Sailor Captures Flyboy

By Jack Doe

Published on Aug 15, 2008

Gay

We were about 3 months into a Persian Gulf deployment aboard the USS George Washington. I was headed to my stateroom to enjoy some porn in private while my roommate was flying. By virtue of being a senior lieutenant in my squadron I was able to live in a two man stateroom. It made cruise just a little easier. Of course one of the best things was only having one roommate and knowing that you had time to yourself whenever he was flying. I walked into the room and was startled to see one of the sailors sitting in the chair at my desk paging through a magazine. I recognized him as one of the sailors that cleaned the staterooms in that area of the ship; a coop cleaner as they were known.

"Whats going on in here shipmate? ", I asked. He looked up and said, "I'm just looking at one of your magazines". He closed the magazine and held it up for me. My heart sank when I saw what it was. It was a magazine that featured transvestites and transsexuals. My secret obsession was T-girls, and more accurately, being a T-girl. I hoped the panic wasn't showing as I said, " I don't know what you are talking about, that doesn't belong to me". He looked at me and smiled. It wasn't a pleasant smile either, almost predatory in nature. "Well, I found it in your stuff, Sir" he sneered. I feigned anger as I said, "You need to get out of here and take your magazine with you!" He got up and started to walk to the door and I figured I had dodged a bullet. He probably just wanted the magazine I thought.

As he neared the door, he stopped and turned towards me. "I'll leave, " he said, "but of course I'll have to report this to my division officer". A smile played at the corners of his mouth as he watched for my reaction. "Well report it to him and I'll tell him that you brought it into my room", I said. "That might work, " he said. He continued, "But it might not either. Are you willing to take that chance?" "Of course, I could just talk to a few sailors from your squadron about finding this in your room. You know how fast mess deck rumors spread. It also wouldn't be too hard to find your home address through some friends in the Admin Department, and as a concerned young sailor I could write your wife to let her know what I found".

My head was spinning and I didn't know what to say. He had me trapped; I knew and he knew it. "Ok, fine, what do you want?", I asked. "You want some money or something?". He looked at me and said, "Or something". I began to feel sick to my stomach as I finally realized what was going on. "What do you mean? ", I said, hoping for the best but expecting the worst. My heart was pounding and my mouth was dry. He held up the magazine. "I want you to be one of these girls. You know how horny you get out here and I need a reliable fuck. " It was my greatest fantasy and greatest fear. I lamely replied, "Well I don't have any clothes like that." "Don't worry about the clothes, I'll take care of that later. The first order of business is your first training session". I sighed. "My first training session?" He unzipped his pants and pulled them down, revealing a long hard cock. "On your knees and get to work". I tried one more time to extricate myself from the situation, "My roommate will be here any minute". His face turned slightly angry as he snatched a flight schedule off my desk. "Do you think I'm dumb and don't know how to read this? " he said in a low angry tone. "Your roommate wont be back on deck for another hour. He sat back in my chair and said, "Now quit wasting time."

I started to kneel in front of him and he shook his head. "No, get naked." I shed my flight suit slowly, the undressing mirroring the undressing I felt occurring inside me. "Turn around slowly so I can what I own". I turned slowly, letting him take in my body. I am 6'2", medium build, with blond hair and green eyes. I wasn't especially ripped or cut, but I stayed in shape. Tall and fairly lean, I also thought I would look pretty good as a woman. I think the sailor agreed because he murmured appreciatively as I turned. He stared at my cock for a moment and said, "Your cock inst very big. But thats ok, since you aren't going to have much use for it." He was right of course, my cock wasn't very big at all when I wasn't erect, and even when erect it barely topped 5.5 inches. And compared to the monster he was wielding, it looked even more pathetic.

"Ok, " he said and gestured for me to continue. I knelt in front of him. I had only been with a man twice before so I knew I was going to be awkward. I grasped the base of his cock and lowered my mouth towards it. I felt completely surreal, almost as if I was floating above the scene and just watching. As I neared his cock he said "Wait!" I looked up at him and he said "You have to ask for permission." "Please let me suck your cock, " I said in a flat monotone voice. "Ok, say it like you mean it " he said,"Or else. Also, call me Sir from here on out." I could tell he took distinct pleasure in that particular role reversal. I repeated myself, making sure to address as I had been instructed. He looked pleased and asked, "Why do you want to suck my cock?" "I paused, and then leaped over the virtual cliff, "Because I love sucking cock, Sir" He nodded happily and indicated that I should continue. "I am just a cock whore, who loves cock. Please let me suck it Sir", I said and I could feel my psyche training already. "Ok, you have permission, " he said. I lowered my mouth onto his cocks and began to slowly bob up and down on it. He groaned and pushed down on the back of my head, trying to feed more of his huge cock into my mouth. My inexperience got the best of me and I gagged. "We'll have to work on that", he said, "Go as deep as you can for now." I managed to swallow another couple of inches, but I still had a lot to go. As I continued to suck, he leaned forward and stroked my cock a few times. "Hmm, your little clit is so hard. You really did want to be a cocksucker didn't you?" he asked, the delight obvious in his voice." I felt the shame wash over me as I realized how easily I had been controlled, giving up without more than a pretense of a fight.

