Reflection free porn video

Reflection By Jena Corso Edited By Angela Meyers I can hardly believe I'm about to post my 100th story on fiction mania, so to celebrate a little I decided to go back in time and reflect on how it all began for me. I'm often asked how I got started down this winding path that at first I thought was so narrow yet realized over years how truly wrong I was. In today's internet and social media era you understand right away that you are truly just one of many but more than two decades ago it was at least initially a struggle to learn it was more than just a few of us. My story is nothing outrageous and hopefully interesting enough but I guess different from some as I was more of a late bloomer. When I write fiction I often wish I could have experienced youthful pigtails and a little frilly dress or even what could be like as a cheerleader or prom queen. I'm envious of those of you at times that felt those urges early in life and enjoyed some private time in their mothers or sisters clothes. Those things instead just came way too late and when I really reflect hearing so many other's wonderful childhood stories sometimes I wonder if maybe I misunderstood some of my earliest fascinations with women and young ladies. I never snuck into my mother's clothes more noticing my cousin's outfits as I had a few older sexy cousins. I was a jeans and sneakers kid loving sports like everyone else and really not interested in girls until the middle of high school. I had the typical posters of hot girls on my wall and I'd say my first obsession was girls in high heels. I loved the typical porn like everyone else but when I think back I always remember loving the girls in their outfits with sexy hair more than them just being nude. There was something more stimulating and sexy to me seeing them in hot skimpy dresses all made up as I know some guys could care less just wanting them naked. I figured we all just like different things and in reality that became an understatement. So we all have our little quirks and a story so here goes. Email me at [email protected] and I love to hear other experiences or be happy to share whatever you want to talk about. I'm here to help any of you searching or just needed someone to chat to while you struggle to find yourself as we journey down our crazy or unforeseen paths. So many have helped me over the years and without you I hate to think of how things would be. This is just about my first weekend and this is dedicated to our little coffee clutch of girls and "gurls" who already know too much!! FYI- names in this story have been changed! *********************************************************************** It all began in 1988 about a year or so after college and during my first real job. I met my girlfriend my junior year and I had been dating Theresa for almost two years at this point. She meant everything to me at that point in my life and we were mostly inseparable. Halloween was a favorite occasion for both of us, and like I'm sure for some of you, is where it all began for me. "Well last year you had your way so this year's my turn, ok?" said Theresa. "Fine, but as long as it's nothing stupid," I said. "I'm not going to Rob's party looking stupid. Don't you remember how hot you looked last year as cat woman? We looked awesome together." "I remember," said Theresa pecking a kiss on me. "Did you think I'd pick something old and frumpy?" "No." I grinned as she pulled my shirt off. "Exactly and it's still two weeks away," said Theresa softly kissing my chest and pushing me back on the bed. "So I'll let you know when I figure it out. Now shut up, because Karen's not back for at least a few more hours." Theresa was pretty good at getting her way but for the most part I never really cared. For whatever reason she always seemed more promiscuous when her roommate wasn't home, but to me I could care less as they each had their own bedrooms on opposite sides of the apartment. Our sex life was never an issue, because as needy as I was, she was even more so at times as it was probably the strongest part of our relationship whether we'd admit it or not. I always thought though there was probably a future together but that really wasn't that important to either of us at this time of our lives after college which was barely in the rear view mirror. A week went past without much discussion about Halloween, as more of the conversation was focused on the two year anniversary of our dating, which was coming in mid-November. Not a chance she'd let me forget it, as she was planning every detail of that weekend together, almost like a wedding. When I got to her apartment that next Friday night, it was one week before the Halloween party when she revealed her plan. "Hey babe," said Theresa, greeting me as I got to her place Friday night. "How was Happy Hour?" "Pretty good. Usual bunch of idiots laughing and ripping each other," I replied, feeling good with a slight buzz. "How was your day?" "Same old shit really," said Theresa with her arms draped around my neck looking at me with her beautiful blue eyes. "So, I was hoping we could just make this more of a quiet weekend and maybe just do a few little things I had in mind." "Quiet's cool," I said, going with the flow. "I'm pretty wiped so I'm fine for crashing out and doing whatever." "Perfect. I figured you'd like that since I've been dragging you everywhere lately," said Theresa with a grin. "Plus I haven't gotten everything yet for Halloween, so in case I need you to try stuff on then I thought we'd have time?" "What? Miss organized hasn't gotten it together?" I teased. "You should have let me just buy you something slutty like I wanted and we'd be all set already." "No, I've got it together wise ass," said Theresa with a smirk. "It's just going to take some experimenting to make sure everything will look right and you'll need some practice. I figured once it's late we'll go out for a walk once it's really dark." "What would I practice at night?" I asked as she took a box from the bag. "Oh you'll need plenty of practice to master these," said Theresa, opening a shoe box. "You must be shitting me," I said, seriously not expecting to see shiny patent leather classic black pumps. "I'm not," said Theresa matter of factly. "Let's try them on. Hopefully they'll fit but if not you'll be coming with me tomorrow to bring them back." "Just return them," I said. "This is not what I was expecting Terr." "Exactly, and you promised not to be an old fart," said Theresa leaning in kissing me and squeezing my nipple. "And I might be able to exchange them if they don't fit, but definitely not return them. They were on sale and so was the dress I got you. Now come on, let's try them on and let's see how you do walking around in here first." "Terr, come on," I whined. "I can't go my to friends party in drag. The guys will abuse the shit out of me." "I knew you'd say that," said Theresa opening a package of tan knee highs. "That party's going to suck anyway and most of your friends aren't going. They're going to the Springsteen concert instead. So I thought maybe we'd go to party at the Limelight instead. It's supposed to be a blast." "Who's going there?" I said anxiously. "Just a few girls from class. Maryann and Paula definitely and I'm not sure if anyone else yet," said Theresa giving him a look. "Paula's dressing up her boyfriend too, so you guys can commiserate together. So no one will be there that would make fun of you. In fact I'm sure they'd just have a good laugh with us and think it was sweet." "Come onnnnnn....." I grumbled. "I'll go there but not in those." "Let's just try on the shoes," said Theresa, lifting my leg and pulling off my socks and shoes. "Humor me. It's just us here anyway." I was pretty grouchy but it didn't take her long to push the legs of my blue jeans up towards my knees before rolling up the knee high stockings. They felt weird, especially once the jeans