Part 11

Chapter 13

To Mark’s huge relief he witnessed Lisa opening her shorts. Without the tight fly holding the dildo in place it would fall out, at least if Lisa hadn’t taken a hold of it to put it neatly back on Mark’s night stand.

Lisa took off her shorts completely and her panties along with it. It was instantly clear that her neatly trimmed pussy was sopping wet. It smelled strongly, not unpleasantly unlike John’s boxers. While it did smell way better to Mark it wasn’t having the same effect on him.

“Since we can’t have sex the way I wanted last night I guess I’m going to have to be happy with just oral, I mean unless you can all of a sudden magically unlock yourself?” Lisa observed Mark’s expression for a moment. He just looked helpless.

“That’s what I thought, well I am not going to sacrifice getting orgasms from my boyfriend just because he is a sissy. So your tongue will have to do. You are going to lick me, and you are going to learn how to do it properly. I mean you better learn cause if you can’t do that I really have no use for you at all. Do I?” Lisa said sternly.

Mark just sat there on his knees, not knowing what to say. He didn’t like this, not one bit. He had never eaten a pussy before and he never wanted to do that either. Yet right now it looked like he would have no choice but to do exactly that. After all Lisa was right, what else did he have to offer? He couldn’t risk losing her either. Losing his girlfriend would devastate him, and who knew how many people she would tell about his little secret if she wasn’t his girlfriend anymore. No, he simply could not risk that.

“Well Marcy, what are you waiting for? Get licking.” Lisa said, but when Mark didn’t react instantly she stopped him. “You know what, I have just been wondering. It really doesn’t make sense to me that a sissy like you would only have some panties. I guess they are really frilly and sissy panties, but still it just doesn’t make sense.” She said closing her legs again.

“Before we continue I want to see your entire collection. I bet a sissy like you just loves getting prettied up for her partner. So that is exactly what we are going to do, we are going to make you really pretty before you get to lick me. Isn’t that exciting?” Lisa asked with a big grin plastered on her face.

Mark was shocked, what was he supposed to do now? What would Lisa say when she saw the elaborate lingerie sets he had? Panties were one thing, but those full expensive sets? It would make the chance that he would ever be able to convince her that he wasn’t a sissy way slimmer.

He waited a minute just to see if she wouldn’t change her mind again, but sadly she didn’t. She just sat there on his bed half naked with her arms crossed over her chest waiting for Mark to take action. Eventually he felt like he couldn’t wait any longer. It was no use anyways, Lisa was clearly not going to change her mind so all he was risking was getting her mad and after having a taste of what a mad Lisa was like he didn’t want a repeat of that.

Slowly Mark got up and walked over to his closet where he opened up the drawer with his lingerie stashed in. With a big smile Lisa appeared behind him looking over his shoulder. “My my sissy, that’s a lot of pretty lingerie you have here. So many pretty matching sets as well. Why don’t you wear them all the time?” Lisa asked.

When Mark didn’t immediately answer Lisa spoke up again. “Well, let me guess. It is because you are embarrassed. Is that it? Of course it is, but I have news for you. I told you I would help you become the sissy you deep down want to be. We have gone over how I won’t tolerate you not going forward with things just because you’re embarrassed. So, from now on you are going to wear a full set of pretty lingerie all day every day. Isn’t that just great?” Lisa asked with a huge smile.

Mark was horrified wearing his lingerie all the time? That was just horrible. Not only was it uncomfortable, especially that overtly tight girdle. It would also increase the chance of him getting found out. He couldn’t just let this pass. No, he had to speak up now. “But Lisa, I can’t wear that, what if people see. Please you can’t be serious aren’t these panties bad enough yet?” Mark pleaded.

“Shut it sissy, when I say you are going to wear full lingerie all the time you do it understood? I told you I was going to help you become who you really are, so you don’t have to hide your true-self anymore and I meant it. I knew it was going to be hard, but I love you and so it is my duty to help you even at those hard times.” Lisa snapped.

