Journey Into the Darkside

That was only the beginning of a night of fantasy realizations for the both of us. Knowing that we planned to make a long night of it, we had dinner and took a short nap. Later, I told her of my intention that she would live one of her wildest fantasies—to see the world through the eyes of a prostitute. In fact, the thought came to me as I watched her standing in my kitchen entrance looking like a whore. Seeing Nicky in that skirt, and remembering the whorish way she had rode my cock and fed me her breasts had me wondering what her reactions would be to 'walking the stroll' (not really prostituting) downtown. I worked out all of the details before discussing it with her.

Nicky was certainly surprised, but as I laid out the plan to her, I could sense her desire to play on the perimeters of sex-for-pay, a wild (and potentially dangerous) adventure, indeed.

We left for the inner city around 11 pm We both knew where the red-light district was, as we both were long time residents of the metropolitan area. Though downtown arrests for crimes committed by and upon prostitutes were commonly carried by the TV news channels, I felt confident that we'd be able to do what we wanted with a minimum amount of risk.

Along with us in the van were accessories to help us with the experience: condoms, two spray bottles of soapy and clean water, hand cloths and towels, a long-handled security guards flashlight, and a thick comforter. They played important roles in how the evening unfolded. And, oh yes... Much of the evening's events were videotaped.

We arrived downtown, and it was obvious that red-light nightlife was in full swing. I drove slowly (as did everyone else), looking for a well-lit, suitable block to play on. It was Friday night, so the prostitutes and 'johns' were visible almost everywhere we looked. The prostitutes leaned into prospective customer's cars, the 'johns' called to them from the cars or alleyways, and the pimps watched everything that moved.

After surveying the layout for about 15 minutes, I pulled into a parking space, and asked Nicky if she was still sure she wanted to do this. She hardly heard me—her eyes continued to take in everything they could about the prostitutes and 'johns' play with each other. I looked at her—she certainly had the appearance of a prostitute. In fact, if a police officer had challenged us at that minute, he would have assumed her to be a prostitute.

"Yes... YES! I want to... I really want to do it!" was her absent minded answer to my serious question.

We went over the ground rules one last time. This was no time to have a communications disconnect. I was responsible for this woman, and I had no intention of losing control in this kind of situation. Nicky's movement was restricted to the block where I was parked, always in front of the van, and she was always to remain clearly visible to me in the van. She could walk up and down the block, but under no circumstances was she to exchange words with anyone, especially prostitutes, 'johns,' or anyone leering at her. She certainly was not to solicit or respond to solicitation from anyone. In the van, I would maintain a constant alert to any trouble. Upon the very first indication that her stroll was becoming too risky, I would shine the flashlight beam into her eyes. Upon my doing that, Nicky was to immediately return to the van. She understood the instructions, and was anxious to get out there.

"Okaayy..."

Nicky exited the van. At first, she just stood there, unsure of herself. But then she moved away, and walked a few steps. Damned, she did look good! I reminded myself that I had fucked her for free a few hours ago. I went into security mode, needing to focus on getting my whore back in one undamaged package. I started the 8mm video recorder on the tripod, to record everything that happened while she was outside.

As she walked a bit further, a car horn blew, and she involuntarily looked at the driver. He yelled to her, "Baby, come here for a minute..."

Now, I'd see if she understood. Nicky continued to walk, averting her face from the car. She moved to the corner, about 20 yards to the front of me, and stood there for a few seconds. A couple of prostitutes eyed her warily, but said nothing. I expected they weren't sure if she was new meat, or an undercover cop. Nicky turned and walked back until she was parallel with the van. I wondered if she was shook, and would get in, but she just looked at me through the windshield, blew a kiss, and mouthed the words,

"Hey! Wanna date a working girl?"

"Hell no," I said. "I get all I want for free!!"

