Jackie Makes Things Right

Relieved but feeling guilty about the deception of portraying herself as an innocent newbie only recently having discovered the idea of doing a guy in his asshole, Jackie hesitated a moment before clicking "Submit."

Was she really doing this?

Her finger tip eased down on the "Enter" key, and in a split-second it was too late to think anymore about whether she should or should not send her electronic note in a bottle into the virtual sea from which she was hoping mpls_ace would pluck it.

**

Waiting to see a reply from mpls_ace to her posting was enormously nerve-wracking for Jackie. Every morning she checked the blog. Two or three times a day she took a break at work to walk around the corner to a coffee shop with free wi-fi to check her laptop, anxious to see if a reply had come in (she did not want--—ever--—for the site's URL to turn up on her work computer). Every night she checked her computer as soon as she got home and then at least two or three times before going to bed.

This went on for five agonizing days.

Then, on a Wednesday night right before she would have gone to bed, she saw it:

"Glad to hear that you've taken a more liberated attitude to pleasing a man in this way, new2this. Don't worry about it if the first guy, or the second or the third, doesn't go for it when you try to ease the suggestion to him. You'll find someone who'll adore you for doing it, I promise. There are lots of guys like us out there."

Jackie's stomach did a flip-flop reading the words that mpls_ace had posted.

The clock on her computer's system tray read "11:26 PM." She checked the time stamp on mpls_ace's post: "10:57 PM."

He might still be at the site!

Because she had waited through five long, anxious days, she had prepared a response ahead of time. Indeed, she had re-written the response maybe a dozen times. Now it was easy to quickly type her message.

"Just saw your words of encouragement, mpls_ace. I have actually been in a situation where I spoiled the evening when a guy asked me to put my finger inside him. That was before I became more curious and accepting. (Guess reading this blog is a pretty good indication of my change of mind, huh?) Anyway, I will take your advice and see if I can eventually find a partner who wants to let me try to take him to sexual highs doing the things I've read about on this site. I'm worried, though, about being inexperienced and saying or doing something foolish as I try to become a good lover in this way. Though I've had my share of sex (not enough of it really GREAT sex though!) and guys tell me I'm good-looking and they like having sex with me (and I don't want you to think I'm out there with tons of different guys, because I'm not), I'm still just in my mid-20s and haven't had any experiences with guys who were adventurous like that tattooed lover who was the first one for you to, well, um, you know."

After a quick read to ensure she had correctly typed the message she had so painstakingly composed, Jackie was satisfied that her email said what she had rehearsed in her head so many times. Her writing and re-writing of the message in the previous days resulted in just enough information to let him know she was a good lay (without saying it like that) and hot. The careful wording, though, also played up the novice-who-wants-to-try-this angle, adding the implication that she was still so embarrassed about doing it but so turned on that she couldn't NOT do it. Jackie thought that might be a big turn-on for Brandon.

She waited. She got up and paced, coming back to look at the screen every few seconds to refresh. She chewed her lip in--—what?--—worry? Excitement? Fear? Sexual anticipation?

She stamped her feet in frustration. "Come on. Please come on!" she said under her breath.

Then it popped up after a screen refresh.

His reply.

"Before every other unattached guy reading this blog makes the offer, new2this, what if we pretend we've just had the equivalent of an online, 5-minute speed-dating encounter and that now the woman can decide if she wants to ask the guy to call her. I know that the internet can be a creepy place, though, so I'll send you an email using the anonymous messaging feature to let you know how to find my Facebook page. Check me out, and if you're interested, email me."

Anonymous messaging? Huh?

Jackie immediately searched the site. In her eagerness to join after reading that first post from mpls_ace, she hadn't really read through the terms and conditions, and she hadn't really checked out other things the site offered. She totally missed the site's ability to let members send anonymous feedback to other members. Brandon (god, please let it be him; after all this, let it be him!) could use the feature to send her an email and in the email include his contact info.

Of course. This protected site members from having other members get their email addresses.

When she navigated back to the postings page, mpls_ace had signed off.

Damn!

