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Hi Guys! I've been looking some more through the site and found someone's post that recommended some hole training. Goal is to have something in there every day. I've modified it for my situation of not getting fucked much. The idea is kinda like working out, you might have chest day, rest day, legs day, rest day, back day, rest day, rest day. So, if my goals are width, depth, duration, and puffy lips, then I need to have days where I focus on those. Ergo, I'm dividing my 7-day week into: Stretch Day, Depth Day, Rest, Grip Day, Rest, Piston Day, Rest. What do those mean? Stretch Day: Goal is to stretch my hole across, get it used to being open wide. To do that, my target is to train with dildos and/or plugs, where I should be able to sit on the dildo or walk around with the plug for some period of time, at least 5–10 minutes. If I can do it longer, maybe it's time to size up. I want my lips trained to welcome in those larger-across objects. The goal isn't pain, but if there's some stretching pain that then feels okay after some poppers, then we're good. This should be progressive, at least 3 sizes each night, starting small and getting larger. Each size should be in for at least 10 minutes. If it slips out because my hole's too loose, size up and add remaining time to that object's time. At the end of the training, which should go for at least 30 minutes, if it's a plug and I can leave it in longer, great. Or, take whatever's in out, and try sizing up to a 4th item. If I can, then that item's the goal for next time. If that largest size I had in (the third item) I couldn't keep in the full 10 minutes, then back to the 2nd one and leave it in longer, then try for the 3 at 10 minutes each for next week. Depth Day: Goal is to stretch my hole deep, and breach the second hole, get both used to being probed, touched, and caressed. I have trouble taking 6" right now, my hole's too shallow. Since the goal is to get used to being filled deep, it's again a case of mostly plugs or plug-like things, or just sitting on a dildo and maybe doing work on my laptop (multitasking!!). I have Topped Toys' Deep Space 70 and 80, and I have trouble keeping the 70 in more than 5 minutes. So, the goal is to keep that 70 in for at least 30. Then let it slide out, and try for the DS 80. If I can get it in, keep it in as long as I can. If not, well, try again next week. [Destroy] Grip Day: Goal is to bust my ring so a top can slide in, nice 'n' smooth. I realize the ideal for this is something that has a gradual taper and then a "snap" closed neck, but I don't really have anything like that. Well, maybe the "Hunter" dildo from Bad Dragon. So, the mechanics of this one are to get the toy in, then bust it out. Over and over again. Really popping my hole, assaulting it, forcing it wide open again and again. Not a gentle stretch except at the start, but really busting my ring. Of all the "exercise" days, this is the one that gets me the hardest just thinking about it. Piston Day: Goal is to practice riding / sliding on a nice dick / dildo. It's not to push depth, not to push width, not to bust my ring, but get used to that sliding motion. If I owned a fuck machine, I'd just strap myself onto it and put a reasonable-sized dildo on and let it go to work at maybe 50 strokes/min. Just ... get fucked. Rest Day: No rest for the wicked. There should be something in my hole no matter what, unless it's really too sore. The idea is simply to use a small plug and go about my business, be it sitting to work, or grocery shopping, or napping. It's been suggested I work more with poppers for this, so I'm looking to get some more, especially for the [destroy] Grip Day. I'm also trying to decide if I should get a chastity device to help focus on my hole more. Anyone have any thoughts on this?

Starting my journey to reach 100 loads this year I started by taking a 135 mile one way trip the Club STL bathhouse. I was there from 12:00pm to 6:00pm. I spent the entire time alternating between being ass up in the dark room, in the sling and blindfolded in my room with the door wide open. In that time I got ONE. ONE GOD DAMN LOAD after a 270 mile round trip. I dont understand the STL bathhouse, ive really never seen much action there but Friday felt exceptionally off. When i was in the dark room there was a young twink getting hammered by a young hot guy. There were 4 older guys watching, stroking themselves. I presented ass up but nothing. When the twink finished the old guys swarmed him but he pushed them away like a vegan getting a complimentary ham sandwich. But the just went back to stroking and doing laps in the dark room. Never did they do anything with anyone. There was another bottom posted on the fuck bench. He was there for several hours with no action. The entire time I was there I saw the twink get fucked and i got one load. That is all i saw. I may have missed some action, but what i saw was dead. This is the shit that really discourages me. The time and money i spent going there for this outcome is a gut punch. But oh well, 1 load down 99 to go. I have a party scheduled on the 16th, so we will see then.

