15 comments/ 18305 views/ 30 favorites The Drill Sergeant By: AmandaSwallows *** While transsexuals are not allowed in the military and there is no way this could actually happen, I found myself fantasizing about it one night while on duty. I hope you enjoy. *** ***** I have seen a lot of drill sergeants over the years. My father was the first, a Marine Corps drill sergeant with two tours in Vietnam. He was the toughest, most intimidating person that I have ever met. I thought, after growing up in his house, nothing could scare me. So far, combat in Fallujah, Iraq was the only thing that has. I joined the Marine Corps after high school and went to boot camp at Paris Island where I met someone that was almost as bad as my dad. I had heard the stories and watched Full Metal Jacket but dad was worse so it wasn't that bad. I've had a nine year career as a Marine and have had the privilege of commanding an infantry platoon and company in Iraq. When I got back from my second tour, the Corps gave me the opportunity to train other young Marines as a commander for Marine boot camp. On my first day, I met the only person who might have been as intimidating as my dad. I hadn't even started the change of command inventories when I ran into her on the way in to see the outgoing commander. I walked up on her bent over and screaming at a male recruit who was struggling to do a pushup. I have to admit that I had a difficult time not staring. Even in the unflattering uniform, I could tell that she had an amazing body. As I walked by, she called the recruit to attention and turned to salute me. I almost tripped when I saw her face. She was absolutely beautiful. It didn't matter that she had her flame-red hair pulled back in a severe bun under the drill sergeant hat or that she wasn't wearing any makeup that I could see. Her light skin was surprisingly clear with just a sprinkle of freckles across her nose and cheeks. The redness in her face from loudly training the recruit emphasized large, almond shaped green eyes and thick, pouting lips. She had an oval face with high cheekbones that any model would kill for and I couldn't help noticing the way her body filled out the uniform very nicely. Since I couldn't stop myself from looking, I pretended to be reading her nametag. I returned her salute with a quick, "carry on Staff Sergeant McAnderson," and continued on before I embarrassed myself with the tent I was pitching. I could hear her shrill voice all the way to the commander's office and it even managed to carry faintly through the door. Most of my Marines were what you would expect from drill sergeants. My senior drill instructor, a Gunnery Sergeant, reminded me of my father. He had a wife and three daughters. The only time I ever saw him smile was around those four women. I had two more family men, one single male and one single female, all Staff Sergeants. They were all very professional and good at their jobs but both my First Sergeant and my gunny sergeant said Katherine McAnderson was the best they had. I'll admit, after seeing her in action with the recruits, I have to agree. She could out run, out swim, and otherwise outperform almost every recruit that came through our company despite her petite, 5'1" frame and curvaceous body. She could even beat each of the other drills at certain things. Most of them, she beat in the pool but she could outrun the First Sergeant too. I was the only one she couldn't beat at anything and for some reason that irked her. We had a friendly rivalry until I left almost a year later when I was promoted to Major. For the first couple of weeks, I couldn't figure her out. Whenever she was anywhere near the recruits, she was the hardest cast-iron bitch that I have ever seen. She had no pity or mercy for any recruit, regardless of age, sex, or beliefs. She managed to make recruits built like pro-football linemen break down and cry. I once even heard a recruit tell her that he didn't want to be a man when she told him to grab his balls and be one. Strangely, whenever the recruits weren't around, she seemed very sweet and feminine. One minute, she was a heartless bitch with no feelings and a voice that could shatter glass, the next, she was smiling and laughing like any girl you'd meet at a bar, talking with a sultry bedroom voice that made my cock jump every time I heard it. Her attitude change was like the flip of a switch and seeing it is still unnerving. It didn't take me long to realize that her professional personality never left the company area. The other drill sergeants understood it and treated her as one of the guys at work but off duty, they saw her as the attractive, single woman that she was. During that time, I also learned that, though she flirted with the others some, she had a hard standing rule to never fool around with a colleague. Of course, the other drills tried, but she always fended them off. She also always seemed to have plans on