Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.
You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.
Click hereJack discretely hung back while his girlfriend and the international superstar walked upstairs, and before long the indiscreet sounds of passion could be heard from one of the bedrooms. Jack knew better than to disturb his girlfriend while at play until invited, though it didn't stop him from imagining the insanely hot scene in his head. He didn't have to wait too long before a New York accent shouted on him to join them.
He found them in the master bedroom, Jennifer on all fours being pounded from behind by Angela in a strap on, her black hold up stockings being the only article of clothing left on her. Angela nodded to her front without missing a beat, the incessant slap of flesh on flesh interspersed with moans of pleasure. Jack needed no second invitation, swiftly discarding his clothes and freed his rapidly hardening cock.
He manoeuvred in front of her, with Jennifer grabbing his cock and immediately attempting to swallow him whole, but in the end settling for bobbing back and forth whilst leaving a few inches for her fingers to stroke. Jack grabbed her swaying breasts and twisted her nipples, which was met by a long loud moan, after which Jennifer briefly lifted her mouth off to encourage him to do more and for Angela to spank her naughty ass. Both complied and very soon after that Jennifer had a long body shaking orgasm before collapsing face first onto the bed.
Angela swiftly slipped off her harness, pushed Jack onto his back and mounted him. He slipped easily inside, Angela's wet pussy evidence of how much she had enjoyed her part previously, and before long she was riding him in a familiar energetic rhythm. Jennifer had rolled onto her side, her neck and chest reddened from her exertion, and watched with fascination as the couple fucked beside her. She took Jack's hand closest to her and held it to her chest, while his other was busy playing with Angela's nipples just how she liked it.
Their orgasms soon followed, Jack thrusting high as his cock pumped deep inside his girlfriend who almost immediately came, her head tilted back, her thighs shaking and a moan confirming that finally all three were satisfied. Angela collapsed forward onto Jack, who held her close while Jennifer stroked her back. She slipped off to the side, leaving Jack in the middle. A few moments passed while breaths were taken and the moment passed.
"Angela baby you were fantastic, though now I have to tell Amy Adams that I let someone else take my strap-on virginity."
"Well I appreciate getting the honour of being your first dildo darling, but I'm pretty sure you know what you're doing with the rest of it. My god, that tongue of yours!"
The two woman partially raised up and gave each other a lengthy kiss.
"I'm really blown away with how chill you are about Jack and other women. Even in the short time I've known you, you invite the gorgeous blonde into your bed regularly, you must know we fucked before I went to my media thing and that's before today is even finished. How do you do it and not go insane with jealousy?"
"Straight in with the big question! Well darling...our lovely Jack is unconsciously attractive to women, he cannot control it. Now I can either let that drive me mad and demand that he is only ever going to be with me. Or I understand that it can be really unhealthy for the women not to be able to respond to it, and know that regardless of what happens he's coming home to me. We have a truly wonderful set of friends that understand this, and most of them find their way into our bed at some point. Sometimes with me, sometimes not."
She smiled then leaned towards Jennifer, and loudly whispered in a conspiratorial tone.
"Besides, I'm not convinced I could keep up on my own...I think of the other women as reinforcements."
Jennifer laughed, but nodded her assent as if to indicate that she understood.
"Plenty of variety in your sex life then. Wow... but damn if it doesn't work for you. So tell me Jack, am I your first Oscar winner?"
Jennifer was being fully tongue in cheek with that remark, and they all laughed, but Jack took a moment to be serious.
"It would be thoroughly indiscreet of me to answer that question in any way Jennifer. I never kiss and tell, just like your visit will be getting zipped into the vault. You need not worry about Debbie either."
"I hadn't even thought about that, but honestly it had not occurred to me to be concerned. So I know you won't answer, but I think there is a very good chance that you'll have fucked every woman that will be around the dinner table tonight, and I'm neither jealous nor consider myself any less special."
A round of hugs followed, by Angela warning that they needed to get ready to go out. She took Jennifer by the hand and led her into the master en suite, which had a large shower cubicle which all three very comfortably fit into. Starting with washing each other's hair and progressing soon to soaping all over their bodies, the sight of the two woman together soon had a Jack fully erect again, with Jennifer gasping with surprise, shortly before turning and guiding Jack into her from behind while Angela stood against the other wall and masturbated as Jack was soon pounding the American woman.