She re-read his suggestion, though, and realized she needed to check her email. NOW!

Her inbox had one new message. It was his.

"Please believe me, new2this, when I say I've never done anything like this. You know, offering to get to know someone better after meeting them on the internet. And god knows that I'm REALLY nervous about this, about what you might think of me, given the subject matter of the blog. But I'm hoping that since you've been on the blog you're at least not turned off by what I've said there AND you'll understand that I'M new2this RE internet hookups. Anyway, don't hold it against me that I'm a typical male, interested in meeting a good-looking woman who's interested in sex. But if you go to my Facebook page and learn more about me (and, yes, the pictures are recent, and they are actually of me) and want to talk some more online, I'd like the opportunity to learn more about you."

Well. The message definitely did not create the impression of a leering internet sex-addict looking to lure a woman into a one-night stand (or worse). There was something about it that Jackie interpreted as sincere, as decent.

In spite of the fact that both of them knew that he wanted her to slide her finger deep inside his asshole, and she wanted to do exactly that. Repeatedly.

He left information about how to find his site, which did not involve the string of letters, "mpls_ace," in any fashion.

Jackie wasted no time going straight to mpls_ace's personal web presence. She was incredibly anxious to find out if it really was Brandon.

There it was—--his picture.

Brandon.

An exhalation that had been building for five days whoosed from Jackie's lungs, and she sagged into the chair in a mixture of exhilaration and exhaustion. She was a tightly strung wire from which the load had been released, and she did nothing for several minutes except smile to herself and gaze at the first photo which had come up on Brandon's Facebook page.

It was him!

**

"Yeah, I live in Atlanta," Jackie typed several days and numerous email exchanges later with Brandon. "I like the South, the weather and the laid-back feel here. But this is a big city, too, and there are cool things to do, like the annual jazz festival that I love to attend."

Their email interchanges had gone well. Jackie was alert to verifying the things she had already known and liked about Brandon (including the picture he'd posted of last summer's day at a beach somewhere with friends for a barbeque; he was definitely the Brandon-body she remembered). She also learned new things about him, things she liked: plans for an MBA in order to be well positioned for a faster rise in the business world, a shared love of Diana Krall's husky vocals and killer jazz piano skills, that he liked to cook several different kinds of dishes.

He seemed to like that she was an intellectual who was comfortable with a good novel or non-fiction title but who also enjoyed an action flick at the movies or a half-hour spent wall climbing at her local gym.

They purposefully stayed away from the thing they already knew the other was into.

It took only a few days, though, before Brandon asked what Jackie knew he would ask: "Can you email me a picture?"

It was the moment she dreaded because, after the few days of discovering more about him, she was REALLY starting to like him, especially knowing what she already knew: beautiful brown eyes, muscular yet lithe body, good sense of humor, skilled with his tongue and his cock. And that cock—--it was beautiful, delicious, and he knew exactly how to use it. God, after all this, she was tempted to employ some ruse that would guarantee the continuance of their online relationship even if it meant making things harder to explain in the future.

Knowing that his request for a picture was inevitable, Jackie had thought a great deal about what to do when Brandon asked. One strategy would be to send a photo of someone else, then hope he would still be interested enough to meet her.

That would clearly not work. He would surely feel tricked when—--if--—they finally met. She had already disappointed him once in Miami Beach. Tricking him would not make things better, no matter how famously they might have hit it off via email conversations.

She knew she had to be up front and honest. That being the case, the best picture would be one Melanie had taken of her in Miami Beach. Brandon would recognize the setting because the shot was in front of the club where Jackie had met him. At least she looked really good in the picture, and the sexy outfit she was wearing probably had something to do with why Brandon approached her later that night.

She had also considered what the email should say. As with her written and re-written response put together ahead of time in case he answered the post she had put up on the blog, this email, too, was crafted very carefully. She revised it after every email exchange they had, trying to add or tweak based on the totality of information she had about him at that point.

