The Dogging Diaries - V free porn video

A note to readers - keep in mind that I never had a plan for these diaries. I'm only sharing them with the world because I can now handle the reflection that comes with reading them. As a result, they don't fit into chapter form all that well and at certain spots things skip ahead if I wasn't writing much at that time or had little to say in my entries. I have tried to find logical breaks to fit into a chapter format for this medium. Hopefully it is working for you and you are able to follow along. As this is Chapter 5, it is possible I've picked up some new readers along the way. All you need to know is that I have delineated each diary entry with a starting and end point notation. Anything written outside of those notations are my present day comments or thoughts about the entry and remembering (to the best of my ability) where my psyche was during that time. I hope this is helpful. Let's continue ... Diary Entry: May 2007 I crossed another line. What the hell is wrong with me? I got home from work last night and I could hear my coke stash calling me. Yet another week night? But I had some wine and I did some lines and before I knew it I was on Craigslist advertising my "services" to whoever wanted them. I posted the ad and then jumped in the shower to prepare myself. By the time I was finished I had about 20 responses. I weeded a bunch out and then set John up for 8PM ($100) and Mark up for 10 ($90). It was clear that both of them were interested in a quick fuck rather than anything resembling a date, so I slipped on a pink bra and slid pink lace boy shorts over my white gaff. I darkened my eyes with Lancome and used a blend of dark grey and pink shadow. I painted my lips a heavy, hot pink and glittered them up. Then I completed my trampy look with pair of 5" silver pumps and waited. I still can't fucking believe I did this at my apartment. John was there just after 8 and I had his cock in my mouth three minutes later. A delicious 7" tube of meat with some nice girth, and even better, once we got down to it he only fucked me doggie for a few moments before he rolled me over and fucked me missionary. I love being able to look them in the eyes, seeing their knowing sparkle that I am theirs, that I am their plaything. Then he decided he wanted me on top, so we rolled over and I got to ride that delicious stick at my pace, angling it just right to engage my prostate fully. Fucking glorious and I came so fucking good, my milk dripping from my clit with each luscious thrust. He was blown away that I can come like that. He smelled so good too. Even his cock smelled like fresh linens. I would definitely see this guy again. John was gone by 9 and Mark was inside me an hour later. It was a typical transaction fuck - a little small talk, the money exchange, he took off his clothes, I sucked his dick, he took off my clothes, he lubed me and then he fucked me doggie. It was OK. Neither guy asked me if I had any condoms and they didn't bring any themselves. Stupid on my part, but how the fuck is Jack checking these guys, anyway? He's not, and I do in fact love to feel a good stiff dick explode inside of my pussy, so what the hell? End Diary Entry Diary Entry: June 2007 Jack was over tonight with a new corset. He says I have to buy my own next time. This one has more boning and cinches down even tighter than the other one. More boning for my boning, so I can get boned. Basic black in color and will go with anything. But it is so tight! I can barely fucking breathe in the thing and I'm already used to wearing a corset. How the hell does a newbie do this? He also wants me to get laser surgery for hair removal. I don't have any hair! He says he can see it sometimes after a late night. The guy is bad for my self esteem. Diary Entry: June 2007 Well, the time is here. I'm going to come out to my family. This is going to suck and I fear the worst but I feel like I have to do it. Kristy is me, there's no other way around it. End Diary Entry I remember this period like it was yesterday. The feelings and guilt I had about not telling my family had been eating me up inside for a while and I felt like I had to do something. I wanted everyone there - mother, father, brother, sister-in-law, sister, brother-in-law, so it took me some time to coordinate the night around everyone's schedules. It ended up taking almost a week to put together and my emotions were a wreck leading up to it. I wanted it all out in the open in one shot, without using my parents as a go-between. I'm not sure I did it the right way or even if there is a right way, but I did it my way. It's funny to me as I read these diaries just how much of "me" is in them. Could I be more narcissistic? The looming issue of telling my parents or family or my job was with me throughout much of this time and yet I wrote about it very little. A couple of entries here or there, most of which aren't published here for the simple fact that they're pretty boring and just little notes. I was way more interested in writing about my sexcapades. And shoes. I have a ton of stuff in here about shoes that couldn't be more useless. Anyway, here's an excerpt of a family focused entry taken from a couple of months before this that I find interesting since I'm on the topic: ... It would be nice if there would come a day when I could just be one of the girls. Just Mom, [my sister], [my sister-in-law] and me sitting around a coffee table talking about the news of the day. Each of us with a glass of wine, looking pretty and just being girls. Could that day actually happen? Acceptance is a tricky thing. I wonder, and this sounds shallow, if they would have the decency to love me the same if I made the transition, but did it poorly. If I got fat or stopped the hormones and the hair removal and just let myself go, would they see me the same? I envision myself sitting with them and when I do, I see myself looking good, being pretty, being a girly-girl and being able to get down to brass tacks about girl stuff. My voice is pitch perfect and I look great. Would it matter if I was ugly? Will it matter if I'm pretty? Does that matter