My Days at St. Mary

Victor felt a bit guilty. Perhaps this really wasn't quite right. This girl was putting her trust in him, and it was clear that he wasn't being entirely honest with her. Yet, it was his sincere intention to be helpful, to provide her the guidance and instruction that she wanted, that she needed. "You can trust me, dear."

"Well, Miss Wilson, it's just that I've never actually even seen one before."

"Seen what?"

"Golly, Miss Wilson, do I have to say, I mean, out loud?"

"Now, Melissa, the more comfortable you become talking about it, the more comfortable you will be actually doing it."

Doing it? Just the thought of that made Melissa blush once again. Imagine doing it! She really couldn't imagine ever really doing it. Well, that's not true. She had imagined it quite a few times. It was just that she was so unsure about it. "Okay, you're right, Miss Wilson, of course you are." She took a deep breath and said, "His penis. I've never actually seen a penis before."

Victor could feel his own growing within his panties. "You've never seen a penis?" It was rather hard to believe. She must have seen at least seen one.

"Well, of course, I've seen pictures and everything." She turned her face away. She didn't want the teacher to see her embarrassment. "I know what it looks like. I've just not seen one in real life and everything."

Victor could have shown her one right now, and would have been very happy to do so, but he could hardly reveal his secret so soon, so quickly, and he wasn't too sure that Melissa would in fact like to see his. It would probably be a bit of a shock.

"Well, honey, I don't know how I can help you with that."

"Oh, I know, I know." She felt so silly. "I mean, I wondered, if, um, you could though, when I do get to see one." Her voice again got real quiet. "Tell me what to do with it."

"Well, honey, there are lots of things you can do with it. You just have to trust your instincts. It will come to you." If they talked about this too long, so would his, in his panties. He reached into his skirt, through the slit pocket and, taking advantage of the fact that she was looking away, adjusted the position of his swelling cock.

She turned back to him, giving him her most beseeching, entreating expression, like she was a child pleading for a new toy. "But, I want you to show me. Won't you please, Miss Wilson?"

"But, honey, it's not like I have one in my office," he replied, holding a stiff one at that very moment in his office, in his hand.

Melissa again looked away. She was thinking of something, thinking very hard, wondering if she should tell her, wondering if she should take the chance. She sighed deeply. She turned back to her teacher. "Miss Wilson, can I show you something?"

"Well, of course, my girl. Of course you can."

"Promise me you won't tell anyone?"

"Absolutely."

"Promise me you won't get mad or tell on me?" She knew that was asking a lot. How could an instructor, particularly the one specializing in discipline, make a promise like that?

But, her faith in Miss Wilson was reassured. "I promise. It will be our secret."

Melissa smiled, albeit quite nervously. She would confess the truth. "Um, well, I have one, Miss Wilson."

"Excuse me? You have one?" How weird could this be? He couldn't believe what he just heard.

"Yes, yes I do. In my purse. I'll show it to you."

He breathed a sigh of relief. Of course she didn't have one. He had seen her cunnie himself, but he had to admit that, for the moment, he was a bit confused, for obvious reasons.

Melissa reached into her purse and pulled out a rubber erect penis. It was actually a pretty good facsimile. It wasn't one of those smooth plastic dildos. It actually looked like a copy of a real one, including even the balls (although hairless) plus some veins and a rather compelling texture. "Oh my," Victor replied.

"Oh no, you're not angry are you? Is this terribly wrong? Oh no, I'm sorry." She started to put it back into her purse.

"No, no, dear. It's fine, really. I was just a bit surprised. I mean, my goodness."

"I know, I know. I feel like a pervert or something."

"Honey, absolutely not. This is good. It's fine to have one of these." He leaned in closer to Melissa. "I have my own penis."

Melissa turned and smiled, this time with a really big smile. "Really?! Do you really? Can I see yours?"

It was a reasonable request but it did take Victor by surprise. "Oh, well, um, I."

Melissa saved him from having to lie. "Well, of course, I'm sorry, of course, you wouldn't have it here. I haven't had mine for very long. I just got it a few weeks ago. How long have you had yours?" She realized that she probably shouldn't have asked that question. It was a bit personal, but they were talking about quite personal things.

"Oh, quite awhile, Melissa, pretty much quite awhile."

