[FM] First time interacial and pegging!

This was almost 2 years ago, I was 27 One of those things that I had been trying for years, i wanted to be pegged, ruthlessly, by someone I barley knew. CL personals were still a thing back then, but I live in a small town smack dab in the middle of the US. I began trying posting ads in Wichita cl looking for someone to peg my ass raw. Not many replies most of which were spam. A few people got my hopes up but ghosted me after some very erotic conversations. I’d given up but hadn’t deleted my ad.
I had been having a rough week at work and had gotten a message through the messaging relay from a lady in a town about an hour and a half away from me. She was very interested in pegging a guy as she had done strapon play with woman. She only sent a couple messages back and fourth, gave me her phone number and wanted me to call her. I was super nervous and axious but called her on a Thursday evening. We talked for about 45 minutes, it was great, like talking to an old friend, I hadn’t seen any pictures but connected decently in a mental standpoint. We started talking about the kinky things and I was so excited.
She asked when we should meet up and I said no idea. We talked about what supplies and equipment we both had, then she started texting me pictures of her holding dildos asking “is this too much girth,” or “longer?”  Jaz as we will call her, gave me a ring after she left the sex shop and asked if was ready for Friday night. I stumbled and told her i didn’t know. 
She had been texting me all Friday morning,  teasing, convincing me to bring things such as my chastity cage. By noon i had called and reserved a hotel room. Went home during lunch and got a bag of things ready, I was a mess the rest of the day at work. Left immediately after I clocked out, it was a white knuckle drive, the longest 1.5 hours of my life. I checked into my room. She didnt get off till 9 or so that night, so i took a shower, gave myself and enema and locked myself in my cage to wait. She called, said she was on her way. My small penis strained inside my cage, i was ready to explode. I threw some clothes on and waited in the parking lot.
She pulled in, and got out, she was a fairly tall, bbw ebony woman. She giggled and gave me a hug and a kiss. I was going crazy, had only been sexually active with a couple ladies in my life. So I was really going out on a limb. She said ” well here I am lets get going.” 
We went to the room, kissed a little, she told me to get naked, so i did. I felt so venerable. She pulled off her pants to reveal some tight boyshorts and asked me to put the harness on her. I got on my knees and put it on her. Jaz softly asked, “yours or mine first?” I didn’t say a word, but picked up mine as it was smaller, still 8+ long but not as thick as hers. She made me put it on the harness so i did, I stayed still for a minute and she said, “well suck it.” I had never done such a thing and I tried to deep throat it and kept disappointing her.
After 15 mins of me being throat fucked she said it was time for my ass.  I got in position and she got behind me. I had done butt play before, but nothing quite this big, and never with a stranger, she put some gloves on and began to lube up my ass. Without warning, she thrust deep into me. I yelped and she told me I was a good little whore. It felt amazing and she proceeded for probably 20 mins or so. I rolled onto my back and she fucked me missionary style. I loved looking into her dark deep eyes while she fucked me deep and hard.  I laied on my side and she told me it wasn’t time for rest yet. “Get into doggy” so I did. About 3 minutes later she began working her dildo into me, its girth was almost twice as big as mine and 3 inches longer. I about passed out as she relentlessly pounded me. I collapsed onto the bed and she said.”Your a good boy, thanks.”
She pulled the dildo from her harness and slipped her pants up over the harness, said ” thanks for the good time sweetie, call me later!” Then she left.
I tried calling her, but must have been blocked, I’d love to make contact again with her again, but she is long gone…

[M] y Sister’s Hot [F] riends Part 1

I thought it would be satisfying to post some of my favourite sexual experiences, most of which involve friends of my sister while we were in our early 20s. She’s 3 years younger and was definitely the social butterfly through both high school and university, constantly bringing around gorgeous young women for me to pretend not to find incredibly attractive. Amy was my sister’s best friend through her late teens and early 20s. She was a tall brunette with tanned skin, perky tits and a tiny little ass who even though dressed like a bit of a tomboy always looked sexy. She flirted with me constantly and even tried to get me alone a few times but I always teased her about being a lesbian. I think I honestly did it to keep her at a bit of a distance since I had a long term girlfriend through the end of high school and most of university who could tell Amy had a bit of a crush on me.

