Tom was in luck and now able to indulge in one of his cross dressing fantasies. His wife, Linda, had left for a full day meeting.  Since his company had cut back Tom was only working three days a week and this was one of his day’s off.  He told Linda he would cut the grass but had finished it and hour ago.

       After relaxing with a cool drink, he started rummaging through Linda’s closet to see if there was anything that he might put on.  While Linda was much smaller, he thought he might squeeze into something.  He found a bulky cotton sweater, not very sexy but at least it would fit and a denim skirt.  From her dresser, he took a pair of panties, pantyhose and a bra.  Shoes would be the biggest problem.  He found a pair of slide sandals into which he might be able to squeeze his toes but his heels would flop over the backs.  They would have to do. 

       Tom stripped down throwing his clothes in a chair in the bedroom then put everything on.  He poured himself another drink and sat down in the den and began watching TV.  While Tom was luxuriating in his feminine outfit, daydreaming about having been forced to shed his masculine clothing he dozed off to sleep.

       Tom was awakened by someone shaking him.  “What the hell is going on here?” Linda’s voice demanded as the cobwebs of sleep were clearing.

       “Err uh” Tom stammered, trying to buy some time.

       “What are you doing in my things?” she demanded.

       “Well ...” Tom started again but was stuck for anything else to say. “I’m sorry, I didn’t know” he stammered.  However, his pathetic attempt was insufficient for Linda who stormed out of the room.  Tom quickly stripped out of her clothes and put his own back on.  When he took her clothes back to her closet she threw them in his face.

       Life was pretty tough for the next few weeks.  He didn’t mind the sleeping on the sofa, after all it had happened to one of the presidents.  There was no communication except for the minimum necessary.  If he tried to go beyond that it was met with icy silence.  She forbid him from using the computer believing that was where he was getting his ideas.  While that was ridiculous, he was still off the net.  Of course he had found support in net chat rooms but it was hardly the cause of his behavior. 

       Strangely, while Linda had never been very good on the computer, she was now spending a lot of time on line.  First she had her brother come over and help her.  He showed her how to find all the sites which Tom had been visiting.  This gave her an insight into his real sexual preferences.  From sissyschool to fictionmania she learned of his fantasies.  Her brother also introduced her to IRC and the chat rooms.  From Tom’s favorites and notify lists she also got acquainted with some of his on line friends.

       Linda met a few Dommes and got into some personal pm’s with them about her problem with Tom.  One in particular was very helpful with advice.  She told Linda about all the benefits Linda might have from going along with Tom’s tendencies.

       About a week after the incident, Linda came home with a shopping bag.  She went into the bedroom, emerging a few minutes later with the bag, went back out to the car and drove off.  Tom wondered what that had been all about but with the communications blackout there was no way to find out.  The next morning after Tom showered he started to dress for work.  He went into his dresser to get out his boxers but found only women’s panties. 

       “Linda, where is my underwear” he called out.

       “In your drawer” she answered.

       “No there is nothing there but your things” he called back.  She came in and explained that since he wanted to wear women’s lingerie, she had replaced all of his underwear with panties and camisoles which was all he could wear from now on.  His own underwear had been taken away and was no longer there.  She also warned him about not trying to replace any of his old underwear.

       “This is what you want, so I am giving it to you” she explained.

       “Be careful what you wish for” Tom thought, as he put on his new panties and camisole.  “I guess I’ve used the urinal at work for the last time” he thought.

       On Saturday, a few days later, while Tom was still sleeping on the sofa, Linda announced they were going to meet someone for lunch.  Tom drove to a location in the next state about 40 miles away.  They went into a restaurant where Lida asked for someone and they were ushered to a table occupied by a sole 30 year old woman. 

       “Hello Ann” Linda greeted her “Nice to finally meet you in person”. 

       “Same here” Ann replied, “Is this the sissy?”

       “Yes this is Tom”

       Tom began a “hello Ann” but was cut off by Ann who instructed him to address Her as “Mistress Ann” or “Mistress”.  “Hello Mistress Ann, nice to meet you” he tried again.  She also insisted that he address his wife as either “Mistress Linda” or “Mistress”.  “Yes, Mistress” he replied.

