Dinah Might

I was out of a job and things were not looking to turn around anytime soon. There were the familiar goto options like fast food and the like but it was still minimum wage and my house payment would chew that up and then some. I'd have a house with no food in it.

I had a friend in the sex industry but I just couldn't bring myself to approach her even though I knew she had the knowledge I'd need to do it. It seemed like the move of last resort so the question became, was I in 'last resort' mode yet? Sex for money always felt debauched and while I loved my friend I also avoided discussions about her profession.

Anna was a reasonably high priced escort who had been in the business for a few years. Knowing my general feeling about her work she never brought it up unless I asked and I was usually not asking. Anna was a beautiful girl so it made sense she'd make plenty in the sex biz. Men were constantly checking her out anywhere we went. If you kept an eye out, men had one eye on their immediate concerns and one scouting out her fabulous ass. Seriously, you couldn't look away.

Having breakfast at her condo I casually broached the unspeakable boundary and asked her how much she made as an escort. I remember dropping my fork on the floor when she told me. If I were making that kind of money I'd be instantly relieved of my new found poverty status. The only hurdle was getting right with fucking guys for cash and I didn't think that would ever happen.

"It sort of depends, Dinah," she said, "on whether you like it or not. The more you like it the more you'll make. Guys can sense when you don't want to be there."

"What kinds of things do you have to do?" I asked.

"Well, open a dictionary on erotica, read it from cover to cover and that's what you have to do. I've had men ask for all sorts of kinky things and as long as you can roll with it you'll be in the money. If you were good at it, they will come back to you endlessly. If not, they'll move on and find someone who is. If there's something you don't want to do it's best to state that upfront. Also, if you have specialties it's best to advertise that too.

Guys who are willing to pay for sex want the forbidden fruit. Something they're really into but can't get from their wife or girlfriend. Expect the unexpected. A lot of guys like rough sex. That can run the gamut from hair pulling to spanking to bondage. Expect requests for anal sex."

Up until now I was just taking casual mental notes but suddenly my senses were on high alert, "Anal?"

"Yup, and sometimes if you're servicing more than one man they'll want double penetration."

"What do you mean?" I asked, afraid I already knew the answer.

"Two guys are fucking you at once, one in your pussy and the other in your ass."

"Holy shit, do you do that?" I asked.

"Yes, I've handled as many as five at a time. Double penetration, one in my mouth and jerking off two others. If you do a party with multiple men that's likely to happen. They're all hungry for you at once."

"Holy shit," I said again.

"One other thing you will quickly find out...what you like, because, believe me, you're going to do stuff and find out you really like it. Nearly every girl likes receiving oral sex but other things will surprise you."

"What surprised you?"

"That I enjoyed a light dose of BDSM. I realize that I'm a submissive with occasional moods of dominance."

"My eyes are glazing over because I don't even know what that means."

"It means I'm into things like getting tied up, spanked, forcibly fucked. That, for the most part, makes me a submissive. I like being dominated. It's a role play. Maybe you'd find out you're a dominatrix or maybe your not into any of that at all."

"Holy shit."

"You've said that already. Welcome to the world of fetishes! I have one client with a foot fetish so it's all about that. He gets his rocks off licking my feet and sucking my toes. Another likes me sitting on his face. One more thing to keep in your back pocket is dirty talk. Never underestimate the power of dirty talk to rev up your client's attention."

"I don't know, Anna, maybe I'm not cut out for this. I just can't see myself doing that. I'm going to have to think about it."

"It isn't the thing for everybody and maybe not for you. Look, if you think you want to try it I've got a client who likes two girls, a duo, and you could come as my partner and then I'd be there to help you through stuff. I can guide the action with you."

"It's just so weird. I suppose if I did it with you I'd find out if I could handle it. I'll call you if I get up the nerve."

I sat on the idea for about a week and the more days of unemployment that passed and the more my prospects were not panning out, the more I was driven to try it. If I just didn't think too hard about getting naked for a stranger then I was fine. I texted Anna to take me on for the client who wanted two girls. She texted back to dress 'sexy as hell' and shave my pussy. "Most guys like it."

Standing nude in front of my mirror, shaving my pubes, I took stock of my black, short Page Boy cut, my long, graceful waistline, great 34B's and rocking legs and thought 'You look like man candy'.

I went through my closet and came up with a skimpy but classy outfit and followed Anna's requirement for the highest heels I owned. When she picked me up, she was blown away by how hot I looked and said, "If he won't fuck you, I'll fuck you myself."

I was nervous as hell and thought more than once about running off but I owed it to Anna to go through with it. We were invited to an upscale hotel downtown where we'd be with some guy for the next couple of hours. My cut was, if I could pull it off, six hundred dollars and I needed the money bad.

