Aunt Betty's Visit Ch. 01

Every once in a while something happens in life that really seems quite strange. That was the case with my cousin Brad when we were both about 20. I never thought I'd be sharing this story with anyone. Since he and I were pretty close at the time and to some degree still are, I don't want to do anything to hurt or embarrass him. And the chance of him reading this exact posting on Literotica is so slim that I don't think I will. Just in case, I'm not going to give out cities and I've changed a name or two. If you do happen to read this, Brad, please forgive me for revealing secrets even though it was over 20 years ago.

The year was 1982. I was 19. It was just Mom and I and we lived in a rather comfortable, though somewhat small two bedroom apartment. When we walked in the front door our bedrooms were to the right and the living room, kitchen and a sliding door to a small deck to the left. We had our couch facing the sliding glass door with a chair on each side of it. You couldn't see the front of the couch from the kitchen. (I had taken advantage of this from time to time, too.) The TV was in a corner by the glass door. The bathroom was right in between the two bedrooms. Both bedrooms were the same size and each had a window, so Mom just took the first one when we moved in and I took the second. We rarely had overnight guests. On rare occasions when we did, it was usually family. Sometimes Mom and I would share a bed. Other times one of us would take the couch. It just depended on who was visiting and what accommodations they needed.

Towards the end of summer Aunt Betty called and asked if we'd be interested in having company for about ten days. She and her son Brad, who was 22 at the time, had some time before he went back to college and were hoping to visit Mom and me. Mom and Aunt Betty hadn't had more than three hours at a time together in the last five years. And they were so close growing up that Mom agreed in a heartbeat. So the plans were made - Aunt Betty and Brad would drive up on Friday night and stay until a week from Sunday. Mom had some vacation time coming and arranged to take that time off work. The local community college I was attending was out for a while, too. So it would be the four of us all week.

Brad and I had always gotten along well growing up. In our early years we lived very close to each other. We had played house as kids. We rode bikes together, played baseball sometimes. We played cards, shared ideas and dreams. We liked the same kinds of movies and TV shows. He was a lot like a brother to me. There were lots of times that one of us knew what the other was thinking before it was spoken. But that was to end. I was twelve when Mom and I had to move. Since then Brad and I had kept in touch, but had grown apart. We just weren't near as close as before. And of course there's the puberty thing - he became interested in girls for more than an outfielder and I had become interested in boys for more than a pretend husband playing house. With them coming to visit, I had hopes of rekindling the friendship from our childhood, of once again being very close to my cousin.

Mom and I cleaned all week. We wanted to be rested so we could sit up and visit if everyone wanted when the time came. And though it seemed so long, Friday was finally here. We really didn't expect Aunt Betty and Brad before 8 or 9 that night, thinking that Aunt Betty had to work all day. Aunt Betty had managed to get off work three hours early, though. It was right at 5 p.m. when they knocked on our door. Everyone was so excited, so happy. There were lots of hugs. I didn't think Aunt Betty was going to let go of me. Brad seemed to hold me long and snug for quite some time too. At one point Mom and Aunt Betty were both teary-eyed. Reality was here - Aunt Betty and Brad were going to be with us nearly ten days and nine nights! Aunt Betty told Brad to go get their luggage and I volunteered to walk out with him in case I could help. Brad was accepting. I probably talked his ear off the entire walk, so anxious to 'catch up' on things. How was the trip? How's everyone back home? How was school? Did he have a girl friend? And dozens of other questions. Brad answered the questions but seemed quieter than I remembered.

We had a simple dinner that evening. I don't remember what it was, but I do remember that we visited the whole time we prepared and ate dinner. And as Mom and I anticipated, we all sat up visiting well into the evening. It was just about midnight when Brad asked about sleeping arrangements. Mom spoke up right away. "Your mom and I will sleep in my room. Sheila has her own room. Brad, I hope you don't mind the couch too terribly. If so, maybe you can arm-wrestle Sheila for her bed."

Brad smiled while the rest of us laughed at the comment. We all took Brad's question as a signal to wind it down for the evening. Aunt Betty and Mom went into her room and closed the door. I told Brad good night and told him again how glad I was that they were visiting, then went to my room. As I was drifting off to sleep I could hear the TV on. But I was wondering what all we might do in the coming week.

