Wanton Desires free porn video

The second part to this story is in production will be a few weeks before it's completed. I'm trying something different here. A lot of my stories that I write in my note books are mainly erotic horror. I dreamed this story about a month ago. I woke up at three AM and began to write it down, eight pages of paper and forty minutes later it was finished(rough draft). When I sat down to type it up, well things got a little interesting and the story got a lot longer. I hope you enjoy reading it as much as I enjoyed writing it. I think writing is the only thing that keeps me sane in these crazy times. This is for ADULTS ONLY, so if your underage please don't read it. Wanton Desires part one "Your my sissy bitch now," Jack Harris said holding Clancy's chin roughly. "You'll do whatever I say. Is that understood?" "Yes," Clancy said trying to hold back his tears. It wasn't easy since his boss caught him wearing panties. Then the bastard threatened to expose his perversion to everyone. "Now we get off at three, so I'll be by your apartment at four thirty sharp. Are we clear?" Jack asked squeezing Clancy's chin harder. "Yes." "Good girl. Now get back to work," Jack instructed releasing Clancy's chin. As Clancy turned to leave Jack smacked his rear end hard, causing the young man to yelp in pain as he left the office. For Clancy the rest of the day seemed to fly by as he dreaded what would happen at four thirty. At break time he was quiet and withdrawn not his usual outgoing personality. A few co workers asked him if anything was wrong, Clancy played it off that he wasn't feeling good and was coming down with the flu or something. Three o'clock came and Clancy grew nervous as he headed towards the time clock in a daze. He grabbed his card and swiped it and headed out the door to his car. As Clancy approached his car he noticed a white paper under the driver side windshield wiper, that turned out to be an envelope. When he got closer. Clancy retrieved the envelope unlocked his car and got in then opened it up. A note fell out and he read it: Nancy, I hope you don't forget our meeting. I'll be at your apartment at four thirty sharp. Your Master, Jack Clancy lowered his head shaking it side to side as the tears flowed down his face. He wiped the tears away and started his car then drove off. "I'm nothing but a sissy fagot," he thought remembering the taste of Jack's cock. "I sucked a cock dressed in panties. Why me? I wish I was dead," He said then snapped and slammed his fist on the steering wheel. "God can you help me out a little," he preyed but there was no reply. Only the steady hum of the tires on the freeway mixed with the occasional thump as they rode across cracks. Twenty after three Clancy pulled into the apartment complex where he lived. He got out and made his way to apartment seven c, where he lived for the past four years. Once inside Clancy thought of nothing but but taking a shower. Clancy was shaking nervously as he stepped into the hot water that was soothing, calmed his nerves, and relaxed him. "How can I get out of this," Clancy thought over and over in his mind. There was no apparent solution to him. The water was turning cold so he got out of the shower toweled off and went into the bedroom. He put on a pair of boxers, jeans, and a cotton tee shirt that claimed Ignorance Was Bliss. Glancing over at the clock Clancy saw it was quarter past four already, "Where does the time go." Clancy went to the kitchen and filled the kettle with water then turned on the stove. A nice cup of hot tea would calm him down as he grew nervous again. He sat at the kitchen table waiting for the kettle to whistle, and watched the clock intently. He wished he could freeze time or better yet travel back in time and be a little more careful with his cross dressing. But he couldn't and now Clancy needed to face the piper. Knock, Knock, Knock. The sound broke him from his day dream and dreadfully Clancy got up and went to the door. He looked through the peep hole hoping it was the police to inform him of Jack untimely death in the parking lot. No such luck as Jack stood in the hallway with that stupid shit eating grin on his face. Clancy contemplated on not opening the door then decided against it afraid of the consequences. He opened the door slowly. "Hello Nancy," Jack bellowed from the hallway causing Clancy to blush a deep shade of crimson. "Hi sir," Clancy greeted jack warmly then stepped to the side to allow him to enter. Clancy closed the door than followed his boss into the living room. Jack turned and the smile was gone from his face. He reared back and slapped Clancy across the face. He grabbed the shocked mans arm and pulled him to the couch. Jack sat down and pulled Clancy onto his lap. He smacked Clancy's ass hard causing him to yelp in pain. Another smack brought tears to Clancy's eyes. "When I come over bitch you are to be properly dressed," Jack slapped