In Progress Part 1
This chapter did not take place at school, but during the same period, and was one of the hottest and hopefully ongoing relationships of my life. The story is in progress, and hopefully someday soon, I will have another chapter on its developments.
Like the best hookups and relationships, this one started quite innocently and with no sexual intention. I was sitting in the library one day earlier last year looking at facebook when I got a bunch of those annoying 'people you might know' on my screen. I usually try to close them because they are all strangers or weird foreigners or old relatives I do not want to be friends with. This time though, as I was looking for the invisible little X to close it, I saw a gorgeous guy in the list. I immediately clicked on him, his name was Taylor, and thank god, he wasn't one of those who had all his information hidden. I first looked at our mutual friends, and realized why he had popped up. He was from my hometown, was in college in a town in North Carolina where I have a bunch of friends living, I also have a bunch of friends who went to his college, he had friends who went to my high school, mine to his, and he had friends who went to my college, and he was even friends with a few of my friends' at grad schools' friends and siblings.
Now I am not one of those types who usually gets in touch with strangers on facebook, but this was too many one-degree-of-separation things. Its one thing when you have 40 mutual friends, but went to the same high school or college, but not when you are connected in so many ways. So I wrote Taylor a message just saying all these weird coincidences and mutual friends we had. I didn't expect to hear back, but did after a few minutes. We talked a bit about our hometown, his school my school. It was nice to reminisce about some of this stuff. I didn't think much about it, but gave him my email to keep in touch since facebook messages aren't the best and don't work on my phone very well.
Later on, I got an email from Taylor. It was nice, and (in my dreams) a little bit flirty. Curious about this guy, I googled his email address. It was an address that seemed like an initial and a name, followed by some numbers, so I thought it might turn something up. What it did turn up was page after page of hits on Tumblr sites!! And man, did this guy have good taste in porn! I spent at least an hour or two checking out all the tumblr sites he had "liked." Now I was pretty excited. A kindred spirit! I emailed him back, and asked what was going on that weekend. He said not much and asked me what I was doing. I told him I was going out with some folks in my program, and hopefully was going to see my FB. Now, I knew this would be intriguing. And sure enough, he emailed back pretty quick and said "what's the dude who's your FB like!?!" I teased him a bit saying who said it's a dude?! But he knew.
After that initial intro, our email communication grew into a pretty frequent exchange that included some flirting, a lot of sex talk, almost real-time exchange about our FBs and conquests, and whatever else. We traded a lot of pictures, which made me realize he was even more of a hottie, especially when I got some sexy pics!! We would email every day, sometimes with some gaps, but would always alert each other to new prospects, or hot sex sessions. I got even more turned on when Taylor told me that he liked guys a bit older, often grad students, because he was pretty discreet around his university. The mirror image of why it was so easy for me to get closeted undergrads at my university!
Him: *********@yahoo.com: Ha I'm a senior at *********. Plenty of hot athletes and frat guys to screw around with but I tend to like slightly older guys. 24-28 ish and I'm not out so I don't like hookin up with other undergrads. I definitely had some hot hookups myself haha.
We chatted about hookups and etc, and when we first were into guys and what our first experiences were. I told him I had a jerk buddy in high school who blew me a few times, but he outdid me!
*********@yahoo.com: ********* high! Football powerhouse for the last decade haha. I remember sucking off this one hot guy in the locker rooms ha.
I asked him how it happened:
*********@yahoo.com: Haha I just got caught staring in the locker room and he called me out one day.
He told me about more of his hookups, past and in real time, and I did to him. We shared pretty much everything, it was super hot. We traded pics of dudes we had been with, critiqued sex, and talked about everything. No holds barred, we shared things about our interests that I had at least never talked with anyone about. Even though I had never met him, I felt like I knew him. He was very smart and articulate, even in late night emails. The more I talked with him, the more he turned me on. He was like me, confident, horny, out to get some, and a baller. I always teased him about when we met up sometime somewhere I was gonna lay a monster fuck on him. He never protested, but said he usually topped. Well I had heard that one before. He said he bottomed sometimes, but didn't always like it. When I asked him if he liked to suck dick, he said:
*********@yahoo.com: oh yea I'm fine with that, even rimming. I just don't really enjoy getting fucked. It hurts :P
It wasn't all sex talk. Most of our emails were just normal how ya doing whats going on type things. Asking about school work and hows it going. But we'd always talk about new prospects, or dudes we were going to meet up with, or dudes we had had sex with. It was awesome to have someone to talk about all this stuff with. We talked in pretty gruesome detail about our sex, what we liked, what happened, and etc. A normal example was when I told him I had had a FB over the night before and he told me about a grad student HE had hooked up with the night before:
*********@yahoo.com: Really? give me the details :) I've been waiting to hear an update from you! We just talked and sucked each other off. He was amazing at giving head though so I think well definitely hang out again.
