Chapter 1

During the summer before my senior year of high school back in 1972, I had just turned 18 and managed to get arrested and charged as a minor in possession of alcohol at a party. I was a pretty good student, but this infuriated my parents and once they paid a pretty penny to get me out of trouble, they began discussing where they were going to send me to school, as they were not going to let me go back to my public high school. They decided on an all boys boarding school on the other side of the state. The school was well-known for its academics, and was similar to a military academy. They sat me down one night after dinner and explained the move, and that it was what was best for me. I was even less interested in the fact that it was an all-boy’s school, much less leaving all my friends at home behind. This was during winter break, and they told me I would be starting there for the upcoming semester. I began packing during the next week and said goodbye to all my high school friends. The holidays passed and I had everything packed and ready to go. My parents drove me up to the school and dropped me off after dinner. They helped me get my bags inside and then we said our goodbyes. I laid around my room for a bit trying to unpack and organize some of my things, but had to report to the first floor at 5 pm. A guy named Brad, who I guess volunteered for this sort of role, showed me around campus that evening. Once it was dark, Brad told me we should probably head back to the dorms for the night. One thing I was grateful for was that everyone had a room to themselves. I felt like I had more privacy than I did at home. Once we got back, Brad handed me my school uniforms, along with some sets of gym shorts and t-shirts with the school logo. I even got socks with school colors, tighty whities, and a jockstrap which I was told was for gym class. He said I should be in uniform at all times with no outside clothing on. Brad told me that I should report to the infirmary at 8:00 a.m. the next morning for my “entrance physical”. What the hell? I thought. Why did I need an entrance physical?

