Chapter 14

 

On Monday morning Mark got woken up rather roughly. It was only 7:30 am, but his phone was going off loudly. Confused he picked it up to see who would call at this ungodly hour. Nerves instantly struck him when he saw his girlfriend’s caller ID pop up.

 

What happened yesterday instantly crashed back to his memory, but even worse was the knowledge that he was supposed to go to CC’s with her. Going to that boutique always made him feel nervous but going there with Lisa after she had shown how dominant she could be really made his stomach turn in knots.

 

Despite not wanting to get confronted with his girlfriend and wanting to get back to sleep Mark didn’t dare not pick up. Slowly with a scared heart he picked up the phone. “H…hello, Lisa.” He stammered nervously.

 

“Aaah, Marcy! Good you’re awake. I was just calling to let you know I will be there in about an hour and a half to pick you up. I thought I call you in time cause sissies probably need a lot of time to get ready right? Anyway, just go about your routine and I will help pick out your outfit.” Lisa stated casually.

 

Mark could feel his stomach turn even further. He didn’t know what he had been thinking, but it had really become very clear that his girlfriend thought of him as nothing but a sissy. “Anyways, I need to get going, see you in a bit.” Lisa finished not giving her boyfriend a chance to even reply before shutting off her phone and leaving him with his stomach in knots.

 

His morning had just started out terrible when he realised that he still had to perform his morning ritual. He only hoped that he wasn’t to late yet since it was supposed to be his first thing he did every morning. Quickly he gave the overtly realistic dildo a kiss. Then he grabbed the soiled boxers of his nightstand and pulled them over his head. The smell instantly turned him on he didn’t realise it though, especially since his cage didn’t seem to hurt.

 

Squirting a dollop of lube on his fingers Mark proceeded to finger himself to another anal orgasm. He wasn’t in the mood at all feeling very nervous about his day. Yet the anal stimulation combined with the scent of John’s boxers seemed to do the trick anyways. It allowed him to finish within 10 minutes.

 

After squirting yet another load into his already soiled panties Mark got up and headed to the bathroom. Once there he carefully washed his lingerie and John’s boxers. His lingerie was hung out to dry and John’s boxers were put in the bag they came in.

 

In a hurry Mark took a shower and rushed back into his room. Throwing on a pair of sweatpants he took the bag of still wet freshly washed boxers and headed outside. He hid them in the agreed upon spot before going back to his room. After all he didn’t even want to think about the questions Lisa would ask if she saw him drop off the wet boxers that were way too large for him.

 

Once in his room the speakers came to life. “Good morning Marcy, haven’t you forgotten something? Something really important?” Came the mocking distorted voice from over the speakers.

 

Mark instantly felt his blood run cold. Had he made a mistake? Was his life over? That after everything he had done to keep his secret. No, it couldn’t be. He fell to his knees and looked up at one of the camera’s before starting to beg.

 

“Please, don’t expose me. I have done everything you asked and more please don’t ruin my life. I beg you. Whatever you think I did wrong just please let me make it up. I swear it was an accident.” He cried out. He was clueless about his misstep, but he had become so used to begging that it was nearly second nature to him.

 

“Shut it sissy, you have done something wrong, you went out of your room without wearing panties. You didn’t Kiss the dildo upon existing or entering either.” The voice over the speakers said loudly. Mark felt his heart drop. He had indeed fucked up, but then again there were way too many rules to keep up with. This was so unfair, he knew complaining about how it was unfair wouldn’t help his case one bit though, making excuses wouldn’t help either so only apologising was left even if it was for breaking a ridiculous rule he shouldn’t follow in the first place. He had just become so conditioned to grovelling to achieve nearly anything.

 

“Please, I’m so sorry. It won’t happen again. I was just forgetful because i am nothing more than a stupid sissy. Please forgive me and don’t expose me I beg you. Please do whatever you want but don’t spread those flyers or make that website public.” Mark nearly cried while begging.

 

“Hmmm, alright. I won’t expose you sissy. There is a consequence though. Your deadline for deep throating that dildo has just been decreased to tomorrow morning 9 am. Be ready or be sorry.” John said through the speakers in the room.

