My Sister's Whore free porn video

My Sister's Whore By Linda Laving [email protected] I was on my knees in a hotel suite, dressed in a black miniskirt, purple spandex blouse, black fishnet stockings and garter belt, and 3" lace up stiletto heels. A group of guys were surrounding me, catcalling, joking and laughing. My mouth was stuffed with a large cock which had just finished draining itself onto my tongue, and just as he pulled it out I heard 'open up', so with a gulp I swallowed the mouthful and quickly opened my mouth again as another guy pushed a cock towards my face and stroked himself, and a large wad of thick goo blasted me in my eye before he adjusted his aim and began to spray his cum between my lips, again filling my mouth. It was the last cock of the evening, 15 different guys had wanted me to suck the cum out of their cocks, and 9 others had jerked themselves off on my face, hair, and mouth. I was my sister's whore. After the last guy drained himself onto my tongue, I swallowed the final mouthful of hot sperm to a few cheers, and slowly stood up and stretched my cramped legs. I wiped the cum out of my eyes, and said, 'I have to use the bathroom to clean up.' The guy who'd answered the door and given me the envelope of money when I'd come in said, 'Sorry, someone's using it.' with a smirk. I asked if I could get some tissues then, and the same guy said 'They're in the bathroom... you'll have to leave now.' and he handed me the long cover up sweater I'd worn into the hotel. I just said, 'Nice group of guys.' and walked to the door which he held open and walked out. The hall was empty, so I walked over to the elevator, hoping I'd get out without seeing anyone. But when the elevator opened, there were two older couples inside who looked at me first with shock, and then disgust. I was a mess, my hair, face, and cleavage were covered with globs of thick cum, and I looked down at my feet and ignored the whispers as the elevator rode down to the lobby level. Fortunately, I'd been to that hotel many times before and was able to get out the back door without a major incident. I walked out to my car, reached in for some paper towels and wiped off the majority of the cum from my face and hair before getting in, and pulled the envelope of money from my panties and counted it. At least that part was okay; there was $1,200 for the 24 guys I'd serviced. Group rate. A few hours earlier my sister Tammy had come into my room and said, 'Chrissie, another job for you.' She handed me a Post It, which said, 'Marriott, suite 523, ASAP, convention group, a few dozen guys.' 'Okay, sis, I'll get ready.' Looking at myself in the car mirror afterwards, sticky with cum and with the taste still strong in my mouth, I thought back to less than 6 months earlier - when I had been a typical teenage boy - and then, fate stepped in with my sister as a witness. It was the summer after my graduation from high school. My mom was working as usual, and my older sister had gone down the shore for a few days to stay with friends, so I had the house to myself. I was still having coffee when the back door flew open and my best friend Tom walked in. 'Chris,' he said, 'you have got to see this!' 'Good morning to you too.' I said. Tom had been my best friend since we were little. Tom is a jock type, good at all sports; a tall well built kid with short dark brown hair and blue eyes. I'm very different, skinny, 5'6, with long straight dirty blond hair down past my shoulders and gray eyes. But we always got along well - and we were both in between girlfriends at the time. 'Check this out.' Tom said, and tossed me a video. I caught it and looked at the front, and saw it was titled 'Hungry Trannies', and there was a picture of a tranny in lingerie on her knees sucking off a guy. 'Where did you get this?' I asked. He replied, 'I traded an old video game for it - let's put it on.' So we went into the living room, slid it into the VCR, and hit the play button. The title screen came on, and in the video a tranny, with a bulge in the panties, was kneeling on a rug in a living room. A naked guy with a large cock, filmed from the neck down, walked into the room and said, 'Open up, I need draining.' - and the tranny replied, in what sounded like a high guys voice. 'And I need my tummy filled.' and turned sideways to the camera as the guy walked over and pushed his cock between the tranny's red lips' I was already hard, and looked over to see that Tom was hard also, so I leaned back into the sofa to watch. Tom lit up a joint, took a hit, and passed it over, so I took a large hit and passed it back. The camera went into close-up and the tranny's face filed the screen as a cock slid in and out of her mouth as she made moaning noises. Then the guy's voice said 'open your mouth wide, I'm going to cum', and he pulled his cock out from between her lips, she opened her mouth and stuck her tongue out, and he stroked his cock twice and a blast of thick white sperm hit her on the upper lip before he adjusted his aim and several spurts of cum shot directly into her mouth, and he kept stroking till he drained his balls onto her tongue where it was pooling up. It finally stopped, and the tranny pulled the cum covered tongue back into her mouth, closed her lips, and swallowed as you saw her Adam's apple move a few times - and then she opened her mouth again to show an empty tongue. 'Geez.' I said, as the camera backed up and the guy starting walking away. 'That's kind of gay, isn't it?' 'I don't know,' Tom said. 'it doesn't hit me that way.' We both took a few more hits off the joint, and I was getting really stoned. 'Good weed.' I said. Tom replied, 'Yeah, dude, it's supposed to be Thai.' When the next guy walked into the scene, Tom said to me. 'By the way, I need that $60 I lent you last week for the video game - you have it, don't you?' 'Ummmm... I don't.' I said, 'My mom had promised to give it to me, but when I came in late for the second time last week she told me she wasn't going to - I'll try to get it soon.' On the screen the second guy was now standing in front of the tranny, and this time she was actively working on his cock, moving her head back and forth and making slurping noises as the guy moaned. I was getting turned on in a way I never had before, feeling kind of warm all over, and it wasn't just the weed. 'You can pay me back with a blowjob if you want.' Tom said, and when I looked over at him, expecting to see him grinning, he wasn't. 'No fucking way.' I said, 'I'm not gay.' 'I didn't say you were,' he said. 'sucking a cock once doesn't make you gay. And besides, look how much that tranny is enjoying that.' I looked back to the TV just as the guy groaned loudly and pushed into the tranny's throat, and she made a loud 'mmmmmmmm' sound as he was obviously draining himself into her mouth. And after a minute he pulled his cock out of her mouth and said 'Show me.' and she opened her mouth wide and turned to the camera, which zoomed in so just her mouth filled the screen and you could see a large pool of thick white cum almost filling her mouth. She leaned back her head a little, gargled the cum, and then closed her mouth and gulped, and opened it again to show it was empty. I was totally hard at this point. 