by Will Bailey

Caution: This Sex Story contains strong sexual content, including Ma/Fa, Consensual, Romantic, Cheating, Oral Sex, Anal Sex, Slow, .

Desc: Sex Story: Shannon was a lovely lady, but I thought she was out of bounds for me. Thank God I was wrong.As always, those looking for stroke stories should go elsewhere.

It was tough for me to get used to the idea of being single again after twenty-two years of marriage. At my age, it wasn't easy to find female companionship -- at least the kind that I wanted. Sure, there were a couple of gold-diggers. I mean, I wasn't rich, but I was pretty well-fixed. I had no mortgage on my home, no car payments or other serious bills, and a considerable salary. As I said, not rich but comfortable.

My job was also interesting. I was the chief software engineer for a medium-sized application development company: Radius. The only problem was that I didn't actually design things any more. I supervised. I could have done without the management side of the job.

There were quite a few pretty young things around my workplace, but I discovered early on that they weren't interested in an old fart like me. Except for the obvious gold-diggers, which I soon learned to spot.

Shannon Peters was a pretty young woman. She had the sort of nice girl-next-door looks that have always appealed to me. Her manner of dress served to emphasize these looks. She was always well-dressed in a neat but sedate style. Her pageboy haircut also amplified the girl-next-door impression. She had very black hair, blue eyes and a very light complexion with freckles -- the unusual coloration that's known as "black Irish." I discovered that she was indeed of Irish descent. Her maiden name was Mahoney, which she hated. She was on the petite side, about 5' 3" or 5" 4", and she was, I guessed, about thirty-five, at least twenty years younger than I. She was also married and therefore out of reach.

Shannon worked in our marketing department. She was intelligent and very good at her job. I discovered this in working with her on several projects. Working with Shannon was always a delight. About three years ago, we were working together. She was putting together a sales package for a new product. I knew from previous experience that Shannon was very bright and very professional. On this new project, my previous experience of her was reinforced.

Since I had been in charge of the software's development, Shannon needed input from me. She was very careful to be sure that her material would communicate the details of the application without misrepresenting it.

Since the deadline was approaching, we found ourselves working over the holidays. We were in my office on the 29th of December. Neither of us wanted to be there, but we didn't have much choice. I noticed that Shannon was unusually quiet and somewhat morose, so I asked if anything was troubling her.

"It's just that my husband is out of town on a business trip," she said, "and he called last night to say that he wouldn't be home for new year's. So I'll probably just sit in front of the TV and watch the Time's Square celebration. Or something equally boring."

"I don't have any plans either. Why don't you come over to my place for dinner, and we'll watch the tube together?"

"That sounds nice, but..."

"Shannon, I said 'dinner'-- nothing more. OK?"

"Oh hell, why not?" She paused and looked down for a moment. "I'll need directions, though. Actually, I'll just take a cab. Don usually drives, so I never bothered to get a licence."

"Why don't you let me pick you up?" I'd bought a new Mercedes CLK 430 coupe in September, and I admit that I loved showing it off. "I'd be happy to provide transportation, Madame."

Shannon smiled for the first time that afternoon. "OK. What time?"

She gave me her address, and we agreed that I'd pick her up at 6:00 on the 31st. The rest of the afternoon went very well. Shannon was able to concentrate much better, and we finished our work early.

"Shannon, that was terrific. Why don't you let me buy you a drink at Charlie's place? Then I'll give you a lift home, now that I know the address."

"Well... all right. But just a quick one. I'm expecting a call from my mother at about 7:30."

We packed up and headed for the bar. It was actually called "The Continental," but everybody in our company simply called it "Charlie's." Charlie was the bartender and manager, and this afternoon he was the only person in the place when we went in. He greeted us warmly.

"I'm glad to see some people. Christ, it's been so slow today. The thing is that not many people actually live around here, so when the offices are closed nothing happens. I'm probably going to close early, but I'll happily look after you. How about the corner booth?"

We sat down and ordered a couple of Charlie's specials. He's one of the few guys I know who actually makes a gin gimlet from scratch. The only problem is that they always taste like more. So we each ended up having a couple of them.

Away from the office, Shannon was an even better conversationalist. It turned out that she had many interests, among them rabbits, of all things. She'd bred them when she was a kid and really wanted a hutch. The problem was that she and the absent Don lived in a high-rise apartment in a building that frowned on both pets and children. I, of course, never had the slightest interest in rabbits. In fact, the only things I admired about them were their sexual habits, but Shannon made rabbits sound interesting.

