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SOFT GUY/TOUGH GIRL By Elizabeth Parris MICHAEL'S CRUSH I had a crush on Lois all the way through grammar school and well into high school which is when this story starts. Lo, as her friends called her, was average height, with green eyes and black hair. Puberty came right on schedule and gifted her with long legs, nice wide hips, a perky tush, and a cute rounded tummy which she soon hid under a panty girdle, the curious foundation garment that was de rigueur for nice and even not so nice girls in the early fifties. Nature cheated Lois out of one important asset; she was almost through high school and still hadn't grown tits! This minor lack didn't stop me from thinking that Lo was as nearly perfect as any human female need be. Lois tolerated me, teased me and made me the target of her moods. Since I was intimidated by most girls for reasons I didn't understand there was no easy way to resist her attitude which was a combination of flirting, teasing, and bullying. She reminded me and everyone else who would listen that she was far above everyone else in our neighborhood because she was the one who took piano lessons and dance lessons. Her mother, an attractive war widow, had attended a fancy women's college in New England which Lo somehow felt was something that elevated her own status. Lo's never asked me to but I took typing, steno and bookkeeping classes in order to fill out my course requirements for high school graduation. All of these courses were part of the Secretarial studies department, hardly a place with a very masculine appeal. We both agreed that learning to be an efficient typist would help when it came to writing up term papers and reports. My unspoken hope was that it would give me a better chance of being in more classes with Lois. Steno might help with note taking but that was stretching it. Maybe, just maybe Lois was making a fool of me. Since I was the only boy in most of these classes, the girls didn't hesitate to talk girl stuff while waiting for class to start. They would congregate in a corner of the room and talk softly about who was letting who get to first base or second base, about the latest fashions both in outer and inner wear. As time went on they either accepted me or thought of me as invisible and chatted in ordinary tones despite my presence. Some of the girls openly admitted or even boasted practicing French kissing with other girls. At first I blushed but soon learned to enjoy listening as the girls talked about their practicing. There were subtle hints accompanied by knowing grins between two or three girls when one of them hinted at activities more intimate than French kissing. It made me wonder whether or not these so-called practices weren't rehearsal but an end in it self. Of course I envied some of the girls who French kissed with other girls. I would have gladly helped them hone their skills by practicing my own yet untested and untasted ability in that art. Excited envy has to be the term to describe my reaction as the girls talked about the latest brassiere or girdle and whether the discomfort of wearing certain styles was worth the added sexiness. As much as I would have loved to try on and even wear enticing and ego boosting unmentionables, I put such thoughts aside as being unattainable. That I no longer allowed myself to yearn to try those fascinating items of intimate apparel didn't stop me from not so unconsciously emulating the sitting postures of my much envied classmates. Sitting with my legs crossed at the ankles or thigh over thigh became my usual way of sitting as opposed to the ankle or calf on thigh favored by most boys. Never again would I allow myself to sit with my thighs spread wide in the tasteless pose that seemed natural to most boys. There were no padded brassieres back then, not really, just breast pads which were universally referred to as falsies. Lo's conceit convinced her that she was beautiful and sexy enough as she was and refused to consider repackaging her underdone cupcakes. Reality set in around the middle of sophomore year when upperclassmen stopped dating her and paid more attention to the more developed girls but, strictly speaking, less beautiful coeds. Thus it was that Lo settled into her books and became what was called a "grind," a derisive term for any kid who spent too much time studying and reading actual books. She also resumed dance lessons which she had given up after eighth grade because the lessons took time away from her playing the role of queen bee in our grammar school and neighborhood. Big mistake because once we were in high school she had competition for guys' attention. She might have been better off continuing her dance lessons which could have gotten her into the high school dance club, a source of status. Taking dance lessons again was intended to create an aura of being an ethereal, arty being, an aura that I was sure Lo was using to give herself an air of mystery and superiority to make up for her lack of more obvious female attractions. In case you're wondering about me, there's not much to say. I was on the taller side of average, wiry, nice looking rather than masculine type handsome, and played guitar not well but acceptably. Lessons might have helped. In freshman year of high school, I tried to switch to the double bass for two reasons; one was that the high school orchestra needed bass players. I also thought I might get into a jazz ensemble which would get me noticed by girls. My mother and father were unsupportive of the proposed change because father wasn't going to waste any more money on my "craziness" which is what the called he aspirations toward culture. My father, who hadn't lived with us for as long as I could remember, was determined to make life as difficult as he possible could for Mommy and me. Although he supposedly made a good living he was always late with alimony and support payments when he sent them at all. Why I wanted to get noticed by girls was something that wasn't clear since Lois was the only girl I ever felt comfortable being around. She sensed early in grammar school that I was drawn to her and that I would do almost anything to win her approval. By the time we were in fifth grade I was meeting her at the local public library to pick out the reference books she needed for school reports and writing the outlines for her. Sometimes she paid attention to what I was doing but when some of the popular boys were around, she just smiled and made goo-goo eyes at them. My ball playing skills were adequate and then some in stickball and handball. My problem was that I wasn't aggressive enough socially and physically to be a really competitive jock. I avoided fights even though I could usually hold my own or even come out ahead. This is as good a time as any to let you know that nature had cheated me in a way similar to the way Lois had been cheated. Before you jump to any conclusions about my anatomy and how well it did or didn't function let me tell you I was well put together down there and my range when I jerked off was pretty good. The problem was when my voice started to change it never got very far. You know how boys whose voices are beginning to change are often mistaken for girls on the phone. My voice never changed beyond that point. There were times when being called "Miss" by telephone operators and information ladies at stores really got me down. That might have been because it was something that was supposed to annoy boys. I soon accepted that that was the way it was going to be for a long time to come so I adapted and even learned to enjoy it. My reasoning was that it was like playing a joke on the person I was talking to over the phone by fooling them into thinking they were talking to a girl to a young woman. It was self-deception since it was unlikely that anyone might think that mine was the voice of