Heres my confession....
Ive always had this thing for anal sex...Freudian psychology and his bullshit may play a roll but I was never touched or done wrong as a child, anyway...

The first time I had anal sex was with a girl in College...she really didnt like giving head but she loved sex..so one night in a drunkin talk I told her I wanted to stick her in the ass, she would be my first...she replied "its been a long time!" lol yeah right bitch you in college fucking everybody lolol... She agreed and I grabbed some "baby oil" lol...I was still using comdoms at the time so I gently proceeded to put myself inside of her...she moaned low and deep until it was all the way in :-) I started to stoke her gently as she told me to not go to fast. Soon after about 5 mins her asshole was open enough to pound!!! I absolutely loved it!!! Of course I came and that was it :-):-):-)

Alight so the next time we linked I told her I wanted to do it again she agreed but this time half way thru the anal session the condom broke. I felt it immediately but I couldn't stop myself...I kept going and it felt so so so so so so good. And actually before this point in my sexual history I had never raw sex..only protected so this sensation was very new :-):-):-):-):-):-):-)

Okay now here is my true confession....A few years later, I had sex with a chick and she was used to anal sex. I trusted her so I proceeded in her raw...about 15min later I looked down at my dick and it was becoming brown...at first I wanted to stop because I started to smell the odor but then I found myself not able to control myself...I LOVE DIRTY ANAL SEX!!!! ITS JUST SOO RAW and NASTY. I LUV I LUV I LUV....I begin to fuck her harder and harder harder and busted a big ass nut in her ass. She then bent over and pushed it all out...I almost fainted from excitment!

My Confession!!!

I used to bang this chick before she joined the Navy, lost contact with her when she joined. Turns out she got married to this Navy dude. She had such a nice body ~20 years ago, sexy legs, nice ass big tits and a petite frame. Her pussy was nice and tight and she was a freak in bed. She was my first anal experience (didn't go to well lol). I recently caught up with her and holy fuck did she let herself go. I'm glad I got to fuck her in her prime. I remember when my dad met her the next day he was like, "She's got some nice tits!" haha. She was the first to ever truly deep throat my cock, she always would tell me, "don't ever ask where I learned how to do this stuff," and I never did. Good memories... sad she let herself go. I would have enjoyed being inside her again! It's those times when you reflect back and wonder what previous lovers are doing and find out, you're like - "damn, I made the right decision!"

What is the best orgasm you have ever had?  As a guy, I’ll never forget the best orgasm I ever had. I had just gotten out of a year and a half long relationship. The sex was great but me and her just didn’t work. I was in my early 20s and just wasn’t looking for another relationship. This one girl though knew I became single and was on the border of being obsessed with me I think. Hung out with her a few times, she did what I said. I’d I told her to suck, she sucked. If I told her to swallow she swallowed. Then I got the idea that well, she will do anything I say, and I have always wanted to try anal. Sure enough, she was willing to do whatever to please me. She came over and we were down in the basement of my house on spare bed, I snuck her in through the back door (pun intended). I fucked her ass and she took it like a champ and when I came, I shot it deep in her ass, it was like fireworks going off in my head. See with my ex the sex was great but she wouldn’t do anal, and I just came in her mouth every time after pulling out of her pussy so this was the first time I didn’t pull out while fucking someone. It was such an intense orgasm I felt like I came a lot and my legs felt so weak to walk. It was absolutely amazing. She knew that I didn’t want any relationship and she eventually went and got a boyfriend not too long after. Though she came to me to help her “train” anal with her because her boyfriend wanted to do it with her. I did it a few times, all were great but it never recaptured that feeling of that orgasm.

I confess i have a hot fantasy of meeting a trucker with a big cock who likes giving and recieving orally and anally and would drop into town every once in a wile to spend some time in his sleeper getting high and sucking and fucking one another. I'm a little chubby and in my early 40's and live somewhere on the I-5 corridor. He'd show up and call my cell, then I'd go to where he parked and get in. We'd make small talk about his week and mine then he'd have me go into his sleeper and remove all my clothes and get myself hard. he'd come back a few minutes later and close off the divider and have me remove his clothes and suck his dick for a bit then he'd sit down next to me and we would fondle one another and he'd kiss me a little then he's put a DVD in a player and start a hardcore porn and pull out a pipe to blow clouds with and we'd take turns smoking while the other sucked our dick. I'd suck his dick and stick a finger up his ass and wiggle it around. lick the head and the shaft then lightly suck his ball and he'd return the favor when I was done. after we had done that for a while he'd tell me to lie down on my side and he'd lie down behind me and start shoving his dick up my ass and slowly empaling me on his thick 10 inch shaft. slowly pushing he manages to get it all in balls deep and waits for me to get adjusted, after a few minutes he starts moving in and out, slow and shallow thrusts at first but gradually building depth and intensity. he puts and arm around me and grabs hold of my cock and starts jerking me off and he has a rather tight grip on it and it feels good. pretty soon he's jerking my cock hard, kissing me on my neck, giving me deep powerful thrusts into my ass and we're both breathing heavy and ignoring the porn thats on, concentraiting on our outright feelings of physical lust for what we're doing, bringing us both off at the same time. Him in my asshole and me on his bed. we both lick it up and kiss passionately afterwards then we cuddle together and give it a rest for a while then repeat what we just did only having me fucking him this time.

