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Super-Earth
- Joined
- Jun 11, 2009
It was late as I was leaving the office. It was nearing the end of our reporting period and we had to catch up on a great deal of our accounts for our clients, so we were pretty busy. It seemed like lately it was one late night after another. It was mild out earlier in the evening, however now at 3 Am it was still chilly even for this time of year. I looked out the window of the office and saw her again. She was standing there, all dressed up for display, looking desperately at all the cars passing by. Nobody was stopping. The problem was obvious. The city had cracked down on prostitution, using mass arrests of johns and even putting the faces of johns in the newspapers. They had been so effective that they had brought the prostitution industry to a halt almost. This couldn’t last forever, but for the time being the pimps that ran these girls were not doing very well financially.
She was young looking, and looked fairly new to the streets. Probably a runaway who found that the streets were far crueler than the situation she left at home. Pimps are natural predators, and a young lady alone, with no-one to turn to very quickly becomes his property. Usually they start nice, acting like a boy friend, spending money on them until one day that the bill comes in and she realizes all the money he spent on her was a loan....with heavy interest. Then brutality and intimidation make her desperate to pay off the debt and soon the poor girl is out there in the streets being abused by strange men in the back seats of cars. The interest grew quicker than her ability to pay and she ended up in an endless spiral of despair and depravity with no way out. Girls like this had nobody to turn to. They were alone in this world and their pimps knew it. They had no hope.
I saw a “gentleman” wearing a very nice suit approach her. The fear in her eyes, the way she tensed in his presence made it obvious that he was her “employer”. I couldn’t hear the words, but it was obvious he had threatened her. She was terrified of this man. Evidently he didn’t care that the johns were drying up and going away. He wanted her to turn over some pussy and bring in the dough or he would teach her a very painful lesson. She knew she had better find someone who would trade money for her flesh before sunrise or she would suffer. She was scared shitless.
Turning away from the window, I went back to closing things up in the office and then headed out. My route of travel took me past her. I admired her form as I walked towards her. I had seen her in the corner store once getting change and had over heard her talking to another street worker and found out that she was militant about use of condoms. This piqued my interest. She was young, relatively unused and std free. As I passed she made her usual inquiry;
“Looking for some company?”
Pausing I turned and looked at her. I had been very busy lately, and hadn’t had any tail for some time due to my work hours, and despite being a prostitute she looked young and fresh, her pale skin blushed from the cool night air, her tender looking legs, and her innocent looking blue eyes.
It was odd that I even stopped, but for whatever reason I did.
“I might be. Want to talk about what we can do and for what cost?” I asked
She started quickly saying how much she would blow me for, and what sex would cost...yadda yadda yadda. What I wanted was anal. I can get a girl to blow me for free, and I can get pussy for free. What I can’t get is any girl to let me stick it in her ass. The few who have even tried, immediately yelped and pulled away, changing their minds rapidly at the first bit of pain.
“Look this isn’t a good spot to talk. Why don’t we meet elsewhere in about five minutes or so?”
She agreed, and I gave her directions to my parking lot only making her go the other way and take a roundabout route to getting there. That way of any cops saw her talking to me, they would see me walk away, and then five minutes later her going in the other direction. On my way, I hit an ATM and took out a lot of cash.
I got to my car and waited, but didn’t have to wait long. She made her way over and looked around, making sure no-body was watching and then quickly got in.
She smiled and asked me what I wanted.
“How much for anal?” I inquired
“I don’t do anal”, she required quickly
“I’m willing to pay well” I said
Shaking her head she spoke, and told me what her offerings were and at what price.
“Look, I don’t need to pay for oral or vaginal sex. I can get those for free” I said, and pulled out a wad of cash that was a 300% mark-up on anything she was offering. “Now if you want my business then I’m sorry to have wasted your time” I say as I gestured to the door.
The cash made her eyes go wide, and she quickly made an eager counter offer
“Hey stud, I can show you a real good time without anal. I can give you a party like you couldn’t imagine” She said seductively, running her hand on my leg.
Shaking my head I responded “No. I want anal, but if you’re not interested that’s your choice. You’re passing up a lot of money though”
She looked, and took a deep breath. She was terrified of going back to her pimp empty handed again. This was more money than all the other girls combined would bring home for the rest of the week, the streets were so devoid of customers.
