Crossdresser Evolution Ch. 07

Recap - Crossdresser Evolution - Ch 01 - 06

I become addicted to masturbating while wearing panties. There was this part of me that was telling me that I CAN'T like this but there was another part that was saying that I DO like it.

I learn about feminized men and I also learn about them sucking cocks and I taste my cum for the first time.

I buy my first bra & panties then my wife helps me buy my own panties. I cum in panties in front of the sales lady and Sue shows me how to suck cock with a dildo.

Wearing panties under my shorts in yoga leads to flirting and friendship with 4 students and the instructor. Then things heat up with the Yoga Ladies and Tom.

Ch 07 Sue takes me cloths shopping - dresses & skirts?—————————————————————————————

The next day Sue said, "Mark, put an a matching bra and pair of panties under your clothes. We are going shopping." I already had or was sharing quite a collection of lingerie. What could we possibly need?

We went to the women's section in the store and Sue asked, "Which dresses would look good on me?" That was a relief that she didn't ask what would look good on me. After we picked out some mini skater and V neck dresses we went to the dressing rooms. She invited me in and she tried on the 1st pale yellow dress. I loved it. It was very short and slimmed at the waist making her look fantastic. It also was a tiny bit transparent so I could just barely see her bra and panty lines through it.

She took that off and handed it to me as she picked up the next pale pink one with a lacy top. I started to hang the yellow one on the hanger when she said, "Wait, I want you to also try it on." I just looked dumbfounded. She said, "The girls and I want to go out and want to include you. We just want it to be us girls though. If we have a guy with us the dynamic is very different. The guys are less likely to think they are available."

I said, "I can't go out in public in a dress. Someone I know could recognize me."

Then she looked at me with those puppy dog eyes and said, "We were planning to go to Crossville so you or we wouldn't know anybody there."

I said, "I'm not agreeing yet but I'll try on the dress for you."

I stripped down to my bra and panties as she slipped on the other dress. I slid on the yellow dress and we stood side-by-side in front of the mirror. It felt a bit strange but daring and a bit naughty. From the neck down I looked damn good. Not that different from Sue. We were similar in size, duh, we were wearing the same size dresses. She started to move her hips and body and the dress moved with her, rippling and swinging back and forth. It was so sexy and so seductive. So I did the same. It felt freeing. The openness of the dress and the flowing of the material was very different than wearing pants that closed off my crotch area and didn't move much at all. Sue stepped back to look at me and I twirled the dress a little and it swung out wider and then settled. She said, "That looks great on you, so sexy. No one would suspect you are a guy when we are done with you."

I told Sue, "That pink dress also looks fantastic on you. I'm curious what the lace feels like."

Sue didn't disappoint me when I slid the yellow dress off, she slid the pink dress off and handed it to me. I slipped it on while Sue got dressed. The lace felt soft and you could see more of my skin through it. I loved the pink, so soft and sensuous. I was looking at myself in the mirror, twirling slightly, watching the dress move with my body when Sue suddenly opened the door and stepped out. Oh no, was this the lingerie department all over again?

A few minutes later Sue was back with another outfit. She said, "Here try this skirt and top on." Fortunately, no one say me wearing the pink dress as she opened and closed the door like before in the lingerie department.

The outfit she came back with was a short jean skirt and a tank top with a built in bra. I slid off the dress and my bra. Then I tried to put the tank top over my head, like I would any t-shirt. I got stuck because it was very tight. Sue turned around and just laughed. "Tom, you have to step into it and pull it up." Who knew? I tried it and that DID go much better. Then I slipped on the skirt. The tank top was very form fitting and felt nice giving my whole upper body a hug. The built in bra had some padding and it, giving me a little shape, it made me look like I had small breasts. The skirt looked amazing. Sue agreed and said, "We will take all 3."

I changed and we took everything to the register to check out. The sales lady asked, "Did you find everything you were looking for and how did everything you found look?"

Sue said, "We both liked everything, they make us look fantastic."

I turned a deep red as the sales lady just smiled and said, "Glad you both liked everything. Which outfit do you like best?"

Sue said, "I think Mark liked the skirt and top best but also loved each of the dresses for different reasons." Sue looked into my eyes and asked, "What did you like best about the pink dress?"

I was about to say it just looked amazing on her when Sue said, "He liked the feeling of the lace against his skin."

Luckily the transaction was over and I just said thanks and started to walk away with the bag. Sue followed.

Once we got to the car Sue said, "I couldn't resist a little teasing but that sales lady didn't over react. Wasn't it just a little naughty and fun?"

"Yes, it was. I wasn't sure what her reaction was going to be but she actually didn't seem judgmental and might have been mostly accepting. Although, it could have been because she was getting a nice commission on the sale."

