Lucky Josh part 5
Introduction:
Two more friends join the list as the story continues
Mistress Rose sat on the bed and smiled at him when he entered the room.
“Hello Josh” she said “I was starting to worry you weren’t going to show up.”
“How could I not show up after the great favor you did me?” Josh smiled at her, closing the door.
“You like Samantha a lot don’t you?”
“Yeah, I think she’s fantastic and superbly trained, compliments to her master” Josh said.
“I can tell she likes you too, she doesn’t show it much but I see” Rose replied “and thank you.”
Josh sat down next to her, taking a good look at her naked form.
Her short blond hair was spiky and still a bit damp, she had small breasts, a small C cup at best and pierced nipples. Her figure was well trained and her legs were a thing of beauty, smooth and perfect.
“Not quite a Mistress like this am I?” she grinned.
“Your body demands respect and personally I find you very attractive with or without your work outfit.”
“Thank you” she said a bit demure, something that surprised Josh.
“I heard that you didn’t mind fantasy play, is that correct?” she asked.
“Yeah, although never before today to be honest, but eh, I must say so far I like it a lot.”
“Good, I have a twofold request then” she started “and for what I am about to ask of you and tell you, I require your discretion and your word.”
“You will have both, I trust you” Josh spoke with confidence.
“Thank you Josh, I appreciate that” she said climbing on the bed beneath the covers.
She held the cover open and invited him in next to her.
When Josh lay next to her she snuggled next to him, between his arm and his chest.
“You know my line of work right? I am a professional Mistress and work in the sex trade, the bondage and s-m part to be exact.”
Josh nodded letting her tell what she needed to say.
“Image is everything in this town, especially if such an image is important for your line of work.”
“I am rather successful in what I do and my reputation is what letting me keep that success.”
“It also means that I have to keep that image up all the time, a strong and domineering mistress, not tolerating a man above her.”
She came up a bit, sliding partly over Josh so she could look at his face.
“I miss being wanted for me, not what I offer or stand for but just plain old Rose.”
“Having sex is easy, if I just wanted a fuck I could call a dozen of men or even some of my slaves but it is not the same.”
“Do you understand what I am trying to say?” Rose asked after a short pause.
“Yeah I do, you want to make love to someone who wants you for you and not the mistress part.”
Rose nodded and smiled at Josh.
“But jumping ahead” Josh said “although I like your mistress side, I don’t need to role play to make love to you, to plain old Rose, I only know you as a kind and trusting woman who happens to dress with a preference for fetish clothing, nothing more.”
“Well, the fact that you are gorgeous does help” Josh finished with a grin.
She smiled and nodded “I knew you’d understand and I am glad you see me that way, don’t ever change that, promise?”
“You have my word on that too my dear” Josh replied.
“Thank you again, now as for my request, the one for tonight is simple, I would like to make love to you like husband and wife, soft slow and tender.”
“The other request is a fantasy and it’s not a request I make lightly so I won’t hold it against you if you say no but please consider it before deciding.”
“What is it?” Josh asked, curious now.
“I have always been the aggressor, the mistress, the user.”
Rose paused for a moment and to Josh it looked like she was gathering her courage.
“I would like to play out a rape fantasy with you.”
Josh was silent for a moment before asking “you want to rape me?”
“No silly, I want you to rape me, I want to feel helpless and afraid while having sex.”
“Have you ever done that before?” Josh asked.
“No, it’s a combination of the image thing and trust, I need to trust the one who rapes me not to go too far or kill me.”
“Hmm” Josh said “it sounds like you want to play it out with an extreme level of realism.”
“Yes I do, you phrased it better than I did but yes, extreme real.””
“I am inclined to do it for you but we’ll need to have a few more discussions before we play it out okay?” Josh said pulling her body onto his.
Leaning on her elbows on his chest she looked at Josh and whispered “Thank you.”
Josh raised his head and kissed her gently on her lips, his hands on her ass.
“Now let’s make the neighbors jealous my beloved wife” Josh jested and turned then on their sides.
They kissed gently for a while, their hands exploring each other’s body with sensual movements.
Josh was amazed and the softness of her skin and enjoyed the caressing immensely.
Rose on the other hand was pleased to find a well defined body under her touch.
After a while Josh broke their kissing and went to her neck, licking it gently and biting it with care.
She held his head in her neck, moaning softly saying sweet nothings.
