How Diana Overcame Her Shyness Ch. 02



Diana’s story continues.

As it turned out, there never was a third date. Not as such, anyway.

For Diana the next couple of days were a blur of desire and confusion, with more than a little bit of guilt mixed in. She was conservative by nature and nice girls simply didn’t do what she had done, in her opinion, especially with a man she hardly knew. She felt as though she were blushing continuously, as images from that evening appeared and reappeared in her mind, over and over.

And yet, she realized, James had been right: she felt calmer, more centered and more self-confident. She was aware of a new sensuousness in her walk, as if someone had lubricated her hips. This proved to be a source of distraction, however, as it also constantly drew her attention between her legs, an area she had largely ignored in the past.

This in turn became another source of embarrassment and guilt. She had woken up the next morning, still half-dreaming, to discover her nightgown rucked up and her hand cupping and squeezing her vagina. And instead of quickly removing it she had allowed herself to drift back into her dream/memory of James touching and tonguing her there, using the tip of her middle finger to stroke her clitoris as she did so. But she had stopped almost immediately when a moan tried to force its way past her lips, as her roommate was still sleeping just a few feet away.

And it had been like that for two entire days: desire and guilt, guilt and desire. She was normally an excellent student but the memories and fantasies left no room in her mind for anything else.

She had to leave one class in the middle of a lecture when she suddenly became aware that beneath her desk-chair she was using the edge of her thumb to stroke herself through her pants as she re-lived, over and over, the moment when James had yanked off her panties and spread her legs apart; the way she had felt, looking up at him, completely surrendered to whatever he might choose to do with her. As she’d snapped out of her feverish imaginings she’d been horrified to look down and discover that she’d become so aroused that some of her moisture had leaked entirely through her panties and created a very small but entirely visible dark patch in the crotch of the light tan fabric of her pants. She’d had to pick up her books and notebook and flee, holding everything awkwardly in front of her, and retreat to her room to change.

She desperately wanted to see James again, of course. She wanted to tell him everything she’d been going through; wanted to see the understanding and acceptance in his eyes; wanted him to hold her and soothe her and tell her that everything was all right.

Wanted him to…

But he had told her to take at least a few days, and they had made no specific plans as to when they would meet again. And Diana knew that he had just been trying to help her, that there was no romance involved, no future to the relationship. He had no idea of the upheaval he had caused in her life. She might not have been crazy about the person she had been but now she had no idea who she was.

That evening she was sitting at her desk, trying, with a complete lack of success, to focus on her homework, as she had been for the past hour. Suddenly she slapped the lid down on her laptop and stood up, startling her roommate, who was reading on her bed. “I need some air,” Diana said, and hurried out, forcing herself not to slam the door behind her.

Diana knew exactly where she was going, even though she had no idea what she was going to do when she got there. She hurried across the campus, her mouth set in a determined line. It wasn’t until she actually reached James’ dormitory that her footsteps slowed and she began to second-guess herself. It was a warm, humid night and she felt sweaty and even less attractive than usual. And of course before leaving she had given no thought to how she was dressed: an old black t-shirt with a bust of Beethoven on the front, an even older pair of raggedy denim cut-offs, and rubber flip-flops.

Not very enticing, she thought.

She didn’t care.

She marched through the entrance, took the elevator to the floor where James lived, entered his suite and, forcing herself not to think about what she was doing, knocked on his door. It wasn’t until he answered that Diana’s resolve deserted her.

James seemed mildly surprised to see her there, but certainly not unpleased. He smiled warmly at her and said, “Hi, Diana. How are you doing?”

Her mind, of course, went completely blank. Then she tried desperately to come up with an innocuous reason for her visit, but she knew “I was just passing by and thought I’d say hello,” wasn’t going to fly.

Fine. She’d come this far, and hesitating wasn’t going to make it any easier. She forced herself to meet his gaze, opened her mouth… Then closed it again and looked down. Raised her eyes and lowered them again several times in succession. Considered turning tail and running away.


Finally, clenching her fists at her sides, she managed to say, “I…I w-want you to…teach me… I want you to sh-show me how to…d-do…d-do things for you.”

Once she had forced the words out Diana was terrified. Would he just laugh at her awkwardness and tell her to go home?

