The Amateur


This story is true.

His ad on Craig's List read like this:

"Very $Simple – m4w – 32 (DuPont Circle)
This is very simple: rich lawyer looking for poor college girl who needs a good time and mutual $atisfaction.

Brunettes a plus; facials are a must and non-negotiable. Send your picture, I'll send mine."

Her reply went like this:

From Sunday, October 24. 6:11pm

how about a SWF brunette graduate student with no recent satisfaction & facing no loan dispersement until January?
i'm south of the circle.
start with a vodka tonic in a dark bar, make sure we have basic mutual chemistry, then?

She attached a photograph of a thin brunette with short hair wearing a tube top, the cute kind that had become fashionable again. She appeared to have small breasts, and was wearing a chunky necklace that drew attention to her creamy décolletage. It appeared to be a group photo, on the edges were visible the arms and shoulders of other women. The face was obscured. It was entirely a lovely photograph; not the kind of girl one expected to meet on craig's list.

From Monday, October 25. 11am

sounds good to me, and i like that tube top. how
about you meet me at the Ritz bar tomorrow at 9:30 and
wear something easily removable.

grad school? What's your field of study.

From, Same day, 12:21 pm

9:30 tomorrow. ritz. sounds good.

easily removable... that'll be fun and a bit of a challenge in this weather.
didn't you promise a pic? after all i sent you one...
this'll give me something fun to think about when the profs have gone on tangents. MA in IR, and it hasn't been all that thrilling this semester.

Oh, and I can't host.

From, Same day,12:58pm

Ask and you shall receive.

I might have some time for a debauched afternoon
tomorrow. How would you be about the Ritz, but at
2pm? I can host, no problem. All you have to decide
is if you're going to swallow, or take a facial . . .

He attached a photograph, not of himself, but of someone who looked reasonable like him. The photo was a reasonable likeness; square jaw, wavy hair, a bright smile. The person in the photo did not have glasses; that was the only major difference.

From Tuesday, October 26. 10:46 am

I have internship/class until 6. somehow my schedule is far closer to a full-time employee than a students.
and were you planning on hosting at the ritz? visiting from out of town?
and with reciprocation, you can do anything... though i think i'd prefer the facial.

From Same day, 1pm

My law firm has a suite that I can usually use; it's
fun, I think you'll like it. A facial [well, maybe
two or three ;) ] it shall be then. And have no
doubt; eating you out is going to be half the fun!

Just wear something that makes you feel slutty. And
do you have a cell # in case I'm running late.
Lastly, how much are you going to charge, and have you
done this before?
Let's make it 9:30 tonight then.

From Same day, 3:51 pm.
--- I'm sure we'll work it out on the spot. and if you're comfy with your firm's suite, i can work around it.

--- haven't done this before (haven't even had a facial before, just on other body parts. new experiences are always more fun...) and as for charging, guess that depends on how long we'll be there and what else we'll be doing. definitely seems like it should be worth either a portion of my rent or several Christmas presents... (always between semesters. why???)

-- and i actually like to get down & try new things, so we'll enjoy ourselves.

-- in the ritz bar? i haven't actually been in their bar; aren't there a couple?

From Same day, 4:04 pm

i mean the bar at the restaurant (which i think they
call The Grill). Don't be late, or I might have to
find someone else . . .

i'm glad to be your first customer, and it will be fun
to be your first facial, too (I can't wait until you
see how you look in the mirror).

i love to fuck brunettes, and I figure we could be
there a few hours. so, how much should I bring with

From Same day, 4:18 pm.

so a few hours... $200. and in some fashion where you won't make me feel like you're going to slap me around and run out... or get me arrested... if you're anticipating late, late night activity, a little more...
and of course, any actual non-oral intercourse must use protection...

She ended the email by leaving the seven digits of her cell phone.

From Same day, 4:22 pm.

hmm a few hours ... $200. and if you're thinking late, late night, then add a bit more. and in some fashion where i won't feel like you're going to either run out, or slap me around, or get me arrested...
cause now i'm getting nervous, though once we get started i'll end up just having fun. not to use a cliché, but it's been a quiet semester.

and from what i've seen online/heard about, rather a bargain.