       “You won’t need that” Ann told him when the waiter handed him the menu.   The two women went on to order carrying on as if he were not there.  They did order him a small cup of broth for his lunch.  The women chatted about several things but whenever Tom was the subject they simply referred to “the sissy”.  About half way through their meal Ann handed Tom a package.  “Go to the restroom and put this on, and return what you are wearing to me” Ann instructed.

       “Yes Mistress: Tom said as he headed for the men’s room.  When he got there he opened the package to discover a pair of pantyhose.  He went into the stall closed the door then pulled down his pants.  He slipped out of his loafers and began taking off his socks.  As he did he heard the door to the men’s room open and someone come in.  His bare feet and pants completely off were visible under the door of the stall.  Even though he cold not see the other person he became acutely embarrassed.  He waited until he heard the door go again before he slipped his toes into the pantyhose.  Just as he did he heard the door again.  He quickly smoothed them up his legs then stood up pulling up his pants.  The men’s room only had one stall and he heard someone trying the door to his stall.  He quickly pulled up his pants and slipped his stocking clad toes into the loafers.  He could hear someone waiting to use his stall so he unlocked the door and emerged.  He got a strange and disgusted look from the elderly gentleman who went into the stall after him.

       Tom returned to the table and presented his socks to Mistress Ann.  “Keep those filthy things off the table” she admonished, causing Tom to shove them in his pocket.  “Slip out of your shoes and stand here beside the table” She ordered next.  Blushing profusely Tom complied.  Just as Ann and Linda had finished checking him out, but before he was allowed to put his shoes back on and sit down, the waiter returned causing even more embarrassment. 

       As they all were seated again Ann explained “A sissy’s feet should never be seen except through nylon.  The sissy should be made to wear nylon hose 24/7 and never take them off except for bathing, changing and by express permission of his Mistress”.  Linda agreed and said she would have Tom go shopping tomorrow to complete his hosiery wardrobe.  The two women then left Tom to pay the check and went out together.  When Tom came out they took their good byes and got back into their cars. Even though Tom and Linda drove home in silence Tom was optimistic that things were thawing.    

       At the suggestion of one of the Dommes she had become friendly with on IRC, Linda ordered a few things on line.  She told Tom some packages would be arriving for her but he must not open or touch them.  When they came Linda took them and put them somewhere causing Tom intense curiosity.

       A few days later Linda broke the ice slightly.  “I’ve done a lot of work on line and seen where you hung out” she began.  “I think I have some understanding of what you want.  I may try giving it to you but strictly within my own needs” she continued, making Tom extremely encouraged.  “First I found this questionnaire on line which I want you to fill out. After I review it I’ll decide further.”

       She handed Tom a 5 page questionnaire which included lengthy instructions.  It listed every imaginable BDSM activity which he had to check off whether or not he had ever engaged in it then rate how he felt about it on a scale of 1 to 5.  One was a hard negative limit while 5 was enthusiasm about it.  Tom set to work and was finished within a half hour.  “Here you are Linda” he said returning it to her.

       She slapped his face.  “You better show respect from now on sissy or you will be sorry” she corrected him.

       “Yes Mistress” he corrected himself.

       “From now on there will be demerits for each infraction with punishment handed out for them later, Understand?”

       “Yes Mistress” he responded.

       “Now first since you have been on a sissy maid site I assume that is the role you desire.  Therefore, I have let our maid go and you will perform her chores when you are off during the week.  In addition I see no reason why you should be allowed to dress in male attire except when you go to work.  So as soon as you come home you will change into some feminine clothing that I get for you.  Of course you will only be allowed to wear nightgowns when you are in bed.  I also noticed you were on some chastity channels so I will take care of that too.  Strip!” she ordered.

