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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."
"And it makes me feel more care free."
"So this isn't the first time you've 'borrowed' someone else's clothes without asking?"
"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."
"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?"
"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.
I hadn't paid much attention to where we were during the conversation until now. Mom was pulling into the biggest full-service grocery store in the county. We didn't usually shop here and I wondered why we would be getting groceries now since we weren't going home anytime soon. But Mom would answer that soon enough.
"Leeann, there's one more thing you have to do before your mother and I are going to believe that you really want to go through with this. If you have anything other than a driver's license with you, put it in your suitcase. That includes your wallet. This is the only place in the area I know of that you can ship a package on Saturday. If you really, truly want to be treated like a sissy, like one of the girls, here is what you do. Choose one of us to go into the store with you. You will personally ask to ship your suitcase back to your home address. Be sure to address it to 'Leeann'. After you've answered all the questions and fill out all the paperwork, you'll ask the one of us with you to borrow enough money to ship it. We'll give you the money and you will complete the transaction. When you walk back to the car without your suitcase, we'll all know you're 100% committed to this."
Brad, or should I say Leeann was speechless. We all sat there in silence for quite some time. Then Aunt Betty suggested we give him 2 more minutes to decide. When he heard that, he quietly asked for the key to the trunk and if Aunt Betty would go inside with him. Both got out of the car, he got the suitcase and we watched them walk towards the door.
"Mom, do you think he'll really do it? And what ever gave you the idea to punish him like this? That had to be embarrassing for him to sit there in front of his own mother and talk about masturbating! I remember how hard it was for me to talk to you about it and we're even the same sex."
"Sheila, we'll find out soon if he'll do it. And I doubt if he considers this punishment. I'll bet he's asking to masturbate by the end of tomorrow."
Knowing Mom couldn't see the back seat well at all I was rubbing myself somewhat hard through my clothes, imagining hearing Brad ask to masturbate and that just possibly I would be able to watch him. I hadn't been in fantasy land very long before we saw Aunt Betty and Leeann walk out of the store. I say Leeann because there was no suitcase to be seen. Aunt Betty told us that Leeann did just as he had been told. Aunt Betty said that she even checked the shipping labels to be sure they said "Leeann". When Mom asked her if there were any reactions to Leeann's appearance, Aunt Betty volunteered that several people looked twice at him and that one or two pointed. She said the most obvious, though, was the person in line in front of them: when she turned around, she bumped into Leeann. When the lady saw his face, she looked a second time at his chest and didn't try to keep quiet when she said "I wish my boobs were as big as yours, boy!" Mom and I laughed at that. I kind of felt bad for Brad in a way, but I was starting to realize that he had brought this upon himself.
Mom headed for the open highway for us to go to the next city. Our conversations the next hour plus were nothing remarkable, just every day chit-chat. Every once in a while I'd have to grin as I looked at Leeann, wondering how well he was going to handle whatever else Mom and Aunt Betty had in mind. Rather than go straight to the mall Mom suggested we stop and get gas first and she pulled into the first station she found. Leeann (it was strange getting used to calling Brad that!) said that was good because he had to go to the bathroom. As soon as he said it he got this funny look on his face, so I asked him what was wrong. Aunt Betty didn't give him a chance to answer.
"Yes, son, you'll be going to the bathroom with one of us. No, you won't be allowed to even close the stall door. We can't chance you jacking off, now can we?"
Leeann's face turned red at Aunt Betty's comments. He rather dutifully got out of the car and while Mom started pumping the gas the rest of us walked into the station. The attendant smiled real big when he saw us, or should I saw when he saw Leeann. Aunt Betty led us right past him and right into the ladies room. I had to kind of push Leeann when we reached the door, but he knew better than to resist too much. I went into a stall to take care of business. I heard Aunt Betty tell Leeann that he had to sit down, that since he wanted to be feminine this week he had to do things as a woman would do them. I finished and stepped out to wash my hands. It appeared Aunt Betty was true to her word - she was standing there with the stall door open watching Leeann struggle to pull up his hose. Aunt Betty told us to wait in the store, that she'd be out in a minute. I couldn't tell where Leeann was more uncomfortable - in the Ladies' room or in the store. The clerk watched him real close. Leeann was obviously trying not to make eye contact with him. In some ways it was really cute!
