His First Time

by Conquered

The windshield wipers squeaked as he got on the Saw Mill Parkway. As he fed into traffic, he exhaled again, to relieve the tension. But it would only be momentary. He knew that too.

Today was going to be both methodically IN his control, and maddeningly NOT in his control.

He had to take the day off work, and plan it around Michelle not finding out about it. Setting his away messages, and his excuses to give him the whole day, which he might need. He didn't know.

On the passenger seat next to him was a "play bag." Overnight bag with a plastic bagged, clean change of clothing. His toiletries so that he came home smelling the same way that he left. Underwear included. Into the same bag would go anything that would smell or look like he had NOT been in the office that day. In a separate compartment was his work material. Blackberry and a file or two in case he had to refer to it.

But there was nothing else. Usually, he would have all manner of bdsm toys, etc. for him and his partner to play with. Today, he was nstructed by Lady S to bring nothing in that regard.

His wallet and keys were all he carried now. And those keys jangled warning bells as he veered off the exit for Tarrytown. He glanced at the directions in his hand, and made a right at the foot of the exit. The motel would be at the side of the road, on his right, about a mile down. He inhaled deeply again. But the tension was not going away that quickly this time.

As he saw the motel up ahead, the windshield wipers swiped the light rain off the windshield, and was oddly in tune with his heartbeat. He was early pulling into the parking lot, and thought of Lady S again, and her instructions. Being 5 minutes early was no better than being five minutes late.

He paused. He was instructed to go directly to the room. But he was early, and instead sat in the car and waited. Looking at the room set off to the side, slightly isolated.

She had paid for it with his credit card, along with a few more trinkets for the afternoon. He had long since given up being able to control how or when she used the card.

He had wisely set the spending limit low on this card, but was still concerned with he had given her the number in a moment of weakness two years ago. She had been "fair" in her usage of it, but a few recurring expenses added up. This is how it all happened with the two of them. Very very gradually she built up her knowledge of him and the weapons she needed to coerce him if necessary into doing what she wanted.

Lady S, as he called her, made it clear that it would be very "unwise" of him to not meet her demands.

"I would start out small with the steps I would take," she said one night to him on the phone, while they were in that mutually hypnotic haze they got into whenever they discussed their "financial partnership." She slowly said, "I'd pick just one vulnerability area -- home, business, neighborhood, friends, family -- and do something small that would probably mean nothing and expose nothing. Until they get a second or third piece of the puzzle."

He could hear her rubbing her pussy through the telephone. Shamefully, HE was getting hard too as they went through this verbal ritual. "But that first puzzle piece might be a meaningless password to a profile, or site that would contain your image or something that would cause you great life-changes. Do you want to go there? Do you want to start this process? Do you want to start this snowball going down the hill, and with it the fear of what you might be unleashing? I have an awful lot of steps I can take to convince you otherwise, don't I, Arthur?"

I shook that image from my head, and looked at my watch. It was time. I got out of the car with my bag, and headed across the way.

Her car was in front of the motel door. The room was off to the side, and they were alone. No one next door for five doors. No one upstairs. Privacy. He inhaled as he approached the door and – as he was instructed to do – simply enter through the unlocked door. It was dark inside.

* * * *

"Right on time!" She laughed. "Stay where you are a minute. We're videotaping this."

I nodded my head. "Say yes, Arthur," she instructed.

"Yes," I replied. We?

"Good," she replied. "We need to just complete a few things first. Why don't you tell us your full name, and such. Some personal information about yourself. Speak clearly for the video camera."

I spoke my name into the camera, and then my address.

"More. You know what I want on here." She was insistent.

I continued. I included my wife's name. My son's. The company I worked for. My boss. My neighbors. My friends. Finally, I paused.

"That's good Arthur. And, you walked in that door on your own accord, correct?"

I nodded. "Yes, Lady S."

"Good. No coercion was used. Could you walk out right now?"

I didn't know what to say. I knew that I couldn't, but I couldn't say that on this recording. I knew what she wanted this recording for, and I had to give it to her.

And then I realized that, then again, I was here on my own accord, really. Lady S and I had been talking about this for two years. She had slowly boxed me into a position where even if I wanted to back out, I didn't know what would happen. But we both know where this was going, and I accepted that. But it didn't make me any less frightening.

"Yes Lady S. I am here voluntarily."

"Good. Now, there is a blindfold and a pair of handcuffs on the chair next to the door. Get them now, put the blindfold in, and cuff your hands behind your back. This is for "play purposes," right? Do you do this voluntarily as well, Arthur?"

"Yes Lady S." And I reached for the handcuffs on the chair. They were cold, hard and real.

