Watching Cindy

Joe's story....

Cindy and I have been happily married for 16 years. We are both successful professional people who are active and visible in the community where we live, near Boston. Cindy is 42. I am several years older. Cindy, who was born in Sweden, keeps herself in great shape with regular workouts, tennis, skiing, running and bike riding. She has the toned body of a woman years younger, and a very attractive face, with bright blue eyes and prominent high cheek bones. She is 5'9" with stylishly cut blond hair. Her legs are lean and shapely, topped off by my favorite kind of butt... not too large yet full and round. Cindy's ass moves sensuously (and obviously) when she walks, whether in her usual tight jeans, nude, or even in a dress. Cindy's breasts are medium-sized, firm and wonderful to touch. I keep myself in shape too.

From the first night we met we have enjoyed great sex, but for some time I was uncomfortable talking about Cindy's sex life before we met. I was still a bit insecure I guess. Basically what we'd each done before was off limits. Until we'd been married for a couple of years we never discussed it at all. Then that began to change. We enjoyed watching porn movies together every couple of months. I began to be aroused by the notion that Cindy was sexually stimulated by seeing other men, naked, erect, well endowed.

I started to comment, saying things like: "Wow! That guy has a big dick! And he is really aroused. I bet you like that, don't you lover?"

Cindy at first would reply a bit shyly, saying "yes, his is big, but I love your penis dear."

Over time Cindy's comments became bolder. She realized it turned me on to hear her comment admiringly about an especially large or especially hard-looking cock on a porn actor. She began to initiate comments, her always deep sexy voice breathlessly saying things like: "Oh my god! Joe, will you look at the hard-on on that guy! His cock is huge! And SO aroused." I'd encourage her, feeling my cock swelling as I listened to her lewd remarks about other men's cocks. I began to seek out stories about her past lovers as well. She gradually became more open. These conversations were a form of verbal foreplay for us, a sexy conversation over wine that would be a prelude to scorching sex. We were clearly moving in a new, erotic direction, jealousy gone, more secure in our relationship, sexually and in general.

In recent years we began to incorporate the theme of "the other man" into the sexual fantasies we acted out. I bought Cindy several dildoes (the first as a Valentine's Day gift), going for more and more realistic ones. A favorite of us both is a very life-like 8" model, thick, smooth, complete with a set of balls, realistic coloring, veins: the complete package. It has a strong suction cup so it can be stuck to a wall, which we put to good use. In our "threesomes" Cindy might suck me, bending over in a standing position next to the bed while she is taken in the pussy by the dildo stuck to the adjacent wall. This is powerfully erotic to me and to her. Another favorite is for her to suck the other man while I fuck her, at times with my face right next to hers, with his penis being worked over by her hot mouth, close up. She acts well and makes it realistic.

We gave the "other man" names, sometimes of men we knew, or actors, athletes, guys from work. Both of us contributed suggestions, created characters. A particular treat for me was fucking Cindy's hot, tight ass and pussy simultaneously with me taking one hot opening and "him" the other. I loved feeling our cocks rub together as we fucked her. I also loved to sometimes just watch Cindy "do it" with the other man. She has a way of making it seem real, teasing herself (and me) as she licks, strokes, sucks, and penetrates herself, ever so sensuously, calculated to drive me wild as I masturbate watching her, listening to her vivid reactions and filthy talk, and most exiting of all watching and listening to her explosive orgasms.

Last year I raised the idea of Cindy really fucking another man, while I watched. She laughed it off at first, saying she had no real interest in anyone else, that it was a great fantasy for her but nothing more. Just talking about it was a major turn-on, and gradually her response began to change. She'd ask if I really wanted that, and we began to think of how we could actually go about getting another man, safely and anonymously...but purely on a hypothetical level, of course. I was going crazy with lust as these discussions progressed, feeling more and more that my now-#1 fantasy might actually happen. Among friends or in public places sometimes I'd look over the men and try to imagine watching Cindy with one of them.

