I had met Mandy on numerous occasions previously. She was a good looking lady, about 58 years old. She had shoulder length blonde hair (probably dyed) and a nice figure for someone her age – not perfect but given that she was nearly 60 then more than acceptable. She had a nice face – her eyes were wide and sparkly, nice smile. She had crows feet at the sides of her eyes and her face now showed signs of her age – wrinkles here and there that actually looked pretty good on her.
She generally wore quite a lot of make up (probably to hide the signs of aging) and nice clothes. What I really liked about her was that she was very flirtatious. She talked a lot, was suggestive, with lots of touching, laughing and flicking of her hair.
She certainly knew how to use her feminine charms to get her way.
I knew Mandy because we employed her company to work for us. In fact we gave them a lot of work. So Mandy spent a lot of time meeting me, flirting with me and trying to keep me happy.
The latest series of meetings we were having were very important to Mandy and her company. We were about to renew the contract and she knew that we had been talking to another business.
So Mandy had contacted my secretary and asked if she could see me to have a chat. The only time I could do was 6pm that evening.
My secretary called me at 6pm to tell me Mandy had arrived. As Mandy was brought into my office, my secretary told me she needed to leave and that I would be the only person left – so I would need to lock up.
As my secretary left the room I greeted Mandy. I was almost lost for words as she took off her coat and I noticed what she was wearing. She was wearing her usual significant amount of makeup – but she was dressed in a very tight red dress which was also extremely short – particularly for someone her age!
The dress was extremely tight around her breasts which looked fantastic, and as she turned to hang her coat up I noticed that it also clung to her arse perfectly. It was tight around her stomach showing off a bit of a bulge (she was 58 after all) which to me looked incredibly sexy. She looked fantastic and she knew it.
We started off with a little small talk. I asked her how her daughter was (she had previously told me her daughter was pregnant).
Mandy beamed at me, ‘I’m now a grandmother Dan. It’s great’.
The small talk continued for a few minutes then Mandy in her usual direct fashion cut to the chase.
‘Look Dan’, she said. ‘We need this contract. It’s too important for us to lose. What do we need to do to secure it?’
I thought for a moment then started to respond. ‘Mandy, we’re going through our assessment at the moment and should have an answer in the next few days.’
Mandy smiled and said ‘Well let me rephrase things. What can I do right here, right now to make your decision easier?’
‘What do you mean?’ I replied.
Mandy laughed. ‘I’m going to have to be more direct.’ She gave me a very sexy look and said ‘Dan, I will do whatever it takes to win this contract. That’s why I’m dressed like this. I’m offering myself to you here and now if it helps us win that job.’
I laughed. ‘Mandy, come on. You’re old enough to be my mum. I can’t just…..’
She cut me off. ‘Hey, less of the old enough to be your mum. I’ve fucked guys much younger than you before. How old are you anyway?’ Mandy laughed.
‘I’m 30’ I said smiling.
‘Christ’ she replied, ‘I am old enough to be your mother.’
‘Look Mandy. I’m not sure where this is going, but…….’ I started.
Again Mandy cut me off. ‘Dan. You’re an attractive guy. I need this contract. I’ve already told my directors that we’ll win it. I am going to persuade you. I’ll do whatever it takes – and I mean whatever.’
With that Mandy parted her legs just enough to let me see right up her dress. Right up to her white lacy knickers covering her crotch. She smiled at me, ‘Dan, I really do mean whatever it takes’ she said.
I sat staring at the site before me. I had a good looking, sexy older woman flirting with me. Her legs were parted deliberately and I could clearly see all the way up to her white panties.
‘Do you like the view Dan?’ Mandy purred. ‘As I said, I need this contract. If you award it to me then I’m yours to use and abuse in anyway you want. You know where I’m going with this Dan. You can fuck me right here, right now as long as you give me that work.’
I was stuck for words, and also noticed a strain in my trousers. The view was giving me a hard on.
Mandy leant back in her chair and parted her legs even more. I now had a complete view of her knicker clad pussy. Her panties straining across the mound of her vagina, a slight crease down the middle and some hairs poking out the side of her knickers.