In some ways his initial reaction was worse; his expression as he looked at her was one of concern more than anything else. He looked past her, gazing thoughtfully into the distance for what seemed to Diana to be an agonizingly long time. Then he returned his attention to her, nodding slowly and saying quietly, “Yes, that would make sense, after…” He left the sentence unfinished, then went on, “I’m really slammed with homework right now though, so maybe in a couple of…”

He stopped as he saw the expression on Diana’s face. “Oh.” He nodded again, his expression sympathetic. “Yes, of course. Come in.”

He stood aside and Diana entered. She stood in the center of the small room, her hands clasping each other tightly at her waist, while he closed the door. He came around and stood facing her, then opened his arms and gathered her into a hug. Diana gratefully surrendered to his embrace again, resting her head on his shoulder and allowing her breathing to settle as she basked in his warmth. He held her like that for a long time.

Eventually he withdrew slightly, taking her by the shoulders and looking into her eyes, asking without words if she was ready.

Diana nodded, hoping that she was right.

Releasing her, James took the chair from his desk, turned it around and sat down, looking up at her. There was so little room between the desk and the bed that his knees were only about a foot from hers. He leaned forward slightly, resting his elbows on his thighs and interlacing his fingers.

“Take off your clothes,” he said quietly.

What? Diana went into shock. Was he asking her to stand there right in front of him and just…strip naked while he watched? Actually, no, she realized. He was telling her to do so.

She blushed violently, tried to speak, “I… B-but…”

James just sat there looking up at her, saying nothing but raising his eyebrows slightly as if reminding her that this was what she had asked for. After a moment, when Diana had stuttered out a few more unintelligible syllables and then fallen silent, he said, “Start with your sandals, Diana.”

Well, that wasn’t so bad, even though Diana knew what would inevitably follow. She slid out of her flip-flops and nudged them aside with her foot. Then she stood there, nervously twisting her fingers together.

“Pull down your pants.”

Diana fumbled with the button on her shorts and managed to undo it, but her hands were shaking so much that she had trouble grasping the tab on her zipper. Finally, with a great deal of concentration, she managed to unzip her shorts, but then her hands fell to her sides and she looked pleadingly at James…though she had no idea what, exactly, she was pleading for.

James regarded her sympathetically and said, “I’ve already seen you naked, remember?” As if she could forget! Diana nodded jerkily, her mouth dry.

“Pull down your shorts, Diana.”

Diana nodded again and forced her hands to obey her, hooking her thumbs in the waistline of her shorts, pulling them down past her hips and lowering them to the floor before standing upright once more. Her panties were a pale violet and she suddenly couldn’t remember whether she was wearing a matching bra or not.

“Now the shirt.”

For some reason it felt less terrifying to have James giving her specific instructions; it was almost as if she was no longer responsible for what was happening because he was telling her what to do. It was strangely exciting to be standing in front of him and being ordered to strip, one piece of clothing at a time.

She crossed her wrists at her waist, grabbed the hem of her t-shirt and pulled it up over her head. Unfortunately the collar caught on her glasses and she had to struggle awkwardly for a moment to get the shirt past her head, her glasses falling to the floor in the process. James leaned down, picked them up and placed them on the desk behind him. Diana tossed her shirt onto the bed.

Her bra, as it turned out, was white, or more accurately somewhat grayish from too many washings. Ugh. Exasperated by her humiliating struggle with her glasses, Diana didn’t wait for instructions but simply reached behind her, unfastened the offending bra, pulled it off and tossed it behind her onto the bed. Then she turned back to face James.

James gave her a moment to recover, then leaned forward and gently lowered her panties himself. Then, resting his hands on her hips, he nuzzled her pubic hair for a few seconds before moving downward and kissing her there, the tip of his tongue finding and teasing her clitoris.


But then he sat back again.

And just…looked at her.

He regarded her calmly, just as if she weren’t completely naked. He wasn’t looking at her breasts or between her legs. He didn’t seem to be waiting for anything. He was just looking into her eyes.

Diana found it disquieting at first and wanted to fidget. Was there something she was supposed to do or say? But as the moment continued she found herself settling down; there was something calming about simply resting in his gaze. Yes, it was completely humiliating to be standing in front of him with her shorts and panties down around her ankles, completely exposed. In fact, having her shorts and panties like that made her feel more undressed than if her clothes were completely gone. And to her surprise she found her nipples hardening in response. Would he notice?