       Tom quickly stripped everything off.  Linda left the room returning with one of her Internet purchases.  She opened it and Tom saw a CB-2000 chastity belt.  The CB-2000 isn’t really a belt as much as a cage but it has the same effect.  She fitted the rings over his balls and the base of his cock then put the cage piece on.  Then she locked it.  The “click” of the lock caused both excitement and fear when Tom heard it. 

       Linda got another one of her packages.  “Put your panties and camisole back on” she directed.  Tom slipped into them easily having worn them for several weeks now.  “With this outfit you will wear only black stockings” she continued handing him a pair of black thigh highs and an black garter belt.  Tom put them on and stood before her.  She then handed him a black cotton maid’s uniform. It had a square neck and a skirt that came to mid thigh.  He covered the skirt with the white half apron she handed him next.  Finally She gave him a pair of sensible black pumps with a 3" stacked heel.

       “Now sissy you can start cleaning this place up.  Vacuum and dust the living room tonight” she ordered.

       “Yes Mistress” Tom replied as he started to scurry off.

       “Wait” she called him back.  “First I don’t think Tom is a very good name for a maid, do You?”.  Tom agreed so she decided  “From now on you will answer to the name Tara”.

       “Yes Mistress” Tom now Tara responded heading off again.

       “Wait” she called him back once more.  “Tara whenever you answer me ‘yes’ or ‘no’ I want you to curtsey also”.

       “Yes Mistress” Tom answered curtseying as he did.

       “That’s better, Tara” Linda said. “You may go now”. 

       Tom scurried off to begin his cleaning, his newly caged cock swelling in its cage.  

         For the next several weeks Tom’s life seemed to improve.  Communications with Linda, Mistress Lida that is, were still somewhat limited. Tom was now speaking more but still only when he was spoken to.  The cock cage was another thing.  During the couple of weeks after he had been caught in her clothes, He and Linda had not had any sex.  Still even though he was sleeping on the sofa by himself he had been able to take things in hand to keep his horniness under control.  Now he had been almost three weeks without any relief.  This made him very attentive to Linda in the hope that She would appreciate it and allow him some relief.  So far he had been unsuccessful but his only alternative was to keep trying.

       Since his cleaning duties only involved two days a week when he was not working, he was only in his maid’s uniform at that time.  At work, of course, he still wore his panties, camisole and stockings but Linda allowed him to wear his own socks over the hose.  While this was quite hot and summer was heating up, he still appreciated that he could keep his condition discrete.  Of course he only had to make sure his pant leg did not rise up too far and show his hose above his socks.  It’s surprising how much attention to detail the mind is capable of when one is motivated by fear of being humiliated. 

       At home he was usually dressed in a cheap house dress or a blouse and skirt, pantyhose and his heels.  Occasionally, usually after dark, Linda might send him outside on an errand such as putting out the trash or picking up a circular from the lawn.  These were always occasions filled with fear and nervousness.  Tom was not allowed to sleep with Linda but she now allowed him to sleep in the extra bedroom.  There had been a couple of occasions when She called him to Her bed to service Her.  He serviced Her orally until She was satisfied then he was sent back to his room.  She also continued to spend time on the computer but he had not been allowed to use it.

       One day she told him that Mistress Ann had invited them to a meeting of Her group and that they would be attending this Saturday night.  She didn’t say any more about it than that.  When Saturday came She told him She had bought him a few new things to wear.  Tom was dressed in a short black leather mini-skirt, low cut satin blouse and strappy five inch heels.  He was also wearing new black lingerie and black thigh high stockings held up by a garter belt.  They set off for Mistress Ann’s with Tom driving nervously - afraid of making any driving mistakes while dressed as he was.  Tom drove cautiously - well within the speed limit and finally arrived at the scene of the party. 

       They parked the car and entered a large banquet hall which had been reserved by Mistress Ann’s play group.  They met Mistress Ann in the lobby and headed for the coatroom. 

       “Have you told the sissy what’s going on” Mistress Ann asked.

       “No, I thought it would be more fun for him to find out when he got here. Beside he might have crashed the car on the way here if he knew” Linda explained laughing.

