An Upside-down “Y”

Kyli pushed her face into the pillow and moaned, "Mmmmhhh."

As Ted's tongue worked, he felt his cock throbbing at its full length and girth and thought it was funny only a short while ago he was wondering if he'd be able to get it up for a third time. His tongue slipped off her squeaky clean hole and he gave the baby smooth skin of her valley a half dozen breathy kisses before he pulled his face up.

Ted dipped his right thumb into the clear lube already melting a little in his left palm. He shifted his body to the left slightly, then smeared a dollop of the gel on Ky's hot little hole. He wasn't surprised when she flinched and tensed.

Kyli was panting. She turned her head to the side on the pillow. "That's... cold."

Ted half smiled. He watched his slippery thumb rubbing. "Still cold?"

She closed her eyes and shook her head. "No. It... feels good."

Ted settled his profile on her fleshy bun and watched his thumb on her hot asshole. His thumb stopped moving and his face went blank. "You... you don't have condoms?" He chastised himself for not having any with him. He hadn't thought he'd need any.

"Huh? Condoms? Why... no, I don't." She wondered if he was worried about getting poop on his cock.Oh god... that would be so embarrassing."Why? Are you afr..."

He interrupted as his thumb started moving again. "I... I think you're supposed to use them for... for disease... health reasons."

"I... I don't have any STDs, do... doyou?" Kyli tensed.

"No. It's... about hepatitis."

"I don't have that, do... you?"

"No."

"I don't understand."

The times he had done anal he had never used one. "I don't either."

"Does it really matter?" She didn't want to stop for any reason.

Ted hated himself for bringing it up, but he was concerned about Kyli. Or was it the guy who was the one taking the chance? Wouldn't you have to have hepatitis to pass it to someone? "No, not... not for us." He again mentally chastised himself for not knowing more about it. Then again, there weren't too many chicks in his past who had wanted to take it up their ass. He'd look it up on the internet soon. He turned his head and gave her cheek a few kisses as his thumb applied a bit more pressure to its circling massage. "This feel good?"

Kyli closed her eyes and stopped thinking about condoms. "Uh-huh."

He hoped he hadn't broken her mood. He moved his thumb and coated it with more lube and returned it to her torrid hole. She flinched again. He heard her giggle softly and briefly. "Cold?"

"Uh-huh." She felt Ted's hand turn, his fingers covered her slit, then a fingertip gently rubbed her already tingling clit. "Mmmmh." Her breathing picked up tempo again. Her hips squirmed.

Ted watched his thumb even while he gave her smooth bun a couple kisses. His voice was soft and low, "That night when you were 18, the 'what if' night, I wanted to make love with you every way possible, Ky."

"Me... me too."

"I wanted to rip your panties off... rip your shirt off and... be inside you."

"I... wanted you to."

"I wanted to be in your pussy, and... and in your ass too." He pressed the tip of his slippery thumb to the apex of her pursed little orifice. "Relax and try to push out a little... sort of." He didn't know how to tell her any better. He felt it on her anus. The tip of his thumb sunk into ass up to the first knuckle. His fingertip switched from circling to crossing strokes over her taut pink pearl. He remembered her confessing to fingering her own ass. The thought made him relax a little. In a way she had some experience with this.

"Oh... oh Ted." Her breathing turned into deeper quick gasps.

"Feel good... feel hot?"

"Yes... yes."

"Remember, tell me if anything gets... ah... uncomfortable."

"Uh-huh. Um... push... push more."

Ted didn't need to be told twice. He kept his fingertip working her clit as he swayed, undulated and applied pressure to his thumb. It slowly slid intoKy's ass not stopping until the large knuckle at his hand was stretching her opening. He felt her torrid ring grip tightly.

"Urrrrrh," Kyli moaned.

"Does it hurt? Should I pull back?"

"No.. jus'... don't move it yet." There was a little pain, like at first when she had first tried two fingers. She knew all she had to do was wait and relax. Maybe it was the drinks she had but she was able to do that sooner than she thought she'd be able to. "Okay. It... it feels good." She wasn't really sure what he was going to do next. What he did surprised her.

Ted poured and wiped off the gel from his palm at the top of Ky's deep crevice, then pushed that hand between the pillow and her abdomen. The middle fingertip replaced his other on her taut clit. The other fingertip curled and coursed up and down between her flared, slippery labs. He knew part of the lubrication there was his jiz still oozing out of her channel but hoped it was also her dew of excitement. He kept his thumb planted deep in her ass, only moving the tip slightly, as his finger at her slit undulated into her channel, curling and stroking within her tight confines.