His hand went to her breast, massaging it and playing with her nipple.
Josh gasped when she took his cock in her hand, her thumb circling over his cockhead.
Following her example he moved his hand form her breast to her slit and she slightly parted her legs, allowing his fingers to go through it.
He was rewarded by a shudder and she tightened her grip on his cock for a moment.
Removing his hand, he came up, licking his fingers.
Turning around, he parted her legs more so he could lick her.
She gasped when his tongue went through her slit, flicking her clit teasingly.
Rose raised her leg more and pushed Josh’s head against her cunt.
It tasted very sweet and she was really wet already so Josh started lapping her juices up, enjoying her sweet taste even more.
He tongue fucked her for a while before returning to her slit and clit.
When he came back to her clit, he felt her lips around his cock, warm and moist.
She pulled his skin back all the way and licked his cock from top to bottom before taking it in her mouth again, slowly moving up and down.
Josh nibbled on her pussy lips, sucking on them to make them puffy and sensitive, teasing her clit all the time.
Her clit was big now, bigger that any clit Josh had seen so far and Josh started to suck on it hard then soft.
Her muffled moans were a joy to hear and Josh continued on her clit, sticking two fingers in her cunt and using his thumb to slide through her slit.
Exploring her cunt, he came upon her inner clit, her reaction showing him where it was as she bucked a bit, going deeper on his cock.
Alternating his sucking on her clit with rubbing on her inner clit he worked her up to the edge of an orgasm.
She was so close that she had stopped sucking him and was jacking him slowly instead.
He kept her there, on the edge, building the sensation higher and higher until he released her.
Rose gasped, inhaled deeply and then screamed her joy, pushing his head as hard as she could with one hand.
Josh felt her orgasm but didn’t stop at once, he continued a little longer making her body shudder.
Turning around again, he continued to tease her clit with his fingers, making her shudder and moan until he silenced her with his mouth, kissing her gently.
With his still wet fingers he teased her nipples, pinching them softly and cupping her breasts with his free hand.
Rose opened her moist eyes and looked at Josh with pain in them.
“Did I hurt you?” Josh asked concerned.
“No love, you didn’t” Rose whispered back “I am used to coming with pain or pressure, not tenderness, I am just a bit emotional, that’s all.”
Josh had a feeling that she wasn’t telling the entire truth but let it slide for the moment.
Rose turned on her back, moving a bit away and spread her legs more, her hand on his near her slit.
With deft movements she maneuvered his hand on all her sweet spots, pressing down when she hit the right spot.
Smiling at her concentrated face and shuddering body Josh was wondering what she was doing when all of a sudden she said “Get in me Josh, now.”
Moving quickly between her legs, he trust his cock straight into her waiting cunt, her lips parted by her hands.
She was so wet that even though he didn’t trust that hard, he slid all the way through to her cervix, bumping it.
“Don’t move” she said clamping her legs around his and her arms around his neck.
Holding him as tight as she could, he could feel her breathing increase and after ten long seconds, her body began to shudder and he felt her coming again.
She moaned loudly as she held on to him, her hips grinding her cunt around his cock and her cunt was milking his cock with incredible strength.
The sensation was unlike Josh had ever felt before, her body sharing her orgasm with him.
Alternating her grinding with slight bucking of her hips, Josh came hard before she’d finished her orgasm.
Almost like every nerve was alive in his cock, he felt intense pleasure and his throbbing cum spraying felt like blows of pleasure.
Surprised and spend, he fell on her, pinning her to the bed, his cock still twitching deep in her.
“That was incredible” he whispered in her neck, still shaking a bit from his orgasm.
“I wasn’t sure it would work” her hoarse voice answered him “but I had to try, you felt so right and I wanted it so badly.”
“Wanted what so badly?”
“To have a bonding orgasm with you” Rose answered as her arms and legs released their death grip on Josh.
“It has emotional value for you doesn’t it?” Josh asked in a tender voice.
“Yes it does, I have trying to achieve it for a while now but something always held me back.”
“With you and your complete trust in me, I felt like we might, you know, get it done.”
“Thank you” Josh said to the emotional woman under him “that was some gift you gave.”
“Trust me when I say it was my pleasure” Rose grinned beneath her tears.
Leaning on one arm, Josh came up a bit to lick away her tears.
She gasped when he moved, his still hard dick sliding a bit deeper in her again.
