Head Of The Senior Class free porn video

Head of the Senior Class by Pamela ([email protected]) This work is inspired by Jody, who many years ago told me that during her freshman year at college she actually did what our main character ends up doing in this story. *** Everything they say about fraternities being a magnet for beautiful, sexy girls must be true, John thought to himself as he made out with Charlotte. She was red hot, gorgeous face and figure, her boobs nestled in a shockingly pink lace bra practically hanging out of her partially buttoned blouse. He had met her not two hours ago at that night's party in the Beta Rho Alpha frat house that he was pledging. After they had danced together about ten times, she had suggested that they find a more private place. Not really certain what she had in mind he had told her about a commons room on the third floor far away from the din of the party. She had grabbed his hand and said, "take me there" and off they had gone up the stairs. Once inside the room, Charlotte closed the door and locked it. She then made a bee line to a sofa, dragging John with her. No sooner had John sat down next to her then she had put her arms around his neck and began tongue kissing him. Perhaps she had had a bit too much to drink, or perhaps she just really dug John, who, in fact, was a pretty decent looking guy. Either way John couldn't complain, though he had never in his wildest dreams imagined that such an exciting thing could happen to him. His previous sexual conquests had been modest at best so this episode was entirely remarkable and unexpected. After kissing John forcefully Charlotte lay down on the sofa and pulled him down on top of her. Her hands tugged on his shirt until it was out of his pants and then she started unbuttoning his fly. For his part John realized that she would probably not object to his holding her lovely breasts so he did so as best he could considering the position he was in. How interesting the experience was, John thought to himself as the scene unfolded. Imagine that, an aggressive woman who was wildly interested in kissing him. Perhaps it was the novelty of the situation, but John had no inkling of where this was headed and did not think to protest as she began tugging on his pants to take them down. She was aiming to have sex with him, he realized, but he was totally unprepared for that. Before he could react Charlotte had gotten his pants down to his knees. She seemed desperately hungry to have sex with him. Taking off his pants, however, was a bad idea as was confirmed a second later when Charlotte suddenly screamed out loud, "WHAT THE FUCK! YOU"RE WEARING PANTIES!" Yes indeed, he was wearing panties. They were bright pink and the ruffly kind with lace everywhere. John tended to always wear panties, though not usually this fancy. He wore boy underwear when he had gym class, or had to go to the doctor or when he was on a date where he thought he might end up naked. But the present situation had never happened before. He had never in his life run into a Charlotte before. "I can explain," John said as calmly as he could. "Yuck, you sicko," she said jumping up. "Of all the guys in the party I latch onto a sicko like you!" "Charlotte, I can explain," he said to her back as she left the room slamming the door behind her. To the empty room he said, "I hope you don't tell anyone, or I'm screwed." He followed her downstairs and to his relief saw that she had left the house. He would have to make a point of avoiding her in the future. *** The next day at lunchtime, Diane was sitting in a booth at the Malt Shop, when she overheard a girl talking in the booth behind her. "I went to the Beta Rho Alpha party last night. You cannot imagine the creepo I ran into. This guy John is pledging Beta Rho Alpha, I thought he's really cute, so we find a place upstairs, and we're, you know, really getting into it. He so turns me on and then I find out he's wearing pink panties. I mean the pinkest, the laciest, totally like a little girl would wear!" "Oh, gross!" "Blech!" "So what did you do?" "I ran out of there as fast as I could. You won't catch me going to any more Beta Rho Alpha parties!" Diane crinkled her nose at the idea of the boy wearing little girl panties, or really any panties as far as that goes. But the really interesting thing was that this guy was pledging Beta Rho Alpha. This could probably be exactly what she was waiting and hoping for: a way to get back at the fraternity she most despised. The fraternity that had pledged her older brother Tim for four months and then during hell week just before the time he would become a brother, had kicked him out because of some mysterious thing that had happened. It had something to do with a scavenger hunt, she was able to learn from a phone call she got from Tim the next day. Exactly what it was no one would reveal. Tim had been so despondent that he had swum out into the ocean and drowned. She was sure it hadn't been suicide, just an act of frustration and anger that had gone awry. Apart from a Hallmark condolence card, Beta Rho Alpha had not been apologetic for what happened and took no blame for the accident. Her parents had filed a complaint to the University but nothing had come of it. The administrators being the morons they were said that without proof connecting Tim's swim to the hazing he had endured the night before, their hands were tied. Only later did Diane discover that the University president was a Beta Rho Alpha alum. Now, a few years later the memory still rankled and Diane was determined to carry out some act of revenge. She would have to figure out a way to use John and his pink panties to take down the entire fraternity and have them kicked off campus. The first step would be to find John and that would have to wait until the next Beta Rho Alpha party, and that couldn't be far off. If there was one thing that one could take for granted about fraternities, it was that they lost no opportunity to party as much as they possibly could. *** Two weeks hence a mixer was advertised at Beta Rho Alpha house and Diane was glad that she'd finally be able to put her plan into action. She donned her most devastating black top and short skirt, where the cut of the top accentuated the projection of her ample bosom and the skirt showed off her wonderful rear end. She was sure she could land John if only she could figure out which boy at the mixer would be him. When she arrived at the Beta Rho Alpha house she saw that there was an open bar with beer and wine and a great dance tape playing in the semi- darkened room. As soon as she entered she could see guys around the room steal a glance at her. A few stirred as if contemplating their next move. Diane saw a boy who looked to be relatively young and she casually walked over to stand near him, figuring that John would have to be one of the younger boys at the dance. The boy gave her the once over and said almost immediately, "who are you?" While ordinarily Diane did not enjoy being hit upon by guys, tonight would have to be an exception if she was to figure out who John was. "I'm Diane." "Cool. You've come to the right place." "Have I? And who are you?" "Chuck. Want to dance?" "Sure, OK." As Diane and Chuck danced, she glanced around the room at the many boys hoping to see one that might be John. Chuck danced with his gaze riveted on Diane and she knew that she would have to get away from him as soon as the dance was over. When the song finally stopped, she cut off any attempt Chuck might make to stay with her by saying, "I'm sorry, Chuck, but I'm supposed to meet John here. I don't see him." "John?" Chuck said, "which John, the brother or the pledge?" "The pledge," Diane said. "That's him over there," Chuck said pointing to a guy carrying a bucket of ice toward the bar. Diane turned to where Chuck was pointing and she saw a cute guy, of slender build, in fact, exactly what she was hoping for. He