 

Not getting his secret exposed was a huge relief for Mark. The new deadline would be a pain though. He still had about a third of the way to go before being able to fully take it in his throat. Unlike the first two thirds his progress was getting harder and slower. It was better than getting exposed though and even though he didn’t like it he still decided to thank the person behind the speaker. After all his life as he knew it depended on that person’s goodwill.

 

“Thank you, thank you so much. I will make sure I can take it all I swear. Thank you!” Mark shouted out in visible relief. Mark had been so focused on preventing his exposure that he hadn’t really stood still by the fact that life as he had known it had been over for a while already.

 

“You’re welcome sissy, maybe you can ask your girlfriend to help you out again. I think she did a pretty good job of helping you yesterday. I bet you just loved it to get your throat ravaged like that.” The voice over the speaker mocked.

 

Before Mark could give a reply, the doorbell rang. It must be Lisa, or at least he hoped so. As much as he disliked the overbearing way his girlfriend who seemed to have made it her job to help him in his journey treated him. She was still preferable to just about any other person. At least she seemed to mean well despite her harsh method. She stuck with him even after finding out about his lingerie, his cage and even the dildo. He couldn’t really blame her for not believing that he didn’t actually want this. After all the evidence against him was insurmountable and it seemed entirely self-inflicted with his lack of a proper explanation. 

 

Mark sent her a quick text to let her know the door was open. At least that was something he had going for him after his trip to the yard. Now he didn’t need to leave the room and face whatever his girlfriend would throw at him for kissing that dildo when entering again. He quickly remembered to throw off his sweatpants since he doubted Lisa would be happy with them.

 

Not knowing what else to do Mark stood there butt naked apart from the pink chastity in the middle of his room, waiting for Lisa to enter. When she did, she instantly had a smug smile plastered over her face while giving him a once over. She was wearing a burgundy coloured skater-skirt, black sheer pantyhose, black vans and a white blouse.

 

“Look at you Marcy, what a pretty sissy you make even without all that lingerie.” Lisa exclaimed taking a step closer and running her hand all the way from his chest to his back finishing with a squeeze of his bottom. “I mean you look so slender and smooth that I wonder how I ever managed to see you as a guy. Then we’re even disregarding that chastity cage and the cute pink pubic patch.”

 

Lisa’s hand had never left his bottom when she suddenly pulled him in close to her body and kissed him full on the lips. Her other hand went up into his longish hair and grabbed it tightly giving her helpless boyfriend no other option that to go along when she forced her tongue in his mouth and started aggressively exploring it wrestling back his tongue that tried to adjust to this new awkward position.

 

The Kiss took more than a minute before Lisa finally decided to let him go after giving him a last quick peck on his lips. “Mmmm my pretty baby. I have to admit the sissy look really suits you, it’s a bit hot even. I just wished you would have confided in me about these urges earlier.” She whispered before stepping back again.

 

Mark stood there completely flustered not knowing what to say or how to behave. He Hated the fact that she kept pointing out how much of a sissy he was, but that Kiss was something else. Even though it was quite aggressive on Lisa’s part he had to admit he liked it. He liked it a lot actually.

 

“Alright, let’s get you dressed so we can get going. There is something missing though. Ah I see, you haven’t brushed your hair yet. Silly me you probably don’t even have a hairbrush. Don’t worry, I have mine with me all the time and we can look for one for you later.” Lisa said after looking critically at her still flustered boyfriend.

 

“Why don’t you kneel in front of your bed so I can take care of your hair before we pick out your outfit?” Lisa asked with a smirk, waiting for Mark to follow her orders which he did rather quickly. Silently she took place behind him on the bed, took out her hairbrush and started brushing. The process was rather quick after all most of the tangles had been removed yesterday. It was just a quick straightening out of his bed head.

 

“Much better!” Lisa exclaimed standing up and examining her work before going over to his closet. She started throwing out all his socks exclaiming. “You won’t be needing those anymore, we’ll donate them to the homeless shelter on our way to CC’s. They always need socks I’ve heard.”

 

Mark was slowly starting to panic. What exactly was Lisa planning? He thought it was just going to be a quick trip to CC’s for another lingerie set and back, but it was slowly starting to look like Lisa had bigger plans. If she took away all his socks how the hell would he cover up his stockings then?