With the house all to myself from Thursday through Sunday night, I suggested to Robby (our gang bang guru) that it would be great for him to arrange a fuck session where we could take advantage of an empty house for a change, rather than renting a hotel room for our activities. He came through within the first couple of hours, which just shows what an amazing track record he has of snagging seriously fuckable women.

He'd connected with Jamie via a Craigslist ad. She's 30, 5-5 120, with blonde-highlighted light brown hair and 32B tits. The photo posted here is the one she sent along with her request to meet. Because it was midday Thursday, Robby was only able to arrange a threesome, since the rest of the guys in our over-50 GB group couldn't make it on such short notice. Jamie was apparently OK with that, though, since this was to be her first multi-guy sex encounter and she wasn't too sure how overwhelmed she might be with more participants. And if her claims could be believed, it would prove the first time in more than a month that she'd had any kind of sex at all.

While waiting for them to show up, I gave Robby some shit via text because, after picking Jamie up from her place in North Denver, he had trouble finding my house on the southeast side. He claimed his GPS was all fucked up, but I was more certain it was operator error. Also on the way over, he "warned" me that Jamie was a bit on the skanky side, but I replied that, given our plans for the afternoon, that was a benefit rather than a flaw.

They showed up at my place just before 1:00 p.m., around 20 minutes late. I'd prepared our guest room in advance by stripping the queen-size bed and putting on a new bottom sheet plus clean pillow cases, setting out a brand-new tube of lube, and adjusting the shades so the room wouldn't be quite so bright. Meeting them at the front door, I saw that Jamie was dressed in a pleasantly slutty outfit: Short green cloth jacket over a black lace sleeveless top with a purple bra showing underneath, a denim micro-mini skirt that barely covered her ass, and over-the-knee high-heeled leather boots. She had her hair tied back in a ponytail and spun around after coming through the door so I could apply the green silk scarf I was using as a blindfold. She'd asked for this as one of the conditions of the afternoon's activities, and I was happy to oblige.

Given the lateness of their arrival and the fact Robby had to leave in an hour to pick up his kids from school, we immediately headed upstairs and got down to business. I helped Jamie off with her jacket and unzipped her skirt so she could slip it off. She quickly removed her lacy top and I unhooked her bra. We all agreed she could leave her boots on for the duration. Meanwhile, Robby was stripping down to bare skin, tossing his clothes haphazardly onto the floor in his haste to start in on Jamie. She asked us to leave her undershorts on -- they were leopard-print boy-shorts -- which was fine because they'd been altered by having two carefully placed holes cut out of the crotch. One showed off her smoothly shaved pussy while the other exposed her tight little asshole. I ran my hand down over her buttocks and slipped my middle finger into her tight, wet pussy while removing my clothes at a pace considerably slower than Robby had achieved. He put his hands on her small, firm tits and began to suck on her nipples, which stood up nicely to the attention. She used one of her hands to tug on his fully erect cock - it was hard even before he took off his trousers -- and meanwhile I disengaged so I could remove the rest of my clothes as well.

Robby suggested she lie on her back, which she did, and he stuck his face in between her thighs to taste some of that sweet, sweet pussy. I thought he might be down there a while, but after only about a minute of some serious licking he stood up, pulled her hips closer to the edge of the mattress, and jammed his seven-inch dick into her wet slit. She had her legs up in the air with Robby pressing his hands against the backs of her thighs to keep them there as he pounded her hard. I'd stroked myself from a semi-hard to a fully erect state and climbed onto the bed so she could take my dick in her mouth. By changing my angle of approach, I was able to slide my entire member into her mouth. Of course I'm less than six inches, so it's not a huge challenge, but I could still sense the tip of my cock hit the back of her throat with every downward thrust, which was a great feeling.

