The Neighbours Situation Ch. 03

I tugged at the bow and it fell lightly to either side of the large box. I slowly removed the lid, terrified of the contents, which felt ridiculous but based on previous events I knew I wouldn't be keen on whatever was inside.

There were multiple bags with pink numbers written on them. I opened number one and found a note which I grabbed and began to read.

"Hello Sissy!

Today's a busy day for you. We know what failure to comply will mean so let's crack on.

1. You will open bag number one and go have a nice bath. Use everything in the bag, I want you smelling nice and feeling absolutely smooth. Do not open the next bag until your task is completed."

I couldn't believe what she wanted me to do, shaving myself smooth isn't something I can just reverse the next day! Given that I didn't have a lot of body hair naturally so it wasn't going to be a drastic change, but what if somebody said something? How do I explain shaving my legs?

None of this mattered as it would be an easier task to explain the lack of body hair than why there are photos of me in a bra and panties... And now a nightdress too, adding to the ammo at Olivia's disposal.

I looked through the contents of bag one. There was a three pack of women's razors, shaving cream, hair removal cream and feminine soaps and shampoos. There was also a moisturizer and deodorant for afterwards. I decided there was no point delaying what I had to do, so I made my way to the bathroom with all of the items and started to run myself a bath.

Whilst idly watching the bath fill I found myself running my hands over my body, feeling the silk and delicate lace against my skin. Again I felt my cock betraying me as it was beginning to stiffen in my panties. I stopped myself and stripped naked, ashamed of the feelings the beautiful lingerie was causing me.

I turned off the taps and stepped into the bath. It took me a long time to shave the little body hair I had. I opened the pack of razors and applied the shaving cream to my leg, then slowly shaved a section being extra careful not to cut myself. As I washed off I felt how smooth my leg felt and was instantly turned on.

I kept at it and almost two hours later I was hairless from the eyebrows down. It had taken a lot of effort and the bath was full of stray hairs. I washed off with a shower making sure to use the soap provided.

I grabbed a towel and instantly felt the difference on my skin. The sensation of being smooth and hairless was extremely sexy and it was becoming increasingly harder to ignore my horniness. I didn't want to enjoy this, but part of me loved it.

I made my way to the bedroom and began to use the moisturizer provided, it had a sweet floral smell to it. I applied it everywhere and sprayed the deodorant which again had a very sweet feminine smell to it. With each task I was feeling less masculine. The humiliation was almost too much but at the same time, so was the aching in my balls.

I knew there was still plenty to do so I went back downstairs to the box and opened the second bag and read the note.

"Now that you are all smooth and smell pretty it's time to paint your toes. A good sissy always has pretty feet! You will make sure they are neat, and if not you will use the polish remover provided and try again until you get the hang of it. I will punish you for any toes I decide are not up to scratch."

I looked inside the bag and found a toe separator, clippers, nail polish remover, a small file and a little pot of baby pink nail polish. This was again something I couldn't explain if others saw it, but at least my hands were safe I told myself. I trimmed my nails and filed them so the edges were smooth, grabbed the spacer and sat on the end of the bed ready to attempt painting my toes.

The first attempt was awful by any standards and I had to remove it, the second a little bit of improvement showed, and in the end it took four attempts until I felt every toe was acceptable. I just hoped Olivia felt the same. Looking down at my smooth legs and painted feet there was no sign of masculinity left.

I went straight back to the box, beginning to feel shamefully eager to read the next task. I opened the bag and again a note was waiting for me.

"I bet you're feeling like a sexy little sissy by now aren't you? We can't have you wearing your bra and panties from yesterday, can we? In this bag you will find some pretty lingerie for you! I know you will love it. And don't worry about the cost, you will pay me back.

P.S.

The panties go over the garter straps, never under!"

Pay her back? I didn't want this stuff, and it didn't even say HOW I was to pay her back! Although part of me was dying to try on whatever she had bought me at this point. I opened the bag and started to remove the contents.

The bra was the same baby pink as the nail polish with lace sides and a slightly lighter floral lace pattern over the cups, with a small white bow in the middle. It was beautifully feminine as was the matching lace thong that laid in the bag beside it.

I clasped the bra on carefully and spun it around. Sliding the delicate straps over my shoulders caused my penis to twitch a little. What was happening to me? I slipped the thong over my ankles and slowly pulled it up. The lace tickled my smooth legs all the way up until it rested between my cheeks snugly. My penis was packed underneath the floral lace and topped by the cute white bow. No wonder women loved these items, they felt incredible.

I reached back into the bag and pulled out a white pair of lace top stockings and a garter belt that matched the bra and panty set. I had seen my ex girlfriend put these items on before, so I felt I had a good idea of how to do it. I clasped the garter belt and spun it the right way. I remembered from the note to put the straps under my panties. I realised at this point I was thinking of them as "my" panties which made me feel like I had been tricked.