Kyli's eyes blinked open. She had never felt anything like what he was doing, especially when his thumb and finger both pulled back then slowly pushed into her again. "Oh... ohgod."

He almost stopped but kept pushing into her slowly. "Feel good?"

"Uh-huh... oh... oh Ted."

He added more gel to his thumb, then continued slowly DP fingering her for another minute. The last two strokes, Ky's ass pushed to meet his probing digits. That alone almost made him shoot his wad. The very last stroke, he kept pushing, the final, large knuckle on his thumb pressuring her anal pore, making it yawn.

Kyli moaned, "Uhhhh... mmmmmhhh."

Ted felt both her anus and channel tighten around his digits as her bottom pushed towards him and her hips swayed and squirmed. His face dipped and smeared over fleshy mounds. The finger on his other hand varied speed and stroke more on her turgid, pink pearl. His finger and thumb slowly pulled out of her pussy and ass. He quickly picked up the lube and squeezed another large dollop on her coccyx, put the tube down, then coated his already dewy middle finger and his ring finger, wiping up a large gob of the clear gel onto his fingertips. He nudged her right cheek to the side with the back of his hand and pulled the other with his face, opening her deep valley.

Her anus hadn't closed all the way after his thumb exited. When he deposited the gob of gel on the little "o," Ky tensed again at the coolness but only for a moment. He held his fingers away as his thumb attempted to gather and push as much as he could of the lube into the little opening. Ky's ass pouted a little higher. He curled all his fingers back except for the middle one. He circled the tip around her hot pore, then pushed the tip inside her heat. It entered easily. He diddled it for a few moments then slowly pushed his stiffened digit into her ass. He felt her anus tightened for a second as his middle knuckle disappeared into her bottom.

"Mmmmmmhhh," Kyli moaned as she pushed up and back to meet Ted's slippery invading finger. When it was all the way in, she felt it turn and twist. "Mmm."

Ted slid his digit out, then crossed it with his ring finger. He turned his hand back and forth working the two tips into Ky's little "o." As more of his fingers moved into her, the "o" stretched wider. Ky's slightly swaying hips stopped. His fingers halted, even the one on her clit. God he wanted to have his cock in her ass. "Ky... I don't want this to hurt you."

"Wait." She was panting. "Wait a second." She didn't want to disappoint him and she didn't want to disappoint herself either. She concentrated on relaxing. "Okay... okay now." She first felt the fingertip on her clit move. It sent a delicious shiver through her and maybe because of it, without thinking her bottom pushed up and back. She felt her anus stretch and it didn't hurt. It felt erotic, hot. She shut her eyes tightly, her teeth gritted at the pleasure of having Ted's fingers in her and not her own. "Yesssss," she hissed softly.

Ted slowly worked his fingers in and back for nearly two minutes. He had to go even slower for a few strokes after he uncrossed them. Kyli got used to the added width quickly though. He turned them now and then and again almost shot his wad when Ky responded by churning her hips with a bit more intensity. He added more gel, then grouped his index finger with the other two. They slid in easily until the middle knuckles.

"Urrrh," Kyli grunted.

Ted stopped but didn't ask if it hurt. Obviously there was discomfort. The finger on his other hand continued firmly but gently working her clit, pushing the nub side to side, circling it with his fingertip, diddling it for a few seconds, then stroking, then pushing it side to side again. Just as he was about to tell Ky that maybe they should stop, she spoke.

"Now... push... push slowly."

Through his own ragged breaths Ted whispered, "If it hurts, tell me to stop."

Ky breathlessly answered, "Push... slowly, push in... I... wanna feel it. I wanna feel you inside me."

Ted did as she instructed, with starts and stops over a minute or so, he finally had all three overlapped fingers buried in her hot hole. Again he almost shot his load when Kyli's hips started churning again, tentatively at first, then with more certainty. He slowly retracted his grouped fingers and then pushed in again.

"Ohgod... oh yes... yesss... ohgod... Ted... I-I want you in me there." She shut her eyes as her hips squirmed. He felt his fingers twisting. It didn't hurt at all. There was just that weird erotic thrill coursing through her body. "Now, Ted... now baby, please."

Ted was still on the edge of orgasm. He wanted his cock in her ass. He slowly pulled his digits back, twisting them the entire way. He pulled his other hand out from under her, held her valley open, and added more gel to her now dilated anus. Once again she flinched at the coolness, then released a very brief, breathy giggle. He quickly used his thumb to work the gel into her torrid cavity, then hurriedly coated his throbbing cock.

