Military School Crosdresser
- 1 year ago
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Military School Adventures 3 free porn video
Disclaimer: This story is not intended for inappropriate audiences. If you are too young to be reading this or this story is illegal where you live, then please do not go any farther. This story consists of sex between consenting men and is entirely based on real life occurrences; the names have been changed to protect the guilty. This story is copyrighted and should not be copied or distributed, all rights reserved.
Any feedback would be welcome; I do ask that all criticism be constructive as I will ignore all flames. If you want descriptions of me or Luke at this point, read Chapter 1. I also suggest reading chapter 2 and that having been said; enjoy the story.
A couple of days later Luke caught up to me and asked if I was going home that weekend or staying on campus. I told him that I was staying this weekend. He said with a grin and a wink, “Good we can go help Capt. Frank Saturday afternoon.” Now in a military school, weekends are pretty much all the free time you get but it starts out with a Friday night all out cleaning session to get ready for Saturday’s inspections. After inspection you have the rest of Saturday off.
After inspection Luke came to my room and said it was time to go help Capt. Frank. I was really nervous; I mean this was a grown man and a faculty member. We went across campus to the faculty bachelor’s quarters and knocked on Capt. Frank’s door. In just a couple of seconds the door opened up and there stood Capt. Frank in just a pair of gym shorts. A quick glance at his crotch revealed that he wasn’t wearing any underwear or a jock strap because his dick, mostly hard, was very evident. I had seen his dick that night he watched Luke and I 69 and it was only 5” long but it was as big around as a beer can! He beckoned us in saying, “Welcome to my humble abode. Can I get you fellas a drink?” We both asked for a Coke and he turned towards his small kitchen and yelled, “Hey Bill, get these fine fellas a Coke.” I almost shit my pants! Who in the hell is Bill and why is he here? My answer came shortly when in walked Capt. Bill, another faculty member, and one of my coaches on the swim team. My mouth was hanging wide open in astonishment. Capt. Bill walked up to me grabbed me by the back of my neck and planted a big ole kiss right on my open mouth. He pulled back and said, “Boy, I’ve been watching you strut around the pool in those Speedos for 3 years now and I find out from Frank here you play around! I’ve been missing out and I intend to make up for lost time.” Whereupon he kissed me again so hard my knees got weak. I should tell you that Capt. Bill was a champion butterfly swimmer who had maintained his swimmers physique. I had to lifeguard some weekends and he would come in and start doing laps; I swear I wouldn’t think he would ever stop. He would come into the weight room, do a hand stand, hook his feet into the inverted sit-up strap, and proceed to knock out 100 reps. Hot body and six-pack abs is the word!
My heart felt like it was going to come out of my chest and I thought I was going to faint and then I realized my cock was hard as a rock. I couldn’t believe this was happening! I looked over at Capt. Frank and he had Luke on his knees with his face pressed into his crotch. I looked back at Capt. Bill and said, “I don’t know what to say. I mean, you’re my coach!” “Look”, he said, “Frank tells me he’s seen you sucking dick and that he got you to clean off his after he jacked off watching you and Luke here. I’ve always fantasized about you and I can’t wait to fulfill those fantasies. If you don’t want to have sex with me just say so.” “No, it’s not that! I always thought you were hot as hell; I’m just shocked”, I sputtered. “Look, get out of that uniform and we can both be naked and it won’t feel as weird. I promise”, he assured me.