“I can....”, she sighed uncomfortably, “Ok, I can give it a try”
“We’re not done yet” I said. “Here is what I want”, as I proceeded to tell her my demands.
“First, I want to go bareback”. She opened her mouth to argue but I cut her off, “Look, I’m not your usual john. I’ve never paid for sex before, and I live a healthy lifestyle. I see you always use them so there is no risk for me since I am certain you are clean”
“I really don’t feel comfortable doing anything without protection” she said
“OK then, I’m sorry to have wasted your time” as I went to put the money away and gestured to her to get out.
“Ok!....OK! Just this one time” she said, knowing she couldn’t afford to pass up this much money. Her pimp was getting brutal with all the girls, but of course being careful not to mark up their faces. He had them all terrified, and this wad of cash would get him to take it easy on her for the next while
“OK, here is what I want you to do. First, I do want a blowjob. Second, once the blowjob is done, you need to get me hard again using whatever techniques you have to get me going, and then when I am hard again, I want to do anal”
She looked at me uncertainly. My reason for wanting the blowjob first, was that I had never experienced anal. Every time I had tried the girl freaked out as soon as I started so I was concerned that the excitement would cause me to cum too fast. That’s why I wanted a blowjob to take care of load one. Then load two would be able to withstand itself for awhile before blowing off. I pulled out a bit more cash sweetening the deal.
She nodded her head, and took a deep breath..”OK”
“One more thing. This is a package deal. There will be no partial payment for partial performance. You do the blowjob but back out of the anal, and you get zero. Until I come inside your ass you get nothing. Once I do that, you get the whole wad of cash” as I fluttered the cash on front of her. She paused for a second, so I put the pressure on.
‘Look, I don’t have all night. I know your market has dried up, and your employer is less than tolerant of you ladies not turning a profit. If you don’t want the money then go!” I say abruptly as I gesture to the door.
“OK” she says quickly, and reaches over
“Not here. Let’s go somewhere we won’t be disturbed.” As I start the car and pull out. I drive us at least 8 blocks away near an industrial park where there is never anybody around at night. I don’t want a cop spoiling all the fun.
Pulling in behind a warehouse, I pull up behind a loading ramp, knowing full well that no-one will show up. It belonged to one of our clients and has been closed down.
“OK, back seat” I say as I get out and move to the back, and she follows. Getting in, I sit back and tell her to go to work.
She undoes my fly and pulls out my cock, which is already very erect. She lowers her mouth onto me, and a chill goes up my spine when I feel the hot moisture of her breath on my flesh, seconds before her soft young mouth closes on the flesh. I close my eyes and try to control my breathing as she works her magic on my cock. She definitely knew how to do this well. I find my entire body gyrating from the sensation as she sucks and licks, working over my flesh.
Gradually my excitement builds, and I reach to grab her hair. Holding her hair, I start moving her head up and down on my cock. She doesn’t like this; I can tell by her reaction, but she is used to it and allows me to. Moving her head up and down rapidly, I thrill at the sensation for several more minutes as I fuck her mouth. Soon I feel my orgasm coming, and start moving her head up and down faster until I climax. As my orgasm starts, I push her mouth down on my cock, forcing the head to the back of her throat roughly.
“Swallow girl!” as My semen pumps into her mouth and she struggles to swallow it all and not gag. I forgot that she was used to using condoms.
Pulling out of her mouth, I feel my cock softening a bit.
“OK, get me hard again woman!” as I command her to get to work
She then uses all her resources, sucking, licking, playing and even grinding her pussy up against it. She removes her panties and starts sliding her young pussy up and down over my cock, not making me penetrate...just teasing.
“Sure you don’t want to put your hot sexy man rod into my soft little pussy instead? I can fuck you in ways you can’t imagine. I just get hot thinking of a man like you in my pussy” she said seductively
Her attempt at incorporating flattery into her suggestion did not disguise the fact that she was just trying to get out of doing anal. Nice try.
“No, a deal is a deal. Now let’s get out and move over to that work bench over there”
We get out and she walks over tentatively, nervous about the ordeal she is about to submit to.