Being an early riser, I was up around 7 even after being up well past 1 a.m. Mom came out of her room just about the same time. She was never very shy, so it didn't surprise me when Mom went to the kitchen to make coffee in just a very thin, short nightie. I walked to the front of the couch in my baby-doll and matching robe to wake Brad up and that woke me up a bit. He was lying on his back with only a sheet covering him. And the tent in the sheet told me he didn't have anything else on either. I decided to have a bit of fun. I leaned down and whispered in his ear: "Hey, sexy. Are you dreaming about me?"

He stirred a bit. Until now I'd never had erotic feelings towards Brad. But that seemed to change almost suddenly. I kissed him on the cheek to try to wake him up a bit more. Just as I stood up from that Aunt Betty came out of Mom's room in a somewhat heavy robe. I decided to cool it and shook his shoulder gently. "Come on sleepy head."

Brad suddenly woke up some and realized where he was. When he saw me standing there he thrust his hands over his groin hiding what I'd already seen. His face turned deep red. I mouthed the words "I'm sorry" and turned and went to the kitchen. Brad wrapped the sheet around him and practically ran to the bathroom to get dressed. There was enough commotion that Mom asked what was going on. Aunt Betty commented that Brad sometimes slept real hard and wouldn't remember where he was when he woke up; that I'd probably startled him. I thought to myself "Yes, I startled him, but not like that!"

None of us women bothered to get dressed before breakfast. Over breakfast we talked about the news and lots of trivial things. We discussed possibilities for the day. Finally Aunt Betty and Mom decided they wanted to check out a newer mall in the next town. I was game for that. When we asked Brad, though, he said he wanted to just stay put that day. He said he wasn't feeling on top of the world and that if he got to feeling better, he might go for a swim. I was afraid I had embarrassed him so bad he didn't want to be around me. Though Aunt Betty and Mom tried to change his mind, I just stayed out of it. The three of us got dressed and told Brad we'd see him that evening, that it was an hour and a half drive to the mall and not to worry about us. Mom told him where to find everything he needed to fix himself lunch. Then we were off.

On the way out of the neighborhood Aunt Betty spotted a garage sale. We ended up not going to the mall, but rather to garage sale after garage sale for the next couple of hours. We found a few bargains and had a lot of fun. I hadn't seen Mom that relaxed and happy in years. As the morning neared an end we decided to go back to the apartment for lunch instead of eating out. Well, that was the event that changed everything - for the day and for the week, and in some ways the rest of our lives. As polite as Mom is, she unlocked the door and pushed it open, then let Aunt Betty go in first with me following. We stopped in our tracks facing the sliding glass door. I think all three of us let our jaws hit the ground for a second or two. Brad was just coming in the sliding door - wearing one of my dresses with obvious signs of a bra and hose under it as well as a pair of my heels. His face turned the darkest shade of red I think I've ever seen. Aunt Betty started to yell, but Mom managed to stop her.

Mom always has been pretty level headed, and I have to say I thought she handled the situation magnificently. "Betty, please take your things to my room, then come back in and sit down. Sheila, please fix us all an ice tea, then sit on the couch. Brad, please sit down on in the chair so we can all four talk."

Brad hung his head and asked to go change first, but Mom would hear nothing of it. She told him that we could all talk while he was dressed as he was, that there were several things bothering her. She went on to say that she suspected there were things bothering him and Aunt Betty, too. Brad started to argue, but Mom just pointed to the chair. I knew better than to say anything then - when Mom pointed, she had taken all she was going to take. Brad must have sensed that, too, because he went and sat down. Aunt Betty came out of the bedroom just as he sat down. She went over and sat on the couch. I took the ice tea over and set it on the coffee table, then took my seat on the couch about the same time Mom sat down in the other chair.

I studied Brad while I put some sweetener in my tea. Brad was a pretty fair size man. But then he came from a "healthy" family. Mom and Aunt Betty are both rather large ladies. And even at 19, it looked like I'd be at least as big as they were if I didn't eat another bite. Now it seemed that Brad took advantage of at least one of our sizes. He had on an older pair of my dress heels and a pair of panty-hose, though I had no idea if they were mine, Mom's or Aunt Betty's. It was very obvious he had a bra on, all stuffed up. And he had chosen to try one of my favorite dresses - a rather thin but not quite transparent one that buttoned in the back from the waist up. There was a hint of my perfume in the air, too. Maybe I stared at him some, but he avoided all eye contact with all three of us.

