Neighbourhood Terror to Sissy Pt. 17

Chapter 19

The drive back home was pretty uneventful, Lisa just sat behind the wheel smiling ear to ear. She had had an awesome day so far, making out with two gorgeous women and now she would spend some quality time with her sissy boyfriend. Marcy was very worried about that quality time. She hoped for sure that it wouldn't involve that dildo going up her ass. There was no way she could take that. She only ever had a finger up there.

Pulling up in front of the house it was early afternoon, more than enough time to have some fun while Marcy's parents were still at work. "Marcy, take the bags out of the trunk and bring them up to your room, then strip down to your lingerie." Lisa simply ordered as she went up to the front door, took the key from under the flower pot and opened up.

Marcy soon went inside and straight up to her room, hoping none of the neighbours had seen her with the Bags from CC's. she went straight upstairs, put the many bags down and stripped down to her lingerie exactly like Lisa had ordered.

Mere seconds later Lisa entered the room smiling down at her obviously very embarrassed sissy boyfriend. "You know this set is so you, with the little cut out for the nipples and your little cage. I just kind of wanted to see it on you again, but you can strip out of this as well and come see me in the bathroom." Lisa said with a big smirk, taking the bag from the sex shop and leaving a stunned Marcy behind in her room.

With a deep sigh Marcy did the only thing she really could do which was obeying Lisa's demands. Not that she really minded getting out of this stupid lingerie one bit. It had caused her enough trouble throughout the day already.

Once she was entirely naked she entered her bathroom only to see that Lisa was now putting up a rather full looking pink rubber enema bag on his shower rod. Instantly Marcy froze in panic, she should have guessed that they didn't but that enema bag for nothing, yet she was nowhere near ready to take this. Especially not one that full.

"Ah here you are, I prepared your enema. Now go lay on the floor ass up face down. This once I am going to do this for you, but after this you will do this on you own. Understood?" Lisa asked firmly, making it clear in her tone that she didn't want to argue.

"Yes Miss Lisa, right away. Is the bag really supposed to be this full though?" Marcy asked nervously, trying to better her situation by obediently getting in position. Yet at the same time posing a careful question to hopefully make her situation a little bit better.

"Well I don't really know yet Marcy, I just started to fill the bag with lukewarm water as is in the instructions. We can always shut the valve if we notice you have had enough. Anyways, first I'm going to give you a good rinse to get most of the dirt out. Then I'm going to give you another rinse with that scented soap so you are squeaky clean and smelling like roses when I finish." Lisa explained.

"Normaly you can just go straight for the soapy rinse in the future. At least as long as you keep up the enemas, you are going to preform one each morning and evening at least. Like that the dirt build up should never get big enough to warrant two rinses." Lisa furthered her explanation while dripping some cool slick lube on his butt hole and on the tip of the slender short pink cock like nozzle.

"Just Relax Marcy, I'm going to show you that if you do this right, you will soon start loving your little enemas just relax and let me do the work." Lisa whispered in Marcy's ear with a smile. She was so excited to start working this small slender dildo shaped nozzle in Marcy's bottom, making it disappear between her butt cheeks. The thought alone made her very wet.

The contrast between what was going to happen, and Lisa's gentle whispers was very stark. She really sounded like she meant well. Maybe this was inevitable. It sure would be nicer not to have to get her fingers dirty every time during her masturbation sessions. What was she even thinking? She shouldn't have to finger herself, but then again, she did, afraid of what would happen if she didn't. For all Lisa knew she really wanted this so in that regard she was only helping or trying to help. Since she didn't come clean about what was really happening Lisa couldn't know right? God this mess really was getting deeper and deeper each day. Marcy thought with a sigh

Maybe Lisa was right, maybe she should just relax, and it might actually feel nice. Things up her butt had started to feel very nice lately. No it shouldn't feel nice, she was a guy, things up her butt just shouldn't feel nice. God what was happening to her?

While Marcy's mind was in shambles trying to fight itself over what should and shouldn't happen. Lisa had brought the slick tip of the dildo shaped nozzle up to her sissy boyfriend's ass. She gently rubbed the tip around against Marcy's rosebud, before finally stopping in the centre and applying a gentle pressure.

