Finally Getting Fucked at College - A sequel to "Losing my cherry at his lakehouse"
After losing my cherry as a Junior in college to an older man I really wanted to get some more cock. Although older men really are my thing, I was also attracted to tops my age that were bigger and more muscular than me. The last time I had gotten some action I had to travel quite far away to the nearest city from where I was attending college. If you have read my last story, I was enrolled in school in a remote mountain town in Upstate New York and I was afraid I would have to travel again to get fucked!
So anyway, here I was during the school year, busy as could be with only my toys to provide any sexual relief for me, wondering when I could get away and have some sweet sex with my man in Burlington. This is when Toby came into my life. I had never spent too much time socializing with the rugby team in my small school, but I had always appreciated their ruggedness and muscled bodies. I did have one friend on the team and one day we were hanging out when he mentioned somehow that Toby was out of the closet, but my friend being very comfortable with his sexuality, had no problem with that of course.
Toby was someone that I had never even thought about hooking up with before I knew he was gay as I'm not into the idea of fooling up with straight guys for some reason. He was about 4 inches taller than me with big, toned muscles which he showed off by wearing tight jeans and shirts all the time. He was clean shaven and had a faux-hawk. His skin was as white as could be it seemed which was funny considering all the time he spent outside. Simply put I went from being pretty attracted from a distance to having a huge crush on him after just a quick conversation in which his sexual preference was casually stated. I started hatching a plan to get closer to this guy.
I started hanging out with my buddy from the rugby team even more than I already had been, which was fun either way as he was a great guy and a good friend. As a result I started to get to know some more guys on the rugby team. One night, Toby and I really got to know each other. I was scheduled to play beer pong on the same team with my buddy when he got a call from his girlfriend and had to go. Toby stepped up to the plate and offered to be my partner for the match. My heart started pounding and I felt butterflies in my stomach. Turns out we were a great beer pong team as I calmed down and just enjoyed myself. We spent quite a while dispatching opponents and having a great time. Toby wasn't aware that I was attracted to guys when we first met. I played it cool and didn't really let on until we had quite a few cups of beer in us and been eliminated from the table. I said I needed to go as I had work the next day and didn't want to be too messed up. I really wanted to say something and figure out a way to spend more time with him but I didn't know how when he gave me the perfect opening.
At this point Toby said, "Man, you sure are a great partner! We should do it again some time."
I replied with a half-drunk, half-serious sexy look in my eyes, "I'll be your partner anytime." THen I winked at him and laughed.
Boy, the look of pleasant surprise that flashed on his face was priceless. He recovered quickly though and said with a broad, knowing smile, "Well that sure is good to know. So, you want to hang out soon?"
I told him I would love to, allowing myself to let him know I was down for some action, biting my lip a little and giving him sex eyes. He took his phone out and I grabbed it confidently and put my phone number into it and said, "Call me. I really want to hang out sooner than later."
He said, "Oh trust me, I will.." with a coy smile of his own. At this point he touched the small of my back and allowed his hand to drop down and slightly caress one of my ass cheeks.
I laughed a little to let him know I liked it and said, "Well, bye for now. See you real soon," and started walking back to my apartment knowing that he was checking out my ass as I walked and really letting it wiggle back and forth to give him something to think about.
Two days later and I was tired of waiting for him to call me. My shift at work had come and gone, with me fantasizing the entire time about making out with this muscled man and letting him have his way with me. It was a monday afternoon, I had just finished classes and I had run out of patience (So soon, I know). I had begun the ritual of playing with my ass. I cleaned my ass out and was in the middle of fingering myself to loosen things up so I could use a toy. Suddenly, I heard my phone ringing. I looked at the screen, and saw a number I didn't recognize. Hopefully it was him! I answered it.
"Hello?"
"Hi. Is this Matt?", I heard Toby say in his sexy voice which was a little deep while also sounding the slightest bit queer, if you know what I mean.
"It sure is! Hi, Toby. How are you?"
