My Friend the Stripper

I think the word at school was that black girls always put out."

"You know we used to say that when I was in school." I interrupted, "Except I went to school in Lincoln and there were no black girls."

"When I got to High School there were about six or seven black girls there and they had heard about me and were pissed because they had to fight off the white boys who thought they were all easy.

Then I met Byron. A black guy with a big dick."

"Bigger than mine, ha, ha."

"It was close," she winked, "The first time we fucked I had a great orgasm. It was the first time I ever came fucking. I came every time with him. We were together for five, six months. Eventually I figured out that I can cum when I'm fucking if the guy has a big dick. While I was with Byron the black girls back off me a little. We weren't friends but they weren't mean to me anymore. But I had a few friends. One girl, Maura, loved to hang out with me. She was always asking questions about sex. She was a virgin but decided she didn't want to be one any more. And she was such a cutie. A genuine ginger. Even her pubes were red, well kinda red. And she had great tits. What they call "puffy nipples". I wanted to suck on them so bad but I wasn't into that then."

"Are you into it now." I asked as my dick started to harden.

"Sometimes, not a lot. I've done it for business and once in a while there's a girl who turns me on, you wouldn't believe what kind of girls I like."

"Let me guess, redheads with puffy nipples."

"Nope I like chubby girls with big tits. And if you can find ''em anymore, hairy bushes."

"I would've never guessed. But I like girls like that too so it's not so crazy. But then again I like almost every kind of girl."

"After high school I started going to Mass Bay Community but that didn't work out too well. And I really wanted my own place. I found a place with one roommate in Attleboro. Turns out she was working at a massage parlor in town. She got me a job there. I was like, I'm fucking guys all the time, I guess I could give a few happy endings and make some money. I did that for a couple of years and then one customer asked me if I would interested in working at the Foxy Lady in Providence. So I said to myself, why not."

"Your career is really moving."

"I don't know if you're making fun of me but I was doing pretty good. Providence was a trip. In Rhode Island there's no law against prostitution, or at least there wasn't then. There was a law against solicitation but no law against sex for money. So the guy had to ask. Word got around pretty quick. The guys knew how to ask. And if I didn't like the guys I would just say, oh no I can't do that. Still the place was pretty sleazy and I was pretty happy when I found the Outcast."

Cherry gave her a signal and Chantelle said she had to go so we'd have to finish later.

Part Seven November 27, 2006

Same day.

After she left Cherry sat down and said, "what do think, Jare, you want a dance?"

"I don't think so, Cher. It just feels weird when nobody's here."

But I was thinkin' Cher looks like the girl Chantelle had just described. I wouldn't call her chubby - maybe just a few extra pounds. She was red headed and had huge tits. They were real and hung down over her chest.

No bush though. In fact, I think if you lined up all the girls from the Outcast you wouldn't find a single body hair.

Then Chantelle came back and said, "The guy left after one dance. I made a dollar!" Waving her dollar.

Then Cherry said , "Hey Jared how about a two on one? Three dances for a hundred bucks."

"Let me see if I've got a hundred." I said fishing through my pockets, "I've got ninety, can I owe you? Wait second I forgot about this." I had a fifty in my other pocket. "A hundred and forty and as many songs as I want."

Chantelle and Cherry replied in unison. "Deal!!"

Once in the private room, Chantelle gave Cherry a really passionate kiss. I guess Cherry was one of the girls she liked.

They took off their clothes and told me to move over. Cherry sat sideways on the couch with her back against me. Chantelle went right to work on Cherry's pussy. Meanwhile, I turn around enough to get both my arms around Cherry and grabbed those giant boobs. Sometimes there's something really special about holding a really big tit. She made some sounds of approval so I kept holding and squeezing them. When I grabbed her nipples - both at the same time - she gave out a loud moan. Chantelle was sucking on her clit while fingering her cunt.

Cherry said. "Harder."

I said." Me?"

"Both of you."

So I complied by squeezing her nipples, which were becoming enormous. She said harder again and this time I knew she was talking to me. I started twisting her nipple really hard and the harder I twisted the more she cried out.

