Training Anna

The breakup

Jenny had been at work 30 minutes before Anna came dragging in.  That in itself was unusual.  Anna occupied the cubicle next to Jenny, and she was ordinarily there well before Jenny came in at 7:30am.  Anna was normally annoyingly perky, every blonde hair on her head in place, outfit perfectly coordinated with her shoes and jewelry.  Today, umm, yeah, not so much.  Dark glasses, hair hastily swept back into a ponytail,  jeans and a wrinkled shirt.  “Damn, Anna, you must have had a hell of a party last night!”  Jenny said casually.   Anna looked down at the floor, took off her dark glasses, and started to cry.  Not fake girly tears, either.  These were honest to God heartbroken sobs.

“Aww, sweety, I’m sorry!” Jenny exclaimed, jumping up from her desk to take the still sobbing Anna into her arms.  Anna threw her arms around Jenny and buried her head in Jenny’s shoulder.  “He… he…. he dumped me!” Anna exclaimed, sobbing even harder.  “What?” Jenny said in surprise.  “You mean Mr. Right?  But … you were perfect for each other!  Heck, you were Ken and Barbie!”   Actually, Jenny had never met the guy.   But Anna was always showing off pictures from the latest adventure she and Ken had gone on.  Jenny thought his name was Josh?  But swear to God he looked just like a Ken doll.  “He said ..”  Anna tried to say through her sobs, “he said the chemistry wasn’t right!”  Jenny disentangled herself from Anna long enough to grab a couple kleenex off of her desk and hand them to her.   “I can’t believe it!” Jenny told her. “Did this come out of the blue?  Had you been arguing?”

“No!” Anna exclaimed.  “Everything was fine!”  She paused.  “Well,” she admitted, “the sex had gotten a little … routine lately.  I read in Cosmo that was normal after a year and a half.  Cosmo had this list of 10 things to spice it up.”  Anna paused again.  “Oh my God,” she sobbed, “he thinks I’m a slut!  A whore!”  “What?!! No, Anna, you’re the opposite of a slut, sweety!  You don’t even own anything low cut!  How could he possibly think that?”  Jenny asked.  

Jenny looked around and realized that she and Anna were starting to attract some stares from around the office.   “Come on, Anna, time for a girls’ conference,” she told her, leading her toward the ladies’ room.

“Okay,” Jenny continued, safe inside the ladies room, “so what did you suggest that was so whorish?”  Anna blew her nose into a tissue and dabbed at her eyes.  “Number 6,” Anna said quietly, “give him a blow job before he’s even fully awake.”    Jenny smiled.  “Aw, that couldn’t be it!  What kind of guy doesn’t like an early morning blow job?”  Anna frowned at the memory.  “Jason doesn’t, that’s who.”  Jason!  Crap, Jenny could never remember his name.   “Seriously?” she asked Anna.  “He didn’t like it?”  “I … ” Anna paused, blushing. Jenny and Anna were work acquaintances.  They normally didn’t talk about their sex lives.  A fact that Jenny was grateful for, actually, since Jenny’s sex life with Sir was, well, a tad bit on the kinky side.  Okay, maybe way on the kinky side.  And Anna was, well, prim, proper, and perky.  

“So what happened, Anna?  It’s okay, you won’t shock me.” Jenny reassured her.  “Well,” Anna sniffled, “I sucked on it for about, I don’t know, 5 or 10 minutes?  And then it went all soft, and he said that was plenty, thank you.  And he never mentioned it again! Is that normal, Jenny? ”  

Jenny looked perplexed.  “Well,” she said thoughtfully, “I’ve never met a guy who didn’t like getting his dick sucked.”  Anna blushed at the word “dick”.  “But,” Jenny continued, ” I’ve heard they exist.”  Jenny thought for a moment, choosing her words carefully.  “What was your sex life before that?  I guess you’d never sucked his cock before?” 

Anna shook her head no.  “He never asked me to.  Sometimes, when he’d had a few beers, he let me be on top, though.”   “And that was the kinkiest he got?” Jenny asked her.  “Uh huh,”  Anna said quietly.   Jenny shook her head in disgust.  “Anna, sweety, you’re well rid of him!  We need to find you a guy who knows how to fuck!”  Anna blushed again, more deeply than before, but her eyes brightened and she nodded her head yes.  

