The Gift Ch. 02

Story Info
Cheryl takes Stevie to his next assignment.
1.9k words
4.65
5k
5

Part 2 of the 3 part series

Updated 06/14/2023
Created 03/23/2023
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

Steve barely had time to register what had just happened. Had he really just given a blow job in a ladies' toilet dressed as a woman?!

"Come on sexy. We've got to make tracks unless you're setting up shop here?". Cheryl stood at the door ready to leave.

Steve gathered his thoughts and moved towards the door.

"Umm, you've missed a bit..." Cheryl said half laughing as she pointed towards the mirror.

Steve looked and saw that his best efforts at keeping the cum inside his mouth had failed and he had some around his chin.

Cheryl moved in close and licked the cum off his face and then kissed him. Steve parted his lips and felt Cheryl push her tongue into his willing mouth transferring a delicious combination of her saliva and Pete's cum into his.

"He needs to get back on the pineapple. Come on let's go. Can't keep the crowd waiting" Cheryl teased and grabbed Steve's wrist leading him out into the bar.

"Crowd?"

Cheryl smiled. "We can talk on the way".

Walking into the bar Steve instantly saw Pete who was talking with two other guys.

He then realised he was now in a public place for the first time dressed as a woman. He hoped Pete would not notice and dipped his head as he walked by.

Suddenly he felt a sharp pain across his ass and instinctively spun round.

"Leaving without saying goodbye are we Cheryl?". Pete was looking even more drunk than before and had a smirk on his face as he looked at his friends for approval of the well delivered smack across Steve's pert backside.

Steve stared at Pete and walked over to him. Not speaking he smiled but then leaned over to one of his friends and firmly kissed him on the lips, winked and quickly walked out following Cheryl.

"That was hilarious! You really are getting into my persona Steve, or should we call you Stevie?"

Steve laughed. "Yes I am. I think you're rubbing off on me Cheryl".

"Ooh in time Stevie. But first let's go to our next party shall we?"

"Party?" Stevie asked nervously.

"Don't look so scared. It will be fun darling. Now leave your car here and I'll drive.

Stevie climbed into her car and Cheryl pulled out of the car park heading down the road leading out of town.

"So have you been to the park of an evening?" Cheryl asked smiling at Stevie.

"Do you mean 'The Park'?"

'The Park' is a notorious dogging spot in the area and frequently made the local news.

"So you do. That's great!" chirped Cheryl. "I've arranged to put on a little show for some friends and you're the headline act sweety".

"God this is getting out of hand. Cheryl I'm not sure I can do that. I mean it's not what I expected or..."

"Stevie. You're doing great and I can tell you're having fun so just trust me okay? I'll be taking care of you. In more ways than one...". Cheryl smiled to herself and turned off the main road onto a small track that after a short while ended at the entrance to a large car park in a wooded area.

"Made it bang on time" Cheryl announced and turned off the engine.

Stevie looked around and whilst the day light was now fading he could just see several cars parked up. Some had single occupants others with couples inside.

They sat for a while and then Cheryl put the car interior light on and leaned over to kiss Stevie.

Her soft lips felt great as he opened his mouth and let her tongue explore his.

She reached down and rubbed his now stiffening cock.

"Touch my pussy" Cheryl whispered as she moved to kissing and gently biting his neck.

Stevie complied and slid his fingers inside her panties which he found were pleasingly wet.

Cheryl moaned loudly and lifted her feet up onto the dashboard giving Stevie more access to her now dripping pussy.

"Use your whole hand. Fist me my little slut" Cheryl was almost screaming and Stevie became aware that the car was now surrounded by a group watching the show they were putting on.

Stevie obeyed his mistress and started to pump his fist in and out of her pussy until she let out a huge cry "Oh god YES!!!". Cheryl almost crushed Stevie's hand as she instinctively slammed her thighs together.

As Cheryl got her breath back as Stevie removed his hand and tasted her pussy juices that had soaked his hand. He was instantly aroused and wanted more.

"Thank you sweety. Now it's your turn. Come on we need to move to the main act for these good people."

Opening the door Cheryl told Stevie to wait at the front of the car as she went to the boot and retrieved something from her bag.

Stevie glanced round and saw several guys of varying ages and states of dress. Some had their dicks out and had clearly enjoyed the show. Others had their phones out filming. Stevie felt a twitch in his panties at the thought he was turning on so many men.

He also saw a woman dressed in a leather mini dress and fishnets who was filming Stevie whilst wanking off the guy next to her. 'Talented' thought Stevie.

"Okay slut get onto your knees". Stevie looked round and gasped. Cheryl was now wearing what can only be described as a huge strap-on dildo that must have been 10 inches long.

"Suck it my little slut. Worship your Mistress"

Sinking to his knees Stevie leant forwards and put the tip into his mouth before gliding up and down the shaft occasionally gagging and choking on the huge length Cheryl was now in possession of.

"That's it. Get it wet slut. It will make the next part much easier for you."

Stevie complied and took as much as he could into his mouth. He thought back to his first blow job with Pete and the taste sounds and smells he experienced as he suckled on this huge weapon of a cock.

Cheryl asked the group if they thought Stevie was ready to lose her virginity. The overriding consensus was yes and as she moved round behind Stevie he realised what was about to happen.

"Cheryl. Please, no don't, I won't be able to..."

"CHRIST!!!" Stevie squealed as he felt the tip of Cheryl's plastic cock split his ass cheeks in two.

