I didn't know what I was thinking. My hands were still shaking from the excitement. My heart raced as I finished verifying my craigslist account. My online ad, which garnished a picture of my plump bottom being spread wide to reveal my sweet hairless hole was titled "Teen ISO Daddy". I stated that I still had my anal cherry, in fact I had never even been with a girl yet. My rear opened up like rose bud, an inviting cherry ready to pop.
I had just started my first year of college and was still a complete virgin. Sure I had tried to get the occasional nude from the girls at school, with little success. I was fairly good looking, with shorter brown hair and emerald green eyes. But the girls wanted the older studs, and I was only now just turned 19. My boyish features were still very prominent.
l always lusted after the porn stars late at night dreaming that I could one day fuck a girl like that, one that was kinky and would do whatever I wanted. But I didn't know how to make a girl be sexual. They all seemed to mind their own business and fantasize about the celebrities on T.V anyway.
Then there was Kennedy. She was my next door sweetheart. Well, she barely knew I even existed. She was a year older than me, And had already started college. I chose to stay living at home, for one cheap rent, but really I wanted a chance to Ben with Kennedy. I had helped her family move in and the moment I saw her I fell in love. Blue eyed brunette with a perfect petite form, and her hair fell like gold from her head. I often dreamed of her straddling my face while I pinched her perfect B cup breasts.
The reason I hesitated was because I wanted to make sure she liked me first. I had invited her to eat lunch with me her first day, and we sort of became friends. We didn't have any classes at school together, and since she was new to town she didn't have a clique to hide behind, yet.
"Dear god I hope she doesn't get too popular. Then I would never get a shot!" I thought to myself. However she Hung out with a different group everyday so I tried not to badger her.
We would talk online and sometimes on the way home, when she didn't have practice. She would tell me about her interests, and sometimes the things some of the guys at school had said to her. But we always had a good laugh about it. I just wish I could work up the nerve to ask her out, this sexual tension within my body ached my cock every night, and I would often wake up having shot a large load in my sleep. Sometimes I even masturbated 3 times a day! I almost always fantasized about fucking Kennedy and cumming all over her face like a porn star. One time after a rigorous masturbating session I unloaded all over her school picture. I took a finger full of cum that plastered the page, and licked it. It tasted really good, but I knew that didn't make me gay.
So then why was I placing an ad for gay sex?
Well.. I had gotten into trans porn at first. It was just so hot seeing girls with dicks go at it. I thought girls were hot, and this way there was no guy on the screen. So it was all just kinky fun. My biggest turn on was facials. I had long been wanting to give one to Kenn. when by accident I stumbled upon a cum eating instruction video. I didn't notice the title at the time because it looked like "CEI" and I didn't know what that meant. But the girl, she looked like an older version of Kennedy! dark hair with a firm jawline and red lipstick that screamed high class slut. I had already watched porn for an hour and I wanted to cum very badly. Before I knew it my legs were up in the air and I was raining down warm salty cum into my teenage throat. After that I was addicted. I watched all of her video's and fantasized that it was Kenn making me humiliate myself. I even fucked myself with a cucumber and would always lap up my cum afterwards.
Eventually it progressed to imagining myself sucking other men's cocks. I didn't consider myself gay. I was just pretending to be a porn star, and porn stars were whores that loved cock and cum. I was just so horny all the time, so that's how it happened. I never imagined a women would be willing to have sex with me without money, so I decided to post in the gay section. I had thought, at the very least I could get my first blow job!
"I'll just pretend its Kennedy." I thought to myself as I began to fill out the first of many ads.
Each day I would re'edit my post. I was overcome by my own sexual frustrations, and my post's got sluttier and sluttier. I would respond to some inquires, but never followed through. I had already came on my own face twice on that particular day. The taste of my own cum lingered on my lips when I closed my laptop and looked outside. Kennedy was heading inside her house from a run! Her nipples were hard and penetrated through her sports bra. I tasted the cum on my lips and imagined it was her tasting my cum.
The next day I checked my email. I had over 12 replies! I looked at a few and was a unimpressed. But one in particular caught my eye. His cock was glorious. About 8 inches, Cut, with neatly trimmed white pubic hair. A small drop of precum glistening at the slit and it just.. invited me to suck it. I replied back to him told him what I was into, and that I was new to all of this.
He replied and asked me for a picture sticking a finger into my virgin ass. I made sure my face wasn't in the frame because I was still worried about getting found out! It was hard to get the angle right with my phone using only one hand. So I used the webcam on my computer and kept my face above the shot. I waited nervously for his reply. My cock started to harden and twitch thinking about how real this all really was!
"Wow! you really are a slutty teen boy. Better hurry over and suck my cock right now. Head to the motel 7 and we'll get a room." He replied.
I read it, reread it. Masturbated my cock a little. Went to get my clothes on. But I just couldn't believe this was really going to happen, and then I got scared. An older man, who I've never met wants to put his penis in my mouth? But what else did he want? All I had to do was leave my front door and walk 5 blocks and I wouldn't be a virgin. But I just couldn't bring myself to do it..
10 minutes later...
I got another message from Daddy.
"Are you ready slut? If you flake, you're going to make me have to punish your puckered little virgin boy hole." He said.
I deleted all the messages. Deleted the ad. Humiliated, I lifted my legs over my face, and jacked off furiously trying to think of Kennedy. But all I could think of was Daddy's magnificent cock, and when I came warm spunk all over my face I imagined it was raining down from his.