Fulfilling Ch. 01

"Scared lookeeloos confide in me" said the ad title in the personals. Like it was written for me. I clicked and it said. "Nothing much more to say. Respond to the ad with the fantasy you're too scared to fulfill. I won't humiliate you. Unless that's what you want."

Okay then.

So I put in my fantasy. Nothing elaborate. I wanted to give head, so I typed that out and sent it off. I shut the computer down. I was a little shaky even having written it. Small as it was, it was a sort of step. I forgot about it for a week. But one night laying in bed it popped into my head again. I went to the email I had to create for the purpose of answering these ads and never doing anything more, despite the occasional eager, sometimes disturbing, reply. There was a response.

"Shouldn't be a difficult fantasy. Any guy would love to help you out. You don't need my help with that."

I shook my head, replied that in my case it wouldn't be that easy, and anyway, there was no hope of me following through. I closed everything down.

The next morning, I checked, wondering what would show up. Probably nothing. I was wrong. "There's something you're not telling me."

Fine, then. I stopped eating and turned my full attention to writing out the entire fantasy, and explaining my embarrassment about the whole thing. I was shaking. My hand kept drifting to my erection. A dot of precum had soaked my pajamas. My finger rolled over it, and then through the opening drawing the slickness down just behind my swollen head. When I hit "send", my cock twitched. I wished immediately I hadn't sent it.

But an hour later, I was checking the inbox again.

"This would be easier over the phone. I answer anonymous calls." The number followed. "There's no reason to be embarrassed. At the least you will find a sympathetic ear."

There was no way I was calling that number. I shut the computer.

30 minutes later, I had the phone in my hand. He accepts anonymous calls. I didn't have to reveal who I was. There was no way he'd know at all.

"Hello, don't hang up." I could hear the smile.

"Do people a lot?"

"Most of the time. But a few call back. Which one are you?"

How could I put this? I sighed. He broke the silence.

"You the one with the animal costume?"

"No!" I blurted.

More quiet as I chewed my lip. He spoke again, his voice warm, like hands wrapping around my waist, pulling me toward something firm.

"You're the one who wants to eat my cum."

I gasped.

"I told you not to be embarrassed. It's a common fantasy, and we can help with the whole thing. Don't hang up."

"Don't be embarrassed? Even if I weren't now, I would be in the situation."

"I doubt it. You're definitely not the first one who has written entirely the same thing to me. And none who followed through ever came out the other side feeling embarrassed. Some were exhausted. Some were a little...full. And all were happy."

"Any of them come back for more?"

"One or two. Look. I'm going to send you a little form to fill out. Answer the questions and send it back. I'll look it over and then send you back instructions. You choose then. You choose the day of. You choose in the middle of the fun. Stops whenever you say."

"Okay," I said.

"It will be better than okay. "

I hung up. Shaking again, like I had a fever. I put the phone down and tried to go back to my day. This was nuts. I never should have called that number. My groin said different. I was in the latter stages of thickness, and everything felt heavy, fully loaded. I put a hand down there, pressed, and the reaction was immediate. I stroked, not daring to open my zipper, ashamed, but I couldn't pull my hand away. My fingers pulled the skin taut, rolled nerves, and I heard the stranger's voice say again "You're the one who wants to eat my cum," and that was it. I wrapped my hands around my cock as it throbbed with an orgasm that ran waves up my body, leaving me dizzy for a moment.

When I got out of the shower, I opened the email and answered the questions.

The next morning there was a response. Reassuring me that this would be easily accomplished, that it was far more common that I was thinking, and that I would fully enjoy myself. "What's more," it said, "You will be fully enjoyed," which seemed a little corny, truth be told. There followed a list of dates, starting at two weeks out. I'd surely be chickened out by then, I thought. At the end of the message was an assurance that if I backed out there was no problem, "but please call so we don't sit around all day waiting." And there was an address. "Feel free to stalk, but don't climb the fence, please." I would chicken out. I knew it.

But I picked the closest date, and somewhere inside hoped that would be soon enough.

Over the next two weeks, I drove by the address. It was a large house in an upscale neighborhood. It wasn't some weird abandoned property. The grounds were groomed, and the gate was a massive iron thing with an automatic gate. There were no cars out front, but the driveway wrapped around the back.

