Sissy's Weekend of Depravity Part 2

Mistress dropped me off and told me to be ready for 6pm the next evening. I spent Saturday sl**ping and recovering from the previous evening’s exertions. I thought back to evening spent dogging, I had been handcuffed and blindfolded before being bent over the bonnet of Mistress’s car whilst a line of men fucked me one after the other until I could barely stand. Mistress told me that she thought “I had taken my own height in cock” that evening. As the time neared 6pm, I started to prepare myself; Mistress advised that she would be bringing my outfit so I made sure I was clean and hairless. The doorbell rang and I sped to the door in anticipation of seeing my mistress. I opened the door and she breezed in as radiant as ever. “Tonight is role-play night, Cindy” Mistress informed me, “and tonight your role is a little sissy whore! and I do mean whore!”. Mistress went on “I’ve rented a room at a local motel for the night, and I’ve arranged for a number of friends from the local fetish club to visit and act as Johns for you to service with your sissy mouth and cunt, I get to play your pimp for the evening! Doesn’t that sound fun?” “Yes Mistress” I replied, “I thought it would, you dirty little girl” she responded. Mistress then opened her bag and began laying out my outfit for the night. She had chosen an ensemble of black latex for me to wear. My outfit consisted of a bustier which fit tightly around my chest and my heavy breast forms which I had left glued on from the previous evening, thong panties, thigh high stockings and elbow length gloves. Once I had dressed, Mistress sat me down and did my makeup and hair. When finished she showed me how I looked in a mirror, I was the picture of a gothic slut. I looked quizzically at her and she said “Men love the gothic look; it tells a man that the girl is kinky and uninhibited. He can do anything to her and she’ll love it! And you are going to be an-all-pleasing-no-holes-barred little hooker slut tonight!” We left my house and drove to the motel; Mistress parked up and said “we’ve got room 69, rather appropriate isn’t it?” “Yes” I replied. “Well not really " Mistress responded “no-one’s going to suck your little clitty tonight but I’m sure you’re going to suck plenty of lovely cock”. Mistress unlocked the door and turned on the light, it was your typical dull dingy motel room. She looked around and said “wait here, I need to get something from the car”. I sat down on the bed and tested its springiness; it bounced enough for me to get an idea of how it would feel as I was pounded by a strong man with his hard cock. Mistress re-entered the room and placed two large bowls on the table by the bed, she upturned a plastic bag she had brought in and I saw the bowl fill with a number of foil squares. Mistress said, “we’ll need a good supply of condoms, I can’t have my little sissy getting pregnant now can I?” I gestured towards the other bowl, “oh that’s for the men to deposit their used condom’s, can’t be having them make a mess on the floor”. As we settled down, Mistress checked the time and told me it was quarter to eight. “Your first appointment is at eight o’clock, you have 8 appointments about 30 minutes apart. They will take what they want from you. Remember this is a role-play so just play your part, I will play my part, just remember to stay in character, they are all experienced role-players so they will perform their parts. This is going to be so much fun!” At 8 o’clock, there was a knock on the door, Mistress opened the door and welcomed the man. He was a dishevelled middle aged man, but physically quite fit. “Cindy, this is “John”, I believe he would like a blowjob”, Mistress looked towards the man who nodded agreement. “John, I believe we agreed on £20”. The man agreed and then passed a twenty pound note to Mistress. Mistress turned to me and said “you know what to do”. I took “John’s” hand and led him to the bed, I undid his belt and opened his trousers, I was pleased to see that his cock was already half hard, it’s always nice for a sissy to see that she has an effect on a man before she touches a cock. I pulled his trousers and briefs down and got him to sit on the edge of the bed. I wrapped my hand around his cock and slowly started to wank it. After a few strokes, I moved in and started to lick his balls, I could feel his cock harden and get even harder as I sucked one of his balls into my mouth. Once I felt that his cock would grow no more, I moved away and picked out one of the foil packets from the bowl on the table. I tore open the packet and pulled put the latex sheath, I held the condom within my lips and slowly unfurled it down his cock using my mouth only, the hours of practice on Mistress’s strapon paying off as I managed to roll the condom down to the base of his shaft. I could hear and exclamation of “Fuck me” from “John”, I took pleasure in his reaction. I pulled back and looked up at him and said “I’m going to make you feel so good baby” before descending onto his cock. I licked up and down the length of his cock, before taking it in into my mouth. I tightened my lips around the head of his cock and ran my tongue against the underside of it before starting to work my way down the shaft. I continued to bob my head in his lap as I took the length of his cock into my mouth and throat. I could feel the reverberations through his body as he became more and more turned on. I could feel him twitching as he became more excited. Hearing a low groan I could feel his cock pulse deep within my mouth as his hot cum spurted out into the condom. I carried on rubbing my tongue against his now deflating cock until it was soft enough to roll the condom off. I chucked the used rubber into the empty bowl. “John” pulled up his briefs and trousers on and stood up. He told Mistress that she had a good little whore before leaving. Mistress told me that I had done and my next appointment would be along shortly. A couple of minutes after eight thirty, there was a knock at the door and Mistress opened it. The man was in his mid-twenties and appeared to smartly dressed, he looked like a businessman on a weekend conference. The Mistress introduced him as “John”. “Another John” I thought to myself, there wasn’t much originality when it came to names. Mistress informed me that “John” wanted to fuck me. Mistress told him that the price was £50 as agreed and he handed over a wad of notes to Mistress. “John” turned to Mistress and asked if it was ok if he got a little rough with the whore. Mistress said "within reason”. “John” ordered me to get on all fours on the bed facing away from him. I complied and felt him spank my ass a couple of times. I felt him pull my panties to the side then heard his belt unbuckle and his zipper unzip before his trousers hit the floor. Mistress reminded him to use a condom; I heard the foil rip and noise of the rubber being unfurled onto his cock. He spanked my butt another couple of times and I could start to feel the redness develop on my cheeks. Without warning I felt his manhood, push its way into my ass. With no ceremony, he started thrusting away. He settled into a steady rhythm and grabbed me by the hips as started to rapidly pound away at my bottom. He grabbed my hair and started to pull backwards forcing me to arch my back as he continued to bang away. He started to spank my ass again hard and I yelped, Mistress sensing my discomfort told him to stop. He sighed and just keeping fucking away at my little sissy hole. His strokes started to become irregular and his breath started to quicken , then with a roar he came , I could feel his hot sticky cum spurt into the condom in my ass, warming my insides. He pulled out, pulled the condom off and tossed it into the bowl. He left without saying a word. My next appointment turned out to be a young man, no more than a boy. He looked like he was only 18 or 19 years in age. Mistress introduced him as, surprise surprise – John. Mistress said “John here is a virgin; you’re going to be his first time, make him feel good”. Once John handed his money to Mistress, I took his hand and led him to the bed; I laid back on bed and slipped my panties off. I spread my legs and said “Come on tiger, make me yours”. The boy grabbed a condom and slid it onto his hard cock. He came over and grabbed my legs and placed them on his shoulders. Before slowly inserting himself into my hole. He started to thrust his cock back and forth into my welcoming cunt, just as he started to build up a bit of rhythm; I felt him tense up and his sperm fill the condom. He looked very sheepish, before saying “sorry” and making a quick exit. Mistress said “I had heard he was great at playing the virgin, I didn’t know he was that realistic”. The evening went on and a variety of men came (literally) and went, I was starting to tire and what was worse I hadn’t come myself. I said as much to Mistress who told “Whores exist for their customer’s pleasure, not their own”. As the door knocked for the final time, Mistress told me to wait a moment whilst she went outside to speak to the man. After a minute or two, the door opened and Mistress led in not one man but two. They were both in their mid-twenties, very fit and looked immaculate. Mistress introduced them as Damon and Steve. Mistress advised that they had paid to take me however they wanted. They quickly got undressed and my mouth began to water as I saw the flaccid cocks, they were both very well hung indeed. They placed me on my knees on floor between them. I needed no instruction; I started sucking on the nearest cock whilst jerking off the other. I switched between the two as the gorgeous cocks became engorged. “What a lucky sissy, I am” I thought as I played with the ever stiffening dicks. Once they were both ready, they had me get on all fours on the bed before they penetrated me, one in my mouth, one in my ass. They built up a quick rhythm as they sawed back and forth into me. As the man at my rear (Steve, I thought) thrust into me I lurched forward onto the other’s cock. At one point, as Steve had bottomed out in my ass, and I had taken Damon’s full length into my mouth and throat. I heard the shout of “airtight” and the slap of a high five being given above me. They continued to use me as an object to be fucked for a while and I felt my pleasure building towards my sissygasm. And then, it happened, I felt my little clitty pulse and my juice spill out. Shortly after, I felt both Steve and Damon cum and the three of us collapse on to the bed. As I lay there in the afterglow, I heard both Steve and Damon dress and leave with Mistress’s thanks echoing in their ears. As I sat up, I glanced across at Mistress who was emptying the used condoms into the bowl. She brought the bowl over and told me “Here is your hard earned reward, lap it up”. I followed instructions and licked the salty cum up from the bowl. Once I had finished, Mistress told me it was time to leave. As we were driving she asked how I had enjoyed the evening, I replied that it was one of the most erotic experiences of my life. Mistress said “Good, I’m pleased you enjoyed it. “, she paused for a second before continuing “I have a small confession to make”. I asked what that was and she handed me her iPhone, she told me to access the last bookmark in the browser. I loaded the page and started to read, I noticed instantly it was a Craigslist ad, it read “Sissy whore for use, this Saturday, O and A levels offered, reasonable rates offered”. I looked incredulous at Mistress who said “That’s right, those weren’t members of the fetish club, they were real John’s and you were a real hooker for the evening. “ I could feel my jaw dropping as she continued “You really were that poor lad’s first time, no role player can fake a premature ejaculation like that.” I could feel my cheeks redden as the realization set in: I had been a prostitute selling my holes all night. I asked Mistress if they were all customers, she replied “All bar Steve and Damon, they are two local e****ts who I hired for the evening to spit roast you, they weren’t cheap, I had to use all the money you earned to pay for them!” As I started to respond, she said “That’s right, you spent all evening whoring your ass, just so that you could hire two men to spit roast you like a suckling pig!! You looked so good impaled on their hard cocks!” As I opened my mouth to protest, she said “Don’t complain, you just said you loved the experience”. I grudgingly agreed. As we drew up at my house, Mistress said “I’ll be in touch”. I got out thinking about what limits she would test next weekend and felt a shudder go down my spine... The End.