From Same day, 7:18 pm

hmmmm, you're not the most obsessive email person i've ever 'met' but I just wanted to send you another email. I'll check this again later, but unless I get some kind of confirmation email that we're definitely on by 9ish, I probably won't make it to the Ritz. I don't want to show up there for no reason!!! (you may not be able to make it...)
of course i may be hearing outraged silence, and just don't know it yet. ;)


From Same day, 9:04 pm

mea culpa! i got totally swamped with a client
meeting this afternoon, and totally neglected to check
the email (which explains why the bar at the ritz was
bereft of sexy brunettes in fuck-me heels).

I'm so sorry! Mea mea mea culpa!

What is your schedule like for tomorrow?


From Same day, 9:58 pm

hmm, i have friends coming to town until the 3rd. we're all running the marathon.
i was thinking of putting myself to bed, though i admit to a few twinges of disappointment.

From Same day, 10:01 pm

and i'm off fuck me heels. the marathon. try in a few months.

From Same day, 10:07 pm

how would you feel about slinking into something sexy
and shimmery and hailing a cab over here for a

From Same day, 10:08 pm

i'll have to go light on the slinky and shimmery, but where am i hailing the cab too?

From Same day, 10:10 pm

do you know The Holton Arms at L and New Hampshire?

From Same day, 10:16 pm

i do; what cocktail do you have available (i do have discerning taste you know.) and which apartment?

oh, and i don't look like a marathoner. this is no hard body. i'm not fat, but any real man will be harder than i am.

From Same day, 10:20 pm
don't worry; if you can give head like a real woman,
then we'll have a good time!

From Same day, 10:22 pm

soooo, are you going to give me an apartment number, or a number to dial, or some further direction than the carriage house.

From Same day, 10:23 pm

all i have is a little red wine; how soon can you be

From Same day, 10:24 pm

within 15 minutes; i only like a few blocks away. probably ten minutes. just have to decide -- panties, no panties?

From Same day 10:26 pm
i'm apartment 503; but don't worry, I'll be there to
meet you. and make it panties--it'll be fun to take
them off of you. shall i see you at 10:40pm?

From Same day 10:27 pm

10:40. black jacket. panties.


Ken watched her from the window of the lobby as she arrived. For the past five minutes, he had expectantly been checking faces, looking for a young brunette in a black jacket. It was amazing how popular a black jacket was these days!

But when he saw her cross the street, he knew it was her. She looked just the tiniest bit out of place. She wasn't just casually dressed running an errand or going home from work late on a weeknight. She wore a leather jacket slightly longer than her waist. The hem of a skirt hung to just above her knees. She had on a pair of black mules; the heel was small, not fuck-me length, but just high enough to give some sex appeal. He knew this had to be her. He thought of the panties she had put on under that skirt, just for him, just so he could take them off of her.

He saw her check her watch, and he checked his. 10:39. Perfectly on time. He pushed through the glass door of the lobby. Dressed casually in jeans a sweater, the nighttime air wrapped around him coldly.

"Hi!" Ken said, smiling. "Are you Anna?" he said with great confidence.

She smiled back. "You must be Ken. Hi."

"You look great. Really cute."


"And your face isn't really obscured like it was in the photo you sent."

She laughed. "No, I guess not. Gosh," she said, feeling the unease of meeting a new person and searching for small talk. "Do you realize how many people are out and about this time of night? Don't they all have to go to work tomorrow?"

"Must be pretty nice to be a full-time student."

"Take away the part about having no money, and yes, it is."

He held the door open for her, and she entered the building. They made small talk during the elevator ride, then walked down the hall and he unlocked the door to his apartment. All of the lights were on; Ken had left it so in order to make her feel more comfortable, more safe.

"Can I take your coat?" he asked.

"Sure," Anna said, and let him. "It's so nice and warm in here."

He hung her coat up in a closet near the door. "Wow!" he said, turning back to her. "You look great! You are very good looking." She wasn't just wearing a pink skirt; it was a pink dress, girlish, lovely, but sexy, sexy in the way that pink has become the color representing strong womanhood. The sleeves stopped a little passed her shoulders, and they were held together with delicate ties.

"Oh, no—"

"No, you are. Do a twirl for me, let me see."

She obliged him, and the hem of her dress fluttered around her. "How old are you?" he asked her.