Girls Night Out

It was a few weeks later when Jenny invited Anna to a get together with the girls at The Outpost, a dive bar up the road from the office.  Anna wasn’t crying at her desk anymore, but she was still clearly heartbroken.  It was always a couple of rounds in that  the conversation inevitably turned to sex, and this night was no different.  “Oh my God, y’all, you are not going to believe what Kevin got me for my birthday!”  Linda told them in a slightly tipsy voice.  “A butt plug!” Linda continued, not even waiting for a response.  “Oh my God, as if I’m going to stick that big thing up my ass!”  The girls all started talking and laughing at once.  “That’s nothing!  Monica told them, “mine gave me a vibrating butt plug last year!”  More laughter erupted.  “Monica, you didn’t!” someone exclaimed in mock horror.  “I did!” Monica responded with a gleam in her eye.  “Don’t knock it till you try it!”  “Okay, okay,” Linda finally said after the laughter finally died down, “so what’s the kinkiest thing you’ve ever done?”  Jenny groaned to herself.  She always had to answer these questions carefully.  The kinkiest thing that she and Sir had ever done involved four other guys and a cane.  But this crowd was clearly not ready for that. 

“Okay, well, once,” Monica said in a conspiratorial voice, ” when Mark was a little drunk, he let me use the vibrating butt plug on him!”  “Oh my God, for real?”  “Oh how hot!” the girls shrieked.  “For his birthday,” Sharon spoke up, “Luke gets to play cops and robbers with the handcuffs.  And I’m the robber!”  More shrieks ensued.   Eyes turned to Jenny.  Clearly it was her turn next.  Jenny smiled.  “My favorite thing involves a good spanking!”  “Oh you bad girl, you!” Monica told her with mock seriousness.    The girls all laughed.  Jenny  looked at Anna, who was sitting next to her.  Anna’s eyes were wide.  Uh oh, Jenny thought. Apparently Jenny had shocked her.  Maybe bringing Anna was a mistake?  “What about you, Anna?”  Sharon asked.  “Ever do anything wild and crazy in bed?”  Uh oh, Jenny thought.  Surely the tears would erupt now.  But Anna surprised her. “Huh!” she said rolling her eyes. “My last boyfriend thought an early morning blow job was too kinky!  Next time, I’m going to find a hot Dom!  A real Christian Grey type!” she said with passion in her voice.  “Ohh, baby!”, “You go, girl!”  “Now you’re talking!”  The girls were very supportive.

As the girls gathered their stuff and started to head toward the door, Anna grabbed Jenny’s arm and held her back.  “Jenny?”  Anna said.  “Can I ask you something?”  “Sure!” Jenny said, knowing that this conversation was headed in a dangerous direction.  “Um, well, were you serious about the spanking thing?”  “Uh huh,”  Jenny said.  “Well,” Anna stammered, “I mean, I don’t want to pry.  It’s just.. well….”  “The Christian Grey thing?” Jenny asked her.  “Yes!”  Anna blurted out.  “I read the whole book in two nights, and I really really want something like that for myself!”  Jenny shook her head without thinking.  “You don’t think I should?” Anna asked with disappointment in her voice.  “Have I shocked you?” she continued timidly.  “No, no, not at all, Anna.  It’s just that, well, that book does not give you a realistic picture of what it’s really like! If you’re actually going to play like that,  if you’re going to explore that world, there’s a lot more talking involved, more ritual, and you don’t jump right into that level of play!  You build up to it over months or even years!”   Crap.  50 Shades of Grey was a sore point with Jenny, and she had just managed to out herself because of it.   “Look, sweety,” Jenny said gently, “you’re still on the rebound.  Take it slow.  Maybe chat with a few guys online!”   “Oh, I’ve already been doing that!” Anna said enthusiastically.  “I got an account on….”  Anna covered her mouth suddenly.  “This is just between us, right, Jenny?”   “Definitely, Anna,” Jenny answered her.  “Let’s keep this conversation just between the two of us.”  “Okay!”  Anna said brightly.  “Good, cause I already made an account on Fetlife!  And I’ve been chatting with all these guys, and one of them says he’d love to train me as a submissive, and he wants to meet tomorrow night!”

