Weekend With Anderson

Chapter 3
Sherry heard Kevin’s moans faintly from upstairs and smiled to herself, “He must be thinking he is the luckiest guy in town tonight and is going to get more pussy than he can handle!” A giggle slipped out and she thought as she laid some leather straps with strong chrome buckles on a large thick table, “Oh yeah he’s going to get more than he can handle alright…just not quite like he’s thinking!” She glanced around the room and satisfied all was prepared according to Helen’s directions, she turned her attention to herself and slipped out of her clothes and into something a little more “Comfortable.”
Helen let Kevin’s cock slip from her lips with a loud slurping sound. She looked up at him and saw he was just where she wanted him…Horny as hell and willing to agree to almost anything just to be allowed to cum in her mouth.
“Does that feel good Kevin? Do you like me sucking your hard cock like that?”
“Oh hell yes! You’re very good at it!” Kevin said forgetting himself momentarily.
She pulled hard on his cock shocking him…”What!?” She demanded.
“Oh…Yes Mistress…Very Much…Thank You Mistress.” He replied apologetically.
Helen looked up at Kevin, less than amused, and continued expertly stroking and sucking his cock. She loved it when he would come close to cumming and he shivered and his knees would fail. She always stopped just at the last moment and then start back at it keeping him on the edge of orgasm for another few minutes…teasing him practically into a frenzy. Then much to Kevin’s dismay…Helen suddenly stopped.
“Alright that’s enough…Now come here.” She directed standing and leading him over to one of the over stuffed leather chairs in the Study. She slipped out her bikini bottoms and sat in the chair lifting a leg up over cushioned arm. “Alright let me see how well you can eat pussy! Come-on, don’t be shy” She said grabbing the back of his head as he was lowering himself into position, “Yeah eat my Hot Pussy!”
She pulled his face roughly into her and ground her hips forward. She wasn’t trying to be a total Bitch about it, but he needed to realize she was the boss…not only at work, but here as well…and he would learn too, just as Sherry had.
Pulling her hair back into a loose ponytail, Sherry looked into a dark metal framed mirror and was pleased with what she saw. She was excited, not only because her lean toned body looked ‘Hot’ in her leather outfit, but Mistress Helen was going to let her play a new role…not just the submissive…but a more aggressive one, at least towards Kevin. Oh this is going to be so much fun she thought…she had been looking forward to it all week after being told of the plan to seduce Kevin. She pulled on a pair of medium heeled black boots that came up to her lower thigh and spun around and headed upstairs to inform Mistress all was ready.
As she neared the Study, Sherry could hear Helen moaning and encouraging Kevin to do one thing or another. She turned the corner and saw Kevin with his face buried between her legs…his head bobbing as he licked her. She smiled to herself knowing both just how good he was with his tongue and how exciting and fulfilling it was to give head to the Mistress…making her kick and scream in orgasm. Sherry just stood patiently, watching unobserved, growing even hornier as the show unfolded before her.
“Oh Yeah! Yeah! Eat it up! Just like that! Don’t Stop! DON’T STOP!!!” Helen moaned as she arched her back and pushed her clit harder against Kevin’s tongue as an intense orgasm swarmed over her! She came hard and Kevin lapped it all up…neither of them giving even the slightest indication that they were aware that Sherry was rubbing her clit through her black leather panties watching them.
“Oh God, now that was some good pussy eating!” Helen panted backing her sensitive clit way from Kevin’s still attacking tongue “Ok…that’ll do…for now. Oh Sherry, How are things coming along?”
“All finished Mistress” Sherry replied, “I brought the collars and leashes up.”
“Good, put them on our little sex slave here” She said pleasantly, smiling reassuringly at Kevin “You’re not scared of a little bondage are you Kevin?
“No not at all, Mistress” Kevin remembered to say thinking that it actually sounded like fun…he had always wanted to play around with it and the thought of actually do so excited him.
He was still on all 4’s and Sherry knelt beside him and put a thick leather collar with a large buckle and a “D-ring” around his neck. She then attached a leash and handed it to Helen.
“Here Mistress” She said starting to move back behind him as she accepted the leash, “Shall I put on the cock and ball harness as well?”
“Yes Dear, of course” Helen said, “We want Kevin to experience ‘all the fun things’ don’t we?”
“Yes Mistress…we do!” Sherry giggled.
Kevin showed a little concern when Sherry reached between his legs and attached a cock and ball harness to him, but he was too horny and curious to actually protest it. He heard the click of a leash being attached to the harness and again the controlling end was passed to Mistress Helen.