“OK, bend over that work bench and spread your feet about a yard apart”
She takes a deep nervous breath and walks over, complying with my command
“I have some hand cream in my purse, it might help” she says desperately. I actually agree it’s a good idea. I want to make the penetration easier so she doesn’t back out.
Grabbing the lotion out of her purse, I coat it liberally over my cock, and then pour some on her butt, just above her anus, allowing it to dribble down.
Grabbing my slippery cock, I touch the head to her anus as she flinches and tenses up, and I use my cock head to spread some of the lotion around her asshole. I stroke my cock head around stimulating her anus for awhile, trying to get her to enjoy it and relax. After awhile I realize it is time to just put the damned thing in.
Leaning in, I press against her anus as she inhales sharply through gritted teeth. I push a little harder and she yelps, pulling away.
“Ow, that hurts”, she says, looking at me with imploring eyes.
“You’re tightening up, and making it worse for yourself. Try to just relax” I say as I position my cock.
“OK, when I say now, I want you to relax your anus, but push with your abdomen, like you are trying to tale a dump. It will cause your anus to open, making this easier.”
I touch the head, and apply slight pressure as she hyperventilates in fear.
Putting a hand on her shoulder, to prevent her from getting away I give her the word.
“Now...relax and push” I say. She does just that, and it does open her a bit, which I take advantage of pushing in, but as soon as I start opening her she starts to pull away, yelping in a shrill voice. Fortunately I have her held.
“Ow...owow..ow..”
“Just relax. As soon as I started pushing in you stopped pushing and clenched. Try to relax. It will hurt a bit at first but only until I get in...now lets try again”
As soon as she pushes and starts to open, I move fast, pushing hard against her opening anus, not giving her a chance to clench. The effect allows my cock head to slide in, opening her tight anus as I slide the base of my cock head past her tight gripping spinchter ring
“AAaiiiiggghh...Ow..ow pull it out...it hurts, pull it out!”
Holding her fast, I don’t let her squirm away, keeping my cock head lodged in.
“Look, if I pull out, I just have to put it in again so why not hold any gained ground?” I say, reasoning with her. “Just remember, other women have done this, they all survived. Soon it will be over, so just think about the money at the end”
She gasps, and her body shudders from the pain of being opened up back there
“Ok...ok” she gasped, trying to catch her breath.
“OK, I’m going to lean in and start working the rest in. Just keep trying to relax and open, it really makes it easier”. She nods her head and takes a deep breath, bracing herself.
Leaning in again, I started pushing and opened her up more as a few inches of my cock slid into her rectum, this causing her to straighten up and scream as her legs started kicking a bit, more twitching than any real direct movement.
“STOP!.......STOP!” she cried, trying to wriggle out from beneath me, as I held her fast, refusing to take it out.
“Look, it’s almost in, just try to relax. The worst part is almost over” I said, trying to re-assure her.
She gasped, and told me to wait before pushing further. She never imagined it would hurt this bad, and was at a loss as to how she could minimize the pain. She was wiggling, taking deep breaths doing everything she could to minimize the pain. The effect of having her tight ring yield and slide snugly over my cock was ecstatic, but her wiggling and clenching was exciting me too. I should have done this years ago.
“Ok, look. I’m going to slowly work the rest in. Try to relax down there and open up; it will make it much easier on you. Once it is in and we start, it is not as bad. Think of that big wad of cash”
Looking back at me in fear and contempt, she reluctantly agreed to let me finish. I then started very slowly working the rest in. She was in terrible pain the whole time, jerking, and yelping, occasionally reaching back and placing a hand on my pelvis to stop me from moving forward. Her expression was one of agony, as she fought to control her reactions. I on the other hand was loving this. It felt so awesome to have her tight little anus resisting my cock, stretching tightly and sliding over my flesh, sending waves of pleasure through my body. I pushed, and tiwtsed, slowly working the whole thing in, trying not to go too fast lest I panic her and cause her to cancel the deal.
“Ooowww....oww......please....OW!..............aaa aiiiii” she cried out as she shook her head back and forth trying to find a way to release the pain from her body. It was agony, but she needed this money bad. When I finally got the whole thing in, she gasped and started breathing heavily. It still must have hurt like fuck, but I had gone as far in as I was going to go.....to the hilt. I held my position for a few seconds, giving her a chance to adjust as I delighted in the sensation of her entire rectum squeezing the entire length of my cock while she wriggled in pain.