Chapter 2

The next morning I woke up and headed straight to the infirmary. I walked in, and there was a young blonde woman working the front desk. She asked what brought me in and I told her I was a new student and I was told I needed an entrance physical. She said okay and handed me a packet of paperwork to fill out. I sat down to fill out this huge packet of paperwork concerning my medical history. It didn’t take too long, as I didn’t have any problems that I had to jot down. I got up and handed her the packet and she said someone would be out to get me soon. I twiddled my thumbs for maybe five minutes when a middle-aged African-American woman opened a door and called my name. She introduced herself as Jeanette and told me she was my nurse today. We walked down a short hall where she recorded my height and my weight. On the short walk down, I couldn’t help but admire her thick thighs and how her fat rear jiggled as she walked. Jeanette showed me to an exam room and told me to have a seat up on the table. The room was eerily bare, with light tan walls and a few mirrors on the walls but no other decorations. Jeanette got my blood pressure while I was seated on the table. “Alright, if you’ll go ahead and take off everything but your socks and your underwear. I’m going to leave the room but I’ll be right back in.” Jeanette said. She left the room and I took off my shirt and my jeans and left them folded in a chair next to the table and sat back up on the table. I heard a knock on the door and Jeanette came back in. The first thing she did was walk over to the sink to get something out of the drawer. “Okay, the next thing we need to do is take your temperature. Go ahead and slide your undies down to your knees and lay down on your stomach for me hon” she said. “I can hold an oral thermometer” I said in the kindest tone possible. “I’m sorry honey, Dr. Williams has a strict rectal temperature policy.” I blushed red in my face and stood up. I climbed up onto the table on my knees, took a breath, and slowly eased my briefs down to my knees, my bulge spilling out in front of me hidden from Jeanette’s view. Then I laid face down on the table with my face in the pillow. Jeanette walked over beside me and snapped on some latex gloves. Next I felt her spread one of my cheeks, and without warning she slid the greasy little rod up my backside. She kept her hand on my rear to hold it in and said it would take around five minutes to register. I laid there, red-faced and bare-assed, just watching the clock tick by. Once the five minutes was up, she took it out and told me I could sit back up on the table. I pulled up my briefs and sat back down, and I could still feel the Vaseline between my cheeks. Next she pulled out a clipboard and began to ask me some questions about my sexual history, and other more personal questions that weren’t on the paperwork. After she was finished with her questions, she told me that the doctor would be in shortly. I sat in anticipation as I waited for the doctor. Around 5 minutes later, there was a knock at the door. Jeanette returned with Dr. Williams and she introduced herself. She looked even younger than Jeanette, and she was also African-American, yet had a slimmer figure than Jeanette. She didn’t waste any time with small talk and began by examining my eyes, ears, nose and my throat. Then she donned some gloves and asked me to lay flat on the table. Jeanette pulled part of the table out and I laid back and stared at the ceiling. Dr. Williams began feeling my joints, making sure they could move in every proper direction just fine. Then she began palpating my stomach and feeling my organs. Dr. Williams then slid the leg rest back in the table and told me I could sit up. She sat down on a stool and told me to stand up. I stood up and she rolled over and yanked my briefs down. I blushed as her and Jeanette were now staring at my genitals. They might have thought I shaved for this, but I was a late bloomer and my butt and my genitals were still hairless. Dr. Williams asked me to bend over and touch my toes. I felt her run her fingers up and down my spine. Next she told me I could stand back up. She began to inspect my penis from all angles, holding it up, down, and to each side. All the attention began to arouse me. Next she cupped my balls while holding my penis up and rolled them around in her fingers. My cock grew in her hand, and I now had a full blown erection. “Don’t worry, that’s a perfectly normal reaction” she chuckled. “That’ll make this next part easier. Lose the undies and lay back on the table for me.” she said. I stepped out of my briefs and laid back on the table with my legs hanging off. “Just gonna have to swab your penis. Just close your eyes and relax” the Dr said. I felt the latex hand grip my dick that was pointed straight up. “Deep breath” she said. I then felt her slowly slide the swab down my penis, which both burned slightly and tickled. She quickly pulled it out and placed it in a collection tube. “Now I need to check your prostate. Roll over on your left side and pull your knees up to your chest.” I rolled over, my stiff cock facing Jeanette in the corner of the room, and I tried to avoid eye contact. “Deep breath for me” Dr. Williams said, lifting my ass cheek up exposing my hole. Next I felt her apply more vaseline to my hole, and she quickly slid her slim finger up my rear. I squirmed slightly as her finger occupied my back passage up to her knuckles. I squirmed slightly. “I can certainly tell you haven’t gone to the bathroom in a day or two.” Dr. Williams said as she pulled her fingers out of my rear. “Jeanette here is going to clean you out and then we’ll proceed with your exam”. Dr Williams left the room. Jeanette grabbed a red bag from under the sink and began to fill it with water. “I’m just gonna give you an enema” she said. “Have you ever had one before?” I said yes, as I was all too familiar with taking a hot soapy bag up my rear. Jeanette walked over and hung the bag up beside the table. Next she attached the hose with an amber colored nozzle that looked quite wide. “I’m going to use a double balloon nozzle to help you hold it in so maybe you only have to take one bag” Jeanette said. “It’s gonna be easiest to insert if you get up on your knees and elbows for me” Oh my, I thought. What a humiliating display. I rolled over on my knees and reluctantly rested my elbows on the table with my ass up high. I looked in the mirror and saw Jeanette brandishing the nozzle up above my butt and greasing it with vaseline. I could feel the cool air in the room all the way from my crack down to my cock and balls that were hanging on full display. “Now I need you to relax and bear down like you’re trying to go to the bathroom, this may be a little uncomfortable.” she said. I pushed back against the fat nozzle as I felt the tip, and I watched as Jeanette tried to stuff the thing inside my tight pucker. I let out a soft grunt as my hole began to stretch. “Push for me honey”. I pushed against the widening nozzle and felt the ridges slip inside me. Jeanette said she was going to inflate the bulbs and to tell me when it was too big. I heard the whoosh of the air as she squeezed. After a few pumps I felt the nozzle push against my prostate and grunted “Oooh. Right there”. She stopped and said she was going to start the flow. There was a soft “click” and I then felt the water rush up my rectum. “Stick your booty a little bit higher for me honey, it’ll help get the water deeper” Jeanette said. I pushed my elbows lower towards my knees and arched my ass up high. I began to pant deeply like a dog as the water filled my bowels. Jeanette placed her hand on my lower back and told me I had taken around a third of the bag. I continued to pant as the water surged up between my ass cheeks. I jumped when I felt her move her latex gloved hand and caress the back of my balls. My cock was already at full attention, and she squeezed it and began to slowly jerk me. “I see enemas make you excited too” she said with a smirk. I blushed and she quit stroking me, but I was still embarrassed. I kept my head down and my eyes peering back between my legs, my rigid penis staring me in the face. My legs and my buttocks were shaking slightly as I was trying to finish the bag. Cramps hit me and I groaned as Jeanette walked over to check the bag. “We’re almost done. Just relax and keep your heinie up high for me, I know you can take it” she said reassuringly. I was relieved when I heard the bag gurgle and I heard another click as Jeanette stopped the flow. “I need you to hold it for at least ten minutes now, okay?” she said. I could only nod as I didn’t want her to see the grimace on my face. I occasionally glanced up at the clock to watch the seconds slowly tick past. Every now and then a cramp would hit me and I would let out a grunt. Jeanette said I could lay flat on my back to help hold it in. I rolled over and laid flat on my back with my swollen belly and my erection in plain sight. Jeanette walked over and began to push and rub on my stomach with both hands. “Does that feel better?” she said as she turned and looked at me. I nodded yes and closed my eyes and leaned my head back. Jeanette began to move lower on my belly with her rubs, and would occasionally brush against my throbbing cock that was pointed straight at the ceiling. I laid there with my eyes closed and let her do her thing. Soon she said I could go, but said she would accompany me to the bathroom to remove the nozzle. Jeanette disconnected the nozzle from the tubing. She told me it was the second door on the right down the hall so I hopped up and began to walk. I opened the door and began to walk when I jumped as I locked eyes with the receptionist. I blushed and quickly moved my hands to attempt to cover my stiff cock. I quickly ducked into the bathroom and Jeanette told me to stand over the toilet and spread my cheeks. I spread my cheeks wide and she deflated the nozzle and pulled it out of me. Next she left me to do my business and told me she would be waiting back in the exam room. Once I wiped myself clean after evacuating the fluid, I washed my hands and opened the door to look around the office. The receptionist eyed me again, but I could only cover my now soft cock as I quickly scurried back to the exam room. I opened the door to the exam room and Jeanette was there waiting. She told me to follow her to another room for the next part of the exam. I asked if I could put my clothes back on and she said I wouldn’t need them. I let Jeanette lead the way, admiring her round ass cheeks swaying as she walked. She led me to a room marked “Proctology”. I saw an exam table that seemed to be tilted, and next to it was a tray with a chrome tube and a jar of vaseline. Dr. Williams entered soon after us, and I stood there in just my socks with my hands covering my junk as I waited for instructions. Dr. Williams said she was going to use a rigid sigmoidoscope to “have a look” up my rectum. “Will it hurt?” I asked nervously. “It may be very uncomfortable…” she said. Those words sure didn’t calm me. Dr. Williams told me to climb up on the table and rest my head on my hands. I put my knees up on the ledge and leaned over the table. I felt her secure the back of my legs and my back to the table with two large straps. She reassured me that it was just for my own safety. Next I heard a loud whirr as my rear was elevated even more so that it was around chest level for the two ladies. I watched them both snap on latex gloves. Dr. Williams then dipped two fingers in the jar to get a large dollop of vaseline. She placed one hand on my lower back and I gazed in the mirrors and watched her slip two fingers in my rectum. I could feel her twist, poke, and prod in every direction. Next she pulled her fingers out and I watched as Jeanette began to apply vaseline up and down the sigmoidoscope. I watched Jeanette hold my cheeks wide open. “Just bear down for me” Dr. Williams said as I felt the cold greasy tip against my anus. She began to push, with no luck, and I felt that the tip was too wide for my virgin hole. “I think it’s too big” I said softly as I gazed in the mirror and saw the heads between my wide open crack. “Okay, now BIG push for me honey” Jeanette said. I pushed hard and some air escaped but I soon felt the tip slide inside me. It was seriously stretching my pucker and I couldn’t help but moan when it slipped in. “Just keep pushing for me hon” she said and I gritted my teeth as the intruder continued to slide into me and fill my rear. The steel tube marched on, and I couldn’t get over the feeling of my rectum being stretched that far and my ass clamping tight on it. It felt like it was straightening out my entire back, and soon I began to pant and grunt “Take it out…oh please…it’s too big” I whimpered. Jeanette rested her hand on my lower back “Just loosen up for me hon, you can take it like a big boy, it’s almost halfway in” she said. Halfway!? There was no way in hell I could take the entire tube up my ass. I glanced in the mirror and blushed when I locked eyes with Jeanette. I saw my pale white moon with the tube sticking out, and the reflection of my sack drawn up tight because I was still aroused. “I’m going to inflate you with some air so I can see” the Dr. said. I felt a rush of cold air up my butt which filled me even more. I continued to watch in the mirror as Dr. Williams’ head disappeared between my cheeks with her eye pressed up on the scope. After peering around some, she continued the journey onward. I knew she was pushing again because Jeanette grabbed my cheeks again and held them apart. I clenched my teeth and tried to hold on my cries as my eyes began to water from the pain. “Final part, we’re going to look inside the edge of your colon. I won’t lie, this is the worst part, so just relax as best you can for me” the Dr. Said. Worst part? I thought. I was already almost crying from the pain! “Deep breath now honey” Jeanette said. I took a deep breath and saw Dr. Williams resume the push up my rectum. I instantly felt a wave of pain radiate from up inside my butt outwards. It felt like my spine was being corrected, but I now know that this sensation was the scope entering my sigmoid colon and going around the bend. The pain caused me to slightly shake my ass when I jumped, as I couldn’t move it too far because of the straps but the pain certainly made me flinch. Jeanette gripped my butt cheeks tighter and squeezed them “Hold your heinie still so you don’t get hurt”. The scope entered my sigmoid colon, and I let out a “Fughhhhh…” through my clenched teeth. My ass cheeks may have involuntarily clenched as well, as the heightened pain caused me to push my hips into the table, my stiff cock trapped beneath me against my stomach, aching to be rubbed. My tears began to fall down my face through my grunts. I finally closed my eyes as I was utterly humiliated by the view of Jeanette and Dr. Williams’ heads between my cheeks with my balls and my cock hanging out. Soon I felt Dr. Williams' latex-gloved hands on the back of my sack, and she announced that the scope was all the way inside me. I breathed a slight sigh of relief. She began to pump me up with more air while pulling the scope out and looking around, the feeling of the exit was much more graceful than the entrance. Once the scope was pulled out of my rectum, Jeanette released the straps holding me in and told me I could return to the exam room to finish up whenever I was ready. I waited until she left the room and climbed off the table. My hole was still sore and I winced at almost every movement of my legs. I stood there and looked in the mirror and eyed my stiff prick. I grabbed it and squeezed, leaning back and beginning to stroke myself. I had to force myself to stop because I was afraid of getting caught. I half walked, half limped back to the exam room. Jeanette was standing by the sink and the surrounding cabinets looking through them. Upon opening the door, this startled me, and I quickly moved both hands to my crotch to cover my still-hard cock. “There you are, I was beginning to think something was wrong!” She said with a slight chuckle. “Can I put my clothes back on now?” I asked. “Not quite, we’re almost done, sit up on the table for me” she said. I sat up on the table still clad in just my socks, and my hands still covering my junk. Jeanette snapped on a pair of gloves and walked towards me. “This part of the exam is much more fun than the last one. I’m going to have to get a semen sample from you”. My cheeks turned red as I pictured myself furiously whacking it while Jeanette stood and watched. “I’m going to massage your prostate, it’s the best way to get a good sample.” Great, more toying with my hole! I thought. “I want you to lay all the way back for me, no need to cover up, I’ve seen it all” she giggled. I laid all the way back as I watched Jeanette bring up some stirrups like the ones that are used in women's clinics. She guided my feet into them and strapped me in. “Don’t worry, this is just a precaution since I’ll be between your legs” she said. Next, she adjusted them so my legs were spread wide open, with my knees bent and pushed back towards my head. “Now just scoot forward some'' she said. I eased forward until the edge of my butt was hanging off the table, which is what she wanted. My crack still had Vaseline all up and down it, but Jeanette still rubbed some in her hands till her gloves were glistening. She sat on a stool and rolled over to me. “Just lay back, close your eyes and relax for me” Jeanette said. I felt her fingers circle my anus so I pushed. My stretched ring was much more welcoming to her warm fingers than the cold sigmoidoscope. I felt her slide her two slim digits up towards my belly button, and she curved them towards the top of my room and began to rub and prod with a “come here” motion. “You may feel like you have to pee, but that’s normal, and I promise you won’t” she said. My cock began to twitch with every curl of her fingers. I wasn’t far from my climax. “Try and hold back as long as you can so I get a good sample hon” she said. I opened one of my eyes for a brief second, and she stared right into mine and grinned. She cupped my balls in the fingers of her other slick hand and began to bounce, roll, and rub them with her fingers. Then she moved that hand and squeezed my cock in the bottom of her hand as she slowly slid her hand down. “Uhhh” I moaned. Jeanette began to stroke my cock while fingering my ass, and the sensation was extraordinary. I knew I was close so I murmured that I was about to blow. “Hold back for me just a second honey” she said, never slowing down. I clenched my cheeks on her finger to try and delay the inevitable, but it was no use. My hips bucked up in the air, and Jeanette must’ve taken this sign as she quickly grabbed a tube and held it on my cock. I shot load after load into the tube pointed back up to my face, through my moans and grunts, filling up the tube till it began to overflow onto my groin. “Good job” she said, carefully removing the tube and capping it while semen leaked down my dick. I laid there in a daze, and I couldn’t bear the thought of having to look Jeanette in the eyes. I watched her rear again as she turned around to set the tube on the counter and she turned to undo the straps. Jeanette told me I could get dressed and that Dr. Williams would be back and left me some Kleenexes to wipe myself. I stood up once she left, wiping my crack and my cock and balls before slipping on my briefs and donning the rest of my clothes. I sat on the table and waited for the Dr to return. Dr. Williams soon knocked on the door, followed by Jeanette carrying an orange tray. She sat the tray down next to the table and I saw two large needles, one with a yellow-amber fluid and one holding a large thick fluid that looked like glue. “This is the last portion of your exam.” she said. “We’re gonna give you a shot to keep the soreness down in your rear, and a shot of antibiotics so you don’t get any of our boys sick” I said okay, and rolled up my sleeve. Jeanette picked up the yellow syringe and said “I’m afraid these have to go in your heinie” Dr. Williams wished me good luck at the new school and left. Meanwhile, I was thinking about taking these shots in my butt! Jeanette told me to slide my pants down to my knees and lay on my stomach. I slid my pants down right at my knees and flipped over, my tight plump heinie covered by the backseat of my tighty whities. Jeanette told me to lift up and she slid my briefs down to my knees, and I could already feel my cock begin to stir again as I pressed it against the crinkly paper on the exam table. “You have such a nice smooth bottom” she said as she rubbed it and squeezed one of my cheeks. I blushed, unable to offer a response. She wiped my cheek down with alcohol and held the needle up high. Next she pulled the skin tight, and without warning, drove the needle home in my fat ass cheek. I flinched, and couldn’t help but let out a “ouch!” as she deposited the fluid. “This one might sting a bit” she said before puncturing my pale skin with the needle. I flinched when I felt the pinch on my backside, and I then felt the thick gunk being pushed into my gluteus maximus. “Ohhhh fuuuuuuu” I groaned as i felt the fluid being slowly leaving the needle. The pain set my ass on fire! I finally felt the needle being removed from my buttock, and Jeanette placed a small band aid on each of my cheeks. “You sure took those like a trooper!” she said. I laid there and waited for her to leave, but it became apparent that she wasn’t until I moved. I propped myself up off the table on my elbows, my cock still as rigid as before my prostate massage. “It looks like you’re still a little excited” she giggled as I pulled my briefs back up while up on my knees. I was embarrassed at all she got to see that today, and quickly bolted out of the infirmary back to my dorm.

