A Walk in the Woods

Becky is the kind of friend you can confide in. She's the kind of friend you can whine to about your spouse, cry with, drink with or tell your deepest hang-ups to. She's the kind of friend who gives you a bath if you're unable. Those kinds of friends don't grow on trees.

So when Becky approached me wearing a scowl, I was ready for anything – including doing all I could to help.

"I'm worried about Tommy," she said. "He seems so aloof and withdrawn. Now that he's started college he should be having a blast meeting new friends and maybe even a girl. Instead, he's spending too much time in his room. If I didn't know better I'd say he was flirting with depression instead of flirting with girls!"

"Tommy's such a great kid...can you think of what could have brought this on?"

"Well, he was doing great at first; but then one by one his new pals started pairing up with girls. Unfortunately, Tommy's so shy he still hasn't found a girlfriend. Maybe he's sad about that."

"Why do you think he's so shy around girls?"

"I don't know. I used to worry about him because he's been such a late bloomer, but now that he's eighteen, he's finally caught up."

"Humm, being less developed than your peers is a terrible thing for a boy. Kids are so cruel during adolescence and being teased or just having to expose yourself in the shower can have lasing effects. Believe me, as a middle school teacher I've seen it all. Maybe Tommy just needs a little help to boost his self-confidence."

"I guess you might be right, but he barely even talks to me. I don't think I've got a prayer of getting through to him; and Tom senior would just scare the shit out of him."

"Actually, I wasn't thinking about you or Tom. I've got a pretty good idea what makes kids like Tommy tick and I'll bet I could help. Would you like me to have a little chat with him?"

"Wow that would be fantastic! Do you really think you could reach him?"

"I think so, but I've got to warn you that what I've got in mind is a little unconventional. It would need to stay totally private. You'd have to promise never to mention our talk or ask him about it. Are you willing to trust me? It's a deal breaker."

"Oh, Audrey I'd trust you with anything – even Tommy!"

"OK, great. I'll give it some thought. Is Tommy still into photography?"

"He was until all of this started, but I don't think he's taken a shot in months."

"Is he coming to our picnic on Saturday?"

"I hope so, but you never know these days."

"Why don't you tell him to bring his camera? Tell him there's an old barn I'd like to show him that would be a great subject for black and white shots. That'll give us an excuse to disappear for awhile. Your job is to make sure he comes!"

"OK, I'll do my best. And thanks so much."

The three days until Saturday were going to be long ones for me. The humiliation of naïve young men like Tommy is a visceral turn-on for me, and I couldn't wait to see how far I could make him go. And ironically, if my plan worked, my friend Becky, Tommy and I would all be winners.

I hardly slept at all Friday night. When morning finally came I was bursting with anticipation. I wanted to be as horney as possible for my encounter with Tommy, and that meant finding an excuse not to have our usual Saturday Sex. My solution was actually quite brilliant. I enticed my husband with the prospect of devoting my entire attention to pleasuring him with my tongue and fingers. At first he resisted, but when I started coating his testicles and burgeoning erection with saliva he melted. By the time I started teasing the underside of his glans with my moist fingers and probing the tip of his penis with my tongue, he was writhing in pleasure. His precum oozed out as I brought him to the edge over and over. When he couldn't stand it any longer he took charge – alternately sliding his hands down the length of his shaft. It was his favorite masturbatory technique. He had a powerful orgasm almost immediately, and the smell of fresh semen permeated the room. It took all of my will power not to join him in my own powerful release, but somehow I managed to convince myself to wait for Tommy. The poor little bastard didn't have a chance!

At last the picnic arrived. When we had finally cooked and eaten our burgers, and I had managed to hold off for what I thought was a respectable period of time, I sweetly asked Tommy if he would like to see the barn I had told his mom about. He didn't seem too excited, but consented to go.

Just before we got to the barn I casually said, "Hey Tommy, can I ask you something?"

"I guess."

"Your mom told me she's a little worried about you. For one thing, she says you having trouble finding a girlfriend."

"Um, I guess that's right".

"Would you like to talk about it a little, maybe I could help?"