"That's a nice age. Still young, but it's the point that real adulthood really starts to settle in."

"And you're—thirty-two, isn't that right?"

"Please don't say I don't look a day past thirty!"

"No, no! I like older men. In my—regular life, I guess—I usually date guys who are a few years older than me."

"That's good; men my age love to date women a few years younger than they are. Can I get you some wine?"

"That red that you promised? Only so long as you don't put any roofies in it," she said with a smile.

"But that's the cocktail I mix best!"

She followed him into the kitchen. "You have a nice apartment."

"Thanks. Look around, make yourself comfortable."

"It has a real sense of guy-ness. Sorta bare bones, but comfortable, designed for comfort." She wandered out into the living room. "Shit! You've got a lot of books!"

"This is Washington," Ken said, brining out two glasses of wine. "Don't we all read too much in this town?" He offered her her choice of glasses; she chose the one in his right hand.

"Shall we drink a toast?" Anna asked.

"New friends?"

"New friends." They clinked glasses.

"I really like your dress," Ken said to her. "Anna—is that really your name?"

"Actually, yes. Is Ken really yours?"

"Short for Kenneth. Look, just to get it out of the way, how about I put the money down here, on this table near the door." He took out his wallet and pulled out some cash. "It's sorta mixed, there's one hundred and five twenties. Is that alright?"

"That's fine. Like I said, I'm not exactly a pro at this."

"Well, I'm glad to help out an amateur." He laid the cash down and put his wallet away. "Tell me about yourself? Do you like sex?"

"Do I like sex?" she took a last sip of her wine. "I guess you could say that."

"On the walk over here, were you most looking forward to the money or to the man?"

"My my, you just go out and say what you're thinking, don't you?" she teased him. "Do you really want to know?"


"A little of both. But mostly, I was hoping you'd live up to your boast and I would get fucked several times tonight."

"Oh really?"

"Yes, it ensures that I'll sleep well." She was standing in the middle of his living room, idly toying with the empty glass in her hand, giving him a glance that was innocent on the outside, but devilish at the core.

"Well, then," Ken said, crossing the room to her. He took the glass from her hand and laid it down on the coffee table. He moved around her slowly, inspecting her, breathing in her perfume. "You smell lovely," he said. "You're quite the package." He touched her lightly as he circumnavigated her slim form. Anna enjoyed the attention, she closed her eyes, knowing that his eyes were on her, up close, focusing on the smallest and slightest things, the little things that made her a woman. The feint hairs on the back of her neck; the little silver earrings in her delicate ears, the smallness of her frame in relation to his manly size. Anna could sense the desire her body was causing to burn through him, a handsome, affluent stranger. She loved the power she could have over a man just by being herself.

Ken with deliberate gentleness, embraced her. He stood behind her and wrapped his arms around her, holding her body against his, rubbing his cheek through her dark hair. He could feel how cold her hair had gotten from her walk over to his place.

"You're a lovely woman, Anna."

"Thank you," she said. She put her hands atop of his, letting him know she liked being held like that.

"I'm going to enjoy you."

"I think you will. I can't wait."

"Kiss me."

She did. They kissed slowly at first, small, closed-mouth kisses. Little get-to-know-you kisses, Anna had always thought of them as. She thought it was interesting—even though he had just laid out two hundred dollars so he could have her at his pleasure, he still kissed her slowly, like a gentleman. He was a good kisser, too; his mouth tasted warm and minty. He brushed his teeth, she thought. She wondered if all men who bought sex were so thoughtful.

His hands began to roam over her body; feeling her back, her sides, the tight marathoner ass through her skirt. He could feel the bra she was wearing under the dress, and slowly massaged her small breasts through her clothes. He liked the feel of them; it was always such a treat to touch a woman there.

Anna opened her mouth wider, signaling that it was okay to kiss her deeper. Ken could not believe his good fortune. After a few French kisses, Anna pulled back. "I don't think you just want to kiss me all night, do you?"

"No," he said naughtily.

"Good. If you did, I might have to give you a refund," she said playfully. "So—what can your little amateur prostitute do first?"

"Well, are you really wearing panties?"

"Here—feel for yourself." And she guided his hand up her skirt. Kenneth felt the soft flesh of her legs. And then his fingers touched intimate cotton. He slipped his hands across her underwear until he found her pussy. Ken cupped her womanness in his palm.

