The Chastity Trap Ch. 02

'How did it go last night, any indication if he'll sign the contract?' Ty's message asked.

Lottie came back into the bedroom and looked over at Steven on the bed, he was still sound asleep, the sheets half covering his naked body. Smiling she thought back to the night before, it had turned out to be a wonderful night and Steven was a very attentive lover.

Unsurprisingly the signing of a contract had been the furthest thought from their minds when they went to sleep, but noticing the folder on the desk she crept over and picked it up, along with a pen from the hotel stationary before putting it on the bed side table next to Steven.

Putting the phone down she grinned as she crawled back onto the bed and pulled back the sheets, before gently cupped the sleeping man's flaccid cock. Lowering her head she licked up the underside of his shaft once more, Steven moaned as he slowly woke up.

By the time he realized what was going on Lottie was once again taking his entire cock into her mouth, only unlike last night she was in no rush to let him cum. Using all the skill she had she kept the moaning man on the edge of cumming for an age, Steven was moaning and groaning in part pleasure, part desperation. Slipping her mouth of his cock she slowly stroked it up and down with her hand, looking up at her lover smiling.

"Good morning lover," she purred.

"Best morning more like, don't stop!" he begged.

Lottie chuckled. "Oh I'm in no rush, besides I need to ask you something."

She lowered her head onto his cock again slowly taking it is and sucking hard.

"Anything." Steven said.

"You're going to sign the contract right? I mean I'd hoped you would then you and me can hook up again." she said breaking off again from his cock. "Besides, Mr Wallace won't be happy if I return empty handed."

Steven chuckled. "I knew it, Ty send his hardest negotiator didn't he. This isn't fair at all!"

"I'm not the hard one now am I?" she said looking down at his fully erect cock. Stroking it up and down with one hand she sucked on his cock head for a few moments, using her tongue to make swirling patterns over its surface.

Steven groaned. "It's not that easy, I mean there are some minor points to agree on first."

"Minor?" Lottie said still focused on his cock. "Surely minor doesn't matter, that's just crossing I's and dotting T's right. I mean surely there are more important things in life."

Lottie was going so slowly now, Steven was on the edge but knew that Lottie wasn't going to let him off easily.

"Oh god this isn't fair. Ok, ok, ok, I'll sign the bloody thing."

Lottie smiled wickedly, his cock still in her hand glistening from all the saliva as she continued to stroke him gently up and down.

"I'll do it ok? Please!" Steven begged, but Lottie simply looked over at the contract on the side of the bed and back at him.

"Damn!" he said reaching over and picking up the contract.

He tried to read it over just to check, but Lottie once again was taking his entire length into her mouth and throat making him groan deeply.

"There should be a fucking law against signing contracts and having blow jobs!" he said before squiggling his signature on the form. "In fact there probably is, its call coercion! There its signed, happy?"

"Not yet," Lottie said sitting up and checking the document, before tossing it over on the bedside table again. "But I'm sure you can help with that too."

Lottie straddled his lap and guided his cock into the folds of her pussy for the umpteenth time and moaned. This was most definitely the life, she wondered if Ty had any other VIP's she could 'help out' with.

By the time they finished it was approaching 11 am, Steven and quickly dressed. "No need for you to rush ok, the room is all paid for until 3pm I think, I need to get home unfortunately."

He sat down on the edge of the bed looking over at Lottie's naked form on the bed. Tracing a finger up the back of her leg he continued over her butt and up her back bringing a moan from Lottie.

"Damn I could stay here all day." he muttered. "You might bankrupt me, but I'd stay!"

Lottie wasn't sure what he mean by that and scowled a little. "Come on, the contract wasn't that bad was it, I mean I assumed by minor they were things that didn't really matter."

"What? Oh no not that." Steven said getting up and collecting his things. He seemed to be thinking about his words carefully, and after reaching into his pocket he pulled out a brown envelope and placed it carefully down on the side.

