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Anal

This is a slight departure for me. Hope you like it.

A short synopsis of this story to date is here, but reading the previous chapters may help.

My wife, Ann, had decided that she wanted to me to fuck other women. She had been reading cuckold stories and decided that she was a cuckquean. This was based on how enthralled and excited she became by imagining me having sex with other women. I was shocked, but she pursued it. Apparently, she has had some voyeuristic tendencies about watching someone she was dating/with have sex with another woman since college. After she realized what she wanted she had me fuck our neighbor Anita twice and I had teased her with a story about me getting a blowjob at my desk while I made her listen and she loved it. It set her off like nothing had ever had before. Then her college roommate came to visit and I fucked her. Finally, I had made the story about getting a blowjob at my desk a reality with Anita. Each time we did something like this, Ann’s libido really got stimulated and we had sex every day, kids allowing. Once we got a few days away from these events, her libido would return to her only wanting sex once a week. I could tell that this was something that actually stimulated her. The question now, was how to proceed.

I was in the ‘What now?’ part of this new adventure. The first two women had been found and set up for me by my wife. If I was going to go out and find someone on my own it was going to be much more difficult. First, it had to be where nobody knew us or they had to be trustworthy beyond belief. Secondly, it’s just not that easy for a 36 year old man to suddenly thrust himself back into the singles scene and find a woman willing to fuck him, no strings attached, while his wife waits at home. I think it must be much easier for a woman because there are more men who will fuck a married woman and just enjoy the moment than there are women like that. Or maybe that’s just my prejudicial viewpoint since I’m a man.

In any case, I had to find a way to do this. Ann was back to her normal self and I liked that horny wife that I got after an adventure with another woman. She was an animal, did almost anything I wanted, and loved sex more than ever.

One week, I was told that I was going on a trip with one of our company Senior Vice Presidents (SVP), Karen Stevens. It was about 200 miles away so Ann and I discussed the possibility of me playing while away. Ann grinned and was all for it. She wanted me to call her and tell her about it as soon as it was over. Just the thought got her so wound up that she jumped me like a horny teenager the night before I left. What really happened turned out to be more than either of us imagined.

Karen, the SVP, was a woman who was about 40 and very well liked within the organization. She was still fairly good looking, with just the initial appearance of her age in her face. She obviously took good care of herself.

I rode with Karen in her nice Mercedes. When we got to our other company location, we had a lot of work to do with the local folks who were scrambling to meet all the requirements that had been laid out by their customers due to the loss of several people. The vacancies had not been filled. I knew the entire operation from start to finish so I helped them out on Tuesday and Wednesday. I had a good time. They were good people, meant well, and were not afraid of hard work. On Thursday, the last night we were going to be there, we finished the orders for our most important customers, and then adjourned to a local watering hole to celebrate. The local folks who joined Karen and me at the bar were two men and five women. So there were 3 men and 6 women at our little gathering and we started about 7pm. By 9, most everyone except the SVP and I were pretty well lit. She was nursing wine and I was drinking mostly diet Coke. I kept thinking I was going to stick around for a while after everyone had had enough to drink, and look for something, or should I say somebody, to pick up. My hotel was right next door. About 9:30, the crowd started thinning. The SVP and then the rest of the group left except for one tiny, 5 foot tall pixie. She was blonde, had her hair in a ponytail, was cute, funny, and probably only weighed about 95 pounds. She had a cute shape, but was mostly a lithe little thing.

As soon as everyone else left she came over and sat next to me. We were having a pretty innocuous conversation until this point. But then again, she had been drinking a lot and with her small weight, I can imagine it hits her pretty fast. “Can I ask you a personal question, John?”

We had been talking most of the time in the office, so I was surprised she even had to ask permission. “Sure, K.” Her name was Katherine, but everyone just called her K.

“Are you married?”

“Yes.”

She stared up at me with big blue eyes. “Happily?”

“Yes, very.”

She looked at me carefully. “I was just wondering. You’re such a good and likeable guy. You just added another tally to my list that shows that women snatch up all the good men and marry them.”

“If you don’t bahis firmaları mind my asking, K, how old are you?”

She looked up at me. “26.” She was slurring her speech a little and her eyes had the can’t-quite-focus stare about them.

“You’re awful young to be so cynical about that.”

