Tag: Prostitution Phone Sex

I Couldn’t Believe It

I did it again, spent all my money partying the other night. I called every dick in town that usually pays for pussy or head to make some money and every one is tapped the fuck out. I even called a gay chick I know that will pay me to knock the bottom out of that ass with my big black strap on. So I broke down and looked in the paper to see if I could get a quick gig somewhere and make some cash. I found an ad for someone that wanted help cleaning before the holidays. I set up the interview and headed over for the job. The chick was a homely as hell woman but she had a nice house so I knew she had money. The first thing she wanted me to do was to clean the guest bed room. She gave me the cleaning supplies and sent me on my way. I was deep into cleaning with my head phones on when I felt someone behind me. When I turned around and saw him the old feelings came rushing back and my pussy was instantly wet. It was my old flame and he still looked hot as fucking hell. It seems he has done pretty damned good for himself other then the homely chick he married. He grabbed my ass and started kissing me hard and I could feel his cock growing against my stomach. I knew what was coming the sex would be hot and heavy, he would spank my ass and make me squirt all over his cock. Nether of us cared that she was home and could walk in at any minute, all we cared about was the raw fucking that we both loved! He didn’t even notice the cell phone recording on the dresser. I will be using that later for a good fuck and money!

Selling My Backdoor Pussy

I remember the first time I had sex for money. I never intended to be an escort,  but I was wanting money for my gender reassignment surgery. When I was younger I wanted to be all girl. I was not yet comfortable with my duality; with being the best of both worlds. I had some boobs thanks to the help of hormones, and long beautiful hair. I did my nails and toes, perfected my makeup, wore beautiful girly clothes. I certainly looked the part. Craigslist still had adult listings then, so I took out an ad as a barely legal college coed auctioning off her “backdoor pussy.”  I made it sound like I was all girl and wanting to sell the pleasure of popping my anal cherry. My ass is my pussy. I was just shy of legal and the boy in me was not a virgin, but the girl in me most certainly was. I was amazed how many guys jumped at the opportunity to fuck my ass for the first time. And offer good money.

The guy that offered the most was obese and rather unattractive, so I went with this Latin Lothario. Tall, dark, handsome, hung and loaded. Young for the amount of money he had. I didn’t ask what he did for a living. All I cared about was that he was gonna pay $10,000 cash to fuck my ass for the first time. I felt like Brooke Shields in “Pretty Baby.”  I was nervous. This was dangerous for lots of reasons. First I was fucking a stranger who could kill me. Second, I was duping him into thinking I was a barely legal teen girl. I met him in a hotel lobby for drinks first. I slipped him some X hoping he would be so high by the time we got to the room he might not notice my cock. We started making out in the elevator. It was a struggle to keep him out of my panties. No way was I gonna let him discover my cock before I got my money.

I went down on him first. Got him good and hard and convinced him the best way to do this was to just force his cock in my ass nice and quick. I laid on my stomach to hide my throbbing cock, spread my ass and told him to take my backdoor pussy. He rammed it in as instructed. He said it was the tightest hole he had ever fucked. He came almost instantly in my ass. It hurt like hell and I bled, but it was over quick  and I had $10,000 cash. I felt a bit guilty, but I now know that if a guy wants to pay for a virgin, well  I should take the money and run. I sold my backdoor pussy a dozen more times and amounted enough money for a sex change operation. But, the last guy who bought my virgin ass, discovered my secret. He was actually so turned on, he paid me more to suck my cock too. He had never been with a shemale and he told me I was the best of both worlds and I should never change.

Well, I didn’t. I just  worked on being the best, the sexiest shemale around. Now when I escort, I get big bucks for being the best of both worlds and I hide nothing. I bet you would pay for the privilege of being with a hot tranny.

Prostitution Phone Sex with Sheila: Alley Whore

I was in downtown LA, East Compton to be exact. Not the best part of town, but my car broke down and I had no cell reception. I started to hoof it and see if I could find a payphone, if they even existed any more. I was pretty scantily clad as I was on my way to meet my step sons for some good old fashioned afternoon delight. Out of nowhere comes some guy around a corner and pushes me to the ground stealing my purse. I’m in the middle of a bad neighborhood with no identity, no phone, no keys, no money. I was starting to panic a bit. No cops in sight. How was I going to get out of the hood. The old fashioned way that was how.

