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 :)
 

[FFM] My husband fucked my best friend in the ass while she ate my pussy.

My previous account was doxxed last week so this is a re-post of one of my favorite experiences.

I’ve known one of my best friends, Lindsey for about 10 years now. She is a year younger than me, with long blonde hair, blue eyes, ginormous boobs and an ass to die for. She’s always been very adventurous sexually so when my husband and I opened up our marriage of course she was the first person I told. We were out at dinner and had a couple glasses of wine at that point and she was very intrigued about the possibility of a threesome with Lucas and I. The night carried on, we went out dancing and kept drinking. We were getting very flirty and openly touching on the dance floor when she made her move and started kissing me while she felt up and down my body. We couldn’t take the tension anymore so we hopped in a taxi back to my house.

A Rendezvous with Daddy [F34/M36][oral]

I pulled up to you standing there on the sidewalk waiting for me. Posted up against a wall like you didn’t have a care in world. Red sweatshirt. White hat. A fuckin smirk because you knew I would make that 2 hour drive without question. I know you’re just as nervous and excited as I am.

I park the car, trying to calm the butterflies that have been building. Increasing with each mile passed. Last minute look over in the mirror for the hundredth time, wanting to impress but knowing you’ve seen me. I can feel your eyes on me. Watching my every move but waiting for me to make that first step. I can see your hands clenching, wanting me to just hurry the fuck up and get out of the car.

Finally, I make my way towards you. Avoiding your eyes, looking down until I’m in front of you. A hand, your hand, finds my chin, “Look at me” you say. I look up at you, searching your face for disappointment and not finding any. “Hi”, I say, throwing my arms around your neck and pushing my entire body into you. Craving the closeness, the feeling of another body pressed up against mine as you wrap your arms around me.

The art of hot sauce and oral sex [FM]

*Bro, this is a dangerous game. I’ve been avoiding this story for that reason. Experiment with caution, my friend.*

I kind of stumbled into this by accident. When I was young I fucked a dude who was very boring in bed, but he once went down on me after eating a spicy dish. I had tears in my eyes but it felt so fucking good I begged him to keep going. I used to have too many insecurities about receiving oral to climax from it, but the pain was so distracting that I came within a few minutes.

So that was fun.

Later when I was dating a woman, I told her this and she almost laughed at me. She was far kinkier than me and obsessed with oral. She immediately got tabasco sauce and put a few drops on her tongue. When she licked me it burned, but it was more of a nice tingle.

“In a scale of 1-10 how painful is it?” She asked as she pulled away.

“Two,” I replied with a gasp.

[MF] My continued relationship with an older woman. Reupload

Due to multiple requests, I have decided to write more details about the experiences myself and Diana shared. As you know Diana although was 55 years old and two children was very sexually inexperienced. To her sex was just missionary and the occasional blowjob, she had never received oral or tried new positions. Her husband had left her for a younger woman. Diana she was lonely, depressed and hugely lacking in self-confidence.

About one month into our sexual relationship, we started to try new things, up until this point it just been missionary sex usually followed by me going down on her. Diana still wasn’t very good at what I would consider dirty/sexy talk. Her way of asking for sex would be ‘Do you want to go upstairs?’. I would drop her off after work, she would invite me in for a cup of tea and we would kiss and cuddle and sometimes she would ask if I wanted to go upstairs. I never said no.

Diana wasn’t comfortable with the lights on during sex so after one session and we were both snuggled in bed. I asked her “Wouldn’t you like to try it with the lights on”

Losing It – Part 7[FF][Dickgirl/Futanari][Oral][Teasing][Bullying]

^﴾ ^Content: ^18+, ^anal ^sex, ^anal ^stimulation, ^asphyxiation, ^big ^dick, ^breathplay, ^bullying, ^cum ^in ^hair, ^cum ^in ^mouth, ^cum ^on ^face/facial, ^cum ^swallow, ^domination, ^excessive ^cum, ^girls ^with ^dicks, ^handjob, ^multiple ^orgasms, ^multiple ^penises, ^non-con ^[dream], ^oral ^sex ^[fellatio], ^prostitution, ^rough ^sex, ^verbal ^abuse ^﴿

# Chapter 7⸻Nightmares

I’m not sure what woke me up. I’m not even sure how I ended up getting downstairs and back into Millie’s bed, to be honest. But when my half-asleep eyes finally peeled open, the silhouetted form that greeted me was impossible to mistake. It seemed that Lizzie and Kim were having a little trouble sleeping as well.

They had taken the opposite side of Millie’s king size and laid opposite us with their heads near the foot of the bed. And they were making themselves at home, to say the least.

