The Escort free porn video

The Escort By Jennifer Richardson I got the idea for this story from a reply I received from a gentleman who I have been writing a series of fantasies. He is into all manner of kinky stuff so I wasn't really surprised when he requested a tale involving him and a transvestite. He is aware that I'm a hetero transvestite and all the previous stories I'd written for him were hetero too. I checked with him and he confirmed his requirements. What he actually said was: "I don't know how I'd react if I was one on one with a TV. So I'd like to you to explore the possibilities with me, think of the payment for the story as if I'm buying your company, like an escort." So I wrote it for him, going into very intimate detail, though I tend toward the suggestive for him more than the erotic here. He was delighted with it and since then has wanted lots more of he and I, I'm quite flattered by all the attention to be honest but he recently invited me to visit with him and from his suggestions I gather what he really wants is to turn his fantasy into reality! I've put him off so far, telling him I have too much writing to do, I haven't really as I've just finished a book, (yes it's tv/ts/shemale.) but who knows? It might go something like this: Executive Relief. When my bank statement arrived I found that I had gone seriously over my limit, the next day my credit card account came and with it was a demand that I pay it off within twenty one days or I would be taken to court. Having recently lost my job the chances of me being able to pay off some, if not any of my debts was going to be impossible. Having absorbed the bad news I went out that evening and spent what money I had left drinking. I was very drunk when I got back home and have little idea what time I finally went to bed. Three days later I received a letter confirming that my advert had been accepted for publication and that a copy of the contact magazine I'd advertised in would arrive in a day or two. I took no notice, believing that there had been some kind of mix up. That was until the magazine actually arrived and I found myself staring at my picture and a description of the services "I" offered. I could only presume that when I'd been drunk I must have taken it into my head that I could earn extra cash as an escort. The picture in the contact mag showed me wearing my long blonde hair swept up from my shoulders, pinned in a chic style that was both sexy and sophisticated. I was wearing a little black cocktail dress and high-heeled sandals. My rose glossed lips smiled suggestively, eyes emphasised with eyeliner and mascara. It was my favourite photo, showing myself off at my feminised best. To be honest my transvestism was a major cause of my debt. There always seemed to be a "must have" dress, pair of shoes or a perfectly gorgeous lingerie set. The advert outlined my likes, socialising, theatre, dining out and such like and was blatantly obvious about my being a t-girl. Thankfully I hadn't advertised my address and all replies, if any, were to come to me via a box number. Over the following four days I received more threatening letters from various companies, from catalogues to a debt collection agency. I was by now becoming more than a little bit desperate; when a thick brown envelope arrived I feared the worst. Panic turned to surprise when I fond that the brown envelope was filled with lots of other envelopes in all sizes. I opened the first and found it was a reply to my advert. The letter was from a man named Robert who lived in a town twenty miles or so from me. He was a financial adviser so this news brought a rueful smile to my lips. He was married with two kids but he said he was very interested in meeting me. He had enclosed a mobile telephone number and suggested I might like to phone him during office hours. I opened the next letter but my mind kept going back to the first. My heart began to hammer in my chest but holding my nerve I picked up the phone and dialled the number. I held my breath while it rang and was about to hang up when I voice answered. "Hello?" I moderated my voice to what I hoped was a feminine tone. "Is that Robert?" "Yes." He didn't add anything though he took a sharp breath as if he was nervous. Not as nervous as I was. "Hi, I'm Jenny, I got your reply to my advert." "Oh, yes, well, I thought that I'd write. I liked your photo." "Thanks, you do know that I'm transvestite, don't you?" "Erm, yes, that's why I chose you." "Your letter says that you're married." "I am, I was just... interested, I've not done anything like this before." "You were interested, or you still are interested Robert?" I asked him, realising that I was taking the lead and that he was allowing me to control the conversation. "I'm still interested." "And you know that I expect a certain... reward for my, company?" "Yes," his voice wavered, "if I pay, it doesn't seem so much like I'm cheating on my wife." I couldn't quite see his line of reasoning, surely cheating is cheating? "I see, do you have anything in particular in mind?" "I was erm... thinking of a drink or something?" He said, his voice catching in his throat. "And when did you have in mind?" I decided to keep prompting Robert, get him making the decisions until I was confident that I wanted to go through with it. "Are you free this evening?" "I'm never, free, Robert." I was starting to enjoy teasing him. "Quite, erm... this evening?" "Possibly, what time were you thinking about?" "I play squash on Thursday evenings, so my wife won't expect me straight in from work. Can you make six thirty?" "That depends where you want to meet Robert." "Erm... do you know the Railway Inn?" It was a small pub not far from the railway station, usually