Clancy's ass again. "Properly dressed means stockings..." Slap, "Panties..." Slap, "A bra..." Slap, "Skirt and blouse..." Slap, "And finally heels." "Am I clear?" Jack asked. "Yes sir," Clancy replied crying like a girl. A silence filled the room as Clancy lay there crying quietly and Jack felt the raw power he had over the sissy. The kettle in the kitchen broke the silence. "Go turn that off, then go in the bedroom and put on some proper sissy clothes," Jack said releasing Clancy who got up. "Don't be long Nancy." Clancy walked into the kitchen in a daze, he took the kettle off the stove and the whistling died. Then he went to the bedroom and began to strip naked. Clancy opened his closet to gain access to his hidden stash of sissy clothes. He stepped into a pair of pink lacy panties. The soft material was gentle against his red soar rear end. He found the match bra and put that on next. Clancy winced in pain as he sat on the bed and rolled up stockings up his legs. He decided to wear his black silk skirt and matching blouse. He pulled them off the hanger and stepped into the skirt, then put on the blouse and fumbled with the buttons. Stepping into the six inch heels he check himself in the mirror to see a guy in woman's clothes then walked to the living room. Jack sat in the recliner a cigarette in hand he watched the young man enter the room. His man hood grew hard instantly at the power he had over his prey. He couldn't wait to break the sissy's cherry. It was too soon for that, he needed the sissy to beg for it first. A blow job everyday would suffice until the sissy begged for it in his ass. Then Jack would own the bitch. He had dark plans in store for Clancy. His own personal slave he could do whatever he wanted to Clancy. The benefits were endless, and no need to worry about some skank getting pregnant, or that time of the month, or worse yet running to his bitch wife. Really what sissy would tattle tale on him., "Mrs. Harris your husband dresses me up and fucks my ass every day after I suck his cock," Jack smirked at the thought. He still needed to take some precautions however. A few of his wife's friends lived nearby. He would need the sissy to move. Then there was the sissy's poor performance at work. He did need a secretary however... Then it dawned on him, yes it did. He would get the sissy to move into an apartment as a woman then fire Clancy and hire Nancy as his personal secretary. Jack stood up and approached Clancy then grabbed him in his hands and kissed him on the mouth. Oh yes he would have a lot of fun with this one indeed. "On your knees," Jack ordered while applying pressure to Clancy's shoulders. Clancy kneeled knowing full well what would come next. Without being told Clancy undid Jack's belt and zipped down his pants. Clancy freed the rather large and hard cock and opened his mouth. Dressed as a woman he began to suck the cock. He paid extra attention to manipulating the flesh in his mouth. He feared another spanking, he despised pain and the spanking hurt. Clancy flicked his tongue around the bulbous head then sucked the entire length into his mouth until Jack's pubic hairs tickled Clancy's nose. All the while the bulbous head pushed into his throat. His gag reflex wanted him to hurl but Clancy held it back. He made himself swallow which compressed the cock head. This was approved by Jack moaning and then rubbing Clancy's head to encourage the sissy. The worse part of this situation for Clancy was his own sex was rock hard in the lacy panties. This act of pleasuring another man while dressed as a woman turned him on. Jack rubbed the sissy's head that was kneeling before him. The skill of Clancy's mouth was pure bliss. Especially when he swallowed and his throat caressed Jack's cock, it drove him nuts. It felt so good it hurt. He was on the verge of orgasm. Trying to delay the inevitable Jack moaned. The power from dressing a sissy up and getting head from her was incredible. He couldn't wait to fuck the sissy's ass and fuck the shit out of it. Pound it so hard to make her cum in her panties. Oh, fun times were abroad. Clancy's eyes went wide as the cock in his mouth tensed then exploded. He didn't want to make a mess so he swallowed the foul liquid as it filled his mouth. The cock kept erupting and Clancy swallowed five times to empty his mouth. All the while his tongue kept massaging the cock. "That young miss just made up for you not being properly dressed," Jack panted. "Keep giving head like that and we'll get along just fine." "Thank you sir. Would you like something to drink?" Clancy asked fearing another spanking. "No. I got to get going. I'll be here every night at the same time," Jack said helping Clancy to his feet. He couldn't bring himself to kiss Clancy on the mouth not after the sissy had his cum in there. He walked to the door. "I'll see you at work tomorrow. Oh, Nancy, you better be wearing panties and stockings and be clean shaved