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Part 1 The End of the Affair It was a rainy Thursday night; I pulled up to the Holiday Inn Express and parked in front of the room number that Stan had sent in a text message a few moments before. I wouldn't call Stan my boyfriend; he is certainly not a boy. He is the married father of two and a man in his mid forties. And it would be a stretch to call him a friend, we have had a sexual relationship for the past three years but that is as far as it goes. We meet secretly once or twice a month in a cheap motel room for a couple of hours of raw passionate sex. The sex is always good since he claims his wife doesn't meet his needs. And I am a 42 year old cross- dresser, gay or bi transvestite if you prefer those labels, and these evenings with Stan are the only opportunities I have to get my special needs met. I check myself in the mirror, I look good. I am wearing a shoulder length strawberry blond wig; my eyes look sultry with long false eyelashes, and smoky eye shadow. My pouty lips are dark red and I am wearing large dangling gold hoop earrings. I have on a tan raincoat, but have only a black waist cinching corset and black thigh high stockings underneath. Now since Stan enjoys the illusion so I am wearing breast forms and a sheath type vaginal appliance. I take one last drag on my cigarette, and step out of the car. I throw the butt down and crush it with the sole of my 3" stiletto shoe. I am not concerned about cigarette breath since Stan and I don't kiss. In fact the very next thing to enter between my lips will be Stan's swollen cock. Out of the corner of my eye I saw a late model Lexus sedan with a woman in the driver's seat parked a few spaces away. I didn't think much of it. I knocked on the door and Stan opened it and I went in. I said "Hi Stud it's been way too long" Stan replied "It has been too long Baby But I am more than ready" With that he opened his fly and the aforementioned swollen cock popped out. I undid my raincoat and let it drop to the floor. I licked my lips and dropped to my knees and took him into my mouth. The woman in the Lexus had gotten out of her car and was peering into the room through a slight separation in the curtains. She rapped on the window and yelled"Stanley How could you!!!" In mid suck Stan's cock disappeared back into his pants as I heard him say "Oh Shit it's my wife!!!" I grabbed my coat and slipped it back on but didn't button it. As I did I said "Stan I'll be going now I'm sure you two have a lot to talk about" He opened the door His wife burst in in tears; if looks could kill I'd be dead. With utter contempt she said "You cheap Slut!" I smiled wanly and headed out the door. I drove back to my place, and I know it seems self centered but I didn't care about Stan and his problems mostly I was thinking about sex and where my next fuck would come from. I dislike going to Tranny bars, while I like men I don't like the kind on men who hang around chasing trannies. On line relationships take a while if you are trying to be discreet and safe and I was horny right now. I went on line, trying to think of anyone I had chatted with lately that I could get to the next step but no one came to mind. Randy44 was on line, he was an older man, and I believe the 44 referred to the year of his birth. We had exchanged emails and chatted on line occasionally for a few months. Initially he had seemed interested in sex but he sensed my lack of interest and we discussed many things including taxes and estate planning. It is not so strange in my male alter ego it is how I make my living. Randy44 wrote "Good evening" I replied "What's so good about it? Randy44 wrote "y so glum?" I replied"Sorry date went really bad, his wife showed up" Randy44 wrote "that does sound bad, can I help" I replied "the only thing that would help is a hard cock" Randy44 replied"Oh I have one, want to cam?" I said "Y not" It took a couple of minutes to get cammed , I lit a cigarette and took a long drag and exhaled. I saw an erect penis on the screen and heard a voice say "I like women who smoke" I replied "Let me see your face" The camera panned up and it was the guy I knew as Randy44 I said "Good now back down to you cock" and went on "You like woman who smoke because you imagine it's your cock that they are smoking. Girls who smoke are dirty girls; they like to suck on cocks" "Grab the head of your cock with your finger tips, that's right, now make little circles with your index finger just like the tip of my tongue would do" I stuck out my tongue and moved it in circles "Now slip your fingers down your cock until the head of your cock touches the palm of your hand, that's right" I opened and closed my mouth in a sucking action and said "Now squeeze your fingers together every time I suck" He did and we repeated this several times, each time a little faster until I saw the cum burst through his fingers. "MMM' I said "I can almost taste it" It sounded like he was breathing heavy I said "Show me your face' It was flushed, but he was smiling. I said "Do you live alone?" He replied "Yes, yes I do" I smiled and took a long drag and exhaled it into the camera And said "Perhaps we should meet in real