Mrs. Tiffany Hollingsworth free porn video

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"Mrs. Tiffany Hollingsworth" As Ted laid me in the center of the king size bed in the master bedroom I could feel my heart pounding and hear the ringing in my ears as my head spun. I was nervous and felt the redness of embarrassment in my face as I gasped wide eyed and choked a dry nervous swallow as I smelled the floral scent of the perfume I wore floating around my head as Ted got into bed and moved in on his knees. I could feel and taste the slickness of the gloss red lipstick I had on as I tossed my head from side to side, my light brown curled hair tussling as I tried to look away, to deny the moment. Ted moved between my legs and swished up the lace edged layers of the sheer, vintage, pink nylon chiffon baby doll nightgown. I heard the whispering swish as the layers of nylon zipped as he fluffed everything up over my waist and out of the way. I then noticed the totally hairless and smooth ladylike legs in tightly gartered nylons and the pink six inch stiletto heeled pumps that were on full display now. I felt the nervous panic at seeing my legs looking like this, my mind reeled again. The totally smooth legs now sheathed in opera length vintage neutral grey sheer nylon stockings, the pink six strap garter belt pulling the tops of the stockings taut, the sheer filmy fabric shining in the faint room light, the nylons zipping as Ted spread my legs wide then bent them at the knees as he eased them over his shoulders. The shiny fabric zipped again as he ran his hands up and down my feminized legs gasping breathless with excitement as I wore the very outfit he'd bought home earlier in the day from a local upscale ladies lingerie store. His vein engorged erection bobbed in the cool room air and glistened in the light from the liberal amount of clear lubricating gel that he'd applied. He took it in hand and as he leaned in between my legs he began probing with it, steering it into me! As we moved on the bed the slippery, layered nylon fabric of the gown slipped down. He quickly fluffed up the lace edged layers of pink chiffon back up over my waist once again. I grimaced at the sensation as I felt the dark pink bulbous head of the large erection as he pressed it against me and worked it up and down. I gasped again and writhed, squirming under him as he found the opening. He worked my nylon clad legs wider still. I began to panic as he leaned in and began to push into me. "N...no, T...Ted, d...don't! I...I c...ca...can't!" I finally stammered in a panic. "Yes you can. Just relax," he assured breathlessly. "We're all alone, nobody's going to see, nobody's going to know, we'll take it easy, just relax now," he gasped urgently as he leaned in pressing more firmly now in an effort to get himself inside before I could escape his grasp and wriggle away. The floral perfume continued to float in the air, the satin sheets and the nylon fabrics whistling and zipping once again as I writhed underneath him. And then I felt him press harder still then felt the bulbous head begin to stretch the opening! I gasped wide eyed as I saw my smooth, ladylike, nylon stockinged legs high in the air now and grunted as I felt him press against me until suddenly, I heard Ted moan with pleasure as he felt the bulbous head begin to enter and I felt myself being stretched. And then still hunched over me he pushed again! I felt myself being stretched tighter still as I gasped in panic and grunted and then gasped in a girlish shriek as I felt the bulbous head finally enter fully stretching me tight! He continued pushing I felt the large vein engorged shaft begin to slide in, one inch and then another. He leaned in and continued pushing as he begin sinking into me, deeper and deeper now. Firmly inside he quickly put his hands around my trim waist and pulled me further down on the mattress then leaned in yet again, my legs even higher in the air now. He then pushed and ground against me in little pushing thrusts grunting softly with pleasure as I felt him continue to sink deeper and deeper inside. I grimaced and issued another girlish gasp as I felt the tight stretching sensation continue until finally felt his hips pressed tight against mine as he ground against me. I could feel his large dangling ball sack as it pressed against my smooth bottom! And then he began pulling out! For some strange reason I felt a sense of relief that he pulled back, that he was going to pull out. But after pulling out only a couple inches he pushed back in tight and ground against me once again. He pulled out again a bit further and then as he hunched over me he slowly pushed himself back in all the way. He then continued this humping, pulling out and pushing back in in longer and longer strokes, the lubricant working to full effect now as his eyes fluttered and he moaned open mouthed with pleasure. "D...don't T...Ted! I...I ca...can't! It...it's t...t...too ti...tight!" I squealed as I writhed underneath him, my nylon clad legs in the air gleaming in the faint room light as I grimaced. "D...don't worry. Mmmmm. F...feels s...so g...good," he cooed with breathy excitement as he began to pump and then thrust in longer and longer strokes! I could feel the strokes getting longer now, how he'd be all the way in, tight inside pressing against me and then how he'd pull out until the base of the bulbous head would stop at the tight stretched entrance and how he'd push back inside in another long full stroke. I could hear the sound of the lubricant, the "splork" of each poking thrust as I grimaced and grunted. And then as his pumping rhythm began, I could hear the "pat-pat-pat" slapping sound as his hips bumped tightly into mine at the end of each long stroke. I heard the bed begin to creak slightly as the gasping and my "ungh-ungh-ungh" grunting from his thrusts continued and the "pat-pat-pat" slapping sound the thrusts made as he had his way. And then I heard the whispering swish of the satin sheets and the sound of my pink, nylon chiffon gown and my shiny nylons zipping as he continued. All dolled up and powdered and perfumed I looked down momentarily between my gartered nyloned legs as he humped me in and out. The little trim "V" between my legs, my flaccid hairless manhood flopping small and useless now, the little nuts in my hairless scrotum looking like marbles, everything looking emasculated, feminized and small in comparison to his large vein engorged seven inch erection, the large egg sized testes dangling in the large ball sack swinging, brushing against the tops of my smooth nylon stockinged thighs with each thrust. The grunts and moans echoed throughout the bedroom now and through the open door and down the hallway and through the house. Thankfully we were the only ones there, the drapes drawn, the large luxurious house dark and empty now in the pre-dawn morning with nobody knowing the wiser as to what was now happening in the master bedroom. Ted continued, working to a fever pitch and as the bed creaked louder and the nylon and satin zipped and swished even louder the "pat-pat-pat" slapping sound continued! I gasped and writhed again, wriggling to squirm away but with him all the way inside now and with him holding my hips and with me on my back, my nyloned legs splayed and high in the air there was no escape. I wriggled my hips and spread my legs wider still but the tight stretching sensation continued, the muscles in my smooth shaved legs flexing tight now under the tightly gartered, sheer grey nylon hose shining in the light from the little lamp on the night stand, the pink stiletto pumps undulating, the heels twitching in the air over his shoulders from each of his thrusts. And then I gasped and grimaced again, wide eyed as I stared at the ceiling and into space. My mind went blank momentarily as the realization was now complete. I was Tim Benson, I'd been living with Ted and had begun dressing like a woman for him during the day, and now here I was all dolled up for the evening in ladies lingerie and being fucked just like a woman! As he moaned and grunted and continued thrusting in and out, in and out my mind began to drift, to drift in thought as to what could have possibly happened to have put me in such a bizarre position! Ted had spotted me at a Halloween party nearly a year before. I'd gone dressed up as a vintage housewife, a June Cleaver type. I had real high heels on and was wearing nylon stockings and full lingerie under my floral rayon house dress. But I took a lot of ribbing when the college friends I was with that night noticed that I'd shaved my legs for the costume. A couple of the girls giggled and wowed when one of them swished up my skirt and slips to reveal my white lace trimmed nylon under slips, my smooth shaven legs and the shiny, seamed beige vintage gartered ladies nylon stockings I was wearing, my long legs on full display now, the sturdy white garters at the top of my smooth hairless thighs straining as they held the stocking tops taut! As I flustered and struggled to swish my dress and slips back down they said my makeup looked too good and gasped when they learned I'd taken a curling iron to my hair instead of wearing a wig. I tried to pass it off as trying to do a good job for Halloween but I felt my party guests, the girls and my guy friends pull away at the sight of me now, at my having done too good a job with my costume. In reality it would have been an amazing and all-out effort for an average guy to look as proper and vintage as I did but for me it was almost second nature. I knew right then and there that I'd really fucked up. But, being my last semester in school I knew that soon I'd be moving on and these friends for the most part would be gone for good. So with a few drinks under the self-belt of my vintage house dress I figured the heck with it and continued with the party. But something else had happened that I couldn't have anticipated. Ted Hollingsworth had finished work for the day and had been sitting at the bar just finishing his second drink. The bartender brought another and he took a sip. He'd been looking over the costumed partyiers when he spotted the tussle at my table as the giggling girls swishing up my dress. There followed an audible gasp from the surrounding tables and from several men at the bar when they got the full view of my vintage ladylike legs sheathed in the tightly gartered old-fashioned ladies hosiery, the legs splayed slightly as my feet wobbled on the high black patent stiletto pumps. He sent a round of drinks over to our table but I didn't finish the drink and got up to leave early. Ted followed me with his eyes noticing my legs and how I minced and wiggled on the heels and how my nylons shined and how my dress swirled as I walked past him as he sat at the bar. He then took note of the scent of my floral perfume. He got up from his chair tossed a twenty on the bar then turned and stopped me a few steps from the entrance and started up a conversation. I figured I'd laugh off this party because I was graduating from college at the end of the semester because I'd be gone anyway. Even though I was a non-traditional student being in my late twenties I figured I'd still be able to land a good job. But up until now it had been a tough go with the rough economy and not that many good jobs out there. Not only that, I'd soon have to move out of my small apartment, relocate and find that job and another place to live. I was about to hail a cab when Ted offered me a ride home in his luxury town car. I took the offer but on the way home during some casual small talk I noticed him looking me over, especially my legs and my black patent leather stiletto heeled ladies pumps. I stayed aloof and made no attempt to get friendly. But Ted, in his mid forties took notice, he was old enough to remember the June Cleaver look. He mentioned my legs once again, mentioning it mainly because he'd happened to be looking my way when the girls swished my dress up exposing the shiny, nyloned legs and my red face embarrassment as I quickly struggled to swish it back down. He said he had a nice house in a secluded, tree lined area of an upscale suburb. Once he knew I was going to graduate school without a job he made me an offer. "How would you like to model for me," he asked. Model? Model what!? I thought. What could he mean? And then he mentioned my legs once again. He said he was an amateur photo buff of sorts with a small studio in his basement. "Just a few legs and heels pictures, maybe a bit of lingerie," he said then insisted. "I'll buy the all the clothes and stockings and lingerie you'll need and don't worry, there will be no face pictures," he