Chapter 3

The next day at school, I went to take a shower. I had gotten up quite early on a Saturday so I was by myself. The showers were open, prison style showers, and I was afraid of being naked in front of the other boys, especially the older ones. I checked around to make sure no one was in the bathroom and set my stuff inside a locker. Next I stripped out of my t-shirt, dropped my shorts, and finally, my briefs. The bathrooms were freezing cold, so I quickly grabbed my bag and headed to the first open shower. I cut the water on pretty hot so I could warm up. The trade off for the cold air in the bathrooms was unlimited hot water. After I soaped up my body, I began to scrub myself clean. While scrubbing my sore cheeks I couldn’t help but reminisce on my exam yesterday and my cock began to enlarge. I soaped up my hands and hung my washcloth back up. I closed my eyes and began to slowly stroke my cock. It felt great as the steaming hot water poured over me. I took my other hand and began to handle my balls, speeding up my strokes with my hand. I thought about having the sigmoidoscope deep in my ass and that was it. I clenched my cheeks and grunted as my semen spilled out onto the shower floor. I almost fainted in my pleasure, and just as it was ending I heard someone say “Bravo, what a show” I turned around and blushed as I saw someone that was already naked join me in showering right beside me. I stammered, and I had no clue what to say. “I was…” I tried to think of a lie. “Don’t worry man, I’m just yanking your chain. Everyone has done their fair share here. Some guys will do it no matter how many are in here, and some help each other out.” he said. I turned and looked at him and he introduced himself as Jack. He was a year older than I was, and we made small talk while I tried to forget what I just let him watch. I found out he actually lived next door to me in the dorms. He told me that he was free and that we should hang out later, and since I had no friends and I was afraid of him spilling my secret, I agreed. Not long after, I finished up washing and quickly made my way out, still embarrassed.

Chapter 4

The next day I didn’t do much, as there was nothing to do until classes started back on Monday. I hung around my room for a while, and during the afternoon I walked around campus to find where my classes were. I showered that evening, alone and headed back to my room. I was getting ready for bed when Jack knocked on my door. He asked if I wanted to come over, and I said sure and followed him to his room. I noticed he kept his room pretty clean, and he sat down on his bed and motioned for me to sit beside him. He said he had something cool to show me, and Jack pulled out some old playboy magazines and started flipping through them. I had never seen one before, and I thought it was cool. Jack asked me if I had ever jerked off. I wasn’t familiar with the term so I actually said no. “You mean to tell me you’ve never rubbed yourself down there?” He asked. I said I obviously had since he had seen me do it in the shower, but that I just had never heard the term. Jack continued to poke and prod asking questions about my entrance exam, as well as things like enemas and rectal temperatures. I was blushing as we discussed the subject and he asked if I thought that having stuff up my butt felt good. I was red in the face but answered honestly and said yes, hoping it wasn’t a trick question to try and poke fun at me. He said he thought it felt good too and was happy to know someone else felt the same way. I laughed and we made more small talk and flipped through the magazine. The pictures, along with my daydreams about my exam, had my cock throbbing. Jack said he was ready to go to bed but that we should hang out more. I was honored to be considered cool by an upperclassman and I agreed. I left his room and went back to mine, with my cock still throbbing from all the images in the magazine. I went back to my room, and quickly stripped down and laid in my bed. With the images still in my mind, I furiously whacked my cock dry until I exploded, using an old rag to clean up.

