The Personals Ad

I'm in the trunk of a car, my hands and feet tied. It's dark, and I struggle to keep myself from slamming into the sides of the trunk as the car bumps and swerves. This was a terrible idea. I'm fully clothed, except for my shoes which are somewhere loose in the trunk with me. Seemingly disconnected from the fear in my head, my cock is hard as it rubs and bumps inside my underwear.

This all started with an ad I posted on an online personals site. After years of trying to find an outlet for my strange kink, the ad was a last-ditch effort to find someone who could do to me the things I crave.

My ad went unanswered at first, and I thought maybe it was a lost cause. There were no other ads like it, and after a few days of silence I figured that was the end of it. And then I got her first text, and it read simply, "I will do this," followed by "how much?"

The ad had been simple, and went something like this. "Wanted: Someone to tie me up and hold me captive. I will pay for your time. No expectations, no strings attached."

I like to be tied up. No, it's more than that; I yearn for it. I live to lose control to another person, to be captive and subject to their whims. It's an odd obsession, I admit it.

I've even paid escorts to tie me up in the past, but it never quite scratched the itch. Too much emphasis on sex, not enough on the craft. Not that there's anything wrong with sex, but I found only momentary pleasure and ultimately profound disappointment in a few experiences that revolved around handcuffs and a quick blowjob.

The idea of posting an ad inspired fantasies of something different, more organic. Finding a perfectly normal person who would partake in my most abnormal desires, and might even enjoy it.

I stared at the reply I had received, momentarily dumbfounded. Before long, I had my reply composed and sent: "$200, you provide the rope and the place"

The reply came back minutes later. "$300."

"Ok," I replied without too much thought.

The next reply took a few minutes to arrive. "Give me your address, I'll pick you up in my car."

"Now?" I asked.

"Now. Address." was the reply.

This gave me pause. It had not occurred to me that I might get a reply to my ad and that the arrangement would start immediately.

What the heck, I said to myself, I want this. I sent my address, tacitly agreeing to the arrangement and the upsell. There were no further texts after that.

I sat and waited, watching carefully out the window to my living room, wondering if each car that came down my block was the one. Finally a car slowed as it rolled down the street, stopping in front of my house. My mind raced, eyes taking in every detail. It was a gray sedan, maybe a VW. Nothing fancy, probably 10 years old and a little dirty.

The driver sat for a long moment, looking through the passenger window toward my house. I stood and walked swiftly to my front door. As I opened the door, I saw the driving stepping out of the car.

My first impression of her was of an average woman, maybe in her late 30s. Black hair, tan skin. She stepped slowly around the car to stand by the passenger door, leaning against the car. She regarded me with likely the same expression I had, one of cautious curiosity.

I began to register more details. She was indeed quite average, in height, weight, and overall appearance. I guessed her to be Mexican or of some other Latin descent. She was wearing blue jeans and a black leather jacket over a white shirt.

Her face was expressionless as she watched me carefully, brown eyes holding my gaze. She took a few steps toward me, and said quietly, "You the guy with the ad?" She spoke clearly and with just the faintest accent.

I nodded. "Kenny," I said simply.

She seemed to relax slightly. "Veronica," she replied.

She stopped a few steps in front of me, saying quietly "I've never done anything like this to be honest, but I could really use the money and..." she faltered, looking down.

I struggled to find anything intelligent to say, so we just stood in silence for a long, awkward moment. Then she seemed to find her confidence again, and said "And I like what you posted. Being in charge."

"Cool," I said, still not sure what else to say. I reached into my pocket and took out the money, a wad of crisp $20 bills. As I stood there with my hand outstretched, I took in a few more details. Veronica didn't seem to be wearing makeup, and it occurred to me that her plain appearance might have been by design, so that this strange pervert she was meeting might find her less attractive.

She stepped toward me and took the money from my outstretched hand, quickly slipping it into a pocket. It hit me that she now had what she wanted, and she could just leave. How easily I could have been scammed in that moment.

Instead, she reached out and put a hand tentatively on my shoulder, saying "alright, come get in my car."