the weekend. I assumed that she had a steady boyfriend but when she showed up to our military ball without a date, I learned that she was in fact single and did not date often. Over the year that I spent in command, McAnderson and I got to know each other very well and I found myself extremely attracted to her. I knew it wasn't professional and could get me into a lot of trouble but I couldn't help it. I did manage to hide it well though. None of my Marines had any idea that I couldn't keep my mind off her and sported an impressive chubby any time I saw her. Their ignorance was the only thing that saved my career. When I handed over command of the basic training company, my Marines threw me a going away party, which doubled as a promotion party. It started innocently enough but just like any other party, add alcohol and things tend to happen. McAnderson had offered to throw the party at her place because it was large and centrally located without kids to put to bed. She lived right off post with a roommate who was out of town. The house had a large living room and a nice entertainment center so the others readily agreed to it. Everyone showed up about seven, after going home and changing. McAnderson looked amazing. When she answered the door, her hair fell in crimson waves down past her shoulders. Artful makeup, almost impossible to see if you hadn't seen her without any, highlighted her stunning features. She wore a green top that managed to be enticing and modest at the same time. The word I would use is classy. Low rise, hip hugging designer jeans emphasized her flat stomach and toned, curvaceous figure. I was painfully aware of my erection for the entire party. Luckily, my pants hid it well. Of course, the alcohol flowed freely. Everyone wanted to congratulate me by drinking with me. I should have known that it was a bad idea. Officers are told constantly not to fraternize with the sergeants because it can only lead to disaster. I let it go because I was leaving and we were celebrating. I was no longer in command, after all. I really didn't think anything was going to happen. I wasn't planning to stay too long so I rode with my lieutenant who's wife was pregnant. Riding with him meant that I could have a few drinks and I figured it would keep me out of trouble since he was leaving a little early. Once we started drinking, everything was going well until he got a call from the hospital because his pregnant wife went into labor almost two weeks early. He wasn't at the party for more than an hour. If I left with him, that would be rude since the party was in my honor. Katherine saved the day though, introducing me to her neighbor. Marry was six years sober and readily offered to drive me home so the lieutenant could go take care of his wife. I told him to go and that I would check up on them the next day. It was probably the worst, and best, decision that I have ever made. The party went on until just before midnight. It was a Friday, so no one felt too obligated to leave early, and we were having a great time. Marry had offered to stay to clean up and I insisted on staying to help as thanks for the ride. Katherine smiled, telling me that I didn't have to but I wasn't really very drunk so I insisted. The three of us managed to get Katherine's place mostly cleaned up in just over a half hour despite two of us being a bit tipsy. By the time we were done, Katherine told me that, if it wouldn't make me uncomfortable, I could stay the night and she'd give me a ride home in the morning. I could tell that Marry was a bit tired and driving tired is almost as bad as driving drunk so I agreed and we told Marry. She smiled a little too knowingly and I immediately felt self-conscious. If anyone found out, we would be in serious trouble but Katherine seemed unperturbed by the idea so I went with it, telling myself that nothing would happen. After Mary left, Katherine brought me a blanket and pillow for the couch. She was limping for some reason and had an odd look of pained discomfort on her face which she was trying to hide. When I asked her, she told me that it's a problem she's had since childhood. I thanked her again for letting me stay with her and we sat down and talked a little more since neither of us were tired. I was polishing off another vodka tonic when the conversation inevitably turned to sex. It started innocently about our personal lives but got pretty explicit after a while. As a rule, I don't tell my tequila stories to my soldiers but she told me a pretty good one so I decided to tell her my favorite story about being in New Orleans for a bachelor party and blacking out only to wake up naked the next morning on a hotel couch tangled with two women that I didn't know. My two straight friends each had a girl I didn't know and the gay couple that we had known for years was tangled together with another woman I didn't know. I didn't remember any of it but according