Tag: Anal

Live Chat Stream 1 – Kayla & Theo

Pepper: Good evening, everyone! Welcome you all to the first online live chat stream of Pepper Fawn’s Late Night Chaterviews with me, your host, Pepper Fawn. You must be wondering about the meaning behind the name of the show. Every Friday night, we bring on our live chat stream a real-life sexy story and the people involved and interview them. We are kicking off the very first night with two special guests, Theo and Kayla. So Theo, why don’t you introduce yourself?

Theo: I’ve been a tour guide in the Tappi regions in Southeast Asia for almost ten years. I love the job, showing people around and seeing the excitement on their faces when they see the majestic mountains and waterfalls.

Pepper: That sounds amazing. I will definitely book a tour.

Kayla: You must. It was the best vacation I’ve had, even though I ended up in it accidentally.

Pepper: And it’s part of the reason we’re here today, right? Tell us what you meant when you said, “accidentally.”

Kayla: For my college graduation trip, My family initially booked the vacation for Tappeni, which was fifty-something miles from Tappi. You may call me an idiot. I got on the wrong train after I had to use the bathroom. So, I ended up in Tappi all by myself. Read more »

My Wife (40F) Sent Me (40M) to Vegas to Fuck an Escort (26F) [MF]

(This was a few years ago, so ages are relative to that time)

My wife and I got married in our mid-twenties, and have been together for a while. Outside of our kids there’s not a single person in the world I’ve ever felt more love for. Since day 1 we’ve had an amazing level of open communication I’d never before experienced. I have always felt like I could tell her just about anything, and she did the same to me.

But like happens for lots of couples, the sex life took a back seat to family & career opportunities. Those parts of our relationship thrived (I legitimately had a “my child is an honor student” bumper sticker) but most of the time we were too tired, if we could even get ourselves some time alone.

Our anniversary is a few weeks before Christmas, and we were able to send the kids to a friend’s and have some time to ourselves. The sex was quick, but good, and afterwords we ended up cuddling and talking about our recent dry spells and what that might mean. Ultimately it sort of came about that while she was enjoying our sex life, she just wasn’t quite having the demand for it that she had in the past. She was incredibly content, and comfortable, and loved our life together, but wasn’t feeling the sort of sexual need that I described. Eventually she asked me what I had been fantasizing about lately. Read more »

SOLD!!! – Pt.13/CONCLUSION

I had a smile when I saw Brianna coming thru the doors. She had gotten me away from Veronica, and I couldn’t be happier.

“Bae, let’s talk.” She said, “we need to understand a few things.”

Sitting me down, Brianna began to talk, “Bill, it took a lot to get you away from that twisted bitch. Veronica owed me a favor, as in a life-saving favor, so I spent it on you. Not to be rude, but please bae, don’t make me regret it.”

“Bri-, I get it,” I responded “At least as much as I can. I was having to do some twisted things for and to that twisted bitch. I knew deep down, I’d never get out, and then you saved me!” I took her hand and said, “Brianna, I’ve had a major fucking crush on you since I was barely a teenager. And now here you are. I can’t believe my luck, and no Bae, you’ll never regret it.” I kissed her, then added “I’m REALLY going to enjoy paying you back…you know, we’ve got two plus hours before mom comes home….” Read more »

SOLD!!! – pt.11

Annalisa Sherrill lived in a really nice set of condominiums along the edge of East Bay. They were double-decker and arranged in groups of three, with each group having a connected parking garage. She parked in her marked space near a wall, and at my direction she walked around to the passenger side. This vehicle had the extended rear so the doors opened very wide. Perfect.

“Step back here, and lose the coat.”

“Here? Someone will see.” Always the games.

“So is that a No?”

Without another word she did as instructed, swiveling her neck constantly looking to see if someone was watching.

“Are you planning to do me in the butt?

“Good girl” I responded. “Very smart. Now bend over into the backseat so I can fuck that ass”

Annalisa genuinely hesitated, looked around, and realized I had planned better than I was letting on. So she slipped back into character. “Please. No. Someone will see. It will hurt”

“I’m giving you what you have asked for, and per you, you paid well. Don’t you want your money’s worth? As to Pain? Maybe Yes. Maybe No. Only one way to find out.” Read more »

SOLD!!! – Pt.9

Brianna was enjoying a breakfast that I had whipped up for her. Cooking was something that I enjoyed, so getting to cook for this incredible lady was better all the more.

“Bae, I need you to know something” She said

“What do you need, Bri-?” I asked, “you name it”

“I need to know that this is more than just sex. Bill, I could….I could…”

I put the utensils down, and taking her in my arms, I said “Brianna Davenport, I’ve had a crush on you since back at the store. This is MUCH more than just sex Brianna, I hope I am showing that, especially after last night.”

“You are,” she said, and returned the kiss. “it’s just this thing with Veronica. I am working on something, but I can’t tell you what it is. For now, you are going to have to see other females that she sets you up with, and that makes me sick. But I am VERY close, you have to trust me.”

