One Trick Penny Ch. 05

Tutorial Session

It had been a few weeks since I'd started turning tricks with my husband, but I was rapidly starting to run into a problem. While trying not to become repetitive, I had to admit I was out of kinky ideas. It wasn't like I'd had much experience with fetishes and dominance before I got married - none really. Oral was as wild as I'd gotten. I was way past that now.

Dave wasn't much help. I was disappointed to learn that while he enjoyed our raunchy sex, he wasn't all that inventive. The burden seemed to fall on me. Even his porno collection was relatively tame; a prospect most wives would be thrilled at, but in my case, I'd hit a dead end. I could only pose with my legs spread apart so much, before it became boring.

I decided to try to find out how real life hookers kept their customers coming back. There was a hotel in the business district that had a reputation for being a place where women with tail for sale met with their money-tricks. The Aventeen was once a high end downtown hotel, but the surrounding neighborhood had gone into decline decades ago. The hotel never quite recovered as the surrounding area revived though gentrification and thus it existed by providing a comfortable place of the higher-end prostitutes to ply their trade.

Wednesday afternoon was the perfect day for my field trip to the Aventeen. Dave would be working late, and I heard the middle of the week was a hotbed of working girl activity. In my dressed down jeans, I sat in a quiet corner of the formerly eloquent bar, nursing a series of iced teas. The place was an oak paneled relic of times gone by. The heavily upholstered booths were dated and in need of restoration, but given the lack of big-spending crowds; the prospect was unlikely.

I watched as women in tiny skirts and impractical heels sipped at Cosmopolitans until some man in a business suit sidled up next to them. Typically, they smiled, engaged in a brief conversation before disappearing from the bar for an hour and then returned alone for another Cosmo.

Interesting at first but I soon realized it told me nothing about their techniques during that unseen hour. However, one woman in particular caught my eye. She seemed somehow familiar. She was small, with dark hair cut into a bob style with bangs. She certainly didn't look like what I'd consider to be hustler, yet she seemed to have the most activity of any of the other women present that day. At last I realized, this was the same woman I'd seen in the adult toy store a few days before.

I decided to approach her when there was a lull in her agenda. I ordered a Cosmo at the bar and carried it over to her table. "Hi, I'm Penny. I think you helped me a few days ago. The rental of the Sybian?" I realized how weird an opening line this was.

She looked me over, without a word as if evaluating my threat versus money making potential.

"Would you mind if I sat and talked to you for a few minutes. I promise I won't be a pest."

To my surprise, she laughed slightly and patted the spot next to her. "I don't take you for a cop; you stick out too much. To let you know, I don't do lesbo strolls. Nothing against it, it's just not my thing."

"No, I'm not looking for a trick. I'm kind of, well not exactly..." I felt silly trying to explain my interests. I hadn't thought out how to tell someone I was looking for advice on how to sell my ass to my own husband.

"I don't take you as competition, either. You'd have some notion of the cost of a Sybian if you were in the trade."

Trying as best I could to explain in a few dozen words my interest in limited prostitution all the while barely taking a breath, I gave a brief rundown of my activities. I figured I'd be immediately dismissed with laughter.

Instead, she looked me over more carefully and casually said, "Oh; you're what we in the trade call a Pro-tender. I've never met one before. My name's Quinn. I'm a good judge of character, and I get the feeling you'll make me money. Sure, I'll answer your questions."

I ordered us another round of the vodka drinks, and we chatted. I pressed for advice on how to keep things interesting for repeat customers. She had several suggestions of acts I'd never thought of. I must have looked crazy taking notes, but I wanted to make sure I got all the details.

I hesitated to inquire, but since she seemed ready to answer anything I could come up with, I asked, "What do you call your profession? Prostitute, hooker, working-girl, call-girl?" Without thinking of the negative connotations I added, "Whore?"

She laughed at my obvious discomfort at possibly insulting her. "I've been called all of those terms and more. I don't take offense at them. Among those of us in the trade, we use the term 'sex worker' or sometimes just 'worker'".

I wasn't that familiar with the term. It seemed to take some of the negative imagery out of it. "Sex worker it is."

"Are you serious about learning this game?"

I nodded my head.

"The only way to learn is to do it...or at least watch someone who knows how to do it. Are you up for watching?"

I thought about where this might go, but decided it would be a worthwhile risk. "Sure. I'd be willing to observe. Would I hide in a closet or something?"

"No, nothing like that, but you'll have to be willing to see some imitate action. Interested?"

"Yes."

Quinn looked around the bar and spotted a man sitting along in one of the booths. "Stay here and don't move. Just smile when I point to you."

Seconds later, she'd gone over to the man and began a conversation. He smiled and fixed his attention on her. Then, she pointed to me and he eyed me as if looking over a side of meat. I concentrated on sipping my drink and tried not to look as awkward as I felt. My heart was starting to beat more rapidly.

