Disclaimer: I do not intend for anyone to mistake this as being true and real. It is a fictional story involving fake versions of celebrities all over the age of 18.
Chapter 3: My Week with Jennifer
Some would see going from interviewing big names like Anne Hathaway and Jennifer Lawrence to visiting the set of the second season of a Lifetime original television program as being a step down. But when that program happens to involve Jennifer Love Hewitt constantly wearing skimpy outfits while pretending to jerk men off, you'd tend to think that maybe it's more of a reward for good work than a punishment.
I was supposed to spend one whole week on set with Jennifer, really getting into the ins and outs of not only her role but her life in general. It was pretty much supposed to be a fluff piece, and Steven Saunders (my boss) specifically told me that this was more of a Christmas bonus than a real hard hitting assignment.
'So this will be your office for the week,' one of the assistants said as she opened the door to a smallish office.
'Thanks,' I said as she walked me inside, it was basically bare, a desk with two cheap looking chairs was all that was provided.
'I hope this will be good enough,' the woman said, clearly knowing that it wasn't the most glamourous of spaces.
'This will be fine,' I assured. 'I don't imagine I'll be spending much time in here anyway.'
She smiled and headed out. 'Jennifer's just finishing up shooting a scene right now, she'll be over here in a few minutes.'
'Great,' I said. 'Thanks.'
She left the room, closing the door behind her. Immediately I moved over to the crappy desk they had provided me with and pulled out my notepad and my trusty Dictaphone, making sure to place them neatly on the desk.
'Let's see what we have here,' I said to myself, pulling out a small stack of folders from my satchel.
There were four separate folders, each from Steven Saunders' private collection, each of them presumably containing a lurid story of sex with Jennifer Love Hewitt. Each were labelled with different years; '2001', '2005', '2010' and '2011' respectively. It seemed that Steven and Jennifer had a career spanning love affair.
I opened up the folder marked '2001' and thumbed through it, reading about a pretty intense first meeting between the two. My goal with reading these wasn't just to read about Jennifer in sexy situations, it was more about finding out everything Steven knew so I could in turn dig deeper with my interview.
It took me all the way to '2010' to get to the really dirty stuff, the sort of stuff I can't imagine Jennifer would ever want anyone else to know, let alone the world at large - something I imagine she wouldn't even talk to her current boyfriend about.
Suddenly I heard a knock on the door. 'Come in!' I exclaimed, quickly hiding all of the folders, shoving them back into my satchel.
'Alright,' Jennifer sung as she opened the door, revealing herself in her buxom glory as she entered the room.
For a moment I was completely taken by surprise. I always knew she had a body to die for but I'd never thought I'd be so up close and personal with it, especially not while she was wearing something that so accentuated her best features.
She was wearing a very simple long pair of tight black jeans, which wrapped around her black lace cleavage boosting top and huge sexy ass snugly, even though she wasn't wearing a belt. Her tits seemed to be held together by the grace of god alone, from the looks of it she wasn't wearing a bra which gave off the impression that they might fall out at a moment's notice.
'Take a seat,' I said, simultaneously standing up and shoving my satchel on the ground.
She took my now outstretched hand, looked down at my half open satchel and smiled at me. 'They really don't take care of you guys do they?' She commented as we shook, referring to the room we were in.
'It's fine,' I said as the two of us sat down in our respective seats. 'I intend to be a very mobile and hands on interviewer, today and maybe Friday will probably be the only days we talk in here.'
'That's a shame,' she said, taking off her sunglasses and lightly shaking her long, wavy, brown and blonde hair. 'I feel kinda comfortable in here, away from prying eyes.'
'Well we are probably going to get quite intimate, this is The Lowdown after all,' I said, looking deep into her eyes, attempting not to stare at her heaving tits too obviously.
'I'm very familiar with how The Lowdown operates,' Jennifer said, leaning forward a little bit, making it almost impossible for me not to gawk at her chest.
'You've had a lot of interviews with us before, with Steven Saunders,' I said, now fearing my neck would break.
'I'm assuming you've read them?' Jennifer said, leaving forward a little further still.
'What?' I said awkwardly. 'Me... read... I...' Suddenly I remembered that she was likely referring to the actual published articles, not the raw accounts Steven kept for himself. 'Yes, of course, I have to do all my research.'
'You can look you know,' Jennifer said, an amused smile on her face. 'It would be pretty harsh if I wore something like this and got offended if a man wanted to look.'
'Oh thank god,' I said, immediately ripping my eyes away from hers and staring right down at her ample cleavage.
'I don't usually dress like this you know,' Jennifer laughed, clearly finding the humour in my unsubtle gawking. 'It was for a scene on the show, I'm usually quite conservative.'
'Conservative huh?' I said as I maintained eye to tit contact.
'Yeah,' she said slowly, catching on that I didn't quite believe her.
I brought my eyes back up to hers. 'Do you mind if we start the interview?' I placed my finger over the Dictaphone's on switch.
'As long as you've had your fill,' Jennifer said, leaning back and sitting upright in the chair.
'I can't promise I won't check in every now and then, but I've finally processed their existence,' I joked as I flipped the switch on.
'That's all I can hope for,' she said smugly, jokingly pushing up her tits.
'That's gonna set me back,' I stated, eyes moving back downwards.
Jennifer laughed. 'I'm guessing you have some questions?'
'Yes,' I said, grabbing my pad and looking at the prepared questions, deciding to leave the questions Steven suggested to last.