“What?!!” Jenny said with alarm.    “Okay, hold on a second here, Anna.  Has he asked you what your limits are?”  “Limits?”  Anna answered with confusion.  “Have you discussed a safeword, or any safety at all?”  “Oh, yeah!” Anna said with more assurance.  “He said that real submissives don’t use safewords!  That safewords are for wannabes!”    Jenny put her head in her hands.  “Did I do something wrong?” Anna asked her.  “Anna, all of that is a lie.  Every submissive has a safeword and you don’t play without one.  Every submissive has limits – hard limits are things you absolutely will not do.  Soft limits are things that you would need to think about and approach slowly before you did them.”  “Like what?” Anna asked, clearly confused.  “Okay, well, for example, ” Jenny paused a second to think.  Her hard limits involved blood play and animals.  But she didn’t want to freak Anna out completely by bringing those up.   “Anal sex is something that some submissives won’t do.  Or certain kinds of spanking, like canes and whips.”  “Oh.”  Anna thought for a moment.  “Yeah, I guess you could call anal a soft limit for me.  I’d want to work up to that.”  “Okay, see?  A good Dom will spend a lot of time beforehand talking about these things with you!  To make sure you’re on the same page!”  “Jenny?”  Anna asked, “what’s your safeword?”    Jenny smiled.  She was too far into this conversation to start denying things now.  “My safeword is mercy.”  “So, Kyle is your Dom?  How did you meet him?”   Anna asked her, filled with curiosity.

“Yes, he’s my Dom.  I met him on a dating app, OKCupid.  But Anna, we chatted for weeks before we ever played, and even then, we started out slowly.  A coffee date.  Then a movie date. Right now, you’re all excited about trying everything out.  There’s even a name for it – it’s called Sub Frenzy.  You just need to be careful, that’s all.  There are some good Doms out there, but there are some bad ones too.  Promise me you won’t meet anyone from Fetlife!”

“But Jenny!” Anna cried, “how am I supposed to meet a good Dom?”  “I’ve heard you’re supposed to try to go to a munch.  Get to know people in the local kink community.”  Anna wrinkled her nose at the thought.  “I’ll even go with you!” Jenny told her.  “I don’t do very well at meeting people I don’t know,” Anna said.  “Jenny, doesn’t your Dom know of any other Doms?  Maybe he can introduce me to someone!”  Jenny sighed. “I’m not sure.  But I’ll talk to him,” Jenny told her.

Lunch with Sir

A few days later, Jenny was having lunch with Sir after a particularly intense session.  She sat down gingerly at the table, both ass cheeks still sore from their play.  “You beat me hard this time!” she told him.  “I’m gonna have bruises!”  “I always beat you hard.  And your ass is too tough to bruise anymore, no matter how hard I beat you.  But you’re welcome,” he told her.  She smiled. “I did cum so hard!” she said.  “That’s cause you’re a pain whore,” he responded.  “Mmm,” she smiled.  “Did I tell you about the girl at work who wants to be a sub?”  she asked him.  “No!  Do tell,” he said curiously.  Jenny filled him in on her conversations with Anna.  “Hmm,” he said. “Well, first off, what kind of titties does she have?”   Jenny rolled her eyes at him.  “I’m serious, here!  I don’t know what to do!  I don’t want the girl going off with some psycho from Fetlife.  But it’s not as if I have a bunch of spare Doms in my pocket, either!”  Sir thought for a moment.  “It might be fun to break her in,” he finally said.  “Show her what it’s really like. Let her try it, see if she really likes it or not.”  Jenny looked at him suspiciously.  “That’s very…. magnanimous of you.” she said.  He smiled.  “And as long as she’s here, I could get my balls and my dick sucked at the same time.  Make the two of you snowball my cum a few times.”    Jenny smiled and shook her head. “Yeah, I knew there was something in it for you!”  She paused.  “Are you serious about this?  You really think it’s a good idea?  What if she falls in love with you?”  “We set the expectations up front,” he told her sternly.  “And,” he continued, “you help her set up her OKCupid account.  Plus, what kind of perverted whore falls in love with the guy who beats the fuck out of her every week?”  Jenny smiled brightly.  “Me!” she said happily.   He looked at her with mock sternness.  “Don’t you go getting all mushy on me, girl!”  She loved it when he called her girl.