dropped back down over them and then it got even stranger feeling my foot in it's angled position as she slipped the pumps onto my feet. "Ok, stand babe," said Theresa taking my hand as I soon found myself standing in heels. "I can't do this Terr," I said, wobbling just a touch as I must have looked ready to kill her as she backup up across the room. "Stop the bull," said Theresa. "Just walk. I've seen you balance on one ski on the mountain and you're a freaking athlete. Of course you can with a little practice, and that's why we're starting now a week ahead of time." I hated to admit it but being a bit of a male chauvinist, I did think I could do anything that any girl could do as she made it seem like this balancing was slightly athletic. After a few steps it was quite strange but actually not as hard as I thought, as seemingly she had bought the right size but certainly would take some getting used to. For me the weirdest part was how I was using some different muscles and even more so how they pinched my toes a bit. She was the type that always loved teaching and instructing, but her instructing me on things like walking in heels was never something I thought we'd be doing. After ten minutes, I plopped down on the couch, having already had enough of this odd sensation. When I leaned down to pull them off, she immediately pulled my hand away, plopping next to me as she clicked on the tv. "Leave them on," said Theresa, grabbing my hand and keeping hold of it. "You need to get used to them and they need some breaking in. If they're broken in a little it'll be much easier once you're out in them, ok?" "I really didn't agree to this Terr," I said apprehensively. "If you really want me in these then how about I just wear them for you here, ok?" "Oh if you're good we'll be doing that too!" Theresa stroked my face and then started a make out session. "And if you're really good then next weekend maybe we'll blow away any of that cheesy girl on girl porn crap you idiots love watching." For the next hour or two we just cuddled and kissed as I sat there trying not to think about my feet, eating pizza and having some snacks. At about eleven o'clock she went into the bedroom, coming out with a long black coat and a pocketbook, holding them out as I had hoped she had forgotten but knew she hadn't. "Walk time," Theresa clapped her hands annoyingly like she always did when she was rushing me. "Let's go up and let's do it. It'll be fun." "Do we have to?" I whined, having no desire to even move let alone walk outside like this. "This coat is huge on me and I wear like 3 layers under it no problem. It'll be fine on you," said Theresa, not taking no for an answer as she held it open and I reluctantly stood. In an instant my arms were inside it and she was tying the belt of a women's black jacket after fastening three left side buttons. She reached up now undoing my pony before quickly rifling her fingers through my hair, rustling it up. She then pushed a pair of large round sun glasses over my eyes and took a tube of pink lipstick to my lips as I was just about pissing my pants about to leave her place like this. "What if someone sees us?" I bellyached. "A little lipstick and your coat are disguising me?" "Believe me! Even if they make you, no one gives a shit," said Theresa. "It's the village on a Friday night, and with your hair all tussled and those sun glasses, unless they walk right up to you then no one's the wiser. No one's even looking and you need the practice. Hold the strap of your pocketbook, loosen the fuck up and let's go." It really didn't make me feel better that she looked both ways as she opened her apartment and then we stepped out. Just walking to the elevator was enough to send my stomach into my throat, but then when it opened seeing an elderly woman inside it almost made me pee my pants. Theresa gave the customary soft hello type grin as I looked down at the floor avoiding eye contact without saying a word, slumping towards the back as mercifully there were no more stops and the door opened at the lobby. We got out, as the elderly woman stayed on heading to the basement and happily there was no one in the small lobby. At night thankfully the lobby was unattended but just the clicking of my heels on the granite tile seemed like I was tossing a firecracker with each step as the sound reverberated so loudly in the small enclosed space. It was hard to shake the feeling of butterflies in my belly as we stepped outside under the streetlights, as the first few groups of people walked right by, never even giving a look. It was only a block until we crossed the avenue but the busy New York streets at least now muffled the clicking in my mind and I was at some peace hiding behind the glasses. "You're doing great," said Theresa before saying. "Either you're holding back on me or you're a natural." "Yeah, I am," I replied sarcastically, sharing a small laugh half annoyed at her insinuation. "Me and my drag friends secretly do this when you're out." "Cool, that's so sexy!" Giggled Theresa. "Let's hop a cab uptown and you can introduce me to everyone." "Ok, I'll pass on that one," I said with a laugh. "Let's just shut up and walk." "See, now that's my man! You're athletic?" said Theresa being her normal ultra-positive self. "Fat girls and old ladies walk in them. It's just practice and we're in no rush. I knew you'd loosen up and have fun with this." "Ok, you don't need to keep reminding me! I just don't want to have to explain this to anyone I know," I said walking. "It'll admit it's not as bad as I thought, but I was always good at balance type stuff." "Told ya so," she said, beaming as we both knew she pretty much always got her way anyhow and even more so got me to admit what she wanted to hear. In a way it was kind of thrilling, even if it was another thing I didn't want to admit as this was not what I expected to be doing on a Friday night. I could see the occasional person give us a glance, but no one really paid us much mind as we had walked a few blocks and like most nights the Village was buzzing with activity. We both always enjoyed walking the streets and experienced all the sights but I just was so self-conscious about becoming one of them. One thing in my favor was that she hated the cold, and when it really got windy she was ready to head back. I held my tongue not complaining, as my toes were tired of being squished and my calves got just a little sore. We had walked about an eight block radius now without a break, and I actually did better than I thought as finally we headed back. "You good or should I get us a cab," said Theresa as I wasn't sure if she could be serious. "Like this no way," I said. "I can walk back." It was about six blocks back and by the last three I was really getting sore. I wasn't sure if it was in my head knowing I was getting close, or just at the limit I could handle. Happily when she turned her key in the lobby glass door there was no one else inside or in the elevato,r as it was completely uneventful getting back to her place. When we got inside, I tossed the coat and glasses on the couch and it was almost the equivalent to opening your ski boots when you stop for lunch, feeling some wonderful relief once I kicked off my pumps. Next I practically raced to the bathroom to empty my bladder, which was half exploding from the combination of cold air and nerves, thankful this was behind me. I washed my hands and took a tissue, wiping off the lipstick before returning to the living room as she was sprawled out on the couch. I sat next to her, pulling off the knee highs and playfully tossing them into her face. She giggled pushing me back and initiated long drawn out kiss, which always seemed to sooth any tension we ever had. "So you did just fine. Feel better now that we're home?" said Theresa running her fingers through my messy windblown hair. "We'll practice a little more and you'll be running in them in no time." "Yeah