She laughed. Then turned on her heels, and began the prostitute strut, as good as any of the other sluts out there. She was into it now, living the fantasy that she'd dreamed of for years. As her confidence grew, she began to look at, but not react to, the johns that were constantly blowing their horns, the guys walking the street who were eyeing her bump and grind buttocks as she strutted her stuff. Once, she just stopped and faced a 'john' in his car, hands on her hips, and spread her thighs as wide apart as her skirt would allow. Nicky was showing that she could do it for real... She could make this sex thing pay—if she really wanted to.

The part she didn't understand though, was the inherent competition that prostitutes engage in. As she approached the corner for the third time, one of the street whores spoke to her. Nicky said she only said 'hi,' but that was one word too many. I shined the flashlight in her eyes, and Nicky came directly back to the van and got in.

She was on such a high as she entered the van! "Oh... oh!!! Did you see me?? I have never felt so slutty in my life!" Nicky was bubbling, babbling, all of the above. Her face was light up like a Christmas tree!

She asked why I made her come back to the van. I explained that she was on someone's 'turf,' and unless she was prepared to fight for her right to be there, she needed to give them their ground back. And, that real prostitutes aren't there to hold polite conversation. If you're there, you potentially are taking money out of their, or their pimp's pockets.

Nicky was still on a sexual high though, and looking for something else to do. Like jumping a building, stopping a train... She was so wired as we moved back towards the suburbs. As we started up the Baltimore-Washington Parkway, she had both legs up, feet on the dash, begging to be masturbated. I moved my right hand between her thighs, and separated her blonde hairs as my fingers moved into the slippery wetness that was her pussy. I rummaged into her and she began to cum almost immediately. She ground her hips forward, trying to get more and more of my fingers inside. I cupped her cunt with three fingers, and pulled her upwards, then pulling out and smacking the wet outer lips with my hand. She loved it.

By now, we had moved onto the Beltway, and headed towards U.S. Route 1 and the small Beltsville suburb. It was past midnight, and there was little traffic on the Beltway, mostly trucks. Needing to maintain control of the van, I had to stop stroking Nicole, but she left her feet on the dashboard. I moved to the middle lane to make sure my driving wasn't interfering with the truckers, but Nicole had other thoughts. She switched on the interior overhead lights, so that her open legs and exposed cunt could clearly be seen by anyone we passed. The trucker who accelerated his rig to keep up with us certainly got an eyeful, as Nicky dug into her feverishly hot pussy, fingering it open to make sure that he saw the treasure buried at the apex of her outstretched thighs.

Fortunately the distance to the Route 1 exit was only a couple of miles. As we moved to the exit lane, he gave a pull on his air horn. Hopefully, he was saying "Thank you!"

I drove the short distance to the adult bookstore we had visited on our first night, with Nicky's feet still on the van's dashboard. By the time I pulled into a parking space, she'd stroked herself to an orgasm, her fingers almost frothy with her cum juices. The usual number of cars were parked across the street and their voyeuristic occupants watched for anything that seemed erotic. That was the game plan for tonight—Nicky needed to be seen, watched, and perhaps used.

I got out of the van, telling Nicky to stay inside and to keep the doors locked. As I approached the door to the store, I noticed there was a lone Latino male leaning against the storefront wall. He eyed the van and Nicky, who still was still busily groping her pussy, her legs wide open. I warily sized him up, to see if he was a threat for the 30-seconds I planned to spend inside the store.

"How's it going?" I asked.

"Okay..." he said. And then, "Looks like you got your hands full."

"Yeah, she's really wired right now... You wanna fuck her?" I asked.

"Man, I ain't got no money." He lamented.

"I didn't ask if you had any money—I asked if you wanted to fuck the girl in the van."

"Hell Yeah!! What do I have to do?" His excitement at the prospect of actually fucking my exhibitionist slut was unconcealable.

"Nothing yet... I'm going into the store for less than a minute. When I come back out, we'll talk about it. On second thought, go over and talk to her. Tell her I said to show you her cunt."

I'd have to move faster, now. My original plan had been to quickly scout the store to see if there was any one there I'd be interested in loaning Nicky to for a quick fuck in the van. Now, I needed to really be in—and back out, within 15 seconds. I went into the store, as the Latino approached the van. No one of any significance in the store. Back out within 15 seconds.

