On-Line Fantasy Turns to Reality

His response was immediate and intense. God, he barely had them for ten minutes before my e-mail chimed and there it was, a video of his wonderfully hard dick spurting all over me while I listened to him describe how much he wanted me more than Stephanie and how he'd done nothing but think about me in the past few weeks despite his best efforts.

I had two objectives in mind for Scott, one involving Bonnie and the other Stephanie. For his fiance I wanted him to cum in her bra and panties which meant getting them in the first place. For his mother I wanted him to become bolder in exposing himself to her. Not to the point of her actually seeing it but as close as he dared.

Having crossed the line, what was the point now in me holding back? The only thing was the price for Scott was steep but I knew that Scott would do anything for another shot of me nude, for another glimpse of my wet pussy. Like any economic situation where a market is dominated by one supplier, the price skyrocketed...

The Stephanie part was actually the most difficult mainly because they didn't live together and so there were fewer opportunities. It also didn't help that now she was aware of his feelings for me and no doubt was keeping a much closer eye on him - and her underwear.

Scott was a horny 22 year-old guy which means he found a way. Somehow he managed to sneak off with her bra and panties, masturbating several times in one day so as to literally soak them with smelly sperm. He was aptly rewarded with a photo of me masturbating as I watched him cumming on her underwear.

Getting Scott to betray the love and trust of his fiance was simple. It was no different than when a married guy contacts me and next thing you know he's betraying his family's trust. They all contact me because they are missing something in their lives that the woman who SHOULD be giving it to them either can't or won't. I'm being kind - I'd say 99% of the time it's because she won't. ALL men have needs and many of them don't handle the frustration of a sexless (or less sexual than they wish it was) relationship well. All I have to do is give them the opportunity. It's not like I seek them out and force them to do anything. In some ways I feel like I perform a community service. If it wasn't for me would they be seeking out someone to meet and actually commit adultery? If they couldn't release their feelings to me, would they cave in someday to their lust and molest their unwilling daughter?

No, getting Scott to tell the truth about his feelings for Stephanie was easy. It was his mother that became the bigger challenge and the more daring it required, the hornier it made ME for him to do it. The prize I offered must have motivated him though - photos of me with a dildo fucking myself. One way or another he was going to find a way to do it!

Scott claimed the hard part (not his dick, the act of daring) was getting the photos to prove he'd done what I demanded. I could understand that as how do you explain to your mom that you want to take a picture of your dick behind her back? Still, since he'd done it once he could find a way to do it again - at least he would if he wanted to see me licking the dildo after I'd masturbated with it.

It was Scott who came up with the solution - clever horny boy! He somehow managed to set up his phone to give a view of his mother's work area. All he had to do was wait for the right opportunity when it was just the two of them and she was engrossed in her work on the computer. To be fair, I had to understand that such a situation probably wasn't the easiest to set in motion but that didn't keep me from teasing him and pushing him.

Then it finally came - the video I'd been waiting for most of all. I opened the file and started watching. The first images were of him setting up the phone but then he pulled away and I could see his mom working across the room again. He was wearing a pair of loose grey shorts and a T-shirt but otherwise barefoot. He turned the camera down to his crotch and there he had his dick out, stroking it with one hand as his mom worked on across the room totally oblivious. God, all she had to do was turn around suddenly to ask him a question and there was no way he could react in time to keep her from seeing what he was doing!

Back and forth the camera angle went, first on his mom and then back to his dick. He must have been super horny as it only took a few minutes before he was cumming all over his hand. OMG, it even spurted out onto his legs and I figured some of it must have landed on the carpeting. He quickly stuffed it into his shorts but that just created a wet spot in the crotch. Just when I thought he couldn't get any more naughty, he got up and walked across the room to his mom and put his hand on her upper back and said something about dinner and such. In doing so some the cum on his hand remained on her blouse! That was the final shot but by that time I was soaking wet!

