Gifted Grifter

Six months after moving in together, Julie and I had adapted to domestic life together amazingly well. For one thing, Julie loved living in New York—the theaters, the dance clubs (I took her dancing regularly), Central Park, the restaurants, and just the variety things that were available. But most nights we just stayed at home like normal people. That might sound pretty mundane, but I think that's where May-September romances often fall apart; the things that interest people born of different generations can be quite different, and the inability to find things to do together on a regular basis can doom a relationship. Julie and I found things we both liked—Adult Swim, for instance—and when we didn't, I would surf the web or play one of my geeky MMORPGs while she would watch TV or play around on Youtube or Myspace.

The way that we earned a living had evolved as well: we had learned that the best stock tips came not from fancy restaurants, but at the health club. We were doing fine before, but now we were doing very well financially; we were able to move out of the hotel and into a rented brownstone—we wanted to buy, but on paper it looked like I hadn't worked in a year and Julie hadn't held a job since she was 18. It was going to be a while before the combination of down payment and credit the bank was willing to give us added up to enough to buy the kind of place we wanted.

But as our trading accounts grew, my fears of Julie leaving me increased. I always felt that she was too attractive to stay with someone like me, and now that she didn't need me financially, it just felt like she was slipping through my fingers. One side effect of these feeling was that I didn't always leave Julie enough room to operate; if a guy looked like he was getting the wrong ideas, I tended to interrupt them. Julie was frustrated with me, because she interpreted it as that I didn't trust her. I suppose in a way she was right, but it wasn't because of her; it just reflected the fact that I didn't feel like I had much to offer her anymore.

Then one day the reverse occurred. Trolling for tips at the gym, a young and hot but flighty thing started chatting with me and—perhaps because I was standing around the weight room doing nothing—asked me to spot her. Julie saw that, and this time SHE came over to interrupt ME. It was clear that we both had issues, insecurities about each other that needed to be aired out. We tried talking about them, but somehow it always seemed like something was going unsaid. On my part, I couldn't just come out and say that I was sure Julie would eventually leave me, it was a slap in the face when she was telling me she loved me and didn't care about anyone else. I just didn't feel like that was going to stay that way. And there was something she wasn't saying either, but I had no idea what it was.

Julie came up with a novel way to get things back out in the open between us. One night she suggested we go to my favorite restaurant. Over dinner, she said she wanted to play a game tonight—a variation on truth or dare, she said, using our mindreaders. We had agreed that we would only use mindreaders on each other if we were both using them; it was a foolproof way of getting the truth out in the open, and we were the only people in the world who could do it. I was all for it—I didn't like the fact that it felt like Julie was pulling away from me on account of our mutual insecurities.

After dinner she went to the bedroom and came out wearing a lacy lingerie vest and panties. "This game is like truth or dare, but with mindreaders," she announced. She had a stack of notecards and two Sharpies. "I'm going to give you a notecard with a question on it. You don't have to answer, I'll be able to see your answer with my mindreader. Then you get to write a question and use the mindreader on me."

I swallowed hard. This was a darn good idea on her part, but it also promised to end up revealing a lot of intimate thoughts. If any of those thoughts disappointed the recipient, it could be very bad. Part of me wondered whether this wasn't actually a backhanded way of initiating a breakup.

"I anticipated that you might be bit nervous about how this might turn out, so I have a little extra incentive for you," she said. "What's truth or dare without a dare right? Well, see this little vesty-thingy I have on? It has just three little ties holding it together. And these panties," she continued while demonstrating, "have only two. For each question we get through, I'll untie a string. When we get through five questions, there'll be absolutely nothing keeping my clothes on. I KNOW you know what to do after that. So what do you say—deal?"

I was going to go along with it anyway, but I certainly couldn't pass it up now. I was already eyeing the little bit of cleavage showing above her top, and lusted to see more.

"Okay, who goes first?" I said.

"I'll go first on the first question, you go first on the second, and so on," she said. "So, here's your first question." She took a notecard, wrote something on one, turned on her headset mindreader, and handed it to me. It said:

What do you really think of me?