We finished our drinks and headed for the parking garage. I was happy to see that Shannon was suitably impressed by my car. She managed to "ooh" and "ah" at all the right things as I drove her home. She lived across town, and traffic was heavy. The trip took a while, but we finally pulled up in front of her building.

"Thanks, Mike," Shannon said. "Thanks for being a friend when I really need one." She leaned across the console, gave me a peck on the cheek, then got out and walked inside quickly.

New Year's Eve 1999 was on a Friday. It finally arrived. I planned to do one of my favourite meals -- a meat fondue. It's a dish I've loved since I spent some time in Switzerland. I'd prepared the broth and the sauces the previous day, and I had a more than ample supply of beef tenderloin. I figured we could have the fondue in the living room in front of the fireplace. It would be nice and cheerful. The potatoes were cut and ready for the deep fryer. The bubbly was in the fridge. It was time to pick up Shannon.

When I got to Shannon's place, she was in the lobby waiting for me. She gave me another peck on the cheek. I escorted her to the car, and we drove away. On the way to my place, Shannon talked a mile a minute. I suspect that she was a bit nervous. I know that I was. We arrived at my house and pulled into the driveway.

We went inside. I took Shannon's coat and hung it beside mine. Then I turned around and got my first real look at her that evening. I think I must have been staring like an idiot. She looked fantastic. She was wearing the sort of outfit she never wore at the office. She was dressed for once in formfitting clothes -- a black sweater and a black leather skirt. They emphasized all the right points of her little form. The skirt had a big zipper in front that went from waist to hem. She looked sexy as hell.

I said, "Shannon, you look..."

"Different?" She smiled and did a little pirouette.

"Absolutely gorgeous," I managed to finish.

"I don't always dress like a nun," she said.

"I never thought that you did. At the office, you always look..."


"Yeah. Businesslike."

"Mike, that's business. This isn't. By the way, this place looks great. Why don't you get us a drink and show me around?"

I got our drinks, and I gave her the tour. I was surprised and pleased at her reaction to my art collection. Over the years, I've collected some choice works by Canadian artists, many of whom are my friends. Shannon had a very good eye and immediately gravitated to the best piece. I was getting used to being surprised by her.

I put the potatoes in the deep fryer and lit the fondue pot. Soon supper was ready. We sat on the chesterfield in front of the fire and ate off the coffee table. Shannon managed to put away a surprising amount of food for such a little girl. Another surprise.

After we finished our fondue, we were both fairly stuffed. I suggested that we have our coffee and think about desert later. She agreed. Then she asked if she could use my phone.

"Of course you can. Use the one in my office upstairs. That will give you more privacy."

"OK, but I'm just going to check my messages. Don was supposed to call today, and I haven't heard from him yet."

Shannon went upstairs while I cleared up and got the coffee and cognac. When she came back downstairs, she was very quiet and crestfallen.

"Shannon, what's wrong?"

She looked at me with tears in her eyes. "That bastard! He doesn't call all day, and then he leaves me a message to tell me that he won't be home until next weekend. Fuck him! Fuck him!"

Shannon dissolved in tears. I took her in my arms and held her. She cried on my shoulder as though her heart were breaking. I cuddled her and stroked her hair for what seemed a long time. Finally, she regained her control. She looked up at me.

"Thanks, Mike. I'm sorry to cast a pall over such a lovely evening."

"Shannon, in your shoes I'm sure I'd be in even worse shape."

She grinned. "But I'm not wearing shoes."

"OK, in your stockings then." I grinned back at her, happy that she found some humour in the situation. "Let's go back to the living room and sit in front of the fire."

We sat down. Shannon looked at me. I was afraid from her expression that she was going to cry again. "Mike, please hold me."

Once again, I took her in my arms. She was very quiet but at least was not crying. I was grateful for that. She looked up at me and gazed into my eyes. I did the only natural thing. I kissed her.

At first it was a gentle, almost brotherly kiss, but that changed. Gradually, we found ourselves in a more passionate embrace, and our tongues found each other. Shannon was a wonderful kisser.

At last, we broke the kiss. Shannon looked down, not meeting my eyes. "Mike, I've never cheated on Don."

"Has he cheated on you."