“Ok, Shall we go downstairs for some real fun?” Helen suggested in a friendly tone…not the least bit sinister or malicious as she pulled Kevin up by the leads.
They replied almost in unison, “Yes Mistress.”
Chapter 4
Once downstairs, Mistress Helen began to lay down a few rules, speaking mainly to Kevin who was in awe of the dungeon like set up his seemingly ordinary boss had for a basement. The walls were all finished in a plaster and painted to resemble a medieval castle and there were large wrought iron candle sticks which supported nearly a dozen candles each casting a warm but eerie dreamlike glow about the room. Catching Kevin’s eye were crude and unusual furnishings which looked to be made of old heavy wood beams of various sizes and lengths that were perhaps salvaged from an old house or barn and partially covered in leather. He was about to say that some of them looked a little ‘uncomfortable’ when he hear his name called.
“Kevin! Pay Attention! As I was saying, Normally Sherry is my ‘Little Bitch’ down here, but since she’s been so good lately, I’m going to promote her temporary from My Bitch to My Assistant …so, of course that leaves the job of ‘Bitch’ wide open! That is where you come in. From now on you will be referred to as Bitch, Slut, Whore or anything along those lines…Got it?”
“Yes Mistress.”
“You on the other hand will continue to refer to me as Mistress or Mistress Helen, and you’ll very politely call our darling Sherry, ‘Miss Sherry’. Now, you will do everything you’re told. You don’t want to find out what will happen if you disobey!
“No Mistress, I certainly do not!” Kevin said just cheeky enough to raise her eyebrow.
“Hmmm, Well Ok…this is how I want to start out.” Helen said.
Helen directed Sherry to remove her leather panties and sit in a well used wooden chair that was bolted to the floor slightly tilted back and made with a low seat, like folding a beach chair. She then ordered Kevin to get on all fours and to go down on her. As Sherry adjusted herself, getting ready for him to start, Helen removed Kevin’s collar leash and replaced it with a shorter double hasped one and locked it into a metal ring in the seat of chair between Sherry’s legs, only allowing him to raise his head an inch or two from her. She also placed thick leather straps on his wrists and attached them to similar rings on the thick chair legs.
“There…Now for the most important restraint.” Helen said laughing, “I wouldn’t try and stand up if I were you!”
Kevin felt her take the cock and ball harness leash and run it through a ring in the floor between his legs and from the angle he felt pulling down on his balls…slightly back towards his ankles. It was a bit tight, but not too bad…he thought.
“Hmmm, Just snug this up a bit” Helen said and tightened the leash through the ring making Kevin gasp.”
“Hey
!” Kevin yelped.
“Hey What Bitch?!” Helen scolded, “Better shut the
hell up or I’ll tighten it even more!”
Hmmm, Kevin thought to himself…I’d better fucking well be quiet, “Yes Mistress” He finally said.
“That’s better…now eat that pussy Bitch!”
“Yeah Bitch, Eat my Hot Wet Pussy! See if you can make me cum on your face!” Sherry agreed.
Kevin did as told and started lapping Sherry’s pussy and clit. He found he was really securely tied…he couldn’t move forward because of the cock and ball harness tied to the floor and or move backwards because of his collar locked to the chair…he was starting to feel a little helpless and not quite so lucky.
Meanwhile as Sherry was enjoying herself, Helen went behind a screen off to the side of room and switched on the hidden web cameras that were hooked up to her computer at work and started recording every move. She returned to the couple in the middle of the room carrying a leather paddle and moved in behind Kevin.
“Hmmm, Nice ass you have there Bitch” She said rubbing it with the paddle, “But not much color to it!”
The first ‘Smack’ shocked Kevin and he tried to lurch forward, but he felt a sharp tug on his balls from the restraint.
“Ow!” He said.
“Oh a little too hard? Did that hurt?” Helen asked.
“Yes! What the Hell?” Kevin said angrily.
SMACK! “What was that Bitch?” SMACK! “Did you say something?” Helen demanded.
Kevin’s ass stung and his balls were stretched tight trying to wiggle away.
“No Mistress, Please Don’t” He managed to plead, playing it a little smarter…he thought.
“Don’t say NO to me Bitch!” SMACK! Left Cheek SMACK! Right Cheek.
Kevin pleaded some more, but it only resulted in more hits of the paddle. Finally he was broken and stopped fighting it. He submitted to her completely, almost in tears…which of course was what she wanted.
“Well there we go…now we’re getting somewhere” Helen said setting aside the paddle and looking to Sherry with a wink, “Ok, now get back to eating that pussy before I get the paddle back out again!”