       “Ok then sissy strip of everything except your stockings garter belt and shoes” Ann instructed.   Tom did giving the rest of his clothing to the girl in the checkroom.  Tom was quite embarrassed standing there practically naked in front of a number of people he did not even know.  Ann laughed when She saw his caged cock.  “I hope you brought the key to that thing” she said to Linda.  Linda reached in Her purse and gave it to Ann who freed Tom’s cock for the first time in weeks.  She then pulled his wrists behind him and snapped them into handcuffs.  Then Ann led them into the main hall.  The hall had a stage on one end and a few tables scattered throughout.  Ann led him to one side where someone had put up a sign that said “paddock”.  A chain had been strung between two pillars and another male whose wrists were cuffed behind him were locked on to the chain.  He too only wore stockings a garter belt and heels.  He also had a sign with the number one around his neck.  Ann pulled Tom over to the chain and attached his cuffs to it.  She put a sign with the number two around his neck. 

       “Linda has entered you in a masturbation contest” Mistress Ann explained to Tom.  “The first one to cum wins.  The people here will be able to bet on you and a portion of the bets go to a cash prize. Right now all the contestants will be on display so the people can decide who to bet on.  Answer any questions they ask you, sissy”.

       “Yes Mistress” Tom replied automatically, while executing an awkward curtsey while practically nude with his wrists cuffed behind his back.  He hardly had time to let all this sink in when a couple approached Tom.

       Both the man and the woman grabbed his ball sac and squeezed it to try to feel its fullness.  “When is the last time you came Number 2" the man asked.  Blushing crimson Tom responded that it had been more than a month.  “How long does it usually take you to cum” he asked next.  

       “A few minutes” Tom explained.

       “How many” the man asked.

       “Probably five or more” Tom told him.

       “Is that from starting soft or hard” he asked.

       “Soft” Tom explained as the couple moved on to number 1.  Tom wished he had been blindfolded since it was even more humiliating watching people who he did not know inspecting and interrogating him.  To someone he disclosed that he had been in a chastity belt for the last few weeks which seemed to interest the bettors. 

   Later Numbers 3 an 4 showed up and went on display.  All evening additional people came by mostly to squeeze his ball sack and ask the same questions.  Tom had been standing in his heels for a couple of hours and was getting quite tired.  However he had no relief, was not even taken off display for a bathroom break.  They had arrived a little after eight and by 11 p.m. the big event finally arrived.  Tom and the other sissies were led to the stage where someone announced that betting would end in three minutes.  There was a flurry of activity on the floor as people got down their last minute bets. 

       Then the announcer called “Jockeys up”.  Some women, including Mistress Ann came up on the stage.  Each was dressed in typical Domme attire with Mistress Ann and the others each carrying a riding crop.  Mistress Ann took her place behind Tom.  The announcer announced the final odds which showed Tom or Sissy Tara as he was called going off at short odds. 

       Each of the participants had his hands released from the handcuffs and was made to raise his hands above his head.  When they all had been released, the announcer called “Ready, set, GO!”  Tom saw the others drop their arms and grab their cocks to begin masturbating furiously.  He immediately did the same but not fast enough to be spared a vicious swat across his bare ass from Mistress Ann’s crop.  There were wild cheers of encouragement to all the contestants from those in the audience.  As Tom just started to get hard he felt another stinging crack of the crop.  This caused him to pump even harder than he had been so that he was now stroking himself about as hard as he could.  After another 30 seconds the blows began raining constantly on his ass causing him to both yelp and pump at the same time.  The vicious beating by Mistress Ann made Tom completely forget how humiliated he was masturbating in front of dozens of people he had never met.  Mistress Ann continued the steady beating as the competition continued.   Tom caught a glance of Number 4 who started shooting a load off on to the floor of the stage which caused Tom to slow down.  Another vicious crack across his ass got him moving at full speed again.  Tom’s slowing up allowed Number 1 to shoot before Tom finally was able to cum.  A minute later Number 3 joined them. 

       The competition completed the four sissies were still standing on the stage a puddle of cum in front of each of them.  “That was a pretty poor performance” Mistress Ann told him. 

