Helen of Troy Ch. 01: The Date

After my marriage to Carly ended in a bitter divorce, I took some time for myself, not dating at all. I needed to heal my wounds, and to find just who I was without the insane influence that Carly had become. It took three years from the time that I filed until the gavel fell in court. That was the time that I needed to find the old me. I did meet another woman. Helen. She was very attractive, to say the least. It took time for us to develop a relationship. My divorce was final just a short time prior to meeting her, and her husband had passed away just a little over a year prior to our meeting. In the short period of time that my life was blessed by her presence (she was killed by a drunk driver), she brought much joy and fun to it. As you'll see in the series of chapters to this piece of my life, she was full of surprises. The chapters will not be in chronological order. But they will be erotic...I hope. They will be full of extramarital sex and multi-partner sex, just some of the topics that this category of 'Loving Wives' is all about. Enjoy.

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THE DATE - Chapter 1

My mind was numbed by the reality of what was about to happen, trying hard to wrap itself around the fact that my wife Helen was dressed to kill, standing before me for approval of how she looked, and ready to go on a 'date'.

All I could say was, "Exquisitely hot!"

Her tall, slender body was sheathed by a navy blue short-sleeved dress that came halfway down her thighs. She wore navy blue satin pumps. Her hair was up in a very elegant bun to show off her magnificent neck. Her jewelry was perfect, as was her makeup and ruby red lipstick.

With that, she walked to me, gave me a passionate kiss, smiled, and told me that I didn't have to wait up if I didn't want to. But I knew that I would want to. And then she was out the door, in her car, down the drive, and on her way. No turning back from a course that had taking a few years to chart itself.

Helen is my second wife. She has been a bundle of surprises and sharp turns for me, never knowing what to expect next from her. We had been married two years, but had known each other in a romantic way for seven years before getting married. We met just nine days after my divorce from my first wife was final, introduced by mutual friends.

My first wife Carly and I had a very exciting sex and romantic life at first. However, after many years and many sexual experiences, a side of Carly that I never knew existed began to emerge. I increasingly accepted that fact that she had become someone that I dreaded growing old with. For our mutual mental well-being, I pulled the plug. I knew that she needed somebody in her life other than the kind of man that I was, and that I needed the opportunity to find someone who I was better suited to be with. That could only come with ending the marriage because we were both 'hard wired' to be who we were. Do I miss Carly? Sure, I do. More so, I miss the exciting sexual adventures that she and I had.

Helen was from a very conservative background. She was of Mediterranean descent, with a classical beauty that is found in that region. She had a work ethic that my first wife was clueless of, and was, therefor, extremely supportive of the needs of my career. Helen 'got me'.

As Helen and I courted, I found myself off balance most of the time with surprises and sharp turns. She had been widowed at a young age a little over a year before she and I met, and she had a daughter. I had been 'coached' that women from the Greek culture often didn't remarry once they were widowed. I also had a notion that, because her culture was conservative, women did not engage in sexual activity unless there was a wedding in the picture. I was wrong on both accounts.

She shared with me that she was not intending to get married, but that the 'once a widow, always a widow' concept was for those that lived in the old country. And, after a few months of talking and late-night phone calls, she invited me over for dinner, and then up to her bedroom. Apparently, the 'no sex without a ring on the finger' rule didn't apply, either.

Oh, could she fuck! She was absolutely ravenous. And she would orgasm so quickly, too, something that Carly often had difficulty in doing. Just my cumming in Helen often made her cum. I liked that. But what's not to like about that?

Whenever we would get together for sex, I would always have to leave in the middle of the night for my own home because she had young children. She did not want to expose them to anything that would upset or confuse them. Plus, she didn't want them sharing with others anything that they saw or heard. Helen was very private and very conscious of reputation. We would not get together every night; maybe two or three times a week. This served to make me extra horny whenever we did get together.