“I do bae, I swear. Brianna, I’ll do ANYTHING to get away from the clutches of Veronica. I can’t stand being manipulated like this.” Read more »

SOLD!!! – Pt.5!!!

Her eyes lit up like Christmas lights. Marlena really got off on being dominated, and I was getting off on dominating her. I took my dick in my hand and pointed at her wet hole. I touched the tip of it to her slit, the damn thing was positively soaked. She moaned LOUDLY as I slid my member up and down her cunt. I would stop at her entrance for just a second and then I would slide right past it just to drive her crazy.

Marlena would whimper like a dog whenever I slid past her entrance. She needed my cock so bad, and began to beg me in a meek voice “P-P-Please Master! Please use your pussy. It – It wants you SO ba-aa-ad!”. I considered this just another punishment for her. She could barely contain herself, her hips were swaying with my movements, whining and trying to get my stiff dick to fall inside her. Read more »

My Punishment from Daddy for Teaching My Brother [siblings; daddy; daughter; anal]

Part One

Daddy had already left my room, but his sperm was still dripping from my pussy. I scraped a little bit of the white liquid onto my finger and smeared it on my tongue. It was still warm. I loved the taste of daddy’s cum. My heart was racing from the orgasm I had, but it was a close-call as well, because mom decided she wanted a late night snack. Just after Daddy had unloaded inside me we heard her footsteps in the hall. I hated rushing, but the sneaking around was a lot of fun.

I pulled the covers over my naked body and just laid there for a while. The last thing I wanted was to run into mom on my way to the bathroom, so I just played with the sticky cum against my pussy lips, enjoying the moment. The thought of drifting off to sleep came to mind, but my bedroom door creaked open again. This time it was my brother, Matthew.

“Kimmy, are you still awake?”

“Jesus, Matt, don’t you know what time it is? What do you want?” Read more »

My wife is owned by another man [FM M] [cuckold fucking]

“Yes, I love you, Christopher,” Leanne said, “That’s why I married you. But this thing with Paul, it’s different. And it’s not cheating.”

“What?” I said, “You’re going to have sex with him! How is that not cheating?”

“He just wants anal,” she said, her tone weary, like she was explaining something basic. She tucked her hair behind her ear. Deep red, in a short, cute style, it looked good on her.

“You don’t even let me near your ass,” I protested.

“Yes, obviously,” Leanne rolled her eyes, “You’re married to me, you get my pussy whenever you want it, I don’t know why that’s not enough for you. But my ass has always belonged to Paul.”

I glared at her. “Fine, your pussy’s mine? Let’s fuck. Right now.” She was sitting next to me on the couch wearing sexy black lingerie that I’d never seen before. I reached over to grab her hips, but she swatted my hand away.

“No,” she said, “Now’s not a good time.”

I started, “But you said–” Read more »

[FM] Seducing my (f/23) girlfriend’s new roommate was more than I bargained for

Recently, I’ve been enjoying a sexual relationship with a gal named Emily who I met out dancing one night last spring.

For those of you who haven’t seen pictures of me (I stopped sharing them awhile back because of some really concerning stalkers – I have a post on it if you want to know more), I like to wear a cross between a “girl next door” and an elegant/fashion-forward styles. I have a long slim torso, long legs, and relatively small pointy tits (b-c cups) and am considered beautiful by many but Emily is very different. She has a punk/goth style. She has a nose ring, lots of ear piercings, short black hair that is usually tussled and spiked in the back, and tattoos all over. Her features are delicate and angular, her lips are plump and firm, and her eyes are big and brown with long, long lashes. Her skin is like porcelain and she’s short and curvy with a long torso, narrow waist, and big round DD tits with high nipples surrounded by dark brown areolae that perk up the moment she’s turned on. Her pussy is usually trimmed into a dark landing strip and it throbs bright red in contrast to her milky white skin. She’s gay (I’m pan) and she likes her clit licked and rubbed as she’s being penetrated with a dildo or strap on. She makes sweet, small moans and gasps as she orgasms, her muscles contract and roll like waves and her cum tastes like salty rose water taffy (I am uncontrollably loud and shake and quiver when I cum). Like me, she’s capable of multiple orgasms and we have spent a number of days shut in during the pandemic making each other cum for hours on end, breaking only to eat and rehydrate. Although we have an open and undefined relationship, Emily has been my main physical and emotional relationship this past year, and she has been very understanding and supportive with my sex life and is an awesome friend as well as a lover. Read more »

He [M] blew his load in all three of my holes [F] (Part 1)

My ex (35M) and I (29F) have been sleeping together for the better part of the last year. I am still madly in love with him, and while a part of me knows he does not feel the same, I’m ok with putting my emotions on the back burner for some amazing sex…which is what we have together. A couple months ago he took my anal virginity, in fact before him I was not into butt stuff, and now almost 2 years later I am begging him to fuck me in my asshole. Read more »