at all? And why is that important to me? ... Telling stuff, I think. Is my entire existence based on acceptance? Where is my self esteem level? Tough question to answer. Diary Entry: June 2007 Fucking laser surgery begins tomorrow. I'm all stubbly because I have to let the hair grow so they can zap it. I feel so gross. To top it all off I ate a frozen pizza for dinner. Right now I'm Kent Dorfman; fat, drunk and hairy is no way to go through life. This sucks. One pizza and I feel like I weigh 300 pounds. Jack would fucking kill me if he knew I ate it. End Diary Entry Diary Entry: June 2007 A lot of reflection going on right now. I could barely concentrate at work today. I think this whole "coming out to my family" thing has me tied in knots. I've been doing a lot of thinking about how I've managed to get to this point as Kristy; how it started, why it started, why I didn't do it sooner. I remember back to the Hustler Magazines I used to look at. It's funny, even then Playboy was never my thing. Even then I liked the sluts better, the ones that were never afraid to show their cooze to the world. The ones with the slutty eyes that seems to say, "if you want me, you can have me." You just knew those girls were down for a good fuck all the time. Thinking about those girls and just wanting to be one of them. Desired. I was thinking about the amount of boy-cum I used up flipping through those magazines, not even desiring the women, but desiring what it must have felt like to them to have men wanting you. I can't believe I was so blind to all of these signs for so long. Playing it up, dating girls (what a joke), being a guy. It's just not ... me. I'm a high heeled party girl and there ain't no way around it. Who could ever think that a reaction to magazine would have started me down this path? Granted, I realize it's more than that, much more and it comes from deep inside, but I have to admit, they played a role. Larry Flynt ... who knew? Everything around me now is feminine; from my clothing to my skin to the candles in my bathroom. I remember the first dick I sucked like it was yesterday. I remember the first time I put on a wig and saw it completely transform my face into something else. I remember the very first time I wore breast forms. Bought at the [one and only local tgirl shop] and they were C cups. Fucking crazy that I had bigger boobs then than I have now. Granted, I had to cover them up because they were fake rather than letting them fly like I do now, but still, I need bigger tits!! Thinking about the first time I used press on nails and trying to get the damn glue off. What a nightmare. So funny to think about now. That first night I went out. God I was so nervous. I remember talking to Shelly and she told me I should shave every spec of hair off of my body. Leave nothing. Eventually I did and now I'm doing laser and have plucked my brows into short, sexy arches. You were right Shelly. Experimenting with makeup, all those nights with Shauna just messing around and trying to get the look down. I think about all the shopping I've done and how I'd be nervous to buy a pair of thigh highs from Kohl's when I was in boy mode, as if they even cared enough to look at what I was buying. So crazy to think about how far I have come. And so depressing to think about how far I still have to go. I can't wait to lose the wigs, more weight, get my breasts done, my lips, maybe pierce my nipples, facial surgery, the list goes on and on. Can I really succeed as a girl? I suppose at this point my B cup boobs are pretty much the answer. There's no going back. Not that I want to. I just used to enjoy the journey. Now part of me just wants it to be over. To be done with the work and the day-to-day. I think it used to be more fun. I think I need to see someone and talk to them about this. Maybe talk to them about the hooking and the drugs. Something. I feel like it's me against the world right now. End Diary Entry Interesting to read that entry. If you asked me before I saw it I would have said that I was so focused on being a good time girl that I wouldn't have made any room for those sorts of feelings. I'm actually relieved in a way to know that they were there. I was definitely confused and feeling melancholy and there's some woe-is-me in there too. Fun to reminisce though. That part is great. I think we as tgirls owe it to one another to pool our knowledge and write a giant "How To" manual for any new girls. We owe it to them. This is hard stuff, hard work and it isn't always fun and you see the bad side of people quite a lot - but the payoff if you're sincere about it cannot be overvalued. It's insanely good for the soul to be who you are and be comfortable with that. Diary Entry: July 2007 It's done. Fuck. Where to begin? I invited my entire family over for appetizers and drinks instead of dinner because I wanted it to be less formal. I think it worked because [my brother] and [his wife] ended up leaving shortly after I made the announcement, something he might not have done had we had a formal sit-down type dinner. Anyway, let me back up. I decided to dress down and as much like my old self as I can at this point considering I have no hair on my body, pierced ears, high arched brows, size B tits, supple hips and weigh way less than the average guy my size. For that I went with jeans (womens), a baggy button down shirt and flip flops. My toes are painted plum. I left that part of me uncovered because I felt (and still feel) like my family needed to be able to see part of me, part of what I am. Had I just thrown on some mythical pair of workboots and didn't have my earrings in and thrown on a Red Sox cap it would have been harder for them to even grasp what I was saying. I have read a lot of information about our community coming out to their wives or family and it is strongly advised the t-chick not just pop out of some corner all hoochie-mama'd up and ready to suck the chrome off a trailer hitch. Reports are that never goes well. I respect that and think it makes sense but I figured this way would be enough for them to dip a toe in and see ... something. [Author's note: I think it's