6 comments/ 52216 views/ 36 favorites Unexpected Strap On By: nt60 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. Unexpected Strap On Ch. 02: Return Journey There I was, lying in the mud, naked. I was handcuffed, with cum covering my chest and face, the salty taste still in my mouth. My ass was sore from my Mistress fucking it for the first time a few minutes before. And now I was left alone. I realized if I was going to get to Mistress in time to avoid my punishment, I needed to get going. I crawled up to my knees and then to my feet (no easy task with my hands behind my back), and tried to come up with a route. I decided the best way was probably to stick to the side streets, which meant I would have to go past private houses, but there wasn't nearly as much traffic and lots of trees and bushes to hide behind when a car came down the road. I set off down the side road, and did have to hide behind bushes and trees on at least four or five occasions, but I'm pretty sure I wasn't seen. The closest I came was when I hid in a yard to avoid a car, and a light in the house came on. I couldn't move to the other side of the bush, because there was still a car coming. As I looked at the house in dread, my female English teacher, Dr. Smith walked by the window. She was reading as she walked by, not looking up and certainly not looking out the window. It looked like she had been reading in bed and decided to come downstairs. Her husband taught in another state, so she was home alone for long periods of time. The car passed but I couldn't make myself move. I think I wanted her to see me standing naked in her yard. I started to grow as I thought about it. She walked back through the living room and I could have sworn I saw her lift her head up from her book towards me, but she didn't look long and turned away. I thought I was safe, but still couldn't move for a second. When I finally started to turn, I heard a voice whisper my name. "Is that you?" Sure enough, by teacher had stepped out her side door and caught me. I froze, like a deer in the headlights, with my mouth hanging open. I started to stutter as she walked out towards me. With my hands cuffed, I obviously could do nothing to cover myself, and I was getting harder with every step and downward glance she took. "Why are you naked? And handcuffed? Are you ok? Do you need help?" "I was playing a game with a friend. She decided that it would be really fun to make me walk across town like this. I'm fine, but I could probably use some help." She smiled at me, and agreed that I probably could, before inviting me inside. When we waked inside the house, I could finally see what it was she was wearing in the light to appreciate it. She had on a light black robe, which went down to about mid-thigh. When we were inside, she stopped clutching the top, letting it open a little, showing off some cleavage that the guys (and some girls) at school had admired often. And I wasn't sure that she was wearing anything at all underneath the robe. Maybe panties, but I was pretty sure that was all there could be. She sat me on a chair in her living room as she sat on her couch, watching and smiling at me the entire time. "I'll be happy to help you, under certain conditions. First, you have to tell me exactly what kind of games you were playing earlier tonight. Then, with my husband away, I need some chores done, so I would hope that you could come by one afternoon and help me out with those. I think I can come up with a good uniform for you. Sound agreeable?" I agreed, and spilled my secrets, not even hesitating to tell her that Mistress had fucked my ass. She was very interested, and confessed that she had always wanted to try wearing a strap-on, but her husband wouldn't let her. When I finished, Dr. Smith decided that we had better get going to get me back on time, and bent down to get her keys, giving me a front row seat to her full cleavage. She of course caught me. "Now, now, it's hardly appropriate to leer at your teacher" "Sorry, but it was right in front of me, and I don't actually have your class this semester," I reminded her. "I suppose not," she smiled. As she walked by, her hand brushed over my now very hard cock. "Now let's get you back to your Mistress." Her legs looked spectacular as she walked away as well. She drove me right up to the door of the dorm, but did not have a key to let me in. She told me good luck and have fun, and that she'd call me about those chores, giving one last lingering look up and down before leaving. As luck would have it, someone came by about a minute later to open the door. She was kind of my protégé, the person who was going to take over for me as the leader of several groups on campus. I was a little concerned about losing her respect if she found me like this, but I also knew I could trust her, and I needed to get inside to make the time. "Jen, could you help me out?" She came over and was understandably shocked at my state. I gave her a brief explanation, leaving out the details of the meadow and Dr. Smith's help. She laughed at my predicament, but let me in, and even looked out for me while we were climbing stairs to Mistress' floor. Once we got to the floor, Jen left me alone and I thanked her. I headbutted the door to knock, since my hands were cuffed behind me. Mistress