I started flashing cars as they passed by. Thinking I could get someone to pull over for a fuck up against the alley wall. I had a bit of trouble at first. Flashing my big boobs seemed to just  get honks and yells. WTF? I am a fine big ass bootylicious MILF in the hood. Certainly someone had some money for a quick fuck or tug and gurgle. Finally this young guy in an El Camino yelled, “How much?” I walked up to his car and said $75 bucks for a 15 minute fuck in the alley. I was all prepared to Blue Light Special myself as I was desperate and $50 would get me a cab, but he agreed.  He parked the car and we ducked into the alley.

I love fucking, but honestly I have never taken money to fuck nor I have fucked in an alley with dumpsters around me and the stench of garbage. But, I lucked out. There was an old couch by one of the dumpsters. Probably disgusting and disease ridden but beggars can’t be choosers. It was better than fucking against a graffiti riddled alley wall with broken glass under my feet. I told my John he had to be on the bottom. I would ride him hard reverse cowgirl, but my ass was not touching that couch. I just thought about seeing my step sons soon and fucked the hell out of that guy. Even let him cum inside me. I was such a filthy whore prostituting myself in an alley in broad daylight. Kind of turned me on being that desperate, that depraved. Had me wondering if I could have a good side career as an alley whore. Something sexy about being an upper class gal fucking in a dirty alley for $75.

My John paid me, and even tipped me and when I explained my situation he offered to take me home and call AAA for me. So, he paid me for sex, fucked me in an alley and was a complete gentleman? My first day as a professional whore was going pretty darn well. I think I may have found my calling. There is something hot and taboo about being paid to fuck.

Diamonds and Pearls: Roleplay Phone Sex

My boss told me that there was a guy who wanted a little role play action and he’d give me money plus some coke.  Of course, I was interested!  The only thing was that I had to wear classy clothes and pearls and shit.  I was supposed to try to look like his young, dead wife.  Anyway, I didn’t give a fuck.  I dressed up and headed over to his mansion. When I got there, he offered me some brandy and gave me a script to read while he went off to do something else.  It was a friggin’ character portrait that he gave me; but, hell, whatever.  I could be this chick for a few hours.  The brandy warmed me and I kept drinking until he returned. 

But, this time, he wasn’t alone; there was a large black guy with him.  He was dressed nicely; but, from his build, he looked like he worked out in the yard for a living.  The old man then told me that I was going to be fucked by Robert, the black main standing there.  The old man leaned toward me and whispered, “He has a very big cock.” He looked at both of us and clapped his hands.  “Take your places,” he said with gusto. 

I sat down on the chair, crossing my legs; and, Robert came in.  He had already rehearsed his lines and knew them by heart.  He said that he was sorry to disturb “the lady of the house” and blah blah.  I reassured him.  And, apparently knowing the script better than me, he began ripping off my clothes.  The elderly man’s breathing intensified and we both could hear it, feet away from his chair. 

He slammed me down on the plush fabric and tore my bra from my breasts.  I asked him what he thought he was doing, and I even called for help.  I thought I was doing well.  Then, I heard the old man huff, “Fuck her!”  I almost laughed, but before I knew it, the man had his big, thick, black cock in my pussy.  I actually think that I said, “Ouch!”  I braced myself and kept thinking about the coke that I was going to score.  Finally, the enormous cock exploded inside of my pussy; and, I grimaced as he removed himself from my throbbing hole.  What a fucking crackpot, I thought, as he left the room; someone else delivered what we had been promised.  I put my clothes back on, collected my money and coke, and got the hell out of there. 

Backfield in Motion

I don’t hate football season, but sometimes I get tired of hearing about it…and it keeps guys away from the strip club.  So, instead of trying to avoid football this year, I decided to embrace it as much as possible.  I started my own little jar where guys could guess the final scores of every game; and, those who guessed ‘spot on’ were going to be rewarded with a free visit to the V.I.P. room.  The trick was that they had to pay to enter; I double-charged them my normal rate for lap dances, but they didn’t seem to mind.  My first winner was an older guy, husky and smelled of whiskey and cigars.  He kinda reminded me of my grandfather…when I was little.  He got the normal slaps on the back and then followed me to the V.I.P. area.  First, he wanted me to jump around in my cheer-leading uniform, yelling for his old football team.  Apparently, he had been a football stud (according to him).  Then, he fell further into the couch and slapped his knees; by the bulge between his legs, I knew where he wanted my attention.  I crawled on top of him and he started calling me “Mary Anne,” his school sweetheart.  I didn’t really care; I just played along. 