I got paid again. I made another tweaker with a huge week long load breed my throat. His cock was so thick and meaty. We had the same tastes and he dominated me in a way only a German SS aristocrat could. A look of superior content and disappointment at the animalistic state my hunger for his cock and the T made me. Debasing myself lower with childlike whimpers and lowering myself as far down as I could with his cock in my throat pussy with a stern glance. He was everything I wanted to be and more. He made me tremble with fear and excitement but calmed his faggot down with signs of affectionate touching, saying Daddy was here.. I asked his cock ring and he gave it to me. His fun was definitely full of chems.

Tonight I had T for the first time and sucked this silver haired older man. He partied the night before so he got me cloudy. Fuck did I love sucking his cock. He thought I did such a good job that he paid me money and gave me some cash for my troubles. It started out with ten bucks but after we were done and I had him cumming down my throat we were up to $50. He was trying to constantly pimp me out. But it just didn’t pan out. I think I’m going to go over tomorrow!

In the early 2000s I met several guys on Craigslist m4m message board. I saw one guy mid 20s white, 5’10”, 150 lbs, vers who lived downtown, so I hit him up since I lived downtown as well. We emailed back and forth a few times and he eventually invited me over to his place. I guess I was more adventurous back then because we didn’t even exchange photos. I went over to his apartment in the afternoon and he buzzed me in. I knocked on his door and he opened it. He was a cute blonde, wore glasses (definitely a turn on for me), and had on a black tank top, jeans, and running shoes. “Am I okay?” I asked him, “I can leave if you want.” ”No, you’re cute,” he told me, “come in.” I followed him inside and he gave me a quick tour of his 1 bedroom apartment. He had a cute little patio and we chatted out there a bit before moving inside to his couch. We hadn’t explicitly talked about having sex, but I was getting good vibes, so when we had a lull in the conversation I pulled his head to me and kissed him. Our tongues dueled for a couple minutes until he pulled my shirt off me. I returned the favor and resumed kissing him, eventually going down his neck and chest to his nipples as I removed my shoes and socks. I knelt down in front of him and took off his shoes and socks, and then unbuttoned his jeans and pulled them down along with his underwear, revealing a curved cut 6 inch cock. I stripped him completely then stood up to remove my jeans and boxer briefs. I just stepped out of my clothes when he leaned forward and took my own 6 inch circumcised dick into his mouth, slowly sucking up and down. After about a minute he stood up and led me into his bedroom and pushed me down on the bed on my back. He go on the bed and flipped around so we could 69. I took his cock into my mouth and he took mine into his and we had a languid mutual blowjob session for about 10 minutes. He pulled off me and flipped around to lay beside me. “I don’t have a condom,” he told me. ”Oh,” I replied. “You should’ve said something. I could’ve brought one.” He took my cock in his hand and started stroking me. I grabbed his and started stroking him as well. His spit from the blowjob dried up pretty quickly so I asked him if he had lube, and he grabbed a bottle out of his bedside table and squirted it on both our cocks. We kissed some more as we lay side by side slowly stroking each other. After a couple minutes he pulled me over on top of him, my legs going in between his and sliding them apart slightly. Our lubed cocks slid against each other as I started to grind on him. His kissing got more intense and his arms were pulling on my back. My arms were wrapped around him as I thrust against him. His hips were grinding up on me as well and eventually as we both pulled back away from each other during our thrusting, my rock hard cock dropped underneath him and started sliding along his ass crack. Every once in a while I would pull back enough so the head of my dick made contact with his hole. He was squirming so much beneath me I couldn’t tell if he was pulling away from me when that happened. I was so horny at this point and just wanted to drive my raw cock in his hole, but we hadn’t talked at all about fucking, other than him letting me know he didn’t have a condom. I decided to test my luck so I wrapped my hand around my dick and placed my fist at his hole so when I thrust through my hand the head pushed against it. Each time I did that it seemed to get a reaction out of him but I couldn’t tell if he was into it. We were still passionately kissing so the only noises he was making were some moans. I thrust again and felt the lubed tip of my cock start to spread his hole. His tongue was deep in my mouth and his arms were wrapped around my body. I thrust a few more times, his hole spreading more and more. Finally I felt his sphincter give way and the head of my uncovered cock sank into him, my fist keeping