Will's Surprise

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Jackie picks up a stranger or two.
5.7k words
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I have been married to Will for 23 years. We were married when I was 19 and he was 23. I was sexually active before marriage, but not easy. Prior to Will, I had made love to about 10 different guys. There was something about Will that broke down my resistance. We made love on our second date. During the years of marriage we tried all kinds of sexual games, from simple role playing to wife swapping. I even danced nude, at a local club a couple of times for him. But he always seemed to want more. During the last four or five years, we have been at odds over my refusal to participate in any more sexual actives, involving other people.

As a result our marriage was not in the best condition. Will had asked for me to let him watch me, make love to another man for a long time. We had tried it once with less than satisfactory results. We selected, an out of town friend, who was discreet. He was so nervous that he could not get an erection, although he did give me several orgasms with his tongue and fingers. My husband wanted me to pickup a stranger for sex. He thought that a horny stranger would not be so nervous. I told him to not even think about it, but I know that he does. Will has told me some of his fantasies, where he watches me with another guy without the guy knowing it or with him present as an observer and/or participant. The thought of giving myself to another man is exciting but due to my upbringing and fear of aids, It did not feel right.

Recently a friend from school, who did some traveling for her company, was in town for the weekend. I visited her at the hotel where she was staying. We talked for hours catching up on old times. She told me that she had picked up a good-looking guy from the hotel bar the week before. He had taken her back to his room and screwed the living daylights of her. I was surprised to hear her story and asked her how she could do that being married and all. She said that her husband encouraged her to do it. They had talked on the phone and when she told him that she was horny, he told her to go get laid. Then he told her that he really wanted her to have sex with another man.

She thought he was kidding her, so she decided to call his bluff. She went down to the bar and struck up a conversation with a man, she called Frank. She told him about the conversation she'd had with her husband. He volunteered to be her lover for the evening but all she wanted him to do was help her play a joke on her husband. They went to a phone and called him, holding the phone so both of them could hear. She told him that a suitable mate had been found and that they were heading to the room for sex. He asked her what he looked like. After she described her pickup, she told him that Frank was nervous and wanted to make sure it was ok with him. Her husband told her it was fine by him, but wanted some photographic proof.

Frank said, "no problem, we will take some."

Her husband said, "great, have fun," then hung up.

My friend was stuck, her pickup was smiling and looked her body over with great interest knowing that her husband had just given his permission. She decided what the hell and went up to his room.

They had taken nine or ten photos of themselves using the timer on the camera. The photos showed them undressing, fondling each other, having oral sex and three or four shots with his member inside her. She said that when she showed her husband the photos he got so excited that he made love to her three times that night. When she left on this trip, he let her know that he was looking forward to more photos. I asked if she was going to pick someone up tonight. She was looking forward to going downstairs to see if there were any likely candidates. As I was leaving, I told her to be careful and have fun. On the drive home I could not get my mind off the things she had told me. The parallels between her relationship and mine were astounding. By the time I got home I had decided on a course of action. Will had a surprise cumming and he did not know it. The more I thought about it the more excited I became.

A few weeks later, Will had made a big real estate deal and wanted to celebrate. Little did he know how much he and I would enjoy the celebration. I reserved two adjoining rooms at a hotel. The rooms shared the same balcony with a four foot fence dividing it. With the lights on inside the room the windows to the balcony turned into mirrors and I could not see out but a person outside could see in perfectly. I told Will that I had made dinner reservations for Saturday night and that we were going to celebrate the big deal then. He wanted to know what else we were going to do.

I gave him a knowing smile and said, "I'll think of something."

"I hope it has something to do with sex," he replied.

"We will see," was all I said.

During the next few days I could not sit still, anticipating what I was planning to do. I decided that I needed a new dress for the occasion. I found a dark blue silk dress with a tight fitting bottom ending about mid-thigh and a bloused low cut top. When I put it on without a bra, I noticed that by bending about 20 degrees my breasts were visible to anyone within three or four feet. I knew that Will liked me braless and figured other men would too. While looking at myself in the dress, anticipating the male reaction I hoped to provoke, I felt my body blush and lubricate. It was hard not to touch myself right there in the fitting room.