important for me to say something about my family so they're not just faceless people. Regardless of the way my story ends - and I'm talking big picture here, the way it ends years and years from now, not the way these diaries read - a reader needs to understand something: my parents are awesome. They both grew up outside of Boston, were high school sweethearts and are still married. Both graduated college at a time when very few people even went. My Dad was a project manager, my Mom a teacher. He did a six year stint in the army after college and they moved around a little bit as a result before settling back in Massachusetts to raise a family. They raised three kids; my older brother, older sister and me. My father was a self made man, not rich but providing for us enough that we all went to college on his dime and leaving a surplus for himself that allowed him to retire early. His Dad moved rocks for a living, so I give the man a ton of credit. And all the while Mom was by his side, raising us and doing her part. They're a great team. Dad could be a bit of a grouch when he was working, but once he retired, which he had done in 2004, he became a new man; happy, smiling, loving. My mother is one of those outspoken ladies who has an opinion on everything. She's a smart lady and she'll let you know that. Drives me nuts sometimes because she has a pretty negative view on a lot of things ... here's an example: if I told my family I bought a Ferrari they'd all be excited, want to see it, touch it drive it, etc ... my Mom would simply say "people die in those things." It's kind of funny in a way. She's such a ball-buster (not very ladylike I know, but that's the word that describes her best). But she has her good points too and I know she loves me. My brother is kind of a douche. Not in a Chet-from-Weird-Science way, but just kind of a self-centered guy who is content to talk about himself a lot and not talk about you very much at all. He's not mean or anything, just a douche. He's always been a pretty big dink to me about the whole transition thing and I get it to a point. He had a brother and then I disappeared. I understand. But still, if you love someone enough that you're deeply bothered by their disappearance, wouldn't you try to make an effort when your brother (me) becomes your sister? Still the same person you loved. But he can't do it. I'm not persona non grata, but we're not tight. I've tried too, but he's not really interested. In an awesome bit of irony, a couple years after this, I ran into one of his friends at a bar one night, he hit on me and I let him fuck me. My bro doesn't know that it happened, but his friend obviously does. Knew it was me too (once I told him) and he still stuck his dick inside of me and fucked me good. He had the hottest cum I have ever felt. Just molten man juice warming all of my insides. Good kisser too. Totally made my nips hard. What happened to that guy? My sister is pretty great. She's the one who over time really gave me a chance, gave us the chance to get to know each other as girls. She's the one I'm closest to fulfilling my hope of sitting around gabbing like chicks about pop culture or sex or something. We're getting close. We do it on the phone from time to time. She's all good for the most part. I say that because she's also the one who knows more of my story than anyone. She doesn't approve and she only knows a little, so I could only imagine her shock and disapproval if she knew I was taking 7 or 8 cocks on some Tuesday night when business is booming.] Back to the diary entry ... Thankfully my parents were the first to arrive. Telling my parents was going to be hard but I felt like if anyone was going to at least look towards the root of my emotions - does this make you happy? Is this truly what you feel like? - it would be them. My mother noticed my painted toes immediately and gave me a "what the hell?" type of comment but I was able to put her off for a few minutes by telling her we could all talk about it together. She wasn't pleased with that, but what are you gonna do? Before long my brother and sister and their spouses were there. I got everyone a glass of wine and then over the cheese plate I dropped the Kristy-bomb. "Look guys, there something that's been going on for a while and been on my mind for a while that I need to tell you." They looked at me and I could feel my tension rising. So I said it, to the best of my ability anyway and I tried to deliver it lightly, not in volume, but light as in breezy, because I didn't want the weight of the situation to overcome me. "I'm a girl." My sister said, "what?" my mother said, "oh, Stephen, no" and no one else said a thing. Fuck-fuck-fuck, this is precisely what I didn't want to happen. Just seems so clich? to have your family flip out or not accept you. Can't we just all be good with this? "I'm a girl. I live my life as a woman." "All the time?" my mother asked. "Every minute I'm not at work." "Oh my God," from my sister. "Like a cross-dresser?" another one from Mom. "No, not a cross-dresser. A girl. I live my life as a girl. There's the clothes, yes, but this is about emotions. It's different." There was a long pause. My brother, evidently now playing the role of Stifler: "so you're gay?" "That's not important right now." My dad: "I don't even really know what that means." Gotta love Dads. "Look," I was fighting to find some words. "It's something that I have felt for a long time now. Something that makes me happy. It's natural for me to feel this way, but I realize it's probably a shock to you, and I wanted you to know because I don't want to be lying to you guys. This was a hard decision. To tell you." God love [my sister-in-law] who chimed in with, "More wine?" We ran the gamut of questions for about another 5 minutes. Five minutes that felt like forever. I told them I wore makeup, dresses, women's shoes - that yes, I was a woman. More questions - how long had this been going on? Did anyone else know? What was I going to tell work? Those kinds of things. And then [my brother] and [his wife] left. I think they needed to process. Hopefully that's what it was and it's