With shaking hands I loosened my tie and shirt and tossed them over the couch back. The whole time Capt. Bill was looking at me with lust filled eyes. I kicked off my spit shined shoes and dropped my woolen uniform pants. Now I was standing there in nothing but my tighty whities and black socks. “Go ahead, let’s see what you got hiding in there for me”, Capt Bill leered. I hooked my fingers in the waistband and slowly pulled them down. My cock sprang up and hit me in the navel. “Whoa son, that’s some cock for a 17 year old!” “Thanks”, I replied while reaching down to take off my socks. Capt. Bill then dropped his gym shorts and a rather impressive 7” piece of meat came into view. I noticed he had trimmed pubes and shaven balls. I still hadn’t gotten the nerve to get a razor anywhere close to my nuts. “Capt. Bill, you’ve got a nice cock too!” Capt. Bill walked over to me and grabbed me by the cock and said, “Look, we’re both naked. I’ve got your cock in my hand. I think we can drop the Captain and just call me Bill; okay”? “Okay, uh, Bill”, and I reached out and grabbed his cock. We then leaned into each other and went into a deep passionate kiss while each stroked the others cock. He broke the kiss and proceeded to kiss down my neck and chest. He flicked his tongue across my very erect nipple and it sent a jolt to my groin that I didn’t know would happen. I groaned out load and he looked up and smiled, “Like that, huh?” “Oh yes”, I moaned. He then dropped suddenly to his knees and engulfed my cock until it hit the back of his throat. I was so caught off guard at the heat of the moment that he sucked me a couple of times and I lost it and came hard. He just kept sucking until I was finished. “I’m sorry; I couldn’t help it”, I said mortifyingly. “Hey, you’re young and we needed to get that first load out of the way so we can enjoy the next one. Now, how about you show me what good little cocksucker you are.” I was relieved that Bill wasn’t upset at me and was determined to show him how much I desired him. I smiled and leaned over and gave his nipple a good suck and then nipped it just a little to see his reaction. Bill moaned and stroked the back of my head. I kissed down his ripped stomach saying how much I had admired it when he did the sit-ups. My chin bumped into the tip of his cock and it shocked me a little. I pulled back and a strand of precum stretched between my chin and his cock. That was all I needed; I had to taste him.
I leaned back in and gave the head a nice long lick sucking up the precum. God it was sweet! I took the head in my mouth and just swirled my tongue around the knob and sucked to try and get more of that sweet nectar. Bill laced his fingers in my hair and stroked me encouragingly. I sank down as far as I could get and held him there. I couldn’t believe I had my coach’s cock in my mouth. The man who had been telling me what to do for over 3 years! It was a truly bizarre feeling. I guess I dazed out for a second and Bill noticed the hesitation and asked, “Everything okay?” It broke me out of my haze and I just nodded, “Hmmm Hmmm.” I then started taking long strokes in and out of my mouth watching to make sure my teeth didn’t nick him. God I was so fucking turned on! My dick had recovered and was so full of blood it felt like it would pop any second. I reached up and started playing with his balls and he moaned and pulled my head down a little farther on his cock. I gagged a little and he let up. I didn’t give him a chance to feel sorry because I plunged right back down determined to try and do a good job for him. “That’s it, suck that cock. You’re a natural.” I was elated that he thought I was doing a good job. He was drooling precum by the bucket it seemed like and I savored it as it seeped down the back of my throat. It wasn’t long before I felt his cock swell and his balls draw up. He started to pull my head up but I shook it back and forth and sucked hard; I wanted his cum and was determined to have it. He let loose a torrent of blasts in my mouth and tried really hard not to spill a drop. I kept swallowing but a little came out the side of my mouth. I made sure he was empty before pulling back and looking up at him. He had that lustful look on him and then smiled, reached down a finger and scooped up the escaped cum and held it to my lips. I opened up and took his finger in to clean him off. “You are one hot little cocksucker. I can’t believe it took this long to find that out! Here drink some of your Coke, it will help with the aftertaste”, he said as he handed me my Coke. “I like the taste”, I replied taking the Coke from him and taking a big swallow. “Come on let’s sit on the couch and take a little break so we can recover.” I looked down at my rock hard cock and then looked back up at him questionably. He just laughed, “I know you’re a young stud but this old man needs a couple of minutes to go again.” “You’re not that old; 25 or so?” “27 actually, but still I need a little break”, Frank said. I reluctantly joined him on the couch and that’s when I noticed Frank and Luke.
Capt. Frank was leaning over the couch and Frank was fucking him up the ass! I was shocked but Frank had this look that said he was enjoying every stroke. “Holy shit”, I whispered to Bill. “Luke is fucking Capt. Frank in the ass”! “Haven’t you been fucked before or done the fucking”, whispered Bill back. “When I was 9, a 14 year old neighborhood kid fucked me but his dick was really small. It seems like a real cock would hurt like hell!” “It might hurt a little at first but if you’re properly prepared, it doesn’t hurt so much and then when that cock starts hitting the right spots in your ass, it’s incredible! Here, let me show you something”, Bill said. Bill pushed me to side to get me to lie on the couch. I lay back wondering what he was up to. He gave me a reassuring smile and then grabbed me by the back of the knees and pushed them back towards my chest. “What the fuck is he going to do to me?” I thought. He then scooted down and gave my dick a long lick up the shaft and I moaned in approval. Instead of taking me in his mouth he moved down and licked my balls. “Man, you need to shave these puppies”, he complained. “I’m sorry”, I replied, “I’m too scared to get a razor anywhere near there.” “There’s nothing to it. Either I can show you or I’m sure your buddy Luke would help you out. There’s nothing like clean shaven balls. I’m sure you’ll get addicted to it once you get the hang of. Enough about that though let me show you something that you’ll like.”