a teenage boy no matter how much I might try. My body never broadened or filled out nor did body hair appear except for a light down along my legs. There was a triangle of thick, dark hair at my groin and some underarm hair. It was more like the body of a girl on the verge adolescence than that of a teenaged boy. Strange to say, I had no problem accepting that this was the way I would always be even though I did get some teasing in the school locker room. I would rather be the way I was than to look like a chimpanzee the way some of the boys did. //////////////////////////////////////////////////////////////////////// AN INCIDENT It wasn't until one Friday night early in junior year outside a local movie house that I got my reputation for never backing down. A couple of senior boys were trying to get Lo into their car. Lo had led them on but then chickened out. She screamed and clawed one of them in the face when he tried to put his hands on her. I jumped in to help her. It was just chance that I ended up standing in front of the bigger guy who happened to be a big-shot jock. My heart was in my mouth as I snarled at the cretin. Much to my surprise, he froze, then took a step back. My fists were at my side leaving me wide open but that didn't seem to matter to him. "Cool it, kid. No one's looking for trouble with you. This cock-tease over here..." Sensing that I had some vague advantage for at least a couple of minutes, I stood glaring at him with my hands on my hips, a decidedly unmanly posture. The jerk still acted like he was intimidated. "Just take your toilet mouth and leave her alone." "We were just going anyhow. No one needs a stuck up..." That did it. I stuck out my arms and threw my full weight at him, knocking him off balance so that he staggered back and nearly fell. "Lucky shot," he said turning purple with rage but still backing away from me much to the amusement of the crowd of teens that had collected around us. "I won't fight you 'cause everyone knows what a faggot you really are," was his parting taunt as he slid into the passenger seat of the car. Lois then told me off! I was suddenly a barbarian who embarrassed her by interfering in her personal business. That was the end of Lo as far as I was concerned. We were little more than nodding acquaintances for a long time after that, not that we were ever much more than that once we entered high school. It was a kind of poetic justice that she was not only not considered dating material by upperclassmen but that she was also teased by some guys and a lot of less snobby girls because of her lack of mammary charms. The girls were worse than the boys because they almost always teased her to her face in the halls and in the girls' locker room. It was a few weeks before spring recess that Lois started warming up to me again. "Mick, why not come over my house and listen to records Sunday night? Besides I need a guy's opinion of some new clothes." "That sounds swell. It's just that I wonder why you want my opinion and not some of those goons you're always smiling at in the cafeteria." "I f you must know, I feel safe around you. Besides that you're one of the few boys ever who has any sense of color or..." "Sure thing," I said without waiting for her to finish her sentence. "Nice of you to ask me to..." I was unwilling to finish my own sentence aloud but that didn't mean I wasn't finishing the thought in my own mind. At least I'm useful to you, Lo. Go ahead and play me for a chump. I'll do almost anything to spend time with you. Even if you poke me and pinch me like you did back in grammar school, I'll stick around and do whatever you ask. //////////////////////////////////////////////////////////////////////// EXPERIMENTING WITH LOIS Lo's mom was leaving to play cards at a friend's house. I thought she looked pretty spiffy for a night of card playing with her lady friends. Mrs. Vaughn assure me that Lois would be with me shortly and suggested I sit down so she we could catch up. Mrs. Vaughn gestured for me to have seat on the couch and then seated herself on a Queen Anne chair facing me. I watched her move gracefully across the room. My eyes locked on her legs made all the more shapely by her high heeled ankle strap shoes and full fashioned stockings with flawlessly straight seams. From my seated perspective on the low couch, I was treated to a glimpse of her dark net petti. I all but blushed openly as I wondered whether she was wearing a girdle or a garter belt and if all her underthings were color coordinated. It was as if my heart stopped beating when Mrs. Vaughn paused in front of her chair, ran her finger tip along the seam of one stocking and in doing so actually raised her skirt ever so slightly but high enough for me to glimpse the back of her thigh a few inches above her knee. Then with a graceful movement, she gathered her skirt and petti, turned to face me and sat. She crossed her legs and let her skirt and petti fall loosely in a way that offered me an unfettered view of her legs right up to the edge of the darker tops of her tinted hose. "Oh do relax, Michael. You used to visit with Lois often. It's been a while, I know, but that's no reason for you be so stiff and rigid. I've always thought better of you than I do of any of the other boys Lois invites over; not that there are many of them. Matter of fact, you seem so much nicer than those catty girls she aspires to be like." Then, almost as an aside, she remarked that my voice was exceptionally pleasant; 'soothing' was the word she used. "With your voice quality you really should work on developing singing skills. Your potential is so much better than Lois's girl friends who cackle around the piano and think they're singing." I immediately wondered why Mrs. Vaughn kept comparing me to some girls and was about to change the subject when Lo' called down from upstairs. "Mother, is Mickey here yet? Just send him up as soon as he gets here." "Michael, it's time for you to go upstairs to be with Lois and time for me to be on my way." She stood, shook out her petti and skirt and moved toward me as I got up from the couch. She glanced over her shoulder toward the stairway as if to see if Lois had come down and the spoke softly. "Mickey, Lois will be away most of the summer but I would like vey much of you would stop by so we can get to know each other better." The upstairs hall looked the same as it did a few years ago when I used to visit Lois often. A minor difference was the few additional family photos on the walls. One caught my eye more than any other: it was Lois looking dreamy in her eight grade graduation photo. It was definitely not thoughts of me that put that dreamy look on her face. At that moment Lo called to be from down the hall. "Come on up, Mickey. I've got some surprised for you." Her voice came from Mrs. Vaughn's sewing room at the end of the hall. No choice but to follow Lo's voice. Lo deliberately stood with her back to me as I stepped through the doorway. She wore a chic skirt with only a single unstarched petti as opposed to the multi-layered, heavily starched crinoline pettis so popular in that era. A not quite opaque blouse allowed her light blue brassiere to show through. I swallowed hard as she eased the blouse out of her skirt and held my breath as her hands moved up and to her front. Although her back was to me, I was all but certain she was unbuttoning her blouse! She confirmed that impression by sliding the blouse off her shoulders and halfway down her shoulder blades. "Close your eyes now and keep them closed," she said softly but with authority. I heard the rustle of fabric and sensed that Lo was now close to me. "Go ahead and open your eyes. You can look but no touching." She stood a couple of feet in front of me, nude from the waist up except for her blue bra. I was astounded by this but also by the fact that Lo appeared to have grown tits overnight. It