Author’s note: My current boyfriend* is less than half my age (27/57) and he recently told me that I am the first M.I.L.F. (his description, not mine) that he’s fucked. What follows is my version of his life since becoming a ‘Toy Boy’. I have shown him the completed story, and he loved it, and he also loves my version of the same story, which I have entitled ‘Ploughing Her Own Furrow.’ Check it out! I hope my loyal band of readers will enjoy them both as much. Even though this is an edited version of real events, (because vanilla life gets in the way much too often) I am obliged to note that all the sex described takes place between consenting adults of at least eighteen years of age. Please consider using the star system to show your approval of this story, and as usual, all constructive comments are welcome.
*Sadly, this is no longer the case, but I had a good time while it lasted and I’ve had his blessing to submit this story for publication.
First of all, I need to establish that I am not your typical twenty-something year old male. Yes, I’m horny all the time, and yes, I love lots of sex, but a lot of my mates think I’m weird, because I am not attracted to girls my own age. My ideal date would be a MILF in her forties, someone who is uninhibited, and if she happened to be a smoker, so much the better. I told you that I’m not typical. I have a huge smoking fetish, despite the fact that I don’t smoke myself. So, that’s my cards laid out on the table. I’m nothing if not honest, and if you don’t like what you’ve read so far, then no hard feelings. Just move on and find some author who writes about what turns you on.
The story I am about to relate began just before Easter last year. I should explain that I’m a librarian in a quiet, small Welsh town. I’m responsible, amongst other things, for organising exhibitions and events in the library, and at the time when my story begins, I had arranged for an exhibition of modern art which reflected the traditions of Easter around the world to be shown in the upstairs gallery.
A week before the exhibition was due to begin, I was informed by my boss that the council had invited a local primary school choir to attend. The thinking was that it would boost the number of people attending the opening night, and it was, it seemed, a fait accompli. I wasn’t happy to have a bunch of sprogs wailing on my opening night, but my boss told me to get on with it and make the arrangements. I did as I was told.
A rehearsal was arranged for the afternoon of the opening. The children arrived, accompanied by two of their teachers, and a young man, whom I later discovered was the bus driver. He had been recruited to carry the keyboard into the library, and once it had been set up, he disappeared back to his vehicle.
When I introduced myself, I had the feeling that I might get something out of this situation after all. The teacher in charge shook my hand and introduced her young colleague. The young woman, whose name was Marion, blushed, shook my hand and immediately began to organise the children into some sort of order.
The older woman smiled at me and began to make conversation.
“Thank you for having us,” I remember her saying at one point.
“I’d love to have you,” I thought to myself. She was quite tall, well built, with a beautiful pair of tits, and it suddenly struck me that her subtle, musky perfume indicated that she might well be a cigar smoker. (Remember, I have a smoking fetish, and I know the smell of cigars very well indeed!) I replied that it was a pleasure to showcase the local village school and all the hard work they were doing at our opening evening. I hoped she wouldn’t notice the bulge in my trousers. Mrs. Simpson, as she had introduced herself to me, was making me very horny indeed.
The rehearsal went very well. Mrs. Simpson was the accompanist, and her younger companion conducted the choir. Much to my surprise, they sounded very tuneful, and they obviously adored their young conductor, because they listened intently to what she had to say, and they all did exactly as she instructed. I found myself looking forward to the evening’s performance.
When they had finished practising, Marion began telling the children the details of what was required of them that evening. I heard her saying that they must wear their school uniform, and that the girls who had long hair must have it tied back out of their faces. It took me back to my own schooldays, when all the children hung on their teachers’ every word. I suddenly became aware that Mrs. Simpson was standing next to me. I inhaled deeply, catching her subtle aroma, and I was aware of my cock stirring in my trousers.
“I’ve arranged for the children to be picked up from here,” she informed me with a smile. “Getting them back to school on the bus at going home time would be a nightmare. So their parents and grandparents will be picking them up from here. I hope that’s ok?”
“No problem at all,” I smiled, “but how are you and your companion going Sahabet to get home if you’re not going on the bus?”
“Marion’s wife is coming to pick her up,” Mrs. Simpson replied, “and I’m staying in town. I thought I’d grab something to eat, come back here by about six o’clock, and change ready for the concert. Will that be possible, do you think?”