life" Then I turn off the camera and signed off the computer. I went got a 10 " dildo put it on my chair and slowly worked it up my anus while jerking myself off. Part 2 A New Day I got up the next morning and went about my drab life. By the way my name is Terence (Terry) Sanderson, and I am a CPA with my own practice. I was married for a while but divorced about six years ago. It took me a while to figure out what I wanted and what I found was my feminine alter ego also named Terry actually Teresa. Terence likes woman but not nearly as much as Teresa likes men. I guess that make me Bisexual but I am me and I don't find labels all that helpful. I am 5"11" tall and weigh 160. Now Mother Nature gave me a few good things and some not so good things. My hands are small and my feet a size 8 which helps with the feminine illusion. I have a nice set of legs and a round ass. But my hips are too narrow and shoulders a bit too broad so I need to choose my wardrobe carefully or wear a bit of padding on my hips. My mouth and nose are OK lips are a little thin but nothing lip-liner can't cure. My eyes are small and dominated by a bit too heavy brow line. I always wear wigs with bangs, and often wear glasses. I also use surgical tape to lift my brow line and make my eyes seem larger. Eye makeup is where I spend most of my preparation time before going out as Teresa. Two of the best things I have going are very soft skin, which my men friends love and a voice that with a lot of practice over the years, I can get high enough that it does not give me away. The pitch is important but even more important is using feminine speech patterns. Now I certainly am not passable. I don't go out in public in broad daylight and carry on long conversations with strangers. I can drive around, ask directions, buy gas, cigarettes, coffee, and of course condoms without any issue. By far, most of the talking I do as Teresa is to men who know about me and are really turned on my sexy husky voice. Enough about me, back to my day. I checked on line and there was a message from Stan saying it was over between us, (no kidding) but there was a silver lining he said his wife had no idea I was anything but a woman. There were several messages from Randy44 trying to set up a real life date, each succeeding message was a little more frantic and desperate. I was not at all sure how to proceed. He was not unattractive but looked his age, it was encouraging to see his cock still functioned but I was concerned about a one and done date. With all the effort I go though to become Teresa once is never enough to satisfy me. However I didn't have any other prospects at the moment and it looked like a long stretch of using the dildo in my immediate future. I was talking to a client about 11AM when I got noticed a message on my Yahoo mail account. I clicked on it and saw it was from Randy44, yet again. But the subject of this one was Professional Advice. Intrigued I opened it up and it said "Dear Terry I recall that in the past you said you worked in taxes and estate planning. I am not completely satisfied that the plan put together by my attorneys optimizes my tax liabilities. I would like a second opinion and even perhaps to engage you to develop an alternative plan. I know it is short notice but I wondered if today a 3PM would be convenient. Naturally I look forward to meeting you in person but I would not think to impose on our cyber friendship so I am more than willing to pay for your time at what ever your hourly billing rate is. Please respond and let me know if you can make it" It was signed Randall Simpson with an address in Chestnut Hill. I had actually heard of this guy, he made a ton of money in computer storage devices in the 90's and sold out before the bottom dropped out of the market. Thinking this could not be for real, I googled him and sure enough I found a picture of Randall Simpson and it was indeed the guy I know as Randy44. Thoughts started racing through my mind. First came sex. This guy was loaded he could afford the best talent out there. I am very good at taxes but not a big time player. This must be a ploy to get me to his house and have his way with me. Oh! but that would be a good thing. I am horny as hell. Then came money. Maybe he does want some work done. I could make some extra money and have sex. That would be an even better thing. What if he just wants tax advice? No he is horny too. Then came the really big dilemma. What do I wear? I was dressed in a nice businesslike blue suit, but the skirt was a little shorter than office appropriate and the white silky blouse showed just a little too much cleavage from my very realistic looking breast forms. And these days not too many real business women wear 3" spike heels. On the other hand I had a chin length blonde wig, very conservative jewelry, a medium red lipstick and nails and very intellectual looking eye glasses. Part 3 One door closes, another opens He opened the door, took my coat told me how lovely I looked We went into his study. There was a large pile of documents on a coffee table He offered me a drink but I declined Then he asked me to take a few moments to look over the documents and added that I should feel free