'You've done a lot of TV in your career, what attracts you about it? Is it the stableness of the work? A lot of actors like how much time they get with their characters.'
'That's actually a common misconception, about it being steady work,' Jennifer answered.
'What do you mean?'
'Sure it's steady, one season at a time, but once a year is finished, unless you're on NCIS or the Big Bang Theory, you have no idea if you're coming back again, it can be quite stressful,' Jennifer explained.
'That's actually an excellent point,' I said. 'So what is it that attracts you?'
'I think it would have to be the relationships you form,' Jennifer said.
'You get to work with the same people every day for what could be years, it's really quite nice,' Jennifer answered, her smile broadening as she talked.
'That's a perfect segue to my next question,' I said, looking from my pad, up to Jennifer's tits and then up to her face. 'You met your current boyfriend on the set of this show, what's it like working with him every day?'
'Oh it's wonderful,' she said. 'He's so understanding.'
'Understanding?' I looked into her eyes as I said this, and she smiled cheekily and let her eyes wander a bit.
'Well, it's kind of a sexy show and well... I'm not always sexy with him,' Jennifer explained.
'Yes, that would be interesting, how does he deal with watching you... well you know... all the guys,' I asked.
'It's all about trust and changing your definition of what makes a relationship work,' Jennifer said.
'So what does that entail?' I asked.
'Well it's simple, if a part of your relationship is being with other men then that has to become a part of the fabric of your definition of trust,' Jennifer said.
'Just so we're clear, you're talking strictly about on set?' I asked, eyeing her down carefully.
'Yes, of course,' she said breaking into laughter for a moment but immediately shaking her head and mouthing 'No.'
I looked at her shocked. She had just admitted to me that she and her boyfriend had an open relationship, clearly though she didn't want the whole world to know. It made me wonder for a moment though, because she clearly wanted to make sure I knew.
'I think we have enough for today,' I said, turning off the Dictaphone.
'Getting too hot for you huh?' Jennifer joked as she licked her bubble-gum coloured lips.
'I just want to savour it,' I explained, smiling at her. 'The questions only get more intimate from here.'
'I'm guessing Steven suggested a couple?' Jennifer said, standing up and putting both hands on the desk. 'I'm also guessing you read the real articles?'
'Is it that obvious?' I asked, staring into her deep cleavage.
'I'm willing to bet they're in that bag you so quickly tried to hide when I walked in,' Jennifer said, leaning even further forward.
Despite the sheer amount of cleavage that was inches away from my face, I looked up into her eyes. 'You'd be right,' I said.
'What do you think?' Jennifer asked, her face now right up to mine.
Her thighs were pressed against the edge of the desk. 'About these?' I asked, referring to her tits.
'No silly, it's pretty obvious how you feel about these, I'm asking about the articles,' Jennifer said seductively.
'I uh... I like them, obviously,' I said awkwardly.
'Did they turn you on?' Jennifer asked.
'Oh yeah,' I said. 'Rock hard.'
Jennifer kissed me softly on the lips. 'Honestly I was expecting to get Steven back but... I guess you're gonna have to do.'
She pulled herself up on to the desk, and slid across until her legs were hanging over my side. 'Whatever you need,' I said as she pulled herself off the desk and onto my lap, immediately wrapping her legs around my waist and pulling me into a deep kiss.
I placed my hands on her ass, pushing them underneath her jeans until I was touching her thong. 'I woulda thought you'd have gone straight for the tits with the way you were staring at them,' Jennifer said as she pulled out of the kiss.
'You don't just start with the main course,' I said before kissing her again, this time shoving my tongue into her mouth.
'Mmm,' she moaned. 'I like your style,' she said as I gripped her ass cheeks tightly.
'Mmm,' I moaned. 'I like your ass.'
Jennifer laughed and pulled out to kiss my cheeks and the sides of my mouth. 'You remind me of a younger Steven,' she said.
'Can we not talk about my boss right now?' I asked as I pulled my hands out of her jeans and placed them on her waist.
'Fair enough,' she said. 'How about I give you something to take your mind off of it.'
Jennifer reached down and grabbed each of my hands and pulled them up to her tits, forcing me to grip the glorious bastards. 'Jesus fucking Christ,' I exclaimed as I squeezed through her lace top, each of my thumbs digging deep into her cleavage.
Jennifer laughed. 'That's better,' she said knowingly. 'All boys are the same.'
'Fuck,' I moaned, as I pulled my hands up to squeeze the tops of her tits. 'I can't wait to release these melons.'
'Maybe tomorrow,' she said, pulling my hands away.
'What?' I exclaimed, feeling shocked and confused as I watched her get up from my lap and stand up straight.
'I just want to savour it,' she mocked. 'It's only going to get more intimate from here.'
'Jesus,' I sighed as I watched her grab her glasses and walk out the room.
'I'll meet you on set tomorrow, around four o'clock? I'm shooting a massage scene, I think it'll be good foreplay for the interview,' she said, grinning at me wickedly as she opened the door and left the room.
'What the fuck?' I said to myself as I looked down, disappointedly at the budge in my pants.
Watching Jennifer give someone a massage was a true sight to behold on its own, so when I watched Jennifer do it on set the next day wearing a sexy nurse outfit... well it more than reaffirmed my belief in some sort of a higher power. Or at the very least, that Jennifer really wanted me to sweat.