"Do you use it? I mean, you know, to, um." It was very hard to say this, but Miss Wilson had made it clear that she should speak about everything, about anything. Melissa did though at least whisper the question. "To make you excited?"

"Oh yes, dear, certainly." He leaned in closer to Melissa, almost whispering in her ear, "I enjoy playing with my penis very much."

"You don't think it's dirty or wrong, or anything?"

"Oh no, dear. It's really perfectly fine to play with an erect penis."

Melissa could feel her face getting red again. It seemed so terribly naughty and wrong to be talking about an erect penis out loud like this, but it was also itself a little exciting. "Would you show me how to use it?"

"Well, Melissa, I would be happy to."

"Oh goodie!" She gleefully handed over the erect penis to Victor.

Victor took the penis in his hand but wasn't quite sure what she wanted him to do with it, and was even less sure that he would be willing. "Um, well, I mean. What would you like me to show you?"

"Well, first, show me how you make a guy happy, you know, what you do with it. What guys like you to do with it."

Victor didn't mind showing her how to handle it. That would be okay. He removed his hand from his own cock, took it out of his pocket, and gently took hold of the fake one's balls to keep it steady. He then demonstrated to her how he masturbated.

Melissa slid over tight against him and leaned down closely to watch as Victor stroked the erect cock in his lap.

He explained how it is helpful to try all sorts of different things, to at times just lightly caress, at other times to grasp firmly and stroke hard and fast, to perhaps tickle the tip with just the tips of your fingers, or then maybe caress the tip with the palm of your hand, or dance your fingers along the stem, like you're playing a flute. That wasn't particularly stimulating perhaps, but it didn't always have to be. It was just good to be playful, to show him that it was just about as much fun for you as it was for him, that you really enjoyed giving him pleasure. He particularly emphasized how a guy is often most sensitive on the underside of the crown. "That's where you may really want to use your tongue."

Melissa blushed at that suggestion. "You would really put it in your mouth?"

"Guys do really like that a lot, Melissa," he replied, avoiding the actual question.

It seemed like a terribly dirty thing to do, but also rather thrilling. She was so happy to be having this discussion with Miss Wilson. Her instructor was being terribly helpful. "Would you show me how to do that?"

Victor furrowed his brow. It was odd. He didn't mind pretending to masturbate the fake penis, particularly as it was sitting in his lap, as if it was his own. And, frankly, he wouldn't mind performing oral sex on himself. He had tried to do so as a kid, but he had never been sufficiently limber. But, sticking this fake erection into his mouth didn't seem quite right. It seemed to lose the sense that it was his own. "Well, Melissa, why don't you try it and I will help you with it."

Melissa's face again got redder. It seemed to be a little embarrassing to be actually doing it in front of the professor. She looked back at the office door. It was still closed. What if someone came in? "Okay, well." She started to lean her face down into Miss Wilson's lap, as if she was going to suck her off.

Victor's cock was straining in his panties as Melissa's face moved closer. He wondered if perhaps he could somehow convince her to wear a blindfold. Then maybe pull his own out of his pants? No, no, that was way too risky. In any case, this position was not a good one for teaching. "Another thing to consider, Melissa," he intervened, "is your position. You can do this in a lot of different ways Like the way you're doing now, for example. But, I can't really see what you're doing if you do it that way. Here, why don't I make room for you, between my legs."

It was rather awkward and a bit risky. He bunched up his skirt so that Melissa could kneel between his legs. "Guys like it this way because they can see what you're doing."

Melissa got into position, blushing as she did so. She wasn't sure exactly why, but it did seem a little embarrassing to be on her knees in between the knees of her professor, about to place her lips on her penis.

Victor placed the erection in his crotch, grasping hold of his own cock as he aimed the fake one at Melissa's angelic, upturned face. "This way, Melissa, he can see your pretty eyes and sweet, lovely lips as you kiss the tip." Melissa smiled up at him, her eyes shining through her glasses, and followed his instruction. She leaned forward, pursed her lips, and planted a long firm kiss on the tip. "Now just caress the tip with your lips." She did as she was told. "And, now, slip out your tongue and tickle the underside." She looked so lovely doing so. It was terribly erotic, terribly exciting, watching this pretty, this sweet, girl making love to "his" cock between his legs. If only it was in fact his cock. It wanted to be kissed now so terribly much.

