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The pits of financial independence

Anal sex – the way of the dogs

Me and Steak went out to dinner last night. I tried to keep my expectations low – as high expectations tend to destroy my dates like a malevolent swarm of deadly nanoparticles (Michael Crichton’s mediocre book is still in my head.)

My main job was to act like myself. I think I act differently when I become nervous – hence the brief nature of most of my relationships.

The dinner was alright. Not bad, not good. We discussed politics most of the time. We agreed on most areas – but we reached a deadlock when Fidel Castro entered the conversation. I don’t like Castro by any means, and I think the world would be a better place without him, but I’m not willing to categorize him with people like Hitler and Stalin. Steak was raised in a wealthy, South American family. He’s a wonderfully nice guy – but he can’t shake off the elitism and didactism that he was born with. At times his high-nosed nature offended me.

He showed zero physical affection in public. He mentioned to me before that that had been a big issue with his previous boyfriend. His boyfriend always wanted to hold hands in public and Steak didn’t. I see both sides of the coin – but I agree less with Steak

Back at Steaks place we lay down to watch TV (what the fuck is the past tense of “lye?”). Maybe hes comfortable with me now and the initial infatuation has passed – because he doesn’t show the non-stop touchy feeley bullshit he used to. God I wish he did.

I ran my hands all down his body and ended up face to face with his cock. I sucked on his lower stomach and then tried to get his belt buckle off. If someone had tied me to a timed explosive with that belt I would have been fucked. It was more intricate and complex than the Theory of Coordinated Management of Meaning. Eventually he helped me and I got it off. I sucked on his dick slowly – like it was a pacifier. I then noticed that he was uncircumcised. Amazing that I could suck a guys dick (and fuck) so many times and not ever notice. I played with his foreskin – I found it fascinating. Nothing repulsive about it.

Then I made it clear I wanted to fuck. He said “Well then sit on top of me.” I couldn’t believe he was so lazy that he didn’t want to move. I said no. Then I suggested, if he wanted to watch TV that bad, that he fuck me doggy style so that he could still get glimpses of his precious, plasma screen. He laughed hysterically at the suggestion. Then we decided to go upstairs to his bed and do it doggy style there.

Honestly it was my first time fucking in that position. People think thats how gay guys fuck, but its not. I prefer face to face fucking.

It took a long time for his dick to squeeze in. Once it did PAIN. I made him pull it out. Then he tried again without asking me. This time it went in all the way. He started fucking me immediately. There is more pain when you fuck doggy style for both partners – later he told me that my ass was so tight it hurt his dick. As always, after a minute of adjusting – I told him to fuck me harder. He did. As he fucked me he ran his hands all up and down my back and shoulders. That was all the intimacy I needed. Eventually his hands settled on my waist – thrusting his pelvis back and fourth like it was his job.

Suddenly I felt an unusually intense orgasm coming on. “I’m cuming….oh fuck…oh FUCK!….OOOOOHHH” I was shocked by the intensity of the pleasure radiating out of my ass. I spermed all over his bedsheets. It was then that I realized that he was at the back end of an orgasm as well. We had cum at EXACTLY the same time!

Afterwards we went back to watching TV. We (rather he) became obsessed with the Wright/Obama incident. We went on youtube trying to find the defaming speech – but we weren’t sure if we had found it. Nothing Wright said in the speeches we saw seemed overtly offensive.

Then he told me that he is anal retentive and that sometimes he takes big shits and they make his ass bleed. Him talking about shitting left a distinct sense of panic in me. I wanted to run away, still in my underwear, down the five flights of stairs to my car. “Oh is this not something we can talk about?” he asked me, detecting how uncomfortable I was. “Oh no, go right ahead and keep talking about it.”

Even though he disrespected me with his shit talk I still love his ass. Its a little bubble butt – entirely hairless and smooth. I kept trying to grab it before I left. We got into a wresting/tickling match over it. Eventually he accepted defeat, lay down on the couch and let me rub and kiss his ass. Then I told him I had to go home. I think he expected me to stay the night – but I didn’t feel up for another night of tossing and turning in a foreign bed.