quite busy from what I remembered. Neither classy nor down market. For my first venture out as an escort it was just about perfect. "I know it, now, Robert, we come to the most difficult part. How are we going to close the deal? Shall I give you a number and you see if you can meet it or not?" "I don't know, I haven't, you know, done this before." "Alright then Robert, I'm going to say seventy five." "Seventy five?" "That's what I said Robert." I crossed my fingers, hoping that I hadn't scared him off. "Okay, how will I recognise you?" I silently let out my breath in relief. "You've seen my picture Robert, meet me at the bar." I rang off and only then allowed myself to shake. I began getting myself ready in the late afternoon. Taking the time to have a long soak in a hot scented bath. I washed my hair with a thick creamy shampoo then conditioned it before rinsing it. After making sure my limbs were soft, smooth and hair free, I got out of the bath and wrapped myself in a big soft towel, heading for the bedroom with my hair wrapped in a towel turban. Once I was thoroughly dry the first thing I did was to secure my silicon breast forms to my chest. They look and feel perfectly natural, even their weight and the way they jiggle slightly when I move. I used a special adhesive spray that holds the forms so tightly against the skin that you can barely see where they join. The adhesive holds them secure until they are treated with a solvent cleanser. Once they are in place you more or less have to complete dressing. Almost as if they are forcing you to complete your feminisation. With my breasts fixed I turned my attention to my toenails painting them with smooth coats of rose pink polish while they dried I turned my attention to my hair. Rolling large curlers into the long lengths, pinning them securely and then used a dryer to ensure my hair was dried evenly. I left the curlers in while I made up my face. I began with a light foundation cream, a pale ivory, smoothing it carefully onto my skin and blending it under my chin to my throat. I lined my eyes carefully with a pencil then applied a thickening, curling, coat of mascara to my lashes. I chose a slightly darker pink than the nail polish, using a fine tipped lip pen to line my lips. I filled in with the same soft rose pink to match my toenails and later my finger nails. I'd allowed them to grow since losing my job and had begun to appreciate how good they looked now that they were nicely shaped. I dusted my eyes with a blend of a soft dusky brown eye shadow and a touch of bronze. Creating a matching look to the picture in the advert. My hairstyle would be similar, though I allowed the soft curls of my blonde tresses to escape a little at the back, falling to the nape of my neck. It looked exceedingly feminine and I'm not ashamed to say that I looked very good, totally convincing in fact. It was now time to get dressed so I picked a white satin, seamless bra and matching panties from a draw. The satin panties always feel so wonderful against my skin; I always shiver at their sensational caress as they slid up my legs to fit tight round my waist. So tight and snug do they fit that I don't need to wear anything to hold my bits back between my legs. I'm left with a lovely smooth shape and no tell tale bump. The front fastening bra feels so delightful round me, I think that clipping a bra in place is one of the defining moments when dressing, where the genders begin to blur before the feminine begins to define itself. I carefully rolled and eased a pair of light tan tights along my long smooth legs. They were reinforced and cling nicely on the hips. I decided on tights for my first night as an escort because I wanted to make sure my customer, Robert, was nicely hooked. If he was a good boy and wanted to see me again I might then treat him to some stockings and suspenders. Stepping into the short black, long sleeved dress and easing up the long zip in the back thrilled me, feeling it tighten about me and cling to my body. The soft velvet feels beautiful to touch and ripples under the fingertips when it is caressed. The sweet heart neckline suggests rather than reveals whilst the hem clings to my legs at mid thigh. I stepped into my three inch heeled black sandals and wiggled my toes, enjoying the sight of the pink varnish nails. Slipping hoop earrings into place and adding a gold coloured band to my left wrist I added a ladies evening watch to my right. I finished off with a broad velvet ribbon choker and a necklace with a pearl drop pendent that sat above the neckline of the dress. Before I could get an attack of second thoughts I picked up my favourite coat, a long tan coloured lightweight trench coat. With a handbag slung on my shoulder I left the house and headed for the nearest bus stop. My pockets were full of loose change for my fare, the last bits of cash that I had. I guessed it was just enough to get me close to the Railway Inn and for one drink if I had to wait for him, I refused to consider the chance that he might not show up. I waited at the bus stop for about ten minutes, not at all worried about being out in public as I was very confident in my look and I'd been out dressed on dozens of occasions. It had occurred to me a week after losing my job that I should perhaps become Jenny full time but at the time it hadn't really been a serious consideration. Once the bus arrived I boarded and heard the driver muttering under his breath about "dumb blondes" when I began to sort my fare out from the coins in my pocket. I looked out of the window on the way into the city centre watching the traffic clogging up at junctions and irate drivers shouting at each other. It was rush hour, so it was all very busy, especially