As Gabe and I walked, he reached up my skirt and played with my ass. I smiled and leaned into him. When he got to my cum soaked panties he gave me a big smile.
"Damn baby, you really got off suckin my dick didn't you?" he chuckled.
I just blushed and nodded. He was right. It was the first time I had sucked a real cock and I got off hard. It was a serious blow to my manhood, but it felt so good I couldn't help it.
"Well don't worry, you're my girl Susan now. And you'll be sucking alot of $20 dicks to make my money back." he said with a nod.
"What!" I said shocked.
"Fuck yeah! You wanted to dress up like a girl and play hooker. So, I bought you for the weekend and I'm playing pimp." he said matter of factly. "For every dick you suck, half goes to me, the other half comes off your bill."
"What? Huh?" I stammered. "Half? What bill?"
He stopped and looked at me seriously. "I'm out $170 and you wanna be a hooker, so I'm gonna pimp you out to make my money back. As your pimp, I'm taking half and the other half comes off your bill."
"Oh" I said as it sank in.
All I wanted, was to dress as a girl and flash in public. Now I was a $20 whore! Not only that I had to pay back $170 at $10 a pop.
"You thought it was fun to dress up and suck dick for money. Well, you'll be doing a lot of it now." he said.
"Yeah, I get it." I replied quietly.
I thought dressing like a girl and having an orgasm while sucking a cock was a blow to my manhood. This removed any doubt about my manhood. I was no longer a man. I was a cheap whore.
When we got to his building, Grady was sitting out front like always. Grady was retired and in his mid 70's. Every time I had ever been there, he was sitting out front with a cane in one hand and a glass of iced tea in the other. This was no different.
"Damn Boy! It's only 10 and you already snagged a white girl?" Grady laughed.
Gabe smacked my ass hard "Damn Straight! This is Susan and she sucks a mean dick for $20!"
"Hell, I got $20!" Grady said as he put down his tea and stood up.
He pulled out a $20 bill, gave it to Gabe and shuffled into his apartment
Gabe stuffed the twenty in his pocket "Time to earn your keep."
I looked at the floor, followed Grady to his bedroom and closed the door behind us. He stood next to the bed, pulled his pants and boxers down. Sat on the bed and looked at me. I kneeled in front of him and stared at his cock.
It was beautiful. It was about an 1 1/2" thick 7 1/2" long stretched out at half mast. It was dark black with a bright red head. My mouth began to water as I studied it.
When I began to stroke it, Grady say's "It don't get hard no more but it'll still go off if you give it a good spit shine."
I smiled and looked up at him as I slowly sucked the head of his cock into my mouth. Grady let out a deep sigh and laid back on the bed. I studied his cock as I slowly sucked more and more of it into my mouth. I sucked it right to the base and felt him slither down my throat.
I slowly pulled back until I was just sucking the head again. Then sucked it all the way back down my throat. It went down so easy I stopped to enjoy the feeling.
I could feel the head of his cock deep in my throat. His cock hair was brushing my nose, his big balls were pressing around my chin and I was looking up at a guy who was enjoying my services.
I smiled, he had paid for pleasure and I was there to deliver. I sucked his shaft in long slow strokes. From it's base to it's tip. Then I sucked it down my throat again. I began to suck it hard and fast like I had done for Gabe.
Just like before, my dick was getting hard so I started to hump at the air again. Dragging the head of my cock across the soft fabric of my panties.
As Grady began to moan, I could feel his cock getting rock hard. His cock tasted so good and it was so hard, I sucked as hard and fast as I could.
Soon, he was moaning and twitching. I felt his cock throbbing in my mouth and knew he was about to cum.
When he came, his cum bubbled into my mouth like thin cake batter. It tasted like Gabe's cum but it was so much thicker. I eagerly swallowed every drop as fast as he could feed it to me.
I loved the way a cock tasted and felt in my mouth, but I knew cum was the real prize. I knew from having my own dick sucked that blowing your load is the pleasure you were after, especially if you were paying for it.
I proudly swallowed the last of his cum and pulled back to look at him. I had just sucked my second cock in less than an hour and it really turned me on.
Being paid to suck cock was turning into the most intensely erotic thing I had ever done. It was a thrill to dress like a girl and suck my girlfriends strap on, but that was nothing compared to being paid real money, by real guys, to suck real cock. This was the ultimate in female role playing!
"Damn! That was good!" Grady exclaimed as he pulled his pants up. "Any time you want to suck a dick you come see me!"
"Thanks, I sure will." I said with a smile.
Grady and I both had big smiles as we walked out of the bedroom. Gabe was was sitting out front where we left him. When he saw Grady's smile he got a big grin also.
"I told you she sucks a mean dick for $20, didn't I?" he laughed.
"She damn sure does!" Grady agreed as he sat back in his seat.
