My Encounter with a Stranger from Craigslist…a true story

After some encouragement from a fellow Redditor I decided to
write about my past sex experiences during my “slutty phase”. When I was younger,
I had a lot of fun and luckily no regrets. This is long so….
 
So, when I was 21 my then fiance and I ended our engagement.
We had been together for 2 years and was only the 2nd guy I had ever
been with. I needed a place to live and I didn’t want a roommate so I took to
Craigslist to look for a place. After responding to several ads I noticed the “Casual
Encounters” section. No idea what it was about but I looked at several of them
and was intrigued. A week or so later after looking at places and answering apartment
ads I took another look at the CE section again and it had my mind racing
around a bit. It had been a while since I had sex and I was feeling it and
masterbating wasn’t doing it anymore.
 
I found an ad from an older guy that was in town on business
and …. well, you know. I replied to his ad and after a couple of emails we
moved it to Yahoo chat. He was coming to town in a few days and staying
downtown in a very nice hotel. We chatted for about a week and exchanged pictures.
He was 45, in great shape and he eventually divulged that he was married. At first,
I was a little mad but we had such good conversations, tons of flirting that I
told myself that would be his problem not mine. I’d never ever been with an
older man (at this point) and always had a fantasy about it. After chatting
more, him being married was also a kinky turn on for me.
 
The evening came for our date and we had plans that I would
meet him at a nice restaurant. I wore a short black skirt, pink thong, a black see-through
lace bra and a very low-cut blouse to show my 34C tits. I walked in and he was
at the bar waiting. He looked hot as fuck. He looked like Leo in Wolf of Wall
Street and was a lot hotter in person than in his pictures. He was taller than
I thought but I’m only 5’5” so it’s not that hard. Dinner was great and the
conversation seemed easy just like our chats. We went back to the hotel lobby
bar and had a few more drinks. The flirting started heavy and he was a charmer.
I got the feeling that this was not his first time playing while out of town.
He could tell I was a little nervous but he kissed me and my apprehension
melted. We kissed again and it made me wet. He could tell and suggested we move
it to his room.
 
When we got in, he poured us a drink from the mini bar and
we both slammed them down and got to it. In no time I was on my back and his mouth
was between my legs. Among the things I learned that night was that I love what
is referred to as a “praise kink”. He was a vocal one too. He was telling me
how much he loved how I tasted. He loved that I shaved my pussy down to a
little strip on top. I had never had anyone do that before and I melted me. I
had my first orgasm of the night…and I was his. He definitely knew how to lick
pussy. Perfect amount of licking, sucking and fingering. He did it like he
needed it. I was learning why one of my friends swore by older men.
 
After another orgasm I got on my shaking knees and took his
cock out. It was beautiful. It was the perfect amount of thick and long but not
too long. I don’t know the exact length but my 7” dildo reminds me of it. I
have always loved sucking a man’s dick. I have an oral fetish and just always
loved having it in my mouth. He was telling me how good I felt and he was
impressed that I could take it all the way into my throat. He let out several “Oh
fuck!”s. His hand on my head and grabbed my hair guiding my mouth up and down
his thick shaft. I couldn’t help but moan. I asked if his wife was this good at
it and he said “hell no” which I didn’t care if he was lying or not, I loved
it.
 
After several minutes I was ready and told him to fuck me.
He asked “How do you want it?” to which I replied “However you want.” We had talked
about it before and he knew exactly what the what I liked and wanted to do. He
grabbed me by my face and lifted me off of my knees, took my top off and undid
my bra. His hands all over me and I loved it. He loved playing with my tits and
nipples as did I. He had strong hands and knew exactly what to do with them. He
commented on how much he loved my body and kissed me all over. And then, he
took me over to the table in front of the mirror, bent me over and slowly stuck
his cock inside of me. I was tight and it took a little bit to get it all in
even though I was soaking wet. I didn’t really notice the mirror at first as I
was just enjoying him taking me. I had never been fucked like this before. He
kept calling me “good girl”, “bad girl”, “dirty girl” and I loved it all. Spanking
my ass. Then he noticed my head was down the whole time and then he grabbed my
hair and made me look at us fucking in the mirror. It was incredible. This hot
married fucking me and my tits swinging back and forth with him pounding me
from behind. I reached down and started rubbing my clit and I came almost
instantly.
 
He grabbed me and threw me on the bed and deftly moved me on
top of him. I got on top and rode and grinding on his cock. His hands were all
over me, grabbing my tits, my ass, lightly choking me, sticking his finger in
my mouth and telling me to suck on it like I did his cock. I was losing myself.
Who int the fuck is this guy? And how did he get so good at fucking?
 
He pulled me down and whispered in my ear to tell him when I
was going to cum. Whispering how good my pussy felt and how wet I was. I told
him I was ready to cum and when I started, he slid a finger in my ass. I wasn’t
expecting that at all and had never had it done. At this point this man could’ve
done anything to me and I would’ve let him. He said he was going to cum and asked
where I wanted it. He said he wanted it on my face. He flipped me over, put his
cock over my face and cam all over it. At this time, I’d never seen a guy cum
this much. It was all over and got into my mouth, neck and tits. I ended up
swallowing some if it as well. I’d always loved swallowing. Still do.
 
We laid in bed for a while and we took a shower together. I hadn’t
moved into my own place yet and I couldn’t go back with cum all over me. We kissed
in the shower and I ended up sucking his cock more and he came again in the
shower and I swallowed him, though it wasn’t was much as before.
 
He walked me to my car and kissed me good bye. When I got home,
he had sent me a Yahoo chat about how much he loved fucking me and I told him I
loved his cock.
 
He came back to town a 2 more times in about 6 months and we
met up and fucked both times. This was the start of my realization that I loved
fucking older married men. Don’t judge :)
 

Source: reddit.com/r/Erotica/comments/zs0kht/my_encounter_with_a_stranger_from_craigslista