Jennifer took only a few minutes before her latest orgasm wracked her body, her legs trembling with Jack holding her close whilst still drilled deep inside her.
"Oh fuck that was amazing. But Jack you're still hard...whatever shall we do?"
Jennifer coyly put a finger in her mouth then beckoned Angela to her. The kiss that followed was spectacular, so Jack who was stroking his length did not take long before he grunted that he was close to coming, which did not seem to interrupt either woman, so he came multiple times, spurting large globs of come on both of them. Once they eventually noticed, each took turns scooping up the cum and feeding into each other's mouth.
They cleaned up and stepped into the bedroom, Angela sharing her dryer as Jennifer swiftly styled her hair, before stepping out to dress in the room where her shopping from earlier in the day waited for her. Jack dressed and waited downstairs and was soon joined by Angela. Jennifer took a little longer but when she appeared she looked every inch the movie star in the blue dress that Jack had seen earlier in the day.
Jack ushered both women out to the car, and slipped behind the steering wheel. Jennifer briefly protested and was insisting they get another car, but Jack reminded her that he needed to be fit to drive her in the morning so would not be imbibing that night.
"I might still be over the limit in the morning and I'd find it tricky to do the driving with a suspended licence. Perhaps some other time, as I enjoy a glass of wine as much as anyone. Except perhaps Angela, she's the connoisseur in that department."
"Darling if I didn't know better I'd think you were trying to say I drink a lot.."
"Then you're my kind of gal Red. A woman needs dependable drinking buddies to make sure they have a good time and all get home safely. What do you say Ange, are you in?"
"Oh sweetie I was never out"
The two woman laughed uproariously in the back seat, but Jack grinned and focused on getting to the restaurant, though now he was starting to think of Jennifer more as a friend than a client, who he admittedly had fucked a couple of times that day already. They soon arrived, and after parking the car Jack followed the two women inside. At the bar already were Sarah, Rachel & Alex who were exchanging hugs with Jennifer and Angela. Jack organised a round of drinks and they were shortly joined by Debbie and Laura, the latter being initially slightly star struck, however Jennifer's warm down to earth personality soon had them all chatting and laughing. Finally in walked Holly who was wearing a rather daring low cut dress which finished mid thigh.
Holly squealed with excitement as she said hello to Jennifer, who looked immediately comfortable and insisted on sitting next to her at the table when they were taken through. Dinner was a fun chatty affair, with stories being told and glasses raised in mock toasts. The two celebrities appeared to be thoroughly enjoying themselves, and before long the meal was almost over.
Angela whispered into Jack's ear.
"You know Miss Lawrence has had her hand up my skirt when she's not been eating. Holly's looking a little flushed too...I wonder if she's been multi tasking."
Angela then gasped for a moment, which left Jack quite sure his girlfriend was being fingered by the actress at the dinner table. He caught Jennifer's eye briefly, and she cast a knowing smile at him. Angela announced she was going to powder her nose and Jennifer immediately joined her. Holly waited briefly before hopping into the chair next to Jack.
"Isn't she fabulous? But also not shy about what she wants, her hand has been up my dress most of tonight. I had no idea she was so into women, but I'm very happy to have found out. Horny little minx, but now I'm very much in the mood too. Do you think she'd be up for an invitation back to the flat?"
"I can find out, but if what I think is happening in the loo just now is happening, I think she might do you in the back seat of the car never mind on a bed. Why don't you let me give you a lift and we can see what happens."
Holly smiled whilst reaching under the table to grope Jack's groin and discovering a swiftly stiffening cock. She gave it a loving stroke.
"I've watched you fuck every other woman at this table, and so I don't even need to ask about Jennifer. But I am so fucking horny Jack I wish I could drag you off to the loo for good hard pounding...only thing is I think I would scream the house down so we can't do that. Promise me you will take care of me even if I can't get Jennifer to drop her knickers...if she's wearing any that is."
They both chuckled and at that Angela and Jennifer returned, the redhead looking marginally flushed but impeccably presented, while the actress was smiling warmly at the women around the table. Angela slipped back into the seat beside him, and whispered rather breathlessly that she'd been fingered rather well to a quick orgasm in the loo, but when offering to reciprocate told they didn't have time but promised to give her the opportunity later.
