The Most Unlikely

by Alistair Acorn

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa, Consensual, NonConsensual, Mother, Son, Grand Parent, DomSub, Anal Sex, .

Desc: Erotica Sex Story: Tale of one of member of a depraved friendship taking advantage of the others family.

Where is the most unlikely place to pick up a willing sex partner? In that place who would you expect to be the most unlikely person?

What if I said a funeral and the person the grieving widow? Well that is where I picked up Hilary Simpson-Jones, a fifty four year old, very severe lady, yes lady. Hilary was a real Lady and the guests at the funeral of her late husband Sir James Simpson-Jones were mostly of that class.

Myself I was there only because my best friend had asked me to go with him. It was Simon's father who was being buried and Lady Hilary was his mother.

I had only seen Lady Hilary once before and nine months prior to seeing her at the funeral and even then she looked a sour faced stuck up bitch. Simon left home because of her constant bickering. She was a snob of the first order. She looked down at any working class person thinking them inferior to her and her social group.

Before meeting Simon I had never mixed with his class as his mother called them. One of the reasons there was such animosity between Simon and his mother was because we were friends. We met the first day we attended university and from that day we were like two slices of bread in a sandwich. We attended the same classes, fucked the same women and came away from university with the same high marks being in the top ten percent of our year. The only difference was I came from a working class family, he from the upper crust.

Hilary was a tall woman, straight backed, her head held high as she looked down her nose at people even in her own social group. She was the bossy type, always wanting to be the centre of attention, chairman of committee's etc.

I on the other hand was about two inches shorter than her, wide shouldered and stocky. We were about as compatible as oil and water, but water and oil can be mixed, it's just knowing what chemical to add. In our case it wasn't a chemical.

Simon and I arrived at the church just as Hilary was standing outside. "Simon, why have you brought that man to your fathers funeral, you know it is family only?" she asked, referring to me.

It was difficult to see her face since a black veil was pulled down on her face, but you could feel the venom in her voice tone.

"Charlie, is my friend, the only true friend I have, thanks to you. If he doesn't come, neither do I," he snapped back.

"Simon, this isn't the time or place to argue over this. Look I can wait in the car, you can see your mother is upset."

"You see even your friend thinks as I do." she replied, but it was the way she said friend that really hit a raw nerve.

She turned to enter the church, but her she heel caught in the sunken rubber mat and she toppled sideways. I saw her beginning to fall sideways so I reacted by catching her, but clumsy. My right hand grabbed her breast and the left her back. What I had was a handful of a lovely firm breast, but Hilary too had reacted to grab anything to stop herself falling and it just happened to be my cock.

The smell of her perfume, her soft breast in my right hand and the fact she was grasping my cock started the blood flowing and I was getting an erection. What she had a hold of was my eleven inch cock, but instead of letting go she held on to me as I pushed her to her feet. Still the hand was on my cock but she was squeezing me gently. Now this action was so strange for a woman who was a prude in the broadest term of the word that I couldn't believe it had happened.

"Thank you Charles must watch where I place my feet," she said letting go and resumed her head up snooty look as she and her group moved into the church. I didn't think anyone else noticed, but I was wrong, Simon had. I doubt if anyone else did though for Simon had turned and shielded his mother from view by the other mourners.

"Did I see my mother hanging on to your cock? She must have felt you are built like a donkey, but she didn't remove her hand. In fact I could have sworn she was enjoying the feel," Simon said in a low whisper.

"Yea, and I was getting a hard-on, so she couldn't be mistaken on what she had a hold of," I answered.

"The randy bitch, I wonder if all her airs is just a cover-up?"

"Simon she is your mother, you can't go around saying thinks like that about her."

"Every woman is someone's mother, so what if it's mine. Why don't you follow it up, you may get lucky. If she done to me what she did to you I would."

"What if it was my mother?"

"I'd still follow it up."

"God Simon, you are pussy mad."

"So are you. Remember what we said, pussy is pussy no matter where it is and remember we share."

"You want to share your own mother?"

"Why not, come on let's get inside."

So that was the first contact with Hilary. The second came at the wake which was held in Simon's home.

I went up stairs to use the toilet in Simon's bathroom suite and was just coming along the passageway towards the stairs when Hilary minus her coat and hat came out of her bedroom. The noise from below which seemed to echo up the stairs was almost deafening and I wasn't sure just what Hilary said to me as I was about to pass her door.

"Pardon, I couldn't hear what you said," I replied stopping and turning to face her.