Mandy laughed as I stared at her pussy. ‘I can see I’ve now got your attention young man’ she said. ‘Now, if I get that contract then you can have me as your personal fuck mommy whenever you like. You can fuck me anytime, anyplace you want. You call me and I’ll come running. You can fuck my pussy. You can fuck my ass if you want. You can fuck my mouth. Any hole you want Dan. I’ll fuck you better than you’ve ever been fucked before.’
Mandy started rubbing her pussy. ‘I’ll let you cum on my face. You can cum on my tits. I’ll wank your cock off for you anytime you like.’
I was now smiling. ‘Mandy – that all sounds very tempting. But you need to do better than that. I can go out and pick up women half your age any time I like.’
Mandy stood up and walked around the desk to me. She pushed my chair back and straddled me, putting her arms around my neck, her face close to mine. She giggled as she sat on me and realised my hard on was pressing into her groin. ‘Dan, you could pick up a woman half my age. But they wouldn’t be as much fun as me? Or as good a fuck? Just imagine what your cock would feel like inside me. Imagine how it would feel to have your cock thrusting in and out of my cunt. A woman my age is much better than some inexperienced twenty five year old. And besides, I’ll let you fuck me bareback. You can shag me without any protection at all – no condom.’
Mandy leant forward and kissed me hard. Her tongue pushing into my mouth. I responded eagerly. I could feel my cock straining against my trousers and pressing into her crotch. She was pushing her crotch hard against me as well.
Mandy broke off the kiss and whispered ‘I’ll let you cum inside me as many times as you want Dan – Bareback, completely unprotected. And I mean completely unprotected – I’m not even on the pill, I don’t use birth control anymore.’
Her eyes sparkled wickedly, ‘Imagine feeling your cock inside me unprotected, your cock head pushing at my cervix and my cunt muscles contracting against your bare uncovered prick. Imagine the danger of having unprotected sex with me – a woman who you don’t really know and you don’t know where I’ve been – how naughty and dangerous does that sound? Then imagine shooting your load deep into me. Imagine trying to make me pregnant. It’s probably unlikely but not impossible – you could give me a baby Dan. I’ll let you fuck me and try to make me pregnant. A woman my age can afford to take that risk – you wont get that with a woman half my age.’
She kissed me hard again.
‘Do you want to fuck me Dan?’ she purred.
‘Yes’ I whispered
‘Do you like the sound of having your own personal fuck mommy that will come running every time you call?’
‘Oh yes’ I said again, pushing my hard on up against Mandy’s crotch.
‘You call, and I’ll be there Dan. Legs spread, cunt wet and ready for you.’ Mandy laughed. ‘This is going to be fun’ she said. ‘God I get so turned on when I act like a total slag.’
This time I leant forward to kiss Mandy. Pulling her against me and down onto my crotch. Kissing hard and franticly.
‘Do you like acting the slut?’ I asked
‘Mmmmm, love it baby’ she replied. ‘When you get to my age, you can’t often get away with it. It seems to be the younger men who love it most. They seem to get turned on by some older slag offering themselves on a plate.’ She laughed.
Then she looked straight into my eyes and smiled.
‘So is the contract mine?’ she said.
‘Probably’ I replied. ‘But let’s see how the next hour pans out first.’
Mandy playfully hit me. ‘Fucker’ she said. ‘You’re making me earn this contract.’
‘You bet. I want you at your slutty best Mandy!’
Mandy kissed me hard again and put my hand on her breast. It felt fantastic – I could feel her tit held firm in a bra under her dress. It didn’t feel particularly big – but was a nice size. I squeezed it hard – probably a little too hard as she gasped.
‘Does it feel nice?’ she asked me. ‘Do you like feeling an older woman’s tit?’
‘Feels great. But I want to see it’ I replied.
Mandy had a very slutty look on her face. ‘Well I guess it’s time I let you fuck me then’ she said. ‘Are you ready to fuck a mature woman boy? Are you ready to stick that cock in my older pussy?’