Soon enough the meal was over, hugs were exchanged and the crowd started to head their own way, though Debbie tipped a rather unsubtle wink to Jack as she left with Sarah, Rachel, Alex and Laura who were on their way to find a bar with a dance floor. Jack then offered Holly a lift home which Jennifer insisted they do, and off they set, Holly and Jennifer in the back seat, Angela beside Jack up front. There was giggling and whispers which were replaced by kissing and moaning in very little time.
Although not looking, Jack couldn't miss the pulling off of the lacy white thong from under Holly's dress, though with the dress pulled up he'd pretty much seen it already. Jennifer swiftly but gently popped Holly's boobs out from her dress and proceeded to suck on the nipples while vigorously fingering her. Loud moans of pleasure emanated from the rear of the car, while up front Angela was a spectator to a spectacular show, and was very soon masturbating along.
Jack certainly wasn't oblivious to it, but gritted his teeth and focussed on arriving safely in the underground parking garage at Holly's flat. They arrived shortly before the inevitable orgasm, which had Holly shaking and moaning very loudly. She took a few moments to compose herself, then picking up her panties and placing them in a tiny silver clutch bag, she stepped out and led the quartet to the lift, then her flat.
"Okay darlings make yourself at home. As hostess I'm claiming dear Jack first, especially since I'd put good money on him having fucked you both, possibly together, at least once if not twice today already."
Jennifer feigned indignation and asked what sort of slut did Holly think she was?
"Oh you're my kind of slut gorgeous. I'm pretty sure you gave our favourite redhead a good time at dinner tonight just like you gave me in the car. But I've observed that once a woman is around Jack for a little while her sexuality is unleashed, and you get to do pretty much anything you want to."
Jennifer giggled and nodded.
"That's actually not a bad way to describe it. You know around Jack, I think unleashed is a pretty good way to explain it. I'm not normally in the habit of fingering a girl I'm having dinner with in a restaurant...unless it's Amy and she kind of demands it...but I had my hand up both your skirts tonight and I loved it. So Jack....you've already fucked me twice today and Red here a couple of times as well. In my experience most men have nothing left in the tank after that, but I'm guessing you're about to show us just how much stamina is left in that gorgeous, remarkable cock."
Jack smiled and as Holly stepped towards him, noted Jennifer and Angela pour themselves drinks and sit down to watch the show. He took Holly in his arms and they enjoyed a long familiar kiss. Earlier he'd noted the back zip on her dress, and deliberately pulled it all the way down, then slipping it off Holly's shoulders to watch it float to the ground. He was vaguely aware of Jennifer making approving noises about Holly's exquisite figure, but had his attention swiftly brought back as Holly unbuttoned his shirt and sucked on his nipples, gently teasing them between her teeth causing him to moan approvingly.
She wasted little time getting him out of his trousers and boxers, pausing only to marvel at the swiftly stiffening cock. For all that he and Holly had fucked many times before, she still was pleasantly surprised that each time she was with him he was aroused and very much into her. As a woman approaching 40 and with three young children, most days off screen she was very much a mum and loved that very much. But around Jack, she always felt desired and completely able to tap into her sexuality. She felt him gently but firmly move her towards the bed, her calves touching against the covers.
Holly sat on the edge and briefly kissed Jack's quivering length, before shuffling up the bed, lying down with her legs parted and knees raised. Jack smiled, turned briefly to Angela who nodded and whispered something in Jennifer's ear which briefly made her jaw drop. She whispered back into Angela's ear, not wishing to disturb the lovers in front of her.
"Eleven inches? Fuck that's impressive, and given how many times we know he's fucked today it's incredible that he's so hard again. I mean blondie is just the perfect MILF, great body and infectious laugh and bubbly personality. Who knew she liked to fuck so much?"
The pair paused their discussion as Jack made his way between Holly's legs and licked his way up her body's, causing loud moans of appreciation. The blonde on the bed was in no mood to wait, and guided Jack's length inside her, her body shuddering as he slowly glided until their bodies met. Then after the briefest of pauses, he slowly withdrew and thrust, settling into a lazy fucking rhythm which Holly's body matching each downward stroke with a push up of her hips.