The poor kid must have really been desperate because even though I could tell it was the last thing he wanted to admit he said, "It's just that I get really nervous around girls and all. I never know what to say and well, you know, I just, I just..."

"Oh Tommy, there's no reason to be afraid of girls. Most of them are probably just as nervous as you are. All you have to do is relax, be yourself and take a little initiative. Most girls would love to hook up with a good looking guy like you."

"You really think so?"

"Absolutely! I'll bet after a date or two most girls won't be able to keep their paws off of you!"

He didn't exactly look comfortable with the prospect.

"Does that idea scare you, Tommy?"

"Um, I guess so. It's just, well, you know, I, I ..."

"Tommy, are you a virgin?"

His body language made a verbal response unnecessary.

"And maybe a little worried about having to get naked if things get serious?"

"Um, well, maybe a little."

"You know what Tommy? There are only three things a guy needs to connect with a girl, and I think you can have all three."

"Really?"

"Of course I do. The first is a just being a nice guy. I've known you your whole life, and take it from me you're head and shoulders above most boys I know in that department. The second is to be squeaky clean. And finally, you need to be at ease with your own body and have a little self-confidence. A guy who is comfortable in his own skin is a real turn-on for girls."

"I guess two out of three isn't bad," he mumbled.

My plan was to control him using a demeaning attitude while playing on his inexperience and lack of self-confidence. With any luck, Tommy was about to lead himself more and more deeply into the depths of humiliation. But hopefully, he would emerge with a brand new perspective. I was feeling very good about my prospects.

"Look Tommy, I've got an idea. I know you've got the first thing nailed – you're a great guy. And I think I can help you with the other two if you're willing to take a chance."

"What kind of chance?"

"Just the risk of feeling a little embarrassed. I think we should check out your body together. With a little coaching I'll bet we can bolster your confidence and double check your hygiene at the same time. This could be a game changer for you Tommy."

"You promise not to tell anyone?"

"Not a soul Tommy – especially your mom."

"And I can quit whenever I want – like if it gets too 'embarrassing' like you said?"

"Absolutely. All you have to do is say so and we'll stop and pretend it never happened."

"Well, I guess it's OK."

"You're being very brave, Tommy. I'm proud of you. Why don't we just go under that tree in the soft grass and sit down?"

When we were settled I said, "OK, Tommy, let's start slowly. Why don't you close your eyes and try to relax while I touch your ears."

I worked my fingers lightly from the front of his ears to the back and ended up pinching his lobes. Then I placed my fingertips inside his ear canals a bit more firmly. He was making a gallant effort not to freak out.

"Tell me how that feels, Tommy."

"Pretty good I guess. It makes me feel kind of funny."

"That's good Tommy. Your ears are one of several erogenous zones on your body. That means stimulating them can help make you feel excited and sexy. Do you think you would like it if some girl probed you ear with the tip of her tongue?"

"Uh huh, I think that would feel really nice."

"And do you think you would have felt that way when you were ten or eleven?"

"No way, I would have thought it was gross!"

"Of course you would have. And that would have been an age-appropriate response, but now that you've matured, you're responding like an adult. You might want to try caressing a girl's ears sometime. That would show her you're a sensitive and caring guy. Girls love that kind of thing. OK, I think we're ready to move on. Why don't you take off you tee-shirt?"

I was buzzing with anticipation as he reluctantly complied with my command.

"That's great Tommy. Does it concern you that you have only peach fuzz on your chest?"

"A little maybe."

"Let me tell you a secret. More girls are turned off by guys that are too hairy than guys with no hair at all. In fact, I'd say you're fortunate not to look like an ape. Do you have hair under your arms?"

"Sure, doesn't everybody?"

"Well, most guys do, but not everyone. Can you raise your arms for me so I can see?"

Obediently he did as I asked.

"You have nice blonde hair under there, Tommy. That's perfect."

He smelled like Old Spice deodorant.

"I'm glad you use deodorant Tommy. You'd be surprised how many of my students I've had to lecture about that. Now, I want to show you something else".

My fingertips played very, very softly on the area around his nipples. I took my time before rolling them between my fingers more firmly. I could tell he was getting into it.

"How does that make you feel, Tommy?"

"Really nice. Even better than the ear thing."