"Brad, I'm very disappointed in you. But I want to see if you can tell me why."

There was a long, awkward silence. You could have heard a pin drop. The Brad, in a bit more than a whisper and still facing the floor said "Because I'm a pervert."

There was another pause before Mom spoke. "No Brad. And unfortunately you just gave me another reason to be disappointed. Sheila, what's my number requirement in this house?"

Hearing my name snapped me out of my watching (staring at?) Brad. But I didn't have to hesitate "It's trust and respect, Mom."

"That's right. Brad, you broke our trust. Sheila and I live by a couple of rules, a couple that we thought you and your mother lived by, too. One of them is that you always ask permission before using something of someone else. When you don't, that breaks the trust, the trust that even your own things will be save. I know your mother was raised that way and I'm sure she at least tried to raise you that way. I know this is going to sound crazy to you right now, but I'll bet if you would have asked that Sheila would have let you borrow almost anything in her room you wanted. But now I know I'm going to have a hard time trusting you and I imagine that Sheila is too. And your mother may have the hardest time of all.

"The second rule I've always had is that whenever Sheila or any of her friends want to try something out of the ordinary in my home they have to ask permission. I won't go into details, but suffice it to say that it has been rare that I've said no. My goal is her and her friends' safety. And I feel the same way about you. You called yourself a 'pervert'. That's the violation of the respect issue. You don't respect yourself or your own desires when you talk like that. Just because you want to try something different doesn't make you a pervert.

"Well, enough of a lecture. Now I want some answers. First, what made you want to dress in Sheila's clothes or whoever else's' you might have on?"

No one spoke for nearly two minutes.

"Brad, none of us are doing anything else until you answer all of my questions. Now, what made you want to dress as a lady?"

Brad spoke very softly "I like the feel of the clothes."

Silence

"And it makes me feel more care free."

"So this isn't the first time you've 'borrowed' someone else's clothes without asking?"

"No Ma'am."

"Brad, I know this is hard to talk about in front of your mother, but when did you start trying on women's clothes?"

"When I was 14."

"Whose clothes?"

"Mom's."

"Go on, tell me more."

Brad looked up with tears in his eyes, the expression on his face saying "Do I have too?" But he continued when my Mom nodded. "On the days when Mom went to work and left the laundry for me to do, I'd wear her things around the house all day. Sometimes I'd even get a dress out of her closet or a nightie out of her drawer." Suddenly he looked directly into Aunt Betty's face and burst into tears. "I'm sorry Momma."

With that, my Mom walked over to him and put her arms around him, giving him one of those hugs that had comforted me so many times. It was as if she was saying to him "It's OK, Brad. You have nothing to be sorry for now. You're forgiven. And we all love you." Mom held him like that for several minutes. When he had calmed down Mom sat back down and the conversation continued.

"So, Brad, do you like wearing women's clothes?"

In a calmer, more normal voice Brad answered "Yes."

"Do you do it for sexual excitement?"

Brad started blushing again. "What?"

"Do you jerk off when you're dressed up?"

Brad looked at my mom, then his, then at me and then back at my mom. In a very quiet voice he answered "sometimes."

"Have you today?"

"No."

"What do you dream of when you do?

Brad hung his head a little and kind of mumbled. "I wonder what it would be like to be able to wear panties and bras and hose every day. Maybe even ladies blouses and skirts or slacks. And heels."

"Is that all, Brad? And please speak so we don't have to strain our ears to hear you."

Brad hesitated. "No Aunt Jenny."

"Well, go on then."

"I fantasize about having breasts."

"So that's what you're thinking about when you get off. Hmmmm." There was a silence, though not as awkward as a while earlier when Mom was waiting on Brad's answer. Then she seemed to change the subject. "Brad, I'm still really troubled with the fact that you took something of someone else's for your own use with out asking. But I admire your honesty. It takes a special male to sit in front of his mother, aunt and cousin and admit the things you just have. What would you do if you had a chance to wear only women's clothes for a week? What would you be willing to give up?"

Brad looked up in disbelief, probably at being asked this question. His tone perked a bit as he answered "Anything I have to - I'd give anything to try it!"

Mom looked directly at Aunt Betty. "Betty, would you be OK if we allow Brad to dress your entire stay here?"