Kim had her panties around one ankle, laying on her side while Lizzie held her other leg in the air. Her shirt was pulled just above her nipple line, and Lizzie’s free hand occasionally took a break from gripping Kim’s neck to handle her exposed breasts. Her hair was braided into low pigtails, which had been brought around her head and tied behind to serve as a makeshift blindfold.

Losing It – Part 7[FF][Dickgirl/Futanari][Oral][Teasing][Bullying]

>Mirrors [for better formatting]

>[Blogger](https://zivzap.blogspot.com/2022/12/losing-it-ch07nightmares.html
)⌁⌁[Google Docs](https://docs.google.com/document/d/1wILCWqmOg0XtjIR1V6CV-99323PJEba2Yu1C0ektp9g/edit?usp=sharing
)⌁⌁[Hentai Foundry](https://www.hentai-foundry.com/stories/user/zivzap/46971/Losing-It/161577/Chapter-7/Nightmares
)
***

^﴾ ^Content: ^18+, ^anal ^sex, ^anal ^stimulation, ^asphyxiation, ^big ^dick, ^breathplay, ^bullying, ^cum ^in ^hair, ^cum ^in ^mouth, ^cum ^on ^face/facial, ^cum ^swallow, ^domination, ^excessive ^cum, ^girls ^with ^dicks, ^handjob, ^multiple ^orgasms, ^multiple ^penises, ^non-con ^[dream], ^oral ^sex ^[fellatio], ^prostitution, ^rough ^sex, ^verbal ^abuse ^﴿

# Chapter 7⸻Nightmares

I’m not sure what woke me up. I’m not even sure how I ended up getting downstairs and back into Millie’s bed, to be honest. But when my half-asleep eyes finally peeled open, the silhouetted form that greeted me was impossible to mistake. It seemed that Lizzie and Kim were having a little trouble sleeping as well.

They had taken the opposite side of Millie’s king size and laid opposite us with their heads near the foot of the bed. And they were making themselves at home, to say the least.

Kim had her panties around one ankle, laying on her side while Lizzie held her other leg in the air. Her shirt was pulled just above her nipple line, and Lizzie’s free hand occasionally took a break from gripping Kim’s neck to handle her exposed breasts. Her hair was braided into low pigtails, which had been brought around her head and tied behind to serve as a makeshift blindfold.

[m]y first threesome mfm

[M]y first threesome mfm

This is my first post, let me know if you like it, and if I should post more.

This happened back when I was with my ex, I was 21, and she was 19. She is absolutely stunning : 1m76, long brown hair (comes down to cover her tits), fit without doing sports, C cup boobs, amazing ass, hourglass shape body. She always has people turn around to check her out when she goes out, she knows she’s super hot, and it made me very proud. I always liked for her to be slutty: dress with short skirts, large cleavage. I always felt like she could be even more slutty, but she had some limits.

Anyway, we wanted to spice up our sex life, so we bought a cheap dildo and played in bed together with it. One day we were talking about common fantasies that people have, and the threesome is quite a popular one. We talked about it, and one day after playing with the dildo in bed, we thought “why not try a threesome for ourselves ? Have a real cock to play with, instead of a piece of plastic”. We talked about it in details, knowing that it is a risk in our relationship, but we feel confident in each other, so why not try it ?

Cucking her ex by accident and training her body to love deep penetration [MF]

22 cm = 8.5 inches

I matched with this hot girl on Tinder. She had a pretty serious profile with some nice pictures which looked promising, though she had one picture showing she had a dark side to her as well. Still, I though it was worth a shot.

After talking a bit, she shared was living with her ex-husband. They had broken up some time ago, but due to economic reasons she chose to stay there until she found someone else. Asking if they were still sleeping toghether, she admitted they were having a fwb arrangement going, which admittedly felt more than just a bit wierd as I heard her ex in the background sometimes while we were talking.

She looked serious from the dating profile, but the more I got to know her the more I realized she was a dirty, dirty girl with a lot of red flags. She loved sex and had been with a lot of men over the years. During our convos, she also admitted making porn videos, including some with her ex she was living with. She linked me to her videos, which were anything but softcore.

Surprise Fling with a Friend After Mutual Heartbreak [mf]

I (M31) had a FWB relationship with a friend from high school (F30) about four years ago. (I’ll call her M.) Though we’re not together anymore, the memory of our time together still thrills me to my core.

M and I were in the same grade in high school and shared a few classes together. I liked her just fine then, but was preoccupied with other girls and only thought of her as a friend. After high school, M and I fell out of touch for a couple of years before spontaneously reconnecting over Facebook. She remained in our hometown while I went to college out of state, but we soon kept in touch on a daily basis – sharing our goals, thoughts, preferences, and daily chitchat with each other. We both pursued relationships with the opposite sex, but both remained single. We continued that way for five years.