assured. I was aghast at such an offer, imagine me Tim Benson a 26 year old man being offered to model ladies lingerie for pictures!? He then offered me a thousand-dollars for each two hour photo session with free food and drink and free transportation to and from his house. He gave me his card and number when he dropped me off at my place. I put the card into my purse and had forgotten the strange offer by the time I entered my building. But then, three months later I'd been out of school for over a month with the money gone, groceries nearly gone and my last months rent payment history. And now, with not being able to land a job and in having to leave my apartment in mere days I was really in a fix! That Friday night I rummaged the back of my small closet and found my Halloween purse, the number and card Ted had handed to me was still inside. After an hour of thought I nervously dialed the number. I was nervous and about to hang up the phone after four rings but then Ted's familiar voice answered cheerfully. Two afternoons work the following weekend earned me two grand in cash! Enough to cover my rent for another three months and get some groceries and buy me enough time to find a real job. But the jobs weren't there. Sure the flipping burgers or stocking Wal-mart shelves McJobs were there but that was an eternal dead end. With no real choice I had applied for a stock clerk night job just to get by, then I waited for the phone to ring. Two days later it did, but instead of learning whether or not I'd gotten the new job it was Ted! Another thousand for only a couple hours easy work was way easier than a month of lugging boxes and stacking shelves so I couldn't refuse. But still this couldn't possibly be any answer to a real job. "You can't find a job and can't afford your apartment. Why don't you move out and live here?" Ted mentioned after yet another photo shoot as he spooled the film from his SLR camera and I sipped a beer. He took me into his dark room and showed me three already framed prints of my "work," My smooth and ladylike legs in the six inch black patent leather stiletto pumps on full display as I perched in a pose on a high studio chair the jet black sheer and shiny nylon stockings pulled taut with tight black garter straps with just a trace of black peignoir lace draping down. 11x14 black and white prints so clear I could see the stitching on the heels and the actual flat knit weave of the glossy, sheer nylon stockings, even the gleam of the steel garter tabs. A very impressive and well lit portrait that looked more like fine fetish art. I couldn't believe those feminine legs were actually mine! I then learned from Ted that men's legs, when presented like mine now were on the large and glossy prints were actually better proportioned than a woman's legs. The calves are more defined and the thighs not quite so thick. The legs looked more 'willowy' and that was the trick. He said then added that it was easy for a man's legs to appear to muscular, too angular but in noting that I was short and slender and slightly built, and that I did little exercise my natural look came out with just the perfect mixture of attractive details. "Gee, maybe you could enter one of those pictures in some kind of leg contest or something, maybe we could win some money," I wondered aloud. "Tell you what Tim," he said as he put the camera down and put a few things away then shut off the studio lights as we returned upstairs. "I've got a few wealthy gentlemen friends who share my interest in fine portraits like these. I've already discretely shown them around to a couple friends. They're interested. Something for their walls in their private office suites. Because their stodgy, blue haired socialite wives don't have legs like that, not even their young kept mistresses. I even have the materials to matte and frame the pictures, to order. But, being 'fine art' they won't go cheap," he insisted. "I'll go 50-50 with you for every print I sell, what do you think?" "How much money are we talking about?" I returned quizzically. "Five-thousand dollars for a numbered print on a very limited and exclusive run," he returned not batting an eyelash. "I've got three guys interested and they've mentioned others they know too. It might just be a fad, but who knows. Class never really goes out of style. And it would sure pay better than stocking shelves don't you think?" He finished. A thousand bucks for two hours work, and then if he moved a print I get another twenty-five-hundred? In cash? This was starting to sound like stable employment. I quickly forgot the fact that to rake in that kind of money I'd have to continue swishing and vamping around his downstairs photo studio dolled up like a vintage Zsa Zsa Gabor. But then again, I figured why not? And then to make things easier he made another suggestion! "You can have the run of the place as it's just you and me living here," he went on. "You can have your own room too. And if you'd like to earn even more money? Well, I could use a little help around the place, you know, some light dusting, housework some cooking," In our conversations during the photo shoots we'd learned more about each other. Ted had an office in town, his own part-time business as a consultant. He'd already made his fortune in real estate and was now helping others buy properties and houses and strip malls and such, a part time job so he wouldn't have to just sit at home all the time. And conversely, he learned I liked to cook and since I was a neat and tidy person to begin with keeping house would be easy. "You can even dress the part of a proper 'housewife' when you're working around here if you like. I don't have many friends or house guests that visit anyway," he insisted. "D...dress like a housewife!?" I guffawed. But he didn't buy my gasping dismissal. "Why not?" He added. "I know your legs already look fantastic, but in watching you swish around in those peignoirs, how you move, I can tell you enjoy it. And especially how you can navigate mincing around on those impossible six inch stilettos, well, it's obvious you've had practice. I should have slipped out of those black patent heels and hopped back into my blue jeans and tennis shoes and hit the road I thought. Even with the possible financial windfall this offer was getting bit too strange for me. He knew I liked the clothes and he'd noticed how I could move in the lingerie and heels. And in my being naturally short, slight and slender, well the numbers added up pretty quick I guess. But with the latest shoot now done and after a couple of beers I felt the crisp, new ten one-hundred dollar bills folded in my hand and realized maybe it wouldn't be so bad to live in a luxury home and do light, part time housework instead of going back to my present circumstance. Aside from the photo shoots, Ted didn't have a problem with my dressing, he seemed like a nice gentlemanly type and even appeared a bit lonely but his offer would sure help me out. I figured I could maybe try his offer for a week or two, maybe a month at most while I continued applying for other jobs. I moved in and then it wasn't long until nearly another year had passed! I felt Ted's breathy humping thrusts once again as the bed continued to undulate and creak then felt the tight stretched sensation as I came back to reality. I immediately felt sickened at how far this strange relationship had gone. My head spun once again as Ted picked up speed his thrusts slapping, pounding fully into me now. "And then he gasped. I began to panic red faced. I writhed underneath him and squirmed as I felt him swell even larger inside stretching me even further, even tighter! He wobbled on his knees as he pressed tight against me, the ball sack pressed tight against my bottom as he held still against me, as deep in as he could get. Then he gave another thrusting, poking grunt as he ground against me then tilted his head back and with eyes closed let out a stuttering pleasured moan as he became weak on his knees! I grunted wide eyed at the sensation and squirmed as I felt the first twitch then the pulsing as his powerful spasms began pumping his ejaculate inside of me, the thick ropes of sperm spurting and jetting out of the tip of the bulbous head shooting even deeper inside. Until finally he thrust a couple more times to finish then pushed all the way in once again. I felt him going soft as he fumbled through the night table. He then took out a pink, paper wrapped object and unwrapped it and handed it to me. "Get this ready," Was all he said. He then pulled out slowly and finally plopped out, the quickly softening erection still gleaming with the clear lubricant as it bobbed between his legs. "Go ahead," he said in a spent gasping tone as he looked on. And then I realized the pink object was a woman's tampon applicator! "Go ahead, get it in so you don't make a mess," he said as he looked on. Ted noticed with satisfaction the dribble of sperm forming at the opening. I took the applicator and worked it against the opening and felt the embarrassed flush on my face as for the very first time I pushed the plunger that sent the white dribble of sperm and the pink applicator deep inside. When I pulled the applicator out only a white braided string remained. "Since you already had a bath I'll just take a shower while you dress for the day," he said as he moved off the large king sized bed and headed for the master bath. I then noticed the faint morning light coming through the white nylon window sheers of the bedroom windows. I swished my gown back down, got up and returned to my bedroom that Ted had fixed into a feminine woman's boudoir only a few months earlier. He'd made sure I had plenty of stylish vintage clothes similar to the June Cleaver look at the Halloween party. Seems that look that was a secret favorite of mine was also a favorite of his. I slipped out of my vintage pink layered nylon chiffon baby doll then swung open the walk-in closet doors to pick out a day dress and started my morning ritual once again then looked to the back corner of the closet. Two packed soft-side suitcases, a baseball bat and glove and a golf putter propped in the corner and a medium cardboard box that contained a couple pairs of mens' shoes a few old and dusty pictures of Tim Benson and friends and such, a few papers and odds and ends and my framed college degree I'd received the year before. After what just happened and remembering my ladylike nyloned legs high in the air and then the tampon my head began to spin again. A hot shower, scrub off the makeup, comb out the hair and stuff it under a baseball cap then get dressed and hit the street then walk to the bus station, I thought. A few more photo sessions had continued on after I moved in and I'd saved most of the money. And with him selling nearly a half-dozen of my leg picture portraits I had another fifteen-grand in cash squirreled away, plus Ted had also paid me for my time in working around the house . With him paying for everything there wasn't any real need to spend my money. I couldn't help but feel sickened and humiliated as I relented and began to dress for the day yet again, and in full vintage housewife regalia! Soon I was mincing around the kitchen preparing breakfast, my heels clicking, my nylons zipping and my dress, petticoats and slips rustling and swirling as my floral perfume continued to float around the kitchen. But as I minced around and set the table I could feel that tampon still deep inside and felt it swelling as it soaked up Ted's large and thick load. I became flustered as I felt my face redden again as my mind reeled. "Mincing around the kitchen just like a proper lady-of-the-house. And that little session this morning seems to have put an even more feminine wiggle in your walk," Ted said with a satisfied smile as he entered the kitchen dressed for the day, the morning paper in his hand as he took his seat at the table then watched me move about the kitchen. He took a sip of his orange juice then snapped his paper open to read the financial section first as he always did. But as I worked and felt that tampon my mind reeled. "I...I don't like doing it 'that' way. I didn't like it last night and I don't like it and I don't want to do it anymore. I don't want to do that anymore Ted," I said with a firm tone in my voice as I shoveled the bacon and eggs onto our plates and returned to the counter to get the toast. "We took it easy, I was gentle just like I said wasn't I? What we did was nobody's business. Nobody saw and no one will know," he reasoned as he folded his paper and set it aside. "It'll get easier once we do it a few more times if you'd learn to relax and get used