She had a really sexy look on her face.
‘I want you to fuck me really hard Dan. I want your cock ramming hard into my cunt. I want you to stretch my pussy wide open. Can you do that Dan?’ Mandy teased.
I laughed, ‘I’ll give it a good go. Having my cock buried in your pussy wasn’t what I was expecting out of this meeting, but I’m pleasantly surprised. I’ve never fucked a woman your age before but I’ll try anything once!’
Mandy hit me again. ‘Don’t be so fucking cheeky’ she giggled. ‘Once you’ve fucked a woman my age you’ll never go back to the younger ones.’
My hand was still rubbing her tit at this point. ‘My tits are starting to sag a bit, and my stomach bulges more than it used to.’ She said rubbing her stomach. ‘But then that’s what comes from having had three kids. A woman’s body changes and you start sagging in all the wrong places!’
‘You look pretty damn good to me’ I replied.
Mandy kissed me hard and pushed my hand down to her crotch, her knickers felt silky and I could feel her hot pussy. ‘Of course that means that my pussy is also a bit stretched these days. I’m going to need a big cock to fill it up.’
Mandy laughed, ‘You man enough Dan? I’ve fucked a lot of guys in my time so I’ve got plenty of experience. I’ve had about 35 years of acting like a slut, had lots of affairs, and hundreds of one night stands. So I know a big cock when I see it and I know how to fuck a guy.’
She was now grinding her knickered crotch against my hand. I could feel the silky rub of her pants and the coarse hair behind. I could also feel the damp patch beginning to form.
Mandy continued. ‘Do you like what you feel?’ she purred. ‘It’s all yours for as long as I have this work. A dirty cunt for you to fuck whenever you want. I’m going to be your personal slag Dan. You can fill my pussy with your cum whenever you like.’ Mandy laughed.
Then she stood up and faced me. She turned around and ordered me to undo her zip. It was one of those zips right up the back of her dress. As I unzipped her, the dress dropped to the floor. Mandy turned and faced me. It was the first time I had been able to admire her body.
She was right – her body did show signs of aging. Her tits were sagging a little – they were small but a nice shape still. The bra was see-through and her nipples were enormous – very long and sticking out against the fabric of her bra. Her belly was not as flat as a younger woman’s and was slightly overhanging – but it still looked very sexy. I could tell that she’d had kids. Her stomach had that look that women never recover from once they’ve given birth.
I leant up and unclipped her bra. Her nipples were huge, and very pronounced. I rubbed her tits and allowed my hands to trace her nipples. Mandy sighed. Her nipples must have been about ½ inch long and were very hard. I pulled them playfully and Mandy gasped again. I pulled a little harder which she clearly enjoyed.
My mouth slid over her left nipple and I could feel Mandy pull my head closer to her chest, encouraging me on.
‘Harder’ she ordered, ‘my nipples are very sensitive – I like it hard and rough.’
I playfully bit her nipple softly, then a little harder. My other hand was pulling her right nipple hard and rolling it between my finger and thumb. The harder I pulled it the more she seemed to enjoy it.
My spare hand reached between Mandy’s legs and rubbed her crotch. She gasped and moaned.
‘Ohhh Dan’ she purred. ‘Yes baby, that’s it. Mmm, go on rub my pussy. Feel my mature cunt.’ Mandy was pushing her crotch against my hand.
I pushed the crotch of her knickers to one side and felt her pussy. It was wet and hot. I could feel her pubic hair against my hand. Her pussy lips were fleshy and pronounced and I could feel them hanging down slightly. She was extremely wet and slippery.
I rubbed my fingers down the entire length of her slit. ‘Ohh fuck’ she gasped. ‘Fuck Dan that feels good.’
As I rubbed her pussy it became wetter and wetter. Her juice was everywhere. Her cunt lips were now extremely well parted and I could feel her pussy begging me to enter her.
‘Fuck Dan,’ Mandy gasped again. ‘You’re going to make me cum. Stick your fingers in me. Come on baby finger me hard.’ She begged.