“Yeah, I know. But I’ve been burned by some real assholes.” She put her head in her hands for a second, then looked up and waved at the waitress.

“Sorry. It happens.”

“It’s just hard for a single girl like me with no obvious physical attributes to attract men.”

The waitress appeared at our table before I could answer that and K ordered another scotch on the rocks. I raised an eyebrow.

She raised the empty glass and grinned. “My father trained me well.”

“Where were we?”

“Talking about tiny, little, unattractive me.” She slumped over her drink a little, her shoulders rounded, the alcohol accentuating her depressed outlook.

I stared at her. “You must be kidding. K, you are a very attractive woman. You have a lot to offer someone. You just haven’t met him yet.”

“Yeah, that’s the problem. I haven’t met him yet and don’t see how I’m going to. Girls like Kimberly wear their tight blouses and flash some cleavage and men fall all over themselves to get to her. I just get completely overlooked. Besides, Kimberly’s so damn competitive I think she’s slept with all the guys I told her about after I broke up with them. She’s a trophy collector.”

“Yeah, but if these guys are motivated to pick up Kimberly due to nothing but her cleavage, then it stands to reason that most of them are assholes. Besides, at that point the two deserve each other.”

“Yeah, I suppose.” She thought about that for a few seconds and continued. “But if one of them is a good guy, then it might be worth it to wade through the assholes.”

I grinned. “In order to find a prince you have to kiss a few frogs, eh?”

“At least she can get someone to have sex with her regularly.” She looked up at me suddenly and blushed.

“I think the alcohol is speaking there.” I tried not to laugh.

She shrugged. “Sorry. I didn’t mean to share that.”

“I understand. I’m not exactly a stud muffin.”

She looked up at me. “Hmph. You’re good looking, have a good job, take care of your people, and are a very nice man. You have it all going for you. Women don’t always want the bad guy who everyone is attracted to. Well, maybe some women do at times, but that’s not who they’ll want to have a permanent relationship with. It’s too dangerous. There’s something to be said for reliable and dependable.”

“I suppose.” I looked at her as the waitress returned with the scotch on the rocks. K drank it down and I flinched. She was tying one on.

I waved and motioned to the waitress. “We’ll take the check.”

K looked up at me and said in a pretty slurred voice. “Hey, I’m not done yet.”

“Yes, you are. By the time the last of that alcohol hits your system, you’re going to be regretting it.”

K grinned at me. “Yeah, I know.”

I laughed. “You must be a glutton for punishment.”

She grinned and looked like she was about to fall off her stool.

The waitress came back by, we settled the tab, and we got up to leave. I helped her along since she was more than a little tipsy and the alcohol seemed to hit her harder when she stood up. We got to the front door. “Where do you live? Can you get home in a taxi?”

She mumbled something, the alcohol really affecting her now, and I knew it was hopeless to ask. I put her down on a chair near the door and went through her purse. I found her driver’s license with an address, but wondered if she could have moved since then. It was three years old. I sighed and looked down at her. She was fading fast.

I picked K up and, holding her around her waist, managed to walk her next door to my hotel. I went to the front desk and asked about rooms, but the young lady there said there were no more available. She looked askance at K as I propped her up. I didn’t try to explain. I just held her up and we took the elevator to the fourth floor. I managed to get her into my room without dropping her. Getting my key out was a chore, but fortunately K was small.

Once we were in, I was glad that my company had sprung for a small suite. It had a small sitting area outside a larger sleeping area. I took K into the bedroom and let her flop down on the bed. She laughed and rolled over. She was ready to pass out.

I rolled my eyes. Shit. What had I gotten myself into now? It was not even 10pm. I was planning on going back to the bar and trying to find a little something. Maybe I could still go back.

K was wearing nice slacks and a blouse. I decided that she might be more comfortable without them. I took off her blouse by rolling her around and she barely responded. She had small tits in a nice lacy bra. I left them alone. I pulled off her pants and she was wearing a cute thong. She rolled over onto her stomach. I was never one to take advantage of someone who was this out of it, but I admit I did give her cute, kaçak iddaa little ass a quick squeeze. I’m not THAT nice a guy. I managed to get her under the covers and then, hoping it was unnecessary, put a trash can right next to the bed.

I watched her for a few minutes. She let out a small snore. I chuckled. I saw that she was resting comfortably and decided to head back to the bar. I wasn’t ready for bed yet.