everywhere. Have a good night Nancy," Jack said then left closing the door behind him. Clancy collapsed onto the couch and crawled up in the fetal position and cried himself to sleep. What was he going to do? How was he going to get himself out of this mess. The next morning came early and Clancy jumped up scared, he thought he over slept. The clock on the wall gave him a sigh of relief, as it displayed five thirty. He went into the bathroom and ran the tub closing the drain. He poured lavender bath gel in the hot water, fearing punishment he wanted to be shaved extra smooth all over. Clancy stepped into the hot water and kneeled. Slowly he lowered himself as the water stung his soar ass, from last nights spanking. After a few minutes the water relaxed his nerves, and there after he lathered up his legs and ran a pink razor through them. Clancy always found It difficult to shave his whole body, he had to stretch this way and that way to reach every spot with the razor. After forty minutes his skin was as smooth as satin. He released the water and turned on the shower to wash his hair. While lathering up his hair with apple fragrance shampoo he decided he would wear his full brief red satin panties and red stockings. Clancy turned off the water and got out he patted his skin dry then wrapped a towel around his chest and another around his hair like a woman would do. In the bedroom he pulled out the panties and stockings and got dressed hoping that no one at work would see the panty or stocking lines through his uniform. That was one of the reason for his current situation. He put on his black swede pants and blue shirt the required uniform at his job. Clancy left the house in a hurry he was running late and that would mean punishment so he would drive just a little faster today to make it to work on time. The entire trip to work he was worried about getting pulled over then being late for work. His nerves where playing havoc on his stomach and he felt like he had to puke. There were no cops and Clancy made it to work with five minutes to spare. He didn't see Jack's car in the parking lot and preyed he called in sick today. How could he face the man whose cock he sucked and sperm he swallowed? He walked slowly to the warehouse then punched in. Clancy read the daily duty roster and saw that he was to clean up warehouse b with a few other co workers one being a Robert Myers. Clancy despised the man. He was tall muscular had a quick tongue and always played pranks on Clancy causing him a lot of grief and another reason why he got caught wearing panties because he was always called to the office. Clancy saw Robert, Mark and Stacy heading towards warehouse b and he caught up to the group. "Good morning Clancy," Stacy said in her usual polite manor. "Morning," Clancy replied. "Whats up dork," Robert laughed. "Not much wise ass," Clancy replied. "We'll like my momma always taught me better to be a wise ass than a dumb ass like you," Robert said then roared with laughter. Mark who was Roberts buddy chimed in with laughter. "Whatever," Clancy said then walked faster to get ahead of the group. "Clancy Davenport please report to Jack's office," A woman's voice boomed over the intercom system and Clancy stopped dead in his tracks. "OOOHHH your in trouble now dumb ass," Robert joked and mark laughed. Clancy just smiled, turned and walked away towards the front office's where Jack had his office. Two minutes later Clancy was in front of Jack's door a sign read: Annual performance evaluations in progress Do Not Disturb Unsure what to do Clancy knocked on the door. "Come in," he heard Jack reply. Clancy opened the door and stepped in. "Clancy good morning. Could you hold on a second Mr. Smith," Jack said and placed his call on hold. "Did you do as I asked?" Clancy shook his head up and down. "Good. Now I have to take this important phone call but when I tell you to enter you will walk in close the door lock it then kneel before me. Is that understood?" Jack asked. "Yes sir," Clancy replied. "Good now go out and wait in the hall and close the door behind you." Clancy did as he was told and waited in the hall. This time of the morning the front offices were always empty and to Clancy it was eerie. "Come in Nancy," Jack called from within the office. Clancy entered the room and closed and locked the door. He turned around and began to undress until he was standing in his panties and stockings. "Very nice Nancy," Jack complimented. Clancy approached Jack and did as instructed. He kneeled then undid the mans belt and zipped down his pants. "You know what to do," Jack said and Clancy pulled the mans flaccid penis from his boxers. Clancy opened his mouth and began to suck the cock. Instantly the cock grew hard and Clancy was bobbing his head up and down. "Oh that's it sissy," Jack moaned softly. "Your mouth is amazing," he stated and put his hands on Clancy head grabbed the sissy's hair pumping his head faster on