“You are still ready to play?” she asked surprised.
“Yes my love” Josh said “how do you want it this time?”
With glee belying her age she said “I want to ride you like a cowgirl.”
They quickly changed positions and without any delay she sat down on his cock.
“I am still so sensitive there, I feel like coming all over again” she whispered to him, leaning forward to kiss him.
After a sweet long kiss, she started to ride him.
Slowly at first and harder after a little while, her hips gyrating while she rode him.
His hands played with her breasts and caressed her body while she worked him hard.
When she sat down and leaned back, supporting herself on his knees, he looked up to see his cock slide in and out of her wet cunt.
The look of delight on her face and the sensations she produced on his cock made Josh buck and grunt deeply, announcing his orgasm.
Rose kept on riding him, feeling his cum shoot in her, increasing her speed to come as quickly as possible.
Josh bucket beneath her, pushing in deeper, first of his orgasm but after he had come because he was becoming really sensitive in cock, the feeling almost too much.
He was relieved that it didn’t take her too long to orgasm as well, wanting her to have this one.
Moaning softly, Rose lay down on his chest, her head just beneath his, a big smile on her face an feeling spend.
“Josh” she softly said “do you think many husbands and wives have such good sex?”
“I have no idea but somehow I doubt it” he grinned.
“So do I” she said snuggling into his embrace.
Josh and Rose lay for a while relaxing when he heard the door open and close softly.
Looking up he saw Sam walking towards the bed dressed in white knee length socks, white panties with Mini Mouse on it and a shirt to match.
Smiling, Josh thought that she looked cute.
“Almost innocent” Rose whispered lazily.
“Shall I?” Sam asked and Josh nodded, spreading his legs.
Sam moved onto the bed and started to clean Josh’s cock with her mouth.
Being in a relaxed state, she got it all in and her tongue took pleasure in playing with his soft cock.
After taking care of his balls she sat up waiting for her next command.
Rose had been watching with interest at her actions and grinned at Josh.
“Can your slave do me as well?” she asked coyly.
“Sure” Josh said and looked at a smiling Sam saying “clean my partner up just as good as you have cleaned me.”
With a passion that surprised Josh, Sam went down on Rose.
With her fingers she removed Josh’s cum from Rose’s cunt and licked it from her fingers, her tongue lapping the thighs all the way around her pussy till every spot was clean of cum and juices.
Only then did she start licking Rose’s cunt clean, taking her time and sucking her lips and clit clean.
Rose was panting softly and was a little flushed, Josh had gotten aroused form this spectacle and had a raging hard on again, despite his slightly sore balls.
He was about to place his cock in Rose’s mouth, her closed eyes and slightly parted lips looking like an invitation when Sam said “Master, Miss Danni awaits your company in her office.”
Both Rose and Josh looked a little disappointed but Josh nodded, getting ready for the next round.
His cock received a wet kiss from Rose who lay grinning on bed with Sam’s head between her legs and said “Do you mind letting her finish me?”
Josh looked at the two women and with regret said “No, Sam I want you to pleasure Rose until she comes before you join me with Danni, understood?”
Sam came up, her mouth wet with juice from Rose and said “Yes my Master, your will is my command” before diving down again.
Josh grabbed his towel again and covered his waist before leaving the room.
Burt stood next to the door, leaning against the wall being sucked by Megan, who was being fucked by his dad from behind.
“Oh my” Josh grinned at the spectacle and saw that the entire room was one big orgy.
Tickling Megan’s nipples for a moment, he saw her turn her head and wink at him, trying to smile with Burt’s cock deep in her mouth.
Josh kneeled down and whispered to Megan “Aren’t you glad we’ve met this afternoon?”
Unable to answer, Megan winked twice with her eye and nodded slightly before assaulting Burt’s cock again.
Grinning Josh got up and looked for the entrance to Danni’s office.
He had to decline several offers from girl only couples, including one from Melody.
“I am so sorry dear” Josh said to Melody “but I have a promise to keep first.”
Fully aware of what Josh was referring to, Melody kissed him gently and said “I’ll take a rain check then.”
Grinning he agreed and quickly made his way to Danni’s office.
He saw her sitting behind her desk, her legs crossed on it and a whiskey glass in her hand.
“Hey Josh” she said getting up “I was afraid you might be spend already but looking at that bulge I can see you are in the mood for some fun.”
