The time came as the video ended. Sarge softly whispers in my ear, asking if I was ready. I wasn’t but I wanted to be. I wanted to be his slut. I wanted him to fuck me like he fucked my wife. Sarge pulled out a large bottle of lube and started slathering it on his cock. He told me to kneel, leaning over and to bite the pillow. This scared me. My body turned cold as I got myself into position. I felt his hand pull the crotch across my ass and put his finger covered in cool lube against my asshole. He swirled it in a circle before applying pressure and it quickly slide in. “Have you ever done this before?” he asks with a rough voice. “No, have you?” I meekly respond. I can feel his finger slide deeper in. I wait for his answer as I feel a second finger trying to make it’s way into my ass. I clench up and he backs off a little before pulling his finger in and out gradually fast. He then slides the second finger in quickly and with a bit of force. I gasped and bit the pillow until the pain subsided. After a few minutes I feel him shift around and pull his fingers out. He placed his warm cock head at the entrance of my ass and said, “I’ve done this before but never twice with the same girl”. He let that process in my head for a full second before plunging half his cock in me.
The pain sears through my body. My asshole feels like it was just exploded. I bite hard on the pillow as he is still. “It’s ok, it’s in, just breath. It should get better.” I barley hear him say as I’m groaning into the pillow. He slowly slides is cock in and out just the smallest amount. I can feel my asshole grip him and each vein that sticks out. He squirts some more cold lube down my ass crack. The cooling feeling provides some relief but it still feels like I am split open. Sarge slides in and out a little more, maybe two inches back and fourth. “There you go, just breath and relax.” he commands. My breaths are shallow and rapid but I try to control them, slow them down. Taking deeper and longer breaths. It’s all on concentrated on. “hhhmmm there we go. That’s a good girl.” I hear him say as he now starts to drive his cock deeper into my body. I’m sure if I look I’ll see blood pouring out but when I turn my head, looking under my body and between my legs, all I see is a little limp dick dripping clear liquid with a tiny sack and a pair of balls swaying behind them. I’m relieved and pleasantly surprised. Gradually Sarge picks up speed and force. It takes him some work but he was able to fit his entire cock in my ass. It made me happy when he told me, I was able to looked up at video and watch Amy get fucked. There was still a bit of pain but not that bad, in fact the sensation of being full was a pleasant one. Sarge grabbed my shoulders and started pulling me even harder against his cock. This hurt and my natural reaction was to pull away and fall forward. Sarge fell with me, continuing his rough pounding into me while I was pinned to the bed with no where to go. I whimpered and grabbed the mattress as he finished. His cock pulsed a few times before it stopped and soon after he stopped. My eyes were filled with tears and jaw hurt from clamping down but I made it. Sarge was breathing hard as he started to slowly slide out of me. His cock already starting to deflate. As he neared the tip, he squeezed out the last bit of cum from his cock and slapped my ass hard. We didn’t talk at all while I stumbled and painfully got dressed. I could feel his cum leak out of me and run down my leg. My asshole could feel the breeze of air on the walk back to the tent. I picture it as the walk of shame many women take after a night out.
I couldn’t sit for two days. I was uncomfortable and shitting blood. I thought I needed to see the Doc but knew there was no other excuse for this type of injury. When I talked to Amy, we avoided the topic other than her saying something about me having fun. I feel like the this long distance has drawn us closer together. We are talking more than ever. She regularly puts Ashley on speaker so she can hear my voice and I get to hear her talk.
My ass’s soreness has subsided but it’s still tender, especially when Sarge walked up to me and smacks my ass. I looked around quickly to verify no one was around, which we were alone for the moment. He told me he wanted to see me again. I tried to tell him I was still hurting but he insisted and threatened exposing me.
