Catching Up Part 5
- 4 years ago
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Harold free porn video
I finally made it, I have a full football scholarship to a small college and I’m away from home, for the first time in my life. I checked in, they had a whole staff to help you if you needed it, but I was fine, so I got my schedules, both football and academic and the key to my room. I knew I was getting a roommate, it was a small school and I was curious to see how the luck of the draw worked for me. He was already in the room and unpacked when I got there, it took me all of thirty seconds to figure out my roommate was gay and I wasn’t too sure how I should handle this situation. He was very shy and very small, I found out later he was only five foot three and slightly built, like a women. He asked if I was bothered by his being gay and I said as long as he doesn’t hit on me, no problem and it didn’t take me long to realize he was a great roommate. He did all the cleaning, he picked my clothes up and after a few weeks, he was doing my wash for me, what more could you ask for in a roommate. Things went real well I thought, we made it to winter break and my roommate had even come out to see me play at the home games, without any major problems. He went home for winter break, but I had a bowl game to play in, so stayed and left the room a bit of a mess when I left.
When I got back my roommate, Harold was his name, was siting on his bed crying, but the room was spotless again. I asked him what the hell was wrong, why was he crying and he said he didn’t mind cleaning and doing the wash, but I could at least acknowledge that he was doing something nice for me, once in a while. I tried for a couple of minutes to appease him, but nothing I said was working and I lost my patience and why I did what I did, I don’t think I’ll ever know the answer. I pulled my pants down and told to suck my cock, maybe that would make him happy. Before I could even blink, he had my cock in his mouth and it took me all of another shocked minute, to realize that he was the best cock sucker I had ever had, suck my cock. Until him, all I had ever suck my cock was a few girls and they weren’t even close to Harold’s cock sucking talent. I stood there with my toes curling as he sucked my prick like he was a musician playing an instrument and I just closed my eyes and let him suck to his hearts content His tongue and mouth were all over my cock, I had never had a blow job that even came close to what he was doing to my cock. My knees were kind of buckling, I was moaning out loud and then my prick started to swell, Harold grabbed my ass with both hands, so that I couldn’t pull out of his mouth. I groaned loud and my cock went off like a cannon, shooting my hot cum into his waiting mouth and he swallowed every drop of my cum. After he licked my cock clean, he was holding it in his hand and looked up at me and said, “Now that wasn’t so hard was it” and I just shook my head no. I had gotten back late and after getting the blow job of a life time, I was ready for bed.
I woke up with a start and an aching hard on about three in the morning and Harold was sitting on the edge of the bed. He said I was making funny noises in my sleep and had woke him up, so he came to see if I was okay. The covers were off me, I had gone to bed naked, my cock was standing at attention and Harold reached over and wrapped his hand around it. His hand sure did feel good on my hard cock, as my cock really needed some attention at that point and Harold asked me if I would like him to take care of my problem. Before I could even answer, he was between my legs with my cock in his mouth and I just lay back and let Harold do his thing to my now, happy prick. He worked out on my cock for quite a while, bringing me almost to the point of shooting my load and then backing off, until I grabbed him by the hair and said, “Make me cum bitch, make me cum” and Harold made me cum so hard, my ass came off the bed a little. I woke up with Harold between my legs, kissing my hard cock, so again, I made him happy and pumped my hot load down his throat. We fell into a routine after that, Harold would suck my cock every morning and night, making us both happy and we finished out the year with our routine, nobody the wiser. He emailed me a lot over the summer and when I told him I had to be at school earlier then him for football practice, he told me he would be there to, so I wouldn’t have to worry about the little things, like cleaning and washing clothes. I will say, I sure missed his blow jobs and was looking forward to seeing him. I had just finished practice and was taking a shower in my dorm, when Harold waltzed into the shower naked and got on his knees to my now hard cock. He licked and sucked my cock like my cock was a musical instrument and had me moaning like a cunt in no time. I filled his mouth with my hot cum and he moaned while swallowing it.
