- The following is not true but is a work of fantasy. This is my first story, please let me know if you enjoy it.
It was the end of November, just after the Thanksgiving holiday, and I was headed home to the east coast after an enjoyable holiday weekend with my family. Being at home with the family all weekend also made it difficult to get away and get off so I couldnt wait to get home, break out some good porn and jerk off. A little about me - I'm 27, 6'0" with brown hair and blue eyes with an average build. Certainly not ripped but also not fat - just your average, everyday guy.
Sitting around in the airport boarding lounge, I looked around to see who else would be on my flight. Always nice to see if there was a hot guy or two that would make a good jerk off fantasy when I got home later that night. I noticed a younger guy - late teens or early 20s I guessed; a little shorter than me with a bit of a nerdy look to him. He was cute and I noticed his nice ass in his jeans as he walked by. I took careful mental notes thinking that he would make a good image to jerk off to later.
As we boarded the plane - I was one of the first on board - the advantage of flying a lot and having high status with the airlines. It was a small regional jet for the hour long flight to Chicago. I enjoy people watching as everyone boards the plane - again looking for nice material to fantasize about later. Soon, the young guy from the boarding lounge got on the plane and started walking towards the middle of the plane. I soon learned he would be sitting next to me which would give me more time to discretely observe him. As he reached to put his bag in the overhead bin, his shirt pulled up and I saw the grey waistband of his Hanes underwear. I assumed they were boxerbriefs since they tend to be most popular. This got me going even more as I have a total thing for guys in their underwear. The thought of this cute guy in his boxerbriefs made my cock jump a little.
The flight was short and we made small talk on the trek to Chicago. I learned his name was Jake and he was on his way back to college in the northeast after the Thanksgiving holiday. I watched carefully as I thought I saw him try to discretely check me out. Not sure - I casually reached down and adjusted my cock in my jeans to see if he had a reaction. He smiled slightly but looked away probably so as not to be obvious that he might have been checking me out.
We landed in Chicago only to find that many flights to the eat coast were cancelled due to snow that was hitting the region. I talked to the agents and found out I couldnt get home that night and they set me up with a hotel room. I was somewhat shocked at the ability to get me a room given all the stranded passengers, but I suppose the airline status may have helped.
As I headed for the terminal exit, I saw Jake sitting in one of the boarding lounges. I walked over and asked if his flight had been cancelled as well. He said it had and he was figuring he would be sleeping on the floor of the airport since the airline didnt offer to get him a room. He said he was rebooked out on a early-afternoon flight the next day so it could be a long time hanging out in the airport. I quickly thought to myself that I could be nice and offer to let him stay in my room but also thought that might be weird since we had just met on the plane. I figured what the hell - if he said no - it wasnt like I would probably see him again so it couldnt be that big of a deal.
I told him I had a room and that he could stay in my room if he wanted - if it wasnt too weird for him. He thought about it for a minute then said that it would be nice to not sleep on the floor of the airport. I decided to push him a little further and said that he might not be able to stay for free - he might have to do something to repay me. He asked what that was and I said there were a couple ideas (I also adjusted my cock again). He smiled and agreed and we headed off to the hotel.
We got to the hotel, checked in and went up to the room. He didnt have much since his luggage was checked but I had my regular bag I always carried on. He said he was going to go take a piss and wandered off to the bathroom. As he peed, I got undressed to my boxerbriefs and laid down on the bed. My cock was already getting hard in anticipation of what might happen. He came out of the bathroom and saw me on the bed - he asked if he should get naked. I told him to keep his underwear on but anything else could come off.
As he stripped, I asked him what he had done with guys. He said not much, just kissed, jerked off and done oral but that he was open to more. He had only been with two guys so was still pretty new. He was hard in anticipation and I could clearly make out his boner in his blue Hanes boxerbriefs.
We started making out as I rubbed his cock thru his underwear. He quickly pulled my underwear down to start jerking my 7" cock but I wanted him to keep his on. I kissed down his chest, sucking his nipples each a little then down to his stomach. As I kissed along the waistband of his boxerbriefs, I pushed his legs open and positioned myself between them. Slowly, I licked his hard cock thru his precum-soaked boxerbriefs. Licked him all the way down to his balls. After spending a little time on his balls, I pushed his legs up and let my tounge lick over the fabric of his boxerbriefs to his butthole. He moaned slightly - I let up and asked if he had ever been rimmed before. He said he hadn't and I told him to just wait under my tounge was on his bare hole.
