Jessica is So Shy

Oh my God. What had happened to this poor sweet girl, I felt totally sympathetic.

I tried to stay calm. I thought for a moment and then I cautiously asked, "I need to ask, do you mean you were alone in your room and masturbating?"

She looked off into space and quietly replied, "Yes."

At that point she started to cry.

I got up off my chair and sat down next to her on the couch, I wanted to help calm her down. Poor Jessica was so upset, and I tried to act kindhearted and supportive.

I let her cry, and I gently stoked her beautiful red hair and whispered a softly, "It's okay, just let yourself cry, it's all okay."

It took her a little while to regain her composure enough to speak. As we sat there, I gently ran my fingers through her wet ponytail.

Finally she said, "I'm sorry, I'm just - so ashamed."

I calmly told her, "No, you can't be. I won't let you be."

"But..."

"No Jessica, it's fine."

"But - when my Mom caught me - she kind of - well - she - she - kind of freaked out - oh my God - she got SO mad at me."

Right then, even though she was still seemed terribly nervous and scared, she was now talking to me clearly. It felt like the need to talk had allowed her open up a little. Or maybe she trusted me a little more, or maybe it was crying that helped.

I said, "Please Jessica, I think you should keep talking, I think it will help..."

She spoke plainly, "It was awful - she really scared me..."

"I think I understand, I've seen how angry your mother can be."

She said, "I feel - so - ashamed."

"Oh Jessica, what you were doing wasn't bad in any way - it's perfectly okay."

She actually flinched when I said that, and she warily asked, "You think what I was doing was - okay?"

I whispered, "Yes, it is."

"Oh my God, do you really mean that?"

"Of course I do, it's okay."

I could tell that just hearing me say that seemed to calm her down - at least a little.

"But..." and then she trailed off. She briefly looked at my face, and then she turned away. Right then, she looked so helpless.

"Please, it's perfectly normal, and if feels nice for you - I think that's beautiful."

She meekly asked, "Really, you think it's - beautiful?"

I tried to answer her as calmly as I could, "Yes Jessica, if you in your room alone and want to do something that feels good - I think it's beautiful."

She looked at me, and she seemed so relieved, "That feels - really nice - hearing you say that."

"Good. It should feel nice."

"It feels SO good that - that you would listen to me, and you think it's beautiful, this really helps, talking like this..."

I smiled and said, "I'm glad, and I think this is the most I've ever heard you speak."

"I think - I needed to - to talk about what happened..."

I was so worried about her, and I was eager to let her know that I was truly concerned. But right then, I could tell she needed to tell me something more, so I coaxed her to keep talking.

"Please Jessica, if you ever need to say anything, I'm here, and I want to help."

She looked at me and awkwardly bit her lip, and it was obvious something else was inside her trying to emerge.

I asked, "What is it?"

"It's - I need to - I think - I need to tell you something else."

I encouraged her, "Please, it's okay."

"I want to - I really want to."

I whispered, "Go on, you don't need to worry about anything."

She carefully said, "This morning I think - I mean - the reason my Mom got so mad, I mean, she really flipped out - when she walked into my room - when she caught me - I was..."

Jessica paused, and she was concentrating so hard on what she was saying. And at the same time, I realized that the room was getting really warm from the wood stove.

I encouraged her, "It's okay..."

I realized how traumatic this was for her, but at the same time I could sense that she desperately NEEDED to tell somebody.

She said, "This is - this is SO hard for me to say. But - when my Mom caught me - I was naked - and - and..."

"Go on..."

"She REALLY scared me - I was so freaked-out that I jumped up off the bed, I grabbed my little red book and I hid behind my closet door, and I was naked - and - she yelled at me - And - On the bed - there was..."

"It's okay Jessica."

"I couldn't help it - I made - a big wet spot on the bed. And my Mom got all fixated on this, on how big the wet spot was - and she was really angry - and she said it was disgusting."

I whispered, "Oh Baby, I'm so sorry."

She went on in a panicky voice, "The bed was really wet and I couldn't - I couldn't help it."

I tried to be soothing as I told her, "I know you couldn't."

She nervously asked, "I can't help it. I mean - I just get SO wet, is there something wrong with me?"

Poor Jessica seemed ashamed by all of this, and I all I wanted was to make her feel better.

