Sorry there haven't been updates in a long time! These stories are about some of my exploits when I went back to school for a masters degree. I have been bi since I was in college, but arriving to a huge Midwestern campus with an endless supply of hot boys put a spike in my sex life. All the stories are true, some details and of course the names are changed. In a few cases, I have added a detail from another event for dramatic purposes, like putting something from a subsequent encounter into the first encounter I describe. I welcome feedback, and particularly would like to hear from guys in school.
Please also look at a fictional series I have been working on: http://www.nifty.org/nifty/gay/college/my-god-my-roommate/ And, as always, please get in touch, I love for readers to give me feedback and tell me about themselves. midweststudent88@yahoo.com Enjoy reading!
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I think it was at the beginning of the school year when Patrick first emailed me. I had put up a few craigslist posts intended to get those beginning-of-college virgins. It had worked great the year before. At a school like that, with 50,000 students, a lot come from small Midwestern towns, conservative suburbs, and strictly religious families and homophobic schools and friend groups. For guys like this, getting to a huge campus is like being set free. They have years of jerk off fantasies and urges that they want to act on. And if they are going to get their cherries smashed, why shouldn't it be me who does it? Having heard plenty of terrible first time stories from guys, I think I am entitled to say that I am a one- percenter when it comes to deflowering dudes. I have never given a guy pain beyond the normal first- insertion discomfort, I've usually made the dude cum from his cherry popping, and almost all the guys whose cherries I've busted have come back for more. So at that particular time, with 8,000 or more new undergrads on campus, I was unashamedly cherry hunting.
The posts I used to make to find these guys had a couple themes. There were those that were aimed at the nervous freshmen: generally along the lines of do you want to explore some new things you've thought about now that you're at college. Talking about how it was the time to experiment etc, and saying that a grad student is best to keep it discreet. Those worked surprisingly well. I had some other themes, like trying something new, or taking a risk before you find a serious girlfriend etc. I had some others that were aimed at fratboys and other cocky bros, not necessarily new students. These were generally along the lines of: you're a pussy hound, you bang tons of pussy, but have you ever wanted to be seduced and fucked like a whore like those sluts you pick up at the bar or parties? Those posts, which I never thought would get a reply, actually got me a really surprising number of frat and bro cherries. And as I've talked about in another story, my apartment complex was almost all out-of-house fratboys. I was good friends with my across-the-stairwell neighbors, one of whom was the president of his frat. I told them eventually I was bi, and word got around, and I had fratboys seducing themselves to me, but that's another story.
So anyway, Patrick emailed me. The usual "s'up" at first, but as we emailed more, it came out that he was desperate to taste and take dick. He sent a few pics, and they showed a skinny smooth guy, cute, who looked way too young to be a freshman. We emailed for a few days, me trying to use all the psychology, charisma, and sexual charm I had to get him over to my place. And him playing along, but always saying he had just cum after whatever crazy sexy thing I had just emailed him. I find that sharing sex stories can get a guy going, also telling him what you're going to do to him. Gets their imaginations working. With virgins, you can tell them things they may never have thought of. But with all the easy to access online porn now, its hard to come up with something entirely new! Anyway, I thought I had Patrick on the hook, and was going to be able to smash another cherry. I was already on a roll that school year, and although I had lost count my first year in grad school, I was pretty sure I was going to break my record easily before the first semester was over.
But Patrick was one of those who just wanted to talk. It seemed like he was always jerking off when we were emailing or IM'ing, which isn't a good thing because they have to build up that horniness to take the leap. And anyways, I am not some free jerk off service. This went on for weeks and maybe more than a month. I don't think we ever were texting, but we would usually trade a few emails a day at least. Finally one day I was at class, and he was emailing about how horny he was and he really wanted to try some things, and on and on. I was hard and leaking trying to pay attention in class. Patrick finally said he wanted to come over. Hell yeah. Class finally ended and I was emailing him every minute about whether and when he was coming over. Finally, just before my next class, he said he was on his way. I really shouldn't have, but I skipped my last class, jetting out of the building and heading to my apartment, which was about a five minute walk. I got there and didn't see anyone hanging out outside. I quickly gave myself a whore's bath since I hadn't showered that morning, and took my comforter off my bed, and spread my "sex sheet" over my regular sheets.
I waited for Patrick. Twenty minutes, thirty minutes. His dorm was across campus, but the buses come every couple minutes and the stop was a block from my place. Even if he walked the whole way he should have been there. Dammit. I emailed him where are you. Disappointed, I made myself a tall drink, even though I had plenty of studying to do later on. I emailed him again. And again. Finally he responded and said he freaked out and lost his nerve and went back to his room to jack off. Fuck.