The two approached the table and she introduced him as Henry. "This is Penny. She's a novice. You know; just learning the ropes. She'll just be watching us."

He agreed to meet us in a room she'd rented in fifteen minutes and left the bar. Quinn and I headed to the fourth floor. "I've got a skirt your size that should fit. You look like you have nice legs. Be sure to show them to him. He's paying an extra hundred to have you watch us fuck. I knew you'd make me money."

"But I don't have to do anything else?"

"Not unless you want to and can negotiate your own price. I don't pander for anybody. I'm strictly an independent contractor. I set my own bookings. Got that?"

"Sure," I said nervously but not completely understanding the entire concept.

In the room, I tried on a mid-length skirt with a slit up the side. The fit was tight, but the material hugged my curves. I sat in a red velvet chair and crossed my legs as the slit slide opened and put my legs on display.

"Yeah, you do have nice legs. You could do very well for yourself, if you ever decide to branch out."

A knock on the door disrupted our conversation, and I caught my breath. Quinn opened the door and greeted Henry, who also acknowledged me.

Quinn removed her own clothes and helped Henry with his. I remained clothed and silent. Quinn, while short in stature, had a slender body, and I saw her appeal. She bent down and began sucking her customer's cock. She managed to work his balls with one hand, while rubbing the cheeks of his ass with the other. Henry was an older man with pepper grey hair and a thin face that betrayed the lines of his years. His penis rose quickly with her technique.

I've sucked a few cocks before meeting Dave and have performed oral on him hundreds of times, so I'd say I'm experienced. I considered myself to have some talent, but nothing close to Quinn's technique. She was an artist in the way she cleanly worked the shaft while simultaneously manipulating the sacrum. Her client was hard as a rock and in a trance from her attention.

Periodically, he observed my crossed legs, which I wiggled slightly for his further enjoyment. He smiled broadly as Quinn slurped away, and he ogled me watching them go at it.

"You're ready for the main event, Henry?"

"Yeah, I can't wait to get into you."

She lay back on the bed, and he moved on top of her. Her legs spread widely apart as he entered her. As he began to pump her, her legs wrapped around him. Her red toenails waved in time with his recurring movements. Somehow, this all felt normal; even comfortable being here. Periodically, Henry glanced in my direction.

"Penny, how would you like to earn a hundred?" he asked.

"I can't have sex today."

"No, I want you to lash me with that horsehair whip hanging on the door knob," Henry said in between breaths as he pounded away at Quinn.

I turned to seeing a long-handled item with strands of course beige hair attached. Quinn remained silent, but looked at me as her firm boobs bounced to the motion of her being pumped, as if to convey the message that it was up to me to decide.

For a brief moment, I mentally debated the morality of actually accepting money to enhance a stranger's sexual gratification. My internal dilemma was quickly settled when I realized I was in a room with a woman being fucked for a few hundred dollars. Whipping him would be the least outrageous thing happening.

I took the implement in hand and let it flail his bottom just as his ass rose up.

Henry winced and shouted, "Yes, harder, please."

I brought the whip down once more, this time with more force and a flick of my wrist. The end of the hair made a snapping sound as it connected with the flesh of his buttocks. It left a small red streak where it met the skin.

"Yes, that's it, Ms. Penny. Tell me what a bad boy I am. I'm an unfaithful husband, that sort of thing."

Once more, I drove the lash across his rear. "You are a pig. You don't deserve your wife. She's been nothing but faithful to you, and here you are whoring around. You should be ashamed of yourself you fucking cheating bastard."

He shouted out, "Oh, yes; that's it. I'm cuming. I'm a whore monger. Yes."

I bit down on my lower lip. I was starting to come myself. Here I was getting paid to be a part of a sex act. My upbringing said I should be ashamed of my participation; I was anything but. I was enthralled and cuming without touching myself. I hoped my climax went unnoticed.

He collapsed on top of Quinn a short time later and rolled over onto the bed beside her. His penis was rapidly losing its rigidity. He stood and began to dress, while Quinn did the same.

"That was wonderful, he said as he handed me a pair of crisp fifties. You have talent." He handed me a card with a phone number on it. "When you can have sex, give me a call." He winked and playfully slapped me on the ass.

He left us a short time later and Quinn said, "Henry is one of the more normal fares. He likes a bit of kink, but nothing too wild."

I looked at the money in my hand and felt an overwhelming sense of guilt. I tried to hand the bills to Quinn. "This should be yours. I was just supposed to watch."

She laughed but refused to take the cash. "Let me guess; you are lapsed Catholic. Only a Catholic would have enough ingrained guilt to try to give away the wages from their sins, and you have to be lapsed to have been here in the first place."

My face blushed. She'd nailed me.

"Tell you what, I'm knocking off for the rest of the day anyway. You can penance off some of your guilt by buying me dinner with your earnings. Ask any questions you want. It might be fun telling you about my life."

~ ~ ~ End of Chapter 5 of 12 ~ ~ ~