Reentering the dating world after years of marriage was at the same time both exciting and nerve wracking. The excitement was the thrill of finding renewed passion in my life, something that had been sorely lacking in my marriage. I had heard that forty-something women, once liberated, are revitalized and sexual dynamos – we no longer have to play by the rules, so anything goes. But where to start? I did not lack in confidence of my attractiveness. A woman knows when she is attractive and even though I didn't stray in my marriage, I knew men found me desirable and that undercurrent of confidence was now about to come to the surface. I'm rather tall, with a short, pert frosted hairstyle that suits my features and conveys my boundless energy and spirit. I'm a bit chesty but long-legged as well, with a slender waist and still do justice to a bikini.
So, I was about to embark on my new life and I knew that there would be a man or men in it as soon as I got my bearings. I had no baggage really. My husband and I never had children. This was not my decision but one in which I really had no say. He informed me that he had been snipped but only after we had been married for several years and I pressed him to begin a family. I felt betrayed. This was information I should have had before committing to a life with him. I was frankly quite naïve when we married, in more ways than one. I had only been with one man before I met my husband, as I was both very selective and health conscious. It amounted to nothing more than a quick fling in college and I really didn't enjoy it at all. He was of course required to use a condom. I don't know which was more irritating – the latex or his technique. When I first met the man I married, we decided to wait until I was on the pill before we had sex. Of course that proved to be an unnecessary precaution as he was a good ten years older than me and had made the decision early in life not to be burdened with children. Though I was crushed when he finally informed me, at least I no longer had to take the pill – the side effects for some women are not pleasant and I resolved never to take them again.
I'm one of those women who are born to plan, so before testing the dating waters I knew that I would once more have to address the issue of contraception – better safe than sorry! Though still quite fertile, I was past the age when childbearing was a good option for me personally. Condoms were not reliable and were irritating as well. There were hormonal implants but I couldn't stand the thought of having chemicals in my body. Several of my single friends used diaphragms but really – having to excuse yourself to slip a shield up inside your vagina before sex was unappealing. My doctor and I after much discussion decided on an IUD as the best option, though she did caution me that they were not 100% foolproof and doctors were still debating exactly the exact mechanism by which they prevented pregnancies. The best information suggested that they did not prevent conception but rather the implantation of the embryo in the uterus. Whatever – this choice made the most sense for me.
I thought long and hard about that rather hard fact and found to my surprise that I found it rather thrilling to think that a man might actually impregnate me. I suppose that it's in a woman's makeup to want to be, well, fully a woman. It obviously was in my nature to have those feelings. The week after the IUD had been inserted, I found myself constantly aroused and obviously very ready to put the device to the ultimate test. Thoughts of taking a man's living seed into my body thrilled me. I spent hours pleasuring myself imagining the man who would be the first to fill me with healthy, virile sperm – not the thin, sterile cum of my husband but the real thing. I longed to be taken and awakened as a woman – to be inseminated for the first time and, who knows, perhaps impregnated as well. I was a woman denied, truly ready to be fulfilled in every sense.
My friend Jan, who had been single for several years, was my guide as I entered the single world. She's a dear friend and though she is a single mother of two wonderful children, she also enjoyed the freedom that her single life afforded her and had a wonderful, open attitude that I admired and wanted to emulate. She had had more than her share of lovers and relationships over the past few years and just seemed to keep it all in perspective. Jan helped me fashion a profile for several of the online dating sites and we had so much fun sharing this new experienc. I couldn't imagine barhopping and knew that she had had good success meeting men online, so I was thankful for her 'expertise'. We both shared laughs about the replies I received, particularly from the younger men. I am no cougar though I was flattered that younger men found me attractive. I learned quite quickly that I was far more attracted to men my own age if not a bit older who were established, secure, attractive, and confident in themselves. I had had several one-off dates and frankly found myself uninspired. I mean, most of the men had been nice enough but were almost too taken with me. One guy even proposed to me on the first date! How silly! I mean, it's incredibly flattering for a man to be smitten with you but I yearned to find the man who would unlock my desires.