My mind went into overdrive. I was still trying to manufacture a scenario whereby I could find out more about this woman when the butchest dyke I’ve ever seen turned up. She kissed Marion quickly, nodded to Mrs. Simpson, and totally ignored me.
“See you back here at six,” Marion said, holding hands with her wife and smiling her goodbye. I turned my attention back to the object of my lustful intentions.
“Would you like to join me for a snack and a coffee?” I began. “I’m on duty tonight, and I usually go to the deli when I’m working late. The coffee is amazing, and they do tasty snacks as well.”
To my delight, Mrs. Simpson agreed to accompany me, and as we strolled the hundred and fifty yards or so to the deli, she slipped her arm through mine and informed me that she was looking forward to getting to know me better. I couldn’t believe my luck, and neither, it seemed, could my cock, which was definitely showing an interest. I had a hard on all the way to the deli!
To my surprise, Mrs. Simpson was greeted warmly by the deli owner when we arrived. The late afternoon rush was beginning to slow down and there were plenty of tables available. We decided to sit outside in the early spring sunshine, and no sooner had we sat down than the owner came up, carrying two menus.
“How are you, Mrs. Simpson?” she smiled, handing over the menus. “We haven’t seen you for a while. You’re still teaching in the village school?”
Mrs. Simpson confirmed that she was indeed still teaching, and enquired about two people called Rebecca and Richard.
“Richard is a solicitor up in north Wales,” she was told, “and Rebecca is living with her partner down in Cardiff. She’ll be thrilled when I tell her that I’ve seen you. She loved you when you were her teacher.”
Eventually, the deli owner moved off to clear some tables and serve other customers.
“Sorry about that,” Mrs Simpson smiled, “as you might have worked out, I taught Mrs. Ellis’s children, more years ago than I care to remember.”
“You’re not that old,” I protested gallantly, and she smiled at me.
“Old enough to be your mother,” she countered, and there was no answer to that. I tried a different tack.
“I hope your husband won’t mind you sitting down for a meal with a young man,” I said. “You know how people gossip in this village. Everybody knows Mrs. Simpson, it seems. I don’t want to embarrass you.”
“My husband understands my needs,” she replied enigmatically, “and while we’re on the subject, please call me Olwen. All this ‘Mrs. Simpson’ malarky does make me feel old!”
Then to my delight, she put her hand on mine and uttered the phrase that will stick in my mind for a very long time.
“I noticed a delightful bulge in your trousers earlier,” she said softly. “You can have me later on, if you’re interested!”
Interested? I almost came in my pants on the spot! But I needed to make some sort of token protest before she ‘persuaded’ me to have sex with her.
“Your husband isn’t going to be too happy that you’ve made such an offer,” I suggested, and in reply, Olwen took her phone out of her bag and dialled a number. She put it on speakerphone, so that when it was answered, I could hear every word.
To my amazement, she told her husband, who confusingly, was also called Richard, that she was sitting with me, and that I’d be coming home with her at the end of the concert. She even asked me to confirm that everything would be over by eight thirty. When I confirmed that it would be, she told her husband that we’d be ready to be picked up at that time, and that she expected him to be polite and respectful.
I heard him mention something about being private, but my head was in a whorl. It seemed that I was going to fuck Olwen later on, and that her husband would know about it, and not threaten to beat me into a pulp.
She looked at me and smiled again.
“I hope you’re discrete,” she said quietly. “If it ever got out that I was being fucked by a gentleman who is young enough to be my son, it wouldn’t do my reputation any good at all!”
I couldn’t believe my ears. This middle aged, respectable woman had just confirmed that she wanted me to fuck her! I think that I managed to stutter something to the effect that I was indeed the soul of discretion.
The opening of the exhibition passed quickly, thank goodness. I know I made some sort of welcome speech, and I know the school choir sang. What I said and what they sung I couldn’t tell you. All I remember about that couple of hours was thinking about fucking Olwen, and seeing her smile and lick her lips in a disgustingly lewd gesture everytime I looked Sahabet Giriş at her.
And then, the concert was over, and everyone was leaving. I stood at the front door of the library, shaking hands and thanking people for attending. My smile was as false as hell. Even as I was expressing my gratitude for their attendance, I was wishing them far away, so that Olwen and I could be alone and my ambition of fucking this sexy MILF could come about.