the cock in his mouth. "You like that don't you? You like having a cock in your mouth and wearing panties?" Jack asked moaning. Clancy lifted his head off the cock there was a meaty pop. "Yes sir," he replied and Jack smiled from ear to ear. He forced the sissy's mouth back onto his cock and made him suck faster. He felt his orgasm approached then rammed his entire length into Clancy's throat and exploded. Pulse after pulse of hot semen shot down Clancy's throat. "Oh, Nancy," Jack moaned as he ejaculated again and again. He held the sissy on his cock to display the power he had over her. In a few more minutes he was about to show even more power. "Oh that was perfect. Your cock sucking abilities are a freak of nature," Jack complimented as he reached behind Clancy and clicked a button. "Thank you sir," Clancy replied his face turned red with shame. "Why don't you have a seat," Jack offered. Clancy got up and sat across the desk still dressed in his sissy clothes. "That's why it pains me to tell you that I have decided to let you go," Jack said. "Why?" Clancy asked tears in his eyes. "Your performance for one is below average," Jack spoke reading the assessment file on Clancy. "Your attendance is poor. The one straw however that breaks the camels back is you don't get along with your co workers. I've had several complaints in the past two weeks from several employees about your attitude and demeanor." "You can't," Clancy said. "Oh I can and I am," Jack smiled as he implemented phase one of his plan. "But what about?" Clancy said. "About what?" Jack asked. "Us," Clancy replied. "What I do for you?" "Oh don't worry that will still continue I will be at you house at four thirty. You however will no longer be employed here." "If I don't work here what makes you think I would ever suck you cock again?" Clancy asked. "Because I just made a video of you walking in here and undressing then sucking my cock. So I will just mail that to your family and see what they say. Also I'll fill out your termination based on sexual harassment of the male workers," Jack smiled. Clancy looked like a deer caught in the head lights of an on coming car. He sat the devastated and the tears flowed down his eyes. "What will I do for work?" "Now, now Nancy. It's not the end of the world. I wont to anything rash if you just continue to be my sissy after work. I'm sure you'll find another job and in fact if you do as I say then when u put us down as a reference I'll make you look like a valuable employee." "Then why did you fire me?" Clancy asked. "Simple. Lowest man um sissy on the totem pole. We had to cut back and you were our newest employe so with regret we had to let you go," Jack got up and approached Clancy. "Listen what we have together could be so much more but your assessment is only fair to the other employees." Clancy wiped away the tear and stood up he put on his pants and fastened them. The stepped into his shoes. He put on his shirt. "I understand. Same time?" "Yes Nancy. Same time I'll see you then," Jack kissed Clancy's forehead and walked the sissy to his door. Clancy walked out and he closed the door. Jack smiled as phase one was in effect. Phase three was going to be devastating and the sissy will come begging on hands and knees. Then phase four he would break her. But he was getting ahead of himself phase two could be broken down into one word. Chasity. Once he could prevent the sissy from masturbating then he would grow hornier by the day. By weeks end the sissy will be begging to be fucked and when he makes the sissy cum in her panties well, game over. Phase three wouldn't go into effect until next week. It turns out that a buddy of his owns the apartment that Clancy is renting without a job and another two hundred dollar increase in rent the sissy will do anything. Clancy drove home his mind in a fog, His rent was due next week and he was broke. He was counting on a full week to pay for his rent. Now without a job he didn't know what to do. Maybe he could get by for a week or so if he talked to the apartment manager. Once home he took off his uniform pulled out a satin night gown and laid down. He cried himself to sleep trying to figure out what to do. Knock, Knock, Knock, The front door rattled and Clancy jumped up and went to the door. He opened it without thinking. "We'll Nancy that does look very sexy on you," Jack said walking into the room carrying a slam plastic bag with him. He put his arms around Clancy's waist held him close and french kissed the sissy. Clancy was in a daze and turned on he kissed back. Jack spun him around and pushed his hard cock against the sissy's smooth ass. "Oh," Clancy moaned his own cock hard and he was horny. "You like that?" Jack asked thrusting forward. "Oh god yes," Clancy panted as his former boss began to suck on his neck. The emotions he was feeling was driving him crazy. For the first time in his life he thought about what it would feel like to be