running off," I said, half ready to kill her. "Can we not think about this anymore tonight?" "Deal," said Theresa initiating another make out session. It was just like any other weekend night now, where we might stay in watching a movie and enjoying each other. She was spitfire in the bedroom, having as great a sexual appetite as anyone I'd ever met to this point in my life, never not wanting to have sex. She was also one of the few girls I had ever met that loved giving oral, never having to be begged or coached, instead initiating and even at times not expecting reciprocation. When I woke up on Saturday, breakfast was ready and she never brought up the subject. That was fine by me as I wasn't pushing it as we had plans that day, so all went without issue. On Sundays I would either go home and watch football with my buddies, or at times stay and we'd watch together. That morning she wanted to go to brunch, which we often did and then came the awkward conversation in a public place. "So I was thinking you were going to stay to watch the Giants and I'll make some dinner for us?" said Theresa. "You've got clothes here, I washed from last weekend so you can stay and go to work from here on Monday." "Ok, cool," I said. "It's the Falcons. They suck so not a lot of guys will be around for it, so dinner sounds good and that works." "Good, then you relax and watch the game while I do a little shopping and then after dinner we'll practice again ok?" said Theresa downing her eggs looking for my reaction. "You're really still making me do this, right?" I said already knowing the answer. "Stop! It'll be fun," said Theresa. "Remember, don't be the old fart you always complain about." There was almost nothing I could say as we got off the subject, enjoying a nice brunch. We went back to her place and one thing I really enjoyed was that she was so easy going, not minding for a moment that I lounged on her couch watching football. Her roommate came home for a while, annoyingly talking up a storm in the background before finally back up again and heading to her boyfriends. In many ways she was an excellent roomie for Theresa, as she was barely ever there on the weekends, as both her boyfriend and parents lived in the suburbs and she was heading to her parents' house for dinner. I watched my football game mostly in peace as Theresa headed out shopping and then finally she returned with the groceries. I loved just smelling her cooking as she worked in the kitchen while I watched football, but the next few surprises were certainly nothing I expected. "So they must have played really well today?" said Theresa, coming in sitting next to me. "You miss me." "Yeah, it was a good game," I said as she turned my face, softly kissing me. "Of course I did." "Good! So dinner will be ready in about an hour, but in the meantime while you're watching the stupid jets?" she said grinning rubbing my crotch. "I can take a break from them," I replied, aroused in seconds. "No you watch and let me just have some fun," said Theresa. "I'll just get a few towels in case." I loved when she undid my pants and by the time she was back with a few towels I already had them off. We both knew what she wanted and like I'd ever fight her about it? I also knew the drill pretty well, as she always have me sit on a towel as her couch was a soft fabric and she tossed a few more on the floor to kneel on. It was no different than any other time as she enjoyed a little foreplay, kissing while she teased me with her nails and then the moment she broke the kiss she was ready for business pulling off my briefs. No matter how much I tried, I really never lasted too long and this time was no different as she was like a wizard with it in her mouth enjoying me as an appetizer as I'm lucky if I held out two minutes. "Ok feel better," she said getting to her knees. "So we should be really relaxed then now right?" "Yes, that was awesome," I said twisting my neck towards the bedroom. "Do you want to go inside?" "Save it for tonight after dinner," said Theresa, tossing a towel over my oozing member. "I'm going to go throw in the macaroni, brush my teeth and just wash up." She did exactly that before finally coming back with a little basin filled with water, placing it near my feet. "Soak them in here," she said. "It's nice and warm and it'll feel awesome." "Really why?" I said as she lifted them right in as soon as she sat it down. "Just do it and don't be a pain in the ass," said Theresa and then went back inside. In just a few minutes she was back with her hands full and here we were like it or not taking the next baby step. "Today?" I said as it was all I could muster seeing the bag of pink razors and shaving cream in her hand. "Already?" "Shush! Not really," said Theresa kneeling down. "I'm just experimenting." That she was as she lathered just the bottom of my right leg and very slowly sliced away all the hair below my calf muscle. I thought I'd actually be more freaked out, but mostly I was awe-struck as it really didn't take long until my ankles and feet were hairless. "Didn't you ever do this in football camp or anything," she said. "My cousin said the guys used to shave their ankles to tape them up." "I wasn't at camps like that," I said as she took some lotion to my feet and lower legs. "Well I guess you could be now then," teased Theresa as she got up. "Just sit like this while I stir the pot and then you'll put on the leggings I bought you?" "Leggings?" I questioned. "Don't be a baby, thery're soft like sweats and they'll look more normal than boy jeans under my coat," said Theresa. "You need to keep practicing in your heels and all I shaved is what would be showing." Everything with her was so damn meticulous as she stirred the pot and then came back, tossing me the knee highs and leggings. "Commando is fine with these," said Theresa. "Now put on everything and your shoes. Knee highs first. It won't hurt to get used to even sitting around in them." She was right that they were pretty comfortable as I pulled on knee highs and then the gaucho length leggings. We made a few jokes, keeping it light as soon found myself sitting in heels and leggings watching the Jets and Dolphins. By half time I stood for the first time facing the toilet bowl in my heels, holding down the elastic of the fly-less leggings, peeing from this strange elevated position. I made sure to give a few extra shakes and use a little toilet paper, mindful of leaving a little wet spot before washing my hands and heading to the table. "Your roommate's definitely not coming home, right?" I asked, double checking for like the fifth time so self-conscious of being this weirdo parading their place in heels. "Again, no and once it gets late we'll go walking and then I'll figure out another night in the middle of the week to make dinner when she won't be here," she said as she served me. "You really think this is how other guys go out in drag on Halloween?" I said. "You think they practice this shit?" "I don't know, and don't be an asshole! I would think they should and it would be easier!" said Theresa giving me the eye roll. "I'm looking forward to having some fun with this, and you already promised not to ruin it for me? I wouldn't ruin it for you? You want me to start rattling off all the stupid shit I've done for you?" "No?" I chuckled, thinking of all the stupid things she was right about. It was fairly uneventful as again we went out walking when it got real late, as the city was much quieter on a Sunday night. From Friday to Sunday I did get a bit more comfortable and already was a bit steadier. The walk certainly didn't seem as long, but what really stuck in my mind was how chilly my bare ankles felt on the cold night now hairless and exposed. It probably was more mental than physical, but in a way whether she realized it or not it was another baby step to my transition as she was transforming me for Halloween from the ground up. When