At last I saw Olwen coming down the stairs and into the lobby.
“That’s the last of them,” she said, nodding to a small group of people making their way out. “Our taxi has just pulled into the car park. I hope you’re up for this?” She looked pointedly at my trousers, and licked her lips again.
“I just have to lock up and put the alarm on,” I replied, my voice cracking as I spoke. She was as anxious to get started as I was, I thought. But she didn’t seem in the least bit nervous. I wished that I could feel the same way as she did!
It was a matter of seconds to switch off the lights, programme the alarm and lock the front doors. As she took my arm and led me towards the only car in the carpark, a tall, well built man got out and opened the back door. I was conscious of Olwen muttering something about leaving the school keyboard overnight, but all I could think of was what was about to happen. Her musky scent filled my nostrils and my head swam.
He smiled as Olwen and I approached the car.
“Good evening, dear,” he said, kissing Olwen chastely on the cheek. “How did the concert go?”
“Swimmingly,” Olwen replied. “The children were excellent. Now then, Richard, this gorgeous hunk of manhood is Jacob. He’s coming home with us, and he’ll be spending the night. I think he’s somewhat nervous about the fact that you are going to be present when he fucks my brains out.”
I felt myself blushing, but Olwen’s husband turned to me with a genuine smile. He offered his hand to shake.
“Hello, Jacob,” he said with what looked to me to be a genuine smile. “Thank you so much for hosting the exhibition and for offering to take care of Olwen this evening. Please don’t be nervous. I’m reliably informed that Olwen is a very considerate lover, and as I’m not equipped to satisfy her, I’m extremely grateful that you have offered to give my darling Hot Wife some pleasure. If it helps to reassure you, I’m sure she’ll return the favour and give you a night of pleasure too.”
I shook his hand limply, not believing what I was hearing. This bloke was encouraging me to fuck his wife!
As she got into the back seat, and I followed her, Olwen said to her husband that she wanted him to take the scenic route home. It seemed that she needed at least ten minutes with me before we got to their house.
“Yes dear,” replied Richard, pulling slowly out of the parking space and indicating that the car was turning left. We weren’t going down the by pass, we were going to be driving through the centre of town. I looked nervously at Olwen. She snuggled up close to me and put her hand on my cock. I shuddered with pleasure at her touch. She moved her face closer to mine and asked me if I wanted to kiss her. She told me that she was going to suck my cock in a moment, and that she didn’t know if I liked the taste of cock breath. Her musky perfume set my senses reeling again, and as our lips met, she started to undo my zip.All I can remember about that exact moment was the taste of her tongue as she slid it into my mouth and the warmth of her hand as she fished my cock out and peeled back my foreskin.
“Oh fuck,” I thought to myself, “I’ve died and gone to heaven! I only hope I don’t cum before she makes good on her promise and sucks my cock!”
I felt a stab of disappointment as Olwen broke off our kiss, but that didn’t last long. She dipped her head and I felt her breath on my cock. Then it was in her mouth, and I groaned with pleasure. I noticed that Richard’s eyes were looking at us in the rear view mirror, and I grinned at him. He returned his gaze forwards, and his wife started to suck my cock in earnest.
There is something about having your cock sucked by an outwardly respectable woman, who is old enough to be your mother, whilst being driven through the town centre, that is incredibly exciting. It was something that I’d fantasised about (the sucking, not the being driven) for a very long time, and as Olwen’s lips and tongue continued to work their magic on my cock, I realised that I wasn’t going to be able to hold back for very much longer.I managed to gasp out a warning to her.
“This is absolutely fantastic,” I croaked, aware that because my mouth was so dry, I sounded like my voice hadn’t yet broken. “If you carry on much longer, I’m going to cum in your mouth!”
Olwen released my cock with an audible plop.
“That’s the idea,” she chuckled. “I want to make you cum before we get home. That way, when I get you into bed, our first fuck won’t be of the ‘Wham! Bam! Thank you, Ma’am!’ variety. Sahabet Yeni Giriş She resumed her sucking, and her tongue continued to tease and thrill my rampant cock.
I heard Richard say from the front seat that we were almost at our journey’s end, and I remember thinking that my journey was almost finished as well. My cock felt as if it was about to explode, and even as I thought about warning Olwen, I knew it was too late.