'Jesus,' I thought to myself as I stared at her deep cleavage.
Her white shirt was unbuttoned to about halfway, revealing her skimpy red lace bra that left nothing to the imagination. She wasn't wearing any pants, just red lace panties which also were left mostly uncovered as the buttons were conveniently unbuttoned at just the right place.
'Get a lot of context for the article?' Jennifer asked after the scene had finished shooting and the entire cast and crew had left for the day.
'I certainly have a lot of flavour text if I need it,' I said, staring up from her cleavage to her lips, which were covered in a sexy red lipstick.
Jennifer took a moment to fiddle with her sexy little nurse's hat. 'Good,' she started. 'Because I really want to give non-watchers a good idea about the kind of sexy show we have here.'
I flipped on my Dictaphone. 'Did you actually learn to give massages for the role?' I asked as I walked onto the set proper, investigating the room they had built.
'In fact I did take a couple classes, it's proved quite a useful skill,' she said, joining me as I walked around the set.
'In the bedroom?' I asked, as I placed the Dictaphone on a table near some candles.
Jennifer laughed. 'In the bedroom, lounge room... any room really,' she joked as I turned to face her.
'And what kind of skills does one learn from a massage class?' I asked, leaning against the massage table set up in the middle of the room.
'Are you trying to get me to show you?' Jennifer asked.
'I wouldn't know what you're talking about,' I said sheepishly, embarrassed at having been caught out.
'Oh really?' She said, walking right up to me, her body practically pressed against mine. 'Because your questions sound an awful lot like the ones Steven asked before I offered to give him a massage.'
'Can't blame a guy for trying?' I said, lightly placing my hands on her hips.
'No, I suppose I can't,' she said, pressing her tits against my chest. 'In fact, I really should be rewarding you for doing your research.'
Jennifer pushed me backwards onto the bed. 'Right here?' I questioned while looking up at sexy Nurse Jennifer. 'What if someone comes back?'
'I've specifically asked for them to give us privacy,' Jennifer said, as she pulled my legs up onto the massage table.
'Well if you're sure,' I said as Jennifer unbuttoned my shirt.
'Trust me,' she said, as she threw my shirt to the ground. 'I know what I'm doing.'
Jennifer made quick work of my trousers but wouldn't take off my underwear for me. 'You want the full experience right?' Jennifer questioned as she threw a white blanket over my body.
I nodded. 'You can take them off now,' she said.
Jennifer licked her lips as she watched me rip off my underwear and throw them out from underneath the blanket. 'Oh, you're an eager beaver aren't you,' she said, noticing the tent that had already been pitched.
'I'm still hard from yesterday,' I said as she pulled back the blanket to reveal my chest.
'Don't worry,' Jennifer soothed as she rubbed my chest. 'I'll get rid of all that tenseness.'
'I'm anything but worried,' I stated as I placed my hands underneath my head, feeling more relaxed than I had in a while.
'How does this feel?' Jennifer questioned as she rubbed the area around my cock, still not pulling away the blanket.
'Little bit to the left,' I joked.
'Like this?" She questioned, taking my cock in her right hand.
'That's it,' I sighed, a broad smile hitting my face as she stroked my rock hard cock.
I stared down her top in her expansive cleavage. 'Wow,' she said, while jacking my still growing cock with enthusiasm. 'This is bigger than I expected.'
'I'm going to take that as a compliment,' I said, looking up from her tits to her smiling face.
'It was certainly meant to be one,' she said, moving her fingers down to lightly massage my balls.
'Fuck,' I let out. 'They teach you that during your classes?'
'Not exactly,' she said, pulling her hand away from my cock just as she was getting into a rhythm. 'Let's see what we're dealing with here,' she said, pulling the blanket back to reveal my cock.
Her eyes widened with joy as she checked my dick out. 'You like what you see?' I questioned.
'I like it a lot,' she said, licking her lips. 'In fact I think I'm gonna need to do this a lot sooner than I intended, I just can't help myself.'
Before I could ask her what she was talking about she had already leaned down, placing my cock in her mouth. 'Whoa,' I moaned, immediately taken aback by the sheer force of her sucking abilities.
'Mmm,' she moaned as she bobbed up and down on my cock, puckering her lips as tight as she could each time she slid it out of her mouth. 'You have a tasty cock young man,' Jennifer said, before taking it in both hands and putting it right back in her mouth again.
It was then I realised just what the age difference between us was. That's not to say she was old by any means, she would only have been 33 years old, but that was still a good 10 years difference between us. The whole thing got me to an extra level of turned on, it made me start to think of her as some sort of a sexual mentor.
'And you got some fucking nice tits,' I said, unbuttoning the single button that was keeping her bra semi covered up.
'There goes my eager little beaver again,' she teased, taking my cock out of her mouth momentarily.
'You gonna finally show me these puppies?' I asked, grabbing one of her tits.
'That's the problem with your generation,' she said, lightly jerking my cock with one hand and grabbing my tit-groping fingers with the other. 'No patience.'
'I can't help it,' I said, as she held my hand over her tit. 'It feels like I've been waiting over ten years for this.'
'Oh,' she smiled, gripping my hand over her tit even tighter and pulling her other hand to softly stroke my shaft. 'You used to jerk off to me as a kid.'
'Guilty as charged,' I said, our fingers entangled around her tit. 'I think I watched Heartbreakers like a hundred times.'
'How old are you Desmond?' Jennifer asked, our fingers now digging slightly into her bra.