Chapter 5

The next time I hung out with Jack in his room, I asked if we could look at the playboy magazine. “You horny little bastard!” He chuckled, but said sure. Jack handed me the magazine and I looked through it again. I looked at Jack over beside me and noticed he was zeroed in on my bulge. I moved the magazine lower to hide it. “You’ve got a stiffy, don’t you?” He teased. I blushed and stammered trying to find a reply. “It’s okay man, that’s normal.” He said. Jack asked if I wanted to play “doctor”. I asked what he meant and he said play like kids do. I mulled the thought and he said if I didn’t want to or if I asked him to stop it would be okay. I said okay and put the magazine down. Jack then told me to stand up and drop my shorts. I was really shy but I didn’t want him to think that, so I stood up and pulled my pants down. My erection was bulging at the front. Jack rolled over in his chair and said he was going to take a look. He gently rubbed my penis through my tighty whities with his hands. My cock was twitching with anticipation. He told me to turn around and face away from him. I did so, showing my tight white ass to him. He grasped my cheeks and I clenched, and he told me to relax. I relaxed my backside, and he continued to rub my butt cheeks. Then he stuck one hand between my legs and started to gently rub my balls. My cock was growing stiffer by the minute. Jack told me to turn around again. “Well now we need to take a closer look” he said. Jack hooked his hands in my waistband and pulled my briefs down to my knees. I blushed beet red as my cock sprang out, staring him in the face. “That’s a normal reaction, don’t be shy” he said. Jack began to inspect my erection as a real doctor would, only much more hands on. I thought I had a decent size cock, but I was always embarrassed because I was behind on puberty with no pubic hair. He lifted my cock up and grasped my balls with one hand. I gasped, as my balls are very sensitive, but he reminded me to relax and only gently rolled them around in his fingers. Pre cum began to rise in my dick. “Turn around so I can look at your bottom now” he said. The word “bottom” made me feel like a little boy. I turned to let him face my bare ass cheeks, which had no hair. My butt was as smooth as a baby’s. He grasped my cheeks again and felt them up and down. “Very smooth” he said in a sly tone. I reminisced about the nurse’s remarks about my butt. Next he spread my ass cheeks, and I could feel the cold air rush onto the skin around my perineum. He rubbed my hole with his finger which gave me goosebumps. Then he stood up and faced me. “Well it’s only fair I show you mine” he said. Jack stood up and swiftly dropped his pants and briefs and stood there nude. I marveled at the size of his cock. It had to be at least 8 inches! Mine was 5 or 6, and it put mine to shame! I didn’t take a look at it in the showers, as I didn’t want him to think I was weird. I reached over and grabbed his pulsing cock with my hand. I maneuvered it up and cupped his large, tight sack as he did with mine. I wasn’t as thorough or teasing as he was, but I definitely enjoyed taking a look. I told him to turn around and he did. His butt was slightly hairy, and there was obviously more muscle underneath the fat when comparing it to mine. I spread his butt cheeks to peek at his little rosebud. “Do you know what your prostate is?” He asked. I said no, and he explained it was a little organ up your butt that made you feel good when you rubbed against it and that it was probably why I liked stuff up my butt. I understood now and told him that the nurse had rubbed it during my exam. “Do you wanna do it again? Sometimes I rub it when I’m jerking off” he asked. I said sure, but asked how. He opened a drawer and showed me a tube of KY lubricant. Jack said he would have to put his finger up my butt. I was unsure, but Jack reassured me that I would enjoy it. Jack told me to lie back on the bed. I laid down, my cock pointing straight up at the ceiling. He told me to bend my knees and spread them and to slide my butt to the edge of the bed. Next he squirted some lube onto his finger. Jack told me to relax, and circled my rosebud with his slick finger. “Deep breath now” I took a deep breath in and instantly felt his finger slip into my rectum. I gasped and my hole must have clenched because he told me to relax again. He pushed his finger deeper and soon turned his hand and began to push his finger against my button. Some thick fluid leaked out of my cock and I moaned. His finger was much thicker than the nurse’s and filled my butt way more. Jack began to rub my prostate more aggressively and my cock was aching to blow. “I think I’m…” I moaned. Jack took his other hand and cupped my balls and gave them a light squeeze. “Oh!” I moaned like a girl as I arched my hips up as my entire body contracted. My load came out like a volcano, erupting down all over my groin. I was still moaning as the torrid wave of the orgasm washed over me. I shot rope after rope up in the air and they landed all the way up from my stomach to my chest. As I collected myself I tried to process what happened. Was I gay? I wasn’t a virgin and enjoyed being with girls, but this was just as fun. At an all-boys school, this was all I had.

Chapter 6

The weekends at the dorms were very quiet. Most kids went home, but I seldom did. Jack never did. He walked in the bathroom on Friday night while I was showering and stripped to join. He stood beside me and asked what I had planned for the weekend. I told him nothing, and he smirked and said we should “fool around” sometime, and gave my soapy butt a slap. I was shocked he did that in the public bathroom, but I hadn’t seen any other boys. I said maybe, and he stood behind me and began to rub my back. “Surely that fat little butt of yours needs a release” he whispered softly in my ear, caressing my soft pearly white buttocks. I blushed beet red and stepped forward to quickly finish washing off. I dried off and quickly donned my clothes and left. I got in bed early and got very horny. I was only in my t-shirt and briefs and I slid them down and began to stroke my cock. I was halfway through when I heard a knock on my door. I quickly fumbled my cock inside my briefs and shot up. I peered through the eyehole and saw Jack. I cracked the door and he asked what I was doing. I stammered, trying to find an excuse to hit the hay. Jack gave me a confused look and pushed his way in my room. Jack quickly looked down at my briefs. He lifted up my shirt and saw my bulge. “You were spanking it, weren’t you?” He giggled. My cheeks filled with crimson “No I was…” I was at a loss for words. Jack giggled and forced his way in and sat on my bed. “Have you ever had your bottom spanked?” He asked. I lied and said no. The truth was my mom still wore out my ass if I deserved it. “I think you deserve a spanking” he said as he stood up. I told him there was no way I was gonna let him spank my ass. Jack stepped towards me and hooked his fingers in the back of my briefs as I turned to walk away. “I wasn’t asking nicely” he retorted. Fighting was no use. Jack was older and much stronger and muscular than me. I tried to run but he pulled hard on the back of my briefs and yanked, causing them to slide down to my knees. Then he grabbed my arm and pulled me back towards the bed. He laid me over his knees, my butt square in the center and my genitals pressed against his knees. Jack hung one leg over the back of my knees so that I couldn’t get up or flail. I felt his gaze on my exposed rump. He softly ran his hand from the back of my thighs to the small of my back, stopping at the underside of my cheeks to jiggle them. “What a fat little ass” he said. Next he removed his hand and I felt the first sharp slap on my cheek. “Oh!” I said. Slap! Slap! Slap! Jack was showing no mercy on my butt cheeks. Slap! Slap! Slap! My cheeks were beginning to feel hot and red. Another slap came right on the center of my cheeks. “Ow!” I said. “We’re just getting started” Jack said. Jack's hands got heavier, and he started working his strokes lower down to the underside of my pearly glutes. Next I felt a slap right on the folds of my ass where I would sit. “Yeowww!” I yelled, arching my back and grimacing. “Stay still or I’ll make this punishment much worse!” Jack smarted. He continued to wail on the seat of my ass, and tears began to fill my eyes. I wanted it to stop. Jack then stopped and began to rub my cheeks again, and I thought he was done. I pushed myself up and tried to get up. “Not so fast” he said. I felt him rub the welts on my ass. “We’re alllllmost done.'' Jack raised his hand and delivered the hardest blow yet on the fattest portion of my butt. “Ouuuch!” I cried and kicked, but it was no use. Smack! Smack! Tears began to slowly roll down my face as my ass was on fire. “Good boy.” He said and patted his damage. “I’ll reward you for taking it like a big boy.” I heard a squirt of lubricant and he spread my cheeks with one hand. I felt his finger circle his target, and he soon slipped his finger in my butt. He was more aggressive than before, going all the way in and began to furiously prod my prostate. I grinded my hips into his knees, aching for my cock to be rubbed. Jack continued to massage me and I grunted as I felt my glutes clench. My hole spasmed around his finger and I shot my load onto his leg. “Uhhh…uhhhhhh!” I groaned and writhed in pleasure. Jack slid my briefs off my legs and wiped my semen off of him. He tossed my last pair of clean underwear in the laundry hamper. “That’ll make you think twice about rubbing one out without me.” He left the room, and I tucked myself in. My cheeks still burned, but I’d be lying if I said the experience didn’t thrill me.

