Debbie Does The Streets #2 - Sit and Listen

To learn more about my newest series, Debbie Does The Streets, read this post.

After a couple days of just blowjobs in the alley and getting my ass torn up, I finally got an interesting hire.  I like those interesting hires, it keeps me from getting bored and I can usually charge more for them.  Such was the case with this client.
This was a hire from a guy I had done before and I guess he trusted me more now and asked for ‘something special’ the other evening.

John told me to strip and sit down on the footstool as he told me about a fantasy he had while at work that day.  I’m always glad to help a client after a tough day.  I like knowing that I’m their stress relief.

“For now, just listen Deb.  That’s all I need”.

Here’s how his story started:

My secretary, Sue, can be such a tease and she was really bad today.  She was getting crazy filthy with me and it got me thinking about having her.  I can never tell if she really wants me or just likes teasing me.  I work in a basement office and she deals with the shop upstairs.  I texted her because I got a call from another employee saying that she was driving the customers crazy.  I wanted them to send her back down to my office.  As she turned the corner at the bottom of the stairs and headed for the extra desk she wiggled her ass in my direction, looked over her shoulder as she slapped it and said, “You’re not getting this”.  However, she teased me more, telling me not to leave my chair or the show would be over.  She slapped her ass again and I could see her G-string as she blew a kiss at me.

There are no windows in my office and I keep the back door locked so I knew that we’d be safe.

John told me he sighed when he heard that, but then decided to think through what could really happen.  His fantasy got more intense.  I got brave once I fell into my fantasy, do you know what I mean, Debbie?, he asked.
I nodded and smile, saying “oh yes, yes I do”.

She walked back towards my desk, I stayed in my seat because I didn’t want to miss out on anything.  I didn’t want to scare her away.

I tell her, “I’ll give you an extra week’s pay if you follow my directions, all for teasing me for months now”.
A surprised look slowly creeps across her face, but no sign of fear.  No verbal answer.
She just comes around and sits on my lap, unbuttons her blouse and just lets me feel her up.  Her breasts feel great in my hands, like they belong there.

“That’s the wonderful thing about fantasies, isn’t it Deb?  They are always perfect.”
“That they are, no fear, no worry, just perfection.”  I answer.

I clearly become rock hard, my cock stays in my pants, but it pushes against her ass through my trousers.

I tell her that I should just make her strip down, tie her to my desk, and cum all over her body.
She laughs it off, at least for now.

I insist that she show me all of that G-string of hers.  Yes, I wanted her to take her pants off right there.  She did it.  I guess she really wants that bonus pay.  I picture her teasing me even more.  She steps out of her pants and looks at my crotch.
“So you want that cock out, don’t you boss?”, Sue asks me.
The tent I’ve pitched for her is obvious now, in fact it’s screaming at her.

I don’t answer her.  I just watch her.  She’s rubbing her puss over the front of the G-string.  It’s so nice.  I watch her as she licks her lips, but my eyes quickly move back to the small rubs she’s giving herself.  Again the tease, “I get to play and you don’t”
My cock twitches as I listen to her and watch the beautiful view.  She’s right; I’m not playing with myself.

Finally, she crawls onto my desk and I rip her G-string right off.  At long last, I get to see part of that paradise I’ve wanted for months.  She even has a nice little fluffy landing strip.

By now, I’m thoroughly engaged in John’s story.  It’s as though I’m in the back of the office watching it and taking notes.  My body is beginning to respond to his descriptions, I’m more aware of my nipples and the warmth between my thighs.

I unbuckle my belt for her and unzip my fly.  Then I kick off my loafers and lean back so I can rub her bra with my bare feet. 

Can you image feeling hard nipples through socks Debbie?  It’s really something.

I let up for a moment and she unsnaps her bra.  Luscious round breasts with hard nipples like candy are presented to me.  So lovely, matched with that pussy of hers that I now know she was worth the wait. 
She gets off the desk and on all fours at my feet, her ass facing me, and lets me rub my feet all over her.  She’s practically purring.