at the bus station, crowds milled everywhere but I was too excited to take too much notice, other than smiling back at people who took an interest in me. I glanced at the station clock and saw that it was already six fifteen and I knew I had a twenty or so minute walk to the pub. I smiled to myself when I considered that it was only right and proper that a girl was five fashionable minutes late. It was nearer ten actually as I saw an absolutely gorgeous ankle length dress in a shop window, shimmering silver from shoelace shoulder straps to the hem. The price tag hurried me on my way. On arriving at the pub I found that both the bar and the lounge were very busy. Thankfully the crowds of mostly commuters parted to let me through. I could feel eyes on me from all directions and was inwardly thrilled. I could sense some of them thinking that it might be worth trying to pick me up. I walked confidently up to the bar and waited to be served. Two men in suits were talking to my left and a young couple were sat on stools to my right. Wherever Robert was, if he was in the pub, he was presumably having a good look at the goods before he decided if I was worth it or not. One of the bar staff was making her way down the bar towards me, I sought out some change in my pocket just as a tall man in a smart navy suit appeared at my side. "Jenny?" He said quietly. I turned and gave him a bright smile, taking in his shock of salt and pepper hair, blue eyes and very handsome face. Even though I was in three inch heels, pushing me close to five eleven, Robert was much taller than me. Around six foot three, broad shouldered, at with a very solid looking build which I put down to his playing squash. He looked very fit indeed. "Can I get you a drink?" I told him I'd have a white wine and watched as he confidently beckoned to the girl behind the bar. His lack of confidence or shyness on the phone had disappeared, measured and assured he picked up our drinks, he ordered an orange juice, and guided me through into the lounge where we grabbed the first available table. He held my coat for me when I took it off and smiled when I sat down and cocked an eyebrow, seeking his approval. He sat close beside me and said that I was even more beautiful in real life! With many more compliments like that I'd have been urging him to divorce his wife and marry me! His eyes lingered on my knees when I crossed my legs; the soft swish of the sheer tights against each other seemed to drown out the noise in the pub. Robert had put my coat on the back of the chair, reaching to the inside of his jacket pocket and removing a brown envelope folded in half. Without attracting any attention he slipped it into my coat pocket. "Thank you Robert." I smiled to him and asked him if he had, had a hard day at the office. His face lit up with a broad smile, "Yes, but let's not talk about work." He emphasised the word work. "You look as if you work out a lot, just squash or do you do weights?" I asked. "A bit of both, though I used to do a lot more, I'm thinking of giving up squash, too time consuming." "You'll have to find something else to do on your Thursday nights then or you'll run to seed!" I giggled and looked at him from beneath my lashes. He gave me an appraising look and slipped his hand over mine for the shortest moment. "I might already have found something." We chatted for another hour, all manner of things, I can't say we had an awful lot in common but we were getting along well enough. I flirted with him an awful lot, touching his hand, laughing at his terrible jokes and paying him a lot of attention generally. "Are you hungry?" He asked, smiling at me. "A little, what have you got in mind?" "Nothing much, I'll treat you, I'll be expected to eat, later." I agreed and followed him out of the pub. The air had a chill to it so I draped my coat over my shoulders, feeling his arm snake round and settle on my waist. I was a little uncomfortable with it for a second and then relaxed. We walked along lie any other couple until we come to a small intimate French restaurant. Taking a snug corner booth Robert wined and dined me as if we were a courting couple. Before I knew it, it was ten o'clock and Robert was hinting that he was soon going to have to make tracks. "I'll give you a lift." "No thanks Robert, there's no need, I'll get a taxi from the station." I didn't want him knowing my address and I didn't think other escorts would allow their clients into their private lives either. "Let me drop you off at the station then?" I agreed, even though the station was only a couple of hundred yards from the pub. We walked back to the pub slowly, his arm round my waist against holding me close to him. I could feel his strength and began to realise that if the atmosphere between us turned in a way that he didn't like I could be in trouble. Robert led me over to a shining red saloon car, probably belonging to his company I thought. He opened the door for me and held it while I got in the passenger seat. He got in the drivers side and settled into the seat, turning to me he smiled and then leaned across me to the seat belt and eased it across me, his hand traced slowly over my breasts. His mouth lowered to mine, feeling his lips warm against mine, provoked equal amounts of panic and surprise. At first I was repulsed but was shocked at myself when I responded. His arm slipped round my waist, my hands reached over his shoulders when his weight lowered onto me. I could feel his hard muscles ripple through his shirt, a hand snaked down to me knee and caressed me. Robert broke the kiss and eased back, looking down at me with a broad smile on his face. The hand moved fractionally under the hem of my dress, I placed my left