seemed to be involved with maintaining the bar that was built into a corner of the room. "Oh, right, there he is," Diane said. She smiled at Chuck and headed out across the crowded dance floor toward the bar. The song "Penetration" by the Ventures came on and Diane quickened her pace to avoid getting tangled up in the dancers. John was behind the counter arranging the ice when she came up to him. He glanced at her and then seeing how gorgeous she was he stopped what he was doing and asked, "can I get you something to drink?" "Sure, make me a gin and tonic." "Coming right up," John said. "Do you like Penetration?" Diane asked. Thinking she was referring to another meaning John was perplexed by the remark. "The song," Diane said. "Penetration, by the Ventures, it's playing now. What did you think I meant?" John laughed and handed her the drink. "Actually, I did kind of think ... I'm sorry." Diane laughed now and she couldn't help but think that despite his pink panties, the girl in the Malt Shop had been way too hard on him. This guy seemed quite likeable and there was probably a lot more to him than just being some kind of pervert. On the other hand, none of this mattered too much, or shouldn't matter. She had a plan to carry out and if it turned out she ended up hurting a nice guy, well that was unfortunate, but far less a pain than she and her family had suffered. Her brother had to be revenged; there was no two ways around that. The song ended and then immediately "Telstar" came on. "Oh my goodness what a strange blast from the past. Who made up the dance tape?" "One of the guys. You want to dance?" John said impulsively. "You can leave the bar?" "To dance with you I sure can." "Great. Let's dance." Diane wondered if he was wearing his pink panties that night, though presumably he had learned his lesson from the previous party. They ended up dancing several times until Diane said she had to go. She knew he would ask her for her number and he did, right on cue. She was sure he would call her in a few days. *** Diane figured that John would wait 3 days and then call her and like clockwork he did just that. They met for coffee at a Starbucks. This time Diane wore a white peasant style top with her laciest bra underneath. It was an outfit that suggested she liked sexy lingerie and that could only help draw John toward her. "So why did you pledge the Beta Rho Alpha's?" Diane asked. "My brother was a Beta Rho Alpha at the University of Akron and he encouraged me to join a fraternity, so it seemed like the natural one." "Do you like the guys there?" "The pledges are real nice. The brothers seem pretty OK also. Of course they're always hazing us." "what do they do?" "They've got a bunch of traditions they call them. We have to address them by Mr. so and so, we have to wear a tie and fetch coffee, lunch or any other thing for them. If you don't cover your stomach when walking past a brother he can punch you there. The first few times they get you by surprise and then you're like paranoid all the time. The worst thing about it is making us spend hours cleaning up their messes on the weekend. Like for that dance we had to scrub the floor for hours. It interferes with my homework. That makes me worry." "I wonder why they have to haze you at all." "They say it gets us closer to together - a shared experience of suffering. That may be true, I don't really know yet." "Are you going to haze the pledges when you're a brother?" "Good question. No, I don't see myself as that kind of guy." "Then why pledge a fraternity?" "Had I not pledged, I'd never have met you, isn't that so? Why did you go to a fraternity party?" Diane laughed. "You've got me there. The truth is I was curious." "I thought you were looking for me?" "Why do you think that?" John hesitated and then said, "because one of the pledges, Chuck, told me that you were looking for me." Diane laughed. "I hope you can keep a secret, but I just had to get away from him, so I just blurted out that I had to meet John. I figured that there had to be somebody named John at the party. Then he asked me if John was a pledge or brother and I chose pledge and the next thing I knew I was talking to you. I hope that you aren't deflated by this revelation, or you don't think me too mean?" "No, no, no," John said, "actually I'm relieved to hear you say that because I've been thinking that maybe Chuck was screwing with me or something like that. As you saw, he is a bit aggressive." "Macho is the word I think," Diane said. "Yeah, I suppose you're right. I don't know why some guys are like that." "Too much testosterone?" Diane said. "I suppose that's it. Personally, I've never been really into being a cave man." "I think that's one reason why I liked you at the start. You seemed more like a gentle man." She said that as two words so that it could have a second interpretation. John blushed. "Maybe I'm more macho that you think: you were wearing that incredible outfit. It was so attractive and sexy. The top was really pretty." Bingo, Diane thought to herself: a guy who notices my clothes. Maybe he's even thinking about wanting my clothes. That would be weird. "Thank you, that's very kind of you. Most men, particularly the cavemen type are only interested in girls taking off their clothes, not what they're actually wearing. This shows that you have a sensitive side." "I hope that's good," John said." Though he tried to sound casual, the fact of the matter was that he was suddenly unsure that he was projecting the right image. Diane had to wonder if it were good that John had a "sensitive side" if it took the form that he noticed her clothing. In any event, she decided, if she was to accomplish what she wanted, she really had to reassure him. "I think that guys should be encouraged to be any way they want to be. There is a continuum and every man is somewhere along it. Some guys are caveman and I think a lot of woman prefer that type, but many guys are not like that. They have feelings and thoughts and are considerate of girl's feelings and many women definitely want that. Sensitive men tend to be sweeter, more considerate and more willing to listen. Personally, I hate dealing with bossy and obnoxious men who think that it is their birthright to tell women what to do." Diane felt like this was a good direction to go. She would emphasize that gentleness was good, that she liked it. Hopefully, in time, John would feel that he could trust her with his secrets. Anyway, he would have to get to that point if her plan was to work. For his part John was relieved by what Diane said. He had always figured that some girls somewhere must like men who weren't macho, who would listen to them as equals and not try to dominate them. He felt the very first stirrings that Diane was a definite keeper, a girl with whom maybe anything would be possible. He said finally, "no definitely, there is no rational basis for men controlling women - it can only be justified outside of rationality." "As indeed it is everyday all over the world," Diane said. *** They had a few more dates together during which, at one point or another, the conversation was about the basic question of what kind of men did women prefer - macho or sensitive. With her radar tuned to listening to every nuance in John's conversation, Diane became convinced that he was invariably the one who brought up the subject. It made sense. He was determined to explore how far he could go in revealing that he was the kind of guy who wore panties. Diane made every effort to seem complacent and even slightly encouraging. She wanted him to open up gradually, build upon a solid basis, so there would never be any surprises and she would not risk undoing all that she had accomplished thus far in the fulfillment of her plot. An unanticipated consequence of listening carefully to John was that she felt herself becoming increasingly sympathetic to his plight. If he had desires to wear panties, like she