Chapter 7

The next morning I went straight to the shower. All I wore was gym shorts, as I still had to do my dirty laundry. As usual, I was the only one in there until Jack came in. I gulped as I saw him in the mirror behind me. He stripped, revealing his massive cock. Jack took his favorite spot in the shower beside me. “How’s that cake feeling today?” he asked, gently rubbing my ass with his hand. “Sore” I said. I had eyed my ass in the mirror before I showered and could still see all the red marks. I would be humiliated if anyone else walked in the shower. “Better keep that heinie clean for me too” he said with a stern tone, and he spread my ass cheek slightly to let water run down my crack. “And maybe come over later and I’ll rub those cute ole cheeks of yours” he said. I said okay and finished showering and left. I had nothing else to do that weekend, and nothing to study for. So I decided to pay Jack a visit. I knocked and he quickly opened his door. “So you’re taking me up on the offer, huh?”. I said yes. “Drop those shorts and lay face down on the bed for me.” Jack said. I stepped out of my shorts and laid on his bed. Jack sat on the bed with a bottle of lotion and worked some onto his hands. “Wow, I did really give you a spanking huh” he said as he began to massage my rear. The lotion was cold and slightly stung on my bottom, but it did feel great to have Jack work on my tense glutes. “Do you want a surprise?” he asked. Jack had worked up my boner, so I said sure. He said I’d have to wear a blindfold, and handed me one. Jack also said he wanted to restrain me, but promised I would enjoy this. I donned the blindfold and Jack told me to lay spread eagle on my back. My boner was of course pointed straight up, and Jack tied my arms and legs to the corner posts of his twin bed. I felt something extremely wet begin to rub the head of my cock. Was he giving me a blowjob? I realized it could only be his tongue, and I felt Jack firmly grasp my shaft while he began to swirl his tongue around my engorged head. “Oh my…” said. I knew I wouldn’t last long at all. Jack began to stroke and twist my shaft while working his tongue. Next he removed his hand and I felt my stiff prick enter his hot mouth. “OH!” I yelled. Jack closed his lips on my organ and began to sloppily slurp my manhood from the head to the shaft. “I think I’m…” I was interrupted by Jack taking my entire cock in his mouth. My hips went up, forcing my cock into the back of his throat and I heard him gag. I shot what felt like a gallon of spunk into the back of his throat, all the while I was moaning and squirming in my restraints it sounded like he was choking trying to take it all. I finally finished riding out my orgasm, and my cock began to shrivel as Jack let it out of his mouth. He untied my restraints and I took my blindfold off and thanked him. He thanked me for being a good sport, and said I took my spanking like a champ.

Chapter 8

It seemed like just being around Jack tended to arouse me. One night we were hanging out as we did after dinner, playing cards in his room. I noticed him looking past my hand of cards at my bulge. Jack stood up and grabbed my stiff prick through my shorts and looked me in the eyes. “Naughty boy” he said. “You need to be punished. Stand up” I stood up and next Jack yanked my shorts and briefs down to my feet in one quick motion. My rock hard erection flopped out and my bare ass was facing him. He forced me over his knees with one hand on my back, my cock trapped between his knees and one of his legs pinning mine down. “You’ve been a naughty boy he said.” I turned my head and saw him grab a wooden paddle. I gulped as there was no turning back. He raised it high with one arm, and I looked away before it began its descent. Whack! The wide wood piece smacked my bare ass. Whack! Whack! Whack! The paddle was large and heavy, but had holes in it so that it still traveled fast. My cheeks were beginning to sting. Whack! Whack! WHACK! The seventh strike made me jump, arching my back and ass up and therefore accidentally grinding my cock between Jacks thighs. He had undoubtedly made this strike harder and I couldn’t help but let out a sharp cry. Jack continued to spank my bare bottom until it was red hot. Next I felt something cool and wet at my anus. With one hand groping and massaging my ass cheeks, Jack slipped his finger up my butt without warning. I moaned and bucked my hips into him, my penis still trapped between his legs. He continued to poke inside me, eventually finding my prostate and rubbing it. “Oohhhhhh. Ohhhh shit” I said. Jack gave my ass one more smack and then told me to stand up. Next Jack stood up and I watched as he pulled his shorts and briefs down to reveal his massive prick. “On your knees. Now.” He said. I dropped to my knees and was now eye level with his massive tool. I had a feeling as to where this was going. “Now suck my cock.” He ordered. I had never given oral sex to a male and my reception from females was limited, but that was about to change. All I knew to do was to emulate what girls do. I moved my head towards his dick and began to lick and tease the purple head. I didn’t want to scrape his massive member with my teeth. I spit on it and began to work my spit onto the shaft. Next I looked up into his eyes and took one hand to cup his sack while I opened wide to accept his massive head into my mouth. I closed my lips around the mushroom shaped head and began to suck. Jack moaned with pleasure. With one hand working the shaft, one tickling his balls and teasing his anus, I began to really go to work and try to make him cum. I was sucking and slobbering aggressively. I slowly took him deeper when I felt Jack's hand on the back of my head and he gave me a firm push. (I was alarmed of course, but we had set boundaries and a safe word in advance) I looked up into his eyes as I gagged and mine swelled with tears as I throated his cock. I wanted to back up but Jack kept his hand on my head and was fucking my face. Jack finally let go and pulled his cock out of my mouth. “Stand up and bend over” Jack said. I stood up and leaned over his bed. I noticed Jack putting a condom on his swollen cock. “Now you’re gonna take my cock like a big boy” he said. He gave my ass a quick smack and began to rub his greasy dick up and down my crack, teasing me. “Spread your ass cheeks” he said. I laid my upper half on the bed and reached back and spread both of my tight white cheeks and waited. I felt the wet tip against my hole. I clenched my cheeks, but Jack pushed harder, and I flinched into the bed, but I was out of room. My knees buckled as his massive head speared my virgin rear, splitting me wide open. The stretch burned and hurt like hell, but that was what turned me on. “Owowowow” I softly moaned. Jack slowly pushed his cock deeper and began to stroke inside me. He was going just deep enough to hit my prostate. I grunted with every stroke as he fucked my tight ass with his hot rocket. “Errgggh…Ughh”. Each stroke teased me more as the tip of his cock grinded against my man button. His cock was easily the biggest thing I had taken up my rear to this point, and although it hurt like hell, the burn and the sense of submission was what made me so horny. After he was done pounding my prostate, he ordered me face down on the bed. I pointed my cock up towards my stomach and he put a pillow down for my hips. Jack climbed on top of me, his knees outside mine so my legs were pressed tight. “Now you’re going to take all of my cock” he said and began to slide his dick between my tight ass cheeks. “Wait no I don’t think I can…” Jack pushed on my back into the bed as I tried to rise. Jack re-entered my tight hole. I could feel that he had taken off the condom. He began to push slowly, and I could feel that he had passed my prostate. “Here it comes” he said. Jack lowered his hips further, beginning to lay flat on top of me. I felt him probe deeper than ever before. “Owowowowow” I softly whispered. “Just push back and take it like a big boy.” He said. I tried again to lift up, but he had both hands pinning me down. Jack grunted and I felt his head begin to straighten out my rectum. “OHW!” I yelped as I felt his hips all the way up against mine, and his balls tucked tight between my cheeks and I knew he was all the way in. Tears began to fill my eyes from the pain of his hot cock that deep inside my ass burned like hell. I could feel every ridge and vein stretching my rectum. Jack quickly began to thrust, pulling his cock all the way out till the head was barely in, then ramming it all the way back up my rear. “Oh!..Oh!..Oh!” I moaned in unison with his strokes, along with his sack slapping against my ass cheeks and his hips forcefully meeting mine. Jack grunted and began to thrust even quicker. He let out one last grunt with his cock buried all the way in. “OHHHH!” I yelped as I felt my asshole begin to squeeze his rigid cock and I clenched my cheeks on his dick. This must have squeezed the cum out of Jack, as I felt his hot load shoot deep up inside me as his erection swelled. I could only lay there, limp, as Jack had just used me as his toy and fucked the cum out of my butt. I still tried to hide my excitement during our playtime, but every second of it thrilled me. I loved the feeling of him dominating my ass.