The moans and gasps as the pair pleasured each other was quite infectious, with Jennifer placing her now empty glass down, and turning to Angela before leaning in, gently sweeping aside the long russet curls and kissing her neck. The redhead moaned rather loudly but did nothing to distract the couple on the bed, with Jack now busily pounding Holly in just the way she liked it, at least if the noises from the bed were anything to go by. Angela gently pressed away her very attentive companion, before standing up, unzipping then slipping out of her dress to reveal she was naked underneath, her small but firm breasts topped by tiny fierce pink rosebud nipples which were aching to be touched. Jennifer paused briefly to drink in the vision, with Angela's curls halfway down her back being the only hair on her body. The redhead moved to straddle the blonde, who begged a moment while she tore her dress off, mumbling that sort of stain wasn't easy to explain to her dry cleaner, leaving only her baby blue lingerie which just about contained her heaving breasts and obviously erect nipples. Angela curled her finger in a 'come hither' gesture, so the blonde stood and followed her out of the room. Next door was another large king size bed, and Angela sat on the edge and widely spread her thighs, exposing her glistening shaved pussy.
Jennifer was about to walk towards her but a raised hand stopped her in her tracks.
"On your knees."
Angela's firm tone left no doubt what was required and who was now in charge, with the American woman pausing almost imperceptibly before complying, her head down as she approached until she felt the gentlest touch on her cheek lifting her gaze upwards.
"Any time you want me to stop, just say 'Omaha'..are we clear?"
Jennifer croaked a yes and received a warm smile in return.
"Pleasure me...I want to see if this New York bitch has a tongue as useful as it is busy."
The blonde's cheeks burned, but more importantly her pussy gushed as she embraced the moment and ceded control to the pretty redhead. She started with some slow long licks, sweeping up the excess fluids around the pussy, before some more daring darts inside which were met with approving words and sounds. However they were gradually being drowned out by the rising cacophony next door as Jack continued to vigorously drill Holly, who was imploring him to fuck her harder and harder until it went suddenly silent for a moment, followed by a wail of pleasure that lasted 20 seconds or more supported a loud bellow from Jack himself as he pumped load after load into their hostess.
Jennifer paused and glanced up with a quizzical look while this happened, but after it concluded she shrugged her shoulders and the redhead pointed back to her pussy, which the American woman gladly resumed licking. The noises from Angela grew louder until eventually her own orgasm arrived, noted by a noisy and uncharacteristic 'fuck' as her legs trembled signalling approval of the efforts of the women on her knees. Angela gently pulled her up and kissed her tenderly on her lips, telling her she had been a good girl, which left the blonde smiling and feeling a deep satisfaction.
Turning to the doorway Jennifer saw Jack with one arm around Holly's waist, the tv presenter looking like she had spent hours at the gym with her skin glistening with sweat and her hair a tousled mess. However the smile told its own tale of a deeply satisfying fuck, whilst Jack's cock incredibly managed up to half mast having watched a global superstar eat his girlfriend's pussy. At this point Jennifer was the only one who had not had an orgasm, and whilst normally she would have been vocal about that, she was mindful of the games she was playing with Angela, and patiently waited.
"Holly I think our visitor deserves a treat after being so obedient. But as our hostess of course you shall decide what that should be."
Jennifer's eyes burned with lust as she looked towards Holly, who paused, whispered something into Jack's ear that caused his jaw to almost imperceptibly drop, before squealing with excitement and disappearing. Jack turned his gaze firstly to Angela who was wearing her 'I'm quite satisfied' look that he had come to recognise when she had a great sexual experience, either with him or one of their friends. Jennifer was still kneeling and all but begging him to fuck, but Jack understood the house rules and waited for Holly to return.
She did not have long to wait. Holly reappeared carrying a large double ended dildo that wobbled in her hand, a pair of pink fluffy handcuffs and a blindfold. Angela confirmed their safe word before the blonde placed her American guest on the bed, put her hands behind her back and carefully clicked the handcuffs shut. This had the effect of causing Jennifer's breasts to proudly jut forward with her nipples a little wet and rather stiff. Next came the blindfold with Holly whispering assurances in her ear, and finally the dildo was presented to her lips, which Jennifer initially licked then tried to fellate, though it was hard going as it was quite thick.