"I know we didn't talk about this at all, Ty didn't really elude to the financials of our agreement but hopefully you are not disappointed by this." He said letting go on the envelope and walking round to the side of the bed. Leaning over his kissed Lottie on the cheek.

"Thank you for the most wonderful time Lottie, I hope you are available next time I'm in town." In moments he was gone, the door clicking shut leaving Lottie alone in the room.

Lottie was still laying on the bed stunned. Suddenly everything had slipped into place, from Ty's request to 'show him a good time' to Stevens comments that 'he'd never don't this before'. She'd just fucked a man for money, the warm fuzzy feeling she'd had just 5 minutes ago was gone, replaced with an almost dirty feeling.

As she stepped out the bed she started to cry, and wanting to get out the place immediately she grabbed her clothes screamed in frustration. How the hell was she supposed to walk out the hotel dressed like this, everyone would know she was a, well, whore surely.

She grabbed her phone and texted the only person she could think of in times like this. She needed a friend, someone that she knew would always be there, would not dare judge her. Throwing the phone down next to the envelope she starred at the offending item for a minute, unable to mount the strength to open it.

Finally breaking her gaze she figured she have at least 30 minutes before help arrived, so she made her way into the bathroom and turned on the huge walk in shower. She could at least wash some of the dirt of her skin, even if she would still feel dirty inside.

***********************************

Malcom had resisted the urge to phone Nula immediately that morning, if he was going to contact her he would at least wait until a civil time. He had waited until just after 10 before sending her a text, it took him over 10 minutes to write the short text.

"Please Mistress, I need to see you. The pain of the cage is too much, I can't go another night."

As he pressed send his hand was actually shaking. He wasn't sure at all if this was the right thing to do, she had explicitly told him not to contact him but the situation was bad. He'd hardly slept after he first woke up, every time he tried to all he could think about was Nula, her perfect behind, her glistening pussy lips. His cock throbbed almost immediately and in the end he ended up helplessly sobbing into his pillow, curled up in a painful ball.

He was surprised that Lottie wasn't home when he woke, he'd gone upstairs and noticed her door still open, obviously she had made good on her word to phone Ty for a booty call as she put it.

He was just about the head out for a walk to clear his head when his phone buzzed to life, it was a text from Lottie.

'Mally, please help me. Can you bring a bag of normal clothes for me to the Grand Street hotel, room 1456. Please hurry, I'm desperate to get out of here but only have my cocktail dress. Not the sort of place to do a walk of shame.'

Malcom chuckled reading the text, Lottie was shut a dirty stop out!

'U R such a stop out, B there in 30.' he shot back.

Rushing upstairs he grabbed a small carry bag out of Lottie's room and from her draws picked out her short denim skirt, white tank top, knickers, bra, socks and sneaker pumps. He figured she'd want comfort having been out all night, but as he packed the bag Emma emerged from her room and shot Malcom a look of disgust down the hallway. He was standing there with her bra in one hand, and knickers in the other.

"Hmmph, perv." She shot at him. "I'm putting a fucking lock on my door."

"It's not like that, I'm just packing..." he shouted down the hall but she was gone.

Malcom sighed as he fished putting the stuff in the bag and left for the hotel. It was a beautiful day, the sun was shining brightly and as he made his was towards the hotel he thought again about Nula, and the situation he was in. Given Lottie knew most of it anyway he'd figured the walk back would be a good opportunity to bounce ideas of her.

No sooner had he knocked on the door to the room had Lottie opened it and dragged him inside. She was wrapped in a large white fluffy towel, her hair still wet from showering. He could see her eyes were puffy, she had been crying.

"Lottie, what's up?" he said but was distracted by the room.

"Wow, this is posh Lots. Take it you didn't just have dinner and drinks." he said spotting the bottle of Champaign and half-drunk glasses,.

Lottie grabbed the envelope and shoved it into Malcom's chest. "Shut it, just shut it right."