Chapter 9

The next week, I saw Jack at dinner and he asked me if I wanted to hang out later. I said sure and he told me to come to his room around 9. I knocked on the door and he answered, and I saw the playboy magazine laid out on his bed. I knew he was horny, and I was too. Jack came up to me as if he was going to hug me, but his hands went right around and squeezed my cheeks. “I want you to ride my cock” he whispered in my ear. I smirked and reached my hand in his pants to grab his swollen cock. Jack took the back of my briefs in his fingers and yanked them down, my shorts coming with them. I teased his cock, sliding my hand up and down the shaft. Jack quickly dropped his pants and guided me towards his bed. He laid down flat with his prick pointing straight up. My hole twitched in anticipation of his dick. He told me to straddle him facing away and lower my butt towards him. I was on my knees and rocked my hips back, feeling his member in between my bare cheeks. I heard Jack squirt some lube onto his dick, and without warning, he slipped his finger up my rear. I jumped but he kept his finger in and teased my prostate. Jack told me to get on my feet and squat down on him. I rolled forward and dropped my heinie, spreading my cheeks and awaiting further instruction. I felt Jack press his tip against my tight pucker, so I began to lower my hips. His head split me open as it had before and I moaned, stopping to get used to the feeling. I lowered myself further and the rest of his rigid cock entered me. I felt it rub my g spot and I arched my back and moaned. I slowly began to squat up and down, letting him enter me just far enough to grind against my favorite spot. “Mmmmm” I moaned. I began to pick up my pace, my cock throbbing with each stroke. Jack eased me forward onto my knees and sat up behind me. He pushed my knees together and said “Now, face down, ass up for me.” I knew he was about to have his way with my hole. I buried my face into the bed and he pulled my hips back and up. Jack slid his cock between my tight cheeks and I clenched, surrounding him. He pulled back and ordered “Now reach back here and spread those fat little ass cheeks of yours” I took my ass cheeks and spread them wide and he quickly re-entered my hole. Jack wasted no time, slowly taking his first stroke all the way inside me until I felt his balls sandwiched between my cheeks. The depth caught me off guard and yelped, clenching my cheeks again, around his sack. Jack grunted and gave my ass a sharp smack. He pulled all the way out until I felt his head stretching me, then slid all the way back in. “Ughhhhh” I moaned. “That’s it, now take it like a big boy” he said. Those words turned me on so much when he dominated me. He pushed in again and the depth was starting to hurt. I was panting like a dog and tears flooded my eyes once I felt him all the way in. I let out a soft pitiful moan again, but Jack continued to slowly pump all of himself inside me. Jack grunted and began to speed up. I kept whining and moaning as I was on all fours, face down and my ass arched up. I had to grab the bed sheets as he continued to relentlessly pile drive my tight rectum. This position truly allowed me to feel every inch of his dick and go deeper than ever. I was worried someone could hear us, but Jack obviously didn’t care, as he was now up to full speed, reaming my tight butt and my ass clapping back against him. “Oh…oh….oh…OH!” The hardest orgasm of my life quickly came over me, as I was moaning and instantly blew my load. Jack grunted and we once again came in unison as he deposited his swimmers deeper inside me than ever.

Chapter 10

Eventually, our hangouts evolved to the point that they were clearly just hookups. One night Jack came to my room, and he told me he wanted to be the bottom for once. I enjoyed being a bottom and loved the submission, but I was open to switching things up and my rectum would surely appreciate the rest. Jack took his shorts off and stood there in his briefs. I told him to turn around and began to rub his bottom. I told him to bend over and continued to slowly caress his cheeks, then moved my hands underneath between his legs, teasing his package. I stepped out of my shorts and began to rub my erection on his ass, again diving under and grinding against his balls. I knew I was driving Jack crazy and I slowly peeled down his briefs to bare his bottom. I loved groping and squeezing his tight ass. I held his butt against my groin, and I began to slip my fingers in between his cheeks to tease him. Next I grabbed the lubricant and worked it onto my prick, still sliding up and down his ass like a hotdog in a bun. “Just fuck me already!” he cried. I pushed in between until I found his hole. I asked him to spread his cheeks, and he put his face down in the bed and spread them wide. I had my eyes on the target now. I eased the head of my cock against his hole, and began to push. I had been inside a woman a few times, but this was entirely different. I really had to push, and Jack gasped when my head finally split him open. “Aaahhh” he moaned quietly as I worked myself in farther. I began to thrust, and I could feel my cock bend up towards his stomach inside him. His rectum was warm like a vagina, but so much tighter. I kept working myself halfway in and out, knowing I was rubbing up against his g spot. Jack started to push his hips back against me with my strokes, until I grabbed his hips and pressed them into the bed. I quickly buried my cock all the way in, my tight sack pressing against his cheeks. “Errrrgh!” he grunted into the bed as his knees buckled. I could tell that he wasn’t expecting all of me, and that he wasn’t used to being on the receiving end. I wasn’t trying to just hurt him, but I certainly wanted to repay the domination. I began to rapidly thrust all of my member in and out, with him grunting with every stroke. I was drilling his rectum trying to hold back my load and he started to climb onto the bed, almost as if he was trying to run. I smacked his ass and forced him prone with his legs hanging off the bed. I climbed on top of him and re-entered, my cock bending down to align with his prone rump. I ramped the pace back up and I heard him yelp. I hooked his knees under my arms and held them up, almost like pulling a wheelbarrow. I continued to fuck his ass, my tight sack slapping against his tight bottom. By now Jack was almost screaming in pleasure as I drove my dick straight up his rectum with each stroke. I felt his hole clench on the base of my cock, and I couldn’t hold back my own orgasm. Jack’s tight ring contracted over and over on my cock, milking out every last drop of my cum. I finally pulled out of him, my cum leaking out of his crack. I noticed all the semen Jack had shot onto my bed, and I knew I’d have to wash my sheets.

Chapter 11

The next week, Jack asked me if I wanted to join the school’s secret society. I asked what it was, and he said it was a society that had been running long before we were alive. I asked what they did. Jack said they all liked to play like we did. I said hell yes, and Jack said he was excited and that I could begin pledging and eventually be initiated. I asked what pledging would entail. Jack said I would be a “free use” pledge for two weeks. I asked what that meant and Jack said I basically was a hole to fuck anytime, anywhere for Jack and two other members. I said okay and Jack took me down the hall so I could meet the other two members I was assigned to. Jack said the initiation would involve him and two other senior members. The two boys were also neighbors, and Jack introduced them as James and Billy. James looked similar to Jack, and Billy was a tad shorter with a baby face and dirty blonde hair. They began to question me about academics and my schoolwork, making small talk as I had with Jack before. I assumed that the pledge period would start at a later date. However, Jack said “Let’s get started tonight. I want you to suck Billy’s cock” I asked if we could start tomorrow, but Jack reminded me that turning him or them down at any point would end my initiation. Billy and James stood in front and behind me and Jack said to let them “take a look” at me. Billy reached for my bulge from the front and squeezed all around, and I flinched because it hurt a little bit. Next James pulled my shorts down and took my shirt off, and I was standing in just my briefs and socks. “You’ve got a little bubble butt” James said as he groped and squeezed my cheeks. I was embarrassed and nervous, and Billy dug his hand in the front of my briefs and squeezed my cock before pulling my underwear down. “Decent size pecker too, no hair” he said. “He’s got a smooth ass like a baby’s too, look at this” James said and turned me around. “Oh my” Billy said. “These two weeks ought to be fun!” he said as he had his turn jiggling my ass. Go ahead Billy” James said. Jack reminded them only my face and mouth were open tonight. Face? I thought. What could that mean? “Get on your knees and get to work” Billy said. I knelt down in front of Billy’s cock and just stared at it. “Just remember, the quicker you make me cum the sooner you’re done” he chuckled. I gulped and pulled his briefs and shorts down and his cock sprang out. He had trimmed his hair, and his cock was about the length of mine and slightly thicker. I began to jerk him off, teasing his sack with my other hand. Clearly this wasn’t satisfactory, as Billy put his hand on my forehead and pushed my head back. “Open wide” he said. I closed my eyes and opened my mouth. I felt Billy’s warm head enter my mouth, and I began to swirl my tongue around it, flicking it all across his tip. “Ohhh fuck” he said and pushed his cock in deeper. I slobbered on his dick and began to bob my head back and forth. “Good boy” he said and moved his hand. I started twisting the base of his cock with one hand cupping his sack, moving my head to throat his organ. “Ohhhh fuck” he said. “Lay on the bed and hang your head off” I laid on the bed on my back with my head hanging off in anticipation. Billy walked over and pressed his prick against my lips and forced himself inside. Soon he began to ram his cock in down to the base, fucking my face. I gagged every time his cock fully entered me. He grunted and groaned and removed himself. “Suck on my balls some” he said and dipped his balls in my open mouth. I began to lick and suck on his tight sack as he dipped them in my throat. “Now lick my hole” he chuckled. I had never licked a man’s ass, and I didn’t really plan to. But he spread his cheeks and dropped it on my face. I closed my eyes and began to slowly lick his pucker, and I was thankful he was clean as I slipped my tongue in once or twice. “Ohhhh yeah” he said. Billy then re-entered my mouth and started forcefully fucking my face. He grunted with his cock all the way in my mouth and I felt his hot load shoot down the back of my throat, and I almost choked. Billy was moaning loudly, his dick down my throat and his sack pressed on my face as I gagged on his cum.