       The announcer gave the official results: “The winner Number 4 Sissy Brenda, Second Number 1 Betty sissy, Third Number 2 Sissy Tara and the loser Number 3 sissy Kendra.” He continued “All right Kendra you are the loser so you have to clean up”.  Kendra had apparently been in or seen the contest before because she immediately dropped to her knees and began to lick up the cum that was in front of everyone.  Tom heaved a big sigh of relief that he had beaten out Kendra.  The announcer gave Brenda’s jockey the prize money, which Tom later learned was $525, and they were allowed to leave the stage.     

       Ann took Tom back to Linda’s table where she allowed him to take off the sign with his number on it. “That was not much of a performance’ Linda observed. “I was hoping that you would earn a little something for all of our work to get you ready.  Well, I guess you will just have to wear this for a longer period before the next time, don’t you” she said retrieving the chastity device from her purse.  Sissy Tara answered in the affirmative and curtsied, as she began to reattach the device.  He heard the snap as the lock was clicked in place and wondered when, and how, he would next get his relief. While he had been anxious for relief for the last several weeks, tonight had not been exactly the kind of relief to which he had been looking forward.  Mistress Ann returned with his clothing then he gladly covered his nakedness with the lingerie, blouse and leather skirt.  While the two Mistresses sat at the table he was allowed to kneel next to it.

       A large burly man approached the table, angrily complaining that he had lost a lot of money betting on the sissy.  “At least I ought to get a blow job for it” he suggested.  Tom blanched in shock when he heard the suggestion.  Until then he did not believe that his evening could get any worse. When Mistress Ann explained that the sissy had not been trained yet and would probably disappoint the man again, the man went off grumbling to himself.  A sense of relief passed over Tom.

       Tom remained kneeling there while the women drank, chatted, and flirted with a couple of dominant males who were attending. After a few hours when his knees were in pain and he was quite stiff the women decided it was time to leave, allowing him to finally rise. 

       The next several weeks went on as before.  On the days he did not have to work, Tom got up and dressed in his maid’s uniform.  He served Mistress Lida Her breakfast, She prepared a list of chores for him for the day which he set off to accomplish after She left.  With his chastity belt he could get no sexual relief.  Even his libido was frustrated since he could no longer use the computer.  Her brother had helped Her to change the password to the operating system so Tom could no longer use it, let alone get on line. When She returned, She would check on how he had completed his chores then sat down to rest while he cooked dinner.  Sometimes She would summon him to massage Her feet or Her shoulders.  Working in sufficiently satisfying massages without delaying dinner required some effort and planning. 

       On work days, Tom still wore his feminine lingerie under his own clothes.  On these days he now had to do all the food shopping which also required more planning.  

       One of Tom’s days at home had been pretty typical.  He got up at 5:30 started the coffee then showered and shaved, including his body below the neck, then dressed for the day. Over his chastity belt, which had not been off for more than three weeks, he put on a pair of black panties.  He pulled on opaque black thigh high stockings which he attached to a garter belt.  A camisole and maid’s uniform complete with a white apron completed his outfit.  Then he slipped his feet into a pair of black pumps with three inch heels which Linda had recently purchased for him. In order to insure his comfort after his feet were measured She chose a pair which were a half size smaller and narrower than his foot measured.  She had chuckled when he first forced his feet into them telling him he would have to make some sacrifices for femininity. 

       Hearing Linda stirring, Tom raced to the kitchen to get Her coffee.  After bringing it to Her bedroom and serving it to Her in bed he stood by attentively.  As he stood there smelling the coffee, Tom always wished he had been allowed to have a cup also but that was no longer allowed, he would simply have to wait.    When She finished and slid her legs over the side of the bed, Tom dropped to his knees and grabbed Her slippers.  He bent over and kissed Her feet before gently placing a slipper on each foot then kissing them again. He remained on his knees until She went into the bathroom. Then Tom rose and made up the bed before hurrying off to the kitchen to make Linda’s breakfast.