 

He wanted to protest, but he didn’t know how to go about it. He couldn’t come up with something to say that would be accepted by Lisa, after all she had already pushed her demands about him needing to wear full lingerie all the time forth.

 

A little digging around later Lisa pulled out the horrid panties she had caught him in the first time. The pink frilly ones with a hole to expose his cage making it look like the stem of a delicate flower. “Let’s go for this one. It was the first thing I saw you in so it can become the first thing I take you out in. Safe for the fact that you’ll be wearing the full set now.” Lisa giggled.

 

She carried on digging out the matching bra, stockings and garter girdle. She didn’t stop there though. Along with the set of lingerie she also dug out most of his other panties without real explanation. Mark just looked at her confused.

 

When she spotted him looking instead of taking action however Lisa gave him a slightly annoyed. “Well what are you waiting for sissy? Don’t worry about what I’m doing, just get dressed in that set I gave you. We don’t have all day to play dress up even though I guess you would like that. We have a lot to do today so chop chop.”

 

With a sigh Mark started to put on his lingerie, making sure that the garter straps were underneath his panties, and the pink cage was hanging out of the front hole. Lisa might have seen him in these panties already, still Mark couldn’t help but blush crimson.

 

“You might not need lingerie to look like a sissy, but it sure does help with making you look even cuter. Even your little caged cocklette is coming to say hello. What’s the matter Marcy? Feeling a little embarrassed? Well I am not the one who bought this dainty set of lingerie now was I?” Lisa taunted Mark whose blush was burning brighter and brighter.

 

“Now let’s look for something to put on top, it doesn’t matter how cute that set looks you sadly can’t go out in public like this.” Lisa said critically before returning to the closet. Mark just felt grateful, no matter how crazy all of this was his girlfriend did at least maintain some common sense.

 

“Let’s go with this.” Lisa announced when she turned around. In her hands she had a white T-shirt, a pair of light blue slim fit jeans and a pair of white sneakers that were worn by both guys and girls. His mother had bought that outfit some time ago in an attempt to get him a more up to date look like most of the younger guys had. The attempt failed since Mark had never actually worn the outfit and now more than ever, he didn’t want to wear it.

 

He had tried it on in secret once before just to check whether it would suit him. Just out of curiosity. He had quickly decided it looked way to clean though before hiding it in the back of his closet. The pants were way to tight for his liking. They weren’t skinny jeans yet, but too tight never the less. The pant legs rose up a little too high as well. A fact he remembered all too clear now that Lisa had forbidden him to wear sock over his light blue sheer nylon stockings with pink back seam. The shoes he had disliked because they were unisex. Girls wore the same style and that alone was to girly for him. The T-shirt was just the wrong colour. He preferred black or dark grey for his T-shirts, on top of that it even allowed his nipples to very lightly shine through.

 

Lisa could see the dismay on her boyfriend’s face and decided she needed to give him some motivation to get going. “Hurry up and get dressed Marcy, otherwise I will shove you out the front door just like you are right now, and you can get dressed right on the street. I wonder how fast you would be if I did just that.” Lisa threatened playfully.

 

It was enough to make Mark worry sick though. In no time he got himself into the outfit his girlfriend had selected which did indeed have all of the sore points he had feared for. His ankles and thus his nylons were exposed and pretty hard to miss over the plain white of his sneakers. The white T-shirt while covering his lingerie, did let the light blue and pink from the set shine through lightly. Not light enough though for Mark. Anyone looking at him would be able to make out the outline of his bra and his girdle.

 

“I…I can’t go out like this. Please Lisa, just give me sweater and a pair of socks. Everyone will be able to tell.” Mark stammered helplessly.

 

“Nonsense, you look just fine. You can barely notice what you are wearing underneath.” Lisa lied. “Not that it matters anyways cause even if you could really notice it I would still insist you go out just like this. It is warm enough to go out in a T-shirt and I already told you I would help you accept who you are. Consider this as a first step.” Lisa countered.

 

“But Lisa,…” Mark whined.