We kept on emailing, though not as much as before. I had a lot of time invested and wasn't giving up so easily. Our emails were usually the 'hey what's up, how you doing today' type of thing, but sometimes they would get very sexy and graphic, and I'd keep telling Patrick that he'd have a lot more fun getting sweaty and touching skin that reading emails on his phone and pulling his pud. He'd always agree and say 'soon'. But soon never came. As the semester ended and the school year picked up again, our emails became less frequent. Right after Christmas break we had a flurry of communication, and I thought I might seal the deal, but it didn't happen. By the end of the spring semester, we weren't talking much. I basically forgot about Patrick over the summer, although facebook told me it was his 19th birthday sometime over the summer and I emailed him to say happy birthday, and we traded a bunch of horny emails that day. When I got back to school, I got on to a fresh cherry crop, and didn't even email Patrick.
Sometime early on in the semester, I don't remember exactly when, I was walking down the street on my way to the bar when my phone beeped several times for an email. I think it was the day we had our softball tournament, so must have been a Saturday. Since it was early afternoon and I was drunk, I am pretty sure that was the day. I was on my way to meet up with some classmates to watch some sporting event, probably football if it was an early fall Saturday. On my old phone I had all my various emails pushed to it, so I got hundreds a day and didn't usually check when a new one came. But I did then. There were three or four from Patrick, and I saw they all had attachments. The first one only had the text 'You like?' and six or seven attachments. I used to have a crappy data plan and was hesitant to download all the files, which were a few meg each, but I did. They were all pics of a naked Patrick. One with cum all over his tummy, the next of his balls and cock, another of his asshole, etc. The next email said only 'I am sooooo horny' and had a bunch more pictures. I downloaded them of course, and these ones were more interesting. Patrick fingering himself in front of a mirror, then with a hairbrush hanging out of his ass, then more of him covered in cum. The next email just said 'can we hang out?' and had more similar pictures.
I was instantly hard despite having been drinking beer since 9 am. I emailed him back immediately that I would love to see him, he should come over. He replied that he was at Jimmy Johns just finishing lunch. I was about a block and a half from Jimmy Johns where I was standing, on the same cross street. I told him to just come now, I was at the corner of Smith and that street. I impatiently waited for him and sat down on a stone wall in the sun where I could look down the slight hill to where he would be coming from. Not many people walk on that street. It's hard to explain, but if you are walking from the more populated student areas, or campus to where the restaurants and bars are, there is a diagonal street that is more direct. It wasn't even the direct way from my apartment, I guess I only went that way because I was drinking and it was the way I rode my bike to work. Anyway, I finally saw someone waiting to cross the busy street one short block down from me, and assumed it must be Patrick.
As he crossed and walked towards me, I took him in. He had on those skinny knee length tan skater- type shorts that were fashionable then, and a tank top. As he came closer, I could see it was him, although it had been a long time since I'd seen a face picture. He was way hotter than I had assumed. He just got cuter and cuter as he came closer. He had wavy light brown hair, worn a bit long, a little button nose, and a friendly looking face and smile. He was slimmer than I had assumed, and had an athletic walk, the sort of arched back, toe-on-the-pavement-first type you see with soccer players. His skin was smooth and clear and looked very lickable, I sort of remembered him being pimply in the pictures he sent me at the start of his freshman year. I got up from my seat on the wall, and walked across the street to meet him.
He had a big smile as I walked to him. "Hey dude, how are you? So glad we finally finally could meet up," I said.
Patrick looked down and just said "yeah, sorry."
"No worries man, just glad we could finally hang out, its been ages!" I said trying to get him back smiling. He didn't have much to say besides one word answers as we walked the couple blocks back to my place. I was hoping he wouldn't freak out. Now that I realized he was a 10 when I thought he was a 7 or 8, I wanted him more than ever. He started to open up after a few minutes. I was asking him some more sexual questions, and he kept looking around like it was illegal to say such things in public, but I could tell he was aroused. "So I liked your pics dude! You been sticking things in your butt?" He kind of nodded. "But you want the real thing now?" I pressed.
"Ya," Patrick kind of squeaked. We rounded the corner and cut across the parking area at my place. There were a bunch of frat boys and some girls out in the courtyard, mostly shirtless, drinking, and playing cornhole. Patrick seemed nervous with all the people, but it was only a short walk to my stairwell. Of the guys out there who lived in my complex, I am sure most of them that didn't already know I was bi had figured it out. There were just too many cute nervous undergrads coming to my door to make sense otherwise. One of the guys out in the sun was a frat boy who lived in the adjacent building and was a regular 2 or 3 am visitor to my apartment whenever he needed a hot cock injection. He gave me a smile and a flip of his head, either teasing, or 'yeah bro-ing' or giving approval of Patrick. I was sure he'd ask about Patrick when I next saw him.