opened the door wearing a towel, looking surprised to see me. "You made it! I didn't expect you to be so efficient. Well come on in and collect your prize!" The door closed behind me and she faced me. She reached for the knot in her towel, undid it, and let it fall to the ground with a "Ta da," leaving her gloriously naked. Her pert breast rose and fell with each breath, the nipples already hard for sucking. Her waist flared out to her hips, leading to her beautifully long legs. She had the prettiest pussy I had ever laid eyes on, perfect, with a one inch landing strip showing the way to the promised land. And yes, the carpet matched the drapes, with the landing strip the same shock of red hair on an otherwise nude canvas. After giving me time to admire her front, she spun to give me the back view. Her ass was even more spectacular unadorned than in those short shorts and yoga pants that she had been torturously teasing me with for weeks. I wanted my hands to be free more now than all night so I could grab her. She walked across the room and threw her arms around my neck, pressing the entire length of her naked body against mine and kissed me hungrily. Her nipples pressing on my chest, her pussy rubbing against my dick, and her smooth legs contrasting with my coarse, hairy ones almost set me off. Her hands began tracing my back, holding my hands before, all of a sudden, my cuffs popped off and hit the floor. Once I realized they were free, they began to explore her. One hand went straight for her tits, pinching and rubbing her nipple, making her moan, and the other took a beeline for her ass, which was just as firm and soft as I had hoped. After a few minutes of her pressing me against the wall, I used both hands to grab her ass and pick her up, walking her toward the bed. I sat her on the bed, and began pulling my hips away to aim my cock. She immediately broke the kiss, telling me not yet. She got up and turned me around, having me lay on the bed as she stood at the side. She stroked my dick a few times before turning towards my face again. She climbed on the bed straddling my face. She looked so beautiful to see her entire body from below. She lowered herself towards me, stopping just short of my mouth, telling me I had to prove how much I wanted it. I reached my tongue out and barely grazed her pussy, but that was enough, as she gasped and sat the rest of the way. It wasn't long after that until she grabbed my hair and rocked her hips, riding my face, screaming my name. Once she had cum twice, she moved down, sitting on my chest, and moving farther and farther down until she was face to face with my cock. She sucked it like I had sucked her plastic one earlier, swirling around the head, licking, deep throating, sucking the balls, a great blow job, and she stopped just short of me cumming. Then she moved up and impaled herself on me. She rode cowgirl like a champ, almost too good for the night I had had. I blew deep inside her after only a few minutes. I apologized profusely as she pouted, but she didn't seem too torn up about it. "You're my slave, remember, we've got a lot of time to get a good fuck in." We started making out again, and she started playing with my dick again, trying to get it hard for the next go round. She started to blow me again, and seemingly decided to take it all the way this time, I held out much longer, proving my stamina before cumming. She swallowed every drop, and told me how good I tasted. Mistress had me give her a back massage after that, to give us a break. At first I sat with my ass on her ass for the upper shoulders. As I slid down to move lower, my cock happened to fall right in her crack, giving me ideas and getting me hard again. As I moved down to her ass, unveiling her asshole to me, I decided to ask. "How do you feel about getting fucked in the ass, Mistress?" "As long as you lube up well, I'm not opposed." I of course jumped off the bed to get the lube, as she turned to put her feet on the floor to offer me her ass doggie style. I lubed up and began to enter her again. She was so tight! She told me that she and another girl had fucked each other with strap-ons and dildos, but mine was the first real cock she'd ever had up her ass. Between her tightness, her moans, and the sight of me fucking her beautiful ass, I succumbed again and came in her ass. She thanked me and immediately demanded that we clean my cock before I fucked her pussy again, so she decided we needed to take a shower. She wrapped up in a towel and told me to close my eyes and count to ten before I followed her. I didn't have a towel, so I just followed her as is after my count. We showered, as she meticulously washed my cock while I played with her tits and pussy. By the time I was pronounced clean, I was also hard again. She reached in her shower bag and produced her strap-on from the meadow, surprising me. She stepped in the harness before stepping back and allowing me to see her in her full glory. She was gorgeous, her pale skin and curves complimented by the harness and the erection sticking out of her crotch. Mistress kissed me, our cocks pressing against each other. She turned me around to face the wall, where I placed my hands for support. The water provided enough lubrication for her to slide into me once I got used to the feeling again. I