Scott seemed to really get off from it as well as during our next chat it was all he could talk about. He seemed more anxious for me to say how much it turned me on than anything. I told him that I'd masturbated while watching it several times. It wasn't true (I only did once) but then did it matter? He ended up sending me another tribute to me and his mom minutes later, using one of her bras that he seemed to keep on hand these days for just such times.

Now what? I'd never actually had anything like this happen before. Oh sure I've had some guys do some pretty wild things, even videoing themselves cumming on their sleeping daughters. Still, nothing was comparable to where Scott was heading. This last video, where his mom was fully awake and just a quick turn from catching him masturbating, had me wondering where this was leading.

It wasn't long before I found out. This time it started out as before with him stroking himself as his mom worked away clueless in the background. This time though, he stuffed his erection in his shorts. being he wasn't wearing underwear, it poked out in an obvious manner but he didn't seem to care. Walking over behind his mom, he stood squarely behind her and put one hand on her shoulder as the other pulled out this dick from the side of his shorts.

As for what happened next, if I hadn't see it on video I would never have believed him if he had just told me. As he talked to his mom he masturbated himself, stroking his dick and occasionally straightening up to lean in closer to her so it oppressed in tight against her. OMG, how could she NOT feel it against her back? They talked and she would gesture about something on the monitor, totally oblivious to her son masturbating behind her back.

Finally he put his dick away and walked back towards the camera. OMG, the front of his shorts were dark with his cum. He must have pushed it back in just as he came, soaking the crotch with his own sperm! Grinning at me, he showed me his hand where I saw strands of cum and then he did something very few men have ever done for me - he licked it off, all with dear old mom sitting across the room working away as if nothing had happened. Wow, if she only knew!

After that I almost felt guilty. Was I pushing him too far? As I've often said, I never really want the guys I chat with to get in trouble. A few risks are OK but Scott was going way beyond the normal boundaries.

As I said, I ALMOST felt guilty...

Crossing the Line

=================

After masturbating behind his mom's back I didn't hear anything from Scott for more than a week which surprised me considering how excited he'd been when we chatted later that day. My first thoughts were that maybe he had finally realized just how dangerously close he'd come to being caught and decided to back down. Then I wondered if maybe he HAD been caught in another such episode. Heck, there was always the possibility that she HAD known what he was doing but waited to confront him until later rather than embarrassing him by catching him in the act.

When I finally saw his e-mail in my Inbox, I have to admit my heart was pounding. What would it say? Had he done anything new? Could he possibly top what he'd done last? Most of all, was everything OK? Well, nothing could have prepared me for what was waiting for me. As so often seems the case, reality trumped fantasy.

The e-mail was HUGE; it must have taken him forever to write. Boiling it down, here's what had happened a couple of days before...

Scott had returned to his mother's bedroom for another round of cum on his mom's clothes with the intent of doing another tribute for me. The house was empty except for him so he'd undressed in his room and gone into her room stark naked. It was a little more dangerous in that if anyone was to pull in the driveway he would have to run back to his room without being seen but it was that extra element of danger that helped turn him on all the more.

What happened next was interesting but didn't surprise me in the least. My mom once told me that men have two heads and only enough blood to run one at a time. Oh so true! When a man gets an erection it's like his brain ceases to function along with most of the safety interlocks in his consciousness. Like how many guys have told me they get caught after they masturbate because they forget to close a window or leave out the evidence? It's no wonder they fall asleep after sex, it's Mother Nature's way of protecting them from doing harm to themselves until the brain wrests control back from his dick!

So anyway, Scott was sitting naked on the edge of the bed jerking off using one of his mother's more lacy bras. Seeing the choices he made in the past when it came to which of her bras he preferred to cum on, he seemed to lean towards the more sexy ones. He'd told me once that he'd never imagined that his mother actually wore anything like those. Those, along with the dildos he found in her drawer, were the inspiration for buckets of cum-filled episodes in her bedroom!