After a year into our marriage, we had developed a great confidence in our relationship. I would say that we probably felt secure enough to explore a little of each other's past. I was very curious about her, knowing that she did not always go with the grain. I had already shared with her the horrors of the latter part of my marriage to Carly and the ensuing ugliness of my divorce from her. As far as Helen knew, I had been with Carly and only a couple of women prior to Carly. What I had not shared with her was full the extent of my sexual activity. Helen began to brag a little that she might have had more sex than I had. If only she knew. But then, she wouldn't have known it because I was tight-lipped about it, and didn't divulge more than I thought she would have already surmised. Until I knew that she was ready for anything that I shared with her, I wasn't going to take any chances of her thinking that I had been sexually active while with Carly and after. But she had opened the door by boasting that she had sex with men other than her husband and me. The challenge was down!

I had to preface any confessions to her with the fact that I wasn't sure how she would handle it. She knew that they predated her presence in my life, so she couldn't be upset. She said she might even find them intriguing. That was the sign that I was looking for. I cautiously jumped out on that limb.

I related to Helen about a foursome that I had been invited into before I met my first wife Carly. A Marine friend of mine had two women with him at his house one weekend...his current open-minded girlfriend and an open-minded ex-girlfriend who remained good friends with him. I was renting one of the bedrooms in his house so that I could get away from the Marine base on weekends. Well, I had the hots for both of them, but when his current girlfriend came down to my room to make out with me and invite me up to my friend's room, I wasn't going to say, "No." I followed her upstairs, and then fucked her while my friend fucked his ex-girlfriend right next to us in bed. What an erotic experience that was! I was introduced into the world of swinging...and I liked it! But that was a one-time experience with them. The opportunity never presented itself again until after I met Carly.

Helen was amazed. She could never have suspected that I would have had such an experience. She wanted me to go into details. I obliged her with as many details as I could remember. She admitted that, while she was watching some porn, she always wondered what it would be like to watch someone screwing in real life. I detected intrigue in her conversation, and tried to play to it as much as possible, making it as salacious as I could without going overboard.

She seemed to be rather accepting of my tale, more so than I thought she would be. The waters had been tested, and they were fine for swimming.

Then I decided to go for a big one...the one that would really test her acceptance and intrigue. After some hesitation, I thought that she would probably like to hear about the first threesome that I had with my wife Carly. Of course, I didn't use the term 'first' threesome, instead just telling her that I had 'a' threesome. I didn't want to push my luck. She never knew anyone that had done anything like that. Well, she didn't know anyone that had ever participated in a foursome, either. But sharing my wife was on a much higher level of sexual experimentation than my foursome was. This really piqued her curiosity.

I was afraid of her being judgmental, but she listened to this experience with great interest. I tried to express just how sexy it can be to see your own wife sharing her body with another man in an intimate way...to be sexually gratified by another man's body and cock. This was a difficult conversation to have, not knowing how she would react. I had to choose my words very carefully so as to spin it in as erotic a manner as possible. She was astonished. She had even more questions about my threesome than she had with my foursome. After all, the foursome was just with some friends. My threesome was with my wife. Mind boggling! She exuded a subdued excitement in her questioning, wanting to pry more and more information out of me.

Was I jealous? Yes, but I was also excited. Did I have reservations afterwards? Yes, but I also had an insatiable sex drive. I couldn't get enough of my wife, seeing her in a new light of womanly sexuality. Carly and I would recount that evening many times to each other, always ending in a hot fuck.

This story and its details seemed to act as a release to the flood gates. She felt like maybe anteing as much up to my experiences as she could. She shared with me that, while she did some heavy date-petting in college, her husband was the first that ever actually got to have sex with her, which began while they were engaged. However, a few years into her marriage, she got the hots for a young man - Greg - that was somewhat of a distant family friend, and that would come often to the night club that her father owned, and where she worked. She wasn't in love with him, and she didn't want to do anything to ruin her marriage, but she did want to have more sexual experience than what she had. She knew that he was keenly interested in her, and she began to warm to the idea of having fun sex with him. So, she ended up asking him to stay late one night that she had to close the club. She recounted that they undressed each other, he guided her up onto a pool table, then fucked her. She found herself looking forward to finding ways to fuck him. They had a sexual friendship for a couple of years, but that eventually fizzled out. They always remained friends long afterwards. Little did I know.

