Chapter 4: Randy pays me [Karen]

Jerry was hardly my only romantic interest, even at work. But by chance, my two regular lovers at the time were not coworkers. With plenty of sex and sex opportunity outside work, I had no need to do more than flirt in the office. And I was afraid that a lover hanging around my desk would screw up what I had going with Jerry. Besides, even with the other guys, the older professionals, I got a lot of pleasure showing off my feminine qualities that I’d miss with a lover. Lovers eventually take you for granted, especially when you want them to notice you. Showing a guy my panties might spice up the afternoon, but only if he considered it a treat.

About a month after Hilda and I became bosom buddies, I got more attention from Randy than even I wanted. He’d been coming on slow for the several years I’d worked there, but something seemed to have recently convinced him that I was a more likely target to hit on than he’d previously thought. What it was I never found out, even trying to read his mind. This mind reading business doesn’t tell me what’s buried, only what the guy’s actually thinking. I could have asked him why he started thinking of me as a loose woman. While he probably wouldn’t actually tell me, a question like that usually brings up the memory to the surface. But I didn’t want to sound angry. I don’t mind being thought of as a slut in a friendly sort of way. A slut has sex for the fun of it. And that certainly defines me. In my book, a girl who has to love a man to bed him is a prude. Hilda and I agree on that one.

But I didn’t want a romantic affair with Randy. He didn’t even particularly turn me on. I’m not sure why. He was typically tall, dark and handsome. Maybe it was just that he wasn’t quite as attractive as he seemed to think. He was married but separated and getting divorced. While he blamed the slow process on his wife I could tell because of my special ability that he was in no more of a rush to make it permanent than she was. He didn’t know why she was dragging her feet, but he found the status very comfortable. A girl couldn’t expect him to make any immediate commitment. Yet he wasn’t cheating either. I knew Randy was only interest in sex, not any sort of relationship.

“Randy, stop it.” I demanded one time when he cornered me in my office. “Look. I know you well enough to know you only want to get in my pants with your dick. No,” I said, shushing his protest with a finger to his lips, “don’t bother denying it. I don’t even mind. If I had any sort of affair with you that’s all I’d want anyhow.”

At this point he had me backed up against the front of my desk, leaning back a bit, away from him. But he was standing so close that his erection was pushing against my belly. We both knew I could feel it perfectly. The fact that I was ignoring the contact was encouraging him.

“Look, I don’t want you for a boyfriend. I hardly even like you. I could imagine having sex with you, but not going out to a movie with you. I’ll tell you what. Pay me.”

“Huh?”

“Pay me. I’ve always had this fantasy about being a whore. I think if I was doing it for money, and had to do it just to please you, I’d find it a real turn on. What does a prostitute get paid? A hundred a shot? Must be more for an entire evening or the whole night. Since I won’t have any other customers you could use my body as long as you wanted, two or three times if you’re up to it, as long as you pay me the going rate for a one shot. If we both like the arrangement, we could go for encores. But I suppose if I’m to be a proper professional, I should try to raise my rates after showing you how good I can be.”

“Why should you want money? You get paid more than I do. I should charge you.”

“Ah, but I’m the woman. You’re the one who’s so horny you’re sticking your penis into my belly.”

My verbalizing of what he was doing made him suddenly embarrassed. He jumped back several feet. It felt good to be able to straighten up, but I kind of missed the pressure on my abdomen. I think I love penises second most when I can feel them still inside my lover’s pants. When we’re both naked, I’m always afraid he’ll put it in me too soon. Only if he takes sufficient time and gets me really ready do I really love feeling it inside me. But if he does do everything right, then I do love feeling it inside me, even more than when it’s still in his pants.

I pretty much knew Randy was not going to be a perfect lover. He would lose patience and fuck me for his own pleasure long before I was really ready. So it occurred to me that, doing it like a whore could make the inevitable sort of exciting. Anyway, unless I tried, I’d never know how realistic my fantasy could be. But it had to be real prostitution, not just pretend.

“Not only will you pay me, but you’ll pay me the going rate, so that I know you aren’t just using me because I’m cheaper that the girl on the street. I want to be your prostitute of choice, not your compliant girlfriend. What do the girls up town charge?”

“I don’t know.”

“Liar.”

“Well, it’s been a few years. Last time I asked one she wanted fifty for twenty minutes.”

“I bet it wasn’t long ago and the price is still current. OK. I don’t work for less than an hour. A hundred dollars. Time after the hour is over is free because I won’t have anything else to do anyway. So you can fuck me as many times as you want before dawn. But a second date will cost the same or more. If I manage to really please you I might try to jack up my fee. Or I might ask for a tip before I leave. Randy, a hundred or more is no big deal for either of us. But it’s what you would pay on the street. I want you to prove to me with your wallet that you like my pussy at least as much as that of a street walker. And if you don’t, well, you don’t have to give me any repeat business.”