assumed he did, it was not because of some sort of sinister deviance. No, he was surely a pleasant, intelligent, witty and gentle man who somehow seemed to be constructed differently than other men. The way she saw it, he had a feminine streak. He was a combination of male and female characteristics and that was just a fact of nature that was not worth criticizing. As time passed Diane began to see that the ultimate reason why John might end up doing what she needed him to do was that he had grown attached to her emotionally. He might even end up falling in love with her. She found herself dreading the idea that she would ever hurt such a kind and gentle man and then she realized that the source of her pain was the idea that she might be growing fond of him herself. She was starting to care for him and that was why she felt uneasy with the way things were developing. On the other hand, things were set into motion that were unstoppable: her highest priority would always be the fact that the fraternity had to be punished. Diane had spent a lot of time thinking about what she would do when she "discovered" that John wore panties. She would have to react to it in some way in order to prove to him that she didn't already know his secret. She definitely would not act shocked, nor would she laugh or make fun of him. No, she decided she would act curious and get him to open up to her about his true feelings, and especially those that led him to wear panties despite knowing that he was surely going to get caught wearing them. A point was reached where Diane knew that her relationship would have to become physical: in the context of a sexual bond between them John would reveal his secret desires to cross-dress thus setting the stage for Diane to gain the essential power she needed to implement her plan. With each new date, hand holding turned to hugging and then kissing. Diane found that John especially loved when she put her arm over his shoulders and she sensed that it was because he favored being put more into the girl's role. Diane then made a point of doing that as often as she could. At first they kissed when they were saying goodbye and then more often, at odd times, like on the street if no one was around, or on a park bench. Diane had to admit to herself that John was a dreamy kisser and she looked forward to a time when she might spend hours kissing him. Finally the opportunity came when they went to a movie together and sat in the back row. Not long into the movie John sensed that Diane was looking at him and when he stole a glance at her he saw a look that conveyed her desire to kiss him. Diane put her arm around him rather forcefully in such a way that made John think that she was a guy who just decided to make out with his date and would not take no for an answer. John could offer no resistance and before long they were deeply kissing. John had never experienced a woman as beautiful and hungry to kiss him as Diane was. With her free hand she held his chin and gently touched his lips as they entered into five minute long kisses in which John nearly swooned with lust. He felt woozy and nearly fainting with arousal as he felt ensnared in Diane's dominant grip over his body. Feminine thoughts entered his brain one by one. Thoughts that he had suppressed for ages. Thoughts of himself as a delicate young girl in a pretty summer dress, perhaps wearing just a wisp of a bra holding her small breasts. Underneath her dress she wore simple white panties that hugged her crotch since she had no penis. She had pencil thin arms with no muscles to speak of. Perhaps she would have tied a pink ribbon in her hair. A little perfect universe of femininity opened up for him inside Diane's embrace and he felt so happy that he wanted to exclaim for joy. For her part, Diane sensed that John had become soft and pliant. She had a strange sensation that she was kissing a girl. She rather liked the equality compared to her typical experiences with guys who always seemed to feel it necessary to show how strong they were while kissing her. After they had left the movie theater, John and Diane would have been hard pressed to tell anyone what the movie was about. Something to do with spies or maybe musicians John thought. As they walked together, Diane teetered on the edge of inviting John up to her place so they could finally consummate their relationship. She hesitated because she wasn't completely certain that John was wearing his panties and she wanted to quickly get past that point in their relationship. If he wasn't wearing them it might be harder for him to switch to them the next time they met. Based upon all that they had experienced in the movie theater, she was certain that John would feel secure enough to wear panties the next time they met, so she decided to wait until then. When they said good night Diane could see that John wanted to tell her something. "I never kissed a girl in that way before," John said. "What way is that?" Diane said. "You know, I became like jelly in your arms. I hope you didn't mind." Diane laughed, "if I did, I had a strange way of showing it. I like you just the way you are John, so please be who you are. That will always make me happiest." Diane figured that if that wasn't telling him to wear his panties, then nothing was. John smiled and said, "OK. Sometimes I'm so insecure it must be annoying, so I'll stop it right now and make sure I'm always myself with you." They had one more long kiss and then Diane went up to her apartment and John went home to his. *** A few days later they met at their favorite Indian restaurant and had a delicious dinner. When they were paying the check, Diane said, "I want you to come back to my place." "Of course," John said. He said it with no hesitation which made Diane think that John had nothing to hide. This could mean that he wasn't wearing panties, or it could mean that he was determined to fully be himself no matter what. She hoped it was the latter of the two. In any event, the die was cast and she would soon find out if they would be entering into the next phase of their relationship. The fact of the matter was that John was wearing panties and he had been doing so on their last few dates. He had decided that he wanted to be found out sooner rather than later since if Diane was going to reject him because of that - and he felt almost certain that she wouldn't - then he wanted to get it over with before he fell even more in love with her than he was already. John and Diane walked to her apartment and in short order were sitting together on her sofa. She had poured them each a class of Pinot Noir. The sexual tension in the air was so thick you could cut it with a fork. Finally, they finished sipping their glasses of wine and they turned to look at each other. In unison their lips moved toward each other's and they began kissing. Diane took her blouse off and John removed his shirt. The view he had of Diane in a lovely feminine bra was overwhelming. He both coveted touching and caressing her lovely breasts as well as wearing a bra like she had on and feeling that he had his own breasts resting comfortably on his chest. Diane was first in removing her trousers until she was just wearing her panties and a bra. She undid the button on John's slacks and pulled down the zipper. She quickly slipped her hand in to confirm if he was wearing panties. When her fingers touched fluffy satin-like material she almost laughed with joy. Her crazy plan had worked flawlessly and she had finally arrived at the moment that she had first envisioned a month earlier in the Malt Shop. "Oh my goodness what have we here?" she said with mock surprise. Not appreciating the humor, John felt a shock the same as had happened a few weeks earlier with Charlotte. "I'm sorry!" John said horrified. "Sorry?" Diane said. "Let me look!" She pulled John's pants down to his knees so his red panties were fully visible. "Oh my, oh my, what