not the kiss-off. After they did I talked to my mom and sister for a while about other things, small talk kind of stuff and then everyone hit the road. My dad didn't say much. Mom said we'd talk more tomorrow. I think she wants to digest this news. Total time, just over an hour. I thought long and hard about maybe changing into something more feminine after [my brother] left but decided against it. Probably the right call to leave the 5" fuck me pumps in the closet. After they left I finished a couple bottles of wine and reflected on the night. No coke though. I stayed away from it. Way to go, me. All in all it didn't go bad and it didn't go good. In a lot of ways it didn't go. There wasn't some big dramatic blow up or breakdown or anything. It was strangely calm. I'm not sure they completely get it. End Diary Entry Diary Entry: July 2007 So Mom called tonight to see how I was doing. I think that's pretty sweet of her. I'm actually doing OK. I'm glad they know, scared of the potential fallout though. That shoe hasn't dropped yet. She'd like to come over tomorrow after work to talk some more. OK by me. Jack called to confirm we were on for this weekend. Does he think I'd skip out on my ritualistic pussy pounding and degradation? Who wouldn't want to be fucked and sweated on by an old, fat guy? It's what I live for. End Diary Entry Diary Entry: July 2007 So Mom and Dad were over tonight for a chat. I don't think they really get it and I'm beginning to think they need some kind of shock to the system to really understand. They kept asking if I looked like a girl all the time and I kept telling them I did when I wasn't at work and it was like they couldn't wrap their head around what that means. The whole thing gives me an ice cream headache. I think I need to have them over and look completely like Kristy when I do. I told Dad I had boobs tonight and his head looked like it might go spinning off, but again, I don't think they're going to fully comprehend it all unless I show them. After all, I had told them that two nights ago. It's going to have to wait though, tomorrow is a "Jack Friday," the start of another hotel room weekend which means I can actually eat something when everyone is done fucking me on Sunday. Mom did ask some pertinent questions about my job and whether I wanted a sex change. I can't answer the job question yet but I told her I didn't want a sex change. She seemed confused. I didn't have the heart to tell her some guys pay good money to fuck a chick with a dick. They would have had to put her six feet down if I said that. Anyway, all of this family drama is going to have to wait because I have my other job to do this weekend and I plan on doing it well. End Diary Entry Diary Entry: July 2007 OMG, so much to write about. It's Monday and I'm a mess. The whole thing is an exhausting intersection of another hooker weekend, my family and my job. I don't really know where to start. First, the weekend, I guess. I got to the hotel at 6:45 on Friday and there was Jack to let me in with his bottles of wine and too much cocaine. My tight little ass has become quite the little earner for him lately and I think he's beginning to feel the effects of my pussy on his wallet. If I can be so vain, the guy has it made. He works another job, is clearly single and spends most of his weekends sitting in a hotel room sipping wine, insulting me, ordering me around, watching me fuck and getting paid for it. Not a bad gig. So I get there at 6:45 after getting partially ready at my apartment after work because whenever I come straight in my sort-of boy mode Jack would always have shit to say about how bad I looked. So I get there in a pair of yoga pants and a light sweatshirt, but looking very much like myself and he starts in on me right away: "What's with the modesty crap? You're a hooker, Kristy, dress like one." "Well, I'm not going to pick up a trick walking from my car to the hotel now, am I?" I shot back. "Don't you fucking talk back to me!!" he shouted. The guy had turned on a dime. "OK. I'm sorry," was all I said, trying to keep the peace. Fucking jerk. I went through my regular routine of taking yet another shower (my 3rd of the day), shaving, primping, makeup and dressing. I chose a black pair of boy shorts, a black tube top and 5" black fuck me pumps. Simple yet elegant. Then I glittered up my dark plum lips and eyebrows and blew myself a kiss in the mirror. I was all come-fuck-me attitude as I made my way back over to the table. "Are you wearing the corset?" Jack asked. "Everyday." I couldn't resist asking - "why?" "Because your shape hasn't changed since the last time." "Jack, I wear the thing 24/7 - and it has changed. I wasn't this hourglassy the last time." He mumbled something shitty to me and then we got down to business. "Tonight is light. Just two guys on the docket, but tomorrow looks like a really good day. I've got four in the afternoon and as many as six that night." Ten different cocks in a day. It's unhealthy to have that much sex. Still, I was here and ready to work and we only had one last detail to take care of. I smiled at Jack and he threw the 8-ball of coke at me. I opened it and dumped some out on the CD case, ready to be chopped. "You really should be paying for this," he said. "Oh, I'm paying for it alright. Ten guys tomorrow." "Yeah, I'm not kidding." he said. "I need to start taking the coke as part of my money." He was serious. "Are you fucking kidding me?" I asked. "No. It's just one more trick." Fucking asshole. I pay about $110 for my share of the two nights at the hotel and 25% of the money my ass makes and now I have to give him another $150? Between the room and the coke that's two tricks that are fucking me for free. I didn't want to argue because he is a steady supply of blow and I don't want to lose that. "OK." I relented. Then I chopped up the coke and snorted two lines up each nostril, a little turbo charge to get my night going. Friday night was pretty uneventful for a while. I ended up having three tricks for a total of $375, which was short for my liking. John was the first inside me, a short but wide cock and he popped within the