Jaime’s Way (Part 1)

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I’d only been married a very short time when my wife came home and caught me masturbating while wearing a pair of panties and a bra. This in itself was bad enough but then she caught me again, and then again. The first time she caught me she was shocked and appalled but the twentieth time or so that she found me wearing panties and bra and with a dildo in my ass she really lowered the boom on me. “Are you a fucking fagot? Is that why you wear women’s undies while you jack off? Do you try and pretend you’re a woman getting fucked? Does that get you off?” Sherry asked. “I, uh …” “I don’t want to hear it! And I certainly don’t want you ruining any more of my things!” “Sherry, I …” “Shut up! I’m talking and you’re listening. Things are going to change around here and starting right now. You’ve got a choice. You can either do as I say or you can just get the hell out. What’s it going to be?” “I’ll do whatever you say,” I answered quietly, hoping I could weather the storm. She smiled but it was more an evil smile than a happy one. “I thought that’s what you’d say.” She reached into her purse and brought out some sort of contraption. “First things first. You won’t be jacking off any longer. At least not without my permission,” she said so sweetly and approached me. “This little device will take care of that.” I finally recognized it as a locking male chastity device. Sherry put it on my cock and locked it in place. Jacking off would now be impossible. Hell, getting a hard on wouldn’t even be possible any longer. Something told me she may have been planning this for a while. “From now on, you’ll only get to jack off when I want you to,” she said with a smile before adding, “and you’ll lick up every drop of your cum.” “Lick it up? But …” I’d tasted my own cum on several occasions but I wasn’t about to admit it to her. “Don’t argue with me or you’ll never get to cum again!” Sherry stopped me with a very harsh tone. “There’s going to be quite a few changes around here. From now on you’re going to be keeping the house clean and making all the meals. When I think I can trust you to go out alone, you’ll be doing the grocery shopping and running errands, but that won’t be for a while. Is that clear?” “Yea, very clear,” I replied. I didn’t mind keeping the house clean, enjoyed it in fact, especially since I always did a much more thorough job of it the Sherry ever did. But I at least wanted her to think she was making me do something I didn’t want to do. “I thought so.” I began that evening, cooking dinner and then cleaning the kitchen. It helped that I liked to cook, and cleaning up, well, that wasn’t so bad either. The next morning, however, things really began to take a turn. When I awoke and reached into a drawer for some clean underwear, I found it there was none. No big deal, I just went to the laundry room and started washing clothes but then I discovered that not only was my underwear missing but I had nothing at all to be washed. “Have you seen my underwear?” I asked Sherry. “Yes but I think we need to get you some new ones. Those were all so nasty and uninteresting that I threw them away. I guess we need to go out and get you a few things or you’ll be running around naked.” “Okay. I’ll go get dressed.” “Wait a second. Here, you can wear these shorts,” she said and handed me a pair of denim shorts she’d just finished cutting the legs from. I didn’t mind going commando so I pulled them on. Man, they were tight. Then I recognized them as a pair of jeans I’d outgrown a year ago but hadn’t gotten around to throwing out. When I pulled them on and finally got them buttoned I saw just how short she’d made them. I mean, only girls wore their shorts this short. “You expect me to wear these out in public?” “Of course, but not until you shave your legs. What’s wrong? Are you afraid of showing your legs?” “No, it’s just that you made them kind of short.” “Those are the long ones,” she giggled. “But don’t worry, we’ll get you some new jeans and some other things. In fact, you’ll have your own panties by the time we get back as well as a couple of bras, some stockings, and even a dress or two.” “A dress?” “Of course, every girl has some dresses to wear.” “Yea, okay, whatever,” I muttered. She had to be kidding abut this stuff. Right? Wrong. When we finally left to go shopping I was wearing a pair of flip flops and a pale pink knit pullover shirt that just barely came to the waist of my very tight and very short shorts. And yes, my legs were completely free of hair. This actually felt pretty good, but I didn’t want to tell her that part. Sherry