She looked at me. "I think so. I'm getting more suspicious all the time."

"You mean all the signs are there."

She nodded sadly.

"Shannon, I have to tell you something." She looked at me again. "I'm not into casual relationships and certainly not with you. I don't know what's happening, but I felt something just now that I haven't felt in years."

She gave me a little half smile. "I know what you mean. I did, too. Do you mind if I ask you a personal question?"

"No, certainly not."

"I know that you're a widower. I've heard that much at work. What happened?"

"Janet was sick for a very long time. When she finally died, it was almost a relief. At least she's not suffering any more."

"But the word around the office is that you don't date -- that you're kind of a loner. Why?"

"Oh, I've dated a few times, but nothing has ever worked out. I'm out of practice, I guess."

She smiled. "You're certainly not too rusty in the kissing department."

I smiled back. "It's the company."

She kissed me again. Soon we were back to the same sort of passionate embrace as before. When we finally stopped, Shannon sighed.

"I'm feeling dizzy. Do you mind if I lie down with my head in your lap?"

"Of course not."

I scooted over, and Shannon stretched out with her head in my lap. My arms naturally went around her. She grinned up at me.

"This feels so cozy. I haven't had this feeling in a long time."

"Me too."

I bent over and lifted her a bit. I kissed her. This time it went on even longer. I was holding her with my left arm, and my right hand found its way to her little body. I began caressing her, at first her back and then down to her legs. I felt that damned zipper. My hand moved down and I found the tab. It was just too damned tempting. I had to find out how the thing worked. Slowly, I began inching the zipper upward.

When I reached her mid-thigh, Shannon reached down and gently held my hand. She pulled back a bit and gave me a serious look. Suddenly, it seemed that she'd made up her mind. She released my right hand, put her arm around me and began kissing me again. I sensed that I'd been given permission.

Very slowly, my hand continued its journey upward. The zipper slid over her stomach and finally reached her waist. With a final tug, I reached the end of its track. Her skirt came apart and fell open, lying to either side. I gently stroked her thighs. Gradually, I gently touched her sex. I felt moisture even through her panties and pantyhose.

I drew back and looked at Shannon. Her eyes were closed, and she was breathing slowly and deeply. I slid my thumbs into her waistband. She lifted up to assist me, and I quickly pulled both panties and hose down her legs and off her feet. I guess that I was afraid that she might change her mind.

I kissed her ankles. Very slowly I worked my way up her legs, kissing and gently licking. When I reached her thighs, she separated them -- just a little a first and then wider. Her breath was beginning to come in little gasps. I continued to kiss my way upward. I reached her sex. She had opened her legs as far as she could. Her centre glistened in the firelight. I kissed it, and she gasped.

My tongue felt its way all over her pussy. Finally, I quit teasing her and began to lick her clitoris. Shannon began to buck toward my face. She was making little mewing sounds. Suddenly she tensed all over and moaned. She was coming.

When Shannon's body relaxed, I began eating her again. It just seemed the thing to do. Soon she was making little noises again. This time, when she tensed it wasn't quite as violent as the first time. I continued to eat.

Soon Shannon was bucking and mewing again. Her movements became almost violent. She tensed, screamed and went limp. I looked up at her. She was out cold.

I wondered if I could get the rest of her clothes off without awakening her. I thought it was worth a try. As gently as I could, I removed her sweater and bra. Her small breasts seemed the prettiest things I'd ever seen. Her pink nipples were erect, reminding me that she was probably a little chilly. Reluctantly, I took a throw from the back of the chesterfield and covered her. Shannon's comfort seemed more important than my voyeurism. She looked like an angel sleeping in my arms. She remained asleep for at least 20 minutes.

At last she opened her eyes, smiled up and me and stretched. The throw slipped off her shoulders. She looked down at herself. "How did I get naked?"

"It was magic. The clothes just seemed to melt away."

"Yeah. Right. My God, what did you do to me? I've never come that hard. I actually passed out."

"I hope it was to your liking, Madame."

"It was fantastic, but please don't do that too often. Not like that. I think you could kill me. But what a way to go!" She frowned a bit. "Don hasn't done that to me in years, and he was never that good at it. But the bastard certainly doesn't mind if I go down on him. He even has a sick joke about it. He calls it a '68'. He says, 'How about a 68? You eat me, and I'll owe you one.'"

