Shirley

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Young guy gets best sex ever from a willing mature.
3k words
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62.6k
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I met Shirley when I was working in a bar in Germany. She was English, which is was what attracted me initially, over 50 with short blond hair, fairly large breasts and had a slightly matronly look about her.

I had met her briefly, a couple of nights before when she was eating dinner with her daughter. But on this particular night, she sitting alone at the bar, getting slowly hammered.

When I was done for the night, she asked if I could keep her company. She wasn't as drunk as I thought and she still had the ability to hold a conversation. But it was clear to see that she was "happy".

She asked if I would buy her a drink as she was out of cash. I had a three free drink allowance and used it to get us both "one for the road".

It was close to 3.a.m when the bar was closing and it was below freezing outside.

I offered to walk her to her hotel.

When we arrived, she asked me if I wanted to come to her room and warm up. I was freezing because I had forgotten to wear a winter jacket, so naturally, I agreed.

Once inside her room, she said she needed to freshen up and slip into something warmer.

She went into bathroom and closed the door.

Now, the walls weren't exactly soundproofed, so it wasn't difficult to hear her peeing and flushing the toilet. Then I heard some shuffling and then the sound of running water in the wash basin.

Finally, after some minutes, the door opened and she came back in wearing training slacks and a sweatshirt.

She sat next to me on a couch in her room and chatted about her visit. It hadn't gone according to plan. She had argued with her daughter, earlier that night and had left her on bad terms.

She also apologised for not offering me anything to drink but she didn't have anything. I told her I'd had enough and that I was bursting for a pee myself.

I went to the bathroom and closed the door. Knowing how noisy it was, I tried to aim my urine stream to inside of the bowl instead directly into the bowl.

As I pee'd, I tried to work out where this evening was going. Shirley hadn't given me any indication that she was remotely attracted to me in any way. When chatting to her in the bar, there were no flirtatious glances or innuendo to give any indication that she was interested in me.

I started to feel disappointed.

When I was done urinating, I washed my hands in the sink and that was when I had a pleasant surprise. Between the wash basin and the shower, a radiator was mounted on the wall. Draped over the radiator was a large pair of pink cotton panties. High legged with a lace frill on the leg holes and waistband. Gingerly, I reached and touched them. They were slightly damp as though they had been just rinsed out. I picked them up and held them up in front of me. It was then that my initial thought about them was wrong. They weren't just cotton. The front panel was cotton, but the rear was a shear fabric. I tried to imagine her large arse filling them and imagined seeing her butt cheeks almost on show. My cock twitched in approval of this thought.

I looked inside and noticed not only a few pussy stains in the gusset but also blond pubic hair, curled up on the soft fabric. I felt my cock start to swell and pressed the gusset to my nose, breathing in deeply. There was a slight musky aroma of her pussy impregnated in the fabric.

Smiling, I replaced them and left the bathroom. The beginnings of my erection starting to show. It also occurred to me that if she was drying these panties out, then she wasn't wearing any under her slacks. it was clearly a time for action and the evening could go one of two ways.

I re-entered her room with renewed bravado.

Shirley smiled at me as I walked towards her. I stood in front of her, bent over, cupped her face in my hands and kissed her. Nothing too heavy, just a touching of lips.

I backed away expecting her to tell me to leave. But instead she said she liked that and would I do it again.

When I leaned in to kiss her again, her hand reached the back of my head and she pulled me closer to her. This woman hadn't been kissed in a while. Her tongue forced its way between my lips and searched hungrily inside my mouth. My cock was almost at full hardness and pushing uncomfortably against my trousers and boxers.

When she let me come up for air, she noticed my bulge.

"Maybe I should take a look at that," she said.

She unbuckled my belt and unzipped my fly. My trousers fell to the ground and I stood before her with a growing bulge pushing against the fabric of my boxers. There was a small wet spot where some pre cum had leaked.

Using her index finger, Shirley traced the outline of my penis from its tip to where it met my scrotum. Then she cupped my balls and gently massaged them. She bent forward and ran her tongue along my hardening shaft. Then she opened her mouth and closed it over the head of my cock, through the material of my boxers.

The feeling of her hot breath on my cock head was delicious. My knees began to buckle and sensing how turned on I was getting, she stopped.

"Very nice," she said, smiling at me. She grabbed my waistband and tugged my boxers over my hips and down to my ankles. My iron hard erection almost poked her in the eye.

"My, oh my. What a lovely cock," she said as she traced the thick vein that ran along on side of my shaft. She wet her finger and made small circles on my bulbous, shiny helmet. Copious amounts of clear pre cum started dripped from my pee hole and she stuck out her tongue to taste it.