drove to let me know she was in charge. At first I was embarrassed to be seen in public dressed like this, and with shaved legs, but that feeling eased away and I almost forgot that I was dressed more like a girl than a guy. Sherry brought me back to reality when we walked into the big discount store. “You know, we should have painted your nails. What girl goes without a good coat of polish on her fingers and toes?” “I could never go out like that,” I protested slightly. “What would people think?” The last thing I wanted her to think was that I was seriously arguing with her. “Oh, I don’t know, maybe that you’re a sissy crossdresser.” “Exactly.” “Well, you are. Okay, maybe not a sissy, but look at yourself in your tight little shorts and cute top. Babe, you are now officially a crossdresser. Hell, you were before this. Remember wearing my panties and bra while jacking off?” “How can I forget?” “So are you willing to admit that you’re a crossdresser?” “Yea, I guess so.” “Then say it out loud.” Damn, this was humiliating. “I’m a crossdresser,” I answered with a mumbling voice. “What’s that? I can’t hear you.” “I’m a crossdresser,” I said in a voice loud enough that three people looked Beşevler escort in my direction. “Very good. Now that wasn’t so hard, was it?” “No,” I answered, my face still red from humiliation. She suddenly stopped and picked up a bra just a shade larger than her own. “How big do you want your titties to be?” “Yours are perfect,” I answered, looking around to see how many people could see me picking out a bra. “Good answer but I think you should have bigger boobs.” She chose a different cup size and put it in the basket before picking out another bra. This one had lots of lace and in general was quite a bit more sexy. Next we moved to pick out some panties. Sherry chose several styles, all of them very sexy and feminine. Obviously she wasn’t worried about the cost since she picked out thongs, sheer bikinis, string bikinis and some that I didn’t quite catch the name of. All in all, she picked out fifteen pair in various styles and colors. From there she picked out nighties for me, short little baby dolls and a long gown that had a slit all the way to the waist. Sherry also found a garter belt and three pair of stockings as well as three pair of stay up stockings and two pair of pantyhose. Next we went to the junior department and she began picking out dresses which I had to try on for her. Several of them she put back on the rack but five of them she placed in the basket. Most of the dresses were of modest length, falling to just above my knees, but one of them was pretty short even by my standards. “Now when you wear this dress you probably shouldn’t wear your garter belt and stockings,” she said in a loud enough voice that I know she was heard by several people. “That is, unless you want to go for the slut look. Even your thigh highs would be better but you’ll still be able to see the top of them.” At a different rack she picked out six skirts that ranged in length from very short minis to full length and everywhere in between. With these she chose several blouses of differing materials and colors. After that she picked up three pair of very short shorts. I mean, these were short enough that my ass cheeks were almost hanging out. “We need to get you some shoes now.” Did she ever! Of course, I had to try on about a thousand pair and then walk a few steps in each before she picked out any. By the time we left that department I had eight pair, most of them with high heels of four inches, some stiletto and some block heels and even a pair of five inch wedgies, which I found to be the most comfortable of all the heels. She also bought me a pair of canvas top sneakers, bright red of course, and a pair of flat leather sandals. Just when I thought I couldn’t be embarrassed any more, Sherry stopped at the makeup counter and asked the girl there to pick out the colors that would look best on me. This entailed her applying the makeup on me several times but when she finally finished I had to admit that I looked damn pretty all made up. Her efforts were rewarded when Sherry began telling her what she was going to buy for me. Naturally, Sherry insisted that I spend the rest of the day wearing the makeup the girl had worked so hard to perfect. Before we were ready to leave the store Sherry also picked out a small purse for me, bracelets, a ring, a necklace and several pair of very feminine earrings. The jewelry had to be paid for in that department to cut down on shoplifting so Sherry whipped out her credit card and paid but only after both my ears had been pierced. Now it was time to make our