'22,' I answered honestly, hoping this wasn't some sort of a deal breaker for her.
'I don't think I've ever been with someone that much younger than me before,' she said, letting go of my cock and looking at me in the eyes.
'It's a first for me too,' I admitted, thankful she was still holding my hand to her chest.
'It's kinda hot... like I'm your sex teacher,' she said, biting her lip and taking my cock back in her hand.
'That's what I was just thinking,' I said, shocked at how similar our minds were.
'Have you ever been with a women with tits like these?' She questioned, our fingers digging deeper into her bra.
'No,' I admitted again, looking into her chest again.
She smirked and pulled her hand off my cock again and also pulled away my hand from her tit. 'It's been a long time since I was someone's first anything,' Jennifer said, reaching under her white shirt with both hands.
'Fuck yes,' I said giddily.
Jennifer laughed as she unclasped her bra, pulling it away and throwing it to the floor, letting her huge tits drop into their natural state. I quickly pulled my hand back up, grabbing her right tit and groping it softly.
'How does it feel?' She asked as I rubbed her perfect nipple.
'Like the first time I ever touched another woman's tits,' I responded, reaching over and grabbing her left tit with my right hand.
'I'm gonna get back to sucking your cock now, which I just learned is the first time I've ever sucked a cock from someone over ten years younger than me,' Jennifer said, before taking said cock back into her mouth, forcing me to lean up slightly and reach around her head to keep both tits in my hand.
I closed my eyes for a little while, wanting to simply let feeling dictate my state of mind. Exploring the sensation of having two huge 33 year old tits in my hands and the full lips of the 33 year old woman wrapped around my hard cock.
'This must be a dream,' I moaned as Jennifer circled her tongue around the head of my cock.
Jennifer moaned and simply kept sucking, bobbing up and down with increasing speed as I gripped and squeezed at her gorgeous tits.
'I'm gonna cum in your mouth,' I exclaimed, feeling the familiar pressure building as she bobbed on my cock.
She quickly pulled my cock of her mouth. 'Mmm, there's one more thing I want to show you before you cum,' she breathed as she took my hands away from her tits.
Jennifer leaned over and wrapped her hanging tits around my wet lipstick stained cock and squeezed them together. 'Are you an angel?' I questioned as she leaned over and spat on my cock, rubbing the saliva onto my cock with her tits.
'I might just be,' Jennifer said as she continued to lather her tits with saliva. 'I might just be.'
I leant up onto my elbows and watched as she titfucked my cock. 'Jesus,' I moaned as those perfect puppies smothered my prick.
'That's right baby,' she moaned, rubbing her tits together around my cock, bouncing them up and down. 'You just let Nurse Hewitt do all the work.'
'Fuck,' I moaned. 'I'm gonna cum.'
'Cum for me baby,' she moaned titfucking me like her life depended on it. 'Give me that cum baby!'
'Ahh fuck!' I exclaimed, cum shooting from my cock all up into Jennifer's awaiting and smiling face.
'That's it baby,' Jennifer soothed as cum shot again, this time hitting her chin. 'Give it all to me.'
'You're fucking incredible,' I panted as I watched Jennifer let of her tits and begin to wipe the cum off her face with her hands.
'Mmm, I know it would taste good,' Jennifer moaned as she licked my cum off her fingers. 'Tasty cock, tasty cum.'
'So I guess the answer to my question is, you definitely know how to give a massage.'
It was a very slow day. I arrived on set extra early, like Jennifer had requested, but because of some unavoidable delays I had to spend most of my time in the dirt cheap office space they had provided for me. I spent most of my free time just analysing Steven's articles, reading and rereading highlights like the time that Steven face fucked her on the set of 'Ghost Whisperer'.
My seclusion had to end eventually though. 'Jennifer wants you to meet her in her trailer,' the assistant said after knocking on my door, interrupting my research session.
'Thanks,' I called out. 'I'll be right over.'
I put away the folders and debated whether or not I needed the Dictaphone. I decided to leave it in the room, after all, if I did manage to ask any questions during the trailer visit, I was sure I could just remember them.
'Come in,' Jennifer called out after I knocked on her trailer door.
'I wasn't sure if I needed my...' I started as I walked into the trailer, but saw no need to continue.
The entire room was covered in candles, and the blinds were drawn to provide ultimate mood lighting. In the middle of all of this romance, on what looked to be a smallish bed, sat a cross-legged Jennifer Love Hewitt.
'You won't be needing that,' she said seductively.
My eyes nearly popped out of my head, she was wearing nothing but white lace lingerie. I could see her nipples through the material, and I guessed, if she uncrossed her legs, I'd finally be able to see her pussy as well.
'Yes,' I said as I closed the door behind me. 'I will remember this.'
As quickly as I could I ran over to her bed, jumping on top of her and practically mauling her body. I let my hands travel everywhere as I pulled her legs apart with my knees and shoved my mouth over the top of hers.
'You're so fucking sexy,' I breathed as the two of us passionately swapped saliva.
'I want you to fuck the shit out of me,' she begged as she started to rip my shirt off, literally tearing the fabric.
I pulled my hands away from her tits momentarily to undo my belt. 'Do I need a condom?' I asked as she pulled my trousers down.
'Just fuck me baby,' she breathed as I kicked away the jeans. 'I'm on the pill.'
My cock grew harder with that fact. Together Jennifer and I pulled down my underwear at the same time, passionately crossing tongues as I threw it to the ground.