hand over it and stopped him. "No?" He smiled. "No, not here." Quite why I added that I don't know, my breathing had quickened and I felt myself getting aroused though the tightness of my panties prevented anything from showing. Robert put the car into gear and pulled the car out of the car park. I glanced across at him, my eyes catching sight of a huge bulge developing in his trousers. I looked up and saw the railway station ahead, Robert indicated left and turned the car onto a different road to the one that went directly to the station, leading instead onto the ramp of a multi storey car park. It was very dimly lit; Robert pulled the car into a slot at the rear of the level and switched off the engine. I had the distinct impression that he had done this before. He turned to me again, both hands reaching for the hem of my dress. I stopped him, holding his hands and fighting my fright to keep my eyes locked on his. I gave a nervous smile and lifted his hands off my dress, glad that he didn't fight me. I put his hands on his knees and raised a finger to his lips, rubbing the palm of my left hand over the solid length in his groin. He gasped but stayed still. Steeling myself I eased down the zip of his fly and undid the button on the waistband. His erection rose through the opened flies hidden beneath the black silk of his boxer shorts. I eased a finger into the top of the shorts and slowly peeled them down to reveal his cock, hot, long and thick. He shivered when I stroked the length from root to tip with the tip of one finger, trailing a nail over the head making him take a deep breath. I was back in control of both myself and the situation. I removed my finger and sat back in the seat, Robert turned to me, eyes wide and his lips parted. "You wanted an escort Robert, that's all you've paid for." I held my breath when I saw his hand move up to the inside pocket of his jacket. He produced his wallet and opened it, pulling out a sheaf of twenty pound notes. He placed two on the dashboard without saying a word. I slipped my hand back over to his erection and began to gently stroke him again. I smiled at him, licked my lips suggestively, he reached to the wallet again and put another two notes on the dashboard. I began to move my hand up and down on him, faster and faster, from the head to the root. I removed the seat belt and leaned across. I touched the tip of my tongue on his cock, tasting the wet salty head. Then swirled my tongue round it and blew air through my lips. I felt him move a hand to the back of my head, stroking my hair. "No." I whispered, removing my tongue and lifting my head away. His hand returned to his knee and I dipped my head down again. I slowly moved my lips down over the crown, taking the head into my mouth, sucked my cheeks in, making him shudder. I soon found a rhythm timing my down strokes with breathing in; while I sucked and licked I nibbled with my teeth and continued stroking up and down his cock. Finally I worked my way down until my nose touched his pubic hair, his huge cock filling my mouth and throat. I could feel his pulse in his rock hard hot flesh and began to work him over again until the first soft moan became a groan and gasp. Faster and faster, greedy now, giving myself over to what I was doing. Never imagining that I myself could get turned on by sucking cock. I went at it the way I'd seen girls doing it in blue movies until I felt him beginning to twitch. I sensed he was close so eased off until I heard him sob. I returned to sucking him off, deep in my mouth and throat, feeling the tension build within him until a torrent of hot come shot straight down my throat, filling my mouth, threatening to choke me until I swallowed. I kept him in my mouth until I could here his breathing recovering, long deep breaths, panting as his penis softened. His head was laid back on the head rest, I moved up his body until my lips touched his cheeks, turning his head I put my lips on his, using him to clean my mouth with his tongue. I moved back into my seat, put the twenty pound notes in my pocket and got out of the car. He didn't object or try to stop me as I made my way out of the car park, my high heel echoing from the concrete walls. I stopped for a drink in the station bar, a tall vodka and lemonade, which I used as a mouthwash; obviously I couldn't spit it out so I swallowed. My mind was filled with what I'd done, images swam in my mind; his cock had been so big that it felt as if it was still in my mouth. What amazed me most was the realisation that I'd liked what I'd felt and liked what I'd done, sucked cock like a pro. The following morning I sat at the breakfast bar and looked at the cash, eighty pounds. I decided to be disciplined with it. It would take more than eighty pounds to pay off any of my debts so I got three envelopes and put one note in each, one to the bank, one for the credit card and one for rent. The twenty pounds remaining I spent on food. I went back to the big brown envelope and sorted through the replies, discarding those that didn't appeal, and that was most of them. I put three to one side. The first was of a man called Gary who owned a car dealership in the city. He said he was gay and single. The second was from Steven, a TV himself who worked as an office manager quite nearby. The third was from an older man of 65 called Charles; he was retired and lived only a quarter of a mile from my house. All three had phone numbers so I took them through to the lounge and picked up the phone and dialled Gary. "Star Deal Motors." "Could I speak to Gary please?" "Speaking." "Hello Gary, this is Jenny, you answered my advert?" "Oh! Yes, that's right. Can I ring you back? I'm at work." "Sorry Gary but I'm a little