We talked all the time, and I felt like I knew him. We'd talk about meeting up sometime, but it just wasn't feasible during school. Then he told me he like anal maybe more than he had let on:
*********@yahoo.com: Fucked this one guy while watching a football game, went over to another's after a night of drinking and we came three times between 2AM and 10AM. I usually don't enjoy getting fixked so I go soft, but I came while he was fucking me twice! First time I came I was on top of him and he was jacking me off as he fucked me. Second time he fucked me on my back so hard my head was hanging off the bed and I came haha.
We discussed fantasies and what we would like to do. I told him that I had recently begun looking at some domination and bondage type porn and it turned my on. He agreed. At one point he told me also that he liked some funky stuff.
*********@yahoo.com: I love the smell of a musky jock after a hot guy has been workin out so no I wouldn't call that weird. Ugh now I have a boner. It's causing a stir in my groin! After a run, the musk of a jock, all of that is hot for me
I began to look forward to Taylor's emails almost desperately. I had another dude that I discussed sex and conquests with, but with that guy (previously described) it was so antiseptic. I was all about how long, how hard, how tight. With Taylor, I could tell there was a sense of fun, of excitement, of adventure, and even of romance. It was really more personal and therefore romantic. I wanted him.
As our emails continued, a small school break approached. They always gave a four or five day weekend sometime in the fall. Perhaps subconsciously, perhaps not, I called my friends who lived in the town Taylor was in school at and asked if they would be around and celebrating one of our friend's birthdays that fell that week. They were having a party, and invited me to come down to North Carolina, and pressured me to do so. I quickly emailed Taylor and asked if he would be there that weekend. He said of course, and I made my plan. I booked a hotel for the Friday night; the party was on Saturday. I told my friends I would drive down Saturday. It was a nine hour drive, but I assured them I would leave early. They wanted me to come Friday because they were having a lunch bbq before the party, but I said I could get away.
When the day arrived, I took off mid-morning. After an uneventful drive through the beautiful foliage of the Appalachians and Smokys, I arrived in the town at about 9:30. I google mapped myself to the hotel, and call Taylor to let him know I was there. He arrived in 20 minutes.
I had brought some beers and wine and even champagne with me, and had it in ice in a bag in the sink. I love hotels that are 'klassy' enough to have ice machines, but leave you a plastic bag instead of a bucket. If I was fuckin homeless, what would I be doing in a hotel!? Anyway, I was so excited to see Taylor, it was pretty anxiety ridden waiting for him, and I had butterflies in my stomach. It wasn't nervousness like meeting a hookup, but was genuine longing, I think. Finally, there was a knock on the door.
My dick immediately twitched and stiffened as I walked over to open the door. With a moment's pause, I pulled it open hard. Taylor rushed in with his arms open and mouth looking like he was going for a kiss. I had just brushed my teeth, so thought we may as well go for a toothpaste commercial moment and we had a hot long kiss. Chocking each other with tongue, I gripped the back of his head tight while my other hand travelled down his spine and rested with my thumb in the waistband of his skinny jeans, and my fingers on his small tight ass. I know its clich‚, but he looked better than all the photos he had sent. He had a very handsome angular face, nice features, stylish dark hair, and what seemed (clothed) as the nice tight body I had seen naked pictures of. (Ahh modern technology and culture where you see people naked before you meet them). He was dressed a bit hipsterish in a cool tight plaid shirt, a little sportcoat, and previously mentioned skinny jeans. I didn't plan on those clothes being on long, but we had to get acquainted of course.