to my friends, it was an all out, no holes barred orgy. She was shocked. We laughed about it and she told me a racy one about walking in on her roommate with another girl and three guys. The subject got around to my strangest sexual encounter so, against my better judgment, I told a story that had never passed my lips before that night. I told her about a time when I was visiting a friend in Los Angeles. I went out on the town by myself because he had other plans that night with a girl he was serious about. When I was out, I met this beautiful woman and turned on the charm. We started drinking tequila and it quickly led back to her place, which was nearby. At first, I thought she was a pro but she never asked for money. We started getting hot and heavy before we even got into her apartment so when she dropped the bomb, it took a few minutes for me to process it. I asked Katherine if she had ever seen The Crying Game. When she told me that she had, I absently noticed that her eyes lit up and her lips parted as she leaned in to me, adjusting a little. Obviously, she was turned on by where the story was going. Obviously, I had a choice to make when I learned that the person I went home with wasn't what I thought she was. While I drunkenly tried to decide what to do, she told me things like, "you don't have to see it or touch it," and "don't go, it'll be worth it if you stay." Katherine seemed extremely interested in the story and hung on my next few words. When I told her that I decided to stay, I watched her lick her lips and shiver a little. I finished the story by telling her that it was actually a good experience and I was surprised to realize that I enjoyed all of it. I don't know why I told her everything, even the parts I was ashamed to remember, like enjoying the feel of that woman's cock as it grew in my mouth and hands. As soon as I realized what I said I stopped, hoping that I could explain or convince her that I was joking. It is strange when you are drunk and think you've put your foot so deep in your mouth that you feel it kicking your own ass. I had a million thoughts in my head of ways to keep her from thinking I'm a gay freak and telling the rest of my Marines but nothing came out. I was frozen until she said something that took me completely by surprise. "Don't worry," she said. "I am really good at keeping secrets." I had no idea how to read the look on her face. Something about her seemed on edge and she almost looked pained. If it wasn't for something in her eyes, and the way she said those words, I would have thought the worst. It was a huge relief to believe that she would keep my secret. I had gotten to know her well enough to know that she never gossiped or said anything that would mar the reputation of anyone without cause. Amazingly, telling her those things and believing that I could trust her made me even more comfortable around her. "Listen," she said after a moment. "I'm, not really tired but I uh... need to change into something more comfortable. When I get back, will you help me finish the margarita I mixed? I've still got some and don't want to throw it out." "Sure," I replied. Now, I can handle my liquor but giving me tequila in any form is just a bad idea. Usually, I know better but her reasons seemed harmless enough and I was feeling just good enough to let her talk me into some strong margaritas, especially after telling her that secret. I still hadn't decided if it was a mistake. Besides, I was tipsy enough to know better and just not care. She got up carefully and limped to the door to her room. I realized that when she talked about changing, she may not have meant it the way I thought she did if the clothes she was wearing were actually causing her pain. A few moments after she closed the door to her bedroom, I heard a grunt and the sound of Velcro ripping followed by a relieved sigh. When I saw her walking back out wearing a sexy, emerald silk nightgown with no hint of pain, I was relieved and a little confused about what could so quickly make her feel better. We sat and talked a little as we drank and she managed to distract me from my questions about what had been causing her pain. That was when I started noticing her advances. The fact that she was sitting there in a sexy, low cut nightgown that showed off her curvaceous, petite figure to great advantage, should have made it obvious what she wanted. Her hair was still down and she was absently twirling a crimson lock as we talked. Her makeup was still on but again, if I hadn't seen her without it, I wouldn't have known she was wearing any. Her ample expanse of creamy white cleavage was on full display in the low cut, open V of her nightgown. The nightgown fell loosely to mid thigh, showing the soft, creamy flesh of her enticing legs and clinging invitingly to her hips and ass. As we talked, I noticed her stop playing with her hair and start absently running her fingers along