busy, I'm free this evening at seven o'clock. If you'd like to 'discuss' things I'll be in The Anglers Arms on Rochester Avenue." "How will I recognise you?" "You've seen my picture." I rang off and dialled Charles. "Good Morning?" His voice was very cultured, rather baritone, I could almost feel the vibrations down the phone line. "Good Morning, may I speak to Charles please?" If he was going to be so polite, the least I could do was be as polite. "This is he." "Hi, My name is Jenny, you answered my advert?" "Ah, indeed, I should very much like to meet you Jenny." "Do you have anything in particular in mind Charles?" "Certainly, I should like to see you in a tight white sweater and short tartan skirt. Wearing black high heels, the higher the better. White knee length socks over black stockings, then I would like you to bend over and let me see your panties, stocking tops and suspenders." "You seem to have it all worked out Charles." "Naturally, I like everything in its place." "I see, where would we be going? The outfit you describe doesn't sound as if it could sensibly be worn out socially." "We wouldn't be going out Jenny, I would like you to visit me, you'd be my naughty niece you see." "I don't do home visits Charles." "That's rather a shame, I'm housebound you see. I was rather hoping you might sit on my knee with my cock pushed against your panties." I was rather taken aback but managed to recover quite quickly. "My time is rather expensive Charles." "And I'm a retired company director who likes coming with my prick rubbing against frilly panties young lady." "Well, I don't actually have the outfit you'd like Charles." "It's all here waiting for you, don't worry about size, the tighter the fit the better. Two hundred pounds for sitting on an old man's knee Jenny." "I see." "Just talking about it has given me quite a stiffy!" "When would you like me to come?" "When are you free?" "I'm never free Charles." "I'd like to see you a soon as possible." "I could be with you in an hour." "I look forward to it my dear niece." "As do I Uncle Charles." He was an absolute darling. I arrived at his large detached house dressed in a short white skirt and black lace top. My black bra clearly on show beneath the top and my stocking tops sneaking into view when I walked. All this of course was hidden under my coat. I had a pair of spike heeled court shoes in the bag at my side, heeled pumps on my feet as walking any great distance in the spikes was out of the question. He opened the door from an inside and on entering he called me through to a wooden panelled lounge. He was sitting in an electric powered wheelchair wearing a long black dressing gown. I took my coat off and laid it over the back of a chair. His ruddy face coloured even more, his moustache twitching. "Jolly good show Jenny! Lovely!" "Thank you Uncle Charles, you're so sweet!" I twittered in response. I saw the front of the dressing gown tent upwards and smiled, raising my hands to the back of my head I untied the ribbon from my hair and let it fall down over my shoulders. "Shall I get changed Uncle Charles?" "Why not dear, you'll find your clothes in that trunk." He pointed t a wooden box against the wall behind him. "I shan't peek Jenny, I promise." "Oh Uncle Charles, I'll be upset if you don't watch me." I did a slow sexy strip and posed for him, showing myself off from every angle, much to his appreciation. It struck me that if he wanted me to wear frilled panties I was going to have to take mine off. I opened the trunk and saw the top, the skirt, the socks and then the panties. Lots of frills and three sizes larger than I normally wear. I turned to face him, finding that he was less than two paces away. I slipped my panties from my waist and slid them down to my stocking feet. Stepping out of them, my cock sprang forward and began to harden. "May I?" His chair moved silently forward, fingers reaching out to encircle my length, he stroked it gently, my disbelief at what was happening disappeared under a wave of excitement. I stopped him and told him he was a very naughty Uncle. Once I'd dressed I perched in his lap, his hands rising to cup my breasts, moulding and stroking me through the tight white top, which left much of my stomach bared. The skirt was flared so it was easy for him to slip his erection under the hem from behind. I could feel the heat burning my buttocks and he began to gently rock me back and forward. This made his cock rub back and forward in the frills. He managed to keep going for an absolute age, never losing the strength of his erection, if anything it got hotter and harder. He managed to slip the head of his cock between my cheeks, the panties between it and my skin. There was no pain; in fact it was a nice feeling, close and intimate. He continued to rock back and forth, the pressure of the head pushing in and out between my cheeks feeling better all the time. His right hand slipped from by right breast and under the skirt, holding my length between his fingers his rocking back and forth brought me close to orgasm and then passed the point of no return when, with a soft grunt I felt him coming into the panties the head of his cock still between my cheeks. The panties were soaked front and back, sticky and creamy. He eased me off his lap and had me stand in front of him. Uncle Charles began to lick me clean, I was hardening again when he stuck his tongue into the mess between my cheeks, even poking the tip of his tongue against my opening. He gently eased my roused cock back between my legs, until it was pointing straight back towards him. He asked me to clamp my legs together and bend over. "I'm going to lick your little clitoris until you come you naughty girl!" He whispered, his tongue