The Cabin

Tom was headed to his Aunt Susan and Uncle John's cabin in the north woods with his mom and dad for two weeks. He had mixed feelings about the trip. He'd miss hanging out with his friends, but the "cabin" was actually an ultra-modern house next to a beautiful lake and he'd have a very cool room all to himself. And even though his aunt, who was a nurse, was something like 40, she was totally hot. She has a lean, athletic-type body that made his heart beat a little faster just thinking about. And it wasn't like he had a girlfriend right now; so he figured all in all two weeks at the cabin would be OK.

The drive up was uneventful and they had burgers for dinner. They sat on the deck and he got to have a couple of beers even though he was only 18. The best part was that his aunt wore this tight fitting polo with no bra. He spent most of his time stealing glances at her achingly beautiful breasts. He loved the way they jiggled under her shirt. As soon as Tom thought he could get away with it, he said he was tired and figured he'd turn in. It was only about 9:30 but he really wanted to be alone. Fortunately, he was able to hug his aunt before leaving the party and feel those voluptuous breasts against his chest.

The next day after breakfast they all went swimming. Tom thought his aunt looked awesome in her bikini. After lunch his parents went fishing with his uncle, but his aunt said she had some other stuff to do. Tom thought fishing was totally lame and fortunately no one pressured him to go.

Tom was sitting on the deck playing a video game when Susan pulled up a chair and said, "Are you planning anything special this afternoon?"

She'd switched into a tight-fitting tee shirt with no bra and a pair of shorts. Her nipples were clearly visible and she looked even hotter than last night. He would have followed her anywhere.

"No, just playing on my computer."

"Great, I've got a brand new video I think you'll be interested in. Wanna watch it with me?"

Tom had no idea he was walking into the ambush of his life. Susan suggested they watch it on the giant flat screen TV in her bedroom.

"Why don't you grab a couple beers while I hook up my computer?"

Tom smiled to himself as he stole another look at her incredible breasts. He was just beginning to relish the prospect of spending the afternoon with his totally sexy aunt when he realized with horror what was on the screen. It was himself, entering his bedroom just after dinner last night!

"Wait a minute, what is this?" he stammered. "Turn it off!"

Now it was Susan's turn to smile. Her plan was working perfectly. Tom didn't know it yet, but this was an afternoon he would remember for the rest of his life.

Susan paused the video and said, "I'm afraid there's something I haven't told you Tommy. When we built this cabin, we included a state-of-the-art security system. And part of that system includes motion-activated cameras placed throughout the house -- including your room. We usually turn it off when you guys are here, but I deliberately left it on last night. And now we're going to watch the feed together."

Tommy was total fucked. If he insisted they not watch the video, his aunt would know there was something terrible on it; but if he agreed, he'd be so humiliated he could never face her again. He was paralyzed with fear. Finally he decided groveling was the lesser of two horrible evils.

"Oh please Aunt Susan. You can't watch this! You don't understand. I, I, I...You just can't! I'll do anything if you just stop it -- anything!!! Please, please, please!!"

"I'm sorry, Tommy, but that's just not an option. I can't believe there's anything on this video that'll surprise me, and I've got the feeling watching it together will be a huge learning experience for you. I know it's hard for you to understand, but I really believe you'll thank me later. Besides, this'll be between just you and me. I don't like playing hard ball, Tommy, but either watch it with me now, or I'll have to text it to your mom.

He really was fucked. She had all the cards. He was literally trembling with fear as he thought about what was in that video. He wished he was drinking whiskey.

"Now just sit back and let's see what we have," Susan said with a victorious smile.

The camera must have clicked on as soon as he entered the room. The picture was clear and amazingly sharp. This ordeal was going to be even worse than he feared. He'd been aching to be alone all day, and the tape showed that he wasted no time getting down to business. He pulled back the spread and propped two pillows up against the headboard. Then he disappeared into the bathroom and returned with a bath towel and his toothbrush. He carefully spread the towel out next to the bed and made sure the drapes were completely closed. He looked at himself in the full length mirror next to the bed and smiled.

Tommy thought he would die. He was desperate to put a stop to this but he had no clue how. It was a nightmare!