After a few seconds I started to withdraw, and got partway out before leaning in and pushing my cock into her bowels again as she tried to straighten out yelping loudly from the pain, as I held her down. I then started slowly fucking her ass, with long slow strokes, all the way out and then all the way is as she grunted and squealed with each thrust into her bowels. For me it was heaven. This was tighter than a young virgins pussy. I wish I could have got a chicks ass years ago. I started moving a tiny bit faster, casuing her to cry out.
“Stop!...Stop!.....slower, you have to go slower, it feels like you are tearing me open!”she whined, looking back at me in pain.
“Look, I didn’t pay to tenderly make love to your ass. I paid to fuck it. Now do you want the money or not?”
‘Yes! It’s just that..” she started to whine. Cutting her off I reminded her of the facts.
“Look, I’m not your usual trick. When does anybody pay you that kind of money? If you want the money you’ll just have to grit your teeth and bear it.”
She looked afraid, and in terrible pain but knew better than to argue. She needed the money desperately.
I continued, sliding my cock in and out of her tight fucking shitter, making her yelp and cry with each thrust into her bowels. Her buttocks were quivering, undoubtedly in an automatic response to the pain. This was heaven. A tight fucking hole, the bitch with the tight hole in pain, and me not having to worry about how she feels. I suddenly realized why hookers were desired. The sex is 100% about the guys satisfaction.
I kept fucking her tight little ass as she whimpered and cried. I started to speed up a bit more, and she suddenly started crying out.
“OK stop....stop, I can’t do this..it hurts”
Holding her still I spoke in her ear, “I’m almost done, just a bit longer” as I started fucking her ass even harder. This caused her to start crying and struggling.
“No...it hurts...it hurts! Pull it ommmmmpph” my hand clamping over her mouth but an end to her fucking whining. Now the serious fucking was about to start as her cries were muffled. I started fucking her ass hard, driving my cock in real viciously, with rough brutal thrusts into her tight resisting rectum as she screamed through my hand, struggling helplessly beneath me. I fucking loved this. Tears poured from her eyes over my hand covering her mouth as I savagely violated her defenceless rectum. The agony must have been intense and overwhelming, because her struggles weren’t even controlled acts aimed at stopping me. She just appeared to be twisting and convulsing as though overwhelmed by pain.
Then I really went nuts. I started slamming my hips forward with all my might, driving my pelvis into her buttocks as my cock repeatedly tore through her gripping anus as the girl squealed pitifully. This had evolved from a transaction to an assault. These risks come with her profession though so she should start getting used to it. I raped her ass savagely for a few more minutes, until I couldn’t hold out any longer and came hard, firing my semen into her bowels as I planted my cock deep inside her. I held her for a good thirty seconds as my cock convulsed inside her battered rectum.
When my last spurt of cum ejected into her bowels, I pulled back, sliding my cock out of her ass which made a small noise as it closed.
She crumpled to the ground in the foetal position, crying in deep hard sobs. I looked at my cock and saw that it was covered in blood. I guess I must have done some damage. For the next few days, every bowel movement would be an ordeal for her.
Pulling up my pants, I reached in and fished out the money I promised. It’s one thing to be rough with a hooker, but rip her off and you’ll be answering to her pimp. Dropping the bills on the ground in front of her as she lay there sobbing, her nose running, her makeup all streaked.
Turning to walk to my car I opened the door and got in. She called out to me and tried to stand, but found it was still to painful to move.
“Wait, I need a second” she sobbed.
“I’m going the other way, you’ll have to get back there yourself” I retorted.
She looked at me pitifully as I prepared to leave her.
Walking back over to her, I reached in to my pocket and fished out a bunch of change, more than enough to catch a bus.
“Here” I said, throwing the change on the ground beside her. “Take the bus”
Getting into my car, I started driving away.
I saw her out there the next night, as she stood there in the cold, still walking funny from her ordeal. When I walked past her later in the evening she didn’t make eye contact. She did not want my business again.
