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Crossdresser to Trans Escort Part 3
This is a continuation of my Crossdresser to Trans Escort series.
After my first fuck for money with the restaurant owner, things escalated. I arrived at work the next morning wearing a pair of black trousers, black blouse and flat ballet shoes. The owner called me into the back office before we opened up for the customers. He was sitting behind his desk wearing a tight black t-shirt which showed off his tanned skin and bulging muscles. ‘I really enjoyed our transaction last night’ he grinned, emphasising the ‘trans’ part as he spoke. ‘Eh, so did I’ I replied nervously. ‘I view you as a valuable asset to this restaurant, the customers love you. And of course, you are a valuable asset to me too. I will give you a small raise, an extra €5 per hour, but you must wear what I tell you to wear, and follow my command whenever I say so’ he declared. ‘Alright, I agree’ I said, standing nervously in his office. ‘Today, I want you to wear this’ he said, handing me a small piece of fabric. I picked it up, it was a very short, thin black dress. ‘This will really lift the customers’ moods, and mine’ he said with a satisfied smile. ‘Okay’ I replied, turning to go to the bathroom to change. ‘Change your clothes here, I insist’ he said, outstretching his hand in a welcoming gesture. I hesitated for a moment, but then he got up and put his hands on my waist, his face just an inch from mine. ‘It’s nothing I have not seen before, sexy’ he said, before kissing me slowly. Then he grabbed my ass and squeezed tightly, before bringing his hands around to my crotch and unzipping my pants, quickly pulling them down. ‘You understand?’ he asked, grabbing my crotch and squeezing the area where my tiny two-inch cock was tucked inside my lace thong, my empty balls already up inside the inquingal canal, undetectable. ‘Yes, sir’ I replied, slowly unbuttoning my black blouse, allowing my chubby little B-cup sized breasts to plop out into the open. He caressed them for a moment then returned to his desk to watch me undress. ‘It is great that you did not wear a bra again today’ he said satisfiedly. I stood there in just my lace thong and picked up the dress. I pulled it slowly up my body. It was strapless and very tight, hugging my body as if it was painted on. My chubby little titties squeezed inside the top of it, creating a nice cleavage. The bottom of the dress stopped an inch above my ass cheeks. I tried to pull it down a bit, but my nipples squirmed out of the dress when I did that. Looks like I would be giving the customers a real show today. ‘Oh, and another little gift for you’ he said, reaching inside his desk drawer and pulling out a box. I opened it, black stilettos, 4-inch heels. They were beautiful. ‘Please, where them today with your beautiful new dress’ he gestured. I slipped off my ballet flats and sat down on the nearby chair to slowly try on my new heels. They fit perfectly and made me feel incredibly sexy. As I sat down, my tiny dress rose up my hips to reveal my bare legs and underwear. There was no hiding my modesty in this dress. It was quite a turn on for my exhibitionist ego. I stood up and walked cautiously around the office in the new heels and dress. I felt amazing. ‘Beautiful, absolutely stunning’ the owner said. ‘Alright, let’s open up and welcome our customers’ he declared. I strutted out into the restaurant again and opened the door. Soon, tourists and locals alike were streaming in. The day passed by quickly as the horny male tourists complimented me and even groped me, spanking my ass as I bent over, revealing my underwear in my tiny dress. Their tips were also quite generous. With the skimpiness of my outfit, I may as well have been wearing nothing. One gentleman in his fifties with a group of similar-aged men wanted to give me a generous tip. The owner noticed and came striding over. ‘Paolo, please, like this’ he said, turning me around and lifting up the bottom of my dress, not that it needed to be lifted up much, to reveal my skimpy thong and of course my chubby ass cheeks. He slipped a €10 note inside the waist of my thong. ‘Oh, a beautiful lady for sure’ marvelled Paolo, spanking my asscheek before slipping three €50 notes inside my thong. I couldn’t believe it. This was more money than I had ever made before. The other gentlemen laughed and cheered, raising their champagne glasses to me. ‘How about her beautiful breasts, eh?’ the owner asked the men, before pulling down the top of my dress to reveal my little breasts. ‘Oooh, so natural, so