“Anal sex?”

“It will cost you extra!” I said in a regular voice, then added in a whisper, “You have to coach me a little here. What should I demand? Would another twenty be right?”

“I should say yes, but I don’t know. Prostitutes try to charge twice for everything. Sometimes you get a girl in your room and she tells you that all she agreed to was a hand job. Actual coitus costs more. I hate dickering after we’ve actually made the arrangements, and the girls know it. But that doesn’t stop them from being greedy. I imagine ahead of time the girl might agree to twenty, but if I suggested it once I had my pants down she’d demand a hundred. Are you supposed to be an honest whore?”

“I think so.”

“Well, than we’ll make it a hundred and twenty for anything I want, including anal sex, cunnilingus, fellatio, even bondage. But I think bondage is usually mostly a treat for the girl. Really, I’ve never done anything kinky with a professional, just with girlfriends. Not even anal sex.”

“OK, I don’t mind anal sex much. Just between us, and before we assume our respective roles, I have to admit a few things. The type of sex I’m expecting is exactly what I usually don’t want but often get from my lovers. If sex was only for my benefit, say I was paying you, I’d want a back massage, say for a half hour. During that time you would tease me by lightly touching my lips and anal opening when doing the insides of my thighs. When I undress you should look at and admire my tits. But don’t touch them. They’re shapely but small, and when a man touches them, at least before I’m ready, his touch only reminds me of how small they are.

“After you’ve excited me sufficiently, you have me turn over, rub my legs, arms, neck and face. Then you start on my torso. Waist, hips, even run your fingers through my meadow and between my lips. It’s better if you don’t penetrate me fully at this time, but won’t matter much if you do. I never mind much getting finger fucked, even when I’m not ready. But you still have to be careful of my tits. Work around them, underneath, above, and on the sides. Try to move closer to my nipples. If I sigh contentedly, I’m yours to do with as you please. And please do something. It takes so long for me to get comfortable enough that not having my tits squeezed when I want it is a terrible waste of opportunity.

“But if I tense up, stay away from my nipples. Anyway, I’ll be more than ready to fuck at that point just about any way a guy wants me, anal or vaginal. In fact, I’m so grateful that I’m eager to reward him for the pleasure he’s given me. But you realize what I’ve described would take much longer than what a whore generally does for a John. I imagine I’d have to pay a gigolo more than a hundred or a hundred and twenty. Only a few of my lovers have had the patience to treat me so patiently. I’m used to being less than fully satisfied. And anyhow, I would never expect a man who was paying me to do any of that. What excites me is the idea that I have to do for you exactly what you want and don’t have to think about what I really want.”

“Would you let me try doing it that way?”

“No. I told you what I want you to do. And anyway, you’d have to be a masseur to do the first part right.”

“Well, I took lessons once. And when I practiced on my girlfriend at the time, she seemed to really like it. I may not be a professional, but I can give a good back rub.”

“Oh! Well, no. First time do it the way we agreed. I really want to live my fantasy at least once. So no funny business. You make me do whatever you want and forget what I said. Otherwise no deal.”

“How about if I paid you more?”

“If I was really a prostitute that would interest me. But I only want to charge so you know your paying for my pussy. And I intend to keep the money. In fact I’ll probably spend it on a bunch on real sexy play things to celebrate my semipro status. But the answer is still no, mister. We stick by the deal.”

I could tell because of my special ability that Randy was dying to see if he could please me in a way that few of my lovers had. It was something that I would not have expected. But I was still determined to be a real whore now that I’d set it up. The idea of selling my pussy instead of just giving it away, had really gotten me excited. Even more than the prospect of a perfect affair. Besides, in spite of his intentions, there was no guarantee that he could deliver. While I was certain he could fork over one hundred and twenty dollars and make me a one time prostitute. Playing the part of a whore had always been a sort of tentative fantasy. Maybe lots of girls think about what it would be like to be used by a man who’s paying for the privilege. But lately, since Hilda had dumped her revelation on me, the idea had preyed on my mind excessively.

It seems any time I arrange anything at work it’s always for that night. I refused to invite him to my apartment. So, I made him meet me on the street and pretend to be picking me up. I almost had a run in with some real pros before one of them realized I was only play acting. She told her friend in a stage whisper that embarrassed me in front of the whole street. I didn’t mind people thinking I was a street walker, practically naked by way of dressing for the part. But for a second all those guys suddenly realized I was just wearing, or mostly not wearing, a costume, that I was a normal woman showing off her body for pleasure. I suddenly felt every bit as naked as I was with the sudden attention I received. Randy, however, saved the scene by acting his part perfectly. After some further negotiations, when he led me away everyone except the two girls were doubting her conclusion.