I stuck two fingers in her pussy. They slipped in very easily and she gasped. Her pussy felt large and open. She could obviously take quite a lot more. I quickly started moving them in and out as Mandy began grinding her crotch against my hand.
‘Stick more in me Dan. I’m 58 for christ sake. I’ve had 3 kids so my cunt’s not as tight as it used to be. At my age you get stretched and things never recover’ Mandy gasped. ‘Stick your whole hand in Dan. Fist me hard. Come on baby’ she continued to moan.
I hesitated. ‘Won’t it hurt’ I asked.
Mandy laughed. ‘Dan, my god. You’re fucking a 58 year old woman who’s had 3 kids. How tight do you think my pussy is going to be? Look at it as another benefit of fucking an older lady. Our cunts are stretched already so you can pound them and fist them till you’re hearts content. I want you to fist me hard Dan – right now.’ Mandy ordered.
I pulled out of her pussy and bunched my fingers together. I felt Mandy’s pussy opening against the tip of my fingers and pushed my whole hand hard against her entrance.
Mandy gasped and yelped as my entire hand pushed deep into her pussy in one go. I felt her cunt resist for a second and then my whole fist was buried inside her. I could feel her pussy enclose around my wrist.
‘Ahhhh fuck….fuck…mmmmm. Dan that’s it baby’ Mandy panted. She leant down and kissed me hard. ‘Now fuck my pussy with your fist. I want you to pull it right out and then ram it back in again – hard baby really hard.’
I did. Pulling my fist right out and then pushing it hard and fast right back in and repeating about ten times.
I looked down at her pussy as I was fisting her. She was extremely wet and her pussy was red and swollen and stretched.
As I pulled out her pussy was left as a gaping stretched hole. Her cunt looked huge as it begged my fist to re-enter her. Her pussy looked like a gaping bucket then it was filled again as I rammed my hand hard into her.
Mandy was screaming in ecstasy and gasping with each thrust of my hand. As I reached the tenth attempt to pull out she collapsed leaving my fist buried deep in her – she shuddered and shivered gasping and moaning, whilst grinding her entire pussy against my buried fist.
‘Fuck…fuck…I’m cumming Dan, yes…yes…ohhhh fuck you bastard fuck…ahhh…ahh’ Mandy screamed, before collapsing against me. Her body shivered and shook with pleasure.
I could feel her pussy convulsing against my buried fist. ‘Ahh….fuck Dan. That was mind blowing’ she gasped laughing. ‘I bet you didn’t think you’d be doing this when you left for work this morning? Fisting a woman old enough to be your mother – you dirty sod!! Christ Dan, that’s no way to treat a grandmother. I can see I’m going to have to teach you a lesson’ Mandy laughed.
Mandy then ordered me to stand and undressed me. I was suddenly standing naked in front of her.
She stood back and looked admiringly at me. ‘Not bad’ she said. ‘I’m going to enjoy fucking you.’
Her hand reached out and grasped my hard cock. I gasped as she gripped it tight and pulled me to her. She pulled my right up against her naked body. I could feel my chest crushing her tits and my cock pressing against her stomach.
She kissed me hard and started wanking my cock against her stomach. ‘I’m going to make you cum like you’ve never cum before Dan’ she whispered. I’m going to make you cum all over my naked mature body.
Her hand was wanking me hard now. Long swift strokes right up and down my entire shaft length. They were fast and hard. Each stroke made me gasp with pleasure.
‘Just think of your hard cock deep in my pussy Dan’ Mandy teased. ‘I’m going to put that cock deep in my stretched mature cunt. Then I’m going to make you cum deep inside me without a condom. Shoot your load deep into my cunt. Then I can go home and talk to my husband with your cum swirling around inside me, dripping out of my cunt. Perhaps you’ll make me pregnant just to teach me not to be such a slut.’ Mandy laughed.
Mandy then stood up and straddled me, lowering herself so that my cock head was touching her wet cunt. Then she started rubbing my cock head up and down her slit as she kissed me hard and moaned into my mouth. ‘Do you like having your cock head rubbed against my cunt opening?’ she teased.