We got to my door and I let us in. Patrick seemed nervous and I told him to sit on the sofa and relax. Did he want anything to drink? Water, beer, milk, or bourbon: end of list. Patrick surprised me by asking for bourbon. The undergrads at that school partied like crazy, but I couldn't imagine little cute Patrick to be a bourbon drinker. I shouldn't say little, Patrick was a bit taller than me, though very slim. He had that layer of baby fat that just made him seem cute and little. Though he was a 19 year old sophomore, if you told me he was 16 I would believe it. I poured him about one finger of bourbon, and myself three.
Patrick took a sip and looked like he had just swallowed toilet cleaner. Guess he wasn't a bourbon drinker after all. But, some guys need the fig leaf of 'being drunk' to submit to their own homosexual desires, so I was happy to play along. He seemed nervous, but eventually began to talk a little. I asked him if he'd found any guys in his dorm or whatever to fool around with, and he said no. He did say that he had sort of been seeing this girl from his hometown the previous spring, and that they had 'hooked up' some, but that it didn't really continue when they were both home for summer. So he was still a virgin with guys at least, and I didn't probe whether 'hookup' meant he'd fucked her, or what. Hookup means a lot more things than it did when I was in high school.
Patrick finished his bourbon and I poured him a little more as I finished mine. When I sat back down I sat with our thighs touching. I put my hand on his knee after a minute, and though I did it slowly so he could see, he still jumped a little when I made contact. He was warm, and once I got my hand onto his inner thigh, it felt like he melted into the sofa a little. Patrick's shorts were cute, but I prefer bball shorts, or soccer shorts or meshies where I can get my hand in there. These were so snug on his leg above the knee, I could barely get a finger in. So I worked up his thigh, squeezing and rubbing, until my little finger bumped into his ball sac. I left it there for a second, and heard him exhale deeply and a little moan escape his lips. I took a handful of his balls as best I could with the tight fabric. I traced the length of his rock hard penis along the line it made in an uncomfortable-seeming position towards his hip pocket. I told him to stand up and he did. I sat on the edge of the sofa and turned him with my hands so he was facing me.
I could tell he was unsure of what was coming, so I pulled him into me and nuzzled my face into his crotch. It smelled good and soapy fresh, and also like sex. I fumbled with his belt, one of those stupid wide fabric things that threads through the two hoops. I finally got it loose, unbuttoned his shorts, and started to pull them down. Being so snug, I had to work them off a little at a time. And I smiled and said "Nice!" when Patrick wiggled his ass to help. I finally got them down, and Patrick had to work a little to get his feet out from them. He was standing there in just his boxers and tank. I told him to take his shirt off and he did. His chest and tummy were perfect. I could tell he was toned and in good shape, but the six pack and abs were covered by that soft layer, which made him seem like you could just eat him up, which I planned to do.
I ran my hands up his lean legs and into his loose boxers, making him shiver a little. His boxers were plaid, those department store own brand type that your mom buys you in seventh grade when you complain that the rest of the guys aren't wearing tighty whities anymore. It seemed a bit silly to wear loose boxers with those ass-hugger shorts, but whatever, it was fun to get up in the leg holes and feel around. Patrick's cock was pushing out the fabric and was trapped up by the waistband. I rolled his balls around in my fingers, they seemed really small, and I couldn't really remember what they looked like from all the pics he had sent. I reached into the fly and guided his cock out. It was a narrow dick, very pink and smooth. It tapered down the end, and his head was oddly small, probably just more than half the width of the base of his dick. I rubbed it a bit and let go. I stuck both my hands down the back of his boxers, easily grabbing one of his small cheeks in each, and pulled him towards me. His dick was pointing up in the air, so as the scent and heat of his cock hit my face, I had to use one of my hands to bend it down so I could wrap my lips around it.