It became harder and harder to re-write it after each exchange because she was truly enjoying their relationship and communication. The last re-write before his request for a picture was at the ready in the "Brandon" folder on her computer. She pulled it up, copied it, and pasted it in:

Brandon, here's the picture you requested. I can't even begin to say how much I hope you still want to write to me after finding out that I'm Jackie from the wonderful time we had together during Spring Break in Miami Beach. At least, it was wonderful until I ruined it, and you'll never know how many times I've kicked myself for being such an idiot that second night with you. I've learned a lot since then, though, and your comments on the blog where we met gave me courage. You'll also never, ever know how much I hope that I will get the chance not only to resume our physical relationship, but to continue getting to know you. What I've learned about you since we began emailing makes clear that there are many, many reasons I want to spend time with you besides desperately wanting the chance to make you feel really good in exactly the way you want me to. It is the very least I can do for someone who is such a fantastic lover and who absolutely blew my mind, giving me the most intense orgasms I've ever had. Please write me back. ---Jackie.

_Please don't let this end it,_ Jackie thought to herself as she attached the picture to her email and hit "Send."

Then she waited.

For two days she waited, thinking the worst. Scared to death it was over.

His email finally came. When she opened it, though, there was nothing in it, and the email didn't even have a subject line.

"Shit! Shit, shit, shit, shit, sh-i-i-i-i-t!" she screamed, knowing he had sent a very clear message by NOT sending a message.

Then she noticed the attachment.

_Probably a picture of him giving me the finger,_ Jackie thought glumly.

Hopes and desires completely dashed, she clicked open the image.

It was a picture of two tickets to the Atlanta jazz festival and a plane ticket reading, "MPLS to ATL."

Jackie blinked, the image momentarily confusing her.

Then . . . FANTASTIC!!!!!

She breathlessly, immediately replied to Brandon's email with one word: "Yes!"

**

Her excitement at getting his email meant Jackie missed the implications of what Brandon had done until she had finally calmed down the next morning after a near sleepless night spent thinking about all the possibilities of resuming an in-person relationship with him. Over her morning bowl of cereal, though, she realized something about the picture he had sent. Those jazz festival tickets were not print-outs of an online purchase; they were real, bought-at-a-ticket-office tickets. And the same was true of the plane ticket—--it was a ticket sold by a ticket agent behind a counter at an airport or bought at a travel agency.

Brandon had worked very hard to arrange things. He had gotten in his car, driven around, spent money, (maybe even having to order the concert tickets over the phone, with the ticket agency overnighting his purchase to him), and then laid out the tickets on his desk in order to take the picture with his digital camera and email the photo to her. For that matter, the tickets were for seats way better than the seats she had, so she knew they cost a lot of money—she had actually inquired about that section of seating on the grounds of the park where the concert was held when she bought two tickets months ago (hoping that by the time the concert came around she'd be seeing a guy she would like to take to the concert). No matter now; she'd give her tickets to Jane, one of her friends at work.

Brandon was very eager to see her!

Jackie's extreme desire to make things great between her and Brandon, coupled with a near desperate horniness to do what he wanted done during sex, meant that she went into high gear on numerous fronts. It was only two weeks until the jazz festival.

Her after-work gym visits would be extended. Though she stayed in great shape anyway, two weeks of extra work and cutting back on carbs even more than her regular diet already did would mean she would be in fantastic shape to be seen nude by Brandon.

Hair. She arranged the salon visit for a couple of days before he would arrive. It would give her time to tweak the styling if she needed to.

Make-up. Jackie arranged an in-home visit by a make-up artist one of her friends at work had recommended. Her friend said the professional's recommendations about make-up, as evidenced by the make-over given as part of the visit, created a dramatically new, sexy look for her. Jackie wanted to see if a new look might add even more sex appeal to her features. Combined with a new 'do, she would look fantastic.

Outfits. Everything she wore during Brandon's three-day visit would be selected specifically to accentuate her best features, to look great on her, to cause Brandon to be proud of the hot woman he was with.

It would stretch her meager copy editor pay, but it would be worth it.