Thoughts don't lie. They told her I really loved her, not just as a sex partner but as a person, that I had never been happier than I was, and that I hoped our relationship would never end—but feared that given the age difference, it was inevitable.

She turned off her headset, pleased to confirm that I really loved her, but more hard questions were to come. "Okay, your turn," she said.

Rather than write anything new, I handed the card back to her, put on my mindreading glasses, and said "I think this is a perfectly good question."

Her thoughts confirmed that she loved me too, that as far as she was concerned I was the only person she had ever met that liked—or even cared to find out about—all of her as a person. Furthermore, she was living a life she had never even dared to dream about, and she owed it all to me. I disagreed with the last part, in that it had taken both of our talents to amass the fortune we were continuing to grow, but this wasn't about arguing—it was about discovering.

Good to her word as always, Julie undid one of her ties—but she undid the bottom one, little fucking tease. Well, at least now her belly button ring was peeking out.

It was my turn to pose a question. I had an idea; I wrote it down on a notecard and handed it to her.

What is your biggest fear or disappointment in me?

She had no disappointments; sure, it would have been nice if I was younger and more attractive, but it also would have been nice if she wasn't a former sex worker; that's just the way it was. She had a strong fear, however, that I would leave her. We were now well-off, and there were always young, attractive women gunning for guys with money. She was afraid that eventually I would find one that was more attractive and/or better able to satisfy me (as if that were even possible) and that I would leave her for the younger woman.

It never occurred to me that she might have fears that paralleled my own.

I took off the glasses and Julie turned on her headset. She did what I had just done, giving me back the card I had just given her. "I would like your answer to the question," she said.

My thoughts ran to my feelings of inadequacy, of being ten years older and not feeling very attractive. Now that she was independently wealthy, I didn't feel like she needed my anymore, and consequently I felt like it was only a matter of time before she left me for some hot young stud muffin. All I could do was enjoy the time we had while we had it.

She frowned slightly, as my answer didn't give her any credit for being faithful. She may have interpreted that as residual from her past, but it was just my assessment that I felt I brought little to the table. I was learning that she didn't see it that way.

She untied the top tie on her shirt. The middle tie was sufficient to keep her shirt maddeningly closed, but now more cleavage was spilling out, especially when she bent to write on a card. I longed to bury my face in it. But then she sat up and handed me the card. It said:

What will happen when I'm old and not beautiful anymore?

The flood of thoughts this card generated had Julie struggling to keep up with it all. First off, just because you weren't 25 didn't mean you couldn't be beautiful; since I was already well past 30, I kind of resented this implication. Maybe I wasn't attractive, but that didn't mean she wouldn't be. After all, the best indication of how a girl will look when she's older is to look at her mother, and her mother was still quite attractive at 45. Furthermore, my feelings for Julie went well beyond her physical attributes or our sex life. It was true, initially that pretty much was our relationship. But now, I loved her as a person, and that wouldn't change if, god forbid, she became horribly disfigured tomorrow.

She liked that answer a little more. She turned off her reader and I put my glasses back on. I wrote a question on a notecard and handed it to her. It said:

Why do you stay with me now that you're financially independent and don't need me anymore?

Her thoughts indicated indignation that I thought of my financial resources as the only reason she was with me, while at the same time recognizing that at the beginning, there was a lot of truth to that belief. But I was more to her than money; I was love, I was support, I was someone—the only one as far as she was concerned—that cared and listened to her. That was more precious than money; she would have stayed with me even if we were living on the street.

I gave her a little smile of appreciation. Julie slowly and deliberately undid the last tie on her shirt, but then crossed her arms across her body to keep it from opening up. She knew that if she let me see her breasts now, I wouldn't be able to think about anything else. Dammit, sometimes she was just too smart.

My turn to go first. Hmm...Okay, maybe this was pretty similar to the last one, but I wrote:

What will happen when a young, attractive man starts paying attention to you?