to smoke I sat on the sofa, crossed my legs and lit a cigarette and started through the documents. It was a very complex arrangement but he was loaded. I had trouble focusing because he kept sneaking peeks while pretending to be reading emails. Finally he came over and sat down next to me. He asked "Well what do you think?" The first thought that came to mind was "about what this pile of documents or having sex" I took a long drag on my cigarette and tilted my head up and away from him and exhaled Then I said "Honestly Randy there is a lot here and it would take me a day just to go through it all. But law firms are usually cautious and I can probably find some things if you want to be a bit more aggressive from a tax viewpoint." I touched his forearm and said"What do you think?" He placed his hand on my thigh and said "I would be happy to more aggressive in any area you suggest. Please have you look into the details. Does anything stick out? " I smiled and said as I glanced at his crotch. "Well you do have one hard asset that should be liquidated immediately." He asked "What would be the best way to accomplish that? I replied "Why orally of course" I knelt in front of him and kissed the tip of his cock, then I kissed his balls, I rubbed my hands up and down his chest while I licked his the complete length of his shaft., then I grabbed his ass with both hands and swallowed his cock whole, he started thrusting powerfully into my mouth, over and over his manhood penetrated my lips, I could barely get my breath, Too soon he exploded, cum going all over my mouth and chin. He backed away. I cooed as I licked the cum off my lips, I took my finger and wiped some off my chin and then flicked out my tongue to lick his hot love juice off my finger. I stood up and said I'm going to freshen up; you just rest and regain your stamina. I came back into the study and he was on the phone, he motioned for me to sit down but I noticed we had knocked the documents in the throws of passion. In a ladylike fashion I bent my knees and picked them up. Then I pretended to notice something and bent over at the waist to seemingly get a closer look. Randy was now staring directly at the back of my thighs and ass. I held that position for a minute or so and then heard him say "I'll call you later, something has come up" I felt his hands on my hips and he said "You have gorgeous legs and one beautiful ass" I glanced over my shoulder and said"Admiration of beauty is a good thing, but beauty is meant to be enjoyed" I heard the zipper as he said "My pleasure" As I felt his rock hard member enter my anus "I replied No the pleasure is mine" I felt him enter me I thought to myself " I have had him ejaculate already so hopefully that will cause him to be longer than usual this time." I am pretty sure he did take longer, but honestly I wasn't watching the clock. As he repeatedly pumped his swollen member into my ass pussy I was in utter ecstasy, moaning and screaming "Yes Yes" as my toes curled. This time when I came back from the bathroom he offered me a drink and I accepted .It was a fine pinot noir. I said "Randy, thank you this has been a very pleasant and unexpected interlude in what promised to be a very dull day" He smiled and said "I agree, by the way do you have a card so I can have you paid for your time" I smiled seductively and said "For what little I did your debt has been satisfied in full" He smiled broadly and said "Terry I am serious about engaging you to review these documents, what would be the best way to accomplish that?' I said "Well we could carry them all out to my car and I could call you in about a week, but they are bulky and heavy. Maybe it would be best if we set another appointment and I could review them here" He beamed and replied"That's a great idea, could you do it all in one more visit?' I frowned and said "There is a lot there, it might take several such visits to get the job done" He laughed and said 'Well that would be wonderful when can you come back?" I replied "How about Thursday, the day after tomorrow." He walked me to the door and opened it for me. I pushed it closed and kissed him on the lips, he responded by sticking his tongue into my mouth. He was startled and said" What was that?" I said"Just a little test" He looked puzzled and I added "You passed" Part 4 A New Affair Thursday started out the same I read some documents and was beginning to fill in some details. He had been married and had a son now 35 who had two children of his own. The first marriage lasted 10 years and ended in divorce with the usual division of assets. He had been married two more times to younger women, neither lasted even two years and both were settled according to the prenuptial agreement. It painted a picture of a man traveling a long journey searching for what he really wanted. After about an hour he asked if I wanted to see the rest of the house. I said sure. He took me directly to the master bedroom. After admiring the decor, I grabbed his hand fell backwards on to the bed and pulled him down on top of me, and said breathlessly "I want you now" My skirt rode up to my hips as I scooted back on the bed, I wiggled out of my panties, threw them aside with my right