School Days Ch. 07


“This is really going to be a fun trip. Don’t you think?” Courtney rolled onto her side on the bed and put her head in her hand. She watched Erin rummage through her dresser, pulling out bras and panties and tossing them into a suitcase.

“Yeah. I still can’t believe they invited us.” Erin held up a pair of black thongs, received her friend’s nod of approval and added them to the wardrobe.

“It’s too bad Melinda couldn’t come. But I understand, with her Dad here and all,” Courtney said. “She really seemed to think we’ll get along with everyone.”

“I trust her judgment,” Erin said. “Besides, I’ve got to believe that when elementary school teachers from Ohio hit Key West in late December something wild has to happen.”

“Maybe that’s why they invited us–two Mom’s–to tag along. To keep things sane,” Courtney suggested.

“Yeah, right. Well, this Mom plans on partying.”

Erin added one last bra to the pile, although in her mind she envisioned going the entire trip without wearing one. Courtney nearly jumped off the bed before the bra entered the suitcase.

“What’s that?” she asked, pointing to the dresser drawer.

Erin looked back down, taken aback by the excited tone in Courtney’s voice. All she saw was more underwear and the tip of a shiny metal object.

“You mean this?”

Almost before Erin could get the words out, Courtney was off the bed. They reached into the drawer simultaneously.

The object came out in Courtney’s hand.

“Erin Mills,” she exclaimed. “How long have you been hiding this from me?”

Courtney held up the shimmering dildo and rotated it in her fingers.

Erin smiled nervously. “Well, you never asked.”

“All this time I’ve been trying to please you and you’ve been fucking this instead. I bet your stupid husband doesn’t know you own this, does he?”

“Of course not. And you know you’re better than any toy I can buy,” Erin said in an attempt to regain some control of the situation.

“Let’s find out.” Courtney grabbed Erin by the arm and dragged her towards the bed. Despite Erin’s protests, Courtney was able to toss her friend onto the bed next to the suitcase.

Erin landed on her back with Courtney, dildo in hand, coming down on top of her. Courtney quickly forced the other woman’s t-shirt up to her neck, exposing the full, round breasts she loved so much. Courtney rolled the dildo over Erin’s nipples to the persistent squeals of her victim. The instant growth of the bright pink skin gave away her true feelings, however.

Courtney moved down and yanked off Erin’s panties, leaving her all but naked. Erin tried to roll over, but Courtney wouldn’t allow it. She had her friend’s pussy in sight and wasn’t about to let it get away now.

Erin’s playful cries were silenced as soon as the dildo contacted her clit. The metal slowly slid up and down over Erin’s flesh, causing her to grip the bedspread and moan.

“Is this what you do?” Courtney asked quietly as she continued to rub the clit.

Erin could only nod and mumble a soft “Mmmm”.

“And then do you move it down to your pussy?”

Courtney demonstrated what she meant. The tip of the dildo disappeared between Erin’s folds of skin and reappeared a little farther down.

Another nod. More sighs.

“And then do you slide it inside your pussy?”

Courtney put the dildo at the entrance to Erin’s hole and pushed. Erin spread her legs and raised her ass off the bed a few inches.

Courtney wanted to play. She only inserted the dildo an inch or two, then withdrew it, watching Erin’s body rise and fall in anticipation of being used.

“Play with your nipples and maybe I’ll fuck you,” Courtney said.

Erin instantly put her hand on a breast and began to manipulate the nipple. Courtney smiled and reinserted the dildo. This time she let it go half way in before pulling it back out.

“Damn it, Courtney. Fuck me. Now,” Erin cried out.

Courtney was too excited to wait any longer. She rammed the dildo into Erin’s pussy until her fingers hit the moist skin. Erin nearly screamed with pleasure as the full length of the object filled her pussy. She thrust her hips forward and prepared for whatever Courtney had in mind.

The dildo easily glided in and out of the pussy, gaining more lubrication with each plunge. Courtney used her free hand to begin playing with Erin’s clit. Now the room was filled with the frantic groans of a woman about to cum. Erin mauled her breasts, the nipples aching as she rolled them between her fingers.

Courtney had made Erin cum often enough to know the signs. When the woman’s legs stretched over the end of the bed and her body rose to meet the constant piston action of the dildo, Courtney knew it was time. She pressed down hard on Erin’s clit and waited for her friend’s orgasm to start.

“Oh, Courtney. Yes. Yes.”