Shannon looked as though she were about to cry again. I pulled her close to me and kissed her neck. "Don't cry, pretty Shannon. I'll never let anyone hurt you again."

She pushed away and looked at me very seriously. "Don't say things like that unless you mean them. I couldn't take that."

Now I was the one in danger of tears. "I just realized how very much I meant what I said. I suspect that I've been falling in love with you for a while. Tonight when you cried I passed the point of no return. However, there's a big obstacle that could prevent any relationship between us -- the difference in our ages."

Shannon looked at me quizzically. "How old do you think I am?"

"I'd have guessed your age at about thirty-five."

"Actually you're very close. I'll be thirty-five in February. I'm a Pisces."

"I'm twenty years older than you. Don't you think that's too much of a difference in ages?"

"Not the way that you just satisfied me, grandpa."

She kissed me again. For a very long time.

Finally, I broke the clinch and said, "Lets go upstairs and get comfortable."

She gave me a pouty little girl look. "Why Mr. Johnson, what are you suggesting? Surely you're not trying to get me into your bed."

"Of course I am. Can you walk, or do I have to carry you?"

"I can walk."

"All right, you go first. I want to enjoy the view."

Shannon preceded me up the stairs. The view was spectacular. Don Peters had to be the world's prize fool to mistreat this beautiful little lady. I vowed to myself again not to make the same mistake.

"Turn left at the top of the stairs, Shannon. Then just go straight ahead."

We entered the bedroom. I turned down the bed and tucked her in. Within a few seconds, I had my clothes off and had joined her. We came together, cuddling and kissing.

"Nekkid cuddles are the best," she sighed.

"They certainly are."

I was hard as a rock. I opened the drawer of the night stand. I hoped that I still had some condoms left in there. It had been a long time since I looked.

"You don't have to worry, Mike. I'm on the pill. Don doesn't want any kids."

I quickly moved between her legs and lowered myself into her, entering slowly and savouring every inch of her vagina. She sighed. I kissed her and began a slow rhythm with deep strokes. Soon our movements became more frantic. I sensed that she was about to come, and I knew sure as hell that I was. If only I could hold out just a little longer...

Shannon cried out and grabbed me in a bear hug. I exploded with a force that felt like my balls were coming out my penis. It was my turn to nearly lose consciousness. Slowly I withdrew and pulled her into my arms.

"Mike, that was the most fantastic lovemaking. I'm afraid to believe it, but it seems as though we have perfect chemistry together. Will it always be this good?"

"Yes, if I have anything to say about it."

We fell asleep snuggling. One of my last conscious thoughts was that we'd missed New Year's. And I didn't give a crap. I'd had the best night of my life.

The next morning I awoke to a fantastic feeling. I looked down my body to the most fantastic sight. There was Shannon's angelic face with my penis in her mouth. I moaned. She looked up and me and smiled.

"Good morning, sleepyhead."

Shannon straddled me and guided my erection into her vagina. Then she proceeded to fuck my brains out. Once again we both came incredibly hard. In fact, we both lost consciousness. I awoke a few minutes later to find a sleeping Shannon lying on top of me. My dick had shriveled and slipped out of her. She was still dripping on my balls. I felt perfectly content. As I cuddled her, I thought I was the luckiest bastard on earth. I drifted off.

I was awakened by Shannon's stirring. She was still lying on top of me in my arms.

"Precious, don't you think we should get up?"

"No," she said in a very sleepy voice, "I want to stay here forever. In your arms."

"And you will, little girl. You will."

We did eventually get up. Then we took a shower together. As you might guess, that fact delayed our getting dressed. Eventually, we were forced out of the shower when the hot water gave out. Neither of us really felt like getting dressed, so I grabbed a couple of my T-shirts and some sweat pants. I put on the pants and a T-shirt. Shannon settled for just a shirt. My shirt came to mid-thigh on her. She looked adorable and about 16 or 17. I felt like a dirty old man. It was a great feeling.

I made coffee while Shannon cooked up some eggs and bacon. We ate at the kitchen table. We took turns feeding each other like school kids. At last we finished our breakfast and most of the pot of coffee.

"Shannon, we have some decisions to make. I don't think either one of us is interested in an extramarital affair. I want you, and I want you out in the open, not sneaking around. How about it?"