 

“No buts, we are heading out right now just like this and that is final.” Lisa said taking Mark’s hand and dragging him along. Mark resisted heavily when he realised he still had to kiss that damn dildo. He had fucked up earlier and he doubted the person behind the speakers would be this forgiving again. He also needed to take along his CC’s bag or he would be in trouble with Linda. Oh god how was he supposed to do all this? How would he explain it to Lisa? There just wasn’t a good way, but he knew he couldn’t afford not to do it.

 

“What the hell is wrong Marcy. We are going out right fucking now. Don’t make me play this the hard way. I want to help you and support your, but my patience is final as well.” Lisa shouted out annoyed when Mark kept resisting.

 

“I…I still need to do something. Why don’t you just go out and I’ll be right there.” Mark explained nervously.

 

“You bet your ass I will not do that. You’re just going to put on some socks and a sweater the moment I am out of your bedroom door? Well forget it, which makes me realise we are almost forgetting those socks.” Lisa stated firmly pulling Marks hand again.

 

“Nooo, just wait! Please, I really need to do something first. Just please leave me alone for a moment. I promise I won’t be putting on a sweater and socks.” Mark retorted.

 

“Well if your really need to do something so urgently you can do it with me here. I won’t let you have any more secrets for me. So go ahead, do whatever you claim that needs to be done.” Lisa said firmly.

 

“It’s just, well it’s kind of embarrassing.” Mark replied his blush turning crimson yet again.

 

“Oh please sissy. What the hell can be so embarrassing after I saw you in that lingerie set you’re wearing now, or the way you choked on that dildo yesterday?” Lisa asked rolling her eyes.

 

Mark’s blush intensified as he slowly started to stammer his response. “I… I nee, I mean I want to Kiss my dildo goodbye and I need to bring my bag from CC’s they want to reuse their bags to be environment friendly.” Mark stammered almost unable to form the words. Oh god why had he said he wanted to kiss that damn dildo he hated it, but needing to kiss it would raise more questions so he just needed to choke up the extra humiliation.

 

Lisa looked at him with a shocked expression for a few minutes before starting to burst out laughing. “Oh my fucking god. You are such a sissy slut Marcy. Kissing goodbye to your toy, but sure go right ahead take all the time you need. God this is so preciously hilarious. Just give me the bag first so I can stuff away your socks. They’ll be easier to carry like that.” Lisa said laughing excessively.

 

With a beet red face Mark handed the oversized pink bag with the logo of CC’s over to his girlfriend. She took it and instantly started filling it with the socks and panties she had taken out. In the meantime, Mark headed to his dildo, but once in front of it he just kind of shifted awkwardly. Despite what had happened yesterday he still didn’t want to do this in front of his girlfriend.

 

Stuffing the last of the underwear into the bag Lisa spoke up. “Well what are you waiting for sissy? Don’t you want to say goodbye to your toy. Don’t mind me, I just want to watch that’s all.” She said to a nervous Mark who had been waiting for a moment where his girlfriend would look away. Now that he realised that wasn’t going to happen, he just leaned down and gave the tip a quick goodbye peck.

 

“What the hell was that sissy? Do you call that a proper goodbye? No, you so badly wanted to kiss your big dildo goodbye so I insist you do it properly.” Lisa shouted at a shocked Mark who didn’t dare object and so kissed it again more tenderly.

 

“No, no, nope you’re doing it all wrong. I mean to actually want to kiss a toy goodbye you must be a real slut. So show that toy how much of a slut you are for it. I mean it’s you who wanted to kiss it goodbye after all.” Lisa said sternly. Mark’s panic only increased as he looked at his girlfriend not knowing what to do.

 

“God do I really have to tell you everything I would really think a slut like you would know how to handle a toy. Never mind though. Just follow my instructions. Place your tongue on the balls and slowly lick all the way up to the tip. That’s a good slut. I bet your mother would be proud of you. Do you still remember how she called me a slut just because I wore a crop top?” Lisa instructed with a smirk enjoying how Mark followed her instructions.

 

Mark on the other hand was out of his mind with embarrassment. Especially the comment Lisa had made about his mother made his stomach turn. If she saw him like this, or his father for that matter he would be kicked out and disowned for sure. No, he just had to go along with Lisa instructions, and it would all be over soon. Once she has something in mind it was Impossible to convince her otherwise.