Cindy and I often exchange private "gift certificates", which entitle the bearer to certain sexual favors. We've used these to expand our sexual boundaries. Cindy gave me one for Christmas that said the bearer was entitled to "fulfilling one sexual fantasy of his choice...no restrictions apply". I'd had one like this before and loved how open-ended it was, how much trust it showed we had. The last one, I'd used to have her act out a fantasy of the "other man" fucking my ass after taking her pussy! She'd responded with shock when I first broached that idea, but when the time came to "redeem" the certificate there she was, eagerly bringing herself off with "Don" then sucking my engorged cock as she pounded my well-lubed ass with the dildo until I shot an enormous load.

This time I told her: "Cindy, my love, I am redeeming this "anything goes" certificate you gave me now. It says it needs to be turned in at least 5 days before the actual activity (we did that to build anticipation over time, which is a powerful sexual tonic). Next Thursday night I am going to"...and here I hesitated, gathering my courage to actually say what I'd been planning for months...then I blurted it out: "watch you have sex with another man!"

Cindy looked at me with a funny look on her face. "Joe, are you serious? Really?"

I gulped, and replied: "Well love, after all this talk and role playing, I've got to admit that the idea of it really turns me on, so I figure if it would be O.K with you, well, yeah. I am serious. But only if it is O.K. for you too."

Cindy responded saying that she shouldn't be completely shocked as for years she'd known how much I loved the idea on a fantasy level, and how the stories I printed and showed her from Literotica were often on this topic too. She finished by asking:

"Say we did it. Who would the guy be? Have you already picked someone out?"

Her questions opened the door for me to go on, to explain the plan I'd concocted. My heart was racing as I tried to maintain a casual demeanor.

"No lover, I haven't picked anyone out . But here's what I've been thinking might work, for me and especially for you. I'd need this to be good for you, or wouldn't want to do it."

"Well then, what is it? Just what have you come up with you naughty man you?" she asked with a wicked grin.

"Wow! She's actually sounding playful about it" I thought, and then, past the first big hurdle, described for Cindy how we might do it. She listened as I described my plan.

We'd go out to a nice high-end hotel bar downtown. This would eliminate any risk of being discovered. The Ritz-Carleton was the example I used. We'd go on a week night, like next Thursday, when there were bound to be business travelers there, men far from home in a city where they were not known outside their business contacts. We'd bide our time, looking over every guy in the bar until we saw one that Cindy approved of, based on appearance. Then we'd make our way toward him so we could strike up a conversation and ask him to join us for a drink. That would give us some time to interact, to see what kind of guy he was so Cindy could decide if she wanted to go forward with him as the "other man" of our fantasies. And of course he'd have to be agreeable. If we were "shot down" it would be embarrassing, but we would simply leave the bar.

"God, Joe, you've really given this a lot of thought haven't you?" she interrupted.

She was taking this all in, taking it seriously! My cock swelling, I went on.

I told her that at any point when she was ready to decide, we'd have a signal between us, so I'd know for sure whether she approved or not. She might say "excuse me guys, but I have to use the ladies room" if she meant "no" and "excuse me guys, I'll be right back" if she meant "yes".

While she was gone, if the answer was "yes" I would figure out how to make the proposition, maybe simply straightforwardly asking the man if he would like to have sex with my wife, that I'd like to watch, and that this was a fantasy we had that we wanted to act on. It sure sounded easy! Of course if her signal was "no" we'd just move on.

I explained why I felt a nice hotel bar was ideal: First, we would be unknown there and could keep it on a first name basis. No one could "trace" us and cause trouble later. Second, there were bound to be business travelers there, and they might be open for an adventure like this, away from home and anonymous themselves. Third, by choosing a high-end hotel we'd narrow the prospects down to people with whom we could be comfortable. And we'd be the ones taking the initiative, with measures built in to bail out if it felt wrong.

Here Cindy added an idea of her own! She said: "I'd want for him to be married! I'd want to see that he had a wedding ring on. It would just feel safer to me if he were."

This was unbelievable! Now Cindy was actually helping design the plan!

I added that we'd be hooking up with a man who was staying in the hotel where we met him so we would have sex in his hotel room. Keeping things on a first name basis, there would be no trace of us for anyone to follow, providing anonymity and security! And the room would be beautiful, well-appointed and safe. Cindy and I always loved sex in nice hotels.

"So, how's that sound?" I asked.