absolutely pretty panties! Ruffles, lace and bows! Just so cute and adorable! The kind of panties little girls wear!" She laughed inwardly to see John's prominent boner barely contained within the panty. As John came to understand that Diane was not upset his heart leapt with happiness in his chest. Oh my goodness, he thought, this was going to go the way he had so desperately hoped it would. "You're so cute in those panties! Take off your pants and let me get a really good look at them." A bit sheepishly John stepped out of his pants and took his socks off and stood in front of Diane in his ruffly red panties. He could feel his heart pounding frantically and his member bulged and throbbed forcing out the front. "My goodness there is a war going on inside your panties!" Diane laughed. "I'm sorry, I can't help it." "No, I guess not. I can't believe how cute you are. Now come here and let me see what's causing all the commotion in those panties." John came over toward her. His ears were ringing. The future he had never let himself imagine even an hour ago now seemed like it had arrived. "You really don't feel upset that I like wearing panties?" "No, why should I? How is it harming the world? I like the idea of you having some feminine qualities and it's sort of cute that you like wearing girly panties. To tell you the truth I haven't seen panties like that since I was a little girl, and it's just sort of yummy to see them on you. Your cute butt nestled in them with all the lace is both funny and hot." John blushed and then his expression turned serious. This conversation had gone way beyond a point he had ever imagined he would reach with a girl and he realized that his true happiness depended on finding out that Diane knew and accepted everything about him. In his mind, the panties were just the tip of the iceberg. The truth was that he wanted so much more. "I need to confess everything to you," John said. "Confess?" Diane said acting as if she did not know what he might say. The truth was that as she had gotten to know John she had thought it likely that the panties was only one little piece of his desires. She had often wondered if he wanted to become a girl through surgery. That seemed like the most extreme thing he could say and she surprised herself by the realization that it would make her sad if he confessed that to her. In fact, such an admission on his part would only make it easier for her to take advantage of him later. "The panties are a part of a whole. I need to tell you the whole story!" He felt tears coming on as he imagined her pulling back emotionally away from him. "The whole story? Do you want to ...." Diane said. "Become a girl? No, no, no!" John said, "at least not the way you mean." Despite her trying not to, Diane felt relieved to hear him say this. "What do you mean?" she said trying to encourage him to talk more. "Look, Diane. The thing is that I know inside myself I'm sort of a girl. I mean I often see myself as a girl. But I also am rabidly heterosexual. I've never desired men and I never would part with my, you know, equipment, because I would never want to not be desired that way by women, by you, I should say. Am I making sense?" "Yeah, I guess so. Keep talking." "The thing is I've only wanted to have sex with women, but at the same time, in the most perfect relationship, I would feel like I was a girl. I don't want to make love as if I am the man, that repulses me. It's only as a girl that I feel anything, and then it's very powerful. You see?" "So you're like some sort of lesbian?" "Maybe you can say that. What I'm saying is that I'm like what you said to me a few days ago. I'm part girl and part boy and I can't be fully happy without both. So I love girls like a man does, but I feel emotionally and otherwise like I'm a girl. Am I horrifying you? It's just that I care too much about you to hide from you the truth about myself!" Diane starred at John with an intense look that caused him to stop talking. He averted his eyes and then glanced back at her and saw she was still looking at him. Finally she turned her eyes away and said, "I've got to think a bit about what you said. It's kind of overwhelming. I need to sort out what I do feel." "Sure, I can understand," John said. He cursed himself for being as open as he had been. "I'm sorry I sort of got carried away. I can understand if you think I'm really sick." "No, no, no, it's not that," Diane said. "I'm glad you said what you did. It's so honest. But you deserve for me to be equally honest. So I have to think about what you said." They were now both sitting on the bed a few feet away from each other. Diane was wearing her panties and bra and John was wearing his red fluffy panties. His boner had subsided but in the present lull he had the chance to take a good look at Diane's beautiful figure and he could feel himself starting to harden again. She was so gorgeous, he so wanted to hold her. To be a girl with her was so unimaginably glorious. They would have the best of both worlds: the right plumbing, but the emotional bond that only two girls could have for each other. From Diane's viewpoint she felt relieved that she now had the whole story. Her instinct that the panties was only the tip of the iceberg had been true, but the iceberg was more interesting than she had imagined since it did seem to leave a place for her, a place for the two of them to have a "normal" relationship. Ultimately, this was something that she would have to place on the back burner. The immediate issue was how to harness his confession to her advantage. Now that she knew what point A was, she would have to figure out the path leading to point B which would be the downfall of the fraternity. After a few minutes Diane said, "if you feel emotionally like a girl, well that might mean wanting to have sex with men, like most girls do. Feeling like you're a lesbian is not putting yourself in the feelings of most girls. For example, I think that many girls, under the right circumstances, like the idea - pardon my crudeness - of giving blow jobs. For some girls the attraction might be the power it gives them over the man, but for many others it probably has to do with their enjoyment of giving another person so much pleasure. That's often a female trait - to care about giving pleasure to others and feeling fulfilled in the knowledge that your man gets to revel in your femininity and your feminine attraction to his penis. I can see how you react to my pretty bra holding my boobs. I see the thrill go right into your mind and I take pleasure in that I've made you happy. It's a feminine thing to get a sort of pleasure in one's vulnerability and intrinsic gentleness and softness in comparison to men. The blow job is particularly special because our complete focus is wrapped around the essential aspect of the male - his erected, hard, blood engorged, hormonally saturated phallus. Not only that, a powerful, male dominated orgasm awaits in his loins that you coax out of him. So your subservience and devotion to his penis spurs him to a climax that in power and momentary madness can never be matched by any woman." Diane's little speech resonated in John's mind. She was alluding to depths of femininity that he had never fully appreciated before, though now that she voiced them, he could see that they would be things he might very well want to experience. Diane laughed suddenly. "What's the joke?" John asked. "I was thinking that many men are nothing more than their penis. Their personalities sort of end right there. After that, nothing at all. Girls are rarely ever that shallow." "Maybe that's why I want to be a girl. To be part of the superior sex." "I don't doubt that for a second," Diane said. "Do you think you would you ever want to give a guy a blow job to help accentuate your feelings as a girl?" The question did not really take John by surprise, since his mind had already begun to wonder if that was