“But Lisa,…” Mark tried pleading again, he instantly got cut off by his determined girlfriend.

“You are going to wear full lingerie sets from now on and that’s a fact. If you are really that embarrassed to the point of not doing it. I can always just take some pics of your drawer here and show them to everyone. I might even tell them about your love for giving blowjobs and how you are training with a huge dildo to become a deep throat champion while I am at it. I wonder if you would still be so shy to wear lingerie under your clothes if everyone knew anyways.” Lisa firmly stated.

Mark couldn’t believe what he was hearing. Lisa would never do something like that would she? He wasn’t sure, she looked so determined that it was frightening though. One thing was certain, he didn’t want to challenge her on this one. It would be disastrous.

“O…okay, I’ll do it.” Mark whimpered pathetically. He had no desire to actually do it, but it was the only way he could even try to keep his secret. The lingerie could still be hidden underneath his clothes at least. He only hoped he would be able to hide it well enough to keep his secret.

“Good, I think I want to see you in this set today then.” Lisa said with a smile fishing out the white panties with the hot pink detailing. It was a horribly frilly set, but it wasn’t even his worst set yet. That fact alone told the whole story about how his underwear drawer was starting to look.

With a gulp Mark gathered the entire set and started to put it on, the bra, the panties, the girdle and the stockings. He suddenly realised that with Lisa’s new demands he was going to wear these and similar items so much going forward that they might as well be part of him.

He really didn’t know how he would handle wearing this overtly tight girdle 24/7, but he would find out soon enough. It wasn’t like he had much of a choice. He also feared that he would no longer be able to skate at the skatepark. The girdle didn’t allow for enough flexibility to do all the tricks he wanted and the fear of falling and exposing his underwear was huge. It wasn’t that unusual to just hang at the skate park, but still Mark was scared that questions would come sooner or later.

Carefully Mark rolled his stockings up in doughnuts before Rolling them up his leg. Just like he had been taught. He even slipped the garter-straps underneath his panties much to the hilarity of Lisa. “Oh my god, you’re even more of a sissy than I originally thought. I mean damn, you even pay attention to keeping your ass accessible.” Lisa laughed loudly much to Mark’s shame.

“I have to say, this outfit really suits you sissy, now why don’t you get up and give me a little twirl, so I can have an even better look.” Lisa said with a smirk plastered across her face. Mark felt sick to the pit of his stomach, but he didn’t dare say no so reluctantly he gave Lisa a little twirl, feeling utterly debased.

“Hmmm it does really suit you, but I do feel like there is something missing. The picture is incomplete somehow.” Lisa said while studying Mark’s look intensely. Mark didn’t really know how to behave or act as he just stood there in nothing but overtly frilly lingerie, awkward in front of his girlfriend.

“Aha, I know what it is. That tangled mess you call your hair really doesn’t suit your style at all. Go sit on the ground with you back to the bed. I’ll take care of it for you.” Lisa said in an excited tone. Mark didn’t have much of a choice. He liked his tangled longish hair. It looked though like a real rockstar in his eyes. Lisa was right though tough was the last thing he felt at the moment.

With a sigh he sat down in front of the bed like he had been told to do. Lisa instantly took place behind him opening her legs, so Mark sat in-between. She took a hairbrush out of bag and started brushing.  It was a tough job requiring a lot of tugging and pulling with how bad Mark had allowed it to become.

“Damn Marcy, do you even take care of that mob of yours? A girl should be proud of her hair, so a sissy should to. I mean you have such nice hair, and a lot of it. If only you took better care of it. Don’t worry though, tomorrow we’ll go searching for some good hair products for you.” Lisa said as she did her best to untangle her boyfriend’s hair.

Mark felt terrible there was a gorgeous girl, naked from the waist down sitting on his bed. One who had confirmed she wanted and would have sex with him and yet here he sat. Clad in frilly lingerie, with a sore throat, locked in a chastity belt while that girl was brushing his hair.

