Anniversary Fling Pt. 04

A short while later, Reed had washed up and Sandy and Jill had showered together. When the two women came out of the bathroom Reed had just finished pulling the sleeper-sofa out and getting an extra pillow from the closet.

"Thank you for letting me sleep here with you," Jill said. "That looks pretty comfortable, but frankly, I'd sleep on the floor at the foot of your bed if you told me to."

"You're such a wonderful, willing pupil for Sandy," Reed said, "but the sofa is for me. The thought of you two cuddling together, naked under a sheet, has my worn-out pecker twitching."

"Oh, thank you!" she said and gave him a hug and a kiss. She reached down and gave his flexible cock a light squeeze and pull, and asked, "Would you like me to take care of the twitching for you?"

"Thanks," he said, "but I think he just needs some alone-time if he's going to recover enough to continue Sandy's lessons tomorrow."

***

Reed was the first to wake up the next day. With a morning-wood hard-on, he walked to the bathroom to take a shower. On the way, he stopped to look at the two women in the bed. Jill was spooned into Sandy's back and the sheet was pushed down far enough to expose their lovely tits. Reed's boner twitched and he whispered to it, "Down boy! The day is just starting."

When he came out of the bathroom, both women were up and dressed. Sandy had picked a short, button-front sundress from Jill's suitcase and instructed her to wear it without a bra or panties. She had her leave all but two of the buttons unfastened, making sure that her petite tits would be easily visible to anyone who cared to look. Before yesterday Jill would never have considered going out in public like that, but this morning it made her naked pussy tingle.

Sandy was dressed in crisply pleated black slacks and a black halter top that left her midriff exposed and pushed her tits up and out. It was certainly not tropical attire; it was dom attire and that added to Jill's pussy-tingle.

On the walk to the dining room for breakfast the warm breeze off the water caused the top of Jill's dress to flutter open, completely exposing one tit or the other, and at one point it blew the back of the dress up flashing her naked ass to anyone walking behind her. As she would have in the past, she made no attempt to protect her modesty, instead feeling more sexy and impish than she ever imagined she could.

They selected their food from the buffet and when they sat down Sandy handed Jill a long-stemmed cherry from her bowl of fruit and told her, "Stick that in your pussy and leave the stem hanging out."

A little shudder of incomprehensible arousal ran through Jill's body as she spread her legs and reached under her dress. She pressed the little fruit against her pussy lips—which were already wet from the walk over—and it popped easily inside. The coolness and the tease of its small size made her quiver and wish that her mentor had given her a plum to shove up her cunt!

"We'll leave that there for a while, and then you can feed it to my hubby," Sandy said as she cut her sausage patty.

While they were eating a couple stopped at their table, and the woman—probably in her forties—said, "I hope you don't mind, but we were walking past your bungalow last night, saw the shades open, and stopped to watch." The guy added, "God, that was quite a show! Stephanie gave me a blowjob while we watched and then we used one of your chairs and I ate her pussy."

Sandy asked Jill, "Did you mind being watched while you ate your first pussy and got fucked from behind in a sixty-nine, sweetheart?"

Jill's pussy leaked around her inserted cherry at the thought of turning other people on while they watched her having unbridled sex, and she answered, "No, not at all! I never thought I could be an exhibitionist, but Sandy has taught me all sorts of things I didn't know about myself."

Sandy smiled and patted her hand and said, "And there's more to come."

When they were finished eating and Sandy pushed her chair back, Jill said, "The, um, cherry?"

"I didn't forget, sweetheart," Sandy said. "Hold it in your pussy until we get back to the bungalow."

Walking with the little sphere right in the entrance to her cunt-hole and its stem sticking out and tickling her pussy-lips Jill had to concentrate on keeping her cunt tightened so it wouldn't slide out with all the pussy-juice she was leaking.

When they got to the bungalow, Sandy told Reed, "Go down and pop Jill's cherry ... out of her pussy. Use your teeth then come up and share it with her."

Reed went to his knees and put his head under Jill's short dress. He licked her wet slit from bottom to top, flicking the protruding stem with his tongue as he went up.

The contact on her aroused pussy made her moan, and when he wiggled the stem she had all she could do to hold the cherry in her cunt-hole!