       Tom’s own breakfast would have await Her departure.  During Her breakfast, while Tom stood beside the table anticipating Her needs, Linda gave him his instructions for the day.  Today would be cleaning a bathroom, vacuuming and dusting, a somewhat typical day, which would allow him a little time for himself.

       After she left Tom grabbed a quick cup of coffee then made a hearty breakfast.  Then he set about his chores for the day.  Since She would not be here he saw no need to torture himself so he slipped out of his too small heels and set about working in his stocking feet.

       He worked diligently for a couple of hours before knocking off and putting his feet up for a rest. He soon dozed off but was awakened by the door bell.  He scrambled into his shoes and raced to the door.  Suddenly he remembered his appearance.  Linda never permitted him to wear a wig or make up so there was no chance to look like anything other than he was - some guy obviously in drag.  Who could be at the door, a neighbor, one of their friends?  Their new relationship, except within the BDSM community, had been carried on in secret.  At the door he looked through a peep-hole and was somewhat relieved to see a delivery man.  He considered not opening the door but reconsidered when he thought of Linda’s wrath if he failed to take in something She had ordered.  Mustering his courage he opened the door.  The surprised look on the deliveryman’s face was met with Tom’s total nonchalance.  He decided to act as if nothing was unusual (which it wasn’t in their household).  Just for laughs he decided to sign for the package as “Tara” leaving the deliveryman something else to add to his story when he told his friends of this experience.

                After lunch, Tom returned to his dusting and vacuuming which continued, except for a few breaks, until about 5:30.  Then he slipped his shoes back on and began preparing Dinner.  He was working in the kitchen with dinner on the stove cooking when he heard Linda return.  He went to the living room finding Her already seated in Her chair.  He hung up Her coat which She had thrown on the sofa then returned and knelt before Her.  He removed Her shoes kissing each foot as he did.  He then began massaging Her feet, kneading first one then the other.  She told him Her feet were more tired than usual so he should keep his massage going longer.  Then he took her shoes to the bedroom, returning with a pair of comfortable slippers.  He again kissed Her feet then placed the slippers on kissing Her feet again.

       “May I return to the kitchen now, Mistress?” he asked. She dispatched him, ordering him to turn on the TV before he did. He called Her to dinner, seating Her and serving Her the meal he had prepared.  As at breakfast he stood attentively beside the table anticipating Her needs as She ate.  He would have his own dinner while he cleared up.

       “You did not do a very good job tonight” she remarked.  “The rice was a little bit burned”.

       “I’m sorry Mistress” he said.  He did not want to explain that it had been cooking while he was massaging Her feet and it would not have burned if he had not been ordered to extend the massage. 

       “You will have to be punished for that, so you remember not to do that again” she continued.

       “Yes Mistress” was his only reply.

       After he had finished eating his own dinner and cleaned up the kitchen, She summoned him back to the living room.  She made him remove his shoes then kneel on the sofa facing the back with his feet handing over the seat.  She got out a steel rod swinging it whistling through the air. 

       “Count” She ordered swinging the rod powerfully landing a stinging blow across his right arch.  The blow stung painfully causing him to shriek but still managed to call out the number one.  “Be quiet if you don’t want to be gaged and for me to increase the number you will receive.” She warned, bending Her arm back for the next blow.  She delivered another blow to his left arch with all Her strength.  The pain was overwhelming and in spite of his best efforts he shrieked again.  “All right that does it” She said setting down the rod and leaving the room.  She returned with a ball gag forcing him to open his mouth so She could shove it in roughly fastening the velcro strap behind his head.  “There will be another ten for your disobedience” She announced, picking up the rod to continue. 

       She resumed landing ten stinging blows on each of Tom’s upturned feet.  With ten blows She was able to land them from toes to his heel so that the whole bottom of his feet could be covered by Her blows.  When She had finished, tears were streaming down Tom’s cheeks and his feet were painfully sensitive.  Insensitive to his pain, she made him put on his already uncomfortable heels.  While he stood before Her she told him that the package She had received today was a surprise for him but since he had been disobedient it would have to await for another day.  Instead Tom was given “Corner Time” where he was made to stand, with his already stinging feet crammed into the too small heels, facing a wall only to remain there gaged until bedtime.