He looked down at the envelope in his hand before holding up, looking confusingly at Lottie. "What is it?"

Lottie was riffling through the bag pulling out the clothes.

"My payment apparently." She looked over at Malcom. "Your cock still locked up?"

"Um yeah, I am." he said confused. "What do you mean payment?"

Lottie dropped the towel there and then, clearly knowing he was still locked meant she didn't care about being naked in front of him. Malcom rolled his eyes and turn round to look in the opposite direction.

"Payment Mally, the man fucking paid me. Like a whore or something." She said shaking in anger. "When I get hold of Ty I'm going to rip his fucking cock off."

"Oh my god Lottie, he paid you to fuck him? You said yes?" Malcom said in disbelief.

"I didn't know he was paying me Mally, I just thought we were hooking up. I mean he was really nice, we got on and I figured why not have some fun. I go to the club, get pissed and pick up strangers all the time, sure this was posher and a bit more arranged but was along the same lines right?"

"Clearly not to him!" Malcom chuckled before looking over at Lottie. "Sorry, I didn't mean to laugh at you."

"Fucking right Sissy, just remember I'm not the only one with a secret to keep. You tell anyone, I mean ANYONE about this and you will pay believe me."

Malcom knew Lottie wasn't messing about, and he nodded frantically. "Sure Lots, not a word. Our secret."

She had finished getting dressed now, and looked around the room at her things. Lingerie was scattered everywhere, and the bed was a complete mess from the rather energetic fucking. Chuckling in disbelief at the situation she held out a hand for the envelope.

"Give it to me and pick up my things sissy. I should at least know how much I'm worth right?" she sighed. "It was such a good night before that as well, he was a fantastic lover."

Grabbing the envelope she carefully open it up and looked inside as Malcom carefully collected her things. She watched him pick up her knickers and chuckled.

"Don't get any idea's sissy, they are my best agent provocateur knickers. I can see you'd like to wear them." she said.

Malcom looked over at her and flushed red, it had crossed his mind as he picked them up what they would be like.

Lottie flopped into the seat as Malcom carefully finished folded her things into the bag, before looking over at the stack of notes she had in her hand. He could see from here they were all £20 notes, and there was a lot of them.

"Fucking hell Lottie, how much is that?" Malcom said in disbelief.

"It's twelve hundred pounds Mally, twelve fucking hundred pounds for one night!" she said shocked.

"Damn, that's a pretty good nights wage given you also got a free dinner and hotel thrown in." she said. Lottie shot him a dirty look, but then glanced back at the money.

Shoving the money into her hand bag she grabbed the contract and stood up, walking towards the door.

"Come on, let's get a coffee on the way home. If you are nice I might even offer to buy it." she said finally smiling. "You can carry my bag, Sissy."

It took them nearly three hours to get home, Lottie did indeed spend some of her herd earnt money treating them both to lunch. Lottie had a wonderful steak dish whilst Malcom had the fresh fish. They sat outside on the veranda of the restaurant, sharing a bottle of ice cold white wine. Neither sad much to each other about what was on their mind, but both relaxed and used the time to process things.

Malcom told Lottie about Emma, and he was pretty sure that in a few weeks he would have moved out. Lottie on the other hand told him not to be so silly, she'd talk to Emma and get it figured out in not time.

When they finally got home there was a box sat on the doorstep, a large pink ribbon held together two grey box's. Lottie bent down and picked up the card, before chuckling and handing it to Malcom.

"It's for you I think, unless you know of any other Sissy's in the house!" she said. Come on, let's see what's inside.

Malcom looked at the card as Lottie opened the door.

'To Sissy, Love Mistress.' A simple yet powerful statement that made his heart skip, she was still thinking of him.

Inside Lottie dumped her bag and sat down on the sofa. Malcom didn't even have a chance to sit down before Lottie had ripped the bow off and opened the top box. As soon as she looked inside she chuckled.

"Looks like your Mistress has bought you some new panties Sissy."