I coaxed as much information out of her that I possibly could about other experiences that she had. She told me about a couple other sexual encounters, but remained a bit tight-lipped about anything more, much to my dismay.

I had presumed that she stayed to herself after her husband died, as was the custom of the old country. But I had to ask. She was reluctant to answer, asking me if I really wanted to know. Of course, I did...and I didn't. I got my answer, though. She had been with another man that she knew from years ago. She said that it was only for company and sex. He was too old for her, but she liked the size of his cock. Ouch. But he became too jealous and controlling as I entered more into the scene (she came to work for me), and wanted more commitment from her. She ended the relationship, then started seeing me.

The "little did I know" part comes in here. While she was seeing and fucking me a few nights a week, Greg and Helen had reconnected. She invited him back into her life. Rather, she invited him back into her bed. This, I was not expecting to hear. I was a bit stunned by it, to say the least. This was one of those sharp turns that I had mentioned at the beginning of this piece.

It took several weeks for me to digest this little gem of information. In the meantime, we did talk about it. As with my discoveries about Carly's sexual past, the more I talked it over, the more of an erotic spin my mind put on it. I came to fully realize that she married me because she loved me and enjoyed sex with me. Her sexual encounters with him ended on her terms when she decided that I was somebody that she could marry.

In time, I found that thinking about it would get me aroused. I eventually ended up getting to know the Greg. He's a good person. He had actually become a client of mine through Helen before I knew about their history. I would try to imagine what it must have looked like, the two of them naked, joined by his cock penetrating her pussy. She told me that he had a vasectomy, so it was safe for her to let him cum in her. She loves it when men cum in her pussy. This only stoked the sex engine in my mind. I would get hard trying to picture his hips thrusting his cock as far into her as he could go, spraying his cum deeply into her vagina. Now knowing how the idea of another man fucking my wife turns me on, her reply was, "Oh, to be a fly on the wall. I think you would have liked it."

Over the following months, whenever we'd have sex, we'd always engage in talk. I eventually got the nerve to ask her if she'd ever wondered what it would be like to be the object of attention in a threesome. She did wonder, but didn't know if she could do it. "But what if it was with Greg?" I asked.

"I really don't think that he would ever go for that," she answered. Damn.

After more months, I decided to try another approach. I had actually warmed up to the idea of her getting together with Greg again for some private one-on-one sex like they had during her first marriage. The truth is, since she only worked part time and he was now retired, there was ample time for them to get together if they wanted to, anyway. I was extremely confident of her commitment and emotional loyalty to our marriage that, if they got together for a fun fuck, it would have been the same as before between two friends who had a sexual connection. That didn't bother me that much. Actually, the more I thought about it, the more the idea intrigued me. So, I decided to bring it up more in our sex talks during some wild, hot screwing.

"Really? You mean you'd be okay with me going out on a date with him, then going back to his place for sex?"

"Well, that's not exactly what I said," was my response. "I'm not talking about anything like 'dating'. But, if you would like to have sex with him, I think that I would be okay with that." I didn't want to open the door for it being anything other than fun sex between friends. Nothing romantic.

It's strange, though, how my sexual mind can take me to places that I never knew existed. Somehow, the thought of her getting dressed to the nines, looking glamorous as she always does, going out for a nice evening, then getting fucked began to find its way onto the erotic palette of my thoughts. I began to find myself creating the scenario, and getting aroused by it. I was on board. Especially if it might lead to him becoming comfortable enough with knowing that I was okay with the two of them fucking. You see, Helen did tell him that she explained to me their past...all the way up to him fucking her while she was fucking me. He was upset at first, and found it hard to believe that I was okay with it. She explained to him, just as I had explained it to her, that hearing and knowing about it was like reading porn, but only better because it actually happened between two people that I know. So, I was perhaps secretly hoping to this would lead to Greg and me rocking Helen's world together one night.