running back and forth over the head of my erection. Bent over as I was and on such high heels I couldn't move without losing my balance. He stroked between my cheeks and I felt a finger slip back and forth over my rosebud. "Is that nice Jenny?" "Oh yes!" I gasped, the finger nudged against me again. "And this?" The finger slipped in easily up to the first knuckle. "Mmmmf!" I moaned and groaned as the finger slipped deeper still until the full length was stroking in and out, all the while he worked his tongue against me until I shot my cream into his mouth. His finger continued to work until my sobbing stopped. "You're a very naughty girl Jenny, but you've earned your pocket money. I do hope you can come again next week? Same time?" He watched me clean up as best I could and then handed me an envelope and bade me good afternoon. I was a little surprised to see his wheelchair turn way and he disappeared out of the room leaving me to get changed. I put everything but the soiled panties back in the trunk. Being nosy I looked a little deeper into it and found a leather corset that was both incredibly soft to touch, like kid glove leather, but with very stiff stays. I wondered just how kinky Charles was but left the corset there, idly wondering what it would feel like fastened tightly about me. Once I was dressed I headed home and again divided the cash into the respective envelopes. This time I sealed the envelopes and addressed them. Putting them to one side for a moment I went though to the bathroom and showered, then back to the bedroom where I dressed again. A white satin blouse, black suit skirt and jacket, over pale blue lingerie. I stepped into a pair of black suede heels and set off to the post box to post my letters with their brief covering letters. I did a little window shopping and then returned home along the high street, passed a branch of a bank which had it's windows full of adverts trying to entice new customers. I went passed it and then thought again. Returning to the bank, I entered and went up to a stand that, among other leaflets, held application forms for prospective new customers. I picked one out and then left before I could be "assisted." I took the form home and read it through. It asked for the details of any bank accounts held but also had a box for those who have never had a bank account before. I filled this box in and all the other details the form required. The one problem was the requirement for a witness to my signature and proof of identity. This was easy enough to forge. It was then that a sudden burst of an idea hit me. I thought I remembered a television advert concerning the driving licence authority; there was some kind of drive to get people to update information on their licences. With this in mind I went through to my spare bedroom, which was set up as a home office from when I'd been doing a correspondence course through a university. Actually I'd dropped out of the course when I'd lost my job but the computer system I'd rarely bothered with since still sat there. I powered it up and set up the digital camera on its tripod. By the time I'd done this, the system was ready to go. I went on line and went to a search engine looking for the licensing authority. There it was, and wonder of wonders I could change my details on line. I checked the camera and took a head and shoulders shot of myself, downloaded the image and saved it on the desktop. I then went to the information pages and ran through what I would need to do. I had to type in my licence number and waited for the page to come up. It took a little while but eventually there it was. It looked exactly like the one in my wallet but had a button that took me to a page, which showed the new licence style, more of an identity card than the old style folded paper sheet. The new card had a space for a photo so I worked out how it was supposed to work and found that you only had to "paste" it in position. I then turned to the boxes where I would have to fill out my details. Everything remained the same other than my first name, which I changed to Jennifer, the Mister changed to Miss. I paused and took a nervous breath. Quite why I was nervous I don't know, I was only sending information to a computer. I clicked on the confirmation of information button and waited, it seemed to take an age but eventually a page came up thanking me for updating the information and that I would have my updated licence in two days at the most. I let out my breath, in two days I would have something that would prove who I was, that I was Jenny. The first step on my way to becoming her full time and all that this entailed. I went out with Gary that evening and was paid fifty pounds for sucking him off behind the pub. He held my face while pumping his slender cock in and out of my lips until he filled me with his hot cream. I didn't swallow, I waited until he was softening and then stood to kiss him, sharing his cream with him much to his amazement. I did another three session's with "Uncle Charles," the money being shared between the accounts, which were in debt whilst opening a new account without trouble at the new bank. My plan was to clear my debts and one by one close the accounts. Once I'd achieved this, and it took some months, I armed myself with a mobile phone and added it to the advert in the contact magazine. "Work" came in thick and fast, I travelled the country providing my services, not realising there were so many "straight" men who had a fancy and fascination for T-girls. The more I experienced the more I got used to sucking cocks, plating and teasing them between my fingers. I was soundly spanked and did so in return, I shafted one man with a huge strap on until he was squealing