something he would be drawn to so as to experience that part of femininity. He thought about himself in that role. It would be a drastic step from where he was now and if he did it, perhaps it would cause uncontrollable changes in his life. Would he still be able to feel content being in love with Diane, for example. "I don't know what to say. How could I rationalize liking the idea of giving blow jobs with the fact that I want to make love to you?" "Well I don't think it's necessarily a contradiction. You may prefer one or the other or both. The question is, as you come fully into touch with your girl side, will she prefer giving blow jobs to being in love with a woman. After all, I can see your boy side wanting a girl to love, but that may be something that dissipates as you grow older." "Right now, I don't think that that is likely to happen since my attraction to being feminine originates in my desire for women. So you see its not like a normal girl who is feminine by birth. I desire femininity due to my adulation for women, my strong passion for them makes me want to imitate them, to dress like them and to revel in feeling feminine like they can. If I go too far away from my underlying maleness I'd cut off the thing in me that drives the whole desire to cross-dress in the first place. By not being male, I lose my desire to be female. Women are feminine, they don't long for it. Only a man can long for femininity. So to answer your concerns about blow jobs for example. I might actually find that to be something that attracts me, but it would be on the level of many feminine things that attract me. It won't mean that I would become a different person if I was to have done it. In any case, I have enough self-control that I would never do something that would lose the trust of a woman I was in love with. It's just a simple question of what is most important to me. For example, many married men are attracted to hot younger women and they never act on those desires because they don't want to ruin the trust they have with their wives." "You make so much sense and I do think I should believe you," Diane said. The conversation was not going where Diane wanted to take it and she decided she would have to take a different tack. "But, the thing is John that I'm obviously falling for you and I feel terribly vulnerable to the possibility that someday in the future you'd come to a realization that you wanted to become a girl. I've read enough to know about men who one day tell their wives that they've decided to become girls. Come to think of it, there's Jan Morris, though his wife was actually kind of supportive of his transformation. I suppose she didn't have much choice in the matter. I think it must be not very fair to the wife, particularly if the guy has known about his desire for a long time. The wives are not being selfish. They love their husbands as functioning men. Why shouldn't they be hurt and angry to find that they can no longer have sex with them?" John felt confused and a bit irritated. Diane did not seem to be trusting him and her words were depressing. How could she know more about himself than himself? "I think you're accusing me of things that I haven't even done, or thought about doing." "I'm sorry, I don't want to not trust you. But I feel so vulnerable to things that you might have not considered so far. You have a tremendous power to hurt me and that power grows the deeper we fall for each other." Cast in this light, John suddenly felt choked up with emotion. Diane seemed to be declaring her love for him and her desire for a future together. He put his arm around her and hugged her. A few tears came to his eyes. "I would never ever want to hurt you." "I know that," Diane said. "What could I do to convince you that I'd never want to cross over to the other side?" Diane took a deep breathe and thought carefully about what to say. "Maybe you need to experience the most feminine things possible in order to really know that it won't trigger desires for fulfillment that you don't even know you have right now." "In other words, you mean give some guy a blow job to convince myself that I don't want to give blow jobs?" "Well I wouldn't put it exactly that way. I wasn't thinking necessarily about blow jobs though that might be the easiest and least risky way to explore your female side." John wondered what were the more risky ways she was thinking about, but decided he didn't really want to know them. Diane continued, "in fact, perhaps we could arrange some nice setting like a darkened room where you could give a blow job or two where it would not be so stark and in your face." Diane laughed, "I didn't mean it that way." John lay back on the bed and thought about what Diane had said. She was obviously giving him permission to give some guys blow jobs, in fact, almost insisting that he do so. It made him wonder if she had some other hidden motivation. "You wouldn't be watching me do it would you?" "Oh, God, no! How gross would that be! No, only you and the guys would know what went on. I certainly trust you enough to believe that you would do whatever you said you had done." "Well, I might be a cross-dresser, I can't deny that obviously, and I'm pretty sure that I wouldn't want to pursue a future in which I sort of became a woman, but if it makes you feel like this will remove some doubts about my real intentions, then I'll do whatever you say. A blow job or two where I can just get in touch with my feminine side in the way you suggested before, is not really a big deal. I'm sure it won't leave a permanent mark." John said this with confidence but a stray thought ran through his mind that he shouldn't be so sure about everything until after he had actually experienced it. Could he possibly find out that giving blow jobs was something he liked and wanted to do? Maybe Diane was right. Until you did it, you really couldn't predict perfectly how it would turn out. Diane smiled inwardly. She had formed an image in her mind of a small animal, like a fox or raccoon being caught in a trap. A door had dropped down suddenly capturing the creature inside. John was now caught and her plan would be realized. At the same time, she felt that a mountain of guilt for what she was about to do to him was looming over the horizon. She would pray with all her might that somehow John would end up being forgiving - once he heard the whole story - and then she would be free to fall totally in love with him. She reached out with her hand and pulled John in close to her so he lay down on his back next to her. She raised herself up over him and put her arms around him and found his lips with her mouth. She gave him a deep, powerful kiss and John began to cry. Never in his wildest dreams had he imagined he could meet a girl who would allow him to be the strange mix of boy and girl that he was. Not just allow him to be like that but actually love him because he was like that. Diane climbed fully on top of John and he felt her breasts in her bra touching his chest. Her hand pulled on the elastic of his panties and he raised up his bottom to help her pull them off. When they were off, Diane pulled off her own panties and then as she resumed kissing John, she directed his member to her opening. Grasping it in her hand, she moved it slightly back and forth to moisten the entrance way. She then impaled herself on his staff with several forceful movements. In a minute she was moving her hips up and down, swallowing and releasing John's cock. Minute by minute their movements grew more frantic until their screams signaled they had reached a climax. *** The next morning when they woke up they had memories of the previous night fresh on their minds. John couldn't help but feel that what had happened was too good to be true and he prepared himself for the worst: Diane telling him that she must have been drunk not to have run far far away from this strange guy who wore panties. Instead, Diane