Straighter Forward

While there were no shortage of guys whom had tried to ask her for her number, one man, in particular, managed to do so in the briefest conversation Milly could never expect. Although she was attached, she was in a relationship with a man who had a thing for such brazen behaviours, somewhat of a mild ‘cuckold’ fetish.

Just like every other nights when she shared her ‘encounters of the day’, this forty-year-old gentleman, seemed to be different from the other ‘boys’. From the way she recounted her short interaction with him, Jay, her boyfriend, could sense the slight excitement, beyond the disbelief, in her voice.

‘You know what he said? He said, I don’t want to know if you are attached, or even married. I would like you to be my sugar baby. Give me your number, I’ll give you the details, and you can decide. So I just gave him my number because I don’t know what to reply.’

To note, Jay, knew who he was too, for he was momentarily distracted by that particular customer he showed up at their workplace. If even he could not ‘ignore’ him charm, how could any other women seated around him resist stealing gazes at his muscular, well-groomed physique?

Upon showing Jay the texts, her own boyfriend was caught dumbfounded by the offer. It was, offensive, dismissive, degrading, yet straightforward, polite, and tantalising at the same time.

‘$500. You will accompany me for no more than three hours, between 7 to 10pm. I will not initiate any physical contact with you. Reply ‘yes’ and I will set up the activities, send ‘no’, and you will not hear from me again.’

As far as ‘creepy old men’ goes, there was not a hint from him – according to her. With such a modest offer, and some assurance of what could happen, there was little resistance for her to turn him down.

‘I’ll text him’ yes’ OK? You won’t get angry at me right?’

‘I won’t. From the way you talk about him, I think he feels safe, and you are confident you can protect yourself right?’, Jay replied with a emotional ‘pinch’, that resonated at both his heart, and his loin. For that amount of money, there was bound to be some risk, and it was her, who decided that the risk would be migitated by his words.

A day prior to the date that they were meeting, a parcel was delivered to her workplace, containing three pieces of clothing. A white, floral sundress, and a white, sporty tank top that was paired with the colour-matched, unlined tennis skirt.

On that very day, she was back home, by 10pm, in their room, with seven pieces of orange, one hundred dollar notes laid out for Jay to see first thing.

‘$700? How come?’, Jay just had to ask. She might have done the worst thing he could imagine, or she might just be that good of a companion. In any case, he knew he had to know, and was prepared to continue loving her no matter how that night went.

After taking a deep breath, she revealed a smile that put one as wide on his face, giving him some insights about the news that was about to hit his ears.

‘So, he came at 7pm sharp, to pick me up in his car. He drove a very normal car, nothing fancy. We went to a private gallery that his friends invited him to, but I just mostly followed him while he shook hands with the people there. It was a weird experience. He didn’t talk much to me there, and no one else spoke to anybody that was following behind the main person. Like if a lady was walking in front of a guy that was following her, people would only talk to the lady. So, since I was just following him, no one else spoke to me.

At around 8pm, we left the place and went to a restaurant that he told me had good steak, and we had dinner there. He just asked me about my life, how am I doing, what did I wanted to do when I was younger, about my family. For some reason, he never asked anything related to my status at all, whether I am single or attached.

After dinner, he drove me to where his house was, but he didn’t go straight home. We just sat in the car, opposite his house and continue chatting. Towards the last thirty minutes, he finally talked about the dress.. ‘

A pause then came, and Jay could feel the mood in the room changing, to an ambiguous one, that he didn’t know how to process.

‘And then?’, he probed.

‘Martin said that I looked sexy in it, and asked if I did what he texted me to do.’

‘What did he ask you to do?’, Jay asked.

‘He asked me not to wear any bra or panties under it.’

‘Did he touch you?’, Jay’s eyes widened as fear struck him.

‘No? But I.. touched him.. ‘


‘He pushed his backrest down almost flat and just lie there after close his eyes and took his dick out. It was so comfortable and quiet and cold in the car, so I just wanted to get some warmth from his dick. After I held it, he got a little bit bigger so I began massaging him. His skin was a little dry, so I used some saliva. He started moaning, and I was turned on by his voice.

It felt so airy under the dress, and also cold, so I took his hand and put it at my legs. His fingers slowly went higher until he touched my pussy, and I don’t know why I just spread my legs for him. After he made me so horny, I wanted him to feel the same too so I sucked him.’

By then, Jay was as hard as his brain was hurting, for someone he loved so dearly to be pleasuring someone else she just met. He couldn’t tell if it was the money, or pure lust that freed her mind, but the pain was somehow addicting enough to let her keep talking.

‘A while later, all I can think of was his dick inside me.. So I climbed on his lap, and rode him. I kept telling him to tell me when he was about to shoot, but he just kept quiet. I was so worried, but my body won’t stop moving. I kept riding his dick and rubbed myself, until I felt giddy.

Then suddenly, he woke up and opened the glove box, and took out a condom. You taught me how to put it on before so I wore it for him, and.. continued riding him. I was tired already but his dick just felt so good. When I finally stopped moving, he thrust his dick upwards so fast and deep I just held onto the roof.

I think I got too loud because he opened his eyes a few minutes later to look around the car. He kept staring at my embarrassed face while I kept moaning. Then about three more minutes later, he stopped and let me fall back down on his dick.

He came into the condom inside me and smiled calmly at me after that. I got off him and he sent me home. I didn’t say anything to him on the way home. After he left, he sent me a text.’

‘What did he say?’

‘Tomorrow, in the other outfit. You will accompany me for no more than three hours, between 7 to 10pm.’

This time, there was no ‘yes’ or ‘no’. But the look in her eyes already told Jay – Y-E-S.

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