Mom came in just as Aunt Betty came out of the ladies' room. Mom told Leann and me to go on to the car, that they'd be out soon. Leeann walked briskly out and towards the car only for us to both find it locked. I tried to make small talk with him to take his mind off of the situation. Looking back I think that deep inside this must have been what he wanted. It was three or four minutes before everyone got back in the car and Mom headed toward the mall. I was a bit surprised when we drove past it, but Mom explained. She had a good friend, Linda, that visited us every couple of months. I knew Linda and Mom had been friends since their teens, but what I didn't know was that Linda owned and operated a full service beauty salon. With Aunt Betty's full approval, we were on our way there for Leann to get a body wax. I giggled out loud and asked playfully if we'd all be able to watch while I watched the expression on Leeann's face change.
Once at Linda's shop it seemed we were going to have to drag Leeann inside. But Linda made a fuss over how cute he was already. The older ladies stood and visited a few minutes while Leeann and I sat down. I assured him that it only hurt for a little while, that he'd be fine. Then Linda came over to us, had Leeann stand up and explained that she had a new lady she was training that would be doing Leeann's wax. Then Linda asked which two of us would be observing. I think my jaw dropped that time and dropped farther when Mom said that it should be Aunt Betty and me! With that settled so quickly, Linda led the three of us to a large room on the side of the building where the new girl (I don't remember her name) was waiting. There were stools for Aunt Betty and me to sit on. Linda told Leeann to go ahead and undress. His fingers were trembling as he undressed. The smile on Linda's and her assistant's faces were priceless. Soon Leeann was naked and laying face down on the table. I'll spare you all the details of the actual waxing, but I do want to tell you that I've not yet seen as stiff of an erection as when Leeann turned over onto his back. Once the waxing was complete, Linda stepped out of the room and left her assistant there. Leeann asked about getting dressed, but was told not to yet, that Linda might want to inspect once more. So there lay my cousin with a rock hard erection in front of his mother, me and a salon employee.
When Linda finally came back in she was carrying something I didn't recognize. She started talking more to me than to Leeann, asking if I remembered her and her son visiting our house last Halloween. How could I forget - her son was dressed as a very ugly but big breasted hooker. Linda went on to explain that she had helped her son with his costume due to his own curiosity and that Leeann was going to benefit--Leeann was going to have rather large breasts attached to his body so he wouldn't have to stuff his bra all the time. Linda applied what I later learned was a special glue to Leeann's chest, then carefully placed the false breasts in place. I might add that the nipples on these were at least as big, dark and erect as Mom's, mine or anyone else's' I had seen when they were aroused. Linda told him to lay very still for fifteen more minutes, but as a reward for being so brave that she'd arrange a pedicure and a manicure. To our surprise, and even more to Leeann's, when Linda stepped out of the room another employee came in and the two started on him right there. Mom came into the now crowded room with Linda standing at the door. Linda explained to the three of us about caring for Leeann's new appendages (the glue weakened in steam, wear a bra or support so they stay in place better, etc.) and what to do if Leeann's they needed reattached. Before Linda left the room, Aunt Betty told Brad (Leeann) "Well, son, you got your wish. You have your own breasts now."
We all laughed at that line. Aunt Betty and I started to leave the room but the employees stopped us, saying that it protected both Leeann and them if family members or friends were in the room until the patron was fully dressed. So we sat back down. I'm pretty sure I stared at Leeann's groin a couple of times; and at his boobs. It looked so strange. I know my crotch was damp. I came to my senses some, though, when it was time for Leeann to get dressed. At Linda's earlier suggestion he started to put my bra on first. I say started because now it was really too small. My male cousin now had bigger boobs than mine! I snickered watching him struggle to fasten it. And then I heard words I'd never heard before: a man asking for someone to help him him fasten his bra! And watching him with his panties and hose was fun, too. He was so careful about touching his cock, as though it was taboo for him to touch it. Or maybe it was that he was afraid he'd have an orgasm if he did. I hated to see that go out of sight. It had been fun watching him naked. But it was time to move on. And there would be plenty more excitement that same day at the shopping center as well as elsewhere as the week wore on.