“I’m cumming!” I yelled, and my voice sounded as if I had my balls trapped in a vice. I sounded like a boy soprano!
“Oh fuck!” I continued, “Look out, Olwen! Here I cum! Oh… fu…ck…ing… hell!”
I shot my first load into her mouth, and to give her her due, Olwen didn’t bat an eyelid. She swallowed it all and continued her sucking, draining my balls which probably had the best part of a fortnight’s worth of cum in them. I’m not a virgin, and my last fuck had been with a girl I’d been in school with many years ago. It did the job, but as I noted at the start of this story, girls my own age don’t really do it for me. Olwen made me cum like a burst water main, and I couldn’t wait to get her into bed to show her what fucking a MILF meant to me.
The car stopped and Richard turned the engine off. He got out and opened the back door, and what a sight greeted him! His wife was still sucking on my rapidly deflating cock, and I looked at him, expecting to see anger and jealousy in his eyes. Not a bit of it! Richard watched intently as Olwen reluctantly released my cock, and slid out of the car. She didn’t say a word, but took Richard’s face in her two hands and kissed him. It suddenly occurred to me that she still had the dregs of my cum in her mouth, and she was transferring them to her cuckold. I was correct, because as soon as Olwen broke off the kiss, Richard swallowed, licked his lips and grinned.
“Thank you, dear,” he said gratefully. “I hope you enjoyed that as much as I did.”
Olwen reached into the car and took my hand.
“Come on, slowcoach,” she said, “It’s time for some real fun.”
I allowed myself to be led out of the car and up the garden path to a large detached house, which looked to me as if it could have been a farmhouse at some point. My flaccid cock was still flopping around as we walked, and I began to doubt if I’d get it up again any time soon. I’d really enjoyed my blow job, but Olwen had totally drained me. As we entered the house, I wondered if I would be able to fuck this incredibly sexy MILF at any point in the next couple of hours.
Richard came in after us, and shut the front door. Olwen kissed me, and started to tongue fuck my mouth. She tasted incredible. I’d never been kissed by anyone who had had my cock in her mouth moments earlier, and even though I could taste my own cum on Olwen’s breath and her tongue, I kissed her back eagerly. I couldn’t believe my situation, but, floppy cock or not, I wasn’t going to turn up the opportunity to fuck Olwen if I could manage it.
Olwen was speaking now. My brain registered that I was being given a choice. Did I want to fuck her in the conservatory, or upstairs in her bedroom? I must have chosen the latter, because the next thing I knew, Olwen had taken my hand and was leading me upstairs.
“Bring us up some water, and my pouch and my lady church warden,” Olwen called over her shoulder to Richard. I knew that I could do with a drink, I thought, but what the hell did she need with a pouch and what had she also asked for? A lady church warden? I’d never heard that name before. I wondered if we were about to have a threesome.
In the bedroom, Olwen directed me to sit on the bed. She started to undress, and indicated to me that I should strip too. I didn’t need any more encouragement, and I began to unbutton my shirt.
She was soon down to her bra and panties, which I noticed were both quite utilitarian, and were obviously worn for comfort rather than to attract a lover. Olwen winked at me as I tugged my trousers and pants down.
“Hurry up and get your socks off, then you can help me with this,” she said softly, indicating her very full bra. I did as I was told, and, standing naked, I reached for the clasp.
I unclipped it and Olwen wriggled out of her bra. My eyes feasted on her two large tits with their thick, chocolate brown nipples. I felt my cock twitch, and I remember thinking that there was some hope of my getting it up again quite soon. As I watched, Olwen slid her thumbs into the sides of her panties and yanked them down.
Oh my god! She was shaved! Her outer cunt lips were pink and plump and they glistened with her juice. I wasn’t the only one to have been turned on by our recent bout of oral sex.
I was about to compliment Olwen on her display of womanly delights when Richard came into the bedroom, carrying a tray.
“What the fuck?” I thought. “I’m not having a threesome with Olwen and her husband!” I turned back to Olwen with a questioning look. She ignored me.
“Put the tray on my bedside table,” she told Richard, “then see to Jacob. He heeds a helping hand I think. Or should I say a helping mouth?”
Richard put the tray down, and I saw a jug of water, two glasses and a long stemmed pipe and a leather pouch on it. Olwen was speaking now.
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