03/08/2023
Currently im a 48 yr old straight single guy in the Midlands UK, lost my wife to ovarian cancer back in 2017. So looking for new friends with benefits. I've met a lot of nice couples and single females over the years. The ones I'm going to post on here are a mixture of some meetings I've had over the last 25 years or so. I hope you enjoy.
This happened way back when I was 20, was probably one of the best ever encounters I've ever had
I couldn't believe my luck. It was my 20th. The parents had rented a large house in Wales for a week. All my friends that came down were going down to the beach, and I had to help my parents with a BBQ they were throwing.
I had tried all the excuses I could think of but they weren't buying it.
'I've paid for you to study at University for 2 years Martin, and we've hired this house for your party' my father said, 'it's the least you can do.'
So I eventually gave in and agreed to help with the cooking and drinks.
As my parents' friends started to arrive, I did the usual thing of being pleasant and polite and making small talk with people who I had known for years.
Then things started to look up a little, my mum's best friend Maggie, her husband Paul and their Lucy arrived. As they walked into the room, Paul shook my hand and quickly moved on to others. Maggie on the other hand gave me a big hug, pressing her body close to me 'Hi Martin, how are you? How's University? I haven't seen you for a while.'
Before I could answer, she quickly introduced me to Lucy, whom I had met before, but then she was a little girl,now she was a 19 year old stunner, long blond hair, a great body with nice sized tits. My immediate thought as I smiled and said hello, was that I wouldn't mind fucking her.
As the party got into the swing of things, people moved outside and started settling into a steady drinking pattern. I kept glancing over at Lucy, who was looking very sexy in a short denim skirt and skimpy vest showing off her figure to maximum effect.
I also couldn't help but notice how good Maggie was looking for a woman of her age. I knew that she was a year older than my mum, which made her 59 or 60 years old. She had short brown hair, a very attractive face with nice wide eyes. Her body was pretty good for a mature lady she was probably a size 14, her tits still looked pretty pert and a nice shape. Again I found myself thinking that I could do all sorts of dirty things with her being a horny young man.
I was suddenly brought back to reality as my dad told me to get more drinks for people. I took orders and went into the house.
I was in the kitchen rummaging around in the fridge, when Maggie entered the room.
'Hey Martin' she said, 'thought you may need a hand.' and gave me a little arse bump with hers
'Thanks' I replied 'but really I can manage.'
Maggie was looking at me in a strange way. She somehow seemed a bit different. She moved towards me and said 'So Martin, I've been watching you stare at Lucy a lot today. You seem to be fascinated with my 's tits, you randy little sod.'
I was shocked and managed to stammer 'What are you talking about Maggie.'
Maggie just looked at me 'Martin relax, I don't mind. I just find it funny that you kept staring. You must be like a dog in heat. I think you fancy her.'
'Well she is very attractive,' I said, trying to act all cool.
Maggie smiled, 'Hey that's my you're talking about young man' she said then laughed, 'anyway, I also noticed you staring at me. Don't deny it, I caught you staring at my tits a few times as well.'
I felt my face redden 'Maggie I'm sorry they were almost out on show, I didn't mean to...'
'Martin' Maggie interrupted 'I don't mind. In fact I quite liked it being admired by a good looking 20 yr old boy. I think I may have gotten jealous if my was the only one getting your attention.'
I was a little taken aback by Maggie's forwardness and didn't know what to say.
There was a little pause before Maggie moved a little closer to me smiling and said 'I don't tend to attract as many admiring glances as I used to so it's nice that someone your age is looking. I used to get a lot of attention when I was younger, but now I think people just see me as another old wrinkled married woman who is past her best.'
Again, I was struggling to say anything. This was my mum's best friend, talking to me in a way she had never done before. I guess the booze and the warm June summer must have been making her talk.
Maggie could sense my awkwardness. 'Relax Martin, as I say, it was nice to get an admiring glance. So what were you thinking when you were looking at me?' she asked with a smile on her face.
'Uh well, ...you know...just the usual' I said hesitantly, 'I, um, was thinking that you were a very attractive woman for your age. And how I would like to see you naked' I blushed
Maggie smiled again 'Really' she said 'an attractive woman for my age....mmm....I think that proves my point doesn't it.'
'What do you mean' I replied
'Well Martin, as I said, I don't tend to attract too many glances these days because people think I am too old.'
