Sissy Caught: First Time Feminization, Crossdressing (A New Woman (Transgender Women and Feminized Men Romance Stories))

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Sissy Caught: First Time Feminization, Crossdressing (A New Woman (Transgender Women and Feminized Men Romance Stories))

Sissy Caught: First Time Feminization, Crossdressing (A New Woman (Transgender Women and Feminized Men Romance Stories))

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That’s my cousin; she’s staying with us for two weeks while her family move to Bessemer, Nic has gone there to help them .” Hold on dear; I’ll be upstairs in a minute, let me put the groceries away. Oh and Nicolas, I want to see you the way you are right now, so DON’T change!” My parents were quite strict so I was extra careful every time I got dressed in my sister’s clothes. Usually all her dresses fit me well and soon I also started to try out some of her bra. It was usually for a very short amount of time. I just put them on wanting to know how they felt and then take it off immediately because I was really scared someone would catch me like that. But this really made me feel so excited. I got everything together, making sure I had what I needed, including a spare pair of hose (always have a spare, I hate runs), my makeup, lube, and the rest of the outfit that I couldn’t easily wear under my man clothes. With that all done, all I had to do was wait…for two more days! That’s like two MONTHS for my level of excitement and anticipation. I wasn’t simply planning on dressing up and prancing around an empty house at night…I wasn’t planning on being the only one to enjoy what I would be wearing! As time passed, I got into a relationship with this lovely girl I met at a friend’s party. We got really close and started to hang out together all the time. Then I asked her to move in with me and she did. I decided to stop crossdressing for good and after that I didn’t dress up at all.

After that incident, we had a long conversation and I had to convince her that I wasn’t interested in men but I did like to dress feminine once in a while. She was very understanding. I was sure she would leave me but she didn’t and now she is okay with me dressing up sometimes but only inside the house. Now, when I think of it, it was better that I was caught because after that I felt really relieved and accept myself for who I am. Well my mom and Dawn grab a hand each and walk me over steadily to the mirror. I am having a hard time, as I have never worn heels before just the clothes. Well they both manage to get me in front of the mirror and it is my turn at the goldfish impression. It all started when my friend found out I was secretly crossdressing. They said they would tell everyone unless I did what they wanted, They literally forced me to crossdress. So, every day after school, I would have to put on their clothes and do as they said. I felt so humiliated and trapped. Every day I tried to get out of it, but they would always find me. After about a month and a half, I was tired of it, so I did something that got me in more trouble than ever.

Blog Archive

The Sweet Stench Of Revenge. A young boy is bullied in high school, yet revenge comes as surely as the passage of time. Enjoy this ten part adventure. As I grew a little older, I couldn’t really sneak into my sister’s room and from the internet discovered that I was actually a crossdresser who liked dressing up as a girl every now and then. I felt a little relived knowing that there were many people like me who loved to dress up. My phone was almost dead, so I hoped it lasts long enough to continue communicating with him, that is if he’s really coming. About 20 minutes later he texts me again…he’s pulling in the long driveway. He finally arrived at the doorstep, I went to greet him, a bit nervous but excited at the same time. He seemed to be excited and a bit nervous to see me as well. He was looking hot in a beautiful red flouncing dress with nice heels. He was slim and looked quite feminine indeed. I was happy with what I was seeing.

I was spending too much money doing this so I decided to hide some of the feminine wardrobe in our store room. My wife was great at her job and she got promoted. She started to have more responsibility at work and would have to fly out without much notice sometimes. He swam a few laps before hearing the garage door open around the side of the house. He thought this was weird as Megan usually just parked in the driveway but thought it must be easier to get the groceries in through there.

After A Long Time, We Talked About My Crossdressing

First, let me explain, my name is Nicolas and I have been dressing in my moms and sisters clothes for the last seven years. I do not know why I do it I just do, I cannot seem to stop myself and the way I feel when I put the silky garments on. I’m only a smallish kid, being only 5’5 and weigh slightly over 100 lbs. Fine you might say but when you consider I was fifteen last month, believe me it is a problem. The amount of ribbing and name-calling I get at school is a nightmare. Later I was watching tv, my dad came and sat beside me said “I don’t understand this, will you tell me about it?”

It looked like her parents had been gone for a few days because Tiffany's blankets and pillow were on the living room couch and her clothes were scattered all over the room. Then, I get a text from him. He asked if I was there. I told him I was, I was ready too. He said he was leaving his house now, which would put him about a half hour later than what we had set up, already being ten minutes late. I have hours, so it’s not a huge deal, but I hate waiting around for someone. Then of course I start to think he’s just playing games, it’s happened before…I’d be all ready, fully done up, guy said he was on his way, never hear from him again. Some people just like playing games. Once puberty hit, crossdressing took on a whole new aspect. I started to realize that I wished I could dress in girl's clothes all the time and that I preferred the way girl's dresses fit my body and how they looked at me. I also began to feel trapped in the wrong body and that I should have been born a girl. These realizations were confusing and scary for me, and I wasn't sure what to do with them. In fact, almost every day I would wear Jody’s under garments. I even wore the panties to bed one night. But they were starting to smell from having been worn too many times. So I reluctantly put them in the wash. I waited a few days, and then dug through Jody’s drawers when I had a chance to find them, or a similar pair.I decided to make her some food as she said she was a bit hungry. She went into the bathroom. I was just going to the kitchen when she called my name really loud. That really frighten me and I thought if I had forgot to hide everything of my feminine stuffs. Then to my horror, my aunt’s voice at the door, saying, ” if you like it so much, why not put it on.” Aunt Marilyn, showed me around and where everything was. Then we left, to go for fish and chips, to eat at Tally’s. On return, aunt took a shower, and offered me to take one after her, which I did, to freshen up. The Dating Game. Mollie Blake’s ongoing serial about David (Diana) and Lucy. From the ski slope to the lecture hall, this is a great look at the unusual world of academia and crossdressing.

I crouched down in my seat at that comment, sure I didn’t have any friends, I was a loner at school but why did mom have to rub it in. We got it for you the other week with the rest of the items you’re wearing. Come on take a look in the mirror.” I espeically care for my kids. I do not know whether it is a joke or not, but my two sons sometimes say they feel shame while going with me, especially when I coax them to go out instead of staying home to play computer games. For this reason, I wear long pants when visiting their school. Tiffany kept at him, "Well, my parents are out of town and Jess and Michelle are coming over to hang out. Michelle thought it'd be fun to invite you over too."As always the dressed up episode had to end and after an hour or so I was putting Tina’s items away where I’d found them and headed down to water the garden. I was stunned to see that they had just been watered. Tina’s brother was also charged with watering the plants while Tina was away, and had stopped by on his way home from work to undertake the task. It still gives me jitters to think of how close I came to getting caught. I even had the radio on up in the loft room whilst I was dressed which is maybe why I didn’t hear him come in but it amazes me that he didn’t hear music coming from the upper floors and go to investigate. I knew him and we always got on well. I had been in the pub with all of them in the past and Tina’s brother was always very friendly towards me so it might have finished well had he caught me. It might be that he sneaked up and saw me otherwise engaged and oblivious and decided to let me get on with it. Maybe that’s why he was always very friendly to me. It if is I wish he’d say something or make a pass at me. Then Bob comes really close to me and holds my hand. I look at him, I was nearly about to cry with guilt. Then with a smile on his face, he says “Well, actually.. I did fantasize about making out with a crossdresser someday. Are you up for it?”



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