Sherry watched as Kevin immediately complied fearing another paddling. She was amazed at how Mistress Helen was able to break someone, even though she had experienced a very similar event herself. She wondered what she was going to like more now that she was going to experience the Dominant side of BSDM. She laid back and enjoyed his hot tongue working her clit and pussy…that question would answer itself soon enough.
After about 10 minutes Kevin had Sherry on the verge of an orgasm and Helen moved in behind him. He was still on all fours, restrained in a very vulnerable position. She started stroking Kevin’s cock with one hand and massaging his ass cheeks and balls with the other. He responded as expected…although he could only move a couple of inches he was hard as a rock and was trying to pump his hips.
“Ahhh! Yes! Damn it Yes! Ohhhhhhh!!!” Sherry moaned starting to reach her long awaited climax. She pushed her soaked pussy against his face and moaned louder and louder as she began to peak.
Helen took that opportunity to slip a lubed finger into Kevin’s ass as she bent forward and whispered in his ear, “Don’t even think about stopping! If you fuck up her orgasm I’ll paddle your ass hard for an hour!”
He didn’t slow, but kept sucking and licking her pussy as he felt Mistress Helen slide a second finger into him and pump them in and out. Suddenly Sherry screamed, “OH FUCK YEAH! CUMMING! OH FUCK!”
“Eat up that pussy juice Bitch!” Mistress Helen ordered, now furiously pumping three fingers in his ass, “That’s it! Eat it all up!”
Soon Sherry came down and recovered a little and Helen told her to get up and go get ready. Sherry knew the plan and stepped out of Kevin’s view behind the screen and slipped into a strap-on harness that Mistress told her to use. She positioned the thick 8 inch cock and tightened the straps around her waist. “Hmmm” She thought to herself, “Now this is going to Rock!”
While Sherry was getting ready, Helen couldn’t resist the temptation to tell Kevin what was going to happen next. He had begged to be let go, he didn’t want it, but she assured him that yes he did…her little Bitches always ended up begging for it.
“Ok Sherry, are you ready?” Mistress Helen asked.
“Yes Mistress, I’m SO ready! I’ve been waiting to do this for a long time!”
Sherry got on her knees behind Kevin and slowly started pushing her cock against his asshole. He tried to squirm away, but only managed to pull on his cock and ball harness making his hard dick swell even more under the tight harness.
“Look!” Mistress Helen said reaching under Kevin and pulling on his hard-on, “I told you he’d want it…they all want to be fucked like little sluts…they are just scared to admit it!”
Kevin was horrified! He tried to ‘think’ his erection away, but it just got harder and harder. “No Please Miss Sherry! Please don’t fuck me!” He pleaded in vain.
“Shut up Bitch!” Mistress Helen said slapping his ass cheek hard, “Go ahead Sherry, stick it in…fuck him good and hard. Loosen him up for me!”
That was all the encouragement Sherry needed, she leaned her weight forward and grabbing Kevin by the hips…pushed the head of her cock into his ass.
Although her appendage was just a strap-on, the feeling of dominance was no less exhilarating as she slowly slid her cock in as Kevin whimpered and tried to escape her penetration. She continued to work it in and by the time her thighs made contact with his ass cheeks, her heart was racing and her pussy was once again dripping with excitement.
“It’s In!” Sherry exclaimed looking over to Mistress Helen.
“Good…now start pumping it in and out until he loosens up a bit!” Helen replied.
“No Please Ladies!” Kevin pleaded feeling the discomfort of his ass being violated and the humiliation of it all, “It hurts, Please let me go!”
Mistress Helen laughed, “Yeah Right! Shut up Bitch…you’re just getting what you deserve.” She picked up the paddle and gave his ass a hard smack.
Sherry felt his resistance giving way and she started to pump harder and with an increased pace. Her thighs actually started slapping into his ass when she pushed forward which in turn pushed him forward pulling tight the leash on his cock and ball harness and Kevin had no choice but to push back against her thrust to keep his balls from being ripped off!
“Oh Yeah! Look he’s getting into it!” Sherry said excitedly.
“Fuck her cock Bitch!” Mistress Helen commanded, “Fuck it and say how much you want it!”
“No! I won’t” Kevin said, his restrained body beginning to break out in a light sweat.
“Come on you little Slut say it!” Mistress Helen demanded again readying the paddle.
“I can’t! NO!”
SMACK! “Say it!”
“Please, No!”
Another smack of the paddle fell, but Kevin wouldn’t relent and say he wanted his ass fucked.
Sherry was still fucking him with all the determination of a Pro-Dom and was nearing her first strap-on orgasm. Each time she banged her cock in, it bounced off her clit and sent intense sensations through her…the harder the thrust, the greater the rush!