Finishing his lick with a tongue-poke into her clit-divot, he went back to the stem. He twirled it in circles with his tongue before opening his mouth and engulfing her pussy as he took the stem between his teeth. After a sucking cunt-kiss he began to pull back, extracting the small fruit with teasing slowness. As the little orb stretched her pussy-lips even that tiny bit Jill groaned and her pussy leaked around it and then drooled when it was finally gone.

Reed stood up with the glistening fruit dangling from between his teeth and pulled Jill into a tight embrace pressing his boner against her pussy through the two layers of their clothes. She sucked in a deep breath as she opened her mouth to accept his gift.

The cherry was warm, bordering on hot, and tasted like pussy. She sunk her teeth into it and pulled, snapping it free from its stem.

"Remember to share!" Sandy said.

As Jill twirled the little fruit around in her mouth, enjoying the mixed flavor of pussy and cherry juices, Reed held her ass and kept her pulled tightly against his cock. She was sure that if he began to rock his hips and hump her burning pussy she would explode in seconds. Breathing deeply through her nostrils, she bit away half of the cherry's flesh and presented the rest to Reed between her lips.

He spit out the stem he'd been playing with with his tongue, went into a kiss with Jill, and sucked the cherry into his mouth. A few moments later, he presented the stripped pit between his lips, and Sandy picked it out.

"I hope we have time for breakfast before you have to leave tomorrow," Sandy said to Jill. "They had some luscious-looking plums in their fruit bowl."

Jill's pussy leaked a little more having already thought about that.

"But, as this is your last full day with us," Sandy went on, "we need to get on with your lessons. Anal 101. Both of you take off your clothes."

Jill looked at the wall of glass with its curtains pulled wide open. A day ago that would have given her pause; today she found that she was a little disappointed that there was no one out there to watch her next lesson.

Seconds later, Jill had her sundress off and Reed had kicked his shorts across the floor. Sandy, still dressed in her "dom" clothes, said to Reed, "Do you remember your offer to let us use you any way we wanted? Well, you're going to be our study-aid for today's lesson. We're going to use your tight little asshole to show Jill what she's about to experience. Now, if you would be so kind as to get on the bed on your hands and knees, we'll get started."

As he crawled onto the bed with his drooling boner as stiff as a pipe, Sandy opened a dresser drawer and took out a bag. "While the two of you were fetching your suitcase yesterday," she said to Jill, "I ordered a few things from the resort sex-shop." She took out a silicone rubber butt plug and handed it to Jill. "Lesson number one is lube and lesson two is relaxing."

They got onto the bed on either side of Reed, and Sandy retrieved the bottle of lube from her nightstand. Handing Jill the bottle, she said, "As much pre-cum as your hubby might be drooling, and even if he slobbers your pucker with his spit, that's usually only good for getting the tip in. Lube is going to make the experience so much easier and so much better for you. Both of you, actually." She pointed and went on, "Dribble a little on the plug and wipe it up and down to get it nice and slippery. Then drool some onto his asshole."

The butt plug was about three inches long and tapered from a narrow, rounded tip to a bulge that was a little under an inch in diameter. Behind the bulge, it necked down to less than half an inch before widening out into a two-inch round base. Its fattest part was smaller than her fiancé's cock, but as Jill wiped the rubber cone with lube she was still quite sure it wouldn't fit up her ass. Not without great pain, anyway.

She squirted a little of the lube on Reed's sphincter, and then Sandy told her, "Okay, nuzzle the tip against his little rosebud. Make little circles to be sure he's well-lubed, but don't push it in yet." To Reed, she said, "Clench your butt, baby. I want to show her what it's like when you fight it."

Reed tightened up, and Sandy told Jill, "Now, try to push it in."

Jill pushed, but the tip of the plug barely spread Reed's tight sphincter at all.

"Push harder," Sandy told her. "I want you to see how strong an unwilling butt-hole can be."

She pushed harder—enough that she was sure it must hurt—but still less than half an inch made its way into Reed's ass.

"Now, relax, baby," Sandy told her husband.

As soon as he did, half of the rubber cone slipped easily into his canal.

"Now, work it in gently. Let his ass get used to it little by little," Sandy said. "Slip it all the way out and then go back in just a little deeper than the last time. Watch how much his sphincter can stretch."

Jill did as instructed and was almost mesmerized by how easily Reed's once-puckered little asshole stretched out to accommodate the huge invasion. As she neared the fattest part of the plug and every wrinkle was stretched out of his sphincter, she said in amazement, "Doesn't that hurt?"