We hugged and I was surprised at how good his naked body felt against mine and I
didn’t mind a bit when he held my ass with both hands and squeezed. Since there
was no one else in our dorm yet, we walked naked back to the room and he was
ahead of me and I couldn’t help notice that he had a cute ass and walked like a
girl. By the time we got back to the room, I had a hard on again and Harold
asked what brought that on, so I told him. He smiled, asked if I really thought
he had a cute ass, I said yes and he had better watch out, I just might want to
fuck his ass. His answer, he got on the bed on all fours and waggled his ass at
me, telling me it was all mine if I wanted it. I started to get on the bed,
Harold said, “Wait a second,” got some kind of lubrication and put it all over
my prick and his asshole. He got back on the bed, said, “Take me honey, take
me,” so I ignored the honey part and proceeded to start putting my cock into his
asshole. I worked the head in, his asshole was so tight, I almost came, asked
how he was and he told me to put it all the way in, he was ready. I pushed
against him, he pushed back and my cock buried itself in his ass, making him
moan like he was in pain. I asked if he was ok, he told me to fuck him real slow
until he got totally used to it, so I began a slow fuck in his ass. His ass was
so tight on my cock, I couldn’t hold it and my cock exploded in his ass, making
him moan, but surely not in pain and I was amazed at how much I enjoyed fucking
Harold in his ass. I took Harold out to dinner and as usual, it was like being
with a girl, but this time, I couldn’t take my eyes off his ass, every time I
got a chance to look at it. When we left, while walking back to the car, I put
my arm around Harold, squeezed him and told him I wanted to fuck him again, he
squealed like a little girl and kissed me on the lips. I know I should have
gotten mad, but after all, he was going to let me fuck him and it was a nice
kiss.
We got back to the dorm, Harold was naked before we got to the room and as soon as we were in the room, Harold had his ass lubed and was doing my cock. He finished lubing my cock and looked at me, saying, “I really like to be kissed before I get fucked,” and I thought, what the hell and kissed Harold. He was a good kisser, it was like kissing a girl, so I put my tongue in his mouth and I thought Harold was going to faint. I put him on the bed, mounted him and worked my cock into his asshole, nice and slow and it went in a lot easier this time. I fucked Harold like he was a woman and he loved it, he made himself cum while I fucked him and he squealed when I shot my hot load up his ass. Now we had a new routine going, Harold would jerk me off, I loved his small warm hands on my cock, or suck me off in the morning and we would fuck at night and I got so used to kissing him, it was almost an automatic thing between us. I would even lay in bed on my back while Harold rode my cock and he would lick me clean after we finished, from time to time. Right before winter break was Harold’s birthday and when I asked him what he wanted for his birthday, he surprised me. He told me he wanted me to fuck him missionary style, like he was a woman, so I readily agreed, thinking this should be interesting. Harold lubed us both up, got on the bed, lifted his legs and spread them so I had easy access to his asshole. I took hold of Harold’s ankles, Harold took hold of my cock and guided it into his asshole. By now I didn’t have to go slow, I just rammed my cock home, Harold grunted and said, “Fuck me honey, fuck me hard, honey,” so being totally used to be called honey now, I slammed the meat to him. I pinned his legs back to his shoulders like he was a little cunt and fucked him hard. His cock kept rubbing against me and it felt kind of nice and besides, at that point, I was so fucking hot, I didn’t care about anything but fucking Harold. He was a great piece of ass, he tried to fuck me back as best he could with me pounding him hard. My prick started to swell up in Harold, he was moaning, “Here it comes honey, here it comes” and as I shot my load in him, he came all over my belly and I liked it, it was so hot on my stomach.