April 30, 2008 Posted by collegehookerboy | gay, sex | , , , , , , , , , , , , | 4 Comments

Infidelity Part 2

I kind of cheated on Steak again.

So I know this hot guy named John. We barely know each other but he had been sporadically text messaging me semi-provocative messages over the last few weeks. I continually turned him down – until Sunday night. That evening I had planned on seeing Steak. I wasn’t sure, though, if Steak really wanted to see me (me being ridiculous again)- so I wrote him a text message that evening telling him I was going to stay home and do homework.

Instead I texted John and told him to cum to my place. He is quite a bit shorter than me, maybe 5′9, but his face and body are chiseled to perfection. He had told me awhile before that he was 32. I could tell from the lines around his eyes and by his rogue gray hairs that he was older – 38 years old I guessed.

At my place we drank beers and talked. We ended up having a really good time. We laughed, downloaded sixties music and smoked cigarettes outside every hour or so. Eventually he leaned in to kiss me. He was a better kisser than most guys – but not nearly as good as Steak. We kissed and then I took my shirt off. We continued kissing. I scratched my fingers up and down his back and he started grabbing my ass and reaching his hands down my pants.

We got into bed and continued. At one point I pulled my face away and said to him “answer the question I am about to ask you extremely quickly. Don’t take anymore than a second. Ok? Alright, what year were you born.”

I have discovered that this is a great way to catch those who lie about their age. Its not easy to calculate a birth year off the top of your head. Instead he looked at me and said “a long time ago.”

I laughed and took my pants off. He tried to suck my dick for a bit, but it only made my hard-on go away. I told him that I could handle it myself. Then I started blowing him. After a little bit I told him “did you bring the lube?”

He walked over and grabbed it. I specifically told him earlier that night to NOT bring vasoline or any non conventional lubes. He followed my instructions and pulled out a bottle of KY. I threw my boxers and a condom at him when he turned around.

I told him we had to be real quite because of my roommate. Right before he stuck it in me I could hear my roommate whispering on the phone in his room. Fuck, i thought, if I can hear that then he can hear everything that we have done/are about to do. I went to my computer and chose a long song, the full length version of ‘Light my Fire” by the Doors, to drown out the sex sounds.

Trying to keep quiet was really hot. I kept shushing him as we fucked. We sucked on each others tongues half the time and the rest of the time we tried to breath as softly as we could. Its making me hard thinking about it.

I’m sure my roommate heard me say “fuck me harder.” Eventually I couldn’t hold it back and I said “Oh fuck I’m gonna cum……” I shot cum all the way up to my neck.

Then I sucked his balls while he jacked himself off to completion. I covered his mouth with my hands when he came – gagging him so he wouldn’t moan too loudly. Then we sat there, me on top of him, for a few minutes. I rubbed his abs and sex sex lines and asked him how old he was. Eventually, after many deflected responses, he told me he was . . . . . . . . . 45! “Damn, you look good for your age” I said, almost in shock.

Afterwards it took him awhile to leave. I’m not the kind of guy that likes to fuck and then kick someones ass out my front door, but he spent a good half an hour hanging out with me after the sex. I just sat and played on my computer while he stared at me. Finally I said “Well, I got lots of homework to do. I’ll see you sometime soon.” We kissed really quick and he left.

Tonight I am going to go out to dinner with Steak. I’m so excited and horny. I keep flashing back to a few days ago when he was putting an condom on his hard dick in the morning sunlight. His dick looked so nice and big. Oh my god I want it so bad.

April 29, 2008 Posted by collegehookerboy | gay, sex | , , , , , , | No Comments Yet

Texas is gross and unfuckable and I have bad self-esteem. Great!

I met up with Texas around 9pm last night. He was house-sitting for our mutual friends – so we had a big, nice apartment to ourselves. He and I met up in the parking garage of the building. He had cut his hair since I last saw him and I thought it looked awful. God knows why I let guys like him flirt with me. He isn’t ugly, but he isn’t attractive. Hes very burley, has blond hair, blue eyes and has perhaps a 5.5 inch cock (cock is the wrong word – prick is more appropriate.)

He is also extremely arrogant and cocky. He makes fuck loads of money and he never lets that fact slip past me. We got drunk and smoked outside with a whole view of the city behind us. At first we sat apart from eachother. Then he sat on the same couch as me. Then he started holding my legs in his hands.