'Are you sure you don't want to pay your debt with a blowjob?' Tom said, 'Maybe put on a pair of your sister's panties and a bra? You know I'd never tell anyone.' I sat there silently, thinking. I'd never really thought much about anything like that before but the video had made me feel different, and really horny. And for some reason, the thought of putting on a pair of panties and a bra excited me, and being stoned made that excitement more intense. Plus, I had no idea where I was going to get the money I owed him. 'Just the one time?' I said 'and you promise we'll never bring it up again afterwards?' 'Promise, dude' said Tom, 'And I'll give you a handjob afterwards to seal my silence.' I got up and went into my sister's room and got a matching set of pink satin panties and bra out of her drawer, pulled on the panties and fumbled with the bra till I got it clasped, and came back out into the living room. The video was still on, the tranny was sucking off another guy, but as I came in Tom turned to me, opened his eyes wide, and said, 'You don't look too bad, dude.' and stood up, 'How about letting down your hair too?' I saw that he had a huge boner, and as I reached back to loosen my long hair and let it fall around my shoulders he opened his jeans and pulled down his jockey shorts and his cock popped out. I'd never seen it before, but it was larger than I'd expected, maybe 7 inches with a pronounced cock head, and it stuck out at a very slight angle. I couldn't take my eyes off it, and feeling my hard cock against the silky panties; I walked over to him and slid to my knees. With the sounds of the video still running, I slid my lips over his cock, and was surprised by the warmth and the softness of his cock inside my mouth. Without thinking much I began to suck and move my lips over his cockhead, but Tom said 'Ouch! Softer dude, and cover your teeth or something.' So I covered my teeth with my lips and stopped sucking so hard, and he began to slowly move his cock in and out of my mouth, and I ran my tongue over the pronounced head. 'Ohh, dude, I'm gonna cum.' he said just a few strokes later, and when I tried to pull back he held my head and I suddenly felt a spurt in my mouth as it began filling up with warm thick cum, and the taste, a salty sweetness, filled my senses. But then, out of the blue, I saw a light flash and heard a click, and I quickly pulled my mouth off his cock to look towards the flash. Tom's cock gave a final spurt as it pulled out, hitting my cheek, and as I stared openmouthed some of the sperm started running down my chin, and there was another flash and click, and I saw my sister Tammy standing in the doorway holding a camera. Tom quickly stepped back and pulled up his pants, said, 'Later dude.' and pushed past Tammy heading for the front door. She said to him, 'Don't forget, I got you in the pictures also.' and I heard the outside door open and slam shut. Tammy stood there as I was getting up off my knees, the video still on behind me. 'Well, well,' she said. 'my baby brother is a fag AND a sissy. How long has his been going on - and in my panties and bra?' I blurted out. 'This is the first time ever! Please don't tell mom!' 'We'll see.' she said, 'I do have to think about this.' I ran from the room to my own bedroom where I yanked off the panties and bra and slipped back into my own clothes - and waited for Tammy, scared to death. Tammy was three years older than me, and going into her senior year at a community college a few miles outside of town. We'd never been close at all, and she'd always done her best to make my life miserable, so I wasn't expecting much sympathy from her. She was about my height, and built similarly except for her hips and breasts. And had brown hair to my dirty blonde and green eyes to my gray ones. Since I'd never known my dad, except for my mom, she was the only close family I had. The next morning, after a mostly sleepless night, I heard my mom leaving for work and I got up and went into the kitchen for some coffee. About a half hour later my sister came out of her bedroom and into the kitchen, poured herself some coffee, and sat across the table from me. 'I decided not to tell mom...' she said. 'Thanks!' I blurted. '... for now.' she finished her sentence. She was staring at me curiously. 'I have some ideas.' she said. 'Like what?' I asked. 'You'll see,' she said. 'but for a start, follow me.' and she left the room and headed for the bathroom. I followed her to the bathroom, where she said, 'Strip.' 'Not in front of you...' I started to say, but she said, 'Oh, please - like I'd have any interest of that type in you even if you weren't my brother. Plus, you're not in any position to bargain.' So, blushing, I stepped out of my clothes, and then she handed me a container and said 'Put this all over your body, every inch from the neck down.' I saw that it was Nair, and started to say something, but she said, 'Do it. Now!' So I began to rub the thick cream all over myself, and when I got everything I could reach, she took the container and got my back where I'd missed a few spots. The smell was awful, and she said, 'You have to leave it on for at least 15 minutes - so in the meantime shave your face, very closely.' I took a new razor, and with the odor of the Nair making my eyes water I shaved carefully in the mirror over the sink. Then she told me to stand in the tub, and she took a washcloth and began to rub the cream off my back, and then she handed it to me to do the rest, and I wiped it all off and then turned on the shower, rinsed the rest off, and washed off with soap, and then washed my hair. I'd never been a hairy boy to begin with but as I stepped out of the shower I looked down and saw that I was as smooth as a baby all over. I dried myself off, and she threw me a pair of pink satin panties and said 'Put these on and come into my room.' I slipped on the panties and followed her, and to my dismay I began to get hard. When she noticed that she just smirked, and had me sit in a chair facing her vanity and triple mirror. She sat on the vanity stool facing me, said, 'Stay still.' and took a tweezers and began plucking hairs out of my eyebrows. 'Owww,' I said. 'that hurts. Please don't do tweeze them too much.' 'Or you'll do what?' she said with a smile. I just sat there as she quickly began plucking hairs, and when she leaned back and saw myself in the mirror, I was shocked. My eyebrows were almost pencil thin, and along with my long dirty blonde hair over my shoulders instead of back in the usual ponytail, I looked somewhat feminine. 'This might hurt a little,' she said. 'but don't flinch.' she said, and she took this plastic thing off the vanity, lined it up over my left ear and squeezed. It really hurt, and when she moved it away I saw she'd pierced my ear with a large gold stud, and then quickly inserted another stud and did the same to my other ear. When I looked in the mirror I saw that the earring studs had a small ring attached to them. 'Please!' I said 'How am I going to explain all this?' 'Don't worry,' she said. 