"Tonight's Girlfriend" with Holly Willoughby
Tonight's Girlfriend
With Holly Willoughby
Written by TPG
CODES: MMF, blowjob, voy, drunk, gloryhole
DISCLAIMER: This FICTIONAL story was written for entertainment purposes only
We had been flirting for weeks on end, so when Holly Willoughby finally made good on her promise to join me for dinner I was somewhat surprised, particularly since I had been pursuing her from the moment we met.
It even got to the point where it was an office joke, with all of our friends and colleagues rolling their eyes any time the two of us would sit-in the same meeting three times a week.
However, despite all the office politics and bullshit, it seemed my persistence finally paid off.
"So, do you still want to go out to dinner?" Holly whispered while sticking her head into my cubicle. "I don't have any plans for tonight, and I fly home in the morning so, I'm free for a few hours... if you're still interested?"
At first I assumed she was merely teasing or putting me on, but when I realised she was serious I accepted the invitation. Even though this was totally unexpected, I wasn't going to miss this opportunity.
"Err, Sure. I'd love to have dinner with you." I told her.
"Good. Pick me up around eight," she insisted. "And don't be late. I can't stay out too long."
The fact that she was a "happily" married woman with three kids never even entered the equation. If anything, it only made her sexier.
As arrogant as it sounds, there was no doubt in my mind that the two of us would eventually fuck. I mean, just one look at the way we interacted together was enough to tell you that we shared more than just the same sense of humor, but a strong mutual attraction.
The fact that she was six years my senior, and technically my boss, only made it all the more forbidden and fun. Holly had even commented on how exciting it would be to play the role of a "cougar" with someone, something she had never experienced in her dating life, but had often thought about.
"So I guess one of your fantasies is to corrupt some young lad?" I quipped over lunch. "Take charge and show him what you like?"
The busty starlet smiled bashfully at me.
"I'm not saying another word. I plead the fifth."
"So I'll take that as a yes."
It was later that evening that I showed up to her hotel to pick her up for our date, and as expected Holly Willoughby did not disappoint. The stunning blonde emerged from the lobby in a short little black strapless number which showed off her womanly figure, and flaunted those big, heavy magnificent breasts.
The ensemble was capped off with sheer, thigh-high stockings which were held up by black suspenders, and accompanied by matching six-inch heels that only pushed her height into Amazonian territory, and accentuated her long smooth legs.
In fact she looked so good I almost tripped over as we climbed into the back of the taxi, where the clever ITV presenter seemed to sense my anxiety and took the time to relax me with some small talk.
"Now I should warn you, my life is pretty complicated at the moment." she stated in her posh accent.
"I know, I know. You're married." I replied while trying my best not to stare at her fantastic tits. "Obviously, it doesn't bother me."
Holly giggled.
"Well actually, about that—" she quipped, "Not sure that'll be the case, the way things are at home."
"You guys going through a little bit of a rough patch?"
"—but let's not talk about that now. Tonight, I just want to let my hair down and have some fun!"
"Yes ma'am,"
Needless to say that we were both in high spirits and eager for an "adults" night out.
Amusingly enough it was during dinner that the two of us got pretty wasted between two bottles of wine, and the alcoholic desserts. So much so that I soon saw a side to Holly's personality few ever knew existed.
"You know, you're actually a really handsome guy." she said.
"oh great, thanks. I think?"
"No, I mean. I don't know why you seem so keen on me."
I could tell she was fishing for a compliment, and by all accounts she really wanted someone to tell her what she wanted to hear, but I decided to play hard and make her earn it.
"yeah-yeah, I'm sure you say that to all the young lads in the office Holly."
"No really. I'm really flattered that you like me but I'm not that special. I'm just your average – soon to be divorced – working mom."
"I think we both know you're more than just average, Holly." I quipped while giving her tits a quick glance.
The blonde vixen laughed out loud and seemed to contemplate something before speaking her mind.
"You know, if this was a few years ago I'd totally be into you, ...and let you date me."
"Let me?" I replied, finding her wording funny. "I wonder what else you'd LET me do to you."
"Guess we'll never know." she teased back while enjoying the wine.
"Guess you're right."
"It is fun to think about though," she added.
And we both laughed.
"You know, I'm not as naive or sweet as everyone thinks." she said a minute later.
"Prove it,"
We both laughed again at the overly sexualized conversation.
"But seriously," she quipped. "I should teach that asshole a lesson, make him pay for dinner with his credit card or something?"