Bill lowered himself back down and suddenly I felt his tongue slide up the crack of my ass. “Holy shit, what are you doing?” He looked up and smiled, “Shhhh, lay back and relax and let coach take control.” I laid back and tried to maintain my composure. I felt Bill’s tongue back in my crack and then it brushed across my pucker. Oh my God, it felt incredible! Bill worked his tongue around my ass until I relaxed and then all of sudden I felt the tip of his tongue enter me. I instinctively clamped shut on his tongue. Bill pushed back on my knees and I knew he wanted me to relax. For a second it reminded me of how he would make us divers sit on the deck with our backs against the wall and pointing our toes out and he would come and step on them if they weren’t pointed enough. I kind of chuckled to myself before Bill’s tongue slid back in my hole. This time I tried to relax and let it happen. The more he tongued me the looser I got and the better it felt and then I felt his finger rubbing around the bottom of my hole. He then slid the tip of his finger in while still licking me. I tightened up again and he pressed my knee back again to get me to relax. I took a deep breath and tried to relax and his finger slid in to the first knuckle. He then wiggled it around a bit to help loosen me up. He kept slobbering all over my hole as he worked the finger in my ass. I was starting to get used to it but still had my eyes tightly clamped shut. “Relax man, you’re going to love this shit”, someone said into my ear. I threw my head to the side and opened my eyes and there was Luke naked and smiling at me. He then leaned down and gave me a smoldering kiss. I was really getting into it when I felt a second finger gently enter me. “He’s got two fingers in me man!” Luke smiled again, “Wait till he gets his dick in you. There’s nothing like having your asshole stretched around a nice dick!” I fired back, “He’s not going to fuck me is he?” “If he doesn’t, I will or Frank will, but you better work up to Frank. It may be short but you’re not ready to shove a Coke can up your ass yet”, smirked Luke. “I could never take that”, as Bill all of sudden put in a third finger. I moaned, “Holy shit, that’s three fingers!” “Yea, but look at your dick, Man. It’s hard as a rock; you’re going to be a bottom slut I bet”, laughed Luke. He then leaned back in for another long kiss. I felt Bill moving around below but his fingers never stopped fucking my hole. Luke broke the kiss and looked down between my spread legs to see Bill kneeling up. Frank was leaning over the back of the couch with a tube of lube and was greasing up Bill’s cock. I realized that I was about to get fucked by a real cock!
Bill pulled his fingers out of my hole and Frank put the tube of lube to my ass a squirted a big glob in me. “That will help some; try and relax. I expect to get to use that hole someday too”, leered Frank. “Holy fucking shit”, I shuddered at the thought. Bill positioned his cock at my virgin (almost) hole and pressed while he told me to relax and enjoy. Even though he had prepped me for a while, it still felt like this was not going to work. All of sudden the head popped past my ring and motherfucker it hurt! I started to slide back up the couch trying to get away from him and he grabbed my nipples and pinched. “Relax and lay still; you’ll get used to it. Calm down!” I tried to relax but the pain was sharp; I thought someone had shoved a hot poker up my ass! I felt a tear run down my cheek and my cock went totally soft. Bill kept stroking my nipples while he held himself in me. I took a very deep breath and let it out trying to relax. Some of the pain went away and I felt like I would live again. “That’s it, just relax and let me in”, Bill cooed. I finally eased up and Bill gently slid another inch in before pulling out until the head was just in. He did it again and it went in another inch. I let out a load grunt but the pain wasn’t near what it was. “That’s it, take that big cock up your tight little ass”, Luke said in my ear. This gave me encouragement and I pushed back a little on Bill’s cock making it go in another inch. Bill moaned and smiled at me and pushed his entire length up me in one more stroke. “You’re fucked now”, said Frank from above me. Bill started taking short strokes in me and then pushed my knees back a little farther. On the next stroke he hit something in me that sent a jolt through me. I let out a moan and looked up at Bill wide-eyed. Bill smiled, “I believe I found the boy’s prostrate!” I don’t know what a prostrate does but I sure wanted to feel that again and I did. He took up a steady rhythm hitting my prostrate on each stroke. That was it – I was hooked. I had never felt anything like it. My cock had returned to all its glory and it was leaking a pool of either precum or prostrate milk; I wasn’t sure. “OH fuck yea, give me that cock”, I screamed! I was in heaven!