Aunt Betty looked a bit shell shocked. I wasn't sure I'd heard right-Mom asked about Brad wearing women's clothes for over a week? It surprised me that it didn't take Aunt Betty long to agree.

Mom looked back at Brad and began laying out the rules. "Brad, I'm sure your mother, my sister will agree with me on everything I have to say. We're going to treat you like 'one of the girls' the rest of your stay. We're not going to try to make you look 'passable', though we'll play with some make up. You'll just have to be content to have a boyish face. We will allow you to dress like a woman all week. But there are going to be just a very few rules for you to follow. You may write down them down if you like, but they are going to be rather simple. First, you must ask permission before borrowing each piece of clothing. The only exception is if something is offered to you. Otherwise we'll expect to hear your request to borrow very specific items. 'Sheila, may I wear your tan sweater today?' Or 'Aunt Jenny, may I wear your purple panties with the lace trim?' "Second, you are not allowed to be alone anywhere the rest of your stay here. You've proved to us that we cannot trust you. So one of us will always be with you...."

Brad basically interrupted Mom right there. "But what about when I need to use the bathroom or shower? Or changing clothes?"

Mom continued: "You should have thought of that this morning. And if you're thinking 'how will I be able to jack off', you may ask permission if you really, really believe you have to. You may or may not be given permission. And again, at least one of us will be in the room with you."

(The look on Brad's face at that moment was priceless!! I've never before or since seen a man's eyes so wide and face so red.)

"Rule three - we're not going to change any plans. You will just go through with all the plans wearing whatever clothes you have available. You will be in public places at times. You will have to make the best of it. "And finally, there will be no 'safety net'. If you really want to go through with this, you'll pack up every male item you have. Then your mother and I will help make sure none of it is accessible to you. "Brad, are you willing to give all of this up to dress up for the week?"

Brad nodded his head yes.

"Sheila, please go get a pair of your jeans, a rather plain blouse and a pair of tennis shoes for Brad. Brad, while Sheila is doing that, put all of your own things in your suitcase and close it up. Both of you get right back here then."

We both went and did what we were told and were back in the living room within a minute or two.

"Brad, take Sheila's dress off and put her jeans and blouse on."

Brad started to go to the bathroom to change.

"No. Right here. In front of us. And you might as well get used to it, because you will be changing in front of at least one of us every time you change."

That got my attention. Maybe I'd get more views of what I saw this morning! I wondered about sleeping arrangements at that point but didn't want to say anything. The three of us watched Brad take my dress off and hang it up properly on a hanger. He stood there in hose, heels and one of my bras, stuffed somewhat full. He started to take the stuffing out but Mom stopped him.

"Brad, you said you fantasize about having breasts. You're going to have them this week. Leave the stuffing alone."

Brad suddenly didn't look quite as enthusiastic.

"Get dressed - we have places to go!"

Brad pulled my jeans on. I picked a powder blue blouse from my closet for him. I had forgotten that it had some embroidered flowers and a bit of lace on the front until he held it up to look at it. I started to reach for it to get a different one, but Mom sensed what I was doing and motioned for me to be still. Brad slowly put it on, then sat down and took off my heels and put on the tennis shoes.

Mom looked around at all of us, smiled real big and asked Brad if he had packed all of his male things. He answered yes, and she told him to get his suitcase and let's go then! Brad seemed nervous, but this was his dream, wasn't it!? We all got in the car and Mom headed out of the apartment complex. I think I had a silly grin on my face, sitting across the back seat from my cousin and seeing him in my clothes was so odd. The conversation in the car was a bit more relaxed than it had been in the apartment. But Mom and Aunt Betty agreed that if Brad was to be 'one of the girls' for the week that he needed a feminine name. They both started tossing out names: Lee, his middle name; Brenda, a name sounding similar to his own; Bobbie, one of his cousin's names that could be male or female. That got us going with "Kim", "Gerry", "Sam" and several others. Then Aunt Betty declared that it should be an obviously feminine name, not something gender-neutral. That surprised me coming from his mother, but I could understand her point. It was pretty obvious, too, that she and Mom would make the decision. They discussed it more while we "youngsters" listened. Soon it was decided that for now Brad would be "Leeann". Lee was his middle name and Ann his mother's. And this seemed pretty feminine.