first time hooking up on craigslist
Introduction:
My true story of my first full experience with another man and meeting a stranger online.
I was 24 at the time. 5’8 tall 190lbs and very hairy. My dick is just under 7 inches and a nice size cut and usually trimmed hair. Not much of an ass honestly and not girly in any way. But I Loved getting fucked like a whore.
I have mostly been attracted to women in my life but have had the occasional experimentation with boys growing up which I may post here later if I feel like it. Here is my story.
My mom called me on the phone during the week one day and asked if I would be able to come over from time to time and watch the house and take care of the dog over the coming weekend. They didn’t live very far, and it really was not a problem so was no big deal.
That Saturday I has really horny when I went over, and the thought hit me to maybe have some fun with myself. I decided that I was going to grab one of my mom’s dildos and give myself a good fucking sense I didn’t have the time to do so normally. After cleaning one that I liked I grabbed a condom and went to town on myself… By the time I had the full length of the toy in my ass craigslist had come to mine and how I wanted to have the real thing.
I laid there with the toy still in and posted an ad “first time looking” after a bit I had a pic and a response that read something resembling “you should let me put my black cock in that tight ass”
After a few messages he was on his way over, and in our text, he wanted me already naked and ready when I answered the door. So, I being a little submissive did as I was told and waited for him.
He was a heavyset black guy with glasses short hair and gym shorts on, looked to be maybe mid thirty.
He seemed nice and gentle enough knowing that It was my first time, so we walked to the bed room and asked if I wanted to suck him off to get started. He told me to get down on my knees for him and I did then after that I didn’t have to take any direction. His pants were off in a second and my face was greeted with his semi flaccid cock.
I want right to work and wasted no time putting it in my mouth to get him hard. It wasn’t my first cock and it wasn’t the biggest, but I remember a musk smell and no taste really at first, but it sure grew to size quickly. I couldn’t deep throat it, but I gave it my best.
He asked if I wanted him to lay down, so I could change the angle. I agreed and got next to him on the bed and started to kiss his balls with some sucking. I did this all the way to his head and slowly wrapped my lips around his cock as I slid down almost the entirety of his cock. I heard a moan escape his mouth, so I knew I did something right. I settled into a little rhythm where I would lick his shaft from top to bottom and then bob my head up and down his cock making it about half way into my mouth for about a minute and repeat.
About 5 minutes into this I felt a wet finger start to play with my ass and boy did it feel good from lightly ringing my ass to fingering me.
7 mins in pulled I off his cock with his middle finger in my ass and asked if he wanted to fuck me now. All he told me was to bend over the bed.
Bent over and completely at his mercy he took his shirt off and put on a condom which we agreed to before. I felt like such a little bitch laying over like that when he applied the lube and I was loving it.
He asks me if I was ready and I said “yes” as I felt both hands spread my cheeks with his cock pushing on my virgin hole.
Thankfully because of my play time before and his slow entrance pain was minimal. He slid it in inch by inch each push checking on me until he had the full length in me and God did it feel good. He gave me some time to adjust and slowly started to fuck me. And there I was laying there bent over a bed completely exposed and at the mercy of a complete stranger fucking me.
He would do a few quick shallow pumps and then slide the length of his cock in me and slowly out. I even got a spanking out of it, I was his bitch for the time being and I couldn’t help but grip the bed and tell him to fuck me harder or even the few times I called him daddy.
It must have gone on for about twenty minutes with a few spots to add lube and readjust onto the bed when I told him he didn’t have to make it last and wanted him to cum for me.
After I said that he laid into me and started really fucking me hard making the bed shake with every thrust. When I could hear him getting close I told him “yes daddy fuck me, … cum in me, please” I don’t know what came over me as he pulled out smacked my ass and slid right back in before I could think.
In less than a minute I felt him tense up and cum.
When I felt him slowly pull out I realized what had just happened… He pulled off the condom and shot a very sizable load into my very willing ass.
The end of the story was uneventful with me cleaning up and him leaving almost immediately as I walked to the bathroom to shower with my now messy ass.