On Saturday night I made Will wait twenty minutes for me after he was ready. After all, a woman has to look the part when she is on the make. I even shaved all the hair from between my legs. When he saw me, his eyes lit up and he licked his lips.

Smiling at me wickedly, he told me, "You look like any man's wet dream. Who are you trying to seduce."

I winked, "I do not know what you are talking about." From the way I was dressed he could tell something was up. I had matched the dress with stockings and a garter belt and I looked as hot as I felt.

When we got to the restaurant we discovered our reservation was messed up and we would have to wait about two hours. We went to the hotel bar for a drink. As we sat there, I could not help wondering if my friend had picked up another guy here a few weeks ago.

I was thinking about her having sex in the room where we talked, when Will said, "that guy over there is giving you the eye."

When I looked at the guy, he winked at me, holding his glass in salute. I nodded thank you and quickly looked away, but not before noticing how handsome he was. He must have come from the pool since he was wearing a tight swimsuit and a tank top. He appeared to be in his middle thirties, trim and firm. The way his suit stretched out between his legs was very promising. When I glanced at him again, he was still looking at me. When he saw my glance, he used his hand to readjust his equipment. What started out a promise turned into reality.

My husband said, "it looks like you have a second date tonight."

"What do you mean by that?" I replied.

"That guy wants you in bed with him, as soon as possible." he said.

I knew he was right but the direction this conversation was going was testing my resolve. I played dumb a little while longer by saying, "oh really!"

Will leaned over and whispered in my ear, "I'll bet that if you went over and exchanged pleasantries for a few moments and then asked him if he wanted to have sex with you, as long as I was present. He would agree."

I thought that the chances this guy would agree were pretty good, now if I only had the courage to stand up and walk over there.

But I said, "he probably won't, but I might ask him just to be sure."

"Well go ahead and talk to him." He said.

"But what if he really does agree?" I wondered.

"What do you think?" he asked.

"Well then I guess I am committed, aren't I?"

"I guess so!" he replied.

I was a little nervous and during our conversation I shifted on my seat and recrossed my legs several times. I discovered that my dress had ridden several inches, above my stocking tops. Realizing that with my legs pointed toward him, he could see my bare pussy each time I recrossed my legs. When I looked at him, the look on his face told me what he had seen. I blushed bright red, realizing that my pussy had made my decision for me. When I looked at Will, he must have noticed the same thing.

He smiled and said, "go on, it will be fun."

"All right, dammit, I will." I said standing up.

With butterflies in my stomach and rubber in my legs, I made my way over to the bar. When I perched on the bar stool next to him.

"Hi, my name is Alex," and held out his hand.

"Jackie" I stammered.

"You are quite lovely you know." He replied in a smooth southern accent, his bright blue eyes stripping me naked as he looked at me. We talked about stupid things for a few minutes.

Bringing the subject back to sex he said, "I really like your hair do, or is it lack of hair with lots of dew."

My pussy contracted at the obvious reference to its hairless condition. "You saw that did you?" I asked.

"I thought you were showing it to me on purpose, weren't you?"

"I guess I was without realizing it." I thought, but said, "no it was an accident."

"Is it ok for me to sit here and watch your accidents or would you like to come to my room for several collisions?" He asked.

There it was, the invitation. I could not believe this was happening this fast. Realizing that this was my last chance to back out I found myself saying, "my husband has always wanted to see me have sex with a stranger, so if you are that stranger and don't mind my husband cumming along with his camera, things may work out or in, as the case maybe."

Alex looked at Will who smiled at him. Then turning back to me, he leaned over, putting a hand on my knee slipping it between my legs, touching my wet pussy, and said, "I'm your stranger and ready to go when you are." The thrill of his touch and the thought of having sex with this guy made me shake with desire.