I told him that he was terrible at making eye contact. He told me it was because he was a thinker – and that he needs to look up to think. Bullshit. Then he said he is always aware of his surroundings and so his eyes are constantly wandering. BULLSHIT.

He grabbed a Disney movie and put it in for us to watch. I took a piss before I climbed into bed. In the bathroom I admired myself in the mirror. I looked really fucking hot. The tan I had gotten that day perfectly complimented my full head of hair and turquoise eyes.

When I got in bed I took my pants and shirt off – telling him it was the only way I could watch a movie comfortably *screech screech here comes the whore train!*

He did the same thing. We cuddled and then he reached down and grabbed my dick. He started jacking me off underneath the covers. I pulled the covers up after a little bit because I wanted him to bask in the glory of my penis’s size and appearance. So perfect, so beautiful, so straight.

Then he gave me a blowjob. God he sucked at it – and i don’t men that literally. It was awful. I have yet to receive a good blowjob. I give amazing ones because I know that you have to suck really hard when you do it and attack the penis with your tongue. I held onto his head and massaged his scalp while he did it. He kept coming up from sucking me off saying “watch your movie” – as if I was so distracted by his terrible hed that I couldn’t pay attention.

Then he grabbed me and had me sit on top of him while he thrusted his pelvis like he was fucking me. He was enjoying himself and he started laughing and lurching me forward so we could kiss. He was acting like such an idiot – I almost felt embarrassed for him.

When the movie was over I saw he was tired. He tried to convince to stay with him for the night – but I told him I wanted to go home. Very quickly I grabbed my stuff and left.

Driving home I began to ponder what I had just done. I had just hooked up with a guy that a) was not attractive b) is not my boyfriend. I concluded that I have terrible self-esteem. I felt a little better driving home when I realized that there is nothing wrong with me and therefore nothing to worry about.

Now I am taking steps to improve my self-esteem. The first step I need to take (which I discovered in a google search) is to stop the negative self talk inside my head. So when thoughts like:

Cyrus, guys only want to get into your pants. None of them like your personality.

Cyrus you will never have a successful relationship. Like always, they will end when the novelty wears off.

Cyrus you’re lazy. You can’t accomplish anything.

Cyrus just give it up and take some vicodin

I will say “NO. LIES!!!”

Also I learned that it is important for my actions to reflect my beliefs in order to acquire true self-esteem. That might call escorting/being a huge slut into question.

April 27, 2008 Posted by collegehookerboy | gay, sex | , , , , | 2 Comments

I couldn’t cum

Yesterday morning I woke up at Steaks place. I was a little hungover from the coke I had snorted the night before – but not enough so to justify the shittyness that was to follow.

At first everything was okay. We got up and went out to have breakfast. Like the last time me and him got breakfast there was little for us to talk about. Half of the time we didn’t speak. It was pretty awkward – atleast from my perspective.

Back at his place I set out trying to seduce him. Finally I said “Do you wanna fuck?” and he said “when my stomach isn’t so full.” Fifteen minutes later we were fucking. It was the first time that we have fucked in broad daylight. We fucked for much longer than usual. He joked that he was going to move me all the way around the bed. Every few minutes he would grab me by my ass and push me a little farther around the perimeter of the bed. I had a hard time keeping a hard on – probably because I had just taken my medication – but that didn’t stop me from cumming in the past. I jacked myself off like a jack hammer – but I couldn’t reach orgasm. Then he told me to sit ontop of him. It was hot, but not as good for me. Eventually I gave up and told him that he could cum. He asked if I was sure and then fucked me ridiculously hard until he came. I liked watching his face from above as he came. Then we kissed. He tried to fuck me a little more so that I could cum – but after a little bit I saw that it wasn’t going to happen.

I jacked off to completion as he took a shower. My cum looked unusually healthy and white – like liquid marble. I should have taken a picture of it – but instead my self created art went down the sink.

Then we went to meet his friends at a pool deck high up in a downtown highrise. We ended up spending three to four hours there. I was so fucking bored. I sat by myself most of the time and tanned while he chatted it up with his coworkers. I hate feeling left out – so I called as many people as I could to keep myself distracted.