The brushing took about 15 minutes which seemed like ages to Mark. Lisa didn’t care though. She paid extra attention to getting every part neatly brushed. She loved having a direct hand in her boyfriend’s feminization and it was quite a relaxing experience for her.

“That looks way better Marcy, I think you’ll agree. Before you go and have a look in the mirror however I want to put some light make-up on you though. I don’t have much with me, but I think you are going to love it. I think it will really suit you. You’re even in luck, I have just the lipstick to match your pretty lingerie.” Lisa announced with a smile, getting up and sitting down in Mark’s lap before he could say or do anything to get out of his predicament.

With a big smile she unscrewed a tube of mascara and started to apply it to Mark’s already long eyelashes. “Delicious, this really makes your eyes stand out. It looks so pretty. I have to give it to you. You really have pretty eyes and lashes to die for.” Lisa explained excitedly.

Mark just cringed at the comment. He didn’t want to have pretty anything. He wanted to be a tough guy, not a pretty sissy. The more time went by the more of a pretty sissy he was becoming though, much to his shame.

With their current position Lisa’s bare pussy was up against his cock making it strain painfully against his tiny cage. At least the cage wasn’t painful all day anymore like it had been at first, but right now when he tried to get hard it did hurt a lot. The fact that he was so close to fucking Lisa and losing his virginity, only a thin layer of satin and a pink cage separating his cock and her pussy, stung extra hard.

“Alright, let’s add some lipstick and then I am afraid I am finished. On moments like these I wished I carried a full set of make up around, but mascara and lipstick can do a whole lot already, and they are pretty practical to carry around.” Lisa said to a Mark who felt grateful. He didn’t even want to imagine what full make-up would look like.

With that said Lisa opened a tube of hot pink lipstick matching the frilly details on his lingerie perfectly. She applied it liberally before dabbing his lips with a tissue and applying another layer making it look really full and luscious.  His lips looked really kissable, or fuckable if only she had a cock.

“Alright, I’m done. Now why don’t you get up and have a look in the mirror. I just know you will love it. I certainly do, I mean I could really kiss you right now, but we don’t want to smudge your make-up right from the start now do we?” Lisa asked with an innocent smile enjoying the look of intense embarrassment on her boyfriend’s face. It was making her all so wet. Having Mark’s now pretty face buried between her legs would feel so good, but first she really wanted to see his reaction.

Getting up and moving in front of the mirror Mark was shocked. He had to look twice to even recognize the sexy girl staring back at him. Her lingerie looked ridiculous, there was a unusual bulge in the front of her panties and her chest looked flat. Apart from that she looked really pretty. Pretty enough to make his cock strain in its cage yet again.

He was scared and horrified. It was crazy to him that a little bit of make-up and neatly brushed hair could do that to him. It made it hard to even recognize himself as a guy. The fact that he was getting turned on by his own image truly fucked with his mind. Slowly he brought a hand up to his cheek in disbelieve, only to see that girl do the same.

Mark’s reaction was far better than Lisa had hoped for. Truth be told she hadn’t expected the result to make such a difference, but in retrospect it was no wonder. Mark’s face had always been on the round baby-faced side of things. It had never been manly, so it wasn’t such a wonder that adding a few girly features would swing the overall perception.

“I guess that means you like it? Am I right?” Lisa taunted Mark breaking the silence. Mark didn’t like it at all but telling that to Lisa wouldn’t help his case one bit. Certainly not now he knows how determined she was, so instead of protesting he just sucked it up and nodded his head.

“I’m so glad you think so too. Well what are you waiting for Marcy? Come over here and lick my pussy as a thank you. You better make it good as well, after all I deserve a big thank you for all the things I have done for you, don’t you agree?” Lisa asked with a smirk sitting back down on the bed and opening her legs wide, exposing her dripping pussy to a still shook Mark.

