Mistress Lindsey has been prostituting me out for a little while now as a way to bring in some extra money. This is the story of a recent “rental” where my boundaries were pushed in a direction I’d never have expected to go in. Enjoy.
Mistress Lindsey was sitting in her large comfy chair, and as was usual for a Friday evening when I was with her, I was on all fours and she was resting her feet on my back. I would often provide this service for her while she watched TV, read the paper, or even from time-to-time did paperwork. But tonight, she had sat there in silence for over an hour (I could see the clock on the DVD player from my position at her feet). It was not permitted for me to speak without being spoken to, and I would probably be punished for addressing her, but I was a little worried.
“Please, forgive me for speaking out of turn Mistress, but is everything okay?” I asked.
She lifted her bare feet from my back, placed them on the floor, and then sat forward in her seat. “Turn to face me slave”
I turned my body to face her in a kneeling position, being sure to keep my body cowered and my head below hers - it was not appropriate for a slave to have their eyeline above that of their Mistress. She raised her right hand and slapped me hard across the face. It stung like hell, but I didn’t make a sound.
“You know what that was for, don’t you?” She asked sternly, with a hint of annoyance in her voice.
“Yes Mistress. I’m sorry Mistress. Please forgive me for my behaviour?”
“You are a good slave” she said “And I know that you care for your Mistress deeply. But you are never to speak without being spoken to again. You do not have that right. Is that understood?”
“That having been said, there is something on my mind that we need to discuss” That was a statement, not a question requiring an answer. I stayed still and quiet and waited for the vision of perfection before me to continue. I am so honoured just to be allowed in her presence.
“For the next few minutes, you may speak freely. Okay?”
“Thank you Mistress” I replied “But about what?”
“I have been offered a significant amount of money to rent you out to someone this weekend” she began “But I am not sure whether to accept the offer”
“How significant?” I asked inquisitively.
“A thousand pounds” she said. I was incredulous.
“Mistress, that’s more than twice as much as normal. Forgive me, but that much extra money would really help you. What is there to think about?”
“It’s a man” she replied.
“You’ve rented me out to men before Mistress, for significantly less”
“I know, but his request is, well... unusual” she said, with an air of mystery and contemplation in her voice.
I was a good slave - obedient, respectful. There was very little I wasn’t willing to do for a Mistress or Master, and I’d done a lot of “unusual” things. Mistress Lindsey calling a request unusual with that tone of voice was, frankly... unusual. I was intrigued.
“What does he want?” I asked.
“He’s a really nice guy” she began. “About six months ago he broke up with his boyfriend of five years. He hasn’t been in a relationship since, and he’s lonely. He wants you to role play as his boyfriend for the weekend.”
That really was unusual. Just in the male spectrum, I’ve been rented by everything from men who wanted to spend the weekend watching me fuck their wives (personally, I’ve never understood that but there you go), to those who tied me over a bench in the garage and completely ignored me other than for fucking me in the ass or mouth once every few hours without saying a word, and all sorts in between. But I’d never heard anything like this!
“Does he know the limits?” I inquired of Mistress.
You know earlier I said that there was very little I wasn’t willing to do? Well, I will quite happily kiss and lick every inch of a man’s body (and I do mean every inch :-)), but I won’t kiss a man on the lips. I know what you’re thinking - “Hold on, so you have no problem sucking a man’s cock and swallowing his cum, but you won’t kiss him on the lips?” I also won’t fuck another man in the ass, although I love taking cock. I am strictly the bitch in guy-on-guy situations. I know, don’t ask me, I don’t understand it either, but there you are. For some reason, I just can’t face the idea of doing those things.
“Yes” she replied. “He said he’s okay with you just working around it, kissing him on the cheek or whatever. There are friends of mine with slaves who would willingly french him all day long, but he specifically wants you”
“Do you have any idea why?” I asked.
“No. He wouldn’t say. He was a little put a back when I asked and he went really quiet. I suspect you just remind him of his boyfriend somehow. What do you think?” she queried.
“I’m not sure how good a job I’ll do Mistress. I’ve never been the boyfriend of a guy, but as long as he knows the limits I’m willing to try if you’d like me to?”
“Are you sure?” she asked.
“Yes Mistress” I replied “But...”
“Go on” she said
“If it pleases you Mistress, I know you usually charge in advance, but on this occasion it may be better not to take his money until after the weekend. I would hate for us to take his money if it turns out I can’t do a very good job”
Mistress smiled. “That’s absolutely fine” she said. “Now, shut up!”
“Yes Mistress” I replied. She slapped me across the face again and normality returned.