“I am” Josh said meeting her halfway.
“There is just one thing” he continued “You know when I said that I would be your friend?”
“Yes” Danni said biting her lip provocatively.
“I really meant it, I believe that we could have a real close friendship and I usually don’t fuck close friends, so I am in a bit of a pickle” Josh finished unable to move his eyes from her dark skinned body clad in white lingerie.
“Oh sweetie” Danni said and hugged him, his towel dropping and his hard cock pressing against her belly.
“Just the fact that you are worried about it, makes your offer even more special.”
“I believe that you truly want to be a friend of me without taking advantage of me or my line of work, if I wasn’t dead set on fucking you, I might be inclined to agree but trust me when I say Josh” Danni continued with a loving look on her face “I accept wholehearted your offer of friendship and offer you mine as well.”
She kissed him softly on the lips, her big red lips feeling soft and tender on his.
“Perhaps a short friends talk before I jump you?” she asked before strutting away, swinging her ass in the most erotic way.
“A drink?”
“Yes please, whatever you are having” Josh said his eyes fixed on her ass.
Danni poured him a whiskey and filled her glass again as well.
“Let’s have a seat”
Josh took his glass and sat down next to her on the leather couch.
“So, about dinner Sunday, what were you planning to cook for me?” Danni grinned.
“I have no idea yet” Josh said “I figured we’d do some shopping together and see what we came up with.”
“Shopping for groceries” she laughed “that’s been a while, I like it.”
“I just thought that a normal day for a regular woman would appeal to you, you know, a walk together, perhaps visit a park or something, taking the time to get to know one another.”
“That sounds wonderful” Danni said “I’ll even leave my business phone with Burt then.”
Josh grinned and took a sip of his drink, the same whiskey she’d given him before and he really enjoyed the taste of it, his face showing his pleasure.
“So” she started “what is the thing that defines a true friendship for you Josh?”
“Absolute trust and dependability” he answered still smiling.
“So no dependency or sexual feelings?”
“Those can happen but are not needed for my friendship, not the way I see it anyway.”
“I see” she said and pondered on his statement for a few moments, sipping her drink.
“I’ll tell you what” Danni said leaning towards him “we’ll exchange a secret we haven’t told anyone ever and we’ll fuck just enough to cover for what the bet entails, making true love or mad sex Sunday after dinner, what do you say?”
“Deal” Josh grinned, pleased with her solution.
“Now about the secret we’ll share, it must be a sexual one alright?” Danni said removing her bra.
Josh just nodded as his gaze was drawn to Danni’s huge breasts and very big nipples.
“Up here Josh” she grinned at his lustful face.
Josh looked back to her face, blushing a bit and saying “you have really beautiful breasts Danni.”
“Thanks sweetheart” she replied and held them up so she could lick her nipples.
Her tongue was wide and very long, licking her nipples while she looked at Josh.
His horny face an open book, he wanted her and his desire to be a good friend was probably the only thing keeping him in check.
Pleased with his restraint, Danni let her breasts drop and said “My secret is this, my first lover was my younger brother, one morning I caught him staring at me while I was changing and I saw he had a hard on, I pulled him into the room and practically raped him, I sucked him first and then rode him through my virginity until I came.”
“That was the only time we’d have sex, he was shot the next day during a drive by.”
Josh saw she a little emotional about it but kept her face straight.
“I loved him, not just like a sister you know, we’d probably have been doing it still if not .. “
“Anyway” she said shaking her head to clear it “your turn.”
“I only have one secret to be honest, when I was fourteen I took advantage of my then step mom” Josh started “one night after a party she was partly undressed on her bed, passed out from whatever and I couldn’t help myself.”
“I just had to suck on her nipples and taste her pussy so I removed her bra and panties and did just that.”
“When I licked her pussy, she started to moan in her sleep and got wet so I slipped my cock in her and fucked her until I came, she never woke up so I covered her and left, feeling a bit ashamed but also very hot.”
“That was so hot” Danni said one hand in her panties.
“Best part is, although not so much a big secret, she took it later on her to teach me about sex and was my lover till I came over here” Josh finished.
“Fuck yeah” Danni exclaimed “I would love to meet her, such a slut, I like her already.”
“I am glad you approve Danni” Josh smirked at her.
“Oh I do” Danni said, her hand a frenzy beneath her soaking panties.
