Sophie Bennett and her roommate, Dolly Duncan, worked for a small local magazine in New York City. Their boss, Mr. Black, had been disciplining their tardiness and other misdeeds with brutal spankings with his belt. While Sophie enjoyed spanking very much, it was all new to Dolly. However, she discovered that she not only liked being spanked but that it made her pussy feel hot and needy.
So much so that she begged Mr. Black to fuck her after a particularly harsh spanking session. To Dolly’s delight, he agreed. But then he’d surprised her (and Sophie) by insisting that he fuck her ass.
“No, please, Mr. Black,” Dolly cried. “I’ve never had anal sex before. I really wanted you in my pussy. It’s fine, you don’t need to fuck me.”
“Oh, but I do, you little cock tease!” Mr. Black insisted. “You don’t get to beg me to fuck you and then turn me down. I’m gonna have your ass.”
“Fuck my ass instead,” Sophie blurted out. “I’ve had anal sex before. Give Dolly a break. She didn’t know you wouldn’t fuck her pussy. Take my ass instead of hers.”
Mr. Black contemplated Sophie’s offer. “I don’t know, the idea of fucking a virgin ass is quite tempting,” he said. “But if you’re willing to take this thick cock up your ass for me in her place, I guess that is acceptable.”
Dolly breathed a sigh of relief and shot Sophie a grateful look. She should feel guilty, but she was so relieved.
“But you’re gonna stay and watch, Dolly, so you know what to expect the next time you’re late. I’m done just spanking the two of you. You both enjoy it way too much. From now on, when you displease me, you’ll get my cock in your ass!” Mr. Black insisted.
Dolly’s eyes flew open wide. She would need to get her act together or risk having to give her virgin ass to her boss.
“Oh, and I want you to play with your pussy, Dolly, while you watch me hammer into Sophie’s sexy little ass,” he added.
“Yes, sir,” Dolly said as she reached between her legs and started fingering her sopping wet hole.
“Now, Sophie, bend over. I need to spank you some more and make those ass cheeks even redder before I slide inside your back door,” he said wickedly.
Sophie grinned. She was hoping that he would spank her more before fucking her, and he didn’t disappoint her.
He took his belt in hand and let the leather bite into her tender flesh.
Smack! Smack! Smack!
“You like that, don’t you, slut?” Mr. Black asked as he spanked her harshly while his cock became as hard as a rock. “You love being spanked, and I will bet you love having your ass fucked, too, don’t you, you naughty little whore!”
“Yes, sir!” Sophie blurted out. “Yes, I love being spanked and yes, I want your cock in my ass.”
Smack! Smack! Smack!
Dolly felt herself get wetter and felt the need to rub her clit. She couldn’t believe how hot it was making her as she watched her boss spank Sophie and talk so dirty to her. It embarrassed her to know that she wanted very much to see his cock plow into Sophie’s ass!
Smack! Smack! Smack!
Sophie moaned as her pussy started to drip.
Mr. Black saw how wet Dolly was too and said, “Well look at how juicy that pussy is!” Then he dipped two fingers into her to get them all wet and used her juices as lube on Sophie’s ass.
Sophie moaned again as Mr. Black worked Dolly’s nectar around her tight little rosebud. He slipped his thumb in her ass and heard her gasp.
“Yes, just imagine how much better that will feel when it’s my cock, you little red-haired vixen!” he said through gritted teeth. He had played around long enough, his shaft needed attention.
Smack! Smack! Smack!
“Suck my cock and get it wet for your slutty friend’s ass,” he said to Dolly. Dolly simply nodded and opened her mouth, and took her boss’s thick, hard rod in to get it ready for Sophie.
As she sucked his dick, he continued to spank Sophie, whose ass was now a bright and angry color red.
He yanked himself out of Dolly’s mouth and pressed the head of his dick against her puckered hole.
“Dolly, watch closely, this could be you next if you don’t behave!” he said as he thrust himself deep into Sophie’s ass.
“Oh, fuck!” Sophie cried out in a combination of pleasure and pain. She’d been fucked in the ass before, but never by a monster this size.
“Oh, fuck, girl, your ass is so tight!” Mr. Black shouted. He grabbed onto Sophie’s hips and started working himself in and out of her as he felt his member gripped as though it were caught in a vise.
He watched as Dolly started rubbing her pussy again. “You’re a little slut, Dolly, getting off on watching your friend get sodomized good and hard.”
He grabbed the belt from off the bed and swatted Dolly’s bare mound a few times while he continued to pump into Sophie.
Smack! Smack! Smack!
“Oh fuck, sir! I want to be next. I’ve changed my mind! I want your cock in my ass too!” Dolly cried out as she made herself cum.