For the next 3-4 months, I saw her out there nightly, plying her trade, letting strange men abuse her for money that she never kept, but passed on to her pimp. I occasionally saw signs of abuse, bruises on her legs and such (but never the face) as her pimp kept her in line. Then one day she was gone, and I never saw her again. What happened, nobody knows. Maybe she was one of the lucky few who escaped the streets and made it to some sort of safe home. More likely she OD’d, or was sold off , killed by a customer or even by her pimp for holding out. Whatever happened was irrelevant. All I care about is that she had one tight little asshole, and I was the first to split it.
She was young looking, and looked fairly new to the streets. Probably a runaway who found that the streets were far crueler than the situation she left at home. Pimps are natural predators, and a young lady alone, with no-one to turn to very quickly becomes his property. Usually they start nice, acting like a boy friend, spending money on them until one day that the bill comes in and she realizes all the money he spent on her was a loan....with heavy interest. Then brutality and intimidation make her desperate to pay off the debt and soon the poor girl is out there in the streets being abused by strange men in the back seats of cars. The interest grew quicker than her ability to pay and she ended up in an endless spiral of despair and depravity with no way out. Girls like this had nobody to turn to. They were alone in this world and their pimps knew it. They had no hope.
I saw a “gentleman” wearing a very nice suit approach her. The fear in her eyes, the way she tensed in his presence made it obvious that he was her “employer”. I couldn’t hear the words, but it was obvious he had threatened her. She was terrified of this man. Evidently he didn’t care that the johns were drying up and going away. He wanted her to turn over some pussy and bring in the dough or he would teach her a very painful lesson. She knew she had better find someone who would trade money for her flesh before sunrise or she would suffer. She was scared shitless.
Turning away from the window, I went back to closing things up in the office and then headed out. My route of travel took me past her. I admired her form as I walked towards her. I had seen her in the corner store once getting change and had over heard her talking to another street worker and found out that she was militant about use of condoms. This piqued my interest. She was young, relatively unused and std free. As I passed she made her usual inquiry;
“Looking for some company?”
Pausing I turned and looked at her. I had been very busy lately, and hadn’t had any tail for some time due to my work hours, and despite being a prostitute she looked young and fresh, her pale skin blushed from the cool night air, her tender looking legs, and her innocent looking blue eyes.
It was odd that I even stopped, but for whatever reason I did.
“I might be. Want to talk about what we can do and for what cost?” I asked
She started quickly saying how much she would blow me for, and what sex would cost...yadda yadda yadda. What I wanted was anal. I can get a girl to blow me for free, and I can get pussy for free. What I can’t get is any girl to let me stick it in her ass. The few who have even tried, immediately yelped and pulled away, changing their minds rapidly at the first bit of pain.
“Look this isn’t a good spot to talk. Why don’t we meet elsewhere in about five minutes or so?”
She agreed, and I gave her directions to my parking lot only making her go the other way and take a roundabout route to getting there. That way of any cops saw her talking to me, they would see me walk away, and then five minutes later her going in the other direction. On my way, I hit an ATM and took out a lot of cash.
I got to my car and waited, but didn’t have to wait long. She made her way over and looked around, making sure no-body was watching and then quickly got in.
She smiled and asked me what I wanted.
“How much for anal?” I inquired
“I don’t do anal”, she required quickly
“I’m willing to pay well” I said
Shaking her head she spoke, and told me what her offerings were and at what price.
“Look, I don’t need to pay for oral or vaginal sex. I can get those for free” I said, and pulled out a wad of cash that was a 300% mark-up on anything she was offering. “Now if you want my business then I’m sorry to have wasted your time” I say as I gestured to the door.
The cash made her eyes go wide, and she quickly made an eager counter offer
“Hey stud, I can show you a real good time without anal. I can give you a party like you couldn’t imagine” She said seductively, running her hand on my leg.
Shaking my head I responded “No. I want anal, but if you’re not interested that’s your choice. You’re passing up a lot of money though”
She looked, and took a deep breath. She was terrified of going back to her pimp empty handed again. This was more money than all the other girls combined would bring home for the rest of the week, the streets were so devoid of customers.
“I can....”, she sighed uncomfortably, “Ok, I can give it a try”
“We’re not done yet” I said. “Here is what I want”, as I proceeded to tell her my demands.