Eventually I made it clear that I wanted to leave – and we left.

Back at his place I rubbed my hard-on against his back. I wanted to fuck again. This time he really didn’t seem interested – so I accepted my defeat. We napped together for awhile and then I told him I was going home.

The day wasn’t terrible like I alluded to before. For all I know, he had a wonderful time. It just felt really neutral and boring to me. I fear he will stop liking me. To combat my emotional pain I met up with Texas later on that night…continue to next blog.

April 27, 2008 Posted by collegehookerboy | gay, sex | , , , , , | No Comments Yet

Cocaine ruins everything – but sex makes it better

Me and Steak have been together for the last 24 hours. I met up with him last night and he took me out to meet a few of his work friends and his bosses. I wasn’t anticipating the dinner to be so formal and so anxiety provoking. I was the youngest person at the table by more than 10 years – as well as the only outside person. I did pretty well, though, and socialized with his cohorts. A few times throughout the night he touched my leg or massaged my back – which I thought was sweet.

After three fucking hours I really wanted the dinner to end. Everyone else talked and talked while I sat with them and chain smoked. My age started showing like a fluorescent light. I felt childish.

Finally we left. Steak looked at me as we were leaving and whispered “Do you want to do a line?”

Yay, cocaine! I know I shouldn’t be touching hard drugs – but when they are offered I can’t resist. My sobriety voice was like some haggered old drag queen fighting with her purse against an angry mob of drug receptors. I said “hellsyea” and we headed back to his place.

The coke didn’t sit well with me. I felt anxious and jittery. Despite the negative side effects – I continued to snort it up. Finally Steak physically restrained me from taking a line. I was pissed and beginning to come down. He went to pee really quick at one point and I ran into the kitchen and snorted one last bump.

Then he told me that I could enjoy myself even if I was coming down. I said “Yea fucking right!” In the end, he was sorta right. Me and him talked in his bed for hours. It was the best conversation we have yet to have. At times I felt he was patronizing me – “Cyrus, why must you do drugs? You need to control yourself and take responsibility” – but for the most part it was a good talk. I started playing with his dick as he spoke to me about his nephews and nieces. He stopped talking, looked down at me and said “this is the one time that you are not gonna see me get hard.” Cocaine makes it extremely hard to get an erection, but I’m hotter than cocaine!. I jacked him off and – to no surprise – his cock awoke like a hungry serpent looking for some Gerber’s Baby Apple Sauce (product placement).  Then I sucked his dick. After awhile he started fucking my face. It hurt and I almost gagged with each thrust. Eventually I pushed down on his hips so he couldn’t move them and then I sucked him off to completion. As always, I like to pull it out of my mouth right when he starts to moan so I can watch him unload – then I suck off all the cum drooling down his shaft.

An hour later we decided to fuck. I had eaten that huge dinner many hours before – so I wasn’t sure if the sex was going to work. I could feel all the food in my lower intestines moving. Turns out I was able to fuck. He fucked me and after 8 minutes or so I shot off on my stomach. He massaged the sex lines above my dick as I was cumming – god that felt good!

Today was terrible. I’ll write about it later.

April 26, 2008 Posted by collegehookerboy | gay, sex | , , , , | No Comments Yet

Someone reviewed my fucking abilities online

One of the very few men that I have allowed to fuck me for money wrote a review about me on an escorting website. I kinda like the review, even though he mentions me puking.

“I met Cyrus at a bar in South Beach. I noticed him dancing without his shirt and I couldn’t take my eyes off of him. Very good looking, well structured young man. He made eye contact with me a few times and then walked over and sat next to me. I bought him a few drinks and we got to talking. He is extremely amicable and funny. He almost had me in stitches telling me about the ‘regulars’ in the bar. He told me that he had recently moved to Florida and that he was working as an escort. After a little more conversation he asked me if I was looking for a “date.” I told him yes – and we quickly left the club for my place. He was extremely intoxicated at this point – stumbling in the street a few times, but I brushed it off with a few laughs. He held my back as we were walking and started massaging the top of my ass. Cyrus is a very sensual kid.