Apparently so, because he reached up with both hands to touch them delicately with the tip of each forefinger, circling them slowly to make them stiffen even further before pinching them gently, making her gasp.

But only for a moment before lowering his hands once more, resting them on her hips and using the edge of each thumb to trace the outline of her hip bones, his gaze never leaving hers. Then he rose slowly to his feet so that they were standing face to face – or would be if he hadn’t been nearly a head taller than she was. Again he appeared to be silently asking if she was ready to continue and Diana did her best to answer in the same manner, even though her knees were once again beginning to tremble.

He took her right hand then, and placed it on the front of his black jeans, holding it there firmly. Diana’s eyes went wide as she felt the bulge there, filling her hand and seeming to grow larger and more solid under her touch.


Her breath quickened as he began guiding her hand up and down the length of his shaft. Oh, she was…

As if reading her mind James said, “Yes. You’re stroking my cock, Diana. Can you say it?”

Diana’s mouth was dry and she had to make herself swallow a couple of times before she was able to whisper, “I’m… I’m sss…stroking…your cock.”

James nodded his approval. “Good.” He continued guiding her hand for a little longer and then released it, allowing her to find her own rhythm. Diana continued automatically, not daring to look down at what her hand was doing. After a moment she mustered the courage to ask, “Am I… Am I doing it right?”

James, his hands now resting lightly on her shoulders, replied, “Yes, that feels very nice, Diana.” He looked at her more closely before asking, “How are you doing? Is this what you wanted?”

Was it? Oh yes. Diana allowed her eyes to close for a moment, allowing herself to be aware of nothing else but the feel of him under her hand, before opening them again and replying softly, “Yes.” And then she surprised herself by adding, “I really l-like…stroking your cock.”

James smiled at her and nodded his approval, then added, “Then you know what happens next.”

She did, and Diana could not believe what she was about to do. Biting her lower lip, she unsnapped and unzipped his jeans – he wore no belt – then opened them and pushed them down past his hips. His underwear was navy blue and the bulge inside them was huge. Diana looked back up at him one more time, seeking permission, and then, holding her breath, hooked all of her fingers in the elastic of his underwear, pulling it outward and then down. His underwear slid down to join his jeans…

And there it was. Diana knew what they looked like of course but, oh my, here she was, standing naked in a man’s room and she had just taken out his cock. This was definitely not how she had imagined these “practice” dates would go. She stared, breathing quickly through her mouth. James said nothing, giving her time.

Did she dare? Diana reached out timidly, barely grazing the length of the shaft with her fingertips. Then again. And then finally gave into her desire, encircling the entire shaft with her hand.

Ohhh… So warm, and so unlike anything else she had ever touched. Diana looked up at James and, knowing that he would ask her to do so anyway, whispered, “I’m holding your cock in my hand.”

James nodded but said nothing more, and Diana took this as permission to explore. She released her hold and used the tip of her forefinger to trace the fleshy rim around the head, lightly teasing the hole at the very top before once again extending her entire hand downward to cover the entire shaft, her fingertips resting on the delicate sack at its base. Gingerly, she began to tease and caress him there… And was thrilled to hear his sudden intake of breath, followed by a barely audible, “Mmmmm.” Emboldened, she began moving her hand up and down the length of him, looking up to gauge his reaction and revelling in the slick texture of his skin under her hand, the tickling of the wiry hairs against her fingertips.

“Mmmm…”, James murmured again, more loudly this time. “You’re doing very well, Diana. That’s just right.” His eyes closed and, as she continued to stroke him, murmured again, “Mmmmm…”

Diana was thrilled. She was giving him pleasure! She, shy little Diana, was holding a man’s cock in her hand and pleasing him – even making him moan! Watching her hand caress him, she moaned a little herself.

James lowered one hand, grasping hers and wrapping it again around his shaft, tightly this time. Then he showed her how to pump it, the skin moving smoothly in her grip as he guided her hand up and down. When she had found the right pressure and rhythm, he released her hand again, returning his own to her shoulder.