was the first to speak and she said, "I suppose we'll have to get you some girl's clothes, unless you already have a wardrobe. Do you?" Relieved by her matter of fact tone, John said, "besides panties, the only other clothes I have are an old bra that I found in a Laundromat. It's not really too nice. So you don't mind if I dress up?" Diane thought about John in the Laundromat. He must have seen the bra abandoned somewhere and then snuck it into his laundry bag when no one was looking. It was fascinating to think of the power inside John's mind that drove him to do that. It was power that she was harnessing to get him to do what she needed. "We agreed last night that it's OK on the provision that I'm convinced that you don't have it in you to want to become a girl who prefers men!" "So I'll do some blow jobs to convince you?" Diane smiled and nodded. "I'll take care of that: find some guys, probably in a nice hotel room somewhere. You can be anonymous. We'll get you all dressed up as a sexy girl. The guys will just think you're a hooker and after an hour or two it will all be over. OK?" "It sounds doable," John said though to have it spelled out by Diane it seemed kind of tawdry. And he wondered how she wouldn't ultimately think less of him for having agreed to do it. On the other hand, he wanted her to trust him and maybe by sacrificing like this for her, she would develop an eternal love for him. As confused as he was, there was no confusion about the fact that he couldn't wait for Diane to dress him up like a sexy woman. He imagined himself with a wig of long, straight hair and a tight sexy dress showing off his boobs. It would be so cool. Beyond this image he could visualize himself getting down on his knees in front of a guy and pulling the guys cock out of his fly hole. He had to admit that there was something about that that attracted him, but there was a big difference between fantasy and reality and he felt sure that when he actually did a blow job, it would not be so appealing. His belief that the blow job test was unnecessary would be vindicated. At least he hoped so. *** That afternoon Diane took John shopping at a nearby Macy's. First stop was the ladies intimate apparel department. John had never had the nerve to be seen in such a place previously, but with Diane at his side he could pretend to be the accommodating boy friend and he felt at ease. In the past he had snuck a peek or two at the racks of bras and panties as he had walked by heading toward the exit or some other part of the store. Now he was immersed in the lingerie as if he were a diver descending deep into an overwhelming and intensely female world. John's source for the panties that he already owned, had come by accident as if by a miracle one day when he had returned to his parent's apartment after school and saw a package in front of the door. It had been incorrectly delivered and he was going to put it in front of the correct apartment when he had noticed that the package had come from a women's clothing store. He had snuck it into his room, opened it and found panties inside with a note to a girl named Beth from a guy named Frank. He felt both awful for being a thief and ecstatically happy, especially when the beautiful panties fit him so perfectly. Every day after that he wished that another package would show up mysteriously at his door, but it never did. Taking a good look around Diane said, "what kind of bra do you think you would want?" She had said it softly so that she could not be overheard by a few women shopping nearby. "It's bewildering," John said. "Let me pick something out for you. If you like it scratch your nose. If you don't, pull on your ear," Diane laughed. "It's like we're spies," John said. In front of them was a rack of Warner's bras and in the distance was a sign advertising Bali bras. "I'm not sure if you're developed enough for a Bali bra," Diane said looking at John, "but on the other hand, we probably ought to get you a bra you can grow into. So perhaps a bra that has some room for bigger breasts will be best. How does that sound?" "That sounds like a good plan," John said. "Some of the Warner's are good for young girls as are the Playtex and Maidenform." Diane strolled through the aisles sweeping her hand over different bras. "I wonder what we ought to get." John whispered, "so many bras, so little time," and Diane laughed. Diane said, "every woman has a different body. Our breasts are all different sizes and shapes. They have to make bras to cover every possibility. On top of that each woman has a different sense of what is comfortable. Some want to be held firmly, some gently, some with a focus on the shoulders, some on the back. Some hate the feeling of underwire, but many love it for the extra support they can get without a lot of elastic. Some girls want their breasts pushed up, some out, some to the side, some to the center, some minimized and some maximized. There is also a vast range of different feelings of femininity. Some women feel naked without lace or little bows. Perhaps it harkens back to when they were young girls and first felt they were pretty. Other women can't stand the thought of lace and they just want complete functionality and nothing more. Then depending on what clothes you are wearing, a tee shirt, a formal blouse, a dress of one style or another, the way your breasts are held can affect the way the whole outfit looks. And how about colors? There are a million different reasons for picking one color or another - to match a top or dress - or to express a mood. And then there is your husband or boy friend who might like to see you in one kind of bra or another. By the time you're all done, you need the thousand different bras you see here." "I don't know whether to laugh or cry," John said. "But the problem is much less complicated really. After trying a few different styles from a few main companies you sort of gravitate to a brand that seems to be made for your kind of body. Like I like the way the Flower Bali feels. It's a kind of special feeling of being held firmly but not too firmly and being pretty without being gaudy. And I think I look really good in them in the way my breasts project when I wear different outfits. So I sort of always buy Flower Bali bras though I do experiment from time to time with others. And there are also high- end bras, like Fantasie and La Perla that are rich in lovely details and very well made and technologically sophisticated. They give a girl a whole different feeling than cheaper bras but most girls can't afford them. I do think it's kind of fun to try out a new bra from a company you've never tried before. It makes one feel like a new woman." "So I guess girls need to try lots of different bras until they sort of figure out which ones they like?" John said with some frustration. "I suppose that's sort of true, but we'll just start with a couple of bras and then go from there. We can always buy some new bras later on so you get to try out more and more. See, here's a cute one you might like," Diane said. She held up a bra that was two toned, sort of tan and gray with a pinkish gray flower design on the strap. Or there is this one," she said and held up a white bra with seamless cups. "What about a pink bra," John said. "Pink is not very practical. You can wear a white bra under anything. A pink bra would not do underneath a white blouse. Of course, there's no reason not to get a bra with lots of lace if that's what you like, and judging from your panties I bet you wouldn't be happy with a plain unadorned bra." "You know me as well as I know myself." "I suppose I do, but you've been very good at explaining to me who you are. Anyway why don't we look for a cute lacy white bra for you." They wandered through the aisles until they found one. It was sweet and perfect, with cute satiny white cups surrounded by lacy decoration. Diane contemplated John for a moment and said, "I'm