"I'm great! How are you doing."
"I'm doing a little better now that you've called," I said with a laugh as I smacked my forehead with my hand. How corny could you be!
He laughed and said, "I bet! So, you want to come over and 'Watch a movie'?"
Clearly we both knew what was going to happen. I told him I would love to and asked hime where he lived. He gave me the address, which was about 15 minute walk from my place near the edge of town. He had his own little cabin set back in the woods. I told I would be there in 20 minutes or so and we hung up. Luckily I was pretty much all set for some sex so I made sure I was cleaned completely, got dressed, and grabbed a couple condoms and some lube. The walk over there was like a dream. I couldn't get there fast enough. About a block away I had to slow myself down so I wouldn't be huffing and puffing with him thinking I had run from my place.
I walked down the dirt road toward his cabin. When I knocked on the door, he opened it with a smile. I smiled back and we said Hi awkwardly to each other.
"So, what kind of movie do you want to watch?", he asked.
"Whatever, I'm up for anything."
"I just got this old Hitchcock collection. You want to watch something from that?"
"Sure! I actually love Hitchcock." (Which is true)
I have no Idea what movie we were watching though. We both settled in on the couch next to each other, not even really touching at first. Our thighs and knees however were before too long pressed right up against the other's. At one point something funny happened and I looked at him and laughed and gave him the look that I thought would let him know he should make a move. Thankfully he took the hint and put his arm around me. When he did this I put my hand on his thigh and rubbed down to his knee and back up again toward his crotch before rubbing back down. We were looking each other in the eyes at this point when he leaned in and gave me a kiss on the lips. We kissed tenderly for a little while, both moaning a little and exploring each other bodies carefully.
At some point, I am not sure when, the tender kissing became full on making out, which eventually led to me putting my hands under his shirt and feeling his rippling muscles. I broke free from his kiss and practically ripped his shirt off. He did the same to me and we went back at it. I was feeling up his chest while we made out and eventually my hands drifted down toward his crotch. I was clutch at his thigh and felt what I though might be some muscle in his leg. It was big, sinewy, and hard. I reached for the other leg to feel his muscles there and realized he did not have this particular muscle on his other leg. I looked down and gasped, "Oh my god!" I said.
"What is it?" he laughed a little at my surprise.
"Is that your dick?", I said pointing down at the snake running down his jeans.
"It sure is!", He said with a huge smile.
"Well, looks liek I just hit the jackpot then!"
He laughed again and said, "You sure did! I think I may have too. I haven't found anyone around here to hook up with pretty much ever."
We began making out again. I was paying more and more attention to his dick through his jeans and he was beginning to thrust his hips back and forth a little as we made out. I let him suffer a little bit, before finally unzipping his jeans which were as taught as could be what with the extra filling in them. I manuveured my hand into his underwear and gently stroked his cock. It was shaven and seriously felt like a python to me. We stopped making out while I rubbed his dick in his jeans. He threw his head back and moaned in relief. While still playing with his dick I started to kiss and suck his nipples. I slowly made my way down his chest and stomach toward his crotch. I pulled his underwear down just enough for his thick, bulbous, and shiny dickhead to stick out from them. I flicked my tongue across his dick head before licking around it and finally taking it into my mouth. At this point I pulled his underwear and jeans down with his head still in my mouth. I pulled the dick up off his belly with just my mouth and got on my knees and front of him. I made eye contact with him, he ran his hand through my hair.
Toby moaned and said, "It feels so fucking good, baby.."
Then I went to town. His dick was real thick. Definitely thicker than anything that had been in my ass before. It was also of decent length, being perhaps 7 inches long. I was loving this thing. My mouth was as wide as it could go and I was getting about 3/4ths of the way in before not being able to go any further. But I could tell I was doing a good job lavishing attention on his massive tool. Sucking and licking and using my hands to give him total pleasure.
Suddenly I felt his hands on my head slowly pressure me to pull of his dick.