We made some small talk and I opened the not-quite-cold-enough champagne. We immediately fell into conversation, oddly as an extension of the hundreds if not more emails we had sent. I deleted most of them, but still had 289 last I checked. This was a 'hotel,' but besides the king bed, there was just a love seat made for one obese person. Crammed next to eachother, we talked about how good it was to meet at last, and before I knew it, Taylor was rubbing my chest, letting his hand drop into my crotch every once in a while. I stood him up, kissed him again, pulled his coat off and threw it away and began to unbutton his shirt. I flicked his nips as the shirt revealed them, getting a little moan and chuckle out of him. I got his shirt off and rubbed his smooth defined chest. Taylor had some nice muscles and abs, but was not ripped or chiseled and his skin was soft to the touch. Very few guys can pull off the whole rippling muscles thing, and Taylor has the perfect combo. I put my arms around him and pulled him in. The skinny jeans were blocking my intentions, so I unbuttoned them and Taylor wriggled out of them. In his boxer briefs he looked great. I pulled him in again and let my hands roam his back and down, cupping his nice little cheeks. They were long oval ass cheeks, narrow, and felt muscular while still soft to the touch. They would probably make a nice little jiggle when spanked, I thought, making my dick twitch.
Putting my fingers into Taylors crack, I lifted him up a bit on his toes, gravity spreading his cheeks and opening his crack so my fingers met and rested over his hole, again, making him let out a long soft moan. Taylor grabbed my crotch, making me release his ass melons. He snaked his hand up the leg of my basketball shorts and said "mmmmm" as his fingers quickly found my nuts. I had thought about putting on underwear, but I knew from our chats and pictures he had sent that Taylor liked hot undies, and I didn't have any that fit the bill. He fondled and tugged on my balls, rolling them around in their loose sac, now making me moan. He quickly shucked my shorts and as I stepped out of them, he lowered himself onto his knees, licked my nuts a little, and then in one long motion, licked up my nuts, up the bottom of my cock, around the head a few times, and then sank down my shaft slowly, keeping his lips tight as a rubber band.
Taylor blew me for a while, and I was getting worried it was working me up too much! He was going up and down my dick fast about 10 times, on the last one taking it as deep as possible before sliding slowly off of it with incredible suction and his strong tongue working all around it before stopping with just the head in his mouth and swirling his tongue all around it and into the piss slit. I pulled him back up and we kissed hard. I pulled his boxer briefs down and my dick jumped when I saw he had something on underneath! As the bbriefs fell to the floor, I saw he was wearing a hot little designer jockstrap! I sank to my knees and began working the full pouch. His hard dick was pointing down and straining the fabric. I worked his nuts and tickled the head of his dick. He had soaked thru the thin pouch material with precum, and I leaned in to lick some off, making him shudder. I nibbled his cockhead while my hands traveled back to feel his little cheeks, pushed together by the jock. I snapped the straps on his ass, making him jump a little, then parted the smooth buns and probed his crack. I felt down to the point where the straps meets and wiggled a finger in till I pushed on his taint and poked his ballbag, which was being crushed down in the pouch by his dick.
I ran my fingers back and forth in his crack, zeroing in on his rosebud. I found it, it was a tight little circle in a little depression in his crack. I twirled my finger around it, again making him moan, and when he jolted for a second when I nibble the tip of his dick, his butthole opened a tiny bit and the tip of my finger went in. It was time to get on the bed. I was so crazy horny. I stood up and flopped onto the bed. Taylor walked slowly over with a humorously funny sexy/slutty look on his face, and a finger in his mouth. I laughed. He made a show of slowly working up the bottom of the bed, licking his lips as he made his way up between my legs. He slid his mouth down my cock and began to work it again. After a few minutes, I flipped him around so he was on top of me and his full jock pouch was in my face. I pulled the waist band down over his cock and balls and began to furiously lick them. I couldn't quite get his head in my mouth at that angle, but I could lick the underside and jerk him while I sucked on his nuts. After a bit, I nudged him forward till the end of the pouch came into view, as well as his hole. He had a prominent hard bump under his balls, which I licked frenziedly. Now, I don't ever eat an ass unless I've just showered with the dude and given him the soapy finger for a good long time, but Taylor was a hottie, and I was so worked up, I made an exception. Finding everything clean, I poked my tongue into his hole, getting a low long moan from him. My finger exploration had been right, he had a little circle of a butthole. To my delight, as I licked and tongue fucked him, the little opening started winking open more and more....this hole wanted to get stretched!
