Back in my college days my roommate and I had simple stripe poker rules; play till your nude and then move to favors.   It is truly amazing how wild things would get at it wasn’t uncommon for some freshman to lose her virginity on a bad hand.    On mate fateful night I had received a BJ from one girl and anal from another.  My roommate on the other hand had no such luck and the girls where gone and only I scored.     I was in the living room killing a few brain cells with my new bong when my roommate asked if I wanted to continue the game.     I asked why bother since the girls are gone.   He went on blabbering about his sexual appetite and how he wanted to corn cob me.     It’s embarrassing to admit this but I thought he wanted to lick my dick.     I asked him “What if I won?”  He then said he would give me a blow job.      I took another hit and thought wow “If I win he’d suck my dick,  if I lose then he licks it”  man he must have really been fucked up. 

 

We played and I lost.   He told me to take my cloths off and he’d be right back.  I figured what the heck and took them off.  He returned with some KY and began stroking himself.   I was a little surprised he was getting hard in front of me, but figured he must needed to  turned on.  As I watch I could help but notice that he was bigger then me.  I was thinking he was at least eight maybe nine when he told me to “bend over”.   I said “for what?” and he quickly replied “So I can corn cob you!”.     I was totally naïve and asked “What do you mean?”.  He then explained in very simple terms “You bend over and I stick my dick in your ass?   Haven’t you ever heard of corn cobing?”.  I told him I had not and he felt sorry and made me a double or nothing bet.   The second hand was to determine if I was to sleep in his room or mine.   I wasn’t really sure what to do but I thought filling up the bowl was a good start.    We played our hand afterwards and I regretfully lost.     At this point I was pretty numb I just headed back to his room to get it over with.   

 

 

He followed me in and I simply asked “Now what”.   He told me to just get on his bed and on my hand and knees.    It was totally humiliating as  he smeared KY in my ass and all over my crack.     He then started to enter me and it was a feeling I will never forget!   His head was really hot but as forceful as was being pushed it was really a cross between soft skin and hard cock.   He tried to enter me for an almost an hour but I couldn’t  relax enough to get his head in.    He then told me “You’re useless, turn around”.   I did and he pushed his cock towards my mouth.   It was gross and I told him he would need to wash first.   As he cleanup,  I should have left but instead headed to my room to get some cherry lube.  When he returned I smeared it all over his cock and close my eyes and started to lick.    It really wasn’t bad and the cherry flavor was really good.    I never gave a blow job before so I just did what I thought felt good.   I knew I would never be able to deep throat him so I just licked around his head and sucked on his head.    I could tell he was getting ready to blow when he got a little harder and thrusted  forward.    I thought about pulling away but instead let him cum in my mouth.    At first I didn’t want to taste  it and just let it shoot down my throat.  Then I pulled back and let it enter my mouth and got my first taste of cum.   It wasn’t at all salty as I had heard and instead it was sort of sweet and creamy.    I had given my first blow job and it was actually good!    I laid there and just stared and his cock wishing it could keep shooting.  I played with and licked it but it just went soft and he stared to snore.    Well a deals a deal so I just went to bed.

 

At about 4am he woke me up and told me “It was time”.  I  looked at the clock and I asked “For what?”.  He then said “To finish what we started”.  I said “You gotta be kidding”  he said “I’m and not kidding and it’s going in this time”.        I knew when he said that “no” was not an option.   I got on my hand and knees and he again lubed me up.   He pushed and pushed but it would go in.    It was a little after 5am when I was thinking how useless this was and how tired was and then it happened.    It must have been the exhaustion then relaxed but now it was in an the pain was intense.     Once he got started he didn’t last long and it was all over by 5:30.  He pulled out and I could feel the cum running out of my ass.   The night was over and he had won!

 

I did learn that I like the taste of  cum but  and I have done some bi oral  with a couple I met.   I’m not really into anything more and given my first time was so painful it’s  unlikely I will have anal again.