He moved between her bound open legs, stretching his own over the end of the bed but holding himself up on his knees and with an outstretched arm. He grabbed his lubed rod and brought the deep read head to Ky's dilated anal pore. He stroked the tip around her hot hole.

Kyli's eyes shut as she whispered, "Ohgod. Yes... yes, Ted."

He took a few deeper breaths. "Tell me to stop... if it hurts."

"Yes... yeah... push in... push in."

He gripped his prick and nudged the tip at the center of Ky's slightly gaping anus. The head was twice as large as the "o." It started to dilate more. He had to shut his eyes even though he wanted to watch. He was already at the edge of cuming. He had dreamed of this moment for years. He didn't want to shoot until he was completely buried in Ky's luscious ass. He could feel her anus contracting against the spongy-firm helmet. He felt her sphincter hugging half the head. He kept pushing slowly and firmly, then just as the lip of his helmet was about to get past the hot muscle, he felt it contract severely and Ky tense beneath him.Dammit!He opened his eyes and looked first at his groin and her luscious ass, then at her pretty profile. Her hair hid a good portion of her face but he saw her eyes shut tightly and an expression of pain.

Through labored breaths he spoke, "Ky... we don't have... to do this." He gulped more air.

"No... no... wait... wait..." Kyli panted more breaths. She concentrated on relaxing.

"You... you push back when you want to." He looked down at her perfect buns again. He didn't move for nearly a half minute, then felt and saw Ky's hips sway slightly. Her sphincter loosened a little. She pushed up and he held fast. They both twitched when the ridge of his helmet passed her sphincter.

"Urh!" Kyli nearly yelped.

"It hurt?"

"Yeah... no... um... just wait. It's jus... ohgod, you're... sobig."

"Ky, I don..."

She interrupted, "No... wait."

Over the next five minutes, in slow increments and adding a lot of lubricant, Ted's cock worked into Ky's tight anus. For the most part, he let her determine when to move, allowing her to push back and take a fraction more into her hot rectum. Ted would pull back a little from time to time, then push in the same amount. A couple times Ky would breathlessly say, "A little more," and he'd nudge a bit more of his throbbing rod into her pouting, seductive ass until she clenched again. Finally there was only an inch of his stiff, pulsing manhood not ensconced in her heat.

She told him to wait as he felt her torrid ring tighten around his staff. He was holding himself up with his elbows, looking between their bodies once in a while, but had to stop that. The sight was too erotic, too hot and he didn't want to cum yet. His left forearm was under her, his hand was at her pussy, his finger playing with her turgid clit. His right forearm slid on the sheet, his hand cupped around and held her elbow. Her arms were still stretched straight, her wrists still in the tie loops attached to the headboard.

He stroked his face through her fragrant, dark brunette hair. His breathing was ragged, so was Kyli's. He felt her anus relax again. He pressed his lips to her ear and whispered, "I'm going to pull back, then... slowly push into you, all the way, Ky. I-I won't last long, this... you feel too good. If... if it hurts, tell me... right away."

Kyli swallowed and took a deeper breath. "Yeah... I want all of you in me... all of you, Ted." She swayed her hips slightly.

His chest rose and he looked between their bodies, at the sensual curves of Ky's luscious buns. He started pulling back. Ky moaned but he knew it wasn't from any pain. When he felt the helmet at her sphincter, he reversed course, denying himself the urge to shove his pulsing prick into the depths of her heat.

Kyli released another soft moan as she felt the entire length of Ted's thick cock slowly slide all the way into her bottom. On the last inch or two, she pushed up and back to meet him. It felt so weird, yet so erotically and sensually thrilling. His finger on her clit alone almost had her at the brink. She felt so full of him, her anus was so stretched, yet the discomfort, sometimes momentary painful discomfort, had disappeared. It was so hot, so erotic, so incredibly intimate, and so naughty yet it wasn't naughty, wasn't bad, and wasn't perverted, they were giving each other what they wanted, what they desired. It was loving, yes, it was love not perversion. She felt so close to Ted, no psychological or emotional or even sexual taboo boundaries separated them. That was what making love should be. What she had always wanted it to be.

