Crossdresser Evolution Ch. 04

Recap - Crossdresser Evolution - Ch 01 - How I got started crossdressing

I was becoming addicted to masturbating while wearing panties. I could feel the arousal but at the same time was ashamed that I was wearing my wife's panties knowing that I would soon be cumming in them.

There was this part of me that was telling me, "I CAN'T like this," but there was another part that was saying "I DO like it." How do I reconcile all these conflicting feelings and thoughts.

Recap - Crossdresser Evolution - Ch 02 - Getting my wife involved

One night after we had been drinking and fooling around I switched my briefs with her pink panties. We went to sleep wearing each other's underwear. In the morning she made me cum in her panties.

I learn about feminized men and how they suck cocks then I taste my cum for the first time.

Recap - Crossdresser Evolution - Ch 03 - Getting Bolder and My Wife Finds Out

I buy my first bra & panties for me.

While reading about feminized men sucking dicks I cum in my panties with my wife sleeping in the other room.

I sleep in panties next to my wife without her knowing. I wear her panties to work but get caught when I get home - "The Talk"

Part 4 - Wife helps me buy my own panties

Sue helps me buy panties for me.

One Sunday morning we were reading the paper together at the table. I was looking at the department store ads and was lingering over the underwear ads because there were more bikini and thong styles than usual. Some with lace others were micro fiber, almost see through. All of a sudden Sue was watching me. I wasn't sure how long she was watching but I was about to find out. She said, "I saw you lingering over each of the department store's ads for lingerie."

I hesitated and started to respond defensively but she beat me by saying, "I know my panties aren't what you like to see on people on the web. Maybe it's time we go shopping for some panties that would be more appealing to you."

I blushed and said, "Really? You want me to own and wear my own panties?"

She said "Sure why not? You can also wear them more around the house if you want. I might also try some different styles. How about we go shopping and maybe we can get some matching ones."

I said "I'm OK with it if you are OK with it."

Underneath I was trying to contain my excitement and debated whether I should tell her that I already had a little stash.

After we finished up we headed out for the mall and went into one of the lingerie departments. I tried to look casual like I was with her shopping for herself. She looked at me and said, "Hey, we're here for you, you need to look and let me know what you would like to wear." I glanced to see if anyone heard her and fortunately there where only a couple of other ladies there.

I started flipping through the hanging panties. Just doing that was getting my dick hard. I found a couple of string bikinis, bikinis and thongs. She looked at my selections and said, "Hmm a bit racy, nice Come over here." She led me to the bra and pantie sets. She pulled some sets that had similar panty styles but also had matching bras.

She said, "Are you game to try sets?"

I hesitated appropriately and timidly said, "I guess?" Then she grabbed a tape measure from nearby and wrapped it around my chest. I about died!! Then she checked my waist and hips. I wasn't sure if anyone noticed but one lady might have.

Sue said, "I want to be sure they will fit ok." She checked the sizes and we moved to the register. She handed them to me and said "I'll meet you in the next department store."

I blushed and could only get out a week, "ok" as the sales person and another lady looked on.

The sales lady laid each bra and each panty on the counter, scanned each price and carefully folded them. I was so embarrassed. Especially when the other lady's friend came up and the lady whispered something to her. I was sure she was telling her friend that the bras and panties were for me. I left as soon as I could and went to meet Sue.

When I got there she was looking through the nighties. She had 2 hanging over her arm. Both mostly see through, one pale pink and one pale yellow. As I walked up she pulled another white lacy one out. She said, "Come with me." I followed her to the dressing room where she got a room and motioned me to come with her. I went in with her and she said, "Try this yellow one on."

I said, "Really, here?"

She said, "Yes. I want to be sure which one looks best and be sure it fits well ." I reluctantly stripped and slid the panties and top on. She said, "It looks nice. How about the white lace one." I tried that one and it was a bit tight so she just opened the door, as a lady was walking by, and went out to get another size. I shut the door quickly as the lady just stared.

