Unexpected Strap On

It was a very interesting and exciting situation I found myself in. I was sitting in a car with a girl, who I hoped to start a friends-with-benefits thing with, as she was driving. The intrigue lay in what I was wearing. She was wearing her usual jeans and a t shirt. I, on the other hand, was completely naked, not even wearing my glasses, and none of my clothes even in the car with us. With my hands cuffed behind my back. We were driving through the small town where we go to college, stopped at a red light. A car is next to us in the turn lane, but does not notice my state of undress thankfully. My new Mistress smiled an evil smile at me.

We eventually turn off of Main Street, and go a few blocks to where there were no streetlights or even paved roads anymore, and found an open meadow that we've hung out in before, and joked that it would make a good place for a midnight tryst. She hasn't told me exactly what she has in mind tonight, just to do what she says. I'm happy to obey and let her explore my submissive side.

She stopped the car, and killed the engine, but not the headlights. She reached across me to unbuckle me and open the door, told me to go stand in the headlight beams, facing the car. I do so, completely naked and unable to hide myself in any way. I've never felt so physically and emotionally vulnerable in my life, I was completely at her mercy, but I loved it.

I could tell she was changing, but without my glasses and with the high beams shining in my face, I couldn't see into what. When she was ready, she walked into the light facing me. "Tell me what you can see," she purred.

"I can't make out much with the light and shadows, but I can tell you're wearing high heel boots that go up to a little below your knees, a red and black corset, and what seems like oddly bulky panties for the rest of the outfit."

She laughed, and said that if that was all I could see, the panties probably do look weird. "Time to see the rest of the outfit in the light," she said, before turning to give me a profile.

My eyes probably popped out of my head at that point, because she looked spectacular from the waist up, and the corset accentuated her body and breasts beautifully, and the red matched well with her hair. Below the belt, however, was the surprise. She was wearing a strap on dildo, as black as the panties it was attached to, and a little over six inches long, or a little bigger than my dick. I was mesmerized and couldn't look away. "I'm glad you like it," she said, "because you two are going to get very acquainted tonight. Get on your knees, bitch."

I don't even remember thinking "ok," I just lowered myself to the ground, eye level with her new appendage. She stepped closer, and just said three words, "suck my cock." I looked up in her eyes, then down at my task, and opened wide. I took it as far as I could, then backed out, licked up and down its length, circled the head with my tongue, and even sucked her plastic balls, barely breaking eye contact as I bobbed back and forth. She placed her hand on the back of my head, guiding me, and talked dirty to me the whole time I was sucking her. "I like the way you look with my cock and balls in your mouth. You're such a good little cocksucker, are you sure you haven't done this before? That's it, take it all in, I want your tonsils to feel the tip of my dick."

When she was finished, she told me to get up and walk over to the car. I immediately did, and bent over at the waist over the hood without asking, expecting that she wanted to fuck my ass, and I was going to give it to her without thinking twice. She laughed, and said that she was glad that was a natural position for me, but that she had something slightly different in mind this time, and to face her. I did as she asked as she explained herself to me.

"Since it's your first time, I want you to face me as I fuck you, so I can watch your expressions. I want to see the uncertainty in your eyes as I rub my cock up and down the crack of your ass. The fear as I press it against your virgin hole. The pain as I pop inside of you, taking your virginity forever. The confusion as you try to decide whether its ok for you to like having a dick in your ass. And finally, I want to watch the pain and uncertainty and confusion all melt away as the pleasure overtakes you. As the ecstasy becomes all you know, and you start to moan and scream my name, and tell me to fuck you harder, deeper, not caring that you are in the open and people could hear. The pleasure will be all that matters then, and I want to see every bit of it."

At this point, she leaned me back against the car, and lifted my legs up, reaching for the lube on the hood behind me. She rubbed her cock with it, before very sensually rubbing it into my ass. Without warning, one of her fingers popped into my ass. It was the first time anything had ever been up there. As I got used to one, she slipped another finger in, then eventually another, and found my prostate. As she played with it and I was starting to moan, she whispered, "That's it, that's where I want to send you tonight."

And as suddenly as she put them in, her fingers were gone. She began rubbing her cock up and down my ass, and anticipation was building, and uncertainty about what I had gotten myself into was growing. She stopped and placed the tip right at my opening. She looked me dead in the eye and asked if I was ready. I nodded nervously.

"Say it," she requested.