tried to keep quiet because I didn't know if any other girls were in there. After a while, though, I couldn't keep it in anymore and moaned. Sure enough, a female voice giggled a stall away, and asked if we were having fun. Mistress laughed back, and confirmed that we were thoroughly enjoying ourselves. Knowing someone was there seemed to turn Mistress on, because she started ramming faster, and since the charade was up, I did not hold back my expressions of pleasure. All of a sudden, we hear an "Oh my God!" from the other direction, causing us both turn our heads. It seemed that in our passion, the shower curtain had slipped over, not coming all the way open, but open enough that there was no doubt to anyone walking by exactly what we were doing. Of course, someone else had walked in and saw our unusual position. I knew the girl, she was the president of a rival club on campus, and once the shock wore off, a smile appeared on her face. The girl who heard us earlier asked what was wrong. "They're fucking in here!" "I know that I heard them." "Oh, no, she's fucking him!!" The one that caught us laughed. This of course got the showerer's attention, and she turned her water off and threw her towel around herself to come see us for herself. She was in all of my classes and started laughing. After the surprise wore off, Mistress started moving again, fucking me with an audience. They loved it and started cheering. She loved it and fucked me harder. I loved it and started shouting, "Yes! Fuck me Mistress! Take my ass with them watching! Fuck me til I cum!" "No, I don't want you to cum yet," Mistress said, and pulled out of me. She stepped out of her harness with my hands still against the wall and my ass pointing at the three girls. She took the dildo out of her strap-on, and pressed it back in my ass. She grabbed her towel and walked away, saying, "Come, and don't drop it." I had no choice but to follow after her, naked and hard and with dildo hanging out of my ass. The girls smiled at me and told me they looked forward to seeing me in class, giggling. I had to walk slower than I wanted to in order to keep the dildo in, and the girls made sure to watch my every step. When we got to the room, we were pawing at each other as soon as the door closed again. She pulled her dildo out of me, then whispered, "Fuck me, slave." This time, she did not stop me from carrying her to the bed. I lay her facing me on the bed as I stood off of it, and placed her heels on my shoulders. It occurred to me that this was the exact position that she fucked me in the meadow earlier this evening. I fucked her long and hard this time, making her cum again and scream for the neighbors to hear. I kept thrusting as I came, and ended up with a couple pumps inside of her before slipping out and covering her with my semen. She looked me straight in the eye, scooped up a glob of it with her finger, and placed it in her mouth sexily. "You must me exhausted, running all over town, fucking and getting fucked all night. Why don't we lay you down?" "Yes Mistress, I am so tired," I said, accepting her offer to lie on her bed. I collapsed face down and must have briefly fallen asleep. The next thing I remember is waking up to cold lube being spread on my asshole. I look back and Mistress is on her knees, wearing only a strap on, even bigger than the last one. She noticed I woke up and asked me to lift my hips, which she promptly stuck two pillows under. "It's important for you to understand that just because you've seen me naked and fucked me doesn't mean we're only going to have regular sex from now on. There's going to be lots of kink in our sex life. And I love fucking your ass, so we're going to do that again to prove it. And to be clear, I am still your Mistress. Those times you fucked me tonight were because I let you and I wanted to get fucked. You didn't decide anything, and you are to do what I tell you, when I tell you. Understood?" I nodded and replied, "Yes Mistress." "Good. Now tell me what you want need me to do to finish the night, slave," she said as she climbed back on the bed and aimed her big black cock at my hole. "Fuck me Mistress. Please fuck my ass." "As you wish, my bitch. I do love when you beg." Just the head of this dildo felt like it was going to split me in two. She went slowly, as always, and took her time getting her cock in me. Good thing she did, because it still felt like it was going to split me in two as it was. Eventually I got used to the new size, and she began fucking me in earnest. She was much rougher this time than our first session, I suppose to make up for me fucking her multiple times and reassert herself. She grabbed my hips, and occasionally moved her hands up to my shoulders, so she could pull me to her as she thrust inside of me. She rammed my ass for a solid forty five minutes to an hour. I moaned and begged the entire time, but could not get another hard on or cum again, I was so exhausted. I just took it until she was tired. Finally, she tired herself out as well, and slowed her thrusting and laid her body on my back. She never even pulled out, just hugged me. After another ten minutes, she finally disengaged herself, and we cuddled the rest of the night away, with her cock pressed against me. We passed out and slept deep into the next afternoon.