We knew the room number and went straight for it. Better not to draw attention to our 'sex for hire' selves. When we got to 601, Anna gently knocked on the door and a man, perhaps 60 or so, medium build, plenty of gray, opened it with, "Come on in, girls. Hello again, Anna," and kissed her on the lips. "Oh my, Anna, who do we have here?"

"Tom, this is Dinah."

"Wow," he said, stepping back to take it all in. "She's a fucking dream. Next time you come don't forget her." He walked over and ran his hand down my back and over my ass. "She's gorgeous. This is going to be fun."

I was still incredibly nervous but tried my best to hide it. He kissed me full on the lips and I reciprocated. "Oh yes..." As he kissed me again, Anna had slipped over and rubbed his ever expanding cock.

He asked if we'd like drinks and went over to the partially stocked bar and took orders. I thought this might help me be a little more pliable when we got down to it. I just kept looking at him trying to imagine what he would do with me. "Anna, here's your gin and tonic and Dinah, here's your Cosmopolitan. Why don't we have a couple rounds and then you girls can entertain me in other ways," he said with a smile. He sat between us at the bar and I noticed his hand moving up the inside of Anna's thigh. "Ummmmm, that's so nice," she said softly.

After the second Cosmo and cruising towards a third, I was indeed 'pliable'. He asked me to turn my back to him and when I did so he slowly unzipped the back of my cocktail dress. It was so sexy how he eased it down my shoulders. I stood up and it dropped to the floor where I stepped out. Then he did the same to Anna and there we were on each side of him in our bra and panties and heels. Before we went in Anna had reminded me that no matter how many clothes come off, unless the client requests it, the heels stay on. Tom, like a lot of guys, liked to fuck girls in heels.

Tom turned back to me and removed my bra. "Dinah, your tits are exquisite beauties," and began to swirl his tongue around my nipples coupled with occasionally sucking them. I don't know how much the Cosmos had to do with it but it felt delicious and I tossed back my head and quietly moaned.

He suddenly pulled my panties down to my ankles, lifted me up so I was sitting on the bar, the panties dropped to the floor and he went after my clit. I was approaching drunk, it was all so surreal and I was dissolving into the perfect sex toy for him. The nervousness was long gone and, in some ways, it felt incredibly liberating.

As he ate me with my eyes closed I opened them to find that Anna was to the right of me and she started licking my tits. The combination of sensations caused me to orgasm and my body shook with pleasure. When he knew he'd gotten me off, he turned his attention to Anna's fucktacular body and removed her underwear the sensual way he had removed mine.

As I turned to take a sip from my drink, Anna said, "Fuck me, Tommy. Fuck my sweet cunt." He went into urgency mode, pulled off his pants and frantically answered her request. She gripped the bar railing while he slammed her. To join in the fray I got down of the bar, unbuttoned his shirt and tossed it away. Then I kissed his nipples while he continued to pile drive her assets.

He was in heaven and I was beginning to understand the point of him wanting two girls. I knew it would soon be my turn to take his shaft and any reluctance to do so had melted away and, as reticent as I was before, now I just wanted to do it. He pulled out of Anna and like a flash I took his cock down my throat. The Cosmos helped to relax my gag reflex as he furiously throat-fucked me. I could barely get a breath it was so intense. Then as fast as that all happened he turned me around and launched into my accommodatingly wet pussy.

Anna started the dirty talk again. "Bang this fucking hot little bitch, Tom. Dinah likes it." Tom, encouraged out of his mind, slapped my rear, and when I yelped he did it more. Then he reached up and wrapped both hands around my throat and kept the cock coming as I fingered myself. Anna ran around to the back of the bar and facing me, reached up and twisted my nipples until they hurt.

OMG, I thought for a split second, I love this. The combination of sensory input was overwhelming. Tom took a lot of time in me while Anna worked the periphery and the next time Tom reached around and twisted my nipples I spasmed with my second climax.

"Anna," Tom demanded, "come and stand next to her, I want to fuck the duo. I have the two hottest pussies in the world to choose from. Feel free to have your drinks, ladies. I'll take care of the rest." We took sips while he fucked both of us. The game became when he was in one of us the other took a drink and vice versa. We were getting hammered and fucked silly all at the same time.

He was loving the setup and didn't want to quit but couldn't hold back any longer. While he was in me, Tom cranked out some strong thrusts and then said urgently, "Take my cum girls." Anna turned quickly, squatted and stuck her tongue out. I just did what she did and Tom, with a roar, came on our faces, the cum running down our cheeks. OMG, what the fuck had I gotten myself into?

"If you need to freshen up, girls, the bathroom's that way," as we went off to clean up and reapply our makeup.

"So what do you think, Dinah? Hanging in there?"