She watched his expression carefully as she continued. His eyes were closed again but every so often he would speak: “Yes, that’s right, just like that.” “Mmmm…keep going.” “A little faster now.”

Then he only made sounds, his breathing becoming faster: “Ahh.” “Mmmm…” “Ohhhh…”

And then somehow Diana knew that she needed to pump him more quickly and squeeze him more tightly, and did so.

“Ohh! Oh, yeah! I’m gonna…” James dropped his hands to her naked behind, pulled her against him and kissed her deeply, his tongue probing her mouth, his cock pressing urgently against her stomach as she continued to pump him. Then he moaned loudly against her mouth – “AHHHHhhhh…!” – and Diana felt something warm and liquid spurting against her stomach. She slowed down her strokes, now suddenly made smooth and slippery by the fluid seeping down into her hand and between her fingers.

James had leaned his head back and was gasping, his mouth open. Diana felt his cock pulse a few more times under her hand, felt a few more warm spurts landing on her abdomen and trickling downward. She had given him an orgasm!

Her feeling of pride was tinged with a little bit of anxiety: should she stop now, was he done? She loosened her grip somewhat but continued to stroke him, though much more slowly. After a few moments James released his hold on her behind and gently removed her hand, saying, “Mmmm… That was wonderful, Diana. You did really well. That felt amazing.”

Diana smiled up at him as he once more wrapped his arms around her waist. She wanted to hold him as well but held back because her hand was still very wet and sticky. He smiled back at her and asked, “Did you enjoy doing that, Diana?”

Diana nodded, shyly. “Yes,” she replied, her voice soft. “I liked it…a lot.”

James kissed her forehead, smiled down at her and said, “I think it’s safe to say you’ve passed Handjob 101.” Diana giggled as he went on, “And judging by your hand,” he reached down and raised it, still dripping with his semen, to eye-level so they could both see it, “you’ve already figured out that a little lubrication can also be helpful. You can use hand-lotion, cooking oil or even your own spit if that’s all you’ve got. This,” he added, nodding at the sticky liquid on her hand, “is usually called ‘cum’, by the way.”

He lowered her hand to her side again. “But now you know the basics.” He looked at her more closely. “How are you feeling?”

Diana was a little startled by the question. She suddenly realized that she had been so caught up in what she had been doing that she hadn’t for a moment felt shy or self-conscious. And now…

She looked down at herself. She was standing naked in front of a man, with her shorts and panties still around her ankles; she had just used her hand to masturbate his cock; that same hand was now covered with his…cum, as was her belly, and both were dripping onto her clothing below.

How was she feeling? As usual, the words she wanted to say failed to appear in her mind.

So instead she raised herself on her toes and kissed him firmly, surprising herself by boldly slipping her tongue into his mouth.

When the kiss ended and Diana settled back onto her feet, James nodded approvingly. “Good.” He reached behind him and grabbed a box of tissues from the desk, taking one for himself before offering her the box, saying, “You might want to clean up a little before you get dressed,” and starting to wipe himself off.

Without thinking Diana grabbed his wrist and said, “No.” Then her eyes went wide with shock. Had she just said “No” to him?

James was regarding her quizzically. Why had she done that?

Actually, she knew exactly why, though she hadn’t known before she said it.

“I – I’m not… I want to…”

And then she sank to her knees in front of him.

James’ puzzled expression changed to one of understanding as Diana took the tissue from his hand and, after quickly wiping off her own hand, began cleaning the remaining semen from his shaft.

When she had finished her task she did not clean off the cum that was still running down her stomach and onto her thighs. Instead, she simply placed the tissue on the floor and remained looking up at him, her arms hanging loosely at her sides.

James stroked her hair with one hand as he looked down at her and asked quietly, “Are you sure?”

Diana nodded, though she was biting her lip as she did so.

“Okay,” James replied. “‘Blowjobs 101,” he added, receiving a tiny smile from Diana in return. “The first thing to remember is that you don’t want to touch this,” using his free hand to briefly hold his still mostly erect cock, “with your teeth if at all possible. Pretend it’s a banana and that you don’t want to leave a single tooth mark while it’s in your mouth.”

Diana felt a brief spasm between her legs when she heard the words, “in your mouth”. But she nodded again and managed to whisper, “Okay.”