Her thoughts were pretty similar to before; it wouldn't matter who paid attention to her, she was only interested in me. In me she had someone who gave her emotional support in a way that she didn't know from anyone else—why would she throw that away on an unknown quantity in someone else?

I took off my glasses and she turned on her headset. She took the notecard, crossed off "man" and penciled in "woman" above it, and handed it back to me.

My thoughts were—so? I had seduced plenty of women in my first year of grifting; none of them held a candle to Julie. Another woman might be pretty on the outside, but as far as I was concerned there was no chance she was going to be as pretty on the inside, if you will, or that she would work as hard to make me happy.

She turned her hip towards me and made a show of untying one side of her panties. But sitting as she was, untying them really didn't reveal anything new. Then she sat and thought for a bit, as it was her last card. Finally she wrote:

What would happen if you became dissatisfied with our sex life.

My thoughts may have been hard to follow here, because I truthfully couldn't imagine being dissatisfied with our sex life. I would have been wildly satisfied with our sex life even if she worked one-tenth as hard as she did at making it great. But maybe she meant as we got older, I thought. Well, I would always be ten years older than she; the way I figured it, I would be unable to respond to the challenge long before she stopped being able to get a rise out of me—if that were to ever happen at all.

Julie turned off her mindreader; it was time for my last question. My thoughts were racing. I loved Julie, and wanted to be with her forever—but I had always dismissed those thoughts as unrealistic. Suddenly, it was clear that Julie's thoughts were in line with mine; she wanted to stay with me, too, hard as that was for me to fathom. It seemed we were both driving ourselves crazy waiting for the other to leave us for someone "better," when it seemed neither of us had any interest in doing so.

I started to write "Do you still see us together in 15 years?" Then I crossed off the 15 and wrote in "10." But as I was writing, I was thinking that I could be pretty sure what the answer would be: she would hope that we'd be together in 10 years and even longer.

It felt like a golden opportunity had just fallen into my lap. I had never even thought about formally committing to Julie because I just expected in time she would find someone else. But it was clear that both of us wanted to be together for as long as we could imagine.

Marriage is a commitment, a statement of good faith declaring the intention to remain faithful to one partner. Yeah, they only work out about half the time; there are no guarantees in life. But it suddenly clicked that I was again doing something I had done before; I had been too afraid of Julie turning me down to risk telling her how I really felt, how much I really wanted to spend the rest of my life with her. Because I didn't feel like I was good enough for her, I hadn't come out and told Julie I loved her; she read it in my mind first. Now, I hadn't considered asking her to marry me because I didn't feel good enough for her. Yet I had just seen with my own eyes (so to speak) that she saw things in me I didn't. Fact is, what it really looked like is that Julie wanted to marry me, too, but considered it to be a pipe dream because she thought of herself as "damaged goods." It appeared as if we both wanted to commit to each other—the only thing missing was the invitation.

I flipped the card over and wrote something else on the back.

"Hey, you're cheating!" Julie complained playfully.

"Maybe," I said noncommittally. I handed her the card, first question-side up.

As I predicted, her thoughts were that she wanted nothing better than to be with me for 10, 20, 50 years. I couldn't help but crack a little smile.

"I don't think I should read the question on the other side; that's cheating," Julie pretended to pout.

"Would it be more fair if I took off my glasses?" I asked. I was all but sure that I wasn't going to need them.

She wasn't expecting that. What question would I have written that I didn't need to use my glasses on? But it was more fair, so she said, "Um, OK, I guess that would be more fair."

I took off my glasses and leaned back in my chair. On the one hand I was nervous—what if I had read the whole situation wrong and she turned me down? On the other hand, I was excited with a confidence one can only have if one can read someone else's mind that we were about to share life-changing moment.

"Should I turn it over?" she asked hesitantly. The rules of the game had changed. I nodded. She turned the card over and read what I had written.

Will you marry me?

Her first reaction was to gasp for breath and put her hand over her mouth. Then she looked at me, unbelieving, tears of joy already welling up in her eyes. Then she jumped out of her seat and knelt in my lap, not noticing that the untied flaps of her shirt parted completely in the process, wrapped my head tightly in her arms and between kisses said "Yes, yes, oh honey, yes, yes, yes."

