I have had a few affairs during my working life. I traveled a lot and was away from home for weeks on occasion. Nights alone in a hotel room or in a restaurant, can lead a person to seek temporary comfort. The affairs were seldom of the 'one-night' variety, but usually involved women with whom I became acquainted through my business.
The encounters usually involved widowed or divorced women seeking tenderness for reasons more valid than mine. While they all brought pleasure the affairs never ended up well. Inevitably they were taken over by a sense of guilt on my part, or by the ladies need for more than I had to give. Misery is one word that describes the situation accurately, or at least the endings of the affairs.
And then there was Anna, my neighbor's wife. I have written about her before. A tiny little lady who had lived next door to me for years, and to whom I had initially paid little attention. She had dressed like a peasant woman, was careless about her hair and makeup, and was married to a morose unfriendly man who worked 12 to 14 hours a day. Her appearance and outlook seemed to mirror her dreary life.
As our children left the nest, my wife, who has a wonderful sense of style and fashion, became friendlier with Anna. Within months she had transformed Anna into a quite lovely perfectly formed little woman, her figure displayed in ever more daring manner. The change in her appearance was matched by a more outgoing and friendly manner.
My 'hello's' over the back yard fence took longer and longer to complete. She began to wear provocative outfits such as halter-tops and shorts, sundresses or form fitting slacks and sweaters. My wife was very correct; Anna had a lovely body.
She enjoyed my lingering looks and suggestive comments, and posed for me as I let her know that she was hot. We had given her an old computer of ours and introduced her to the Internet. When technical issues arose she would ask me to help her. One day while resolving her problems, we fucked in her computer chair. It was glorious, that tiny little lady sitting naked on my lap, her beautiful little bum bouncing up and down like a jack-hammer. And all the while she rambled on, "we shouldn't be doing this, it's my fault, what about Marg and Hugo, this is so bad."
This occasion was followed by months of erotic exchanges initiated by me but in response to her eager acceptance of my suggestive compliments. We exchanged E-mail, telephone chats and 'over the back fence' leers and comments. One on one contact did not occur again for some time. But it was fun, it turned me on and I believe her as well. I was ready to meet her again whenever she might want to, but basically we just enjoyed the banter and suggestive chat.
We met again one morning in her house where I introduced her to some of the activities that I had described to her over the phone, and that she claimed were new to her, such as shower sex and mutual oral sex. And once again, it was pure damn pleasure. She enjoyed my delight in her body all the while while claiming that she did not see what I saw in her. She despaired that her breasts were too small, her legs too thin but provocatively preened to feed my obvious interest in them.
Our electronic play continued. It became part of our lives. I usually dropped a suggestive comment by Email every day or so, or we met on Instant Messaging or by telephone. I would send her erotic video clips from the Internet. Our contacts always depended on my being alone or at my downtown office. Anna was always at home by herself from early morning to late evening. Hugo just worked his ass off and it was easy to believe that he was too tired to bother attending to Anna's needs.
In retrospect, she probably was not as naïve as she let on, but it played nicely on my mind. It made me believe that I was her sex guru. And no matter how crude I might be in language or suggested action, she always responded properly and without the use of coarse language. But she let me know that I was turning her on. "Goodness Jim, I could not possibly let you do that! Have you ever done that before?"
For example, my cock and her pussy were always 'it'. I never "fucked' her, I 'took' her. She always protested that 'we shouldn't be doing this', that 'it was wrong' that 'she should not be enticing me like she did', and so on and on. That approach just served to arouse me even more.
We met in her house again, and I barely got out alive. She could come again and again it seemed, and once we were into 'it', she did not want to stop. I was usually quite content with some extended foreplay and one ejaculation. The time between ejaculations for me increased like progressive square roots.
I became concerned about creeping into her house through the back yard. It would not be long before someone noticed it. It became obvious that Anna was ready to meet more often, as our chat between contacts increased in heat and eroticism. I suggested to her that we meet downtown.
Anna's only excursions to the outside world were for shopping. She took the bus to a nearby mall. I asked her to take a bus from her same bus stop to meet me at a hotel. She was reluctant at first, seemingly more relaxed having me 'take her' in her own surroundings.