He fell forwards but was picked up by one of the guys and looked up to find himself facing a fully erect cock inches from his face.

"Take a deep breath and push out like you're having a crap" the guy helpfully advised.

Stevie did just that as Cheryl pushed deeper into his ass and he felt the full 10 inches slide inside him.

He gasped and fell forwards again only this time his face hit the dick in front of him. The guy grabbed his head. "Suck on this it will take your mind off your ass being broken in"

Stevie obliged and opened his lips to let the dick slide in as Cheryl started to fuck his ass. Each thrust made him gag on the dick in his mouth and from the sounds coming from him it was having a pleasurable effect on the man who was now moaning "Suck it bitch. Take your spit roast like a true slut"

God he was right. He was being spit roasted and it felt amazing.

He heard a groan and looked to see another guy furiously wanking his cock and stepping closer towards Stevie. Letting out a cry he exploded cum all over Stevie's face. This triggered the man he was sucking to also cum and fill Stevie's mouth. Swallowing quickly to take it all in Stevie was now fully into his first gangbang and was loving every moment.

Both withdrew only for another two to step forwards and start to wank in Stevie's face. Both came within seconds drenching Stevie's face and his dress.

Cheryl was pumping hard now and encouraging others to cum on her slut. Stevie was in his own slutty heaven and had never been so turned on as he was right now.

Before anyone else could step forwards the woman in leather knelt down in front of Stevie and said "Here let me help you with that" as she proceeded to lick the cum off his face before kissing him deeply and passing the cum into his mouth.

Stevie was at a complete loss. All of his fantasies were coming true and ones he hadn't even considered.

Then suddenly the sound of a siren filled the air and everyone quickly dispersed running for their cars.

"Oh crap!" Cheryl uttered as the headlights of a police car lit up her deep inside Stevie.

Cars sped out of the car park taking advantage of the distraction being offered by Cheryl and her playmate.

"So what do we have here then?"

A tall police man walked over shining his torch into Stevie's face and then Cheryl's.

"Cheryl?"

"Hello Tom. Long time no see" Cheryl replied with a very self-assured tone given the circumstances.

"So who's your trick? She looks well used. Did you hammer the big one into her?"

Stevie looked in disbelief at Cheryl. She's done this before?! She knows the police officer?!

"Yes she's my newbie but has talent"

"Usual fee?" Tom asked looking at Stevie in mild amusement.

"Yes. But you need to use protection as I haven't put her on meds yet."

"That's fine." Tom replied and smiled down at Stevie.

"Okay up you get and show me your wrists"

Stevie stood up and held out his wrists. His thoughts racing. Was he about to be arrested? What would that mean? Would the papers get to know? Would he be outed as a crossdresser?

The handcuffs slid over his wrists behind his back and he was hauled over to the police car and pushed onto the bonnet.

"Okay sweet cheeks. Time to pay your debts to society."

Stevie looked back but could only see Tom unzipping his fly. Cheryl leaned down to Stevie and whispered "Don't worry, he never lasts long just make noises that he's the best fuck you've had okay?"

Cheryl then dropped to her knees and expertly slid a condom onto Tom's erect cock using her mouth.

Before he could protest he felt Tom's cock at his twitching hole and surrendered to the inevitable.

Tom shoved his hard dick deep inside in one movement forcing Stevie to whimper which seemed to further encourage Tom.

He picked up his pace and started to groan loudly with each thrust.

Stevie was in heaven and despite the pain was feeling like a complete woman.

"Do you like your sentence bitch?" Tom growled as he smacked Stevie's ass whilst pumping even harder.

"Yes Sir. You're magnificent and making me cum" Stevie moaned in as feminine voice as he could muster whilst feeling Tom slam into his ass.

Tom grunted loudly and withdrew his cock. Ripping off his condom he exploded over Stevie's ass cheeks.

"Now clean me bitch!'

Stevie slid off the bonnet and looked up at his latest conquest.

Without hesitation he sank to his knees and began his task.

Tom groaned as Stevie licked and swallowed the remaining cum off the now spent dick.

"Okay, I think justice has been well and truly served here," Tom said as he bent down and unlocked the handcuffs.

"Now I suggest you both move on before I call for back-up".

To be continued

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
3 Comments
AnonymousAnonymousabout 1 year ago

A lovely erotic tale. 4 Stars

AnonymousAnonymousabout 1 year ago

This is one I can really sink my teeth into although not when taking it because I doubt they would appreciate it. This is a real winner. It leaves questions to be answered but gives so much to keep me entertained so I don’t mind waiting for the answers. I really love how Stevie has no idea what he stepped into but is riding it out like a champ, no matter how sticky he gets. I cannot wait to see what’s next and what meds Cheryl is going to give him and will he take them willingly or will he need to be forced or will he be tricked. This is going to be getting even better. My kind of 5⭐️💎.

Share this Story

READ MORE OF THIS SERIES

The Gift Ch. 01 Previous Part
The Gift Series Info

Similar Stories

Roberta Slut Wholesome story of a slut mother and her tranny girl.in Transgender & Crossdressers
Sissy Whisperer An awakening of a sissy.in Transgender & Crossdressers
Good Girl Ch. 01: Discovery Sissy discovers herself with unexpected help from a friend.in First Time
Sam's Noises Who knew I'd discover such a great slut in prison?in Transgender & Crossdressers
My White Boy Sissy Pt. 01 Black football star makes white boy nerd his sissy bitch.in Gay Male
More Stories