Sue came back with another size. I opened the door just enough and let her in. It then occurred to me that anyone who saw her fully dressed going back to this dressing room knew I was the one trying this lingerie on. I just switched to the next size, she said, "That looks great!" and handed me the pink one. Then she stepped out again. I changed into the pink one quickly so she, at least, wouldn't reopen the door while I was in the middle of changing.

She took her time coming back and I was left staring at myself in the mirror. My dick was hard and there was a wet spot forming. Then the sales lady asked, "Is everything ok in here?" I had to say yes but now she knew I was in there alone with no pants and barefoot since she could see under the door. OMG!

Sue came back at that moment and asked, "Mark, can you please let me back in?"

I did and the sales lady was there just looking me up and down. Then she said, "You'll have to buy that one now that you made a mess in it."

Sue looked at the wet spot and said, "He just likes the feel of the fabric."

With that she reached down and started rubbing her finger in the wet spot at the head of my dick. The sales lady didn't move, busted watched. I couldn't help it and I started to cum in the panties within what seemed like seconds. The sales lady just said, "Now!! There is no question." She handed me a plastic bag, and said, "Just take the rosa-blanca.ru off, put that mess in this bag and bring the rosa-blanca.ru to the register." She walked away mumbling something about a mess.

We bought the pink and yellow ones and then left. As soon as we got into the car Sue started laughing hysterically. She said, "The looks on your face when she opened the dressing room door was priceless. Even the look on that customer lady's face was great. She was in shock seeing you standing there in that lacy lingerie. I wasn't sure whether she notice how hard your dick was or not but I'd love to know what she was saying to herself in her head. I thought the sales lady was going to have a cow when I made you cum in those panties right there in the store. I couldn't believe how fast you came."

I just sat there looking at Sue while she went on and on. She evidently had enjoyed my embarrassment quite a bit. I only said, "I'm glad that I could provide such great entertainment for you. Now can we go home?"

She acted all offended and said, "Isn't that what sissy men like you like, being humiliated?"

I said, "No, I did not like being humiliated. I would much rather be encouraged to wear lingerie but not be humiliated."

She looked at me inquisitively and said, "Oh. I was reading so much about others and I never asked you, but your dick was so hard the whole time and you shot a load of cum within about 15 seconds of me touching you?"

"Yes, it was arousing but it was totally embarrassing." Those people were probably all judging me as some sort of pervert or something. Whatever it was, none of them approved of me trying on lingerie in the store and probably not wearing it at all. It doesn't feel like a "manly" thing to me. I'm sure they don't see it as a manly thing. I like wearing girly things but I'd rather keep it private."

She paused for a minute and said, "What if someone was ok with you wearing girly things?"

"I don't know. I hadn't thought about that and even if I was ok with it, how do you find out if someone is ok with it? Not something that comes up in normal conversations."

She had this inquisitive look on her face again and started the car to go home.

Sue comes home with a toy.

We continued to play, read stories and have sex like before but now I had my own panties, bras and teddies. I was also wearing a bra and panties almost all the time I was in the house and sleeping in the teddies. We got tired of having to wash things out every few days until Sue came home one day with a bag of about 10 bra and panty sets. She just said, "Now we don't have to do laundry so often."

I also noticed that she had another bag but she didn't say anything about it. That night we were reading stories on the web. The story we were reading was about training a guy to suck cock. They were using a dildo for him to practice on. Sue said, "I'd like to see you suck a dildo to see if you'd like doing it."

I hesitated for a moment and said, "I might be persuaded to try it but I think fantasizing is probably better."

She asked, "If I had one would you try it?"

"I guess I would at least give it a try but we don't have one."

That was all she needed. She reached into the drawer and pulled out a 7" life-like dildo. It was a very real looking dick. It even had veins running down it and a ball sack.

She said, "Here, just touch it."

I did and it felt soft but stiff, a lot like my erect dick. I could even move the top layer of the skin-like covering over the inner part of the dick, a little like the skin covering my own dick while it was erect. She stuck her tongue out and erotically licked up the underside of the dick. She did that several times as I watched.