As I said, two heads... one allowance of blood. It must have been one of his more intense moments with his erect dick demanding all the blood while it remained firmly in control of situation as he never noticed the shadow at the doorway...

"Just as I thought," his mother said softly but firmly.

Instantly Scott tried to react but there was no place to go and nothing to hide himself with other than her bra. Without thinking, he used the bra to cover his erection as he sat there on the bed with both hands over his crotch. As I read his description of the situation, I almost laughed at the mental image. It reminded me of a time when I was babysitting and I walked in a boy's bedroom while he was jerking off using his sister's panties. Similar situation... same reaction.

"Well don't stop now, as close as you are you may as well finish," she said rather matter-of-factly with her arms crossed.

Of course it wasn't nearly that easy for Scott. Another case where fantasy meets reality and it turns out the actual results are quite what the imagined ones were. For instance, I had to wonder how many times he'd masturbated thinking of this exact scenario? But then I'm sure in every one the story line went something along the lines of where she immediately stripped and sat on his dick or something equivalent. Well, now she was actually there but she wasn't undressing and kneeling to suck his dick like she was supposed to!

"C'mon Scott, do you really think I don't know what you've been doing lately?" she asked. Her tone was gentle but Scott was too traumatized to say anything.

Interestingly, but not surprising to me, his dick stayed fully erect. I say not surprisingly because I remember way back when Steve and I had only been having sex for a few months. Sure, he'd had plenty of other girls before me but he was the only guy so far for me and it was like I couldn't get enough of his dick in me. We were doing it in the basement of his house one day when everyone was supposed to be gone but right in the middle of things his mother interrupted us. Just as Scott described to me how his erection refused to budge, so it was with Steve's dick inside of me. Yes, he stopped humping me at the sight of his mother but he didn't pull out or even give a hint at deflation. If anything, every few moments he would instinctively pump me just once as if he couldn't control himself.

"You know Scott, I was OK with the panties, maybe even the bras, but now you've pretty much ruined a few of my favorite blouses," she said with a soft smile that blunted her words. "I was going to say something the other day when you pulled that stunt in the family room but I figured sooner or later I'd catch you."

Scott just sat there, unable to move or say anything. Then to his horror, as if it had a mind of its own, his hand jerked his dick as it gripped him through the bra. His mother didn't say anything about it but she couldn't have missed it.

"I tell you what, I'm going to take a shower so you finish up before I get done. Then we're going to have a talk, OK?" she more or less demanded and then added, "Oh and PLEASE, put my bra in the laundry and not back in my drawer when you're done. That's really not cute."

With that she turned and left. Scott, being a 22 year-old horny male, did what any other 22 year-old male would do in this exact situation - he finished jerking off! Whether it was his overactive imagination or a reaction to the erotic nature of the situation, when he finally came he groaned loudly and spurted a HUGE load of sperm leaving a slimy mess in both of the bra cups. It was like once he started ejaculating the loads would never stop!

Now that he'd cum it was like reality set in. back yet again to the two head analogy. It's like after a man cums and the blood rushed back to his brain, THAT's when he realizes what was going on when he was too engrossed with making himself cum. Oh my god, his mother had caught him! More than that, she hadn't yelled at him, well other than to tell him put the used bra in the laundry when he was finished. OK, so it wasn't quite up to the level of his fantasies, but it wasn't the disaster he'd always feared might result if he'd been caught.

Not really knowing what else to do, he dropped the violated bra in her hamper this time and walked slowly back to his room. As he got dressed he wondered what his mother would say when she was finished cleaning up.

As it turned out, she said the one thing he least wanted to hear - nothing. Even if she had yelled at him it would've been better than leaving him hanging as if nothing had happened. She had said she was going to have a talk with him but when she came out of the shower she was wearing a long cotton robe as she passed his open bedroom door and then she shut the door to her bedroom behind her. Not a word...

That night it was just her and him for supper and throughout the entire meal Bonnie chatted about her day at work and such, never once making any reference at all to the recent events. Poor Scott was on pins and needles the entire meal, waiting for that moment when she would suddenly lower the boom but that moment never came.