"Put one on your right wrist first, Arthur. Then the blindfold. Then the other cuff, behind your back. Let's hurry now."

And I did it. Got the blindfold on, and clicked the cuffs locked behind my back.

"Turn around," she said. "So I can have a photo of this. Of YOU putting yourself in bondage. How lovely." I heard the faint click of the camera, then her heels moving toward me. She turned me around and started guiding me slowly across the room. She talked as she did. "This afternoon is for a purpose, and we both know that. For you to prove your commitment to me, and this Thing we are in. Get to your knees slowly and stay still." She helped me down, and I obeyed her. I stayed stone still.

I heard her rustling around. Then I heard a second person across the room. Also moving something. I sensed the light in the room had gotten brighter. Floodlights, perhaps.

Then, Lady S was next to me again. She played with my hair a moment. "I'm going to take the blindfold off, and you're going to look directly into the video camera again. Do not look up. You'll answer my questions accordingly."

"Yes," I replied. And she lifted the blindfold from my eyes again. Two lights were shining on me. "Do NOT look up at us. Understand?"

She said. All I saw were four naked legs in front of me. Two female legs -- Lady S -- and two strong male legs: whose I did not know. Then the light went on on the video camera.

Now, the male legs advanced forward, as Lady S moved behind the video camera.

"Now you know, Arthur, what you are going to be doing, don't you? What I want this video of."

"Yes," I replied.

"Tell me. Tell the video camera."

"You want a video of me sucking a cock for you."

"Will this be your first cock, Arthur." She kept using my name.

"Yes it is."

Now the man in front of me began stroking his cock. It was thick and appeared long. The camera, however, was trained on me, and did not show his face, which was above the frame. My face was the star of this production.

"And you are doing this voluntarily, aren't you?"

"Yes Lady S."

And with that, the cock was in my face. "Then start, Arthur. Start sucking."

And I took my first cock into my mouth. It was an odd sensation. Hard skin. Thick.

The man's hand now was on the back of my head. Very slowly, he began to kick up a rhythm. Slowly into my mouth. Then slowly out. "Hmmmm. Looks great, Arthur. Keep it up."

He started getting harder. My hands were still tied, and I began to feel frightened.

Lady S and I had always spoken about a condom for something like this. But there was none in sight. But I could say nothing, as his cock was in my mouth.

"That looks great. Now turn toward me a bit." And I saw a flash, as she was getting digital stills of this. I glanced up and saw that Lady S. was wearing a mask to hide her own face from the camera, should it appear.

"I want to see him go deep. Take it all in, then hold it." And as his cock went deeper into my mouth and then my throat, the Man whose cock I was sucking moaned, and he held my head.

"Hold him there," she instructed the Man. Then a flash. Then another. Then he let go, pulled out, and I was allowed to rest a moment. Lady S. put the camera on pause.

The flashing light shined. She changed the cartridge on her camera. "Ok, now the money shot."

Now I began panicking. I pulled my mouth off the Man's cock, and gasped out to her.

"You said that you wouldn't make me take a cock bareback. Please have him put a condom on before he cums."

Both Lady S, and the Man above me now huckled. "I don't think so, hon. You're going to get a mouthful of cum." She said matter-of-factly. "Regardless of what I promised you before, that's what I came here to see."

"Please no! I'll do anything!" I begged. I was truly frightened.

And with that, Lady S gave a small laugh. She walked over to me and ran her fingers through my hair "Anything, huh?"

"Yes," I replied.

She then walked slowly over to the door, where my pants were. I heard her doing something, then, a moment later, she came back to me with my wallet in hand.

"Let's see what we have here," she said, as she looked in my billfold area. "Twenty, 40, 60, 110, . . $180?" She took the cash out, and held it in front of me. "You expect to buy a condom from me with this?" She took the money anyway, and tucked it in her black bra.

"Please! Please don't make me take his cum in my mouth!" I begged. My heart was pumping.

Silence for a moment, then she began looking through the wallet again. She pull out a credit card. "This is your play card, isn't it?" She said, as she held up my Republic Bank Visa card. I nodded. "What is the limit?"

"$1500 I think."

She then reached for her cellphone, and began dialing the phone number on the back of the card. "Get that cock back in your mouth," she snapped, and I began sucking again.

I could hear the automated voice from the cellphone give punch-in choices. Lady S was making them. Then, after a few choices, she moved to me and held the phone to my ear. "You want a condom? Then you're going to do one simple thing: You're going to raise the limit on this card."

The voice on the other end of the phone now came up. "Customer Service. How can we help you."

I then spoke into the cellphone. "Yes, I'd like to raise my limit on this card."