'I didn't mean that Maggie, I think you're stunning' I said thinking I had upset her.
'I know,' she laughed. 'So Martin, tell me, do you find older women attractive?'
I thought for a moment 'I've never really thought about it before, but as I said you are an attractive woman Maggie, but you're also one of my mum's best friends so I'm not sure we should be having this conversation.'
Maggie thought for a moment then said 'I know I'm your mum's best friend, but don't let that frighten you I won't tell her if you don't. What I want to do Martin, is show you how sexy a woman of my age can be. I have needs you know, ones my husband is not catering for, and it's nice when a sexy young man shows me a bit of attention. This will need to be our secret, but I can tell you like me flirting with you. I can see it's turning you on, so how about we stop messing around and cut to the chase.'
I was now starting to realise where this conversation was going 'what about your husband? What if he finds out or catches us?' I said.
'We'll just have to make sure he doesn't find out won't we' Maggie said. 'Now take those drinks out to people then come back and meet me in the upstairs toilet, make sure no one sees you and be quick.' she winked at me and then left the room
I picked up the tray full of drinks and quickly walked outside to the guests. My mind was working overtime thinking about what was going to happen. I found myself looking at Maggie's and husband thinking about the conversation I had just had, I remember thinking to myself, I think I am going to fuck your mum, I think I am going to fuck your wife kept going around in my head. But I just smiled and handed them their drinks.
I sorted the drinks and quickly went upstairs to the toilet. I knocked on the door and Maggie answered. She smiled as she saw me and in a very sexy way said 'I thought you weren't coming Martin.'
She locked the door behind me and looked at me 'I'm glad you came up' she said, 'So you like the idea of being with a woman old enough to be your mother do you?'
'Yes' was all I could say, my mouth was dry, my heart was racing, I was a bag of nerves.
'You do realise I'm 60 Martin. I'm not your young skinny supermodel type. I think I'm in pretty good shape for my age, but I've had three kids, and that takes its toll on a woman's body. Maggie moved her hands up to her tits and started to push them upwards 'At my age your tits start to sag a bit, but the nipples are still as sensitive as they always have been', she took my hand and placed it onto her left tit and started rubbing it over her breast. 'What do you think?' she asked.
'I think they're fantastic tits,' I replied, rubbing her entire boob and feeling her hard nipple against the palm of my hand. 'You wouldn't know they are drooping, honestly.'
'That's what a good bra does for them. Trust me when the bra comes off they are not as pert as they used to be.' She moved my hand down to her stomach. 'My stomach is also not as flat as it used to be again that's what kids do to you Martin.'
I was now rubbing my hand over her stomach and pulled up her top to reveal her belly, my hand now rubbing her bare flesh. I could see that it wasn't flat and that she had obviously had kids and stretch marks, but also thought that the bulge was actually quite attractive it wasn't fat, just normal for a old woman 'Maggie, you've got a fantastic body' I said 'I don't like the supermodel look, I want a real woman, with a real body and real curves just like yours.'
Maggie purred 'Good answer Martin, just what I wanted to hear older women like me need their egos massaging a bit now and again. Now, I want you to take my knickers off' she said exuding the authority that a woman her age had.
I hoisted up her skirt to reveal some rather plain white knickers and quickly pulled them down over Maggie's thighs letting them drop to the floor. As I did, her pussy was revealed to me. It looked fantastic, not shaven, but her hair was neatly trimmed. Her outer pussy lips were looking very swollen and fleshy and unlike some I had been with, her lips were slightly long, and I could clearly see that she was quite wet and moist.
'So' Maggie smiled at me as I admired her 'do you like what you see? Not too disappointed?' She took my hand and pulled it in between her legs. I felt her wet swollen pussy against my hand and fingers. 'Feel it Martin, rub my cunt' Maggie whispered in my ear 'feel what an older woman's fanny is like. Stick your fingers into me. I've had three kids, so my pussy has been stretched a bit over the years. I hope you don't mind, it's not as tight as it used to be.'
My hand was now rubbing Maggie's pussy as my fingers started pushing her fleshy outer lips apart. I started spreading her lips wider with my fingers, exposing her wet gaping hole. Maggie's breath was getting heavier in my ear as she gasped.
'That's it Martin, rub my clit' she whispered, 'stick your fingers into me, quick before anyone misses us.'