That night was like the other, he laid out the lingerie and wig and waited for me. I was expected to put it on as soon as I arrived. It still had the scent of lube to it. After getting dressed Sarge ordered me to my knees and to suck his cock. He used the most forceful tone I’ve heard yet in our private sessions. I was scared, both of doing what he said and of not doing what he said. I slowly got down on my knees, sitting on my legs. I look up at him as he starts to unbutton his pants and pull his cock out. It nearly hits my face as is droops heavily down. “Well, don’t just stare at it.” he sternly touts. I reach up with my hands to grip the base and he slaps them away. “Just your mouth.” I cautiously slow my hands and open my mouth, moving my head to his cock. I start slow as I feel his cock start growing and stiffening in my mouth. The feeling is utterly erotic and I can feel my cock strain against the satin crotch. I feel Sarge’s warm hands slide over my head. He places each hand on the sides of my head. I know what’s coming. I try to pull away and say no but only a mumble can be heard as he holds my head in place. Instinctively I reach up to pull his cock away from my mouth and he quickly pops the side of my face, “No hands, put them behind your back” he callously says. He slowly and gently pulled my head back and forth across his cock. He then starts going deeper. I gag but he just holds my head still. I feel another slap against my face as I must have reached up again. I grab my hands and hold them tightly together around my back as I hear “Breath through your nose, relax and breath through your nose.” in a calm soft tone. “Don’t panic, just breath through your nose.” he says. That night I got my first lesson in deep-throating. I still needed lots of practice but it wasn’t a bad start I’m told. Once Sarge had his kicks gagging me half to death, he tossed me against his bed, with me bent over laying on the mattress. I felt the familiar drag of my lingerie across my ass and cold lube down my ass crack. He didn’t foreplay with me much as quick fingering and in he went. I squealed loudly due to the sudden insertion. He reached over and covered my mouth, smashing my face into the stiff mattress. Sarge starts thrusting and was slow to remove his hand off my mouth. “You’ve got to be quite!” I hear him say between thrusts. The pain wasn’t as bad as last time but everything was still tender. I don’t know how long this went on, I tried to picture Amy. I Imaged how Amy felt taking this big cock. The faces of pain and pleasure she made flashed through my head. Sarge makes one last thrust and holds, I knew it was over. His cock pulsed in my ass again and he slowly withdrew it. We got dressed quietly again and I left; making the same sore walk of shame with cum still draining down my leg.
I counted the days left on deployment as I laid in my bunk that night. Just under 3 months left, 87 days. If Sarge fucks me every 3 days, that means I have… fuck! 28 more times of this. Can I really make it that long? Will my ass make it? I fall asleep wondering how is ass fucking a thing? Who enjoys getting their ass fucked? Must be by a little dick. Then all the times I begged Amy to let me put it in her ass cross my mind. Never once did she agree.
I couldn’t sit for another day or two. This cycle continued until near the end of the deployment. About two weeks from going home he stopped coming to find me. I had grown accustomed to our ritual of my abuse. I had actually started to enjoy it and as the days grew closer to heading him, I craved his cock. I knew going home, things wouldn’t be the same but, I wasn’t ready for it to end yet. I knocked on his Pod and he turned me away. He told me if I came back he would make me regret it. I was disappointed. The man that has been fucking me for 6 months just stopped. I had to know why. I didn’t care what he did, as long as he fucked me one more time.
Three days before leaving I show up at his door knocking again. He was somewhat pissed to see me when he opened the door. I was worried he was going to turn me away but he invited me in. “You know what this means right?” he says while searching through things. “Yes, I’m a bad girl and am going to get punished?” I respond is a playful manner as he pulls out the customary lingerie. I couldn’t stop the smile from growing on my face as he tossed it on the bed and told me to get dress. He had to piss and he’d be right back. I quickly got dressed, even lube my ass for him already in case he tried to put it in dry. I waited and anticipated what he was going do. I wanted to try to look more like a girl and tucked my stiff dick all the way back. It was painful and uncomfortable but, it gave me a smooth and mound like appearance in the crotch. It took Sarge longer than expected to return. But, as I heard the door open, I was posed laying provocatively across his bed.
I was greeted by Sarge, saying this should be fun. He opens the door wider and I can see several guys gathered behind him. I am alarmed and try to cover up but Sarge walks in and brings two other guys with him. “What’s going on? Who are they?” I nervously and in a panicked tone ask. Sarge picks me up and tosses me on he’s roommate’s bed. He reaches into his pocket grabs a fist full of zip ties. I fight but each of the guys grab my limbs and hold me while Sarge places me in a kneeling facing away from the door on the bed. My feet and arms are bound together. My ass is in the air and exposed as Sarge slaps it and says “Ok boys. I lied, it’s not a girl but a sissy boy. I’m sure most of you would put your dick in anything at this point, ENJOY.” He then pulls the bottom of my lingerie over as he always did. After 9 months of masturbating, most young men would fuck anything that moved.
I could hear the rattling of belts and a few cheers before I felt the first guy start in. He quickly came in a few thrusts and sighed, dismounting and walking away as the next guy started fucking me. I lost count of how many guys fucked me but Sarge estimated it in the 30 range and a few of them went twice. towards the end, the smaller guys were fucking my mouth because I was to gapped for them. I was literally covered in cum. Guys would shoot cum across my back, on my ass, and some walked around and shot it in my face. By the time the last guy was done, I was exhausted, humiliated, and loving it.
Life was never the same again.
Source: reddit.com/r/sexystories/comments/doyvfk/mfcucksissy_solder_gets_fucked_in_more_than_one