I thought Patrick was going to collapse as I tightened my lips and pushed down his cock. I gave a few long slow sucks up and down, and then pulled off a bit to work his head and piss hole with my tongue. I don't know if it was because his cock wasn't too long, or because it was so narrow, but I could get it almost all the way in my mouth. I have a bad gag, and with a big or thick cock, I can usually only work on the first few inches. But Patrick was loving it, and I made more noise than necessary, slurping and sucking, to let him know I was enjoying it. I did not want to make him cum though. A lot of nervous young guys and virgins will get nervous and leave once they cum. This had happened to me plenty while in grad school. Don't they realize you can cum a bunch of times and its fun!? I finally pulled off of Patrick's cock, lifted it up, gave a few licks along the cum and piss tube on the bottom, and the sucked his nuts into my mouth. Patrick's dick was of an average length, maybe five inches or a little more, but looked small because it was so thin. The only thing that made it look proportional was his tiny balls. They were really unusually small, and tightly packed in a round firm sac. I could get his whole sac and both nuts in my mouth easily, and I did, sucking on them and rolling each around between my lip and tongue.
Patrick was still moaning and his legs were shaking uncontrollably. I sort of guided him back onto the sofa. I stood up and took off my shorts, leaving me standing there in some colorful briefs I had put on in hopes of seeing this hot preppy kinky frat boy I'd banged a few times in the past couple weeks. I pushed my bright orange cotton covered boner into Patrick's face. I knew a beginner wasn't going to give me the treatment I like, but I wanted to see what he would do. I love when a guy works me over in my briefs. Gets them all wet, works my nuts, snakes his tongue in the leg holes to get my balls and even my hole wet. But this kid wasn't going to do that. He reached for my cock with a shaking hand and took a hold. After a few strokes his eyes lit up, perhaps at the thickness, or my big fat dickhead, the opposite of his. After a minute, he took the head of my dick, which had made a little wet spot on my undies, into his mouth. Well, not really, he just kind of wrapped his lips around it. "You can take it out" I said, softly.
Patrick slowly and carefully pulled out the waistband until it was free of my cockhead and pulled my undies down below my balls. Now, probably for the first time in his life, he had a hard leaking mancock in front of his face. He was breathing fast, and reached out to hold it again. Without warning, he closed his eyes and pushed his open mouth forward until the first three or four inches of my dick were in his mouth. He started sucking on it, and was doing a pretty good job, apart from some errant teeth. He got bolder and took more and more in, until I felt my head hit his throat hole and he of course gagged and pulled off. I told him it was fine, it takes practice, and he went back to it, although a little more conservatively. I enjoyed his eager but unskilled slurping for a while, and then eased my dick out of his mouth and kicked my undies off. I knelt down in front of him and pulled his boxers down. He pulled the fly off from around his steel hard cock and lifted his little butt so I could pull them down.
It was time to get this hot little guy even hotter. I got between his legs and sucked his thin dick for a bit. I pulled him out so he was on the edge of the sofa, and really went at his nuts. I got bolder and licked under them for a while, craning my neck to get deeper and lower. I lifted his legs a little, and got my first view of the pucker I was going to destroy to get at the cherry deep inside. It was almost invisible. No obvious hole or indentation. Just a little off color skin and a little ruffle where his tight little slit would be. After I admired it for a second, I may have been a little aggressive. Instead of working my way down, I just poked right on his opening with my tongue, and started licking it hard and rough with my whole tongue. It felt like he was having a heart attack. Panting and mumbling and shaking around violently. I lost hold of one of his knees. I kept at it, licking his crack up to his balls, circling his soon-to- be-loose boyhole, and remembering ever few seconds to put my tongue rigid right on his twat and push. I could tell he was clenching his hole, I don't know why. Natural instinct? He was loving it, but maybe that last step he just couldn't get to: opening up and giving me his asshole.
I ate him out for a good long time and got him up on his knees leaned over the back of the sofa. I ate his hole and kept trying to punch my tongue into him. Gave him some nice vacuum action on his pussyhole. I pulled back and used a trick I'd discovered. He didn't have much of an ass nor an asscrack and his valley was wide, I spanked him lightly on the insides of his cheeks and then with just my pointer and middle finger, thwacked him right on his quim a number of times. Spanking a guy right on his hole seems to confuse it, and it worked on Patrick. I could visibly see his hole wink open and closed. I got my mouth back on it and sucked and pushed my tongue in. His hole was so damn tight and hot, it was curling my tongue up. I alternated between eating his smooth sophomore cunt, spanking it, and then pushing a finger in. I did this a long time, and he just kept moaning and pushing back on me, good signs. I finally asked if he wanted to take a shower, which is often my way of getting a guy to take that final leap. You can really work an ass over in the shower! He said no, he wanted to "do it." Hot damn.