After a few minutes of fucking her while standing alongside the bed, Robby suggested it was my turn to squeeze my dick into that pussy. We helped flip her over -- her equilibrium was compromised somewhat by the blindfold -- and I entered her from behind, doggie-style. It had been a couple of months since I'd had sex, so this was a welcome opportunity and I made the most of it, thrusting enthusiastically as Jamie reached down with her right hand and rubbed it briskly across her clit. Meanwhile, Robby had opened up the small bottle of Astroglide he'd brought with him and suggested we DP the girl. She was definitely on board with that idea, so we maneuvered ourselves into position with me on my back and her on top, facing me. She reached down and re-inserted my cock into her pussy and leaned forward so I could suck on her tantalizingly erect nipples. I moved my legs together and Jamie did the same with hers, which allowed Robby to climb aboard and straddle the two of us. He squirted some lube onto his index finger and worked it into Jamie's rear hole, removed it quickly, and leaned forward while pressing his cock's head against her anus. She balanced on one hand above me while reaching back with her other hand and pulling her butt cheek aside to provide him greater access. A deep grunt from her, plus added pressure on my dick inside her pussy, told me he was in her ass. I lay still with my hands on Jamie's hips while Robby did all the work. He pounded her ass with enthusiasm and some deep penetration while she ground my pussy against my lower body. I saw Jamie's chest flushing red and moved my hands from her hips to her tits, tugging insistently on her nipples to match the rhythm the two of them were playing out above me. After a couple of minutes, Jamie let out a big groan and announced she was cumming.

By this point Robby was starting to run out of gas, so he pulled out of her ass and stepped across the hall into the bathroom so he could find a towel for wiping off his dick. Jamie rolled off me and onto her back, but she was clearly far from done. Neither was I -- so I climbed off at the foot of the bed and pulled Jamie toward the edge, pushed her legs up into the air and told her to hold them there (which she did by looping her arms around the backs of her knees), and then I sank my cock into her ass. It was the first time I'd done anal in probably 20 years, and it felt terrific. I was soon pounding her with balls-deep thrusts, and she let go of one leg so she could reach down and mash her fingers against her clit in a rapid-fire manner. Meanwhile, Robby crouched next to her face and stuck his newly cleaned-off dick into her mouth. She sucked him enthusiastically while I fucked her ass; then her butt muscles clenched and she was suddenly in the midst of her second orgasm.

Once it passed I withdrew, especially since my legs were shaky from all the thrusting that I was hardly used to anymore. Robby decided he wanted some more of Jamie's asshole, so we switched positions and he stood at the foot of the bed with his dick inserted all the way into her poop-chute. After about eight or ten thrusts he announced he was ready to cum, so he pulled out and shot a nice thick glob of white goo all over her pussy lips, with some coming to rest on her shorts. I was positioned behind her, with her head cradled in my lap, so I reached down and used two of my fingers to scoop up some of Robby's ejaculate. Then I popped my fingers into Jamie's mouth and she sucked them dry.

By now it was time for Robby to split, but I wasn't quite ready to call it quits and Jamie agreed to let me take her home. As Robby dug around on the floor for his discarded clothes and started to put them on, I finally pulled off Jamie's blindfold -- it was simply too much in the way after all this time -- and convinced her to get on top of me, 69-style. Robby said a quick goodbye, to which Jamie was only able to reply with a muffled grunt, since at that moment she had my entire cock in her mouth. I licked her pussy, sucked on her clit and slipped a finger into her ass, hoping to induce a third orgasm, but she came off my cock long enough to explain we'd made her pretty sore down there, so instead I pulled my face and hands away from her crotch and simply let her do her work. About three minutes into this latest activity I said, "OK, finish me off." Jamie took that as a cue to get me to cum, so she wrapped her hand around the base of my cock, sucked harder on the head, and shortly thereafter I was pumping my jizz down her throat.

She wanted to smoke a cigarette (Marlboro!), so she slipped on her black lace top and I led her toward the deck that's just outside our back door. She also wanted something alcoholic to drink, so I unscrewed the top off a tiny bottle of Barefoot Moscato and poured it into a juice glass. Classy presentation, eh? By now it was nearly 2:30, so rather than begin another fuck session -- we were both pretty sore at this point -- I suggested I drive her home. We got dressed and hit the road. On the way there, we enjoyed an interesting conversation about local politics, the police -- she was on probation for her 2nd DUI, thus a suspended drivers' license and the inability to drive -- and other non-sexual elements. As she exited my car she stuck her head back inside and gave me a warm kiss on the lips. "Tell Robby I'll be in touch again soon, OK? And next time, a couple additional guys would be all right." She'd obviously enjoyed herself!

