Sissy Friends Forever Ch. 03

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

"Is everything OK with you?"

"No," he said simply. I felt bad for him. I put down my purse and got on the bed beside him.

"Want to talk about it with someone?"

"I don't know."

I rolled over and put my arm around him to comfort him. "Please tell me what it is, David."

He rolled towards me and put his arm around me too and squeezed me tight. To my surprise he started to cry. I didn't know what to do. I just held him for a few minutes until he opened up to me. "That's the first time I've had sex in ten years. I thought that was what I needed, but when you held me just now," he sobbed, "I realized I just wanted to be hugged. I just needed some human contact, I want someone to love me."

I kissed him. "You can hug me for as long as you want, David."

"But then you'll be gone and I'll be alone again."

I considered for a moment. "Maybe I can help."

We talked until his time was up. I felt bad about leaving but I knew Cindy was waiting for me and she would break down the door if I didn't make an appearance on time, so I swiftly made my exit and got back to the car.

"Right on time!" said Cindy as closed the door. "I guess he got his money's worth and I trust your cum addiction is fully satisfied now?"

"Nope. He only wanted anal."

Cindy's mouth fell open and she raised her finger. "You know, I didn't think of that."

"You really are the dumbest bimbo."

"Thank you, sweetie."

"Well, due to your incompetence, I guess I'm just going to have to find something else to suck then." I looked at Cindy, then looked down at her skirt and met her eyes again. I licked my lips suggestively. I kept the key to her chastity cage on a necklace around my neck. I pulled it out of my dress, while lifting her skirt with my other hand. I wasn't really going to suck her, but just wanted to make a point about how in need I was.

"Ah ah, no, no." She pushed me away and waggled her finger at me. "I'm not on my sissy period."

"Fine then. I got my own stash." I pulled down my panties, hitched up my skirt and felt around between my legs for the condom. I pulled it out and showed it to her. "Still got his cum in me and you're not getting any." I tipped it up into my mouth and swallowed down the few drops that slid out.

Cindy cracked a smile. "Oh my lord. Want kind of monster have I created?"

I sat back in the seat with satisfaction from tasting the salty nectar I craved. "A ravenous cum slut."

"Glad to hear it, that's what I was going for. But let's just tone it down a little." She snapped her fingers in front of me and said "Reset!". I was unceremoniously thrown off the train and my perspective shifted in an instant. Suddenly I didn't want the condom anymore and dropped it into the footwell.

"Well that's working then."

"Oh Cindy, it's amazing. When I let myself just slide into it and really roll with it, I am desperate, like a drug addict or something."

"So are we doing this again?"

"Absolutely."

"Great. I'll keep your profile up on the web and see what fortune brings." She held out her palm expectantly. "So, hand over the money to your pimp like the obedient little hooker you are."

"Money?" I suddenly had a terrible thought. Cindy looked at me with exasperation.

"You didn't?"

"I forgot to ask for the cash."

"So you fucked him for free?" Cindy burst out laughing. "You are the world's worst call girl."

"Doh!" I slapped my forehead. "It's your fault, you turned me into a cum addict, that was all I was thinking about. I can't go back now."

"Yeah you're a real Belle De Jour. No excuses. You owe your pimp $150."

"Can I pay you in spanks?"

"Well, I suppose that will have to do."

"Fine then. Call at an ATM and I'll get you $150 cash right now." She loved being spanked more than just about anything. There was no way she actually wanted the money.

"No takebacks. You said you'd spank me. I'm going to be over your knee most of the evening to cover this one." Cindy started the car.

"There's just one more thing."

"What?"

"Don't get mad, but he was really really lonely and sad and..."

"Oh, no."

"I said I'd help find him a boyfriend."

"Aaron! This is Eric all over again. You're a soft hearted moron, you know." She turned to me and smiled. "And I can't help but love you for it."

...

I was sitting on the couch with Cindy lying in my lap. We'd had a long day packing for our honeymoon. It was just so tough for a girl to decide what she might want to wear. We'd got so much stuff I'd had to book extra luggage with the airline. We'd packed at least a dozen outfits each and of course our respective French maid costumes. As part of our extensive itinerary, I'd rented an old château and we were going to take photos of ourselves cleaning it and serving there.

I put my finger between Cindy's plump lips and she started sucking it instinctively. She seemed deep in thought. After a few minutes she stopped sucking and pulled her lips away from me. "Do you think there's a maximum amount of pleasure a girl could feel?"

"Well marrying you must be pretty much up there."

"No you're wrong. Sadly you'll never know true pleasure," she got up and put her face close to mine, "because that's marrying you." She kissed me. How lucky I was to have someone so in love with me. "But a girl can only marry her Aaron once. How can I recapture that level of ecstasy?"

I thought for a moment. "Have you seen the movie Barbarella?"

"No, I've heard of it, kind of, I think."

"It's an old sci-fi film from the 1960s. Part of the plot is there's a machine that causes a woman to have so much pleasure it's nearly fatal."

"So, where do you buy these machines? Asking for a friend."

"Hmm... let's see what we can do."

I led her by the hand through to the guest room. I snapped my fingers, ordered her to obey me and told her to take her clothes off. There was a small desk with a laptop on it. "Cindy honey, can you clear the table and move it to the photo backdrop please." As she got to work I started rooting through her boxes of shop stock.