Making plans

Jenny drove to work the next morning with a whirlwind of thoughts in her head.  She told herself that she wasn’t Anna’s keeper, that it wasn’t her job to teach her to be a submissive.  But Anna reminded Jenny of herself when she had first gotten into BDSM.  Jenny had done some stupid things herself when she first started.  There had been one Dom she’d played with once who had really scared her, a few others she never did play with who had given her the creeps.  She would feel horrible if Anna played with the wrong guy and got hurt or traumatized.   On the other hand, she didn’t know how she felt about sharing Sir with another girl.  Was she really afraid that Sir might find Anna to be a better sub than her?  But Sir had always wanted to try playing with another girl, and this did seem like a good opportunity.   Jenny sighed in frustration.  She was arriving at work already, and all she had done was to talk herself in circles.    Still not knowing what she intended to do, Jenny decided to invite Anna to lunch.

“So how’s it been going?” Jenny asked Anna as the waitress finished taking their order.  Anna sighed. “Not well,” Anna told her glumly.  “Oh no, why?” Jenny asked with concern.  “Well, first of all, you were right about Fetlife,”  Anna said.  “Oh?”  Jenny asked.  “Yeah,” Anna answered, “that guy who wanted to meet me?  As soon as I mentioned limits and safewords and meeting up in public to get to know each other, he flipped out on me, started calling me all kinds of nasty names.  I ended up having to block him!”  “Geez, what a creep!”  Jenny said sympathetically.   “And I even got the guts to go to a munch!” Anna continued glumly, “but no one even talked to me.  They were all talking to each other and they just ignored me, ”   “No way!  How rude!  I’m sure they’re not all like that!” Jenny told her.  “I don’t know, Jenny, maybe this isn’t right for me after all.  I mean, I’m getting all excited over this and I’ve never even tried it.  Maybe it won’t be as hot as I’m thinking it will be.  I wish I could just try it out, just to see what it’s like.”

“Well,” Jenny said uncertainly, “maybe there’s a way for you to do that.”  “Really?  How?” Anna asked her more brightly.  “Did your Sir know of another Dom?”   “Well, no,” Jenny replied. “But he said he wouldn’t mind doing a play session with you, just to help break you in.  That is, if you’re interested.”  “Really?!!” Anna practically shrieked.  “You’d do that for me?!”  Jenny giggled at her excitement.  “Shhhh!  The whole restaurant can hear you!”  “Oh, sorry!” Anna whispered.  “Sir has been looking for an opportunity to try adding another girl to a play session,” Jenny told her.  “There are a few things he’d like to do that take two girls.”  “Like what?” Anna asked her.  “Well,” this time it was Jenny’s turn to blush, “like sucking his dick and his balls at the same time.”  Anna’s face wrinkled with concern.  “But Jenny,” she said, “I don’t know how to do that!”  Jenny smiled reassuringly.  “Anna, that’s the best part about being a submissive!  If you don’t know how to do something, if you’re doing it wrong or you’re not doing it the way he likes? He’ll just tell you!”  “I like the sound of that!” Anna said.  

“Okay, so you’ll have to set yourself up with an account on Kik.  The three of us will talk about what you can expect, what your limits are, stuff like that, and then we’ll set a date.  And in the mean time, do you want me to help you set up a profile on OKCupid?”   “Could you?!” Anna asked.  “I tried myself, but all I’m getting is married guys calling themselves ‘Daddy Doms’.  What’s that about, anyway?”  Jenny rolled her eyes.  “That means they’re looking for an easy side-piece.  Did you use the word ‘submissive’ in  your profile?” Jenny asked her.  Anna nodded her head affirmatively.  “Yeah,” Jenny told her, “calling yourself a submissive in your profile attracts lots of creeps.  You can say things like ‘I’m looking for an assertive man’, or ‘my perfect man isn’t afraid to take charge’.  Something like that.  Call me tonight, and I’ll help you work on it.”