the neckline of her nightgown. Even after everything I had been drinking, I couldn't ignore such an obvious open invitation. Our conversation quickly escalated to kissing, though I couldn't say who started it. Things were getting a little intense when she pulled away sharply and put a hand out to stop me. Part of me was angry that she would go this far just to stop now because the Marines tell us we can't fraternize with each other. I was about to try to press my advances again when she spoke. "Sir—uh... Alex... I, um... wasn't planning on this or anything." Something about the way she said that made me sit quietly and let her continue. "I didn't... I mean, when you told me your stories, I thought... well... since you trusted me... and then, what you said, about the girl in L.A..." She stopped. My mouth was dry and I wasn't sure what I was going to say but I managed a soft, "what about her?" "I'm... like her." Right then, my world flipped on its ass. I suddenly realized why she was in pain and limping earlier. I realized what the Velcro and the sigh in her room must have meant. I even wondered how she managed to hide it in the pool when we swam until I realized that she was always the last out of the pool and always had a towel around her waist when she wasn't in the water. Again, I had a choice to make but this time, my choice was easy. She was a beautiful woman who was just like someone who had given me an amazing night that I still fantasize about nearly two years later. The moment I grabbed her face and kissed her hard on the mouth, her hands were all over me. My shirt was off in record time and she moved down to lick and suck on my nipples. She pushed me back onto the couch and climbed between my knees, licking and sucking her way down my abs while she undid my belt and started pulling on the buttons at my fly. I heard a muffled "damn button flies" before she ripped open the fly on my pants and yanked both them and my boxers down to free my turgid cock. She gazed at my rigid eight inches with a look of happy surprise before licking her lips and then wrapping them around the swollen head. Her tongue worked circles around the head as she kneaded my balls and lightly stroked my shaft, rolling my eyes back in my head. She was absolutely amazing. She ran her tongue and lips on the underside of my cock down to my balls, where she proceeded to suck and lick each one thoroughly before licking and nibbling her way back up to suck the head back into her mouth. She worked her way down my shaft slowly, lingering on every inch and letting her tongue dance around my cock as it slid slowly into her mouth and down her throat. I was amazed at how much of me she could take in her small mouth and couldn't believe it when my head slid down her throat until her nose hit my pelvis and I could feel her chin on my balls. She held me like that before sliding me back out only to take a breath and then slide me right back in. This time, she managed to stick her tongue out and lick my balls, making me groan with pleasure. The whole time, one of her hands was constantly cupping and kneading my balls while the other ran up and down my abs, sometimes scratching lightly and occasionally pinching my nipples. It was far and away, the best blowjob I had ever experienced. Her speed increased slowly until her head was bobbing up and down in my lap. Even with the alcohol in my system, I had to grab her hair to get her to slow down just so that I wouldn't waste myself in her mouth. When I almost couldn't take it anymore, I yanked her head off my dick and pulled her up to kiss her hard. As her body pressed against mine, I finally felt the hard length of flesh that she had been hiding so artfully. My cock jumped in response and I knew that she felt it when she moaned into my mouth as our tongues danced. I reached down and slowly began pulling the silk nightgown up to reveal a body that I had wanted to see naked since I first laid eyes on it. She was better than I had imagined. Standing naked before me was a curvaceous but fit woman with an amazing body and a not-so-little something extra. Her legs were phenomenal, toned and muscular without being bulky. Her ass was perfect. There's no other way to describe it. It was firm and round, curving perfectly out of her legs and flowing into hips meant for grabbing and holding on to. Her abdominals were well defined without being overdeveloped and her breasts were just spectacular. They must have been at least a large C cup if not a D and seemed to defy gravity while still looking natural. When I reached out to caress them, they were definitely natural and I watched her nipples stiffen and stand out like two pencil erasers, begging for my tongue. Last, but certainly not least, a good six inches of impressive meat rose out of the waistband of her panties. Slowly, I reached out and pulled her panties down her legs, freeing her swollen cock. When she was finally