taken in the rear by a man. Jack broke off the embrace and walked into the living room. "Come Nancy, my cock needs your mouth," he said sitting down on the couch. Clancy strutted to the couch and resumed his all to familiar position at Jack's feet and undid his pants. He opened his mouth engulfing the entire cock into it. "Oh god," Jack moaned in approval then slowly worked his hand down the length of the satin gown and began to caress the sissies pantied ass. while his cock was being manipulated by Clancy's mouth he sat up and his other hand joined in the fondling of the satin covered ass. Jack couldn't take it anymore as the slurping of Clancy's mouth on his cock drove him over the edge he erupted filling the sissies mouth. Cum leaked out of Clancy's mouth and he licked it up. He was actually beginning to enjoy the taste of sperm. "Now for your surprise for being suck a good sissy. Go to the freezer and fill a bowl with ice," Jack ordered as he stood and put his manhood away. Clancy grabbed a bowl and an ice cube try he twisted it to pop the cubes and empty them into the bowl. Then he returned to Jack. "Lift your gown and open your panties," He instructed the sissy, who complied subserviently. Jack took the ice cubes and dumped them into Clancy's panties. "Ow that's cold," Clancy cried and the desired effect wilted his hard on. "I know but for my present to fit you have to have a soft clitty," Jack explained and Clancy looked at him puzzled. Jack pulled a clear plastic penis shaped chastity device. "Whats that for?" Clancy asked but in his heart knew already. "For you my dear. So you stay true to me and aren't masturbating while I'm not here," Jack lied. "Now pull your panties down." Clancy did and Jack fed the small penis into the plastic device. The he attached a ring around Clancy's balls and secured the two together he inserted a key and a click confirmed that Clancy's click was secure. "There now all set. Pull your panties up," Jack said then surprising himself he kissed Clancy full on the lips even though he just swallowed sperm. "Phase two complete," He thought as he rubbed Clancy's clitty through the panties. Clancy squirmed as his clitty grew hard but was compressed by the chastity device. Jack broke the kiss. "Well I have to run I got a few errands to take care of. Nighty Night Nancy," He said then left closing the door behind him. Clancy was horny he rubbed himself through the gown but it was no use. He couldn't get hard because of the chastity device and it prevented him from feeling pleasure. He gave up and went to the bathroom to take a long hot bath. Jack was being kind to him and he was starting to like servicing him even though it made him gay. Clancy lay in the tub relaxed. Tomorrow he would go out and find a job. Then he would ask his land lord for a two week extension everything was going to be alright. He fell asleep in the tun and woke up several hours later freezing. He got out and climbed into the warmth of his bed. Soon he was fast asleep. The next day Clancy had put in eight resumes at local companies that were hiring. He went to his landlords apartment. Tom Riley agreed to the two week extension and Clancy was feeling positive. Then when he got home and received a phone call for a job interview in the morning his day was perfect. He laid the package he bought on the bed and got undressed. All day long while he was out he kept thinking about sucking Jack's cock. It turned him on to no end, so he went to the adult toy store and bought something sexy to wear tonight. A pink satin boned corset would turn any man on. Clancy stripped and wrapped the corset around his body, he sucked in his breath and zipped it up. As the corset compressed his waist and chest his clitty tried to get hard but the chastity device forestalled its attempts at erection. Clancy sighed and rolled up black stockings on his smooth legs and attached the eight garters to them. Next he stepped into the matching satin thong and pulled it up. His clitty stuck out making him look well hung, due to the effects of the chastity device. He put on his heels then strutted to the bathroom. He applied a almond foundation then he powdered his face with rose blush. Next he did his eyes with amber mascara. Clancy didn't like his eyebrows so he plucked them into a feminine arch. He painted his lips fire engine red to complete his look. Now all he had to do was wait, so he decided to sit down and watch TV. He watched a girlie flick on TV when there was a knock at the door. Clancy checked the peephole and saw Jack excitedly he opened the door. "Well Nancy, you outdid yourself this time," Jack greeted him warmly. "Thank you sir. I did this for you," Clancy replied as Jack grabbed him and kissed him deeply in the doorway. Jack slid his hand down to Clancy's clitty and began to rub vigorously. He closed the door with his free hand and led Clancy to the bedroom Clancy thought this to be odd as he always sucked