'I'll tell mom it was my idea. And by the time college starts you'll be able to leave the earrings out whenever you want.' I sighed, and sat there, and then she began to put makeup on me. 'Pay attention,' she said. 'I won't be doing this for you forever.' 'I won't be doing this to myself.' I said. She replied, 'We'll see about that.' She started with a foundation cream all over my face and neck, then powdered all over that. As I sat there, she used various eye shadows, eyeliner, curled my eyelashes with a metal implement, brushed mascara on, used a pencil and brush on my eyebrows, brushed on a few different shades of blush powder, and then used a pencil to outline my lips and filled it in with a deep pink lipstick. She then said, 'Hold out your hands.' and used a file to taper my nails into ovals, and then had me turn away from the mirror and lift my feet up one at a time so she could paint my toes deep pink to match my lipstick, and finally did the same with my fingernails. As my nails were drying she took a hairbrush and began to brush my hair, teasing it out a little at the sides and on top and then sprayed it with hairspray. My nails were now dry so she went in her drawers and pulled out a pink satin bra and some sheer pantyhose and told me to put them on. She left the room for a few minutes and I heard the water running and she came back in with 2 small water balloons, which she slipped into the bra. 'These will work for now' she said, and from her closet she pulled out a short halter top sundress, white with pink flowers which she told me to put on. Finally she attached a gold chain around my neck and on my right wrist and clipped some long dangling chains on my ear studs, then handed me a pair of shoes, white mid heel slides and told me to put them on. I slipped into them, and surprisingly they were comfortable, and then she turned me towards the full-length mirror and I looked at myself in shock! I not only looked like a girl, but I looked a lot older with all the makeup, and as I stood there next to my sister I realized that we were almost exactly the same size, except her hips were a little wider and I was a few inches taller. 'Not bad,' she said. 'eventually you'll learn to walk in higher heels and do your own makeup and hair. The voice is going to need some work, though.' She threw me a small white purse and said, 'Put your wallet in here, there's already some makeup and a brush in it - then we're going out.' 'I am not going anywhere!' I said. She sighed, and then walked over to the computer and pushed a few keys. The screen was filled with a picture of me on my knees with Tom's cock in my mouth - and when she pushed another key the picture changed to a close up of my face with cum running down my cheek and chin, and pooled up in my mouth. 'Okay,' she said. 'for the last time. I've emailed these pictures to a mailbox for safekeeping. So destroying this copy won't help.' I sighed, realized I was totally blackmailed, and picked up the purse and went to the garage door. We got in her car and she started driving away. 'Where are we going?' I asked. 'You'll see.' she said, so I leaned back against the seat and gave up. We seemed to be heading in the direction of her school, and as we drove down the highway I noticed we were both getting looks from guys passing us or being passed. It was a very odd feeling for me. We soon got off the highway onto some side streets, and I realized we were heading towards her small off campus garden apartment. And soon we pulled up in front of it. 'Let's go.' she said, getting out of the car, so I followed and we walked to the door that she opened with a key, and as I walked in behind her she called out 'Cathy?' We were in her living room, and one of the two bedroom doors opened and her roommate stepped out. Cathy was a small petite redhead with blue eyes, and she stared at me for a minute - and then recognition crossed her face and she said 'Wow! Tammy, I had no idea your brother could look like this.' Tammy smiled and said, 'This is now Chrissie. Did you get in touch with the guys like I asked?' 'They should be over in a few minutes.' she said - and right then the doorbell rang, and Tammy walked over and opened it. 'Hi guys! Come in and make yourselves at home.' she said, and stepped aside as 5 large guys followed her into the living room. 'Guys, this is Chrissie - Chrissie, the guys.' I stood there as 5 pairs of eyes looked me up and down, and then one of them said, 'Is this the slut that needs training? Not too bad looking, really.' I must've looked really confused, because Tammy turned to me and said, 'Chrissie, while you might be enthusiastic about sucking cock, you definitely have some things to learn. And our friends from the football team here have graciously agreed to let you practice on them.' 'Tammy, please!' I said, 'Don't make me do this!' 'Chrissie, for the last time I have only one word to say.' Tammy said, 'Pictures. Okay, guys, who's first?' Tammy said to them, and a guy with short dark brown hair and brown eyes stepped forward. Tammy threw a pillow on the floor, and told me to kneel there, and resignedly I did. And the guy opened his belt and dropped his pants, and then pulled down his boxers to expose a soft cock about 5 inches long. He stepped over in front of me, his cock a few inches in front of my face. And knowing what I had to do, and with no choice in the matter, I opened my mouth and took his soft cock inside as the two girls and 4 other guys watched. 'Soft, and cover your teeth,' Tammy said. 'use your tongue along the shaft, and move your lips in and out slowly.' The cock in my mouth was really silky feeling, and as I did what I was told, started to get firm, and then hard, and the cock head became pronounced. 'Now suck gently, and keep your tongue underneath and flick the tip over the spot where the cockhead meets the shaft on the outstrokes.' she said. The guy was now rock hard and about 7" long, and when a faint taste of cum (precum?) hit my tongue I knew I was doing it right. In the background I heard the others laughing and making rude comments, and I saw a flash and heard a click, and thought 'shit', but 2 pics or a dozen were all the same. And involuntarily I was getting really turned on, and my cock was really hard in the panties I was wearing. I heard, 'Speed up the rhythm a little.' so I began to move my lips a little faster along his shaft. The guy was moaning softly, and then groaned, and I felt a small pulse against my lower lip just before my mouth started flooding with a warm stickiness as he began to fill my mouth with cum in repeating spurts. I could feel my tongue being covered, and then overflowing, and without thinking I swallowed, and could feel the sticky mass sliding down my throat, as another flash went off. The cock, already softening, slid out from between my lips, and I looked up to see my sister smirking, with the camera in her hand. 