'Put it in me Des,' Jennifer urged as I pulled up her lingerie, revealing her pink shaven pussy to me.
I shoved my cock deep into her cunt. 'Fuck yes!' Jennifer moaned.
I gripped her waist and continued to fuck her while the two of us kissed and continued to search each other's bodies. 'You cunt is so fucking nice,' I moaned while I ploughed her.
'Ahh fuck right there yes!' Jennifer exclaimed, gripping my back tighter as I railed into her.
I ripped her lingerie down, letting loose her jiggling tits. 'These are so fucking nice,' I said gripping and squeezing them.
I leant down and shoved one of them in my mouth, sucking on her nipple while continuing to ram her. 'You feel so good baby!' Jennifer moaned.
I shoved my face between her tits and motor-boated them, making sure I didn't lose my fucking momentum in the process. She dug her nails into my back, clearly pretty happy with the level of dick I was bringing into her.
I pulled back from her tits and leant backwards, gripping her waist and penetrating her as hard as I could. 'Fuck yes, oh baby, right fucking there!' Jennifer screamed as I brought her closer and closer to climaxing.
'You want me to make you cum?' I questioned.
'Fuck yes please!' She begged. 'Make me cum!'
With that I pulled her upwards by the waist and filled her cunt. 'Cum for me baby,' I seethed.
'I'm cumming!' She screamed, tits jiggling like crazy as she finally came hard on my cock.
I leant down and gripped her tits, jamming my cock in and out of her with slower deliberate movements. Making short work out of making myself cum hard and deep inside her snug pussy.
'Holy shit,' she moaned as I laid down on top of her. 'The control you have... I thought I was supposed to be teaching you!'
'Are you ready?' I heard Jennifer call out from my kitchen.
She had me sitting naked in my dining room, sitting on one of my chairs, waiting for her to come out of my kitchen with some surprise. 'I'm ready alright,' I called out.
'Here I come,' she called out. My cock was already getting hard with excitement just thinking about what she had prepared.
Nothing in my imagination could prepare me for what walked out of that kitchen though. Jennifer Love Hewitt walked out of my kitchen, wearing what could only be described as a see-through dominatrix outfit.
'Thank you god,' I exclaimed, salivating as I watched the sexy woman who was approaching me.
'This is all me baby,' Jennifer said, stopping in front of me. 'And a little bit of the devil.'
Jennifer pulled out a set of handcuffs from behind her back. 'Jennifer,' I exclaimed, I had never read anything like this in Steven's journals.
'Oh yeah baby this is the real deal,' Jennifer breathed, reaching behind me to cuff my hands to the chair, making sure I wasn't going anywhere.
'Holy shit,' I said, shocked as I watched the woman stand above me, my body completely under her control.
'Well I had to do something to turn the tables,' she said, running her finger along my hardening cock. 'You surprised me yesterday... I won't let that happen again.'
'What are you going to do to me?' I asked, in a mock scared voice.
'Why, I'm going to fuck you of course,' she joked, placing her legs over my thighs and straddling me.
'Do your worst,' I said as her cunt hovered right above my cock.
'Oh boy, I intend to,' she said as she lowered herself onto my pole, a look of absolute pleasure washing over her gorgeous face.
'Yes,' I breathed, a feeling of ecstasy coming over me. 'I missed that pussy.'
'And it missed you,' she whispered, letting the entirety of my cock into her.
'Fuck,' I moaned as she leant down and kissed up my chest, my cock inside her.
She continued to kiss up my chest until reaching my neck. Next she took my chest in her hands and rubbed it down in a similar fashion to when she was giving me a massage. 'You want the ride of your life baby?' She breathed as she kissed from my neck up to my cheeks.
'I think you know that I do,' I responded, defenceless toward her barrage of kisses, eventually culminating in a soft passionate kiss on my lips.
She placed her hands on my shoulders. 'Like this?' She said as she popped her pussy over my cock, causing me to buck instinctively.
'Yeah baby,' I moaned, eyes rolling into the back of my head as she popped up and down on my cock, her tits slightly jiggling with each bounce.
'Fill me baby,' she moaned, gripping one of her hands on my face as she rode me like a bull.
'Ride that cock,' I called out, letting her kiss me deeply.
She shoved her cleavage in my face as she rode me. 'You feel so good!' She exclaimed, gripping into my shoulder tighter.
'Are you getting close?" I questioned, judging based on the look of ecstasy on her face that she was in fact ready to cum.
'Nearly baby,' she moaned, grinding on my cock faster and faster, making sure it went exactly where she needed it to. 'I'm gonna fucking ahh!' She moaned.
She kissed me hard on the lips and gripped the back of my head tighter. 'I'm fucking cumming!' She exploded, screaming as she finally came.
'Fuck!' She panted, slowing down. 'Are you close?' She questioned.
'Finish me off baby,' I urged. 'I want to cum in your mouth.'
She nodded and climbed off my cock. 'I don't usually do this,' she said, bringing herself to her knees. 'But you are one hell of a lay.'
'Thanks baby,' I moaned, looking down as she took my cock in her mouth, immediately attempting to push as far inside as she could.
'Deep throat that cock Jennifer,' I moaned as I watched her attempt to engulf my entire dick. 'Fit it all into that sexy little fuck mouth of yours.'
She moaned and managed to fit it all in, holding it down before quickly needing to come back up for air. 'I can do better,' she said, somewhat apologetically.