occurred to me that these might have been falsies but falsies didn't have nipples and the outline of Lo's nipples showed through the flimsy cotton fabric of her bra. The bra, as pretty and as modest as it was, didn't quite contain her boobs which were visible as soft swells of flesh above the edge of the bra. The sudden change from a day earlier seemed impossible but true until I noticed the tiny brass safety pin on each bra cup where the strap was attached, a sure sign the falsies were pinned in place. "You can stop staring now that you've figured it out. I thought if these falsies could fool you, they can fool anyone, any boy, any girl." Had Lo somehow guessed that I spent a lot of time studying ads for bras & girdles in the Sunday Times Magazine? (In the fifties the Sunday New York Times Magazine was referred to in the advertising business as the "girdle gazette" because of the large number of ads for foundations garments that graced its pages.) A greater fear than that popped into my head; Lo might possibly have sensed that I wondered how these exclusively feminine might feel to the wearer and that I longed to try them on. That isn't quite honest. It wasn't that I simply wanted to try on these enticing unmentionables. No, I wanted to wear them and other exclusively female accessories for longer periods. Thinking about this as I jerked off over these ads was overwhelming, so overwhelming that I dared not plan to make my fantasy into reality. Bliss is the only word that adequately describes Lo's air of calm and serenity as she finished speaking. Happy for her though I was, my thoughts ran wild. The only girl who didn't completely intimidate me simply by being near was standing in front of me wearing nothing above the waist but a bra and I stood there not knowing what to say of do. "Come on, Mickey. Say something, anything." Her voice was soft but with an underlying intensity. "Be careful, Lois." "What ever do you mean by that? Once I show up in school looking my age, you know what I mean, they'll stop calling me nasty names and..." "Lo, they won't. You look fantastic and you do look your age with or without those things in your bra. Think about it for a minute. Show up in school or around the neighborhood, everyone'll pick up on the sudden change. They'll make your life a worse hell than before." She was biting hard on her lower lip as I spoke. Tears started to form in her eyes giving her a sad beauty. Her sadness turned to anger which I was afraid might be taken out on me. "Mickey, you're the only person in that entire high school that cares enough about me to tell me what I should be told and not what they think will get something from me. Lying bunch of shits!" "You know, Lo, maybe of you started with a smaller size..." "I could never afford that. Mommy treated me to these so I could look more...more mature in some photographs she's having taken of me for a summer program application. And I was silly enough to think I could wear them to school." Her shoulders heaved as if she was crying silently. I was stupid enough to try to make a joke of her undoubtedly expensive and certainly very convincing falsies. "That would be silly. You're so beautiful and so sexy without them. Forget those cows and their dumb jock boyfriends. Just get by on what you have until you start meeting guys who are grownup enough to appreciate you for who you are. Anyone could look good if they stuck falsies like those in their bra." "Anyone?" She started to turn toward me. "Yeah, anyone!" "Even you, Mickey?" I felt my face grow warm and knew I was blushing. Lo had touched on a secret fascination that had been part of me for as long as I could recall. Perhaps a desire is a more accurate word to describe what I felt. Ever since I could remember I envied girls for their clothes which allowed them so much more than boys. Little girls could get almost anything they wanted from adults by flashing a smile or showing their pettis. As they grew a tiny bit older they quickly learned more effective ways to get what they want from grownups and boys their own age and older. Girls could express their moods by crying, whining, stamping their feet or simply pouting. Boys would have been ridiculed or spanked on the spot for showing behavior like that. But boys could never ever hit a girl even if she teased him mercilessly or even hit him. Since I was considered 'pretty' for a boy, I had wondered if wearing pretty clothes like girls the girls wore would allow me those same privileges. My mind raced from reflecting on this idea of female privilege to what it might feel like physically and otherwise to wear a well filled bra and then slip on all the other feminine finery so well hidden under clothing in that more modest era. That my cock was responding to these fantasies was obvious to me and had to be obvious to Lois. The look on Lo's face went from hopeless gloom to cheerfully serious in a few seconds. "Mickey!" Lo demanded my attention. "I just know you want to cheer me up." Her eyes were focused a few inches below my belt. "I challenge you to prove that anyone, just anyone including you would look good in a bra and expensive falsies." I tried to think of some reason to refuse even though I wanted more than anything to go along with her unstated idea that I try on a bra. "Oh, just forget it. Here I was absolutely convinced that we could be real pals again. Forget what I said and if you ever tell a single soul, I'll make you sorry and don't think I can't." Was she teasing or did she really mean what she said? Lo had me intimidated while managing to keep me turned on by her not so absurd suggestion that I try on her bra. Of course I was terrified that she might blab about how she got me to do it. But who would believe her? Then I considered that a lot of cliques thought of me as a faggot, so there might be enough kids who, whether they believed it or not, would have another excuse to make my life miserable. "Okay, Mickey. You really think you've got me fooled. Well, you don't. I can see that you want more than anything to go along with what my idea. You know it'll be fun." She paused and looked at me like a cat about to assault a canary. Her eyes twinkled as she tilted her head and thrust her tongue out of the corner of her mouth to moisten her lips. "I get it! Once you wear my bra for even a few minutes, you're going to need to try more of my things and before you know it you'll want your own stuff. But you're afraid you'll feel guilty. Don't deny it. I'm right, aren't I?" A sheepish grin was all that the response I could muster. Lo was on the mark with everything she was saying. "Well, Mr. Mickey, allow me to take responsibility for what's about to happen. That way you can't blame yourself." Again with that catlike leer, she launched herself at me so that her hands struck my shoulders and the full force of her body hit my midsection sending me sprawling on my back with Lo landing on me. By the time I caught my breath, Lo was sitting astride my chest with her knees holding my shoulders down in a schoolyard pin. Managing to raise my head gave me an unfettered view of Lo's panty crotch. "Like what you see, don't you," she said in a voice that was both mocking and sensual. "Of course you, do. I better check, though to make sure that the rumors about you aren't really true." Lo was completely in control bit physically and emotionally as she leaned back and ran her hand over my crotch feeling both my hardening dick and my balls. Although I loved ever second of it, there was enough macho in me that I just had to make an effort to resist so I tried to buck Lois off me. Her response was to grab my balls through my jeans and squeeze. She smiled down at me as I grimaced at the sudden and unexpected pain. Her hand patted my now hard cock. "Ohh, he likes being pinned down by a girl. Would it be the same with any girl or am I the special girl, the only