to it. You might learn to like it," he assured. "No! Fuck that! I don't want to do that anymore," I blurted, stammering out the toughest Tim voice I could muster while I stood there with my hair curled and made up and with gloss red nail polish and in nylons and heels and full lingerie and in a dress and even a woman's vintage apron tied around my waist. I could feel the coolness of the pearl necklace around my neck and smell the floral perfume floating around my head and then feel the studs of the pearl earrings in my ears I'd only had pierced two weeks prior that were an additional feminine reminder that took the punch out of my protests. And then it was Ted's turn! "Let me ask you Tim. Where did you think this was going? Huh?" He asked bluntly. "We're both adults here." He reiterated the story he'd told before, about how he'd been married twice. For some reason it felt like he was conditioning me. But he continued saying that today's woman was too macho, to competitive to man-like. Plain-Jane slovenly unkempt women these days would never return to dressing like I was now as a hyper-feminine vision of a vintage housewife. He'd bought them clothes and encouraged them but it was too much and after a short time both marriages ended in divorce. I'd been a hard luck case that stepped into his ideal role of a 'housewife' and all because I had done too good a job for a Halloween party. I'd been offered easy money for the "photo shoots" and it was, and Ted had kept my little secret. I never told him that I liked to wear dresses, that I liked the feel of women's things but after looking me over I guess I didn't have to because he'd already figured things out. "You do a good job in the kitchen Tim and keep the house nice and neat and everything but what does it take, ten-fifteen hours a week, at most? And anything major like carpet cleaning or fixing or painting we hire that done. The rest of the time is yours to keep your hair nice, do your nails and makeup, try on clothes and dress as you please, to swirl and mince around the house to your hearts content. I don't associate with many people but a few know I've hired a Tim Benson on to help him out while he looks for a job. I never mentioned your alter ego or our arrangement have I when we've been seen out with you in 'male mode'? Is it that tough? Is it that big a deal to ask that you 'do it that way' once in a while? You can live like a woman if you want but in doing so and in me always seeing you around the house like that you must realize that I am a man and I have my needs," he finished. I swallowed a bite of egg and toast and washed it down with some orange juice then dabbed my lips. "Yeah, but it's too much Ted. Maybe even though it won't be near as easy on my own, maybe it's time I hit the road, you know?" I explained and shuddered slightly letting him know I felt the previous evening was too embarrassing and just too much for me. "You live on a gated property, in a three million dollar home in a large secluded tree lined lot. I've spent thousands on redecorating your bedroom into something feminine that suited you and thousands more on a new wardrobe for you to wear around the house. Then I dropped another eighty grand on a new car for you. Beats walking or taking the bus doesn't it?" He mentioned. "Yeah, a pastel pink BMW two door coupe," I returned. "A perfect choice for a ladies car," he returned with his 'lady' notation as if with the car and then the tight stretching I'd gotten with me all dolled up the night before was some sort of a plan to pull me even deeper into his idea of a feminized lifestyle. I didn't like where this conversation was headed as I squirmed nervously in my chair at the kitchen table. I felt my silky lingerie slide under my shiny rayon dress and felt my nyloned thighs slip and zip and then felt the tampon swell larger still as my head began to spin again! I felt cornered and he knew it. "You've got zero net worth, a worthless degree and you've saved a few thousand dollars? Even if I gave you that car and you sold it how long would everything last with you in another apartment until you had to get a burger job, hum? You want to grind it out, and quit dressing? Can't be fun clopping around a dingy apartment in thrift shop ladies shoes and things, and what if you get discovered. Women don't like 'your type' Tim. Single, alone and broke for the next 40 years? Tragic," he reasoned as he finished his breakfast. "I have to get to the office. You think it over today," he said as he finished his coffee, wiped his lips with a napkin then folded his paper up. And then as I stood in the middle of the large kitchen looking like June Cleaver in my apron and teetering on the high stiletto heels he left for the office. I was now fucked and in more ways than just last night! I had the kitchen back in shape and the table and counters wiped down in another ten minutes just like a normal day. I'd already done most of the housework the day before and aside from maybe a half hour of light dusting after lunch that was my day today. I could take a leisurely nap, read a book or watch a few movies in the home theatre. For now I decided to head back to my bedroom. My bedroom. Frilly and feminine and pastel and filled with white French provincial furniture. Another feminizing aspect, everything upscale with no expense spared. The lighted vanity filled with every manner of women's makeup and hair care things, expensive salon stuff from the best department stores, some things I still wasn't sure how to use just yet but as Ted had mentioned casually "I'd eventually learn all the tricks of the trade until it became second nature," Another thought that sent a chill up my spine. The dresser drawers brimmed with every manner of lingerie and foundation garments and vintage nylon stockings in every hue and shade. The vintage stuff Ted couldn't find he had custom made to order and in my size. As I swung open the double doors to the walk-in closet I saw another sight. Rows and rows of women's dresses, skirts, blouses and gowns of every description. And underneath, row upon row of the high stiletto heels that Ted liked, most with five inch heels and several more with a full six inch heel. Most of the dresses and gowns were classic and vintage and a lot of it had been special ordered. There was a section of the closet that had a few contemporary women's clothes, clothes designed for me to blend in with the local upscale ladies and shoes with lower heels to match and even jackets and car coats and a full selection of ladies purses, scarves, gloves, everything any ten upscale ladies could ever need or want. But then I got another chill when I looked into the back corner of the large closet. My "Tim Benson" identity in the form of those two black suitcases and the sports equipment and the large cardboard box I'd brought when I moved in were now gone! My head spun as I returned to the room and sat on the quilted pink satin comforter covering my bed. Still in my frilly vintage apron and house dress I sat there like a reincarnated June Cleaver. The feminine room an exquisite feminine boudoir, almost too "girly-girl" for even the most feminine of real women in the classic old days, and most certainly way too feminine for the women of today. Surrounded by the ultra-fem and without a stitch of male clothing or even my "Tim" identity I choked a dry nervous swallow and swooned as my head spun. I then picked up the receiver of the pink princess phone that sat on the white night stand under the small lamp with the frilled white shade and dialed. "Where's my clothes!" I barked as soon as Ted picked up on the other end. "Just relax will ya?" He returned. "Try on some makeup or lingerie or dresses or something, or take a nap if you want. Or, why don't you take a look at those new swim suits I picked up for you. You can go downstairs and hop into the tanning bed and get a nice start on bikini tan lines if you like," he said then finished. "Look, I've got a client coming in in a bit, I'll be home later this afternoon, we can talk more then," he assured as he quickly ended the call as if it was just another day. Maybe for him it was but not for me! I slammed the phone down and finally got up and straightened the slippery, pink satin comforter on the bed then moved out into the hallway and down the stairs and into the huge living room the dress rustling, the nylons zipping right on cue as I minced and wiggled along. The place was a palace though, If I worked for a thousand years I'd never have a place like this, or as nice a car to drive either for that matter. I thought about calling a couple old friends. Friends from my old home town 200 miles away, maybe see what Jimmy or John or Dave were up to lately. Since I'd moved out with Ted my college friends were gone, moved out and away now and I'd drifted away from them and everybody else for obvious reasons. And the women? Sure I always liked the babes but with the way I was, no matter how understanding a woman I met would be it would soon be no dice. Had to be. So, going "hey guys, I'll pay for plane tickets, take a break, come on out, I live in a mansion now. We'll shoot some pool, watch a movie, toss the steaks on the grill and tap a keg and take a swim in the pool out in the four-season patio and talk about the old times and how things are going. And Ted being a nice guy, well he wouldn't mind. I nearly dialed the operator when reality hit me like a bag of hammers. I was living as a woman! I had to laugh as their questions flooded my mind. "You live with a guy!? You live as a housewife!? And what's with the dolled up fem outfits!? You don't really like all that stuff do you!?" The retort? "Well, Ted likes it and dressing up isn't so bad, not really, once you get used to it. And now I live like a billionaire socialite but have to do it as a woman. Not such a bad trade off when you think about it really." Yeah, Tim Benson, hopeless closet cross dresser who stumbled on his high heeled feet and right into a man of means, and a man who was every bit as far out on the edge of fetish reality as I was, but from the other side of the fence. A perfect out of this world match, a one in a million shot, the absolute perfection as the moon and stars aligned. Unbelievable! We'd gotten along so well in this arrangement so far that that aspect didn't even need to be mentioned, we both read each others minds and knew! Was I gay? No. Really? Naw! What was happening was a continuation of the fetish. I'd read it in college in some ancient, dusty out-of-date psych study. It started with sheer nylons for me as a kid, seeing them hanging dry over the shower curtain rod shining in the light. Should I try them on? NO! The memory clanged sharply. But, yeah, I did and then I was sunk and I knew it. The book said that no matter how you start you nearly always end up fully dressed and made up and everything. It's just a matter of time, the progression of such an accursed affliction. And the advanced cases of CDism being determined to be TS in followup, a man actually trapped in a woman's body. But that wasn't me, it couldn't be me. I minced around the place as the morning sun streamed through the large living room windows. I looked at the paintings, perused the books on the shelves and looked around like an impressed visitor, but now I was living here and had the run of the house and as I moved I could feel the earrings dangling in my ears, smell the perfume and feel the luxurious swish of the expensive lingerie under my vintage house dress and feel the frictionless zip of the shiny, sheer nylons as they made their "shick-shick-shick" sound as I minced around the room. From head to toe and from the skin out I was now wearing it all. Ted had seen to that. He knew what he liked and what I adored, and just what was needed for the satisfaction and constant soothing of my psyche. My mind reeled at the situation. Did I miss the baseball caps and the blue jeans and T- shirts and tennis shoes and stuff? And just a comb through my hair in the morning and a shave every two days or so to keep my thin-wispy beard at bay. Then a spritz of Right Guard and I was off. A routine that shortened my now daily routine by at least an hour! But I did adore the clothes. The hairdos and makeup and long nails and dangly jewelry secondary but essential for a complete polished look. And as the months had passed the complete daily routine had become second nature. And then my head spun once again when I remembered that large pink box from the downtown upscale "Lady Grace" lingerie and dress shop that Ted had brought home the day before. And what had happened next. And then his words from that morning came back clear as