the rest from going the rest of the way in. He arched his back up, thrusting his hips against me, kissing me harder and his arms pulling my chest closer to him. I let go of my cock and wrapped my arms around him as his legs came up and wrapped around my back. My bareback cock sank balls deep into him. He broke off our kiss and threw his head back. “Oh fuck!” He cried. “Are you okay?” I asked slowly starting to pull out. “Yeah,” he replied, “I’ve never fucked without a condom before, it feels awesome.” ”We can stop if you want,” I told him. “No,” he said, “you can keep going. I’ve been wanting to do this for a while now but couldn’t find anyone who was willing. Everyone always uses a condom.” “Do you want me to pull out before I cum?” I asked him. “No,” he said, “I wanna feel you shoot in me.” He grabbed the back of my head and pulled me into another passionate kiss. I started fucking him like crazy, so turned on that this cute twink was willing to take my cock bareback and wanted my load spilling into his unprotected ass. My uncovered dick slammed in and out of him as he thrust back against me, his legs and arms pulling at me trying to get me deeper into him. After a few minutes of me railing him he eased up a bit and grabbed his cock and started furiously jerking off. My own orgasm was slowly building, driven by the fact that my semen would soon be flooding this ass for the first time. I felt myself go over the edge, the orgasm ripping through my entire body as jets of cum streamed out of my cock into him. His own cock started spraying at almost the same time, sending cum up into his chest and face and even the headboard behind him. I collapsed down on to his cum soaked chest, my raw dick still buried inside him. I kissed his lips and started licking the cum off his face before pulling my cock out of him and laying down beside him. “Fuck,” he said, “feels like I lost my virginity again.” “Thanks for letting me be the one to do it,” I said. We kissed again and we lay there for a bit until I said I had to go. I got dressed and kissed him and left. A few days later I called him and asked if he wanted to hook up again. He agreed, so I got cleaned out and lubed up my hole before heading over. He buzzed me up and when I knocked he opened up the door and when I walked in, I saw that he was completely naked and his cock was already hard. I followed him to the bedroom and quickly stripped as he lay down on his back on the bed. I straddled him, my ass pressing down on his cock. “You taken a load bareback, you wanna give one?” I asked him. “Only if you’re cool with it,” he replied. In response I lifted up and grabbed his cock and placed the head at my already prepared hole. I slowly slid my ass down the length of it and started riding it. “Fuck, I’m not gonna last long,” he said after about thirty seconds. “How long is not long?” I asked. He grabbed my hips and gave three quick thrusts and moaned, and I knew he was breeding my unprotected hole. “That long,” he said, “sorry.” “Don’t apologize,” I told him, “that’s all I want when I bottom. An ass loaded with cum and a satisfied top.” I pulled off him and lay down next to him. “Thanks,” he said, “if you wanna get off you can fuck me.” Five minutes later I dumped another load in his ass.

I was leaving a gay bar late one weekday night after dancing for a couple hours and was about to cross the street when I heard my name. I turned and saw Dave, a twink with a 9 inch cock that fucked me in a bath house the previous year. He gave me a hug. "Where you headed?" he asked. "Oh I'm just headed home," I told him. "You?" He gave me a smirk. "I'm thinking about hitting up the other bath house. Wanna come?" "Hell yeah," I told him. We walked over a couple blocks to the bath house. This was an older one that had been around a while. We went in and got a couple lockers and were given towels, neither of us wanted to spring for a room. We went to the locker area and the place was pretty much empty. We took our clothes off and I looked at his soft dick, knowing that it had already shot a load inside me, and knowing that I was going to be bending over for it again in a couple minutes. I wrapped the towel around my waist. "I'm gonna hop in the shower real quick," I told Dave, "I was dancing like crazy earlier." "Okay," he said. "Come find me when you're done." I went into the shower area hung up my towel and cleaned myself off, making sure to soap around my hole. I stepped out of the shower and dried off, then went to swap towels for a dry one. I found Dave near the front as he had just purchased a small bottle of lube. I grabbed a condom from a container mounted on the wall as I was in one of my safer sex moods. "Let's explore a bit first," Dave suggested, "I've never been here before." I agreed since it was my first time so we wandered around for a little bit with his arm around me. The place had the normal things, a hot tub, showers, rooms, a couple slings. The only indication that anyone else was there was some moans coming from one of the rooms. Otherwise, we didn't see anyone. Not surprising since it