one you'll submit to?" I raised my head in a feeble attempt to nod that Lo was the only girl who could mean anything to me. It was then that the dark spot on her panty crotch caught my attention. Given my naivet?, this slowly growing apparently wet spot was a mystery at which I could only guess. Meanwhile Lois was growing impatient with my silent answer. "Mickey, love, you're not answering my question. Nodding "yes" is an impossible answer when I've asked you to make a choice." "Okay, Lo. You're the only girl I would ever want to please. But, but your panties..." "Mickey, it surprised me too. I've never ever been this hot before!" With that confession, Lois stood up, smoothed her skirt down as she watched me sit up leaning back on my elbows. Taking me by the hand, she helped me onto my feet. My heart beat rapidly, both from being aroused by having been so easily overpowered by Lois and by the fact that she was now directly in front of me. I held my breath as she unbuttoned my polo shirt and raised it over my body to my chest. No further hint was necessary as my hands took over from hers. As the shirt fell to the floor, floor Lois stepped away from me and opened her dresser drawer. "You're special to me, Mickey, but I'm not nearly ready to show you my tits. But we both we want you in a bra. As for my tits; soon, I promise but not tonight." Lo took out a bra similar to the one she was wearing and then from the back of the bottom drawer produced a pair of ordinary falsies. The scene that was being played out was doubtlessly meant to entice while frustrating my long hidden urge to wear feminine foundations if only for a few moments. My eyes went back and forth between Lois's scantly clad upper body, more specifically the bra itself, and the items she was removing from her dresser. It felt as if Lois was guiding me closer to the moment when my fantasies would evolve into actuality. My sense of the possible forced me to reject that thought as just another facet of my perverse and what I believed to be my unique wishes. As my mind raced from hope to gloom, Lois took a small cloisonn? box from the drawer, opened it and withdrew a few tiny brass safety pins, mates of those that were holding the breast forms in their place in her bra. As she started to pin the cheaper falsies into the second bra, she turned to me and spoke softly with a wry smile. "Don't stand there gaping, Mickey. Take off your cami, er undershirt so I can teach you to put on your own bra. You do realize there's a lot of catching up to do!" I wondered if I could ever learn to be dexterous enough to maneuver miniature safety pins with the ease Lois did. I doubted it. She faced me directly and, in mock amazement, began to deride me for having only gotten no further along in removing my undershirt. "Gosh, Mickey, what on earth are you waiting for? Do you want to break the mood, slow things until we're both bored with waiting? I get it. You want me to really take over! Remember you're asking for it!" Her mock amazement turned to convincing impatience and then to anger. She flung the bra I was to wear at me with such speed and fury that I was barely able to catch it. I couldn't help but be aware of the feel of the bra in my hand nor fight the need to look at the detailing, the shape and texture. I'm sure Lois had sensed I would focus on the bra and not keep my eyes on her because she rushed at me, grabbed the edge of my polo and yanked it over my head but stopped short of pulling it off me. Unable to see with the shirt over my head, I started to panic, to grope wildly toward wherever I thought Lois might be. I had held on my own even when I came out the loser in fights against bigger and stronger boys. This was different. Lois, although similar in size and weight to me, was incredibly fast. She would move in and jab my tummy, poke her finger into the pit of my belly and then move out of reach. Her foot would lash out against the back of my knee causing it give way almost completely so that I has to struggle to retain my footing. Mercifully, Lo brought this encounter to a close by grasping the shirt, twisting my body like a steering wheel as she used her foot to sweep my legs out from under me. As I lay panting on the floor, I gathered my wits and caught my breath enough to sit up and pull the offending polo completely off. Lo dropped to her knees beside me and frantically apologized with tears in her eyes. "Poor Mickey, you could have been hurt. Honestly, I really didn't mean to get carried away like I just did. It's just that I was afraid you'd leave. I just know you'll forgive me." After a very brief pause she added with gloating smile, "You wouldn't dare do otherwise." I nodded and started to get up but Lo leaned over my body and ran her hand over my tummy. "Gosh, you're skin is so smooth, not at all like those apes who try to make out with me at parties or at the movies. They take my hand and put it against their disgusting furry bodies while they try to cop a feel." There was genuine hatred in her eyes, hatred directed at the boys who had tried to make out with her. "Just 'cause I'm flat, they thought I'd fall all over them just to get a date. I showed them every single time. It was easy to hurt them by just grabbing their precious balls and squeezing. Most of those goons just shrieked like the pussies they really are. A few of them just screwed up their faces trying to pretend I wasn't hurting them but not for long. Those were the ones I made cry. Of course not a single one of them would ever tell anyone that flat Lois hurt them and hurt them badly so no one'll ever know the price of trying to get a cheap feel from Lo." Lois kissed me gently on the lips and then bounded to her feet as if this expression of anger and hatred at boys who thought she would come across out of thankfulness to anyone who paid attention to her despite her obvious lack of certain charms. She extended her hand to me and helped me to my feet. "I'm sorry you had to listen to me go on about those drips. Say, we've got to stop wasting time and get going with...you know. She picked up the bra that was intended for me and started to hand it to me but paused. "This won't work," she said as her face fell. Then she reached for my pants, undid my belt and fly before smiling once again. "Wearing guy's pants with a bra is going to make you look silly. You're going to have to wear panties in order for this to work." I was elated at the thought of dressing in bra and panties even under these weird circumstances but dared not let on that this was fine with me. Trying to look like I was having trouble making up mind was anything but easy as Lois eased my pants down to my ankles. She couldn't help but notice the hard-on that was pressing against my white cotton boy briefs. Lois turned from me and again opened a dresser drawer, not the same drawer form which she took the bra and falsies. As I hoped, she took out a pair of cotton panties, the cotton of which was so much finer and more delicate than my coarse underpants. "These everyday panties will do for a beginner like you. Little girls who haven't had a period shouldn't be allowed to wear cute big girl undies and certainly not undies that are meant to turn on...turn guys on and maybe even more important, to turn themselves on." By now I had willingly taken of my pants and laid them over a chair. Lois nodded approval as she looked me up and down. Feeling embarrassed as her gaze lingered at my half hard dick. I crossed my hands at the wrists in a pathetic attempt to cover up. Rather than tease me or berate me again, Lois unzipped the back zipper of her skirt and guided to her ankles before stepping out of it. The outline of her legs showed through the white diaphanous petti. It evident that her Van Raalte panties matched her bra. My disappointment at her not removing either her bra or panties was only momentary. With her skirt draped