Hi all. About five years into my bi life (I had been with enough men and done enough different things I felt pretty experienced and no longer was nervous) I was on a business trip to Chicago. This was back when Craiglist still had men seeking men ads. I placed an ad that I'd be in town and would like to have some fun, and could host at my hotel. Like always I got a lot of low quality responses and several people that replied they were interested, then never returned another email.

One seemed more serious - he replied quickly, answered questions, etc. He said he loved getting his cock sucked and may be willing to give me a handjob, but mostly he was more of a top. That's fine, I love sucking a nice cock, so we agreed to meet. He would be on his way home from work and could come to my hotel. I said I'd meet him in the lobby (always a good way for both guys to be able to change their mind at the last minute if something didn't seem right). He was as advertised: 40ish, good shape, clean cut, wearing slacks and an oxford. I must have passed his test because we said hello and headed for my room.

I let him in and locked the door behind me. He quickly undressed down to his boxers, then said he'd like me naked and on my knees. I quickly undressed and as I knelt in front of him he said "there you go, kneel cocksucker. You want me to feed you my dick don't you"? I nodded yes and he said "beg me for it, tell me what you want". I said "please let me suck your cock, I want to lick it and suck and taste it". He slid his boxers down and revealed about 7" of nice thick cock, circumsized, closely trimmed pubes. He was semi-hard and said "work that fucking cock slut, make me hard". I eagerly went to work, as always putting all my attention into pleasuring the man. I felt him grow hard in my mouth and he said "oh that's good slut, you're a great cocksucker, suck that fucking dick". I had always been with respectful guys on an "equal" footing. This was new to me but wow did I like it. I felt so dirty and slutty. My own cock grew hard. He put his hand on the back of my head and slowly started face fucking me. I had been face fucked before so thought he wanted to be in control so just let him take charge. He said "what are you doing? I didn't tell you stop sucking...worship my cock, slut".

After a few more minutes of this he pulled his cock from my mouth and told me to stick out my tongue. I did. He slapped my face and tongue with his cock several times. Each time saying "you love this cock". He said "you want my cum don't you"? I nodded and he said "it doesn't matter what you want. I'm going to cum in your mouth and you're going to swallow it, aren't you slut"? I nodded again. He jammed it back into my mouth. Holding my head he thrust deeper until my lips were touching his stomach - I had his entire cock in my mouth. It was hard to breath. He held it there, then pulled it all the way out, then thrust all the way back in. He did this several times while saying "you love me fucking your cum hole don't you"? I could only grunt.

After a few minutes he said "show your best cock sucking skills. Worship my dick better than anyone has before". I took the challenge! With my eyes closed I focused on giving the perfect head. I used my tongue on his shaft as I sucked, I massaged his balls, when I tasted precum I'd quickly lick it up". He turned nice. "Oh that is good, suck that cock baby". I had been promoted from Slut to Baby lol. "Wow you are one fantastic cocksucker". Another couple of minutes and he directed me to finger and play with his ass. I took the hand that had been massaging his balls and quickly found his asshole. I massaged around it and very gently eased a finger partway in. He gasped "oh yeah that's perfect, keep going". It didn't take long from there before he moaned "oh yes I'm gonna cum" and he thrust deep in my mouth and shot an absolutely huge load. I could feel 4-5 thick spurts flow. My mouth quickly filled, I swallowed as much as I could but felt some drip out. He said "there you go baby, take my cum. Show me you love my cum". He finished shooting and as I he slowly withdrew I sucked his shaft to clean it off, then swallowed the rest. He held his cock for me as I licked it all over, making sure it was clean. He then quickly got dressed, said "thanks, that was great" and left. I was rock hard to jerked off into my hand, then licked that up as well. My head was swimming!