hand while I held my private parts up and out of the way with my left. Then I wrapped my legs around his neck and pulled him toward me, I reached out and guided his cock into my anus, and whispered "OK Randy Make me feel like a woman" He was like a wild man, I felt like I was going to split in half, but I was enthralled watching him, all the passion, his face contorting, his heavy breathing, and the wild thrusts. The initial pain subsided and a deep sense of pleasure developed. It hurt but as the song goes it hurt so good. Now he wasn't anything special in the equipment department nor was is technique all that different. I really wasn't sure why I enjoyed sex with him so much, but I was glad I did As incongruous as it seems, I explained my ideas and what it might save him with us both sitting there naked. He actually listened and asked some good questions. Then he asked if I would be willing to talk to his attorney. I paused and asked "What do you have in mind? a phone call? a meeting at his office? He said"Oh I think a meeting here would be good" I said"and you would expect me to be.... He said "As lovely as you are today, but with clothes on" "OK" popped out of my mouth before I thought about it He said "Great I'll set it up" I now went back to my scribbling and thinking with a new sense of urgency I felt his hand around my ankle as he pulled my right foot toward him and placed it in his crotch. My attention was diverted from tax avoidance schemes and I rubbed my foot against his balls. Randy moaned. I kept that up for a minute or so until his cock was erect. Then I moved my other foot over and caught his penis between my feet. Sliding then up and down his shaft, over and over until cum burst out of him. It got over my stockings as well as him. He said he was going to clean up. And I said I need to wash out these stockings He said "You seem busy; It was my fault let me do it." I said " Why not, but you have to remove them" I stood up and he knelt in front of me, reached up shamelessly high on my thigh and started to slowly roll the stocking off my right leg, caressing my inner thigh as he did. By the time he finished my left leg I was so hot I could think of nothing but cock. I knelt down grabbed his neck and pulled his lips to mine passionately kissing him, then we tumbling to the floor with me on top. My mouth was devouring his tongue as my right hand reached for his cock. Sadly it was soft. I worked my way down his chest sucking on his nipples, kissing his belly but when my mouth got to it's intended target it was still soft. He squirmed out from under me. I said"It's all right Hon" He yelled back at me "No it's not!! I want you," I smiled seductively sat back down on the sofa, slipped off my panties, hiked up my skirt and spread my legs far apart. I said "If you really want me here is part of me you can have" His eyes grew wide, I could tell this was not something he was totally comfortable with, but it had to be what he secretly desired. I hadn't done anything for him that anyone of his wives or countless women could not have done. No if he was obsessed with trannies it was this that he secretly desired. I licked my lips as I stroked my meat and said "Come on you know you want it" He just stared at it without moving Finally I stood up and said "Well I guess I was wrong, anyway I should probably get going" Without uttering a word He walked over to me, put his hands on my shoulders and pushed me down to a sitting position, then he knelt in front of me, he lips inches from my cock. I said in a husky whisper"Touch it" He wrapped his fingers around it I let out a sigh and said"Stroke it please!!!" He started moving his hand up and down my shaft Then I said " Suck it Randy Suck it!!!" Hesitantly his lips parted and moved to within a quarter on an inch of the tip of my cock He froze. I acted; I thrust my cock into his mouth and clamped my thighs around his head so he couldn't pull back. At first nothing happened I said breathlessly "Pleasure me Randy" His lips slipped down my shaft, slowly I moaned loudly and shouted "That's it Baby Come on do it" He slid them back and sucked hard once and then again I moaned all the louder and said " Yes Yes that's what I need" I squirmed and moaned and he sucked more vigorously Just as I was about to cum, I pushed him away and my cock spasmed, shooting out a load of cum onto his chest. Breathlessly. I moaned "That was wonderful, You are great" He was really pretty average but I felt he needed the encouragement. He sat silently with a deer in the headlights look. I went into the bathroom and got a damp wash cloth and cleaned him up, I put myself back together and gave him a peck on the cheek saying "Thanks for everything Stud, you were great" and let myself out. He sent an email the following day saying he wouldn't be able to keep our appointment on Thursday. I didn't hear from him over the weekend. I gave it a good deal of thought. I certainly hoped my seducing him into a blow job hadn't blown the affair. Physically he was nothing special, he was old more than 20 years my senior, and while in decent shape and distinguished looking, he would never be considered hot except perhaps in the geriatric ward. But I