When I got back to the bar I entered and it was lively. Things were pretty busy by the bar and over near a small one-man band, but open by the door. There was a small table there and I sat down. The waitress had just come over and taken my drink order when the crowd at the bar parted enough for me to see a woman at the bar. She was dressed in a very nice skirt, blouse, and jacket. Her heels were not too high. I was looking at her from the side and her shape was evident. She was nicely built, carried herself well, and looked very good from this angle. Then she turned and I was flabbergasted. It was the company VP, Karen, who I had come to this location with. She was laughing and joking with some others at the bar and then noticed me. Her smile melted away instantly and she stared at me. She said something to the others and then made her way over to me.

“Hello, John.”

“Hey, Karen.” I looked her up and down in an obvious manner. “Wow! You look great.”

She almost looked like she was going to blush and looked down. She hesitated for a second. Then she looked up at me and sat down. “Thanks. I was — uh — you know — just having a late drink.” Her hesitation, not to mention her change of clothing, left no doubt that she was doing more than that.

“Yeah. Your friends looked like they appreciated you joining them and I have to say that I approve of this outfit. You look wonderful in it.” She had always dressed well, but she had never highlighted her assets like she was now.

She looked back over at the group. There were 4 guys and two girls there. They looked like they wanted her to join them, but she was having second thoughts. “Well, I’m going back to the hotel now.”

“Hey, don’t cut your night short because of me. I just came for a drink, too.”

“No, I really should get back. We have to leave in the morning.” She stood up.

I got up, too. “Well, I’ll walk you back to the hotel.”

She just nodded and we started walking to the hotel next door. Half way there I decided to see what was up. “Not that it’s any of my business, but it looked to me like you were there to have a little fun.”

Her head jerked up. “What? What do you mean?”

“C’mon, Karen, it was obvious that you were looking for a little, uh, companionship shall we say?”

Suddenly, tears came to her eyes and she stopped. “Oh, god.”

Shit! I felt bad. “Karen, I’m sorry. I didn’t mean to pry. That’s your business.”

She turned to me and thrust herself into my arms. She started crying on my shoulder. “I’m sorry. I can’t — I mean I don’t know what to say.”

“That’s fine.” I patted her back as we hugged. Something was going on. She had always been the consummate professional. She was a strong, vibrant woman at work. Something must really be bothering her. Could she be feeling guilty about being caught? Or maybe she was feeling guilty that she even considered it.

She pulled back and looked me in the eyes. “Want another drink? I need to finish off this drunk.”

“Uh, sure.” I was not sure at all but thought there was no choice in the matter.

“Okay, let’s raid the bottles in my room.”

“Okay.” I followed her to her room. When we got there I sat down on the couch while she retrieved a couple of the small liquor bottles from the small refrigerator.

She held up a couple of bottles. “Whiskey?”

“Great.”

She gave me a glass and the bottle. She had no ice, so I just opened the bottle and took a swig. She chuckled and did the same with her bottle. “Maybe I should explain.”

I held up my hand. “You don’t have to. It’s none of my business.”

She stared at me for a long time. I was starting to wonder what was going through her mind. “I’m going to tell you anyway. You’re a good guy and I trust you.” She took a deep breath. “My husband left me three months ago for a woman who was 25. Twenty-fucking-five. Can you believe it? I’m 42 and I gave him 22 years. I wasn’t even out of college when I got pregnant and we had two kids by the time I was 23. The last one just went away to college. I managed to go back to school and get my degree. We both worked hard and were successful. I thought we were entering a new era with the kids leaving home for college, but it wasn’t to be. He told me that he hasn’t loved me for a long time and he has been having affairs for several years. Finally, he fell in love with this 25 year old. Shit! She’s only 4 years older than our daughter. The bastard. Now I’m alone and feel miserable. I want to still enjoy life, but when I was in that bar trying to get reacquainted with the younger crowd I realized that I had nothing in common with any of them. I was lost and kidding myself about being able kaçak bahis to do that.” She stopped and looked at me.

“Karen, you are a beautiful woman. You are not a youngster but you still have a lot to offer the right person.”

She looked at me. “I’ve known you for a long time. You’re a good worker, nice looking, and a very nice guy. If you weren’t married, I’d attack you right now.”