I called her from my downtown office. "Hi Anna, I want you, catch a bus and I will meet you down here. I'll get a room and we can take our time making love. Please Anna, I need some pussy."
Anna giggled, "You use such bad words Jim. I doubt that you are that much in need of me. I have never met a man in a hotel room. It seems so forbidden, to meet a man for sex like that. I don't think I can do it Jim."
"Ah you will love it Anna. I will get a beautiful room overlooking the bay. We'll make love right away and then shower and I will order lunch with wine. And then back in the sack for a few hours. We can try some things you have never tried before. My cock is aching at the thought of being in your tight pussy."
"Oh Jim, you make it sound so interesting. But it would be a bad thing to do, meeting like that. What about Marg? What about Hugo? You know we should not do things like this. What hotel are you suggesting we meet at? Does the bus stop close to it? I have never taken a bus downtown. What ever would I wear?"
I was pretty certain that I had her hooked now, so I continued on as if it was already decided that we should meet. "Just catch the Main Street Express bus, it leaves every 30 minutes from your bus stop, get off at the corner of Duncan and Main. I will be waiting for you at the bus stop. I am not sure what hotel yet; I will book it right now. Catch the bus at eleven and I will be waiting. Wear whatever you wish; you won't have clothes on long once I have you alone. Don't wear bra or panties. It will make you hot being in public without them. It makes me hot to think about it anyway."
"Oh you are bad Jim. I have never left my house without bra or panties. I am not sure how it would feel sitting on a bus without panties. I am sure I would feel wicked," she giggled.
"You are wicked Anna. You are a witch. You drive me wild when I think of licking and fucking you. By the time you get down here without panties, your pussy will be all slippery and trembling thinking about what I will do to her."
"Oh Jim, you say such bad things, but you make me all excited and all I can think of is you having me and using me. Be sure you are at the bus stop!"
There was no doubt that I would be at the bus stop, and in fact I was there 15 minutes early. She looked great, wearing a form fitting light summer dress and heels. It was obvious that she was not wearing a bra, and from the embarrassed look on her face, it was probable that she was not wearing panties. She was carrying a little handbag so I presumed that she had brought something else to wear home.
"This is awful," she giggled, "what will all these people think. They must know that this is not a business meeting. What will the hotel people think?"
I smiled, "It's a city Anna, nobody even looks at others down here, so nobody knows or cares what we will be doing in fifteen minutes. But what does your pussy think? Did you wear panties? Is she ready to play? I bet that she is nice and wet for me? I hope she is ready, I might lay you with your dress still on."
She grabbed my arm and squeezed her tiny tit on it. "You are so bad Jim," she said, "And yes 'it' is all excited, I keep rubbing my legs together to keep it calm. I might pass out before we get to the room."
She slid passed me as we entered the hotel, her hip brushed my lap and rubbed my stiff cock. "Oh my God," she whispered to me. I had already checked in so we went straight for the elevator. We were alone the last few floors and I pulled her to me for a passionate kiss, my hands sliding down her back to her beautiful little cheeks.
"Ah damn Anna, you don't have panties, want you right now right here," I moaned. However, the elevator stopped before I could act on my threat. My hand was shaking so much that I could barely get the key card into the slot.
As soon as we entered the room I closed the door by pushing Anna back up against it, simultaneously lifting the hem of her dress to her hips. I was fondling her ass and kissing and licking her face and neck at the same time. I soon had a full hand of pussy with my fingers in between her legs as I ground the palm of my hand on her mound.
Anna tried to cool me down, "Oh Jim, not so fast, you are rushing me too much, let's settle down a bit." All this as her fingers fumbled at my zipper and belt, my pants dropped around my ankles. "Oh it feels so big, so hot," she moaned as she pulled my cock out of my shorts and slipped it between her legs. "Slow down, we should go to the bed, don't you want me naked?"