'You're a fucking pro,' I said, closing my eyes as she took my cock back in her mouth, this time deep throating it with relative ease and holding in it for much longer.
She came back up for air for what would be the last time of the night. 'Cum in my mouth baby, I want to taste that cum again,' she begged as she took my cock in her mouth again.
She almost immediately deep throated it again, and instead of just holding it there like the previous two attempts, she managed to actually bob her head a bit, bringing me closer and closer to cumming hard in her mouth.
'Fuck baby,' I moaned, feeling my cock coming to a point of no return. 'Just like fucking ahhhh!' I came hard deep into her throat.
She held it in her mouth for a few seconds, sucking down my fluids as my cock slowly faded. 'Mmm,' she said after guzzling down all of my cum.
'You're a goddamned cock sucking Mozart,' I joked through heavy breathing.
'Thank you baby,' she said as she pulled the key from out of her cleavage. 'I still have a lot to teach you after all.'
'It's been a pleasure having you around Mr. Drake,' the assistant said as I approached the door to my office.
'Thanks Stephanie,' I said, placing my hand on the door. 'It's been a pleasure.'
She smiled and turned away, off to do whatever it was she did when she wasn't delivering me messages. I smiled and opened the door, certainly not expecting to find what I did on the other side.
'Wow,' I said simply as I stared at Jennifer, who was sitting on my desk facing me, wearing a green and black cheerleader's uniform.
'Thought I'd do something special for your last day,' Jennifer said, biting her lips and spreading her legs. 'I'm not wearing any panties.'
'This is pretty special alright,' I said, looking mostly at her extreme cleavage as I approached her.
'Did you always grow up wanting to fuck a cheerleader?' She questioned as I wrapped my arms around her, pulling her into a kiss.
'Mmm,' I moaned, noticing her hair, which was done up into pigtails. 'Not really a huge thing where I'm from, but they always looked sexy in the movies.'
'Just say yes,' Jennifer said as I placed my hands on her waist.
'I'm not going to lie to you, but you have unintentionally stumbled upon to one of my real fantasies,' I said as I moved one of my hands up her skirt.
'Oh yeah and what's that?' She asked as I gripped her bare ass.
'I've always wanted to turn you around and fuck you against a desk,' I whispered.
Jennifer let me turn her around, slowly facing herself toward the desk as I lightly pulled her up skirt. 'You're a dirty, dirty boy,' she breathed.
I undid my belt and pulled down my underwear, letting my hard cock press up against her ass. 'Being rough is a big part of this fantasy, so I'm going to say and do a lot of mean shit,' I seethed as I placed my hands on her bare hips.
'What am I in this fantasy?' She asked, looking back toward me and smiling mischievously.
'You're the wannabe cheerleader fucking her way onto the squad,' I breathed as I softly kissed her neck.
'And who are you?' She asked, bending herself over the desk and pressing her ass cheek even harder against my cock.
'I'm the coach who's going to fuck you and leave you high and dry,' I said, pushing her by the back so that her tits were pressed against the desk.
'Oh Mr. Drake, thank you so much for letting me join the team,' Jennifer said in a fake southern accent.
'Miss Hewitt,' I said, in my best American. 'You're a perfect fit.'
I shoved my cock deep into her soaking wet cunt. 'Thank you Mr. Drake!' She exclaimed, thighs pressed against the desk.
'I just have to make sure you're a team player,' I exclaimed, pulling my cock out and shoving it hard back into her again.
Jennifer moaned. 'I'll do anything for the team!' She called out.
Each time I drove my cock into her was harder than the last, before long her bare thighs that were ramming into the bench were starting to bruise. 'Fuck me harder Mr. Drake!' Hewitt cried out, clearly not worried about the pain.
Eventually I leaned in closer to her, ramming my cock harder into her and gaining enough momentum to gain free use of my hands. I did what any normal guy would do in that position and rip down the straps to the cheerleader outfit, letting lose her glorious tits.
'That's it baby,' I exclaimed, gripping her ass with one hand and one of her tits with the other.
Jennifer moaned and I squeezed her nipple. 'Ahhh fuck yeah baby!' Jennifer moaned.
I leant back in again and took my hand off her ass, grabbing her other tit with it and pulling her up slightly so I was fucking her with pure momentum. 'That's it fucking earn it baby,' I exclaimed.
'Fucking ruin my pussy Mr. Drake!' Jennifer exclaimed as I rammed into her.
I pulled my hands off her tits and shoved one in her mouth and one back on her ass, changing my movement to a more deliberate upward fucking. She started screaming and came right then and there, squirting on my cock to prove it. Once I knew she was satisfied I pushed her face down on the desk and really started laying into her.
'You wanna take one for the team baby?' I said through gritted teeth.
'Do whatever you want to me,' Jennifer managed, her voice muffled as her thick lips were pressed against the desk.
'I'm gonna fuck you in the ass,' I informed her, still pumping hard into her.
'Take my virgin asshole baby,' Jennifer begged. 'I'll let you fill anything if it means getting on the team.'
My eyes lit up with excitement as I pulled my cock out of her cunt and levied it against her asshole. Without a word I shoved it deep in, the tightness of it sent a completely different form of pleasure through my body. From the looks of Jennifer's face and the sound of her moan, I could tell that it did for her as well.
'You're my perfect little team player,' I breathed as I fucked her asshole.