Wednesday came around, I was back for dinner and to sleep over but the night would be a bit more eventful. "No seconds today ok?" teased Theresa as she served me. "I made us a nice salad and just your favorite ziti. We've got to watch that figure of yours." "Not funny?" I said, knowing what she meant. "But I never gain weight if that's what your teasing about!" "I know you jerk, and I've always hated you for that," she said with a giggle, getting up and softly planting a kiss. "Eat while I run the tub for us and I'll be right back." In five minutes she was back, wearing only a short silk nightie hovering over me with a grin on her face as I could barely finish my dinner as she rubbed my shoulders and then kissed my neck. "Had enough?" she whispered in my ear. "Almost," I mouthed as unbuttoned my shirt right at the table while I engulfed a few last strands. Before I could really even think, she was leading me from the table and stripping off my pants in the bathroom. We would often share a hot bath or shower together, but this time I already knew it wasn't going to be how we normally relaxed. I'm not really sure how long we snuggled in there in each other arms but there wasn't much conversation. The softest kissing and fondling was wonderful, but the minute it got heavier she pulled back and stepped out of the tub. "I want to get this part out of the way today ok," said Theresa, getting more serious pulling the plug on the tub. "Just don't be squirmy so we have no problems please." As the water drained, she opened her vanity and took out two packages of pink razors. I already kind of anticipated her agenda but quickly it was crystal clear when she lifted my leg and covered it in a foam gel. I really did nothing but watch as ever so slowly she'd shave a section from my leg and rinse the blade under the tub's fawcett. I couldn't believe how many razors she actually used, as I wasn't sure if that was necessary but didn't know better. It was a much longer process than I expected, as a dozen razors and my legs were completely smooth and she turned to my arms. She did use a scissor first on my arm pit hair, but that was done in no time. I had little hair on my chest, except mostly the naval and when she had me stand it was strange having just the little fuzz wiped from my butt cheeks and around my hole. Standing there I'll always remember thinking how much better my body looked hairless, easily becoming rock hard when she covered me in lotion. I was hoping she'd be going down on me just then, but she'd be saving that for later ready to go for our walk. After a few minutes, I was soon back in my leggings and heels and then it was like any other night in the bedroom when we got back. I left work early on Friday like she asked and I was completely unproductive that day, anxiously awaiting the night. I was dreading being seen like this, yet was really curious about how all this would turn out. I remember how happy to see me she was when I got there, as we had a nice early make out session and then off to the shower I was sent. It wasn't my first time using her shampoo or conditioner as she instructed me, but the flowery body wash I had never used before. As much as she had tried squelching my nerves, I still wasn't really too keen on this whole cross dressing for fun thing as I came from the shower, seeing her waiting. Theresa licked her chops, eager to get to work on me, certainly did nothing to ease any of my butterflies as I walked over. It was pretty nerve racking as I found myself sitting there in nothing but a towel as she brushed through my wet hair. I glanced back at all the cosmetics, hair tools and clips on the table until she smirked, enjoying my angst, twisting my head back forward. It wasn't the first time she had ever brushed or done my hair, as I always loved to sit like a puppy dog being scratched, enjoying her long nails on my scalp, neck and back. This time though was completely different as I soon found my head enclosed in another towel which she wrapped turban style. When she came around the front, she was like a doctor inspecting my face for any spot I may not have shaved to her liking and then actually lather eda few spots on my neck, sliding against the grain. Since she had been almost obsessing with this, in a way I was curious about how I'd look all made up, and she began rubbing in a moisturizer all over my face. For the most part I really hoped she'd hate how it turned out and we could just make this another of our bedroom games, but I knew that wasn't her intention.. While it sat absorbing into my skin, she took her tweezers, just doing some minor league shaping and cleaning of my brows as she knew I was pretty fidgety already. "Chill! I'm not doing much," said Theresa before I could complain. "You know I'm not arching them like I really should." "Not funny!" I stammered, giving her a look. "Lighten up please," she said plucking a few more. "Thick as they ar,e they're already better than what Brook Shields has and probably no one but me will even notice the minor clean up I should have been doing on you all along." I rolled my eyes as it actually didn't seem like that much as she now opened a little snack table next to my chair. It was almost creepy at first as she opened a package of long nails and she measured them against each finger until she matched the width. Once she did there was just some quick wiping and slight buffing to rough them up before quickly she snipped the end off of a five second glue tub. It was a rapid process now adhering them to my digits as quickly she opened another snack table on the other side and within minutes I had huge claws on both hands. How the hell could any girl do anything with these I thought, until she began clipping the length and shaping the edges. Why they didn't just come out of the package like this I wondered, as it seemed like quite a bit of work but I guess that was just how guys think. In a way I was mesmerized at how they took shape and color, as I wasn't sure how long she was working on them but before I knew it the evening news was over. "So that's a pretty red, right?" said Theresa as if she cared about my opinion anyway. "I know you always like mine red and I kinda debated it in my head, but I like this for you." "Does it matter if I did or didn't either way?" I teased back. "Of course it matters," she teased planting a soft kiss. "They're your nails now." She was so giddy with her teasing it really didn't matter anyway as I was at the point of just get it over with already. Little do you realize how weird it is to keep your fingers fanned out for a continuous period, or how hard it is to not even tap your fingers or not touch a thing while they're wet. The elongation of your fingers really does seem to slenderize your hands, though and it's hard to not glance at them continually, especially when the top coat is added and they appear so glossy. In a way it was good that she finally started on my face as I again had to raise my eyes level as she started my foundation. "Oh here goes! Time to get you pretty," she teased, heavily dabbing at my chin and neck area. "Hope this shit works like they say." "And if it doesn't?" I said curiously as she patted away. "And nothing?" said Theresa. "It just means you'll be the prettiest girl out there with a five o'clock shadow. Now hush, It'll work. They know there's shit there at the place I got it." She was so focused now, constantly turning my chin sliding from side to side and angle to angle as she finished concealing the pores that had been close shaven and then applied another layer of foundation. One of the oddest sensations yet was having my lashes squeezed with her lash curler, and then I couldn't see much as she brushed at my brows. I followed her commands as she had me roll my eyes up and then over as she worked with her pencil and then held my eyes between her fingers, lining them. My eyes were opened and closed constantly, especially