I pulled back enough to see her eyes, "Yes, I want you naked. But first let me put my cock in your pussy, maybe it will settle me down." I reached down and lifted one of her legs up in the crook of my arm, crouched down and worked my knob around, parting the lips and worming it into her.
"Oh Jim, this is not right, I shouldn't have come down here like this, it's my fault, I tease you too much, oh goodness." All this babble as I was pushing my cock relentlessly into her.
The relief of feeling her hot little pussy around my cock calmed me and I was thinking, 'This is too fast, just got in the room and I'm ready to get off, better slow it down, take more time, don't want to end it now.'
I pulled out of her and lifted her dress off. God what a perfect little woman, hardly five feet tall, everything in proportion, sweet little pert titties jutting out, round hips and ass, and the tightest looking shaved pussy I had ever seen. And despite her protestations about 'should not be doing this' her eyes blazed at me, she was ready to be 'taken'. I carried her to the bed and lay her down, stepped back and removed the rest of my clothes.
She spread her legs wide open and reached out for me, "Oh Jim, take me, do what you want with me, it is so wrong, but use me for your pleasure."
Well I certainly did that. The problem was that I was sure that she was ready to fuck steady for four hours or more. And I had my limits. But with careful planning I got through the ordeal. After the first session, I ordered room service for lunch. She hid in the bathroom when the attendant brought the lunch. We hurried through the meal, sipped some wine and showered and fucked again. She did not complain but I could sense she could have stayed in the bed for the entire time.
What had my wife and I produced here? From a forlorn little housewife dressed in drab clothes, to this provocative little lady who could fuck like a feeding piranha. I was beginning to think I had bit off more than I could chew. But her words were always sweet and lady like and constantly reminded me that I was a great lover despite her stated reluctance to seduce me.
We met several more times at the hotel. It was not difficult at all to convince her that she should do some downtown shopping. And in fact it soon became obvious that she was available virtually any time that I desired her. It was still all very pleasant and fun to me, there was never any pressure from her for more meetings; she was just ready when I wanted. And so we continued on, teasing and cajoling on the phone or by Email, and she continued playing the shocked but fascinated object. More often than not when we did meet it was I ending the sessions for a variety of reasons, while she always seemed to be prepared for more.
Her attitude fascinated me. Despite her protestations before during and after our meetings, she did not display any emotion other than that she loved doing 'it' with me. There were no feelings of guilt or remorse apparent in her expression or body language that might confirm her negative words and statements. In addition there were no words or actions that indicated that she wanted anything more than to fuck me on occasion. It was all quite perfect, for me at least.
During one of our erotic telephone exchanges I commented on her apparent insatiability, suggesting that she wanted more sex than I could provide at one time.
She responded, "Oh Jim, why do you say that? Of course I enjoy when we do it. I do have many little orgasms when you are in me, and when you do stop, I could do it again easy. But if you are not ready then, I don't mind, I love the way you use me. Are you angry with me for that?"
"I am not angry at all Anna. You are a wonderful lover and I enjoy every minute of our encounters. But sometimes I worry that I cannot give you enough. Maybe I should get some help," I suggested.
"What do you mean? What kind of help? You are just teasing me aren't you," she said seriously.
"Did you ever think of a threesome with two men Anna? You would be certain of getting all you wanted that way." I was half serious and half pulling her leg, provoking her to see what kind of reaction I might get from her.
"My God Jim. Two men at once? However could I do that? I have never thought of that. My goodness Jim, how crazy."
She seemed quite certain about her lack of interest, so I dropped the matter and we turned to some other erotic subject.
And then she blurted, "Did you ever do that Jim?"
"Do what Anna," I replied innocently.
"Do a threesome like you said, with another man and a woman."
I pondered this for a few minutes. Despite all of the provocative subjects that I had raised with Anna, I had never related experiences with other women. Finally I said, "Yes, I did share a woman with another man on one occasion."
Her voice was more subdued as she said, "What did you do? Did you take turns with her? Were you all in bed at once? Did you both do things to her at once?"
"Something like that Anna. It was all by chance. My partner and I were on a business trip and picked up two ladies in a singles bar one night and invited them back to our hotel." I was ready to leave it at that, but Anna was on the scent.