enjoyed the sex and to be truthful more than most sex. I had never had sex with a man that I had any other relationship with so the fact that Randy and I had a business relationship added a dimension and a level of complexity that was new to me. He sent an email on Monday that said that on Tuesday we would be joined by his attorney Mark Fuller. It was short sweet and oh so businesslike. I was crushed, it seemed as though the affair was a fait acompli, and what was left was purely business. I have done many such presentations but never in a dress and heels. I was nervous as can be. Also I had no idea what if anything he had told Fuller about me but I decided since I would be advocating an aggressive approach I should also be aggressive and would push business attire and decorum to the edge. I picked out an outfit, a gray skirt suit. The skirt came to just above my knees, I wore a white silk blouse that buttoned up the front but I didn't button it higher that my breast forms. I debated the wig for quite a while, maybe the chin length wig was best since that was the one I had worn each time had gone to his house, but I preferred the shoulder length wavy blond wig. In the end I needed confidence so I went with the longer one. I took my time and did my eye makeup; they looked smoky although I planned to be wearing my glasses anyway. Lipstick and nails were a light shade of red. And I wore a strand of pearls and drop pearl earrings. I stepped into a pair of 3 inch pumps. Mark Fuller was not what I expected, he was not a stodgy partner in a musty law firm he was about my age, handsome, with a shaved head and looked to be pretty buff under the Armani suit. After the introductions I plugged my laptop into the projector on the small conference table in Randy's study. Naturally I leaned over from the opposite side of the table that they were on so they both got a chance to look down my blouse. I stood for my presentation; actually I struck as many sexy poses as I could while pointing out things on the screen. I maintained eye contact with Mark, and he with me. I threw in phrases like liquidating hard assets that I knew would get to Randy. When I finished he said it was very intriguing concept and that he may have a few questions I said"Feel free to contact me Mark" with a distinct come hither look At that point Randy interrupted "As the client I would prefer that the communication go through me" Mark said "Of course" and said his goodbyes. Randy looked at me and said, "A very professional presentation" I said "Thank you very much" He said "Mark knows about you" I looked at him with an icy stare and said "you should have asked my permission" Randy said "I'm sorry" Then I smiled and said "Well if he knew he didn't seem uncomfortable at all" Randy looked angry and said "He's married with 3 kids" I snapped back "Most of my men are!!" Then he took my hand said with a very sincere look. "Terry I want you!" I smiled and replied "And you can have me" He said "No I mean more than sex, I want to possess you" Now this was getting a little heavy. I thought to myself, how ironic this is the most regular sex I've had in years and he wants more. But it wasn't just sex he wanted more of; it was me, or the persona he saw as me. Now hard to get, is not a role I can play with any sincerity, but impossible to possess now there was a meaty (excuse the pun) role that I savored. I said"Randy I have enjoyed the last two weeks immensely but I am not a whore, I can't be bought and possessed like your house or your car. For better or worse I could never be completely monogamous. I am very attracted to you, the sex is great, and I want more, but it won't work if you want more of me than I could ever give" He looked disconsolate. With some regret I said "I better be going" Sadly I got into my car and drove down his driveway and out the gate. This was the only time I had come to his house that I hadn't got screwed, and it had been a full week since I had any sex. I went home and had a couple of drinks, and stewed over my dilemma. With the occasional image of seducing Mark Fuller flitting though my mind. Well in truth that was the answer to the question that had been troubling me. No matter how much I enjoyed Randy, he could never completely satisfy my physical needs. Regular sex with him in a safe environment is definitely the smart thing to do whether there was any financial reward or not. I was totally truthful when I told him I was not a whore at any price. But doing the smart thing isn't always the most exciting thing. I was less than totally truthful when I said I couldn't be monogamous. The whole truth is I am a slut. The next day a package arrived from Randy I opened the box. In it were a slinky red dress and sling back mules, and some nice vintage type jewelry. The enclosed note said "I would be so pleased if you would wear this on Thursday." I called him immediately and said "Randy darling thank you so much, it is gorgeous but it is hardly suitable for an afternoon business meeting" He replied "I was thinking about 8PM and the only business I have in mind is monkey business" I laughed and said"Hmmm Let me check my social calendar, yes! I am available" He was in a white tuxedo jacket