when the liquid liner came out, but nothing seemed normal about watching her open the package of the false lashes. They seemed so long when she peeled them from their packaging before measuring them against mine. She trimmed just a touch off the length, then measured again before taking a little tube coating the edges with glue. I could oddly feel myself grow slightly aroused as I watched her pink lips blow on them until they were tacky enough for her liking but that semi-erect state quickly faded once she carefully pressed them into position. "Ok pucker and suck in your cheeks," said Theresa as suddenly I was a puffer fish while she enhanced my cheek bones. She took a compact type applicator under my eyes and across my nose and chin before switching brushes constantly now. She changed to big and small brushes a few times, even brushing my forehead and under my nose. "Ok, eyes closed until I tell you please," said Theresa as I saw the smallest applicator approach as I closed them up. You actually never realize how soft and soothing it is to have your eyelids stroked as she added and blended my shadows, having me open and close on command. It's the exact opposite though the first time the little eye lash brush separates your lashes as your natural reaction is to close them as she used her finger to hold mine open. I had rubbed my eyes many times but never before recognized how sensitive the lash hairs actually were, as she had blended my natural ones with the falsies and began coating them with mascara. Just the simple movement of her wand was so bizarre as they reverberated with each stroke as she stepped back a few times, taking in all her work and making adjustments. "Almost done then I guess?" I asked, actually curious what the hell I might look like. "Getting there," said Theresa, sharpening a maroon colored pencil. "Rome wasn't built in a day right? Now open wide and hold it ok?" She loved all those stupid slogans or expressions, as one of the qualities that I both loved and hated about her was her quick wit and wise ass personality. Theresa knew when to be serious in life, but also was never one to shy away from any chance to zing just about anyone but especially me as I stretched my mouth wide open as she lined my lips. When she finished, she opened three or four tubes of lipstick, holding them near my face before making her selection. Funny part is she mostly sported a more natural lip color herself, but soft pinks were not part of what she was considering for me, instead all I noticed were a steady supply of reds. In general she never really wore that much makeup, except for big nights out or a special occasion but obviously the girl next door look wasn't in my cards, as she unscrewed the little applicator from my selection, greasing my lips. When she finished she was squishing her cheeks, thinking as she seemed happy with her selection and then unfolded a bed sheet. She then draped it over me and secured it in the back with a safety pin before unwrapping my makeshift turban. This in a way was nothing new as she trimmed my hair every once and a while since we'd been dating and she was the go to girl for her friends always doing their hair for a big occasion. She took a little spray bottle now, spritzing my damp hair and then took her comb, raking through it. My hair was rocker length long, four or five inches on my shoulders but certainly not half way down my back like hers or most other girls I knew. She was not a professional hairdresser, but the most artistic person I had ever known, always extremely creative with herself, always sporting different looks. She was the girl that loved changing her hair color and style from curls to straight to wavy to whatever at times. That was her thing. For me it was a characteristic I loved about her, as there was something about a girl being a chameleon that just made her that much hotter. In a way it was like never eating the same food twice in a row, or maybe in my mind I was dating almost different people each time, even though it was still her. It was something that has stuck with me my whole life ever since, and so has my first time experiencing being in that proverbial hair chair, almost like one of her nieces or girlfriends instead of her boyfriend getting a trim. "OK, just don't be nervous, alright?" said Theresa seeing me fidgeting as she slid the long end of a rat tailed comb horizontally just above my right ear and inserted a long silver pin. "Maybe I wouldn't have been if you didn't say that right?" I said rolling my eyes as she repeated it on the left side now. "Like it matters," said Theresa sarcastically. "This is no different than the other dozen times I trimmed your hair. Now hush. I'm just cleaning it up like I normally do, just this time doing a little something different. You know more appropriate for tonight." "I figured as much," I replied, as on top she just twisted it a few times and pinched it under a jaw clip. "But probably more than a little something if I know you." "Maybe?" she giggled, as in reality she was right that she had done this before, as she was my unofficial hair trimmer as it had been at least two years since I had been to the barber shop which I hated anyway. On weekends I normally wore my hair brushed straight back sitting behind my ears, hanging loosely on my shoulders but she hated it messy which was often the case, even though she did like it long as we both loved the eighties hair bands. My father hated it long and sloppy, which mostly made me rebel even more, keeping it long since high school and at my job it didn't matter as I wasn't the only guy longish hair. Where Theresa and he agreed though was to at least look neat, so usually for work I sported a low slicked pony. Back then it was cool to idolize Steven Segal which a lot of us did even though I looked nothing like him. At first, she worked in the back, stretching and snipping as I really wasn't nervous at all about her trimming too much. I knew she loved my hair and wouldn't fuck it up, so initially really nothing was abnormal. What I saw slide down the sheet were the tiniest of trimmings, as she moved up the clips and then did the next section from above my ears and down. Again it was pretty much little trimmings as she worked really slowly, pinching and cutting as I already had some layers in my hair so it was still pretty normal. "Ok then?" I said as she pulled out the top clip and then combed it all straight down covering my face, as I knew something was different now as this was something she hadn't done before. "Just straightened the ends," said Theresa, now creating a middle part a few times until it was perfectly straight to her liking. "Now this is the time I have to get this right, so chin up and don't move your head or you will have something to be nervous about." It was like she was creating an upside down "T" shape part on my head now as she created a horizontal part about just behind each ear which spanned from one side to the other. This gave me a long section on each side that hung forward down across each cheek as I peeked through the gap in the middle from the part like a shaggy dog. When she had sectioned the hair to her licking, she twisted the entire back into a man bun type knot, pinning it under a big jaw clip and then came out in front combing furiously on each side. "I haven't parted my hair down the middle since grammar school," I said trying to stay relaxed as this was really strange. "Maybe not, but I remember those pictures your mom has. You were so cute back then but don't worry you're about to be really cute again," Joked Theresa as around her wrist now she had two small bands and when she was finally happy with the sections she had created then she gathered each side. She then wound in the band, creating something between a partial frontal pigtail and a weird princess Leia twist, temporarily pinning the desired sections before she took her hair dryer and removed