When we got home I got out the skirt and top and put them on. I hung around the house for the rest of the evening in them. I noticed that I had to adjust how I sat so I wouldn't show off my panties. If my knees weren't, at least, close to touching each other you could see my panties.

I also noticed that I was in a constant state of partial arousal and my panties were wet the whole evening. No doubt this was partly caused by Sue rubbing my leg and inner thigh while we watched TV but some of the wetness was caused by the feeling of dressing in the skirt and tank top. Toward the end of the last show Sue's hand started going higher and higher until she was rubbing my dick through my panties. It didn't take long before I came in the panties. I could get used to all the attention if it meant cumming this much.

The next day I came home and put on the yellow dress. Sue had taken out the lining so it was more see through than before. Sitting in it caused the same problems the skirt did as far as showing off my panties.

We had a repeat of the night before, ending with me again cumming in my panties. This went on for over a week and I was feeling extremely comfortable wearing the skirt and dresses around the house. Of course having Sue rub my dick under my dress or skirt through my panties until I came had a definite affect, I LOVED wearing the dresses and skirt.

On Saturday morning, I got up and put on the skirt and top like usual, then went to the kitchen to get breakfast. I got my cereal ready and then usually I go out to the end of the driveway to get the paper before I pour the milk on my cereal.

I shouted out to Sue, "Hey, I'm going out to get the paper" and I headed for the front door. I went out, without thinking that I was wearing a skirt and ladies top. I headed down the walkway and over toward the driveway. Halfway down the sidewalk toward the driveway I realized I was out in public in a skirt. I quickly looked up and down the street to see if anyone else was out. No one!! I quickly made a beeline for the paper and headed back toward the house at a fast walk. Halfway up the walk I heard a car coming. I didn't look but quickened the pace. I stepped into the house just as the car was in front of our house. My heart was pounding. Did they notice? Did the car slow down? Did I know them? ...

Sue stepped into the living room and I was standing with my back against the front door. I was breathing hard and probably looked a bit panicked.

She looked at me and said, "Did you just go out to get the paper dressed like that?"

I said, "Yes, I did!! I didn't even realize it until I was almost to the paper. I didn't see anyone outside but a car went by just as I was coming in. God, I hope they didn't notice me in this outfit but they seemed to slow down a bit in front of our house."

Sue said, "But that is a nice outfit, so maybe they were admiring you and the outfit" as she started to giggle a little.

Then I just lost it. I burst out laughing. When I calmed down a bit I said, "What the hell, I love dressing like this, who cares anymore."

After I was calming my laughter, Sue said, how about I call the girls and see if they want to go out together tonight?"

I said, "Sure," not knowing that she meant with me in a dress.

Now remember, the whole idea behind me trying on and buying dresses was for the girls and I to go out, with me in a dress.

After breakfast Sue went into the other room and started calling the girls. After an hour or so Sue came in and said, "They will be over at about 6:00 to help you get ready."

I said, "Me get ready? You all think I'm going to dress as a woman tonight, don't you?"

"Why, of course. What did you think?"

"I thought we were just getting together and going out, not with me dressed as a woman." Then I couldn't believe what came out of my mouth next. I said, "How about I just wear a denim skirt and a shirt that could pass for a man or woman's shirt and no makeup or wig, etc.? Just a guy wearing what he wants to wear"

Sue looked at me quizzically for a moment and said, "Sure that should work. There is nothing other than people's fixed thinking that say you should go all-out to look like a woman. You should be able to wear whatever you want. You'll probably get a lot of looks but to hell with them. I think I can convince the ladies to stand by and with you, though it shouldn't take much convincing."

Through the day my mind kept looking ahead to the evening. Working in the yard alone didn't help things. I just got more and more nervous about what might happen if we show up at the restaurant with me dressed in a skirt. Was I crazy to do this? Could this turn ugly if some tough guy decides he doesn't like me there dressed in a skirt? Will this turn into a bunch of people just hassling me and maybe the ladies for being with me? To say I was anxious was an understatement.

I finished up in the yard and had to take a quick shower. When I got out Sue had already laid out my favorite denim skirt and a fairly nondescript red women's T-shirt. There was also a red lace matching bra and panty set.

Sue called in from the other room and said, "I hope you don't mind but I put out my suggestion for an outfit for tonight. I thought you would want to wear your sandals with it."

As my dick was getting hard, thinking about what happened the last time I wore that bra and panty set I responded with, "This outfit will be perfect, especially if you were thinking about the last time I wore this bra and panty set when you were picking it out."

Then she peaked around the corner, saw my hardening dick and said, "Mark, I was going to ask you if you'd like us to repeated that night but judging from your erection I think I know the answer and I agree with your dick. I would very much like to do that again. I'm usually pretty horny after a night out with you and the ladies."