James continued, “Another food you can think about is an ice cream cone. To start with, imagine that it’s melting and you want to catch all the little dribbles before they fall off. Use the tip of your tongue.”

Diana nodded, her expression serious and concentrated, then leaned forward, opening her mouth and extending her tongue, almost wishing she hadn’t cleaned the trickles of semen from his cock. She started with the briefest of licks, barely touching his shaft before looking up to see if she was doing it right. And when he nodded she continued, becoming more bold, using more pressure and tracing the path of the imaginary dribbles up the length of his shaft, glancing up at James periodically and feeling a thrill of pride when she saw his eyes close and heard his barely murmured, “Mmmm…”

And then, just because she wanted to, Diana turned her head slightly to the side and began kissing her way from the base of his cock all the way to the top, softening her mouth and allowing her tongue to moisten him along the way. When she reached the very tip she lingered there, holding him between her lips and teasing the opening with the tip of her tongue, eliciting another moan of pleasure from James.

Oh! She was being so naughty!

Without removing her mouth she looked up at James, and found him looking back at her, his eyes half closed with pleasure.

“You’re doing really well, Diana. Now imagine that the ice cream is beginning to melt even faster, so you need to get it all in your mouth.”

Diana didn’t hesitate. Opening her mouth and being careful not to graze him with her teeth, she lowered her head, breathing quickly through her nose as she felt the head of his cock filling her mouth.

Mustn’t let the ice cream melt, she thought to herself, and began slowly lapping around the huge cap, raising and lowering her head as she did so, letting her moistened lips linger on him as he slid between them.

“Ahhhh….” she heard James sigh. “That’s right, just like that.” She looked up at him, and he continued, “Good. Keep looking into my eyes if you can. That makes it even sexier.”

She removed her mouth from him long enough to whisper, “Okay,” started to lower her head again then stopped and added, “I… I have your cock in my mouth,” before continuing.

And she quickly discovered that he was right: looking directly into his eyes while licking and sucking on his cock was by far the sexiest thing she had ever experienced. She felt like a naked little slave-girl…

Oh! That thought, that image, sent a jolt between her legs. And her hand, seemingly of its own volition, drifted down there and was quickly covered with wetness as her fingers sought and found her clitoris.


Yes, she was a little slave-girl whose only purpose was to please the cock in her mouth. Oh god, she loved that! She began stroking her clit with a fingertip in rhythm with the bobbing of her head as she pleasured his cock, reveling in the way James was looking down at her, his eyes once again half-closed. She was doing this to him! She, nerdy little Diana, was the cause of his arousal!

A moment later James raised his hands and rested them on either side of her head, grasping it gently. Then, little by little, he took over the rhythm, sliding his cock in and out of her mouth more quickly. At first Diana tried to match his pace but quickly realized that she only needed to be still.

To be his receptacle.

She continued to meet his gaze, and stroked her clit in rhythm with his thrusts. Now she felt even more like a slave-girl: a possession to be used for his pleasure.

“I’m fucking your mouth, Diana,” James murmurred, beginning to thrust even more quickly. “I’m fucking your mouth with my cock.”

Oh! Diana was rocked by another jolt between her legs and had to fight to remain still. She wanted desperately to say it back to him, to say, “Yes, you’re fucking my mouth with your big, hard cock,” but she would do nothing to disrupt his rhythm. She was his little slave-girl and he could do whatever he wanted with her. She tried to nod ever so slightly and show him with her eyes that she was his.

He began thrusting harder and faster, his eyes closing and his breath becoming more rapid. A moment later he opened his eyes long enough to say, gasping somewhat with the effort, “I’m…going to…come…in your mouth now…mmm…ahh…Diana. And…ah…ah…ah…you’re…ah!…going to…unh!..swallow it! AHHHHHHH!”

As he continued thrusting, Diana felt, and then tasted, his semen as it spurted onto her tongue and against the back of her throat; it was hot, salty and somewhat bitter. She didn’t care. Oh god, he was shooting his cum into her mouth! And she was swallowing it! She fought her own orgasm just long enough to make sure she got every drop, then threw her head back, her mouth wide and gasping, as the convulsions shook her from her hips to her shoulders until she almost fell over.