Play date

Jenny drove up Sir’s driveway right at 11 am, just on time.  She didn’t see Anna’s car.  The door opened for her as she approached it, and she stepped into Sir’s living room, loaded down with her toy bag, her purse, and her after-care bag.   She looked up at Sir, smiling submissively.  Jenny’s transition to full submission began the moment she stepped through the door.  Sir kissed her, then sniffed the air around her.  “Vanilla,” he said.  “I always smell like vanilla to you!” Jenny complained.  “Yep, just different kinds of vanilla,” he responded.  “Think she’ll show?” he asked.  “I think so!” Jenny responded.  “She seemed really excited about it!”  Just then they both heard the sound of car wheels on the gravel driveway.  Anna was here.

Anna was nervous as she came through the door. She looked amazing – not even recognizable as the shy, modest girl that Jenny worked with.   Her low cut tank top showed off nice C-cups that Jenny didn’t even know she had.  She had on a short, flared skirt and thigh highs that peeked out from under the skirt, finished off with a set of black fuck me pumps on her feet.  Her blonde hair went straight down  her back, and her heavily made up eyes and lips looked appropriately slutty.  

Sir stood in front of her, looking her up and down, but not touching her yet.  “Very nice,”  he said to her in his low, growly Dom voice.  “Good girl.  Now, stand there, and watch until I tell you to do differently.”  “Yes Sir,” she said meekly.  Sir turned to Jenny.  “Against the wall, whore,” he ordered her.  Sir kissed her roughly, hauling her tits out from the top of her low cut top.  He pulled each tit to his mouth, sucking and biting at the nipple, making her groan in delight. 

Sir pulled away and pointed at the floor.  “On your knees, you know the position. Anna, on your knees right next to her.”  The two women obeyed instantly.  Sir stood in front of them, looking down.  “May I take them off, please?” Jenny asked him, staring at his shorts.  “You may,” he told her.  Sir wore no underwear, and his hard cock popped out as soon as Jenny pulled the zipper down.  Her fingers fumbled on the belt before finally pulling the shorts down and off, and freeing his cock and balls for worship.

“Anna,” he instructed, “always start with the balls.  Take the left ball into your mouth and suck.”  Anna did as she was told, stroking his scrotum gently before pulling the left ball into her mouth.  “Good girl.  Now pull on it.   Harder, I’ll tell you when to stop.”  Sir groaned in pleasure as Anna pulled and sucked. “Jenny, right ball,” he ordered. Jenny moved in, her face touching Anna’s, and sucked his right ball into her mouth, pulling it hard.  “Oh, yeah,”  Sir groaned.  “Okay, enough,” he told them after a few minutes.  “Anna, you’re going to learn how to suck cock the right way,”  Sir finally said.  “Take it in your mouth.”   Anna gingerly took the tip of his cock into her mouth.  “Good girl.  Now deeper.  Long slow strokes, in and out.”   Anna bobbed her head up and down on his cock, pulling it into her mouth a few inches.  “Good girl,” he reassured her, “now deeper, and more slowly.”  Anna sucked his cock more deeply into her mouth, taking more and more in until she was gagging on it.  “That’s it, good girl!  Get that hot throat snot up  on it!”  Her eyes were watering and drool was escaping  from her mouth, but she kept at it.  “Jenny, balls,” he ordered in a low voice.  Jenny lowered her head under Anna’s and sucked his balls into her mouth, pulling them down and sucking rhythmically.  “Ohhh, fuck yeah,” Sir groaned.   After a few minutes, he told the girls to switch.  Jenny took his cock into her mouth, sucking it deeply until the head hit the back of her throat.  Anna fumbled a bit to try and fit both of his balls into her mouth, but she finally managed, her eyes widening with the effort of keeping both of his balls in her mouth.  “Oh, fuck, I could cum right now,” he said.  This time he let them suck longer, finally telling them that was enough for now.

