One day when I was 18, I was having a regular bowel movement and a noticed a few drops of blood. Scared to death, I immediately told my mom who calmed me down but told me we would look into it. She had a friend who was a nurse, and she told me we would go see her before deciding what to do next. I begged her to ignore it, even though I was originally scared, the thought of people inspecting my butt scared me more. She told me her mind was made up and that if I gave any more fuss she would spank me. Next she stepped to the house phone and I could hear her talking to her friend, Michelle, and explain the situation. I was already red in the face. She hung up and told me to get dressed and that we were going there right away. The short drive to Michelle’s house was quiet, but I was extremely nervous. My mom had a stern talk with me before we got out of the car and reminded me that there would be no back talk. I said yes m’am and we went inside. Michelle greeting us warmly, although it felt awkward given the circumstances. She told us to follow her into the bathroom. “Well there’s no use in delaying it, go ahead and drop your pants for me hon” she said with an awkward smile. I gulped and blushed and stepped out of my gym shorts, revealing my package held tight in my white briefs. Michelle told me to turn around and rest over the sink. I saw her behind me in the mirror with my mom standing at the door. I felt her smooth fingers hook into the back of my waistband and I turned. “Now don’t be shy, I’m just taking a look here.” she said and slid my undies down to my feet. “Okay Robert, I’m just going to take a peek at your heinie” she reminded me. I felt a hand on each of my cheeks and she forced them wide. The rush of cool air along the inside of my crack gave me goosebumps. “I don’t see anything out of the ordinary” Michelle said as she opened a drawer next to me under the sink. “But I think I should take a feel”. I saw her snap on a latex glove and grab a tub of vaseline and started to connect the dots. I looked over at my mom and she had the look on her face to remind me to behave. Michelle gazed at me in the mirror and explained, kindly, she was going to stick her finger up my butt. She promised me it wouldn’t hurt and that it would only last for a few seconds. I said okay and she open the tub of vaseline and took a large dollop out on her finger. She disappeared behind me, and I felt one hand spread one of my cheeks again. “Just going to rub this on first”. I twitched as I felt her greasy finger circle my tight hole. “Now push like you’re trying to go to the bathroom” she said. As soon as I did that, I felt her finger slide right in. Strangely enough, it felt good. I pressed my cock and balls into the sink in hopes to hide them, but my prick soon stiffened against my will. I felt Michelle turn in and out inside me until I the rest of her hand meet the inside of my ass cheeks. Once she was deep enough, I felt her rub a small bump and it made me jump. She pulled her finger out of me and took her glove off. Michelle explained to me and my mom that I had a small internal hemorrhoid from what she could feel. She asked if I or anyone in my family had ever been to a proctologist. I had never even heard of one, but my mom said no. Michelle said since I had developed a hemorrhoid at such a young age that she recommended going to see one for a check up just to be safe. My mom said okay and thanked her for her help and advice. Meanwhile, I tried to hide my erection and stuff it into my underwear. I got dressed and we left the house and once we got in the car I asked my mom what a proctologist was. “It’s the butt doctor”. Oh boy I thought. I begged her to let me wait it out a little while but she said she was booking me the quickest appointment available. I pleaded and pleaded for her to give it time, and she finally snapped. “That’s enough from you young man. You’ve earned yourself a spanking”. This whole ordeal made me feel like a child. We got home and my mother grabbed my ear and yanked me inside. She told me to wait by the couch and dashed to her room. My mom returned with something I hadn’t seen in at least a year. The spanking paddle! I didn’t always get spankings with the paddle, so although I didn’t see it as a big deal, I had really set her off. She sat on the couch and explained to me that this was a serious matter that she was concerned about because she loved me and said I needed to be concerned too instead of fussing. Next she sat on the center of the couch and spread her legs. With one swift jerk, she dropped