Even though I let her know that I was accepting of her having sex with Greg, she still would not allow herself the pleasure, assuring me that it would never happen again.

Usually before sex, Helen and I would get high on weed. Weed makes my orgasms very intense and protracted. It also lowers our inhibitions, and lets my imagination loose, which, in turn, fires up my libido. I tend to get very verbal, talking about how I love knowing that other men pumped their sperm into her hot pussy. I would let her know that it turned me on to imagine seeing another man's cock buried in her vagina, then watching his cum seep out of her hole. I would ask her if she loves men cumming in her, and she would always say, "Yes!" I would also ask if thinking about it turned her on. Again, "Yes!" And there were times when I would ask if she loved it when Greg came in her. This brought her to earth-shattering orgasms.

I was quite certain that, while she insisted that she did not want to have sex with others, she loved thinking about it. It was an aphrodisiac for her. Seeing as how the thought of fucking other men triggered tremendously explosive orgasms for her, it was clear to me that she was warming up to the idea.

When I told her that I was okay with her going out with Greg for an evening of fun and sex, giving her the green light, she was only mildly surprised. After all, she already knew how much of a turn-on it was for me. But for me to give her a free pass...?

She didn't rush into it. She would call him up on a few occasions, just to reestablish the connection, and to get him interested in her again. She would let me know everything, though, because that was the ground rule. I didn't want anything happening behind my back. I had been abused that way by Carly during the decline of our marriage. It's not a good practice, and opens the door to far too many potential issues. Hell, having extra-marital sex could open that door to begin with, even if it's consensual. No need to further complicate a delicate situation.

The weeks passed, and she called me one day to ask me if it was okay for her to have coffee with Greg that afternoon. Of course, it was! And I was anxious to get home to hear what she had to say, wondering if any prurient conversation came out of their meeting.

When I got home, she greeted me with a kiss and a smile. I was on pins and needles. I asked if they discussed anything interesting. Her smile got broader, and she said, "Yes, we did."

"Okay. I'd like to know. Tell me about it."

"Well, it was difficult to talk because we didn't have much privacy some of the time. I told him that I missed what he and I had...our friendship...and what came with it. He said that he thinks about that a lot, and misses it, too. I then told him that you would be okay with it, knowing that we are very dear friends...and that you and I are so confident in our marriage that we don't think this will hurt it in any way. But I did tell him that he has to understand that this is what it is, a friendship with benefits, and that it can't be anything more. Did I do well?"

"You did well. How did he take it?" I asked.

"Of course, he understood the terms. And, of course, he's going to be okay with it if it means that he can fuck me again. He seemed excited. I'm excited, too. It's been so long since I've been with him in that way. I'm only hoping that he'll still be as turned on by me as much as he used to be. I'm much older now."

"Don't worry," I said. "He's a man, and you're a beautiful woman. His cock won't fail either him or you, I'm sure of it!"

"Okay. Then the next step is for me to call him and see if he'd like to go out some night. Of course, we'll go over to the next county for dinner so as to be discreet. But then I'm not sure what will happen after dinner."

"Yes, I think you are sure. I am, too. He's had years to reminisce about you and fantasize. He'll be up for getting you alone to fuck your brains out. Just be sure that you're ready for it."

"I'm pretty sure that I'm ready," she said with a smile. My cock twitched.

Well, the call was made. The date was set. My heart raced.

She had been giddy all day, catching me looking at her, and shooting me impish smiles in return. As she got ready, I'd occasionally dart in and out of our bathroom and dressing closet to see just how she was preparing herself, knowing full well that he'd be seeing all of those undergarments as he peeled them from her body. My cock grew hard and heavy at just the thought of her standing naked in front of him. I began to detect a slight case of blue balls at the thought of her on her back on his bed, and him pistoning his hips between her spread legs, driving his engorged cock in and out of her pussy.