Kevin was turning delirious, but still wouldn’t say he wanted it! Although he found he was beginning to like it…he was ashamed and his cock gave him away…fully erect with pre-cum dripping from its tip. He just couldn’t admit it out loud to the two dominant women.
Helen could see his resistance and decided to let it go for now…she would have him begging. Besides it was better that he hold out a little longer…she didn’t want Sherry to break him! She wanted him to surrender while she fucked him with her cock.
Sherry was still pounding away and finally started to cum. She thrust hard into Kevin, her cock making sloppy noises and Helen could tell that he was nice and loosen up.
“Oh Fuck I’m Cumming!” Sherry yelled, “FUCK MY COCK BITCH!”
Sherry was hot with sweat from her excitement and her exertions and her blonde wet hair clung to her young lustful face. Her muscled arms
and buttocks flexed and tensed as she thrust one last trio of times into Kevin and then and collapsed s
huddering onto his back.
“Oh My God! Fuck! I’ve never came like that!” She said laughing, “Shit! That was Great! Really Different…I LIKE IT!”
“Yes My Dear…and you’ll have plenty of opportunities for more. But now it’s my turn.” Mistress Helen said and finished strapping on her own harness and cock.
Chapter 5
Helen got behind Kevin and knelt down to check if he was at the right height for her. Satisfied she looked up and saw Sherry starting to take off her harness off and said,”Wait Sherry, not yet. Undo his collar leash and sit back in the chair and have him suck your cock now.”
Sherry gleamed, “Yes Mistress!”
“No, don’t wipe it off Sherry…it’s his job to clean up his own mess!”
“Yes Mistress” Sherry said again…naughtily.
Kevin couldn’t believe it. He had thought he was going to be doing all the fucking! How wrong he was! Now not only was he was going to get fucked again, but he was going to have to suck a cock as well…his only redemption was that at least no one would know.
Mistress Helen squirted lube into her palm and stroked it on her large 2 1/4″ diameter cock…grinning as she noticed that she couldn’t fully encircle the thick cock with her hand. She reached down under Kevin and loosen his cock and ball harness a notch or two, just enough so he would be able to maneuver slightly to accommodate the huge strap-on. Reaching around the front of his thigh with her lube covered hand she found him still fully erect and began to stroke him…she always found that if aroused, a man was more receptive to a thick cock. Not that it matter much, he was going to take it one way or the other.
While Helen prepared to penetrate, Sherry released the collar leash and sat in the chair waving her used cock an inch in front of Kevin’s mouth.
“Open up…come on, you didn’t think it was so bad last week when you wanted me to suck yours after you fucked me!” Sherry said. Knowing he didn’t have a choice and fearing another paddling Kevin replied, “Yes Miss Sherry” and opened up.
“That’s a good Bitch” Sherry said laughing while guiding the shaft into his mouth “Suck my nasty cock!”
Mistress Helen continued stroking Kevin’s cock with one hand and steered her cock toward his ass with the other. Kevin winced as he felt it press against his already well lubed hole.
“Ok, Bitch just relax and take it…you know you want it.” Helen pushed a little harder.
“Humph!” Kevin mumbled around the cock in his mouth then pulling free said’ “No way! Please Stop!”
“Hold that cock in his mouth Sherry…I don’t want to hear his whiny shit anymore!”
“Yes Mistress” Sherry said grabbing Kevin’s head and slamming it down on her cock.
Mistress Helen regrouped and grabbed him squarely by the hips and pressed forward. Kevin’s hole unwillingly gave way to the massive invader and its mushroom shaped tip popped in.
“Humph, Humph!” Kevin mumbled to no avail.
“Oh Yeah! Come on Bitch!” Helen said watching as the head of her favorite cock disappeared between Kevins cheeks and into his ass. She licked her lips and preceded to work another few inches in before slowly pulling it out. She grabbed it’s base and slapped it’s head down against Kevin’s asshole a few times and pumped it between his lubed cheeks.
“Here it comes now…the whole thing!” Helen said and pushed the head past his opening and continued until its whole length was inside.
Kevin bucked wildly against the invasion, but stretching his balls on their leash caused him to stop. He couldn’t believe how big the cock felt inside his ass and he wanted to push it out but couldn’t…she keep pumping it in and out no matter what he did. He tried to protest, but Sherry held his head firmly pumping her own cock down his throat.
Mistress Helen was thoroughly enjoying herself. She loved her ‘Bitch’ squirming even more than when they finally turned and start begging to be fucked harder. She could feel her pussy becoming extremely wet and the strap from the harness that ran between her legs slipped back and forth between her lips. She continued slowly fucking Kevin for another 5 minutes before she felt that he had loosened to her cock’s size. At this point she pulled most of the way out leaving in just the head…then she slammed it back in. She repeated this several times and thought he was starting to push back against her. She tried it again and yes…he definitely was! She motioned to Sherry to let his head go and let the cock out of his mouth. When he was free, she pumped him two more times and judged his reaction…he was responding like and old whore enjoying a good romp in the hay!