first five minutes. Fucking great that they're all named John. How many John's can there be? An hour later was a different guy and I can't for the life of me remember his name (probably John). Same thing as the first, a typical suck and fuck, doggie style. His cum felt heavy in my bottom. I remember that. Xavier was last and a complete godsend; a toned and lean beautiful black man with a luscious 8" torpedo. I have only had one other African- American inside me and I'm definitely beginning to understand what all the fuss is about. For one-on-one sex, this is the best I have ever had. He took his time with me, making me deepthroat his entire enormous cock by holding onto my hoop earrings and not letting me get away. I choked back my gag reflex like the good whore I am and took it all with everything I had. Then he picked me up and gently tossed me on the bed, before tearing off my panties with one strong pull. I can still hear the sound of the fabric tearing and it gives me chills. I can see his strong hand reaching towards me on my right hip side and ripping them off of me; his slut, his plaything, his whore. I felt the familiar grease on my pussy and let out an involuntary moan as Xavier prepared me. Then he drove into me with one shot. I cried out and then bore down on him, milking his cock with my muscles and grinding my hips back into him with each delicious thrust. He felt huge inside me. "Ungh. Yeah baby, ooh," I cooed. "Take that fucking pussy, yeah." My pussy was still stretching to take all of him and I bore down to let him take me to the hilt. I needed this fuck, to be mounted and taken with animalistic brutality. "You fuck me now, baby, you fuck me good," I cried. "Stuff that fucking dirty cunt, yeah." Xavier felt huge inside me and I maneuvered my prostate love button into just the right angle. Divinity. He was so big and so thick that I could feel every movement to my core. He had such a strong, consistent pace that I was able to move in tune with his body and his dick so well. We were one. I could feel my first orgasm beginning to build and I centered all of my focus onto the buzzing in my cunt. Such a fucking and such a fucking build up as I held out as long as I could before Xavier's magnificent cock took me over the edge. I felt myself swooning under his torrid assault and I screamed in glorious rapture as I felt my orgasm rip through me. By now I was completely wanton, an open sexual channel for my young stud, a tgirl harlot desperate to take all he could give me. I could feel my clit dripping with each thrust and at that moment there was no other place or person I ever wanted to be or be with. I was completely conquered, taken and breathless with lust as the tears began to stream down my face. "Please, never stop," my mind cried. "Never stop fucking me. Never stop taking me to this place," as my eyes closed in yet another glorious rapture, the milky ropes of release now pouring from my cockette. He was milking his cum pig for all she was worth and at that moment I was proud to be his sow, proud to be opening my ass for this man with the beautiful black cock and the rhythm of an angel. He could have done anything he wanted with me and I would have obliged with batted eyelashes and a cunt on fire. Finally his ride ended with a deep moan and his own delicious explosion of heavy, thick streams of cum into my pussy. I clenched my cunt onto his shaft, milking every last drop, begging him emotionally to never pull out of me. I felt my tears well up in my eyes when he did. To show my gratitude I reached my hand between my legs, gathered some of his angelic seed and put it to my lips. Normally I retreat to the bathroom once they cum but with Xavier I lay there spent, in my own cooling milk, and watched him gather up his clothes, admiring his rippled body, secretly hoping he would extend his hand and take me with him. He thanked me - and I thanked him, something I had never said out loud before to a trick. I don't think he really knows just how good of a fuck he is. Please see me again. I need you. Once he was gone Jack couldn't resist. "Like it much," he said sarcastically. I smiled, satisfied, "so fucking good." Jack looked at me for a minute, sizing me up and down. I actually felt a little self conscious. Then he unzipped his pants. "Come over here," he ordered. I hesitated for a second. Who was he to just order me? And then it hit me full on. He's my pimp. Maybe not in a back-alley hooker way, but my pimp nonetheless. And if he orders me to do something I better do it. A whore needs to know her place. So, content in the knowledge that sometimes a hoe needs to bow down, I slithered off the bed and crawled on my hands and knees until his stiff dick was bobbing in my face. Then I bowed my head to my pimp and sucked his cock. And that was it for Friday. I had laid off the coke pretty good that night and the pounding Xavier had given me had left me wrecked, sore and tired. After I finished sucking Jack's cock I had a cigarette, a couple more sips of beer and climbed into bed, the thoughts of my gorgeous Xavier dancing in my head. I wish they were all like him. Sadly ... they are not. Jack woke me on Saturday at 9:30. My first trick of the day was due in two hours. "We've got a long day ahead," "I already knew that," I said, as I wiped the sleep from my eyes. I had gone to bed without showering or taking off my makeup, so the linens were smeared with eye liner and covered in glitter. "I've got the maid coming up in about 10 minutes. I told them you would be in the shower and they can skip the bathroom, but they should make the bed up and empty the trash. I'm running out to get the paper. I put your coke in your purse if you want it. Just go easy. We've got at least 12 hours today." And with that he was off. I got up, stretched and had a cigarette. Right as I finished the maid knocked at the door. I grabbed my coke, a cold beer, dove into the bathroom and called, "Come in!" I locked the bathroom door to ensure privacy and opened my beer, enjoying its cold crispness even at 9-something in the morning. Then I turned on the shower for cover and chopped out two nice lines