Crossdresser Evolution Ch. 03

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

I was becoming addicted to masturbating while wearing panties, though there was still a feeling of shame surrounding it. 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. 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 sissy or feminized men and I also learn about them sucking cocks. I taste my cum for the first time.

Ch 3 Getting Bolder and My Wife Finds Out

Buying my first panties.

After looking at underwear ads and pictures of both men and women in bras, panties and other lingerie I was itching for something more exciting than Sue's underwear. I went into a couple of department stores during my lunch hour but lost my nerve before I could purchase anything. There were always too many people and I was SURE they knew I was going to wear them myself. Then it got close enough to the holidays that I told myself that people would think I was buying things for my wife instead of always thinking they knew I was shopping for me. I also went mid-morning when it wasn't so crowded. I picked out a matching bra and panty set. It was pink with a bunch of lace along the edges. The panties were string bikinis. I also picked up a yellow thong. It was very sheer. I figured it would leave very little to the imagination. When I went to the register the lady just asked if I found what I was looking for, I said yes and we didn't say any more than was necessary to finish the transaction. I hid my stash under the car seat and headed back to work. Now I would have to get them into the house without detection. I stopped in a shopping center parking lot on my way home, removed all the rosa-blanca.ru and hangers and dropped that stuff in a trash can. Then put the bra and panties back in the bag ready to be brought into the house and stashed away. That time came later that night while Sue got ready for bed and I was taking out the trash.

Cumming in panties while Sue sleeps.

A couple of days later I brought home some stuff from work and told Sue I had some work to do but would just do it after she went to bed. She decided to just go to bed a little early so she could get some extra sleep and I could finish up earlier. I started doing my work while Sue got ready for bed and then continued for about 15 minutes after she got in bed.

Then I went downstairs and retrieved the pink lacy bra and panty set. I quickly dropped my pants and underwear. I slid the panties on and before I could pull my pants on my dick was getting hard. Then I slipped off my t-shirt and slipped my arms into the bra. I had taken Sue's bra off many times but hooking the bra took me a couple of minutes. I finally got it and slid my t-shirt back on over it. I went to the powder room just to see if the bra was very visible. It was only a B cup but when looking from the side it was fairly visible. I did love the feeling of the bra hugging my chest. At that point I wasn't sure why women always wanted to take off their bra. I loved it.

I went back to the desk, opened the browser and typed in men cumming in panties while wearing panties. I switched to images and started looking at the men wearing panties with erections stretching them. At that point I wished that I was sitting there only wearing the bra and panties.

I alternated feeling my dick down my pants and feeling my chest under my shirt and through the bra. I fell into some pictures that had captions and short stories on them. Men saying what they liked about being feminized, women coaxing or forcing their husbands or others to try on panties, bras and other women's clothing. Then I noticed that the ones that made my dick jump were the ones where the women were getting their husbands to think about or even try sucking on a real guys cock. Some had great descriptions of the guy's dick pulsing in the husbands mouth as it pumped cum down his throat or into his mouth.

After I hit a series of about ten with good descriptions and some GIFs with the husband being "helped/encouraged" to suck a guys dick I came in my panties. I wasn't really prepared for this and the cum was showing wet right through my sweats. I got up and went to the bathroom to clean up before it got too bad.

There I took off both the bra and panties, re-dressed and re-stashed the bra and panties. Then I went back to the computer to delete the browser history. Check, check and check, everything cleaned up.

I started to repeat this once or twice a week, each time going through the cleanup to cover my tracks. I had no idea how to approach this with Sue if she caught me. I started to wonder if I was gay since dicks in panties and sucking dicks was turning me on so much but when I "tried" to look at guys in public trying to imagine their dicks or sucking their dicks I felt repulsed. I still REALLY liked looking at women and their buns or cleavage. Always looking for panty lines, panty waistbands or their butt cheeks hanging out of their shorts or peeking out from a short skirt. I absolutely love short jean skirts.

One night Sue got up to see when I was coming to bed. I was almost ready to cum. Since I was so engrossed in the pictures I almost missed that she was coming. I closed the browser and acted like I was working. She came in and asked how much longer and I fumbled but said about 5 minutes. I stayed hunched over the desk slightly thinking that if I didn't she would see the bra through my t-shirt.