When I was 19 years old and in college in Florida, I got really heavy into drugs. Mainly party drugs like coke and ecstasy, and of course plenty of weed, but on occasion other drugs as well. I was out of control and living one big party life on my parent's dime while they struggled mightily to pay for me to have the opportunity they never had and go to college. Looking back I feel like a total asshole about it now as they wanted nothing more than for me to be successful and not have to struggle...sorry, I digressed.

Anyway, since I had no money and wanted to keep up my partying lifestyle and since I was always very athletic, in shape and considered "good-looking", through one of the people I met in the party scene I ended up doing some modeling to make some extra money. Pretty low rent stuff, nothing glamorous, but a couple hundred bucks a week.

This quickly evolved into the opportunity to do some "videos". It started with just masturbation videos of me lying in bed, or on a couch or in the shower jerking off. I figured I was going to do it anyway so why not get paid for it and I was getting paid $100-200 per day that I did a shoot. I could sometimes do 3 or 4 scenes in a day. The guy running the operation said he was impressed by my "re-load" ability and also that I had just the right cock for it...I'm about 8 inches, decently thick and my dick looks perfectly formed from shaft to head and can blow pretty big loads even after only a little break in between. I knew that these were primarily for gay guys to watch but I didn't care. If someone gets off from seeing me, so fucking what. I did these for a while and then he asked one day if I'd want to do some full sex movies and photo shoots and showed me some of his portfolio and all things considered the chicks looked pretty hot and we were now talking more like $300-500 per day so I jumped right at the chance.

It was a crazy scene and pretty much everything you wanted was at your fingertips. Women and drugs galore. Parties every night after shooting. We were all in the 18-22 age bracket so it was just a no responsibility show. But as quickly as I made money it went back out the door on drugs and partying. Then one night when we were partying at the main house this director used for shooting videos, him and a couple of the other "big wigs" in their operation asked me if I would be willing to do some more hardcore shit. At first I was thinking they meant bondage, s&m type stuff, but they quickly made it clear they were talking gay action. I immediately said not a chance, I was straight and no way I could do it. They pushed the matter (and a coffee table with a big pile of blow on it) and said that all the actors in their gay shoots are straight guys because that is the look they wanted in their videos, strong masculine men, not femboys. The guys just do "gay for pay" and they also said I could make up to a $1000 per shoot depending on the circumstances. At that point my eyes lit up and I think they knew they had me. I asked them more questions and they said I could be strictly a top and receive blow jobs, that I didn't have to get fucked or suck or kiss anyone if I didn't want to. I could also do bi scenes where a female actress or two would be involved. I said, what the fuck, let's give it a try.

The next week they had scheduled me in for my first scene. I was shaking like a leaf prior to which was totally not like me. In the other stuff I had already done I was totally calm and had no issues getting naked, getting hard and fucking in front of other people. It was a one on one scene with me and another guy. I was going to be swimming naked in the pool and then get out and immediately go to the lounge chair next to the pool when the "pool guy" was going to show up to service the pool and eventually me who was masturbating while watching him clean the pool. I actually was having a difficult time getting hard which was totally not the norm for me, but he came over and began blowing me for a while and soon enough I did get fully hard. I had sunglasses on and just kept my eyes closed and picturing hot women. I put on a condom and ended up fucking him in a few different positions and then to my surprise he end up blowing his load on my chest as he was riding me, then slid off my cock, dropped back down and sucked me to completion taking my load all over his face.

I said afterward that it wasn't that bad, but I didn't think I wanted to do it again...until I got my next offer and more cash. It went on like this for a while and me just doing the fucking and getting sucked. I still was primarily doing straight shoots though. Then the director came to me with a proposal for a scene. It would be me and this girl I had done some straight scenes with and we would be a "married" couple and then another guy who was coming to our house to do some repairs. But he wanted it to be a scene where me and her completely serviced this guy. We all were going to suck and fuck each other, no holds barred type stuff. I was extremely hesitant but he offered up my biggest payday yet and it was a good chunk of money for 4-5 hours of total "work". I was so far gone into the scene at that time that I agreed and said let's do this.