I could feel her rubbing my cock up and down her entire wet opening. I looked down and could she her labia hanging down either side of my cock head. She was actually wanking me against her spread pussy.
I couldn’t take any more of her teasing and grabbed her hips, pulling her down to my cock. I felt my cock head against her wet gaping cunt entrance and trust up as I pulled her down onto me. I gasped as my hard cock entered her easily and slid right up to the hilt.
Mandy gasped at the same time and trust herself down with equal force. She squealed and looked at me. ‘Fuck Dan’ she gasped. ‘That feels fucking fantastic, but stop. Please, I was only joking about bareback sex. We can’t, it’s not safe. I might get pregnant, we can’t risk it.’
I looked at her slightly concerned. She stared at me then laughed. ‘Ha Ha’ she giggled. ‘Only joking, you should see your face.’
I called her a bitch and thrust my cock hard into her. She laughed again and responded equally forcefully.
Mandy was now riding my cock really hard. Her hips were thrusting back and forth expertly.
Her hands were clasped around my neck and she was leaning back which seemed to accentuate her downward thrusts. ‘Uhh… fuck Dan. Fuck me, fuck me hard. God, I can feel you hard in me. Uhhh…mmmm, fuck my cunt.’
I looked down between our bodies and could see her thrusting down on me. Each time she pulled up I saw my cock come out of her wet pussy, and then disappear with each downward thrust. I could see her mature stomach wobbling with each thrust, and her tits bounced up and down.
She came quickly whimpering in my ear ‘Uhhh fuck Dan. That’s it, I’m… I’m cumming. Yes keep fucking me. Fuck my old fanny, fuck my used cunt. Uhhhh…fuuuck….ahhh.’ Then she collapsed gasping onto me.
A minute later Mandy looked at me and smiled. ‘Thanks Dan – I needed that.’ I then felt her pussy clench around my cock. She giggled. ‘How does it feel having your cock stuck inside a woman old enough to be your mum?’
‘Fucking fantastic’ I managed to say. Then another clench.
‘It’s weird isn’t it?’ Mandy said. ‘You’ve got your cock buried deep inside me. Completely unprotected and we don’t even know each other that well.’ She laughed and then started thrusting again.
This time she was rampant. Long, hard, deep thrusts which she knew would make me cum quickly.
Her rhythm was quick and effective.
‘Come on Dan. Fuck my pussy. Fuck me hard.’
‘Fucking an older woman must be your dream fantasy. Go on fuck my mature older woman’s fanny.’
‘I want your cum inside me Dan. Shoot your load in me. I want to feel your cum deep in my cunt.’
I gasped and then thrust up in one final push. My cock erupted inside Mandy’s pussy and I heard her gasp as she felt my cum drench the inside of her cunt.
As I kept thrusting Mandy started laughing whilst doing her best to milk every drop from my cock.
‘Ohh that’s it Dan. Give me your spunk. Let me have it. Spunk in me.’ She encouraged.
A minute later Mandy lifted herself off me. As she did I saw my spunk drip out from her pussy. Some landed on the floor, and some dribbled down her inner thighs.
I looked at her and said ‘dare you to go home to your husband with my cum dribbling out of you.’
Mandy laughed ‘Don’t worry lover, I’ve no intention of wiping anything away. I want to feel your cum dripping out of me as I talk to him.’
With that she chucked her knickers to me ‘Here, keep these as a memento. And just remember – that contract is now mine. Here’s my number – just call me any time you need a good fuck and I’ll be there.’
Mandy smiled, kissed me and started getting dressed.
I looked at her and said ‘Best contract I ever entered into Mandy. By the way – you would have got the job anyway as you had the best bid. But I like this new arrangement. Just make sure you’ve got plenty of lube, because your cunt might get a bit sore – I’ll be making good use of it!!’
Mandy roared with laughter and replied, ‘Dan, my cunt can take anything you give it and more. Bring it on lover.’
Mandy then turned and left my office.