With the dildo only being as thick as about two fingers and it being well lubricated. It really slipped in with ease. To Marcy's surprise it didn't even hurt, not even at first. Sure, it was a small slender dildo, nothing like that monster standing on her nightstand, but still.

To her horror it even started to feel good rather quickly as Lisa slowly worked it in and out of her butt, the tip and shaft rubbing over that special spot in her butt in a teasing way. A few strokes in Marcy couldn't help herself but let out a soft moan. Marcy's face instantly turned crimson. This shouldn't feel good and yet it did. Lisa just smile triumphantly as she continued slowly fucking the sissy's ass with the dildo shaped nozzle.

Marcy's mind was racing. This really shouldn't feel good, especially not with a dildo. Doing this with her fingers was one thing, but using a dildo, something shaped as an actually cock only made it feel so much more girly and embarrassing. It were the last feelings Marcy needed since simply using her fingers was plenty embarrassing and girly already.

Lisa just kept on working the dildo nozzle in and out of Marcy's butt. It wasn't long after that first moan that Marcy started leaking precum, which was nearly instantly followed by continuous moaning. Just as Marcy started to near the edge of her orgasm Lisa released the valve in the tube just behind the nozzle making a steady stream of lukewarm water flood deep into her butt.

With a mischievous glint in her eyes Lisa kept on fucking Marcy's butt with the nozzle while she was being filled up. The strange not entirely unpleasant sensation of being filled mixed with the continuous rubbing of her prostate eventually sent Marcy over the edge. With a loud moan she erupted on the bathroom floor, cum shooting from the tip of her cage while the nozzle kept on fucking and filling her.

Shame set in very quickly after her orgasm. A shame that was only made worse realising the person who had gotten her into this fucked up position had probably seen it all. A sham accompanied by cramps as the nozzle kept filling her up to a very uncomfortable point. "Miss Lisa, it's starting to hurt, please stop the flow." Marcy grunted out as the cramps only grew more intense.

"Just a little bit more Marcy, we are all most there. A little bit more and I'll remove the nozzle so you can go empty yourself." Lisa said as she kept the valve open for a few more seconds until she could see a tiny hint of swelling in Marcy's stomach. It was a delicious sight almost like Marcy was dealing with an early pregnancy.

"Alright, that should be enough. Now you just have to stay in place for a little bit so the water can soak loose as much as possible." Lisa said while she shut the valve but kept the nozzle inside to prevent Marcy from releasing anything.

After waiting for about a minute Lisa spoke up again. "Okay Marcy, I am going to pull the nozzle out in a few seconds. You are going to squeeze your butt shut as tight as you can when I do that. I know the pressure is big, but trust me you'll want to keep clenching that butt of yours until you can safely evacuate using the toilet bowl."

"Three! Two! One! Clench!" Lisa shouted as she pulled the nozzle from Marcy's butt. The sissy instantly clenched it shut and rushed over to the toilet. Once in place she let go with a deep sigh of release. What followed was a seemingly never-ending foul stream hitting the toilet bowl. It lasted over a minute until all of it was out. Marcy's belly was deflated yet again, but most importantly, the cramps were gone.

"There's a good sissy, now give it a quick wipe, flush and get back in position." Lisa said with a broad smile on her face. Marcy followed the orders, flushing the foul-smelling liquid mess down before moving back to the place where she just came on the floor.

"You can lick your cum up while I deliver your soapy enema. By the time you're done licking your butt will smell like roses. At least as soon as you evacuated your bowls again." Lisa grinned pointing at the by now cold white goo laying on the tile floor.

With a deep sigh Marcy got down on her hands and knees a bit further back this time so her face was where her caged clit had been last time. Moving her butt up she started licking the cold goo. It felt and tasted disgusting. Sure she had tasted cum before. She had been made to taste cum, but never to suck it cold off a bathroom floor.

While Marcy was busy licking Lisa shoved the nozzle back into his butt. She had added the soap of what remained of the water in the enema bag. It was very strong smelling soap, but she guessed it had to be given the place it went.

Opening the valve the rest of the bag emptied into Marcy's bottom. It was enough to cause slight cramps, but not nearly as much as earlier, something Marcy was grateful for. "Okay, now we'll just let that soap work in so your butt has time to adopt the sweet roses smell. This is the only kind of enema you'll need if you keep up the schedule. Since you're not complaining I assume it's not as bad as the last one so I advise that you keep to the schedule." Lisa said sweetly.