My wife got caught….[f]

We recently covered up our windows with Halloween decorations so we no longer can see in or out of our windows by our doors.

Last night, my wife had to run out to her car to check for something. Usually she is always in a sports bra and tiny sleep shorts with her ass hanging out and barely covers her pussy (actually, its always visible when she is seated).

My wife came back in after looking for 5 minutes… I thought it took a little extra for her to look for something.

She told me the neighbor was out walking his dog. She was “embarrassed” that she was in her tiny shorts, and bra in front of him. She then preceded to go bend over and look for the item with the door open, and her ass out. I can only imagine how hard he got with her pussy visible. Somehow she was looking for quite some time while he slowly made his way up the street. Needless to say, after she came in, her pussy was dripping and needed a little attention from me.

In the backyard [MF]

(Sorry for any mistakes. English is not my first language)

I had been fucking this guy for a while now. I was 20 years old at the time, still in college, and he was about 12 years older than me. We had been fuck buddies before becoming friends and I’d like to tell you some of the insane stuff we did together. He had an open relationship with his girlfriend and their only rule was not to make that public. Both of them could fuck anyone they wanted, for as long as they wanted, as long as nobody knew about it.

We used to chat a lot and things would get hot quite often. And there were nudes, a shit load of them. Sometimes I would be in class and get a message. “I want to fuck you right now over a table and hold you by your hair until you beg me to stop”. I would get wet instantly. And of course, I did the same to him. I would wait until the middle of the afternoon when I knew he had meetings, and just start flooding his phone with my ass and the description of how I would suck his dick if I were under his table at that moment.

The New Normal (FFM)

“Babe, do you know where my new pair of red panties went?” I asked, taking the last of the laundry out of the basket and folding it.

Nick looked up from his computer. “Uhm, no? Are you sure you put them in the hamper?”

I looked around with a frown. “Pretty sure. This is the second week in a row I’ve been missing underwear – I’ll be going commando every day next month if this keeps up.”

Nick laughed. “Maybe the washing machine has a thing for you, keeping your panties to itself.”

That put a small smile back on my face. “Well, keep an eye out for them at least. They might’ve stuck to your clothes or something.” I put the folded clothes back in the basket, taking them over to the closet.

“Will do. And I’ll tell the washing machine to only keep your old ugly underwear, not any of the hot new ones.”

TEASER: Short term detention facility [Fm] [Fembots] [Chastity] [Prison] [mind control] [long background].

**This is a small teaser for a long story I’m writing, inspired by a series of audio scripts I wrote a few month ago. Tell me how much you like it, and if you want to read more about the interaction between this fembot and her prisoner. I feel like a teaser is completely inline with this story, where edging, tease and denial will play quite a big role.**

You knew that anthropomorphic robots were a thing. You were fascinated, strangely unsettled by the videos visible on the internet from some specialized companies. But you were not prepared to this.

“– Good evening sir. Can I see your ID?”

The robot in front of you looked as if it was a warm and welcoming hotel host. Or rather hostess. Clearly. More considerate, more human in facts than all the people you saw since you went out of this taxi two hours ago, centuries ago. You hand it, or her perhaps, your driver’s license, with the paperwork left from your brief brush with the “normal” penitentiary administration. She, well it took them, sorted and stored them in a drawer in a few, efficient movements, while continuing, conversationally.

One night with Katherina – Part 18 [M+F][prostitution][no.sex]

*This story is the result of a long term roleplay exchange through* r/dirtypenpals

*It features Mathis (u/lmczpn) in first person ordering and enjoying a prostitute, Katherina (u/aurora_w), who is competent and experienced in the anal arts, but touches on some other kinks along the way*

***Katherina:***

At first your touch produces an enjoyable moan, but as you begin putting pressure on the kinks it quickly turns to winces and grunts of pain, so you try to be a bit gentler.