She went into the kitchen and was reading the paper so I thought I had time to take off and re-stash the bra and panties. I went into my closet and quickly took off my t-shirt and the bra and slid on my sleeping t-shirt. As I was doing that I noticed that the bra had left visible lines in my skin where it had been. I hesitated for a moment admiring the bra lines. I took off my pants and admired the panties for a moment but then heard Sue coming. I had no time to remove the panties so I put my boxers on over the panties, I slid on my sleeping pants and shoved the bra in the bottom of my underwear drawer as Sue came around the corner.

I went to brush my teeth and slid into bed beside Sue with the pink lacy panties under my boxers and sleep-pants. My heart was racing as I rolled over toward Sue and gave her a hug and a kiss goodnight. All I could think was that I was lucky to have been able to get the bra off. With her hugging me, I was sure she would have noticed it.

I slept part of the night with my hand down my pants caressing my dick through the panties. I woke up with a woody and went straight in to take a shower. After noticing the panty lines in my skin I temporarily stuffed the panties between my sleep cloths. I hope Sue doesn't come in before the panty lines on my skin fade. The cool water felt good as my woody softened and relaxed. After dressing in my closet I stuffed the bra and panties in the front of my underwear and went down to re-stash everything. Finally, I could relax a bit (or so I thought, remember, I didn't have time to delete the browser history and at this time I had forgotten about it).

The next day I went to work as usual. I went to change when I got home and found a pile of my folded laundry in my closet so I started to put it away. What surprised me was that mixed in with my underwear was the pink panties that I wore the drunken night we had switched underwear by accident and Sue had made me cum in the next morning. I just put the pile in my drawer, an "honest" mistake. At that point I was unsure what I was going to do with them but they were under 2 pair of my underwear so I had a couple of days before I couldn't say that I didn't see them.

My mind was racing with what to do with Sue's panties but later that evening I thought that I might get away with another "honest" mistake. I could "unknowingly" put them on in the dark one morning and wear them to work. That would open the door to a conversation about how comfortable they were.

The morning arrived and I purposely got up a little early, thinking that I would not turn on the light so it wouldn't disturb Sue. I had gotten out the pants and shirt I would wear so I didn't need the light in the morning. I quickly showered and went into my closet to dress. I slid her panties on in the dark. The silky material felt much nicer than mine, would Sue believe that I was so sleepy or in such a hurry that I didn't notice the material was different? I was going to take my chances. I got dressed and headed for work.

The panties were a bit distracting at work and when I needed to use the bathroom I had to be sure no one got a glimpse of the pink material of the panties. I was leaking precum all day thinking about me wearing panties with my coworkers all around, unaware of what I was wearing. I also wondered if there could be any other men at my workplace that were wearing panties right then. At one point I questioned whether I had forgotten again to delete the browser history from a few days before when I was almost caught looking at men wearing panties. I could not remember specifically deleting it so I had to check tonight.

For now I had to think through the current situation. If I got caught by Sue wearing her panties, my story was going to be that I only noticed ofter I got to work, that I noticed the movement of the material against my pants felt different. I thought about letting Sue know when I talked to her on the phone but chickened out. Then I thought I would tell her as soon as I got home but I opted to not tell her then either.

I got home and went straight in to change. I had just gotten my shirt unbuttoned and was sliding my pants down when Sue walked by and stepped into my closet to say hi. She just stopped short and stared at her pink panties on me as I pulled my pants back up. She said drop your pants. I want to see what you have there. I see that you have been enjoying my panties all day, they are quite wet with precum. I started to tell her I put them on by mistake this morning and she stepped closer, gently put her hand over my mouth and caressed my dick through her panties. I just stood there as my dick got really hard. It took about 2 to 3 minutes before I filled her panties with cum. She wiped her hand on my shirt and said, now you can get dressed but please keep those panties on under your jeans.

I stepped out of my work pants took off the shirt and put on my jeans and t-shirt. The feeling of cum and her panties made me stay horny. She put a towel on my chair while we ate so the cum would not get on the cushions. Everything else seemed to be as usual.