Jack's cock on the couch. Jack pushed Clancy onto the bed then lay on top of him kissing and feeling his sissy up. Clancy grew hot and his cock strained in the chastity device. He was turned on quickly by the experienced mans manipulations of his body. Jack slid the thong to the side and began to rub Clancy's anus. This was the first step in making the sissy beg. He wouldn't break the sissy tonight, it was too early for that. He just wanted to arouse the sissy to no end then make him beg to suck his cock. "Oh," Clancy moaned as the tip of the finger just stretched his anus. He was panting and reeling on the bed. "Does that feel good?" Jack asked. "Oh god yes," Clancy moaned. "Good now open your mouth," He commanded and Clancy did. Jack undid his pants and pulled out his cock. He slid forward and rammed it into Clancy's mouth. "Suck me," He ordered and Clancy attacked the cock with such abandoned. He was so turned on that he manipulated the cock in such a way that it exploded within two minutes, "Holy shit," Jack moaned loudly as his cock erupted with such force that the semen poured out Clancy's mouth because he couldn't swallow it fast enough. "My god," he moaned pulling from Clancy's mouth and spewing cum onto the sissy's painted face. When his cock finally finished it's hosing on Clancy's face, Jack sat back on the bed totally spent. Clancy who was still horny took the wilting cock into his mouth. "Oh you naughty minx," He moaned as his cock was being pleasured. It took a few minutes for Clancy to get the cock hard. He flicked the bulbous head between his tongue and cheek. He wanted more cum and the only way to get it was to manipulate the cock in his mouth. "Oh god, just like that Nancy," Jack moaned in pleasure. Clancy kept up the stimulation of the tool in his mouth. He swallowed it deep so that the head went into his throat then did his patented swallowing. His manipulations payed off as the cock erupted into his mouth and he greedily drank every drop. "Oh my god," Jack screamed in pleasure. He lifted Clancy up and kissed him with cum still fresh in the sissy's mouth. Jack laid back and closed his eyes soon he was asleep and snoring softly. An hour later Clancy was nudging Jack to wake him. "Oh, Nancy how long have I been asleep?" He asked groggily. "Only an hour sir," Clancy replied. "That was the best blow job I've ever had," he said. "Thank you sir," Clancy smiled at the comment. "I got to go," Jack jumped out of bed and went into the living room. "Nancy, I'm going to be busy for the next few days. I'll see you on Friday," he said turned kissed Clancy goodbye and left. "Okay," Clancy said closing the door. Clancy got up the next morning and got ready for his interview. He made it to the appointment with plenty of time to spare and sat in the waiting room for his interview. "Clancy Davenport?" A young woman called. "Hi," Clancy said shaking the woman's hand. "Come in have a seat," She smiled closing the door so they could have privacy. "Well Mr. Davenport I've gone over your application and made a few phone calls to your previous employers," She smiled warmly and Clancy preyed he would get this job. "There however a discrepancy with your last employer. They told me you have a poor work ethic and didn't get along well with your other co workers. Here at Encore solutions we are a team based operation and we're looking for team players who can work together without complications." "I don't understand?" Clancy said. "I don't think Encore solutions can help you so I'm sorry. We'll keep your application on file maybe something different will open up for you in the future. Have a good day sir," She said warmly then stood. "Thank you for your time," Clancy said as he got up on the verge of tears he left her office. The rest of the day dragged as Clancy drove home then sat on the couch watching TV. Another girlie flick caught his attention and the day flew by. Knock, Knock, Knock, Clancy looked at the clock and it was four twenty. Excitedly he got up thinking that Jack decided to show up. He opened the door and was greeted by his land lord. "Clancy, I'm sorry to show up like this but we have a problem," Tom greeted. "Whats wrong?" Clancy asked. "Well the other day the building inspector noticed that there wasn't a fire escape for several apartments so I have to raise the rent in order to have them installed. It'll be an extra two hundred dollars a month," Tom explained. "I'll have the money in two weeks," Clancy stated. "I'm sorry but if you can't have the money by next week I'm afraid you'll have to move out. Since you didn't sign a lease, you really don't have a leg to stand on. I'll give you till Wednesday to come up with the money. I am truly sorry about all this. Have a good day," Tom said then left he didn't understand why his friend wanted him to do this but he owed it to him. Clancy was a decent tenant, no complaints from anyone, always on time with the rent, and very quiet