was a weekday night and the clerk said it was pretty dead. We found a little alcove with a padded seat on in and he pushed me down on it, and he leaned down and kissed me, sliding his tongue into my mouth to taste mine. His kissed his way down my chest and stomach and opened my towel revealing my rock hard 6 inch cock. He took it his mouth and expertly slid up and down it as he fondled my balls. He sucked me for a couple minutes and then stood up so I could take off his towel, revealing his 9 incher starting to chub up to full glory. I grabbed it and leaned forward, taking it in my mouth and he quickly went hard. "Fuck I missed this cock," I told him, "Can't wait to have it inside me again." He poured some lube on his hands as I leaned back and he started pushing into my hole with his fingers. "Actually I don't like being fingered," I said. "Oh sorry," he replied, and started rubbing the lube onto his hard bare cock. "Better use one of these," I said, holding up the condom. "We didn't last time. Everything okay?" he asked. "Yeah, all my tests were negative," I said, "I'm just trying to be responsible." "Okay, but you'll have to open it," he said. I can never do it with lube on my hands." I opened it up and rolled it onto his cock. He added more lube and I leaned back as he put the condom covered cock at the entrance to my ass. He started pushing his massive dick into me and slowly got the head past my sphincter. It felt like he was splitting me apart, but I knew from last time once he bottomed out I would be okay. He pushed in halfway and started pulling out and pushing back in again. It felt a little rough so I asked him to add a bit more lube. He pulled out and added some more, and slowly pushed all the way in. It was a little better, but still a little rough when he started pumping again. He did that for about a minute when I felt the condom snap. "Damn," I said, "I think the condom broke." He continued to fuck me. "Yeah it did," he said, "it feels amazing. Maybe it's a sign?" "What, that we shouldn't be using one?" I asked. He grinned and nodded at me, pushing balls deep in me. I playfully pushed him back and he slipped out of me, the condom bunched around the base of his dick. "Go grab another one," I told him, turning around on my hands and knees, "so you can keep fucking me." He took the broken one off and tossed it in a trashcan nearby, there were containers on the walls all over the entire so he didn't have to go far to get a fresh one. He tore it open with his teeth and rolled it on and lubed it up, lining up again at my already gaping hole, and slowly pushed back inside. He fucked me for a couple minutes but it was still feeling a bit rough. "Can we stop for a bit?" I asked him, "it's still feeling a bit rough, I think I need to relax a bit more." "We can go to the hot tub," he suggested, "maybe that'll loosen you up a bit." I agreed and he took off the condom and we wrapped the towels around us and went to the hot tub. I admired his form as he stepped down into the tub. He was a little shorter than me but rail thin, a total twink which made that massive 9 inch cock stand out even more. We settled down in the hot tub and just relaxed for a few minutes. "You know I totally thought you were a bottom the first time we met," I told him. "Yeah, most people do," he said, "but I'm a total top." "Yeah, I found that out," we both laughed. "So you were trying to fuck me that night?" he asked. I nodded. "But I turned the tables," he said. "Hey I didn't mind," I told him, "you have a great cock, bet most people are happy to bottom for you." "A lot of guys can't take it," he replied. "It's definitely a work out," I said. "And you were the first guy in 2 years to let me fuck him without a condom," he said. "Yeah, I was a bit drunk that night, so made some bad choices," I said. "Seemed like it was a pretty good choice to me," he said, "as I recall it was after the hot tub at the other place and when we were making out in the room, you were on top and it just slid in." "Yeah," I nodded, "you were leaking so much precum we didn't even need lube." "Hey I used spit!" he said. We both laughed. "I remember it so well because you pulled me balls deep in you with your legs when I was cumming and you came at the same time," he told me. "Yeah, you were balls deep," I said, "that's probably why it took so long to leak out of my ass. I remember walking and was almost home and then it just leaked into my underwear." "Fuck that's making me so horny," he said. I reached over underwater and grabbed his cock. "Let's get out and finish what we started," I told him. We kissed for a bit and then he followed me up the stairs out of the tub. I was drying my hair when I felt his hands on my hips. I looked over my shoulder and he leaned in and kissed me. I felt the bare head of his cock at my hole; he lined that up perfectly. I moaned as he slid his raw pole into my already lubed ass. It felt so amazing. He broke off the kiss and whispered in my ear, "you sure you don't want another load?" It was hard to saw no with that magnificent dick 9 inches deep