my pants and my gym shorts down to my knees. I blushed as my genitalia stared her in the face. Next she forced me over her knee, and used her other leg to pin my legs down so I was bent over her knee. I put my hands on the floor and waited. Truthfully, spankings occasionally turned me on, but I knew this one would not be delightful in the slightest. “Young man you have earned yourself twenty swats. You will count aloud. If you are not loud enough, the swat will not count. If you move or shift before a swat, it will not count. Do you understand?” I said yes ma’am and awaited the worst. Whack! “One!” I said. Whack! Whack! Whack! My cheeks started to burn as I counted. The fifth strike yielded an audible slap that is only heard when the buttocks are struck right down the middle. (I’m not a sound scientist or anything, but if you’re into spanking I’m sure you catch my drift) “Yow!” I cried out and arched my ass up off my mothers knee. “You’ve earned yourself 5 more swats” she said. Whack! Whack! Whack! The burning sensation intensified and my eyes began to fill with tears. Mom continued to alternate from cheek to cheek, showing no remorse as I continued to count out loud. After about 15 strikes, she began to vary her height along my bottom, ranging from the top of my thighs to the top of my crescent moon that was displayed over her knee. Whack! Whack! Whack! The next strike caught the underside of my bottom and she delivered the blow well enough to cause me to cry out again and jump. “Five more”. I began to cry. Whack! Whack! Whack! My ass was on fire. I don’t know if I had ever been spanked this hard. I was beginning to think I’d have bruises. I cried and cried to no avail as the strikes on my ass cheeks continued until I finally said 30. I was relieved but still teary eyed. She explained why she punished me again, which was really because she was concerned that I wasn’t concerned enough about my health and it worried her. I pulled my pants back up and limped to my room to retire for the night. Once I was sure she was asleep, I snuck to the bathroom and found a small jar of Vaseline. I happily yanked my briefs off and climbed into my bed with it. Next, I laid back and spread my legs with my knees to my chest. I dipped my finger in the jar and worked my finger up my hole. My cock stiffened, and I lathered Vaseline all up and down it. I began to twist and stroke while fingering my rear and it wasn’t long before I had the orgasm of my life, to that date at least. I slept pretty good that night, albeit with a sore set of buttcheeks. The next day, Monday, my mom told me she had gotten me an appointment at the proctologist for the following day at 8 a.m. As I ate my breakfast, she passed me a sheet of paper from the office detailing the required “prep” for the visit. I couldn’t help but wonder what that even meant. I read down the sheet. “No solid foods by mouth 12 hours before the appointment” Ouch. The next line followed “Enemas till CLEAR before the appointment. It is recommended that you start the enemas AT LEAST 12-24 hours in advance in order to achieve a clear return. I had a lump in my throat. Mom had given me a small syringe enema before, but that was it. I know my sister had endured one of the more serious enemas from a bag because I peeped at her when mom gave it to her. I read on and the sheet detailed recommended enema supplies and instructions, including positions. There was also a note that any enemas that had to be administered in the office would result in upcharges. We didn’t really talk about the prep and I went off to school. I told my buddies about what I had endured the weekend and what was coming up. One of them was clearly alarmed upon hearing “proctologist”, and I poked and asked why. He didn’t want to tell me, but he finally told me that his older brother had to the same Dr I was going to and that they tilted his butt up and stuck a tube in it. I gasped. I shivered at the thought. I hoped I wouldn’t have to endure that much. All I could think about at school was my sore bottom in the desk seat, as well as what else my bottom would endure in the next day or so. When the bell rang, I didn’t even want to go home. When I got off the bus, my mom told me it was time to take my first enema. She told me to follow her into her bedroom and I did. She had a pillow on the bed with a towel over it. “Lose the undies and wait on the bed” She clearly wasn’t in the mood for sass, not that she ever was. Next I heard the water running in the bathroom. I took off my jeans and my underwear and sat on the bed, hands