Role Playing with Michelle Ch. 04

The stories in this series were written at least a year ago before I knew about Literotica. The previous one (chapter 3) is posted here.

If the object of the New York authorities were to increase prostitution and depravity, they could not better accomplish it than by their present policy towards the unfortunate class that everybody endeavors to ignore, but who suffer and cause more guilt, crime and misery than even bad rum can justly be held accountable for.
- Walt Whitman,
Brooklyn Daily Times, June 20, 1859

It was mid-January 1975 when my girl Michelle came up with an even more ambitious role-play. At that time were just starting the second semesters of our sophomore years at the City College of New York.

I listened to her plan one night at her apartment in Long Island City. This scheme, like the game we played the previous fall, involved using her Dodge Coronet again. She was going to play a streetwalker and I, in the car, would be the cruising John. We had to make some concessions to practicality; she would wait out of the weather in a coffee shop until I drove up.

I asked her, "How do you come up with these things? You should be both a playwright and an actress. Or maybe a movie director."

"Maybe I will; I've got to do something when I get out with this worthless degree."

Like the previous role-play, this one was going to be done outdoors, on location and it would unfold in real time. Being in these things was almost like acting in a movie sequence although of course there could be no retakes.

As the creator of the game, Michelle would sort of be the "leader" or "director;" she had more knowledge of what the "script" would be than I did. As the "follower," I would be reacting to what she did. However, it was within the rules that I could throw a curve into the action and come up with my own surprises that would change the course of events.

*******

On the appointed day she needed some time to prepare for this role, so I spent the afternoon doing some errands with the car. She would take a cab into the city. Later, after dark, I pulled in front of a hydrant by the coffee shop on West 38th Street in Manhattan. It was a clear night and the temperature was in the upper thirties. Had it been much lower than that we probably would have postponed the game for another date.

She saw me pull up and she came out. We looked at each other and she made a gesture at me; I nodded and crooked a finger at her. When she was at the passenger side window I rolled it down; she leaned over and said, "You've got some money to spend?" I thought for a moment that the woman standing there might not even be Michelle. The voice was hers but the rest of of the person I knew seemed to be elsewhere.

Her straight brown hair was covered with a strange black-haired wig with curly styling. Her face was amazing; I had rarely seen her wear any but the lightest make-up and now she was covered with it. Her lips had a dark reddish-purple color and she had thick green eye show. She seemed to have powdered the rest of her face so it was even paler than normal.

The whole get-up looked hastily applied and smeared on rather carelessly. It was a Medusa face with black snaky coils on top that was peering at me from just outside the car; the effect was more unsettling than erotic. She wore a long dark raincoat that hid most of what was underneath but I had noticed her black high-heeled boots.

I said, "Yeah, sure, I've got money to spend."

"Good, just so I'm not wasting my time. Okay sport, open the door and let me in the back seat."

Why back there? She lounged across the seat and said, "Drive somewhere, west of here. Just cruise around."

As we pulled away she opened her coat to reveal her black clothes underneath. I had never seem these garments before, but I'd call it a classic dominatrix look. She had a bustier - is that what that thing is called? - and very short skirt. Her legs were apart to reveal even more: black lacy panties, a garter belt with straps holding up sheer dark stockings which were tucked into the boots.

She looked out at the passing buildings while I I was trying to get a better look at her and still drive the car. The good-natured Michelle I had known since last October had turned herself into this example of hard-edged, sinister raunchiness. I was impressed with her costuming talents. When stopped at lights I turned around and stared at her. She rubbed her crotch and said, "What, you've never seen a woman and her twat before?"

After a few minutes she directed me to a street - I think it was 58th or 59th - west of Eleventh Avenue. There was a Penn Central freight yard on one side and an old power house on the other. We parked in front of a tall step-in van that gave us a modicum of privacy, although the street seemed deserted.

She got in the front seat with me. "So what are calling yourself tonight?"

"I'm Jimmy. . . " Pleased to meet you?