Jan knew this – she knew me too well, and one day we were sharing a glass of wine after work and checking my account when she saw a message from a man she knew quite well. His name was Don and she told me that she had 'dated' him for a few months soon after her divorce. I remembered her telling me about him a few years ago – a lawyer, charming, never married, great in bed, but a player. I recall that he had 'dumped' her in some way but didn't recall the details. She filled me in quickly enough. Don had been the first man that she slept with after her divorce, when she was vulnerable and desperate for affection and romance. And for a time he had provided both. Jan had really fallen for him only to learn that Don was far more skilled at the game than she was. Don was a lifelong bachelor and knew how to string a woman along, particularly women who were recently divorced and needy. Jan didn't regret her time with him but couldn't handle the fact that he was fairly open about having a 'stable' of women. Jan had 'the talk' with him about her needs and soon enough he simply stopped calling. Men! I knew that she carried a bit of a torch for him so I asked her what she thought about him contacting me.
"He's out of my life now, so if you want to reply to him, I have no problem with that. Just understand what you're getting into – that's all. He's fun and sexy and smart and a total player." I hesitated. Jan laughed. "He's also incredible in bed. He turned me inside out! He's amazing. And he's got the most beautiful cock I've ever seen."
"How so?" I asked.
"He's just one of those men who knows what a woman wants. And," she giggled, "he's got this gorgeous, big cock! And the trouble was he was using it on all of these other women. I got tired of being one of his fuck toys!"
I thought about that – a known bad boy. It frankly excited me. "Maybe I'd better just delete his message," I said unconvincingly.
She laughed out loud. "No, I wouldn't. Go ahead and reply. Just know what you're getting into in advance. You won't ever have it so good – trust me! You owe it to yourself – just keep your expectations in check."
I felt the rush of doing something naughty when I hit the reply button. We both crafted my response, which was open and inviting of further contact. I suggested we meet for drinks. We didn't have to wait long for his reply. "Sure. When and where?"
Jan smiled at me and simply said, "Enjoy."
We made a date for the following Friday then and there. I pressed Jan for more details – girls will be girls, after all! Don had it all – looks, money, charm, a great lifestyle, and incredible skills in the bedroom. And he was almost sixty? Jan thought I was overmatched and I think in some way a bit jealous but she was thankfully still supportive. My imagination went into overdrive immediately and I thought of giving myself to this stud. I so needed to do just that and why not Don? Might I very soon be taking the same cock into my pussy that Jan had enjoyed several years before? I found that in some way to be exciting. And it was excitement, not commitment, that I yearned for – someone to scratch my itch. Don certainly seemed to be a likely candidate. I spent several days before our date imagining giving my body over to his pleasure – and mine! I was so ready for such a man – would he know that? I felt certain that he would ready me in an instant. That too was exciting. Unlike Jan, I was engaging Dan knowing full well what to expect. Forewarned is forearmed!
We were to meet in the lobby bar of a very nice hotel close to both of us. And I dressed for effect, going to lengths to show off my body, particularly my long legs and generous cleavage. Jan had told me he was a sucker for great legs. Hers were great but mine were equally sleek and I smiled as I looked in the mirror. Not too bad for 45 I thought! I arrived about 10 minutes late, as I wanted to make an entrance. Sure enough there he was, sitting relaxed and confident at the bar and I smiled at him as I walked up to greet him – his eyes never left me. I had never felt sexier and more desirable.
And, goodness, he was charming from the word go. I almost forgot that he was just a test case of sorts and found myself delighting in his company. And handsome! Oh my – he was so handsome! I relaxed immediately and found myself completely taken in by his easy, confident manner. What woman could resist such a man?! Not me! It took all of my willpower to stay cool and in command of myself. We chatted for over an hour and I knew very quickly that I wanted him – and knew for a certain that he wanted me too. But when he suggested that we go to his place to continue the evening, I declined.
"Another time," I replied.