Mark decided not to answer that question. He felt bad enough as it was and so he just dropped to his knees to perform his duty. He didn’t like what Lisa had done at all, but none of that mattered. He didn’t want to lose his girlfriend as well as have his secret out so there really wasn’t a choice to it.

Leaning forward Mark extended his tongue and slid it in Lisa’s pussy. The feeling was kind of gross, but Lisa really didn’t taste too bad. It was a slightly sweet, slightly sour taste with a pleasant smell. At least to Mark. It had nowhere near the effect on him like the sweaty unwashed cock smell he had been sniffing from John’s boxers for so long already.

If this had been a mutual thing and just foreplay Mark would have probably even enjoyed licking Lisa’s pussy. With how forced this had been and after all the humiliation he had endured without even a possibility that he would get off himself, this just sucked. It was just a chore now.

Lisa threw her head back, this felt so good. Mark’s tongue was nowhere near as good as Stephanie had been, but it felt great none the less. He was a decent pussy licker, not good, but certainly not bad for what was his first time. The fact that Lisa was already overtly excited and just loved the fact that she was kind of forcing Mark to eat her out certainly helped in how good it felt. With Mark it felt way more special than it had with Stephanie.

Mark was a little clumsy with his tongue, but she could feel that he was trying his best. It was not bad either. Just not as good as she had been used to from past girlfriends or Stephanie. Mark was her first boyfriend she got to lick her pussy though and that on its own helped a lot in how good it felt.

He licked up and down Lisa’s pussy, going straight for her clit after a few licks. He had read up about this subject some time way back in the hope to impress a girl with his skills. He had read you had to stimulate the pussy until it was really wet, working up your girl before going for the clit. It did seem like Lisa was insanely wet already though.

It seemed like it had been a good decision as he got reward by loud moans coming from his girlfriend. She was clearly having a good time. He hadn’t expected her to suddenly grab his hair and pull his face tightly against her pussy, making him struggle to breath. This hadn’t been in any of his guides. All he could really do was struggle and try to get free, but in his current position he had no leverage to actually get free.

A few seconds of struggling later he was suddenly met by a very tight pressure on the sides of his face as Lisa clamped her thighs shut tightly. Lisa had put Marks face in a death-lock before she suddenly started gushing wave after wave of her juices in her boyfriend’s face as an intense orgasm rocked through her body.

By the time she finally came down from her orgasmic high she was exhausted. Mark wasn’t really the best lover when it came to licking her pussy, yet this had been the most intense orgasm from her life. She was surely going planning to enjoy Mark’s tongue a lot more in the future.

She released his head and fell back on the bed still breathing heavily. Mark in turn did the same falling back on the floor. His face was coated in a hefty amount of his girlfriends’ juices, and while Lisa’s heavy breathing stemmed out of post orgasmic bless his was caused by a lack of oxygen after being smothered in Lisa’s pussy.

It took a few minutes until Lisa had caught her breath enough to sit back up. When she did she instantly burst out laughing. “Oh my god Mark smelling like sex with all that smudged make up you look like a cheap whore instead of sissy. Quite frankly the look suits you as well.”

Lisa got up slowly and picked up her underwear and shorts putting them back on. “Anyways, I should get going now. Don’t forget I want to go to that shop with you tomorrow and I want you in full lingerie.” Lisa said leaving Mark’s room and closing the door behind her.

Mark just laid there in disbelieve. He had just been intensely used and now Lisa had just left? It all felt so surreal, but the strong smell of pussy sticking to his face certainly let him know that it was all too real.

John had been watching the whole thing with a lot of interest. His cock had never left his hand and over the duration of Lisa’s visit he had shot a wad of cum in his boxers three times. He grinned thinking about how Mark would get a pair of extra crusty boxers tomorrow as a reward for the show he put on.

He might not be happy about this girl messing with his grand plan, but he couldn’t deny it had perks either.  He hadn’t felt the need to watch porn in a long time, well at least not anything other than what he caught on the camera’s in Mark’s room.

