Surprising ReconnectionbyDr. Dandy©
It had been years since I had since one of my ex-girlfriends, and as we had both moved on and found happiness elsewhere after our mutual decision to stop seeing each other, we had stayed friends in a casual once-in-a-while e-mail or chat. We had started dating after meeting at a Christmas party, where she had been standing alone sipping tea and being a bit of a wallflower. She was petite in a very good way with long dark hair and a face that was cute and verging on a mature woman's true beauty. Together with her high cheek bones, Slavic accent, and attention to her appearance, she was a real gem of innocent allure. I got her number and we started having coffee together once every two weeks, at which point we got to know each other and I learned to really liked her for who she was; the thing was however that I was somewhat older than her and had been around the block, whereas she was fresh out of her parents' house and had literally no experience with men. It took a long time by my reckoning for anything to develop, but for her it was quite quick I suppose, the budding of a first real relationship that was more than whispered telephone calls and secret crushes.
We would meet and talk about everything and anything, and over the course of a few flirtatious meetings, I started including issues of human sexuality into our conversations. I was very open with her about sex in general, which made her blush incessantly at first, but it was clear she was curious. I didn't pressure her for any actual action, just talked with her about it as a natural part of life. That was apparently the right approach, and we started kissing, then petting over the course of a few weeks. We graduated to her jerking me off and the first time she saw a man cum her hand was on my cock with my hand wrapped around hers, helping her squeeze out my load. After that things heated up and we were rubbing up against each other naked and even started taking sexy pictures and short videos of her, which she seemed to truly enjoy. Something about the camera watching her made her very frisky and in every picture (where you can see her face) she is smiling like crazy. We actually took pictures of the head of my hard cock pushing up into her virgin pussy slick with her excitement, though not fully penetrating her. It only got hotter from there.
When we did finally start having sex, she was nervous but very eager to learn what I liked, so I taught her and we made jokes about me teaching her. The sex warmed up from just exciting to damn hot, and she truly mastered the art of the blowjob. To top it off, she was one of those women that are blessed with a magic pussy. Now I know that magic pussies are considered a myth by many men, and having slept with more women than I probably should have, I understand why. Most women have a pussy that feels great yes, but they don't actually actively grip and squeeze your cock during sex. Hers however did, and I tell you, it was fucking fantastic to have such a tight, magic and virgin pussy shape itself to the first cock it finally took inside. The sex was great for longer than it had ever been with one woman, and I came to love her for her innocence and optimism. She was beautiful in so many ways. The one thing that had been lacking for me though made our relationship slowly peter out as we approached our fourth year together, and I longed for another kind of relationship. I intimated these things to her many times, and when I finally called things off by spelling them out clearly, she surprised me by saying she had thought for some time it was over already and that she understood. I was actually relieved, because I cared for her a great deal, but knew that long-term we would have a rough go of things. We held hands, we hugged, we said goodbye. Contact itself only slowly faded until it got where it is now, an every once-in-a-while thing.
I moved on to someone else and so did she. Hers turned out to be a black man, which she had originally been very adverse to even considering. Her family was, to my mind, racist and extremely conservative in religious terms and in a way, after what she and I had done together, it didn't surprise me as much as it could have. During our time together, I had actively encouraged her to view pornography on the net, giving her sites and showing her things I liked, while supporting her in finding those things that excited her. One of my favored forms of porn that we would watch together while sucking, licking and fucking each other silly, was gangbang porn with one woman and many men, frequently white women getting fucked by big black cocks. I remember her being nervous and shy about it at first, but she seemed to quickly accept and enjoy it. So, needless to say, after we broke up and she ended up with a black guy, I didn't have any right to be surprised. I was concerned she had been suckered by a guy who wanted her for residency reasons, but life is live and learn, so I kept my opinion to myself and supported her for as long as it kept her happy. In fact, she is still with him today and they have moved in together, with her talking of marriage and children on the horizon. So here's to hoping that works out for her.
But. And this is a biggie. After not seeing her for a few years and having moved on, I kept coming back in my mind's eye to just how good sex had been with her. How she had learned to suck cock like a true pro, fuck cock with her magic pussy, and to smile and enjoy it the entire time. And of course I had the pictures to prove it, pictures that I viewed whenever I was desperately horny or out of sorts, a private masturbatory refuge where I could view and jerk off to the memory of some of the best sex of my life. Of course, when our relationship ended, I had said I would take care of the pictures, which was understood as me deleting them, and I actually had. But after doing an old system restore following a computer crash, I found I had the pictures on the backup disc. When I looked at them again and was going to delete them, I just couldn't, beautiful memories are so much more immediate with a visual reminder and I just couldn't bring myself to. At those moments I would think of how we would joke and say we would be lovers forever, even if we broke up, even if the other moved on etc., and that would make it somehow more real in the moment and I would inevitably shoot a great hot load while watching her fuck me on the screen. That went on for almost a year before I had fantasized enough and thought enough about it to actually want to try to do something about it. But how?