This was great news to me as the five-star spread we were enjoying was in danger of sending me broke.
"If you really want to teach him a lesson, why stop at dinner?" I suggested. "Maybe you should treat yourself to some shoes, some lingerie, maybe even a dirty weekend away?"
To my surprise Holly really seemed to enjoy this idea.
"And where would I go, and who would go along with me... let me guess!"
I shrugged at the implication.
"Hey, sounds like a good idea to me, just saying."
That being said, we left the posh restaurant a few minutes later and went over to a nearby pub for more drinks, where Holly was now well and truly drunk. In fact between her intoxicated state and those six inch heels, she was having a hard time walking straight and now leaned on me for support.
This of course led to her inadvertently rubbing those big famous boobs of hers against my body, which I'm sure wasn't lost on her either.
"—did you hear what I said?" she slurred. "You better take care of me tonight, I'm trusting you."
Once inside the pub we grabbed out drinks and found a nice secluded spot to sit, but that only lasted a few minutes before Holly felt compelled to get up and go to the dance floor, showing me her moves while I sat and watched.
As expected, it didn't take long for her to gain some fans, and I watched as two admirers jostled over who could dance and grind up on her, all while she looked back at me with a seductive look on her face.
When she finally had enough and returned to our table, we watched with amusement as her two new fans got into fight, and were ultimately thrown out of the establishment.
As predicted, Holly really seemed to get a thrill out of it all knowing that she was the cause of the fight, and giggled how it had been years since anything like that had happened to her.
"What about you," she then slurred playfully. "Sitting here the entire time, watching those boys fight over me. You got a kick out of that didn't you, watching them run their hands all over me?"
She wasn't lying, I did get a thrill out of it.
Holly giggled, "I know you better than you think mister."
"Do you, now?"
As the two of us joked around, Holly now sat with her knees on either side of me while I placed my hand on the inside of her thighs, running my fingers up and down her soft, skin.
"Err... you better stop that," she remarked at one point, as though trying to sober up.
"Stop what?" I teased, while running the tips of my fingers further up and inside her short skirt.
"That, what you're doing." she grinned. "If you keep it up, I might do something I might regret."
"Like what, have a little fun?"
As I spoke, I let my thumb gently graze across the front of her panties, causing Holly to inhale sharply. Even from that slightest of touches, I could feel the heat emanating from her sex.
"When was the last time you had some, fun... like that?" I whispered into her ear.
Holly didn't answer, and instead helped herself to another swig of her pint while her body answer for her, as she inched closer to permit me to now caress her pussy through her underwear.
"...it's been a while," she added a minute later. "Too long. I almost forgot how much fun it can be."
Over the next few minutes Holly and I proceeded to do more shots together, while I noticed her legs seemed to spread more and more.
"You know, if you weren't here tonight I probably would have gone home with those boys earlier."
"—both of them?" I replied over the music. "You really think you could handle that?"
Holly simply smiled.
"Sure. I have before."
Wow.
"Are you REALLY that randy right now?" I asked.
"Hey, you're the one sitting here trying to finger me under the table the last half hour."
"I don't hear you complaining." I quipped back.
"Exactly." she winked back, "Guess you're all out of excuses then."
Jesus I thought, as I boldly slipped the tip of my finger underneath the elastic band of her panties to finally make direct contact with her cunt. There sheer heat from her pussy was extraordinary, and almost threatened to burn my finger.
"Are you sure you want to do that here?" she teased. "You have no idea what you're getting yourself into."
Any suspicions I had about her state of mind were then answered with her next comment.
"How about we go someplace else," she suggested.
The next few minutes almost seemed like a blur, as we collected our things and made our way back out into the night air.
It was while stopped on the side of the road waiting for a taxi, that Holly surprised me again when she noticed an adult bookstore across the street and insisted we go inside.
"Come on, let's go check it out." she giggled. "I've never been inside one of those."
Now of course, as drunk and horny as I was at that moment the last thing I wanted to do was waste any more time screwing around, and just wanted to get her back to her hotel room to ravage her body, so I was somewhat crabby by the time she dragged me into the seedy establishment to look around.
"We should probably get you back to your room, so you don't miss your flight in the morning."
"No, not yet. Look at this place. Have you seen anything like it?"
But naturally, all I wanted to do was leave.
"Hey. Don't forget, I'm still your boss remember?" she teased. "So you have to do what I say."
Not wanting to ruin the moment, I played along as we perused the isles.