The girls both sat back, mascara running down their faces, out of breath from the effort.  “Good girls,” he told them.  Jenny smiled in pleasure at the words and looked over at Anna.  Anna gazed up at Sir with adoring eyes.  “Okay so far?” Sir asked Anna.  She nodded her head yes and smiled up at him.  Sir stroked Anna’s hair softly.  “You’re very submissive, you know.”  Anna smiled even more brightly, whispering “thank you Sir”.    Jenny felt a twinge of jealousy at the exchange, and yet was very turned on at the same time.

“Get up, girls, it’s time for maintenance spankings,” Sir told the girls.  Anna’s eyes widened and she looked over at Jenny.  “It’s amazing, Anna!” Jenny reassured her.  “Over to the bench and bend over,” Sir ordered them. “Anna, did you bring your vibrator?”  he asked her.  Anna nodded.  “Well, get it out, you’re going to want it.”  Anna scrambled to obey .

 Jenny and Anna  bent over, side by side, with their hands on the bench.  Sir walked around behind them, pulling up their skirts and pulling their panties in to expose their ass cheeks, his hands stroking their asses softly.  He came over to Jenny’s side, groping and fondling her hanging tits.  Then he walked over to Anna’s side, stroking her tits through her tank top.  “Mmm, gonna need to let them free,” he told her, moving his hand up onto her back and undoing her bra fastener with one hand.  “Take it off,” he ordered, and Anna slipped the straps off of her arms and pulled the bra out of the front of her tank top.  “Much better,” he said, pulling her now freed tits out of the front of her top.   He fondled her tits and pulled her nipples with one hand while stroking her ass with the other.  Anna groaned in pleasure.    “Remember,” he told her softly, “you must ask permission to cum.”  “Yes Sir,” Anna whispered.  

“Okay, Jenny, start buzzing,” Sir told them.  “Anna, you watch.”   Anna watched Jenny as she put her cordless vibrator to her clit and turned it on.     Sir stood next to Jenny as she buzzed, rubbing his hard cock against her ass cheek.  “Oh oh, Sir, may I cum please?” Jenny gasped.  “Tell me when it starts, whore,” he told her.  Jenny groaned out “it’s starting!!”    Just as the orgasm reached it’s peak, Sir struck her right ass cheek hard with the paddle he had in his hand.  Jenny screamed out in pain and pleasure.  “May I have my second, please?” she whispered.  He whacked her left ass cheek as she let out another scream.  Over and over he struck her, her cries sounding more and more like an animal in heat, finally relenting when they got to the tenth stroke.   Anna watched with both fear and excitement on her face,  amazed at the way Jenny continued to groan with pleasure even after the swats had finished and the vibrator had turned off.  “How many times did you cum, whore?” he asked Jenny.  “Five,” she said in a low, dreamy voice.  

“Anna, your turn,” Sir said, walking over to Anna’s side.  “Start buzzing.”  Anna obeyed, moaning  as the vibrator pushed her toward orgasm.  Finally she asked, “Sir, may I cum please?”  “Yes you may,” he told her.  “Tell me when it starts.”  As her orgasm started he hit the paddle against her ass cheek, not as hard as he had hit Jenny, but hard enough to make a satisfying “WHACK” as the paddle hit her ass.  Anna’s eyes widened and she let out a loud moan of surprise and pleasure.  “Oh oh, Sir, I need to cum again!”  “Ask for your second,”  he reminded her.  “May I please have my second?” she asked, desperation in her voice as she tried to hold back the orgasm.  “Yes, you may, and you may cum, too,” Sir told her, the satisfaction apparent in his voice.  Her cries of pleasure got louder with each stroke of the paddle.  By the seventh stroke, she was gasping for air and barely able to stand.  “That’s enough, slut,” Sir finally told her.  Anna stood up, still quivering all over, and turned to Jenny.  Jenny took her in her arms, her hands running down Anna’s body and stroking  her now reddened ass. “Oh that was so good!,” Anna said breathlessly, “I had no idea!”  “How many times did you cum, slut?” Sir asked her.  Anna was silent for a moment.  “Ummm, three I think?” she said uncertainly.  “The last two seemed to go on forever!”  Jenny giggled.  “I told you it was amazing!”.  