I put on the bra and T-shirt first, hoping that my erection would go down so putting the panties and the skirt on would be a little easier. I was wrong but stretched the panties over my dick as I tucked it in. I slipped on the skirt and the bulge from my now partially erect dick wasn't too noticeable.

I slipped on my sandals and admired my outfit in the full-length mirror. This felt right for me but I was still a bit apprehensive about what the evening would bring.

Sue had found a restaurant across town that was supposed to be good and was just far away enough that we would be unlikely to see someone I would know. For insurance, I put a bag with a pair of jeans and a T-shirt in the back seat and Sue and I headed out to meet the ladies.

We got to the restaurant first, put our name in and sat in the waiting area. I could feel everyone's eyes on me but I just tried to focus on talking with Sue.

I was having a hard time and glanced at the couple across from us. The lady's eyes and mine met and we just smiled at each other.

Sue quietly said, "Who are you smiling at?"

I said, "The lady over there."

Sue glanced around the room, as did I. Most everyone was looking at us or at least me. Then Ann, Jane, May, Fran and Elsa walked in. Sue and I got up to greet them with hugs all around. We were standing in sort of a circle chatting when I glance at a guy sitting with what was probably his wife. He was probably in his mid thirties fairly fit looking. Our eyes met and he smiled and nodded his head slightly at me. I smiled and nodded back at him. Then I heard him tell his wife that he needed to use the restroom, got up and glanced again at me with a smile and seemed to be gesturing with his head for me to follow him.

I wasn't sure what was happening but my curiosity got me and I told Sue I'd be right back. I wasn't far behind him but when I got into the men's room the guy was standing at the urinal. There was no one else in there and I took the urinal next to him, lifted the front of my skirt, pulled the waistband of my panties and pulled out my dick to pee.

Then he said, "I like the outfit but how come you aren't trying to look like a woman?"

I replied with, "Because I'm not a woman, obviously, and I don't want to be seen as a woman. I just like some traditionally women's clothes."

The wall between the urinals was fairly low and he leaned over to look at me. He said, "I see you like the panties to. I'd love to see you in just your bra and panties."

I said, "How would your wife feel about that?"

He said, "I think she would have a problem with it. She doesn't know that I like looking at cross dressers, shemales and transgender guys."

I asked, "Do you only like to look or have you tried on panties or other women's clothing?"

He hesitated and I could see that his face turned quite red and then said, "When I was a kid I tried on my sister's underwear and a couple of times I've tried on my wife's panties."

Then another guy came in so we both zipped up and washed our hands without another word. On the way out he slipped me his card (Steve) and said, "If you think we could work something out so you could show me your stuff I would be eternally grateful."

I said, "I might be amenable if we can get both of our wives onboard. I think Sue would be ok with it and if you need some help with your wife, Sue and I might be able to help."

Back in the waiting area, I glanced back at Steve and he gave me a discreet thumb up gesture and I just smiled back.

Then our table was ready so we all followed the lady to our table and sat down. I noticed a few minutes later that Steve and his wife were sitting one table over. Steve was facing us and his wife had her back to us. He winked at me before I got back to reading the menu.

We all chose our meals and the waitress left to put the order in. I said to the ladies, "Well, that was an interesting conversation in the men's room. The guy one table over in front of me with his wife asked if he could see me in my bra and panties. He also told me that he looks at cross-dressing guys, etc. Then, when I asked, he told me that he had tried on panties a few times.

"He slipped me his card and we exchanged code because someone else had come in, basically saying he'd like me to show him my "stuff." I said it might be ok if we can get both of our wives onboard. His wife doesn't know anything about his web surfing for cross-dressers or panty experiments."

"Sue, if it is ok with you I think I might want to call him tomorrow and see where this goes."

Sue said, "Sure, you have my curiosity up to."

Throughout the meal I was kind of playiny with Steve. I would let me legs open up until I saw Steve looking and then I would just smile at him and close my legs." I'm sure he had a very clear view of my red lacy panties. During some of the more racy parts of the conversation with the ladies I was getting quite hard. I made sure to show Steve that I was hard, even reaching under my skirt at one point to adjust my dick in my panties.

Sue smiled at me a couple of times when she realized that I was flirting with and teasing Steve.

On the way home Sue and I talked about my flirting and teasing Steve. It was interesting how what I was doing to Steve, was similar to what women regularly do to men. Seeing a woman's panties evidently is rarely an accident.

Needless to say, when we got home Sue followed me up the stairs grabbing at my ass under the skirt. It was minutes before we were naked and all over each other. I brought her to orgasm orally first and then she sat on my dick and tortured me until she started to cum again. Then her vagina squeezing on my dick put me over the top and I push up as far as I could inside her and let loose wave after wave of cum inside her as her orgasm started to subside.

The next day when I woke up it didn't take long for me to remember my interactions with Steve and I started to think about whether I would go forward with calling him and what would I say and do.