Aunt Betty and Mom were both smiling as we left the salon. Brad/Leeann seemed to be walking a bit funny, probably because of the combination of his erection and his boobs. The shopping mall was our next stop. I'd seen enough surprises in the last four or five hours that I didn't even want to guess what to expect next. And I'm glad I didn't try. Leann had no way to even begin to hide his boobs as we walked into the center court of the mall. Aunt Betty and Mom set the pace - a leisurely, relaxed one. Leeann seemed especially anxious to go into a store, probably just to get out of the potential line of sight of so many people. Instead of going into a store, we "window shopped" clear to one end of the mall and half way back. That's when Leeann and I were led into (can you guess?) a women's clothing store. The four of us browsed for a few minutes before a clerk came over to offer assistance. That's when Aunt Betty proved that she was backing this 100%. She authoritatively told the clerk that her son (and she emphasized "son") needed at least 2 bra and panty sets, a nightie, and a nice pantsuit or nice slacks/blouse combination, but that we didn't know what size. Leeann was standing right there and basically just looked down at the ground when he heard his mother speaking.
The clerk led Leeann toward the sales counter at the back of the store, got out a tape measure and started to measure him. Aunt Betty interrupted and explained that he had on one of "his cousin's" bras and it seemed much too tight. She suggested measuring him topless. As you well know, stores want to make sales so they try to keep the person with the money happy. So Leeann was led into a fitting room with Aunt Betty and Mom standing just outside the door, keeping the door open enough for them to see in. Leeann dutifully took off MY blouse and bra to be measured. The clerk had a noticeable smile on her face as she turned and announced "46DD" to the three of us. I very distinctly remember this, since I thought I was big at the time wearing a 44D. (I've put on a lot of weight since then, too.) I knew Brad/Leeann was stocky and that the falsies were sizable, but this surprised me. The clerk gathered five or six different bras for Leeann to try. Aunt Betty made him come out of the fitting room in every one of them, too, but wouldn't allow the door to be closed as he changed. She reminded him that there would be no privacy because he couldn't be trusted. She and Mom basically chose the bras for Leeann, then asked for matching panties. The clerk indicated that she wasn't sure just what size due to Leeann's build, but did offer that he could try them on over his own underwear. Again Aunt Betty proved her dedication by looking directly at Leeann and telling him while the clerk was standing there that he could try them on over the panties and hose he had taken from my room. The clerk turned her back to the two of them and was basically facing me, trying to stifle her laughter. I smiled at her real big. Again, the fitting room door was never completely closed, but Leeann was never on blatant display either. Once sizes and styles were established, Mom asked the clerk if Leeann could change into these now to try on other clothes. The clerk took Mom's credit card to the register as insurance. And when the clerk said "OK," Aunt Betty asked her for a pair of hose for Leeann and a bag to put my clothes in. And even though Leeann would be naked from the waist down, the door never went completely closed! Mom and Aunt Betty stood where one would have had to strain to see in and watched him change, then bagged up all of my clothes.
Aunt Betty turned to me then and asked me to sit my bag of clothes by the sales counter. I complied and walked back over to her. She then asked me to stand by the door but to keep it open. She wanted to look for slacks and blouses. Again I did as asked. Aunt Betty seemed to be shopping for a long time, so I tried to engage Leeann in conversation. Was this at all what he expected? What was going through his mind? He admitted that he never dreamed anyone would push him this far and that he was scared. He said he was scared of someone he knew well finding out about this and of people making fun of him. I tried to comfort him the only way I could think of. I reminded him I'd been fat my whole life and that you learn to ignore people making fun of you. Then he confessed something I've never told Mom or Aunt Betty: he lied about dressing up for sexual gratification. That was one of the primary purposes - to "get my rocks off" I believe were his words. (Mom and Aunt Betty pieced it together later, but I never told based on a promise I made to Brad.)