“First, I want to go bareback”. She opened her mouth to argue but I cut her off, “Look, I’m not your usual john. I’ve never paid for sex before, and I live a healthy lifestyle. I see you always use them so there is no risk for me since I am certain you are clean”
“I really don’t feel comfortable doing anything without protection” she said
“OK then, I’m sorry to have wasted your time” as I went to put the money away and gestured to her to get out.
“Ok!....OK! Just this one time” she said, knowing she couldn’t afford to pass up this much money. Her pimp was getting brutal with all the girls, but of course being careful not to mark up their faces. He had them all terrified, and this wad of cash would get him to take it easy on her for the next while
“OK, here is what I want you to do. First, I do want a blowjob. Second, once the blowjob is done, you need to get me hard again using whatever techniques you have to get me going, and then when I am hard again, I want to do anal”
She looked at me uncertainly. My reason for wanting the blowjob first, was that I had never experienced anal. Every time I had tried the girl freaked out as soon as I started so I was concerned that the excitement would cause me to cum too fast. That’s why I wanted a blowjob to take care of load one. Then load two would be able to withstand itself for awhile before blowing off. I pulled out a bit more cash sweetening the deal.
She nodded her head, and took a deep breath..”OK”
“One more thing. This is a package deal. There will be no partial payment for partial performance. You do the blowjob but back out of the anal, and you get zero. Until I come inside your ass you get nothing. Once I do that, you get the whole wad of cash” as I fluttered the cash on front of her. She paused for a second, so I put the pressure on.
‘Look, I don’t have all night. I know your market has dried up, and your employer is less than tolerant of you ladies not turning a profit. If you don’t want the money then go!” I say abruptly as I gesture to the door.
“OK” she says quickly, and reaches over
“Not here. Let’s go somewhere we won’t be disturbed.” As I start the car and pull out. I drive us at least 8 blocks away near an industrial park where there is never anybody around at night. I don’t want a cop spoiling all the fun.
Pulling in behind a warehouse, I pull up behind a loading ramp, knowing full well that no-one will show up. It belonged to one of our clients and has been closed down.
“OK, back seat” I say as I get out and move to the back, and she follows. Getting in, I sit back and tell her to go to work.
She undoes my fly and pulls out my cock, which is already very erect. She lowers her mouth onto me, and a chill goes up my spine when I feel the hot moisture of her breath on my flesh, seconds before her soft young mouth closes on the flesh. I close my eyes and try to control my breathing as she works her magic on my cock. She definitely knew how to do this well. I find my entire body gyrating from the sensation as she sucks and licks, working over my flesh.
Gradually my excitement builds, and I reach to grab her hair. Holding her hair, I start moving her head up and down on my cock. She doesn’t like this; I can tell by her reaction, but she is used to it and allows me to. Moving her head up and down rapidly, I thrill at the sensation for several more minutes as I fuck her mouth. Soon I feel my orgasm coming, and start moving her head up and down faster until I climax. As my orgasm starts, I push her mouth down on my cock, forcing the head to the back of her throat roughly.
“Swallow girl!” as My semen pumps into her mouth and she struggles to swallow it all and not gag. I forgot that she was used to using condoms.
Pulling out of her mouth, I feel my cock softening a bit.
“OK, get me hard again woman!” as I command her to get to work
She then uses all her resources, sucking, licking, playing and even grinding her pussy up against it. She removes her panties and starts sliding her young pussy up and down over my cock, not making me penetrate...just teasing.
“Sure you don’t want to put your hot sexy man rod into my soft little pussy instead? I can fuck you in ways you can’t imagine. I just get hot thinking of a man like you in my pussy” she said seductively
Her attempt at incorporating flattery into her suggestion did not disguise the fact that she was just trying to get out of doing anal. Nice try.
“No, a deal is a deal. Now let’s get out and move over to that work bench over there”
We get out and she walks over tentatively, nervous about the ordeal she is about to submit to.
“OK, bend over that work bench and spread your feet about a yard apart”
She takes a deep nervous breath and walks over, complying with my command
“I have some hand cream in my purse, it might help” she says desperately. I actually agree it’s a good idea. I want to make the penetration easier so she doesn’t back out.
Grabbing the lotion out of her purse, I coat it liberally over my cock, and then pour some on her butt, just above her anus, allowing it to dribble down.