The following morning started out pretty much as normal. I knelt on the floor by the table as Mistress ate her breakfast, then licked her to orgasm. Mistress wasn’t usually in the mood to have me pleasure her with my cock in the morning, but she loved having her pussy eaten while looking out of the window drinking her tea. That was how I earned my breakfast. When she was sated, she placed my bowl of cereal on the floor and I masturbated into it (Mistress Lindsey doesn’t allow me to eat anything that isn’t laced with cum). I then ate my cum soaked breakfast directly from the bowl on the floor without using any utensils.
After breakfast, Mistress told me to get ready so I packed a small bag of things, cleaned myself thoroughly (if you know what I mean) and then took a shower. I like to keep myself clean and lubricated at all times when there is anal play involved in my weekend - it helps with the spontaneity and significantly reduces the discomfort, so before getting dressed I filled my ass with lube and pushed a butt plug into it. The size of butt plug to choose is a tough thing to gauge - on the one hand an ass which hasn’t seen any action for a while needs to be given time to relax and stretch out, but at the same time when a guy is fucking you he wants to feel like he’s the biggest thing that’s ever penetrated you, so it’s also important for his cock to be a tight fit. I figured since I was playing the role of a gay boyfriend my ass would probably be fairly relaxed, so I went with medium. Half an hour later the doorbell rang.
I went through to the front room to see Mistress Lindsey talking to man a few years older than me (about 38). He was about six-two, and really well built. He obviously worked out. He had stylish stubble on his face and short-cropped hair. He looked good. Really good.
“Mick, this is Steve” Mistress Lindsey said. Steve waved sheepishly but didn’t say anything - he was clearly nervous.
I stepped forward and shook his hand. “Hi Steve” I said “Great to meet you”
“I have to run a some errands for a few hours” he said. “Here’s my house key and address. Let yourself in and I’ll catch up with you there around lunchtime”. He handed me a key with a keyring that had an address on it. He was obviously prepared. “I’ll see you later” he said, and he turned to leave.
I took the initiative and stopped him. “Steve” I said “I’m sorry, but I have to ask. Is there anything in particular you want from me that would make you happy this weekend?”
“No” He said. “Listen, just be yourself, only... you know... gayer”
I grinned. “Okay” I said. Then it occurred to me that I should just start right now, so I leaned forward and kissed him on the cheek. “I’ll see you in a few hours” I said. With that Steve left.
Just be myself, I thought. That was going to be trickier than it sounded. I love having sex with men, but I’m not gay. I didn’t even class myself as bi. How was I going to make sure that this went well. I figured I had two choices. I could either pretend that he was a woman, or I could imagine how I would want to be treated by a girlfriend and try to replicate that behaviour. Since I was the “girlfriend” in this scenario, I decided to go with the latter.
I said goodbye to Mistress, popped my bag in the car, and went to the supermarket before going to Steve’s house. I bought a bottle of white wine, stuff for a salad including cherry tomatoes, and bread for making melba toast. Then I popped Steve’s address into the sat nav and headed off.
This guy was clearly loaded. His house wasn’t even visible from the road it was on, and it was huge. Holy crap, I was starting to feel a little intimidated. I focussed on slotting into character. “Be impressed” I thought. I let myself in and popped my bag and the stuff I’d bought onto the kitchen counter. It was 11:45, so I figured I had a least half an hour before Steve arrived - he did say around lunchtime. “Be myself” I thought. Okay, what would I do?
I stripped naked and popped my clothes into my bag. It was probably going to take quarter of an hour to make lunch and five minutes or so to lay the table once I’d found everything, so I figured I had about ten minutes spare. I decided to use that time wisely, so I went to the bathroom, took the butt plug out of my ass, and topped up the lube. Since I was going to be walking around naked I decided to leave the butt plug out. I waited a few minutes for my hole to contract fully before heading back to the kitchen.
Steve walked through the door at 12:20, by which time I’d laid the table, poured two glasses of wine, and almost finished preparing the salad. “In here honey” I shouted, and he walked into the kitchen to the sight of me standing naked at the kitchen sink rinsing the last of the lettuce.
“Wow” he exclaimed “Now that’s a vision to come home to” I walked over to him with my semi-erect cock bouncing in front of me and kissed him on the cheek.
“Go change into something more comfortable” I said “lunch is almost ready” He grinned at me but didn’t say anything. “GO!” I said in a deliberately fake exasperated tone, and I turned him around towards the door and gave him a gentle tap on the behind. Wow his ass felt nice. I made a mental note to explore it in more detail later.
I was sitting at the table when he walked back through the door a few minutes later in just a pair of boxers. The moment I saw him my cock hardened and I’m sure I licked my lips reflexively. Man, he looked good. Ripped abs, muscular legs, strong arms. From the looks of it he had a pretty decent package under those boxers too. Later, he was probably going to fuck me. Wow! If I was a woman I’d be making a real mess of the expensive upholstered kitchen chair I was on.