a bell, "you think it over today," he'd said. But as chilling as things now were where was this going? It still hadn't registered. And then, in mid afternoon I heard Ted's car pull into the garage. Moments later he entered the kitchen and set his briefcase on the table as he greeted me. He pulled me close around the waist. He smelled my perfume and my nylons zipped and my house dress swished and I teetered on the stiletto heels as he pulled me close and nuzzled my neck. But I felt tense and distant after "thinking" all day and pulled away. "What's the matter?" he asked. "Ah, just a bit tired I guess," I added in the small conversation of just another day. But I knew it was much more than that. After I'd moved in and after my initial embarrassment in dressing like the lady-of-the-house every day Ted began treating me as a woman. Sitting close on the couch in the evenings, him with his arm around me feeling my silky dress and brushing his hands over my smooth nylon stockinged legs. It was his enjoyment, innocent at first but unnerving to me. Then the afternoon greetings, the hugs and the little kisses as he'd pull me close when he returned home. He'd encouraged me to swoon slightly and lift and bend one of my shapely nylon clad legs in classic vintage fashion as he held me. And he'd kept an eye on me to encourage my "ladylike" manners and movements. Women's clothes and the high stiletto heels dictated much of my movements but he wanted shorter wiggling steps, limp wrists and more poise and grace. I guess over the past year I had learned by osmosis and constant practice, as I had done with the hair and makeup. I grabbed two beers from the fridge and handed one to Ted as the after work routine settled in once again. "Where's my suitcases and stuff?" I inquired as I leaned against the kitchen counter. "Ah, you don't need all that stuff anymore," he said as he waved passing it off. "You didn't answer my question," I insisted. "I took all your clothes and sports stuff to the thrift store yesterday. Your papers I tossed at the office, alright?" He finished a bit miffed after being put on the spot. "That was my stuff Ted! Your clothes don't fit me, they're way too big. What am I supposed to do when we go out or I have to run errands or go grocery shopping," I returned. "I'll take care of the errands and you can have the groceries delivered. Problem solved," he added. "And going out to movies or grabbing some fast food or going out to eat or just taking a drive or a walk in town window shopping, what about that? I don't mind being home most of the time but the thought of not being able to go out at all bothers me a bit," I added a bit rattled now, not fully understanding what he meant. But then the other shoe dropped. "I'd just as soon that you didn't wear any men's clothing anymore. If you go out just dress in a contemporary ladies fashion. I think you'd blend in pretty well after living here as long as you have. The nervousness of going out as a woman will diminish over time. And you can start going to the salon, you know, just like a regular lady, weekly appointments for your hair and nails and make overs. And you could start laser electrolysis to get rid of that wispy beard of yours. You'll never have to shave again. I know of a full service ladies spa near my office," he rattled off like it was now matter-of-fact. "And your name, Tim Benson, that doesn't work anymore either. I was thinking of something more fitting now. How about 'Tiffany' that's a nice ladylike name. Nothing masculine about that. Getting used to 'Tiffany' and with you dressed only in women's things, it would be so much less confusing don't you think?" I gulped the last of my still cold beer and tossed the bottle under the sink, then I grabbed another from the fridge, twisted the cap and took another sip. "What are you talking about Ted?" I stammered back. He didn't waste any time in continuing. "I don't think it would be a great idea if I was seen out and about with Tim Benson anymore. Buddies and all, even though people know that I'm just helping a college kid get back on his feet we should just get some distance from that," he said as he looked at me, my thoughts still not coming into focus as he waited then finally erupted. "Oh come on Tim! Like I said, what did you think this was? We're both adults here! Figure it out. I enjoy seeing a vintage June Cleaver swirling around the house and all but what kind of arrangement is that really. I mean long term? Kinda runs out of steam after awhile doesn't it? And then after last night, well you made it clear that you don't like doing it 'that way.' And like I said, I have my needs you know," he said as he downed his last swallow of beer, handed me the empty and waved for another, appearing a bit tired now but determined as I handed him another beer, then took my open beer and an unopened third beer to the kitchen table. I plopped down in thought, crossed my nyloned legs and smoothed my dress and slips as Ted took a seat at the table as well. "I've been talking with a doctor friend of mine. He's a councillor and an MD. He's got experience with male-to-female transsexuals and he's been looking into a few things for me," Ted started. "After a cursory meeting and a physical he'll start you on female hormones and a testosterone blocking agent. Then he'll start working on changing your paperwork so you can continue on as Tiffany instead of Tim Benson." "Wha, what!? What the fuck are you talking about Ted!?" I gasped nearly spitting my beer across the kitchen floor. "I...I'm not one of those! I'm not a Transsexual! I'm not some man stuck in the body of a woman," I assured. "Well, you certainly aren't much of a man now are you Tim?" He reasoned smiling as I shrunk and cringed at the sensation of all the silky clothes I now had on. "A college degree to be sure but with no real job and no prospects. Few friends and no chance of any real relationship with any women. That's just your situation, the way it is. I didn't set that up. Go ahead, look at yourself. Are you really a man Tim. Humm?" "Well, there's no way I'm starting on female hormones!" I shot back. "You don't like doing it 'that way' you said, isn't that right? Well my doctor friend insures me that once on female hormones after a time your male thoughts will begin to fade. Depending on where in the spectrum you are. And if you are only just a cross-dresser he tells me that that's still enough to start with. After a few months you'll start thinking like a woman and your mental state will be more in line with you dressing and living as a woman and then getting used to a man's attentions. A year or two more and all that confusion will end and your life as Tiffany will be second nature," he said with assurance. "What the fuck have you been smoking!? Nobody can be sure of any therapy like that!" I said stymied for anything else to say as my stomach churned and my head spun at the fact that he'd already gotten with a doctor friend of his and it would only be a paper shuffle to start me down the road as a woman! "We've already been through Tim Benson's future. You want to leave? Heck I'll steak you, put you up in a nice place, let you keep your new car. I'll buy you another 'Tim' wardrobe. I'll foot your bills for another five years anywhere you want to live, within reason. Go ahead and look for a real job, real friends and then try to find a real woman. Oh, but then there's that little problem that always comes back to haunt isn't there? Finding a woman who won't think you're a freak. And then once your secrets out no more friends and no more job. It doesn't matter there's all the LGBT rules and laws on the books. An employer learns about Tiffany and suddenly you'll be a 'difficult' employee, 'argumentative' with few friends. You know how it goes. And then, either way it's McDonalds or Wal-mart and no car and no benefits and a crummy apartment alone?" Ted finished with a quite masterful stroke. It was genius and it was airtight! I felt sick. My head spun at the very real thought of spending the rest of my life on high heels. "Maybe we could continue on for awhile." "There's no future in that," he continued. "Take the councilling and start the pills. Give it a month or two to see how your thoughts measure out. You're lucky really," he said as he looked me over. "You're what... five-foot-five, a hundred and twenty pounds dripping wet, you've always been short and slight and almost naturally hairless. You're not a swish or effeminate but you're learning," he said with a chuckle. "You've got naturally fine features. You're lucky with your prissy mind set that you aren't six-foot-three and two-hundred pounds with rough features and hairy as a gorilla. But as Tiffany you stand a real chance. Redo the hairline, resculpt the nose a bit, enhance the cheekbones and you'd be nearly undetectable. A little practice and only a gynecologist could prove you weren't born a genetic woman," he theorized. "And I stay on, living here full time and permanently? And how do you explain what happened to Tim Benson? And then where did your new live- in Tiffany come from?" I returned. "I didn't say it would be smooth sailing all the way. But I've already put a few things in motion. With the doctor/councilor and a few other things. The Tim/Tiffany connection may never be found out about. It's really nobody's business. But, that's a chance we'll have to take. If it ever comes under question I'll just come out with it. Tim was transgendered and I helped him along then got along so well with Tiffany that things just clicked. And if they don't like that explanation, fuck 'em! I don't tell anybody else how to live and I'm financially stable enough and own my own business and independent enough so that it won't matter anyway. If I lose clients I'm still solvent," he finished. "So, it's all planned out then?" I gasped nervously. "It's a work in progress. You see the doctor early next week and we'll go from there," he reasoned. After such a wide ranging conversation most nearly all involving Tim Benson I had no choice but to realize that his life was nothing more than a miserable dead end. But Tiffany? That was a whole higher level I didn't yet fully understand. But, as I looked up from the table I took the chance and agreed to see the councillor the following week. And then, strangely, I could taste the lipstick and feel the earrings in my pierced ears. My head spun again as I squirmed in the chair and I felt the full silky sensation of the women's clothes I had on. The frictionless breezy feel, the zipping of the sheer nylons and the feel of the slips and skirt of the dress mocking me now, a portent, me falling down the rabbit hole into a feminized world, with me totally and utterly feminized with no way out, no escape! I was apprehensive to take the passenger seat as Ted drove to the clinic the next week. I felt nervous and beside myself in being out dressed as a woman for the first time and it showed. I still had my nice lingerie and garter hose on underneath but now wore a simple long skirt and ladies low heeled boots and a simple blouse and a lady's coat with a matching purse. My makeup was more plain and minimal and my hair was combed in a plain style. Yuck! I didn't look like the slob soccer moms and looked upscale but dressed this way I worried I might be seen as a guy-in-a-dress, especially when getting out of the car in front of a mental wellness clinic! Doctor J. F. Milton, MD greeted me in his office as I entered. Ted stuck around for a bit chatting and then went out to see the receptionist and go over some of my paperwork before he took a seat and picked up a magazine. I took a seat and set my purse down as the doctor looked me over without a smirk or a chuckle. He seemed professional in his job as I was far from flawless. But he seemed to understand. Then the conversation started, the cross dressing came out but I didn't seem to fit the profile of being TS to the level he had expected. However, he'd had several conversations with Ted and after knowing our situation and after a quick meeting he wrote me a prescription for the female hormone estrogen. I'd done a lot of reading on the subject and mentioned I'd need a testosterone blocker as well but he only gathered my file and had me follow him into an out-patient exam room. I noticed the padded examination bench had stirrups, and that a nurse was already there working! He had me step behind a curtain and undress and then put on a hospital gown. I'd just had a physical so why was this needed I wondered. But, I was assured that my case history was already well documented. He had me lay back on the table and before I knew it the nurse was starting me on an