Erin massaged both breasts and began fucking the dildo as if she hadn’t had sex in months. Her body shook each time Courtney shoved the thick toy into her and between her legs giresun escort Erin felt the familiar spasms of a long, long orgasm.

“C’mon, babe. Cum for me,” Courtney urged her.

Erin’s body flailed on the bed for over a minute as the orgasm raged on. It wasn’t until Erin was nearly limp that Courtney let go of the dildo, still buried deep in Erin’s pussy. She watched the woman squeeze her pussy tight around the toy one last time, then pull it out herself.

“Oh my God. Take that with us,” Erin said.

Courtney quickly tossed the still-wet toy into the suitcase and leaned up to kiss her friend.

When Erin was able to move again, they reconvened in the kitchen. They went over the list of people taking the trip to Key West while sipping coffee.

Tim Heller was a 35 year old math teacher who was married, but well-known for not limiting his dating habits because of it. Melinda had warned her friends that the man was an octopus around women, but was actually too much fun at parties to ignore.

Cheryl Martinsek was the one person Melinda specifically mentioned by name for Erin and Courtney to keep an eye on. A 29 year old first grade teacher with beautiful short blonde hair and a body to die for, Melinda suspected her of leaning towards women but she had no proof. Cheryl was single and seemed comfortable around anybody. Erin and Courtney agreed she might be fun to get to know better.

Paul McFadden they already knew from their dealings with the kids’ school. He was probably the best looking man either woman had ever seen and was clearly the most eligible bachelor at the school, if not the city. At least that’s how Erin and Courtney felt and he was one of the main reasons they agreed so quickly to take the trip. He appeared to be around forty and rumor had it he was single only for the purpose of having as many women as he could. Erin and Courtney wanted to get in line.

If there was a surprise among the attendees it would have been Lynne Ferguson. Neither woman expected the thirty five year old, straight-laced, quiet teacher to even consider a trip to Key West. While very attractive and apparently happily married, she never sought out friends for after-school partying or weekend get-togethers. Erin and Courtney surmised they might go the entire trip and never see or hear from Lynne after she got to her room.

That was the group, for better or worse. Erin and Courtney knew one thing, if nothing else: they would have a good time. And the toy would go with them.

They had heard plenty of stories from friends and family about Duval Street in Key West. So it was almost with awe that, after arriving at their hotel in the Florida city, Erin and Courtney took the short walk down to the famous avenue. The group had arranged to meet back up for dinner, but for now everyone was on their own to explore, shop or get into whatever trouble they could.

A large cruise ship could be seen not far away, so the mid-afternoon crowd on the street didn’t surprise the two women. Music streamed out of a large, open air bar on the corner. Many people were taking advantage of the seventy five degree weather by sitting at outside tables. The dress was casual, to say the least, and the women were not out of place in their shorts and t-shirts.

They agreed to save their drinking until the nighttime and continued down the street. They passed boutiques, artists’ shops and tourist traps of various types. And they declined an invitation to have their pictures taken with a large boa constrictor draped over their shoulders.

“Now, if he had suggested putting the thing between my legs I might have listened to him,” Erin said.

Courtney was still laughing when they saw Lynne’s familiar face in the crowd. She was stopped in front of a tattoo parlor peering into the front window display.

“Go ahead. Get one,” Courtney said as the women approached.

Lynne turned as if caught trying to steal something. “Oh, hi. No. I’m not into this kind of thing.”

“You seemed to be awfully interested for not being into it,” Erin said.

Lynne smiled. “Some of these are SO strange. Why would anybody want that on their body?”

Courtney pointed to the back of the display. “Look at that dolphin. Isn’t that pretty.”

All three women looked at the light blue shades of the dolphin in mid-air, ready to re-enter the water. “Yeah. That one’s OK,” Lynne admitted.

“Then get it,” Erin said in her most matter-of-fact tone.

“Oh, no. I’d never…I mean…”

“C’mon. Get it where nobody but you would see it. Who would know?” Courtney said.

Lynne laughed nervously. “That could be just about anywhere.”

Erin and Courtney did have to laugh at her answer, but they were getting into the selling job now.

“Hey. Fifty bucks. How can you go wrong?” Courtney asked.

“Yeah. C’mon.” Erin grabbed Lynne by the arm and the women began to go inside. Lynne protested the entire way but found herself inside the shop along with her traveling buddies.