in pleasure. Another wanted to be tied up and slapped; yet another wanted me to dress him as a little girl and be allowed to suck on my breasts. He came in his nappy when his lips sucked on my jutting silicon nipples. On a Friday evening I returned to the house just in time for my mobile to ring. "Jenny?" "Yes." "Hi, it's Robert." "Hello Robert." I deliberately sounded cool, as I wasn't sure how he had felt after I'd left him in the car park all those months alone. "I was wondering if we could meet?" He asked. "What do you have in mind?" "I've been at a conference for the week, I'm travelling back tomorrow morning and have a room booked at the County Hotel for tomorrow night, I'm not expected home until Sunday evening." He explained. "So?" "So I'd like you to come and stay at the hotel with me." "Overnight?" "Yes, drinks, dinner and then, well, bed." Bed? Could I do it? I had no doubt what he meant, but could I go through with it? Give my "virginity" to him? The thought frightened and thrilled me at the same time. His enormous size concerned me but it would surely be the icing on the cake as far as my "womanhood" went. Jenny would be complete, my long journey to truly living as and being her fulfilled. I found myself agreeing. "I'll be there at seven in the evening Robert." "I promise to make it worth your while." "Of course you will Robert, I'll meet you in reception. You can make out a check to me, and sign it. No cheque, no evening." "How much, I mean, what should I make it out as?" "You just leave that to me darling." "But Jenny!" He objected. "I hope you enjoy your stay Robert, I hear hotels can be very lonely." "Alright! Alright, just, well, don't go too mad will you?" "You'll get your money's worth Robert." I told him and then rang off. As soon as I was ready in the morning I took a bus into town, to a certain boutique where I bought a wonderful sheer silver sheath dress and a soft black wrap, more of a shawl than a cape. To go with it I bought a pair of high heel silver strapped sandals and an evening bag. Back at the house I took an age getting ready. The dress was so sheer and soft that I had to wear hold up stockings, slightly sparkling and very sexy. With them I wore tight white satin panties and my favourite satin bra with the shoulder straps detached. When I saw my finished look my breath was taken away. I'd never looked as feminine, sexy and sensual, I felt as if I had finally found Jenny's true self and revelled in it. I took a taxi to the hotel; the driver kept glancing back in his mirror to look at me, a broad smile on his face. The soft silver silk scarf wound round my throat hiding my Adams apple, my breasts were beautifully outlined though you couldn't tell they weren't real. On leaving the back seat of the cab paid the fare and turned away, hearing the driver whistle under his breath. I entered the front door of the hotel, supremely confident, at ten past seven and saw Robert leap from a leather armchair to my left. I pretended I hadn't seen him and moved across towards the desk. Robert hurried to intercept me and kissed my lightly on my cheek. His left hand took my right and I felt a rolled up piece of paper being gently pressed into my palm. I took in unobtrusively and had it safely tucked away into my evening bag. Robert escorted me to the restaurant and made a big show of ordering for me. I made certain everyone knew we were together, touching his hand and keeping as close to him as I could without over doing it. As Jenny I loved the attention, feeling as if I was Roberts girl, perhaps engaged and so in love. The meal was perfect as were the accompanying wines. Robert was the perfect gentleman; a wonderful host and I allowed myself to revel in his flattering attention. After a large glass of brandy his hand strayed over the starched white tablecloth to hold mine. My eyes logged on his and I gave him a soft knowing smile. He stood up and came round the table to hold my chair for me. I collected myself and wrapped the wrap over my shoulders, feeling his warm breath on my skin. I linked my arm in his and allowed myself to be guided from the restaurant through to the lifts in the lobby. We travelled up alone in the lift to the fifth floor. I wrapped myself round him and drew him into a tongue tangling kiss that left him breathing heavily and with a long hard bulge in his trousers. By the time we reached the room I was buzzing and in full control. Once in the room he locked the door behind us and then crossed to me, removing the wrap and lowering his lips to my shoulders, kissing and nibbling me softly until my head tilted back against his shoulder. His hands slipped up from my waist to caress my breasts, then rose again to ease the thin shoulders straps down over my arms. The dress dropped to the floor and I stepped from it. Turning to push him back a little. Pushing the jacket off his shoulders and then working the buttons of his shirt open. He kicked off his shoes and socks until he felt my hand opening the button at his waistband and then slowly lowering the zip of his fly. Pushing his trousers down over his hips to fall at his feet. Robert stumbled a little, kicking them from his feet. I slipped my hand up and down his length captive within his boxer shorts until he gave a slight groan. In one smooth motion I pushed his shorts down to feel the heat of his cock under my fingers. I caressed him before slowly sinking to his knees, feeling his fingers working at my bra clasp. Kissing and licking at the huge purple head of his cock, blowing softly on it, my bra fell away and his strong hands held my shoulders steady when I slipped my lips over the head and began feeding it into my mouth. Sucking harder, lashing my tongue against the hard