Waiting for a few minutes Lisa eventually took out the nozzle again and allowed Marcy to empty herself in the toilet. The smell was no longer foul. In fact it really smelled like roses which made Lisa giggle. Even the water in the bowl looked pretty much clear.

As she watched Marcy dry herself with toilet paper, Lisa walked up to the sissy. She pulled Marcy up, spinned her around and knelt down behind her. Spreading the sissy's butt cheeks Lisa moved in closer and took an audible sniff much to Marcy's embarrassment.

"Chelsea was right, you really do smell like roses back there. I was sceptical at first but here we are. God you're such a sissy. Not only do you look pretty, now you even smell pretty. Squeaky clean inside and outside, ready for use. In the future when I stick a finger up your butt I will only tolerate getting a finger smelling like roses back. So keep up with your enema regime or you'll be sorry." Lisa giggled, getting back up and giving Marcy's butt a playful smack.

Marcy just stood there mortified. The person behind all this blackmail had certainly heard Lisa's demand as well and unlike with her girlfriend she knew that person would give her real trouble not doing her enemas. Like it or not, she would have to preform an enema twice a day until she could find a way to get rid of this god damn blackmailer. At least he would only need a toilet to go pee going forward, not that it was a comfort at all.

"Now let's get you ready for some fun. Why don't you start brushing your hair while I get everything ready? Here, you can keep this one, and remember at least one hundred strokes. It's something else you will do every morning going forth." Lisa said handing Marcy her hairbrush from her purse before leaving the bathroom.

Letting out another sigh Marcy started brushing her hair mourning the end of her quick morning routine. Normally she was up and ready in a few minutes, having a quick piss, shower and throwing on her boxers. Now she needed an enema, to brush her hair one hundred times, which would take a few minutes and putting on lingerie took way longer as well. The tight girdle, clasping her bra and most of all attaching her garter tabs to her stockings were still a pain to deal with. She was slowly getting better and faster at it, not that she was proud of that fact.

Marcy was nearing the end of her hundred strokes when Lisa re-entered the room with one of the big bags they had brought from CC's. Marcy looked a little confused. Lisa had been away for too long to simply grab a bag no?

Lisa went behind Marcy's back and placed her hands on the sissy's hips to guide her forward and in front of the mirror. "Now watch carefully Marcy, I am going to show you everything you need to know to recreate the look from back at CC's but in the future I expect you to be able to do it yourself." Lisa explained taking place behind Marcy and taking the brush.

"First you need to find the split in the middle of your hair. Once you found that, you'll brush all the hair on the left to the left and vice versa. After thoroughly splitting it with the brush you'll gather it up between your thumb and index finger which you'll place in a circle. The next step is to replace your thumb and index finger with the ribbon Linda was so kind to give along as well. You loop it around with one hand then release with your hand and tie the ribbon off in a bow like this." Lisa explained carrying out all her steps as she was explaining them.

Mortified Marcy looked on. She knew exactly what Look Lisa was going for now. It was a look she had hoped to keep secret from her blackmailer, knowing she would spend a lot more time in it if the person behind the camera's found out. It was not something she wanted to do, but neither was arguing with Lisa especially now that Linda had convinced her spankings were good for sissies.

Left with no other choice Marcy carried out the same process with the other side of her hair completing the two darkbrown pigtails look with the floppy pink tartan bows like she had worn up on stage at CC's. It instantly made her look a lot more girly. Even naked she really looked more like a flat chested girl than a guy lately. At least as long as one disregarded the cage between her legs.

Lisa then went to the big pink paper bag and fished out the backpack belonging to the outfit. Opening it up she fished out the tube of bubble gum pink frosted lipstick. Pressing her front into Marcy's back Lisa opened up the tube and started to apply a thick coat to the sissy's lips.

"Here we go, a nice thick luscious coat of lipstick. Now smack your lips together a few times to spread it nice and equally. If you want to add an even thicker coat you just have to dab your lips with a tissue lightly then reapply the lipstick." Lisa informed looking over Marcy's shoulder with a smile.

Marcy just nodded her head nervously, and the lipstick and pigtails weren't the only reasons for her nervousness. When Lisa had pressed into her back, she could have sworn that she had felt a big hard bulge at her leg.