"oh wow, how do you think I'd look with one of those ball-gags in my mouth?" she'd giggle. "—what about tying me up tonight?"
Truth be told, in all the time I had known her I never imagined her to be so kinky and open-minded. It was actually quiet eye opening.
Ultimately we wandered passed a hallway in the back which read "viewing booths" where I jokingly asked if she wanted to see a show, and surprisingly enough the married mother of three gave me a cynical look but agreed.
"—I'm game if you are?"
With that, we purchased some tokens from the front desk and ventured down the murky hallway and into the very last booth. Inside it was dark and creepy and consisted of a single chair and TV on one wall, while the other was left blank and featured a hole in the center.
"Well this is fine place you've taken me on our date," she whined playfully.
However before I could respond, a movie suddenly flashed across the scene which quickly caught our attention and featured two burglars breaking into a house in the middle of the night, who stumble across a sleeping blonde.
"oh, come on!" Holly whined. "—who sleeps like that? ...this is ridiculous."
Then the sex started, and despite the silly plot it got real hot real quick.
The actress on screen proceeded to suck both of their cocks with deliberate slowness. She then lay back on the bed as one burglar stuck his cock in her mouth and the other began eating her pussy.
I glanced over at Holly and could see she was stunned into silence. I could tell from the expression on her face that this was probably the first x-rated video she had ever seen.
The guy eating pussy then switched to fucking her as she kept sucking his buddy's cock. He then went on to nail the blonde right there on her bed, before they switched positions again. She was now on all fours between the two of them, sucking one cock while the other guy fucked her from behind.
"oh jeez," Holly remarked through bloodshot eyes. "This stuff is pretty explicit, isn't it."
I took this opportunity to slide my hand around her belly and pulled her body close to mine, allowing Holly to feel my hard cock poke her in the butt.
At first I assumed she was so distracted that she didn't even notice, but a few minutes I felt her reach back and give me hard on a good proper squeeze. I responded in kind and reached up to fondle her tits, as we now stood there in the dark booth watching the porno together.
"Does this sort of stuff turn you on?" she asked without taking her eyes off the screen "—watching two guys bang some half naked bimbo?"
"Sure, the more the merrier." I answered honestly, as I brushed her hair to one side and kissed the back of her neck.
It was this action more than any other that finally made her respond with a soft moan.
When I repeated the action while firmly cupping and squeezing her breasts together, she turned to say something and I immediately kissed her hard on the lips, only to feel her melt into my arms and thrust her tongue into my mouth!
I didn't waste time scooping those huge natural tits out of her dress, to leave her standing there completely topless.
Amusingly enough Holly was so drunk at this point that she didn't so much as kiss me than slobber into my mouth. Not that I was complaining of course, since I really enjoyed swapping spit with her.
She really seemed to respond when I took each nipple between my thumb and forefingers and gently tweaked and twisted them about.
"ugh... you're really pushing your luck you know that," she purred.
"Just keep your eyes on the screen," I told her while playing with her fun bags. "—watch the way they fuck her."
Holly could only moan as I now groped her soft breasts, squeezing and kneading them for my own amusement while she watched the threesome unfold.
"Mm, yeah—" Holly cooed at one point. "I wouldn't mind a little action like that. Bet you've got something back here for me don't you?"
But as if on cue, a stranger from the booth next door suddenly took this opportunity to stick his cock through the hole in the wall, which immediately startled us both.
"Whoa... what the hell is that?!" Holly yelped with surprise.
While my initial reaction was one of amusement, Holly immediately panicked and back up against the opposing wall.
"I'm not staying here with that THING poking through the wall like that!"
"Holly, relax." I chuckled. "I got you. You're safe in here."
Nevertheless, the TV presenter appeared "sobered" by the incident and now wanted to leave, but as she turned towards the exit I suddenly pinned her up against the door, and slipped my hand underneath her short dress and buried two fingers into her dripping cunt!
"what are you—uummpphhfff!!"
Despite her objections, Holly's body seemed to capitulate almost immediately. In fact I dare say it had been years, if ever, that someone had man handled her in such a direct and crude way. It clearly turned her on.
As we kissed each other deeply again I motioned for her to spread her stance for me, as she now dared me to fuck her!
Instead, I shifted her over towards the mystery cock where I continued to finger and probe her, while inviting her to reach down and grab hold of our guest. I think she was initially ashamed to grab it, but after a little more "convincing" she eventually obliged and now gripped and stroked the strangers cock in her hand.