'I can see that you're a quick learner - and from looking at your cock you're loving the lessons.' she said, and everyone laughed. I'd never felt so humiliated in my life, but at the same time I'd never been so turned on. Another pair of pants was dropped and another cock was in my face. This one was already hard, and longer, about 8" but tapered at the tip. I took it in my mouth, and began sucking it the same as the last one. As I began to move my lips up and down the shaft my sister said 'Take it deeper.' but when I did the cockhead hit my throat and I gagged. My sister said, 'Relax, go slow, and hold your breath on the instrokes.' and when I did I found that I could take the cock in my throat without gagging as long as I didn't leave it in there. So I began to slowly move my mouth up and down his shaft, and was now letting his cock slide into my throat as my lips went to the base of his cock, and my nose was pressed against his pubic hair. The flashes from the camera were now coming steadily but I barely saw them anymore, and the guy I was sucking off was moaning while everyone else catcalled and laughed. And then he groaned, and with his cock all the way in my throat he held my head there and exploded, and I fought gagging as my throat quickly became flooded with his sperm fluids. But I couldn't swallow like that and the next thing I knew I choked a little and a stream of cum began to flow from my nostrils, around my mouth, and into his pubic hair. He pulled out, and I heard my sister say, 'Clean his cock and pubes.' and I grabbed a quick breath and began to lick his cock clean and then sucked the globs of cum out of his pubic hair - and finally I reached up and used my fingers to clean my upper lip and chin off, and my sister said 'Lick your fingers clean.' So I did, and during all of this the camera was steadily taking pictures. 'These will be some cool pics.' my sister said, and everyone laughed. I was now in a daze, and felt lightheaded, so I said, 'I have to use the bathroom.' but my sister said, 'No - you're not done yet.' So I stayed on my knees, and the next 2 guys took their turns before me as I sucked the cum out of their cocks with a combination of the techniques I'd just learned. By the time the fifth guy stepped up, I had to pee really badly, and said so, but my sister said, 'Not yet - only one more to go.' The last guy had the largest cock yet; probably 9" and wide, and I quickly went to work on him to get it over with so I could pee. I began to blow him, and by now my throat was stretched, I guess, because I was able to get all of him into my mouth and throat. But then I heard Tammy whispering to him, and all of a sudden he grabbed my ears and began to thrust into my throat forcefully, but before I could react, he pushed in, hard, and blasted my throat with cum. I choked again, and then my bladder opened and I began to pee and could feel the warm urine running down my thighs, and at the same time my stomach spasmed and as his cum was sliding down my throat, my stomach contents were coming up, and with his cock still plugging my mouth, a mixture of cum and vomit streamed from my nose and began to push around my lips, and when the guy saw this he pulled out and stepped back very quickly as I leaned down and vomited in my own lap, and then gasped for breath. After a silence, the room broke into laughter as I kneeled there in a puddle of urine, covered with cum and vomit, and as the camera flashed again and again, I heard my sister say, 'Well, I guess Chrissie's a full fledged slut now - thanks for your help guys.' And as I kneeled there I began to cry, my tears sliding down my cheeks, as I heard people leaving as the door opened and closed. I looked up at my sister and said 'Why do you hate me so much? I wish I was dead.' and I leaned forward, sobbing. She walked out of the room, but a minute later I heard footsteps coming back into the room. 'Come on, get up sweetie.' she said, and when I looked up to see who she was talking to, she was looking at me - and she had a soft look on her face I didn't recognize. She reached down to help me to my feet, and then picked up the pillow I'd been on and threw it in a large garbage bag, and threw some newspapers over the mess on the floor. Then she said, 'Let's clean you up.' and I followed her into the bathroom where she told me to undress, and I did, completely, and put everything into the garbage bag she was holding. Then she turned on the shower, handed me some oily pads and said 'Use these for your eye makeup first.' and left the room. I wiped off the mascara and liner in the mirror and stepped into the shower and stood there as the hot water rinsed the mess off of me, then I used soap and the rest of the makeup came off and I finally washed my hair. I stepped out and began to dry, and she came into the room and handed me a long white satin nightgown to put on. And when I did she took me into her bedroom, where the bed was turned down and told me to lay down. I did, and fell asleep almost immediately with the taste of cum in my senses - and my dreams were of me as a little girl... and they seemed somehow familiar. When I woke up the sun was streaming in the windows, and when I looked at the clock I realized I'd slept for many hours, and it was now Saturday morning. I got up to go to the bathroom, and I saw my sister sleeping on the couch, so I let her sleep and went to make some coffee. As I was finishing my cup, I looked up to see Tammy standing in the doorway. 'I called mom last night and told her you'd be staying here this weekend' she said 'Cathy went away to visit her parents.' 'Why, so you can humiliate for the whole weekend?' I said, and looked away from her. But she just said 'No, we're not going to do anything like that ... I promise. Why don't you go take a shower and shave while I'm having my coffee' So I did take another shower, and shaved even though there was barely stubble coming through from my light beard. I didn't have any guy clothes there, so I slipped the nightgown back on, and went back in the kitchen. 'Grab something to eat' Tammy said 'while I shower', so when she left the room I made some toast and had another cup of coffee. And a little while later I heard her call me, and I got up and found her in her room, all dressed in jeans and tee with little makeup. 'Sit down' she said, and when I did she sat in front of me and started to put makeup on me again. And when I asked her what was going on, she said 'You'll see ... but you'll like it this time - pay attention, I'm putting daytime makeup on you' She put a liquid foundation on me this time, and just a little powder, and when she did my eyes she put the eyeliner on in a very thin line, used pastel eye shadows, a single coat of mascara, and barely touched my eyebrows with a pencil. She brushed on a light pink blush, and then did my lips with a light pink lipstick. My hair she left in its natural center part, my nails were still polished deep pink and she put a thin gold herringbone bracelet on my wrist as the only jewelry besides my pierced studs. Going to her dresser she threw me a pair of panties and a bra to put on, and she'd saved the water balloon falsies. And then she handed me a pair of short white slacks ('Capri's' she said) and a bluish green 3/4 sleeve tee, and finally a pair of white flat strap sandals and a white shoulder bag. I looked at myself in the mirror and it was even odder than the day before - because even without the heavy makeup I still looked like a normal