The day came and again I was nervous. I did all my usual prep on my "manscaping" and where I normally do everything I can to keep myself fresh down below, this time I added the step of the diet one of the other male actors recommended and his full enema routine to completely clean me out. The worst thing on a porn set when anal is involved is having a shit accident. It came time for the scene and we were in the bedroom on a king size bed where I was fucking the girl for a while then the "repair" man came in, he joined in with me "thinking" he was just going to play jointly with my wife but then he starts licking my balls and ass and pulling out my cock from the wife's pussy and sucking on it. We go through some more motions and she is sucking him then she tells me she wants to see me suck him and this is it, the moment I took a cock in my mouth. I did what I had to do and then after he fucks her it was my turn to take his cock. I was laying on my back as she sat on my face and then he started fucking my ass. Hurt like hell but I had to put up a good front. He even made a comment that got into the video about how tight my ass was. Anyway, we finished the scene after everyone had been fucked and sucked and I went out that night with some of the other people from set and we got destroyed on drugs and booze. I was fucked up beyond belief and when I got home that night I said that was it, I was done. Absolutely no more of all of it. The drugs the porn, nothing. The next day I called up the director and said to pull me from the stuff he had me scheduled for the next week. He tried to convince me and told me what a fucking amazing job I had done the day before, but I told him I had to get out. I couldn't handle the life and really was regretting all of it. I pulled the plug that day and never looked back.

So, somehow through all of this I didn't flunk out of school. I ended up completing my degree and living out a pretty mundane, boring college life and working a bullshit part-time job in one of the offices on campus answering phones and shit. Really nobody in my "normal" life had any clue about what I had done. My parents were none the wiser about anything I did partying or whatever and were proud as could be the day they saw me get my degree. I started a job with a top consulting firm and in the decade plus since, have worked hard and progressed so much in my career that I look at the "crazy" money I was making from porn and laugh at how little it is compared to now. I am engaged to a very attractive and smart girl who is an attorney and makes plenty of money herself, but also has no clue about my prior life.

I guess my biggest fear is that one day I am going to come on here and see one of my videos front and center. I know they are out there in various places on the web, but they obviously weren't under my real name and the look I had back then was very different than it is now where I am clean cut hair, have a beard, and even back then in a bunch of the scenes I had bleached blonde hair for a while and a deep Floridian tan. I guess my real name and SSN is on file with the porn company somewhere so that could somehow get out, but generally speaking I got away free and clear without any repercussions. Crazy the journey our lives take.

I confess that I have just returned from the local sex shop with my very own dick ;) I've always wanted to bang my boyfriend and tonight that will happen.

Upon walking into the store I was a bit nervous and didn't know what to buy. Then a worker caught sight of my confusion and came up to me and my bf. She helped us pick out the perfect strap on. It is the original Realistic Cock by DocJohnson. I hope all goes well ;) we also got platinum silicone lube. I don't want to tear his ass. I can't wait to shove it deep inside of his ass and make him cum from his first anal orgasm. mhmm.