I pushed one finger into Maggie's pussy. It slipped in very easily with no resistance at all – her pussy did feel like it had been through three kids. My mind was racing, partly with lust and partly with fear that someone would come to the door. I was thinking to myself that here I was in the cottage we've rented, locked in the bathroom with my finger shoved up my mum's best friend's pussy.
Maggie brought me back to reality 'Martin we need to be quick otherwise people will miss us' she was breathing heavily. 'I need more than one finger to fill me up' she hissed, her hand went down to mine. 'I told you my pussy is not as tight as it used to be, stick more fingers into me now, make me cum quick we don't have much time' she hissed.
I had a moment of sheer lust, and quickly pulled my one finger out, bunched all my fingers together and quickly pushed them against Maggie's open pussy. My four fingers and thumb all entered her at the same time stretching her wide open. 'Fuck that's it Martin thats what this old pussy needs' she moaned as my fist was embedded into her pussy up to the knuckle. I pulled them out slightly when I felt resistance, and then pushed my whole fist harder against her pussy. My entire hand quickly disappeared into her as she gasped and moaned hard into my neck. I felt her pussy muscles tighten along with her entire body as she convulsed and orgasmed gasping hard into my neck to drown the noise. My hand was now fisting Maggie hard in and out of her pussy and she orgasmed against me.
As her orgasm died down, Maggie looked up at me smiling. She looked down at her @@@@@@@ crotch. Her wet cunt was spread open and my entire hand was embedded up to the wrist all wet all down my arm. 'I told you I needed filling up, didn't I?' she said. Her hand went down to mine and pulled my whole fist out of her. I watched my hand leave her pussy all loose and stretched it gaping open.
Maggie was now very quickly undoing my trousers. They dropped to the floor and her hands started rubbing my hard cock. This is it I thought, I'm about to fuck a old woman in the bathroom.
'I want your cock Martin' Maggie said. 'I want your cock and all the cum inside it' she purred as my boxers dropped to the floor.
Maggie's hand grabbed my cock as if it was going to escape. She took a really hard firm grip and pulled me in between her legs. I felt Maggie's wet pussy against my hard cock head and started to push forward.
Maggie said 'Hold on Martin I've got other plans for you' she smiled with a lusty, dirty look on her face. 'I want your cum all over the outside of my cunt.you can fuck me but I'm going to make you cum over my pussy. Then I'm walking out of here and going to talk to your mum, my husband, my knowing that I have your cum all over my cunt feeling it dribble down my inner thighs as I speak to them'. After she let me have a few thrusts in to get me moist She then pushed me out and was now wanking my cock really hard and quickly over her opening which felt great.
I started to protest 'Maggie slow down, I need to.....'
Maggie kissed me hard 'Martin don't worry you will fuck me and fill me I promise, just not now later on' she said. ' Look down there' she said 'how many boys your age have experienced an old woman wanking their cocks against their pussy just relax and enjoy.'
I looked down my cock head was being wanked against Maggie's swollen stretched pussy glistening after being inside her all covered in her juices.
Maggie was whispering in my ear 'Go on Martin, cum on me. Spunk on my pussy. I want your cum all over me. Come on spunk my pussy now.'
I felt my orgasm building and could not hold back any longer. I exploded all over Maggie's spread pussy. As I did she pressed me hard against her @@@@@@@ hole rubbing my cum all over her cunt and against her inner thighs. I kept cumming over and over again, thrusting in Maggie's hand as she rubbed my head inside her pussy lips and said 'That's it Martin, keep cumming on me, go on I want it all...'
My orgasm subsided and I looked down. Maggie let go of my cock and started rubbing my cum all over her pussy and thighs. She looked at me as her hands scooped up a big handful of my cum, then she pushed her fingers and my cum up into her pussy 'there you go that lot will dribble down out of me while I'm talking to your mum' she said laughing.
Maggie's cunt was a complete mess of spunk. It was all over her pussy, her thighs everywhere. I watched her scoop another load in her fingers and push my cum up her pussy. 'What happens if you get pregnant?' I said being a young man I didn't yet know all the facts of a ladies life cycle.
Maggie laughed 'Bloody hell Martin im old, it's pretty unlikely'. With that she quickly started putting her clothes right, straightening her skirt and top and looked in the mirror. She quickly made herself presentable, then picked her knickers up.
