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Jackie's Surprise Entrance

"A quiet, utterly respectable middle-aged woman shows me you never can tell"

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I had had my eye on Jackie for months. She was a casual employee at the newsagents/wool shop next to the off licence I worked in, and she would wander in from time to time and hang around, looking at the shelves but never buying anything. I concluded that she was probably lonely. One of her colleagues had told me she had been a widow for five years. She went to the Methodist church up the road, but I got the feeling she wasn't just religious, but using the place for company.

She had medium-length fair hair flecked with grey, although she was only about fifty years old. Always soberly dressed in a sensible dress or skirt and jumper, she was in quite good shape, with nice big breasts safely guarded by a sturdy bra, so they didn't wobble or protrude much. She was probably proud of them, but was too straightlaced to flaunt them. Her hips were wide and drew my attention to her midsection - attention she could not deflect, because there was no way of hiding them. Even when she wore a loose, voluminous skirt, she was broad in the beam.

As quiet and introverted as she was, I sensed she was dissatisfied with her life and the lack of affection or maybe intimacy. She had no children to comfort her and make her feel loved. I will admit I felt guilty about my feelings for her. Not guilty about fancying her, because there is nothing you can do about that, but about wanting a sexual relationship with her rather than a proper loving one in which sex would be a part. But another part of me felt what she needed was not a nice man to take her out for tea and cakes on a Sunday afternoon, but a lusty man who might still do the tea and cakes bit but would then take her home and make love to her.

Do I mean make love? With someone like Jackie, I didn't feel it could be described as fucking, or even having sex. Would she be capable of having it off with a man? She would probably think that sounded too naughty, too clandestine, and sly. No, it would be making love, even though the love part was short-term and lasted no longer than a couple of hours of build-up during a nice, innocent outing, plus half an hour of kissing and seduction, followed by the act itself and a period afterwards when we would slowly but inevitably float back down to earth. Seduction was what she needed. Only then could she allow herself to be drawn in, making it someone else's doing, not hers.

Timing was going to be crucial here. From the way she used to come in and hang around, I was pretty sure she was interested in me, but one wrong move could blow the whole thing, making her feel cheap.

And so it was that one afternoon when my manager was on a late lunch, Jackie drifted in and we chatted idly for a few minutes.

"Ruthie's off this afternoon," she said. "Going home as soon as I get back."

"Who else is on?" I asked.

"Just me," she said. "Boring." And with that, she left.

As soon as the manager returned, I made an excuse about buying a paper and was soon in the wool shop, where Jackie sat behind the counter doing a crossword.

"To what do I owe the honour?" she asked, putting the puzzle magazine away.

"Thought I'd come and see you for a change," I said, my natural conversational cool deserting me because I was on the prowl and felt she would detect that. She probably could tell, but was that a good thing or not? Only bad if she didn't want to receive my advances, I know now. Unprompted, she started telling me about her social life, chapel outings, and how a man she knew from the social committee had taken her out on his new Harley Davidson. It reminded her of her youth - as it no doubt reminded the mid-life crisis man of his.

"Oooh!" I said playfully.

"Nothing like that," she responded. "I don't need that, just a man to get out and about with."

She was leaning on the counter with her hands flat. We both went quiet and I instinctively began twirling a finger around one of her knuckles.

She pretended not to notice for a few seconds but suddenly became self-conscious. "What are you doing?" she asked, not quite sharply but nervously.

"I'm tickling your hand," I replied.

"Uh huh," she muttered and then, to my surprise, turned her hand over and held my finger. "You're a naughty man," she admonished gently. "I told you, I don't need that." She dropped my finger abruptly and then felt bad about it. She patted my hand. "For a minute there I thought you were going to ask me out," she said very quietly.

"We could go for a drink," I suggested.

"Just friendly friendly," she said pointedly but weakly.

"Okay," I said, putting my hand on hers as innocently as I could manage. "When are you free?"

"Tonight," she said. "Or is that..."

"Tonight is fine," I said brightly, relieved and hopeful.

I picked her up at her neat little semi-detached house and we went to a quiet pub in the country.

The conversation was a bit stilted because we both knew it was just wasting time before the main event. Or rather she knew and I hoped. At that stage we were scrupulously polite, not giving anything away.

When we got back to her house, I said, "Well, that was nice. I'll, err, see you at work," but she put a hand on my arm and said,

"Don't you want to come in for coffee?"

This was innocent, chapel-going Jackie talking, so I tried not to read anything into it. Coffee it would be. A quiet, civilised end to the evening. All the same, she was sitting next to me, warm and fragrant and relaxed - except now she wasn't as relaxed as she had been in the pub. Something had changed, but she clearly liked my company or she wouldn't have invited me in.

I sat in Jackie's quiet, ticking house, on a practical tweed sofa while she made some decaf. When she entered and had put the cups on the small glass coffee table, she went over to the sideboard and took out a bottle of Kahlua. Waving it at me, she asked, "Yes?"

I only lived down the road and would be well able to drive after one or two liqueurs, so I accepted and she poured us a glass each and sat next to me.

"I don't do music," she said defensively, reading my mind. "I'll put the telly on if you like." And that's what she did. Newsnight, with the sound turned down low. She sat back contentedly, relaxed again.

The air crackled with electricity and I put my arm around her, drew her to me, and kissed her. She kissed slowly and gently but happily. It was nice, like being loved with her tongue. I put a hand up her skirt and she pulled back and removed it, then looked into my eyes and kissed the tips of my fingers.