teenage girl. Tammy grabbed her own bag and said 'Let's go', but all of a sudden I was terrified about going out like that, and told her so 'Oh, please' she said 'the only stares you'll get will be admiration from boys, no one will suspect you're not a girl' We got in her car and started driving, and after a few minutes I finally said 'I have to ask you - why do you hate me so much? I've never done anything mean to you.' Tammy sighed, and was silent for a minute ...and then she said 'I was thinking about it all night - I felt terrible about how mean I was yesterday. And I finally realized it had been building up since that time, many years ago, when mom punished me because of you' 'What are you talking about?' I said 'I don't remember anything like that' 'You really don't, do you?' she said, and was silent for a few minutes. Finally she said 'When you were really little, you were the cutest thing. I'd always wanted a sister, and you were always fascinated with me. So from the time you were about 5, whenever mom wasn't around, I'd let you come in my room and put on my clothes. You'd let me put mom's makeup on you, and we'd always play girls games. You were like my little sister for years.' 'Then, when you were 9, mom caught you dressed like a girl and freaked out - and you told her that I'd made you do it. I was punished, and you weren't, and I was so angry ... and I guess the anger never went away' When she said this, the memories all came back - of me being a little girl - of my mom being angry - and of being told that little boys couldn't wear girl's clothes. I'd blocked it all completely. I told her to pull over to the side, and when she did I leaned over and gave her a big hug, and she started crying. 'I'm really sorry' she said 'I won't hurt you anymore. Do you want to go back and we'll try to forget any of this happened?' But sitting there, as a girl, I realized that I didn't want to let this go back to before. Everything had changed. Anyway, to keep a long story short, Tammy and I had a wonderful weekend. We went shopping for me, and she took me to a hairstylist who layered my hair, gave me long bangs, and added some highlights. I figured that with a little gel I could keep it hidden in a ponytail like before. And we went out to eat, got to know each other all over again, and before I knew it the weekend was over and it was Monday morning. I still didn't have any guys clothes, and I knew my mom would be at work when I got home, so I got up and did my own makeup, and it wasn't bad. I blow dried my hair and borrowed a pair of long hanging earrings I could put through the rings in my ear studs, and I slipped into a new cotton halter top sundress I'd bought that weekend, and a pair of white sandals with a 3" heels. Tammy drove me home and said she'd call me, and I walked into my house for the first time as a girl. It was only 10AM by the time I got there, and knowing I had the house to myself for the day I went to the bathroom and peed, got a glass of orange juice and put the garbage on the back steps, then went into the living room and turned on the television. I was watching the news when the back door burst open and Tom came through the door yelling 'Dude, are you home? I jumped up to run in the bedroom but before I got there he came into the living room. 'Chris?' he said, staring at me. When I didn't say anything, and he continued 'I've been trying to call you since the other day and ... ' he stopped, and then burst out with 'Geez, you look unbelievable! What the hell happened?' I sighed and sat back down and said 'It's a long story, but I just got back and everything's OK - and I guess it's Chrissie, not Chris, at the moment' He just sat there staring for awhile, but then he said 'I've been thinking about the other day constantly, and I came over to tell you I was sorry. But seeing you like that is making it all come back ... you look so hot.' When I looked down and saw that he was hard I started getting horny myself. So I told him to sit down, and he did. I reached over and started rubbing his cock through his pants, and he groaned. 'Take off your pants if you want to' I said, and as if in a daze he undid his belt and dropped his pants and his shorts to the floor. Without a word I slid to the floor at his feet, pulled off his shoes, and then pulled his pants off his legs, and kneeled between his feet. And then I leaned over and took his cock inside my mouth and slid my lips down his shaft all the way, and he groaned again. I began to gently suck on his cockhead, and lick across the end, and then slid my lips up and down a few times slowly, letting his cock enter my throat before sliding back out again. He began to moan, and I didn't want him to cum too quickly, so I slid my mouth off his cock, and then straightened my back and looked at him. We were both breathing hard, our faces less than a foot apart. And then without thinking about it I leaned forward a little and kissed him lightly, and slid my tongue out a little between his lips. And instead of backing away, he opened his mouth a little and we began touching tongues lightly, and kept kissing. I reached up with my left hand and stroked his cheek as we were kissing, and with my right hand I started slowly stroking his cock. He moaned, and I leaned down to take his cock in my mouth again, and began to suck very slowly and gently - and then he blurted 'I'm going to cum', and as I felt a pulse along my lower lip, his cock began to flood my mouth with his juices, and I drank them down as spurted. Within a minute he was done, and slumped back and I leaned back again to look at him ... and found his staring. I got up and moved over next to him on the couch, feeling really strange about the whole thing. I leaned back myself, not looking at him, and waited for him to say something. But instead, he reached over to put his arm around my shoulder, and leaned over and kissed me again. We sat there touching lips and tongues, and then he pulled away and said 'Can I do something for you?' 'If you want to' I said, and he reached under my sundress and began to rub my cock through the panties, and then slipped it out the side and started stroking it. We were still kissing, and then he slid off the couch, and kneeled between my legs and took my cock in his mouth. It felt nice, and warm, but I wasn't hard, and as he sucked it, my cock got firm but not stiff. But it was turning him on and I saw that he'd got hard again, and was stroking himself as he used his mouth on my cock. 'It's not going to happen' I said 'I'm not sure why, and it feels great, but I'm not going to be able to cum like this' He looked up and said 'That's OK' and leaned over to kiss me. We kissed in that position, he was stroking my cock and his own, and then he said 'You are so hot it's driving me crazy'. He reached under my balls and began to run his finger across my asshole lightly, and then lifting my cock out of the way he leaned way down and began to run his tongue wetly across my ass crack, and then slipped a finger into my ass. I made a soft noise, and then he said 'Can I fuck you?' I'd never once in my life thought about that, but it seemed right all of a sudden. 