IV. She laid me back on a pillow and I began to feel spacey as the doctor put my feet in the stirrups. He then wheeled over a tray and put on a surgical mask. He loaded a syringe and I felt the first needle stick. I tried to protest but then I began to fade out as if I was in a light sleep. And then it was over as quick as it started as I woke up. The doctor was just snapping off his latex gloves as he finished looking me over. "Put your girdle in your purse for the ride home Tiffany" he said. "I want you to stay loose and comfortable down there and in a week, ten days you'll be good as new," he assured. An "out-patient" procedure I was told. Within ten minutes I was able to get dressed and limp back into the reception office where Ted was waiting. My steps shortened as my crotch felt pinched tight somehow now. And the doctor hadn't given me the testosterone blocking medication I'd be needing. But Ted merely collected me and soon we were in the car and on the way back home. I had trouble sitting and felt another pinch and was so uncomfortable I finally swished my long skirt up and pulled down my white ladies nylon briefs. My mind reeled to see my little manhood and my hairless scrotum and the two incisions on each side of the now empty sack. My testes were gone! They'd been clipped and I'd been neutered! I eased the nylon panties back up gently and swished my skirt and slip back down as my head fell back against the headrest spinning, my ears ringing now too! "I thought you said 'try it out for a while,'" I said as I glared at Ted. "This is no trying anything out Ted, my nuts are gone!" "Just relax now, everything went fine. The doctor seemed to agree with me. And, he mentioned that the female hormones will act a lot faster with no testes in the way," Ted said. "You won't need the testosterone blocking agent now and the doctor said that within a month all the testosterone now in your system will be gone and you'll switch over fully to the female hormones. And there shouldn't be any side effects just being on estrogen. You'll have check ups to monitor your medication as we go until you balance out." We stopped at a pharmacy and Ted went in and moments later came out with a small plain brown bag which he handed to me. I opened the bag and looked at the large bottle of pink pills, take one each morning with breakfast the prescription said on the label. It was lunch time as Ted pulled into a drive through to order a large bag of burgers and fries. I was exhausted and knew that I wouldn't be doing any housework or cooking for the next few days. But Ted already knew that. I healed up slower than I thought but within ten days I was back in the doctor's out-patient exam room having my stitches out. And then as the days went by I continued taking one of those pink pills with every breakfast. What a joke I thought. No nuts and gobbling these little pink pills and no changes. But then as the weeks began passing I started noticing the tenderness in my chest. And, my areolae and nipples were turning a darker shade of pink and were indeed getting larger, the surrounding tissue filling out and getting puffy! I also noticed the hair on my head was getting thicker and more luxurious while my body hair had diminished, my skin was softer too. I also began to notice mood swings, the emotions and how I'd get upset at the slightest thing. Part of it might have been the tenderness and tingling in my budding breasts but now I was definitely noticing the changes. And my dresses even started fitting easier too. Another visit to the doctor and all was fine. I still wore my silicone forms at home but now I was an "A" cup for real. The doctor slid a box and a jar of cream across his desk. "The cream is hormone laced and I added an anaesthetic to stop the tenderness and tingling. We've had good results with it, you rub it on your breasts at night. And then," he went on as he opened the pink box and took out some clear tubes and two clear plastic globe like objects. "After you rub the breast development cream into your chest you put these on," he said holding them up to his chest. "They're suction, breast pump devices, you hook the tubes up to the little motor that's in the box and pump your breasts up tight. Not too tight but snug. Once you're pumped up, unplug the tubes and leave the globes on for ten minutes a night, three nights a week. But, use the breast cream nightly," he said as he put everything back in the pink box. I was soon on my way home once again. And aside from this new added routine I didn't look much different. "I thought you'd have wider hips and a more slender waist and at least by now with those globe things bigger boobs," Ted said exasperated as he looked me over one evening before I went to bed. "Well, you're the one who had everything all planned out, you tell me!" I blasted back in another head spinning emotional outburst. And then a few more months flew by. Turns out that Ted needn't have worried. As time went on the estrogen really kicked in, aided by now additional hormone injections I did at home once every two weeks. My hips did grow wider and rounder and my waist trimmed down to feminine proportions. But the most noticeable change was that I was now a full "C" cup! The torpedo shaped breasts I'd started with had grown out a lot more and had rounded out and were now taking on weight! I had to relent and visit "Lady Grace" for my first brassiere fitting! "I...I'm a male-to-female transsexual," I said nervously and in a whispered tone to the elderly lady in the women's fitting room as she looked me over noticing I wasn't that "womanly," I was sure I was about to get tossed out but Ted had already had a talk with her and she seemed very cooperative and pleasant. It might not have hurt that Ted owned the strip mall her "Lady Grace" dress and lingerie shop was situated in. But still, in this instance the cat was indeed out of the bag. In about to be fit for new brassieres I had no real choice but to confide in the fitting lady. She even had smaller silicone forms I could switch to to keep the same chest size so my dresses and blouses would continue to fit every day until I finished filling out. How large I'd fill out was anyone's guess. But so far the pink pills and the cream and the suction globes were working overtime. Tim Benson, or the idea of him began to fade now, as did my emotional outbursts. And when I got my new drivers license photographed as Tiffany Hollingsworth it was strange to see the word "Female" on the identification. I then learned that this was possible as since I was neutered and on female hormones I couldn't be a male anymore and under my doctor's care my new status was granted. And as more time passed the other paperwork that drifted in reflected my new female status. "A hair set, a perm!? And salon nails and pedicure too?" I gasped after supper a few nights later. "The bra fitting was embarrassing enough and now you want me to go to an actual beauty salon?" I asked as Ted stood by. He'd found a picture of a vintage ladies hairdo online and printed it out. "That's the kind of hair set I want to see you in from now on," he said excitedly. "I don't suppose this beauty salon is in another building you own, is it?" I meekly asked. "Nope. You'll have to pick a place, a nice one of course but you'll be on your own this time. Maybe ask for a chair in the back or something. Tell them it's for a costume party, I don't know. You'll get used to the new routine," he assured. And he was right. I sure didn't look, or feel much like a "Tim" anymore! After looking through the yellow pages and found a place or two we drove over to the location, something off the beaten trail, something upscale and suburban. We finally settled on a salon only a couple miles from the house. I was still nervous about going and when I did I watched my demeanor and kept my voice soft and as ladylike as I could. Then, to try and clinch the deal I wore a low cut blouse and a new demi-cupped shelf bra to show off my ever growing breasts. The fleshy orbs stood out and jiggled, and with my trim waist and my wider hips I felt I might just get by. This change-over program was tougher and more nerve wracking than I thought. I never imagined going to this level, maybe that was the problem. The day of the appointment I gritted my teeth took a deep breath before pulling the door to the salon. The bell on the door "dinged" and I soon found myself at the receptionist's desk as "Tiffany" ready for "her" appointment! I got a chair towards the back and the stylist was soon working me over giving me a cut and style and then a set. Meanwhile I got a pedicure in gloss red and then had a manicure with long ceramic salon nails glued on tight and then lacquered with the same gloss red polish. By the time the lady working on my hair combed out the first section and rolled the hair I braced for the sensation as the first pink curler was then rolled and pinned tightly to my scalp. My head spun, here I was as Tiffany getting my first roller perm hair set, and in a vintage style! My head was soon festooned with over three dozen curlers arranged in neat rows and I was being led to a seat under a large hair dryer. I was on my "high maintenance" way now! Ted had me change into a June Cleaver house dress a few of the ones I'd been able to have altered for my new feminine shape, and the black patent leather stiletto heels with beige seamed nylon stockings even. He then marveled at the total package, the long, gloss red salon nails, and my new eyebrows that had been plucked into a high and feminine arch. He marveled at the change in makeup which included false eyelashes and was wowed by the tightly curled and styled and very authentic vintage ladies hair set. He finally pulled me close and danced me around the living room for a moment until I told him I'd had enough for the day. He relented. Gad! Was I being "bitchy" now!? Or maybe it was how I looked these days, especially now after my first salon treatment. I'd done everything Ted had wanted after his impassioned and quite logical argument in favor of his plan. It was a quiet evening. While he sat in the La-Z-Boy watching TV and I sat on the end of the couch nearby I asked when he wanted to do my facial work. A couple days later after contacting the doctor/specialist a clinic was located and I was scheduled in a months time. But this time the thought of a multiple day hospital stay got me wondering and worrying about the complexity of my facial feminization surgery. We checked into the clinic after a three hour flight and a long cab ride. After I settled into my room Ted found a nearby hotel with room service. I was processed quickly and then after tests in the morning I was scheduled for surgery. Another needle stick, but no out-patient stuff now. This time it was the full operating theatre. I was out before I had time to allow my blood pressure to get out of hand. I was being wheeled back to my room and being told that the surgery went off without a hitch and frankly, even better than planned. Spectacularly actually I think were the words the pleased surgeon said as he looked me over checking the bandages while was still groggy and quite out of it. After being wheeled into my deluxe private suite I was in and out for two days. Then, on the third day the pain set in! "Nurse! Nurse!" I yelled in screaming pain as I laid awake on the third morning after trying a sip of liquid breakfast through a straw. I'd found the morpheme drip in the remote button on the bed and had pressed it so many times with my thumb that I'd maxed it out, to no effect or relief! It felt like someone had worked my head and especially my face over with a ball bat. Not a kiddie junior league wiffle ball bat, no, we're talking the Michael McGuire/Louisville oak slugger, and that fucker was on his full steroids and wearing a glove too! I felt the tears rolling down my cheeks and under the bandages as if I had been slicing onions. It wasn't sadness but mostly the searing pain that registered in thumping waves with each heartbeat. But still there was some sadness in my thoughts. What the fuck had I done!? The nurse flitted by with concern and returned with a doctor who put me back out with an injection. Day four, the twilight of sunset. Another pump of the morpheme drip and I actually felt better now. But over the past days I'd lost another eight pounds. I was too sore to even eat a liquid diet. I could only lay back and watch television and there was nothing on but commercials! Ted had been in and out but because I could only mumble and looked like a mummy there wasn't any point in him staying to watch commercials. He did seem a bit alarmed at the swelling and how wi