"Man, this feels so good, baby, but what I would really like is to play with your ass before I come. Can we do that?", He said with a glimmer of hope in his eyes.
"Of course. If you want to fuck me, we have to use a condom though. I have one in my jacket." I said as I stood up and began to walk over toward the door where my jacket was hanging.
"Don't worry about it! I have one right here."
He pulled a condom out of his jeans. "Let me just grab the lube real quick then." I said smiling. I was over the moon knowing I was about to get fucked soon.
"oh ok", he said. "Why don't you drop your clothing on the way back." Meanwhile he kicked his jeans off his feet and took his socks off making him totally naked.
On my way back to the couch, I undid my pants and quickly removed them. I wasn't wearing any underwear, as I didn't see the point for a meeting like this. When I reached him we were both standing up. We embraced each other. I was running my hands up and down his broad back muscles and he was holding my waist and feeling the way it curved down into my ass. He then grabbed both my ass cheeks and gave them each a little slap.
"Man, you have such a great ass!"
"Thanks.", I replied demurely.
We then kissed passionately for a minute or two. During it he had begun to probe my crack. A finger brushed past my hole and I felt electricity run up and down my spine originated from my anus.
He pulled out of the kiss and told me I should get on my knees on the couch with my ass facing out, grabbing the back of the couch. I took the position, arching my back and spread my legs enough to give him open access to my asshole. He started rubbing my asscheeks. I turned my head and he gave me a big kiss before kissing down my back. He stopped just short of my crack, which was fine with me as I am not really into rimming. He got on his knees, grabbed the lube and poured a bunch into my crack and onto my hole. He started rubbing it into my ass, brushing my asshole with his fingers. I was pushing back into him, just begging to be fingered.
Then he asked, "Ready to be fingered, baby?"
"Oh my god, please!", was my only response.
I then felt his finger press against my ass. Slowly, he applied pressure and I pushed out enough to feel it pop right in smoothly. I moaned loudly. His finger was quit thicker than mine. Although it presented no challenge to me it stretched me that much more than when I finger myself to open up my ass. He quickly bottomed out with one finger and began to finger fuck me slowly. I had the familiar feeling of electricity spreading from my asshole which I knew was bound to become more and more intense. He then added another finger and then another until he was really stretching me with his finger fucking. I threw my head back and just enjoyed the ride gasping and moaning a bit. This went on for a couple minutes. He was really making sure I was nice and loose, moving his fingers up and down and side to side while fucking me steadily.
Suddenly he pulled his fingers out and said, "You think you are ready to try taking me now?"
Man, was I ready. "I think so Toby. Go nice and slow."
"Don't worry Matty, I will.", he reassured me.
I rested my head against the back of the couch and watched him milk his cock to get as hard as could be, open up and put on a condom, and put some lube on his big dick, which all served to give me a little fluttering in my stomach as I anticipated having my brains fucked out of me. He poured some lube on my hole and quickly put his dick at my loosened opening to catch it before it slid down my crack onto the couch or floor. At this point I picked my head up, arched my back and opened up my hips as much as I could in response to his cock taking the position. I closed my eyes and focused on relaxing my ass muscles as much as possible.
Toby slowly pushed forward with his hips. In response I pushed out and moved my hips toward him. All the sudden, I felt a pop and his massive head popped passed my ass lips and inside of me. A feeling of uncomfortable fullness overtook me and I just moaned/ whimpered loudly in pain with a little pleasure.
Toby asked, "Are you okay?!" with concern in his voice and I quickly said, "Yes, Yes. I'm fine, just stop for a second." I was pushing back just enough to make sure he didn't pop out. I was breathing heavily, trying to relax as much as possible. My ass lips were stretched wider than I had ever felt and I could feel them pulsating to take this invader. After A minute or two, the discomfort was replaced with a warm fullness and I knew my ass lips had finally decided to accept the width of his dick.
"OK. You can keep going slowly, Toby". I turned to look at him. He leaned forward and gave me a big kiss on the mouth.