She threw her arms around his thighs and rested her head against his abdomen, gasping, as a second, and then a third wave passed through her.

A moment or so later she felt his hands resting on her head once more, stroking her hair. She looked up to see him smiling down on her, his eyes gentle. He smiled and said softly, “I think we can safely give you an A+ in Blowjobs 101. Whew!”

Diana giggled and then asked, more seriously, “Did I do it right?”

“Yes, you did. You did very, very well, Diana. Especially for your first time.”

Diana flushed with pride as she gave him a huge smile and whispered, “Thank you.”

James reached down with both hands, offering to help her to her feet, but Diana felt strangely reluctant to let go. Something about kneeling at his feet, with her arms around him and the taste of his cum still in her mouth, felt so natural and right that she wanted to stay just as she was and savor it. But she knew she wouldn’t be able to explain it and so she took his hands and began to rise. But she noticed there was still a dribble of semen on the head of his cock, and stopped long enough to kiss him there and lick it up before getting to her feet.

She had forgotten that her shorts and panties were still around her ankles and she stumbled as she tried to get her footing, but James caught her by the shoulders and then gathered her into his arms once more. She kicked off her shorts and panties and pressed herself against him, but…

She pulled back slightly and looked up into his eyes…then down again. Then back up as she tried to force the words past her lips: “Could you… Could you be…naked too?”

Again she was warmed and reassured by his smile as he nodded. Without hesitation she pulled his jeans and underwear down to his ankles, then crouched down to remove them as he lifted first one foot and then the other. She tossed them onto his bed and then quickly pulled his sea-green polo shirt over his head as he raised his arms to help her. The shirt joined the pile on the bed and Diana allowed herself one moment to take him in: the dark curly hair on his chest and stomach and surrounding his now softening cock; the strong legs and arms; and the torso, not muscular but well-shaped.

James stood there easily, allowing her to look him over. But Diana quickly stepped back into his embrace and they stood there for a long while. Then Diana whispered, “Thank you. This was wonderful” She hesitated, then continued, “Do you think that sometime you could…take my vir- M-make…love to me?”

James pulled back slightly and looked down into her face, his expression serious. “I’m not sure that would be a good idea, Diana.” He looked off into the distance, thinking, then went on, “Call me old-fashioned, but I think the first time you make love it should be with someone you really know and like and care about and trust, and who feels the same way about you. Someone you’re in an actual romantic relationship with. I’ve just been showing you some of the basics.”

He took her by the shoulders. “I do like you, Diana, I hope you know that. And I want to tell you something: it’s time for you to start liking yourself. It’s time for you to stop thinking of yourself as someone who isn’t good enough and start seeing yourself as what you are: a gift. You’re smart, you’re really nice, and yes, you’re actually quite attractive. You need to see these things about yourself so that other people around can see them too. Especially guys, who tend to be kind of clueless,” he added with a smile.

He went on, “Now, I’m sorry, but I really, really have to hit the books – if I can stay awake. You’ve kind of worn me out, young lady.”

Still naked, he crouched down, one knee on the floor, picked up her panties and held them out for her to step into. He slid them up to her waist then repeated the process with her shorts, zipping and fastening them, before turning to retrieve her bra and shirt from the bed. Noticing that her stomach was still shiny with his now mostly dried semen, he asked, as he got back to his feet, “Do you want to clean that up?”

Diana looked down for a moment and then back up at James. She shook her head solemnly, and took the bra from his hands, slipping it on and fastening it behind her before reaching for her shirt and slipping it over her head. One of her sandals was missing but she spotted it halfway under the bed.

Now fully dressed again she turned back to James, who, smiling, retrieved her glasses from the desk and gently settled them on her nose. It was a strange reversal, her being dressed while he was still naked, but he seemed completely comfortable with it. She stepped into his arms for one last embrace. He kissed her tenderly, then looked into her eyes and repeated, “You are a gift, Diana. Make sure the next guy knows and appreciates that.”

He released her and then stepped around her to open the door. “We’ll see each other soon, though I’m probably going to be buried in here for the next few days. Take care, Diana. Good night.”

“Good night, James,” Diana said softly, smiling up at him as she stepped out the door. “Thank you.”

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