Despite the wild things we had done while we were together, I knew she took a disparaging view of sex outside of a relationship or affairs of any kind. You could take the girl out of her church, so to speak, but not the church out of the girl. That meant that I was going to have to think laterally to get around her morality, and that is no small task. Fortunately I knew it could be done, to an extent. I mean, we had done just about everything sexually a man and woman can do together short of additional partners, even those things I am sure she had been taught were 'sinful' or 'wrong'. But doing those things in the context I was hoping for would definitely be something she was opposed to. But what about those things we said, about staying lovers? It was a foolish thing to think she took that seriously, but that was going to be my in. I thought about it for a while, off and on, and realized that even if she shot me down, she knew me well enough to expect something like that from me sooner or later.
I let the first hint drop the next time we got around to chatting online, right after she told me in fact that marriage was on the horizon. "Oh," I said delightedly, "that's a big step. But at least then we can follow through on that agreement we made so long ago."
"What do you mean?" she asked. From the tone of her voice she really wasn't sure, but I knew that her man was home with her, so I couldn't be sure. "We had an agreement," I said, "don't you remember?" It became clear she didn't realize what I meant, especially after she asked three times in a row and I told her to think about and I was sure it would come to her. She wasn't too satisfied with that, which was fine by me, it meant she would think about it until she figured it out. That was one of her good traits, a bit naive sometimes but when she was curious she would try and try to figure something out until she got it.
After that conversation was a long quiet spell where we didn't hear anything from each other for some time. She moved in with the guy and I kept moving forward in my life. Then I hit a rough patch where I just wasn't inspired by life that much and realized I really needed more excitement and something risqué and perhaps even dangerous to spice things up a bit.
I started scripting outrageous conversations in my mind, going over the top with the things I could say, scaling them back, turning them sideways, making them subtle, smoothing things with humor and seemingly harmless intentions. It wasn't going to be easy, like most seductions, it had to be in stages and I tried to think them through carefully and with deliberation. Just thinking of it made me feel like a monster, but sometimes it is feels good to feel so bad, as paradoxical at that seems. I am sure if you are reading this, you know what I mean.
Then the day came when we finally did get in touch again. I entered a smiley face in her chat box and she replied.
"Hey, how are you!?" she replied.
"Doing okay, thought I would drop a line and say hi."
"So what's up in your life?"
"We moved in together and I am working full time at a hotel as a hostess. Working sux!"
"Tell me about it! College life was totally different, it takes time to get used to."
"So are you home alone? We could talk a bit if you have time."
I put my headset on and could feel my heart starting to beat faster. I reached down and starting rubbing my shaft through my pants, enjoying the erotic deviancy firing through my brain. It took a minute, but then the familiar tone of an incoming call began to chime and I clicked accept.
"Hey!" I said as the swirling camera icon spun before connecting. And there she was, sitting in a strange room I didn't recognize but with some of her things in the background that I did. Dolls and doilies mostly. Very girly and quite cute. She looked great, long dark hair open and framing her face that was more womanly and attractive than I remembered it. She had grown up quite a bit since I had seen her last, some three years ago I realized, this could be more challenging - and entertaining! - than I may have hoped for.
"Hey back" she said smiling and showing her perfect teeth. The camera had framed her upper torso and face nicely, though the headset did detract from the picture somewhat. During our time together she had been almost fanatically thin, which I had never really cared for. With just two or three kilos more than she liked, her womanly curves came out without making her appear overweight at all, and her breasts and ass were lush and delectable. I could tell that now she was weighing in right around where I liked her, at least the new guy was feeding her right. She was wearing a pale blouse and I could see the straps of her black bra through the thin weave. As the conversation started rolling, I surreptitiously started to rub my now growing cock through my pants, enjoying the feeling of pressure on the head as my thumb ran over and pushed it.
I let her do most of the talking, which isn't difficult with her. She gave me the rundown on everything from work ("Sux!") to family (disowned because of black boyfriend, warrior princess sister going crazy) and of course the boyfriend himself. I listened and interjected little comments or witticisms here and there to keep things moving forward. Then it was my turn. I gave her the run down on work and the other recent news before turning the conversation back to her.
"I'm glad to see you looking so well despite what's going on otherwise, it looks like overall you are feeling pretty good."
"Well, I try to keep looking on the bright side, no use worrying about things I can't change."
"More like looking on the dark side," I said. "Who would have ever thought." She laughed a bit at my pun as I continued. "Speaking of which, I guess you can probably confirm that old saying my father was fond of: 'once you go black, you never go back.'" She gave a good laugh at that blushed a bit. It was nice to see her modesty in a way, it made the challenge all the more sweet. "Well?" I asked.
"I am really happy with things, considering we're getting married, yeah, I guess I'll never 'go back'."
"That's not really what that phrase suggests," I replied. "It's really just sex, in this case if you could ever be satisfied by white cock again." I smiled wryly as she registered what I had said and her mouth opened in a little 'o' of astonishment before she blushed furiously and giggled like a girl.
"Well, if I'm ever single again I'll think about it," she tittered.
"Funny," I said, "that's not what we agreed on."