I rolled the stockings up my legs carefully as I didn't want to damage them, as I knew Olivia would punish me. I found the clasps very tricky and it turned out my earlier confidence was misplaced. After some time I managed to fasten them and straighten them up.

I ran my hands up my legs and the feeling was so erotic. My touch sent shockwaves of pleasure through my smooth nylon clad legs. This sensation was too much and I started to rub myself through my panties. I could see the image of a sexy woman's body in the wardrobe mirror which only made me rub myself more. I laid back and closed my eyes, taking one hand and placing it under the cup of my bra and pinching a nipple. I began to rub myself through the lace more frantically and brushing my feet together.

All of these sensations were too much and before I could stop myself I was arching my back on my bed as I felt the strongest orgasm I've ever had pulse through my entire body. I could feel the warmth of my semen spraying down my cock and balls inside the panties and leaking over my ass. I laid there stunned for what felt like forever.

I sat up and looked down at the mess that I had made, my panties now soaked in semen and leaking out onto the bed. I felt utterly stupid and humiliated at the fact I was shaved and wearing these things.

But what made me even more ashamed was that I had began to enjoy it and just experienced the most intense orgasm of my life by rubbing myself like a woman would. I wanted to take all of this stuff off and just forget everything. I sighed as I knew that wasn't an option, I would only have to dress up again later if I did.

I grabbed the bag the lingerie came in and placed it under me, made my way to the bathroom and began to clean myself up.

I removed the panties and realised I needed to get them cleaned ready to wear again to Olivia's house tonight. I went downstairs and washed them by hand and left them on a radiator.

I wasn't quite ready to get back to the box yet, I felt ridiculous dressed like this and I didn't want it getting worse right now. I knew I was against the clock so I would have to get back to it soon. I made myself a bit of food and tried to relax for a little while.

I sat and thought of ways out of my current situation but they all ended with the same result. I realised the more I went along with her games the more blackmail material Olivia had against me. Why had I been so stupid? I should have just respected her privacy and left things alone. I felt utterly powerless to what she wanted.

Time was passing and I knew I only had a few hours until seven. There were two bags left in the box and I knew I needed to deal with them. I made my way over to them and grabbed bag number four. The note was short.

"Some jewellery for sissy. Make sure you're wearing it for me."

I looked at the two small boxes in the bag. The first contained a small silver necklace which read "SISSY" with a little pink jewel in the dot of the i. The second had a smaller matching item which I realised was an anklet. I put both on and moved onto the next bag, just wanting to get these stupid tasks out of the way.

The note read:

"There's one item of jewellery left..."

I reached in and found a little satin bag which had a bit of weight to it. To my horror, I pulled out a silver plug with a pink jewelled base. There was also a bottle of lube.

This was too far, I couldn't insert this into me. I had never had any interest in that kind of thing nor did I want to. I sat staring at it for a while. I picked up my phone and texted Olivia.

"Olivia I'm sorry but this plug is a bit much, you can't honestly expect me to put this in!"

She replied within minutes.

"Well sissy girl, that means you are on bag number 5. So you're all smooth and in your pretty new lingerie. And you can't forget what you are as you have it hanging around your ankle and neck! In answer to your text... Yes I expect you do insert that plug, and if it isn't done within the next 15 minutes, expect an email."

As always, I knew what this meant. I had come this far and the choice hadn't really been mine from the second Olivia walked into her bathroom and caught me with her panties in my face. I needed to do this and it needed to be quick. My phone buzzed again.

"Also it's MISTRESS, you disobedient little slut! You have five minutes to send me a picture of that plug in that sissy hole of yours. You don't deserve fifteen."

I panicked and grabbed the lube. I applied plenty and probed at my hole with a finger. I had never done this before and was very uncomfortable. I slowly worked my finger inside and started to massage inside with lube to make it ready for the plug. I grabbed it and covered it with lube and positioned the head at my opening.

It was a little painful but I started to accommodate it fast. I realised I had two minutes left and began to work harder. Just as I was starting to really panic I felt the largest part slip and the base of the plug was firmly against my opening.

I stood up and felt very full. Every move that I made, the plug reminded me it was there. It was very foreign to me, yet not unpleasant. I bent over and snapped a picture. I had sent it to her in just under five minutes to my relief.

"Good girl, don't you look all pretty! You weren't designed to be a man, it's blatantly obvious, Now get your panties on and come round here. I don't feel like waiting until seven."

I breathed a sigh of relief and then the nerves gripped me that I would be facing her like this. I put the now dry panties back on and instantly felt the back section pushing the plug firmly into my ass. I covered up with a t-shirt and sweatpants and made my way to the door, the plug pushing into me as I moved, and I was embarrassingly getting turned on by it.