I told him it was time to see what his blowjob skills were like and I laid back and let him work on my cock. I didnt expect much for a kind of nerdy kid with not much experiance, but it felt amazing! He worked my balls and cock head, deepthroated me and got me rock hard. I knew I wanted more of this guy - I pushed him back on the bed and quickly pulled his boxerbriefs off.
I took his cock in my mouth and started to suck it. Bobbing up and down on his cock and tasting his hot precum. I deepthroated him while I played with his balls. As I sucked him more, I let me finger explore his tight asshole. I didnt penetrate him but just ran my finger around it slowly. He was clearly very tight.
I let me tounge explore his balls - sucking each a little and licking his sac all over. I pushed his legs further open and licked underneath his balls. As I pushed his legs up a little, I ran my tounge back and forth across the base of his balls and the very edge of his hole. After teasing him like this for a minute or so - I shoved his legs up and let me tounge go to work on this tight virgin butthole. He moaned loudly while I gave him the best rimjob I could. I licked my finger and slowly slid it into his asshole. I finger fucked him with one finger for a while, then slid in another. I pulled my finger out and went back to work with my tounge - this time tounge fucking him just a little.
I stopped rimming him and asked if he wanted to feel my cock in him. I'm mostly a bottom, but topping this hot tight hole I knew would be amazing. He shook his head yes and I went to my bag to get a condom. I slid it over my cock and grabbed a small bottle of lube from my bag. I worked lube into his hole with my fingers then put the tip of my cock at his hole. I asked him one more time if he wanted it and he said yes. I started to push in slowly knowing it would take some getting used to. He winced in pain and I asked if he wanted me to stop. He said no and I penetrated him more.
After almost a minute to slowly penetrate my whole cock into his butt, I finally had it all the way in. I let it sit so he could get used to it then slowly started to fuck his ass. From his moans, I could tell he was getting more used to it and I sped up my fucking. Soon I was pounding his butt with all I had - I knew I could get off in no time. I reached down and grabbed his cock to start jerking it. He moaned loudly and I felt his asshole get tigher on my cock - a second later - he was shooting ton of cum all over his stomach. My own cock was ready to explode and I shoved my cock all the way in and started to unload in the condom. I slowly pulled my cock out then reached for his boxerbriefs on the floor. I wiped his cum off of his with his boxerbriefs and tossed them over into my suitcase.
We laid on the bed tired from our hot fuck session. We made out for a while then crawled under the covers and went to sleep. I few hours later, I woke up to his hard cock against my butt. I rolled over and grabbed it to start jerking it. We kissed some more and he asked if he could find out what it feels like to fuck a guys butt. I was instantly hard and my hole twitched with the thought of this guys beautiful, 6.5" cut cock in my hole.
I grabbed a condom and some lube. Eagerly, I got on my back, pulled my legs up and open my hole to his hot cock. He was hesitant at first - barely pushing in and hardly fucking. I pushed back towards him and got him to penetrate me further. Soon his whole cock was inside me. I told him to pound me like I did him and he quickly got to it. The feeling of his hot cock pounding my asshole was hotter than I imagined. It didnt take long for me to bust my nut all over my chest. As I came, I could feel his juice shooting into the condom inside me. We quickly cleaned up and went back to sleep.
The next morning we woke up and had to get ready to leave for our flights. Jake said getting fucked was very hot and he wanted to feel my cock in him one more time. We had just enough time to fuck and still have time to shower and get to our flights. I went to my bag but found that I didnt have anymore condoms. I told Jake that we could fuck but that it would have to be bare since I was out of condoms. He thought for a moment then said that was ok - he was curious what it felt like to have cum inside of him.
I quickly lubed my bare cock and slid it into his waiting ass. I knew that bare it wouldnt take me anytime at all to shoot my load. As I started to pump his butt, I grabbed his cock and jerked. Then I pulled out and told him to get on all fours on the bed. I started to fuck him doggy style while reaching around and jerking his hard cock. A few minutes later, I was ready to cum. I shoved my cock deep into Jake and started to shoot my load deep into his asshole. As my cum flowed into his hole, Jake started to blow his load all over the bed. As I pulled my cock out - I saw a little of my cum drip from his hole.
While Jake recovered, I jumped in the shower and got ready to go. As Jake showered, I got dressed. When he came out, he asked where his underwear was and I told him that I was wearing it. I was totally turned on my wearing this cute guys cum soaked boxerbriefs and I wanted them as a momento from our hot encounter. I thew Jake a pair of my dirty boxerbriefs from my bag and told him he could wear those or go without. He put my underwear on and finished getting dressed.
We exchanged emails and phone numbers on the way to the airport promising that we would fuck again if we were in the same place.