We had been having these catch-ups for about 3 years now. Heather, Sally, and I have known each other since uni, and we re-connected when we all ended up back in Sydney after having lived all over the place. We sort of adopted Jane and Julie along the way. We are all in our mid-thirties, they are all married, either officially or de-facto, except me, who has been divorced now for about 18 months after throwing out my cheating gambler of a husband. Eventually Heather looked at me and demanded I tell them about my love life. They all sort of admired my single status, while also resenting my freedom, and being glad that they didn’t have to put up with all the crap I went through as a single woman looking for love, or at least, looking for sex.
Sally filled up our wine.
I paused for a moment, undecided if I wanted to share. Two months ago, we had shared sexual fantasies that we had either explored or were too nervous to try. There had been some surprises about what my friends got up to, or thought about getting up to, behind closed doors. When it was my turn, I shared that I had two fantasies that I played with when I masturbated; to be a prostitute, being paid to be a man’s fuck toy and secondly, I wanted to pay for sex and to be able to order a man around and demand how I wanted to be satisfied. The others had accused be of being a control freak, whether in control or under control, and I had had to agree with them.
Eventually I looked around the group, took a swig of wine and shared that I had fulfilled both fantasies, sort of. They demanded details.
“OK, girls club rules,” I insisted.
“We don’t talk about girls club,” they all chorused.
“I went online and found a male prostitute to fuck, and then I told him that I wanted to pretend that he had bought me. That I was his fuck toy.”
There was a stunned silence for a bit while they thought through what I had told them, then the questions started.
“How did you find him?”
“How much did it cost?”
“How long did you have him for?”
“Was he worth the money?”
“Was he a good fuck?”
“I just googled male prostitute. I had to filter out the gay sites, and there are heaps of those, but I found a range of options of men who only fucked women, all with amazing photos of very fit bodies and most with assorted dick picks. I messaged a couple, and most seemed OK, except for one who was a bit creepy, but I eventually decided on a guy named Phillipe who looked southern European, with delicious looking skin and a nicely curved cock. I particularly liked Phillipe’s dick pics because they were artfully done, nice lighting rather than lying along a ruler like some of them had been.”
There was a stunned silence.
“Go on, please.” asked Julie.
“Phillipe was very professional. I told him about my fantasy of being his paid fuck toy and he agreed immediately. We discussed price and how it would work with him paying me. I agreed to pay him double and for him to give me half back in cash in payment for my services. We agreed what he should be wearing and what I would wear. We discussed condoms, he required them for all customers unless they had a recent STD test. He sent me a copy of his most recent test which was only the previous week, so I also had a test and we agreed that we didn’t need condoms. Then he sent me a list of sex acts that he was OK to perform, and I had to fill it in and send it back to him, explaining what I was OK with. He called it a ‘Yes’, ‘No’, ‘Maybe’ list.”
“Holy shit,” exclaimed Jane.
Sally filled up our wine, again.
“Wow, what sort of things were on the list?” asked Heather.
I took four copies out of my bag and passed them around. They all went very quiet as they read through them. Several of them were shifting around on their seats and Sally’s nipples were clearly showing through her top.
“Which did you tick” asked Heather?
“I’m not going to tell you” I told her with a smile. “You can make up your own minds what you think I would have chosen, or what you would choose.”
“After I got this list from Phillipe, I had a look online and there are lots of these lists available. Some are much longer than his, so I suppose that he filtered out some things that he wasn’t interested in.”
“What sort of things,” asked Julie.
“Some of the lists I saw had poo and pee stuff as well as serious bondage and humiliation stuff. I’m glad that they weren’t in his list. Anyway, I sent back my list and we agreed on a date and time. I booked a hotel room, met him there and we fucked ourselves silly. I was his fuck toy and paid him to do it. So, who else is going to share?”
“Ah ah ah… no way… details now,” instructed Sally.
“No way,” I told her.
“Way,” they all almost shouted at me.
“Are your sex lives all so bad that you need to hear about mine,” I asked.
“Not bad,” offered Julie, “just unadventurous.”