Meanwhile they watched as Tommy took off his tee shirt and shorts while gazing at himself in the mirror. He stood there for a while before pulling down his white cotton briefs. His penis was soft and he stared at it for a few seconds. Then he turned sideways, still staring at his penis, grasped the tip and stretched it away from his body -- checking himself out. Finally he laid down on the bed and propped himself up with the pillows.

Susan was salivating. Tommy's body was lean and fit. His young penis was perhaps a tad small but she loved it! She thought it was cute that he was worried about its length; but maybe she could help him with that later.

Tommy was numb with embarrassment. But he was powerless to do anything but sit and watch in pure dread.

Back on the video, Tommy's hands moved quickly to his penis. Still soft, he started stroking himself with both hands. His right hand moved down the length of his shaft and was quickly followed by the other. He continued stroking like this, alternating hands. He was methodically using his fingers to stimulate the underside of his glans. It only took eight or ten cycles for him to get hard, and he took a short break to admire his erection before starting to stroke again. He continued on like this, eyes closed, luxuriating in the experience.

Susan paused the video and said; "Now Tommy just try to relax. So you're masturbating. Big deal. Did you think nobody would figure out what you were planning when you announced you were going to bed at 9:30? Your mom even said something like, "I wonder what he's got up his sleeve?" and we all smiled about it. What else would a healthy 18-year old boy be planning under such circumstances?"

Great, Tommy thought. The whole family's been laughing at him behind his back. How can this get any worse?

"Besides, you have a gorgeous body, Tommy! So young and strong -- just look at that beautiful erection and how quickly you got hard! And I love the way you're stroking yourself! I've never seen that technique before. Have you always masturbated that way?"

Tommy just sat there with his head spinning. Things were happening so fast! He was mortified that his beautiful aunt was watching him jerk off, let alone asking him all these questions about it. Was he doing it the right way? Was it wrong to use both hands? But he liked what she said about his cock, and the way she was using words like "masturbation" and "penis" was kind of exciting. Finally he managed so say, "Um I guess so."

"What do you like to think about when you masturbate, Tommy?"

Once again, he just sat there, hoping she wouldn't make him respond.

"I've got all day, Tommy. Now just stop being such a baby and answer my question."

"My old girlfriend used to let me let me feel her up and sometimes she wouldn't wear a bra. Her nipples always got hard and she said it felt really nice when I touched them. I like to think about that sometimes."

"That sounds nice, Tommy. Did you do anything else when you made out with her?"

"Not really. After we'd gone out for a while I tried to touch her, you know, inside, but she said it was wrong and we broke up."

"That's too bad Tommy, but at least you have a nice experience to think about when you touch yourself."

Susan started the video again. Tommy continued his two-handed technique for several more minutes, but then he paused and got something out of his computer case. It was a ruler! He carefully used it to measure his erection, frowned and began stroking again. He took another measurement a little while later.

As if things weren't bad enough, it was now obvious that he was worried about the size of his dick! His mind raced for some face-saving explanation, but he couldn't think of one.

Susan couldn't help but smile. "I guess it didn't get any bigger the second time, huh? It's too bad men have to be so worried about the size of their penises. You know, it has nothing to do with how much of a man you are. You have a beautiful, healthy erection that most girls would love, Tommy. And even though it doesn't really matter, as a nurse I can tell you that you have nothing to be ashamed about in the length department! You probably don't believe me, but it's true."

The next part of the video was what Tommy was dreading most of all.

"OK Tommy, let's see what happens next."

After the measurement, Tommy put his toothbrush handle in his mouth to coat it with saliva. Then he pulled his knees up to his chest and began using it to rub all around his anus. He was really enjoying this sensation. Before long he positioned the tip directly in the center of his opening and began to probe inside, going a little deeper each time. In the meantime, he encircled his penis with the thumb and forefinger of his right hand and began firmly rubbing up and down on the underside of his glans. After a while he settled into a steady motion where the toothbrush going in and out of his rectum was synchronized with the fingers stroking his cock. He was in ecstasy as he pumped away and began to vary how far he penetrated each time. He loved the sensation in his anus as the handle moved in and out. Finally, he inserted the toothbrush deeply enough so it stayed put by itself and he went back to his two-handed stroking. This time his hands were moving much more urgently, and it was clear the end was in sight. After perhaps 20 strokes, he jumped up, and ejaculated all over the towel. His semen erupted forcefully in five or six bursts and landed mostly on the towel. When they stopped, he squeezed the last few drops out of his softening penis onto his fingers and wiped them off on the towel. He removed the toothbrush and put it back on the nightstand.