 

“Now wrap your lips around the head and slowly lower it until you can’t go any further. Once you are as far down as you can go stay there for five seconds then slowly come back up. When you reach the head once more let it pop out of your mouth with a nice popping sound and give it a tender kiss.” Lisa carried on her instructions.

 

Lisa felt herself get wet as she watched how her boyfriend worshipped the dildo like a two-dollar whore. Mark himself was surprised that he was able to take the dildo down three fourths of the way instead of yesterdays two thirds. Yesterday his throat had just been so sore from Lisa’s throat fucking that he couldn’t manage more.

 

It did give him hope though since he only had today left to get himself to take it all. With Lisa’s plans to take him to CC’s and the homeless shelter he didn’t know how much time he would have left to train himself.

 

The thought that he could take it down further than expected was a relief, but at the same time it was a huge point of embarrassment as well. What would Lisa think of him? Sucking that huge toy down all this way?

 

His cheeks burned brighter as he finished up his instructions while Lisa complimented him. “Well well, just look at you. If my memory serves me correctly you couldn’t take that cock that far yesterday. I bet you must have been training all night you dirty slut.” She said with a wink feeling another wave of arousal surge through her. God she felt so powerful ordering her boyfriend around while he was on his knees.

 

Mark wanted to defend himself claiming that it just wasn’t true. He knew that wouldn’t be believed though. After all he even surprised himself. He could suck that dildo down way further than yesterday and that was a fact.

 

“Anyways, now that you gave your dildo a proper goodbye we can get going. Just take that bag because there is no way I want to be seen carrying around something from that obnoxious shop you seem to like that much.” Lisa said delivering yet another stab to his ego.

 

He nervously followed his girlfriend downstairs and out of the door where she had parked her car. At least that was one advantage of going with his girlfriend. He didn’t need to get on a bus with other people. At last he would be able to avoid those two girls who had been humiliating him since his first bus trip. It was the only upside he saw to this whole endeavour though.

 

Once out of the door Mark closed up and dashed to the car as fast as he could. He prayed none of the neighbours had seen him. When he reached out to open the car he was mortified and nervous when it didn’t immediately open. “Lisa, open up!” He hissed.

 

“Watch your tone Marcy! My car’s receiver is broken so I have to open it manually.” Lisa explained calmly walking to her car with no sense of hurry at all. She had also be quite loud when saying it making Mark’s panic rise even further. It seemed to take forever until the car finally opened, but once it did Mark instantly got in with a loud sigh of relief.

 

Lisa slowly got in herself then watched beside her with a smirk seeing her obviously nerve wrecked boyfriend with his big pink bag on his lap. “Alright Marcy let’s go an hit up the centre for the homeless first. Then I’ll take you to your precious boutique.” Lisa said as she pulled out of the driveway and steered her car in the direction of the city.

 

It only was a short drive until they pulled up in front of a big concrete building in a shadier part of town. A couple of dirty looking people with worn up clothes were hanging around. Mark knew the cause of this place was noble, yet he couldn’t help from feeling creeped out by it. It was just so far removed from his life in the suburbs.

 

“Let’s get out of the car Marcy and you better get out quickly with your bag or I swear you’re going to be sorry.” Lisa stated to her nervous boyfriend. It was necessary or Mark wouldn’t even think about leaving the safety of the car. Definitely not in a place like this.

 

His nerves only increased once they had gotten out of the car. All eyes seemed to be glued on them. True they looked very out of place here, still Mark couldn’t help but feel it was cause of his bag and what he was wearing underneath his clothes.

 

The worries soon got confirmed as an old homeless man shouted in their direction. “Are ya wearing a Bra underneath that you fucking pansy?” he asked in a rough sounding voice.

 

Mark was shocked, and Lisa certainly didn’t put him at ease at all when she whispered in his ear. “He is just Jealous of me Marcy, I bet he has never seen a boy as pretty as you. Hell he probably wishes that you were walking at his arm instead of mine. I bet he would love you to play with his tool the way you play with your toy at home.”