Randy took me to a hotel room. His wife had kept their apartment and his temporary quarters weren’t much, so he’d rented a fancy room, paying much more for it than he was paying me! I liked the touch. The cost didn’t impress me any more than an expensive dinner. But the thought was what counted. When we walked through the hotel lobby, I stayed in character, while Randy, my John, was embarrassed escorting a girl wearing next to nothing who was obviously a whore. My blouse was transparent. No padded bra. But my tits are adequate when visible. They make up in quality what they lack in quantity. Unfortunately, under several layers of clothes they hardly assert themselves without help. So all of my bras are padded.

When I undress with a lover, once my blouse comes off, I quickly remove my bra and toss it away. Any man with any experience will know it was padded. But I don’t have to remind him of the fact. Nor do I like him examining the evidence. He can examine, all he wants with his eyes, what was hidden. As much as I don’t like my breasts handled at this point, I love having them looked at. When I was out on the street, I was deliciously aware of the fact that every man going by was seeing me naked.

My dress was a translucent beige slip. Before picking an outfit, I’d checked out a few street walkers and decided that they were mostly wearing sexy undergarments instead of outer wear. Some high style gowns are pretty revealing, but these girls wanted to look sexy while also cheap and available. Randy had arrived exactly on time about ten minutes after me. It was a long, exciting ten minutes. The worst part was that I got several near hits and didn’t know what I’d do if either guy had consented to my ridiculously high asking price. Did they like me because I didn’t seem interested. The other two girls were sexier.

Under my slip-dress I had on skimpy black thong panties. I wanted the contrast to make them visible. The little triangle of black material seen through the front of the slip advertised my pubes much more blatantly than my pubic hair would have. The even smaller triangle above my buns only made it obvious that my fanny itself was also quite visible. Randy later told me that no pro had ever embarrassed him the way I had. Those girls always have some way, or some extra clothing to put on, so they can quickly become considerably less exposed and they use the cover-up going to and from their beat, and when they go somewhere with their John. Walking through the lobby still naked was not keeping in character as I had thought!

In the room I refused to act like I knew Randy from anywhere. It was my way of reminding him to treat me like a professional. I made a point of not telling him my last name, and giving him a false first name. I think I told him to call me Mary – “like the virgin”. Randy tested me by immediately grabbing my tits. Not hard or anything, just firmly and possessively. And I forced myself to act positively. Like a pro I pretended that I loved it. The funny thing was that I did! But I haven’t learned to like having them quickly attacked, except when I’m selling myself. As my lover I’d still want even Randy to keep his hands off them. Then he demanded I suck him until he got good and hard.

I can’t say I love fellatio. I’ve never minded it and sometimes do enjoy it a lot. But do you know what whores do today? They put a rubber on the guy and suck the rubber! I can’t think of anything more disgusting for the girl and hardly anything more frustrating for the guy. Randy says he thinks few guys want it any more. I didn’t hold the line on that issue, and gave him head the way we both wanted me to do it!

I should have charged him something extra for that. But how would I respond if he simply said go ahead and use the rubber? I wanted his prick naked in my mouth even more than he did! I guess Randy hadn’t had a good blow job for a long time. He seemed willing to let me suck his dick practically forever.

“Mister?” I kept pretending I didn’t know his name. “Isn’t there something else I can do for you?” I asked in my little girl innocent voice.

“Of course. Get on all fours. Do you have any lube for your ass?”

“Oh goodie.” I responded as I got a dab out of the tube and spread some around inside my hole.

Then I handed him the tube and presented him my hinny just like I would my back at the beach for sun block. It’s always more interesting when a man feels around inside you. Besides, he has much better access to my ass hole than I do. A finger fucking with KY is much more sensuous than using saliva in either hole. But after thus blessing both my orifices, he seemed to loose interest in imbedding his penis anywhere in my crotch.

Oh well. It was his nickel and he was the customer. I had no more right to complain about a fuck withheld than I did about receiving one. At this point, after impaling me with his fingers, he made me lay down on my back again, and spread lube on his penis. My vagina was already so well prepared for impaling that this made no sense. I had just about decided that he was going to ask for a hand job when he sat down on my chest, his erection pressed into my cleavage. Except I don’t have cleavage! My breasts aren’t big enough to touch each other or give a man even the suggestion of a tit fuck. If I’d allowed myself to fall out of character I would have cried. Nothing else I could imagine a man doing to me could so clearly point out how tiny my breasts were. There was no way this would give him any pleasure, other than to embarrass me!

But I told myself that this was only a job. And the customer got what he wanted even if it was just to embarrass me. If he wanted to insult me that was his business. What he was doing to me was only something most women would welcome. Even other women with small tits must have learned to like it. So I laid there pretending to like the feel of the slippery underside of his penis rubbing my sternum. When I looked up at him, though, his eyes were closed and he had a look of extreme pleasure on his face. I soon realized that he loved rubbing himself on my female chest, even with it’s undersized padding. It made me realize that, small as I was, this man still seemed to find my upper body more than adequate. That smile on his face erased every thing bad I was thinking about him! If he’d spent the next hour playing with my tits I’d have probably loved it! So when he turned me over again, laid down on my back, his manhood pressing down into my business district, and reaching under me, cupped my breasts, one in each hand, I actually enjoyed it.