beautiful’ the men exclaimed. bet siteleri Paolo squeezed one of my breasts and spanked my ass again. I was on display like a circus act, in the middle of the afternoon on the outdoor terrace of the restaurant, being groped and ogled by horny middle-aged men. Little did they know about the tiny pathetic piece of flesh that dangled between my legs. It was safely tucked inside my lace thong. ‘You know’ the owner said, ‘This girl has a truly remarkable body, she has something a little special’ he announced, rubbing my crotch area with his hand. ‘If you would like to see, maybe you guys can come back later this evening’ he offered. ‘Hmmm, Paolo pondered, ‘I love a lady with a bit of mystery, I shall see you at 10pm this evening for some wine and a good look at this intriguing, beautiful lady of yours’ he said triumphantly. With that, the men got up and left. I quickly pulled the top of my dress up. The other customers in the restaurant had witnessed the little show, most seemed to enjoy it, a novelty. I brought the empty plates into the kitchen. When I came out, the owner stopped me. ‘Tonight will be a lot of fun’ he said. ‘Paolo is a dear friend of mine and my oldest customer. I trust you will do whatever takes his fancy, to keep him satisfied, for the good of the restaurant’ he said. ‘Well, eh, what exactly will I have to do?’ I questioned. ‘Relax, Paolo is a great guy. Besides, he gave you an advance payment just now, right?’ he said, referring to the €150 stuffed down my thong. ‘Eh, ok’ I said reluctantly. My feet were already begininng to ache in the new high heels, coupled with the seering heat.
After a busy afternoon, the restaurant began to quieten down around the evening time. Around 9:30pm Paolo made his triumphant return. He was a slick, middle-aged Frenchman who wore expensive suits and kept himself in decent shape. His dark-brown skin had endured plenty of sun on the south of France, usually on his yacht. ‘Your wine, sir,’ I said to him, pouring him a glass of his favourite. ‘Thank you, thank you’ he said extravagently, slapping my ass before picking up the glass and swirling it around. ‘I could not wait any longer, I have been thinking about you all day, so I came a little early’ he said, a grin on his wrinkled yet handsome face. ‘Okay, I have closed up the restaurant now, Paolo, it is not so busy tonight anyway’ said the owner, locking the door. ‘Perfect’ said Paolo, gesturing me to come and sit on his lap. The owner nodded and I made my way over to him and sat down. I marvelled at the expensive fabric of his suit trousers. My tiny dress had risen up my ass, so my thong was on display. Paolo pulled down the top of my dress to get another look at my tits. ‘Mmmm, so soft, so beautiful’ he said, caressing my breasts with pleasure. Then he slowly slid his hand up my legs, from my ankles up to my crotch. He caressed my crotch area through my thong. ‘Nice little pussy’ he said, licking his lips. ‘Stand up, let’s take a good look at you’ he ordered. I nervously stood up and pulled my dress down until it reached my ankles, then I stepped out of it and left it behind me on the floor. I stood there wearing just my tiny lace thong and my black high heels. ‘Come on, take it off’ Paolo gestured impatiently. I slowly pulled my thong down, my tiny cock flopped out from between my legs. ‘Oh my!’ exclaimed Paolo. ‘I knew you were a special girl!’ he said. My thong hit the floor and I kicked it away. Paolo unzipped his trousers and a huge 11-inch cock sprung out, the tip already moist with pre-cum. I kneeled down, naked in just my heels, and proceeded to take his massive rod in my mouth. I licked it slowly from the base until the tip, then engulfed it with my lips. I could barely breathe as Paolo stood up and grabbed my head with both hands, proceeding to fuck my mouth hard. I slipped back onto my ass, my head still in my hands. One of my shoes slipped off as I pulled my legs in front of me. The cold wooden floor stung my bare ass cheeks. My tiny cock and balls had disappeared between my legs as my mouth took the giant, warm rod of flesh. After around five minutes of face-fucking, Paolo pulled slowly out of my mouth, his cock dripping in saliva and pre-cum. He slapped my face and then grabbed my throat, pulling me to my feet. I stood there naked, wearing one shoe, having endured a brutal face fucking, nervous and frightened as to what was coming next. My asshole was still sore from the hard fucking by the restaurant owner the previous night. With his hand still around my bedava bahis throat, Paolo took a step back and eyed me up and down, scanning