Crossdresser Evolution Ch. 02

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

I was becoming addicted to this new way of masturbating very quickly, though there was still this feeling of shame surrounding it. I made sure I deleted the browsing history and then went to the bathroom to clean up. There I saw myself in these cum soaked pink panties. I could feel some sense of arousal but at the same time was ashamed that I was standing there wearing my wife's 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 just shook my head, took them off and jumped into the shower to get ready to go to work. After the shower I re-stashed the cum filled panties back in the ceiling, finished up some little decorating things so Sue would think I was fully productive while I was here and went on to work.

All the while trying to reconcile all these conflicting feelings and thoughts.

Ch 02 - Getting my wife involved

I just shut down all these feelings for a few days after that but then they periodically started popping up again. There was that part of me that liked wearing the panties and was determined to see what these other guys where doing to get more ideas. There was also this thought that if others were doing this that I could eliminate this shameful feeling about me liking to wear panties.

Well, one night, Sue and I were fooling around and I helped her off with all of her cloths except her panties. I just kept feeling her through them, her buns and her pussy. Then I moved them aside to get her more aroused by fingering her clit. I also got down and was giving her oral with her panties moved to the side. All the while I was massaging her through her panties. If I was honest with myself, I was getting just as much arousal from the panties as I was by her.

Right when I thought about how much I was focusing on her panties Sue asked why I wasn't taking her panties off. I felt defensive immediately and tried to think of something other than what I was really thinking. I could only come up with a half-truth that sounded plausible. I said that I liked massaging her through the silky material. She just looked at me funny and paused for a second that felt like an eternity. My dick had totally gone flaccid by now. Then she said as she took off her panties, that is crazy and that I could do a better job orally with them off.

I just got back to work and gave her the oral orgasm that she was looking for. After she finished she asked if I minded waiting until next time we fooled around to have intercourse. I just said ok blindly after the panty comments. She just rolled over and went to sleep without putting her panties back on.

I grabbed my t-shirt and underwear but her panties were with my t-shirt and I didn't see my underwear. I put on the t-shirt and decided to put her panties on. Then I saw my boxers and decided I had better put them on over her panties. I usually get up before her so I would be able to take the panties off before she was up. I did wake up before her and went into the bathroom to pee and took off her panties. I just dropped them by the side of the bed so she would not know I wore them.

I switch from boxers to briefs when the weather gets cold and my underwear is almost exactly like Sue's except mine has the double panel in the front and hers has the extra layer down in the crotch only. ALSO mine are just cotton and hers are a spandex/cotton blend.

Well, one night after we had been drinking a bit we were fooling around I handed her my briefs with her t-shirt and she put them on without thinking. I also put her pink panties on and we went to sleep.

In the morning I got up next to her, spooning with our whole bodies against each other. She reached around and found my crotch and started massaging my dick through her panties that I was now wearing. After about a minute, I think it registered with her that I was wearing her panties. She sat bolt upright and looked down at my panty-covered dick and I was already leaving quite a wet spot of precum in her panties. I blushed big-time as the smile of recognition came to her face.

She took her index finger and started to run circles on my dickhead through the panties. Then as the panties got wetter she started running her finger up and down over the sensitive part under my dick head only going up and over my dick head to get more precum for lubrication. I was so high I couldn't move. She said, I see you like the feel of my panties while wearing them too. I didn't say anything nor did I have to, it was obvious from my state of arousal and the extreme flow of precum.

Then she stopped. She asked if I wanted her to make me cum in her panties. I said yes with NO hesitation. She then asked if I like the feel of wearing her panties. She had already made the statement but now she wanted me to say it. I said, yes I like the feel of wearing your panties. She just smiled and restarted running her finger up and down the underside of my dick. Then she cupped my balls through the panties and with one gentle squeeze I started cumming in her panties. I couldn't move while she just kept the slow stroking of her index finger going until my dick was finished and softening.

She just got up without saying anything more and went into the bathroom. Nothing else was said all day. When we got into bed that night I was expecting us to fool around and have intercourse. When I started to initiate she asked what I was doing. I said I was initiating sex like you agreed last night. She said I had my orgasm this morning in her panties. I said that wasn't intercourse, just masturbation. She said that it seemed like I had as much fun with that as I normally do with intercourse. I just looked at her with my puzzled look on my face and rolled over to go to sleep.

Learning about crossdressing and sissy men.

Over the next few weeks nothing seemed to be significantly different but the thoughts about wearing and masturbating with panties would come and go each day. I went down once to check on the panties in the ceiling. They were quite crusty and smelled of cum. I thought I should wash them before I wear them the next time.

One evening Sue said she wasn't feeling great and said she was going to bed early. I started to watch a little TV but the thoughts of panties invaded my head. I finally succumbed to the urge to look on the Internet again.

I checked on Sue and she was out cold. Then I went in and typed men cumming in panties into Google. Some of the hits were of stories. I clicked on one that was about the first time this guy got caught wearing panties. He had been wearing his sister's bra and panties when she walked in on him. She encouraged him to finish masturbating while she stripped down to her bra and panties. Then after he came in her panties she scooped up some of his cum and encouraged him to eat it. It didn't seem to take much encouragement and he ended up eagerly eating his cum for her.

I wasn't sure how much of his motivation was that it was turning her on or how much he just wanted to eat it.

In the story, the next day the sister asked her brother to put on a matching pink lacy bra and panty set. She had him prancing around in front of her full-length mirror when her boyfriend walked in. The boyfriend looked at the brother and just smiled. He said to the sister you were right, he would put on the bra and panty set. I can't believe it but others will with these pictures as he snapped a couple of pictures with his phone.

The brother was mortified and pleaded with him to delete the pictures. The boyfriend said there is one thing you could do. He proceeded to unzip his pants and drop them to the ground. The kid knew he wanted a blowjob and knelt down and gave it to him while wearing the bra and panties.

The story was so detailed and I was leaking precum like mad into my briefs. When the boyfriend came in his mouth the description was so detailed about his pulsing dick and the flood of cum into the brother's mouth that I came in my pants after the description of the third pulse of cum into his mouth as he swallow it all.

I quickly shut everything down and went to clean myself up in the bathroom. I took off my pants and underwear. I was about to wipe out what cum I could when the thought of the brother eating his own cum came into my head. My dick was also starting to rise again. Instead of wiping out the cum I brought my underwear to my nose and breathed in the smell of my own cum. Then I extended my tongue into the glob of cum and tasted it. From there I sucked my underwear into my mouth and sucked the cum off of it.

I looked up and saw myself in the mirror with my underwear in my mouth and felt that feeling of shame well up inside again. I put my soggy underwear back on and crawled into bed next to Sue who was sound asleep. In the morning my underwear was dry but a bit crusty. I showered and went off to work. I figured if Sue even noticed she would just think I had a wet dream and forget about it.

That night when I got home I had this sinking feeling that I didn't delete the browsing history from last night. I went in acting like I was checking on a bill payment and erased the history. I needed to be more careful.

Part 3 Getting Bolder with Panties & Masturbation in them