This was nuts.

I called the number, taking care to make it anonymous again. "I went by the house," I said as soon as he picked up.

"Still ready?"

"I don't know," I said, letting out a shaky breath. "I'm pretty sure I'm going to back out."

"It's okay if you do, but I'm setting things up anyway. I've picked out some nice things here. I think you'll like your dress."

"I'm going to look ridiculous in a dress."

"You won't. And you won't feel ridiculous. And when you see the reaction you'll get, you will forget all these notions. We have a few ways of making you at ease."

"Are you going to drug me?"

He laughed. "No. No drugs. Some wine, if you like. Or you can bring your own if you're worried."

"Wine will probably be needed."

"It shall be done, then."

I called a few more times, and each time we had the same conversation. And then one morning I called, just after looking at the house again. I was parked down the street, certain everyone in the coffee shop inside could tell I was some kind of pervert making pervert calls. A pervert too cowardly to indulge.

"Look, I can't do it. I'm sorry. There is no way I will be anything but embarrassed and stupid looking."

He sighed. "What it we do it right now? Where are you?"

"Down the street, actually. No way."

"Look. I will get things set for your arrival. Low lights, instructions, your outfit. You can come in and prepare at leisure. Psych yourself up and see how you feel once you've got yourself situated. Then you can just throw yourself into it instead of being in this terrible state of anticipation. The experience will be a bit smaller than intended, but certainly enough. And you can always come back." His voice was soothing, and he had a way of saying the word "come", and it called to mind my explosion in the kitchen at the memory of his voice.

"I'm on my way," I said, afraid that if I said "I'm coming," I would lose it, and the desire would surely melt away.

The gate opened as I pulled into the drive. He'd told me to pull around on the right side, around the back of the house, and then into a door with a potted fern out back. The house had shutters, and they were all closed. I sat in the car a moment, shaking again. I decided. I threw

he car in reverse, and was about to drive away when I noticed something on the step outside the door: a pair of black heels pressed next to each other. "We record nothing. It's a deal for all involved, believe me.

"We make it nice. If nothing else, you see your outfit. You can try it on. Leave after. You will regret not trying."

I put the car in park, leapt out, and snatched up the heels as I dove through the door.

I was in a dim, cool room. I threw the bolt. As my eyes adjusted to the twilight, I saw a table with a low light illuminating a glass of wine. Beside it a chair. Nearby a screen behind which I might get dressed. And on the wall beside me a shelf loaded with dozens of shoes, the sort I would have begged a girlfriend to leave on while we fucked. And beside that a dress hung on a rack. Something black, another gray, both in the same style. There was a tone, and then I heard the stranger's voice come over the intercom.

"I hope you find things to your liking. I am over on the wall beside the table with the lamp. There's your wine, if you haven't spotted it. There's a shower if you want to wash up a bit before. Once you're ready, you can let me know over the intercom by pressing the button and talking, or you can just step into the house and start walking to your right. I'll certainly hear your steps. Behind the screen you'll find some underthings. Try them on and then the dress. I think you'll be happy with their effects. You'll also find inspiring images. Think of them as you. I'll leave you be, now."

I went straight to the wine and took a sip. The shoes clicked together, reminding me they were in my hand. I looked at them.

Why not?

I stripped off my shoes and socks, and then decided to wash them quickly before putting on my new shoes. I did this with my eyes closed, in a bathroom lit in the same dim orange way. It smelled like vanilla. I went back out, giddy now, and picked up the shoes. I started to put one on and then decided to sit. I didn't have any practice in heels. Surely I would totter.

"Just try" I heard the stranger say, and I slipped one on. It made a light sighing sound as it slipped over my bare skin, and my cock thumped against my briefs. I took a sip of wine, feeling my foot stretched in the shoe, running my hand over the smooth skin along the top. I slipped the other on and stood, wobbling a little like drunk socialite. The cuffs of my pants brushed the skin, reminding me what I was wearing. I picked up the wine and walked over to look at the other shoes. They were lines up side by side, toes aimed out. Straps hung down from some. I ran my hand over them, sipped my wine and licked my lips. There were simple white stiletto sandals, glittery pumps, a pair of leather caged heels that I knew I couldn't do. It would have to be something with a closed toe, or I'd spoil the entire thing, but with each step I felt more ready. Behind the shoe were some of the inspiring images. Women posing in the heels. In various stages of dress. One was wearing pumps very much like the ones I wore. She was kneeling front of a man, his pants open, his cock deep in her mouth. She looked at the camera. She looked at me.