“What position would you like Josh? Want me to ride you so my tits get in your face or from behind so you can play with them?” she asked holding her tit to her mouth with her free hand.
“Since it will be a fast one, how about you stand bend over your desk and I fuck you from behind?” Josh offered.
“Sounds like a plan” Danni said and walked to her desk, clearing some space.
She then bent over, placing her breasts with care and spread her legs and arms saying “do me Josh, do me good and fast.”
Josh took up position behind her, smelling her arousal and feeling her wet cunt through her panties.
Pushing her panties to the side, he placed his cock in front of her cunt and slowly went in.
“Fuck yeah” Danni exclaimed again, her cunt dripping wet and eager for more of Josh.
Steadying himself, he grabbed her hips and started to make speed.
Soon he had a good pace and Danni’s moaning and cursing encouraged him to go faster.
Her cunt was spraying her juice with each slam as he rammed into her and he saw her roll forward and backwards on her breasts.
The fact that she supported herself on her breasts was an extra turn on for Josh and with her able cunt muscles she made him come hard and quick.
“Oh shit” Josh said when he started to pump her full of cum.
His knees got week and he had to hang on to her hips to stay standing.
“Shit alright” Danni said “I was so fucking close.”
Josh felt himself get soft despite the super sexy and arousing woman in front of him.
Feeling a bit guilty he said “Just wait Danni, I would never leave you hanging.”
Down on his knees he opened her cheek’s a bit so he had better access to her cunt and started to lick her.
“Oh my god, you are going to eat me, while you just fucked me and shot me full of your jizz?”
“That is so fucking horny” Danni almost screamed, moving her cunt as close as she could to his face.
“Damn Josh” Danni panted, so aroused that she was almost out of breath “nobody has ever done that, that is so sexy, please let me watch, please.”
Josh moved a bit back and Danni turned to sit on her desk, her moist cunt leaking on it.
Reaching up, Josh had better access now and started to work on her for real.
He used his finger trick on her and soon she came like a hurricane, grinding his face in her pussy with all her might screaming “fuck yeah fuck yeah oh baby yeah.”
She didn’t spray but her juices flowed with force and Josh kept on lapping it up, teasing her slit and clit all the time extending her orgasm.
After a while she let his head go, dropping back on her desk breathing heavily.
Josh licked her a few times more for good measure and stood up.
Looking at her lying on her desk, her face in state of bliss he really felt for her, more than he realized and said so “Danni, I really like you a lot, more than I should perhaps but there’s something about you that, I don’t know, makes me want to hold you and hug you, keep you safe and fuck silly.”
Danni looked up with glazed eyes and said “I know, I feel the same Josh, few men have made me feel like you did just now and that was a quickly, imagine how I’ll feel after Sunday.”
“It kind of scares me you know” she continued sitting up and pulling him into a hug.
“I know” Josh said softly “every woman I have had the pleasure of with the exception of Burt’s companion gave and took something from me, none of the women saw it as just sex and neither did I.”
“I am a bit overwhelmed to be honest, heh, a second secret for you Danni” Josh smiled weakly.
“All these wonderful women telling me I enriched their lives in one way or another, it’s rather big you know, I feel like I cannot let them down, they trust me and yet, it’s not one girl you know, it’s a handful.”
“Josh dear” Danni said soothing “it will be alright, you are special and you have enriched all of our lives with your youth and honesty, you never pretended to be more than you are and you never offered more than we could take, you are wiser than you think.”
“I can understand that you feel overwhelmed but trust me when I say, these women, myself included know what a treasure you are and will treat you accordingly so just be yourself, that is all we ask.”
“Thanks Danni” Josh whispered and Danni was reminded of his youth and vulnerability.
“What are friends for” she whispered and held him for dear life.
Josh relaxed in her warm embrace and felt lucky and save, he was glad Danni would be his friend, any doubts he had melted in the embrace.
“You know, for such a beautiful and wise friend. You can be foul mouthed you know” Josh grinned causing her to shake with laughter.
“Josh love, you haven’t heard anything yet, I was civil just now” she replied, happy that her talk had made him feel at ease again and glad their friendship was as strong as it was even after such a short time.
Holding him she felt at ease and home, he made her feel needed and wanted without demands.
Chiding herself mentally she said to herself “don’t you fall in love baby girl, he’ll make a better friend for it.”