'Fuck my ass harder!' She exclaimed. 'Fuck it like my pussy!'
I was slightly hesitant at first, afraid I may hurt her, but I decided to just do what the lady asked. I rammed as hard into her asshole as I could, making sure to grip her waist as I did, for maximum leverage.
'Oh fuuuck yes!' She moaned in the lowest decibel I think she could manage.
I picked up the pace and attempted to truly fuck her butt like a pussy, but it proved too much and before long I knew I was going to cum. 'I'm gonna cum in your asshole,' I exclaimed, pulling my right hand off her waist and placing it in the air above her currently filled ass.
'Cum in me baby!' She moaned right before I slapped her hard on the ass cheek. 'Fuck!'
'You're my little cheerleader slut,' I said as I continued to both slap and fuck her butt.
'Cum inside me! Fill my asshole with your cum!' Jennifer begged, clearly nearing a second climax herself.
'Ready for it baby?' I questioned as I could feel the cum rising.
'Fill me!' She breathed and I was done, cum shot out of my cock hard up into her asshole.
'Holy shit,' I panted as I pulled my cock out in time to cum again, this time all over her ass cheeks.
'I know baby,' Jennifer breathed as she pulled herself up, tenderly attempting to lean against the desk but finding herself unable. 'I'm gonna need to lie down after that... face down.'
'I can't believe it took you 33 years before you got butt fucked,' I said, leaning up next to her. 'Looks like the student has become the teacher.'
Jennifer playfully slapped my arm. 'You know I was just getting into the roleplay when I said that right? I've probably been butt-fucked more times than you've jerked off.'
'I just wanted to thank you for a great week and what is sure to be a great article,' Jennifer said over the phone.
'What did you have in mind?' I responded, my cock already half hard just thinking about it.
'Drinks? My place?' Jennifer suggested.
'Sounds perfect,' I said somewhat sweetly.
It didn't take me long to get to her place, it actually wasn't really all that far from mine. I felt pretty good about the whole situation, although I had no idea what she had up her sleeves for our final meeting, what could possibly upstage anal? I knocked on the door, full of excitement about what was about to go down, and then something happened that I didn't expect.
'You must be Desmond,' a man I recognised to be Brian Hallisay said after opening the door.
'And you're Brian,' I said, stretching my hand out in hopes that this wasn't some sort of ambush.
Thankfully he took my hand and shook it. 'Nice to meet you, come on inside.'
He walked me through a set of hallways, heading in no clear direction. 'It's so great to finally meet you, you know, put a face to the name, Jennifer will not shut up about you.'
'Really?' I questioned, as I followed the man into what was for all I knew my death.
'Oh yeah, she practically begged me to let you come over tonight,' Brian said as we turned into a living room. 'Take a seat, Jennifer will be out in a minute,' he said, making to leave the room while pointing me toward the couch.
'Uh...,' I said, moving toward a couch and sitting down.
'You want a beer man?' Brian called out from what was probably the kitchen.
'Yes please,' I called out. 'I certainly need a fucking beer,' I said to myself quietly.
Brian came back in with two beers and threw one to me, before sitting down on the couch right next to me. 'You know, usually Jennifer never talks to me about her fuck buddies, so you must be really special,' he said.
'Wait... what?' I exclaimed, nearly spitting out my beer. 'You know?'
'Do I know?' Brian said, looking at me like I was crazy. 'What do you think you're doing here dude?'
And suddenly, as if on cue, the lights went down and a door to our right opened up and out stepped a purple and black haired Jennifer Love Hewitt.
'Oh...' I said to myself, looking at her cleavage boosting black lingerie.
'Just enjoy the show man,' Brian said, placing his hand on my shoulder. 'Just enjoy the show.'
There are a lot of things in this world I need to be asked to do, going for a physical, paying my phone bills and even sometimes putting on a condom. Watching and enjoying this show was certainly not one of them.
Cheesy rock music started playing, as if from nowhere, it was probably something like 'Cherry Pie'. No matter what it was, Jennifer was dancing her heart out to it, letting her tits jiggle with each seemingly rehearsed step she took.
'She do this often?' I questioned as Brian took a sip from his beer.
'With a guest? No... this would be a first,' Brian answered, not ripping his eyes away from his sexy girlfriend.
She performed every stripper move in the book, popping her pussy, bending down while sexily looking up, all the way to joyfully rubbing her tits. If I didn't know any better, I would have guessed that Jennifer was a full time stripper.
Eventually she zeroes in on me, walking over to my seat and giving me a lap dance. I looked over at Brian, who was happily watching the two of us. I gave him a look as if to ask if he was okay with what was happening. He merely nodded, smiling almost manically and pulling his beer up for what looked like a toast.
Jennifer turned around and bent over, putting her ass in my face. Brian nodded at me, and mouthed for me to grab it as she twerked and even made a gesture with both hands demonstrating as much.
I happily did as she suggested and placed both my hands on her nice round ass. 'Eager beaver as always,' Jennifer said over the music.
'I can't help myself,' I responded as she stood up, slightly moving her butt closer toward me.
'I suppose you want to fuck me already?' Jennifer said mockingly.
'Uhh... well of course,' I said. 'But what about...'
'I'm cool with it,' Brian responded, making me remember he was sitting right next to me. 'I've always wanted to know what it was like to watch my girl get railed by another man.'