"I'm ready," I uncertainly responded.

"No, say it, tell me what you want me to do."

I saw the hunger in her eyes as I finally caught on, and told her "fuck me. Fuck my ass with your cock."

She smiled and pressed her hips forward. Fuck it hurt as she got past my sphincter, causing me to gasp in pain.

"Relax it," she coached. "Let me in and it won't hurt as much. Once I'm all the way in, you'll get used to my size and we can enjoy it."

I tried my best, but it still hurt. Was this what it was like when girls lost their virginity? Or just when they lost their anal virginity? My body was slowly being invaded as she rocked her hips, moving a little farther in every time. By the time her balls were pressed against the top of my ass, I felt full to the brim.

"How are you feeling?" She asked.

"Like I'm about to pop. Good thing that's all you have, I'm not sure I could take any more."

"Sure you could," she smiled encouragingly. "But this is all we need tonight for your first time." Then she reached for the back of my head, leaned forward, and kissed me, shoving her tongue down my throat before I knew what was coming. It was the most intense kiss I had ever experienced, with my ass full and my mouth attacked at the same time. She finally released me, and simply said, "Now let's fuck."

And fuck we did. She moved slowly at first, creating a void and then slowly refilling it, hitting all the right spots on the way in and out. Then she picked up speed, and started talking again as she did.

"You've never been on this side of fucking before, have you? Look at that, you're hard already. How does it feel having a cock up your ass? Even more, how does it make you feel to have a cock shoved up your ass and like it? You're a big person at school, involved in lots of clubs, and heading up organizations. What would the folks at school say if they knew you liked getting fucked in the ass? You haven't even seen me naked. Now I have you out here with no clothes, having sucked my dick and now taking it up the ass! It's very easy to see who really wears the cock around here! I was originally planning on letting you fuck me later tonight, but now I really like the idea of you being my bitch. You might never see me naked now. In fact, I may just have you get naked whenever you come to my room, to show who's in charge. You're going to be my bitch, my slave, my little subservient ass slut."

Her words and her fucking were getting me even more embarrassed and aroused at the same time. I was imagining her fucking me with the entire girls' dorm watching my hard cock bounce against my stomach as she rammed into my ass. As she worked up, I didn't care if they did. She fucked so good, the pleasure was overwhelming. I couldn't take it anymore, I started to moan and talk back.

"Please, fuck me. Fuck me harder! Take my ass, it's yours as much as you want it! Let the other girls know! Let them watch! I don't care, just fuck me more! I'm your bitch, your slut, your slave! Oh god, just please fuck me harder!"

And with that, I came. She never touched my dick or balls, I came purely out of prostate stimulation and the most intense experience ever. My cum landed all over me, I even gave myself a facial. Because my mouth was open in a moan of pleasure, some even landed in my mouth, the first time I tasted semen. Is it always that salty?

As I came down from my orgasmic high, she began to pet me.

"That was so hot, baby, thank you. I love that you are willing to be my bitch. I promise I'll fuck you all the time. I might even let people watch, since you seem to like that, as long as they know that you are MINE. In fact, let's start a new game now. Get up, kneel again, and close your eyes, don't open them, no matter what I do."

In that moment, I would do anything for her, and didn't question it. She put her cock on my face, then started slapping me on the forehead and cheek with it. Then all of a sudden, she kissed me, hard, making me forget about the situation I was in. When she finished, she threw me to the ground, and because of my handcuffs, I couldn't get up easily. I heard the car door open and close, then the engine start up.

"Mistress?" I asked, questioning for the first time tonight.

"You can open your eyes, now, slave." She was sitting in the car, ready to go. "The new game is this, I'm going back to my room, where all of your clothes are, as well as your phone, wallet, and keys. Your have to make it across town just like you are. If you make it to my room within, say, a half an hour, I'll let you eat me out and maybe even see me completely naked. If you take longer, then I call some of the girls in the dorm and let them watch me fuck you in the lobby. As a final incentive, the faster you get back, the more treats you receive, and the longer it takes you, the more girls I call to watch your humiliation. Sound good?"

Without waiting for an answer, she drove away. I was now laying on the ground, naked, dirty, handcuffed, with a freshly fucked ass and cum all over my face and stomach, all alone. I stayed in stunned silence before realizing that I was about six blocks from my clothes and new mistress, and I was going to have to traverse that span as is. And the clock was ticking.