That night when he was ready for bed, his mother appeared at the bedroom door. She was wearing the red satin pajamas Scott and his brother had chipped in together to buy her last Christmas.

"Here, use these and when you're done, just ask me for some more," she said matter-of-factly as she took her hand from behind her back and offered him a pair of panties and a matching bra, "At least this way you won't ruin my expensive ones and my drawer doesn't reek of old cum."

Scott automatically held out his hand without a word but the curiosity in his expression spoke volumes.

"Good grief Scott, get over it," she huffed, rolling her eyes, 'Do you somehow think you're the first boy to do something like this? I guess you don't know that your older brother started doing the same thing when he was even younger than you goodness sakes. But then he was a panties guy."

Now THAT revelation really surprised Scott. His brother had certainly never mentioned anything like that to him but then he was four years older and they didn't exactly talk about personal things, let alone their masturbation practices.

Bonnie laughed a little saying, "Where did you ever get the idea to put my things back in the drawer when you were done? Do you have ANY idea how horrible your junk smells after a day or so? I knew from the first time what you were doing. All I had to do was open the drawer and the odor hit me like a truck."

"And you don't mind?" he finally blurted out.

Bonnie paused for a moment, considering her words carefully. "It's just a phase I think most boys go through when it comes to their mothers. Ok, so you're a bit of a late bloomer but it's sort of nice to know I can still excite a young guy. After all, it's not like I'm exactly an eighteen year-old teenager anymore."

"Oh mom, you're beautiful!" Scott blurted out before he realized what he was saying.

"Well you're not so bad yourself," she said suddenly grinning. "Damn, I'd love to know where you got that monster from, certainly not your father."

Scott blushed. Listening to his mother compare his dick to his father's wasn't exactly something he was accustomed to hearing.

"Seriously," she went on, "You're hung! Oh yeah, you're going to make Stephanie one happy girl someday."

With that she left him after which he immediately made use of one of the bras she'd left him. he was so hard after what she'd just done and said it didn't take long before he was spraying cum all over it. Indeed, the events of that day changed Scott's relationship with his mother in ways he'd never dreamed could be possible. It didn't hurt that typically it was just the two of them in the house as his older brother had moved out and his father travelled for his work more than half the time, Even when his dad wasn't traveling he all but lived at his work office.

The first set of underwear she gave him barely lasted a week and that was using each of them twice or even three times before he dutifully dumped them in the hamper. At first it was awkward to ask his mother for a new set of panties and bras. Sure she'd told him to ask but he put it off as long as possible until the set she had first loaned him was practically saturated with sperm. She smiled at him as she went to her drawer to pick out a few new sets saying, "Now don't wait so long next time, OK? Damn, I don't know if I'm ever going to get those last ones clean again."

All this time Scott was still chatting with me, letting me know each day how things were going. While at first he was excited about his new relationship with his mom, at the same time I noted a growing sense of disappointment. It was like now that his mother knew what he was doing - and even approved of it and encouraged him, it was like it wasn't as hot to do it anymore. Sure he still did daily tributes for me using her photos and others of me and Stephanie, but the edge seemed to be missing. I didn't hear that same sense of lust and urgency in his voice as he masturbated, almost like it was being something mechanical.

As his frustration became more and more pronounced, finally during one of our chats I challenged him, asking him to tell me what he really wanted.

The response was short and sweet. "Fuck her."

I paused at the keyboard and finally wrote back, "Then why not do it?"

The screen remained blank for what seemed to be hours although it was just a few minutes. Finally an even shorter answer appeared.

"OK."

That was it. Just one brief word and he dropped off-line leaving me to wonder where this was all going. It was both excited and frightened all at the same time. Excited because I wondered just how far his mother was ready to take this. Frightened for the same reason - what if she decided enough was enough and started asking too many questions about where he was getting all these crazy ideas from?