 

After a slight pause Lisa continued. “Would you like that? To have a real tool to play with instead of a silicone cock? Real warm flesh and blood that can shoot a real load of cum in your mouth? A real cock with it’s own smell and taste instead of sterile rubber.”

 

With a horrified look Mark looked at the homeless guy then at his girlfriend. He couldn’t believe what he was hearing. It made his stomach turn. Hell he didn’t even dare walk up close to this guy afraid of what he might smell like, let alone actually touching him or tasting him. The mere thought of that made him want to puke.

 

Lisa knew full well how grossed out Mark must have been now. She honestly liked having so much power over him with just a few words. She hadn’t looked to specifically gross him out. It was just the first thing that came to mind that would have a big impact. Besides it might also be a good threat to get him moving quickly here, because if she was being honest, she herself didn’t feel that at ease here either. It was just an excuse to get Mark out and about for longer.

 

When Lisa started guiding her sissy boyfriend into the building there were no objections at all. He just meekly followed along wanting to be out of here as fast as he possibly could. “When we get to the donation desk I want you to fish out all your socks and put them out for the person standing behind the desk. Then I want you to say that you want to donate all of your socks since you discovered the joy of wearing stockings. Is that understood?” Lisa asked sternly.

 

Mark’s look told her everything she needed to know. He was positively scared. Being cruel was so easy. It almost made her forget that she was supposed to keep up her act of understanding girlfriend. Time to make that right.

 

“I know how hard this is baby, but I have to be stern otherwise you will back out and that wouldn’t be good right? I only want what’s best for you and I believe that admitting your love for feminine things to someone else is a great first step in accepting yourself for the sissy we both know you are. It is the sole reason why I came here. There is no way you will ever see any of these people ever again, so it doesn’t really matter what you tell them.” Lisa said softly.

 

As weird and embarrassing as it all was, it did also somehow make sense when he viewed it from Lisa’s point of view. He really believed she wanted the best for him going of the information she had, after all she had seen him do and ask for it was no more than logical that she viewed him as nothing but a huge sissy.

 

Nervously Mark walked up to the donation desk, pulled along by his girlfriend. He knew he had to do this right. He couldn’t disappoint his girlfriend, the only one who knew and accepted his situation trying her best to help him going of the information she had.

 

The donation desk was a big, grey and standing in front of a storage room. Behind the desk there stood an older woman. Her hair was obviously dyed blond and held in a tight bun on top of her head. She looked stern, plump and just like she already had enough trouble for one day. “What are you two youngsters here for?” she asked sternly.

 

“I… I’m here to donate my socks since I discovered the joy of wearing stockings.” Mark meekly stammered raising his pink back as he started to lay pair after pair of his socks on top of the desk looking around nervously if no one had overheard him. He knew there was no way back now. His socks were lost for good.

 

The woman behind the desk looked at him surprised, raising an eyebrow as she gave him a once over, looking him up and down critically. Her eyes widened as she caught a glimpse of his bright lingerie that was shining through his white T-shirt.

 

“Fucking sissy, why do I always have to deal with the freaks? Kids these days fucking unbelievable.” The woman grumbled under her breath as she collected the socks and carried them away to the storage room before returning to the desk. “Thank you for your donation. Every little bit helps.” She said in an annoyed tone obviously just reproducing a studied text she had to say.

 

“Y…you’re welcome.” Mark said before turning around and rushing out carrying the pink bag that still held a lot of his panties. Lisa just giggled as she rushed behind him right to the car opening it up for him to finally return to a somewhat safe setting.

 

“You did great baby, I am very proud of you.” Lisa said gently, taking Mark’s chin and turning his head to give him a big intimate kiss that blew his mind. It instantly turned him to putty in her hands as he once again got the confirmation that Lisa really meant the best with him.

 

“Now let’s go get you a nice reward at your favourite store. I never thought about going there, but if I’m honest I look forward to going there with you and learning more about what it is that you like.” Lisa said. It was true in a sense after their visit she would have much more liberties with how she treated her boyfriend while still claiming it was in his best interest. Linda and her had discussed how they would act like they didn’t know each other and how Linda was an expert on sissies. That way Mark would only be able to blame the stern tall store owner. With a big smile on her face Lisa drove off.

 

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