“I don’t want to hurt you, Mary Anne,” he said, “but I really want to make love to you.”  I begged him to enter me, trying to sound like someone out of a 1960s film.  He gently slid his cock inside of me and told me how warm and tight I was; he was actually pretty sweet, I thought, even though calling me someone else’s name was a little creepy.  “Now, you know what I want to do, Mary Anne,” he said.  I was confused.  “I want to play in the backfield.  You know that’s my favorite.”  I understood and got on my knees while he spread my ass cheeks apart and spit in my asshole.  He spanked my buttocks and I jumped; he reassured me that I always liked it.  Pushing inside my tight ass, he shoved every inch of his manhood inside of my thin anal walls.  He was thick and stiff; and, as he pumped inisde of me, he continued to tell me that he had won every football game for me.  Only for me.  I tried not to bust out in laughter.  And, after he came inside of my ass, I turned around to suck his cock.  He kissed me on the forehead and told me that his Mary Anne would never do that.  As he left the room, I could hear his voice shouting, “Touch down!”  Whether the football team had scored or not, I have no clue; but, at least I had one happy customer and a wad of cash!

Fucking Machine

Every so often, I’ll look at the classifieds.  My most recent focus was to find an entertainment system to replace the one that got distroyed during a party last weekend.  Well, I found the perfect one that I wanted; it matched and everything.  The only problem was that I needed a couple of extra hundred dollars.  I kept looking through the classifieds and was struck by one entry in particular: “Nice burbs couple looking for 1 healthy young girl for 1 hour. Pays $500.  Discretion req’d.”  I talked to the husband on the phone, and it seemed safe enough…plus, he sounded very friendly.

When I arrived, he and his wife were waiting behind the door.  They looked like any normal couple and were in their early 40s, I guessed.  They brought me into the living room and showed me a contraption…it was a huge machine, about five-feet long, with a dildo on the end of it!  I was shocked.  The man explained that he had bought the contraption for his wife, but she was afraid to use it.  And, that’s where I came in: he was going to experiment with the machine on me while the wife watched!  I blinked in shock; but, I was kind of getting excited! 

I sat on their nice, white sofa after de-robing; and, watched as the husband put a condom on the dildo…then lube.  I smiled at him, although I was a little self-conscious about being totally naked in front of strangers.  I tried to position my body so that the dildo was aimed at my crotch.  I crunched my toes into the couch and prepared myself; the machine did look a little scary, but I knew my pussy was getting wet after staring at it. 

He started it up; and it moved really gently inside of me.  Then, he asked if he could speed it up; I nodded.  It started ramming me until it was at full speed.  I was breathless because of the pounding!  I continued to squirt, my juices shooting over the coffee table.  And the wife, her arms previously crossed, was becoming enthralled.  I leaned my head back and came so many times that I felt like my body wasn’t my own!

My pussy, sore and throbbing, still wanted more; but, the husband stopped the machine.  I could tell the couple was ready to experiment on their own.  But, hey, I was paid a lot to be fucked…and, really well, too!

By Hook or by Crook

My co-worker and I were out on a binge night; we’d been saving all of our tips in order to score some really good shit.  But after dancing, drinking, and even playing some slots…we were out of cash.  We were walking out of a casino when we heard a guy call after us.  Turning around, we looked at him; he was a handsome businessman, maybe even a lawyer.  “I’m looking for a date.  How much?” he asked and moved his finger between us both.  We looked at each other; we were high, but we didn’t understand why he was asking for a dance in the middle of the street.  Probably thinking we were stupid, he walked closer and whispered that he was looking for a date.  It dawned on us that he thought we were hookers!  We weren’t offended and I could see that my friend was thinking the same thing: let’s keep the party going.

He agreed to our price and led us to a less than swanky motel.  He explained that he was sleeping somewhere else, but they had cameras; and, he couldn’t be caught on tape with us.  He gave me the money that he owed us and I put it in my corset.  My friend began grinding on his hips, dancing for him and kissing him.  I noticed there were a couple of handcuffs by the bed.  He was demanding that I come over there and bend over; he told me that he loved porcelain asses.  I swayed my ass while he rubbed it.  He ripped open a condom rapper with his teeth and started unloosening his pants.