naked, I noticed red marks across her lower stomach, hips, and upper thighs. They looked almost as painful as the ones prominently displayed on the shaft of her cock and on her balls. I guessed that she had some sort of strap system that kept it nearly invisible. Now I understood where the other, meaner half of her personality came from. If I had to strap myself into anything that looked that painful every day, I'd want to scream at someone too. The Drill Sergeant I reached out to touch it gently; careful to watch for anything that might cause her pain. Her cock jerked a little in my hand as I grasped it. It wasn't quite as large as mine but it was still thick and hefty, probably a couple of inches or so shorter than my 8". On her 5'1" frame, it looked huge. A soft sigh escaped her lips as I began to lightly stroke her, feeling the smooth, soft length of her. Reaching out, I cupped her balls, realizing that they were almost a handful, and squeezed them lightly, eliciting another moan. I had never done what I was about to do and was a little apprehensive about it. Tentatively, I leaned in and licked the head of her throbbing shaft. I tried to work the shaft and knead her balls while I was doing it but I wasn't sure if I was doing it right. Her cock jerked in response and I took that as a good sign. Slowly, I slid it into my mouth and worked as much of the rigid length down my throat as I could. It wasn't much but I went as far as I could and then let her slide out and let my tongue attempt a swirl around the head. It was definitely not as easy as she made it seem earlier. Before I had been doing it long, she stopped me and pulled me up to kiss her. She was breathless and trembling with excitement. We collapsed back onto the couch kissing and groping each other like a couple of high school kids. We weren't there for more than a couple of minutes before she got up and pulled me with her into the bedroom. We kissed on the bed some more and then she reached over to the nightstand and came back with a condom wrapper. She slid the condom on me and then grabbed a bottle of lube to rub all over my cock before climbing on top of me and easing herself down onto my throbbing shaft. The sensation was amazing. I slid easily into her tight little ass but once she was impaled on me, she worked the muscles inside of her to give me sensations like I have never felt before. As she worked herself up and down my shaft, I realized that her ass was as talented as her mouth. She was able to grip me more tightly than I had ever felt. It was almost like being squeezed by a very slick fist. I gazed down at her amazing body and noticed her cock standing rigid with need. I grasped her in my hand and jacked her off as she worked herself on my shaft. The tempo increased quickly and I could feel her balls slapping my stomach as I struggled to continue jerking her while she bounced up and down on my cock. Shuddering to a stop, she eased herself off and leaned in to kiss me hard. I rolled her over and kissed her like I meant it before working my hand down her body to the solid length of flesh between her legs while I licked and nibbled on her ample breasts. When I stopped, I rolled her on to her stomach and pulled her up to her knees. I moved behind her and licked the back side of her balls while reaching around to jerk her off a little, hearing her moan in pleasure and feeling the quivering need that throbbed in my hand. Finally, I got to my knees and began easing myself inside her. As before, her ass gripped me in ways that I still can't describe. Her ass was slick and tight but responded to my entry by opening to me before clamping down and milking my shaft as I slid it in and out of her. I gripped her hips and began vigorously pounding away at her amazing ass, feeling our balls slapping together with each stroke. Grabbing a handful of hair, I drew a long moan out of her as I pulled her up to grope her breasts as I continued to pound her. I looked down at the front of her body and watched as she jacked herself off while I slammed into her ass. I started getting close when she breathlessly begged me to stop. I halted with a final stroke, leaving myself inside of her while my hands continued to knead her breasts and pinch her nipples. "Are you ok?" I asked. "God, yes," she said breathlessly. "But I want to be inside you before I cum...if you'll let me." When she said that, I almost came in her ass right there. I had to control myself as I carefully slid out of her. I had never done this before and was both nervous and excited. After my first time with someone like her, I wondered what it would feel like. The opportunity to try it was almost as big a turn on as actually doing it. She lay me down on my back and moved between my legs. She slid the condom off me and went down on me, again rolling my eyes back in my head and making me worry that I was going to cum down her throat. I had to stop her after