the clip on the back section. "Yeah I can't wait?" I said sarcastically as she stretched a multi-prong extension cord behind me and I tucked my chin looking a back seeing all the tools being plugged in. "Stop peeking, and these are hot!" said Theresa as she removed the clip in the back and turned my face forward. "How much did you trim? I only saw little clippings but it looks shorter?" I said as I noticed the ends of my hair on my shoulder seemingly shorter as I wanted to reach up, but was buried under the makeshift cape. "Almost nothing but now it's a little more straight across," said Theresa combing through it. "But just don't panic when I'm done, because it'll look even shorter once I put in some curls." "I figured you were," I said already seeing the curling iron and stuff. "Now stop distracting me. I've got so much to do and let's get out the dampness," said Theresa switching on her hair dryer. First she wiggled her finger through the damp hair, separating and hitting it with the blow dryer. It really didn't take that long as she used her round brush until the back was blown out to her liking but then she started again clipping it up sectioning the back. At the right nape of my neck now, she stretched a small section and then I felt it being coated with something sticky and then immediately felt the tension. It was only but another moment now before I experienced my first hot roller as from behind I could hear the canister open and felt her wind it in. The warmth on my neck actually felt really soothing, yet I was somewhat surprised by the weight as ever so methodically she filled the back of my head. I counted nine rollers going in as I wasn't sure if that was a lot or a little but what I did know was they seemed fairly secure as I moved my head slightly feeling them barely move. Theresa came back in, now untwisting the left side and then stretching it forward combing through it. It was a much wider white comb that she was using now, as it encompassed a much longer section compared to the little rat tailed comb she had before as she raked through it over and over. She stretched it a few times and each time dropped it oddly across my face before finally I noticed the scissors positioned in her hand. In general she was a loose yet confident young woman, but I'll never forget what I thought might be a hint of nervousness as she again checked the length against my face and then pinned my hair between her fingers at an angle. I can remember almost feeling like pissing myself when I watched her trim away a pretty long section as it slid right down my cape and then her staring intently as she lifted the next length below it stretching and snipping much less. "Theresa?" I gulped questioning her. "Was that a lot?" "It's nothing. I'm just shaping a little," she said stretching and making some fine snips. "Please just trust me ok? I know you're stressing about this whole thing but it's no biggie so please don't stress me out too. You know I've been thinking about this all week, so maybe just close your eyes until I finish. It's just some new layers and either way you really need them. You know I've been dying to fix your hair, and you've needed something that you've been avoiding. I promise this is going to work for you after Halloween is over." "You know I hate when you get like this," I said as she untied the other side. "You know I said I'd do this but I didn't sign up for a haircut here too." "I know," said Theresa leaning down kissing my cheek. "But I love you and you still needed it anyway." "Did I?" I said sarcastically rolling my eyes. "Hey!" she said purposely startling me. "Let's not forget tonight I'm wearing the pants and you're wearing the dress." She knew I hated when she made references like that as every once and a while we'd fight about control. As much I cared about her, we did have a power struggle from time to time, as one thing she was, was a strong minded take charge Italian woman. "Somehow I feel like that's been happening more often than not lately," I said shaking my head slightly as she combed over and over trying to make my point. "Yeah and if I didn't take charge half the time, you'd be a messy fat wreck on the couch for most of your life doing nothing," said Theresa straightening my face before stretching and measuring the other side now. "Tell me I'm wrong?" "Ok, ok," I giggled. "You made your point." "Exactly," Grinned Theresa as she snipped down the left side ever so cautiously. "Now close your eyes and stop annoying me so I can finish. Remember, you promised me you wouldn't ruin the fun right?" "I did," I said rolling my eyes. "Hey I saw that!" Theresa laughed, combing all the hair right in front of my face. "And don't be a little bitch until I finish making you one ok? Eyes closed, chin up a touch and don't move!" She always loved her own jokes, always keeping it light as she used her round brush now instead of her comb before making a few small snips. When she finished trimming, she switched back to her comb stretching each side over and over seemingly measuring with her fingers to make sure they were even and then one last time brushed it straight down it still easily covered my eyes and ticked my nose. I knew it wasn't really too short and I had layers but no longer did I really think much about my weird Halloween hairdo instead worried about what I'd have to deal after the weekend when I'd be back in the office. She certainly had never been a girl that would fly by the seat of her pants so I knew she had ulterior motives and this one might have been to get rid of my current look or just tell me she was bored of it. She wasn't one to hold back her feelings either as we had talked about things like that in the past but with her sometimes you learned to expect the unexpected. Most of my life I did like the strong minded take charge type woman but she was certainly the strongest of any I had ever known normally hating more on some of my clothes than my look. She switched on her dryer now, blowing out each side of my hair and then when the moisture was mostly gone used her round brush turning it away from my face. Out of the corners of my eyes, I could see it oddly pushed back away from my face kind of flipped outward as she jumped from side to side. When she stitched it off and then put down the brush she quickly had her curling iron in hand. "Look down and be still until I tell you," she said as she stretched the section right above my right eye. "These things are so freaking hot." Even though I was glancing down, I could certainly see her forearm right in front of me and the wire hanging across my chest. It was impossible not to glance up a few times as the little squeak of the curling irons clamp being pinched open was apparent, and I felt every movement of it being manipulated, angling into place as it slid down my hair. I really didn't know if it was my imagination thinking I was hearing my hair sizzle when she wrapped it, or was it just the heat near my forehead and scalp when she rolled it up tight. It didn't even seem like it was in there that long when she released the clamp as it was almost a surreal like moment feeling it spring back when she released it. "Oh I think I'm going to love.. love.. love this on you!" said Theresa getting excited as she wound in the next section slightly lower down as she rolled it above my ear as I glanced up at her. "Stay looking down. Very hot honey, but I think my intuition was right." "That part I can tell obviously," I said looking down as the second curl was unrolled. "Try not to burn me please." "Of course I won't, but the good news is these really hot irons ones bake in the curls really fast so this won't take that long," said Theresa unrolling the next section. "Fantastic?" I said sarcastically. "And the even better news is I think I shaped it perfectly!" said Theresa, patting them with her palm pushing them together and then curling the fourth section. "They already look