"Mmmm, very tasty," she said and slid the rest of my cock into her mouth whilst cupping and squeezing my testicles. I told her I needed to lie in the bed as my legs were starting to buckle under her delicious ministrations. I climbed onto the bed but she told me to scoot to the end of the bed so that my legs draped over the edge of the mattress.

She knelt on the floor at the end of the bed. Taking my hard penis in her hand, Shirley lifted it up and opened her mouth. Her lips closed around one of my balls which she gently sucked on. Her tongue slid between the crack of my arse as she stimulated my perineum.

Shirley put her hands under my thighs and lifted my legs up and over my shoulders.

I was at my most vulnerable. My arse was on display and as I watched, her head vanished as I felt her tongue my anus. My cock twitched uncontrollably as Shirley rimmed my brown starfish. She let go of my legs and asked me to get on all fours. As I knelt on the bed with my arse in the air, Shirley tongued my anus once more, but at the same time she reached around, grabbed my cock pulled it backwards. She stopped rimming me and her mouth closed around my cock. The feeling was mind-blowing. She started to massage my anus with her fingers, as she sucked hard on my cock. I felt a slight intrusion as she slid her finger deep into my rectum and massaged my prostate.

I couldn't hold it any longer and my balls released their cargo. I shot long streamers of hot, sticky semen onto the duvet. As she continued to massage my prostate more, I just kept on coming. I couldn't believe how much semen I had.

When I finally had no more left to give, Shirley removed her finger from my arse.

"I hope that's not all you've got," she said, eyeing up the sticky, white mess on the bed covers. "This is the biggest cock I've ever played with and I need you to fuck me senseless with it."

She removed her sweatshirt and I saw she wasn't wearing a bra. Her ample breasts swung into view and she straddled me, pinning me to the mattress. Her big, beautiful globes of pink flesh had large, thick nipples that were begging to be squeezed, chewed and sucked. I wasted no time in grabbing them and fastening my lips around them. She moaned as I chewed on her nipples and she ground her crotch onto my cock.

"Go on, suck my tits," she moaned. "Bite my nipples. I love that. It sends a tingle to my cunt."

I chewed hard on her raspberry sized nipples and she shuddered.

She stood up at the end of the bed and I sat up. I knelt down in front of her and started to pull her slacks down. I could smell the familiar musty aroma of her sex as I pulled her pants over her hips. A large, slightly unkempt bush of blond pubic hair came into view and I buried my nose into it as I tugged her pants to her ankles.

She kicked off the garment and stood naked before me.

Shirley had what you would call a "pear shaped" figure, but the years had had not been kind and there was a slight ring of fat that ran around her waist. But she wasn't fat, by any imagination. Cuddly would be a better description, although I doubt that she would have taken any comfort in that.

Shirley raised her leg and stood on the edge of the bed, giving me a lovely view of her delicious, pink gash. Her pussy, which was surrounded by a mass of curly, blond hair, was open and looked inviting. Her labia were thick and juicy and her cunt hole glistened.

She reached down with both hands and peeled her pussy lips apart. Her scent was intoxicating and I opened my mouth and fastened it to her opened hole.

My tongue went straight into her wet pussy and I licked at it, like a kitten licks his milk. I found her clitoris and went to town on it, flicking my tongue over the hardened bud and sucking on it.

She shivered, moaned and shuddered and told me she had to lie down too.

I asked her to get on all fours. Her big beautiful arse was now in view, with a delightful pink, puckered anus, that was surrounded by whispy, blond hairsand crying out to be licked, poked and fucked.

I licked two fingers and inserted them into her soaking wet pussy and began to finger fuck her. As she moaned, gasped and groaned, I bent forward and rimmed her arse hole with my tongue. I used my thumb to rub her clit as I continued my assault on her two holes.

She suddenly stiffened.

Her cunt clamped onto my fingers as she let out a loud gasp. Hot, sticky pussy juice erupted from her hole and showered my hand. I licked two fingers from my free hand and inserted them into her anus and began to finger fuck her arse hole. Having the fingers of both hands servicing both her holes at the same time only served to heighten her orgasm even more and I could feel her body going rigid. I can't imagine the emotions she was going through, but the way her pussy was squeezing my fingers, she threatened to cut off their blood supply.

Her body went limp and she collapsed face-down on the mattress.

Panting and out of breath, she whispered, "The best fucking orgasm ever."

"I'm not done with you yet," I said and I turned her on to her back, raised her legs in the air and pushed them apart.

My rigid cock slipped quite easily into her soaking wet vagina and I went in all the way to my balls.