We chatted casually over lunch, having the odd laugh and just trying to get more comfortable around one another. He complimented me on the food, and I told him to go relax in the lounge while I cleared up the dishes. As I loaded the dishwasher, I reflected on how things were going so far. It was early days, but I thought I was slotting into the role fairly well. Enjoying it even. He seemed comfortable, and pleased at seeing me walking around naked, rather than surprised and uncomfortable which had definitely been a bit of a gamble. He did say to be myself though, and I love being naked.
I walked through to the lounge to see Steve lying back on the sofa with his muscular arms behind his head watching TV. I thought about it, and decided that a “coupley” position was required here, so I laid down in between him and the back of the sofa, with my head nestled in the crook of his arm, and hooked my upper leg over his for comfort. My cock was pressing against his thigh and I began to harden. I elected to ignore that - it was probably fairly normal in this situation right? I snuggled in close and let out a little “Mmm” to let him know that I was comfy.
“What do you want to watch?” he asked.
“Something funny” I said, figuring it would help us to relax a little more “other than that I’m easy. Surprise me” So he brought up his media library and put on the first American Pie movie. It’s a fantastic film, and I’ve seen it loads of times, which was good because honestly I wasn’t paying that much attention. I was busy trying to absorb the situation I was in, whilst admiring the feeling of this man’s body against mine. I was slowly getting more and more worked up, my cock had been hard since I’d first lied down next to him but I was beginning to feel the need for more than just the sensation of my cock pressing against his thigh.
One of my arms was effectively trapped underneath my body, but the other was resting on those incredible abs. I began drawing little circles on his body with my fingers, feeling the tone and shape of the muscles underneath his skin. I moved to running my hand up and down the length of his torso, before drawing circles again on his chest.
“Mmm, that feels nice” he moaned lightly. His nipples were hard, so began running my finger around one without touching it. I then moved across to the other nipple and repeated the process. I glanced down to see a massive tent in his boxers. I repositioned my head so that my mouth was right next to the nipple nearest me and kissed it. He gasped and pushed his chest up towards me, pushing his nipple into my mouth. I could feel its hardness on the end of my tongue, so I started flicking it gently. “Mmmmpph” he moaned.
While I continued to work his nipple with my tongue, I moved my hand down to his crotch and began running my fingers gently along the length of his cock through his boxers. I hadn’t been doing that for long when he pushed his hips further forward instinctively. Staying on the outside of his boxers, I started massaging the head of his cock between my thumb and the tips of my fingers. He moaned again and began slowly thrusting his hips, pushing his cock into my hand. He wasn’t saying much, but every signal I was getting was telling me to keep going.
The tip of his cock felt incredible under my fingers. I needed to see it, so I gingerly undid the button on the front of his boxers, slipped my fingers inside and withdrew his member. I literally gasped, and he spoke for the first time since we’d finished lunch.
“You like?” he asked. I looked up at him and he had a smile on his face. Clearly he knew that he was a little more than the average guy.
“It’s magnificent” I replied, wrapping my hand around the base of his cock and slowly moving it up and down in full length strokes.
“Uugghh, that feels good” he let out “It’s been so long”
“Well, I think we should do something about that” I replied, looking into his eyes “I want you Steve, please”
He shuffled away from me slightly, and for a moment I thought I’d gone too far too quickly, but then he turned to face me and rolled me over so that I was looking at the back of the sofa, and facing away from him. More importantly, my ass was facing that incredible cock. To start with he just pressed his body tightly against mine, pressing his cock between my ass cheeks. As if the feeling of that strong, tight body pressed against me wasn’t enough, feeling the hardness of that amazing cock pushing at the cheeks of my butt was sending shivers down my spine. Without even thinking I pressed my ass back hard against his cock, and began circling my hips slowly. “Hmm” I moaned, “You feel so good!”
He moved away from me, and I let out an unmistakable whimper of frustration. “It’s okay” he said, “I’m coming back” I heard him spit a few times, and then heard the unmistakable sound of a man stroking his own member. He didn’t need to do that, but I deliberately hadn’t told him that I’d lubed up - I figured it would spoil things for him if he knew my ass was permanently ready for drilling, given he was hiring me for a “normal weekend”. It was nice that he was doing it though.
He started to move back towards me, so I reached behind myself and spread my ass cheeks, but he paused. I didn’t know what else he was planning to do, but I couldn’t wait any longer, I needed that cock in me. Now. So I reached out, took his cock in my hand, and started guiding the head towards my desperate hole. “I don’t want to hurt you” he said.
“You won’t baby” I replied “Please Steve, I’m ready, I need to feel you inside me. Please”
With that he relaxed his body, and let me guide his cock to where I needed it to be. The coating of saliva meant that it slipped between the cheeks of my behind easily, and my whole body shuddered when I felt the head of his cock press against my hungry asshole. He held it there for a moment, then started to slowly increase the pressure. I could feel him pressing more and more incessantly against my eager hole. I did my best to relax as much as possible, waiting for that distinctive “pop” sensation when my ass finally gives and grants him access. Then it happened.