purchases and go home, which was all fine and good except the line to the checkout looked to be a mile long. By now at least a hundred people had seen moving about the store and I had received all sorts of stares and even a few smiles. Since I’d never even seen any of these people and probably would never see them again, I really didn’t care what they thought about me and crossdressing in general. After we were in line about fifteen minutes Sherry smiled sweetly and said, “I’m getting hungry. You go on through the line and pay for all this and then meet me across the parking lot at Boogie Burger.” “Me?” “Yes, you. If anyone asks about anything in the basket you are to tell them it’s for you. Here’s my credit card. Oh, and be sure you ask if anyone, especially one of those good looking guys, will help you carry everything to the car.” “Okay, I can do that,” I smiled. I was used to everyone’s stares by now and, in fact, I kind of liked the idea of dressing like a girl, especially if it meant I could jack off every now and then. I waited in line for what seemed like an hour before I finally got to the cashier and I’d noticed more than one guy checking me out. Even though I was obviously a guy dressing more like a girl, I couldn’t help but see a certain amount of lust in their eyes and that made my heart race a little. To me it was obvious what they’d like to do, and somehow I found that to be quite pleasing, and more than a little exciting. “Wow, did you buy out the store?” the cashier asked when it was finally my turn. “I tried.” “Looks like you did a pretty good job,” she laughed, ringing up item after item. “Ooo, sexy,” she crooned as she rang up the panties. “Yours?” she asked and held of the bras. “Yes.” “You sure they’re not too big?” “Falsies.” “Ah, I didn’t think about those,” she said with a smile. It was no wonder she didn’t think about them, I thought after taking a second look at her very large titties. “Um, do you think I could get some help carrying these to my car?” I asked as I handed her Sherry’s card. “Sure thing,” she answered and smiled. “Hey Mike, will you help this lady with her bags?” “Sure,” Mike replied and began gathering my bags. He was sure giving me the once over and Çankaya escort bayan suddenly I felt that all too familiar tingling between my legs. Although I liked the way he looked at me I was a little confused why I was feeling aroused by his attention. “I can’t wait to get home and try on a pair of these panties and that pretty black bra,” I told the cashier in a voice loud enough that Mike could easily hear. Damn, I was flirting with him without giving it any thought! “You’ll love it,” the girl said as I signed my name to the receipt. “New wardrobe?” Mike asked, carry the majority of my new clothes while I pushed the basket. “A whole new me,” I laughed and found myself putting a little extra swing in my ass. When we got to the car Mike handed me the bags while I leaned in and placed them. Of course, my tightly clad denim covered ass was just waving at him, distracting him quite a bit. I knew he was watching me and even wiggled my butt a little for him. After everything was put away in the car Mike went back inside the store and I stood watching him. Funny that I noticed he had a very fine ass. When he was inside I locked the car and walked across the parking lot to Boogie Burger. “You are such a flirt and tease,” Sherry laughed when I was in the restaurant. “Huh? Me?” “Don’t even pretend you didn’t know what you were doing, shaking your ass at that poor boy and bending over like that so he could get a good look. You were all but saying, here it is, take it.” “Is that so bad?” “No, not really, I do it all the time.” We ate our burgers and left the place after Sherry took me into the ladies room to freshen our lipstick. Because of the chastity cage I was wearing I had to sit to pee, just like a girl. “One more stop,” she said with a smile and pulled into an adult book store. “You want me to go in there dressed like this?” “Get used to it. Your days as dressing like a man are over with, buddy. Now come on.” “What are we getting?” “You’ll see,” she laughed. The first thing she picked out was a video about transvestites having sex with me or with each other. Then she began looking at sex toys and I was starting to get a sinking feeling because she was looking at strap on dildos and I could just imagine what she was planning on doing with it. The one she finally decided upon was ten inches long and at least three inches around. Not only did the size concern me but it also came fully functional with a squeeze bulb that actually allowed it to shoot its own cum. Sherry picked