I was still worried about cumming from the insane blowjob, so I rolled out from underneath him and flipped him on his stomach. I climbed on top of him and hugged around his shoulders and licked his neck and nibbled on his ears. He was wiggling around, and humping the mattress. I used his motion to wedge my leaking prick into his crevice, and began dry humping him, working my dick down over his hole until it went into the bottom of his pouch and bumped his nuts. I was really getting worked up now, and so was Taylor. A few times on the downward journey, I nudged at his hole. It was tight as a drum, this was going to take a little work. I decided to take a break...I moved down his body until I was between his legs. I wrenched his legs apart and dove into his ass. Now, I love eating a nice butt, but there is no danger in it making me cum. I figured I'd get his hole nice and ready, while letting my orgasm subside so it would be a nice long fuck.
I ate his ass like crazy. Once it was nice and slick, and open from my tongue fucking, I worked a finger in. Spitting on his hole, I worked a second finger in. Taylor was writhing on the bed, and pushing his ass back onto the invading fingers. I ate his ass a bit more, trying to get as much saliva as I could on there. I pulled away and let a large glob of spit slowly drop, hitting perfectly on his hole as it winked open. I put my thumb in my mouth and worked it into his hole. At the instant I felt his prostate, he jumped and let out a yell/moan. I rubbed it a bit, and then pulled out. His hole was now opening and closing, but not all the way. I scooted over so I was laying on top of him I rubbed my dick in his slimy crack until it found its mark. I had my arms around his neck and worked my dick around, pushing and probing at his slot. He was moaning, and pushing back, so I increased the pressure a bit and the head of my dick lurched in. I let it sit for a few seconds and then began little pumps, moving up his ass tube a quarter inch as a time. When I was about halfway in, something gave way, maybe his sphincter had given up the battle, and all of a sudden, my pubes were mashed against his ass. I usually like to enter a dude face to face, but this more animal-like and dominating approach oddly seemed appropriate given how hot everything was.
I gave Taylor a few moments to get used to it, and began some slow pushes in and out. In a minute or two, I was picking up speed and pushing in a bit harder. After just a minute more, I felt his ass crush my dick and he yelled: "I'm cumming, fuck, I'm cumming!!" I felt him jerk about ten times. I pulled out and flipped him over and saw his face for the first time in a while. He had a dreamy smile on his face. I quickly rolled a condom on my slippery dick and lifted his legs and pushed into his open hole. This angle was much better and I could feel the top of my dickhead slide across his prostate. I felt I was getting a lot deeper and probing new areas of his pipe. I pushed in hard and deep as I leaned down to kiss him. Normally I would feed him his nut, but it was in a big puddle underneath him. While kissing, I couldn't get the leverage, so resorted to fast little strokes, just an inch or two out and then back to the bottom of his hole. I broke the kiss and leaned back up. I love to watch my dick go in and out of a beautiful guy's tight hole. There is something about seeing the hole just stretch to accommodate. As I've mentioned before, my favorite is to pull it all the way out and then shove it back in. Seeing that little sphincter rubber band winking and closing before being rammed two inches open in a heartbeat is exhilarating. I love seeing the effects of my fucking, a nice hard dick leaving pre everywhere, and those balls bouncing to the rhythm of my pounding.
I picked up the pace a bit and was really letting it travel in Taylor's tight hole. He had told me he doesn't like to get fucked for long, but it didn't seem the case here. He had already cum once, and I was going to ride that ass for a good long time. I fucked in different angles, put his legs in different places. I know for myself, the maximum feeling in my ass is when my legs are far apart. When I cum from a bj or jerking off, I always spread my legs as far as I can, and can really feel my ass. So I really pushed Taylor's legs far apart and hit his chute hard. His eyes were wide and his mouth was open. I let his legs close a bit and pushed them back with my shoulder as I leaned in. This position allows the deepest penetration, and I slowed down a bit to make sure I was getting all the way down in his ass before giving a final hard little shove. I put my fingers in Taylor's mouth and he sucked them like a hungry calf. Taylor had nice big low hanging balls, and I hadn't gotten to play with them. They had slipped back into the jock pouch while Taylor's nice size dick was sticking out the waist band, holding it in place so it had made a large puddle of precum. I scooped up what I could and held it at his mouth while his long tongue darted out to clean it off. I pulled his nuts out the side of the pouch and grabbed his ball bag above his eggs. Stretched out in their sac, I gave a little tug every time my dick his bottom.