"Just enough to feel really good," he replied. "Sandy hasn't pegged me in a long time. You're really good at this, by the way."

"Okay, next time push it all the way in," Sandy said. "Watch his butt-hole swallow that knob."

Jill withdrew the plug all the way and watched his sphincter shrink back down to its wrinkled pucker. She then pushed with more force than before and watched the little ring of flesh expand and keep expanding until the fat bulge had stretched it taut. As the knob passed through his sphincter it snapped shut around the plug's neck, actually pulling it the rest of the way into his ass by itself.

Reed's boner jumped and drooled and he let out a low moan.

"Leave it in and wiggle it around a bit," Sandy said.

Jill held the plug's base and twisted it so its tip would be making little circles up inside Reed's ass.

His cock jumped and twitched and drooled, he arched his back, and groaned, "Oh, fuck! You tease!"

"Oh, you love it!" Sandy replied to her husband with a chuckle. To Jill, she said, "You're tickling his prostate; his version of a clit. Now, pull it out and go back and forth a few times—all the way in and all the way out—to get him totally relaxed and used to the stretch."

She pulled the plug out and then pushed it back in in one smooth motion, fascinated by how easily Reed's sphincter expanded to accept the fat bulge. With each full-depth insertion, she was amused when the plug poked his prostate and he let out a little hum and his cock-twitched.

After several pokes and a few prostate tickles, Sandy said, "Leave the plug in his ass this time and come over here." She got off the bed and went back to the dresser. From the sex-shop bag, she took out a realistically shaped rubber cock about seven inches long and more than an inch and a quarter thick.

"He can take this in his ass?" Jill said as she took it and then giggled as she shook it and watched it wobble.

"Well, we're going to find out," Sandy replied. In fact, she already knew, because they had a slightly larger rubber cock at home that Reed occasionally took up his ass.

Just as Jill noticed what appeared to be a mini-cock protruding from the bottom end of the dildo, Sandy took a harness from the bag, and told Jill, "Put this on and work the dildo through the hole there." Jill quickly realized that the mini-cock would be grinding right against her clit when she did. Her pussy was already tingling as she stepped into the black nylon straps.

As Sandy cinched the straps tightly around her hips and ass, Jill played with the rubber cock, sliding her fist up and down its length and forcing its smaller end between her pussy lips and against her clit. "Oh, Jesus!" she moaned as she gave her new appendage a twisting grind into her clit.

"Fun, huh?" Sandy said. "Now you have some idea why guys like to jerk off so much."

Back on the bed, Sandy had Jill coat the dildo with lube and then extract the plug from her hubby's butt. Sandy pulled Reed's cheeks apart as Jill crawled up closer with her glistening rubber cock in her fist.

"Rub the knob around on his pucker a bit," Sandy said. "Let him know what's coming. Then push forward gently and watch how his tight little asshole stretches out to welcome the fat knob."

As she pushed against Reed's sphincter the other end of the dildo pressed into her clit and she let out a moan just as the rubber cock-head was swallowed by his ass and he let out a moan of his own.

With Reed's asshole tightly clenched around the neck of the dildo just behind its thick-ridged rubber knob, Sandy told Jill, "Do that a few times. Fuck his tight little ass with just the tip of your cock." To Reed, she said, "You like a nice tip-fuck, don't you baby?"

"Oh, God, yes!" he groaned with his face in the pillow. "Poke your fat knob in and out of my ass! Stretch my pucker out and get me ready for your whole fucking cock!"

Jill tugged back, removing the pressure against her clit as she watched the taut ring of Reed's asshole go from being rolled inward to stretching outward as it seemingly tried to hold her cock-head inside. Its amazing elasticity fascinated her, but perhaps more surprising—and certainly more arousing—was Reed's moan of obvious pleasure at the unnatural expansion. Could getting one's asshole stretched around a stiff cock really feel that good? He sure didn't seem to be acting and it made her own asshole tingle a bit in anticipation.

She poked the big glistening knob in and out of Reed's ass half a dozen times, each push giving her clit another wonderful rub and each time going in a little bit easier as his sphincter got more and more used to the repeated invasion.

On the next push, Sandy told her, "Shove your cock all the way up his ass this time! Nice and slow so he can enjoy the added stretch of your fat shaft and feel your knob poke his prostate!"