I didn't need any more permission than that and quickly shoved my fingers in Jennifer's panties, ripped through her stockings and pulled them down. 'You have any idea how much money that cost?' Jennifer questioned as I ripped her panties all the way off, exposing her pristine pussy.
'I know I don't give a shit,' I said, pulling her down and forcing her to grind on my crotch.
She reached behind her and unzipped my fly. I undid my belt and the two of us together began pulling my trousers and underwear off, just far enough that my cock was free to penetrate Jennifer's awaiting pussy.
I pulled her down and shoved my cock up into her pussy. 'Fuck I love this cock enough that I forgive you,' Jennifer moaned as she gyrated on my prick.
'I love this fucking ass,' I moaned as I gripped her ass cheeks and bucked my cock up and down into her pussy.
She bent forward and bounced her cunt up and down on my cock. 'How's the view?' She asked while riding my cock reverse cowgirl.
'Could be better,' I said as I unclasped her bra, ripping through the rest of her stockings to release her iconic tits.
Her lingerie fell to the ground and the remaining stockings scattered over her body made her look like she's just spent a night working the streets. 'You're so fucking sexy,' I exclaimed.
'You're telling me,' Brian said, who was now standing up right in front of Jennifer, pants around his ankles cock hard as a rock.
'Give me that cock baby,' Jennifer moaned as she took Brian's cock in her hand and jerked it off.
'Best fucking handjobs right Desmond?' Brian said as he groped his girlfriends exposed tits.
'Suck his cock,' I commanded, bending over as I stood up and fucked her in a standing doggy posititon.
'You wanna Eiffel Tower me?' Jennifer questioned as Brian rubbed his cock along her face.
'I wanna treat you like the fuck toy you were born to be,' I said, piling my cock into her and slapping her ass.
'I'm gonna fuck your pretty little mouth baby,' Brian said before shoving his cock into her awaiting mouth.
The two of us rammed into Jennifer in almost unison, my hands were tightly gripping her perfect round ass and his were doing the same to her head. 'You ever done this before?" I questioned Brian while I doggy fucked his girlfriend.
'This is my first time,' Brian responded, eyes rolling his head as Jennifer presumably did something extra hot with her mouth. 'I'm sure she's done this plenty of times though,' he admitted.
'She comes across as a real expert,' I said, harshly smacking her ass again.
'Best fuck I've ever had,' Brian said, pulling her hair slightly.
'Do you mind if...' I started, looking over at Jennifer's mouth. 'That looks really good, do you wanna switch?'
Brian shrugged. 'Not gonna turn down this piece's pussy.'
I pulled my cock out of Jennifer and Brian pulled his out as well and the two of us discarded our remaining clothes. We circled around Jennifer as she got up. 'Boys, as much as I like being filled from both ends, do you mind if we take a different approach, standing bent over is not comfortable.'
Brian and I shrugged. 'What did you have in mind?'
Jennifer pulled Brian down to the floor and lowered herself on his cock. 'Good call baby,' Brian exclaimed as she rode his dick.
'Perfect,' I said as I approached her cock in hand and ready to enter her mouth.
Jennifer moaned as I shoved my cock in her mouth, gripping her tits as I let her mostly do all the work. 'Fuck this is amazing,' I moaned, squeezing her tits and lightly bucking into her mouth.
'Really fucking give it to her man,' Brian said, as she gripped Jennifer's ass.
Not one to disappoint I gripped the back of Jennifer's head and shoved my cock as hard as I could into her mouth. She moaned and spit and saliva drooled out as I skull fucked her. 'Like being filled up?' I questioned as I fucked her face.
Jennifer merely moaned, unable to really respond to me. 'Fuck yeah baby, ride my fucking pole!' Brian exclaimed.
We kept at this for a little while, I switched between focusing on face fucking her and playing with her tits while she blew me. Eventually though I knew there was one thing I wouldn't be able to not do.
I pulled my cock out of her mouth. 'Wanna take the mouth again? I want fuck these tits,' I said, gripping them with one hand and her cheek with the other.
'Get her on the couch,' Brian said as Jennifer climbed off his cock.
Brian and I grabbed Jennifer by the arms and threw her down on the couch, wasting no time as I straddled my waist and pressed her tits together around my cock. 'This has been a lifelong dream,' I said as I began fucking her glorious tits, the wetness from her mouth and pussy being more than enough lube.
'Fuck my tits baby,' Jennifer moaned, before immediately having her face filled with Brian's cock, he wasted no time gripping her head and skull fucking her.
I gripped her nipples and let her squeeze her tits together while I fucked the shit out of them. 'I'm gonna fucking cum all over your face,' I exclaimed as I rammed between her melons.
'Me too,' Brian said as he face fucked her.
'You're gonna taste a lot of cum tonight,' I said as I twisted her nipples.
Jennifer moaned loudly and I couldn't help myself, as much as I wanted to keep fucking her tits I knew I was about to cum. I pulled out and started jerking, aiming directly at her face. Brian did the same, tugging at her cock like a mad man as the two of us readied to cum.
'Cover me!' Jennifer moaned.
Immediately we both started to gush cum, quarts and quarts of it spilling all over her as she smiled and licked it up.
'I can't fucking believe it,' I said as I shot another load on her nose.
'Incredible,' Brian said as he shot one more load on her cheek.
'What a week huh?' Jennifer joked as I shot one final load all over her lips and chin.
'It's gonna make one hell of an article,' I said.
End of Chapter 3.
Aug 14, 2018 in anal