Aunt Betty's Visit Ch. 01


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!

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