We walked the short distance to her car, and as quickly as I started toward the passenger door, I realized Veronica had something else in mind.

Walking toward the back of the car, she withdrew her keys and quickly popped open the trunk. "Hop in," she said quietly, "before anyone sees us."

I looked at her incredulously. "Oh come on," she said with a wry smile, "the hostage always rides in the trunk, right? It's a short ride, you'll be fine."

Peering into the trunk, I saw that it was lined with black cloth, and was clean and empty save for a few pieces of rope. It was at this moment that I became aware of my cock stirring in my pants as I realized that rope was probably meant for me. Throwing caution to the wind, I turned to sit on the rear bumper of the car, then scooted myself backward into the trunk.

"Good job," Veronica said approvingly, still standing behind me, one hand of the open trunk door. "Now turn so you're facing the front."

I slowly did as she said, laying on my back, then turning on my side facing the front of the car.

"Hands behind your back," she said. He voice was firm, but not mean.

Realizing this was the point of no return, I hesitated for just a moment before steeling myself and putting my hands behind my back as instructed.

Facing toward the dark end of the trunk, I couldn't see what Veronica was doing, but I felt the rope go against first one wrist, then around the other. Around both several times, then in between, then around again. Finally I felt her tie one knot, then a second.

I waited, expecting the trunk to close, but it didn't. After a moment, I felt her tugging on one of my shoes, pulling it off, then pulling the second one off as well. My socks quickly followed, and I was barefoot. A moment later I felt her tying my ankles together similar to how my wrists had been tied.

I was enthralled by the sensations. Sure, I'd been tied up before, but never like this. The strangeness of the situation, the danger, made the feeling more real than ever before. My cock stood at rigid attention in my pants.

"You ok there?" She asked.

"Yeah." I said, with more certainty than I felt.

"Good," she said. "Let's go."

I braced myself for the trunk to close, but it didn't. Instead, I felt Veronica's hand touch the top of my head, then begin sliding down my neck. Her touch rolled over my shoulder, then across my body to my chest. It continued down my body, across my belly, and then just for the briefest and most fleeting moment, across my crotch. Her hand made just the lightest brush over the raised lump in my pants, then quickly down my legs, across my bare feet, and off.

Was that intentional? Did she mean to touch my cock? I couldn't be sure she would even had noticed, but I also couldn't glean any other purpose in what she had done.

With that, quickly the trunk was closed, and I plunged into darkness. I heard Veronica step around the car, open the driver's door, and get inside. The door closed, and almost immediately the engine started, drowning out all other noises.

Within moments the car was in motion, and I found myself trying not to hit the inside walls of the trunk as the car bumped and turned.

It was hard to measure time in the dark, still air of the trunk. I guessed maybe 5 minutes had passed when the car slowed, then stopped. The engine turned off and I heard the car door open then close.

The trunk popped open and blinding light hit my eyes. After a moment of squinting my eyes adjusted, and I could see Veronica looking down at me, waiting for me to be able to see. I couldn't help but notice her silhouette with her arms raised, hands on the top of the raised trunk door. Her body was a study in gentle curves, with her white shirt rising to show some dark skin as the black jacket parted with her raised arms.

She looked slightly amused as I blinked. "Go ahead and wriggle your way on out," she said, and I scooted my legs over the edge of the trunk, sliding to a seated position on the bumper. She knelt down and quickly untied the rope around my ankles, saying "we can't be attracting too much attention while I get you into my house."

With my feet untied, Veronica said "Up you go." I stood, my hands still tied behind my back. She quickly put her arm around me like we were buddies, and we walked side by side up three steps and through a metal door into a small, blue house.

Stepping into what seemed to be a small living room, I noted a couch against one wall, and a small television sitting on a table against the opposite wall. Aside from those furnishings, the room was empty.

Seeming to sense my thoughts, Veronica said "I just moved in here a few weeks ago, and I don't have much furniture. It's nice enough, and the rent is cheap."

I stood awkwardly in the middle of the room as Veronica closed the door behind me. "Well, make yourself at home," she said, gesturing to the couch. She quickly shrugged off her leather jacket, tossing it into an unseen room. Her white t-shirt was not tight, but revealed feminine curves and the outline of a bra, one white strap of which was just visible across a tan shoulder beside the shirt's oversized collar.