'I won't be needing these' as she tossed them to me. 'Have them as a memento'. With that she opened the door and checked it was all clear. She looked back at me, smiled and said 'It's all clear see you soon for the next encounter' then shut the door behind her.
I sorted myself out in the bathroom, then went downstairs to rejoin the party. My dad bumped into me as I was walking outside. 'Good I was just trying to find you, can you man the BBQ and serve some food please' he said. I need to go to the bathroom.
I started walking over to the BBQ and glanced over at Maggie. She stood talking to both my mum and her husband as if nothing had happened. She looked over at me and gave me a sexy smile as I walked past.
As soon as I took my place behind the BBQ a queue of people formed. I could see Maggie and her at the end moving closer as I served the food up. The two of them were last in line. Maggie smiled at me. 'What do you want to eat Lucy?' she said.
Lucy was thinking, but Maggie quickly interjected 'How about having one of Martin's sausage' she joked. Lucy looked horrified 'Mum, shut up you idiot' she said 'You're embarrassing bloody hell'. Lucy looked mortified and quickly grabbed some food then stormed off to sit down.
Maggie looked at me in a sexy way 'She can't take a joke can she' she said. 'I'll have one of your big sausages Martin please'. Smiling, I put one on her plate. Maggie was looking at me, then glanced over her shoulder at the party to see if anyone was looking. They were all too busy eating. She turned back to me and said 'That looks nice, but it probably needs a bit of the chef's sauce'. Her hand quickly went up her skirt, she scooped around and her fingers reappeared with a glob of my cum on them. She wiped my cum onto her sausage, took a big bite and said 'That tastes much better' then walked off.
As the party went on, my mind was all over the place. I couldn't stop thinking about the dirty and unusual encounter I had had with this woman old enough to be my mother. Was I going to shag her? Would she tell my mother? Would she get pregnant? Was she some kind of slut? I had all sorts of questions going around in my head. But most of all I was really horny I had to fuck her. I was desperate to fuck this gorgeous older woman. I kept watching her talking to her husband, talking to my mother wondering how much cum she could feel dribbling down her thighs. She did give me the odd sexy glance when no one was looking, which just made me even more horny and she knew it.
At one point she passed by me and stopped just long enough to say that she had just been talking to my mum and felt a long trickle of My cum going down her thigh. She then chuckled and walked off to talk to another guest.
After about 10 minutes, Maggie suddenly announced that she was going to get a drink and did anyone else want one. She ended up taking an order for about 7 drinks. My mother offered to help her, but Maggie announced 'No, don't worry, I'm sure Martin wouldn't mind giving me a hand'.
I was more than happy to spend time with my newfound sexy old woman 'Yeah no problem' I replied.
The house was such that you could walk in the patio doors, through a long lounge and some double doors which were open at the end into the dining room. There was a bar that the owner had created at the end of the dining room which looked a bit tacky, but they liked it. When you were at the bar you could see right through both rooms to the patio outside into the garden. All the guests were sitting just to the left of the patio door so as to not block it.
I followed Maggie in towards the bar. As we reached it she stopped and looked at me. She had a look of lust on her face that I had only ever seen in a porno movie before. 'Listen Martin' she said quickly, 'I want you to fuck me behind this bar doggy style. I'll bend over and start making the drinks. You pull my skirt up, and fuck me hard but be really quick we don't want to get caught. Just pretend that you are making some drinks as well. Don't worry about foreplay or anything like that just quick hard fucking and cum in me as quickly as you can.'
'Maggie I haven't even got a condom' I said.
'For fucks sake Martin, I've already told you don't worry about that fuck me raw and cum in me. I'll sort something out tomorrow, but I'm hardly likely to get pregnant' Maggie moved behind the bar.
I moved in behind her, feeling very conspicuous. She told me to relax and pulled up her skirt. I could see her bare arse sticking out at me and her fleshy pussy lips between her thighs. She started sorting drinks out and pushed back against me as if to encourage me to get a move on.
I pulled down my zip and pulled my cock out of my trousers. It was hard and immediately flopped down between Maggie's ass cheeks. I heard her giggle as she felt it against her. I moved back and positioned my cock against her cunt. I was thinking this is it I'm finally going to fuck her.