'Do you have condoms?' I said 'I don't want any cum in my ass.' 'Yes' he said. 'Then be gentle' I replied. He pulled a lubricated condom out of his wallet and rolled it over his dick, and I leaned way back on the couch with my ass off the edge and lifted my legs up onto his shoulders. And, still kneeling, he put his cock right against my sphincter and pushed slow, and then his cock popped inside my ass and I screamed softly. 'Sorry' he said, and with his cock just barely inside me he leaned over to kiss me. I was almost bent double, my ankles still on his shoulders, and as we kissed he slowly pushed inside me till he was fully in. It hurt, but felt wonderful at the same time, and he straightened a little and began to fuck my ass very slowly, and every time he pushed in I softly moaned, almost a squeal. And then I felt him tighten up, and he pushed in hard, and as I felt his cum filling the condom inside my ass, we both moaned together, and he leaned in again and we kissed as he spent himself inside me. He finally started getting soft, and pulled out, and looking down I was surprised to see so much cum in the condom, since it was his second time in a row. He stood up, and I leaned over, slid the condom off his cock, took his soft cock in my mouth to clean it off, and then took the end of the condom between my lips and squeezed out all the cum onto my tongue - and before I could swallow it he leaned down to kiss me, sliding his tongue into my mouth and into the pool of his own cum which still covered my tongue. He moved back and I stood up and swallowed, and all of a sudden the whole situation seemed very surreal. A few days before we'd been best friends, buddies, and now I don't think either of us knew what we were. It was a little uncomfortable, and as he dressed and I rearranged my clothes, neither of us said a word. There was an awkward silence, and then he said 'I'd better go' and I said sure, not looking at him as he left the house through the kitchen. I ran a bath, wiped off most of my makeup, removed my nail polish, got in the tub and sat there till the water turned cold. And then I dried myself off and went into my room and put on guy jeans, baggy T, sneakers, brushed my hair back with a little gel and put it in my usual ponytail, and sat in the living room, in silence, waiting for my mom to get home from work. The next 3 days were a fog. My whole world had been turned upside down and I didn't know what to do to turn it right again. I didn't feel comfortable enough to get dressed as a girl and go out alone anywhere, so I practiced makeup without getting dressed, and then washed it off as soon as I was done. I kept expecting Tom to show up or at least call but he didn't - and I left him a few messages but he never called back. So I sat home, mostly just laying on the couch with the TV off, and when my mom came home I had dinner with her and I found her staring at me a few times, looking like she wanted to say something. But she didn't, and afterwards I went to my room, closed the door, and lay on the bed, doing nothing. On Friday morning, I was still in bed and my mom had just left, when I heard the back door open, and a few seconds later my sister Tammy came into my bedroom, yelling 'Wake up' I groaned, but got out of bed and went into the kitchen where she was pouring 2 cups of coffee. 'How are you?' she asked, and I just answered 'Confused' We sat down at the table and I told her how I'd been feeling, and she told me she had a present for me, and threw a few prescription bottles onto the table. 'What is that?' I asked, and she told me she had a pharmacist friend who'd got them for her. I opened the bottles and saw that the first was filled with dark purple pills that said PREMARIN on them, and the other had yellow pills with SV printed on them. 'They're hormones' she said 'the purple ones are estrogen, and you take one with each meal, the yellow are progesterone, which you take in the morning' 'Why would I want them?' I asked, and she replied 'Because you're a girl, ... haven't you realized that yet? And they'll make you feel better emotionally' I was silent for a moment, but then said 'OK, I'll give it a try', and washed down one of each. I then told her about Tom on Monday, and she asked if I'd liked getting fucked. I told her I had, but only because it was so intimate - and that I wouldn't want to do that with just anyone. Then she asked me right out if I liked sucking cock - and without thinking I told her that I did, very much, but not under a situation like she'd put me through the previous week. 'Well, here's an idea, then. I've found on the Internet that there are a lot of guys who specifically like girls like you. And since we both can use the money, maybe we can become business partners' she said. 'What exactly do you mean?' I answered 'I'd set up dates for you as a transgender escort and do all the leg work and qualifying, and we'd split the money. The going rate seems to be around $200, it wouldn't be hard work, and you'd be able to express your desires at the same time' she said, and smiled. I sat there, thinking about it, but finally I said 'We can give it a try, but I can back out at any time. OK?' 'I'm glad you said that' she said, and smiled again 'because you have a date tonight, at 6PM' For the next few months I spent most evenings on dates. A small percentage were real dates, where the guys wanted to take me out first, and these were almost always OK - though a few of the guys were old enough to be my grandfather and very few were above average looking and most somewhat below. And most were just 'dates' in their hotel rooms where I'd show up at their room, have sex, and leave. Tammy had adjusted the rates somewhat, so that $200 was for 2 hours, with another $100 per hour after that. But the guys who wanted real dates always had money, it seemed, and didn't mind. Tammy worked all the details for me, and the real dates had a night allocated for them, and when the guys wanted hotel 'dates', she'd frequently line up 3 or 4 in a row, and sometimes in the same hotel, so I'd just go from room to room. The most frequent hotel was the large Marriott convention center, where there always seemed to be a lot of guys who liked TG girls. I was probably averaging about $600 a night, and keeping half and the money was rolling in. But the sex wasn't nearly as much fun as I'd thought it would be. There were a certain percentage of guys who were basically just looking for a blowjob, and those were the most fun. In most of those cases I'd go in the room, and be on my knees in minutes, my mouth around cocks of all sizes and shapes, and usually after the guys unloaded their cum into my mouth I'd barely have time to swallow before they were ready for me to leave. I'd always show the guys my cum-filled mouth before I swallowed, and there was always a percentage that wanted to cum on my face. But I wouldn't let them do that unless it was the last date of the night and they were willing to add a few hundred bucks. I did love sucking guys off, though, and it was always a thrill to be able to bring guys to an orgasm with my mouth, and to have it filled with sperm. I learned to sense what a guy was looking