“Yes… right here” she often will guide you to the sore spots.

You lose yourself in kneading her soft flesh, sitting on her thighs and buttocks so you are surprised when you hear the doorbell ring.

***Mathis:***

I´m pulled from my reverie by the ringing of the doorbell, I had almost forgotten that we had ordered food, I was so focused on giving an enjoyable massage.

I get up from the couch, and set my bathrobe right again. I grab my wallet from the kitchen counter and proceed to the door. We exchange money against a plastic bag with our food in it and the delivery guy wishes me a good night before I close the door. If only he knew. It would be the night of my life.

One night with Katherina – Part 17 [M+F][prostitution][banter][no.sex][massage]

*This story is the result of a long term roleplay exchange through* r/dirtypenpals

*It features Mathis (u/lmczpn) in first person ordering and enjoying a prostitute, Katherina (u/aurora_w), who is competent and experienced in the anal arts, but touches on some other kinks along the way*

***Katherina:***

“So..victim blaming.. is that where we’re at now..” she teases while pointing a finger to your breast.

“You should have seen the look on your face, when I took your dick back in my mouth. Like a child on Christmas eve!”

You turn her around, and as you gently knead her neck with your thumbs, she utters a soft moan of relief.

“Well I could do with a massage…” she evaluates out loud

“But..” and she turns around looking at you, “I don’t know about you, but I am really hungry right now…

***Mathis:***

I just smile in response to her teasing, it really feels like we are getting along well. I shrug my shoulders. “Who wouldn´t be happy to have your mouth wrapped around his cock?” I answer rhetorically as I continue kneading her muscles.

Do as I say [NC] [M] [f/m] [blkmail] [huml] [mast][Mdom] [oral] [reluc] [voy] [huml] [anal]

I waited for this moment, literally weeks worth of walking, timing, getting a routine and plotting the actions to pull this off. Having realized that the President of the HOA has a smoking hot daughter in her senior year of high school, the same
President who is also my boss at work, almost makes this too perfect. When my wife had taken the kids to her parents for a weekend pool party, I knew this was my chance. I waited on the other side of the parking lot, knowing that a midnight curfew
always meant a 10:30 hookup for his daughter and her boyfriend, around the corner from her home, I would have 45 minutes before they drove away…
Sure enough at 10:05 the camaro pulled into the parking lot, killed it’s lights and went down the service road to the dead end clearing. Waiting 10 minutes I followed,with my own lights off and everything setup for my plan.
Luckily my wife never asked why I purchased the ultrabright flashlight or the spotlight that plugged into the cigarette lighter… as I pulled up and left 20 feet between us I knew I was timing it perfectly. Even in the pitch black I could see the car was rocking and heavily fogged up. Clearly they were celebrating the big win at school where I’m sure he had done some game winning score or, maybe they were just horny. So I carefully set the spotlight on the left side of my cars roof started my camera and grabbed my flashlight. It was now or never….

Bought my [F]iance a [M]ale Stripper during her Bachelorette in Vegas. [CUCKOLD]

A while back I posted that I was going to pay for a big dicked stripper for my fiance and her friends while they celebrated her bachelorette party in Las Vegas. [HERE](https://www.reddit.com/r/SluttyConfessions/comments/aaf1o8/my_fiance_is_going_to_vegas_for_her_bachelorette/)

P.S. I use Dude/man in place of my name and “Fiance” for her name.

My fiance and I decided to do a joint bachelor/bachelorette weekend in Las Vegas this past summer. The way it worked was they girls and the guys would be staying in separate hotels and besides the hanging out on the flights coming in and leaving we did not see each other once the entire trip.

Us guys had a pretty typical “boys” weekend in Vegas. We spent hundreds on blackjack and twice as much on stripper and drinks at the bar. I won’t lie I had my fun with “Rachel Ann” at the strip club but that alone is another story :)