"I thought you said that you shared a woman. But you had one woman each." Anna was obviously intrigued by the story. She wanted to know more.
"The women were sisters, one married and one recently divorced. I was with the divorced gal, she was quite nervous, her first time out since her divorce. We started necking while Brad, my partner, took the married gal into the bedroom. We could hear the sounds of them fucking very soon after they left us."
"Oh my God, just like that? With her sister in the other room? Are you sure they were doing it?" Anna was aroused; I was beginning to know the signs, even when she was protesting.
"Oh, no doubt they were fucking. Brad is a pussy hound. He seldom misses when he gets a woman alone. She was telling him how big his cock was while he was humping her. We could hear them clearly." I was warming to the story.
"But what were you doing? Your lady must have been embarrassed. Were you touching her? Oh goodness, I could not imagine doing anything like that." The tone of her voice suggested that she was imagining it right then.
"I had her back on the sofa, her head against the arm rest and her bra unhooked. I lifted the bra up and was sucking her nipples." It was time for some detail; this could be the catalyst to entice Anna for another trip downtown.
"What was she doing? She must have been worried about her sister being taken. Were you touching her below?" I could mentally picture Anna at this time, touching herself below.
"Oh yes, I was rubbing her with my cock as I sucked her nipples. I had her skirt around her waist. She was wearing pale blue panties with lace trim. I rubbed her pussy through her panties as I sucked her nipples and then pulled the panties off. I stood up and dropped my pants and shorts and was just getting back between her legs when we could hear Brad getting off in the other room. He was moaning loudly as he come."
Quietly Anna said, "Did you put it in her?"
"Well no, this was the bad part. Just as I was about to cover her and put my cock in, she cried out and jumped up. She said, 'So sorry, I can't do this', and grabbed her panties and jacket and raced out the door."
"Oh, poor you Jim. That must have been awful. All ready to make love like that, and then she was gone. What happened next?" Anna knew there had to be more to the story.
"I was very disappointed. Especially since Brad had been successful and got laid. He would remind me of this forever. I had just pulled my shorts back on and sat back on the sofa, when the other lady came out of the bedroom and asked what I had done to her sister. I explained and she apologized, telling me that she had pushed her sister to get out for a night and to move on with her life after her divorce. She said, 'Obviously it was too soon, and I should not have urged her to come out.'
I still had a hard-on and she soon noticed it. She had pulled her bra and panties on in the bedroom, but now she stripped in front of me and said, 'Let me make amends for the family,' and knelt in front of me. I lifted my butt submissively as she pulled my shorts off and took my cock in her hand."
Anna interrupted, "Jim, that is crazy, she had just had another man in her, and now she is holding you. How could she do that? I don't think that I could."
I said, "Be honest Anna, that makes you hot doesn't it. You sound hot to me anyway. I bet it makes you hot to think about doing two men."
Anna did not rise to the bait but said, "What happened next?"
"Remember the first time I fucked you Anna? You sat on my lap in your computer chair. Remember?"
"Of course I remember Jim. I will never forget it. I had just wanted to excite you that day, with my tight body stocking. And you took me and used me. Why do you ask?"
There was a question about who used whom that day, but I was not going to debate it. I continued, "Because that is what this lady did to me. She straddled me there on the couch and sat down on my cock. She had big tits and as she pulled me to her, she placed one tit on each shoulder. She whispered 'Your buddy did not get me off, I bet you can.' I got her off all right, but it was all through her efforts. I just held still and she bounced away until she came. Just like you did to me in the chair Anna, I could not have stopped you if I tried."
"You are bad Jim. I am sure you did not want me to stop that day either. But what did it feel like to be in a woman just after another man had been there? Was it different?"
"It is called a 'wet deck' Anna. And yes it was quite different. Her pussy felt all relaxed and open, and sticky. It feels something like when we do it a second time. Except of course, it is another man's cum in there."
"Thank you for sharing that story Jim. It did excite me. Did she stay the night with the two of you?" Anna's breathing was heavy and labored; I could sense it even over the phone.