the perfect tenant. In fact this is the first time he had been late with the rent. Tom shrugged his shoulders and left. Clancy closed the door fell to his knees in tears. What was he going to do now? He couldn't come up with that kind of money in two weeks let alone next week. He went back to the couch where he laid down depressed. He didn't eat dinner that night and fell asleep on the couch listening to the news. The next day Clancy got up and ran a bath, that he soaked in for two hours then decided to dress up maybe that would help his depression. He put on the sexy corset did his make up and put on his favorite Black silk skirt and blouse. Once dressed he started cleaning the apartment. All his worries seemed to evaporate as he cleaned. He didn't think about not having a job or money to pay the rent. He was hungry and with little money really couldn't afford to buy food. He took his mind off that by watching TV, or doing laundry, Vacuuming seemed to help also, but as the day wound down thoughts of being broke and homeless started to creep into his thoughts. Teary eyed he sat on the couch and pouted. What to do? Knock. Knock. Knock. Clancy opened the door. "Good after noon Nancy," Jack greeted and Clancy hugged him. he was shaking like a leaf on tree during a swift summer breeze. Black tears from the mascara streamed down his eyes. "Whats wrong?" "I have no money I can't pay rent no one will hire me," he balled on Jack's shoulder. "What am I going to do?" "Shh not to worry," Jack said rubbing Clancy's back and closing the door with his free hand. "Patience, Jack. Fuck the sissy then begin phase three," jack thought and smiled horny as hell, from not have sex in two days. "Here let's go into the bedroom," Jack said arm around Clancy's waist as he guided the sissy to the bedroom. Once there he started to kiss and caress Clancy turning the sissy on. Clancy fell on to the bed and Jack landed on top of him. Jack kissed him deeply while sliding his hands behind Clancy to play with the sissy's ass. Jack pulls the satin thong aside and rubs his finger across Clancy's rose bud. He goes in circular motions and Clancy moans. He applies pressure to the anus and his finger slides in. "Oh, my god that feels so good," Clancy moans. "You like that? You like my finger in your ass?" Jack whispers into his ear. "Yes," Clancy moans. "Here it comes," Jack thought smiling. "Do you want more?" he asks. "Oh god, yes. Fuck me please," Clancy begged and on cue Jack rolled him over. He pulls the satin thong down and unzips his pants. Jacks cock is hard and he needs to be careful, slow, and delicate to properly break Clancy in. If Jack plays his cards right the sissy will beg to be fucked harder. Jack grabs lotion off the night stand squirts some in his hand and strokes his cock, he guides the padded helmet to Clancy's anus. Slowly he applies pressure he wants to be gentle the rough fucks will come in the weeks to follow. Then he will tie Clancy up and abuse his ass like never before, but now he needs to caring and loving. Clancy arches his back as the bulbous head stretches his tender ring of flesh. "Oh god," he screams in pleasure. Jack pushes every forward the tightness of this virgin ass is heavenly. He wants to thrust hard but shows incredible restraint. The head slips in Clancy's eyes roll back the pleasure he is feeling at this moment is unforgettable, his cock strains in the chastity device. He want to release it, to stroke it, to feel it explode. But he can't it's locked away and the sex he is having is driving him insane. Why did he wait so long to experience such a sweet pleasure? He can't answer that question he can only enjoy the sensation of inch after inch of hot flesh ascend into his bowels. The feeling of fullness the constriction of the corset, the confines of his chastity it is simply to much. "Oh my fuck me faster," he begs and jack complies. He knows he won this game the sissy bitch is his to do with whatever he likes. But not tonight, oh no that will come soon enough. Tonight he makes love to the sissy. He wants her to cum in her chastity to experience an anal orgasm. "Oh yeah just like that," Clancy screams as a meaty thrust fills the air, he is close to an orgasm he will never forget. Jack too is close to orgasm but he needs to hold out for the sissy to cum first. Once that happens the deed will be done, The deal will be sealed and it will be play time. Jack rams harder and sends Clancy over the edge. "oh my, Fuck me harder," he begs. "I'll do whatever you want," He screams as his body tenses up and his cock explodes in the chastity device. Streams of semen pour from the plastic tip as Clancy experiences his first anal orgasm. His anus compresses sending jack over the edge and he explodes sending his seed deep withing the sissy's bowels. Jack grabs Clancy by this hair and kisses him deeply. He won. The next time they have sex Clancy will do whatever jack wants. To be continued........