“A couple of anal sluts is what you girls are!” he said gruffly as he put the belt down and started hammering into Sophie’s ass.
“Oh, God! Oh, fuck! Oh, my God, yes! Fuck my ass hard Mr. Black!” Sophie screamed. “Fuck me like you own my ass. Like I’m your personal anal slut, sir! Please, God! Oh, fuck, I’m cumming!”
Dolly was writhing on the bed next to them as her own orgasm had her screaming as well, “Oh, fuck! I want to be next!”
Hearing these two women talk like such decadent sluts, combined with the tightness of Sophie’s ass, had Mr. Black unable to hold back anymore. He grabbed Sophie’s tits and squeezed hard while he emptied his seed deep in her dark cavern.
He pulled out of Sophie and put his cock in Dolly’s face, “Suck it, you little whore. Suck me hard again so I can take your ass too.”
“I don’t think I can really take it in my ass, sir, I was just so turned on watching you fuck Sophie’s ass,” Dolly protested.
“You’re going to learn to not be a cock tease, Dolly,” Mr. Black said. “Open up that pretty little mouth and get sucking.”
Just then, the phone rang. Mr. Black contemplated letting it go to voicemail, but he was afraid it might be someone wanting to advertise, and he could hardly afford to lose a potential client.
“Saved by the bell, missy!” he said, laughing wickedly. “But if you’re late tomorrow, your ass is mine!”
He left the girls to clean up while he wiped off his cock and answered the phone.
“Dolly, you can’t keep teasing him like that,” Sophie said. “He’s not kidding around.”
“How bad did it hurt?” Dolly asked curiously.
“His cock is really fuckin’ big!” Sophie admitted. “But after he got going and I could relax a bit, I have to say that it was the best ass fucking I’ve ever had.”
Dolly blushed, “I want that, but I don’t know if I could handle a dick that size in my butt.”
“If you want, we could practice with a dildo,” Sophie suggested.
“Really? You’d do that for me? Help me get used to a dick in my ass so I could let Mr. Black fuck it?” Dolly asked.
“Sure, I’d be happy too. Just one condition. I get to taste that pussy of yours while we practice,” Sophie said suggestively.
Dolly blushed again, “Can I taste yours too?”
Sophie laughed and nodded, “We can start tonight and practice all weekend, that way you’ll be ready for that thick meat to pump into your tight little anus.”
Dolly shivered, but she was so happy that Sophie agreed to help her out.
That night, after dinner, Sophie told Dolly to go into her nightstand drawer and pick out whichever dildo she wanted to try in her ass.
Dolly looked appalled, “You keep a whole drawer full of dildos next to your bed?”
“Where else would I keep them?” Sophie asked.
“Are they, um, clean?” Dolly asked.
“No, I just fuck my cunt with them and throw them back in the drawer,” Sophie said rolling her eyes.
“Oh!” Dolly exclaimed.
“Oh, come on! Really? I was kidding! Of course, I wash them after each use. I’m not gross, I just like to cum a lot!” Sophie chided.
“Oh, well, of course,” Dolly said, feeling stupid. “I’ve just never seen this many dildos all in one place before.”
“That’s just the top drawer,” Sophie teased. “You should see what’s in the bottom drawer!”
Dolly’s eyes got big, so Sophie said, “Come on, already, pick one.”
Dolly picked two, actually. One reasonably sized, and the other one closer to Mr. Black’s girth.
“Smart thinking,” Sophie said. “We’ll start with my fingers, move on to Mr. Relationship Dick, then wind up with Mr. Oh My Fucking God.”
“You name your dildos?” Dolly asked.
Sophie shrugged, “Yeah, doesn’t everyone?”
Dolly undressed and got on Sophie’s bed, waiting for directions. Sophie undressed as well and tried hard to remember that, while they’d agreed to taste each other, the prime directive was helping Dolly practice taking a cock in her ass.
“I’ll go first,” she said. “Lie back and open your legs for me, Dolly. Let’s get you good and worked up so you are begging for me to stick a finger in your ass.”
Dolly didn’t argue and within minutes found herself moaning as Sophie did magical things with her tongue. Soon, she felt a finger dipping in and out of her pussy, collecting juices, and rubbing them on her little tight hole. Then, just the tip of her finger invaded Dolly’s ass.
“Oh, my God, Sophie!” Dolly cried out. “That feels so good!”
“Beg me to slide the whole finger in you, Dolly,” Sophie taunted. “Beg me to fuck your little ass!”
Sophie continued her onslaught of Dolly’s clit and labia with her talented tongue. Dolly bucked and moaned and, right before she came, she begged for Sophie to stick her finger in all the way.