She jumped at the remark, and I could see her remembering our last conversation as she said "Hey! Yeah, what was that about last time, when you said we had an agreement? What agreement were you talking about?" My cock throbbed in my pants and I leaned back in my chair. On her side of the screen, she could see I had reclined a bit, but my left hand was below the edge of the desk where she couldn't see my fingers actually stroking and pressing on my hard shaft and swollen head. She could however, if she was observant, notice my wrist moving ever so slightly as my fingers below rubbed and slid over the tent in my pants.
"I can't believe you don't remember," I laughed, "I thought for sure you would have got it by now, especially with the whole 'never going back' commentary."
"Sorry," she said with a little frown of confusion, "I really don't get it." I wasn't really surprised by her answer, it was like that with her sometimes.
"Oh boy," I replied in mock exasperation, "good thing one of us remembers. We agreed to remain lovers, even if one or both of us got married."
The look on her face was great, running from listening and trying to remember, to her eyes widening as it registered and her mouth opening in a nervous half-smile as she tried to think of a proper way to respond. The good girl in her came and she gave a half-hearted laugh to go with her half-hearted smile, "Yeah well," she said, "I do remember that, but I couldn't have known I would be happy like this at the time. We were together and making those kinds of agreements while you were teaching me just seemed like...well, like we were joking or teasing each other about the future. It was actually a hopeful thing back then, and sure at the time it sounded adventurous, but things have changed." As she said this, I watched her face closely, she had always been good at saying the right thing, but frequently her expression would reveal something more. It is at this point I think she noticed my left hand under the desk, as I could see her eyes focusing downward on the screen and a hint of nervousness crept into her voice.
"Awww...!" I exclaimed in faux earnestness, putting on a glum face, "I guess I'll just have to learn to get by with nothing more than pictures of memories." By the time that registered with her, I was singing the first verse of Dean Martin's "Memories are made of this" to tease her.
"Hey! I thought you said you would delete those!"
"I did actually," I replied smoothly, intentionally shrugging my shoulders and looking like a kid caught with his hand in the cookie jar, "but recently I reinstalled my backup files, and I found an old backup of them there. After looking through them and enjoying them again I couldn't bring myself to delete them a second time. Sorry. But don't worry, they are very safe and nobody else is going to see them. I mean, my God, I'm in those photos too, last thing I want is somebody seeing what I look like while fucking. How embarrassing would that be?" As I had been saying this, I had opened the folder on my computer that contained the pictures of us and started looking at the thumbnail previews in the overview. I could tell at that point that she was very probably aware of what my left hand was up to, but I didn't stop. She had watched me jerk off on cam before, while we were dating, and to be honest that wasn't far from my mind. I knew at that moment she was thinking about the pictures and videos we had done while together, I was certain she had understood that by "enjoying" I meant I had jerked off to them. Together with the image her mind likely conjured when I talked about how I look while fucking, a dribble of precum surged up the shaft of my cock and lightly lubed the head before absorbing into my underwear.
"Umm...," she started hesitantly, "... I can't really be upset with you, I kept my copies too." She shrugged and smiled ruefully, "But it's nice you at least deleted them once."
"Oh really?" I asked, seizing the unexpected opportunity, "And when was the last time you looked at them?"
She blushed again before telling me it had been a few months. I could see her eyes still focusing near the bottom of her screen, where my wrist could be seen slowly moving in small circular motions. "Oh, it must have been a few months ago now. And when was the last time you looked at them?" she asked, trying to divert.
"Honestly?" I said, "I am looking at them right now."
Her face appeared thunderstruck, "Uhhh..." she said hesitantly, now obviously staring at the bottom of her screen, a war of emotions on her face, not all of them good for my cause. "Well, maybe we should hang up so you can.... get on with things there. I don't want to interrupt anything."
"You aren't interrupting me, don't worry," I said with a wink and smile, "talking about it shouldn't be awkward for us, it's not like you haven't actually participated in the past."
"Yeah, but things have changed, I'm not sure I'm really comfortable with where this is going."
"Wait a minute, you were already with your boyfriend a few months ago, in fact it has been quite some time. So you actually looked at our pictures since you've been with him. Is that what's making you uncomfortable?"
"No, it's not that, it's just..." she flattered her hands a bit in air, "well maybe. And knowing you are looking at them right now and our history and everything, part of me is kinda embarrassed and I feel like I shouldn't be talking with you about that, like its cheating or something. You understand, don't you? That shouldn't happen."
"Well, on the one hand," I said raising my right hand from where it was on the arm of my chair, "I do understand. But," I continued while using my right hand to point at my left, "on the other, words aren't action and we are sitting like 300 kilometers apart." I decided to go light on the offensive and followed that up with, "You need to get over that overly prude upbringing of yours entirely someday, you'll enjoy life more. We aren't actually doing anything. And even if we did, so what? It's not any different than watching a movie online, right? I mean, you do still enjoy watching porn don't you?"
As I had been talking I could see her struggling with herself, trying to disentangle the knot of emotions and find a clear message that would crystallize what she was trying to get at. You could read it in her face and by her body language, which had gone all stiff and careful. Of course, I knew exactly what she was driving for, and I was throwing down detour signs as fast as I could think of them. The last question brought her up short and she cocked her head as if considering something.