With that I pushed my cock straight into her. She was still wet from earlier. Maggie let out a low groan and at the same time pushed herself back against me ensuring that my cock was as deep as it could be.
'That's it Martin. Fuck that feels good, now fuck my pussy, use your young cock to teach my older pussy a lesson, cum inside me deep and hard' Maggie said under her breath. 'Reach up to the cupboard above my head and pretend to get some glasses out – that way you can push deeper into me' she said.
I reached up and started rummaging around. I was thrusting my cock in and out trying to be as casual as possible, and all the while knowing my orgasm was building quickly. As I pushed my cock deep into her, Maggie pushed back against me each time giving us both as much pleasure as we could possibly get. I knew I was not going to last long and felt my orgasm building.
'I'm going to cum Maggie' I said about reaching the point of no return.
'Uhh...Fuck Martin' Maggie whispered 'cum up inside me, fill me up, fuck my mature pussy Martin....go on put your cum deep inside me, see if you can give me a baby' Maggie laughed at the last comment and was trying to look like she was making drinks.
I gave one last thrust and knew that was it, I was cumming.
Just at this moment I heard a voice calling. 'Maggie, we need three more beers love' her husband shouted. I was horrified to see Maggie's husband's face at the patio doors about 4 metres from us. 'Is that all right' he said.
I had reached the point of no return, I could not stop. I was well past that point, I was pumping a load deep in her pussy but all I could see was Maggie's husband looking in through the rooms, with just the bar between me and his wife. Maggie clearly sensed that I was frantically trying to stop and panicking. She just pushed herself back against me and my cock as I exploded my cum deep into her. Her pussy muscles tightened their grip around my cock as she pushed back against me and I felt my cum shoot deep inside this sexy mature woman, but all I could see was her husband looking at us, but completely oblivious to what was happening behind the bar.
To my horror Maggie then started speaking to him as I was pumping my sperm into her. 'How many do you want Paul?' she said as she kept thrusting herself back against me, milking my cock for all it was worth. Her pussy muscles had gone from being very slack upstairs to now having a vice grip on my cock. 'Do you need anything else?' she said.
'That's it love I've asked everyone' Paul replied.
'I'll bring them right out' Maggie said with a bit of breathlessness to her voice, 'Martin is just helping me so give me a minute.' Maggie's husband disappeared from view and I relaxed slightly.
Maggie was still pushing herself back against me as my orgasm subsided and my cock started to grow limp. 'Did you enjoy that Martin? Fuck I thought he was going to catch us just as you spunked in me' Maggie laughed quietly. 'That was such a turn on, you were cumming in me as my husband watched. I've never felt so fucking turned on in my life. I just couldn't stop myself.'
I was still in shock, 'Fuck Maggie he nearly caught us. I can't believe you started talking to him.'
Maggie laughed again 'that's all part of the turn on Martin. My husband talking to me whilst I act like a complete slag fuck another guy that turns me on.' Maggie moved forward and my limp cock fell out of her pussy.
Maggie's hand went down to her pussy. I could clearly see the creampie I had left her with. For the second time that day her cunt was awash with my spunk. But this time it was deep inside her. Maggie rubbed the excess cum dribbling out of her pussy across her @@@@@@@ lips then straightened up and turned to face me.
'Don't worry' she said, 'If I get pregnant I won't come after you but us oldies normally can't get pregnant after the change.' With that Maggie, knelt down behind the bar and put my cock into her mouth licking off the excess cum with a smack of her lips. She then tucked my cock away and zipped up my trousers.
Maggie then stood up, straightened her skirt, picked up the tray of drinks and made her way outside.
One hour later................
I was upstairs in my room, thinking about what had happened when there was a knock
My thoughts were interrupted by my mother knocking on the door.
I wandered downstairs to find guests leaving the party. My mother was kissing people as they left.
The last to leave were Maggie and her family. As she came past me, she put her arms around me and whispered in my ear thank you for helping out. She gave me a big hug pressing her body against me. As she kissed me on the check she whispered 'and thank you for being such a good fuck we'll do it again soon.'
I whispered back 'Thank you for showing me how good an older woman can be.!'
Maggie looked at me with surprise as I gave her a quick kiss on the cheek and walked off.
I was still spent and just wanted to get to bed.
We continued this for the next 4 years on and off, before she finally passed away at 65, to date she's still the best over 60 I've ever fucked unless you want to change my mind…..