It settled me right then on the ones on my feet.

I chose the black dress in a sudden fury, and clicked across the floor.

Behind the screen was a chair, a rack on which to hang my chosen dress, and some other, curious items. A note explained their use.

And there were more images. Women kneeling before cocks, women licking them, stroking them, smiling. One woman was smiling up from a ring of them surrounding her. Another had one in each hand, and she looked directly at me. There was a line of spittle from one of the cocks to her mouth, and I could see her chest was splattered with cum.

All of the women shared a quality: they all had my eyes, at least those who were looking into the camera when their moment was captured.

My mouth was watering.

I slipped into the garment. Designed to cover up the places I wasn't willing to shave. Designed to tame my hard cock. It had looked like it would be uncomfortable, but it was the opposite. I had to still myself for a bit. Moving was pleasurable. The fabric inside, tight against me, caressed like lips. It felt almost like I was fucking.

This man was a genius.

The women watched me get dressed. I imagined them cheering me on, telling me I could look like them. I was them. I had drained the wine now, and it was working.

I went to the chair, sat down, and leaned over to the intercom. My finger trembled and I had trouble hitting it, but I finally managed. "I think I'm ready," I said. "No I'm not."

There was a long pause. "I'm sure you are. Did you like the wine?"

"Yes. I definitely can't drive right now."

"Well then. You have time to kill."

"This has worked with other people? I'm a guy in a dress, fuck sake. Didn't even put on makeup or a wig." I felt myself wilting.

"It does. May I come in? You'll have to buzz me in. It's a button there under the table. You know me, and I know your secrets. I can perhaps put you at ease." It seemed right. I did trust him, by now. I hit the buzzer, and he said, laughing, "I'm not there yet. I'll knock when I am. It will take me a bit. Big house. In the meantime, there's a set of headphones inside the drawer in your table. They're set to play some...inspirational sounds. Try the

on. I'll knock loudly."

I pulled open the drawer and found the headphones. I slipped them on and heard the distinct sounds of eager cocksucking. Moans from a woman and a man intertwined, but her sounds dominated. Her pleasure as she worked on him. "Cum for me," she urged. She moaned, and then begged again, then I heard her voice change. A sound of delight escaping from her full mouth. The "mmmm" that accompanies appreciation of delicious food, and the sound of her withdrawing the surely spent cock from her mouth to thank him for the reward.

That was right when he knocked, and I was hitting the button before I knew what I was doing.

I jumped up at the door opened, ripped the headphones off as if I'd been caught doing something wrong. He stepped into the room wearing a gentle smile and a pair of black pants I recognized instantly. He was taller than me if I hadn't been in heels, slender, perhaps a little older, and not offensively handsome. Masculine enough. He had a glass of wine in his hand.

I shook my head as he crossed the room slowly. I glanced down at the pants. "Those happen to be my favorite of the shoes."

I glanced over at the screen, and made a gesture that felt surprisingly feminine. He understood, and nodded.

"Okay," I said.

"Thank you," he said.

"I look stupid."

He shook his head. He had stopped a distance from me, as if approaching an animal that might bolt. "Bullshit."

His expression didn't change. "A challenge then. I'll prove you don't look stupid. I'll prove you look as sexy now as you do in that photo over there. The one where you're making the noises you just heard over the headphones. Remember them?" He was edging his way toward me now. He came close enough that he brushed against me as he put his wineglass on the table. "Accepted?" he asked, and then he stepped back. "Get on your knees for me," he said, not waiting for an answer. "Please. Trust me one more time."

I lowered myself down, shakily, to my knees, the heels clacking on the ground as I did.

Now he stood before me, arm's length away. I looked up at him. He was moving his arms. I heard his belt hiss and the buckle clink as he undid it, and he gestured with his eyes for me to watch while he unbuttoned his pants. He drew the zipper down, walking towards me. He wore gray underneath, and I could already see what he was going to show me before he pulled it out. "Does it look to you like I think you look stupid?"