only a few seconds. When she stopped, she gave me a minute to catch my breath before pressing the head of her lubricated, latex covered cock against my ass. "You have to relax your muscles completely when I enter," she said. "Otherwise, I could hurt you." "Ok," I said and tried to relax my muscles. Slowly, she pressed herself against me and I felt the head enter. The sensation was painful but the throbbing in my cock and the amazing pleasure of the experience made me forget it almost immediately. As she slid deeper, I felt a sharp pain somewhere inside me and felt her stop with just a little pressure. "You're still clenching," she said in a voice that sounded almost strained. "Just relax and concentrate on opening up." I tried to loosen up but every time she pressed against that spot, I felt a sharp pain until something finally gave and she slid in, opening me up to sensations that I had never imagined. I moaned out my pleasure along with her as she slid in. It was like nothing I had ever felt before. I felt a little pain that was slowly fading away and being replaced with something that I can barely describe. It was like I could feel her rubbing the inside of my balls and cock at the same time. Each stroke sent powerful shudders of pleasure across my body. When I felt her grasp my cock and begin to stroke it, I thought I was going to loose it right there. "No," I gasped. "I'll cum." I watched her smile and chuckle a little as she released my cock and grasped my hips, pulling me into her for a better angle. When her strokes started increasing in speed, I could hardly contain myself. I watched her breasts sway heavily as she thrust herself inside of me, the muscles of her toned body contracting as they drove her cock deep into my ass. The way she looked coupled with the sensation of her filling me completely was almost enough to drive me over the edge. Her breathing grew ragged and I could tell that she was close. My cock jerked in anticipation, bringing me so close to the edge that I didn't think I was going to be able to stop myself. After a few more thrusts, she slammed into me with a harsh moan and began spasming. I felt the throbbing of her cock as she emptied her load into my ass. If she had continued to pound me while she came, I would have been finished. As it was, I had to try hard not to cum. I wanted to be inside of her when I did. As though she sensed my desire, she eased herself out of me and quickly took me into her mouth. Only moments after she came inside me, my cock was buried to the hilt in her throat and she was kneading and pulling on my balls as her other hand slid under and began to caress my ass. When I felt two fingers slide inside me and begin stroking whatever part of me that was causing so much pleasure, I was done. My balls tightened in her talented hand and I could feel myself clenching around her fingers as I erupted in her mouth. It was the most intense and amazing orgasm of my life. I exploded down her throat as she continued to bob her head up and down on my cock, draining every drop of cum from my throbbing balls. I completely lost myself in the sensation. I grabbed the back of her head and shoved her down onto my cock as I emptied myself, feeling her swallow every drop. I lost count of how many times I fired a gob of hot, sticky cum and was amazed at how easily she took the load with nine thick inches of hard, spasming cock shoved down her throat. When I finally finished and let go of her head, she slowly eased me out of her throat, sucking hard and gripping me tightly with her soft, thick lips to get every last drop. When she was finally at the head, she carefully continued to work my balls and suck, swirling her tongue to clean me off completely. I could barely stand it. Finally, she let my cock wilt out of her mouth and smiled up at me, giving me a look that I will never forget. Her green eyes held complete satisfaction and the smile she gave me was one of exhausted contentment. She climbed up my body as I surged up to meet her, kissing her hard and pulling her the rest of the way to an embrace. I could feel our cocks rub against each other as her breasts pressed against my chest. Our tongues danced until we were too tired to keep going. We lay there in utter, blissful exhaustion for a while until she pulled me back to kiss her and then got up, leading us to the bathroom. The rest of the night, we couldn't keep our hands off each other. We had sex again in the shower before actually cleaning off. By the time we were done, we had used up all the hot water and were so tired, sleep hit as soon as our heads hit the pillow. We saw each other in secret for a few months until I had to leave the base to go to another duty station. I keep in touch with her and see her as often as I can. We know that we can't have anything serious because of the rules in the Marines but, so far, it's been nothing but fun and we're trying to keep it that way.