Just like Mark and Lisa John had also been surprised with how good the sissy looked with neatly brushed hair and make-up. It certainly was something he would have to keep in mind for later. He was also more than pleased with how Lisa had pushed Mark to wear full lingerie all the time from now on.

Well it looked like it was time to taunt the sissy a bit more again. It had become one of John’s favourite activities and he simply refused to miss a chance to do so.

“Hello Marcy, did you have a good time seeing your girlfriend? It certainly looks like it from where I’m sitting. You look spend. I also didn’t know you liked to be called Marcy, but obviously your girlfriend knows you better than I do. I just knew you had always been a sissy despite what you might claim. Anyways, I promise you I will respect your wishes and call you Marcy from now on.” John spoke into the speakers with a hearty laugh.

Mark blushed heavily although he had endured so many of his tormentors taunts already the words still stung heavily. God how had things gone this far out of control? Things had gone to far to go back. Now the only way he saw was going forward and hoping that everyone just grew tired of him and left him alone.

“I do have to say that freshly fucked whore look does really suit you Marcy. Maybe you should go for it more often. Isn’t it fun to have such an accepting and understanding girlfriend? I for one really enjoyed the show. It looks like you have a lot of work to do before Wednesday before you can really deep throat that cock like the sissy you’re supposed to be, but I am sure you will manage. You already made such good progress.” John laughed.

“Too bad you didn’t get to cum unlike your girlfriend. Some partners are so inconsiderate right? I mean your girlfriend appeared to have the orgasm of a lifetime and you were left hanging. Now to be fair you are the only one to blame right? If you had been honest and told her you like it up the ass now I am sure she would have obliged. She did seem to like having a cock after all.” The taunts continued.

Mark felt more devastated than ever. His girlfriend had only just violated him. He Hadn’t recuperated from that yet and now John was making him feel even worse about himself. It hurt all the more since he knew it was true. Stimulating his ass did seem to get him off. It had been the only way he had gotten off since he was put in that damn cage.

Without a doubt that dildo would have been way to big and not have felt good at all, but he guessed that to his intense shame he did like it up the ass. His girlfriend would have probably been way to happy to fuck him as well with how enthusiastically she had fucked his throat. He would never tell her he liked it up the ass.

“Luckily for you I am a generous Master. You are allowed to cum for me, so go ahead. Go wash your face then install yourself nice and comfortably on your new sheets, pull those wonderful smelling boxers over your face and go at it. Finger your boy pussy like the pathetic sissy you are.” John taunted to Mark’s intense embarrassment.

When Mark didn’t immediately react a loud and clear, “that was an order!” Came over the speakers.

Sighing deeply Mark got up and dragged himself towards the bathroom. He felt exhausted, but he knew he couldn’t afford to rest. In the bathroom he groaned spotting his face in the mirror. The mascara had ran and his lipstick was smudged big time. He was glad that he could at least get rid of all that.

Johns intentions hadn’t been pure though. Telling him to wash his face was purely to make sure that the scent of Lisa’s pussy wouldn’t interfere with the scent of John’s unwashed cock stuck in the boxers.

It took a few minutes until Mark managed to get his face clean of all the makeup, but in the end, he managed. With his face finally rid of the makeup he could see a bit of his old self again. Still even without the make-up he ended up looking very girly. People who didn’t know him as a guy probably wouldn’t even recognize him as one.

“Alright sissy now enjoy your masturbation.” John taunted. With a sigh Mark got on his bed, the satin sheets feeling so weird and slippery against his nylon covered legs. Reluctantly he pulled the still strong-smelling boxers over his head. His cock instantly strained against its cage, but less so than the first times.

It wasn’t his reaction of arousal to the smell that had decreased. The arousal only got stronger the more masturbation sessions passed. His cock was just slowly learning not to react by getting hard anymore. It couldn’t get up in its tiny cage and only ended up hurting him. The difference was too small for Mark to really notice, just like what had happened with his reaction to the smell of John’s cock.