I felt the most incredible sensation inside me as his body moved closer by a few inches. “Uugghh” I moaned, and I started to breath quite quickly. He didn’t move. He was quite the gentleman, and he waited for my ass to acclimatise and release the pressure on his cock a little. I could see stars. The mixture of pain and pleasure emanating from my ass was out of this world, but I wasn’t sure what would happen next. The thing is usually when I’m whored out, whether it’s to a man or a woman, once I feel something penetrate me it means I’m about to be fucked rigid which I really, really like. But this was a completely unknown situation. I was his boyfriend. I decided to stay put and let him make the next move.
He ran his hand slowly over my behind and then up to my hip, where he gripped firmly. Then he very gradually, very deliberated, slipped the entire length of his cock into my ass right up to the hilt. I could feel the outline of the head moving inside me. Feel every vein in his shaft as it slid inside. “Oh Steve” I moaned “You feel so good”
He moved his hand up from my hip, wrapped it around my torso, rested his head on my shoulder and said “Mmm, so do you” into my ear. I ran my hand behind me to his incredible ass, and then pulled him towards me as encouragement. Without releasing our embrace, he began moving that beautiful cock in and out of me in long, slow strokes.
“Oh Steve” I groaned “Steve!” I continued to feel every vein as he made love to my ass. Felt the ridge around his cock head just as he reached the end of his stroke. Felt his public hair pressing against my behind at the other end. I could feel his firm butt cheek tensing and relaxing in my hand. Then I felt him start to move his hand down my body towards my cock. I didn’t want that, but I didn’t want this to stop either, so I moved my hand slowly to his and redirected him to my ass.
“Don’t stop” I groaned out. I couldn’t believe this was happening so quickly. I could feel the heat building in my ass and balls. I was going to cum. Nothing had touched my cock, but I was going to cum. “Oh Steve” I moaned out again. “That feels so good. Steve!” Then...
“Mmm, Mick. I love you” I felt his entire body start to tense. You know that way men do when they really want to speed up at the end, but they want to keep the sensation going at the same time? Steve was going through that right now. But had I heard him right? Had he just said what I thought he had? Oh shit. My balls were about to explode. I was right on the edge of one of the most intense anal-only orgasms of my life. I couldn’t think straight. The only thing I knew at that moment was that I wanted to hold on and cum with him. I didn’t know what to do. I had seconds. He couldn’t possibly actually love me, he’d seen me at Mistress Lindsey’s fuck parties lots of times, but he’d only known me five minutes, and I was acting a part for that. It had to be a role thing, right? I went for it.
“I love you too Steve. Oh God, I love you!” At that exact moment he slid his cock all of the way into my ass, and he was gripping me so tightly it felt like he was trying to push it right through me.
“Oh! Mick! Arrgghhh!” he screamed out. I felt his cock spasm violently inside me as his groan continued, and I could feel his warm goo filling my ass. It sent me over the edge.
“Uugghh. Steve! Uugghhh! I love you! Ugh! Ugh! Yes! YES!!!” I felt the heat travel quickly up my shaft and ropes of cum shot from the end of my cock as I had one of the most intense orgasms of my life. Made all the more intense by the fact that he was still groaning in my ear and his cock was still spurting jets of cum into me! Fuck, my ass felt so full and warm. I felt Steve’s body suddenly relax behind me. He started to move away from me, but I grabbed his arm and held him there.
“Not yet” I said “Please don’t pull out yet” In my experience one of the most painful things about anal sex is the sensation of having a large, fully erect cock pulled immediately out of you. Not only is there a horrible sensation of sudden emptiness, but you sphincter is deeply uncomfortable while it tries to rapidly return from a width it was never really intended to get to. But, I also really didn’t want him to let go of me yet.
I think that’s what he wanted to hear because he immediately pressed his body back against mine and said “Mmm”. He just held me for a few minutes. Held me as his cock slowly deflated inside me. Held me as we both came down from the high of the orgasm we’d just shared. After a few minutes, I rolled forward slightly and his now soft cock left my ass with a distinctive “pop”. Although I felt suddenly empty without him inside me, I could still feel the incredible amount of cum he’d deposited. It was amazing. Then I spotted my spunk all of his undoubtedly insanely expensive leather sofa.
“Oh crap” I said “I need to get something to clean that up” Steve looked down at the mess I’d made.
“It’s okay” he said “I’ll get it” and without a moment’s hesitation he leant forward and licked up all of my cum until the sofa was spotless. I’d never seen a man eat my cum before. “You go freshen up, and I’ll make us a cup of tea” he said, but I didn’t want to. I wasn’t letting any of that cum out of my ass until I absolutely had to, and even then if I had my way I’d be trapping it in a glass and drinking it.