Grabbing my slippery cock, I touch the head to her anus as she flinches and tenses up, and I use my cock head to spread some of the lotion around her asshole. I stroke my cock head around stimulating her anus for awhile, trying to get her to enjoy it and relax. After awhile I realize it is time to just put the damned thing in.
Leaning in, I press against her anus as she inhales sharply through gritted teeth. I push a little harder and she yelps, pulling away.
“Ow, that hurts”, she says, looking at me with imploring eyes.
“You’re tightening up, and making it worse for yourself. Try to just relax” I say as I position my cock.
“OK, when I say now, I want you to relax your anus, but push with your abdomen, like you are trying to tale a dump. It will cause your anus to open, making this easier.”
I touch the head, and apply slight pressure as she hyperventilates in fear.
Putting a hand on her shoulder, to prevent her from getting away I give her the word.
“Now...relax and push” I say. She does just that, and it does open her a bit, which I take advantage of pushing in, but as soon as I start opening her she starts to pull away, yelping in a shrill voice. Fortunately I have her held.
“Ow...owow..ow..”
“Just relax. As soon as I started pushing in you stopped pushing and clenched. Try to relax. It will hurt a bit at first but only until I get in...now lets try again”
As soon as she pushes and starts to open, I move fast, pushing hard against her opening anus, not giving her a chance to clench. The effect allows my cock head to slide in, opening her tight anus as I slide the base of my cock head past her tight gripping spinchter ring
“AAaiiiiggghh...Ow..ow pull it out...it hurts, pull it out!”
Holding her fast, I don’t let her squirm away, keeping my cock head lodged in.
“Look, if I pull out, I just have to put it in again so why not hold any gained ground?” I say, reasoning with her. “Just remember, other women have done this, they all survived. Soon it will be over, so just think about the money at the end”
She gasps, and her body shudders from the pain of being opened up back there
“Ok...ok” she gasped, trying to catch her breath.
“OK, I’m going to lean in and start working the rest in. Just keep trying to relax and open, it really makes it easier”. She nods her head and takes a deep breath, bracing herself.
Leaning in again, I started pushing and opened her up more as a few inches of my cock slid into her rectum, this causing her to straighten up and scream as her legs started kicking a bit, more twitching than any real direct movement.
“STOP!.......STOP!” she cried, trying to wriggle out from beneath me, as I held her fast, refusing to take it out.
“Look, it’s almost in, just try to relax. The worst part is almost over” I said, trying to re-assure her.
She gasped, and told me to wait before pushing further. She never imagined it would hurt this bad, and was at a loss as to how she could minimize the pain. She was wiggling, taking deep breaths doing everything she could to minimize the pain. The effect of having her tight ring yield and slide snugly over my cock was ecstatic, but her wiggling and clenching was exciting me too. I should have done this years ago.
“Ok, look. I’m going to slowly work the rest in. Try to relax down there and open up; it will make it much easier on you. Once it is in and we start, it is not as bad. Think of that big wad of cash”
Looking back at me in fear and contempt, she reluctantly agreed to let me finish. I then started very slowly working the rest in. She was in terrible pain the whole time, jerking, and yelping, occasionally reaching back and placing a hand on my pelvis to stop me from moving forward. Her expression was one of agony, as she fought to control her reactions. I on the other hand was loving this. It felt so awesome to have her tight little anus resisting my cock, stretching tightly and sliding over my flesh, sending waves of pleasure through my body. I pushed, and tiwtsed, slowly working the whole thing in, trying not to go too fast lest I panic her and cause her to cancel the deal.
“Ooowww....oww......please....OW!..............aaa aiiiii” she cried out as she shook her head back and forth trying to find a way to release the pain from her body. It was agony, but she needed this money bad. When I finally got the whole thing in, she gasped and started breathing heavily. It still must have hurt like fuck, but I had gone as far in as I was going to go.....to the hilt. I held my position for a few seconds, giving her a chance to adjust as I delighted in the sensation of her entire rectum squeezing the entire length of my cock while she wriggled in pain.
After a few seconds I started to withdraw, and got partway out before leaning in and pushing my cock into her bowels again as she tried to straighten out yelping loudly from the pain, as I held her down. I then started slowly fucking her ass, with long slow strokes, all the way out and then all the way is as she grunted and squealed with each thrust into her bowels. For me it was heaven. This was tighter than a young virgins pussy. I wish I could have got a chicks ass years ago. I started moving a tiny bit faster, casuing her to cry out.