over one arm she walked to her closet, took out a hanger and hung the skirt before returning it the closet. Each of her movements were fluid and graceful, enhanced rather than concealed he panty encased loins and tush. As she neared me, Lo paused and allowed her petti to fall in a heap around her ankles. She had become a modern incarnation of Venus rising from the sea, in this situation a sea of white gossamer. My hard-on was raging once again. "Copy what I do. You're such a natural at this that I just know won't need step by step instructions. Are you okay with that?" I nodded and whispered, "Oh, yes, Lois. I'm more than okay with it." "Gee whiz, Mickey, when you talk in the sexy whisper you're unbelievably sexy." She moved toward me, took me in her arms and kissed me. Her hand grasped the hair in back of my head and forced it back so my face was up. Lo's breath on my neck tickled in away that I had never known. Then her lips closed over the skin of my throat. Facing me again as she took a breath, an odd look came over, part pleasure and part hunger but all sex. Her mouth covered mine; her tongue probed my mouth before she pushed me away. "Mickey, I know this is hard for you to believe but I've never ever kissed a boy like that. Don't look at me like that. You're wondering how I can kiss like that without being taught. You're right but it wasn't taught to me by those clumsy drips called boys. No, I learned from girls at summer arts programs and we practiced until I became really good at kissing. And I practiced with girls from school until they used what I taught them to keep their boyfriends interested in them and their big ugly cow tits. But, Mickey, darling, you've shown more talent in that quickie kiss than all those girls and their jerk-off boyfriends combined. I promise we'll finish the lesson but first we have to finish changing." Lo's anger both intimidated me and heightened my arousal. To be controlled by an attractive girl my age appealed to me in ways I couldn't understand. All I knew at that moment was that my cock was beginning to twitch. Watching Lois turn partly to the side, thrust her bottom almost imperceptibly caught my complete attention while clearing my mind of any stray thoughts. "Just do what I do," she said matter-of-factly. My imitation of every nuance of her movement was received with approval by the girl was well on her way to becoming my mentor in the art of sex. She got as far as wiggling her panties down to the base of tush when I had what amounted to a premature and spontaneous ejaculation. Lois, rather than being angry was amused. "Now that that's over, we can go on without worrying ...at least for a few mutes. Wow, you pants are soaked. Get rid of them in my hamper. Wipe yourself and I'll help you get into your panties." She repositioned her panties leaving me exposed as if it were the most ordinary situation in the world. My mind tried to make sense of what she had just said. Oh, my Lord! She really said 'panties.' Can't be. I must have heard her wrong or it's some kind of crazy wishful thinking. This is something I've dreamed about but now it's getting me scared! "Mickey, stop being a slow poke. You're not scared of what you really want, are you?" "I'm not scared at all. It's just, just that I wasn't ready for this, not all at once." "Take them by the waist band," Lo spoke in normal conversational tones as she handed me the panties. "That's how we girls do it and then hold them and look to see which way is the front." The soft cotton felt so good between my finger tips that my hands began to quiver as I felt renewed energy start to flow through my groin. It felt good to be standing thee nude but for my socks, the blindingly white cotton panties held front of me like a ritual object raised toward heaven in a rite meant to assure that my innermost dreams would be reality. But this wasn't simply a ritual, it was an ordeal imposed by Lois as if she were the priestess charged with testing me, the neophyte hoping fro acceptance into a mysterious and wonderful cult. "Good work." Lois's voice cheered me on. "Now step into them, hold the waist ban, leg opening at the same time if you can so they don't get too stretched out. Neat work! Didn't I say you're a natural? No watch me." Lo guided me to the bed and sat me on the edge and then positioned me so that I was reclining against her pillows with one leg on the bed and the other draped over the edge. It was a seductive pose that felt ever so right even without the bra and falsies I was already thinking of as my own. She again opened the dresser drawers and took out two items and placed them on the dresser. Facing me again, she repeated the quick but very seductive and feminine doffing of her panties. Unlike a few moments ago when she demonstrated this move for my instruction, she ended holding the panties between her thumb and forefinger while nonchalantly allowing me a prolonged, unfettered view of the perfect triangle that was her thick, dark pubic hair. She beckoned to me to approach her which I did without hesitation but trying to appear casual. I took the panties from her hand, went into the adjacent bathroom where I dropped them into the hamper where my cum soaked underpants had ended up. Do I need to add that I managed a few furtive sniffs of her panties? Lois had gotten her fresh panties on as far as the top of her thighs when I walked back into the bedroom. She turned her back to me as she pulled the panties into place and then hooked her thumbs under the narrow elastic leg bands adjusting the back of the skimpy panties to fully conceal s much of her tush as they possibly could. Lo slowly turned toward me caressing her bare waist before gliding her finger tips over the satin panty that clung to her hips. Be assured that these were the brief panties that were almost the only style to be had in the fifties yet this pair was so different from those that had so aroused in ads. The waist band rode low enough on her rounded tummy to reveal all but the very bottom of her deep belly button. Confusion began to override all other thoughts and emotions as I silently struggled to anticipate what was expected of me. It became plain that Lois remained very much in charge and that she would control what was and what was not going to happen. Again she stood directly in front of me and sneered derisively as she studied me from head to toe and back again. The slightest nod from Lo reassured me that I was somehow worthy; but of what? With deliberate slowness her hand moved toward my chest; so slowly that a sense of apprehension and anticipation began to overwhelm me. Her palm moved lightly over my nipples creating sending chills through my chest leaving me hoping that Lois would teach the why girls reputedly enjoyed having their breasts caressed. That disdainful facial expression that was both a smile and sneer said it was not to be, at least not then. Her hands rested on my shoulders, gently at first but with ever increasing pressure. Her nails dug into me skin as she pressed down hard enough for me to drop to my knees in front of her. My eyes were level with her tummy as she placed a hand on each side of my face and moved me to inches from her deep belly button. "Mmm," she aid softly. "Your breath tickles so nicely. Go ahead, kiss me there." Lo pressed my face against her tummy. "No, you silly creature; not just your lips like your kissing an old aunt. Use your tongue." Lo's admonition somehow made me react instinctively. I lowered my chin so that I could run my tongue over the front of her panties from a few inches below the waist band to her belly button. Her skin was cool as my tongue circled, wiggling as it moved. Lo's reaction was to shove me onto my back. "Oh, Lo, I'm sorry if..." "Stop sounding so corny. Don't even think about feeling sorry when you're pleasuring me. It just felt too good to..." Without finishing her thought Lo