"Ok I'm Tammy, you remember those movies with Debbie Reynolds and then Sandra Dee, Tammy and the Bachelor and so forth? So Jimmy, are you in a hurry tonight or do you have some time - because I have a package deal for you if you have the time and the cash."

She was leaning in on me and she had lowered her voice. I looked into her eyes but I didn't see Michelle in them. Her eyes had a blankness, but I also detected anger and hurt in them too. How does she do it, is her acting really that good? Or was I projecting what I expected to see?

I said, "I've got time and money."

"All right, it's a three part deal, see. The first is right here, you can have a blowjob for . . ." She quoted a price. "That is a very good price for this city as you should know. Then I'm feeling pretty hungry, so you'll take me for some dinner. The Market Diner would be fine." That place was around 44th and Eleventh, some distance to the south of us.

She continued, "Then, if you're still up to it, we'll come up here again for a very special deal."

"Which is?"

"It will be a surprise. Don't worry, you don't have to take it if you don't want it but I'll bet you will. Meanwhile, I assume you're ready for part 1, so pay up."

We had considered using Monopoly money for these scenes, then we decided that real cash would capture the verisimilitude that we wanted. We would just pretend that the amounts were much larger and really matched the figures discussed in our dialogue.

I peeled out two tens from my wallet which she then stowed in her purse. In her next movement she unzipped me. Michelle had a talent for blowjobs she used for this. She lay across the seat as I sat behind the wheel, and she used a combination of sucking, licking and kissing that was very effective.

I let my role-playing mind roll and said things to her. "Oh you little fucking whore, you dirty bitch, suck on my hot Italian sausage." It sounded more than a little silly but I was getting into the spirit of the event. "Yeah, sweetie, leave that purple lipstick all over my cock."

Probably I was much more relaxed than I would have been with a real prostitute. Being with a hooker had never been a major part of my fantasy repertoire. This game was just realistic enough to confirm my suspicions: if it had really been a stranger sexually servicing me in exchange for cash I might not have been able to perform at all.

When I came she took all of into her mouth, and I assumed she was going to swallow which is what she sometimes did in real life. But then she opened the passenger door and spit it all into the street. She turned back and said, "Hey man, you got a handkerchief I could borrow?"

I did, but I also expressed my dismay. "You just spit it out the door."

"So what, you were done with it, so was I. Let's face it, my obligation to your splooge ends when it leaves your cock."

I detected a bit of Michelle wittiness in that and I laughed. She said, "Look at those condoms out there."

There were indeed several used ones on the sidewalk. She said, "This is where the rubbers hit the road." She laughed, or rather cackled, in a way that I'd never heard her do before. "Yeah, there are eight million stories in the Naked City and half of them wind up in the business side of a Trojan-Enz."

Then she said, "The Market Diner, let's get there already."

In those days of depressed real estate values the diner could afford to have its own free parking lot even though it was on the edge of Midtown Manhattan. A lot of cab drivers went there though so did many other New Yorkers who were perhaps at loose ends.

Tammy put on sunglasses before going inside. I then realized that she hadn't worn her regular glasses all evening and I knew she must be missing a lot visually. With her raincoat tightly closed she didn't get attention from anybody in the place. When I ordered a tuna sandwich she said, "Oh no, buddy, if you eat tuna fish the evening ends now." That seemed odd, because Michelle had never objected to tuna before; this must be a Tammy preference. I deferred to her and ordered something else.

Talking to her was rather difficult. Instead of the lively Michelle, I had this rather sullen person to contend with. She was willing to listen to me describe myself, most of which was true except for some change of details like that I went to Lehman College in the Bronx.

I was reluctant to ask her about herself. What would I say, why did you become a prostitute? She did however have opinions about why I was a john. The main idea was that college girls didn't put out except for a very high price. "Like if you take them someplace like a diner on Kingsbridge Road, don't expect even a handjob."

She went on, "If they're feeling particularly expansive, and they think you might take them to a better restaurant, they might let you give yourself your own handjob while they watch. Or maybe they'll be reading their sociology textbook while you jerk off and moan about how beautiful they are." Then she switched to the voice of some self-regarding college girl, "Please, sweetheart, don't make so much noise, I have an exam tomorrow."