“Tell me you want it Bitch!” Helen said again slamming the cock in his ass.
No response.
“Come on Bitch, Tell me how much you want it or I’ll stop!”
Kevin fought with himself because he knew he wanted it…in fact he was thinking he loved it! Needed her to Fuck him till he came! Finally he relented and pleaded, “No! Please Mistress! Don’t! Don’t stop! Fuck Me! Please!”
Helen grinned widely finally having broken his male ego and pride.
“Oh so you like it now? Tell me you love being fucked like a little Sissy Bitch!”
“Yes Mistress! I love your cock! Please fuck me and make me cum!” Kevin responded.
Helen pumped him several more times and smiled at Sherry who was still sitting in her chair trying not to giggle at the site of her boyfriend becoming a cock hungry slut.
“You can cum Bitch, but not before I do once more!” She quicken the pace as the huge cock now slid easily in and out of Kevin’s ass.
“Oh Yeah! That’s it! Come-on Fuck Me Back! Hmmm, Oh Yes!” Helen’s hips slammed against Kevin’s ass as she buried the whole 10 inches deep inside. She started to cum hard and reached around his waist and milked his swollen cock in time with her orgasmic spasms. Sherry stopped watching from her chair and quickly wiggled underneath Kevin.
Helen was still cumming when she saw Sherry going under Kevin. She had told Her earlier what to do at this point and just kept pumping hard into Kevin’s ass.
Sherry’s mouth replaced Helen’s hand and after just a pump or two she felt his cock tense ready to explode.
Kevin was in ecstasy. He could feel his asshole clinch around the huge cock as Mistress Helen shuddered in her orgasm and Sherry pumped his engorged cock in and out of her soft mouth. His whole body tensed as he exploded into Sherry’s mouth. He wasn’t sure if it was possible he could of sworn that he had a multiple orgasm with that cock in his ass. It was the most dramatic climax he had ever experienced!
Sherry caught most of Kevin’s cum in her mouth and as instructed…didn’t swallow. Instead she retreated out from under him looked to Mistress Helen who was still shuddering from her massive orgasm and pulling her cock out of Kevin, motioned to Sherry, “Spit that cum out onto his ass…I’m going fuck it deep into him!”
Sherry carefully spit out the cum onto Kevin’s stretched asshole and Helen’s already glistening cock. Helen then pushed the cock back in and it made a loud gushing noise.
“Oh Yeah Fuck that cum in Mistress!” Sherry laughed, “Cum in his Ass!”
Mistress Helen fucked Kevin for a few more minutes, “Do you like cum in your ass Bitch?” She asked pumping steadily and hard.
“Yes Mistress” Kevin replied.
The dominance she felt at this point overtook her and although she had planned on stopping…She Didn’t! Her cock was just sliding in and out too good with all the cum on it and besides, she really wanted Kevin to remember his first Fuck! In no time she surprised that she was on the verge of another orgasm and grabbing a handful of Kevin’s hair, she jerked his head back and forcefully asked,
“Who’s Bitch are you!?”
“Yours Mistress!” Kevin eeked out.
“Damn Right, Fucking Little Slut!” Helen agreed and let go of his hair and placed both hands on his shoulders and pulled herself into him.
Kevin was shocked to feel himself grow hard again. Certainly he wasn’t really a Slut for Her Cock!? Was He? />His ass took her thick 10″ strap-on as she pounded away to another climax…he had a feelin
g he wasn’t going to be allowed to cum this time and he was right! Suddenly Kevin heard her moan loudly and push deep and hard into him. Leaving it buried… her body shook in a powerful climax…her hands clasping and digging into Kevin’s flesh. Finally after several minutes she withdrew and laid back exhausted…her sweat covered tanned body glistening in the candle light.
“Mistress, shall I untie him?” Sherry asked feeling a little sorry for her Boyfriend.
“Yeah go ahead…we have what we need” She said with a smirk, “You see Kevin…we have you on video begging for me to fuck your ass! From now on you are going to be our little Bitch whenever we want or I’ll let our little secret out…do you understand?”
Kevin was horrified! His only redemption was that no one would know and now this! But grateful the fucking was done, for now anyway and said, “Yes Mistress, I understand…I’m screwed.”
“Yes you are!” Helen hugged Sherry and laughed, “And we’re just getting started.” Helen looked thoughtfully at Sherry and said, “So what shall we do the rest of the weekend…Hmmm, I suppose some more training is in order.”
“Yes Mistress, I think he needs a lot more!” Sherry giggled as she bent towards Helen and started whispering a devious plan in her ear.