"Damn, Joe, you are something else! What a mind! What can I say? It sounds really possible. And if you really want to, I guess I'm game to try. And I did give you that certificate."

"So next Thursday night?" I asked, still trying to sound casual, my heart beating like a jackhammer.

"That's five days from now, and that's what the certificate I gave to you says."

We embraced and between kisses I told Cindy how much I loved her, how sexy she was and how lucky I was to have her as a wife.

I was totally preoccupied as Thursday approached. We decided to refrain from sex during this time to heighten the excitement and tension. Finally it was Thursday. We both came home a couple of hours early to get ready. Both of us tried to act normal, as we showered and got dressed, not easy! When I came out of the shower I saw that Cindy had on her sexiest undergarments. She had donned simple black silk "boy leg" panties, the legs so short that her very shapely ass cheeks showed provocatively from below the material. She wore a matching bra that slightly pushed up her lovely 36 C breasts, making the cleavage look wonderful. And she'd added a very special touch that she knew drove me wild, thigh-high silk stockings. She was putting on make up, her long blond hair piled on top of her head, as I entered the room and let out a low whistle.

"Wow! You are some hot babe Cindy. This is going to be unbelievable!"

"We'll see Joe. I hope so." she said in response.

I put on the clothes I'd planned for the big night, wanting to look casual but classy... grey wool slacks, a black silk-like shirt and a grey sport coat.

Cindy slipped on a simple black dress, short to show off her great legs, and low-cut enough that the tops her breasts were visible. With her simple gold necklace, and finally her sexy 3 inch heels, she looked perfect...totally sexy and very classy.

"Some lucky S.O.B. has no idea what he's getting tonight" I thought as we walked out to the car. I had been semi-erect most of the day and was very conscious of my cock as I got into the car.

The ride to Boston was a little quieter that usual as we tried to make small talk, but with other things on our minds. I didn't really want to talk about what we were about, in fear that Cindy would change her mind. As we parked in a garage near the Ritz-Carleton, which overlooks the Boston Public Garden, I felt spaced-out and admitted to Cindy that I was a little nervous. She said: "me too."

I was amazed to be among people walking this way and that, going about their normal lives. It somehow seemed very strange to me doing what I was doing and feeling the way I did.

We walked into the bar, a took a small table with a good vantage point. I ordered a good bourbon for me and Cindy got a Cosmopolitan as we looked around. It was about 7:30 P.M., kind of quiet, with maybe 8 or 10 people in the bar, five of them men who appeared to be alone.

"Quiet night. Everyone is probably up in their room, jerking off to a porn movie" I joked.

"Like you do on business trips, right sweetie? Wonder if they call their wives as they are doing it like you do?" she replied, smiling sweetly, teasing me.

That was a favorite for us when I traveled on business. Man! Cindy was a sexy woman, even over the phone! She looked great now, sipping her drink, trying to look relaxed.

"Well? See any prospects?" I asked her after maybe ten minutes had passed and our first drinks were nearly done.

She picked out one, then another. Each time I had to take care not to feel like "Why him? Is he that attractive?" Both turned out to have zero personality and Cindy to my relief gave the "no way" signal as she went to the ladies room, and I excused myself from the "prospect" while she was gone.

Cindy returned each time laughing, commenting about how lucky I was she didn't pick that guy!. I laughed, agreeing. I saw her eying the growing crowd of men in the bar. She looked so eager to find the right one! I was losing my courage a little after the two near misses. Cindy took a long sip from her fresh drink and said "wait here just a minute. I want to check these guys out."

She stood up, then moved very slowly around the circular bar through the small crowd, walking her sexiest "fuck me" walk. I watched the men react, enjoying the show as their eyes followed her around. She certainly was relaxed now! And trolling the bar no less! That ass was a magnet!

When she returned, Cindy sat down next to me and said: "Joe, I think he's here now. Did you see that dark-haired man in the blue shirt come in?"

"I think so, but didn't get a good look at him."

"Well I sure did! Let's go meet him, shall we?"

Cindy sounded so sure of herself. I was excited and a little intimidated at the same time as we walked over.

He was at a small table, alone. We both said hello and asked if we might join him. He looked a little puzzled, but then smiled, his white teeth flashing, gestured to the two empty chairs and said: "Sure. Help yourselves."

