Sissy and Neighbours

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I had finished work late. I decided to take the shortcut through the woods. As it was a hot day I was wearing a short skirt and a white blouse. I am a 20-year-old male transiting into a woman. I have been on hormones for the past two years. As it was later in the evening and there was no one around, I decided to remove my short skirt. My back gate was right next to the park. If I had taken the safe route, I would have had to walk around the park, and that would have taken about 20 minutes.

The time was 9 pm, and the wood was empty. I was nearly halfway home when I heard dogs barking in the distance. I knew a few people who took the dogs out for a walk. There was one couple that lived next to me. They had two golden labradors. They were an older couple about 10 years older than me. I decided to put on my skirt to finish off the walk. As I put my skirt back on, both dogs were pounding in and barking madly. I would normally dog-sit and take them out for walks.

"Hey boys, I will be over tomorrow to take the two of you for a daily walk."

I got down on my knees and started to pat their heads. As I got down, Hannah and Sarah appeared.

"Hi Lauren, how is work going?"

"Work is going great, Sarah. It is finally the weekend. Are you ready for your time way?"

"Yes, we are looking forward to it. Thanks again for babysitting while we were away. We need to get home to pick up the bags. I'm so sorry to ask but could you drive us to the airport tomorrow morning. You can stay over at our place tonight if it makes it easier as we need to be at the airport at 9 am for a noon flight. Only if you can?"

"Yes, I can. I just need to see if there is enough petrol in the car. But there should be enough."

"OK, cool. Come over when we can."

"Ok, cool, just give me about five minutes to grab some clothes for tomorrow, and then I be over."

"Ok, just come over. We have clothes for you to wear for tomorrow. There are clothes that we would like to show you to see if you want them before we throw them away. They used to belong to our lodger before she left last month. She said to give them out as her new place doesn't have enough space to store them."

"Ok, cool, I will take a look, Hannah. I just need to grab the car keys for tomorrow. After I drop you at the airport, I take the dogs to the woods near the airport for their morning walk before we head back."

"Ok. Also, remember, on Wednesday, they have their six-month checkup. There is nothing to pay as it is included in their pet plan. Thanks again for taking them. we appreciate it, and so do the dogs."

"That is ok. When I learned about it, I booked a meeting with them to sort out their billing software with the newly installed print. I could have done it remotely, but as I was there already, I decided to do it face-to-face. As well as trying to get them to upgrade the network and desktops to bring them into this decade."

"I see the owner can be hard to spend out money but he does have a thing for trans and shemales."

"How do you know?"

"I spot him out on a date with Harry dressed in a beautiful blue summer dress. He spotted me and smiled. The following week he sold his rundown car to Mr Thomas the owner of the veterinary. You are much more attractive and feminine than Harry. I must say the first time we met you we didn't know that you were trans until a year later. Both of us had crushes on you and still do. You hot. The clothes we have might be able to help you on Wednesday."

"True be told I fancy Thomas either though he 50. He looked fit and I saw him running in the woods and he was dead handsome. He has a built body. I dream about him taking me every night."

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