I was so surprised at my pleasure that I hardly noticed his rod insinuating itself into my rectum. Randy’s about normal in size, so done carefully the way he did it, it didn’t hurt at all. As I said, I hardly noticed it. I just couldn’t get over the fact that this man seemed to love my tiny tits, and I loved having him hold them. I wonder if large breasted women miss feeling themselves completely cupped in a man’s hand? Probably not. If fact, until that night I’d never even enjoyed the sensation. Yet a man with average size hands can completely and firmly claim my entire endowment. For a few minutes that night I felt I was surrendering myself, by way of my tits as proxy, into his hands, and loved that form of surrender much more than just having my crotch possessed by his manhood.

The bliss I felt, replacing my usual dread didn’t last all night. The rest of the evening I enjoyed it whenever he touched my nipples, but probably no more than most girls would. It was only those first few minutes when it was a mind blowing ecstasy. Randy may have sensed this because later he gave my tits only a normal amount of attention. He was still fucking my ass when I came down from cloud nine. I may have actually climaxed because where my pussy was pressed into the sheets there was a large wet spot. My ass was so wide open and receptive that I actual started tightening my sphincter trying to increase the pleasure for him.

“Oh! That feels good.” he responded.

He then stopped fucking me and just held himself as far inside my fanny as he could reach. I quickly realized that he wanted me to squeeze his stationary member with my muscles. It’s about the strangest way two people can fuck, and quite enjoyable. Any girl can easily squeeze her lover with the opening of her ass hole. Some especially talented girls can do it with their pussy opening as well. I’m not one of these women. But I can give my lover a squeeze fuck with my ass hole, although before that night I never imagined doing so.

“No. Oh yes! Oh my!”

I accomplished more than I’d meant to and made him pop his cookie right then inside my fanny. With as little experience as I’d had with anal sex, I couldn’t remember a guy actually ejaculating inside there. It was a little disappointing because he hadn’t even entered my vagina yet. Nor with so little warning could either of us enjoy his climax much. He just had one chance to shove himself inside me as hard as he could and went off like the proverbial fire hose.

His limp penis felt big inside me and annoying. He wanted to pull out almost immediately, but only did so when I indicated I wasn’t enjoying it much either. Sometimes after vaginal sex, I want my lover to stay inside me for hours. Or so it seems, since he never does. But this first experience with an ejaculation in my anus taught me that my ass hole had no such desire to remain plugged.

We took turns in the bathroom. I watched while he washed off his penis, but made him leave while I wiped and washed up my rear. One of my earlier preparations, expecting some anal sex, had been the use of an enema. But I still felt like my fanny was probably a shitty mess. The toilet paper gave no evidence of this, but I still felt a lot cleaner when I was done. When I came out of the bathroom I had a towel wrapped around my waist.

“No. Stay completely naked. Don’t argue. The customer gets what he wants. And even if I’m temporarily indisposed, I still want to see every square inch of your loveliness.”

Actually, I wanted to stay naked. But I also wanted him to demand it. He played his role perfectly. It seemed silly that he was paying me for this because I was sure I was enjoying it far more than he could be.

“Would your honor want a taste of my loveliness then?”

His penis may have been indisposed, but his lips and fingers were fine. I’ve been kissed everywhere, even tongued in my anus. Randy skipped giving me that particular treat, but I can’t think of anywhere else he missed. Sometimes he was finger fucking me in both holes with one hand, cupping one breast with the other, and sucking on my remaining nipple at the same time. My tolerance to breast stimulation was still holding. I loved it.

As I’ve said before, my best fantasy is lying naked having my back rubbed. But we’d agreed to avoid that this night. By the time Randy started in again doing my entire body with his tongue, his member was more than ready to be more than a spectator. I couldn’t wait for him to decide to use me in the conventional way. But it was his call. I didn’t even suggest that he take me before he decided to do it himself. The result was, that by the time he did fuck my vagina, I wanted it more than I ever had, or have since. When I’m not getting paid, I guess I always ask for it long before this point.

The actual missionary sex was about as good as it gets. Which means I had a whopper of an orgasm. But even with that physical pleasure, I don’t think it was as spectacular as I’d been expecting. They say anticipation is the best pleasure. Sometimes it is.

—————————————————————————–

There were three chapters before this and several later. Karen has the ability to read men’s thoughts, especially those that include lust for her. This chapter seemed to need the least amount of rewriting, so here it is.

Love and Kisses, Cathy

---