I noticed him looking at Cindy, who leaned forward to pull her chair up, no doubt giving him a great look at her lovely breasts. We made introductions and small talk. This time it came easily. His name was Steve and he was in Boston on business from Los Angeles. I noticed the wedding band on his finger. My heart was pounding as he and Cindy seemed to hit it off immediately. she was laughing as they spoke animatedly about L.A., where she had gone to college.

Steve was very good looking, with sharp features. He looked to be roughly 30, maybe even younger! He had thick jet black hair, combed straight back and lively dark eyes. His skin was quite dark, which set off his white teeth that showed often as he spoke and smiled. He was sitting but looked to be of average height with a compact build. Steve explained that he'd just come from a workout in the hotel gym and was leaving Boston in the morning.

"Not too early I hope" blurted Cindy with a laugh.

Steve looked at her quizzically, but she recovered, saying "you know, with the time change and everything"

"No, not too early, but I'd be fine anyway. It's 3 hours earlier in L.A. , so I am full of energy now."

"I'll bet." said Cindy, looking him straight on.

Then, quickly, she got up saying: "Excuse me guys. I'll be right back."

I t was the "yes" signal! I felt my body go a little weak. We'd only been talking with Steve for maybe 6 or 8 minutes, and it had been mostly him and Cindy talking, and now it was up to me to proposition him! Him, a guy who seemed so "normal". Suddenly the plan seemed kind of outrageous and I considered backing off. But I couldn't. If I did it was certain Cindy would never, ever go along and try this again and my chance to fulfill this long time fantasy would be gone forever. I decided to push aside my doubts and go forward.

"Steve. I have to ask you something. I hope you don't take it wrong. (It was much harder to figure out how to do this than I'd imagined, now that "he" was here, a real person.) Ahh, what I mean is, Cindy and I, we've had this idea for a long time and tonight we decided to, to do it."

"What are you talking about? I don't follow you." Steve looked right at me.

Realizing I needed to be direct, that there was nothing to lose if he said "no", I gulped and said in a near whisper: "We were wondering if you'd be O.K. having sex with Cindy. She is hot isn't she? And she likes you. She picked you out and you two hit it off so well. You know?"

"Picked me out? For real? Man, you are asking me to have sex with your wife? What is this all about? I don't get it. Are you up to something? Am I on camera or something?"

Steve looked around for a hidden camera, then back at me, his face becoming thoughtful.

"I mean, she is very attractive and everything, but I just met you and you guys are married."

"Yeah Steve, that's true. We are. But nothing is up at all. We just wanted to act out our favorite fantasy. Well, mine anyway, and Cindy wouldn't be going along if she didn't like it too. You see I'd be there too, in the room, up in your room here at the hotel. Watching it happen."

There! It was out! Up to him! I felt so relieved, regardless of Steve's response. I hadn't "chickened out". I did notice my hand shake a bit as I raised my glass to my lips.

We could see Cindy returning, smiling as she approached the table. I knew she smiled a lot. Including when she was nervous.

"Hi guys. How are we doing?" she asked brightly.

"I asked him honey." I said. She flushed, looking at Steve. "And?"

"This is kind of unbelievable" replied Steve. "Can we sit here, finish our drinks and talk about it a little more?"

I held Cindy's hand tight under the table. She squeezed mine. Excited!

Steve kept his cool, asking us to tell him more about ourselves, about our fantasy and all about our plan to carry it out, how we picked him. As we spoke he remained somewhat dispassionate but I felt the tension releasing and felt us all becoming more comfortable. He shared some of himself too. He was married and had been for seven years. Happily. But he believed in living life, not closing himself to new things. He was intrigued!

We talked and ordered another round. After another 15 minutes, Steve stood up and said: "Let's talk more upstairs shall we?"

Cindy and I stood up immediately and followed him silently to the elevators, got on and watched in silence as he pushed the 26th floor button. I noticed he and Cindy were the same height, making me feel tall in the elevator with them. We looked at each other and smiled as we rode up. Steve told us he had a great room with a view of the Public Garden and the city beyond. Cindy and I held hands, licking our lips, saying little.

"Welcome to my humble quarters." Steve said, as he opened the door and held it for us to enter.