Then she said, "It's easy, you just have to run your tongue up the underside to get things rolling, or in your case oozing. You always started to leak precum like mad when I used to do this to you."

Then she put the dick right in front of me and said, "Just try it. I think it will turn me on so much to see you licking a dick."

I tentatively licked it from the base by the ball sack up and over the tip. I did it several times, each time looking more erotic and sensual than the time before as Sue encouraged me and said how great I was doing.

She pulled it back toward herself and started to lick it again but after a couple of times she got up over the head, opened her mouth and slid just the head of the dick in. I could see that she was working her tongue around the dick head, mostly concentrating on the underside as I could see her tongue out of her mouth but sliding up and down the sensitive part just below the head.

She backed off and said, "That will drive most guys crazy. When I used to do that to you, you would be ready to cum very quickly."

She said, "Let me show you," as she slid off her chair and down in front of me. She slipped my panties down, my dick popped out and she started to do the same thing she showed me on the dildo to my dick. As she said, I was ready to ejaculate in about a minute or two but she stopped just before I ejaculated in her mouth.

She said, "This is where I have a little fun. I stopped just before you were ready to go. I can slowly and gently deep throat you or just settle back and gently lick up and down your dick."

She began to demonstrate and it was driving me crazy. I was just on the edge of cumming and I would try to thrust my dick in and out of her mouth or just get in deeper as she tormented me by taking me to the edge and then backing off.

Then she just stopped abruptly, pulled my panties back up in place, tucking my frustrated dick back in my panties.

She sat back in her chair and slid the dildo back to me, saying, "Now show me what I just did to you."

I was so damn frustrated but I just said ok and tried to copy what she did. I could feel the shape of the dick head in my mouth and felt like I just wanted to suck hard on it but Sue saw where I was going and encouraged me to work with the dick head like she had done to me.

She pulled it back toward her again and I was getting so into working the dick head that I tried to follow it.

She again started licking the underside and then worked the dick head a little. Then she started bobbing her head up and down, taking more and more of it into her mouth. I could also see that she was applying more suction when the dick slid back out of her mouth.

Then she slowly lowered her mouth over the whole dick until its balls touched her chin. She backed off and alternated sucking with taking it all in. I could see her throat move when she took the whole thing in. Then she explained how she relaxed her throat so the dick head could go into her throat and she could get the whole dick into her mouth.

She said, "You might start to gag but you should just back off a little, relax and try it again." She gave me the dick saying, "If you hold it you will have more control if you start to gag."

Again, I repeated the sequence, applying more suction was much more fun, knowing that it would have driven me crazy.

I was a little apprehensive at trying to swallow the whole thing but Sue said, "Now try going a little deeper with each movement." She also started running her finger over my wet panties. I was surprised that with her encouragement I was getting more and more in my mouth. Her rubbing on my panty covered dick didn't hurt but I was also getting used to relaxing and opening my throat. I just kept going until I suddenly felt the ballsack on my chin before my gag reflex kicked in a little. I backed off, relaxed again and went all the way down with my chin pushing on the ballsack.

At the same time Sue caressed my dick through the panties. I held there with the whole dick in my mouth for a few seconds and her caressing my dick. Then I shot a load of cum in my panties. I kept sucking hard on the dick until I finished unloading in my panties and slowly slid back off, sucking as I went. Sue continued to massage my cum filled panties and said, "You did that like a pro. I am so proud of you!"

The next time I sucked the dildo she read a story about a guy's first time sucking dick. Sue synchronized the guy in the story cumming in the guys mouth with me cumming in my panties. Sue scooped up some of my cum and wiped it on the head of the dildo. I knew what she wanted and without a word I sucked the head back into my mouth and cleaned the cum off. Sue repeated it until she couldn't scoop up any more.

From that time on, when we read stories about sucking cock Sue had me suck on the dildo as she read them. She got very good at making me cum in my panties at the same time the guy in the story would cum in someone's mouth. Then she always fed me my cum on the dildo.

Part 4 Wearing Panties in Yoga Class