I laughed at that, but generally Tammy remained sealed off from me. I thought she might have a colorful streetwalking story or maybe some views about the job itself. But none of that was forthcoming.

She had no dessert, but she did get a coffee to go. Then it was back up to the freight yards, in front of the same step-in truck. She had us get in the back seat. As I sat there, she kneeled on the floor facing away from me, lifted her coat and lowered her skirt and panties. She said, "Now, for a very reasonable price of you can have anal." Again she quoted a cost.

"Anal?"

"Intercourse in the ass. Don't tell me you've never heard of it."

"I've never done it. "Well I'll show you how. You can't just shove it in there."

This time I brought out three tens. Those also went into her purse; she took out a small plastic jar. "Petroleum jelly. Get your dick out."

I wasn't particularly erect to start but she worked on it for a bit. Then she took more out and smeared it on her own backside.

I said, "Wow this is really romantic."

"If you want romance get one of those Lehman bitches and take her to whatever the hot restaurant is right now."

"Do women really like this, I mean anal?"

"Some women I think; for me, I can take it or leave it. If you really want to be a good guy, fondle my pussy while you're doing it so I'll feel something and I won't have to count sheep during the whole thing." It occurred to me that hookers probably did often have to mentally zone out during the actual sex; Michelle must have figured that out already.

Then she said, "Okay sport, let's get to this already. But listen to me; be gentle going in. Just push a little until it fits. Don't try to go all the way in to the hilt. When you move, go easy with it. If it hurts me I won't be shy about letting you know."

I pushed my erection against her and then it struck me: this wasn't really some streetwalker called Tammy, this was my sweetheart Michelle who had always been so kind to me. I rarely if ever had fantasies about anal sex, and I had never wondered what it would be like with Michelle. I saw her look back at me with those green-lidded Tammy eyes.

I could have bailed right there. Maybe Michelle had lost her perspective in her enthusiasm for this experiment. But then I decided to trust her, to take this role wherever it might lead.

Going in was easier than I had expected; she grunted slightly at the penetration. She said, "My pussy, you were going to fondle it, remember?"

My left hand held her hip, my right hand handled her in ways that I knew she liked. Meanwhile I kept up a slow but steady rhythm. I think I liked it more than I had expected; it was very tight in there. I decided to add some dialogue, "You little whore, I love putting my cock up your ass, do you like it?"

"Jesus Christ, you think you invented sliced bread the way you're going on about it."

Again I detected Michelle's wit, and I laughed. I suspected, with my hand stroking her, that maybe she did like it too. That thought encouraged me and within a few minutes I was ready to donate. I felt my role required more talking, so I did, "Take my hot sperm up your ass Tammy, take it, please take it." A moment later she said, "Okay, I took it." I fell back on the seat to catch my breath; she turned on her side to give me an appraising look.

She let me calm down and she said, "You know the problem Jimmy, when you have it in your cunt it generally stays there but when it's in your butt crack it dribbles out all night. What a mess. Thus . . ."

She opened the door and stepped out. She squatted down and shat my semen onto the sidewalk. I could hear it gush out.

This was the the night's most disturbing event yet. I'd seen her pee outdoors when she really had to, but I thought of her as a classy lady and this crude behavior didn't seem at all like her. She stood up, shrugged, and got in the front passenger seat, indicating that I should sit next to her.

When I was there behind the wheel she reached into her purse and pulled out an object. She pushed a button and a blade sprung open; it was an impressive switchblade knife. The line between playacting and reality became very blurred. We hadn't discussed anything like this and I was caught unprepared. I hoped for a moment that the blade was rubber but it obviously wasn't.

I said, "You already have my money; that's most of what I brought."

"It's the car I want."

I was beyond acting now, "You greedy little whore, you have no right to do this, you planned this shit from the beginning."

She didn't hold the knife too close to me, she just aimed it in my direction. "Greedy? I've got a debt to pay to some people you don't want to stay indebted to for long. I decided along the way that this was a good opportunity."