covering my nether region. My mom returned with a douche syringe and a mixing bowl full of soapy hot water, along with some Vaseline. “You act like I’ve never seen your wiener before.” She chuckled. I blushed but smiled and moved my hands. Mom sat the bowl on the nightstand along with the syringe. “Get on your elbows and knees with your heinie facing me” I got into the humiliating position, and I could feel my moms gaze at my most forbidden area. She rubbed a dollop of Vaseline on my hole. I knew this was going to turn me on, and I hated I had to endure this with my mother. “Here it comes” she said as I heard her draw up a syringe full of soapy water. I braced myself and felt the nozzle enter me. I grunted as it hit my prostate and I felt a rush of water enter my rectum. There was a trickle of water down my balls as she pulled the syringe out. I endured around four more loads, and had a raging erection. My balls were drawn up tight and I was ready to blow out of that end more than I was my rear. By this point I was panting and sweating slightly. I buried my face in the pillow, pushing my ass up higher. “Good boy. I know you’re enjoying this” she giggled again. Another surge of water and I was cramping. The next load leaked out a little more than a trickle, tickling my testicles as it landed on the towel beneath me. “Mom I need to go” I said. “One more honey. And you’ll have to try and hold it. The longer you hold it, the less enemas we’ll have to do” I said okay and took another load up my butt. It was strange to me how turned on I was by this, and it showed me that I was VERY anal erotic. I laid there with my ass up high, desperately trying to hold in the water. My mom pressed a towel in between my cheeks and I pulled my knees in tight, curling up into a tight ball with my ass elevated. My erection was still throbbing. I was panting heavily and after what felt like an eternity, my mom let me go to the bathroom. I got up and ran, my cock swaying and bouncing along the way. It took me forever to release it all, but I lost my erection in doing so, thankfully. My mom told me that was it for now and that I could go rest. I took a nap and after dinner, mom told me she was going to drop my off at Michelle’s for the rest of my enemas. More embarassment. She said she was trained better and that it would be best for me. Then she went and dropped me off and said she was going to run some errands. It was 8 by now, so no more real food. Michelle greeted me and led me to the bathroom again. She was a single mom like mine, and her daughter was two years older than me. Michelle had a towel laid out on the floor. “Alright, you know the drill, you’re gonna have to strip down for me. No reason to be embarrassed.” I blushed and stepped out of my jeans and slowly slid my briefs down. Michelle filled the bag and added some soap and shook it. She hung it on a towel rack nearby. “You can lay on your back for me sweetie” she smirked. I laid down, genitals on full display. “Spread your legs and pull your knees up to your chest” she said as she knelt between my legs. Michelle donned two gloves and lubricated me and the nozzle. “Relax” she patted my leg. The nozzle entered me and I was still holding my knees up like a baby. “I’m gonna start it now” she said. Click. The water rushed in me quickly. I grunted as my bowels began to fill and of course, my member had woken up. It was sticking straight up in front of Michelle, poking out of a small sparse bush. “Oooh” I said. “You know, that’s a perfectly normal reaction. I enjoy my enemas too” she said and gave me a wink. I blushed and didn’t know what to say. “I think I’m getting full” I said. “You still have a little less than half the bag, you need to take it all and hold it” she said and gave the bag a sharp squeeze. “Ahh” I moaned. I stared at Michelle’s breast as she was on her hands and knees holding the bag. She caught me when I had moved my stare to her large rear, as her thong was poking out. The thoughts caused my erection to stiffen even more, and now my balls were drawn up. “Naughty boy” she said and crawled closer, almost like a cat. “I know this is stressful and you’re all wound up. Do you want me to help you relieve some of that stress?” She said. “I….uh….I don’t…” I stammered. This definitely wasn’t appropriate, but I was sure as hell not gonna say no. Michelle began to tease my cock with her fingers, tapping it from the head to the shaft, tickling up under my balls. “Ohhh…” I moaned. “You’re being such a good boy, I think you deserve a reward.” She said. Michelle