Chantelle and I did our work for ten maybe fifteen minutes before Chantelle started to come.

First she said through her heavy breathing, "I'm gonna come," then "oh I'm cumming."

It was something to see. Cherry was just writhing with pleasure, moaning and sighing and whatever other sounds you've heard. Then she hit her climax. Her legs shot up and she started shaking and screaming. Chantelle moved away but kept her finger in Cherry's pussy. I was still twisting her nipples. Fluid was coming out of her pussy. It seemed to go on forever but finally she caught her breath and sat up.

"Jesus Christ, you guys should be arrested for that. Two against one it wasn't fair." Then she added, "it's a good thing you didn't go for three song deal."

A few minutes later, feeling rested enough, Cherry rolled over on top of me. She had her back to me so I could grab onto those melons and was slowly bounce on my lap. She started develop a nice rhythm and was gliding up and down over my dick.

Chantelle came over and started playing with my nipples (which I like a lot). Then she stuck her head between Cherry's back and me and thrust her tongue in my mouth. Out of instinct I responded but then briefly I wondered if this was good for our friendship. Never mix business with pleasure, she always said that. But I thought to myself, fuck it I'll work that stuff out later.

Then Cherry stood up. What a sight to see. That flaming red hair and those big tits dripping with sweat.

Cherry kneeled in front of me and started mouthing my cock through my pants. And then in an instance she had taken my pants and shorts down far enough for her put my dick right in her mouth. Holy shit. She's giving me blowjob right here in the private room.

"I could always tell you were big but you've got a monster here."

Chantelle had to stop to take a look. After all this time she'd never actually seen it.

"Ok ok so it's big. Does really make any difference?"

Cherry had great blowjob skills. She was alternating a few minutes of handjob a few minutes of blowjob. With her free hand she located two spots that I never knew about but were really good. First she would rub my "taint" and push into it and the spot within my balls where you can feel the shaft of my cock. She pushed lightly on that spot and it was good. She was stroking my dick and I was very close to cumming then she put her lips right on the crown of dick and moved her finger into the opening of my ass. That was it!!! I just came like a firehose. Cherry made sure to swallow every drop.

"I made sure I swallowed every drop of your cum."

"Thank you, that was unbelievable. But you know after I cum I really don't care what you do with it. I never really understood the whole swallowing thing."

"Oh I'm sorry I thought you'd like it."

"No, no don't be sorry. Please. It might've been the best blowjob of my life. I'm just saying you don't HAVE to swallow. If you like it great, have as much as want but I don't think there's gonna be any seconds today."

Part Eight December 20, 2006

This day wasn't much different than all the rest. I had a dance with Amber then one with Devin. Chantelle had said that if we were gonna hang around I had to spread my dances out.

Next came Chantelle. Something was different. The dance was, at best, average. I didn't even cum.

"Chantelle, is there a problem?"

"No why?"

Why do women always do this. You ask them what's wrong and they say nothing until you're practically begging them.

"Come on, Chantelle , I know something's wrong. I think it's that kiss. Isn't it?"

"Yes it is. I mean I like you. You're a great guy but it's still business and I can't start mixing business with pleasure."

"I understand but we are pretty good friends at this point. I'm not crazy about being business."

"No you're not business, I'm not sure what to call it. But I shouldn't have kissed you like that. I was a little high. I had done half an Oxy and then when you bought me that drink it got me really high."

"What's the deal with Oxy? It's all I hear about these days."

"Oxy is time release Percocet. So if you crush it and snort it it's like taking a whole days worth of Perc in one snort."

"How much drugs do you use?"

"Not a real lot. I do some. Sometimes I need a little help to get through a night here."

"It's dangerous. Yes?"

"It is. Easy to OD, easy to get hooked. That's why when I'm running a game on a guy I use perc. not Oxy."

"So let's get back to the "game."

"So what? You writing a book?"

"No but it would probably be a best sellers but it would put hundreds of girls out of work."