I probably shouldn’t have, but I fixed him another drink back at my place. I couldn’t help but think how lucky he was that I wasn’t Jeffery Dahmer or anyone else that would take advantage of his young, drunk ass.

We both shared a cigarette and then he asked me if I had any porno. I pulled out my computer and we started watching some. He told me he was getting turned on and he undressed himself and showed me his dick. It was nice, big and hard and so I started sucking it. I was surprised at how turned on he was – he truly seemed to be enjoying himself. Then he reached into my pants and pulled out my dick. He played with it for a little bit and then led me into the bedroom. His ass was nice and round. It had a little bit of hair, but it seemed naturally smooth. He was so tight that it took a few minutes of adjusting before I could really fuck him. He was biting my arm and stroking his dick as I fucked him. Eventually I watched him moan and shoot a load off on his stomach. I was so turned on that I busted a nut almost at the same time he did. We lay on my bed, sweaty and panting, for a few minutes before we got up to clean ourselves off. A little while later I heard him vomiting in my bathroom. Not the most attractive thing in the world, but I wasn’t too surprised.

I paid him $300 plus a nice tip. When I gave him the tip he pushed me against the wall, grabbed my dick and shoved his tongue down my throat. I felt myself getting horny again and I asked him if he could stay but he said he had school early the next morning. Then he said he wanted to show me something real quick. He walked me outside to a high-rise building across the street and had me go inside an elevator with him. I was a little confused – then he pressed the button for the top floor and we shot up with an all glass view of the entire city of Miami. It was very romantic and charming. He held onto me and nibbled on my neck the entire ride up, then he took us back down, walked me back to my building and left with a quick wink.

He text messaged me the next day and apologized for his drunkenness. He told me that he rarely ever gets that sloshed – and I truly believed him.

Cyrus was an amazingly good fuck. He has this certain air of innocence and quirkiness that I love. He also is really hot and sexual. I would love to see him again; I just have to make sure he isn’t too drunk.”

Nice review, ain’t it? 6 out of 6 people found that review helpful!

April 25, 2008 Posted by collegehookerboy | gay, sex | , , , | 3 Comments

Mr. Popular I am

God I haven’t felt this popular since highschool! I’ve gotten 22 text messages in the last few hours…..Oh! Now its 24.

Steak texted me to tell me he misses me.

Texas texted me, like always. He likes me. Hes rich, but not that attractive. I’ve made out with him and grabbed his dick before. The day I fuck him is the day I need to go to self-confidence rehab.

Yikes. 26 messages!

The ugly guy from Pennsylvania has accounted for half the messages I’ve received. I went outside for a quick smoke and he texted me 6 times. “Cyrus, where are you?” “I guess one day you’ll call me back.” “lol why aren’t u txting me back”….etc.

Why the fuck am I even letting him entertain the thought? I wouldn’t fuck him unless he gave me $10,000+.

I’ve been reading “Prey” by Michael Crichton. I think the books concept is pretty decadent and predictable. Nano particles killing people…come on! Whats gonna destroy the world next, Michael? Scorpions?

Besides that, my day had been fine. Except that I found a scorpion in my refrigerator. And there was another one in my car, come to think of it…

April 25, 2008 Posted by collegehookerboy | gay, sex | , , , , , | No Comments Yet

I’m a bad person

I got my phone messages from last night early this morning. One was from Steak. He sent it as I was being fucked in my John McCain. “Hey sexy man – how are you? I miss you. I was hoping you could come and stay with me tonight. Call me as soon as you can.”

Then he texted me and said he wanted to give me a key to his apartment.

Shit I feel bad.

I always said I was different than other gay guys. I never wanted to be a promiscuous, non-committal f-a-g. Looks like it was a self-fulfilling prophecy. Maybe I didn’t want to be that way so intensly that I brought it upon myself. Maybe “The Secret” isn’t total bullshit.

Kiss my ass, Rhonda Byrne!

April 23, 2008 Posted by collegehookerboy | gay, sex | , , , | 2 Comments

I fucked someone else….with VASOLINE

I ended up going out looking for ass last night. I found a guy whose name began with a C and was followed by a vowel (Carlos I think). I’m not a slut if I remember atleast the grammatical structure of the name.