prick between my lips. I felt him tremble and eased back gently, lapping at the slit. His hands lifted me up from my knees, taking me into his arms he kissed me deeply, caressing and stroking me everywhere until they reached my panties, they fell to the floor and I felt his fingers ease between my legs, stroking my still hidden cock trapped back between my thighs. Another finger slipped onto my bum and slid between my cheeks, probing against my rosebud. I lowered my lips to his nipples, nibbling and sucking at them. I felt myself being walked back toward the bed and allowed myself to be guided and turned. He pushed me forward gently until I was kneeling. Robert stepped away and went over to his bag, I watched him over my shoulder. He took out a tube and returned to me while he unscrewed the top. I stuck out my right hand and he squeezed a large dollop of lubricant jelly onto it and then watched me grease his cock while he worked a lot more between my cheeks, one finger then two slipped into me feeding the cool jelly into me. He moved and positioned himself behind me, standing at the foot of the bed. I bent over and wiggled my bum at him, again reaching back to hold his huge hard cock. He took my hand off him and pushed it away, I wasn't to be allowed to guide him. He was going to take me, make me his and I allowed it. He spread my cheeks with one hand and pushed the bulbous lubricated head against my entrance, nudging it back and forward to further spread the jelly until he slipped back and forth. Roberts's hands came to my hips and held me firmly. "Ready for me darling?" I could barely find words, giving only a soft groan when I felt him push. Gently he fed me the head until he penetrated me. I gasped at the feeling and pushed with my muscles, feeling ever so stretched. Bit by bit, inch by inch until I moaned loudly when I felt his balls against mine. Then and only then did he begin to withdraw, all the way back until only the head remained within me. In long tortuous strokes he began to shaft me. At first and for quite a while I fought the dull aching pain until I was able to relax, then I began to pick up his rhythm and began moving against him. He moved harder and faster, filling me, shafting me, screwing me until I was sobbing and moaning in ecstasy. His hands clamped me tightly; as if he was afraid I was going to escape. That was the last thought on my mind, I wanted more and more of his masterful cock, I wanted to make him come in torrents deep within me, to make a woman of me, to make me his woman. I heard him beginning to pant and moan: "Yes Jenny, babe you're so tight!" You hot bitch, you're so beautiful, I love it!" His excitement drove him on; a hand reached beneath me and encircled my cock, allowing his thrusts to push me back and forth against his hand. I came to climax in seconds, hugely, wonderfully. Spurting through his fingers then feeling his hand pushing my head down to the bed. I eased down so my bum was higher in the air, staying still now so he could take complete possession of me. I felt him struggling to keep control until finally he exploded. The feeling of his cock spurting within me gave me an incredible thrill, he continued to drive his full length back and forth until he was spent, staying deep inside until he subsided and then eased out and he collapsed on the bed beside me. Over and over again that night he pleasured me. He laid me on my back with my legs tightly locked round his waist, a pillow under me so he could pound in and out of me. It felt wonderful, looking up to see this strong muscular man above me, his cock in my "bumpussy" as he called it. He sucked on my "cockclit" until I was hot for him, again and again. Finally we slept, his arms folded round me, my body moulded to his, his cock still rigid within me. When I woke early in the morning I sneaked from bed to bathroom and showered. He was still asleep when I returned to the bedroom where I tidied my face up and brushed through my hair. My entire body ached so I slipped back into bed beside him. Facing him I watched his eyes open slowly, a smile grew on his lips. He propped himself up on one elbow and looked into my face. "I don't want you to work any more." He whispered. "So you want me to get a 'proper' job?" I asked with a mocking smile. "No, I want you to work for me, all you have to do is be there for me when I can find the time." I didn't grasp what he was saying at first, he rolled me onto my back and lowered himself full length on top of me, his awakened prick lying beside but dwarfing mine. "I'll pay your rent and expenses, you can be my bit on the side!" He laughed softly. "You can't be serious!" I giggled, feeling his cock nudge between my aching cheeks once more. "All executives worth the title have a Mistress Jenny and I want you to be mine!" As he said it his cock penetrated me, making me groan as the hard thick length split me in two. He began to feed it back and forth until I was sobbing quietly. "Yes, yes, yes! Love me Robert!" So I receive him two or three times a week, he found a Doctor who prescribed me a hormone course and now, a year later my tits are big enough to squeeze his cock between. My mouth meeting the head on every stroke until his cream floods my mouth. His wife suspects nothing, his kids are away at college and my wedding dress is nearly finished. The service will be private, at the house of his closest friend, his friend is the best man and the vicar is his closet boyfriend. When I say Robert's friend is to be the best man, he will be for the service, in the bedroom he isn't as big or as good as Robert, Robert is still my best man but he loves to see James shafting me while I suck him off. James? Oh yes, he gets executive relief as well.