I figure I’ve waited long enough, fought hard enough, to start taking my prize.  I let my cock loose then drop to the floor with her, move her G-string aside and take four quick laps at her pussy. 
Debbie she was so sweet!
She turns, looks over her shoulder at me and says, “Ummm, you’re not done”.

“It’s funny Debbie, but this is where I started thinking of you”, he tells me
“Really?  Why?  I’m just your whore, that you use every couple of weeks”
“It my fantasy, that’s why”, he said sharply, and then continued.

I just wanted to feel her hand on my cock.  The other great thing about fantasy is that you don’t have to say much.  So she takes hold of my cock and starts to stroke me.  It’s then that I hear footsteps coming down the stairs.  Her stroke stops midway. 

Debbie, it’s you!  Dressed in just a G-string and a bra.
Now I get a real twinge in my pussy.

Sue’s back is to you, but when you just say ‘hello’, she turns around to see who’s speaking.  I tell her to keep stroking me for now.  You just watch Debbie.

For the first time I can see that John is visibly getting hard.

You know, I’m surprised but she seems to be a real expert, at least at hand jobs and I tilt my head back just enjoy the pleasure of feeling a woman’s hand, other than my own, on my cock.

It’s now that I tell Sue that she’ll earn her bonus soon.  I tell her to suck my balls while she’s on her hands and knees.  I help her out by standing up and pulling up on my cock.  Funny, but she doesn’t seem used to this.  So I tell you, Debbie, to tell her what to do.  You give her some quick instructions, like telling her how to kiss them and enjoy them to the fullest.  Sue quickly seems to get better.  I wink at you and moan to let you know that your instructions were being followed just right.

Then, Debbie, you drop to your knees, not in front of me, but behind Sue.
I watch you spread her cheeks and tickle her asshole with the tip of your tongue.  For the first time I hear Sue moan out.  Although it’s the first time I’ve heard pleasure from her, I can tell she’s enjoying herself.  However, her moan took her mouth off my balls and I’m sorry Debbie, but I yell at you for doing it.  Then Sue yells at me! 

Since I am the boss, I shut everyone up by saying, “everyone back to work!”

Sue gets back to sucking my balls and you get back to licking and enjoying her asshole and her warm slit.

John paused there, so I asked
“And? Then what?”
Truthfully, it was getting late and even though I was being paid for all this, it was taking up more time than most.

That was it.  After John finished telling me the whole story, he said to me,
“So it’s late, and now you know why I need you to suck me off now”
“If you have a friend that’s close by that can come by and eat your ass, that would be perfect.”

Then he moved to me and I assumed the position, finishing up my night, the way I often do, on my knees and swallowing an exploding dick.

I look forward to more interesting evenings, but until then, I’m out on the street humping my ass for my pimp.

Debbie Does The Streets #1 - Bar None

Since the nights, and the days, are getting colder now I sometimes hang out at the local dive rather than at my usual spot at the end of the alley. The other evening I was sitting there nursing a glass of Coke when I heard a voice behind me saying, “Hello Miss Slutty”

It was one of my regulars so I turned around when I heard his voice. He whispered in my ear then grabbed my wrist and pulled me to the bathroom. It’s not my favorite place to service my Johns, but it’s not my choice, something my pimp points out to me on a regular basis. He closed the door behind us and fumbled for the light. Assuring him that I could service him just fine here, he replied with an attitude of ‘let’s see’.

I had a new pair of fishnet stockings on and he requested me to show them off for him. Turning around slowly in the small space seemed awkward but it was his dime. Once I was facing him again, I lifted up my short skirt. I thought it best he knows that I didn’t have any panties on, only the garter belt holding up my stockings.

“That’s fucking amazing!”

In no time I was slammed up against the door with a loud bang. He slid his hands down the back of my legs and dove nose deep into my ass. Next, I felt his tongue swirling and flicking around my pussy lips. This isn’t a very common thing that I experience, especially with this guy, but I wasn’t going to say no to him. Not that he had to, but he felt the need to explain to me why is was tongue fucking my ass and fingering my pussy. It was that he wanted to get me good and ready for a hard fucking.
Next, I heard cheering from the other side of the door, even though I knew it was the football game it felt sort of good to hear it.

