Erotic Adventures of Brandon & Cheryl Ch. 03

Story Info
Cheryl has a surprise encounter with a mysterious stranger.
1.2k words
4.17
22k
1
0

Part 3 of the 10 part series

Updated 10/31/2022
Created 01/29/2006
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

At this same time, Cheryl and Tommy had finished their 'session' and Cheryl was hanging out on the second floor balcony out back, bullshitting with some old girlfriends and having some drinks. "So, how's Mark?" Asked one of her friends.

"Oh, I dumped him a long time ago." Replied Cheryl. "The asshole thought he owned me."

Another friend of Cheryl's said "Yeah, but he had some really big feet." Laughing.

"Don't be deceived." Cheryl said back. As they laughed, Cheryl was completely unaware that she was being eyed like a hawk from a distance. She broke away to use the bathroom and when she walked in, she heard someone else come in behind her, and the lights went out. Cheryl opened her mouth to start to talk, but didn't get a chance.

"Shhhh." Came a sexy sultry older female voice that she tried to identify, but couldn't. Cheryl felt some skinny hands and very long nails scrape over her breasts and trail down her body. Though surprised, Cheryl went with the flow. She then felt her unknown partner's long, silky hair tumble over to brush her shoulders as the stranger necked her passionately and viciously pinched and scratched at Cheryl's snatch.

The stranger whispered to Cheryl "I'm gonna make you mine, cutey." Cheryl then realized that this 'woman' had a sizeable erection, which was poking her leg hard. Cheryl had never fucked a shemale before, but was relishing the new experience. "Now.." The stranger said between necking. "I want you...to turn around." The stranger broke away and finished "and put your hands in front of you, wrists together." Cheryl started to worry before she was assured "Don't worry, it'll be alright. Think about it. Would I do anything stupid with this many witnesses who could have seen me walking in? Now hands forward." She asked gentler this second time. Cheryl done as told, kind of nervously, and felt a pair of handcuffs being placed on her. "Now, on your knees and don't say a word." Cheryl done as told and felt the stranger's, who we'll call Shem for now, hands playing with her hair. Shem's fingernails trailed down Cheryl's face to her mouth, then worked themselves in.

Cheryl sucked "Mmmmmm." She then felt the finger come out of her mouth as a large, veiny cock rested it's head at the tips of her lips. Cheryl sucked hard on the tip and then lunged forward.

She was stopped. "Nah-ah-ah. Do only as I say, darling."

With that, Shem ordered her to stand still and grabbed the back of her head with both hands. Shem started to slowly push in as Cheryl's head stood in place and she sucked and tongued Shem's large erection as Shem pumped slowly. After a few minutes of this slow, sensual blowjob, Shem stopped Cheryl again and said "Now, we're going to pick up the pace a bit, honey." With that, she started humping Cheryl's face like a piston. Cheryl gagged and she could feel tears running down her cheeks when Shem stopped in her to the base and stayed momentarily, causing Cheryl to blow hard. Shem then pulled out and told Cheryl to get up. Shem then led Cheryl to a cushioned bench and had her bend over on her hands and knees over it.

Shem toyed around with her, fingering her wet snatch for a minute or two. Shem then pulled a vibrator from somewhere and slipped it into Cheryl's mouth, muffling her moans as she sucked hard. The vibrator was very realistic. It felt almost like the real thing, or as close as a toy could come anyway. Shem positioned herself at the entrance to Cheryl's hot vagina and pushed in just a little as Cheryl squirmed. Then without any kind of warning at all, Shem pulled back and slipped into Cheryl's ass as she pulled the toy from her mouth.

"Aaah!" Cheryl screamed. The toy was then inserted into her horny womanhood as both holes were worked simultaneously.

Both were moaning as Shem talked shit. "You like that, whore? You've gotta be punished for your sins. You've been a naughty little girl." Cheryl then felt a lash from something leather strike her back, but was turned on by it as she continued to be pounded into oblivion and gyrated back into it. "Yeah, that's it, slut!" Shem said as she whipped Cheryl again.

"Fuck yeah!" Cheryl yelled, cumming hard. Then, Shem pulled out and had Cheryl sit on the toilet. Shem spreaded Cheryl's legs to missionary position and grabbed Cheryl's neck as she locked their hips together.

Shem breathed heavily into Cheryl's face and then spat on it. "You ready?" she asked. Still grabbing her neck, almost choking her she shoved her entire length into Cheryl's warm, trembling cunt and started pounding hard. Shem was very well endowed and pounded the back of Cheryl's walls hard, causing her to scream from pain and pleasure, orgasming again and again. Then, Shem came hard, filling her up with what seemed like a gallon of fresh cum. Cheryl cooed in delight, still not saying a word. Shem spoke again. "One more thing. Bend over one more time. I gotta give you something."

Cheryl done as told happily, and then felt something small, hot, and metal-like burn her ass. At first contact, she yelled in pain, but she was still in awe of the whole situation. She was released from her cuffs and a second later, the lights were back on as the door closed. Cheryl ran for the door angry as hell about the "memento" the stranger left on her body. She looked around and seen that it was obvious that she(/he?) was gone. Cheryl looked in the mirror at the still-aching burn on her bottom, when she realized that it was a mark of some sort. She had been branded like cattle. She asked her friends if they had seen anyone come out of the bathroom in the past half hour. They all said that they had been there the whole time and seen noone but her enter and leave. Cheryl was shocked and told her story.

Her friends laughed as if they thought Cheryl was just toying with them. Cheryl then shown them the mark and they freaked. Cheryl told them not to make a big scene. One of her friends then told her that she had seen that symbol before. According to local legends, it belonged to Esmeralda, "The Erotic Witch". Apparently, this was a shemale witch who showed up to various parties of this type doing exactly this sort of thing with very few select hot guys and gals. Also, according to this legend those who bore her mark would receive one gift from her(/him?) later in the form of a spell. It would not be known what this spell would be until it happened. Noone had actually seen Esmeralda, and most though she was just a dumb story. Miranda left for home after that, and didn't even bother to look for Brandon. Some of her friends were curious whether or not this was true, and some were even jealous. Cheryl didn't know what to think herself, but a part of her couldn't help but wonder about the spell part of the legend. Anyway, she left to head back home tired and worn out.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
Share this Story

Similar Stories

Tranny Tales Ch. 01 Can't remember her name -revised.in Anal
Geek Girlfriend Ch. 01 Jack makes a masturbatory mess all over his laptop.in Transgender & Crossdressers
Becoming a Rubberdoll Ch. 01 Cody gets the interview of a lifetime.in Transgender & Crossdressers
Robin and Jimmy Olsen - Sissies Ch. 01 Former sidekicks out on dates with hunky superheroes.in Celebrities & Fan Fiction
Mommy 01: Drunken Sex Mommy calls me over after a late night out drinking.in Transgender & Crossdressers
More Stories