into my ass, but I managed to pull forward off of it. "No," I said, "we should be responsible." I led him into the room where one of the slings were and climbed in it while he got another condom and rolled it on. He lubed it up and placed it at my hole and thrust in and started fucking me again. Once again, it felt a little rough, so after a few minutes I had him pull out and pointed to a nearby bench for him to lay on figuring maybe a different position might help. I lifted his condom covered cock straight up and lowered myself down on it. I rode him for a couple minutes, but it still felt like he was ripping me up. I was straddling him on the bench and I stopped completely bottomed out. I reached down and picked up the bottle of lube. "It feels like the lube isn't working," I told him as I scanned the bottle. It was just water based lubricant, nothing special. He shrugged, "maybe it's not compatible with the lube that's already on the condom." "That would suck," I said, "then we'd have to stop." "We wouldn't have to," he grinned up at me. "Do you mind if I just jerk off while sitting you like this?" I asked. "Of course not," he replied, "I can just jerk off after." I started jerking off while he watched me. His cock felt good in me, but I really liked how It felt when it was moving across my prostate. I stopped jerking and pulled off him. "What's wrong?" he asked me. "I just want to try something," I told him. I rose up off his cock and pulled off the condom and tossed it in a nearby garbage can. Dave looked at my quizzically as I held his cock straight up and lowered my unprotected ass onto it. His look of confusion turned to pleasure as I bottomed out on his raw cock. I slid up and down it a couple times before settling down again. He raised his eyebrows at me. "Better?" he asked. "Yeah, it's not rough anymore," I replied, "maybe it was the lubes reacting to each other." "Maybe it's psychological," he smiled up at me, "maybe you just crave a hard raw dick in your ass." "Yeah, but it's risky," I said. "I think you like the risk," he said. "and I can prove it." "How?" I asked. He flexed his cock and I jolted as it rubbed my prostate. "Because my hard raw cock is still leaking precum in your unprotected ass. You would've pulled off by now. I can pull out before I cum if you want me to keep fucking you, but I think you'd rather let me breed you." I couldn't tell if he was only joking, but he was right. I liked the risk, I liked the feel, I hated how clinical condoms felt. I wanted skin on skin and I wanted cum dripping from my ass. Dave rolled forward so I was on my back and he was in between my legs. His 9 incher stayed in the whole time. He slowly pulled all the way out of me and grabbed his dick. "See?" he asked, pointing to the precum leaking out his piss slit, "that's what's been leaking into your ass the last minute. I could feel it leaking out into you. You want more?" I put my hand on his cock and brought the head to my hole again. "Fuck yeah!" I told him, "fucking breed me. Don't pull out, fuck me til you cum." He pushed forward and I watched between my legs as that monster cock slid in, skin to skin. He started fucking me. There was no pain or roughness this time, just fullness. He fucked me on the bench for a couple minutes until he pulled out and picked up the lube and our towels and led me back to the little padded alcove in the hallway. We were both completely naked and I could see the lube glistening on his cock. He pushed me forward onto the padding on my hands and knees. He knelt behind me and put his raw dick back into my ass and started thrusting. "I knew you were a cum slut the last time we fucked," he said, "you begged me to shoot my load in you." "And now you're going to do it again," I told him. He slammed deep into my ass, "you know it, and anyone who walks by us is gonna know you're taking it bare and that you're a cumslut." He fucked me doggy for about 5 minutes, alternating between grabbing my shoulder, hair, or hips, all the while thrusting his 9 inches bareback into me. He flipped me over onto my back and entered me again, and we started passionately kissing as he went balls deep in me. I started to jerk my cock faster and felt my orgasm starting to grow. I had my legs around him as his naked cock pounded my ass. I started whispering in his ear, "fuck that ass, I want that fucking load, breed my ass!" He pushed himself up while fucking me and looked into my eyes, "I'm going to fill your cunt with my load. I'm getting close!" I started squeezing my ass so it was milking his cock and it made him moan. I felt my own orgasm rising as he looked at me. "Fuck I'm gonna cum!" he cried and thrust in and out of my ass he spilled his seed into me. I was so turned on knowing this hung twink just shot his semen into me my own orgasm hit and I shot all over my chest and belly. He collapsed down on the pad next to me and his cock popped from my ass with a squelch. I felt his load start to stream out of my stretched hole. He held me close and we talked before a bit before getting up and heading to shower the cum off.