Tommy was reeling with emotions like fear, humiliation, embarrassment and shame at what they had just seen. He must be really sick. How could he do such a thing? It was one thing to jerk off; but using his tooth brush to stick up his ass was totally perverted. And Aunt Susan saw the whole thing!

Susan was creaming in her jeans. Tommy's show was way better than she expected!

"Now listen to me Tommy, because this is important. There's no reason for you to be embarrassed or ashamed about what we just saw. In fact it was totally natural and beautiful. Given the hormones ravaging the body of boys your age, it would be astonishing if you hadn't masturbated at least once last night. In fact, that's the whole point. Your mom knows you've been masturbating, and she's worried that you might be feeling conflicted about it. Since I'm a nurse she asked me to help. I knew you had absolutely no choice but to masturbate last night, and that's why I wanted you to make this video. Masturbation will be an important part of your life whether you like it or not, Tommy, and by watching it together, I can help you learn that you can feel good about it. You should be able to masturbate whenever you need to without feeling guilty or ashamed. I knew it would be a hard lesson for you, but it's a critical one!"

Tommy was overwhelmed with emotion and conflicting thoughts. Not only did his mom know he was masturbating, but she discussed it with Aunt Susan! How would he face his mom again? And having Aunt Susan watching him not only masturbate, but measure his dick and stick a toothbrush up his ass made him tingle with embarrassment. He was devastated.

"How are you doing Tommy?"

"Fine," he said sarcastically.

"OK Tommy. I know this has been awkward for you; but now it's time for us to have an honest, conversation about this important part of your development. I sure you understand that the only way I could be sure you'd open up was if you were confronted with the evidence. Let's start with some basic facts: First, ALL boys your age masturbate (so do virtually all girls). The urges your body is experiencing give you absolutely no choice. Telling a boy not to masturbate would be like telling a bird not to fly. You need to grow up and accept that fact. Masturbation is not an option for you, Tommy -- it's a psychological and physiological imperative. Beating yourself up about it is just plain stupid."

"Second, ALL boys your age measure their penises at one time or another due to inherent male insecurity. This insecurity is based on the misconception that you need to have a big dick to be a man. Nothing could be farther from the truth. Nevertheless, as I said before, even though you probably won't believe me, as a nurse I can assure you that you have nothing to worry about in that department."

"Finally, not all young men insert objects into their rectums when they masturbate; but it's also not uncommon. It's a very sensitive area and one that many boys experiment with even before they discover true masturbation. There's nothing wrong with using your body for pleasure, and anal stimulation is no exception. So I don't want you to think you're sick or perverted for doing what feels good."

"Do you have any questions, Tommy?"

Intellectually, he knew what Aunt Susan was saying was probably true, but he was still freaked that she saw him do it all. Especially the part with his toothbrush. He still felt like a sicko. He just stared into space with a blank look.

"OK, Tommy, now it's time for you to answer some questions. How often do you usually masturbate?"

Oh, my God, he thought, "Haven't I been through enough!"

"Tommy, I know these can be embarrassing questions, but you may never have another chance to be fully honest about this subject, so why don't you just forget about being uncomfortable and tell me the truth?"

"Um, OK. I guess I usually do it once a day -- sometimes twice."

"That's good Tommy. See that wasn't so hard! Most young men your age masturbate at least once a day. Where do you usually do it?"

"In my room, I guess. Sometimes in the shower."

"Have you done it at school, or other places away from home?"

"I guess I did it at school a couple of times, but only between periods when no one would come into the bathroom. Sometimes I start thinking about it and I just can't wait."