I just smiled at the praise and stood next to Gabe. Gabe got up and grabbed my ass.
"We gotta go make some money Grady. You take care and if you need anything, call me. The next one is on the house." he said as we walked up the stairs to his apartment.
When we got to the apartment, Gabe ushered me to the couch and got us both some sodas. He gave me one and sat in the chair opposite me while eying me up.
"Damn, you're hot! When did you start dressing like a girl and calling yourself Susan?" he asked "We've been working together for years and I never would have guessed."
I blushed and reminded him of the role playing games I had told him about Some of the old standards; Burglary/Rape, Picking up a hooker, French Maid/Sex Toy. I told him how Sandy had bought a realistic looking strap on and asked me to be the maid.
I told him how apprehensive I was at first. But once I tried it, I couldn't get enough. I told him how in the last few months, I had collected a pretty slutty wardrobe and often practiced dressing, walking and talking like a girl.
I told him what a thrill playing a girl had become for me. It was exactly opposite my normal personality and had turned into a rather thrilling escape from my normal life. He agreed that it was radically different than my norm.
He then told me to take off my blouse and skirt so he could "Examine the merchandise" as he put it. I stood and took them off. I fidgeted with embarrassment, under his gaze, as I stood in only my bra and panties.
He told me not to be embarrassed and to show some ass. I turned and bent forward slightly. He stood behind me, telling me I had a nice pussy and a hot ass, while easing me into the kitchen. Once we were standing in front of the table, Gabe eased my panties down, rubbed his growing bulge against my bare ass and whispered in my ear.
"Ever been fucked by a real cock?"
"No" I moaned and pressed my ass back.
"Ready for me to pop that cherry?" he asked as he ground his hips into my ass.
I reached between my legs, pulled out the butt plug and freed my cock.
"Uh ok" I said a little unsure.
Gabe quickly pinned me face first onto the table. I instantly began to struggle, but he had me completely overwhelmed. My arms were flailing and my panties were tangled around my knees so I could hardly move. When I felt the head of his cock against my asshole I squeezed it as tight as possible.
"No!" I squealed.
Gabe held me down and slammed his cock in hard and fast as I continued to struggle. We both groaned as he buried himself balls deep into me.
"Uh! No! Stop! Uh!" I complained.
Gabe just kept fucking me hard and fast as I flopped around squealing. My ass hurt like hell and his balls were banging against mine. I kept fighting as best I could, but I was getting nowhere. His cock was so deep in me, it felt like it was about to come out my mouth. Gabe was fucking me silly and I couldn't stop him.
My asshole started to spasm around his hard driving cock and I began to squeal with delight. My asshole squeezed tight and my hips started to buck as my orgasm swept through me. Cum shot out of my soft cock and I began to meet his thrusts.
Gabe laughed, grabbed my hips with both hands and started to fuck me even harder. I regained my balance and pushed hard against his invading cock while meeting his thrusts.
After a couple more minutes of that, an intense mini orgasm swept through me. I fucked back even harder. If this is what women meant when they talked about multiple orgasms, I wanted more!!
Gabe was slamming the whole length of his cock into me in hard fast strokes. He was pounding my guts hard. I pushed hard against his thrusts like I was trying to shit out his cock, but he pumped into me effortlessly. We were both moaning and groaning but that was drowned out by the loud wet slapping noise of his belly meeting my ass.
As he plundered my ass for all it was worth, I felt another orgasm building deep inside me. I began to squeal loudly and squeeze my asshole tight around the massive piece of meat that was plowing into it. When I did that, it was like flicking a switch.
I came so hard, I jumped, cried out and just about fell over. Gabe began to laugh again, but held me up while he just kept fucking me hard. My eyes rolled up into my head and I was kicking and drooling the whole time I was cumming.
When I came to my senses, I looked down at my cock. It had a butt plug taped to it, it was still soft and only a few drops of cum dribbled out. I had just had the most intense orgasm of my life by being fucked in the ass! I hadn't touched my cock and it didn't even get hard.
No sooner had I made that realization, than Gabe drove his cock as deep into me as he could get. It felt like it was driven all the way into my throat when it started to throb. I squeezed my asshole tight again and got ready for the hot sperm enema I was about to get.
I stared straight ahead with a dazed look while Gabe emptied his balls deep inside me. For some reason, I had an immense sense of satisfaction knowing I had just been used to satisfy a stiff cock. I was an anal slut and I had a butt load of baby batter to prove it!!
At first, I was embarrassed to dress like a girl and suck a strap on. Then I was humiliated when I came while sucking cock. Now I had just gotten fucked up the ass, had three orgasms and the last one REALLY rocked my world.
Fuck my manhood! It was long gone! Fuck being Jim the construction worker! I was Susan the happy hooker! Anal Slut and $20 dick sucker!