for breakfast. There's something about these types of days - 10 scheduled cocks - that just brings out the coke whore in me. Give me a date with one guy and maybe I'd do a little. Tell me I have to get fucked all day long and deep into the night and I will throw on my fuck-me heels and blow lines the whole time while an endless string of guys dump their hot spunk into me like the cum catcher I am. It's like when I know I'm going to be degraded I use the drugs to degrade me even further. I fucking need that feeling of being an open cunt or something. Is this all I'm good for? I'm a cum dumpster ... and I kind of like it. WTF? By the time I got out of the shower the maid was gone, the room had been cleaned and Jack was back. I was wearing green, having settled on the boy shorts and matching bra being my best options when it came to turning tricks. I added a pair of jet black thigh highs and 5" black fuck me pumps. I used extra mascara, dark and thick on my lashes and smoked out my eyes with liner and shadow right up to my brows. It was pretty caked on and there was no mistaking what I was. It was 10:30 and I was a tramp ready for a day of opening her legs for money. Then I added my glitter, sashayed into the room and did a couple of more lines. Adam was right on time at 11:30 AM. I was his first tranny and the young boy was doing his best to please me by putting my little clit into his mouth and sucking me for all he was worth. Poor thing. Between the hormones and the coke, I can't get hard anyway and my cockette is well on its way to shriveling away to nothing. I don't need it for my sexual pleasure anymore, so it makes no difference to me, but I think he thought he was doing something wrong. I pulled his mouth off of me and returned the favor. His 6" of dick was nice and clean and I lubed him up good with my spit. Then I got down on all fours on the bed and offered my ass to him. I think he was having some problems with Jack being in the room because he was a pretty timid fuck. I'm a professional, so I gently slid my hips forward and back and did a lot of the work for him, massaging his cock with my pussy muscles and eventually milking the cum from his cock. He had paid in full so I wanted to make sure he got his money's worth and got to cum before he went soft again. Mission accomplished. Eric was next at 12:30, a chubby guy with a non-descript 6" cock. He fucked me pretty good (doggie again) and moaned softly when he came inside me. Tom was an older guy, probably in his mid-50's. Graying hair and gray pubes. He took his time with me and let me ride him, so I was able to angle his dick into my g-spot and I got a nice cum out of it before he exploded inside me. Thank you, darling. I'm glad you enjoyed the ride. My scheduled fourth never showed. By now it was around 3:00 and I was feeling no pain, a mix of a few beers and plenty of coke. I was lounging on the bed when Jack came over and put his cock in my face. I opened and took him inside me, savoring my pimp's dick. "You work for me don't you," he taunted. "Mmmhhmmm," I mumbled through a mouthful of cock. "That's it slut, suck my cock, you fucking whore." I doubled my efforts, rolling my tongue along his balls and pumping his stiff shaft with my hand. He tasted good and I knew all my fucking had turned him on by the sheer hardness of his prick. This wasn't going to take long - and it didn't. "Yeah," he teased, "I'm going to give you my cum, my gift." I mumbled again into his cockhead as his thick streams began to fill my mouth. I pushed his dick past my gag reflex and took the last two or three ropes directly down my throat. He moaned when I deep-throated him and shoved my lips into his pubic patch, holding me there until I was gasping for air. Then he pulled out of me, zipped up his pants and went back over to the table. I went to the bathroom to clean myself up a little bit, touch up my makeup and plump my lips. I did a few more lines and had another beer as Jack kept working the computer, looking for more tricks. "We probably have enough," I said to him. We still had six more scheduled. "Never enough," he shot back. "Time is money." He really is a fucking asshole. How much pounding can my pussy take? I had a 5:30 that was in and out of me in 20 minutes. David, as he preferred to be called, had a decent 6 to 7 inches of love that I hungrily gobbled down my throat before he flipped me over, slid my panties down and fucked my ass until he dropped his load inside it with a grunt. Then he was gone. Full price. I should have known the whole weekend was going too easily. Guys were in and out and were paying full price and my ass was holding up pretty well. There wasn't a lot of small talk and everything was just rolling along. Good times, good coke and good money. This was getting easier. Then Martin came in. Martin wanted to tie me up and dominate me for $250. Jack had talked to me about it earlier in the week before he booked the appointment. I was fine with it, figuring Jack was going to be there and I loved the thought of being tied and forced to submit. He got there just a few minutes after 7:00 and carried a mysterious duffel bag of his "tools" with him. He sat down and we talked for a couple of minutes, just small talk really, nothing focused on my desires and few about his - he liked getting head and he wanted me to obey without hesitation. He paid in full and I was now his "slave" for the next hour. I didn't realize at the time just how brutal it was going to be. He started by laying out the ground rules, most of which I already knew - he was to be addressed as Master Martin or Martin, I was only to speak when spoken to, I had no say in what he did, etc. He told me to lose my clothes, including my heels, which I thought was odd since all guys seem to want me in heels to the point where now I always leave them on without thinking about it, even if I'm completely naked. He sat me on the bed with my legs about a foot apart. Then he slid in behind me up near the pillows and cuffed my wrists behind my back and added a thick, leather collar to my neck. Finally, he produced a small "cuff," reached between my legs, pulled my two