Chapter 12

The next day I saw James, and he said he wanted me that night. I knew there was no backing out and all day I could only think about what I would have to endure that night. After dinner I went to shower and headed back to my room. My hair was still wet and I was still naked when I heard a knock on my door. I cracked it open and looked and it was James. He must’ve seen I was nude as he said “Perfect timing” and barged in. He undressed and I watched as his cock flopped out of his briefs. Boy was it LONG! It wasn’t quite as thick as Jack or Billy’s, but it was certainly the longest. He sat on my bed with his legs spread and said he wanted a lap dance. I walked over and turned around so my butt was facing his and began to grind my ass against his prick and his sack. I forced myself backwards so that his cock stood straight up between my cheeks and began to “bounce” my cheeks around his shaft. “Mmmhmmm” he groaned. I felt him squirt some lube down my crack and he grabbed my hips and held me up above his cock. Then he lowered me onto his dick, and I pushed back as I felt his head slip up inside me. I began to ride him, my legs spread wide and my knees bouncing as his cock slid up inside me. I was going slow, teasing my prostate while jerking my cock. I began to move back and forth, grinding on him forwards and backwards. Then James grabbed my hips and slammed them all the way down on his erection. I yelped and arched my back and tried to jump, but he held me there. The length of his cock going right up my rectum so soon caught me off guard. James began to take over, ramming his helmet all the way from the edge of my entrance to deep up my rectum. James then pushed me off of his cock and threw me onto the bed on my back. My legs were hanging off the bed and he forced himself between my legs, spreading them far and wide while keeping my knees back up high towards my face and told me to hold them there. I held the back of my knees with my hands and he looked me in the eyes and began to rub the head of his cock up, down, and around my ass, rubbing himself all the way against the bottom of my sack down to the bottom of my ass crack. I moaned as his helmet re-entered me, and I pushed back to help me accommodate his enormous prick. The sensations that this position produced were incredible. I was moaning loudly as James grunted with every stroke, driving his long cock all the way into my butt with his hips meeting mine. I found James more pleasurable and learned that the depth of anal penetration was more important to me than the width. I kept my legs spread wide with my knees held back and I really wanted to try to hold back my orgasm but I couldn’t take it anymore. Without even touching my dick, my cock shot wad after wad of sperm up towards my face. James also came up my ass, and I watched his semen leak out of my anus onto the sheets.

Chapter 13

The next morning I was in the shower when Jack walked in. He quickly undressed and joined me, right beside me, as he often did. He began to soap himself up and out of the corner of my eye I noticed him stroking himself. I quickly cut my water off and began to walk away to claim my clothes. “Not so fast” he said and he grabbed my wrist. “I wanna make sure you’re nice and clean.” Jack said as he began to rub my cheeks. “Bend over and spread ‘em” he said. I nervously widened my stance and bent over, reaching back to spread my ass cheeks. I felt Jack’s fingers caress the inside of my ass cheeks. He reached one hand under and cupped my balls and fondled them. Without warning, he slipped a soapy finger in my rear. I knew it was soapy because it burned my insides. He poked around and withdrew his finger. “Hold still now” he said and I felt him push his soapy cock inside me. I yelped from the stretching and burning and tried to run but he grabbed my hips. “Don’t run now, you know the drill, take it like a big boy” he said. I was erect now, and grunted as Jack pushed his cock further up inside me. “Ohhhh” Jack moaned as he held my hips tightly and continued to ram his dick up towards my butt. This position provided great stimulation for my prostate, as it allowed Jack’s cock to naturally curve on the way up my rectum. I had my eyes closed because of the hot water pouring on my front half. I leaned over a little more to put my hand on the wall of the shower to allow me to brace myself. I cupped my sack and began to stroke my engorged erection as I gently began to rock back on Jack’s erection. “Erggghhh…mmmmhmmmm” I tried to stifle my moans as I knew we were in the shared showers. “Bend all the way over” Jack said. I leaned over to about 90 degrees, which pushed my ass deeper towards Jack, causing me to let out a loud moan as I felt my cheeks meet his hips. I used both my hands on a rail attached to the wall in front of me. Jack spread my cheeks wide and pushed even further. I whimpered and my legs began to fold. Jack picked my hips back up. “Stay still and take it like a man…unless you want out” he ordered. He moved his hands back to my ass cheeks and spread them again. He slowly pulled back, his soaped-up dick burning in my rectum. Then he began to stroke away. My knuckles were white, tightened around the rail holding on for dear life. Then Jack sped up, using the full length of his dick to pound my backside. I was moaning and whimpering with every stroke as he gave me “backshots” while I was trying not to collapse on the floor from both pleasure and pain. I was worried about all the noise we were making and hoped he’d cum soon. Then, it washed over me. I felt my ring begin to contract on his cock, and my semen sprayed all over the wet floor as Jack shot his up my ass. We had yet another simultaneous orgasm, and I almost collapsed on the floor as my legs and my glutes were shaking. Jack pulled his cock out of me and gave my ass a slap. My hole was raw, and I could feel his cum leaking out of my butt.