Sophie continued to eat Dolly’s juicy pussy and finger-fuck her asshole. Dolly came hard and begged for Sophie to stop and let her catch her breath.
“Mmmm, you taste delicious, Dolly. Take your time, catch your breath. We can be done for tonight if you want,” Sophie suggested.
“I’d like to taste your pussy still if you don’t mind,” Dolly said shyly.
“Of course, but we can do that tomorrow,” Sophie offered.
“Yes, that would be great,” Dolly agreed. She was so grateful that Sophie could see she was feeling awkward. “Um, thanks for making me cum so hard. Are you sure you can wait till tomorrow?”
“Yes, no worries. We can play after breakfast if you’d like,” Sophie said.
“Thanks! You’re the best roommate ever!” Dolly said as she hugged Sophie.
When she got into bed, Sophie nearly took one of those toys from her drawer but decided to wait until tomorrow’s playtime with Dolly. Leaving herself just a little frustrated might help ensure an orgasm since Dolly had never gone down on a woman before.
Sophie smiled as she drifted off to sleep. She was looking forward to helping broaden Dolly’s sexual horizons.
The next morning, Sophie woke up to the smell of waffles. It made her tummy growl. She went out to the kitchen and saw Dolly making breakfast.
“What’s the special occasion?” Sophie asked.
“I just thought it would be nice to have something fun for breakfast,” Dolly said grinning.
Sophie giggled, “I’ve been offered dinner in exchange for sex, but this is the first time anyone has fed me breakfast for it.”
Dolly blushed, “I’m so out of my league here, and I am nervous. When I’m nervous I like to cook.”
Sophie smiled, “Well, who am I to argue? I love waffles!”
The girls enjoyed breakfast and innuendos, then it was time to do the dishes. When Dolly bent over to load the plates in the dishwasher, Sophie gave her ass a playful slap.
Dolly moaned, “Oh, goodness, Sophie! Will you spank me before we try the dildo in my ass?”
“I’d be happy too! But I hope you didn’t fill up too much on waffles, because you promised to eat my pussy this morning, remember?” Sophie grinned.
“I’m just worried that I won’t do it right,” Dolly admitted.
“Wait here,” Sophie said.
She came back in a moment with her paddle. Then she said, “Come into the living room, I am going to spank your little ass until you are begging me to stop and let you eat my cunt.”
Dolly’s eyes widened, but she found herself in the living room, slipping off her panties and bending over the couch to offer her ass to Sophie.
Sophie began with gentle spanks and worked up to more vigorous paddling.
Smack! Smack! Smack!
Dolly moaned loudly.
“If I didn’t know better, I’d say someone is becoming addicted to spanking,” Sophie taunted as she continued to paddle Dolly’s ass.
Smack! Smack! Smack!
“Oh, God, it feels so good!” Dolly cried out.
“I told you this would happen. The more you get spanked, the more you crave it,” Sophie said as she continued to paddle Dolly’s adorable little ass.
Smack! Smack! Smack!
“Oh, fuck, please Sophie, let me eat your pussy!” Dolly cried out.
“I’m sorry, what was that? I think you need to say it louder,” Sophie teased.
“Please! I need to eat your pussy!” Dolly screamed.
Sophie set the paddle down and took Dolly by the hand into her bedroom. They got on the bed and Sophie spread her legs.
“Just lick and suck and you can’t go wrong,” Sophie urged. “I’m so fuckin’ horny from spanking you, you should have no trouble making me cum.”
Dolly was nervous, but Sophie’s words made her feel more confident. She gingerly flicked Sophie’s clit with her tongue and was rewarded with a sensual moan.
“Feels fabulous, Dolly, just keep doing…oh yeah, that’s it…fuck yeah!” Sophie encouraged. “Jeez, girl, you’re a natural!”
Dolly was too engrossed in what she was doing to answer. But knowing she was making Sophie feel good was really exciting.
“Yes, oh fuck, Dolly, put your fingers in me!” Sophie begged.
Dolly slid two fingers into Sophie as she continued to suck her clit. Sophie bucked and moaned, then she arched her back and gushed into Dolly’s mouth.
Dolly was pleasantly surprised that she found Sophie’s juices very tasty. She was very proud of herself for making her friend cum so hard.
After Sophie caught her breath, she looked mischievously at Dolly and said, “Okay, now it’s time to work the Mr. Just Enough dildo in your ass, then we can try Mr. Relationship dick, and eventually graduate to Mr. Oh My Fucking God.”
Dolly giggled, but within moments she was moaning instead. Sophie had lubed up her tight little asshole and started working in a relatively slim dildo.