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"Naughty," she said playfully. "Do you know how long it's been since anyone put a hand up my skirt? Give me a minute." She stood up and walked into the kitchen, then came out and went somewhere, presumably into the bathroom. After a couple of minutes she left that room too and went into what I gathered was a bedroom, where she stayed for just a few seconds.

When she came back into the lounge I feigned nonchalance with my open hand next to me, where she had been sitting. She looked at it, then at me, and she sat down on my hand. It felt as if we were daring each other and she had trumped my misplaced hand with her deliberate rump and undercarriage. I attempted to stimulate her but with zero mobility in my right hand, I had to pull it free.

"Sorry," she said. "That was clumsy of me." She sat back and looked at the TV for a few seconds before saying, "You can kiss me again if you like."

I needed no further invitation. This time when my hand went automatically up between her thighs, she allowed it. But she didn't part her legs, so I had to slide my hand down in the gap at the top, at her crotch. Her breathing became faster and shallower. I played with her clitoris through her big, sensible pants. She put a hand on my leg.

"You're not going to have me here," she said suddenly and I examined the words for possibilities, like a barrister seeking to expose hidden meanings. Before I could come to a conclusion she stood up and took my hand. "Let's go through there," she said softly, nervously.

I followed Jackie into her bedroom, where a small bedside lamp gave the room a romantic air. A framed photograph had been laid flat, face down. She stopped and put her arms around my waist and we kissed again. This time my hand was inside her knickers in a flash and she wriggled a little but didn't flinch. She put a slender hand inside my shirt and stroked my side, but was waiting for me to do something.

I pulled my hand out of her vagina and unzipped her skirt. It fell obligingly to the floor and she stepped out of it. Her bare legs gleamed, pale and soft. The knickers were beige. I fell to my knees and kissed her mound and she put her hands on my head. I pulled the knickers down to her ankles and he stepped out of them. Her pubic hair was abundant and untrimmed. I put my nose to her clitoris and gave it a rub.

She sat down on the bed and lay back, exposed and inviting me in. I wrapped my arms around her thighs and pulled her to me, then licked her. Her pussy lips were big and shapely and sealed. I parted them and put my tongue between them. She tasted clean and almost neutral, as if her sex organs were household ornaments that were kept neat, tidy, and dusted.

She sat up and removed her blouse, then her bra. Her breasts were full, pale and freckled.

"You not a boob man?" she asked invitingly.

"You have beautiful breasts," I said, undressing quickly while she watched, led astray by her natural feelings as they surged over her normal "respectable" behaviour and inhibitions.

I felt her breasts and kissed her nipples, which made her squirm with delight. Then I headed south again but when I began to lick her she pulled back.

"Can I ask you a favour?" she said. "Can I turn over? I want you to lick my bum."

Again I had to remind myself this was straight-laced Jackie talking. She turned over and moved her knees so her bottom was presented to me. Her anus was dark, almost purple. It looked good enough to eat, so I moved in and licked it. She sighed, then moaned with abject pleasure. "Oh my God," she said. "That is so lovely. Make me cum."

I licked Jackie's arse as if it were the most natural thing in the world, which it probably was before some prudish generation decided it was the act of an animal. No one in the world would have described Jackie as an animal, yet I was discovering there was much more to this woman than met the eye. She began breathing heavily and making noises into the duvet where her face was buried. Noises like "Aaah" and "Ohhh" and "Yes". Then she gave a final cry and collapsed.

I kissed her bottom politely and moved up to cuddle her.

"It's been such a long time," she said, kissing me enthusiastically. "Now there's something else I need you to do." Taking my exhilarated cock in her hand, she said, "Up the bum. Please."

Reading something in my eyes, she added, "It's just what I prefer. Do you mind?"

Mind? Was she crazy or what?

"Yes?" she said. "I'll get some gel." She made a quick trip to the bathroom and came back with a tube of KY Jelly, which she handed to me. Back on her knees, she buried her face in the covers again as I lubed her up. I couldn't believe my luck. Nice, ordinary, woman-next-door Jackie wanted me to fuck her up the arse.

I moved in behind her and she shuffled down until we got the angle right. When I pushed slowly but steadily she grunted, then squealed briefly. As the head of my cock popped in, she began talking as if she were in a narcotic trance.

"Yes, your willy up my bum. I like your willy up my bum. Your cock up my arse. I love it." She continued in that vein while I pushed deeper and deeper and she moaned with ever more guttural lust. "Fuck my arse. Oh yes. I have always liked it more up the bum. Ohh. Ohhh."

I began to grind against the sides of her entrance. She was completely used to having me in there now, and when she squealed, it was with the confidence that pain would be closely followed by pleasure.

Then she yelled at the top of her voice before subsiding, spent and satisfied, whimpering sweet nothings.

After we had composed ourselves, we began to talk on a more intimate level than before.

"Did you enjoy that?" she asked.

"It was wonderful," I replied. "I have to say I was a bit surprised, but..."

"I know," Jackie said. "I was surprised myself at first. It happened by accident one Saturday afternoon when me and my husband were spooning. Our sex life was very tame, but we were messing around and his willy just pushed in there and it hurt but was very exciting. So we went out and bought some KY, then came back and did it properly." She paused and looked at me intently before adding, "And you're the only other man I've ever even been with, so don't think it's something I..."

I stroked her arm and kissed her gently on the lips.

"I am honoured, Jackie. I loved fucking you up the bum and I want to do it again. But it's our secret."

Written by silverseeker
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