"So the basic idea is to get the guy to fall in love with you. Maybe it would be more accurate to say addicted to you. Drugs and sex help a lot."

"I could see getting addicted to you. Do you think you could've played me?"

"I don't think so. I think you would've caught on."

I thought to myself, "I'm not sure. If she was playing me really hard I might've gone for it."

Back to the game.

"Yeah so you start with the handjobs while you're getting him into getting high when he's with you.

A great move is to get him to take on a trip. Like to Atlantic City. A jacuzzi suite in AC works very well. Two days of handjobs and Percocet in a jacuzzi goes a long way to getting him on a leash."

"No fucking?" I asked.

"You try to keep it to handjobs, then maybe blowjobs but eventually you gotta fuck."

"So where's the money?"

"Oh you wouldn't believe how many ways there are to get money. At first you let him know that you hardly make any money at the club and you got a habit. You ask for a little help. A thousand here, a couple of thousand there. And shopping! It's amazing how much these guys will buy you if you play it right. He'll buy you a fur coat for five grand and then you return the next day."

"So how much can you make?"

"A game that goes a month or two can be worth ten thou. If you get one going two, three months you can really run it up."

"So how much do you make?"

"A hundred thou, maybe more. I made over a hundred fifty last year. At one point I was playing two guys at once. That was crazy."

"What do you do with all your money?"

"I've got a Corvette."

"That's nice but.."

"I've also got a nice condo in Milton. I keep $800 a week for myself, everything else goes to my stepbrother. He's a stock broker and invests everything for me. When we were both living in the house in Canton we'd fool around a little. It's our little secret that keeps him from talking about my life. I'm gonna quit when I get to a million. Then I'm gonna finish school and live my life. I'm getting pretty close."

Part Nine March 4, 2007

Chantelle was happy to see me. "Hey, where you been?"

"I've been pretty busy. Had to spend some time in Dallas." I told her.

"Did you find a dancer to play with," she said smirking.

"Well I went to a couple of clubs. They're pretty wild down there. Big clubs. Lots of girls. Three or four stages. I think some the girls do tricks in the back room but they do have cameras."

"That's the best thing about this place - no cameras. So did you hook up with one these girls?"

"No all those lights and everything, it was turn off. I've been spoiled."

We had a girl here a while ago who was whoring on the couches. We complained to Jack about. It changes the place and ruins our games. You know Star? She's the master of the game. Truth is I think she takes it too far. I don't like it but who am I to judge. Anyhow, she had this guy who just lost it all. He got strung out really bad. She'd take him downtown and do deals in the street. He'd pay twenty percent more than anyone else (he had no idea) and the man would cut his dope a little extra. Then he'd kick back some to Star. This guy was buying Star everything. He even bought her a car. He left his wife and kids, got an apartment and had Star over all the time. Then she made the ultimate move. She got pregnant. She was gonna leave him and hit him up for child care. That's like an annuity. As it turns out the guys wife contacted his best friend and they got all the details. They offered Star $150K lump sum and had her sign an agreement. Star had already played him for over half a million. She took the deal. This guy really didn't deserve this. I was pissed when she used to come in laughing about the whole thing."

I interrupted, "But she had a baby she had to take care of, no?"

"You're not gonna believe this. She was never even pregnant."

"Wow! That really does suck."

Part Ten. September 22, 2007

On Monday September 22, 2007 I got a text message from April. She said, Meet me at Capital Grille in Chestnut Hill tomorrow night at 6:30. Be there!!

In the two years I knew Chantelle she had never reached out to in any way. Our entire relationship existed in Easton, Ma at the Outcast Bar. I didn't know how to take it. I was scheduled to leave for Chicago tomorrow for a really important meeting. One that could net my company fifteen million dollars and $375K for me. I spent the next four hours trying to reschedule this meeting for Thursday. In the end everything was OK but I was taking a big risk just to meet Chantelle for some unknown reason.