fell to her knees next to me, covered my mouth with hers and massaged my balls through my panties. I was powerless to stop her, powerless to react in any way but to passively accept her ever more passionate attentions. Lo's mouth moved over my exposed throat, her tongue darting in and out, alternating with gentle nibbles of her teeth. Meanwhile the hell of her hand glided over the underside my cock. I writhed while experiencing more intense arousal than I had ever dreamed possible. Moans turned to high pitched whimpers as Lo pulled my panties below my balls. As she clutched my balls, she brought her face to my chest, ran her tongue in tightening circles around my nipples driving me into frenzy. Each time I moved to hold her, to reciprocate her every caress, her hand tightened on my balls forcing me to stop out of pain, pain which heightened my arousal and made me long for Lo to inflict more and other agonies on me. Now she sucked my nipples as her hand grasped my cock. Then Lo suddenly paused and sat back on her heels looking triumphantly down at me. A pearl of precum had formed on the tip of my dick. Lois picked it up on her finger tip and held it a few inches from lips. I complied with her unspoken demand by raising my head and taking the drop of precum onto the tip of my tongue, savoring the taste and swallowing before sucking gently on her finger. "Mickey, you're so willing to please me that I 'm going to do something to you that I never thought I would do to any boy, ever." I thought of asking what she was going to do but her hand covered my mouth before I could say a word. Lois put her index finger to her mouth in the classic "shush" sign. I lay panting in fear and anticipation as she shifted so that one knee was on each side of my head. Her fingers encircled the base of my cock as her tongue circled the rim. "There's really so many ways to make this last but I know you won't hold out." That said, she took my cockhead in her mouth. I was twitching now as electricity started to generate in my groin. Lois took her mouth from my cockhead, pressed the shaft against my belly and licked the under side of the shaft from base to head. I held my breath as her tongue again circled the rim. My cock throbbed as she took the head into her mouth. She milked the shaft as I exploded into her mouth in wave after wave of orgasm. Lo's panty crotch was dripping wet as she sat with her knees drawn to her chest looking at me as I lay depleted of cum and strength. "Yes, it really is true that men and boys are helpless after being brought off by a female who knows her power. You liked that, I know. We'll have to keep practicing together but next time it will last. Oh, and you're going to satisfy me by...by lip service Watching every nuance of Lo's movements as she got to her feet, I wondered what she meant by "lip service." Lo distracted me from wondering what she meant as walked toward the door to the bathroom and unselfconsciously lowered her panties to the top of her rear cleavage. She stood just inside the bathroom doorway as she allowed the panties to fall to her ankles before kicking them aside. My jaw dropped at the sight of her back completely nude but for the narrow blue band of elastic fabric across her upper torso. With the flexibility peculiar to girls and women, she reached behind her back and unhooked the closure of the bra. Then she kicked the door closed. My cock, despite the recent exertions, was no longer quite flaccid as the sound of the shower came from the bathroom. A few minutes later Lois emerged wearing a bath towel as if it were a sarong. "Your turn," she announced. "Don't be such a prude. You do need to shower, you know. And don't worry about your underpants. They're gross to begin with and even more gross since you came in them. Oh, just relax, I'll wash them with some of my things and you can take them next time you come over." "But what'll I wear under my jeans?" "Really, that's a silly question. You can wear nothing or you can borrow a pair of my panties. Plain cotton will work and no one will ever notice. Mickey, get that dazed look off your face. You know you want to wear my things. Just admit it and we'll both feel a lot better." A moment's hesitation and a deep breath and I knew I would no loner deny my secret fantasies, at least not to Lois nor to myself. "Lo, you can't begin to know how right you are. Help me, please." "I promise," was all she said. Lois watched as I came out of the bathroom wearing only the yellow cotton briefs she had left on the vanity counter. Without thinking I emulated Lo's gesture by hooking my thumbs into the leg bands and slowly guiding the panty over my bottom. My reward was two fold. First was the effortless way and graceful way I was able to move through this classic feminine ploy as if it was something I had been practicing forever; second was the nod of approval and delight that this got from Lois. By now she had dressed in a cowl collar top and slacks, slacks that though not tastelessly tight flowed over the curves of her hips and accented her pert derriere. Seated now at her vanity table, Lo held her hairbrush over her shoulder as if beckoning me to approach. I took the hairbrush form her and slowly brushed her hair while furtively studying my own reflection in the vanity table mirror. My firm slender torso was all I could see but that made me focus my attention on the yellow panties that so nicely highlighted the outline of my dick. Even the most casual observer would be able to see that I was circumcised. Lois reached up, took the hair brush from me. "Now it's my turn to play the lady's maid." I looked up at Lois's reflection as she brushed my hair. This felt both erotic and natural as my cock began to stiffen. Long suppressed memories returned; visual recollections of my mother brushing my hair, hair that was kept too long for a boy's. "It would only take the least touch of lipstick to completely transform you. Relax, though. There's not enough time. Now get dressed." There was no hug at the door as I left but there was a kiss. Lois brought her moist lips to mine, pressed them over my lower lip and then slid her tongue into my mouth. It glided over the roof my mouth. I started to wrap my arms around Lois only to be rewarded by the edge of Lois's fist slamming into my balls. "Not now, Mickey. Neighbors might see. There'll be more to come, I promise." //////////////////////////////////////////////////////////////////////// ONE SMALL STEP I walked toward home with the realization and hope that this was the first step in a new road, a road that would allow me to discover what I could really be. First I would need to learn the intricate mysteries of feminine lingerie and foundations. Magazines would be my first source. It would be foolish to buy "Coed Life & Fashions" or "Seventeen" at the local news stands but I resolved to buy these and other fashion magazines away from the neighborhood. By the time I got home I was wondering about buying everyday panties at a five and ten away from home. //////////////////////////////////////////////////////////////////////// BACK TO SCHOOL That Monday morning Lo came up to me as we entered the school building. "Mickey, you're acting like a drip," she admonished. "I don't get it." "If you enjoyed our Friday visit half as much as I did, you would have called." Then she slipped me an envelope. "Put this in your notebook and read it in private." I looked at the envelope as I stowed my things in my locker. It was a blue envelope with scalloped edging on the sealed flap. It was addressed to "MIKI." The feminine spelling of my nickname made my stomach jump. In class I practiced writing my name as "Miki" or Micki" with tiny hearts replacing the dots over the 'i' before deciding I preferred "Miki" as being more different from the male spelling I had been saddled with for too long. There was no point in lingering around the