But the most fun, the most arousing preparations involved getting ready to explore Brandon's snug, warm asshole with her fingers and with a strapon dildo. That she would also be playing with his gorgeous cock, feeling it inside her as he stroked her to a killer orgasm, well, that in itself was enough to make her randy beyond belief. Their re-meeting place—--a blog about man-fucking—--assured all of it, though--—all of the various kinds of sex they would have, including the nasty, erotic, mind-blowing, first-time-for-Jackie sexplay that she knew was going to make her a basket-case of exhausted satisfaction with a man who might turn out to be THE ONE.

Her online education meant she had long since decided on the dildo she would get--—a feeldoe--—and the harness was also chosen based on multiple recommendations from women posting about their choices for man-fucking equipment. But now there was a reason to go ahead and buy everything she would need. The next-day delivery charge was worth it, and Jackie bought TWO bottles of an anal lube that had been recommended by several women, all of whom agreed with the saying that "too much lube is just enough."

_Oh, my, oh, my, my MY my my,_ thought Jackie the first time she slipped the bulbous end of the feeldoe dildo into her pussy. It felt so good in multiple ways. The delicious, filling sensation was wonderful, and the little ridges strategically positioned for clitoral stimulation were a thoughtful, arousing enhancement.

She looked at herself standing before her bathroom mirror, the phallus extending from her crotch, held securely by the muscles in her pussy walls. The recommendations she had read about the feeldoe all advised a harness when fucking as insurance that it stayed in place, but for gentler action—--like giving the man a visual he would never, ever forget the first time he saw his woman sporting a deep purple erection—--harness-free activity was a delight.

Jackie agreed, standing before the mirror and moving this way and that to see what effect the motions had on the cock sticking up from her crotch. It felt . . . certainly good physically, but good somehow psychologically, too. The power trip explanations in women's descriptions of why they enjoyed strapon fucking their men immediately came to mind the first time Jackie moved around with a hard-on. It broadcast her ability to penetrate her partner, to be the one going inside of him. In that instant, the erotic allure of donning a strapon to become the one with the large, erect sex organ who would use it to fuck her partner's surrendered orifice became crystal clear for Jackie.

What a rush! It felt fuckin' great!

She left the dildo in place and practiced walking around a bit, seeing it bounce in front of her and adjusting to what she needed to do with her pussy to grip the end that was nudging against her G-spot.

Oh, it felt REALLY fuckin' great.

She wasted no time heading into her bedroom to lie back on the bed, legs hanging over the side, and grasp the base of the shaft sticking out of her pussy. She began to handle the fake cock so it caused an internal message just the way she liked it. Some of the women said they used the feeldoe to masturbate . . .

That thought prompted her to pause her self-pleasuring for a moment and retrieve one of the bottles of lube. She poured some into one palm and coated her cock. (By now, in an amazingly short time, the dildo had become "her cock.") Excited, she walked back to the bathroom, enjoying her rapidly increasing facility in moving with the dildo, and again looked at her nude body in the mirror. This time, though, she stroked HER COCK the way she had seen countless guys in videos do it, sliding her fist up and down the stiff shaft.

What would Brandon think when he saw this? It sure as hell was turning Jackie on to see it. The sight plus the sensations inside her pussy really revved her up. Knowing she would be back in front of the mirror to practice, right now it was impossible to do anything but head back to the bed, re-position herself as she was before, and resume masturbating. Getting used to the dildo and how to use it for her own pleasure were going to be very, very important.

When she fucked Brandon in the ass, she wanted to bring herself to a blinding orgasm. The act itself, even completely divorced from any physical sensations, would be incredibly arousing and a total psychological rush. But being practiced at moving in ways that intensified her physical, sexual pleasure meant she would be able to double-dose on the supremely erotic nature of the act.

Jackie blew into the first orgasm unexpectedly. The thought of seeing him in front of her on all fours, spread open, with the dildo sliding deep into his asshole pushed some kind of automatic trigger that meant even a little physical stimulation would have brought on an orgasm. Added to the incredible sensation of the bulb end of the dildo bumping against her G-spot as she manipulated the end protruding from her crotch, the mental image set off sizzling fireworks.