"Alright, now put on your full outfit, then join me in your bedroom so we can start having our fun." Lisa said leaving a now distraught and made up Marcy behind. Well not really made up, just a coat of lipstick and the hair. It did change a lot of her appearance though.

Dressing up in the complete sissy schoolgirl outfit took Marcy over 10 minutes, 10 minutes in which she was sure she was being watched. 10 minutes in which she was nearly certain that her blackmailer was making plans to put her in this outfit more often.

She wasn't wrong either. Next door John had been very pleasantly surprised when he saw Marcy and Lisa move back in the sissy's room. Especially when Lisa helped Marcy with an even girlier hairstyle and lipstick, or with the enema for that matter. To John it was like a hot private peepshow. Both participants knew he was watching which made it even better. Especially knowing how embarrassed Marcy was being over this.

Ever since the two of them had entered Marcy's room John had been stroking his cock. He was rock hard and now seeing Marcy in her new outfit he was looking forward a lot to using the sissy in person. Everything in due time though. He would certainly make sure that Marcy got a lot practice strutting around in those tall heels. Of course all under his masturbatory supervision.

For now, he was curious as to what Lisa had planned exactly. The girl might be a bitch for coming between him and his prize, but the girl sure seemed to know how to put on a show. No matter how much John hoped he was yet to see her naked. The girl was smart enough not to show skin. Instead she made Marcy put on the show under her guidance.

Strutting into her bedroom Marcy was very nervous. Walking in heels, especially ones this tall was an awfully hard chore for her. It was only made possible using Linda's tips as to how she should walk. Sticking out her under arms, wrists limp and walking heel to toe which brought a sway in her step.

She had tried walking like she did in sneakers, but she instantly felt like it wouldn't end well. For starters she was way less balanced than when she was walking like Linda instructed. Secondly, she knew it would serve as an excuse for Lisa to give her another spanking.

Lisa was sitting on the bed with a big smile on her face. Marcy looked marvellous in her outfit and she was all hers to play with now. Even the flat chest wasn't really a distraction. Marcy did by all means look like a hot sexy girl. A girl who would soon discover a nice big surprise.

"Now Marcy, why don't you get that cute butt of yours over here and get on your knees in front of me?" Lisa asked. Seeing the awkward unsteady yet overtly sissy way in which Marcy walked to her was a joy to watch. As was the way she slowly sunk down to her knees at Lisa's feet.

"There's a good sissy, now rest your hands on my knees and slowly slide them up my thighs. Take my skirt along when you reach the edge of it." Lisa said giving Marcy a pat on the head between her pigtails. It gave her such an enormously powerful feeling.

Marcy was worried about what was going to happen, but she decided to just go along with Lisa's instructions. She felt so very embarrassed sitting here in front of her girlfriend like this, but she had to carry through. Lisa would probably just want to be eaten out, which was as close to real sex as Marcy was going to get with her girlfriend. At least she hoped it would be. Technically getting fucked by that dildo would be closer, but she certainly didn't want to go through that.

Sliding her hands over Lisa's nylon covered thighs, Marcy suddenly ran into a big bump. Dragging the skirt further up revealed that the bump, which was probably the bulge she had felt earlier. Was caused by the big dildo, held to Lisa's leg only by the sheer black nylon of her pantyhose. Unable to help herself Marcy looked up at her girlfriend with a shocked expression.

"What's the matter sissy? Isn't this a nice surprise? I thought you would have loved seeing your favourite toy. Now just continue sliding your hands up until you have my skirt lifted above my hips, then fish that big dildo of yours out of my pantyhose." Lisa smiled continuing to stroke Marcy's head.

Nervously Marcy reached insider her girlfriend's pantyhose and grabbed a hold of the thick dildo. Slowly but surely she moved it up the leg, until it got up high enough to fish out of the waistband of the pantyhose. The dildo looked huge on Lisa it was a big dildo for sure, but on her 5'6" tall girlfriend it simply looked disproportionate.

"Mmm what's the matter Marcy, don't you just love my big juicy cock? Now don't lie, I know you do. Why don't you give it a kiss, just like I showed you this morning?" Lisa moaned, she might not be able to feel the sensations of the dildo being handle like she would if it were a penis, but seeing the way Marcy was handling was hot enough to make her plenty wet.