pretty sure a 36 will fit you. And I suppose a C cup. We'll have to get you some nice breast forms to fill out the cups properly." "Are you sure? Where can we get them?" "We'll look on the internet. In the meantime I have some falsies you can use. They're just foam but they'll do." "It's very pretty," John said staring at the bra in Diane's hand and thinking that it would be his to wear. "I can't thank you enough," John said. Diane smiled and said, "I think we should get you a pink bra anyway. You can wear it under opaque clothes; I know it will make you happy to get one." John was so happy he didn't know whether to cry or to laugh with gaiety. "We also might as well get you a Flower Bali. Maybe it'll fit you as nice as it does me." After Diane took one off a rack she and John scouted around looking for pink bras and finally got a cute one. Diane also picked out a few panties here and there and then led John to a rack of slips. When she felt that no one was looking she held up a half slip to John's waist and said, "we really have to check the length. You'll need a half slip to wear under some of the skirts. We'll also get you a full slip." After Diane found everything they needed they went to a cashier and paid for the bras, panties and slips. When they left the counter Diane said, "we've got you some nice bras, panties and slips. We'll get some hose for you and then we'll take you to the girl's shop downstairs and get you some skirts and dresses and I guess you'll also need a pocketbook and other accessories." They spent the better part of two hours finding the other items. Diane tried on dresses and skirts and from seeing how they fit herself decided if they would fit John or not. Based on this approach they were able to get a number of nice things for John to wear. Among John's favorites was a pretty pink skirt, a cute light blue dress, a pale pink blouse with some ruffles and lace and a really sexy skin tight silvery top. The last two purchases were shoes and a wig. The shoes they got at a warehouse store where Diane helped John to surreptitiously try on the girl's shoes until they found a nice pair of heels that fit him. The wig they bought at a wig shop just for the fun of it: it would give John a chance to make a complete transition. "I've got plenty of makeup," Diane said, "and I'll donate some to your cause." While they were travelling home John said, "I can't believe how nice you've been to me. This has been a very special day for me." "Shopping is fun with you. You're so appreciative." "It's so incredible. I feel like you know the inside of my mind, intimately." "I do think I sort of get you now. The truth of the matter is that you're jealous of girls. Jealous of the fact that we get to be feminine and you don't. Isn't that a big part of it?" "I don't think I've ever really thought about it that way. I've wanted to dress and look like a girl but I guess you could say I feel some jealousy." "Jealous that we get to wear bras and panties and you don't?" "Yeah, but just as much I guess I've wanted to be free to be gentle the way a girl is." "Gentle? Not all girls are gentle!" "I guess not, but if I were a girl I would be a gentle one. I would wear the prettiest clothes I could find, like the clothes you helped me pick out today, and I would just try and be the kind of girl that everyone liked and thought was pretty." They were quiet for a period of time until John said, "I am jealous of you being a girl. It's a kind of daily pain I feel that I don't have breasts, that my panties have this bulge in them. You know how often I thought that it would be wonderful to have my panties just flat going over my pubies. But I understand that it's never going to happen and I can accept that." Diane looked at him, "never?" "I know you're not as sure as I am. Anyway, I'm going to give some blow jobs as proof aren't I?" "You still don't mind?" "I haven't any choice. I want to make sure that it's never ever going to be an issue between us. Anyway, when are you planning to find me the guys to suck off?" "Well as soon as you've gotten comfortable looking like a girl, we'll set it up." If the truth be known Diane was having second thoughts about her plan. She was very deep into the deception and yet she could not deny that there was something about John that she found compelling. Was it his honesty, his willingness to "come out" in front of her? Was there something special about having a cross-dressing boy friend that fulfilled her own needs in a way that she had never realized before? Whatever it was, she could see that they had gone beyond the point where there would not be hurt feelings. The only thing she could control was how much hurt: the sooner she confessed to John the full extent of her deception, the less the ultimate pain he might feel. Still, as much hurt as she might eventually cause John, it was also true that she was the source of his greatest pleasure since she had given him an outlet to be the girl he wanted to be. The best course of action was not to say anything just yet. *** When they arrived back at Diane's apartment it was tough for John to contain his excitement. The many packages lying on Diane's bed held the means for him to fulfill a fantasy that had filled his mind for years. The pretty bras and skirts, the panties and hose, the blouses and the makeup, the shoes and wig beckoned him and his heart pounded in his chest. A portal was about to open to a world he had so desperately wanted to be in and now through Diane's love and kindness he was about to step through into it. Diane looked at John and said, "well, are you going to see if everything fits?" "Oh sure," John said, "where should I begin?" "Probably you want to take off you clothes. That's probably a good idea." John laughed. "Oh, OK. Are you going to watch me?" "I wouldn't miss it for the world. Besides, I can give you some girl to girl advice if necessary." John sheepishly removed his clothes, including the panties he had been wearing all day. His member was noticeably swollen in anticipation of the treat to come. "We've got to do something about your leg hair. I'll draw a bath for you and you'll have to shave it all off. We can't have you putting pantyhose on with legs like that. You'll also have to shave your armpits. Fortunately your chest hair hasn't come in yet." John had occasionally thought about shaving his legs but had never had had the courage to do so. Now it looked like the time to throw all caution to the wind had come. "One thing I've always wanted was to have my toe nails polished," John said not knowing where to go with the thought. "Sure, sounds like a good idea. Some nice bright red? Is that what you had in mind?" "Yeah, red would be perfect," John said. He couldn't wait to see what his toes would look like. The nice thing about toe nails was that he could keep the polish on until the spring when he would begin to wear sandals. Unfortunately, he would just as much like to have his finger nails bright red, but that was out of the question. The bath water was ready. Diane had put in some bath oils as well as foaming bath beads and John gingerly stepped into the tub and immersed himself in the fragrant water. Diane kneeled down next to the tub and gently washed John's back and then his arms and legs. He then felt her hands move in towards his private parts and with one hand she grabbed his butt and the other his balls. "Oh my goodness John, these really need scrubbing" she said while John writhed in pleasure and exclaimed his thankfulness to the deity in the form of a series of "oh God's!" and "lord above!" "You get so religious," Diane laughed. She continued to manipulate him until John began making a series of sounds almost like a death rattle. From a girls perspective that was maybe the nicest thing about have sex with men: there was never any ambiguity in their reactions to being felt up. Hit the right spot and they jumped around and made sounds. It