Will and Alex backed me into the corner of the vacant elevator. I closed my eyes and tried to figure out whose hands were whose. By the time we reached his floor, my dress was bunched around my waist from the bottom up and the top down. My breasts and nipples were touched and kissed. My pussy and clit were touched and invaded by several different hands. Once we were safely in his room. Will took a seat on a chair near the bed. Alex and I sat on the bed. Alex turned me toward him and kissed me very senuously. When he broke the kiss, he stood in front of me and pulled me to a standing position. Moving his hands to my shoulders, he slid my dress off of them. Pulling off his shirt, showing me his well-developed chest. He began to nibble on my neck and on down to my breasts. He licked and sucked them for a few minutes, while his hand worked my dress the rest of the way off. Reaching behind me he undid my garter. Pushing me back on the bed he removed his shorts. His member bounced up when it was released, I watched it bob while Alex rolled my stockings off. It was larger than Will's, about seven inches long and pretty thick. He urged me into the middle of the bed and crawling between my legs, putting a finger on each side of my pussy, he held me open and lowering his head, he licked my clit.

I had been anticipating this moment for almost a week but the reality turned out to be much better than my imagination. His tongue was sending jolts of electric pleasure through my entire body. I felt him shift on the bed, then a finger began to probe into me. My hips began to move as I felt my orgasm start to build. As a second finger began to move in and out of me, Alex increased the speed of his licking. His fingers found my g-spot and began to rub it. Without conscious thought, my legs moved farther apart giving him better access to my sex. My body was trembling and I could feel my orgasm begin to peak. Then there it was, my hips pushed my pussy onto his fingers. Sitting up he replaced his tongue with his thumb, rubbing my clit from side to side and sliding two fingers in and out. As I was cumming down the backside of my orgasm, I looked at Alex. He was stroking his very hard dick and I knew that in a few seconds that dick would be put inside of me. Glancing at the chair I discovered Will was not in it. Looking around I spotted him with his camera. He had been taking photos and I did not even know it. He gave me a big smile and blew me a kiss.

Alex began to position himself between my legs, drawing my attention back to his intentions. I felt him slide part way in then stop.

When I looked at him, he said, "do you want my hard cock deep inside you?"

I nodded my head and moved my hips toward him.

"No" he said, pulling almost all the way out, "say it!"

The sex goddess took control of my speech and said, "I want your hard cock deep inside me, now!"

The word, now, became nnnooooowww! Alex had begun to slide his member into me as the sex goddess spoke. He hit bottom on the word, now. He began to fuck into me at a steady pace. My hands grabbed the back of my knees pulling them out and back, spreading myself as I moved my hips into his. I thought his size would be a problem but as wet as I was, I was able to take all that he could give. The sensations his larger cock was giving me were new and erotically thrilling. Alex began to increase the speed and depth of his thrusts. The angle of his cock entering me caused my clit to rub against his thrusting member. My orgasm came from nowhere, sending me over the edge with no warning. Alex must have felt my muscles contract. He buried himself inside me while my pussy spasmed, which made it more enjoyable. After I relaxed, he pulled out and asked me to turn over.

I heard my husband tell Alex, "put a couple of pillow under her hips."

I love this position and Will knew it. In this position, I lay face down with the pillows under my hips. This elevates my pussy and Will says, when I spread my legs, the view from behind is breathtaking. My ears were listening when, I spread my legs and wiggled my butt. Sure enough I heard two sharp intakes. The bitch in me realized the power I had over these two men slash boys. All I needed to do was threaten to get dressed and go home. They would give me anything they could, to keep me right where I was. Fortunately for them, I was in exactly the place, I wanted to be. Alex moved between my legs and placed his hard penis against my pussy. I put my hand underneath me between my legs and grabbed his cock.

Alex started to slide his member in and out of my hand. Each time he slid in, his cock would bounce on my clit. It felt silky hard and very big. He changed the angle of his thrusts and slid back into me. Now it was my turn to take a sharp breath. My fingers moved to my button and began to stroke it, the way only I know how to. Alex was pounding in and out of me, moaning how good I felt and looked, to him. My body was on fire. I don't remember ever being this turned on. His cock was driving into me and I was driving my pussy onto him. My orgasm was almost there, when I heard Alex say he was getting very close. Then wham it hit me, I pushed and held my pussy up, letting him thrust into me over and over and deeper and deeper again. My pussy was clamping down on him each time he pushed in. I felt his cock begin to swell and pulse deep inside me, as he came and my orgasm washed over me.