She looked into her coffee mug for a while. "I love you, Mike. I do very much love you. I guess that I've been slowly coming to the realization that my marriage was over. I just didn't want to admit it. I didn't know what to do if I left Don. Hell, I guess he left me a long time ago in many ways. I'm tired of being a convenience for him. I won't do that again for any man."

I noticed for the first time that she wasn't wearing her rings. Some time between supper and now they'd disappeared. She noticed where I was looking.

"They're in my purse. I'm not going to wear that bastard's rings any more. I seriously thought about flushing them down the toilet. Instead I think that I'll just leave them in the apartment with a 'Dear Don' letter."

"Do you mean," I said, daring to hope.

"Yes, you silly old fart. If you want me, you've got me."

Now it was my turn to cry.

We finally did get dressed. I drove her to her apartment. I helped her pack some suitcases and carried them to the car. I put the suitcases in the trunk, and we drove home.

Home. What a great word when you have someone wonderful to share it with.

The rest of that weekend was spent getting to know each other, in bed and out. I'd never been so much in love, and I allowed myself to believe that Shannon felt the same way. No one could be that good an actress.

On Sunday morning, Shannon delivered yet another of her surprises.

"Mike, have you ever tried anal intercourse?"

"Well, once or twice when I was a lot younger. But it's not my preferred method of love making. Why do you ask? Have you tried it?"

"No. Never. Would you try it with me?"

I was quiet for a few minutes. Then I asked softly, "Darling, why are you asking this?"

"I have my own reasons. Just please believe that it's important to me. Maybe just this once. OK?"

"OK. I'll be as gentle as I can."

I found some lube in the john, and it turned out that there were condoms in the night stand. I put one on. Shannon got on all fours, and I gently applied the lubrication to her anus and my penis. The condom was lubricated, but that lubrication presupposed that one's partner would produce some of her own. Butt holes don't do that.

As gently as I could, I introduced my penis into her. Shannon grunted a few times, her head buried in the pillow.

"Precious, am I hurting you? Shall I stop?"

"No, no. Keep going slowly."

Gradually, I introduced nearly my full length into her.

"Are you all there now?"


"Then fuck me. Please."

I slowly stroked in and out of her. Gradually, the friction became slightly less and her grunts less frequent. I reached around to her clitoris, attempting to give her some pleasure of her own. She spread her legs slightly to ease my access.

"Oh, that's nicer. Oh yes, fuck me. If only those bastards at work could see sweet, prim little Shannon getting fucked in the ass. Or most of all that son of a bitch Don. Keep on fucking me. I want you to come in my ass."

The sight before me, the heightened friction of her anus, and the feeling of her sex proved too much for me, in spite of my concern for Shannon. I accelerated my manipulations of her pussy.

"Oh darling baby, I'm coming. Oh my sweet, dear little Shannon."

"I'm coming, too. Oh Christ, here it comes!"

We both collapsed on the bed. I withdrew from her, careful to keep the condom on and intact. I kissed Shannon and hugged her gently. Then I went into the washroom to clean up.

When I returned, she was crying. Not with the huge racking sobs of two nights before. She was gently crying into her pillow.

I held her to my bosom. "Precious, please don't cry. I'm so sorry that I hurt you. I'll never do that again."

Shannon smiled at me through her tears. "Don't say never. And please don't apologize. I came, didn't I? And I'm not the kinky sort of person who can come when I'm in pain. Just give me a few minutes. I feel like I need a shower."

When she returned from her shower, she looked a lot more like herself. She laid down beside me and put her head on my shoulder. I asked, "Now do you want to tell me what all this is about?"

"To be honest, I think that I just figured it out in the shower. Don has pressured me for years for anal sex. I refused for several reasons. To begin with, I had a very middle-class Catholic upbringing on the Prairies. Like a lot of good Catholic girls, I had trouble enough accepting that my genitals weren't filthy, much less my anus. Then there was also the fact that I now know that I didn't trust Don not to hurt me. Badly. He'd never have been worried about my needs, the way you are. I'm sure that anal intercourse with Don would have been pretty brutal. It would have been an asshole fucking an asshole!"

Shannon giggled at her joke. I was a bit taken aback at her choice of language. In the mouths of many women, those words wouldn't have shocked me at all. I began to realize that I had to cut Shannon more slack. She had to develop her personality in ways that she'd never allowed herself to do.

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Story tagged with:
Ma/Fa / Consensual / Romantic / Cheating / Oral Sex / Anal Sex / Slow /