“Hey like that my slut?”
How else could I answer but in the positive? This was the best treatment I had in months. I was soaking wet now so I asked how he wanted to be serviced. He wanted something a bit different this time, telling me as he pulls his cock from his pants, to feel my tits on his cock. So, I pulled up my sweater and hiked my tits up and over my new red lace bra. I like how my tits feel when they stick out like that. My nipples were as hard as his cock by now and he rubbed the tip of his leaking cock across them. Momentarily he slipped into the crevice between my tits, but I knew in the confined area it just wouldn’t work well for me to have him fuck them.

“So let’s get down to it, what do you like to do to whores in bathrooms?”

He wanted to fuck me up the ass because it would be so dirty. Even though he was rock hard, the best way to get in shoved up my tight hole, I lubed him up by quickly licking and drooling on his cock first. Even though I wasn’t really sucking him off I was still making those tasty slurping sounds I always do when I savor a man. However, I thought I heard something else.
I soon let his cock drop from my mouth and asked,
“Do you think the guy that just came in can hear me slurping on your cock?”

Too involved with me licking his dick, he hadn’t even heard anything else.
“What guy baby?”

Maybe John thought I was paranoid, but I explained that I thought I heard someone come in. I tried to pass it off as just someone that had been too drunk to notice. Well, it made him just as curious as I was. The door to the stall wasn’t closed all the way, if it were I wouldn’t have been able to perform all the requested services. John looked out and I was vindicated, the drunk was walking out the door and he left it half open so the people at the bar had a fairly clear shot of the two of us.

He was quick to point out that he knew they were all thinking, ‘lucky bastard’. He groaned as I lapped and drooled on his cock just a bit more and slapped my tits hard with both hands. “So you ready to take my ass hon?  I have to get back out on the streets or my pimp is going to be disappointed in me. That’s not a good thing.”, I said wanting to take my money and get on with my evening.

It was then that he told me that when he looked over my shoulder and out at the bar there were guys rubbing their cocks.
“Here’s an extra $100, now I’m going to fuck you on the bar”, he said as he dragged me out of the bathroom and pushed me into the gang that had gathered there.
“In fact I’ll give you another $100 if we find another girl to join us”, he added.

I’d done stud parties before so this wasn’t new to me. I figured I’d get some extra money and it was warmer in here than the street. Not to mention the bar smelled better than the bathroom and was cleaner, so I didn’t fight it, not that I really could if I wanted to.
I fell into a seat at the bar, my tits bouncing and my skirt hiked all the way up, I asked, “What does a whore have to do around here to get a drink?”

Before the stunned bartender could say anything, John answered by pouring a bottle of vodka on my face, saying, “I’ll show you”.

He bent me over the bar and without any warning drove his cock up my ass. The crowd cheered as they watched me wince and John pound my ass. The bartender ran to lock the door as guys started to pull their cocks from their pants. John did a final few deep strokes, pulled out of me and came all over my ass cheeks.

No need to go into all the details, but as I’m sure you can imagine, the next 90 minutes involved me getting used up faster and harder than I had been in a long time. Money started being slapped down on the bar as I was given drinks and alcohol or cum or both were poured over any part of body that could be reached. I was forced on my knees to suck off guys, at one point 5 in a row. I had swallowed so much cum that I was actually getting queasy. Other than that I was basically fucked while I was bent over, either up the ass or doggy. One guy insisted on shoving a beer bottle up my ass while he fucked my pussy. What really surprised me was the one of the few women that joined in the crowd. She used ice tongs on my nipples as she ate cum out of my pussy.

After what seemed an eternity the bar mostly cleared out, I picked up the twenty and fifty-dollar bills from the bar, straightened myself out and left. I went straight to my apartment. After counting the money, along with my initial charge of $200 for John, I had another $1720. I figured I was covered for the night and went into to soak in a warm tub.

Tomorrow is another day.