Freelance Encounter.

Jessie reached John’s room as planned at 8pm and she understood that her freelance job would usually require to have sexual intercourse with her clients. Rarely she would enjoy the session like how a lady would wanted, but it was the money that kept her doing it. The flexible hours, minimum pay, all helped to give her life some sort of organisation. Back to John, he had an unusual request that Jessie had not done before, to put a chastity belt with a two inch dildo attached to it. Trying hard to contain her sigh, she took it from him with a smile and slipped it on after a quick shower.

The belt was slightly obvious under her one piece dress that had a diamond shape cut out around the sides of her waist, but with some adjustments, she got it on and her panties had to be left in the room. They hopped on his car and he drove her for dinner at one of the food stalls opened for the night crowd. She was instructed to order the food at the counter and she got to keep the change for just two S$4 meals paid with a fifty dollar note. The dildo in her went off as she spoke and it had gotten her knees to shiver for a few seconds. An awkward shift of her hips caught quite a few eyes but she was still safe.

Dinner was done at a normal pace and he drove her further out to a packed carpark. This man clearly had some fetish she could not understand.

John: ‘Hold my hand and we’ll walk one round around the carpark.’

They went from the first floor to the fourth, that was open air and the cooling weather definitely helped to sooth her mind. The toy once again came on and she felt more willing to let her moans escape through her glossy red lips. The surrounding was facing some flats and the rest was pretty much unblocked.

John: ‘You can take that thing off now.’

Jessie: ‘Right here?’

John: ‘Yes.’

She turned her head around quickly to make a quick scan and her dress was lifted, high enough for her to find the belt buckle and remove the dildo that had made her felt so sexy in public. John then brought her to the little shelter where the stairs lead up to and placed her against the side that was not facing any buildings. He leaned onto her and started to kiss her lips lightly, switching between pecks and french.

Somehow, his kisses had brought memories of her ex-boyfriend back and she realised he had been missed a lot, so much so she almost cried. His palms that was on her back shifted to her hips, to slowly lift her dress up to expose her pussy. She did not resist him and let him pull it higher. Her fingers went without instructions to her clit and she placed her legs apart, beginning to touch herself freely. He hugged her closely and gently gave her ears a lick.

John (whispering): ‘You like it?’

Jessie: ‘Mmm~’

Her own fingers had done a great job making her wet and the noise of his belt being undone was a signal for her to do what she needed. Sliding her back down the wall, she held his dick that was about 5 inches, taking a whiff before bring her mouth to it. Starting with a kiss at the tip, her lips did not opened too wide before she sank her mouth down his shaft, until it reached his base. Perhaps it was a good thing he wasn’t too long, she could still do a deep throat for him.

Jessie did not rush through and was blowing him quite steadily, sucking him hard and going at unpredictable speed. So far, he only held her head and not forced her in anyway. He was turning into someone she enjoyed pleasing. Close to five minutes later, he brought her to her feet and he took his time rolling the protection on. As a favour, she helped him with that and rolled it with her mouth until the rubber ring was as far as it would go.

John: ‘Trust me okay? I won’t let you fall.’

That sentence did sound a little scary, but she knew he was different. He held the back of one of her knees and raised it to his rib level. With just one leg balancing herself, she then understood what he meant. John went as close as he could to her and bent his knees slightly to let his dick glide into her pussy. Although it did not feel as good as doing it without a condom, she was happy with his gentleness. Very slowly, he made thrusts not more than once at a time, until the leg in the air went behind his back, yearning for something wilder.

His elbow held onto her leg behind him and as much as he could, supported her by holding her sexy slim waist. Right then, he moved faster and the whole package of a sensual sex was fulfilled. Her body was enjoying every bit of him, not just sex. From his kissing, to the skilful thrusts he could do. She only felt how her pussy accepted him strokes after strokes. In less than two minutes, her other leg had wrapped around him with a light jump.

He caught her and pressed her against the wall while pounding excitedly, caressing every inch of her intimate cave. With their close body contact, her clit was stimulated by his prickly pubic area, driving her confused with the senses. First there was vaginal satisfaction, then came the clitoris teasing. Her first orgasm came quick and it had hit her really hard. John’s firm grip allowed her to relax her arms hanging on around his neck and the trembling of her body (from the climax) was given enough time to recover. Of course, she did not just get one orgasm from his position given his unhurried pace.

The two of them went into the shelter after a while and she was asked to bend over the railing. With no questions, she complied. His dick penetrated her again and the crazy fuck began. With her mind being pushed to the limit, she realised that it was this that was missing from her ex, the considerate factor that this client had managed to capture. Her hands held on to the rails tightly as he pounded hard into her, making her drip her thick cream onto the floor.

His hands did not stay long on her butt or lower body. They went to her breasts under her bra and gave them some love as well, rolling them between his fingers not too hard to cause any pain. All that stimulation drove her crazy and her moans was getting louder by the minute. Despite knowing that, he did not try to silence her but went faster and faster.

John (whispering): ‘Shooting! Shooting!’

She gave him a light push backwards and turned around quickly, kneeling on the floor with a thud and yanked the rubber off. She then pulled him by grabbing his butt, pushing his dick into her mouth and just threw her face at his pelvis. On and on she went, with her fingers masturbating herself to another orgasm, it was so comfortable doing it for this man unlike others.

He lost control for that moment and grabbed her head with two hands, thrashing his dick at her until the point of no return had passed. The eruption of his love juice flooded her throat and although the first few waves were extra sticky, the last few were more watery and it flushed the load down into her gastric. He stepped to let her catch her breath, but not before her body shivered again, with her wet fingers at her pussy. The sight of her throwing her head back was priceless given that her job was done, but she showed her how much she enjoyed having sex with him.

John rested for a while before helping her to his car, panting and cleaning at the same time.

Jessie: ‘You don’t exercise a lot do you?’

John: ‘Hehe. Caught by you.’

Jessie: ‘Looks like we need more work out to get you fit again – down there.’

The smile remained on his face for as long as she was with him. They took a shower together with less foreplay and more ‘love’, kissing and touching each other so sensually she wanted to give him another shot for free. But it wasn’t his style to take advantage of her. They were done in a while and the call to notify him that the time was almost up disappointed him a little.

John: ‘Where do you stay?’

Jessie: ‘Around Thomson.’

John: ‘Okay. Wait here until I call you. Let me leave first.’

That wasn’t hard to do. She spent the time alone to touch up her make up and get her dress straightened. It took about five minutes for him to call and she picked it up almost instantly.

John (on phone): ‘Jessie, you’re still in the room right? I’ve extended the room to overnight. Have a good rest. It was a tiring day for me, and you should be as well.’

Jessie (on phone): ‘Oh my god, serious? Thank you so much! Call me soon yeah?’

Why wouldn’t he RTF right? Hehe. What’s RTF? :P

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