We stopped kissing long enough to look down and watch as she now leisurely jacked him off.
"I can't believe you're making me do this," she blushed.
"Don't act like it's beneath you Holly," I hissed from behind her. "We both know you're really just a horny little SLUT that loves cock!"
Surprisingly enough Holly never stopped stroking the cock, even as I pulled the rest of her dress down her body to leave her standing there in the middle of the video booth in nothing but her panties, stockings, and heels.
Seeing her stand there like that in all her glory, I instantly mauled her neck while I fondled those lovely round tits with both hands, provoking several moans from her throat.
As we continued to mess around Holly then jumped with freight, when the cock she had been stroking suddenly withdrew and was replaced with a hand, which now searched around trying to feel her ass and legs.
"okay, okay, this is just too weird!" she whined, as I held her there against the wall despite her objections.
"Just give it a chance, let him have a feel around."
"What, no way." she half giggled. "He's a complete stranger, I have no... oohhh."
Holly then interrupted her own train of thought when the guy not only massaged her pussy through her panties, but in one swift action buried two of his long fingers deep inside her cunt.
"yeah good. Play with her cunt." I growled while groping one breast, and holding her by the throat with the other.
"ooh god, I can't believe I'm letting you...!" she moaned mid sentence as I leaned over to suck one of her exposed nipples.
"Why don't you take your knickers off Holly," I suggested. "Like a good little slut."
The British beauty responded like she was in a trance and immediately peeled her silk underwear down her legs, allowing our mystery friend to snatch them up as a keepsake.
"ugh god," she whimpered as the two of us now worked her over. "I don't think I can stand much more of this."
"Is it turning you on?" I teased, while tweaking her nipples. "The way some stranger is playing with your cunt, Holly?"
"ugh, jeez." she grunted, as her perfect set of 34-DD's jiggled freely. "You guys are going to make me cum."
Noting this, I immediately pulled out my cock and before she utter another word, I pushed her down onto her knees and buried my rod into the back of her throat!
To her credit, Willoughby sucked me enthusiastically from the moment her lips made contact with my sex-flute, her head bobbing up and down over my staff as our friend was forced to merely observe.
In fact the Brighton-born model seemed so intent of getting me off, that I watched her skilfully suck on the tip while massaging my crown jewels with her fingers.
The entire world around us almost seemed to fade into the distance, as she sucked and slurped me hard with her mouth. That was until we heard our "fan" groan with frustration, as he was now relegated to beating off while watching the action unfold.
Holly blinked up at me appreciatively as I placed my hand on the back of her head and proceeded to fuck her mouth. Unfortunately for me this only lasted a minute or so before she suddenly stood up and directed me to sit in front of the television screen, so she could move to straddle and ride me.
"Fuck it," I heard her quip. "I need you inside me!!"
To my delight, the voluptuous blonde was so wet that she managed to take my cock all the way inside her in one fluid motion, while the weight and sheer size of her butt swallowed me whole.
As she carefully lowered herself down into my pork-sword, I just about thought I had died and gone to heaven, my eyes rolling into the back of my head.
Behind her, the two luckiest burglars in porn history were still tag-teaming the blonde girl on screen, while our "friend" was now audibly beating off in the next booth, as Holly began to roll her hips back and forth and worked my pole.
I couldn't believe how snug she was. Her ass was so big that it seemed to almost add addition padding and tightness to her pussy. It was just about the sweetest, warmest snatch I had ever fucked, and gripped me like a velvet glove.
Willoughby glanced behind her at the screen every so often as she rode me hard, using her hands to steady herself with the back of the chair behind me.
It seemed the visuals on screen, really turned her on and before long, the sound of flesh slapping against flesh could be heard throughout the booth as she now SLAMMED her sloppy-wet cunt down on me, again and again.
"ungh, unngh, unngh... fuck."
"Take it, baby." I encouraged, while squeezing her tits. "Take it boss. Ride my cock!"
My cock was taking some real punishment as the burglars now stood over the blonde girl in the video and jerked off all over her tits. At this point Holly was so SOPPING wet, that her cunt actually left a ring of white slime around the base of my shaft, while she bounced above me.
Fearing that I might come prematurely, I directed her to stop and switch positions, which she did by getting up and turning around, to carefully back herself up until she could sit down on my rod and ride me reverse cowgirl-style.
We both groaned as she initially impaled herself again, and for good measure, I gave her thick round rump a sharp smack which really seemed to rile her up.