Courtney gümüşhane escort did the talking for the group, explaining to the owner what Lynne “wanted”. When they couldn’t talk him down from the fifty dollar cost, Erin and Courtney offered to split the cost with Lynne if she just got it done. They were somewhat surprised to see Lynne consider the offer and more than a little shocked when she suddenly said, “Sure.”

The owner escorted them back to a small room and asked Lynne where she wanted the dolphin.

“I think here.” She pointed to a spot well below the top of her shorts, on the right side of her waist. “Maybe just at the top of my swim suit.”

“OK,” the man said. “This is a lot easier with your shorts off.” It was clear from his tone that he was leaving it totally up to Lynne.

Erin had already convinced herself that, if it was her, she’d gladly take off her shorts for the young artist. There was something about his rough, unkempt look that attracted all three women even though they didn’t know it collectively.

“Sure,” Lynne answered, kicking off her sandals and pulling down her shorts. She wore a pair of blue panties that were brief, but not quite thongs. Her body was even more striking without the shorts that it was with them on. Her tiny waist, shapely hips and long legs made everyone in the room take a second and third look. Only Courtney was in a position to see most of Lynne’s ass and she could hardly take her eyes off of it.

“OK. Sit down and we’ll tilt the chair back. Is that OK?” the man asked.

“Yep.” Lynne slid into the dentist-like chair and clung to the arms as it reclined. This scene was almost too much for her friends, who looked at each other and exchanged knowing, lustful glances.

“Show me where you want it,” the shop’s owner directed.

Lynne looked down, pushed the waistband of her panties a little lower and placed her finger just inches from her clit. “Here.”

Erin and Courtney both wondered if they, as sexually open as they were, could have done the same thing without being half drunk. Maybe Lynne already was and they didn’t know it…or she was braver than they thought.

Even under the bright lights of the artists’ work area Lynne’s skin showed no imperfections. As the man leaned down and readied his tattoo machine, Erin and Courtney had to marvel at how smooth and silky Lynne’s skin was.

A moment later the curved body of a blue dolphin was appearing on top of the faint tan line on Lynne’s waist. If the line was any indication, the dolphin would appear to be jumping out of her swimsuit.

The man’s hands, by necessity, were sometimes on the edge of Lynne’s pussy. He pulled down on her panties with one hand while applying the tattoo with the other. The woman’s sleek legs were slightly separated, motionless during the entire procedure.

“Does it hurt, Lynne?” Erin asked.

“Not really. Just a little. Like pin pricks.”

The man used a white cloth to wipe away at the tattoo as he progressed. He was working on the animal’s tail and just a hint of light brown hair sneaked out from under the woman’s panties near where he worked. He was almost done, it appeared to the onlookers.

When the full outline of a graceful dolphin was etched into the customer’s skin, the man put down his machine, took the cloth and wiped the entire tattoo one last time. However, before pulling away from Lynne he looked up at the other two women and winked.

Neither Erin nor Courtney knew what he meant until they saw his hand and the cloth slide inside Lynne’s panties. The woman’s legs twitched at first, then actually opened a few inches wider.

“Ahhh,” Lynne sighed approvingly. She made no effort to stop him.

“Does it hurt now?” he asked.

“Not at all.”

He tossed the cloth aside and quickly returned his hand to Lynne’s clit. Erin and Courtney watched his fingers maneuver under the material of her panties. Once again, Lynne spread her legs a little wider. The man now had easy access to every inch of her pussy.

His fingers slid down and found the moist area between the lips surrounding the entrance to her pussy. A little lower and he was able to put just the tip of one finger inside her. Lynne moaned.

Pushing the panties down with the top of his hand, the man inserted most of one finger inside his customer. He felt the warm wetness and rubbed the inside of her pussy. Lynne lifted her body to meet his hand.

This encouragement led the man to return to her clit and begin a more earnest stroking of the engorged flesh. He found the nub and massaged it with long, smooth strokes.

Lynne realized she was going to allow him make her cum, if that was his desire. So she pulled up her t-shirt and took one of her bare breasts in her hand. She played with the nipple while everyone else in the room looked on. Erin and Courtney desperately wanted to take the smallish breasts in their mouths, but decided not to disrupt the unbelievable scene.

It wasn’t long hakkari escort before Lynne announced she was about to cum. The artist continued his steady rubbing, occasionally inserting a finger or two into her pussy. A long, loud groan declared the start of Lynne’s orgasm.