Aunt Betty brought three or four outfits over for Leeann/Brad to try on. Each one had some part of it very obviously feminine in its own way, things like strategically placed lace or colors and patterns. He had to try each one on and walk out into the store to find Mom. He knew that there were several other shoppers in the store, but also knew he'd best do exactly as expected. Aunt Betty was choosing outfits as he tried them on, but wasn't showing him which ones she chose. He was trying on the last one she had for him when Mom came over smiling. Mom wanted Leeann to try on a dress and a skirt/blouse outfit "just for fun". Brad argued that he should be allowed to close the door to try these on, but was shown no mercy. In fact, I think Mom and Aunt Betty purposely moved nearer the entrance of the store because of this. I "had to" keep the door open and make sure he didn't play with himself (read as "I had the privilege of seeing his erection through his panties and hose"). After evaluating each outfit, Leeann had to come back to the fitting room and wait for anything else. Once he was out of the skirt and blouse, I stood with the door open while we waited for our mothers to pay out. Leeann was still in only a bra, panties and hose, waiting to see what he'd be wearing. Aunt Betty brought over one of the pairs of slacks he'd tried on - one that seemed very snug and had no pockets - and an very transparent white blouse, short sleeve, low cut in the front with not really a lace, but a very nice feminine trim up the front. As soon as I saw it I knew there would be no hiding his bra in the front or back! I thought I saw tears in his eyes while he was dressing. He asked what to do about his drivers license and change to which Aunt Betty responded that he'd have to carry them for now and we'd try to find him a handbag soon. She told him to get dressed and they'd meet us at the food court for a cold drink.
As Leeann and I walked out of the store and toward the food court I noticed that rather than going way ahead of us that Aunt Betty and Mom were watching from a distance - watching both Leeann's actions and peoples' reactions. As you might expect, there were lots of people looking towards us with lots of different reactions. And there were a lot of people that didn't even notice. Leeann walked faster than when all four of us were together. I lagged behind a time or two so I could see what his ass looked like in those snug slacks - and it was cute. Near the food court I had opportunity to turn and look at him. He was a sight! From the neck up he looked like a teenage male with his boyish face and wavy brown hair. Below the neck to just below his waist he looked womanly with noticeable nipples (even though they were false) capping off very large breasts in a very stylish bra visible under a nearly transparent blouse neatly tucked into a pair of snug slacks. That's where the sight took a strange turn - his erect penis was very well outlined in spite of (or because of?) his hose and very snug slacks. I may have even licked my lips when I saw that! Mom seemed to just appear behind me and I'm sure she saw it too, but she looked Leeann in the face and just said "looking good!" We got a soda, found a table, sat down and just visited for a while. We visited long enough it seemed Leeann had forgotten about his situation.
Mom volunteered for she and I to take all the packages to the car. It was during that walk that Mom shared with me that she had suspected Brad of trying her lingerie the last time he stayed with us. She told me about how her drawer had been rifled trough some and how there were unusual stains on one of her favorite pairs of panties. Mom also started talking about sex some. She and I have always had a very open relationship, but I wasn't sure I was ready for what I heard. She told me that one reason she looked so forward to Aunt Betty's visits was the great sex. I almost dropped the bags I was carrying. Mom and Aunt Betty!? Up to that point I'd experimented some with other girls, but this I had trouble imagining. Mom said something to the effect that Aunt Betty ate her better than any man ever has and twice as good as most. Then she added that Aunt Betty had a bit of a kinky side to her, too. We got to the car about that time and at least on some level I was very thankful that we were able to change the subject. Maybe it was because I was getting awfully turned on at this idea. While Mom had been telling me these things my imagination had even wandered to the point of me being in bed with one or both of them.