pretty good. I'm so psyched!" I sat there basically just biding my time now as she flipped over, curling the other side now and then she jumped back and forth re-curling certain spots. She used a combination of her little pick, her fingers and the round brush making adjustment after adjustment before against re-rolling a few spots on each side until finally she was seemingly pleased. I had actually always loved the scent of her hairspray except now it was being liberally applied across the front portion of my hair as she covered my eyes with her palm. When she finished she switched her dryer on low and softly warmed each side setting the hair spray and then stepped back for a moment admiring her work. She then turned her attention to the back, unravelling a hot roller and feeling the hair as I heard it being placed back into its canister. "Ok, they're cool," she said enthusiastically. "Almost done! So you excited or what?" "Now as much as you are obviously?" I said feeling curler after curler come out. When finally they all were back in their holder, she used only her fingers separating the sections and kind of tugging at them. For just a moment I was able to forget my situation, enjoying her nails on my scalp and then she began liberally spraying the back. "Ok, time to get you dressed. Damn, its so cute on you," she said, circling me like a wolf and then unpinning the sheet. "I think your hair and makeup came out amazing! Aren't you just dying to see yourself all dressed!" "Not like you are?" I said nervously as she looked at me like a pleased paren,t like I got a got report card as I happily finally stood from the chair stretching my back and rolling my neck. It was ever so weird as I could feel my hair kind of roll with me as I cracked my neck and reached up, feeling the back of my sticky hair before touching the front. "Hey no touching! Don't fuck it up already or I'll kill you," said Theresa pulling away my wrist. "I worked hard on that and it's not like what you're used to having hair where you can play with it. Now let's hope everything fits right but it should! Let's go! Towel off please!" All I could do is really give nothing more than an evil grin as she couldn't wait to pull away my towel and I stood there naked now. She was in full production mode now, stretching open a little black panty brief as I stepped in, thinking in all my years dating she's never helped me on with my underwear before. "Oh that's too weird," I said trying to reach down and adjust it as it rode right between my cheeks. "It can't stay like this, it's maybe too small. It's like a super wedgie. Help me fix it." "One sec you big baby, but that's how its supposed to be, they said," said Theresa lifting the elastic. "Give me a second and we'll adjust it." "I'm trying to myself, but I never had these stupid nails," I said, already wanting to get it off grabbing at the elastic between my cheeks. "Fix it, I can't stay like this." My first experience in a gaff made my curls feel normal as immediately the elastic like cords between my butt cheeks made this completely unbearable, and I struggled to adjust it at all with my long nails. I was twisting around like a Mexican jumping bean, so uncomfortable as her giggles pissed me off even more and then she stopped me from fidgeting. "Hold on a second," said Theresa, pushing down the front beneath my naval but that did nothing. "Yeah that won't fly." "Good because that doesn't feel any better," I said confused, looking down seeing there was still a lump in front. "Because we didn't tuck it right like they told me," said Theresa looking down at my little bulge. "It doesn't happen automatically obviously, and they told me the trick they all use if this doesn't look right, because that's definitely going to show in your dress. Give me a second here." I never minded her hands anywhere near my junk, but obviously this was a little different. It was a momentary relief as she pulled down my panty a few inches to my hips and then reached around from behind, pulling back my junk. Unfortunately for me I now had experienced exactly what the gaff was designed to do once she tugged it back in place and tightened the elastic near the base of my spine. As she held them together, she wrapped a small piece of duct tape around the top of the elastic cords right at my tailbone, which pretty much cemented them to stay put tightly between my butt cheeks. "Yup I think we got it now," said Theresa, softly sliding her hand over my now flattened crotch. "No that can't be right! This is really annoying," I said getting antsy. "I can't stay all night like this." "Just try not to think about it for now and give it a few minutes ok," she said squeezing my hand. "Please just let me finish and then we'll see what we can do to make you more comfortable. You know I'd never harm my favorite little friend down there right?" "This is so fucked up," I said as she always knew exactly how to twist me. "You are so lucky I love you." "See, that's my girl," teased Theresa, softly tapping my ass and then opening a package of pantyhose. "Now except for maybe wearing a bra the rest of your outfit won't be uncomfortable." I held her shoulder as she knelt, rolling them and lifting my foot as she rolled them over my ankle and then had me put it down as she did the next one. She was right that actually the hose weren't uncomfortable as I had already experienced knee highs, instead just felt peculiar when she snugged them up tightly adjusting the control top. The extra control was something that really didn't matter anyway, as I was a maybe solid 158 lbs soaking wet at the time with not an ounce of belly fat. At 5'8" I wasn't tall of course for a guy, but not a midget either as it worked for us as Theresa was only 5'3," Even in weekend stilettos, it didn't seem like she could look me straight in the eye but that really didn't matter much today as I was soon to be the one in heels. I had a thin but solid frame and a decent muscle tone with a slight v- shape, being pretty athletic. I was not a gym rat weight lifter type at all, but it still looked pretty weird seeing my toned bicep next to a black bra strap as she now buckled up the back. It really wasn't as uncomfortable as I thought it might be, and as weird as it sounds I was pretty much captivated when I saw her open the package of false boobs. "Wow, they're heavier than I expected," was all I could think of as she slid in the inserts, creating my mounds. "You like those I guess," she said getting a kick out of me cupping them with my hands as she adjusted the straps a few times and pushed at my chest. "Seems so weird them being there," I said, half not wanting to admit it as I was always a boob guy and she knew it. "Look how red I made you! Don't be embarrassed," said Theresa smiling. "I know you like them big, but I didn't want them too big. That's a B- cup falsie in a C-cup bra and with your natural flesh under there it looks like you're filling out the C-pretty well. Now I'm dying to get that dress on now and see how it looks. Worst case there's plenty of stuffing tricks we can do if you don't fill it out right." "Thank goodness for that." I gulped nervously, knowing I was near the end. She walked into her bedroom now and then came right back out with a black dress on a hanger in her right hand and my all too familiar pumps in her left. As she stepped in front of me, she dropped my shoes to the floor and I was almost more anxious than nervous now, but regardless of how I felt the moment had arrived. In the back it had a little zipper that she opened, taking it from the hanger and then crazy as it seemed I was stepping right into it. It really was so soft and kind of stretchy, as the poly-blend material was form fitting as it rode up my body as she guided in my arms. This whole thing was as quick as putting on a sweatshirt, as before I could even blink she had already zipped up the back and was out in front of me inspecting