I took a deep breath, and calmly spoke, "No Jessica, don't worry, there is nothing wrong with you."

She meekly whispered, "But, I feel so bad."

"I can't make your mother's reaction go away. All I can say is - what you just told me - about the getting wet like you do - it sounds like you are perfectly normal and healthy."

"Do you really think so?"

"Yes, don't feel bad - it sounds beautiful."

Right then, I was so worried I had said too much. I mean, I had just called the big wet spot on her bed "beautiful" and I thought it might have come across as really awkward.

She looked up at me and meekly said, "You really think - it's beautiful?"

"Yes. I do."

"If I tell you something, please don't think that - I'm bad - okay? Please?"

"Don't worry, I know you too well to think anything bad about you."

"You know my little red book, I showed it to you at the store?"

"The one with the pictures of your father?"

She whispered so quietly that I almost couldn't hear her, "I need to use that book - need to look at the pictures - when I'm alone - like this morning."

I was so surprised at what she was saying. I thought before I spoke.

"Jessica, I know your father must have loved you very much. And I don't want you to feel bad, about anything. Love is a beautiful and confusing emotion."

She whispered, "But..."

"Please, I think it's perfectly fine if you want to look at those wonderful pictures. Anytime you want to, even if you are all alone in your room. It's okay."

She looked at me with those big sad eyes of hers, and whispered, "Thank you - I really appreciate you saying that."

I smiled and said, "I'm glad - and please, don't feel bad about anything you've told me."

It felt so wonderful to be helpful with someone who was so vulnerable. For some reason, I was filled with a sort of heightened emotion.

She said, "This feels really good to talk to you - like this."

"It feels good for me too."

She quietly said, "That was really emotional, to say everything like I just said."

I sat there next to her on the great big couch, and I gently rubbed her shoulder, tying to be reassuring and comforting. After saying everything she said, she seemed emotionally exhausted.

Right then, I realized that the room felt way too warm, the wood burning stove had obviously gotten really hot from the load of wood I added a little while ago.

I looked at Jessica and said, "The room feels nice and warm now, doesn't it?"

She nodded yes.

I put my hand on her shoulder and said, "I'm going to take this towel off - okay?"

She kept looking at the floor, and she quietly whispered, "Okay."

I gently took the big towel off from around her and set it on the floor.

I rubbed her more, along her back and shoulders, and her big thick hooded sweatshirt was still wet from when we were out in the rain.

Then she looked across from the couch, on the coffee table in front of her, and she seemed bewildered.

She softly asked, "Is that my drawing?"

On the table was the simple sketch of that one frail little flower inside a glass of water. It was in a frame, and it was facing us.

I continued to softly rub her back as I said, "Yes, I found it in the store the day you dropped all those sketches. I wanted to give it back to you, but I thought it was so pretty that I kept it instead. I'm sorry - I couldn't help it."

In a quiet voice, almost to herself, she said, "My dad used to frame my little drawings too."

She looked at me with this haunted faraway expression that I didn't understand. We sat in silence for a long time, just staring at each other. I was amazed at how lovely she looked.

Finally, I asked, "Jessica, you are still wet, are you cold or anything?"

"A little."

I said, "Maybe you should take your sweatshirt off, it's all wet."

As soon as I said that, I was aware of how forward it sounded, but before I could apologize, she whispered again.

"Okay. If you think I should."

She sounded so lost and vulnerable, that it left me confused. She had just been really talkative when she shared the events from earlier this morning, and now she was just giving short replies.

I cautiously asked, "Are you sure it's okay? I mean, you have a shirt on underneath, don't you?"

She softly said, "I have another shirt on, it's okay."

But she didn't do anything, she just sat there looking nervous.

I said, "Do you want me to help you."

"I think so..."

Jessica was wearing overalls, and her wet sweatshirt was under the denim shoulder straps. So I reached up and I carefully undid the clasp for the closer strap. And it felt so funny, because my hands needed to touch her sweatshirt a little bit, and the claps was so close to her breast.

But she let me do it.

I gently pulled the strap off her shoulder, and let it fall behind her.

Then I reached across to the other shoulder strap, and the way we were sitting on the couch, side by side, I needed to lean out a little bit in front of her. I took my time and undid the little metal clasp in front as gently as I could.