The walk back to the mall wasn't as intense. Aunt Betty and Brad/Leeann were still sitting there calmly talking. We joined them and everyone seemed care-free for a while. That ended when Mom said something about finding Leeann a handbag and shoes. Leeann went from calm to very shy, maybe even nervous in half a second. But he stood and followed when Mom took the lead. We all started through the other half of the mall. I'll spare you many of the details about Brad/Leeann shopping for shoes. But I do want you to know that he tried on lots of them in all shapes, sizes and styles. And that it seemed with every pair that the bulge in the front of his slacks grew bigger. I did notice, too, in the last store he tried shoes on that a rather large wet spot appeared at the tip of his erection. I asked him in a whisper if he came. He said no, but that every time the sales lady knelt down in front of him he could see down her blouse and even see her nipples. This happened to be the store where Aunt Betty chose a basic black pump for Leeann and found a matching purse. But this time she made Leeann ask if he could wear the shoes out of the store. "Poor guy" I thought to myself!
Now that Leeann had a few things of his own to wear Mom and Aunt Betty just wanted to browse around. I suggested that he might want to go to a sporting goods or electronics store. But Leeann insisted on staying right with the us. I bet we browsed another couple of hours in the mall before Aunt Betty suggested we go to dinner. And all the while Leeann was right with us, looking about as sexy from the neck down as I could hope for. I bet he was embarrassed by his erection though. You could tell he tried to hide it a few times with the way he carried things. While we were walking towards the restaurants, Mom said she needed to use the ladies room and suggested we should all go. There was the panicked look again! Mom took his arm and told him he had to make a choice - he could go in the ladies room with us or one of us could go into the men's room with him. He just stared straight ahead with a dumb look on his face. So Mom made the decision. We had made our way into a major store where the restrooms wouldn't be near as busy. Aunt Betty was a few steps ahead, opened the door, looked back and nodded. That was Mom's cue to take Leeann right on into the ladies room. Since Aunt Betty nodded, I was sure the facility was empty but learned otherwise upon entering--Two of the five stalls were occupied! Mom led Leeann into the first empty stall and stood there with the door open. When he first stood facing the stool, Mom grabbed his shoulder to remind him to turn around and sit down. Aunt Betty and I took care of business. I had my hands washed first so I went over to stand in Mom's place. I smiled at Leeann, who was just ready to stand up. This made the second time I was able to watch him struggle to try to position himself for comfort, get his pantyhose straight, and so on. I could so enjoy this! Aunt Betty snapped me out of my fantasies when she told Leeann to hurry up so he could wash his hands.
I think a horrified look crossed Leeann's and my faces at the same time. Aunt Betty used the male pronouns and there were still other ladies in here! Leeann stepped out of the stall and to the sinks to wash. Another lady was standing there and looked very oddly at Brad/Leeann. Aunt Betty looked at her and smiled. To my amazement nothing was said. I later learned that had anything been said, Aunt Betty was going to claim that Leeann was mentally retarded and that some days the only way to keep him calm was to dress him like his Aunt.
There were a couple of nice restaurants in the mall, so we decided to just eat there. Except for a few stares and the waiter looking hard at Leeann (basically trying to look down his blouse) dinner was uneventful. Dinner conversation was very relaxed and didn't focus on the events of the day. We all even had desert. And it was during desert that someone mentioned sleeping arrangements. Mom smiled real big - a smile that others might not recognize as mischievous. But I did. Then she told us that she thought she had that figured out, but it would be better to discuss it on the drive home. After hearing that I was anxious to leave. Fortunately I didn't have to wait long. We were parked on the opposite end of the mall, so Leeann had the chance to walk all the way through it one more time - this time all the way through in his own ladies shoes and carrying a purse!
Leeann got his share of looks, stares, grins and giggles walking back through the mall. And we didn't go straight to the car, either. We stopped and browsed in several stores. Neither Mom nor Aunt Betty were shy about holding up dresses or nighties to Leeann even when several people were near by. As we finally exited the mall Leeann let out an audible sigh. Mom asked him if he was OK and he just said that his feet were killing him, that he was really looking forward to sitting down. We all laughed at him over that, knowing that he was in just a pump. We started joking some about what he'd be like in a spike heel.
Once in the car and headed home we talked about several events of the day. It was almost as though we were tiptoeing around the sleeping arrangement discussion. We were within ten minutes of home when Leeann got brave soul enough to ask. Everyone was silent for a bit, waiting for the wiser, older sister (Mom) to speak.