His cock and his finger on her clit had her at the brink for minutes. She couldn't hold back any longer. "Oh... y-your f-finger... Ted... oh... ohgod...you're in me so... so deep... s-so b-big... I-I... y-you... c-cum... oh... oh..." Her hips started churning more and more intensely. "Push. Harder.Push!" She felt his groin grinding against her ass, not only shoving his cock as deep as possible into her bottom, but forcing her body towards the headboard, straining the tie loops around her ankles. That last sensation threw her into orgasm. "Ohgod... ohgod... now... now... T-Ted... n-n-NOW!"

Ted had been holding back so long that when he let himself go, it was almost painful. "AHHHH!" Without thinking, he shoved even harder into her ass.

"Ohhhh!" Kyli felt his thick cock surging, pumping viscous heat deep in her rectum as her body went into erotic convulsions.

Ted couldn't have held back after her shouts. He had hoped to slide in and retract at least a few times but it would have been impossible to restrain himself that long. This was incredibly perfect as is. As Ky's ass shoved, swayed, jerked, and twitched, he kept pushing into her and grinding his hips, as his fingertip continued playing with her pink pearl. His entire dream had been realized. The dream had always been that Ky would want this and get as much pleasure from it as he would. And it seemed, no, it definitely was true. She loved his cock in her ass. He felt the last ripple, but still kept pushing and grinding although with less intensity. He was gasping his breaths as he lowered his chest a little more to her sleek back. His grip on her upper arm lessened. His finger slowed then stopped on her clit. He pushed his face into her dark, fragrant hair. He gulped a few breaths before trying to speak.

"Ky... I love you."

Kyli was still trembling and twitching. She had to swallow a couple times before she could whisper, "Ted, I love you so much."

Two minutes of relative silence passed, only the sound of Ted's breathy kisses on her profile, neck, shoulders could be heard and of course their labored breaths. They both felt his cock shrinking. When it finally slipped out, they both flinched.

Kyli released a breathy giggle. "It got small again." She drew in a deep breath. "God... you were sobig."

He knew his finger had probably felt huge in her bottom too. "Ky... are you okay? I didn't hurt you, did I?"

"Uh-uh. Didn't hurt." She closed her eyes as he gave her a dozen moist kisses on her upper back. "Um... but..."

Ted instantly raised his head. "What?"

Kyli felt her face flush. "I... I think I have to um..."

He smiled and gave her shoulder a kiss. "Like you have to take... ahh...poop?"

She shut her eyes. "Yes." She heard his breathy chuckle. "Shut up."

"Can you get the loops off your wrists?" He knew she didn't have to defecate.

"I... I don't know." She blinked, then her brow pinched. Ted started working the loops off her wrists. "Ted?"

"Yeah?"

"It's weird. It... it kinda feels like... like you're still inside me."

He half smiled. "Really?" He knew it was the 'ghost' of his cock.

"Uh-huh, but... I... you know."

He got her other wrist out of the loop. "Yeah, I'll get your ankles free."

"I... I really don't want either of us to move, but..."

"Yeah, me either but you need to... ahhh...sit down." He gave the corner of her mouth a kiss, then slid off the bed. As he took the loop off her first ankle, he gazed at her pussy and ass. He only had partial view of her anus in the deep valley. It was still dilated but already closing. Both her pussy and ass were leaking his seed. He freed her second ankle.

"I... I don't think I can move. I... I've had too many orgasms." She giggled.

Ted sat on the edge of the bed and again wondered how drunk she was. He wondered that about himself too. He stroked his palm gently over her ass and up her back. He leaned down and kissed her shoulder. "Want me to carry you to the bathroom?"

She giggled softly again. "Mmmmm... That'd be nice, but I think I can make it." She drew in a deep breath then started sliding towards the edge of the mattress. Ted stood up. She looked at him. He was smiling. She grinned. "I... I never had a night like this, never... I never felt this good."

He took her hand and helped her up. "Neither have I." He wrapped her in his arms, then they kissed, their tongues dancing once more. They held each other closer. Ky was the one to slow the kiss, then hugged him even tighter.

"Ted, I love you so much."

"I love you, Ky."

"I have to go to the bathroom."

Ted chuckled and pulled his arms away as Ky did the same. He took her hand. "Mind if I watch as I start us a shower?"

"You're gonnawatch?"

"Yeah."

"You're soweird." She was about to tell him no, but then realized how open and intimate they had just been. What difference did it make if he actually did watch? She glanced at him. Was he just kidding? He had always been weird like that though. She remembered as kids and teenagers, him watching people, and insects, and staring at odd shaped trees, and all sorts of things.