"For sixty, Tom has some serious energy. I thought he was never going to take a break. In answer to your question, thank god for Cosmopolitans. I'm just trying to go with everything and..."

"And what, Dinah?"

"I was shocked at how totally I was getting into it sometimes. I came twice"

"I noticed...and so did Tom. He's going nuts over you."

As we walked back into the room Anna playfully pinched me on the rear and I jumped a little. Tom saw it and laughed. "Get your drinks and sit with me, girls." We sat on each side of him with our legs crossed and his hands caressing our thighs.

"Look, girls, I know I booked you for two hours but this is the best duo I've ever had and I want another shot at you beauties before you leave. Could we add another hour? I'll compensate you well."

"It's a big 'yes' from me. I love that cock, Tom. How about you, Dinah?"

"Yes, Tom, I'd love to," I said.

"Great, girls."

We talked a bit longer while Tom recharged his batteries. Mostly small talk and such but Anna mentioned that this was the first time I'd ever done this. I didn't immediately get why she was mentioning this.

"Oh fuck, you're kidding," he gushed as he looked at me, "you're one of the most delectable girls I've ever had the pleasure to ravish. I hope we have many more meetings. I've been in love with the spectacular Anna since I met her and now you join her? I'm completely under your spell. I don't care how much it costs I want you girls every week." For someone who often questioned their own sexual prowess, I was flattered that he wanted me so badly. I also knew it was just sex. I did a lot of other things well. It was just that I wasn't expecting to like this and now I could easily see making a lot of money, at least for awhile.

Now, emboldened by a well-fed ego, I reached out and took hold of his flaccid dick, leaned over and sucked him back to life while Anna got down and licked his balls. He was hard in no time and pulled Anna to her back on the sofa seat, tore off her panties and started drilling her. I went to the bar, made a round of drinks and came back to the blistering fuck.

Tom had her by the ankles. He told me to take one of her legs while he put it to her. He was sweating heavily and grunting. Anna was grunting as well. Then he stopped on a dime and said, "Let's go to the bedroom, girls!"

We followed him not knowing what was next. On the bed were straps on all four corners and Tom said, "Strap her down, Anna, and let's enjoy our girl here." I had no idea what was happening but laid down spread eagle as Anna cinched the straps down on my wrists and ankles.

Tom and Anna crawled around me like birds of prey. Moving their hands all over my body. I closed my eyes and let it wash over me. Tom put his mouth over my pussy and went at it with the same intensity he had fucked Anna with. I orgasmed again, a strong surge through my whole body.

"Turn her over, Anna," he told her.

She loosened the straps, I turned over face down, my hips elevated on a pillow and she tightened the straps again. Tom caressed my legs as he approached my vulnerable ass. He penetrated me and then began pumping as hard as he had Anna. He grabbed a handful of my hair to help him drive his cock that much harder. OMG, I'd never had rough sex like this, ever. The bed was shaking and creaking as he did me. Anna stayed at his side, one hand on my butt cheek, French kissing him while he did it. In between his ten minute crusades he would slow up and run his forefinger over my anus. I thought that might be the prelude to anal sex but it didn't happen. Then he would grab my hair and get back to work.

Finally, unable to hold back any longer, he shot a warm stream of cum up my back and, like that, he exhaled and was satisfied. Might I add, more than satisfied. Anna released the straps and Tom extended his hand to help me out of the bed. He was so galant that you would never have guessed that he was humping me like a wild animal just five minutes earlier. He was sixty and fucked like a teenager.

I got my things together while Anna settled up with Tom. I'd done it and survived. When we got out in the hallway and Anna handed me a thousand bucks in cash. I just couldn't believe it. I'd done three hours of spreading my legs and had four orgasms for a thousand dollars. I'd have to consider my feelings about it all later, but for now I was relieved to have had a job...

And apparently one I was naturally very good at.

On the car ride home Anna told me how out of his mind he was about me and, "Beg her to come back with you...next week...tomorrow, I don't care, I just want that gorgeous girl."

"The only other girl he's gotten this crazy about was me so I think he'll pay just about anything to fuck you again. He's like afraid that after your first time you'll never return because we tied you down and he fucked you so hard."

"Really, I didn't mind that. In fact, when you twisted my nipples in the middle of it I never got more aroused. I was aroused by all of it. I was only afraid when I was on the bed he might fuck me in the ass and I wasn't ready for that yet."

"Yet? Are you saying you're interested in more adventures? If you are I'd love you as my regular duo partner. We'd make a killing."

"Ya, I guess I'm saying that. The money's too good and I'm feeling very naughty. You were saying there might be surprises and you were right. I got comfortable real fast and, this is weird, I wanted it. I was almost jealous when he was screwing you. Actually, it's freaking me out."