They continued the lesson for some time. Melissa found that the fake penis didn't really taste that good. She wondered if a real penis would taste better. It probably would, or at least it should. But, that didn't stop her from really working hard at it. In fact, Melissa soon found herself really enjoying it. She plunged her face down onto the cock and then bobbed her head up and down, slobbering and slurping the erection in and out of her mouth. She did it in all sorts of different ways, as Miss Wilson had instructed, often smiling up at her, like a proud student displaying her talents.

After awhile, Victor knew that he would have certainly cum by now if this had in fact been his cock and, with his surreptitious fingering of his dick through his dress, it wouldn't be much longer anyway. "You're doing great, Melissa, really, really nice. You see, it just comes natural."

Melissa wasn't so sure about that, as Miss Wilson had been giving her quite a few pointers and suggestions. In any case, it was awfully fun to pretend like this. She was beginning to feel as excited as the penis. "Golly, Miss Wilson, I didn't know that I would enjoy doing that so much, and it's not even a real one."

He lightly caressed her apple red cheek as she smiled so gleefully up at him, her eyes sparkling through her spectacles. "It would so neat if I had a real one to play with. I could then make it squirt and everything. That would be so cool."

"Yes, yes, it would." That would indeed be cool. He couldn't disagree with that.

She hesitated to say the next thing, what she wanted to do next. "You know, well, um."

He cupped her chin in his fingers. "Go ahead, Melissa, what would you like?"

"Can you show me now how to use it, you know, to excite myself?"

"I would love to, Melissa." That was probably the most honest statement he had made.

"Oh goodie!" She leaped up from the floor and flopped onto her back on the couch, her face all aglow with the thought of what was about to happen next. "You know, Miss Wilson, it got me kind of excited already, doing that."

"Well, Melissa," he replied, shifting his own position on the couch. "I must admit that it got me a little excited as well."

"Really? Cool." She had been so terribly worried about Miss Wilson's reaction to wanting her to teach her like this. She would not have been at all surprised if Miss Wilson had just sent her out of her office to go take a cold shower. But, instead, she was actually enjoying it herself. "You know, most of the time while I was doing it, you know."

"Doing what, Melissa?"

Melissa smiled knowingly. She knew that Miss Wilson wanted her to speak openly about these things.

"Performing oral sex," she said quietly.

"Is that what you would call it, if I was a guy?"

"Golly, Miss Wilson, okay, okay. Most of the time when I was going down on it." That wasn't what he really wanted to hear her say, but she was getting better. "I was thinking that it was some guy. I was imagining that it was a cute guy I knew. But, a couple of times, when I looked up at you, at your face, I even thought it was your penis."

"My what, Melissa?"

"Miss Wilson! Please!"

"You need to say it, Melissa."

"Okay, okay, your cock. Your big hard cock! I pretended that it was also your big hard cock I was sucking." There she had said it, and she was happy that she had.

"Well, Melissa, if I did have a 'big hard cock,' as you so indelicately put it, I would be very happy to have you suck on it."

Melissa giggled at the thought and their little playful pretending. "What do you want me to do now?"

"Well, first, why don't you lift up your skirt and I will take off your panties."

Melissa giggled some more as she did as she was told. She wiggled and squirmed her legs as she felt Miss Wilson's hands moving up along her smooth, white skin, past her milky thighs to grasp the waistband of her panties. It was the hands of a woman, but it did still feel so terribly exciting to be having someone else, someone so much older and mature than her, pull down her panties, particularly for the purpose of using a penis on her.

Victor hesitated before he pulled them down. He first wanted to admire them. Thank goodness the girls of St. Mary were not required to wear a uniform, as was the case at Templeton. They were free to select their own panties, and he admired Melissa's. They weren't really sexy panties, but they were awfully cute. They were a tight yellow cotton with little pink hearts all over them. "I simply adore your panties, Melissa."

"Oh, thank you, Miss Wilson." She was pleased. They were among her favorites. "You don't think they're too childish looking do you? I mean, well, do you think a guy would like them?"

"Oh yes, I'm sure he would," he replied, as he slowly pulled them down.

Melissa lifted up her bottom to help Miss Wilson get them off. She felt so proud. She felt so all grown up, so womanly, but yet still very nervous and self-conscious, knowing what Miss Wilson would now see, and what she was about to do.