A few minutes later, Alex moved off me. My husband rolled me over and smiled at me, showing me his hard cock. He took me in his arms kissing me and sliding his cock into me at the same time. He then went on to make love to me as only long time lovers can. He gave me another orgasm, cumming with me explosively. When we looked around, we found that Alex had left. We rested in bed for ten or fifteen minutes. Our stomachs reminded us that we had not had dinner. So, we took a quick shower and left Alex's room. Dressed again, in my man killer dress we headed for the restaurant.

I felt great and was still excited by what had just happened. Will was all smiles and puffed up with pride at having me for his wife. At dinner, after we ordered, the waiter came back with an expensive bottle of wine for us. He told us it was from the man at the bar. We looked up to see Alex. I went to him and gave him a big kiss and a hug to say thank you. He told me that it had been a real pleasure getting to know you, then he left. Will is not a wine drinker, so I managed to consume three quarters of the bottle during dinner. By the time we were paying the bill, I was feeling pretty tipsy and very horny. Will told me he had to use the bathroom. I went to the bar with my glass of wine to wait for him. As I walked to the bar, this really cute kid about twenty-five gave me the eye. I sat two stools away from him and boldly watched him back.

He smiled and moved next to me saying, "hi, I'm Mike, and I think you are the hottest woman I have ever seen."

This was a bold cocky young man, but he had just met his match. The wine and the erotic nature of this night combined with the itch that was developing between my legs, prompted me to say in my Mae West voice, "Why thank you, big boy, but is that a pickle in your pocket or are you just really glad to see me?"

"Oh that's no pickle ma'am, I am, really, glad to see you," he replied.

Once the ice was broken, with a few minutes of normal conversation, during which Mike told me he had just won 20 thousand dollars playing craps but was here alone and wanted to share his good fortune with someone. I asked him what he was going to do with all that money.

"I would like to find a woman like you, who would be my lover to night." He replied.

"How much is it worth to you?" I asked.

Mike thought for a moment, while his eyes moved over me with x-ray vision and said, "I'll give you two thousand dollars to have sex with me, the way I want."

"What exactly what is your way?" I wondered.

"I want you to dance naked for me, while playing with yourself. I want you to show me your body openly, putting your fingers inside and cumming for me. Then I want you to fuck me like a found lost lover."

His good fortune was certainly rubbing off on me. While I was thinking over his proposal, I saw Will cumming back from the bathroom. I waved him away thinking, this is perfect, now I'll get to use the hotel rooms I rented. Will would get to watch this young man fuck me, without him knowing he was being watched. And he was going to give me two thousand dollars for something I was more than willing to do anyway. I told him his terms were acceptable, but after we were done, he would leave when I told him to. He said that would be fine since he had an early flight home. I gave him my room number and told him to meet me there in thirty minutes, which gave me time to freshen up. I gave him a nice kiss and rubbed my breasts on his shoulder on the way out. Will followed me out pretending that he did not know me until we were on the elevator.

"Where are we going?" He asked.

"To my room," I replied showing him my room keys.

"What are you planning?" he asked.

I repeated the conversation Mike and I just had. I told him that I intended to fuck Mike silly and he could watch without Mike knowing it. Will was clearly very excited about the sexual turn around of his wife. He asked what had caused it. I told him about my girlfriend and her husband. He said we should meet her and her husband, maybe something interesting would develop. That is an interesting possibility I thought. When we got to my rooms and he discovered how well, I had set things up he was very surprised and happy, to say the least. I straightened my hair, fixed my make up and added more perfume. Will told me how sexy I was and how much he loved me for giving him his fantasy. I told him that the pleasure was and will be all mine. The wine, Alex and the expected sexual encounter with Mike had me floating along side of my own, personal sex goddess. Here I was a middle-aged woman ready to fuck a kid half my age. My pussy tingled at the thought, when I heard someone knock on the door, a sexual jolt ran through me which almost made me cum. After giving me a very passionate kiss and sliding a finger up me, Will went next door leaving the balcony and connecting doors ajar so he could hear as well as see what would happen. I decided to be bold and earn my money by giving Mike more than we bargained for. I vowed that he would never think about an older woman again without his dick tingling from his encounter with me.

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