. She felt used and discarded. She was lying alone while watching her boyfriend look at and make love to another woman in a way she could only dream of. Try as she might she could not think of one single thing she had better than Penny. Her roommate could steal her boyfriend anytime she wanted, with hardly an effort.

Given all the excitement Ted couldn't last too long, the same also held true for Penny though. They are moaning and breathing heavy. Kissing and nibbling each other's bodies, moving in unison toward a shared climax. Penny says in a sweet gasping voice. "Oh god, you're gonna make me cum Da..err...Teddy...come on..." He is plowing into her as hard as he can. The sounds of their bodies coming together filling the room. As one they cum together. They clutch onto each other as the buck and writhe and ride out their bliss. After a long satisfied guttural hum Ted finally collapses on top of her.

"Whoo!" Penny sighs contentedly. "You two are something else!"

Rolling Ted off of her she gets up. "And I am going to need another shower." She laughs and kisses Ted on the cheek. She then crosses the room and kisses Jennifer on the cheek. "Thank you guys! If you could PLEASE keep my secret I think this might be the beginning of a wonderful friendship."

She cheerfully picks up her robe and heads back to the shower.

Ted lay on Penny's bed. Jen lay on hers. Both of them spent and exhausted. Both of them having experienced the best sex of their lives. They stare across at each other, into each other's eyes, and don't say a word. They would never be the same.