The cheery Customer service woman then asked, "I can help you with that. What would you like your limit raised to?"

Lady S was listening and whispered to me "$10,000."

I looked up at her, but her eyes were stone serious. "Just fucking do it!" she hissed. "$10,000?"

"I'm sorry but we can only raise it today to $6000. And your have been approved for authorization for that amount. I would just need your pin number and the answer to your security question. Your pin first."

I paused, looked up to Lady S, and said into the cell "5679." Both she and the Customer Service woman noted it.

"And now the answer to your security question: Who was your third grade teacher?"

I looked up to Lady S. "Mrs. Goodman." She smiled also, as the Customer service woman said. "Alright. You've authorized us to raise the limit on your card to $6000. Will there be anything else today?"

Lady S said softly to me, "Tell her that you have to leave, but that your wife will be changing the security question and pin number."

I paused. She wanted to have control over this account. I had no choice.

So I told the customer service woman what Lady S had asked, and when she asked for me to put my wife on, she took the phone, and walked into the bathroom of the motel room, where I could not hear her complete the call.

And as I tried to listen, the Man grabbed my head and shoved his cock into it again. He spoke his first words. "Looks like you're fucked. She's gonna change the pin and passcode, and the account will be hers. You won't be able to get back in to lower the limit again. You'll just get the bill each month. Fucked man."

A few moments later, Lady S came out of the bathroom with a smile. When she put her cell phone away, she came out of her pocketbook with two condoms in her hand. She held them up to show me. Lady S then reached into her purse again and came out with a tiny sewing kit. She plucked a sewing needle from the kit, and then began punching holes through the foil and spearing through one of the condoms over and over. She smiled while doing this.

Lady S then approached me with both condoms, and put them behind her back. She mixed them up behind her back, then came out with both hands, the condoms hidden in her palms. I would have to choose which one I would get. "Let's see how lucky you are today. Fifty-fifty chance, honey. Your choice."

I paused a moment, then chose the one in her right hand. She instantly tossed the other one over her shoulder. "Blindfold him again," she instructed the man. "I want this to be a surprise for him."

I was in the dark again, and I heard her opening up the condom, and reaching to hand it to the Man above me. He rolled it onto himself, and in a second, I was again sucking his cock. Lady S started the camera again.

He pulled me to his cock again. I could taste the latex, which was worse than his bare cock. Not knowing whether the condom was broken or not was making me nervous. Had I made the right choice?

His cock started getting harder and bigger in my mouth. Lady S was breathing faster. "Suck him! Do it now. Harder."

Then she moved back across the room again, and came back. Now she took my blindfold off. "Keep sucking. I wanted to show you this." And in her hand was the condom she had tossed across the room, that I didn't choose. The foil was riddled with holes.

"Ok? Feel better?" She asked, comfortingly. And I nodded through teary eyes, taking his cock into my throat for the first time. She cheered. "Yes! Alright. What a great cocksucker."

His pace picked up. She now rubbed her pussy, watching. "Keep sucking. Don't disappoint me," she urged. "Just imagine how I'm going to pillage this credit card. I'm going to keep it at the limit every month. It's your job to keep it going. Got it?"

Now, the Man grabbed my head with both hands and began pumping into my mouth. "Take it all, Arthur. Do it." And I heard Lady S now humming a vibrator over her clit. "Come on! All the way."

And with that, I felt a sudden rush of cum in my mouth! I tried pulling away, but I couldn't. "Hold him there. Hold him. Make him take it all," she urged. And my mouth was filled with his cum. What was happening??

Lady S put her mouth right to my ear, "You'll lick anything that drips out of your mouth off the floor. You'll hold it in your mouth for the camera."

And the Man pulled out of my mouth, and I saw that his condom was riddled with holes just as the other one was. "Let's see the cum." And I showed the camera. "GREAT shot."

"Now, fucking swallow it, Arthur! Do it RIGHT now." And I had no choice. It was all in my mouth now.

When he was finally all done, she came over to me and ran her fingers through my hair. "The condom you picked, I had already punched with holes, so you couldn't win. Both would have leaked. This is what I wanted. I wasn't going to let you get away with it." And she kissed my cheek, and hugged me.

"You'll probably be fine. There's nothing you can do now about it anyway."

And with that, she eased me to my feet, and over to the bed in the room, and bent me over the edge, and because my arms were behind me, I fell face first on the bed. My ass in the air.

"Now, hon, it's time for you to start bidding on how much you would give to keep that cock out of your ass." And both she and the Man began laughing, and I was held face down.

"Let's start the bidding at $1000," she said. As serious as a car wreck.