“Mmm, that feels amazing!” Dolly moaned.
“Good, now let’s try the next one. You finger your wet little cunt while I work the mid-sized dildo into your slutty ass,” Sophie said.
Dolly was so turned on that, even though it hurt at first, eventually, she couldn’t help but beg for more. “Oh, God, my ass is so filled up! More, Sophie, I want more!”
Sophie continued to fuck Dolly’s puckered hole until Dolly screamed, “Oh fuck, I think I’m gonna cum!”
“Hold off, Dolly, don’t let yourself cum! I want you to be completely aroused and needy when this big dildo goes into your tight little butt. Your excitement will make you want this cock in your ass even more,” Sophie explained.
She grabbed the lube again and made sure Dolly’s ass was good and ready for the giant-sized dildo. She decided to tease Dolly a bit by giving her rosy bottom a few playful slaps.
“God, Sophie, you’re killing me here! I need that giant dildo in my ass!” Dolly cried out.
“Here,” Sophie said handing her a small vibrator. “Tease your clit while I pull out Mr. Average and slide in Mr. Huge!”
Moments later, after the dildo exchange had been made, Dolly was bucking and screaming.
“Yes! Fuck! Oh, God!” she yelled as her orgasm hit her like a ton of bricks. “Holy fuck!”
Sophie grinned and said, “Well, my friend, I think you are ready.”
Dolly panted in agreement. She was exhausted, and it felt so good!
After the girls showered, they came back together in the living room. Dolly wasn’t sure what to say at that point. Did having sex make them girlfriends? Or was this just for fun?
Sophie sensed something was up with Dolly, “Hey, are you okay? I hope that wasn’t too intense for you.”
Dolly smiled, “Oh, no! I loved every minute of it!”
“Good!” Sophie acknowledged.
“Maybe next time we can enjoy something more sensual?” Dolly asked, testing the waters.
Sophie was taken aback, “Dolly, are you saying you’d like to keep having sex with me?”
Dolly wasn’t sure whether to admit it or not, but she found Sophie so sexy. Still, she was afraid to be vulnerable, “Well, yes, but it’s okay if you don’t want to.”
Sophie sat down next to Dolly and kissed her lips softly, “I would like that very much! If I’m being honest, I’d like to see where this goes between us. Not just as fuck buddies, although I’d settle for that if that’s all you want to give, but as a couple.”
Dolly grinned, “Are you asking me to be your girlfriend, Sophie?”
“I guess I am, Dolly,” she answered.
“Then yes! But if it doesn’t work out, I don’t want to lose you as a friend or a roommate,” Dolly said biting her bottom lip.
“We’ll take it slow. The dating part, of course. I don’t think I could slow down the sex with you if I tried!” Sophie admitted.
Dolly kissed Sophie back, “I never realized I liked women before. But this feels really good, Sophie!”
Sunday, after they did their assigned cleaning chores, they plopped on the couch to watch some TV. But they ended up more interested in each other than anything on television. They took turns licking and sucking each other to many orgasms that afternoon, and they practiced on Dolly with the giant dildo one more time.
Monday morning came, and the girls toyed with being late, but they decided not to provoke Mr. Black quite so early in the day.
However, after lunch, they were late coming in because the elevator was crowded, and they decided to take the stairs.
“Well, here I thought we’d have a day when I didn’t need to discipline the two of you. Looks like I’m going to have to spank you and make you my anal sluts this afternoon after all,” Mr. Black said sternly.
The girls looked at each other and decided not to protest. They simply went into the back room, removed their panties, and got on the bed to wait for their punishment.
“I got a new toy over the weekend,” Mr. Black grinned wickedly. “Meet my new rubber paddle. It packs quite a punch, according to my wife.”
“You spank your wife?” Dolly asked incredulously.
“Oh, yes,” Mr. Black answered. “At least once a week, sometimes more if she’s sassy.”
“Does she know you spank your employees?” Dolly inquired further.
“Who do you think suggested it as a means for discipline here in the office?” he chuckled.
Sophie laughed and Mr. Black grinned.
“I’m going to start by giving you each a very hard spanking. Then your asses will feel the wrath of my cock,” Mr. Black explained. “Somehow, I have a feeling that this won’t teach you a lesson either. But who am I to complain? I have two willing anal sluts and I’m going to enjoy every thrust. Are you ready?”
“Yes, sir,” the girls said together.
Suddenly the door opened, and a stunning blond walked in.
“Oh, I have one more surprise for you, ladies. I’d like you to meet Mrs. Black, she’s going to help with the discipline today,” he grinned.
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