up a set of leather cuffs and asked. “When I fuck your asshole with this thing, am I going to have to restrain you? If you even remotely think so, then we’ll have to get two pair of these.” Of course there were a couple of guys within hearing range so they knew I was going to get fucked with her new dildo. “Uh, no, I’ll be good,” I answered quietly. “Oh, go ahead and smile, baby, you know you’ll love it,” she exclaimed. “Besides, whether or not you love it, I’m going to love fucking your pretty little ass tonight.” Sherry gave me her credit card and once again I made our purchases. The cashier gave me a very knowing look when ringing up the sale. While I was busy I lost track of her and didn’t realize she was making preparations for me to really expand me sexuality. “Come on, I want to show you something,” Sherry said, suddenly at my side. She lead the way into the arcade area and walked purposefully to one of the booths. We were inside and she fed the machine some cash and a video began playing. The girl sucking on the hard cock was obviously not completely female. I mean, she had a dick between her legs that made me jealous. I was totally mesmerized watching the long cock sliding in and out of her mouth. A part of me wondered if I could ever have the balls to do something like that. I found myself becoming very aroused, not because I wanted her to suck my dick but because I actually wanted to do the sucking. “Oh look,” Sherry said, nudging me and pointing to a hefty dick coming through a hole in the wall. Even though I was highly aroused, the idea of touching another guy’s cock wasn’t really on my list of things to do, no matter how I might be dressed. “Go ahead, touch it. Hold it. You know you really want to.” “Hell, I might hurt it,” I laughed, using maybe just a little too much macho. “Touch it, silly, don’t rip it off.” “I, I can’t. Come on, Sherry, I’m not a queer.” “No, you’re just a sissy crossdressing fagot. Like this,” she said and wrapped her hand around the large cock, slowly moving her hand up and down its length. I thought to myself that if she wanted me to do this, I could probably do it, especially since no one would know about it. “Jack him slowly. Just like I’m doing. Then after a bit just lean down and kiss him.” Which is exactly what she did. Seeing her kiss the stranger’s dick and then seeing her tongue snake out and lick the head was a very erotic sight. Then, without any hesitation, Sherry took the hard cock deep into her mouth. I knew from personal experience just exactly how good she could suck a cock. Most men probably would have been jealous to see their wife sucking a cock as she was doing but I wasn’t. In fact, I was happy just to sit back and watch even though she was actually just showing me how to do it in an attempt to get me to do the same. She pulled away from him, kissed the head of his dick, and smiled up at me, “Your turn.” I stared at the throbbing shaft and slowly reached out, drawn to it like a moth to a flame, until my fingers made contact. There was no sudden lightning bolt striking me dead so I let my fingers wrap themselves around him. In all my life I’d never touched another man’s dick and now I was holding him gently, slowly stoking him. “You’re doing Escort Cebeci fine,” Sherry whispered. “Now lean down and have a taste.” I could feel my own cock growing within the confines of the cage but I knew I couldn’t achieve an erection. Actually it was painful getting as hard as it was and then I felt myself deflating even though I was still highly aroused. “Do it! Kiss his cock! You know, way down deep inside, you really want to suck him. Just do it!” This was an act I had fantasized about during my many jack off sessions. Somewhere in the back of my mind, I knew I wanted to feel a man’s hard cock sliding over my lips. So without even thinking about it, I found his dick directly in front of my mouth. The next thing I knew my tongue was plating over the head of the magnificent dick. That’s the moment I knew I was going to suck him; that I was going to be a cocksucker; that I wanted to be a cocksucker. I didn’t kiss his dick but just opened my lips and slowly took him into my mouth. Feeling the smooth hardness of the throbbing cock sliding over my lips was absolutely wonderful. “See? It’s not so bad, now is it? Don’t worry, you’ll be getting lot’s and lot’s of practice. Before you know it you’ll be a first class little cocksucker.” What had been fighting words just a few days earlier now didn’t sound so bad. In fact, I discovered that I liked being called a cocksucker. I knew that I crossed a through a door that I could never return from. Never again could