Victor did enjoy immensely what he did in fact see. Melissa had the cutest little pussy. It had just a sprinkling of hair, more like a peach fuzz than a bushy growth. It did nothing to hide from view her sweet charm: a pure delicate slit traversing the soft tender mound, which at the moment was glistening with her feminine dew.

Melissa covered her eyes. "Don't look at it, Miss Wilson," she implored, "it's embarrassing."

"No, no, Melissa," he countered. "It's really wonderful. So very, very pretty."

Melissa spoke from behind her hands. "You really think so? You think it's pretty?"

"Oh, I think it's just lovely. It's good enough to kiss." He sorely wanted to do that.

Melissa though was quite surprised. "Will guys really kiss it down there?"

"Well of course, Melissa. I mean you just got through kissing him pretty good down there."

She pulled her hands from her face. "I guess."

"Would you like me to do it, Melissa? Just to see what it would feel like?"

"Oh no, no. I think that would be too weird. I mean, you being a woman and everything."

Well, here was finally one detriment to the disguise. "Oh, I really wouldn't mind, Melissa."

Melissa again feared that she might have offended the professor. "Oh my, no, I mean, I think it's okay for people to do that, but, well, it's just not me."

Victor didn't press it. He didn't want to have the girl do anything that she didn't want to do, or wouldn't enjoy. It did seem funny though, as it would be the same lips touching her if he took of the disguise. Well, in any case, he picked up the erect penis.

"Oh my," squealed Melissa as she saw Miss Wilson pick up the erection. "I can't believe I'm really going to do this."

"What are you going to do, Melissa? Or, more precisely, what am I going to do?"

Melissa beamed but flushed as she said it, "You're going to put your erection in my cunnie."

Victor was, sort of. He felt like a mirror to the real Victor Victoria: a woman pretending to be a man pretending to be a woman, but then, actually he was perhaps the real Victor Victoria. That had just been a movie. He really was a man pretending to be a woman pretending to be a man. He would prefer not to be pretending at all but, still, it was also strangely erotic to be using this artificial penis on the young lady, helping her to learn how to pleasure herself, and be with a man.

Victor spoke softly, "It's nice to first just caress your cunnie with the penis; softly, gently, moving it up and down the lips, exploring its shape, its curves, with the tip of the penis."

Melissa could feel her heart quickening in pace. This was all so very dirty: the professor using a penis to play with her pussy. She watched the penis, her first penis, slide up and down her young fresh lips. It was so terribly naughty that she actually felt uncomfortable looking further. She pulled her skirt up higher to cover her head, to hide her face.

Victor smiled at her shyness, hiding beneath her upraised skirt, but it was clear that she was enjoying it. "It's really very helpful to play with it like this, to get you moist and ready for it to be inserted."

Melissa was breathing heavily. "Don't talk about it like that," she protested.

"But, sweetie, it's your own loveliness that gets moist, moist with your arousal, moist because you want my penis."

"Yes, ma'am," she whispered.

"And, what is it that you want?"

She replied ever so softly, "I want your penis, your erect penis."

"No, no, Melissa, not just my erect penis."

"Oh ma'am, must I say it again?"

Victor pulled away the penis, but did not deny her entirely. He slid his thumb up her lips, to gather her moisture, and then applied the thumb to her clit, softly pressing down as he circled it around and around. "Oh, Miss Wilson," she gasped.

"And, what is it that you want, my Melissa?"

"Oh, ma'am," she confessed, "Your cock, ma'am, your big, hard cock!"

He brought it back to her lips, firmly placed it against the gate of her femininity, and pressed it inward, as he continued to circle his thumb around and around her clit.

"Oh, ma'am!" Melissa gasped, clasping the fabric of the couch with her hands, pressing back against her cock with her pelvis.

He worked it in slowly, not plunging so hard as to hurt her. Instead, he slowly screwed it in, pushing in a bit, then pulling back, in a bit further, then drawing back, and Melissa met his screwing with her own squirming and thrusting, feeling rather obscene in doing so, but losing any sense of modesty to her lust, to the passion that was overwhelming her.

As it was overwhelming Victor, as well. He was up on his knees, ostensibly to get a good angle to work, but also to be able to lift up his own skirt, and with Melissa's face, her eyes, covered by her skirt, he withdrew his hand from her clit to withdraw his cock from his panties.