He began to moan as I continued to suck and I could feel his cock pulsing in my mouth. "Mmm, I'm going to fill your mouth with my cum", he whispered hoarsely, "and don't you spill a drop!". I continued to milk his cock hungrily. My domination was complete at this point and all I could think about was pleasuring him. Suddenly, his cock began to spew the contents of his balls into my mouth. I choked a little as I was caught off guard, but managed to chock the initial load down. He continued to pump his salty cum into my mouth and I swallowed every drop. He held me on his cock until it was completely empty.

"Stand up", he said. I did so and he looked at his watch. "Hmm we still have some time. Bend over the chair, slut". I did so and I heard him rustling around in one of my drawers. HE pulled out my the belt to my service khakis and doubled it up. He smacked me on the ass with it and asked me if I liked it. I thought for second about the question. I had never really fantasized about being spanked, but I found I did like it, even though it stung. "Yes Sir, I like it" My face turned red once again as I realized the situation I was in. The young sailor had me completely at his mercy and was playing me like fiddle. He methodically continued to spank my ass and I could feel it getting warm and red. He went to the medicine cabinet and pulled out some hand lotion and massaged into my ass cheeks. He then put some on his finger and thrust it violently into my ass. I jerked at the intrusion and he smacked my ass again, now with his other hand. "Be still!". He then worked the finger in and out of my ass. I could help but moan a little. "This ass is pretty tight, has it been fucked?" he asked. I said "No Sir it hasn't". "Well its about to " he said.

I didn't think there was any way he could be ready again already. But he was a young man, and had been on deployment for a few months now, so he probably didn't need much time. A quick glance over my shoulder confirmed the fact that he was ready. He pressed his hard rod up against my ass and said "Well, you know what to do." "Please my fuck my ass, Sir" I said. My request was genuine and heartfelt this time. There was nothing I wanted more at that moment then for him to treat me like a slut. He pressed against my tight asshole and I felt the head pop past my sphincter. He kept the steady pressure on and slowly slid into my ass. I bit my lip to keep from moaning with pain. It felt nothing like I had imagined and the pain was intense as his cock stretched my virgin ass. It felt like a bar of steel being pressed into my guts. He continued to push and I thought I was going to be ripped in two. I felt his hips meet my ass and I realized I was now filled with about 8 inches of cock, if not more. He started thrusting in and out and slowly the pain began to subside as my ass stretched to accommodate him.

"Feel good, doesn't it whore? Your ass is so tight, it was made to be fucked by a man like me, " he gloated. He knew he had completely captured me in less than an hour and that I was completely at his mercy. He increased the pace of his thrusts and moaned. "Its not going to take long, you are so damn tight", he said breathlessly. "Fuck me hard Sir, " I said in fierce whisper, "I want you to fuck me hard". He didn't need much encouragement and thrust harder and harder. "Here it comes bitch", he said. He convulsed as he began to shoot his hot ropes of cum into my ass. It again seemed like an eternity. He pulled out of my ass and it popped softly as he withdrew. "Don't move" he said. He reached into his pant and pulled out a small wrapper and tore it open. I realized it was a tampon and he saw me watching. "I've been planning this for a while," he said with a grin. He placed the tampon in my ass and said "I want you to keep this in your ass until you shower again. It will be a nice reminder of your new place in the world.

HE walked around the front of the chair and shook his head. "You are dripping all the floor, you dirty slut. Get down there and clean up your mess, "he commanded. I immediately dropped to the floor and began to lick the pre-cum up. When I was done he told me to lay on my rack. I did so and he said, "Now jerk your little clitty for me, slut." I didn't need to be told twice and grabbed my hard throbbing cock and began to jack off. "Put your feet in the air, whore."I did do and he pressed my ankles towards my head until my cock was pointed right at my face. I was already close to cumming and knew it was going to be a lot. "Cum bitch", he said and seconds later I exploded. Wave after wave of cum hit my face and open mouth. "Now lick it up as much as you can". I eagerly licked my lips and as far as I could reach with my tongue.

He checked his watch again and said "Well I better get going so my supervisor doesn't know wonder where I am". He wrote something on a piece of paper and dropped it on my desk. "Meet me at the compartment number tonight at 2400." "Yes Sir, " I replied. He smirked and said "Good girl" as he walked out of the room. I pondered for a moment the events that had just happened. It was intensely pleasurable but I was also filled with shame and loathing. Tear filled my eyes as the full import of what I had gotten myself into filled my mind.

To be continued... (if I get good feedback) My first attempt so be gentle. Contact me at slavewriter69@yahoo.com

Next: Chapter 2


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