We went back to my bedroom and I had him lie on his tummy. I ate his ass like crazy, spitting and drooling on it as much as I could, and working as much of my spit into his twat with a finger as I could. Once his asscrack was like a slip and slide, I got up on him and started rubbing my cock in his crack, making him moan even louder and say 'oh fuck' over and over. Every few journeys my cock made through his crevice, I would stop over his hole and push a little bit. Not enough to jab it in, but enough to open it a little and let his pussy know what was coming. After a while, when I would center my cock on his hole, Patrick would push back, and I could see that he was pushing out his ass too, instinctively trying to poo to open his shitter up to me.
Finally, on one try, I pushed a little harder than before and the head of my dick lurched into Patrick's eager cunt. He gasped, and his sphincter crushed down on my dick like it was trying to bite the head off. I knew he was ready and eased my dick out. I flipped him over on his back and gave him a deep kiss, my tongue battling his tongue. I sucked on his nips, and went down to his leaking and still mega-hard cock and gave it a few deep hard sucks. I told him, like I had many other virgins: "baby, I'm going to fuck you now. You will love it, just relax and enjoy." Cheesy, I know, but it helps. I lifted his legs up and apart, and Patrick helpfully grabbed the backs of his knees and held them there. I knew I was going to need some more lube for this guy so I grabbed the tube from the night table and liberally slathered up my cock, and shoved as much as I could up his gash with one then two fingers. I thought about putting on a rubber, but this hot little tease had strung me along for a year, and he was going to get the full experience. Plus, there was no chance he had anything.
When I first tried to enter him, Patrick's hole was closed up tight. I tried the trick of pushing a finger in then trying to run my cock alongside it, but that didn't work. I fingered him a bit, and tried to push in, but that didn't work either. I jerked his dick a bit and he seemed to relax, and I tried again, but it was like trying to push my cock through a thick steak. Finally, I spanked his twat a bit more, jerked his cock a few times, and then took a hard hold on his little balls. Patrick breathed in quickly from the pain, and at that moment, I pushed in at least a few inches. His body went rigid from the unexpected penetration. I could feel his ass tighten, and then loosen. When Patrick relaxed, I un-gently shoved the rest of my cock into him, getting another gasp and moan out of him.
It's been several years, and I quite honestly don't remember all the details of that first fuck. I know I fucked him hard, that he came twice while I was inside him. I remember thinking that I couldn't believe how tight his cunt stayed the entire time. It was like pulling out of playdough each time. I remember the first time he came that I almost did too, his tight little passage gripping my cock with his spasms. I only fucked him harder after that, not in a mean way, but sensing that he wanted to be wrecked, ruined. After that first orgasm, I just laid into him, pulling all the way out and slamming back in. I lifted his little ass up so I could get that upward angle and really beat up his prostate. It must have been a good fifteen or twenty minutes while I was pounding his puss and he was moaning and saying "fuck fuck goddam" over and over when he tensed up and shot another load on his soft hairless tummy. I knew my time was up and gave him another dozen hard stabs before I flooded his guts.
Unlike most young guys, especially virgins, Patrick cuddled with me for at least ten minutes. Me touching his spent dick and probing his loose hole a little. Finally he said he needed to clean up, and I invited him to shower with me. Normally I like to shower with a guy before or after sex, but Patrick made it clear, I guess, though not saying so, that he just wanted to shower himself. Fine by me. I had another drink while he was showering. When he got out and dried off, I called him over to the sofa. He sat down, naked and nervous, and I kissed him. We made out for a little bit before he broke away. I offered him a drink and refilled his glass. I tried to talk about what had happened, but he was back to one word answers, although his hard dick made me understand he had loved it. After a while, I was hard again too, and tried to talk him into an encore. I thought I had him there, but he said he had to be going. I leaned over and sucked on his dick for a minute, but when I stood up and tried to raise his legs, he wasn't having it.
Sadly for me, he got up eventually and recovered his clothing from around my apartment. He finally said so long, and we kissed by the door for a while as I kneaded his little ass and pushed my fingers into his deflowered twat as best I could given his tight shorts. He left, and I did soon after to catch up with the gang at the bar.
While Patrick was showering, I had called myself from his phone, and I texted him a bit through the afternoon and evening. He had had fun he said, and was glad he'd taken the step. I talked him back over the next day for a repeat performance, which was hot as hell because he was more relaxed and really verbal and into it. Despite my efforts, I didn't see him again for a few months. But it was awesome all over again. I saw him once spring semester, after bumping into him on campus. The last time I ever saw him was after my final exams for school when I was hanging out and drinking with nothing to do. I think it was the last day the undergrad dorms were open, and I got a call from Patrick. He was over to my place in fifteen minutes, and it was as hot as the first time.
Love to hear from you. Email me: midweststudent88@yahoo.com