It was this new position which allowed her to use the power of her thick strong legs to steady herself and dictate the pace of our fucking. It also allowed her to watch the lewd action on the screen, whilst giving me an unforgettable view of that phat rump as it swallowed me whole over and over again.
This continued for a few short minutes until Holly suddenly gasped when she looked over at the wall and realized that our friend had slipped his member back through the hole again, only this time he had slipped on a condom.
We both knew what he wanted, and the notion alone literally triggered an orgasm.
"Holly, babe..." I growled behind her. "I think someone wants to fuck you too."
"ugh, unngh, no way... no... ohmigod." Holly moaned at the idea (of letting a complete stranger fuck her).
"Keep going," I encouraged while slapping her ass harder. "—don't stop now. Ride my fucking cock, you little slut!"
"Oh. God—" she yelped. "I'm gunna cum again. I'm gunna cum all over your cock..!!"
"—do it, Holly." I urged. "Cream all over my dick boss!!"
It was only now as I felt her pussy squeeze and constrict, that I realized I was in serious trouble. I had to do something quickly otherwise I too was in danger of blowing my wad early, so I pushed her off me and forced her down to her knees.
The look on her face was priceless – one of surprise and confusion – as I stood over her pretty face and took her by the back of her hair and crawled her over to the strangers cock.
"Get over here...!! You know what I want to see," I hissed. "—show me how much you love cock! I want to see you suck this guys dick."
Without missing a beat, Holly eagerly took his large member into her mouth, causing him to let out an excited moan.
I watched as her mouth began to move back and forth over that latex-covered penis, her hand clenched around the base like a vice. Her other hand reached up to grab my cock, which she stroked sporadically the whole time.
"Good girl, keep doing that." I told her, while playing with her excited nipples.
When I heard her audibly moan around the strangers cock in glee, I directed her to keep servicing the cock in her mouth while I manipulated her onto all-fours, giving me access to that thick round rump.
Surprisingly enough Holly didn't object as I entered her from behind, while she continued to suck and slurp all over the cock in her mouth.
I grabbed hold of her wife hips with both hands, and began to fuck her with a steady rhythm, and she was now unceremoniously spit-roasted right there in the booth, by her co-worker and a complete stranger!
Within a matter of minutes her body shook with an orgasm as she kept slurring her pleasure.
"..oh yes..oh yes...oh..god."
I pounded her from behind causing her to yelp out loud and wail uncontrollably while we fucked her senseless.
"Ugh. God. Ugh. God." she cried with a mouthful of cock. "ohmigoddd,"
"Suck his cock, Holly." I growled while slapping her huge ass. "—suck his cock while I FUCK this big ass!"
Suddenly, Holly pulled her mouth from his penis and hissed urgently at him.
"—please." she almost begged. "I need you to cum!!"
Just hearing this submissive tone from her was enough to set me off.
While most times I could usually feel an orgasm approaching, this one arrived without much warning. My cock throbbed inside her pussy, as wave of intense pleasure coursed through my body and culminated in a feeling of overwhelming relief and satisfaction.
I couldn't remember the last time I had blown my WAD so deep inside a (married) woman, much less a busty MILF like Holly Willoughby, but boy was I making up for lost time.
I literally buried my wick as deep as humanly possible and exploded with the power of two Hiroshima bombs, gripping her chunky hips so hard I was sure I'd leave hand prints on her flesh, as thick spicket's of love-slime filled her womb again and again.
There were brief moments of pause between each spurt, causing Holly to sigh erotically with each corresponding deposit. This apparently set off our friend who quickly snapped off the well-used condom and suddenly announced his own orgasm.
"—fuck, gonna cum!!" he grunted as he blasted his load directly across her gorgeous face.
The first shot struck Holly directly in the eye, causing her to grunt and recoil in horror. The second came fast and made a perfect shot into her gaping mouth, gagging her briefly.
Holly grunted and swallowed hard as the twitching member was thrust back into her open mouth, and gulped down his gooey seed... while I still continued to deposit my seed inside the busty MILF on the other end.
"Yeah. Polish him off." I hissed while tapping the end of my spent cock against her ass. "—that's so fucking hot."
"Oh. God. Look at this mess!!" The Morning host huffed with one eye sealed shut.
As she sat back up and wiped her face, I chuckled at the sight of her seated there naked on the cold floor, utterly soiled in some strangers hot gluey jism.
"Guess we made a new fan, tonight."
https://thumbs2.redgifs.com/ShowyWar...restricted.gif