for in a blowjob, and I'd use my lips, tongue, and throat in whatever way satisfied them. I'd rarely even have to use my hands, but when a guy needed it I knew exactly how to use my fingertips along his shaft or scrotum to enhance his experience. And I found that if I timed it just right, a finger slipped into a guy's asshole would drive him crazy, and usually cause his cum to forcefully blast my tonsils. And the cum itself was also wonderful, I loved the variety of it, sometimes thin and watery and sometimes thick as snot and a challenge to swallow, and every load had a taste all it's own, with endless combinations of salty, sweet, spicy, musky, and bitter. And I especially liked it when there was volume, and it would almost fill my mouth and I could feel it sliding down my throat as I swallowed it. But it was always good. But, the thing that was becoming disenchanting was that the majority of guys were looking to suck my cock instead of the reverse. And while I didn't mind this, it wasn't a turn on, and as the hormones started kicking in I really couldn't get hard at all, and those guys were always disappointed when that happened. And a much larger majority of guys than I'd expected wanted me to fuck them, apparently this was a major fantasy among certain types ... getting fucked up the ass by a girl. And not only couldn't I do this physically, but the thought was fairly repellant to me as well. And as for me getting fucked? Well, this was the one thing that Tammy always screened for upfront, since that wasn't going to happen. I was probably averaging about $4000 a week and keeping half, which wasn't bad at all. But by the end of the summer it was getting old, and Tammy and I talked about maybe changing things around a little. My breasts had started to grow, not a lot yet, but enough that with the right bra and those half moon silicon enhancers I could get some cleavage. I'd taken some voice lessons and with some practice I'd learned to modulate my voice so that, while it was not high pitched, it was indistinguishable from a normal female voice. I'd had some laser hair removal, and while it hadn't gotten rid of everything, a good percentage was gone, and I was visiting an electrologist to clear out what remained. And my cock, from the hormones, had pretty much stopped getting hard - though I could still jerk myself off if I wanted to, and it could probably be sucked off by someone really good at it if I was so inclined. But I wasn't so inclined, and I'd learned to tuck my testicles back up inside myself, and with some surgical tape and a small panty liner I could make my cock just about disappear. I was staying with Tammy most of the time these days, and one morning she came into the room and said 'Chrissie, I know you want a change, and I've been researching and have some ideas about that also. With your cleavage, and what you've done with your appearance, I'm sure you can pass with the straight guys, as long as we go for strictly the blowjob crowd. I've talked to a few of the desk guys at the convention center, and they told me they're always being asked if they can set things up with a hooker for groups. They're willing to work with us, they'll get their cut from the johns themselves and can look out for you at the hotel, and all you'd have to do for them is give them free blowjobs when they want them.' So I said 'Let's work out the details, then', and Tammy did. I began working the convention circuit after that, and we'd worked out some standard rates. We were charging $100 a guy with a minimum $600 callout, and groups over 12 got a group rate of $75 each, and 20 and above got a rate of $50 each. For that the guys would either get a blowjob or could jerk off on me or in my mouth. No fucking, no kissing. And there was a 15-minute maximum per guy, if they didn't cum by then, they paid anyway. I actually liked the work a lot better than before, the guys were more straightforward, and I liked the quantity, most were a dozen guys or more. The second night doing that I got a call for a group of sales guys, and when I showed up there had to be 50 guys there, and most of them were in their 30's and better than average looking. I started off in my lingerie, on my knees in the living room of the suite, with a cock in my mouth as the rest of the guys stood around cheering and making comments. But after the first half dozen or so blasted my mouth with their cum, the crowd got really wild, and they started crowding around as I took on 3 at a time, one in my mouth and one in each hand, and as one shot his load of sperm into my mouth, I'd move my lips to one in my hand as another took his place in my now empty hand. I was in a fog at that point, my mouth almost continually being filled with cum, and whenever I heard 'I'm cumming' I'd take my mouth off whatever cock I'd been sucking and face towards that voice with my mouth open so that guy could push his cock between my lips and release his load of sperm. Quite a few weren't making it in time and I was taking quite a few shots in my face and hair as well, but most were feeding me their cum, my mouth and teeth were covered in goo, and there was a constant flow of sperm down my gullet as I swallowed mouthful after mouthful. And in an amazingly short time (I found out it had only been 2 hours, after I wiped enough cum out of my eye sockets to read my watch when it was over) I'd serviced the whole room. I stood up and the guys cheered, and after I cleaned myself up fairly well in the bathroom and came out, I was handed an envelope by a guy who said 'There's $2,600 here - for 52 guys, right?' 'Right' I said with a smile, and when I got home and told Tammy she was amazed. 'Geez' she said 'you must be full. That had to be a quart of cum' 'Probably less than that' I said, but I could feel my stomach sloshing as I walked in to take a shower. In my personal life, though, things were more complicated. I'd moved in with Tammy since her roommate had transferred out, so that had made things a lot easier, especially with mom. And college was starting and I didn't know what to do about that. My tits were getting noticeable, my eyebrows were pencil thin, my nails almost an inch past my fingertips, and my hair was layered with bangs, and had been streaked. There was no way I was going to be able to get back to passable guy mode, so I decided to attend classes as a girl. My student ID listed me as male, but I never had to show that, and to everyone I met I just introduced myself as Chrissie. A few people I'd known from high school were also going there, but as far as I knew, none had made the connection. Except one ... Tom. On my very first day of classes, I went to the cafeteria to grab a sandwich, and saw Tom sitting alone at a table, so I went and sat across from him. 'Hi' I said 'Hi' he said back 'You really look great, you know' 'You never called me or returned my calls' 'I really am sorry' he said 'you don't know how much I wanted to' 'Then why didn't you?' I said. He didn't say anything for a few minutes, but then blurted out 'Because I'm crazy about you, and it's all too weird for me. A few months ago we were best guy buddies, and now?' I was a little stunned, but said 'I'm sorry to hear that. It was a wonderful experience for me, maybe the best of my life.' 