I was pretty sure it was something good. I put on my best date outfit. My Zegna Cashmere blazer in a color they called Eggplant. A white Talbot shirt, a very subtle Talbot striped tie in black, red and grey. Dark tan gaberdine pants, white socks (yes, white dress socks. My signature when I go out). And my Allen Edmonds split toe penny strap loafer in tan. The finishing touch was a white linen pocket square folded just right. I checked my look in the mirror. I was looking good.

The Capital Grille is a sophisticated steak house with classic and impeccable design. Chantelle was sitting at the mahogany and brass bar wearing the classic little black dress cut just low enough to show a bit of décolletage, a discreet slit at the thighs and a lovely string of pearls. Her makeup was toned down from what I was used to. She looked fantastic. Other men sitting nearby were looking at me like I was the luckiest guy in the world.

As I approached, she got up and gave me a big hug and kiss. Her perfume was unmistakeable - Chanel no. 5. This was gonna be a special night!

"Jared, Jared I'm so happy to see you. I was afraid you weren't gonna make it." She said smiling ear to ear. "And you look awesome. Boy you dress up well."

"Thank you, and you look and smell fabulous."

"Let's go to a table. I've got a lot to tell you."

"The Maitre d brought us to a nice table in the middle of the floor."

"Do you have a table that's a little more private." I asked.

"Certainly sir."

I ordered a V.O. Manhattan straight up, Chantelle was still working on her cocktail.

"I can't stand the suspense. What's up Chantelle?"

"Not Chantelle, April. And you know how I always say never mix business with pleasure? This is pleasure! There is no more Chantelle. Saturday was my last day at the Outcast. I am now a pretty wealthy, full time student."

I felt ecstatic for her, "that's fantastic April. Tell me everything."

"Last week my stepbrother, Darrel told me that I had to get my money out of the market fast. It's about to crash. In fact, the next day Lehman went BK. But he made a play on this fund that buys credit swaps or something like that. I had $900K, he invested $200K in this company and two million on Friday. I know have almost three million dollars. Can you believe it?"

"Yes I can believe it. I've been in Scion for a couple of years. I made a bundle myself. I'm assuming your stepbrothers play was something related to Scion. I also have to say you deserve it Jill. You've worked hard all these years. It's a great time to look ahead."

"He did mention that name." April said.

We had a great dinner including a couple very ample drinks. We talked everything except dancing. April talked about her dreams for the future. She was truly a different person. Gentle, thoughtful, articulate and truly happy.

"Come on, I want you come to my house,"

"Of course, it would be my pleasure."

"I think you might have to drive. Those drinks hit me kinda hard."

April took my hand and we walked toward her white Corvette convertible. When she told me she had a nice car I had a feeling it was a Corvette, it was the right car for an exotic dancer on her way up.

The top was down as we drove through Brookline to the VFW Parkway. It was little cold but seats were heated and she had the defroster blasting. I had to ask April to slow down a little.

We turned onto Blue Avenue towards Mattapan but turned towards Milton. Milton is a wealthy suburb of Boston with really impressive homes and estates. But it borders dorchester so there is a section that's less affluent. Still a nice suburban area just not as stately as the other parts of Milton.

April lived in a two family house on Blue Hill ave. A lot of developers have been buying up these two family house and converting them to Condos. April's house was very nice. A turn of the century Victorian painted kind of a grey / blue with white trim. The entrance was a front porch with carved columns and a beautiful oak door with stained glass. April's unit was the first floor. Really nicely decorated with contemporary comfort furniture and mostly maple tables and trim. She gave me a quick tour, then sat down at the kitchen table and laid out a couple of lines.

"Oxy?" I asked.

"Yea, but just a taste. Then we'll to a line of coke. It's a great combination. And it keeps you a little more alert."

I'm not really much into drugs but I figured what the hell. This was a special night. Besides I really trust Chantelle, I mean April.

As promised the combination was really good. I think I could best describe it as just feeling really good.

We moved to the coach with two glasses of Chardoney. April leaned towards and gave me a nice soft kiss. The kind of kiss that says I really like you. We explored each others mouths in a way that was somehow different. Tender and relaxed. As though we had all the time in the world.