balls down hard and cinched the cuff down tight at the base of my clit, pushing my balls down and away from my body, stretched out away from me. That didn't make me very happy, since my cockette and her two friends are pretty much off limits to people. I'm a girl. I have holes. I thought about protesting but didn't. I should have. He clipped a short measure of chain into the cuff binding my balls and attached it to ring on my collar. After a couple adjustments I was completely immobilized. I couldn't straighten my neck. If I moved it at all, it tugged on my ball sac. If I jerked my head, I was in danger of having them ripped off. So I was forced into a head down position, tethered to my own sex. Martin carefully rolled me on my side and placed a riding crop to my lips. I could feel myself being tugged on even in this simple motion. "Beg me to use it," he taunted. I didn't like where this was going. "Please Martin, use it on me." He began to lightly slap me with the crop all over my body - my hips, my ass, shoulders and back. Gradually he picked up the ferocity of his slaps. He would hit me and my body would react, tugging on my testicles if I made even a subtle move. He showed me the wooden ruler before I felt it and seconds later he began to spank my bare bottom with it. I could feel the heat spreading on my ass and thighs. The cuffs on my hands were tight. There was no escape. He unzipped his pants and stuffed his cock into my mouth. It was hard for me to suck it because every movement caused me pain. I did the best I could, lapping at his cock with my tongue and bathing it with my saliva. As I did he continued to spank my with the ruler. As if this wasn't enough I felt the cool grease being applied to my pussy. "I like my girls to be loose," he stated. "Are you a loose girl, Kristy?" "Yes Master. I'm a loose girl." He slapped my ass. "Are you a loose girl?" "I'm a loose girl." Another slap. "Tell me!" He slapped me again with the ruler. "Yes, yes. I'm a loose girl. I'm a fucking whore and a loose girl!" "Are you a fucking slut?" Another slap. "I'm a fucking slut! I'm such a fucking slut. I have a dirty pussy and I need you to fuck it!" I must have had my eyes closed because he told me to open them and when I did I saw that he was holding the biggest dildo I had ever seen. It had to be over a foot long, but it was the girth that made me moan - at least 4" in diameter at its widest. It would split me in two. "Please no," I begged. "Oh yes," came his reply. "No, no, please!" "Shut up!" he shouted. I whimpered. "You're going to take this cock in your pussy and you will do it now, my loose girl." More grease on my ass, then more on the dildo. Then more on me as he worked two fingers into my pussy. "This isn't your first cock today, is it, slut?" "No Martin," I admitted. "Such a dirty girl. Such a loose and dirty girl." I could feel the tip of the monster sliding into my bottom. "No, please." Deeper it went, as my ring began to stretch to take what he was going to give me. I bit down on my lip as I felt the hard, rubber dong sliding into me, preparing me to be stretched beyond anything I had ever experienced before. I thought of Xavier and his big dick and some of the others I had taken in my time. This was twice that. It was huge, the giant, bulbous head, followed by the enormous shaft, a massive torpedo. I thought about whether I would bleed, whether my bowels would hold out. Would I ever be able to be fucked again? I cried out in pain as it passed the halfway point and then what must have been the three- quarters mark. This was it. This was the widest part. My ass was on fire, engorged by this beast, this uncompromising man and his hard rubber, God-like phallus. I was moaning. My body convulsed and I felt a sharp tug on my sex. I needed to remain still, to take the monster to my hilt. Martin reversed the dildo and I felt my ring contract for a moment before he resumed his torture, sliding the demon into me deeper than it had been before. I bore down the best I could, a wanton slut who had naively given all control to this man. I could feel his hand at the base of the dildo touching my bottom. I was nearing the end. He pushed into me and I grunted and then screamed, my cunt squealing in pain like a wounded animal. The white heat was blazing and I couldn't see anything. I was involuntarily writhing on the bed, the tug at my sex no longer my biggest problem. Martin reversed the dildo again and with a short warning plunged the rest into me. I was taken, defeated and he screamed in victory. That's when it got worse. Getting the monster to the hilt inside me was only the first step and I realized this the moment he slid part of the dildo out of me and then pressed it back in. He just didn't want it all inside me; he wanted to fuck me with it. I bucked and I screamed, searing pain shooting through me, as he began to quicken the pace. "That's it, my loose girl, you will learn to love the size, darling," Martin teased. "You will learn to worship it." I gritted my teeth as he continued to fuck me with the beast, establishing an in-and-out rhythm and adding slaps to my ass and thighs as he did so. Then the ruler was back as the dildo continued its pounding in his other hand. He reached around and tugged on my leash as he fucked me deep and hard, all twelve inches buried inside my white-hot cunt. I was gone, completely at his mercy - the dildo firing in and out of me as the slaps and the spanks and the tugs sent me into subspace and complete sexual overload. I was a greased pig, filled with lube that was now seemingly all over me. He began to fondle my nipples until they were erect. Then he pinched them, rolling them harshly between his fingers as my pounding continued. I was gone, oblivious to everything. An overloaded whore. Martin was working the massive dildo in and out of me with abandon, as if it were a standard size. I was squealing in pleasure and pain. I swooned and was thunderstruck as my orgasm blazed through me and the milk began to leak from my clit - my own body betraying me yet again with this degradation. Is there no limit to my nymphomania? In and out, in and out. More