was fun to say the least and she felt herself getting juicy between her legs. Much to John's frustration, Diane suddenly stopped and said, "I think you're well scrubbed and ready to come out of the tub now." "Give me a minute to collect myself," John said. Besides the fact that he could never get his panties on at this particular moment, he also knew that he was liable to have blue balls until finally, he hoped, Diane and he could make love later that evening. After a few minutes John got out of the tub and Diane helped dry him off. "You know you've given me blue balls," he said as he could begin to feel the discomfort. "I thought that was a myth," Diane said. "No, no myth. Ask any guy." "I'm sorry, What can I do to help?" "It's OK, it'll subside in a little while, but we'll have to make love later." "Good," Diane said, "in fact as soon as we get you all dressed up. Then we can play lesbians and romp together." John laughed. He would never have allowed himself even the fantasy of being a lesbian, and now it would come to pass. "So go put on some panties," Diane said. John selected one of the new panties, pulled off the price tag and put it on. Apart from the obvious, almost laughable difficulty he had tucking his organ into the light shiny pink material of the panty, the panty fit him quite well. "You are a perfect size 7 panty," Diane said, "and what bra do you want to wear?" "The pink one?" Diane emptied the bag containing panties and bras on the bed and picked up the pink bra and handed it over to John, "here you go." John took the bra from her and proceeded to put it on. He felt electrified with excitement. "It's comfortable," he said. "You are so definitely a 36C." Diane left the room and came back with the falsies she had mentioned in the store and gave them to him. He put them in his bra cups. "That's really nice." "I'm sure it will look and feel more realistic once we get you some nice silicon breast forms. Now put on your pantyhose and then your slip." John sat down, opened the package of pantyhose and took a pair out. He had often dreamed of wearing pantyhose and now he would get to have the experience. "I definitely need your help," John said, flustered at how he should proceed to put them on. "I've never taught anyone how to put on pantyhose," Diane said. "I guess for most girls it's their daughters that they teach, not their boy friends!" She came over and sat next to John and showed him every step of the process: lining them up, rolling them up, placing them over the toes on one foot, pulling them up, and then the other foot. Then came a little jig that pulled them up higher until they snugly held his rear end. John then put on a slip and then a blouse and skirt. Diane then applied some makeup to his face, doing his eyes, cheeks and lips and placed the wig on his head. The last thing was his shoes that had one inch heels. That John felt content didn't do justice to his emotion. No, he felt like he was arriving at a central place of his being that had, unseen, been drawing him nearer and nearer since he had been a young child. There would be no turning back anymore, he could never again suppress these desires and he was lashed to Diane for his happiness. He felt a vulnerability that sent shivers down his spine. It would take just one word from her saying that he looked ridiculous or that she thought he was pathetic in some way and his whole world would come crashing down around him. To be so happy and to find that it was based on reality and not fantasy was truly overwhelming. That Diane loved him for himself was a miracle; he had never in his wildest dreams imagined that such a woman existed. It was all very new to him. To be wearing pantyhose and a skirt and a woman's blouse and bra were deliciously new and exciting feelings. John allowed himself the luxury of feeling the feminine fabrics against his skin and he walked back and forth noting the gentle tugs and pressure of women's clothing. The hair on the wig gently brushed his cheeks and he savored the link it gave him to womanhood. As John starred at his image in the full sized mirror he felt a reverberation back and forth between seeing a voluptuous, sexy woman, recognizing that it was himself, appreciating the fact that a deep primal womanly persona in himself had appeared, loving the recognition of that persona, then being jolted back to realizing that it was John dressed up to look like a woman. After the jolt of recognition that brought him out of his reverie, he would see the beautiful hot girl in the mirror again and the process would repeat. Round and round the feelings played in his mind until he broke off his view and the cycle ended. To gain peace of mind he would have to accept the fact that he would always be part John, but the times when he could feel like a girl would always keep coming too. And when they came he could allow himself to just feel this side of himself through and through: he didn't need a reality check that he was still a boy also. He took another look at himself in the mirror and this time let the connection to that woman deepen, widen and fill all the recesses of his mind. Being a girl washed over himself and he felt gloriously happy. I am so truly a girl he felt deeply in his mind and then turned away when another thought of John started sneaking back in. He would work on that; in time he might be able to allow himself to be a girl without being haunted by John. "So what do you think?" Diane said. "You're a magician." "Nonsense. You are you. You're the pretty girl in the mirror. No amount of make up could create the pretty girl you see." "I feel so wonderful, Diane," he said tearing up. "I never ever thought that I'd get to be a woman. I mean I feel so much like I'm a woman. It's like some inner peace has been reached that I'd always been denied from having before." Diane took a good hard look at John and she felt a great pang of happiness in seeing how happy she had made him. There was no doubt in her mind that he was the winsome girl she saw as much as he was the male he had been heretofore. She found herself feeling great affection for him. Why do most women overlook the great advantage there could be with a guy like John? You had the chance to be on the same page emotionally with your partner. There would be no great divide separating you from the closeness and intimacy that so often was impossible to get with a real guy. Yet, they had all the right equipment for entertaining you. You could have your cake and eat it too. *** In the next several weeks Diane gave John many opportunities to dress up as a girl. Gradually he became more and more comfortable in the role of Diane's lover and "girl" confidant. Despite the nagging thought that a time would soon be coming when Diane would have him experience blow jobs, John was utterly content with his life. Diane did not share the same feelings, however, since she was increasingly wracked with guilt at the thought of how she was taking advantage of him. If she hadn't a desperate need for taking down the Beta Rho Alpha fraternity house, she wouldn't need for John to take her little test: she would accept his word that he wasn't interested in having his plumbing changed anytime in their lifetime together. Behind the scenes, Diane arranged the special evening that she needed for her plot. She had rented a private room at a nearby casino and had sent invitations to the senior class of the fraternity requesting their presence at a special party sponsored by a wealthy alumnus of the University and Beta Rho Alpha who wanted to show his appreciation for all that he had gotten when a student many years earlier. Diane had contracted with an escort service to provide a half dozen girls to flirt with the guys. Music would be playing, an open bar would be provided with everything from beer to whiskey available. Diane had even arranged for a private poker game to be run with a dealer from the casino. Each of the brot