"I know it is a bit noisy, not what you would expect at a funeral. Come inside I want to ask you something," she said backing into her room and holding the door open so I could enter.

"Wow, some bedroom you have here," I exclaimed as I looked at her large bed with the pink coloured deep pile carpet and the mirrors covering three sides of the room and the windows at the other. Everything was frilly and ever so feminine.

"Yes and all to myself. My late husband never once came into it, well maybe just to wait on me."

Was she telling me her late husband never fucked her or was he past it. I couldn't care less if I offended her or not, "So you must be a bit frustrated, lying here thinking what a man could do to you in all this softness."

"I am, but I only want a man who has a large enough penis that could fill me up."

Her reply shook me, especially coming from her high society mouth. She no longer had that nose up in the air look about her but a smile which curled the corners of her brightly painted mouth. She reached behind her and I heard the key turn in the lock. Still the smile as she stood leaning back against the mirror backed door.

"Well you know I have a large penis you gave it a good feel at the church. Do you think I could fill you?"

"Oh, I'm certain you can, want to try?"

"Look lady, I'm willing to try any woman who is willing and you seem to be as willing as anyone I've ever met."

"Even though I am your best friend's mother?"

"So are you any different from other women?"

"I'm a great deal older than you are."

"So what has that to do with it?"

She reached under her dress and down came a pair of wide legged French frilled knickers and her stockings. She was still leaning against the door and smiling. "Well get your trousers off, I'm ready."

I still wasn't sure if this was just a trick to get me to drop my trousers and then she cry rape.

"All in good time. First you get on the bed, or better still take off the dress."

"No, the dress stays on. I have guests downstairs and I don't want to get dressed again, but I'll get onto the bed if that is what you want, but I would much prefer it if I was on top."

She crossed over the room and hitched her dress up and knelt on the bed. I hoped I was doing the right thing as I kicked off my shoes and dropped both my trousers and underpants and lay down on top of her counterpane. My hardened cock was now visible and her eyes were open wide as she stared at it as I lay back on my elbows.

"Oh yes, that will pleasure me no end. I've never seen one as large as this, are you sure a woman can take that thickness?"

Nothing about the length, just the thickness. She wasted no time though getting over my legs and now I got the smell of her warm perfumed body. When she lifted her dress and let it fall over my stomach I got the combined perfumed and aroused female smell blown into my face.

Hilary had her hand under her dress and the first I felt was warmth engulf my shaft as it slid up her warm passage. As she slid down her head was thrown back, a smile of contentment on her face and a long expulsion of air out of her mouth. She may have liked the feeling, but I loved it. Soon she was sitting on my things with our pubic hairs pressed together and it was then she looked at me.

"Charlie you will always be welcome here. We may have gotten off on the wrong foot, but this feels like heaven."

"Your not so bad yourself Hilary," I replied, using her forename for the first time.

"You mean for an old woman?"

"No, there is no difference between you or one my age."

"So age doesn't put you off?"

"I told you before, no."

Nothing more was said as she started her back and forward thrusting of her hips after she rolled her hips to get comfortable. The feeling of sliding up and down her lovely tight grasping vagina was really turning me on and I tried to keep time with her as she fucked herself on my cock. Always with a strange female the first time never lasts long with me and I spurted my load into her flooding her upper crust pussy.

"That is lovely Charles, now I will have a reminder of you for a few hours."

"Let me stay the night and you can have more than a reminder."

"Let me think about it, but just let me sit here a bit longer."

She sat with eyes closed grasping and releasing my cock trapped in her warm pussy and slowly I started to harden again. Her eyes opened and the red coloured corners of her mouth tilted up. I knew that she wanted more but this time it was to be my way.

I quickly got out from under her, but I had to withdraw first and I got behind her, pushed her head down and threw the dress over her back, exposing her wide fuckable rear end. Oh I wasn't going to shovel shit this time, so I guided my sticky wet cock towards the lovely little mound below. The lips opened and in slipped my cock. Being expanded only seconds before I slid in until our bodies touched.

I took her hips in my hands and pulled her onto my invading shaft and she wriggled her hips to get more in.

"Oh, yes, drive it in as far as you can, it has been years since I've had a man this way. Oh Charles you are a darling," she said as I again drove my cock deep into her body. We had been at it only a few minutes when there was a knock at the door and a woman's voice asked.

"Hilary, it's mother are you all right darling?" In an upper class snobby voice.