I sat on the couch, somewhat uncomfortably as my hands were still tied behind me. Veronica came around to stand in front of me, looking me up and down, saying "Well, you wanted to be tied up and captive, and here you are. Not really that tied up though, let's fix that."

She left the room for a moment, quickly coming back with more pieces of rope like the ones that had been in the car trunk. She knelt by my feet and started to re-tie my ankles. She seemed to know what she was doing, and had my ankles tied together again quickly.

The ropes around my wrists and ankles felt tight enough that I didn't think I would be able to just slip out. I figured I might be able to find the knots with my fingers and eventually untie them, but I decided there wasn't really any need.

Veronica regarded me for a moment, then said, "No, not quite done." With one hand against my chest she pushed me gently backward on the couch, then finally into a laying position facing the back of the couch. I lay there for a moment wondering what she had in mind, then quickly found out when I felt a rope being connected from my wrists to my ankles.

"This is a hogtie, right?" She asked, rhetorically. I sensed that she was kneeling behind me, and I could feel both of her hands resting on my upturned hip. "Now I think you really aren't going anywhere."

As Veronica stood up I tested my bonds, pushing and pulling to see if any might come loose. Nothing budged, and even more than before I was sure that there wouldn't be any easy escape from this.

She laughed lightly, saying "Keep squirming, I kinda like that. I don't think you're going to get out on your own though." She watched me for another moment, then continued, "Well, you're tied up and captive like you wanted. What next?"

After a pause, I responded "Uh, I don't know. This is what I wanted. I wasn't really sure what to expect."

"Uh huh." She said, quizzically. "Well, I'm going to sit and read my book and see if you can get yourself out of this." I rolled back to my other side so I could see her, just as she pulled up a metal folding chair a few feet away from me and proceeded to open a book and start reading.

I wriggled and squirmed for a few minutes, blindly trying to figure out where the knots where that were holding the rope around my wrists. I wasn't trying that hard to escape, but eventually I found a knot with my fingers, and just as I found a loose end to try to work, Veronica looked up from her book and stood.

"Ah, naughty." She chided. "Do I need to make this harder for you?"

She took a step so that she was standing over me, reaching down to quickly pull the knot I had found out of reach. She paused for a moment as if considering what to do, then suddenly she had the pulled the hem of my shirt up to my navel, and her fingers were working the button on my pants. With the button undone, she proceeded to unzip the fly and started pulling my pants down over my underwear.

"Oh, did I distract you?" She teased as she finished pulling my pants down around my knees. She withdrew her hands and stepped back to regard me, smiling openly.

"You know how ridiculous you look right now?" She asked mockingly. "I didn't know grown men still wore tighty-whities." This was in reference to my white briefs, now in full view.

"I..." I stammered lamely, "I didn't realize I'd be doing this when I got dressed this morning."

She stood over me, arms crossed over her chest, laughing quietly. Then she leaned over again and pulled the back of my underwear down exposing my ass, leaving my cock snagged in the front. She laughed harder now, saying "Look at you, ass out and tied up." I felt totally humiliated, looking up at this stranger standing over me, her breasts bouncing lightly up and down as she laughed.

It seemed like she caught me looking at her chest, and her laughter faded away. "Do you think I'm pretty?" She asked, her tone more serious.

"Y-yeah, of course," I replied genuinely.

"Hmm, thanks." She said smiling, "of course, from where you are you'd have to say that."

I was telling the truth; she wasn't stunning but she was definitely pretty. She was neither skinny nor large, and the smooth tan skin of her face was marred only by a few subtle blemishes that could easily have been hidden with makeup if she chose to wear it.

Her eyes held mine for a moment, and then her hands were tugging at the hem of her white t-shirt, pulling it up over her head in one smooth motion, then dropping the shirt to the floor. I was entranced by the sight of her white lacy bra, and her dark-skinned belly and shoulders. No tan lines, I realized, concluding that her skin color was not from the sun. Next she unbuttoned and peeled off her jeans, leaving white panties and smooth legs.