Jill pushed her hips harder against the added resistance and was rewarded with a long, low groan from Reed and a harder, longer grind against her enflamed pussy-lips and clit. Just as the fattest part of her cock disappeared within his impossibly stretched asshole, his body flinched, his cock jumped, and he grunted, "Oh fuck!"

"You just poked his prostate," Sandy said. "Keep going and shove that whole thing up his ass!"

With a continuous moan from Reed as the pseudo-cock rubbed across his prostate, Jill kept leaning in until her hips were against his ass-cheeks. "Now, swivel your hips a little bit," Sandy instructed her. As she did, Reed grunted, "Oh, fuck!" again, and she moaned, "Oh, shit!" as the cock-stub on her end of the dildo ground into her pussy and clit.

"Now, fuck him!" Sandy directed. "Fuck his ass the way your surprised hubby is going to fuck yours on your wedding night!"

She began rocking her hips and as the rubber dick poked and slid back and forth over his prostate Reed kept moaning and groaning into the pillow and his cock kept twitching and drooling.

With her hands on his hips, she began to increase her speed, and as if he wasn't in the room, she asked Sandy, "Can he cum this way? Just from getting his ass fucked? Without jerking off or anything?"

Sandy chuckled, and replied, "Let's ask him. How about it, honey? Are you going to blow a load just from getting your ass reamed by Jill's fat rubber cock?"

"Fuck, yes!" he groaned. "In about twenty seconds!"

"If she makes you cum will you be able to get hard again for the other half of our lesson? Fucking Jill's tight little ass?" Sandy asked him.

"Hell, yes!" he answered. "I guarantee it!"

"Then fuck away, little one!" Sandy said and gave Jill's ass-cheek a stinging slap launching her forward. She then began timing light smacks, alternating between her two cheeks, with her thrusts up her hubby's ass.

Between the sight of Reed's asshole stretched and taking the full length of her cock, the feel of the other end of the cock working her pussy and clit with each shove up his ass, his moans and groans into the pillow, and Sandy's repeated slaps on her own ass, Jill quickly growled out, "I am going to fucking cum, too!"

"Go ahead, little one!" Sandy as she scratched her fingernails into the reddened spots on both of her cheeks. "I know you'll have plenty left for your lesson!"

A moment later, as Jill wiggled her cock deep in his ass and thereby grinding it into her clit as her cunt erupted, Reed's cock shot a spurt of cum into the towel that Sandy had placed under him. It had been a long time since he had had a hands-free orgasm, and it felt wonderful! His cock throbbed two squirts on its own and he could have reached under and milked at least twice as much jism from his balls, but he knew that leaving his orgasm half finished would ensure that he would have a proper erection when it came time to fuck Jill's little asshole.

As Jill slowly extracted her fat rubber cock from Reed's ass for the final time, Sandy began unfastening the harness. "I wonder if Jay would let me do that to him," Jill said as she watched Reed's stretched-out sphincter shrink down, but not quite close up all the way. "God, that was hotter than I could ever have imagined!"

As Sandy set the dildo and harness aside, she said, "Well, you can have this as my wedding gift to both of you, and you'll be able to find out. Right now, assume the position and we'll continue our lesson."

With her reddened ass in the air, Jill rested on her forearms with her head turned and lying on a pillow. Reed sat on the bed with his dick still half hard as he watched his wife put her face between her pupil's ass cheeks and tongue her tight little virgin asshole.

Only a short while ago Jill would have been nervous as hell knowing what was going to follow Sandy's tender tongue-treatment of her pucker. Now, the anticipation made her pussy tingle.

The feeling of the cool lube as Sandy dribbled it onto her sphincter made her suck in her breath, and when Sandy played the tip of the butt-plug around her rosebud it made her quiver with eagerness. But as soon as she pushed the nose of the rubber plug into her anus, Jill involuntarily clenched her ass tightly.

Sandy gently ran her fingers over one of Jill's ass-cheeks and said, "Now, what did we just learn about relaxing?" She scraped her nails over the still-tender red spot and added, "I'd hate to have to punish you because you don't remember your lesson."

Jill chuckled, and replied, "Maybe I need that as a reminder."

Sandy brought her hand down and landed a glancing slap with her fingers at the same time she pushed the plug halfway up Jill's ass and then held it there. The quick snap of pain made Jill forget her asshole momentarily and the rubber cone slipped in easily.

Sandy rotated the lubed plug back and forth and applied a little more pressure, but Jill had clenched up again. "I see you need another reminder," she said and brought her fingers down on the same spot.