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Charisma and Tiffany Part 4

Charisma and Tiffany, Part 4 By Cal Y. Pygia While bathing her in the shower stall, before pissing on her and making her drink the warm, golden beverage she'd poured from her bladder, Charisma had planned to fuck Tiffany in the ass with the aluminum Little League baseball bat she'd brought into the shower stall with her for that very purpose. The bat would have opened the shemale's asshole even more than Charisma had when she'd fist-fucked Tiffany, inserting not only her fingers and...

4 years ago
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Katheryn and Tiffany

Kathryn was laying in bed, thinking about her son, Derrick. He was coming home from college tomorrow. She was ecstatic, after all she hadn't seen him in almost three months, not since his second semester of college started; which meant, she hadn't fucked him in over three months. He was twenty-one now and they had been having a sexual relationship for over three years. She wasn't sure why she desired or craved him as much as she did. She wondered, why is sex with him so much better than with...

1 year ago
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Blue Balls 2 Tiffany Teases

Summary - Tiffany continues to tease her older brother and discovers her father is affected by her youthful charms as well. Previous Story Summary - Tiffany learned a naughty trick to play on her brother. Note – This is a work of fiction, make-believe and sexual fantasy. It is not based on real people or actual events. You must be 18 or over to read these stories. The author does not condone any sexual activity among persons under 18 in real life. In real life, incestuous relationships,...

2 years ago
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Baby Tiffany

BABY TIFFANY By Betty Noone It was Christmas Eve and Jack Winston and his wife Cindy were relaxing, enjoying the fire in the fireplace after having opened the presents they gave to one another. They have been married for five years and were deeply in love. There were no children, and Jack knew that there could be none before they were married, as Cindy had a genetic condition that prevented her from getting pregnant. Jack was a vice-president and junior partner in an...

1 year ago
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Tiffany Crosses the Color Line

Tiffany Crosses the Color LineCHAPTER ONE** Tiffany's journey continues as she is turned into a black streetwalker. **NOTE: This trilogy picks up where "Tiffany Gets Decorated" left off. To learn more about these characters and how they got into this situation, you may want to read that series first - D---Kyung Mi -- Kaitee for short -- never ceased to amaze me. As a graduate level psychology student and academic prodigy, her knowledge of the human mind was stunning. And, as Tiffany's roommate,...

2 years ago
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Tiffany Tries a Hamam

Part 1 Tiffany was furious with her parents. What were they thinking, sending her to this godforsaken place? She wouldn't have minded a summer in Rome or Paris but no, they had to send her to Istanbul. Just because she got in a little scrape back home in Tennessee, her parents decided that she should spend some time with her uncle, a career diplomat, and his Turkish wife. Istanbul! It was foreign to her in every sense of the word. The smells, the language, the cuisine and the customs were...

1 year ago
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The Trouble with Tiffany

I returned home from the meeting in a good mood. The new client was pleased and had agreed to a long-term contract. I was pleased with myself for closing the deal. As I pulled in I saw Tiffany's Jeep in the driveway.I entered the house to find Pam and Tiffany in the kitchen. Pam was wearing her usual shorts and t-shirt. Tiffany was wearing a very short white skirt and a white tank top. Her huge breasts hung freely with her thumb-sized nipples showing through the material."Hello, handsome,"...

Swingers
4 years ago
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Tiffanys New Boss Chapter 2

Tiffany sprinted from William’s office sobbing her eyes out and straight to the bathroom where she washed her mouth out with cold water. She brushed out the dried up cum that had become matted in her long locks and scrapped her hair back into a ponytail.She headed to her car and sped away from the haulage yard and back to her house where she enjoyed a nice hot shower, she desperately scrubbed her face and hair hoping that it would make the memory of what just happened in William’s office...

3 years ago
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Tiffany

" ... but don't you think he's too young for that?" Mom asked and I held my breath waiting for his answer. "He's going to be thirteen," Dad said. "That's old enough, believe me." "I don't know," she sighed. "It's a lot of money and..." "When I was Josh's age, I wanted one more than anything else in the world," he cut her off. "My parents couldn't afford it, but we can. It'll be good for him, you'll see." "I hope so, John," she agreed reluctantly. They were quiet...

3 years ago
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One of the many sexual encounters of Chase and Tiffany

Chase + Tiffany lesbian scene  One of the many sexual encounters of Chase and Tiffany Tiffany Andrews and Chase Walker first met in an orphanage at a very young age. Even though Chase was three year older than the other girl they both looked the same age. The parents of Tiffany were killed in a ski accident in Colorado, and the parents of Chase were murdered in New York; so they had something in common from the start. Because the girls didn?t have any other relatives there were put for...

1 year ago
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Kathryn Tiffany and Derricks Vacation

Derrick pulled the car into the motel's parking lot. They had arrived at Corpus Christi at 4:30 P.M. It took them eight and half hours to get here from Dallas. Derrick looked over at his girlfriend sitting in the front seat aside of him. If all goes according to plan, this vacation will mark a new step in their relationship. He looked at his mother sitting in the backseat. Kathryn winked at him and blew him a kiss. Yes, he thought, it should be one helluva week. Kathryn said to the two...

3 years ago
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Charisma and Tiffany Part 2

Charisma and Tiffany, Part 2 By Cal Y. Pygia Tiffany's six cocks filled Charisma's six cunts and, although the sorceress was on top and, therefore, able to move faster and with more force and agility than the supine shemale, Tiffany, nevertheless, felt overwhelmed by the welter of sensations that had, as it were, laid siege to her consciousness, dividing her, as it seemed, into six selves, each of which was assaulted by the sea of emotions, physical sensations, and lust that...