After another cock and ball sucking session, Sir announced it was time for titty torture.  “Anna, you’re first this time,” he announced to the girls.  

Anna sat in the chair as Sir handed her Jenny’s vibrator with the g-spot attachment.  She inserted the curving rubber attachment into her pussy and placed her hands behind her back as Sir cuffed them and clipped her wrists together behind her back.  He placed a blindfold over her eyes.  “Best you don’t see what’s going to happen to you,” he told her.  Jenny watched from the side as Sir fondled Anna’s tits and pulled her nipples.  Anna’s tits were C cups – smaller than Jenny’s, but with nice plump nipples.  “Oh God, I need to cum!” Anna cried.  “Cum then, slut,” he told her.  As Anna started to cum, Sir picked up the paddle he had used on their asses and began hitting the tops and sides of Anna’s tits.  Anna moaned and screamed as the whacks and the orgasms tore through her body.  “Oh God yes, I need to cum again!” she cried.  Jenny had never seen Sir torture another girl’s tits and she was completely turned on.  She licked her lips and squirmed, surprised at her own urge to grab a paddle and hit the girl’s tits herself.

Sir had switched from the paddle to the cane and was lightly fluttering the cane against her nipples.  Anna’s screams increased in intensity as orgasm after orgasm wracked her body.  Finally they heard a very soft “Mercy please!” come from Anna.   Sir put the cane down and turned off the vibrator.   He stroked Anna’s hair and let her rest her head against his stomach as she breathed heavily, struggling to return to earth.  “Good girl,” he told her, “well done.”  

Jenny was next and she squirmed with excitement as she put the g spot attachment of the vibrator in her pussy.  She put the blindfold on, then moved her hands behind her back, grabbing the seat back in “honor bondage” instead of actual cuffs.   Sir switched the vibrator on high and grabbed his favorite 1/4′ lexan cane.  As the first orgasm approached, he began caning her tits, striking the tops of them over and over.  “Oh, oh, yes, my Sir,” she cried as the cane lashes intensified her orgasms.  Finally Sir put the cane down and picked up the clover clamps that he had laid out.  As Jenny continued to orgasm, he attached the clamps to the base of each of her nipples, allowing the black chain attached to the clamps to dangle between her tits.  Now as Jenny began to come again, he began to hit the chain with his cane.  With every cane stroke on the chain, the clamps tightened against her nipples.  Jenny’s moans and cries increased as the pain in her nipples intensified her orgasms.   Finally Sir began to hit her nipples with the cane, starting with a gentle flutter stroke as he had done with Anna, and increasing in force as Jenny’s orgasms drover higher and higher.  At last he decided she had had enough, and he put down the cane and turned off the vibrator.  As he took the clover clamps off of Jenny’s nipples, he looked over at Anna, who was watching in awe.  

“Wow, did you do that to me?” she said in amazement.  Sir laughed  “You got the junior varsity version, slut,” he told her.  “How do you feel?” he asked her.  “Amazing!” Anna said.  “Like a limp noodle!”  “Well don’t get too relaxed because you have one more job to do.”  “What’s that?” Anna asked nervously.  “It’s my turn!” Sir said.  

Sir sat in the chair as the girls sat on the floor in front of him.  He looked down at the girls.  “You’re gonna take turns until I say so.  Then Jenny, you’re on cock and Anna, you’re on balls until I cum.”  “Yes Sir,” the girls said in unison.  Jenny took Sir’s cock into her mouth, sucking it fully erect as Anna took his balls in her mouth.   Anna let go of his balls and came up to Sir’s cock, her lips meeting Jenny’s as their mouths surrounded the shaft of his cock.  Up and down the girls ran their lips, his cock nestled between them.  Finally, they exchanged a deep, hungry kiss as Jenny stroked his cock with her hand.  Anna took his hard cock in her mouth, working it slowly in and out as he had taught her, as Jenny sucked and pulled his balls as hard as she could.  Back and forth the girls went, worshiping his cock with their hungry mouths, until at last he groaned “now”.  Jenny took his cock in her mouth one last time, taking the head all the way to the back of her throat and pushing it up against the roof of her mouth with the back of her tongue.  She felt his cock swell even more, so hard it almost vibrated, as he groaned out his orgasm, his cum filling here mouth as she continued to slowly move her mouth up and down the shaft.   “Okay,” he finally told them, and the girls sat up, Sir’s cum still in Jenny’s mouth.  