I felt something move over me and I opened my eyes to see what it was. There right before my eyes was a cock I recognized. Just then a mouth went around my cock and I almost lost it. Luke had positioned us in a 69 position while I was getting fucked for the first time. Luke had his knee right beside my head and he used it to push my head so it hung over the edge of the couch. He then started tapping his cock on my lips encouraging me to open up. I opened my mouth to take him in and in that position he had straight shot down my throat. Again, for the second time in a few minutes, I had a rude awakening as he slid in until his balls were resting on my nose and forehead. I started gagging and he pulled back making saliva rush into my mouth. He then started taking short strokes so I wouldn’t choke. “Holy fucking crap! I’m getting fucked, and it’s amazing! And, I’m getting blown and I got a cock in my mouth! Good God what else can there be?” And, then I remembered Frank, “Oh shit; where is Frank?” On one of Luke’s up strokes I looked past his balls and there was Frank stroking his lubed Coke can cock and moving into position over my head. I saw him take his lubed finger and put it Luke’s ass. I felt Luke moan around my cock sending vibrations up my spine. I then watched Frank slowly put that monster right in Luke’s hole. “My God, he’s taking that monster”, I thought! That momentary distraction had gotten me back down from my eminent orgasm or so I thought. About that time Bill really pushed back on my legs and started long stroking me, slapping his balls on my ass every time he bottomed out. Every time Frank pushed into Luke he went down on my cock and his cock went down my throat. It was sensory overload and I felt my balls draw up for a monster cum. I let loose a torrent of cum into Luke’s mouth and my ass pulsed around Bill’s cock. That did it for him and I felt hot sperm flood my ass. It’s a feeling I will never forget. All of that was too much for Luke and the next thing I knew, my mouth was getting flooded with another hot load of cum.
Frank wasn’t done with Luke yet. He pulled Luke with him as he sat back on the couch. “Ride my cock Luke boy! Make me cum!” Luke leaned up placing his hands on Frank’s knees and starting bucking up and down. I slid off the couch to the floor to get a look at that Coke can going up my buddy’s ass. Bill handed me a towel and said sit on this don’t get cum all over Frank’s rug and then he slid off and snuggled up to me to watch also, putting his arm around me possessively. I couldn’t believe it; Luke was actually getting hard again. I couldn’t help but think, “What makes that thing hook the right so much?” But man was he really slamming down on Frank’s cock. All of a sudden he grabbed his cock and stroked it really fast. Next thing he was cumming and cum was flying everywhere! He fell off of Frank to the floor and Frank moaned and grabbed his cock and started stroking. “Fuck, I’m going to cum”, screamed Frank! Bill grabbed me and pushed me toward Frank, “Get in there and don’t waste a drop!” I reacted to my coach’s orders and scooted over between Frank’s legs and opened my mouth. Frank moaned and shot the first blast right in my eye and it stung like hell! I clamped my eyes shut but left my mouth open to receive the next rope right on my tongue followed by two more. I stayed there as the last dribble fell onto my tongue and then swallowed it down. I wasn’t prepared for what Frank did next as he slid his fat cock right into my mouth. “Clean me up Cadet”, he ordered. I thought, “Oh my God, I’m sucking my friends ass juices of this motherfucker!” but an order is an order.
We all stood up and I helped Luke up off the floor. He looked at me with a smile and said, “Man, that was intense!” I just laughed and shook my head in agreement. I felt something cold against my arm and looked to see Bill handing me a fresh Coke. I turned it up and drank half the can. I had never felt so sexually drained in all my life. Frank looked over at the clock and said, “You guys better get back to the barracks and shower up before mess call. Oh, and don’t drop the soap!” We all laughed and started getting dressed. Coach looked at me and said, “We have about 5 months left until you graduate and I plan to take advantage of it! Next time though, I’m going to teach you how to fuck me.” I grinned at him, “I’ll look forward to it but I just might get Luke to let me fuck him first! I need to find out if I’m a bottom or a top or somewhere in between.” “Well have fun finding out, and oh, be careful and don’t get caught”, he returned with a stern warning. Luke and I left and went back to the barracks. Since I was a cadet officer, I had a private room with my own shower instead of the community one. I told Luke to come to my room so we could shower together. We soaped each other up but were out of time for more fun. I couldn’t help but wonder what was next, but for right now, Damn! -->
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