When she had the table positioned I told her to lie over it. I was looking through her selection of restraints and discovered a metal pole with two loops of metal on either end.

"Cindy, what's this?" She looked up from the table.

"It's a spreader bar, for restraining your ankles." It looked like fun. I went over to Cindy and locked each of her ankles into it, then I figured out the length of the bar could be extended. I widened it, forcing her legs apart by about three feet.

I looked through her collection of butt plugs and found four types where the packaging said they had a vibrating feature. I took them all over to Cindy. "Which one of these is best honey?" She gestured at a pink plug. I turned it on but nothing happened. Batteries not included. After raiding the TV remote I lubed her up and pushed it in about halfway. "Is that good?"

"A little further in," she said.

"Tell me when." I pushed the butt plug in gently until she indicated I had found the right position for her. I switched it on and it started buzzing. She gasped.

My next target was her nipples, which were hyper-sensitive due to her hypnosis. I wondered how I could find some sort of mechanical way to stimulate them. Then I realized I didn't have to. In her state of obedience, she'd be compelled to do whatever I wanted. I found a pair of fuzzy handcuffs linked by a chain and metal collar. I looped the handcuffs through the collar and put it on her. Then I put her wrists in the restraints. She had just about enough slack to reach her breasts.

"Cindy, play with your nipples until told to stop." She started lightly brushing her nipples and immediately breathed in sharply. "Tease them honey, pull and twist." She got a little rougher with herself and started moaning and closed her eyes.

I took her phone and started recording. I thought I'd capture something for her porn profile at the same time. I moved the camera all around her to show the setup and then put it in the stand. I went and leaned against the wall and just watched her as she panted. After a few moments, I left her alone and walked out of the room closing the door. I thought it would tease her if she didn't know how long she was going to be left in this position or if I was coming back.

I heard screams of pleasure, shouts and moaning. After about ten minutes I went back in the room. She'd managed to stand and was waddling in the spreader bar away from the photo backdrop, still twisting and flicking her nipples. "Hey you! No escaping. Back on the table!" I ordered. She immediately leaned back over the desk. I switched the camera off and started spanking her rapidly. She let out a short yelp with each stroke. "You do not move without permission."

When I'd given her about fifty spanks I squatted down in front of her face. Her eyes were rolled back in her head and her mouth was open. "Aaron..." she started to say something.

"Who told you to speak?" I pinched her lips closed with my fingers, then I snapped my fingers in front of her face. "Good girl!" I hypnotically triggered her to go into a state of bliss. She slumped with her eyes closed, her hands hung loosely from her collar by the restraints. I got on my knees in front of her and lifted her chin with my hand, then started kissing her. When she woke up she started automatically pinching her nipples again. "Good girl!" I repeated again about a minute, snapping my fingers. She slumped again and I kissed her until she woke. I didn't normally use this trigger multiple times in a row as I thought it might be too much, but I did it a third time and kissed her again.

When she woke up for the third time, she was panting hard. I thought she might be hyperventilating. She seemed exhausted. I decided it was time to let her go. I pulled out the butt plug and released her from her obedience. Her wrists immediately slumped away from her nipples. I unlocked her wrists quickly and her hands flopped to the floor. "You OK honey?" I asked as I removed the spreader bar.

"Mmmm..." she didn't seem to be able to respond and was still breathing heavily. I was concerned I'd gone too far. I kicked off my heels and lifted her up. She could hardly walk. I swept her up in my arms and carried her through to the bedroom and lay her down. I knelt over her worried. "Cindy honey. Talk to me."

She didn't say anything for a few moments, her breathing slowed and then she finally answered me. "Christ almighty Aaron." I was relieved she was speaking.

"I was panicked there for a moment." She smiled. "I thought you had reached fatal levels of pleasure."

"I nearly did. I had about ten orgasms, I think my brain exploded."

"Yay!" I slid my hands up her body, dangerously close to her nipples. I knew they'd be raw by now.

"If you touch my nipples, I'm going to slap you." Cindy pointed a warning finger at me. "I think I need about a week to recover from that."

"That's what I hoped."

"I think I'm going to go bare-chested for the rest of the day." She stretched, arching her back and pushed out her huge boobs. "I don't think I can even wear a bra right now."

"Works for me."

"Oh, do you like women's bodies do you sissy?"

"No," I said furtively. "I love men with hairy chests and big dicks." I slid my hands up and down her and stared at her breasts longingly.

"I think you lie. More hypnosis for you."

"So how do you rate the Barbarella machine out of ten?"

"Eleven."

"Do you think you reached maximum pleasure? Is there a twelve?"

"Let's get packing up some stuff to play with. On our honeymoon, I want to aim for twenty."

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

READ MORE OF THIS SERIES

Similar Stories

Becoming My Sister Pt. 01 A boy's obsession with his sister changes his life forever.in Transgender & Crossdressers
"Maid" to be a Cuckold Pt. 01 Sam goes from husband to sissy maid.in Transgender & Crossdressers
Taking a Delivery Wife arranged for me to take a delivery from a trans friend.in Transgender & Crossdressers
Play Date A young CD has a play date with her sissy friend.in Transgender & Crossdressers
A Change in Routine A couple explore the husband’s feminine side.in Transgender & Crossdressers
More Stories