"That's normal for young men your age. Sometimes the urge to masturbate is so great you just can't help yourself. I'm curious about something else, Tommy. How often do you insert things into your rectum?"

Even though Aunt Susan said it was normal, he still felt like it was something he shouldn't be doing. The image of him pumping his toothbrush in and out of his asshole flashed into his mind and he felt like a sicko again.

"I really don't do it that often Aunt Susan. Honest. Sometimes I do it as kind of a bonus because I like the way it feels, but I really don't do it that often."

"Now, Tommy, there's no need to be defensive. As I said before, it's a very sensitive area. I've given enemas to lots of men and almost all of them get erections when I insert the nozzle. Sometimes even a rectal thermometer is enough to make them hard. It's natural for you to crave such feeling sometimes -- especially if you've been looking forward to an extra special session. Just one more thing, Tommy -- why do you use a towel?"

"I guess because I don't have to worry about cleaning up afterword. There's a laundry hamper next to my bed and I just grab something and put it back when I'm done."

"By the way, Tommy, that's how you mom figured it out. She noticed the stains one day when she was doing laundry and started looking for them after that."

Tommy was mortified that his mom was monitoring him like that. What's he supposed to do now? She'll know he's onto her if he stops; but if he doesn't he'll be telegraphing every time he does it.

"I don't want you to worry Tommy. Your mom told me she felt proud when she discovered the evidence. It means you're becoming a man! Just between you and me, she told me it was a big turn on for her!"

Yikes, what's he supposed to do with that?!

"OK Tommy, we're almost done. We've already talked about the technique you like to use. By the way, most boys figure out what feels best when they first discover masturbation and then stick with it -- sometimes for the rest of their lives. Do you have any questions for me?"

He shook his head.

"OK, then let's recap. Like all 18-year old boys you masturbate -- usually at least once a day -- which is a natural, healthy and beautiful part of your life. You have a lovely penis and easily obtain erections. You like anal stimulation and do it occasionally when you're looking for an especially satisfying experience. Until now, you've felt conflicted about your masturbating (particularly the anal part) due to guilt and shame; but you do it anyway because of strong natural urges that you can't control. Does that pretty much sum it up, Tommy?"

Tommy was actually starting to relax. Aunt Susan made what he's been doing seem like it's not that big a deal. He still had a lot to process, but maybe things wouldn't be so bad after all.

"Um, I guess so Aunt Susan."

"Wonderful. So you're feeling better about your masturbating?"

"I think so, yes."

"Tommy, have you done it again since last night? Maybe in the shower later last night or this morning?"

Tommy shook his head, a bit sheepishly.

"Then after all this talk you must be about ready to burst! We've got time before the others get back. Would you like to do it now?"

The idea hit Tommy like a freight train. Aunt Susan was right. He was desperate for relief, and the idea of doing it while she watched was unbelievably exciting. He was practically hard already.

Susan knew she had him. And the prospect of watching her young nephew stroke himself made her tingle with excitement. Poor Tommy didn't have a chance.

"Now don't be shy Tommy. This'll be just between the two of us. And can you think of a better way for me to help you come to terms with your masturbating than to offer my support and encouragement while you do it?"

Tommy's heart was pounding, and he just stared at Aunt Susan helplessly.

"Don't be nervous, Tommy. Why don't you stand up and take off your shirt?"

His athletic body made Susan drool.

"Very good Tommy. Now your shorts."

Tommy knew he was well on the way to a full-blown erection, but there was nothing he could do about it.

"I know your penis is getting hard, Tommy. You don't need to be embarrassed -- just go ahead and take off your shorts."

Susan was viscerally enjoying the show. Tommy's erection was awkwardly positioned in his tight briefs and he tried to surreptitiously adjust it to a more comfortable position.

"OK Tommy, don't be afraid. I can already see your erection, so just go ahead and pull down your underpants."

With Tommy finally unveiled, it was time for her next move.

"Your penis is so beautiful Tommy! Just like on the video. Do you like showing it to me?"

Tommy was swirling with emotions -- and the idea of showing himself to Aunt Susan and thinking about her judging him was so exciting.