They're also erogenous zones, Tommy. See how they responded to my touch? It's more noticeable with girls, but guy's nipples get erect when they're caressed too. Once again, your body is functioning as an adult Tommy – not like the boy you were a few years ago. Now let's take a look at your finger nails."

They were remarkably clean and well trimmed. I've seen way worse – even on girls his age.

"Excellent Tommy. You've done a great job with these. You get an A-plus in the hygiene department. Long dirty fingernails are a turn off for anyone, but especially a girl you're trying to get sexy with. Why don't you take off your shoes and socks and let's see how you're doing with you toenails?"

They were a bit on the long side, but far from disgusting. Nevertheless, I decided to let him know who was in charge.

"I'm afraid there's a bit of a problem here Tommy. You need to do a better job of keeping your toenails neatly trimmed. Toes and toenails are very important to girls. They like to make them especially pretty by painting them and getting pedicures. It's very important for you to clean between your toes every day. The last thing we want is for girl to find toe jam while she's sucking them."

I made him separate each of his toes so I could perform a thorough inspection. Fortunately for him, his toes were clean enough that I could hardly resist sucking on them myself.

"OK Tommy, I think we can move on. It's time for your jeans to come off."

He was a bit more hesitant, but seemed resigned to the fact that he had little choice in the matter. After a little hesitation he unzipped and slowly pulled them down.

"You have very strong legs Tommy! Good musculature with just the right amount of fuzzy hair. Once again, most girls don't like guys that are too hairy. Those legs are a definite strength."

It didn't take a genius to figure out what came next, and I could tell my young mark was bracing for the finale.

"OK, now comes the hardest part Tommy. I need you to take off your underpants. And it's important that you understand no matter what we find under there, I don't want you to be embarrassed or ashamed. All guys think they need a big penis to be a man, but I'm telling you it simply isn't that important with most girls. The three things I've told you about are much more important, so I don't want you to be afraid to show yours to a girl. Even if you think it's too small. And you should remember that practically no boy thinks his is big enough, so you're not alone in being worried about it. You probably don't believe all of this Tommy, but it's true. Now just take your time, and when you're ready go ahead."

He was visibly squirming and I was loving every minute.

"I don't think I want to do this part Audrey. Really, I'm feeling much better about myself and I think I'll be OK now. I appreciate what you've done for me but I think it's best if I just get dressed and we go back to the picnic."

"We can do that if you really want to Tommy, but I don't think it's a good idea to chicken out now. You've been doing so well, and if you can just find the courage to go a little farther you won't be sorry. I know you're scared, but this is the very most important part of the examination and I'd hate for you to miss it. Just try to be brave one more time and you'll be glad you did."

I almost felt sorry for him as he agonized over the decision. He knew I was right, and I was betting his need to be macho would not allow him to take the coward's way out. Thank God my bet paid off.

"Are you sure no one is going to find us?"

"Yes Tommy, I've been here lots of times. It's my secret place. In all the years I've been coming here, I've never seen a soul."

Finally he took a deep breath and slowly pulled down his boxers.

As I suspected, his penis was definitely on the small side – slender and a bit disappointing in the length department, but still adequate. Nevertheless, his feelings of manliness undoubtedly took a hit every time he compared himself at the urinal. But there was a wonderful surprise.

"Oh my God, Tommy, you're not circumcised!"

"Is that bad?" he said defensively, "My parents told me they didn't believe in it because they don't think it's natural."

"Oh no Tommy, it's a very good thing! You have something that I'll bet none of your buddies have – a foreskin. Do you have any idea how interested girls will be in that? I guarantee the first girl you show yourself to will tell her friends, and in no time you'll have them beating down your door. This is wonderful!"

"You really think so. I've always been worried about it since I'm different from the other guys."

"Well mark my words, they'll be singing a different tune soon. It does present a bit of a problem though. There's no way we can check to be sure you've been keeping yourself clean under there while you're soft. And it's imperative that we do so because if you aren't, gunkey stuff called smegma can accumulate and it would be an immediate turn off for any girl. So I know you weren't expecting this Tommy, but I'm afraid you're going to have to get an erection before we can finish. I promise this will be the last thing I'll make you do."