       On Tom’s next day off he would get his “Surprise”.  After dinner he was told to change into his nightgown and bring the package which had remained unopened to the living room.  Tom hurriedly changed into his white stockings, white garter-belt, white ballerina style velour stretch slippers and ankle length white nylon nightgown, his usual sleeping attire since Linda had caught him wearing her clothes. 

       He anxiously carried the package to Linda who was in the living room.  Linda asked “It’s been what almost a month since you’ve cum?” He said it was 35 days.  “Would you like to cum this evening?” She asked, causing him to agree immediately.  She took the package and went into her bedroom.  She told him to wait for her in his bedroom where Tom lay on his bed waiting with great anticipation.  Linda came in having also changed into Her own nightgown.  When Tom saw Her he could not help noticing the prominent protrusion in the front of Her nightgown.  She smiled pulling up Her skirt to reveal a strap-on with a massive dildo attached. 

       “Get on your knees, unless you want me to use this without any lubrication” She commanded.  Tom leapt from the bed obediently.  Linda had placed a condom on the dildo which She ordered Tom to begin sucking.  He sucked vigorously trying to get as much salvia as possible on the instrument.  “I guess you wish this was a real man’s cock” She observed, causing Tom to try to shake his head while still sucking.  “OK that’s enough, get up on the bed on your belly” She ordered. 

       Tom pulled down the covers and lay face down on the sheets.  Linda got on behind him pulling up his skirt exposing him from the waist down.  “Help out by spreading your cheeks” She ordered next.  With his virgin ass-hole exposed lay there.  Linda forced the huge tool up to his tightly closed sphincter, causing Tom to jump and Linda to laugh.  “This won’t hurt, ...... much” She added after a long pause.  She then began forcing the huge tool into his tightly closed anus.  “Relax and let it go in” She continued.  Easy advice to give but not easy for Tom to follow.  He felt it force through his sphincter muscle and penetrate him.  It felt like it was five times the size it was and that it would split him in two.  Linda kept pushing until it was in a good six inches when She began to withdraw it.  Before it came out She thrust it in again.  She continued finally establishing a rhythm as She pumped it back and forth in Tom’s tender hole. 

       Linda continued for about ten minutes, during which time Tom actually began to feel aroused.  Aroused as he could be considering his cock was imprisoned in the chastity device.  Finally Linda withdrew and made Tom roll over.  To Tom’s surprise he saw a puddle of semen on the sheet.  Tom had not felt the usual enjoyment of ejaculation, and in fact did not even know that he had done so.  It would be his first experience with pressure on his prostrate causing semen to be forced out without any feeling of release.  “There you’ve been allowed to cum. Now clean up after yourself.  Lick it up” Linda ordered.  Dutifully if not happily Tom licked the sheets until everything was off the surface. 

       Tom was to find out that this would be the only way that he would get to cum from now on.  This however would not be his only sex.  Linda would summon him to her bedroom where he would be made to put the strap-on on over his chastity device.  He had to participate in all of the foreplay that he had done before, kissing, sucking Her nipples, before finally mounting Her with the strap-on.   Once he had satisfied Her he was dismissed to his own bed where he usually spent a frustrating night after his own arousal.  Other times he would be summoned to Her bedroom where he would have to service Her orally before being once again dismissed in frustration. 

       Some time later Tom began to reflect on his new lifestyle.  Was this what he really wanted?  While he wanted to cross-dress he was not sure he wanted it 24/7.  Certainly he wished to be back on the Internet.  Naturally he longed to be out of the chastity device and to have regular sex again.  still he loved the spontaneity of not knowing what was coming next, since Linda had looked at where he went on the Internet most of what She did was in his comfort zone.  Strangely, he took no action to change his new lifestyle.  It was not even necessary to try to top from the bottom.  So he thought things would not be changing soon.