cum, milky ropes now erupting from inside me. I swooned again, thick streams of prostate milk now pouring out of me with each thrust. I was truly a sow, my milk being taken from me at the hands of this man. With each deep insertion I saw stars and when I came to I could see the milk streaming from me, pooling on the bed. Then more slaps and spanks. I was being fucked to death, or so I thought. This couldn't continue. I didn't have any more milk to give, did I? Out and out it poured from my sexual well. Would I drown? And then it stopped. Suddenly he was done, removing the monster from my cunt in one motion. I could feel my pussy gaping. He unchained my neck and released my hands. I was free for a moment before he brought my wrists over my head, binding me to the headboard face down. Martin lifted my ass to him and I waited breathlessly as he slid his pants off. His dick was rock hard and he was inside me a moment later. I could barely feel him in my cunt, so open I was from the dildo. But I could feel his body and his motions and I knew he was sawing back and forth inside me, lost in his own perversions of fucking the loosest girls he could find to fulfill his fantasy. I was a gaping cunt to him now and he was driving into me with a force that moved me with each thrust. I could feel his balls slapping into me as my wide open hole welcomed his cock. I felt him shiver and I knew he was close. I tried to massage him with my pussy but it was just too open and I couldn't establish a grip so I concentrated on feeling his orgasm and I felt it splash inside of me as he moaned and held me tight, the waves of pleasure rippling through him. "Kristy, so good," he warbled. "Thank you my dear." Martin untied me from the bed and I spun around as fast as I could. I was so worried about his cleanliness after the dildo and I was shocked and thrilled that he remained clean through the process. I worried about my own health. My pussy was gaping. It felt so open. Would it ever contract? I remained on all fours as Martin went into the bathroom for a moment and had a drink of water. Then he gathered up his tools, kissed me on the lips and left an extra $50 on the foot of the bed. When he was gone I gathered myself up and headed for the bathroom. Jack tried to say something but I gave him the "1-minute" finger, shut the door and stood there dazed. I was shaking. I felt like I had ripped open. I wasn't sure whether to sit down or bend over. I chose to bend over. Then I vomited. I eventually sat on the toilet. Nothing came out. I still took a second to wipe any remaining cum away and when I did I realized I could have easily put four fingers into my pussy without discomfort or stretching or anything. I was wide open. It took me a long time in the bathroom to compose myself and what I just realized is that Jack never checked on me once. Fucking prick. Finally I was able to stand and walk back into the room. I was still naked and shaking. Jack was on the phone as I gingerly tried to sit down. I was able to, thankfully. Then I got back up and went to my bag to find something, anything that would keep me warm. Nothing. It's the middle of summer. I didn't have a sweatshirt or anything. I hooked my bra and threw on the yoga pants I normally wear home. Then I sat back down and tried to stop shaking. I opened a beer. Jack hung up the phone. "What the fuck are you doing? Your next one could be here any second." "Jack," I was all fucked up. "I can't. I can't do it." "What do you mean?" he asked. "You have to. We've got appointments. We've got clients." "I can't. There's just no way." He looked at me, like he needed an explanation or something. "My ass is on fire. You have to cancel." "Fuck you. Fuck you I'm not canceling. We have like six or seven more guys coming tonight. Now get the fuck back in there and get ready." "Jack," I was trying to remain calm. "I can't. I'm hurt." He got up from the chair. "You're not hurt. It wasn't that big." Wasn't that big? He was standing over me now. "Go get ready," he said again. I didn't like where this was going. I sat in silence. "Get your fucking ass into that bathroom now." I just sat there. "Now!" he shouted. I didn't move. That's when he grabbed me. I tried to get away but he was too quick. He picked me up and threw me onto the bed. I tried to scramble off but he was on me in a flash. He slapped me hard on the head and wrapped his hands around my throat. "You fucking do what I tell you to do! You fucking hear me! You fucking hear me you whore!" I looked away and he grabbed my face and forced me to look at him. "You hear me you cunt? You fucking do what I tell you to do!" "Fuck you!" I snapped back. Then he punched me in the face as hard as he could. I cried out and then I cried as I stared into his eyes. I was stunned. Thankfully I think he was too. His rage ebbed away enough that I think he caught himself. I was crying. Hurt. Feeling new emotions. He rolled off of me. "You're a fucking asshole," I whimpered. I had to leave. I had to find a way to get out of there. Jack was silent for a while. "You fucking do what I tell you to do," he quietly said. "That's what you do - what I tell you." No, I thought. No fucking way. Not anymore. There was a knock at the door. Jack looked at me and I looked at him. "You - in the bathroom now. And not a fucking word or I'll fucking kill you." His exact words. I'll fucking kill you. I shuffled as quickly as I could into the bathroom and locked the door. I heard my next trick come in and start the small talk with Jack. Then the bathroom door opened and Jack threw in the rest of my "hooker outfit" and shut the door. I checked my face in the mirror. I had a welt, not a shiner, but more of a bright red bruise from the punch. My throat had marks from his hands. I should have run right then. Just right out the door in my bare feet and off into the sunset. Instead I caked on the makeup to cover up my bruises, plumped my lips, fixed my hair and slid back into my panties, thigh highs and heels. Then I walked back into the room and let six more guys whose names I will never know fuck my abused pussy in front of my abusive pimp. End Diary Entry