I leaned all the way on top of him and grabbed the handcuffs.  “Let me do that,” I whispered seductively.  He smiled like it had been his idea all along.  I clasped the cuffs around his wrists to the posts.  “Oh, kinky!” he said and was becoming more excited.  We both knelt down and sucked his cock for fun…and for a picture.  My friend continued to take pictures as I got up and rummaged through his wallet.  We took all of his cash, which was a huge wad.  “Hey, what are you doing?!  You’ll never get away with this!”  Do you know who I am?!” he screamed.  “Nope,” I laughed, “but thanks for telling us that apparently other people do.”  My friend shook her camera phone in his face.  “So you best not do anything stupid and tell on us,” I instructed before playfully slapping his cheek.

We resumed our partying for two more days on the cash we’d gotten.  A week later, when we finally desired to return to work, our boss told us that word on the street was that there was some congressman or something who had been tied up by two hookers.  He’d escaped before the reporters got there only because the hotel clerk had been bribed to remove some cuffs with a bolt cutter!

Cum One, Cum All!

The other day, I went shopping at one of my favorite XXX stores.  I could barely focus on choosing an outfit, because my pussy kept drooling over all the sexy men that I noticed disappearing to the back.  After browsing, I changed into the sexy getup that I’d just purchased, and made my way to the back, too.  It’s like they all smelled my pussy when I entered.  I walked the halls once, just to let the men get a good look at my firm tits and round, jiggly ass.  Finally, I picked a booth, and one by one, I sucked and fucked every stiff cock that needed relief.  When I was done, I had a swollen, wet cunt and an empty box of condoms.  But, I made some extra cash, got a few good orgasms, and met a couple of really cool guys.  I hadn’t had that kind of fun in a long while.  I’m going to have to go shopping a lot more often!

The Early Days

You would never know it to look at me now. Strong, self confident, sexual and sensual. A large and lovely woman who knows how to please a man and loves doing it. There is nothing more satisfying then to give a man his every kinky fantasy and desire and let him know that I love it as much as he does. If you see me in my fancy lingerie, with the nipples of my soft and lickable tits standing at attention just for you, My pussy wet and begging to be licked and sucked, you would never know how I came to know sex. Daddy loved me very much, it was just us and he worked hard doing construction. One Friday night Daddy got real fucking drunk with his buddies from work. I fell asleep in his bed that night while watching TV and when Daddy fell into bed drunk there I was. Daddy started kissing me like a woman, his breath smelled like bear and his rough beard scratched my face. He pulled my night shirt up and started sucking on my tits while his hand reached between my legs. I knew it was wrong but it felt so good to have Daddy rub my pussy like that. I never felt like that before. Pretty soon my panties were off and Daddy was pushing his long hard dick in between my pussy lips. He covered my mouth with his so that when he pushed all the way in I couldn’t cry out. It really hurt at first but then it started feeling really good. Soon Daddy groaned real loud and I felt him squirt inside me. He held me close and I fell asleep in his arms listening to his heart beat. When things got hard Daddy would sell me to his friends, 20.00 for a blow job, 50.00 for a fuck and 80.00 if they wanted my ass. I didn’t mind helping Daddy make money in fact I kind of liked the attention. But no one made me happier in bed then Daddy did. He taught me all the kinky things men like and just how to keep them happy. I still keep Daddy happy when I can.

“Truck Stop” Pussy

Once a week, my Daddy has been dropping me off at a popular out of town truck stop.  I dress real casual (so people can’t tell I’m a whore) but, I have a back-pack full of sexy panties and bras, a pair of high heels, a couple of sexy short dresses, perfume, condoms, whiskey, smokes, and horny-pills and money to pay for showers and meals and everything I need to get real clean again,after some hard work fuckin’ n’ suckin’ them trucker dicks. cause’ after being on the road for a week or two, you need to fuck.  These men are away from their wives and girlfriends and need a nasty lil’ cum catcher like me, so they can unload their heavy balls sacks.  I work the truck stop for 16 hours. Hell-I usually suck and fuck about 50 guys, each shift.  The best thing is suckin’ dick in the sleeper of their trucks.  I like dick suckin’, cause it’s real quick and I can swallow a lot of cum loads in a short amount of time.  Hell! sometimes my belly gets real full with cum and I don’t need to buy a meal.  I love me some truckers. I earn me some good money at the truck stop, cause hundreds of truckers stop in each day.  I meet paying customers in the diner and when I work my way down the line of semis. There is a lot of good business in these parts!