He was clearly taken by surprise and probably mortified at the prospect of getting hard for me. He was blushing like the innocent teenage he was.

"But I can't get hard unless, I um..."

"That's right Tommy. All you have to do is touch yourself like you do when you masturbate, and before long we'll be in business."

He was mortified. Not only was he tastily admitting that he masturbates, but he was getting maneuvered into showing me how he does it. Things were turning out even better than I'd hoped. My panties were soaked.

"Now Tommy I don't want any excuses. We both know you need to do this. Just close your eyes and do what comes naturally. It might help to think about something you usually do when you play with yourself. I'll let you know when you can stop. Now just suck it up and be a man about this. It'll all be over in a few minutes and then we'll be done. Do it now Tommy."

Much to my delight he spread his tee-shirt out on the grass in front of the tree and sat on it. He closed his eyes and heisted. I figured he was either conjuring up his courage or one of his masturbation fantasies. A few seconds later he cradled his testicles in one hand and began moving his foreskin up and down with the other. It took maybe ten strokes before he had produced an impressive erection (like most guys with smaller penises his expanded to a very respectable size), but I couldn't resist making him continue for a few more minutes. I was savoring the fact that this young hunk was openly masturbating at my command. I could barely resist joining him, but finally I gave him permission to stop.

"That's very good Tommy. You have a good enough erection for us to proceed. Now I need you to pull back your foreskin so we can see how well you've been taking care of business."

Hesitatingly he used the hand he had been stroking himself with to comply with my command.

"No, Tommy. Use both hands so you can pull it back all the way and I can see everything."

Obediently (if a bit awkwardly) he used both hands to expose himself fully. He was scrupulously clean.

"Wonderful Tommy. Not a trace of gunk under there. I'll bet the fresh air feels nice. If I were you I'd do exactly what you're doing now the first chance you get when you're with a girl. You'll be showing her something she's never seen and she will love it!"

A large drop on precum emerged and clung tenaciously to his opening. It made me think of the session with my husband this morning, and the thought sent a new wave of excitement through my body.

"That's called precum Tommy. You've probably seen it before. It lubricates the inside of your penis so your seminal fluid can come out more easily when you ejaculate. It's yet another thing you can show to girls. Are you starting to see how much you have to offer Tommy?"

The drop was getting bigger and I decided to make my next move.

"Oh Tommy, what have I been thinking? You must be about ready to burst. We've still got lots of time so why don't you just go ahead and finish what you started?"

"No way! I can't do that!"

"Of course you can Tommy. Remember, no one will ever know, and if you go back to the picnic now, you'll be miserable. It's not healthy to get yourself so excited and not take care if it. Go ahead now Tommy, you know what to do."

"But I'd feel so ashamed."

"That's nonsense Tommy. Masturbation is a fundamental part of your development. It helps prepare you for sexual intercourse later on and provides a safe and appropriate way to address the powerful urges all adolescents get. And besides, every boy does it. I'll bet about a million other boys your age will be doing it at exactly the same time. In fact, lots of guys do it all their lives. Would you believe my husband did it while I watched just this morning! He'd kill me if he knew I told you, but it's true. Please, please don't tell him I told you."

Tommy's eyes were wide.

"So how often do you do it Tommy?"

He took a deep breath and said, "I guess almost every day."

"That's good Tommy. Do you do it in your bed before school?"

"No, I usually do it in the shower."

"Did you do it this morning?"

"I guess so."

"I see. That explains why you're so clean under there. Actually, doing it in the shower is a great idea because you automatically keep yourself clean and you don't have to worry about the mess when you're done. Where else do you do it?"

"I guess I've done it in some bathrooms at school. I'm afraid to do it where someone might catch me."

He was feeling more comfortable now.

"I hope you're beginning to understand that even if they did catch you it wouldn't be anything to be ashamed about. Tommy, I want you to promise me that you'll try not to feel guilty about your masturbating from now on. In fact, I want to you feel good about it. Try doing it in some new places. And you don't have to do it the same way every time. Try experimenting with some different techniques. Sometime, you might even want to do it for a girl. And she might do it for you. Girls like to masturbate too you know."