grasped my cock and began to slide her hand up and down. Then she grabbed my balls and gave them a slight squeeze. I moaned again and she pulled in closer. She spit on my cock and began to stroke quicker, but still rather slowly. Her eyes met mine and I was shocked when she lowered her head down and took me in her mouth. She bobbed up and down on it, slobbering all over my teenage dick. I heard noises that I had never heard before, and they were sinful. I bucked my hips up, which caught her off guard but as she gagged at the base of my dick, she squeezed my balls and I emptied my young semen down her throat.My mom woke me up the next morning and told me I had to take one last enema to be sure I was clear for the appointment. I groaned but she came into my room with the bowl of water and the syringe with me still in bed. Mom told me to slide my briefs off, so I did, then she laid a towel on my bed for me to lay on. Next she told me to lay on my back and spread my legs. My morning wood was still at full attention. She gave me a smaller, quick enema, and let me release right away. I got dressed and we headed to the office.Once we got to the office, my mom checked me in and the front receptionist had a questionnaire for me to fill out. I had to answer all these questions about my bowel habits and things of that nature. I waited nervously with my mom to hear my name called. I looked around the waiting area at the others waiting. There was a girl who appeared to be around college age, and also a blonde lady who appeared to be around 30-35 years old. It turned me on knowing that they were here to get their butts examined too. I really got hard when I remembered the horror story about the tube up the rear, as I fantasized watching them undergo such a procedure. I knew I needed to stop before I started the exam with a raging erection. Next I heard my name called and a young nurse came out to greet me. I couldn’t help but think about how awkward the situation was, given that this nurse watches people get their butt examined all day. My mom followed me and I asked her to stay behind, but she insisted that she was coming with me. I knew better than to argue. The nurse escorted me into an exam room and took my vitals. Then she said the doctor would be in shortly and that I needed to strip down to my socks and underwear. I stripped down and handed my mom my clothes, and looked around the room. There were a lot of mirrors, but the room was pretty bare. It scared me. I sat on the table clad in just my tight white briefs. Soon Dr. Rodgers entered and introduced himself and the nurse, Angela. Angela was an older brunette woman who looked to be in her mid forties, while Dr. Rodgers was gray haired and looked to be in his fifties or sixties. “Alright we can get this rectal exam started. Bent over the table and drop your briefs for me.” Rodgers said. He seemed like a no nonsense kind of guy. I stepped down and faced the table, pulling my briefs down just below my cheeks. I heard the snap of a latex glove and the Dr. wheeled over on his stool. He hooked his hand in my briefs as I felt the latex against my butt, and yanked my briefs below my knees. I was embarrassed as I’m sure they were wondering why my ass cheeks were so red. Angela walked behind him and then I felt him spread my ass cheeks with both hands, eyeing his target. Next I heard a farting sound and I turned my head around and saw Dr. Rodgers with a clear lubricant glistening upon his fingers. He told me to hold still, and pried one of my cheeks open. Next I felt the cool lubricant on my hole as he slipped a finger inside me. Dr. Rodgers had much more thick, burly fingers that I had ever experienced. He entered me all the way till I felt his knuckles on my perineum, and he began to sweep and rotate his fingers, palpating my rectum. He felt around for quite some time. Angela looked on at my tight, perky ass as Dr Rodgers continued to poke and prod up my tight rear. I grunted as he finally hit my hemorrhoid. He told me he knew that was a hemorrhoid and that they needed to get a better look to rule out other complications. Better look? Here we go. I thought. He explained to my mom and I that he was going to examine me further using a rigid sigmoidoscope, and pulled a big metal gun out of a drawer to show it to us. Horror story. The damn thing was huge. It looked to be at least 12 inches long. Tears began to swell my eyes as I stood there with my briefs still down. “Will it hurt?” I asked. “It may be uncomfortable” Dr. Rodgers said in an unassuring tone. He told me I had to lose