2 years ago
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Milking Time B1 Chapter 1 Tiffanys Arrival

This story involves a group of shemales who live on an island thatexists in our world, but they chose to remain mostly isolated. That's partof the reason I also call them amazons.The shemales in my stories have genitalia that start at JohnHolmes' size, and then get much, much bigger. (This is a work of fantasy afterall.) So if extreme size is not to your liking, I suggest you go elsewhereand pick another story.This story is copyrighted and may not be posted anywhere without myexpress written...

1 year ago
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Charisma and Tiffany Part 3

Charisma and Tiffany, Part 3 By Cal Y. Pygia Tiffany didn't hate Charisma, not exactly, although, the more she thought of how the sorceress had treated her, how she'd abused her, the more the shemale fumed. Not only had Charisma changed her sex, from shemale to female (and back again, thank God), but she had also equipped her with a half dozen cunts, including one in her forehead and one grown from the roof of her mouth, in which, with an equal number of penises newly sprouted from...

1 year ago
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Kathryn and Tiffany

Kathryn was laying in bed, thinking about her son, Derrick. He was coming home from college tomorrow. She was ecstatic, after all she hadn’t seen him in almost three months, not since his second semester of college started; which meant, she hadn’t fucked him in over three months. He was twenty-one now and they had been having a sexual relationship for over three years. She wasn’t sure why she desired or craved him as much as she did. She wondered, why is sex with him so much better than with...

Incest
1 year ago
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Charisma and Tiffany Part 1

Charisma and Tiffany, Part 1 By Cal Y. Pygia As a beautiful shemale, Tiffany De Vine had had a lot of superb lovers, both male and female, but she couldn't get Charisma off her mind. She'd met the sorceress when she'd bought one of the brassieres that Charisma had designed. Actually, as she found out later, it was the only brassiere that Charisma had ever designed. It was, Tiffany supposed, a sort of bait, and it had done its work; it had caught Tiffany as surely as any lure had ever...

3 years ago
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Blue Balls 1 Introducing Tiffany

Summary - Tiffany plays a naughty trick on her older brother. Note – This is a work of fiction, make-believe and sexual fantasy. It is not based on real people or actual events. You must be 18 or over to read these stories. The author does not condone any sexual activity among persons under 18 in real life. In real life, incestuous relationships, particularly when an under-aged person is involved with a parent or adult, often causes deep psychological damage. This story is provided for...

2 years ago
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In Tiffany and Amys bedroom

This was turning out to be a weird night. Now, all of the sudden, some mysterious woman comes in the bedroom, and asked Amy who I am. "This is Tonya, you remember. I told you, about her," Amy replied."The one, you fucked in the sauna?" The woman asked."Yes, that one," Amy replied.The woman came towards us, and got down on her knees. I immediately wondered if, Amy had been cheating, with me. Then the woman, put her hand out."I'm Tiffany, and you are?" Tiffany asked.Tiffany? That name sounded...

Anal
3 years ago
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The Standoff Miss Tiffany Saloon Owner Joe ORiley Sheriff

The year was 1882; the west had started to settle down and many of the old wild, rough and tough towns were no longer that way. Such was the small cow town of Apache Creek, AZ; at one time it was famous for being one of the roughest towns to drive cattle through. A town that use to be run by crooked Sheriff Williams, who looked the other way when cattle were rustled or a cattleman was robbed.Now it had settled down and the old sheriff was gone, replaced by Sheriff Joe O’Riley, an Irish bloke...

Historical
3 years ago
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Jacob And Tiffany Naked in SchoolPart 2A Tuesday

Personal log (voice), J. J. Stone, captain of the Flying Dutchman, 1204 EST October 27th 2006. It was 12:04am. That is what my alarm clock said in those bright neon numbers the nearly blind could read at twenty paces. With my vision, I could not see them from further away than three feet. These thoughts I should not have running in my head. I should be having my post midnight fantasy about now. The noise that interrupted my sleep sounded again. I turned over and looked. There was a new...

4 years ago
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Tiffany does a Caribbean Cruise 1

I had knee replacement surgery. Big improvement. I could walk without pain. They didn't tell me the truth about the convalescence, though. It was much slower than anticipated. Based on their schedule, Tiffany and I had scheduled a week long Caribbean Cruise. Several weeks before the cruise, I realized that I wasn't going to be in tip top shape. When I took the pain meds, I was a zombie. Sleeping 20 hours a day. When I weaned my self from the meds, the pain was really annoying. Back to...

3 years ago
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Breakfasts with Tiffany

Gilbert unlocked the door to the apartment and walked in. It was Saturday morning, so he expected to be alone. His younger roommates spent every weekend visiting with their families. He had kissed his family goodbye six years ago, and never looked back. Well, almost never, he thought as he strode through the living room and into the kitchen. He opened the refrigerator and noted with annoyance that there were only two beers left. His roommates had once again left him hanging.Jason and Kevin...

2 years ago
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188 AVIS AND TIFFANY Mutual pain

188 AVIS AND TIFFANY Mutual pain My black lover Jerry called and told me he would be coming by to pick me up and he wanted me to dress in a blouse and skirt, no bra and with hose and ankle strap stiletto heels and to bring along my white sheer nightgown. As he drove up I went out to meet him, got in his car and leaned over and kissed him hard and long. As I settled back he looked at me, “You love me?’ he asked. “With all my heart” I replied. “You’ll do whatever I ask of you tonight?” he...

1 year ago
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Tiffany visits Uncle Dave

Tiffany looked out the window as the plane approached for landing. Florida looked so different from her home in Ohio. Of course she looked forward to the warmer weather.She was still surprised that her mother had allowed her to go and visit Uncle Dave. He was kind of the black sheep of the family passing on working on the family farm in favor of something to do with the internet.Most if the family had nothing to do with him except for Tiffany's mom. Over the years her mom had quietly slipped...

3 years ago
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The Metamorphosis of Tiffany

The Metamorphosis of Tiffany Tom put the cap back on his beloved red lipstick and admired in his wife's vanity mirror his latest masterpiece. He blinked at his reflection which showed a semi realistic looking woman albeit a trashy one. His long false eyelashes setoff his smoky eye makeup perfectly. It was just the look he was going for. After years of surreptitious practice, he had cultivated a real talent for applying cosmetics. It had taken months but he now had the slutty...

2 years ago
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Jacob And Tiffany Naked in SchoolPart 2B Tuesday

Monday, just after school Jacob sat in the unfinished command seat with his usual annoying calm. "Check the screens." I did. There were a bunch of cars boxing the ship in from all sides. I thought I saw something in common about most of the drivers. "System! Give me distance enhancement, ten feet." "Acknowledged." The ever-obedient computer replied. I could see the insides of those cars so clearly I thought I could reach out and slug those idiot drivers. But I could also see what...

1 year ago
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Kathryn Tiffany and Derricks Vacation

Note : This story is completely fictional! Never try to do it in real live! This is the last, at least for now, in the Kathryn stories. If you have not read any of the others, I would suggest you read them before you read this. Keep the sending feedback, I enjoy getting it and try and answer all of them. I hope everyone enjoys this story as much as the others. Derrick pulled the car into the motel’s parking lot. They had arrived at Corpus Christi at 4:30 P.M. It took them eight and half hours...

Incest
3 years ago
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Breakfast with Tiffany Part 1

Breakfast with Tiffany (Part 1) The nature of my work required me to travel. When I was younger the novelty of travelling, and being paid for it, was exciting and had a certain holiday feel about it but now it was just boring and I longed to get home and get back to the routine of a home life. I was on the second day of a three-day trip to Amsterdam and I had decided to avoid the obvious tourist attractions of the red light district and the coffee shops and have a quiet night with a meal and a...

2 years ago
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Breakfast with Tiffany Part 1

Breakfast with Tiffany (Part 1) The nature of my work required me to travel. When I was younger the novelty of travelling, and being paid for it, was exciting and had a certain holiday feel about it but now it was just boring and I longed to get home and get back to the routine of a home life. I was on the second day of a three-day trip to Amsterdam and I had decided to avoid the obvious tourist attractions of the red light district and the coffee shops and have a quiet night with a meal and a...

Oral Sex
4 years ago
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Training TiffanyChapter 2

Tiffany's birthday came round. I'd had a word with Hannah, but it was unnecessary; she was already organised. We had a very fancy meal – all the household staff, and Jon Sparrow together, with waiting staff hired in so no one was left out. Hannah had obtained a very elegant dress for the birthday girl, and she looked every inch the young lady. At the end of the meal, before we began handing her presents, I stood. "My friends, a toast. To Tiffany, who has reached or exceeded our every...

1 year ago
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Jacob And Tiffany Naked in SchoolPart 3A Wednesday

Personal log (voice), J. J. Stone, captain of the Flying Dutchman, 12:30am October 27th 2006. Scotty was finally content. He had discovered that sharing a bed with two passionate humans was not the best way to get an undisturbed night's sleep. His owner usually tossed and turned for about 20 minutes before he got comfortable. Scotty thought his owner acted much like a cat. Then he would curl up next to him and start purring contentedly. But not last night. Last night Scotty's owner...

3 years ago
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Tiffany Gets Decorated

CHAPTER ONE**Tiffany and David meet for her first humiliation in a restaurant.**Tiffany looked at me, her big, dark, almond-shaped eyes staring at me over the rim of the glass. It was her third glass of water -- lukewarm, no ice -- and she drank it in one long draw. Then, she set the glass on the table and lowered her eyes."Does that please you...Sir?" she said softly. There was just the slightest hint of anger in her voice.  I smiled. It was silly, it still felt awkward, but it was feeling...