I see you walking down the alley and I just smile but look down. No one else is around and we meet up. You ask how I am but I just stand there silent. You look around and grab my hair and pull my head back slightly, you kiss me and push me against the wall. "I asked how you were!" you ask again in a very demanding tone as you back up and push against me. I just look at you as my hands move to your cock. I start to rub it outside your pants as your hands move to my breasts. You squeeze them and go under my shirt to grab my nipple. You pinch it as I let out a moan, I kiss your neck and whisper 'I need your cock, that's how I am Sir.' Your other hand moves to my breasts as you push against me playing with them. You kiss me one more time as I moan and can't help but get wet from your power. I push you away for a moment and slide down the wall to my knees, your left arm straight as your hand pushes against the wall, your right hand takes your cock out and holds onto it. Before you know it my lips are pushing against your hand as your cock lays on my tongue in my mouth. I move in but you won't move your hand. I move out as my tongue glides on the bottom of your cock and pushes up to make you hard. I get to the tip and it pops out of my mouth. I move back into your hand, you finally move it to put it on the back of my head. You grasp my hair but don't pull me in, you are more or less just using my head as a resting spot. I move forward and sit up slightly for a better angle. I move all the way in and then out. You spread your legs a bit more as your cock grows in my mouth. My lips tightly holding on I start to go in faster, deeper, harder. I move out and start to suck. I love your cock SIr, I need your cock sir. Your grasp becomes harder and you pull my face into your cock. I gag and choke but you hold my head there. You hear people walking and you notice someone looking down. You move your back towards them to make it look like you are just taking a piss. I smile and tilt my head so I can continue to get your cock as far in my throat as possible. You hold my head close to you as I move down slightly. Your cock pushes into my throat. I feel it gets past the point of gagging and holds it there for as long as I can. You don't make a sound but your cock twitches. I start to suck harder and lick faster, pushing my tongue up and down, moving my lips in and out, making them massage your massive shaft. My tongue glides side to side but then I go in deep again. My tongue gets pushed with your big shaft, I push up, I move out as my tongue slides back and forth on you shaft. I move to the tip but just suck and worship. You notice a garbage bin down a little ways so you grab my hair and pull me up. You push me to the garbage and turn me around. Again, I am silent, all I have is a smile. You push my head down as my fat stomach gets pushed against the side. I am bent over in a perfect position. You pull my pants down and shove your cock in my pussy without warning. I scream and my moan echoes in the garbage bin. I hear you laugh as I feel your cock stretching me, pushing into me, feeling your power. I spread my legs a bit more but it makes your cock come out. You grab my hips and stand me up taller, you slap my ass and push me back in, almost lifting my feet up, your cock goes back into my pussy easier this time. "Fucking whore, stretched out already huh" you say as you rub your hands on my back and push your cock in and out of my wet, tight pussy. "this isn't going to work" you say loud enough for me to hear but soft enough so no one knows what you are doing. You pull out and I try to turn around but your strength won't allow it. You see a couple of milk crates by the dumpster and push me to them. You push me over them and the height is perfect. You take too long and I turn around and shove you cock in my mouth and suck harder than before. You stand straight up and stretch slightly. "Fucking cunt!" you tell, maybe to get others to know what you are doing or just to make me listen. I look up at you and your devious smile comes out. You grab my hair and stand me up, you pull my shirt over my head as my tits pop out. You kiss my nipple and bite them slightly, sucking on them, rubbing them with your hands, making them yours. You turn me around and push me over the crates. You shove your cock in my ass and it makes me moan louder than I ever have. "Fucking bitch, I was going to be nice and slow but now..." You slam your cock in deep, holding my hips. I bite my lip and bite my shirt that is over my head. "Shut the fuck up! I don't want anyone to know I am fucking a fucking anal pig!" you tell me and just hearing those words make my pussy leak so much it leaks onto your leg. You reach down and wipe up my juice and pull your cock out. You rub it on you cock and slam it back into my ass. You push hard, fast, fucking your little anal pig. I am about to cum but I try to hold it in, you push one, two, three more times and scratch my back. I start to tense up and you know I want to cum. "CUM" you demand and my legs start to shake and give out. You hold my hips and your big cock in my ass and cum deep. You cum so much it oozes out around your cock. I cum so hard I shake and almost fall over. You pull your cock out half way but then slam it back in. You reach around and touch my clit barely and I start to converse and cum again. You thrust your hips in deeper, holding it in my ass, moving slightly side to side, Making me your toy, controlling me with your cock. I feel your cock twitching in my asshole, I try to get strength to push you away but I can't believe how much I am cumming. "I need to fucking piss pig!" I try to look at you and start shaking my head. My shirt has come down slightly but you pull it and choke me with it. You pull me up but then slam me back down, the milk crates barely holding upright. You take your cock out very slightly and I feel it, I feel a warm liquid filling my asshole. You stand up and push your cock into my ass as if you are standing at a urinal. You pull out and the piss shoots out as you continue to piss on me. It drains down my asshole and eases into my fat pussy lips. I feel it, I feel the hot stream of piss and I can't help it. You see me completely lose it and orgasm. I turn to my side and you push me back on my stomach. You finish pissing as I squirt and cum streams down my thigh into my pants. You shove your cock deep one more time into my pussy. "I want to feel your worthless pussy cunt!" Your tip hits a spot in my pussy and I lose it, you pull my shirt and choke me and I cum one more time. It makes me cum so hard I pass out and go completely limp on the milk crates. I come to as I am on the ground with my pants around my knees and shirt covering my face. I have milk crate marks on my stomach and your cum and piss all over me. You are gone. I get a note that says "you may have more cum than just mine in you, get cleaned up"

Last night I was thinking about a convo I once had with another guy about anal orgasms, I've never tried any kind of assplay and didn't want to start, but I was bored and a lil horny, but not hard, and something possessed me to go ahead and try something. So I went into the bathroom and tried getting a finger in, wasn't too tricky, didn't get too far before I ran into some shit, but I 2'd and tried some more, and then two fingers. I felt around in there, but wasn't sure what angle to look for so I kinda just felt around hoping something would feel right, but didn't feel much. I thought maybe it just wasn't reaching it. I kinda got carried away and decided to stick something up there, the only suitable thing was the handle of a toilet brush which I lubed with some vegitable oil and stuck between the mattress so it would hold itself, then got into kind of doggy and backed into it.it felt cold and weird, and I had to bend kinda funny to get it in smoothly, at one point like a dog lifting its leg. I didn't do too much back and forth action, just kinda tried to get used to it or find whatever spot I was looking for. didn't really get much out of it, but I wasn't even hard, I had already fapped that day so didn't have much to go on, that might have been where I went wrong in this experiment, I shoulda waited until I was really horny. But I did feel my dick when I was about to stop and I was dripping a lil bit of clear cum, so maybe I just had empty balls to start. anyhow, didn't get much out of it but was probably doing it wrong, and when I pulled it out again I was probably 7 inches deep, at least from where I held it as I pulled out, but I got worried when I saw a redness mixed in with some of the stains, thought I may have hit something, like a polyp or just ripped a lil. but I'm not too "butthurt" atm, maybe on the outside a lil, and I've been farting more today. idk, maybe I need something softer to practice with, and that led me to thinking about letting someone fuck my ass, but I'd have to get head or ass in return or it wouldn't be worth the effort. then I started thinking I've become exactly what I didn't want to be when I first had that convo. Now I'm kinda mixed up about what I wanna do.