and black pants He had transformed the pool area into a tropical scene we danced slowly to "As time goes by". He caressed my ass. I was melting. Finally I said "It is a good thing you have money" He said "Why" I replied '"Because you obviously went to great and unnecessary expense to seduce me" He laughed "seduction builds the anticipation" I smiled and said "I don't even like foreplay" I said" this doesn't change anything" He replied "I never give up and I always get what I want" I replied"Not this time pal" He took my advice on his estate and paid me a fat fee. We continued to see each other about twice a week for sex. But I refused any further payments. Every once and a while Randy would try to get me to commit to him but I always refused. He suggested that I should live full time and is will to pay for facial feminization surgery, but again I refused. Finally about a year later, I was at his place one afternoon; he was being particularly ardent in fucking my ass, when he suddenly stopped. I yelled "Come on old man, I am almost there, don't stop now!" but there is no answer, and no response. In a panic I turned around, his eyes were rolled up, he had a smile on his face and his prick was still hard, but he was dead. Shock and grief consumed my body; tears came pouring out of my eyes. I didn't know what to do. Quickly I called Mark Fuller. He told me to get out of there and that he will take care of notifying the authorities. I went to the cemetery, dressed in black and with large dark sunglasses. It seemed like the right thing to do. Mark came up to me and said he needed to speak to me and would call the next day. Mark called said that he needed to discuss the estate with me, I assumed he wanted to talk about taxes. He asked that I be dressed as Teresa. I thought it a bit odd but remembered the first time we met he seemed to like me. He came to my house and said "Terry I am the executor of Randy's estate. In a letter of instructions, separate from the will Randy had instructed him to appoint me as the trustee of the largest trust fund he had that included most of his assets" He continued. "The fees for handling the duties would be considerable probably far more than you are making now from your practice". Then Mark let out the kicker. "But, Terry the one stipulation is that in performing any work for the trust you must present as a woman" My mouth dropped open. Mark went on "I am empowered to use any means I deem necessary to check up on you". He also said he was authorized to pay fro any surgery I desired to assist me in this matter. I was stunned, and I thought back to randy saying he always gets what he wants, and he never gives up. Even in the grave he was still trying to possess me. I said I would think it over and he made an appointment for the next day. Mark came to my house at the agreed upon time. I was in a very low cut white blouse, and scandalously short black leather skirt and knee high black leather boots. I let him in and asked him to have a seat; I could tell he was uncomfortable. He asked "Terry will you accept the appointment as trustee and abide by the conditions?" I replied "Well Mark, first we need to better define the conditions. Exactly what does it mean to present as a woman? If it was sufficient to merely dress as a woman I would have thought that Randy's letter would have said just that. So if he meant it to mean more than that, I would interpret that to mean performing acts that a woman would do. So, is it sufficient for to verify compliance for you to fuck my head, my ass, or both?" Mark squirmed as his face flushed. He replied "It was not contemplated that I would engage in such acts" I interrupted"Oh how kinky! you have to watch me do it with another man" He was clearly flustered and replied "There is no requirement about sex acts, it will be sufficient for you to be dressed and to speak as a woman whenever you have to perform your duties as a trustee, who in my opinion would be whenever there are face to face dealings with me or representatives of my firm." I replied "Well under those circumstances I accept the appointment, but Mark, if you aren't coming yourself please send a handsome young male associate" He shoved document in front of me which I signed. He got up and said "I'll be on my way" I said "Oh one more thing, I am thinking of breast implants, do you think 44DD's are the right size?" As he walked towards the door, he said "Do what ever you wish and I will reimburse you for the cost" I decided one D was sufficient. I gave up my practice, and my male persona, moved to a bigger nicer house a few miles away. Mark never came back to see me on business or otherwise, but true to my request he always sent handsome young men. True to my interpretation I always conducted Randy's business in scandalous attire, usually a top that was completely see through so the young attorney would have no doubt they were doing business with a woman. Occasionally I checked them out to make sure I was dealing with a man, you know you can never be too careful. But every time I slipped my lips on some young lawyer's cock, I thought of Randy and hoped he was either looking down or up at me with approval and saying, "Old Guys Do Rule!"