I watched as she stood for a moment in her bra and panties, aware that this was taking an unexpected but very pleasant turn.

Veronica eyed me for a moment, then reached for the metal chair she had sat on earlier, pulling it close and sitting down with her knees against the couch. Her gaze traveled down my body to my crotch, half exposed with my hard cock still inside the folds of my underwear.

She reached out a hand and took hold of my cock through the cloth of my underwear. I shuddered involuntarily and she smiled. "You seem to be enjoying this," she said simply as her fingers traveled the length of my cock and traced the outline of my balls.

"I'm enjoying this too," she said after a moment, "having you helpless like this is kinda turning me on. Which gives me an idea..."

She trailed off in thought, then stood up suddenly and walked quickly out of the room. Feeling momentarily disappointed that her attention had been diverted, my cock strained against fabric of my underwear longing for more.

Veronica re-appeared a moment later carrying what looked like a hand-held massager. A vibrator, I realized, but not the cock-shaped kind, this was the type that had a round plastic head with little soft bumps. It was white and had a long power cord, and she fumbled around the room for a moment looking for the closest outlet. I was captivated, in helpless anticipation watching her maneuver around the room in her bra and panties until finally she found a plug.

Holding the massager in one hand, she returned to the chair directly in front of me on the couch. Her bare knees were once again up against the couch so that we were nearly touching. She pushed a button on the massager, and it started to emit a buzzing sound, and I could see that the round end was vibrating. She parted her legs slightly and brought the vibrating end down into the crotch of her panties.

Almost immediately her eyes closed and a contented smile occupied her face. She continued to hold the vibrator against her crotch, moving it very slightly up and down. As the seconds passed, her mouth opened and she began breathing heavily. Her eyes opened again and fixed on me as her breathing grew faster and faster. I realized how aroused I felt watching this happen, knowing that she was fueling her pleasure with the visual of my bound body in front of her. I was helpless to do anything other than watch as she began to shudder. She gasped as orgasm gripped her, her chest heaved up and down as the waves of orgasm waned. My greedy eyes tracked her breasts bouncing inside the white lace of her bra.

She let out a long sigh, breaking her gaze on me for a moment to look down. Both of us registered the growing wet spot on her white panties where the head of the vibrator had been.

"God I love this thing," Veronica breathed. "The problem is, once you get yourself with one of these, you never want anything else."

She eyed me again, her gaze starting at my eyes, but moving down to my crotch where my cock, hard as ever, had made its own tiny wet spot in the cloth of my underwear.

"I wonder..." she began, but didn't finish the thought. She started the massager buzzing again, and held it out toward my crotch. She let the vibrating head come in brief contact with the head of my cock, and I felt a jolt shoot through me. It felt great, almost too intense even though it had just touched me for an instant.

She had been watching my reaction carefully, and she said, "How did that feel?"

"Um, good. That's... intense," I said.

She nodded and smiled, then pushed the massager back against my cock through my underwear, this time a little further down the shaft. My eyes closed involuntarily, it felt really good.

She continued to move the head of the vibrator down my cock until eventually it came up against my balls. This was an entirely different sensation, just on the line between pleasure and pain. It still felt great, but also like I was getting kicked in the balls 60 times per second. I flinched slightly, and Veronica took note, pulling the massager away for a moment.

"Too much for these guys?" She asked, probing my balls through my underwear with her other hand.

I didn't answer immediately, and she frowned, finally saying "Alright time to lose these." And with that, she grabbed the hem of my underwear, still partially pulled down on the back side, pulling them all the way down to my knees and exposing my cock to the cool air.

"Oh hello," She said playfully to my cock. "I'm actually not a big fan of dicks, to be honest. Single-minded and leaky, if you ask me. But I need to see what I'm working with."

She pushed the vibrator back on my cock, and the vibration felt even more intense without my underwear in the way. She held it firmly against the middle of the shaft, and it felt glorious.

"I..." I started as I felt the first stirring of orgasm arrive. "That thing is going to make me come in like 10 seconds."

"Really?" She said in amusement, pulling it away. I let out a small involuntary groan.