Mark didn’t waste any time he just plunged his finger in his hole like he had grown used to by now. His butt didn’t resist the intruder anymore. Instead it seemed to welcome it. It didn’t even start as an uncomfortable feeling anymore. It just instantly felt good. Just like before Mark went for that special spot within his butt making him get off within a few minutes.

He caught his breath from yet another intense orgasm, not even bothering to remove the smelly boxers from his head first. The smell was still just as disgusting yet somehow without realizing it he craved the scent as well. He liked and Hated it at the same time.

“Enjoy your day sissy, I am going to give you the afternoon off. Enjoy it. All rules still apply though. You still have to masturbate before you go to bed and you still need to be able to deep throat that dildo by Wednesday.” John said before making the speakers go quiet.

Mark couldn’t believe it, frankly he didn’t believe this would be the last he heard from his tormentor today. It would certainly be a welcome change though. Yet it wouldn’t make much difference, he wasn’t planning on going to the skatepark today, or out of his room at all for that mattered. Not now that he needed to wear lingerie all the time.

Honestly, he didn’t know what he should do with this time. It had been what felt like an eternity since he had been able to plan things on his own. He often had days where he wouldn’t leave his room before, but lately that had changed. Just to escape his tormentor. Usually he filled his time with gaming then, but he didn’t feel in the mood for that at all.

He didn’t have any books, nor any series he wanted to watch. Mark really had no idea of what to do in his room all this time. Eventually he did start a game of counterstrike, just to kill some time. His focus was severely lacking though, and he ended up making his team lose on more than one occasion.

The teams he was on were rather salty as well, throwing all sorts of insults his way like “Girls shouldn’t be on their big brother’s computers.” Or, “Damn even my girlfriend plays better than this.” Sitting there in full lingerie with a pair of cum soaked on these kinds of remarks really stung, enough so that Mark decided to quit the game.

One game down he tried another one. An MMORPG it was a long time ago that he had played something like this. Upon opening his account however he decided to quit already. He had forgotten that all his characters he had made were women. Back in the day when he still played this game frequently he had made female characters because they had sexy armor and costumes. He had always liked to imagine controlling a sexy girl in a lewd outfit.

It seemed ironic now that he had basically become one of those “girls”. He was forced to wear lewd outfits and his moves were controlled by someone who ordered him around over a speaker. Someone he didn’t have a single clue about who it was.

Eventually Mark just decided to turn off his computer. Having literally nothing to do Mark eventually sighed and took the dildo. He hated it, but if he wanted to be able to deepthroat it by Wednesday he would really need to train, that much had been proven. Not that deepthroating was a skill he even wanted to possess, but he had come this far so it would be stupid risking his proposed sissy identity from getting out now.

For the remainder of his afternoon Mark trained with that dildo every now and then, keeping long breaks in between tries, but he kept going nonetheless. It was more out of sheer boredom than anything else.

By the end of the day Mark was able to swallow the dildo for about two thirds of the way. It was a huge improvement, but those last inches would probably be the hardest to be able to get down his throat.

Surprisingly the one behind the speaker had kept his promise and not contacted him again for the remainder of the afternoon and evening. It was still early yet Mark did decide to go to sleep. The confrontation with his girlfriend had been a draining experience and he was really exhausted. Besides, he had nothing else to do anyways.

Following the rules Mark fingered his ass to climax again while smelling John’s discarded boxers. He gave the dildo he had just practised so much on a goodnight kiss and drifted off to sleep, worrying about how his trip to CC’s tomorrow would go. After how Lisa had treated him today, he was really worried about how she would act at the store and especially what the combo Lisa and Linda would give. He didn’t know the two had met already.

(If you like my story and would like to see more and support me please consider joining me on Patreon: www.patreon.com/Fibaro . If you don’t want to or can’t then don’t worry, everything will eventually be available for free, but it’ll take a bit longer to become available.)