'So how have you been?' he asked 'Been seeing other guys?' 'Just a few' I lied 'but none were like you. And there's no one else I've even considered letting fuck me.' At this, he started blushing, and without even looking I knew he was hard. 'Do you have any classes now?' I asked. 'Not for an hour or so' he said, so I said 'Let's go outside for awhile, it's nice out' So we went out onto the campus, and I led him over to my car, parked in the shade. We got in, and I turned towards him and said 'I've really missed you. Especially as a friend', and he suddenly leaned over and kissed me. We sat in the car, tongues touching, and then he groaned and I saw he was painfully hard. 'We both have classes soon, but let me take care of that first', and I reached for his belt, but he opened it himself, and slid his pants down. We were parked in a quiet section of the lot, so when his cock popped out I leaned over and took it in my mouth. I softly sucked and tongued his cockhead, and he moaned softly, and within a few minutes he said 'Oh, geez' and my mouth began to fill up with his thick cum. I kept my moth around his cock till he started to get soft, but didn't swallow, and when he was finally emptied I carefully slid my lips off without spilling any, sat up, and swallowed it down. 'That was so great' he said. 'For me too' I said. I leaned over and gave him a soft kiss and said 'Can we see each other sometime?' 'I'd like that' he said, and we both got out of the car and headed back, and I was very surprised when he took my hand as we were walking through the busy campus. And at the door to the lecture hall, I said 'Bye', and was even more surprised when he leaned over to give me a quick kiss before going inside. On Saturday, Tammy and I had gone out shopping and to lunch, and I'd gotten another set of ear piercings as well as a tiny nose stud which I'd been wanting - and we'd both had our nails done, mine in a fuchsia color. We got back to the apartment and walked inside to find Mom sitting at the kitchen table. 'I knew something was going on' she said 'you've both been avoiding me. Chris, what is this all about?' I didn't know what to say, I just looked down at my fuchsia toenails. Tammy jumped in and said 'Mom, it's never been Chris, and you always knew that. It's always been Chrissie.' My mom looked like she was going to cry, but then she said 'I think I always did know, and didn't want to admit it' 'I'm sorry, mom' I said. 'There's nothing to be sorry for' she said 'things are what they are. Are you happy?' 'I am' I said. 'Then give me a hug' she said. And that was that with mom. During the next few months' life was really busy. I finished up my electrolysis and my breasts had reached a B cup and seemed to be still growing. School was going OK, and attending as a girl hadn't been a problem at all. I just made sure that I scheduled my swimming class last thing so I could shower at home afterwards. And I was working more than ever. Tom and I were seeing each other regularly, but mostly during the day because I was working most evenings. We'd been going out and doing things together, and the sex afterwards had been wonderful. He still liked to suck on me, but from him I didn't mind, and one time I was even able to cum in his mouth - and he was ecstatic about that. But I especially liked the kissing, and having him softly fuck my ass, and usually he'd pull out at the end and let me drink down his cum. I still hadn't told him what I was doing for work, though, and that was something I'd have to deal with eventually. The hotel guys were setting up jobs for me almost every night, conventions during the week, and local things on weekends, Rotary Clubs, Elks, and even a bachelor party or two. All the guys at the desk had been collecting on their free blowjobs regularly, and usually they wanted it right at the front desk. I'd kneel under the counter as they stood in front of me facing the counter and they came in my mouth as they looked out at the lobby. I was now averaging about $6,000 a week and keeping half, and had more money than I knew what to do with. The most unusual night was when they set me up during a magazine convention with the staff of Ebony magazine. I walked into that suite and found myself the only white person in the room. I'd sucked off several black guys in the past but this time there were a few dozen, mostly large, black guys, and I knew the cocks would be even larger ... and they were. I learned, for sure, that black guys do have bigger dicks, and also that they generally didn't get as hard as white cocks, but did blast out much larger quantities of cum. The first one I took in my mouth was probably 10" long, and wide, but I didn't have a problem at all with that. It was the throat fucking that got to me a little. He wanted to fuck my throat, and I was fairly used to that, but not with a cock that size. So I fought back gagging and breathed through my nose as that black cock slid in and out of my throat, and when he started to cum he pushed all the way in, held my head in place, and grunted, and the volume was more than I could take and I choked, my mouth plugged by cock, and cum started flowing forcefully out of my nostrils and down my chin. He finally pulled out, and I coughed a few times, still catching my breath as a second large black cock was pushed against my lips. This guy did the same thing, but I stopped for a minute and said 'you can fuck my throat, but if you hold my head, I'm leaving' 'Alright, white bitch' he said, and I relaxed as he fucked my mouth and throat, but when he started to groan I moved my lips out to the head and took his cum in my mouth this time. His sperm was very thick and flowed like a faucet for a long time, literally filling my mouth. I had to gulp a few times while he was still unloading to make room for the rest, but eventually he was drained, and it was on to the next cock. Every single cock that used my mouth that night was at least 8" long, and a few must have been 12". And not one would let me just suck them off; they all wanted to fuck my mouth and throat. And every single load of cum they deposited in my mouth was a choker, and had me swallowing before they were done unloading. By the time the first dozen guys had used my mouth as a pussy my throat was sore and my jaws hurt from keeping them open. And by the time the 25th, and last, cock finished draining itself onto my tongue my throat was on fire, my lips raw, my jaws aching, and my eyes red from coughing and gagging. My stomach also ached like I'd overeaten a turkey dinner, and when one of the guys handed me my money, it was the toughest $1,250 I'd ever earned. And I made a note to never work an entirely black group again. But, all in all, I realized how lucky I was. I was now the girl I'd been suppressing all my life, my sister had become my best friend and business partner, I was making more money than I knew what to do with, and I was working at a job I really loved - sucking cum from cocks. As my sister's whore. *** Author's Note: If you liked this story, please drop me a line. [email protected]