And then I reached around behind her, and pulled the strap off her other shoulder, when I was done, I whispered a quite, "There, that's better."

The front panel of the overalls gently fell down into her lap.

I took hold of the fabric of the sweatshirt along side her hips.

I said, "Can you lift your arms up for me?"

And she obediently put her arms over her head, and I tried to lift the sweatshirt up, but it was tucked in and too tight to lift. I realized there were buttons on the overalls, on each hip.

I said, "Jessica, I need to undo these buttons, is that all right?"

She didn't say anything, she just nodded yes.

I put my fingertips on the hip nearest me and undid the three buttons. It's funny, I was moving as slow as I possibly could, carefully undoing one button, and then slowly undoing then next. And she stayed perfectly still on the couch, and let me undo the buttons. She was being so still and quiet, and for some unknown reason, it was so mesmerizing for me.

To undo the other three buttons on the other hip, I had to reach across her lap, and I needed to get really close to her. She never moved, she stayed so still. And I moved as slow as I could. And being that close, I could hear her softly breathing, and I could smell her sweet shampoo.

When I undid the all the buttons, I tenderly said, "There now."

Then I put my hands back on her hips, and I took hold of the thick fabric of the sweatshirt at her waist.

And then I said, "Okay, can you lift your arms again?"

And she obediently lifted both arms above her head in a funny childish pose, and I was struck by how cute this made her look. I began to pull her sweatshirt up and over her head, and I could see she was wearing a white t-shirt under it. The act of lifting the damp sweatshirt made the t-shit lift up too, and I suddenly saw her tummy. She was much skinnier than I would have ever guessed, and the pale skin around her belly button was dotted with freckles.

I continued to lift, and then she said, "Oh, stop, please stop."

I was suddenly scared, like I had upset her.

She softly said, "My glasses."

It took a moment for me to realize what she meant, and I let go of her sweatshirt and let it fall back down. Then I took her little librarian glasses off and set them on the couch.

Without me asking, she lifted her arms over her head again, and looked at me with her big eyes. It was the first time I had ever seen her without her glasses, and she looked so much younger without them.

Then I put my hands on her sweatshirt, and lifted it up again, as slowly as I could. Again, I saw her tummy, and her belly button, for a moment before her t-shirt fell back down.

When the sweatshirt was up and over her face, I slid it off her arms. She helped a little, but it was me who pulled it all the way off her hands.

Now Jessica was sitting one the couch with me, wearing a baggy white tank top t-shirt and the front of her overalls were flopped forward in her lap.

I said, "Jessica, I don't think I've ever seen you with your glasses off."

"I hardly ever take them off."

"I know."

She said, "It's just - I really need them to see."

And then I picked them up again, and put her glasses back on for her, she had to hold so still as I carefully slid them behind her ears.

I said, "I love your glasses, I've always thought they look really cute."

I then I put my hand back on her shoulder and caressed her as gently as I could, and then I rubbed, and she seemed so influenced by my touch. She responded by leaning in a little toward my hand, and she rubbed her cheek against my hand, the way a kitten would nuzzle it's owner.

I was so moved by Jessica's peaceful gesture, that I kept my hand on her shoulder, and I was amazed by how soft her skin felt.

She whispered, "You've been so kind to me."

I tenderly caressed her pale freckled shoulder, and with her spaghetti strap tank-top, I was touching her bare skin and carefully traced her bra strap with my fingertips. She seemed so helpless.

I told her, "There is something wonderful about you, and it feels nice to help."

She quietly said, "You've been - like - like a father to me."

Hearing her say that made my heart melt. I was overcome with such a beautiful longing.

Then I said, "Jessica, your shirt, its a little bit wet too."

She replied submissively, "It is?"

It was only a tiny bit damp, hardly at all, but I continued talking.

"Is it okay if I help you take it off?"

There was a long pause, and she seemed so vulnerable, and finally she softly replied, "Okay."

And then she lifted her arms again, and I slid a little closer to her on the couch and I very cautiously reached along each hip and began lifting the fabric of her baggy white tank-top up and over her head.

It slid off easily, and I carefully set the shirt on the coffee table in front of us. Now I was looking at Jessica's amazingly pale skin, and her plain white bra. She was sitting so still, and I could tell she was terribly anxious.