my briefs so I stepped out of them and handed them to my mom. Then I turned around with my butt facing my mom, while Angela adjusted the table so that there was a shelf on the lower end. I rested my knees on the shelf below and hung my upper body over the table. My ass was in perfect view for my mom, and I could feel the cool air along with everyone’s hot gaze on my crack. All I had on was my socks, as I stared into the mirror ahead of me, locking eyes with Angela. I watched her lubricate the scope. Looking at the instrument struck fear in me, as the metal tube was extremely long. “Is that thing going to go all the way in me?” I asked. Dr. Rodgers responded yes, and that it was necessary. Angela plugged the scope in and tilted the table to about 45 degrees with my head down and my ass up. This slid me forward and I felt my genitalia press into the paper on the exam table. Next I saw Dr. Rodgers hold the instrument up and point in between my spread ass cheeks. He told me to bear down like I was having a bowel movement. Then I felt the ICE cold metal meet my anus. I arched my ass up high, and Dr. Rodgers began to push with his toy. I grunted as the scope stretched my anus to a new record. I moaned when it finally entered me. Dr. Dodgers attached what looked like a squeeze bulb to it and put his eye up to the lens. Strangely, my cock began to stiffen. “This might get uncomfortable” Angela said. Dr. Rodgers squeezed the bulb and I felt a rush of cool air up my rectum. He continued to explore deeper and while it was well lubed, the stretch of the metal against my anus burned as he continued to let the scope enter my backside. I looked at my ass up high in his face and was utterly humiliated. Angela also had her eyes on my ass during the exam. I felt another rush of air and Angela told me it was about a quarter of the way in. A quarter?! I thought. I had already submitted to this exam for about ten minutes. My legs began to fall asleep so I laid my head down on the pillow and tried to rest. I felt the instrument hit new depths and he began to guide it side to side slightly along the way. Then it began to get really uncomfortable. “Errrgh” I grunted as the probe pushed deeper into my backside. Once it hit my hemorrhoid, I yelped and arched my butt up further. “Hold still young man” Dr. Rodgers said in a stern voice. Tears began to slowly fall from my eyes as the pain of the scope sliding past the hemorrhoid was unbearable. As he pushed deeper along the journey, I felt his hands against the back of my sack, letting me know it was almost all the way in. I kept looking into the mirror and saw my ass still up high with the tube slightly protruding from my backside. I couldn’t bear to look my mom in the eyes but I did see Angela look in the mirror at my tear soaked face. “Big push for me now” the Dr said. I pushed back against the scope and was met with a sharp pain as it felt like it was trying to straighten out my bowels. I moaned and my cock stiffened. I didn’t know why I was so aroused. Then Angela told me it was all the way in and I breathed a sigh of relief. I laid there in submission as Dr Rodgers continued to peer up my rectum, occasionally moving the scope side to side deep within me. Finally he removed the scope, and there was an audible pop as my ravaged hole closed shut. My ass was on fire now. Angela moved the table back down flat and told me I could sit up. I lifted myself and sat up, my cock angrily aroused and my balls wound up tight. Dr Rodgers said he saw no other hemorrhoids and that I could let it resolve, but enemas would never hurt to avoid them in the future and help me go to the bathroom. He told my mom he was going to give me a shot of steroids to help with any inflammation in my backside. He wished us a great rest of our day and left the room. Then Angela opened a drawer and grabbed a vial and a large needle. “This has to go deep in your tushy honey.” She said with a frown. “Lay face down on the table for me.” I got up and turned away from my mom and gently pressed my cock against the table. Angela swabbed my right ass cheek and patted it. “Relax your bottom for me” she said. Next I felt the prick of the needle pierce the center of my glute, followed by the burn of the medicine being deposited deep into the muscle. She wiped the injection site and placed a band aid over the hole and told us we were done. Mom handed me my clothes and told mr she was proud of “taking it like a big boy”. I limped out of the office, seeing another boy about my age with his mom. I hoped he knew what he was in for.