She frantically fucked the owner’s fingers when they were in her and accepted the stroking of her clit by raising her hips off the chair. Her breasts heaved up and down along with the rest of her body, at least whenever she wasn’t clutching at them. Lynne wanted to scream out but knew the little shop wasn’t the time or place for that. Instead, she clung to the chair and came harder the more he rubbed her clit.

When she was done, little droplets of sweat lay on her forehead. She used her shirt to cover her face and wipe it off. She used the few seconds of quiet to compose herself again.

She lowered the shirt while the artist pulled up her panties.

“Well,” Lynne sighed. “That wasn’t what I was expecting it to feel like.”

“Some day you’ll want another on the other side?” the owner asked.

“You can count on it.” Lynne was stepping out of the chair and reaching for her shorts. Everyone watched as she put them on, covering the beautiful dolphin in the process. “I think we owe you.”

“Fifty dollars,” the man said.

“Plus your tip.” At the same time she said it, Lynne’s hand landed on his crotch. As she suspected, his cock was still a little hard from his making her cum. She gripped it for a second, then quickly unbuttoned his shorts and pulled down the zipper. The shorts fell to the floor and the outline of his bulging cock was plainly visible inside his tight briefs.

“It’s your turn to sit down,” Lynne said.

The women watched as the man reclined into the chair. Lynne ran her hand up the length of his cock, then pulled off his underpants. Courtney and Erin stared at the thick shaft as Lynne threw aside his briefs. They both wanted to have it, but understood it was Lynne’s right to make the first move.

It didn’t take her long to lean over and take the cock in the palm of her hand. It grew steadily harder as she massaged it and soon she was gripping a fully erect penis. She licked the tip.

“Come on, girls. Help me,” Lynne said to her two friends.

Courtney quickly positioned herself opposite Lynne. That left little room for Erin and she chose to move up towards the man’s head. At the same time that Courtney and Lynne began to jointly lick and suck his cock, Erin pulled up her shirt and hung her ample breasts over the man’s face.

He eagerly reached for one of Erin’s breasts and guided the nipple inside his mouth. His lips closed around the soft, warm skin and he started to suck on the breast. Erin closed her eyes, concentrating on the incredible feeling of the man’s tongue flicking back and forth across her nipple.

Courtney and Lynne both licked his cock, taking turns putting it deep into their mouths. Shiny precum appeared at the tip and the women’s tongues lapped at it enthusiastically.

Several minutes went by with Erin eventually taking off her top and Courtney rubbing the tattoo artist’s cock against her breasts. When his actions indicated he was about to cum, Courtney and Lynne went back to licking his cock from end to end. Then, with one of Erin’s breasts in his mouth, he began to cum.

Lynne was the first to get a blast of the man’s cum on her face, but Courtney couldn’t avoid the sprays of cum that came out of the throbbing cock. Lynne finally shoved it between her lips and took the rest down her throat while Courtney licked away. Erin nearly screamed with pleasure as the man bit down on her breasts during the long orgasm.

When it was over, the women found clean cloths to wipe off the cum that had splashed onto them. Fifty dollars was handed over to the tired, but satisfied, owner and the women walked out of the shop reliving the experience all the way back to the hotel.

Inside Courtney and Erin’s room, the message light flashed on their phone. Courtney listened to the recording.

“It’s Paul,” she announced to her roommate with a big smile. She listened some more.

“We’re meeting in the lobby at seven for dinner.”

“Good,” Erin said. “I can’t wait to see who leaves with who after that.”

“Isn’t that whom? Anyway, who are YOU leaving with?” Courtney asked, flopping down on the bed.

“Whomever asks first.” Erin flashed her friend a fiendish smile.

“I want all the details,” Courtney demanded.

“Oh, I imagine you’ll be there with me.”

The women rested for a while before showering and getting dressed. Erin decided this may be the best opportunity to wear her colorful sun dress with the spaghetti straps. The dress’ plunging neckline was sure to reveal liberal amounts of her braless chest. Meanwhile, bikini panties awaited anyone choosing to remove the very removable garment.

Courtney went with the more traditional jeans (tight) and tank top (tight), hoping not to come across as too touristy. Her goal was to come across as available and willing, especially to the gorgeous Paul McFadden.

The small group formed in the lobby, Cheryl being the last to arrive. Paul informed them that he had made reservations at a nearby seafood restaurant and they marched out into the warm evening air, following Paul’s lead.

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