If you’d like to read what happens the rest of the weekend, Please leave a comment

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Weekend With Anderson, 6.0 out of 10 based on 1 rating

No Responses to “Weekend With Anderson”

  1. Ramrod says:

    Very hot story!

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  2. SubDude69 says:

    PLEASE let us know what happened that weekend; wish it happened to me:)

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  3. cj says:

    best every got top end it tell more

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  4. brakeman256 says:

    I am a 34 year old male. I have alway’s thought about being fucked with a strap- on by two or nmore domme’s.I would really appriciate it if you would send me the rest of what happened the weekend.

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  5. brakeman2562001 says:

    I am a 34 year old male. I have alway’s thought about being fucked with a strap- on by two or nmore domme’s.I would really appriciate it if you would send me the rest of what happened the weekend. I live in NC and if is is something you do please let me know.

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  6. MICHAEL_MICHELSON says:

    MY G/F AND I WOULD LOVE TO HEAR WHAT THE 2 OF YOU DID TO KEVIN

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  7. oneniceguy118747 says:

    i would love to hear the rest

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  8. marcislut says:

    i’d love to know what else Mistress Helen does to Kevin and even to Sherry. maybe he screws up and the tape is broadcast…..

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  9. isaaccox says:

    I love this story, please tell more.

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  10. T-amuck says:

    Continuation of this story is in-work, Thanks for your comments!

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  11. Yoshi says:

    Absolutely a great story, would love to read more about this interesting threesom

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  12. D says:

    loved the story, would love to read the rest of it

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  13. SexualOverdrive says:

    gr8 story. would love to read the rest of it

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  14. SexualOverdrive says:

    gr8 story. would love to read the rest of it

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  15. brakeman2562005 says:

    oh how i would love to be fucked like that by two or more dominatrix. i would also like to read what happen’s the rest of the weekend.

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  16. M says:

    Loved the story. Dieing to know what happens the rest of the weekend.

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