“Stop!...Stop!.....slower, you have to go slower, it feels like you are tearing me open!”she whined, looking back at me in pain.
“Look, I didn’t pay to tenderly make love to your ass. I paid to fuck it. Now do you want the money or not?”
‘Yes! It’s just that..” she started to whine. Cutting her off I reminded her of the facts.
“Look, I’m not your usual trick. When does anybody pay you that kind of money? If you want the money you’ll just have to grit your teeth and bear it.”
She looked afraid, and in terrible pain but knew better than to argue. She needed the money desperately.
I continued, sliding my cock in and out of her tight fucking shitter, making her yelp and cry with each thrust into her bowels. Her buttocks were quivering, undoubtedly in an automatic response to the pain. This was heaven. A tight fucking hole, the bitch with the tight hole in pain, and me not having to worry about how she feels. I suddenly realized why hookers were desired. The sex is 100% about the guys satisfaction.
I kept fucking her tight little ass as she whimpered and cried. I started to speed up a bit more, and she suddenly started crying out.
“OK stop....stop, I can’t do this..it hurts”
Holding her still I spoke in her ear, “I’m almost done, just a bit longer” as I started fucking her ass even harder. This caused her to start crying and struggling.
“No...it hurts...it hurts! Pull it ommmmmpph” my hand clamping over her mouth but an end to her fucking whining. Now the serious fucking was about to start as her cries were muffled. I started fucking her ass hard, driving my cock in real viciously, with rough brutal thrusts into her tight resisting rectum as she screamed through my hand, struggling helplessly beneath me. I fucking loved this. Tears poured from her eyes over my hand covering her mouth as I savagely violated her defenceless rectum. The agony must have been intense and overwhelming, because her struggles weren’t even controlled acts aimed at stopping me. She just appeared to be twisting and convulsing as though overwhelmed by pain.
Then I really went nuts. I started slamming my hips forward with all my might, driving my pelvis into her buttocks as my cock repeatedly tore through her gripping anus as the girl squealed pitifully. This had evolved from a transaction to an assault. These risks come with her profession though so she should start getting used to it. I raped her ass savagely for a few more minutes, until I couldn’t hold out any longer and came hard, firing my semen into her bowels as I planted my cock deep inside her. I held her for a good thirty seconds as my cock convulsed inside her battered rectum.
When my last spurt of cum ejected into her bowels, I pulled back, sliding my cock out of her ass which made a small noise as it closed.
She crumpled to the ground in the foetal position, crying in deep hard sobs. I looked at my cock and saw that it was covered in blood. I guess I must have done some damage. For the next few days, every bowel movement would be an ordeal for her.
Pulling up my pants, I reached in and fished out the money I promised. It’s one thing to be rough with a hooker, but rip her off and you’ll be answering to her pimp. Dropping the bills on the ground in front of her as she lay there sobbing, her nose running, her makeup all streaked.
Turning to walk to my car I opened the door and got in. She called out to me and tried to stand, but found it was still to painful to move.
“Wait, I need a second” she sobbed.
“I’m going the other way, you’ll have to get back there yourself” I retorted.
She looked at me pitifully as I prepared to leave her.
Walking back over to her, I reached in to my pocket and fished out a bunch of change, more than enough to catch a bus.
“Here” I said, throwing the change on the ground beside her. “Take the bus”
Getting into my car, I started driving away.
I saw her out there the next night, as she stood there in the cold, still walking funny from her ordeal. When I walked past her later in the evening she didn’t make eye contact. She did not want my business again.
For the next 3-4 months, I saw her out there nightly, plying her trade, letting strange men abuse her for money that she never kept, but passed on to her pimp. I occasionally saw signs of abuse, bruises on her legs and such (but never the face) as her pimp kept her in line. Then one day she was gone, and I never saw her again. What happened, nobody knows. Maybe she was one of the lucky few who escaped the streets and made it to some sort of safe home. More likely she OD’d, or was sold off , killed by a customer or even by her pimp for holding out. Whatever happened was irrelevant. All I care about is that she had one tight little asshole, and I was the first to split it.