He was a good looking Latino guy with semi-long, straight black hair and a chiseled, well structured face. He looked like one of those hot, poor Peruvian guys that you wanna fuck so bad but can’t because they like fucking poor, white girls. He acted straight in every way, but clearly was after my ass.

I told him to follow me back to my place. He did. I was a good 5 inches taller than him, so I was a little weary of the sex. He also claimed to have an 8 inch penis. I told him that was too big. Then he backtracked and said it was either 7 or 8. I knew then that he was a liar.

I walked outside to meet him as I finished up my bowl of Honey Bunches of Oats (Tastes like a mouthful of Joy! *black woman laugh*) He didn’t seem too interested in conversing – unlike earlier when he had been talking my ear off. I brought him into my room. I told him my roommate was sleeping in the bedroom nearby – so we had to be quiet. My roommate wasn’t there – I just said that so that he wouldn’t murder me. I took my shirt off and he took his pants off. I grabbed his dick and started sucking it. His dick was the perfect size and width for sucking. I could shove it all the way down my throat – yet it wasn’t small. Maybe 6.5 or 7 inches at most.

Then he got into my bed. I sucked him off and then licked his balls. Maybe its just me, but Latino guys don’t really have balls. Steak doesn’t have much of a ball sack, either. He said “do you like it?” and I said “mmmhmmmm.”

Then he turned me over and asked me for a condom. I gave it to him and then I asked him if he had brought the lube like I asked. He then proceeded to pull out a tiny jar of VASOLINE! I have read a million times that you should never use oil-based lubes – since they can easily tear a condom. I expressed some anger, but then let him continue. He stuck his dick in for a bit and I told him to stop. PAIN. I made him pull it out. Then he put it in again. PAIN. I held his chest so he wouldn’t move. After 30 seconds or so he started to move. Very quickly it started to feel good. Really good. I stared up at him but he didn’t return my glance.

I felt an orgasm coming. I told him to fuck me harder. Right as the orgasm was surfacing he pulled out and, for whatever reason, jacked himself off through the condom as he crossed the finish line. I came, but his dick wasn’t in me when I did.

Then he quickly grabbed his clothes and asked where the bathroom was. He went into the bathroom in the dark and flushed the condom down the toilet. I guess thats what everyone does. Then we exchanged a few awkward smiles and he left.

The sex pacified the pain I felt over Steaks lack of communication.

I’m scared hes doing what I’m doing. To find out, I came up with a genius idea. Since I know he has ass-cruised on craigslist before, I am going to put up an irresistible sex ad and see if he takes the bate.

“I’m a 19 year old college student looking for a hot, Latino top to fuck my brains out. I like guys with long hair and nice dicks. I live (insert a location within a few blocks of steaks apartment building). I also love watching Ellen’s stand-up comedy and smoking Parliament Light cigarettes.”

April 23, 2008 Posted by collegehookerboy | gay, sex | , , , , , , | 3 Comments

I have a sex drive! Finally

My sex drive has been coming back recently. Yes I am a slut and a prostitute, but the truth is my sex drive has been out of commission for years as a result of severe drug abuse and substance abuse medications.

Today in my communication class I was fantasizing about fucking my big, juicy steak. I couldn’t sit still – I wanted him to fuck me so bad. I kept flashing to the look he has on his face when he fucks me. It starts off as this comforting, adoring smile – and then turns into a sinister, demonic fuck face.

I really want to date him. He told me that he wants me to stay with him for a whole week sometime soon – when I am done with most of my finals and when his work load decreases. I’m not sure if I want to stay with him for that long, so I agreed to a weekend. This happened last Sunday. He also told me he would text me the following day to tell me if he was going to be re-locating for work after this summer (aka leaving me forever). He never did. I was really upset the last two days about his lack of communication – so I texted him saying that I wanted to fuck him and he promptly responded by saying “sooo hot.” Maybe he just isn’t the text message type. He never has texted me unless we are about to meet up.

His lack of attention is making me want to cruise for ass. I know I shouldn’t, but I might. There are lots of clubs in this city. And I got the whore-super-highway right at my fingertips.

April 22, 2008 Posted by collegehookerboy | gay, sex | , , , , , | No Comments Yet