my slutty tranny body with his hungry eyes. He grabbed my tiny cock and balls and squeezed tightly. ‘I guess these are not much use to you’ he said mockingly. ‘We may be able to do something about them further down the line. Transform them in a way. Although I do love a good whore with a little cock’ he said. ‘Turn around’ he ordered. I spun on the spot and waited for further action. He bent me over the table and immediately slid his large cock inside my tight asshole. I screamed in pain as the thick rod penetrated my anus ring. ‘That’s it, little whore, sing to me’ he said menacingly as I shrieked in agony with every trust of his massive cock deeper inside my bruised and fatigued asshole. The restaurant owner was standing leaning behind the counter the whole time, watching the whole thing unfold. After ten minutes of sheer agony, bent over the table fully naked having my asshole fucked by Paolo, he slowly pulled out of my asshole. He gestured for the owner to join us. My body was dripping in sweat, barely able to withstand the onslaught on my aching anus. Paolo spun me around and grabbed my head with both hands again, pulling me down towards his cock. The restaurant owner came behind me and I realised his trousers had already been unzipped, he had been jerking off while watching me get fucked by Paolo. Now it was his turn. He lifted up one of my legs and slipped his massive rod inside my brutalised anus. Even though Paolo’s massive cock was in my mouth, my scream of agony was still audible. ‘Not long to go, little whore’ said Paolo menacingly, slamming his cock hard and fast in my mouth. The restaurant owner had already built up a good tempo of fucking my ass. ‘Business as usual Paolo’ he said, chuckling heartily as both men fucked me from both ends. My tiny, pathetic cock and empty balls hung limply between my legs, swinging uselessly with each thrust. Soon, I felt a warm explosion of liquid in my mouth as Paolo blew his load in my throat. A warm gasp of satisfaction beamed from his face. I choked on the semen before Paolo pulled out, then he held my mouth shut and waited for me to swallow.I barely got it down my throat while the restaurant owner still fucked me hard and fast. Paolo gestured to me to lick the remaining semen from his hard cock for a moment, then zipped up his pants and poured himself a glass of wine. Meanwhile, the restaurant owner was still plowing my anus. I couldn’t bear it any more, the pain was too much. I passed out while he was still fucking me.
I awoke some time later and felt something cold and hard underneath me. I realised I was outside on the restaurant terrace, under a table. I was fully naked. There were not many people around so I was guessing it was after midnight. My whole body was aching, especially my anus. Between my legs was a sticky feeling. I realised it was a mix of the restaurant owner’s cum, which had dripped slowly from my asshole after he had ejaculated inside me, when I was passed out, and sweat. I shivered for a moment then slowly got to my knees, then crawled out from under the table. There was a waist-high fence around the terrace, so the people passing by could not see the naked slut on all fours on the terrace. I made my way to the door of the restaurant and attempted to open it, but it was locked. I saw that Paolo and the owner were inside, drinking wine and smoking cigars, laughing and telling stories. I knocked on the door. They waved at me and laughed again. I knocked again. The owner slowly stood up and came towards the door. I was kneeling outside completely naked. ‘Hello, whore’ he said, grinning. ‘Well done, you made Paolo a very happy man tonight. He has not had this much fun in quite a few years’ he said. ‘Can I please come in?’ I asked, still on my knees. ‘No, your shift is over for today. Come back tomorrow.’ he said coldly. ‘But, I’m naked. Can I please have my clothes?’ I begged. ‘No, you can get them tomorrow.’ he replied. ‘What? Please! I can’t go home naked!’ I pleaded, grabbing his legs with my hands. ‘He lifted one of his feet and used it to shove my legs apart, then proceeded to stomp down on my tiny cock, crushing it against the cold, hard floor of the terrace. ‘Seems like you need to cool off, little whore’ he said menacingly. ‘A good naked walk is just what you need to change your attitude. After all, you couldn’t even stay awake for when I was fucking you, after I bought bedava bonus you those lovely gifts this morning’ he said, pressing down firmly on my tiny cock. I shrieked in agony. Then he turned around and closed the door, locking it behind him. I was left naked on my knees outside on the terrace, my asshole and tiny cock in agony. I slowly stood up. The street was empty. My feet were aching after wearing the high heels all day in the heat, so with each step I winced on the hard cobbled stone street. I walked as fast as I could down the street until I got to the corner where I needed to turn. With each stride, my little boobs jiggled and my tiny cock flopped up and down, inflicting more pain on the tiny blob of flesh between my legs.I peered around the corner and spotted two couples walking across the street from a taxi. I watched as they entered one of the apartments. Then I waited for the taxi to drive off before turning the corner and continuing down the street. This street was also empty at first. Then from one of the side streets up ahead I heard footsteps. A police officer emerged from the alley. I quickly ducked in behind a group of large flower pots nearby, hoping he did not see me. The police officer proceeded in my direction. I huddled nervously behind the flower pots, which contained reasonably large palm trees. I shuffled around to the far side of the pots as the officer drew nearer. My heart rate increased as the officer approached. Would he spot the naked tranny whore hiding behind the pots, on the street in the middle of the night? Would he punish me in more ways than one? I closed my eyes as he approached. I heard the footsteps continue and realised that he had passed by, oblivious to my presence. I breathed a sigh of relief and slowly emerged from behind the trees. I quickly continued along the street, as fast as I could go. A car raced around the corner and I quickly covered my crotch area with my hands. The driver sounded the horn loudly, thinking I was just another naked whore. I continued on to the end of the street, then I heard the car turning around and speeding back in my direction. Again, the driver sounded the horn as he sped past. Thankfully, Nastia’s apartment was just up ahead. I broke into a run and my small titties bounced violently with each stride, as my feet ached every time they hit the pavement and my tiny cock and balls swung between my legs. Eventually I reached the apartment door. As I did not have a key, I needed to press the buzzer for her to let me in. I pressed the buzzer a few times, but no reply. Then I remembered she had said she was staying at her boyfriend’s house tonight. I panicked. Naked, aching, standing outside on the street. I looked around, a few cars were passing by. Again the horns sounded. I just needed to get inside. In desparation, I buzzed our neighbour’s button. ‘Hello?’ she queried after a few minutes, probably after getting out of bed. ‘Hi, Justine, it’s me. Sorry to disturb you but I was working late and forgot my key, could you please buzz me in?’ I asked. ‘Sure thing, dear’ she said. She was a slender French woman in her late fifties. Long, brunette hair, elegant, well-maintained body and always wearing the best fashion. The door buzzed and I gleefully pushed it open and slipped inside. As quick as I could, through the pain, I made my way up the cold staircase to the second floor. My bare feet pattered across the cold, hard floor of the building as I made my way to our apartment. I kneeled down outside the door and searched for the spare key under the mat. Just then I heard the door behind me open. ‘Looking for this, honey?’ said the woman. It was Justine. I turned around to see her dressed in a stunning silk robe and red lace lingerie and stockings, as well as dark red high heels. She marvelled at the naked, exhausted whore who was kneeling in front of her. I pulled my legs together and covered my breasts with my hands. Justine strode forward and pulled my legs apart, then stomped down on my tiny cock with her sexy red heel. I cried in agony with whatever strength I had left. I had endured enough torture this evening. I had been fucked by two men so hard that I had passed out. One had given me a tip but then they had kept both the money and the clothes, leaving me to walk home completely naked. Now my neighbour was crushing whatever remained of that pathetic piece of flesh between my legs. ‘Oh yes,’ marvelled Justine. ‘I think you better come with me, love’ she advised me, turning around and slowly walking towards her door. ‘It’s the only way you’re getting this back’ she teased me seductively, waving the key to our apartment as she winked at me. I mustered up the strength to slowly crawl into her apartment door. She closed it behind me and locked it.
To be continued…
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