Chapter 14

The night of the initiation, Jack knocked on my door and told me to follow him. He led me to the library and pulled a book on a bookshelf. It opened a secret door, like something out of a movie. Jack shut it behind him and led me to a dark room where two other boys were waiting seated. “Well, let’s get started” Jack said. He rose from the center chair and grabbed a long rectangular paddle from behind him. “Oh hell no. I’m not having my ass spanked again” I said. “Oh you don’t have a choice. But that earned you ten extra swats.” Jack said. I turned around and started to run to the door. Billy and James chased me down and each grabbed one of my arms. I was still trying to run and flailing my legs. They pinned my back down to a table and strapped my waist over the table. Billy and James pulled my arms forward and strapped them onto the table as well. Then I felt Billy reach around my waist and unbuckle my pants, quickly dropping them to my ankles. I was bent all the way over at the waist, and I looked up ahead of me into a mirror and saw all the boys were staring at my rear. “You weren’t lying Jack, that boy does have a fat ass!” Billy chuckled as he slapped my ass and squeezed. My erection began to stir even though I was blushing and extremely nervous. “I gotta feel this!” James said. James walked over and took one of my cheeks each hand and lifted them up while squeezing. “Fuck, I love this ass. I can’t wait to stroke it again!” he said. That last comment made me shiver. Was this gonna turn into an orgy?” James grabbed the waistband of my briefs and tugged them up, giving me a slight wedgie. He continued to rub my cheeks “Damn I wanna fuck your tight little ass!”. “Not now James, we must continue” Jack said. Jack stepped behind me and pulled my undies down. Now I was bent over and bare assed in front of three guys, about to get spanked. Jack rubbed the paddle up and down my rear, from my thighs to the top of my ass. “Now Jim, you are to take thirty swats. You will count aloud after each stroke. If your count is not heard, or if you try to dodge a stroke, you will receive five more. Are we clear?” I could only murmur yes. I turned behind me and watched James and Billy grin as Jack raised the paddle up high. It felt like slow motion as he swung the paddle towards my bare ass. The sting lit me on fire and I yelped. “One” I said as my legs were shaking. “Not loud enough!” Jack struck again. The crack of the wood on my rear was like a gunshot in the room, and it certainly hurt like one. “ONE!” I screamed as tears were already in my eyes. SMACK! SMACK! SMACK! Jack was right about one thing, this was intense. If Jack’s previous spankings were a tease, this felt like a parent trying to give out the worst punishment possible. Jack continued to wail on my ass with the paddle, with every stroke arousing a scream out of me to yell the number. After fifteen strokes, I felt like someone had literally set my bottom on fire. I was begging Jack to stop and said I’d do anything, but he showed no mercy. I eventually laid my head down and just took the strokes. After he was done, Jack came over and began to rub my cheeks. They were still blazing and I could feel the welts from the large paddle. Billy undid my restraints and I instantly reached for my briefs to pull them up. Billy smacked my warm ass and told me to get up on the table on my hands and knees. I got into position and he re-secured my ankles and hands to the table. I looked in the mirror and saw James behind me and I watched him unbuckle his pants and slide them down with his briefs. James was even more “hung” than Jack. His cock was skinnier, but it had a good inch on Jack’s cock. “Now, let’s see you take on two dicks at once” Jack said with a grin. James stood behind me and rubbed his slender organ up and down my ass crack. “Stick it out for me” he said with a slap on my rear. I didn’t really know what he wanted, but I stuck my butt back towards him as far as I could. Next I felt his tip against my hole and he opened me up. No warm up or anything of the sort, as Jack had done with me. “Ohhhhh fuck.” he said and gripped my hips. Next Billy came around to my face. He unbuckled his pants and out sprang his erect cock. GEEZ! Was this just a club for guys with massive cocks? He began to rub it himself and stared me in the eyes. “Open wide for me!” he said. He pressed his head against my tight lips and I eased them open. Billy pushed my forehead back allowing him to see my eyes. Now, back to things on my rear. Once Billy was satisfied, James began to fuck my butt. There were slow strokes letting me adjust, but then it seemed he was on a mission to cum as fast as possible. I was breathing heavily through my nose as Billy also slowly fucked my face, when suddenly James buried his tool all the way up my rear. I lurched forward and tried to scream, but the lunge only let Billy further down my throat as now I felt his sack against my lips as welll. Tears ran down my face as I gagged, and James was grunting as he left his dick buried all the way in my ass. It felt like it could poke out of my stomach and reached deeper than Jack’s cock ever had. James resumed plowing my open rear, and my cock was throbbing as I felt his mushroom head repeatedly slide all the way out to the edge of my anus, then all the way back out my rectum. “Ohhhh fuckkkk” James said. “This is the best ass I’ve ever had!” Billy brought my attention to him when he decided he wanted to have more fun. He started pushing his cock deeper down my open throat, forcing himself past my lips over and over. Billy grunted loudly and said “Ohhhh shit I’m about to cum” my eyes widened as I certainly didn’t want his cum in my mouth. I tried to shake my head to say I didn’t want to swallow, but Billy only grinned at me. “Uh…ergh…open wide” Billy said and he pushed my head down to the base of his cock. I gagged and choked again as I felt his member begin to pulse in my mouth and deposit its contents. Billy’s eyes rolled back in his skull as I was forced to accept his cum. His orgasm soon finished and he pulled out of my mouth. I let out a hacking cough, as I could feel the semen stuck on the back of my throat. Billy stuffed his weiner back into his briefs and pulled his pants up. “Great job! I enjoyed that show” Jack said. James pulled out of my ass without finishing. I was happy for the break, but I assumed I was done. “Now, time for ten more strokes!” Jack said as he ran his hand up and down the paddle. I looked in the mirror and saw him pull back his weapon. SMACK! “ONE!” I yelled as I flinched due to my stinging cheeks. SMACK! SMACK! I continued to count aloud, grateful for the straps, as I would have been hunched over in agony, earning me more strokes. Jack delivered the rest of his blows. The final blow hurt so bad I yelped again and a tear ran down my cheek. “Now he’s taken some, it’s only fair to let him give some.” Jack said as he untied my restraints. I stood up and pulled my briefs and my pants up to cover my crimson red ass. “Billy, take your pants off and hop up on the table” Jack ordered. “But…I…” Billy stammered. “You are the newest member Billy, and Jim serviced you, it is only fair.” Billy blushed and dropped his pants and his underwear and stepped out of them. He climbed up onto the table and rested on his knees. Jack then lowered the table and tied down Billy’s wrists and ankles. I could tell Billy was younger than Jack, as his rear resembled mine: hairless, smooth and plump. “Now, you know the drill, face down, ass up” Jack commanded. Billy put his head down on the table and his pale rear up high. “Good boy” Jack said. James handed me a tube of lubricant and Jack told me to have my way. I could see the fear in Billy’s eyes as I walked behind the table and stared into the mirror. I began to stroke his soft, silky cheeks, which drove me mad as I loved the feel of a smooth ass. I slid down my pants and stepped out of them, then began to grind my bulge against Billy’s moon. I couldn’t wait to fuck him and I yanked my briefs down and my cock sprang out ready for action. I squirted some lube on my member and began to slide my head up and down Billy’s spread cheeks. Pre-cum began to leak from my cock and I knew it was go time. I grabbed Billy’s hips and pulled them back towards my erection and eased my tip inside Billy. I grunted, as he was much tighter than Jack, I figured he hadn’t been on the receiving end as much. I looked at Billy’s face in the mirror and his mouth fell open. “AH…” he whispered. I slowly forced my cock deeper. “Push back against me and open wide” I ordered. I wanted revenge. Billy arched his heinie higher and I rammed my cock all the way in to the base. “OWWWW…Please, it hurts” he whimpered. I began to furiously ram my dick in and out, the clapping of his smooth pearlescent cheeks against my hips starting a concert in the room. I was angrily dominating Billy’s rectum and he continued to moan and began to softly weep. I was trying to hold back as long as possible as Billy’s tight rear was squeezing every vein and ridge on my cock. Throughout my thrusts I reached under Billy and began to stroke his dick down towards me. “Ohhhhh” Billy moaned. I slowed down and pulled Billy’s cock down and back towards me. I could feel it squeezing between his testicles, and began to stroke it back towards me like I was milking a cow. “Uhhhh….uhhhhuhhhh” Billy grunted and I felt his semen spurt out over my hand. I miraculously managed to hold back my own load, and pulled out of his rectum. “Final test” Jack said as he stood in front of me and dropped his pants. “As a pledge to your service to others, you must make me cum in 3 minutes or less” he said. He stared at his watch as it ticked “1…2…3…go” he said. I didn’t know where to start. I dropped to my knees and quickly took his cock in my mouth. I licked his head with my tongue, swirling around it over and over. Then I took it deeper, grazing his head against the roof of my mouth. I kept one hand on the base of his shaft, stroking him as I continued to bob my head. Finally, I decided I would have to deepthroat him as he announced I had two minutes remaining. I looked up at his eyes and moved my hand towards his sack. I used my other hand to reach around and grab his ass cheek to push him closer to me. I opened my jaw as far as I could and took his cock all the way in my mouth. I gagged, but I heard him grunt and felt him clench his ass cheeks. I took my head off his cock and held it up towards his face. Next I began to slowly flick my tongue across his balls. I knew when they started to draw up tight that he was close. Then, I took his dick back in my mouth and began to suck. Jack said I had one minute left but I knew I had him close. I continued to slob on his cock, taking it deeper and deeper until I started to gag. Finally I knew I had to finish the job. I reached around with both hands and grabbed his ass cheeks and squeezed, causing him to jump slightly. I took his dick as far as I could, with it laying across my tongue pointed towards the back of my throat. As I swirled my tongue around his shaft, I slipped one of my wet fingers against his anus and drove it in. Jack moaned as his ring began to bite against my finger and he shot his sperm down my throat as I began to gag. I continued to gag and slurp every last drop of semen off his cock. Jack removed his cock from my mouth and offered his hand to shake. I stood up and shook his hand, and I was welcomed into the society.