He was standing at the window, looking wide-eyed at Nicky, and she was putting on a show for him, indeed! She showed him the widely splayed pussy that she'd been finger fucking for almost 30 minutes now, and asked if he wanted to suck it. His mouth was salivating at that idea. I put a stop to it.

"You want to fuck her?" I asked, again. He could only nod, "Yes!"

I asked Nicky, "Do you want to fuck him?" She was so hot she would have fucked the long-handled flashlight on the floor of the van. (hmmm...)

"Okay, this is how it will work, if we decide to. It will happen in this van. You will use a condom, which I will supply. Finally, when either she or I say 'enough,' it ends right then. You understand that?"

He agreed, and we only needed to decide where to go. I saw the service station across on the other side of the intersection, and chose it as the location. We pulled into the station which was closed, and moved to the air pump, to be as inconspicuous as possible. The rear of the van was arranged to provide as much room as possible. I remained up front, to keep a lookout, and to provide security for Nicky as she whored herself out to this stranger.

Nicky moved to the back, and the stranger undid his pants. He wasn't very well endowed, nor erect, but that didn't really matter. What mattered was that Nicky be fucked by a stranger, to complete the thought of her being a total whore tonight. What was begun in the inner city was to be completed out here in the relatively sterile environment of a suburban community.

I watched him don the condom—he had some difficulty getting it to stay on. He complained... I told him it was either the condom, or we end it right then. He was clearly not the best candidate we would have chosen for something like this. There are those who just don't perform well on command.

Finally, with Nicky on all fours, her face between the front bucket seats, he was able to penetrate her, and began to rhythmically fuck into her. He was able to maintain his stroke for about five minutes, then I could tell that he'd lost his erection. Nicky was doing her best to encourage him, but he was obviously challenged beyond his ability to perform. He asked for another condom, and I gave him one. I really wanted to see Nicky's face as a stranger erupted his seed into her.

I decided to help a bit. I turned about in the front, and positioned myself facing Nicky's mouth, my cock out and available to her if she wanted it. She strained forward and pulled on the head with her mouth, getting me instantly erect and excited. I pumped into her mouth, hoping the stranger would appreciate a three-some effect. He continued his labors for awhile, and then went limp again. He mumbled something about having masturbated a couple of times earlier that evening. I'd had enough, so I told him to withdraw. He wanted to try to continue, but it wasn't working. He was having a negative effect, instead of the rock-hard cock exploding into my slut that she and I had envisioned.

I dismissed him (he wanted to 'borrow' 20 dollars for his 'services.' I declined), and Nicky and I drove away from the area. Minutes later, on the lonely country road back to Greenbelt, I drove into a pull-in and directed Nicky (still in the back) to clean herself up. She was quite disappointed by the lack of success in being well-fucked by the stranger. But she found the spray bottles and began to liberally spray the soapy water onto her pubis, following that with a clean rinse spray, to manage the cleanliness issue until we could get home.

So, our 'prostitute/pimp' role-play came to an end. I chose to never do that again.

Reaching home, I parked directly in front of the house. Instead of going inside, I moved to the back of the van, joining Nicky there. She was sprawled out on the comforter on the floor, a bit quieter than the slut she'd been earlier. I took her face in my hands, and held her, just quietly embracing her. After awhile though, I began to fondle her breasts, then suckled them vigorously enough to make the nipples 'pop out.' As I did so, my hands were busy, nubbing her clitoris and squishing in and out of her perpetually wet cunt. She raised her hips, and ground them at me, as if she were trying to belly-dance fuck my hand. I worked back at her cunt, again (always again) trying to fit my hand inside of her tight pussy. She moaned, throwing her pussy at my hand now, and got up on her knees, her breasts and face on the rear seat. She pushed back at my hand, which was working feverishly into her. Her hands were free, so she reached back and pulled her cheeks as far apart as she could manage. It still wouldn't work. I could feel the frustration within her. Nicky wanted to be stretched outrageously by something which would could be jammed into her pussy.