The others were all nodding in agreement.
“But I’m taking this list home to Paul,” said Julie.
“What were you wearing,” asked Julie, forever the fashion police.
“I bought some new lingerie, a bra and panties set that were more lace than substance in midnight blue and grey stay up stockings. I wore these heels,” and I waved my four inch shoes at them, “and we had agreed that I should go for sexy executive look, so I just wore a black skirt that was really too short to actually wear in an office and a button up pale blue silk shirt, with a few buttons undone to show off the top of my bra. I also wore a gold anklet, just because an anklet always makes me feel slutty for some reason. So only clothes that you could wear for your guys if you wanted to.”
“So, you knocked on his door at the hotel” asked Sally”
“You are going to make me tell you everything, aren’t you” I groaned.
“Yep” replied Sally.
Sally filled up our wine yet again, we seemed to be thirstier than usual.
“We had agreed to meet at the bar. I had shared a photo of myself and of course I had his photo from his web page. He saw me walk in and greeted me like a long-lost friend, friendly kiss on the cheek, holding my hand, leading me to his table. I immediately felt relaxed with him. He had got there early to make sure he had a table in the corner, and he was in character straight away. He slid an envelope across the table which contained my payment. I made a point of counting it then put my hand on his thigh, under the table and thanked him. Our drinks arrived, which he had billed to the room, and he was very forward in telling me what he wanted from me, how he was going to take me. He reached over and undid two more buttons of my top, exposing more of my cleavage, then he ran the backs of his fingers across my breasts along the edge of my bra. It felt like he was claiming me in front of everyone in the bar. I moved my hand up to stroke his cock through his pants and I found him already hard. I saw a man at the bar watching and he said something to his mate who also looked around. It was incredible erotic. I felt so slutty, but also so empowered, knowing that I had engineered this.”
“So, we went up to the room. As soon as the door was closed, he pushed me against the wall and he started kissing my neck, biting my ear, groping my breasts. I had told him earlier that I didn’t kiss customers, but now I regretted that, but went with it. He was wearing a suit and I pushed his jacket off his shoulders, and I had his belt undone, and unzipped him and reached in to find his cock. It felt really fat, compared to what I had seen in the pictures, and that got me really wet. He had my shirt undone and then told me to kneel in front of him.”
“I’m not sure I want this level of detail” interrupted Jane.
“Oh fuck, I do,” said Julie and the others agreed. “Keep going, this is better than Literotica.”
“He gave me his cock to suck. I licked around the head, teasing him a bit, ran my tongue along its length, then took him in my mouth, stroking him with my hand. He started pushing further into my mouth, fucking my mouth. He had his hands wrapped in my hair, controlling my head, but I had my hand around his cock, stopping him going too deep. I slipped my other hand up under my skirt so I could touch myself. He was getting vocal, telling me to take him deeper, to suck harder, telling me what a sexy mouth I had and how amazing I looked on my knees with his cock in my mouth. Then he sort of held himself still for a moment, told me he was coming, told me to swallow it all, then he erupted in my mouth, maybe four or five big spurts of cum that I felt hit my tongue and spray around my mouth then lots of little thrusts as he emptied himself. I licked him clean, and he helped me to my feet. I had paid to be his fuck toy, and this was a great round one.”
“His cock was softening, not going really soft, you know that sort of half hard stage. He told me to undress him, but to do it slowly, sensually, to use my hands and mouth to explore his body as I did it. I started with his tie, and asked him if he wanted to tie me up with it later, which was on my list, then I started undoing his shirt, kissing down his skin as it was exposed, sucking on his nipples which he seemed to really enjoy, holding my head there and trying to push his little nipples into my mouth, moaning quite loudly.
“Lots of guys like having their nipples sucked,” offered Megan.
“I know Greg does,” said Sally.
“Anyway, when his shirt was off I had him sit in a chair so I could take his shoes and socks off then pulled his pants down and threw them in the corner. That just left him in his underpants but his cock was still hanging out. It looked a bit weird, so I just pulled those down as well and gave his cock another kiss.”