I sat I was heterosexual because I had become, or at least accepted, that I was bisexual, if not gay. I was happily sucking the cock Sherry had made available to me when I realized she was taking photos of me. But what the hell, I’d done the same thing to her many times, snapping shots of her naked or with my dick buried in her somewhere, so I figured it was payback time and just kept on sliding my mouth up and down his shaft. When I felt him grown harder and thicker in my mouth I knew what was about to happen but I didn’t slow down. Seconds later I felt the hot and creamy sperm firing out of his dick and into my very willing mouth. The taste was very similar to my own cum but maybe a little bit stronger and there was quite a bit more than I’d ever shot. “Open your mouth and let me see it,” Sherry laughed. “Then you can swallow it like a good little girl.” I knew she was going to take a picture of me with a mouthful of cum but I did as she requested while the cock pulled back through the hole. “Wow, he really gave you a load,” she said and snapped the picture. “Now swish it around your mouth and then you can swallow. How do you like the taste of a real man’s sperm?” “It’s not so bad,” I answered after swallowing. “Good. You’ll get to where you really love it,” she said with a smile and then nodded back to the hole. Looking I saw that a different cock was waiting for its turn. This one wasn’t as long nor was it circumcised. “Go ahead, cocksucker, give him a blow job.” Shrugging my shoulders, I began sucking this one. The initial flavor was different, having a slightly bitter background taste, but not bad either. I figured this was maybe a trace of piss that had been trapped beneath the foreskin. “Tastes different, doesn’t it? That’s his pee. You’ll like it after a while.” I sucked him for quite a while before he began spewing his cum into my mouth. I already knew that his cum would taste different, and it did. But the bottom line was, I liked the flavor. Over the next three hours I sucked one cock after another, enjoying each one more than the one before. Then, just when I thought I was finished, the door to our booth opened and a man stepped inside. “Okay, sissy, get on your knees and suck my dick,” the man smiled and lowered his zipper. “Wait a minute,” Sherry said and smiled back at him. “Let the sissy cocksucker fish your dick out of your pants. She needs to learns how to do it.” Kneeling before the man, I slipped my small hand into his pants and found him to be going commando, which was good because when I found his cock I was shocked by the size of it. The only time I’d ever seen a dick of this size was in a porno movie, and I was supposed to give him a blow job. “Oh my goodness!” I exclaimed in total amazement when the full length and extreme thickness of his beautiful cock was on display. “And it’s loaded for bear. Just be warned, I haven’t had any for three weeks so I’m on a hair trigger.” Smiling up at him, I replied, “I understand and it’s okay.” I lifted his hardened member up and leaned to bring my lips to the bulbous head so I could kiss it. When I began licking him from tip to base I didn’t think I would ever get to the end. After I did I began working on getting the head into my mouth, thanking my lucky stars that I wouldn’t be expected to deep throat this monster. My mouth was stretched open as wide as possible without unhinging my jaws but I managed to get him inside, as well as three inches of his shaft. “I can’t believe he got you inside,” Sherry gasped and took three or four pictures. “Yea, most girls can’t get that far,” he laughed and placed a hand on my head. “Ooo, yea, girly, that feels so fucking good!” Because he referred to me as girly I felt even better and tried to get more of his cock into my mouth but that was impossible. Instead I concentrated on the sensitive head of his cock, hoping he really was going on a hair trigger. Sure enough, after only ten minutes or so I felt him shudder. This was the signal I knew came just before the reward I wanted. He held he on the sides of my head and erupted into my mouth, quickly filling me with creamy hot cum. Then he pulled out and began blasting away on my face, giving me my very first facial. I’d done this to Sherry once or twice but until today had never thought I’d really be on the receiving end. All the while Sherry snapped one picture after the other. It want until she showed them to me that I saw how happy I looked. “You know, it wasn’t until today that this little cocksucker had ever sucked a cock,” Sherry laughed. “Really? Damn! Well she does a good job,” he replied.

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