Poor Harold was in a bit of shock because he came on me, he kept saying how sorry he was, so before I pulled my cock out of his ass, I kissed him and told him it was ok, I liked it. We slept together after that and I wiil tell you I loved sleeping with him, I would put my cock in his ass crack, wrap my arms around his warm, soft body and go right to sleep. Harold had started a new thing, he was rubbing my ass in the morning while he was sucking me off, using some lube. I let him because it really did feel good and after about a week of him touching my asshole, I didn’t flinch any more and a few days after that, just as I started to cum, Harold rammed his finger up my ass and I had the most amazing orgasm ever. It made me cum like I never had before, I loved it. Of course after that, Harold did it every time he gave me a blow job and then one night after our missionary style fuck, I was holding Harold like he was my girl, which I guess he was, I asked him what it felt like when I came in his ass. He tried to explain it to me, but wound up telling me I should try it to see and for the next few days, I thought about it. Harold’s cock was not big and now he was putting two fingers in my ass, I thought, what the hell, why not and when I got back to the room that afternoon I told Harold to lube my ass up and fuck me. I got on all fours and felt like a little cunt, but Harold was pushing his cock into my ass, so I didn’t have time to think about it. His cock was bigger then his fingers, but not too much bigger and it went up my ass rather easily. Harold started fucking my ass, had hold of my cock at the same time and was jerking me off, while he fucked me. I was really surprised at how good his cock felt in my ass and I started moaning, bringing Harold to say, “You like it, that’s my honey, you like it.” He fucked me for about five minutes, now using me like I was the girl and I really liked being fucked up the ass.
After about five minutes, I felt Harold’s cock swelling up in my asshole, he rammed his cock home in my ass, stiffened and shot his load up my ass. His cum was hot, real nice and hot and I loved how it felt shooting up my ass, loved it so much, I came and Harold didn’t even have hold of my dick. Our routine changed again after that afternoon, now Harold would fuck me first, then I would fuck him and I wasn’t even looking at girls anymore, just wanted Harold. After a few weeks of being fucked by Harold I had a whole new attitude, so when he had just finished giving me my morning blow job and I was holding him while we talked. He asked if I was ever curious about what a dick tasted like, since I liked having my asshole fucked and cum in. Well old Harold had me thinking again and after a few days of pondering whether I should suck Harold’s cock or not, I opted to try and the next morning Harold and I did a sixty-nine. When I took Harold’s cock in my mouth the first time, I was surprised at how silky it felt in my mouth and how much I liked sucking on it, it tasted so good. I tried to do to Harold what he did to me and it seemed to be working, he was moaning while sucking my dick now. After a little while, Harold’s cock started to swell up in my mouth, it felt even better now in my mouth, I could feel my cock growing in Harold’s mouth and then I felt his hot fluid fill my mouth, bouncing off my tonsils. I tasted and swallowed his cum at the same time, it was a bit salty, but otherwise I liked the taste of Harold’s cum and I have to admit, I liked the feel of his hot, hard cock in my mouth. That moment when I took Harold’s cock into my mouth, changed my life forever, Harold and I never wore clothes again when alone, when Harold got hard, I either sucked him or fucked him and we would make out while watching TV, we were like boyfriend and girlfriend, except we now both sucked and fucked cock.
Our senior year brought another party into the picture, a tranny came to our campus as a student and after we got to know him/her, I invited him for a sleep over with Harold and I. Our routine changed again after that night, both Harold and I found out we loved to fucked in the ass while sucking on a hot cock and our tranny friend had a big cock for us to enjoy and it only took a couple of ass fuckings to get used to the size of his cock and for some reason, his cum had a really nice taste to it, so we all got an apartment together. We started off every morning in a daisy chain sucking cock and I got to liking having my ass used as a pussy so much, I made both of them fuck me every night, so I could feel their hot cum shooting up my ass. After graduation, our tranny moved back home and Harold and I started our own business and Harold’s female next door neighbor, who was Harold’s best friend with money, became our third partner and also took over our lives. She moved in with us, loves fucking both Harold and me with a strap-on, makes us put shows on for, sucking and fucking each other and she dresses us up like a pair of whores, makeup and all, for her amusement and truth be known, both Harold and I like being made to look like whores and fucking each other while wearing woman’s clothes, it definitely adds to the excitement, especially when she tells us what good little whores and sluts we are. Like I said, my life changed dramatically and for me, it was all for the best, I love Harold and his sweet cock.
Rowan
- 20.03.2023
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