school steps at dismissal time other than to catch a glimpse of Lois. She was nowhere to be seen so I took the city bus home and went directly to my room. It made no sense but I locked the bedroom door behind me before slipping off my shoes and opening the note from Lois. Dear Miki: Last night was wonderful. I felt so free when we did what we did and now know we're both ready to become, not become but explore what we really need tobe. I was unkind, even cruel to you. You had become my way of getting back at all those creeps who still torment me, only now they do it mostly behind my back my back. You must know that you're a target of their ridicule just as I am only they avoid you because you sometimes fight back. Thinking about that has given me an idea. My mom will, if nagged enough, will let me take all kinds of self-defense classes and then I can train you. That way we both can hurt anyone who dares to torment us. That's not the only reason I'm writing this note. You see, I've never been able to cum with a boy before. Yes, girls can cum but it's much harder for us than it is for boys. Just seeing you in panties and imagining what you would be like if you were wearing hose and heels or even makeup. And with your voice there's no one who wouldn't be instantly convinced you're really a girl. Please, please let's get together next time my mom is out and go just a bit further. We can't know where this will take us but I just know it will be special. Love, Lois PS You can keep what you borrowed. The note left me breathless. How far could Lois and I take this and how special could it be? The thought of wearing makeup overwhelmed me but not nearly as much as her suggestion that I might be convincing as a girl. Of course, the only thing I had borrowed from her was the yellow panties which she said are now mine to keep. That, I promised myself, would be the beginning of my feminine wardrobe. But that wardrobe would have to be limited to basic panties until I learned more of the intricacies of lingerie, foundations, heels, hose, skirts and dresses; just for starters. That was no reason to delay shopping for my own things. The school week seemed to drag on forever once my plan for the next Saturday was set in my mind. I would get up early, dress casually but presentably and go downtown where there were some large five & tens as well as ladies specialty shops where I could window shop. Another reason the week was going so slowly. Lois was glum to the point where she avoided almost everybody including me. The obvious cause for her prolonged lack of social interest was, in my mind, guilt over what transpired between us plus concern over the existence of the note she had given me. That simple and sincere note, if found by the catty crowd and their jerk-off boyfriends, could ruin both of us. Lois had been dawdling around the school building after school. This may have been because she needed to use the library or talk with her favorite teachers or guidance counselor. My plan was to catch up to Lo, as if by chance, as she was leaving school and walk home with her. Starting out with small talk might open a chance for her to tell me what was on her mind. I positioned myself at the end of the office corridor where it connected to the main lobby and sat with my back against the wall while patiently memorizing chemistry formulas. The school was eerily silent when a door in the guidance corridor opened and I heard a weepy sounding Lois profusely thanking Miss Lamont but for what? I couldn't even guess. A sidelong glance down the told me that they were now standing in the doorway of the office anteroom. Miss Lamont's voice reassured Lois that everything would end well and that she would not be abandoned. That meant there was a better than even chance that whatever things Miss Lamont was referring to might end up not well at all. Another glance down the hall and I saw Miss Lamont take Lois's hand and gently pull her back into the anteroom. Then the sound of the door closing. A moment or two later the door reopened and Lois stepped into the hall looking furtively in each direction before walking toward the lobby. The back of her skirt was awry! Something other than guidance had gone one between Lois and Miss Lamont in those last minutes. It was an effort to reign in my imagination. Lo was startled to see me sitting there as she walked into the lobby. At first I was intimidated by her reaction. "Michael, you've been lying I wait for me, haven't you? Can't you see that I've been all but hiding from everyone this whole week?" She paused and stared at me. "I'm just so glad that you can't take a hint. I so need to talk to someone my own age and you're the only one I can trust. Please walk home with me." "Lo, thanks for trusting me as your friend. Sure I'll walk home with you. But, your skirt..." "What about my skirt?" "It's all caught up in back. Your panties might show." "Oh, really!" She was indignant now. "If that's the case, you should be able to see them from where you're sitting. Tell me, what color panties am I wearing?" "Red, shiny red." "Oh, my gosh. That could have been so humiliating. Thanks for being a pal and telling me. I thought I could trust Miss Lamont. She actually let me walk out of her office like that. I'll be glad to see the last of her even though we've been...we've been kind of close." We were out the building now and walking along the quiet streets. "Lo, what do you mean by "seeing the last of her." Is she leaving school or are you?" "It looks like I may have to leave no matter what happens. Mother has a new job out of town so either I go live with my father who is horrible or move away with Mother when I'm starting a special friendship with you. Swear you'll visit me over vacations and summers." "I swear I'll do everything possible to visit you every chance I get." "Everything?" "I said it and I mean it." "Okay, but will you do everything and anything? Before you answer let me explain something. My father always looks for every reason to prove Mother is an unfit parent so if a boy stayed with us even for one night he would make trouble." "Are you saying I would need to pass as a girl in order to visit you?" "Yes, I am." "Lo, for you I'll do anything and everything." We stood inside the side door to Lo's house. Wordlessly we put or school books down and looked at each other. Lois again took charge as she brought her face to mine and firmly held my wrists as she guided my hands to her tush. Our kisses became more probing as she edged her skirt upward so that it bunched around her waist. My hands trembled as she guided my finger tips to the sleek surface of her panties. Then her hands rested on my shoulders but unlike that evening when we were alone in her house, I needed no hint, no pressure to drop to my knees. Lois turned her back to me and pulled me close. Pressing my cheek against the cleft of her panty covered bottom, I inhaled her exquisite girl scent. Bringing may face between her lower cheeks, my tongue probed her rear access eliciting deep sighs from her. Suddenly Lois spun around and shoved me onto my back. "Michelle, it's not fair to get me going when there's no time or place to satisfy me all the way." Did I hear her right? She called me Michelle! Was she losing it or was I? "Miki, I don't want any seedy acts between us. Maybe it can be different when you visit..." Lo's voice faded away like a distant radio station. I picked up my schoolbooks and walked home. I never saw or hard from Lois after that. //////////////////////////////////////////////////////////////////////// GUIDANCE WITH MISS LAMONT Lois disappeared from school at the end of the week. A "For Sale" sign appeared on the lawn of her house. A few weeks later a moving van parked, four men loaded it and then drove off. It left me feeling empty but also gave me the feeling that I could get back to normal and stop wondering how far