her selection. "Put your shoes and let's see what works here," said Theres,a taking my shoulder as this part was no longer foreign to me. "It's no good?" I said curiously. "No! That's not what I meant. It fits pretty well actually like I expected, so don't worry you're going out in it," she grinned before stepping behind, unzipping the back. "No need to try on the backup." "You bought me another one," I said surprised. "I picked up a few things just in case it didn't fit, but its not like I don't know you measurements or body inside out as I've bought half you decent clothes, haven't I?" she said as her hands were all over, feeling the fit and moving it. "I guess." Kind of in awe of myself in a dress, staring at my legs. "I saved the receipts to take them back next week if I needed to anyway," said Theresa. "Just a few adjustments, but this was my first choice by a mile anyway. I expected some and without you dress shopping with me I knew I had to pick something that wouldn't be unforgiving. If you want we can try on the other too, but this is a little less showy for today and I think you'll be more comfortable in it." "Like there's a chance of that," I mumbled as she just smiled, inspecting me. "Don't forget we'll be dressing up again on Monday," Smiled Theresa. "That's Halloween night, but let's just take it one day at a time for now ok, and I'll decide later about what we're doing Monday after today?" "How about I get through today first," I said sarcastically. "Oh you'll be fine, but I've got to fix those pretty boobs of yours first," said Theresa, unzipping the back. "You're needing just a little more adjusting in the middle." "Ok?" I said looking down watching. "This little trick I think you'll appreciate," she said touching my flesh. "Appreciate boobs on myself," I said having to laugh at her thinking as she pushed the dress off my shoulders. "Or maybe you won't," she said pulling out the falsies. "Just hold your arms out a little and don't let it slide down. Just think of me letting you in on one of our little secrets." She then pushed the straps down off my shoulders for a moment and then unclipped my bra in the back. From the table she took the black roll of duck tape she had used to tighten the elastic on the gaff, but never did I think it would have another purpose or this would be how it would be used. I had never seen her ever use anything but scotch tape on a present, but instead now she ripped off a sizable piece and then pinched together my little fleshy chest. It's pretty amazing actually how much cleavage could be created knowing I really had none, as she taped near the bottom of my pinched boobs and then added the second piece of tape underneath the first. When she finished, she re-buckled the bra and then re-inserted the falsies. She pulled the dress back up over my shoulders and then re- zippered the back before straightening the sides. "Ok, can't see the edges now. They're not huge but they look pretty decent," said Theresa, inspecting me. "Twist for me and let's make sure they stay in place well. How do they feel?" "I don't even know how to answer that," I said, peeking down and twisting a bit. "Pretty damn shocking honestly." "Ah finally a compliment I guess," she said. "But they'll look even better in a second. Be still as I can't get this on your dress or you will be changing." I didn't even know there was more she could do as she then carefully took a brush, working between my cleavage. It took her a few minutes but then I glanced down, pulling in my chin as I could see how she had contoured the gap to add some dimension to them. When she finished, she opened a box filled with jewelry as I was now trying rings on my fingers. For the most part not many of them fit, but then she found a cubic zirconia cluster ring with an open back as she was able to bend open the slit in the back of the band, expanding it so it fit on my left ring finger. Fitting the pinkies wasn't that bad then shortly a small pearl ring was on my right pinkie and a swirl rhinestone pattern fit the left. She then opened a new package she had bought with a flex band costume onyx oval gemstone ring, surrounded by faux diamonds, which set easily, covering the right index finger. A couple rings on each hand were enough to satisfy her anyway, as nothing else fit. A bunch of costume gold bracelets and one bangle easily fit over my right hand, and a little gold watch looked almost lost on my left wrist. She held up a few different earrings against my ear, weighing her selections before finally deciding and pulling off the backs. "I should have made you pierce that other ear. Would have been much easier!" she lectured, half teasing and half serious as I'll never forget watching her bend the posts of the black and gold tier drop chandelier earrings as she fitted them into the clip on extensions and then pinched them to my ears. They felt so tight pinching my lobes as she took out my left ear's little stud. I didn't expect how annoying they actually felt, as I guess I had sensitive ears as she looped a necklace around my neck. Her last touch was getting down on one knee as she closed the clasp of a gold ankle bracelet around my left ankle and then stood, stepping back just staring at me. I remember trying to figure out if she was focused, zoning out or something was wrong as I stood there almost like I was drenched in a surprise rain storm, feeling completely bamboozled by her spacing out. "Are we finally done?" I said trying to get a reaction. "Do I look that weird?" "No, no, no! I'm loving how you turned out. Sorry, just running through everything in my head for a moment," she said. "There's some little things here and there I was thinking about, but I was making sure I didn't forget something. Come on you must be dying to see how pretty you look, so come get a good look at yourself in the bedroom while I get dressed." She wasn't wrong as I was probably even more curious than I ever expected to be, as I couldn't stop looking down at my boobs and legs for the first time in a dress. I was already somewhat decent at walking in heels, but being in a stretchy skirt instead of pants was certainly a new sensation. As guy,s we just wander around walking without really much perception unless there's a strong gust of wind or a rock in your shoe. Yet seconds into my first steps as a girl, I couldn't help but notice so many unexpected feelings, as I guess the excitement of my reveal or the butterflies in my stomach heightened my senses. I had already grown cognizant of my curls kind of bouncing as my head moved with each step, but the sound of my earrings softly tinkling near my eardrum and rebounding off my cheek was just so foreign. I was also so aware of the tiniest little things, like bracelets jingling on my wrist or my heels clicking on the floor, but what makes this all the more strange is weirdly your mind soon accepts these things as somewhat normal. It was a good thing I was wearing a strong deodorant, as I could feel my entire body perspire as I followed her into the bedroom. It wasn't like I didn't know exactly what was happening and normally I'm not the nervous type at all, but for whatever reason this was not something I was at all comfortable with, even though it was only Halloween. "This is fucked up," I said really only half looking at myself at first. I was hard not to look up and down, mostly surprised at how skinny I looked in a dress. In reality it wasn't that surprising because I had good tight abs and a thin frame, but the first thing I couldn't look past was how I looked with boobs, now that I was looking straight ahead at them instead of just peeking down seeing mounds. She had certainly pushed them up and out so well, creating some decent cleavage I couldn't believe it was mine and whatever she had done with makeup really drew my attention to them. I had nice long looking toned legs in my shortish length skirt, but the reality was that I didn't ha