"Our biggest concern with Leeann is can we trust him? Leeann, you betrayed our trust by, in your words, borrowing things. You say you don't do this for sexual pleasure, yet your cock's been hard almost all afternoon. I don't think we should trust you not to masturbate in bed. I'm a very light sleeper but I also believe that you can probably be very quiet when you're masturbating. So, Betty, I want you and Sheila to take her room. It's every bit as big as mine with the same size bed. Leeann, you're going to sleep with me in my bed. And in case you have some other crazed ideas, I do mean sleep.
"I think we can all use a good nights sleep after today's events Now it's getting late, so when we get home we'll all get changed into our nightgowns and have a snack. Then its off to bed."
We rode silently the rest of the way home. Once there, everyone pitched in to carry all the packages inside. Mom cleared out one of her drawers and made Leeann remove the tags and fold most of his newly acquired things. I say most because she and Aunt Betty had saved a couple of surprises for him. Once things were put away, Mom announced that we should all get ready for bed. With that, Aunt Betty got her suitcase and moved it into my room. We heard Leeann ask what he was supposed to sleep in. Mom told him he could borrow one of her gowns or that he could ask me. With that she showed him two of hers he could use - a pink one that was so short it would barely cover his ass standing up and a white very transparent one. So he asked if he could see what I had that he might borrow. I offered a black translucent knee-length with slits in the front and back and lots of lace and a see-through teddy with snaps in the crotch. Mom was standing in the doorway and saw Leeann reach for the black nightgown. She cleared her throat.
"Remember the rules? I didn't hear you ask."
Leeann blushed a little when he asked "Sheila, may I borrow your black night gown, the one you just showed to me?"
I couldn't help but smile as started to hand it to him. I looked at Mom before he had it in his grasp. "Mom, shouldn't he have to change into it in front of all of us?"
Mom thought for a minute - actually I think she was just trying to make Leeann squirm. Then she answered "He doesn't have to change in front of all of us unless everyone is willing to put on the same show. But he will not be left alone - one of us will be watching when he changes. Brad...I mean Leeann...come back to our bedroom."
I handed him the gown and they both went to Mom's room. We could hear Mom telling him to put things away as he took them off. I could picture what was going on when Mom asked if he was going to take his panties off. Then she told him that no one else in the house would have panties on under their nightgowns so he wouldn't either. I looked at Aunt Betty and she looked at me and we both just grinned real big.
I picked up my nightie and started to go to the bathroom to change. Aunt Betty looked at me with a question in her eyes. She spoke very softly and asked me if we could both just change in my room. After Mom telling me about the two of them I think I was a bit nervous but said sure, why not. She undressed rather quickly and was standing naked when I got down to my bra and panties. She told me to turn around and, when I did, she gently unhooked my bra. She slid her hands to the front of my body as she took it off of me. It felt good!! I turned back around hoping to feel her hands on me more but she had stepped back and was pulling her gown on. I pushed my panties down and stood there in front of her for a prolonged second, then reached for my nightie. As I was pulling it on she stepped into the living room. Little did I know how much fun this week was going to be.
I was the last one into the living room, but I realized immediately how sexually charged the air was. Leeann couldn't hide his hard-on. He could keep it covered while standing up, but the slit in my gown was just right that when he sat down his penis stuck out through the opening. And Mom wouldn't let him keep it covered with his hands - it was too much like playing with it. But Leeann had reason to have a hard-on. Mom's gown was cut so low that it barely covered her nipples and so thin that they were very visible through it. Aunt Betty's nightie was more substantial, but so short her pubic hair peeked out when she sat down. And I had decided to wear the teddy that Leeann had turned down. It was almost as low cut as Mom's gown but not quite as thin. And it was a bit snug and kept trying to pull up into my pussy.
The atmosphere was sexually charged. Though we were allegedly watching the news, I don't know if any of us could have told anyone else what was newsworthy that day. As soon as it went off the air, Mom spoke up saying we should all get a good nights sleep. Well... that was a great way to get us all into our respective bedrooms, but I don't believe much sleeping was going on. I'll have to tell you about the night and more about the week in the next installment!!!!
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Posted by ATCFNM at 5:21 PM