"Oh Mother, go away, I'll talk to you later," Hilary replied, but trying to keep a calm voice as she drove her hips hard back against my thrusting. She never missed a stroke as she spoke.

"Are you sure you are all right you sound as if you are crying," her mother persisted.

"Crying with pleasure is more like it," I said leaning forward and speaking in her ear, to which she laughed.

"Was that a man's voice I heard?" the mother asked.

"Don't be silly mother." Hillary said as I once again filled her pussy with my sperm.

I fell on top of her and took a handful of breast in each hand and resting on her forehead she pressed my hands hard against her chest.

"Oh Charles, twice I feel like a new woman."

"I will certainly be back for more if you want me to. God I could fuck you all night you randy bastard," I said in her ear.

"I am that and more. Now let me get up and sort out my mother," she said as I slipped out of her warm moist pussy.

I got off the bed took a moistened tissue and wiped myself of her sticky oily lubricant and put on my clothing. Hilary just placed a tissue between her legs and then replaced her panties and stockings. She smother down her dress and combed her hair smiling all the time at me.

"Stay in here for a few minutes after I leave and then you can come out," she said unlocking the door and leaving the room.

I could hear her talking to someone and their voices slowly receded, out of hearing. It was then I left her bedroom and made my way downstairs.

"Where the fuck have you been, I've been looking all over for you?" asked Simon.

"Why, what's the panic?"

"Can you make your own way back home, I've latched onto a sure thing and she lives in the opposite direction. I'll try and line her up so you can poke her as well. It's that woman standing by the window," he said pointing to a woman in her forties who was ultra thin and kept on looking over at him.

"Go on, tell me about it when I see you next."

"I may stay the whole weekend."

"Well tell me on Monday then," I said pushing him gently in the back towards her.

Within minutes they had disappeared leaving me standing alone. Not for long though Hilary stopped but only for a few seconds.

"Simon gone then? Stay the night, you won't regret it," she said moving on mixing with her guests.

A woman of the same vintage as Hilary, but not so well preserved came over and spoke with me. "Noticed you are on your own like me. You are Simon's friend aren't you, I'm a great aunt of his, doesn't come to see me very often, not the same as when he was a lot younger. You wouldn't like to come and have a chat with an old woman now and again would you?" she asked.

I didn't think she expected the answer I gave her, "Sure, I'll come and have a chat or anything else you want to do," I replied.

"Wonderful, just wonderful, I so much like to talk with a young man. I'm in all day tomorrow, well after church that is."

"I'll come and see you tomorrow afternoon then and we can have a chat. Where do you live?"

She told me and I wrote it down. She told me about her roses and how she spends her days. I tried to look interested while I gave her the once over. You could tell she had money, by just looking at her, the rings, necklace and bracelets she was wearing. Nothing to speak about in her looks except she was quite plain. What her figure was, was hard to tell with the loose dress and coat she was wearing, but she wore her dress ankle length. Anyway, black wasn't flattering.

She excused herself after half an hour and the guests thinned out leaving only Hilary and her mother who was a little lady, but quite active and she smiled a lot.

I dined with the pair of them, watched TV and chatted. When I went to bed Hilary stopped me as we went up the stairs. "You know where my room is. Wait until after eleven and come to me I'll be waiting. You know I can still feel you inside me yet, oh Charles, I hope I have made you happy and you won't forget me."

"No way Hilary, see you later," I said leaning forward and kissing her on the mouth for the first time. She hesitated slightly and placed her arm around my neck and pressed her mouth against mine. She wasn't used to kissing men that was for sure for there was no sucking of the lip or tongue use at all, but that will come.

After a long soak in the tub and well past the hour that Hilary had suggested and wearing only a dressing gown I found in the bedroom I made my way to her bedroom. The only light that entered the room was from the drawn curtains allowing in the pale light from the night sky. Being no moon the only light was really from the stars. All I needed was to see the outline of the bed and the lump to show someone was in the bed. That was confirmed and I dropped my gown and being hard and ready climbed in under the sheets.

The only thing that was different was that it wasn't Hilary but Constantine her mother. As I got in she held out her arms for me, so this was no accident, but prearranged. Not that I worried as long as she had a working pussy I couldn't care less, also I took delight in shafting those so called peers of the realm.

"Well Constantine, this is a surprise. Who put you up to this. Hilary?"

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Story tagged with:
Ma/Fa / Consensual / NonConsensual / Mother / Son / Grand Parent / DomSub / Anal Sex /