Lottie picked up the top pair and held them up to Malcom. It appeared to be a pink thong, the material was a soft looking lace similar to the black pair he was forced to wear home from his encounter with Nula.

"Wow, these are actually pretty expensive knickers Mally, they are from Fox and Rose! There's a note inside as well".

Malcom was humiliated, his face was burning red as Lottie took out the note and read it aloud.

"Dear Sissy, you looked so cute in those panties yesterday I just couldn't bear the thought of you having to put back on those ugly boy things you wear. I've splashed out on a full set of undies for you and expect you will be eager to always wear them. With love, your Mistress. Nula."

Lottie put down the note and looked up at Mally. "That's so cute Mally, she really likes you and just wants what's best. Let's go throw that boy stuff out right now."

Lottie paused however and looked at the back of the note, there was more writing.

"P.s. You will need to read the care instructions carefully, and I expect you to throw out all those nasty boy undies you no longer need."

Malcom sighed. "What is it with care instructions, I mean Emma had a go at me last night before doing your washing." Malcom said.

Lottie looked up at him nervously.

"Please tell me you didn't do what I think you did. Tell me you didn't just shove everything into the machine." She said. "If you have ruined my clothes sissy..."

Malcom held up his hands. "I didn't wash anything as I didn't know what I was doing ok, Emma wasn't exactly forthcoming you know."

Lottie breathed a sigh of relief before opening the second box. "Ok good, I can't believe you just shove everything in Mally, you will learn to separate..."

But Lottie stopped as she opened the second box before bursting into laughter. "I love this woman."

Malcom looked in horror as Lottie held up a bra that matched the first pair of panties Lottie showed him, it was clearly a set.

"You are going to be super cute Mally, let's have a fashion show shall we?" Lottie said chuckling.

"Lottie please." he begged, but Lottie simple sat back grinning.

"More wine Sissy, then I expect you to try on every set for me."

For the next hour Malcom was made to try on every set of underwear he had - there turned out to be 14 sets in the end. Lottie marched him into his room and made him kneel on the floor as she went through his underwear draw pulling out every pair of boxers he had. She threw all of them one by one into a black bin bag, before tying a knot in it and taking it outside to the bins.

Malcom sighed, hoping his humiliation was over, here he was sat on his own floor in noting but a bright pink thong and matching bra whilst his best friend threw out all his undies. It was about to get worse however as Lottie pulled him back into the living room and made him kneel on the floor in the centre of the room.

"You have a lot to learn it seems sissy, let's see what you tube can tell us about doing laundry correctly shall we?" Lottie said grabbing her iPad and quickly pulling something up. "Ah yes, this is perfect."

She put the feed onto the TV and the screen went black for a few moments, before pink writing came scrawling across the screen.

"A Sissy maid's guide to : Laundry." said a female voice.

Malcom looked over at Lottie who was watching him intently, he went to open his mouth to beg her to stop but she held her hand up and pointed at the screen.

"You will be tested after Sissy, I suggest you pay attention."

The video started, it showed a whole pile of mixed laundry and a rather beautiful woman clad in a latex top and shirt standing over it smiling.

"Don't know where to start on the laundry sissy, let Mistress Household teach you the ropes."

The video proceeded to go through every step of doing the laundry, explaining the separation of colours, the identification of delicate items for hand washing, and the different settings on the washing machine. Mistress household, as she referred to herself, seemed to speak to the camera as if talking to a three year old child.

The video moved on from using the washing machine to treating delicate items, such as lingerie and Malcom couldn't help but become aroused as Mistress household reviewed an number of different types of lingerie, along with explaining how there were to be washed. By the end of the video Malcom's cock was straining in its cage.

"Did Sissy enjoy looking at all that dirty laundry, did it exited you to think of hand washing all those cum covered panties?" Lottie teased. "I hope so, I've got lots for you to do after this weekend!"

Malcom groaned, it seemed his life had just got twice as complicated.