"What is it, drugs I assume?"

"You little punk, paying to fuck girls in the ass, who are you to make judgments?"

I was going to say, but you offered it, when I thought of another defense.

"You've bluffing me. You wouldn't murder me right here in the street. And I'll - I could report the car stolen after you take it."

She looked at me with something like pity. "First of all, I don't murder people - well maybe if it were a life or death self-defense and even then. However, you might, I don't know, lose part of your ear, which you could mail to one of your Lehman girlfriends."

An artistically inclined hooker, I thought. Then she said, "As for reporting the car stolen, Jimmy, you've got to do what you gotta do for insurance reasons. Just don't mention any chick in a raincoat peddling blowjobs. It will get awkward for you if the police get too involved. I've got some other people out here keeping track of me who you really don't want to mess with."

She was sneering at me; her painted face looked horrid. "You're way out of your college-boy league. Now give me the keys and your license."

As I hesitated, she said, "You're getting the license back." She tapped the glovebox, "You've got a notepad in here? I can't hold the knife and take notes at the same time." Of course Michelle knew there was a pad in there; it was her car.

I dutifully copied my information onto the pad, and she carefully compared it to the license. She said, "This is my bit of insurance, now I know for sure who you really are. That's a long way uptown, but we wouldn't be taking the fucking 2 train for that trip." Who was "we? A pimp?

"Could you at least drive me up to Columbus Circle?"

She stared in disbelief. "You pathetic loser, you can't even walk a few blocks in the winter. Now get the fuck out of the car."

I was surprised by how fast I complied. She slid over behind the wheel and started the engine. I was about a foot away, standing in the middle of the street, and she rolled down the window. She patted her hip. "Jimmy, thanks for going easy on my tender little rear end. A lot of guys have no consideration for a girl's hiney."

She continued, "The car will probably be parted out by tomorrow or whenever; I'm not sure. Don't try anything stupid or your balls may get parted out too."

Then she turned on the lights, stepped on the gas and the car was beyond me. I had been about to say more and I yelled it out anyway, "You bitch, you just knew I'd be an easy mark, didn't you?" A couple of seconds later the car was at the end of the block and then around the corner.

It was several blocks uphill to get to the Circle. On this January night the streets in that area were deserted. Once there, I wasn't so eager to get back to Long Island City but I didn't feel like going any other place either. When I got off at 23rd-Ely I was still feeling shaky as I walked to her place, passing the parked Coronet about a block away. I was reluctant to ring the bell when I got there but I knew I had to.

**********

She answered the door, outwardly looking the same as before. She still had her black wig on; her raincoat was open and her make-up was intact. But now it was Michelle there with a genuinely warm smile. Tammy had vanished. God, this girl really has acting talent.

But besides my relief I felt unsettled; her acting was almost too convincing. She sensed something about me and didn't hug me as I stepped into the room.

She said, "Hey, that was pretty intense, that little drama I staged, wasn't it?"

"You - you pulled a knife on me."

"Paul, sit down. Have a little cognac, it's cold out there."

I hadn't had any such consideration from her during the time she was Tammy, and I wasn't ready for it. She had to pour the drink for me.

She said, "Okay, it's something I made up, I knew about it ahead of time."

"It was certainly impressive, but man, I think I was actually scared. Is that silly?"

She was sitting next to me on the couch, touching my arm but not pushing too close to me. She sensed that I was in an uneasy mood.

I said, "And there's also, well you know. . ."

She leaned forward, "I know, we had anal sex."

"Have you ever done that before?"

"Yeah, about three times, and as Tammy said, I can take it or leave it. You, however, liked it more than you want to admit." I didn't know what to say so I said nothing. In the months I had known her I had found out very little about her previous boyfriends.

"We can do it again sometime if you really want to - well, maybe."

I was still gaping at her when she finally started kissing me. After a while she pulled back and said, "You got make-up smeared all over your face now. You know, I deliberately did a bad job with the make-up. Although maybe I should wear it a little more often. Time for some maturity. Would you like that?"