She said it jokingly and maybe it was the alcohol talking, but I upped the ante. “What’s stopping you?”

“You know what’s stopping me. You’re married and I won’t do to another woman what has been done to me.”

“And if I could convince you that it was okay, you’d really have sex with me?”

“Of course. But there’s no way you can convince me of that.”

“Wanna bet?”

“I think I already did. If you convince me I’ll have sex with you, if not, we don’t.” She grinned like she knew that it was not possible for me to convince her.

I pulled out my phone and her eyes went wide. I dialed my wife. It was just after 11pm. I hoped she was awake. She answered on the first ring. I put it on speaker. “Hey, gorgeous.”

“Hi, baby. Lonely tonight?” Karen looked at me quizzically.

“A little bit, but I’m in the hotel room of a beautiful woman.”

“Yes?” Her voice dropped like we were conspiring to do something illegal. “Are you going to fuck her?” Karen’s eyes went wider and her mouth came open in surprise.

“What do you think?”

“I think you should show her a good time and then come home and tell me about it. I can’t wait for you to tell me how you ravished her and fucked her good.”

“Yeah, I can’t wait for that either. You’re always so hot when I tell you about fucking another woman. Your libido is high for days after that.” Karen just continued to stare at me.

“Oh, yes. I’m turned on just thinking about it. Make sure you call me and tell me all about it tomorrow morning. I want to get off listening to it when the kids are at school.”

“Okay, hun. I’ll tell you all about it. I just have to finish the seduction.”

“I have confidence in you, honey. And you are a great lover. She’ll be missing out if she passes up your mouth. You eat pussy like a rabid lesbian.”

I laughed and Karen put her hand over her mouth to keep from letting herself be heard as she tried to hold her guffaw in. “Okay, honey, I need to go. I want to see if this beautiful woman will let me fuck her.”

“Wait. Before you go, tell me what she looks like. I want to imagine you fucking her while I get off.”

“She’s about 40 years old, 5′ 7″, and very attractive. She has brown hair and brown eyes. Her body is very nice. It’s obvious that she takes good care of herself. She has a small waist and nice full womanly parts, you know, hips and tits.” Karen raised her eyebrows on that one. “Anyway, I’m sure I’m going to have fun seducing and discovering how good this woman’s body really is. Gotta go.”

“Okay, make her cum a lot. Love you.”

“Love you, too. Bye.” I hung up.

Karen stared at me. “Wait a minute. She really lets you fuck other women?”

“It’s a long story, but yes, we found this out recently. I’ve only had sex with two other women since we discovered this. Evidently, it turns her on and gets her off. It actually stimulates her libido and makes our sex life much better.”

Karen was watching me carefully. “And you really think you can seduce me?”

“Is that the right word now? Is it necessary? We both know what we want and we are consenting adults. It just depends on what you think about having sex with someone from the same company and same town. We don’t work in the same organization, but if you are not comfortable with it, then we won’t do it. It’s up to you.” I paused. “But you did bet me.” I stood up and held my hand out to her.

Karen thought for a moment and stared at me. Then she got up and put her hand in mine. “I’m horny, a little drunk, and haven’t had sex in four months. You think I’m going to pass this up after what your wife said about your mouth?” She grinned. “My husband didn’t give me oral sex.”

I looked at her mischievously and leaned in close. Since she had used such proper words, I wanted to make it dirty. “You mean he didn’t eat your pussy?”

She grinned, averted her eyes, and blushed. “Yeah, that.”

I pulled her in and kissed her. Her lips were soft and receptive, as was her tongue. She was soft and cushiony to hold. She was a full figured, beautiful, sexy woman. I had no idea what may have happened between the two of them over 22 years, but I was going to try and give her a night to remember.

I broke our kiss and she looked up at me. I led her into the bedroom part of the suite and next to the bed. “Stand here.” I then slowly unbuttoned her blouse and kissed the tops of her nice round tits. She didn’t say anything, just let me continue. I removed the blouse and then knelt and felt around for the zipper and catch for the skirt. I found it on the side and released it. I slid the skirt to the floor to find that she was wearing hold-up stockings and satiny looking black panties. It wasn’t a thong, but it showed her assets beautifully. I kissed her stomach and she flinched a little and giggled. I kissed down over her mound and then grabbed her by her hips and turned her around. She cooperated easily.

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