"Oh my fucking God!" she exclaimed. "You really know how to fill a woman up."

I knelt back and started to slide back and forth, in and out of her pussy. She urged me to fuck her harder and faster. I moved my hips back and forth with more speed.

There was a delicious squelching sound as my penis stirred her thick juices.

I turned her onto her side and fucked from her from that position. She reached down and rubbed her clit as I slammed my cock in and out of her cunt, pounding her pussy, as hard as I could.

Having already come on the mattress when she wanked and rimmed me, I had some trouble in reloading, but that was okay as she was clearly enjoying the experience of being fucked by my cock.

She told me to lay on my back and she straddled me again.

She moved up my body and lowered her dripping wet, hairy cunt onto my face.

"Lick me and taste my juices," she demanded.

I opened my mouth as she lowered her vagina onto my face and sucked away at her thick, juicy labia. As I licked her clit, she started to come again. Her sweet juices flooded into my mouth as she rubbed her slippery sex over my face.

Then she turned around and bent forward.

I felt her grip my thick shaft and then the familiar warmth as she sucked my cock into her mouth again.

We stayed in the 69 position for some time, as she had orgasm after orgasm. I licked her cunt and sucked on her clit, whilst three fingers slammed in and out of her arse. I felt her suck harder than ever on my cock as she inserted a finger into my ass to stimulate my prostate again.

Pussy juice was dripping off my chin and a trail formed along my chest as she moved down my body. She gripped my cock once more with her hand. I looked down and had a great view of her open, wet pussy and gleaming pink arse hole. She pointed my cock to her open pussy and I watched as it slid in.

She rode me "reverse-cowboy" style for a while, having more orgasms than any woman I had ever known. Flooding my cock and soaking my balls with her warm, sweet juices.

I still wasn't ready to come and so I just laid there and enjoyed the show.

Then, without warning, she moved forward and my cock slipped out of her hole. But she gripped my slippery shaft again and I watched as she pointed it at her anus. Slowly, she sank her ass onto my iron hard cock. I watched as the helmet disappeared from view, slowly followed by the rest of my thick shaft.

When my full length was inside her ass, she stopped for a moment.

I couldn't see what she was doing but I can only assume she had her eyes closed and was savouring the feeling of my cock filling her arse.

Slowly she began to rock back and forth. I could see she was also stimulating her clit as she rode me. Her movements became increased in tempo as she continued to ride my cock up her arse.

She moved faster on my cock, riding me like a Derby winner. Then she went rigid and warm juices flooded my balls another orgasm washed over her.

She stopped and climbed off me.

She climbed back on the bed, on all fours and demanded, "Put that hunk of meat in my bum and fucked me hard."

I knelt behind her, pointed my cock at her ass and pushed it in.

God, she was tight, but after so many orgasms, she was well lubricated. I held onto

her hips and drove my cock all the way in until my balls were slapping her pussy.

I increased the tempo of my thrusts and she seemed to increase the gripping of her

muscles around the girth of my cock.

Slowly I began to feel my own orgasm approach and I let her know that I was going to come.

"Do it!" she screamed. "Fuck me and fill my bum with your spunk!"

I let go and pumped copious amounts of semen into her, spraying the interior of her rectum with my hot sticky cream.

Her arse gripped and squeezed me, forcing more and more semen out of me.

As my orgasm subsided, my cock deflated and slid from the vice like grip of her rectum. Semen dribbled from her anus and ran down the crack of her cunt. She reached under herself and rubbed the thick, creamy liquid into her pussy and pubic hair, before turning onto her back.

Semen matted her pubes, but she simply rubbed it in and licked her fingers dry.

As I watched her rub more semen into her pubic thatch, I remember thinking that this was by far, the nastiest woman I had ever had the pleasure of fucking.

"Mmmm!" she exclaimed. "You taste real good," as she slurped my thick sticky fluid from her fingers. " I think I am going to have to suck you off and make you come in my mouth."

I told her that I was spent. I had nothing more to give and this was the best sex I had ever had in a while.

She assured me that she could make me come again. It might take a little time, but it would be fun making it happen.

She leaned forward, clamped her mouth around my still hard shaft and started to suck my cock. She worked on my penis for a full twenty five minutes. Licking my penis, sucking the head, sucking my balls and ferociously wanking me.

Finally, and with a degree of pain I might add, I finally shot my load into her mouth and she drank my semen down like it was vintage champagne.

We collapsed into each other and fell asleep.

The next morning...well, let's just say, we didn't go out much.

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chytownchytownover 4 years ago
Anal Shirley???***

That is a nasty story ,but so hot!!!! Thanks for sharing. Damn that was nasty!!!!!

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