1 year ago
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Jacob And Tiffany Naked in SchoolPart 3B Wednesday

Personal log (voice), J. J. Stone, captain of the Flying Dutchman, 7:50pm, October 27th 2006. I was singing to myself as the Flying Dutchman flew along. "It's Pinky and the brain. It's Pinky and the Brain. One is a genius, the other is insane..." I changed my voice slightly. "So what are we going to do tonight?" Then I spoke in my normal voice. "The same thing we do every night. Try to take over the world!" Now why would anybody want to take over the world? Have they no idea the...

2 years ago
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My client Tiffany

Introduction: This is about how i eventually got Tiffany into bed, all be it reluctantly on her part If I get enough positive responses I will post parts two and three! Ever since my husband caught me having sex with my best friend Lisa, and likes the fact I like to fuck girls, my cravings women have grown immensely. Plus now that I dont have to suppress those feelings I can act on any situation that comes my with his approval. Previously I would shy away from other women flirting with me or...

1 year ago
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Playtime Stories Ch 4 Tiffany and I are joined by

4. I agreed to Tiffany’s promise of more fun at her place. She was a talented ass-fucker and although I’d just cum in the porn booth I could already feel my cock-craving returning. 30 minutes later we were pulling into a two-floor townhouse in suburbia. Tiffany gave “Pet” a bullshit story about how I wasn’t able to go to my gay lover’s house because it was so late. At first he was a bit put off but then she added “Besides, you made a mess on her. The least you should do is clean her up…” ...

3 years ago
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Tiffany Takes it Seriously

One event in my calendar that I always look forward to is Sabrina’s sexy girlfest. It coincides with her husband’s annual golfing vacation and enables five horny women to meet up at her delightful country house for a weekend of sexy female fun. We enjoy a simple diet of fruit, champagne and orgasms and when we're all in the hot tub together we share some of the highlights of our sexual encounters during the previous year. I use a small Dictaphone to record all the graphic details so it’s a bit...

Hardcore
2 years ago
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Tiffany does a Caribbean Cruise 2

Mark guided them to the Sky Bar on the highest deck. Obnoxious modern music was playing, but it wasn't too loud. After receiving their drinks, Mark commented. “ You are a great fuck. Your pussy is tight and you are flexible. You suck cock well too.” Tiffany smiled and looked down into her drink. Her head was reeling. She must have wanted this to happen. Why else the change of outfit? Something subconscious, she guessed. “Go into the ladies room and push two fingers as far up inside you as...

3 years ago
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Jacob And Tiffany Naked in SchoolPart 5 Friday

Personal log (voice), J. J. Stone, Captain of the Flying Dutchman, 9 am, October 28th 2006. The hospital room I was in was rather quiet. The machines did their subdued beeping as they did what they were supposed to. But like any place there was quiet, it was about to be shattered. I woke up muttering. "The fluctuations in the density drives adjustments are causing the changes in the effective simulations of reality. Those fluctuations are caused by frequency adjustments. So what would...

1 year ago
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This slutty girl named Tiffany True Story and ou

This is a true story, I've wrote it off and on over the period of a week or so. There is a little bit of inconsistency because some of the details I had forgot. Names haven't been changed, I just didn't use my own name.When I was 19, I was fortunate enough to land a really good job through a family member. Although I wasn't much to look at, it didn't take long for girls to start noticing me (or my money) - where I live, good jobs are hard to come by and even 8 years later most of my friends...

3 years ago
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Buying the Family Next DoorChapter 3 Tiffany

Tiffany had her seventeenth birthday party early that evening. In addition to her mother and sisters, several of her young girlfriends were there. Shortly before the party was scheduled to break up at about eight PM, I saw a strange car pull into their drive. Even though I had never seen him, I knew it was Tiffany's lowlife boyfriend. He was actually her ex-boyfriend. He just didn't know it yet. He seemed to have a bad attitude as he purposely walked up my neighbor's drive. Without even...

2 years ago
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Tiffany My Teenage Slut

When I walked in, Tiffany was laying on my bed. When she had asked me what she should wear I told her to surprise me. She was dressed in the classical plaid school-girl uniform complete with an unbuttoned white blouse that barely covered her C cup breasts and her tight tummy on display for my viewing pleasure. Her legs were bent at the knees with white thigh-high nylons that came up and over her knees, covering her perfect long legs. The sexiest part was her plaid skirt that strategically...

1 year ago
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Tiffany does a Caribbean Cruise 3

I awoke from my drug induced nap just in time for lunch. I was laying on my back gaining energy when she opened the door. “Hey baby, I missed you.” I was stroking my cock and leering at her. “Nurse, I need some help here!” Tiffany had an expression halfway between a grin and a grimace on her face. “Just a second, let me visit the ladies.” She inspected her self and found a small semen deposit on her hair near the top of her head. She cleaned it with a washcloth and came over to the bed. “Well,...

1 year ago
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The United Kingdom of Zoo A fake BBC documentary seriess5e19 Tiffany Black 36

Series 5, Episode 19 - Tiffany Black (36) We open with our beautiful shot of the United Kingdom – from space ... Pause for a moment – just long enough to notice that this week the shot includes lines of longitude and latitude ... Then we fall toward the planet at hyper-sonic speed, dropping from a low-Earth orbit toward the country, staying on the zero-degree line of latitude ... Dropping toward the south, toward the huge urban spread of London ... Staying on that imaginary line – right into...

1 year ago
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Tiffany s birthday

Hay sweaty what do want to do for your birthday? Well mom the girls from my cheer leading squid are come for a sleep over can we get some pizza and can you get Dewitt out of the house for the weekend? He’s always trying to seek peeks at us when every the girls come over. Don’t weary sweaty I well handle him, my stepmom walked out tiffany’s room (my stepsister ) an striate in to my room with out knocking, there I was standing in front of the murrain naked with my cock in hand just jerking off...

1 year ago
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Tiffany birthday

Hay sweaty what do want to do for your birthday? Well mom the girls from my cheer leading squid are come for a sleep over can we get some pizza and can you get Dewitt out of the house for the weekend? He’s always trying to seek peeks at us when every the girls come over. Don’t weary sweaty I well handle him, my stepmom walked out tiffany’s room (my stepsister ) an striate in to my room with out knocking, there I was standing in front of the murrain naked with my cock in hand just jerking off...

3 years ago
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Tiffany does a Caribbean Cruise 4

Tiffany returned to the cabin as I awoke from another nap. We spent the afternoon walking around the ship and marveling at the number of things to do and see. Ice skating rink, sports bars, buffet, burger shop and of course bingo. But the wave machine was the most interesting feature. Powerful pumps created a moving current and people (mostly men) were lined up to try their skills. Many lasted only seconds before the current knocked them to the side of the tank, but some guys were pretty...

3 years ago
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Jacob And Tiffany Naked in SchoolPart 4B Thursday

Chapter 78: Tiffany Ship's log, Acting Capitan Tiffany French. 8:40am, October 28th 2006 I had put the Major and his Marines in the various chairs. They were demonstrating curiosity levels usually reserved for small children. So I told them they could be as curious as they liked but not to touch anything. So they sat and watched like tourists at a planetarium. Suddenly one of the Marines pointed to the holographic display. "Is that a carrier?" "Joe, put the thing that Marine is...

3 years ago
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Gambling with Tiffany

GAMBLING WITH TIFFANY I left school as soon as I could, the only subject I was any good at was maths and then it was mental arithmetic that I excelled at, not the fancy theorems. I was lucky in that I got a job in a large department store that had branches all over the country. Pretty soon I got onto their management training scheme and was moved to a major city. The pay was reasonable, but I didn't know anyone other than the people I worked with. One Saturday night I drew out some...

3 years ago
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Making Love With Tiffany Smith

Several years ago, I was sharing a house with Tiffany Smith while I worked at the local shopping center. I was not long out of school and had decided what to do with my life. My rural upbringing had seriously cramped my style, so I moved to the city in the hope of finding adventure, excitement, and girls.

Tiffany was Thirty five years old, and trying to become an actress and part time Hostess. She was slim and pretty, with long dark hair. She had a firm figure, and every morning I was treated...

2 years ago
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Jacob And Tiffany Naked in SchoolPart 1B Monday

Science class went as it usually did. Jacob and Mr. Schuman got into a deep argument again on the fundamental interactions of density as it related to forces within reality. They went at it for ten minutes again, losing the rest of us 3 minutes into the argument. I did sit next to him though. I didn't do anything else to get his attention. I just watched him scribble the answers to the science experiments in the lab book before Mr. Shuman finished explaining. In other words science class...

3 years ago
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SubSlave PVC Maid Tiffany

So where to begin with my good little slutty slave maid, well I suppose its starts with our agreed sessions on a Friday or Saturday where Tiffany being a good little crossdressing slut that she is would be waiting for my arrival dressed as requested in her PVC maid outfit. All our desires and kinks were already agreed before we started our sessions so we both knew what to expect, however there was something about turning up for a session to have the front door open to be greeted by your PVC...

2 years ago
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BREAKFAST AT TIFFANYS

BREAKFAST AT TIFFANY'SThe following is a true story that actually happened to me. I am really not fucking concerned whether you believe it or not. I just feel it needs to be told...for anyone willing to listen. It begins in the hallowed halls of Central High School, where I attended.There was this girl named Tiffany, whose guts I absolutely fucking hated and believe me the feeling was mutual. As far as looks go Tiffany and I were about dead even. As far as popularity goes, (I may have been...

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