Suddenly, she asked, "Why did you bring the flashlight tonight?'

"To make sure you knew when I wanted you to return to the van," I said.

"No, Sir... It was more than that."

I wondered what she could be getting at. "No... It was to make sure you knew that I wanted you back inside the van."

"No, Sir," she insisted. "It was because you wanted to fuck me with it right here, wasn't it?"

"No..." The light bulb went on.

"Is that what you want, Nicky?" I asked. "Do you want me to fuck you with the flashlight?"

"Well, Sir... I think that's what YOU want, isn't it?"

"Hold on a minute, baby... Let's see if that works."

The flashlight was one of those long (about 15 inches), and thick (almost 4 inches in circumference) black security flashlights, with a metal ribbed case. I placed an oversized condom on it, and unrolled it to the extent I expected that Nicky could accept. Before I used it, I showed it to Nicky, eliciting a sharp intake of breath from her.

"Is this what you want, baby?"

"Yes, 'Daddy,' your little slut needs that big black 'cock' deep inside of her."

She began to sigh in anticipation, pushing her cunt backwards, searching for the penetration she needed. I moved the phallus to her cunt lips, and let her do the rest. Nicky needed no further encouragement. She pulled her lips open, and rocked back, taking an initial two inches inside of her. I rubbed her ass cheek with my free hand, watching lustfully as she began her next penetration onto the light. Her pussy rocked back again, this time accepting almost five inches, but she didn't relinquish her hold this time. She held it, and began to engorge herself more and more onto it, crying out in need, now working her ass side to side and back and forth.

I held position. I was hypnotized at her desire to be completely stretched, and pummeled by this cock substitute, and couldn't wait to see her cum all over it. I didn't have to wait long. Soon the van was rocking in tune with Nicky's fucking motions, and she began a low howl; guttural sounds were emanating from deep within her, and she begged me to put the end of the flashlight on the floor. I put it down, and she moved there with it. I simply held the light fast in one place, and Nicky rode up and down on it for a couple of minutes. I could tell it wouldn't be long, because she was in her own 'space,' not knowing or caring about anything except her primitive need for release. As she began to orgasm, Nicky fell to her side, and started a long low scream which increased as her orgasm built in intensity.

"Hu-Hu-HU-HUUU..." and finally let go, thrashing about in the van, her breasts heaving, mouth trying to suck in air, her eyes vacant. I had to stifle her scream. If the neighbors hadn't heard our play in the van, they certainly would have been awakened by a scream of the magnitude Nicky was ready to let go.

As she calmed down minutes later, I asked if she was all right. She said she didn't know.

"What happened? What did you do to me?" she asked.

"I did nothing... I simply watched you let go and become the sexual person you wanted to be. I only provided the means for you to express those needs."

"Well, let's go in the house, because I want you to do it, again."

We went inside.

The End of the Beginning

Every story has an ending. I see the end of this story as only the end of my initiation into the D&s lifestyle. I enjoyed the gifts that Nicky bestowed upon me for a bit over six months, and our relationship had many twists and turns. One day, I received a telephone call from Nicky. She told me that her husband was returning from the Northwest. I asked why she thought I'd be interested in knowing that. She had already told me that he was there, and the reason. But since they were separated, it never occurred to me that reconciliation was an option. Worse, she had to acknowledge that he'd gone there on the basis of this being a 'trial separation,' and that he'd always expected that they would reunite upon his return.

Nicky didn't know what to do. After he returned, we saw each other only a few more times. Then, I received a last telephone call. I was at the bowling alley, of all places. Nicky was on her way to overnight with a patient in Ocean City, Maryland, and asked if I would go with her. I explained that I had to bowl that night, but as I thought about it, I decided to get a bowling substitute, so that I could spend time with my beloved Nicky. We arranged that she would pick me up at the bowling alley within the hour. She never showed.