my G/F has always refused anal sex. i mean she would freak out if my dick even touched that hole. but i tore that ass hole up yesterday.

let me tell you how this all went down. it started a few days ago. we was laying on the couch watching tv. and she jumped up for some reason and kicked me hard in the balls. and let me tell you if i wasn't already laying down i would have went down. she laughed and grabbed my balls through my pants and started jerking on them. she backed off laughed and i was almost in tears. she came up saying i'm sorry and start rubbing my dick then she undid my pants pulled them down to my knees and started rubbing my dick again. i was thinking she going to give me a i'm sorry blowjob. I WAS WRONG. she grabbed my balls and started pulling me off the couch on to the floor and started pulling me down the hall.

i don't mean in a playful way i mean. i'm going to fucking hurt you way. i manged to get one leg up and i kicked her as hard as i could in the pussy she turned loose i grabbed her hair and pulled her to the living room and yelled what the fuck are you doing. you need to get the fuck out of my house now. i wasn't playing she laughed and said she was trying to be just a little kinky. she striped and said want to fuck now. i told her to get the fuck away from me and get the fuck out of my house now.

she got on her knees and started sucking my dick not touching me with her hands i was ready to forgive her even though my balls was killing me. blow jobs seems to over rule anything. then she bit me and i mean clamped down on my dick. first time ever i tried to knock that bitch out. she stood up and kicked me in the balls.

i don't know how my dick and balls was black and blue with deep red teeth bites hurting like hell but was hard as a brick. she ask what i was going to do because i had her pinned down on the coffee table. i spun her around and no lube no nothing and i was balls deep in her ass i took my shorts and stuffed them in her mouth. i fucked that ass and they only lube i used was spit when i felt my dick getting dry.

i fucked that ass for over 45 minutes at least i know because mash was just coming on when i started and it went off and the brady bunch over half over when i pulled out and came and pissed all over her.
picked her up through her out the front door and locked it. i'm sure she had cloths in her car she always does but she left.
i thought she would be calling the cops but she didn't and this morning she called and ask if she could come back that she is sorry she went to far. but never thought i would get her back the way i did.
i told her give me a few days and we will see.
but all her cloths are already packed and in the garage and all the locks have been changed.
i'm kinky but not that kinky.