She held my face in her hands and said, "Oh honey, I can't believe you really want to...oh, honey, no, I hope you don't think I suggested this game as a way to..."

I quieted her with a kiss.

"There is nothing that would make me happier than if you would walk down the aisle with me and say 'I do.' I've just never asked because...well, because I couldn't imagine why you would ever say yes," I explained. "But in the course of this game it became clear that we have both been afraid of the same thing—losing each other to someone else. So—let's do something about it! I want to declare to the entire world that I love you, and only you, and I want nothing more than to spend the rest of my life with you. I'm just sorry that, like an idiot, I don't have a ring to give you."

"I don't need a ring," she said, kissing me from above. She had that lovely, soft-like-warm-butter feeling in my arms that she gets whenever I've done something that makes her feel especially close to me and she wants to do anything in her power to make me happy, too.

"Oh yes you do," I smiled. "I don't want there to be any doubt that YOU are NOT AVAILABLE." I put my arms around her, looked up at her kneeling on my lap and kissed her.

Putting my arms around her opened the untied flaps of her vest; from where I sat I swear it looked like her breasts were trying to reach towards my mouth of their own accord. It was only then that Julie remembered that she was, for all intents and purposes, already naked.

"Hmm-hmm," she chuckled, "it won't take much work to make love, now will it?" She held my face in her hands and kissed me. Then she shifted slightly and placed her left breast right on my lips, offering her nipple to my grateful mouth. She let me suck her tit hungrily, then she shifted back and kissed me some more.

There is something special about sexual first times—first time with a new partner, first time in a new place, first sex as man and wife. But arguably none is more special than the first sex after becoming betrothed. Up to that time, you may have had all the sex in the world—Julie and I did pretty much did—but no matter how much you loved the person, there really was nothing to stop either of you from deciding to move on to another partner without warning. Wedding night sex is special, even if it's not the first time you have sex, because it's the first time you have sex committed to your spouse. But the first sex after you get engaged is special in an even more emotional sense—it's the first time that you know for sure that your partner wants you above all other possible partners in the whole world. You have just agreed to promise that your partner is the only person you will ever have sex with again. That knowledge makes the first sex after engagement a highly emotional experience.

Any other time Julie would have been happy to blow me, sucking me off if I wanted it. She had stripped for me, posed split-beaver naked for me, teased me, been submissive for me, swallowed every last drop of my cum, and used her tongue on my dick as an alarm clock. Most of the time she was even willing to open her ass for me if that's what I wanted. But on this occasion, the only kind of sex that would do was to couple my penis with her vagina. Face-to-face, body-inside-of-body—sex that was the epitome of intimacy.

Not only was Julie already basically naked, she was rocking up and down—and she hadn't even taken my dick out of my pants yet. She was, however, so wet that she was leaving a damp spot on them. Kissing me, gently rocking herself in anticipation, she freed the beast. I was pretty hard, what with Julie sitting on me like that. She stroked my cock, coaxing it to become even harder. Once it met with her satisfaction, she lifted herself up higher, guided my penis to her private entrance, and then nestled herself down on my cock. She closed her eyes and wore a face of pure pleasure as she slowly rocked up and down, feeling my dick rise and fall within her.

It was a good thing she was on top. We guys, we tend to be orgasm-driven. That's the point, after all, isn't it? Maybe, but at that time and place, it wasn't the only point for Julie. She just wanted to feel me be inside her, a tangible manifestation of the deep emotional connection we shared. She rose and fell slowly, like ocean waves crashing upon the sand. And she wanted me to be as far into her as possible; she adjusted herself so that her legs were even wider apart to facilitate deeper penetration on the downstrokes. Sometimes she would hold my face and kiss me, necessitating small strokes. Other times she would put her arms on or around me, permitting longer strokes and deeper penetration. But the constant was her being able to feel me deep inside her, fusing our two persons into one at the point of contact.