Lois and I could have gone in our one on one games. By now I had put together a respectable collection of fashion magazines which fueled my solitary sex play which was often further enhanced by the yellow panties that once belonged to Lois. Spring break was rapidly approaching; the summer vacation wasn't far behind. I had hoped somehow to reconnect with Lois for the summer but that was not to be. In a last ditch effort to get at least some clue as to where she had gone, I stopped in Miss Lamont's office before classes to introduce myself to her as Lois's friend. Perhaps she could give me some hint on how to find Lois. Miss Lamont was affable couldn't give me any information, specific or otherwise. "Of course, I recognize you. Lois pointed you out to me several times in the weeks before she left. She was very concerned that you might be hurt by her sudden forced move. Close the door so we can chat openly." That was the beginning of my special relationship with Miss Lamont. Miss Lamont didn't seat herself behind the desk but positioned her chair to the side where we could face each other directly. "Do have a seat and relax," she said as she gestured toward a chair. Her almost serene style made me comfortable at once. "My goodness, you move so gracefully for a boy." My face grew warm with blushing but not only over this much appreciated comment. As Miss Lamont crossed her legs so that her skirt slipped high enough for me to catch a glimpse of her stocking tops. "Michael, I need to put you at ease so we can talk freely. Lois told me every thing that went on between you two at her house. She felt terribly guilty about not being able to continue what was started. Her fear is that something might have been awakened in you that couldn't be brought to fruition unless you had help. We shouldn't really discuss it now, at least not until you've thought this through. Just understand that I'm willing to guide you if you choose to follow your instincts however far you need to. "Don't be concerned, Miki. We'll do our work away from school and there'll be no fees or costs. Think it over. At some point you may want to explain things to your mom and dad." "Just to my mom. My dad is gone. Miss Lamont, I'm pretty sure Mommy, I mean my mother, will be okay with this as long as I don't get caught at it by other kids." "That won't be a concern. How can you be so sure that your mother will go along with this?" "When I was little she treated me like I was a sissy and she was always telling me that she was meant to have a daughter." The warning bell for homeroom sounded and I left the guidance area knowing that Lois had left me in safe hands. //////////////////////////////////////////////////////////////////////// A DAY IN THE BLUFFS My chat with Miss Lamont allowed me to open my mind to possibilities. I hadn't the least clue as to how "we'll do our work away from school" or even what that work might be. My sudden fear was that my inhibitions would take over and I would remain stuck being an ineffective twerp. This fear motivated me to action. That Saturday morning I took the subway to the downtown shopping district. I browsed through a five and ten lingering among the counters that displayed girls' panties and hosiery. I looked at a slip of paper from my pocket as if checking sizes. Then I selected two multi-pair packs of unadorned cotton briefs; one in pastels, the other brights. The middle aged counter lady accepted the money I handed her without making me feel like a pervert. I tensed as a smile crossed her face. Had she realized from the first that I was buying these for myself? Not at all. "It's a rare young gentleman who has the confidence to buy a gift of unmentionables for a lady." The next hour or two was devoted to window shopping and wondering toward the fringes of the shopping district and into the area called "The Bluffs" so named for it being situated on high ground overlooking the harbor. It was set off from the commercial district by an abrupt change in street patterns. A few streets featuring upscale restaurants led to tree lined streets with well maintained brownstone and federal period homes. The pre-war apartment buildings were no taller than six stories and often had interesting stores in ground floor commercial space. I was fascinated by those shops that featured artistic and original jewelry, shops that sold accessories such as belts, shawls, scarves, and hats. The boutiques that offered hand sewn one of a kind skirts and blouses along with offerings in the other shops resonated with me. I knew at once that this was the style I would be most comfortable with as I began working with Miss Lamont. The streets were unfamiliar yet I felt calm and at ease wandering through what seemed to be the promised land of my dreams. A smile appeared on my face as I resolved to explore my special reality with or without Miss Lamont's guidance. The next street had a few restaurants featuring cabaret performances each evening. I resolved to lookup 'cabaret' in the dictionary as soon as I got home. This turned out to be unnecessary as a s display of photographs in a small glass window at the door of one such place was all the explanation I needed. One showed a young woman at a piano accompanying herself as she sang. Another showed a girl seated on a stool holding a guitar. "Contemporary Folk Interpretations" announced the card under her picture. Cool jazz piano was a staple in almost all of the cabarets with folk interpretations a close second. Most of the girls advertised as folk singers were dressed in the style I had already decided to adopt as my own. It might be helpful to return one evening to see just how these young performers carried themselves, how they moved and how they coordinated their ensembles and accessories. The sun was high in the sky and I was feeling a little hungry. Would I have enough money to cover a lunch, even a very light lunch in any restaurant or tearoom in this fascinating new world? It was too embarrassing to count what money I had left in the street. Then I noticed a brass plaque affixed nest to the entrance way of a corner apartment building. CORLISS LAMONT, Ph. D. Clinical Psychologist/Psychoanalyst By Appointment Suite 1-A That had to be my Miss Lamont! That the first and last manes matched was too much for coincidence. I stared dumbfounded as Miss Lamont walked out of the building lobby. She was wearing a severely cut navy blue dress with a sliver pendant and matching cuff bracelet worn over black leather gloves that covered her wrists. Off black stockings and t-strap black leather shoes called attention to her superb legs. A matching cape and slouch hat added to the dramatic effect. Oh my gosh. It really is her. What if she thinks I've been following her or something like that? I was hoping I would become invisible or that the sidewalk would open and swallow me. My near panic was unfounded. "Of all people to run into! Michael, out for a bit of exploration or have you been shopping? I'm delighted to see you here in The Bluffs. I'm sure your going to love this area. You'll fit in just fine once you know your way around. I was just on way to lunch. How about joining me? My treat, of course." Miss Lamont slipped her arm through mine and we started off. She pointed out a storefront that was divided into a jewelry and accessory shop on one side and a clothing boutique on the other. Next door was ladies specialty shop, the term used back then for shops providing intimate apparel and foundations. "I own and oversee these boutiques," she explained proudly. "I started with a small custom clothing shop where I made all the clothing by myself and from my own original designs. The business grew and allowed me to afford graduate school." We were soon seated in a small tearoom ordering from a waitress about my own age when I felt comfortable enough to ask Dr. Lamont she went from creating original clothi