I am writing this to you this because I have to. My master is making me share my story as part of my punishment for being a sissy faggot bitch. My name is Toby, I own a construction company that has about 10 employees and we are fairly successful. Successful enough that I don’t need to be at work much and have a fair amount of spare time. This is where my problem began. I Started jerking off to porno like all the time. It was all that I could do. 2- 3 times a day, always to porn, and the porn got harder and harder. One day I stumbled across a porno vid of 2 guys. The one guy was fucking the other guys mouth hard. I was intrigued and for the first time I came to the thought of 2 guys. Immediately afterwards I was disgusted and ashamed that I had just jerked off to gay porn. wtf.. Im not gay. I deleted the memory and cache off my comp and figured that I would never need to worry about it again.
A week or so passed and had forgotten about my gay incident. Life was normal, my gf Candice and I had just moved in together, things were going great. One night I was one the computer and got deep into rape porn and other hard-core stuff. I found myself jerking off to gay porn again. This time I didn’t get discouraged and went all out and fingered my ass while jerking off watching gay porn. Afterwards I was slightly ashamed but not as bad.
This trend continued and I started jerking off to gay porn daily. It was just normal for me. I also started experimenting with anal. By using cucumbers with condoms on and anal pumping myself. I was becoming a real pervert.
At some point some night I discovered craigslist. I started to play with it and even started to contact and reply to some of the ads. That’s not exactly true. I really started to reply to ads. All the time. I would be setting up dates with guys and standing them up. I became known as a time waster. And that’s what I was just a tease.
One night I got brave with all the dates and I actually was so horny that I figured I will maybe try to suck a dick. I picked one ad with a guy with a nice clean looking dick and set up a meeting in a deserted parking lot.
So there he was with his blue mini-van. I can remembering being so nervous approaching the passenger side door. He rolled down his window and for the first time I saw my master.
“why your as good-looking as you are in the pics” Master exclaimed.
“thank you, you are too, so you want to do this?” I replied
“for sure! Hop in.” master encouraged
I got in his mini-van and he lite up a cigarette. Hew was about 38 years old, clean shaven, a little over-weight but still handsome. He had tattoos and I quickly noticed his scare on his face. I didn’t want to say anything about it and just ignored it.
master was rubbing his dick through his pants “so lets get down to business”
he pulled his dick out and I immediately went down on him. His dick was about 6-7 inches long and not that thick, he was circumcised and his dick tasted like soap. He held the back of my head lightly pushing down every so often.. I really didn’t like to tell you the truth and was hoping it would end soon. He started to pump my face harder and came. I spit it all out and it was not pleasant at all. He was pissed cause I made a mess and he actually slapped me on the back of the head. I didn’t react because I just wanted it all over with.
“Get out, you worthless slave.. you should be punished for not swallowing. “ I looked at this guy like he had 2 heads. Slave? Punished? This guy was sick in my mind, I just got in my truck and left.
In my mind I was never going to suck another dick again but I wasn’t gone for 20 minutes when I noticed that my wallet was missing. I quickly grabbed my i-phone and checked my email to see if buddy had contacted me. I opened it up and saw and email from him with an attachment. I open the email and it reads “he sissy, looks like I got your wallet. I also want you to check out the nice new video I have. You will come back to this parking lot immediately and clean up your mess.” I was shocked. I opened the attachment and my heart sank.. It was a video of me sucking masters beautiful cock. He must have taped me in the act. Fuck me I thought.. this prick has my wallet and all my info and a video of me sucking his dick.
I immediately got in my car and went to the parking lot. When I got there he was waiting outside his car. I pulled up and got out really nervously.
“Well, I’ll make you a deal, you clean that up in my truck there and let me fuck your ass while doing it and Ill delete the video. If you don’t then I will be emailing it to all your employee’s, your girlfriend, your parents. I have all your personal info and I can make this happen. So its your choice. You be a good bitch and finish what you started you go on with your life. You don’t and you go on know as a dicksucker.”
“fuck you man.. Ill call the police.” I retorted.
“go ahead. I just got out of jail, I’m not afraid.. where do you think I got this scar.. plus you do that and I’ll fuck you up.. now I am going to forgive you if you immediately get in there and start cleaning..”
He was serious.. fuck me.. I slowly bent over and leaned in and started to wipe the seat with my hand..
“I have nothing to wipe this up with I pleaded..”
Master then came up behind me and yanked my pants down to my ankles and started to push his dick against my asshole.. it slide in but still hurt. I was so nervous about someone catching us I just wanted it to finish.
“here lick it up.. lick up your mess you fucking pig slut” he pushed my head into the mess…
so here I was, bent over with my face in a pile of cum and getting my ass fucked. How did this happen? How did I get myself into this? I wasn’t licking the mess up and master didn’t seem to care. He was fucking my ass like he was trying to kill it. After about 2 minutes of hard fucking I sensed he was getting close to finishing.
“please don’t cum in me,” I pleaded
“shut your mouth you fucking slut. I will cum where I want” he replied
“do you have any std’s” I asked concerned as there were no condoms, but Master didn’t respond and he started to push hard hurting me..
“uhh, uggh, ugh, take it you bitch,” master slowly relaxed still deep inside me “ I don’t know if I have and std, I’ve never been tested. You gunna get tested in a month or so and tell me, I don’t have anything serious, they would tell you in jail.”
Wtf I thought?? Anyways.. I had done my part. He gave me back my wallet and promised to delete the video.. I didn’t really believe it. I kinda at that point new that my ordeal was not over. But I wanted out of the van as fast as I could. I quickly pulled up my pants and I got in my car and left.
When I got home I felt sick to my stomach, I went to the shower and didn’t get out for an hour. I washed and washed and washed, I couldn’t get clean. When I got out of the shower I noticed that I had a text message, it was master. Now that he had my info he knew who I was he had me pegged. The text was simply another video… I opened it and it was a video he took while he was fucking my ass.
“do you think I would let your sweet ass get away now did you?” the text read