She didn't say anything, but she was letting me stare at her, and I was amazed at how pretty she was, her white bra seemed so intoxicating, and her breasts were a little bit bigger than I would have guessed since she always wore such baggy clothes. Her shoulders were narrow and that made her breasts seem so perfect. But it was the white color of her skin, and the display of tiny pink freckles that seemed to hypnotize me.

I looked at her beautiful skin and her perfect breasts, and I was shocked at how lovely she looked.

I was immediately aware that her nipples were easy to see under the thin white fabric of her bra, they seemed incredibly hard and prominent.

I told her, "Your freckles are very pretty."

And she looked down at her own chest, and it was impossible for me to know what she was thinking. For the next little while, we both sat there in silence, She seemed so distant, and I could tell that she was lost in thought.

For me, it felt so sensual sitting so close to Jessica, and seeing her without a shirt and seeing her bra was dreamlike in its power.

She sat there, staying still and looking down at her own chest, and it was obvious she was seeing the same thing I was seeing, her nipples seemed so obvious through the thin fabric of her bra.

I wasn't sure what to do, I was so overwhelmed by the beautiful sight of her distinct nipples, for a moment, all I either of us could do was stare.

I was really nervous, but I put my hand back on her shoulder and I touched her bra strap with my fingertip.

Just like before, she responded by leaning in a little toward my hand, and she tenderly rubbed her cheek against my hand. It felt so sincere.

I was completely smitten by the sight of her pale skin and her lovely little bra. I began to trace the edge of her bra. I ran my fingertip down the thin strap along her shoulder until I was under her breast, and I let my finger slowly glide under both cups of her bra. And she was attentively looking down at my hand, watching my fingertips.

The way we were sitting on the couch, I needed to reach across her, and it felt a little bit awkward.

I quietly asked, "Jessica, can you face me a little more."

And she obediently turned and sat with her knees pointing toward me. We were facing each other as much as possible as we sat side by side on my couch.

I said, "Thank you, that's better."

I continued to trace the underside of her breast, and then up the outside of the thin whit bra strap - all the way up to her shoulder. And she was looking down, fixated on my fingertip as it slowly moved along her pale skin.

And then from high on her shoulder, I slowly traced the inside and began moving my fingertip back down.

Jessica stayed perfectly still as she let me run my finger along her bra, all along the inside her cleavage. Her breasts were beautiful and round, and after I did it once, I retraced the line and did it again.

When I touched her as slow and delicately as I could, she would shiver a little bit, as if I was tickling her.

And she was looking down, totally focused, watching my finger.

We both watched as her nipples got even harder, it was something so hypnotic to watch them get just a little bit more apparent under the thin fabric of her simple white bra.

Finally I had to stop, it just felt too forbidden, and I was worried that it was unfair for someone so shy. I moved my fingertips from her bra, and then I ran my hand along her leg, along the blue denim fabric near her knee. I was trying to be as supportive and kind as I could be. I couldn't help myself, and I know it must seem ill-behaved, but I said, "Jessica, your overalls, its feels like these got wet in the rain too."

She replied meekly, "They feel wet?"

"Jessica, I think, maybe, we should take them off."

And almost silently, she said, "If you think so - Okay."

I was shocked that she said yes, because she was acting so quiet and nervous.

"I think it will better, if you lay down. It will be a little easier."

Before I knew what was happening, she was lying on my couch, and I slid down so I was sitting near her feet, and calmly took both her shoes off, and then her socks. All the while she was lying there, looking up at me with this bashful expression.

I began to pull her overalls down off her hips, but she was lying so still that it was a little bit hard.

I asked, "Jessica, can you lift your bottom up, just a little?"

She obediently put her hands down on the couch, and arched her hips up to help. I was at the end of the couch by her feet, sitting and pulling.

They began to slide off easily, I said, "There, that helped."

It took just a moment, and the overalls were off and on the floor. Now Jessica way lying on my couch, on her back, wearing nothing but a white bra and a pair of simple white panties. And I was immediately aware that her panties were wet.

Jessica was lying there, so still and quiet. I was staring right between her legs, and the thin fabric of her underwear, I couldn't help it, she was so close, next to me on the couch, her pale legs were slightly parted I could see how wet her underwear was.