Neighbourhood Terror to Sissy Pt. 12

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.