We were both sweating and panting by now, my sweat dripping onto him and mixing with his. I let his balls go and grabbed both ankles, pushing his legs back and opening his hole up so I could concentrate on some good old fashioned buggering. I was really working it hard, and Taylor was moaning and saying dirty things every once in a while. "Fuck me." "Breed me." "Pound my tight ass." This sort of thing. Until after a few minutes just a: "Oh SHIIIIIIIT!!!!" I looked down and his cock jumped a bit from its confined position and shot a big glob of cum into Taylor's belly button. Hell yeah, I began to pound him slow, keeping it deep. After that first glob, a steady stream of cum came out of the bright red dick. I had never seen anything like it. Just a slow steady stream. I dipped my finger in the pool and took a taste. Not bad! I scooped up some more and stuffed my fingers in his mouth. I could feel his tongue on them like on my cock earlier. I kept drilling out his hole as Taylor's eyes closed and his head sank in between the pillows. After just a few seconds he said quietly, "oh man, that's so good, but take it out. That's enough"
I was shocked! Here I had fucked two hands-free cums out of him and NOW he wanted me to stop!? I pulled out and felt his hole. It was open and twitching, and when I pushed my finger in a little ways, I could feel his heart beat. His chest was heaving, and I tenderly asked: "Are you sure babe? You seemed to be enjoying it! I can cum quick, promise."
"No man, its too much, sorry."
"No worries dude, that's ok," I said, probably kind of dejectedly. He slipped out from the bed, leaving me kneeling there. He slipped his jock off and stood there for a second. I wasn't sure what was going on, but I desperately needed to cum. After a short pause he walked over and pushed me onto my stomach. He pulled me legs straight and apart and parted my cheeks. He licked up my crack and then focused on my hole, licking, sucking, and pushing his tongue in. It felt awesome. After a few minutes, he reached up under and pulled my dick down and the condom off. It was kinda painful, but I forgot about that when he started licking the underside and working my nuts. He flipped me over and moved up onto me. He rubbed the still large amount of cum in and around his navel onto my dick, and then pushed those lips right down to the base of my dick. His lips were so tight, they scooped all of his cum off my dick on his journey down my pole. When he got back up off my dick, it was a horny sight to see his long tongue lick around his mouth and catch all his nut, it looked like Scooby doo.
Even after the exhausting fuck, he hadn't lost any energy in sucking dick. I used all my energy to keep from cumming. I may have lasted 20 minutes, regaining strength when he would lift my legs and work my balls or hole for a minute. Finally, after a while longer, I could tell the end was near. He was rolling my balls around in his hand and sucking with a lot of force while pushing up and down my shaft and his tongue torturing my head with pleasure every time. A couple times he took it deep enough to lick my balls! At that point, I gave up, and immediately felt the cum rising. My legs were shaking uncontrollably and I felt my dick swell impossibly more. "Oh shit dude, that's so good. You're gonna make me squirt. You want that load. Fuck!" Taylor sped up somehow, and in a few seconds, I was flooding his mouth with what felt like a gigantic load. He kept sucking when my long orgasm was done. Usually I don't like that, but it felt good. He released my dick, and just licked softly around the head and my pee slit. He got up on his knees and we both laughed when I pointed out the used rubber was plastered to his chest. He came up for a kiss. I don't usually like to kiss a dude who has my cum in his mouth, but this seemed like a special time and a special guy, so we had a minutes-long hard wet kiss.
I had hoped to hang out and get to know Taylor better and drink some. I guess we knew eachother better now, but were both exhausted. Taylor went to the bathroom and I watched from about 10 feet away as he pissed, oddly erotic I thought to myself. It was probably about midnight, and Taylor crawled up next to me as I pulled the blankets up. We must have dozed off pretty quick because I don't remember talking about anything. When I woke up, it was a few hours later. Taylor was snoring softly and we had settled into a nice spooning position. My arm was over his chest, holding him tight to me, and I could feel my dick squeezed between his cheeks. I moved it a little, and it slid easily. I could feel it stiffening, so I gently moved it out of his crack. I pulled the blankets down carefully, until they were about at his knees. He stirred a bit. I lifted his leg up slowly, opening up his asscheeks. My dick was now hard as a nail, and I moved it closer. I tried to remember where the target was, I didn't want to miss. His crack was slippery with all the lube that had leaked out. I slid my dick from his balls up to where I felt a little depression. I held his chest and pulled him tightly to me as I thrusted forward and skewered him balls deep. Taylor jolted away with a moan and inhaled like those in movies when a drowning person has been saved and takes their first breath. To be continued.