"Oh my god," he moaned.

"That feels good, keep it right there," Anna said. Ken could feel the heat she was radiating. He rubbed up and down her slit, feeling for her clitoris. She let out a little cry when he found it, and he began to rub light circles around her clit.

"I want to unwrap you, Anna, I want to see you naked."

"Oh do you?"


She unbuttoned her dress, undid the tie at the waist, and it fell open, revealing a pair of small breasts in a simple white bra. She stepped away from his hand, and lifted the dress over her head. She tossed it down on his couch, and stood there, wearing a white bra, a small pair of purple cotton panties, and those low-heeled black mules.

"Turn around," Ken commanded softly. She did. "Stop," he ordered when her back was to him. "You have a great ass," he said. "Bend over, show it off to me."

Anna did as she was told.

"You are not soft at all," he said. She righted herself, and he came to her. "Just in the right places," he said, one hand grabbing a fistful of her ass, the other softly clamping down on a breast. "I am really going to enjoy fucking you, Anna."

"Well, let's get it started. You could feel that I'm ready."

"Okay." He sat down on the long leather couch. "I think you know what to do."

"Oh? Does this big time lawyer want his poor grad student to suck his dick?" she said in a faux little-girl voice. "Is that it? Do you want your little amateur prostitute to blow you? Are you going to give her that facial you promised?"

"Yes, but—wait a second. Go get the money on the table."

"Alright. And bring it over here?" She asked, quizzically. "Yes." Not sure what was up, Anna retried the cash and came back to Ken on the couch.

"Kneel down," he said, taking the cash from her. When she was settled in position in front of him, Ken slipped the cash under her bra straps. The money rested on her shoulders, secured by the straps. "That's nice," he said.

"Oh my god," Anna said, blushing self-consciously. "I am such a slut!"

"Honey, you are so sexy. I hope you enjoying sucking dick, because I can't wait to feel you do it."

"Oh yeah?" she challenged him. "Do you want to see this pretty face of mine—this cum virgin face of mine? That's what you want, isn't it? To cum on my face? To shoot that hot white cum on my pretty face?" She was undoing his pants.

"Oh, yeah. You are so sexy Anna. Oh, fuck yeah!" he exalted. This twenty-seven year old brunette graduate student, this amateur prostitute, had taken his cock in her mouth.

"You've done this before," he said, feeling her mouth moving up and down on his cock. "You've given head before."

"Mmm-hmmm," she moaned.

"Do you like it?"

She nodded, eyes open, looking right into his.

"You are so wonderfully, exuberantly debauched."

She giggled.

The blow job lasted for awhile, and Anna thought it was going to last until he came on her face. As she knelt there, sucking this strangers cock, his money stuffed in the straps of her bra, Anna realized if being a whore meant sucking off men with tasty cock's who could get so turned on just looking at her in her underwear—maybe she shouldn't just be an amateur whore. She had to go to grad school, but why go through grad school poor!

"I want to see your cunt, Anna. Show me your cunt."

She stood up. "You like ordering me around, huh? Does that turn you on? That you can do pretty much whatever you like?"


She hooked her fingers into the waistband of her panties. "What if I didn't want to show you my pussy? What if I didn't like it when you called it what you did? What if I said that would be extra?"

"Then I'd ask nicely. Pretty please can I see your sweet cunt."

"Well, when you put it that way—" and keeping eye contact with Ken, Anna lowered her underwear to her ankles, stepped out with one leg, and then kicked her panties at Ken.

"Ta da!" she said. Her body was so slim and fit. There was a soft mound of dark hair covering her pussy. "You know," she said, "I think we should switch places."

Ken agreed, and she helped undress him. She enjoyed feeling and seeing his male body, much as he enjoyed feeling and seeing her female form. She liked how his cock stayed at attention—how do they do that? she wondered to herself.

"Can we go into the bedroom?" she asked. "It's better for me to get head when I'm lying flat on my back?"

"No problem." He led her into the bedroom, pulled her onto the bed with him. They bad out some more; he took off her bra and put it down atop the dresser near his colognes. He kept the money there with her bra. Returning to the bed and to her body, Ken worshiped her breasts with his finger and his mouth.

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