He sat for a few moments, recovering from the strong orgasm, as the girls waited obediently.  “Now,” he told them as he sat up, “snow ball it between you a few times.”  Jenny turned to Anna and moved in for a kiss.  As the girls lips met, Jenny opened her mouth for a passionate French kiss, pushing Sir’s cum into Anna’s mouth as she did so.   Anna pulled back and opened her mouth, proudly showing Sir his cum.  Then she leaned back into Jenny, kissing her and pushing the cum back into Jenny’s mouth again.  As Anna kissed her, Jenny’s hands moved up to cup Anna’s tits, her fingers fondling Anna’s nipples.  Anna moaned in delight, her hands going to Jenny’s nipples to reciprocate the attention.  Jenny kissed Anna again, giving her back Sir’s cum as her hand moved down from Anna’s tits to her wet and swollen pussy.  Her fingers stroked Anna’s clit, circling it as it hardened, then moved into Anna’s pussy to finger fuck her.  Jenny looked up at Sir.  “May I please?” she asked him.  He knew what she wanted to do, nodding his assent. 

Jenny pushed Anna back until she was laying down, then leaned down between her legs to lick her clit with quick, flicking strokes.  Anna groans were muffled by the cum that was still in her mouth.  Finally she looked up at Sir.  “Mmmph!  Mmmph!” was all she could manage.    “You may cum,”  Sir told her.   As Anna’s orgasm finished,  Sir’s voice reached her ears.  “Snowball it one last time to Jenny,” he ordered her.  Anna sat up and kissed Jenny gently, pushing the cum back to Jenny once more.  Now Sir handed her Jenny’s Hitachi.  “Make her cum, slut.  She has to cum before she can swallow.”    

Jenny leaned back against Sir, spreading her legs for Anna.  Anna pressed the vibrator against Jenny’s pussy, spreading her pussy lips to get full contact with Jenny’s clit.  Anna pressed the power button and slowly increased the intensity.  Her free hand moved up to Jenny’s tits, pulling and twisting first one nipple, then the other.  Finally, as Jenny’s excitement increased, Anna put her fingers into Jenny’s pussy – first two fingers, then three, finger fucking her as Jenny approached orgasm. “Mmmph!  Mmmph!”  Jenny moaned, her lips still  holding Sir’s cum.  “Not yet,” Sir said wickedly.  “I’m enjoying the show too much.”  “MMMMMPH!!!!” Jenny moaned as if she was being tortured.   Pathetic noises came from her still closed mouth as her eyes begged him to release her.    Sir waited several seconds before responding as Jenny wiggled and squirmed and looked up at Sir in desperation.  “You may cum,” he finally said.  The noises increased in intensity as Jenny came hard around Anna’s fingers.  Finally Anna turned off the Hitachi and pulled her fingers out of Jenny’s pussy.  Jenny looked up at Sir, awaiting his command.  “You may swallow,” he told her.  “And then clean up your dirty pussy juice from her fingers.”  Jenny did as she was told, sucking Anna’s fingers slowly, tasting her own juice on them.  “I hope you liked it,” Jenny asked her softly.  Anna smiled dreamily.  “I had no idea it could be like this,” Anna told her.

It was a week later when Jenny met Sir for their next playdate.  “Guess what, guess what?” she blurted out as soon as she walked in the door.  “What, what?” he asked her with amusement in his voice.  “Anna has a coffee date with a Dom!”  Jenny said.  “He’s only had one sub, but he sounds really nice and hot and perfect for her!”  The words all came out in a rush.  Sir smiled.  “And are you happy for Anna, or are you happy that you don’t have to share me anymore?” he asked her.  Jenny paused, considering her answer.  “Well… maybe a little of both,” she said honestly.  “I really liked playing with another girl, but I like having you all to myself, too.”  “Good,” he answered.  “Cause taking care of two whores is a lot of work.”

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s