His cock took up nearly all the remaining distance between us. It stood straight out, hard, and thick, the head shiny, taut with excitement. "Now close your eyes. I won't do anything, I just want you to imagine."

I obeyed, half hoping he would just shove himself into my mouth and end the questioning, but he didn't. "There you were in the photo, kneeling before me just like now, sucking until I thought I would go crazy, moaning, begging me to cum for you until I couldn't hold it anymore. My hands tangled in your hair, I filled your mouth with so much cum that it spilled out of your mouth and onto your dress. You pulled me out of your mouth, swallowed, and licked me clean. Then you got up, and went on your way while I crumbled into that chair. Now open your eyes."

I opened my eyes, and his cock was still hard before me. He slipped a hand behind my head. He didn't pull me towards him. I moved forward, slowly, until I had pressed the tip of his cock to my closed lips. I parted them just enough that the opened around the slightly firm head, caressed the smooth skin. It was a sort of kiss, and when I pulled away from it there was a slight smacking sound. I moved back, out of breath, breathing through open lips. I looked up at him. He smiled. I looked down and he had put a hand around his shaft. He ran one finger forward along the bottom, and a glistening bead of precum formed. "That's because of you," he said. "Taste it. Just lick it off. I'm in no hurry."

I leaned forward, stuck out a tentative tongue, and licked the bead from his cock. It tasted like saltwater, It spread over my tongue and clung there. I opened my mouth again, inhaling, but this time I moved forward and took his head into my mouth, pressing my lips hard around it, and lolling my tongue over the skin, pressing the hole in the tip of his penis, trying to get more precum out by licking and then by sucking. I tasted more of his salt, and, running my tongue along the bottom of his shaft, I took him more into my mouth. I was whimpering, breathing hard through my nose, pushing him deeper. My jaw clicked as I worked.

And then suddenly gagging. I pulled back, gasping, trying to not ruin the mood by throwing up suddenly. I sounded like I'd just broken the surface after nearly drowning.

He pushed breath out of his mouth. "Wow. I told you you were good. Take it easy."

I opened my eyes. There was a line of spit connecting my mouth to his cock. "Come here," I whispered, and pulled him toward me, into my mouth. I grabbed his ass and worked my mouth over him, back and forth, moaning. I moved a hand to feel his balls, hoping my hand wasn't too cold for him, and I massaged them, willing them to make plenty of cum.

I pulled his cock out now. It was soaked in my spit, and I kissed it, looking up at him, rubbing it on my lips. "Am I good?" I asked him.

"Oh yes," he said, putting his hand through my hair. "Listen, when I come, I'm going to pull back so it fills your mouth and doesn't go straight down your throat. I want you to taste it."

I responded with the "mmm" from before, and put hand on his shaft, stroking it while I held his head in my mouth and rolled my tongue over it in circles. Then I pushed him into my mouth again. I sped up, and I ran my hand in counterpoint to my lips, twisting a little. Rewarded with his moans. I recognized them, and I pulled away. "Are you going to cum for me?" I asked, and kissed his cock. "Are you going to cum in my mouth?" I kissed it again. Then he finally pushed me himself, whispering something unintelligible, and he thrust a few times deep into my mouth before regaining control, releasing me, and letting me return to my work.

And he did let me work. I would watch his shaft disappear into my mouth, my lips shrinking in and swelling as I took him in and then pulled him away. I experimented, putting my hands behind my back, letting him flop completely out of my mouth, I would move in with no hands and suckle at the base of his penis. He responded well to this, calling me a "good girl", which made me smile and suck harder, to prove I was.

Then he said. "Okay okay okay." I had him in my mouth. I looked up. "Put your hands behind your back again," he said. I obeyed, and pretended they were tied. I wanted to grab my heels, but they were out of reach unless I squatted down, which wouldn't work unless he was cumming on my face. I fiercely wanted that. I almost begged for it, but he told me what he was going to do to me.. "Stay right there," he said. "And keep looking at me with those beautiful eyes."

He wrapped a hand around his cock, and began stroking himself. I groaned, and could barely keep still as I felt him jerking off into my mouth. He wanted me. I looked at him, moaned tried to make him see I was begging for him to fill my mouth with his cum. I stopped licking, and placed my tongue under his swelling head, making a place for it to land.