He then grabbed both my ass cheeks and started applying pressure. Slowly, his dick moved further into my ass. As it moved along my insides it put pressure on every wall, sending my nerve endings firing like crazy. Each time he went deeper I felt pain but when he pulled out and pushed back into to that point it felt like fireworks going off and I couldn't get enough of it. Be fore too long, with the help of plenty more lube, Toby was pistoning in and out of my ass with just over half of his dick. I was moaning in an almost feminine way, pushing my ass back to meet his every thrust. Toby was holding my waist and telling me how great my nice tight ass was and how sexy I was. Occasionally he gave my ass a light smack. During this and without me realizing it, Toby had worked his way into my ass further. It wasn't until he hit my second sphincter that I knew he was almost all the way in. I felt his dick head slam my second muscle wall and I cried out a little.
"Oh sorry, Baby. Are you ok?!"
"Yeah! Wow, you must be almost all the way in huh?", I said feeling back there. I was surprised to find just and inch and a half left of his cock outside my asshole. "Ok. Just go slow and apply pressure. I am sure we'll get over this hump."
Toby started rubbing my back, waist, and ass cheeks to relax me. Meanwhile I breathed deeply and focused on pushing out my ass muscles to try and relax that sphincter. For the second time that afternoon, this time in a much more pleasant way, I felt my ass muscles release, and his dick head gained access through my sphincter. This time, I felt pure pleasure and warmth as his dick stretched my inner recesses, his balls rested against my taint and he was pressed right up close to me.
Then we really started to fuck. With me fully stretched loose and open, Toby began fucking me in short strokes deep and then he switched to long dicking me. He pulled almost all the way out before slamming home with a whack of skin against skin both wet with sweat from the sex. We really settled into a groove. I had my eyes closed, just enjoying the feeling of my asslips being spread, my insides being stretched, and my prostate being nailed over and over again. I was on cloud nine, moaning and whimpering. Toby was grabbing my ass and my waste and riding me like noone's business.
Eventually he said, "I'm gonna have to cum soon, Baby!"
"I want to come too! Let me get on my back and we can cum at the same time with you inside me!"
Without saying anything, he just pulled out. I flipped around and threw my legs to each side of me with my ass hanging over the edge of the couch. Toby Grabbed my legs and pushed them back which lifted my ass up giving him access to my ass hole, which was wide open by now. With one movement he pushed his cock all the way into me as I moaned and threw my head back.
"I'm going to come in like 30 seconds," he said, out of breath.
"OK, fuck me baby. I'll cum right after you," I replied.
Toby began to feverishly bang me as hard as he could. The couch which had honestly dealt solidly with all the fucking beforehand was rocking and creaking a little bit in rythm with his thrusts. I had begun jerking my cock lightly, waiting for him to blow before really applying pressure. I was gasping with every thrust in blissful pleasure.
Suddenly Toby let out a moan/howl and slammed all the way into me, sending an electric charge throught the core of my body. It felt like he had actually felt a way to go deeper than he had already made it inside me. I felt a flood of boiling warmth fill the condom as he came inside me. As he pulled out the littlest bit and slammed in again continuing to empty his balls, I jerked my cock harder and within seconds began to shoot ropes of cum into the air. It bounced off his chest and showered my sweaty, wet body. My mind went blank and was filled with an explosion of euphoria as I was overcome with the feeling of having my ass filled with Toby's big dick which I had just felt explode hot semen inside of me along with my own explosive orgasm.
Eventually, both our orgasms subsided completely. I came to with Toby barely holding himself off of me with his dick still fully buried in my buzzing, spent asshole. We were both soaked with sweat, sticky from all my cum, and breathing hard. Our faces were beet red from exertion. We looked at each other, started laughing and had a big sloppy, tired, wet kiss.
"That was ammaazzing!", Toby said.
"It sure was!", I agreed.
"We should do it again sometime."
"We should do it again soon. Really soon!"
He laughed and gave me another sloppy kiss.
Of course, we did do it again soon!