The talk.

After dinner Sue said we needed to talk. Needing to "talk" is never good. And now I was sitting there in her cum filled panties waiting for what she wanted to talk about.

She pulled up a chair and had me move my chair so we were sort of knee to knee facing each other. She said she was on the computer earlier (my heart sunk and I probably blushed) and was looking for a web site she had been on a few days ago and she noticed some of the other history. She said that she wasn't mad at the moment but was disappointed and a bit confused.

I had no idea what to say but just sat and listened. First, are you gay? I probably sounded defensive but I said no and explained how I was not attracted to the thought of being with an actual man but that looking at men and women in panties was stimulating. Then she asked why I was wearing her panties to work today and did anyone else know you were? I said no one knew and that I had gotten dressed in the dark in a hurry and didn't notice the panties until I was getting out of the car. Why didn't you tell me? I was embarrassed. I thought I could just change when I got home and forget about it. Well you clearly enjoyed it. How could you forget about it? Especially after seeing what you have been looking at on the web? I blushed again and just said I don't know.

After a couple of minutes she said, I want you to tell me what is going on in your head when we relook at some things on the web.

She got up, took my hand and the towel and we walked in to the computer. She had 2 chairs in front of the computer and put the towel down and said take off your t-shirt and jeans and sit here, I want to know what you are thinking about and know how they are affecting you.

She sat in the other chair and pulled up a document with several links on it. She clicked on the first link and pictures of women in panties came up. There were front and rear views. There were all different styles, colors and fabrics. There were thin to fat women, some with very visible cameltoes. She asked which ones I liked and what I liked about them. I said I liked most of them. I liked the really sheer ones the best. I also liked the ones that had a bikini bridge or you could almost see the women's pussy lips or extremely large clits through the panty material. I liked almost all rear shots because the panties accentuated the curves of their buns, whether they were small or large. I liked imagining the feeling of the different materials. Again, the sheer ones gave more of a hint of what was underneath. Tight or snug fitting was always better and the pastel colors were better with my preference being pinks and yellows. I saw her glance periodically at my crotch. I think she was checking to see if I was aroused which might mean I was being truthful. I was slightly aroused at that point.

The next set of pictures was of men with erections wearing panties. She asked what I saw and thought. I blushed but said quietly that I saw the same sexy panties and how they were making the men extremely aroused. I imagined how it would feel to be wearing those panties myself. She looked down and saw that my dick was a bit more aroused and she said, ok. Truthfully, I knew that I was more aroused. I went on to say I liked most of the same things about the men wearing panties as the women. Of course the cameltoe was replaced with the outline of the man's dick through the panties and of course bigger was usually better but keeping it inside the panties was usually much sexier than big and hanging out all over the place. My panties had mostly dried by now but now I was getting them wet again with precum. She reached over and ran her finger through the wet spot a few times and then clicked to the next link.

What came up were gay men having sex. She asked what do you like about these. I figured this was a trick question but my dick would probably be the final judge. I said they weren't my preference. The guys giving blow jobs were somewhat arousing along with some of the large cut erect cocks. They just seemed so perfect. The uncut dicks where not as arousing as the cut ones. I had forgotten about my state of arousal until she noticeably looked down. I was happy that my state of arousal was not as intense.

The next group were each of 2 men and 1 women. The women were wearing panties or panties and a bra watching or maybe encouraging one man wearing panties or bra and panties to suck the other man's dick. She asked what turned me on about these. Oh no, another trick question. This one gave me away because I knew I was again really hard in no time. I said that the panties on both the men and woman were great as before. Then she looked down at my crotch and said, I'm thinking there is more as she poked my dick that was hard as a rock. I quietly said that watching the women encouraging the man wearing panties to suck the other man's cock was arousing to me. My dick was acting as a lie detector so I felt trapped into telling the truth, as embarrassing as it was. She started to run her finger over the wet part of my panties again but didn't stop as she flipped through more of the pictures. She stopped and we read a couple of the short captions and stories about the women feminizing the men and encouraging them to suck the dicks. they said if they wear panties they should act like a girl and suck the cock or because they knew the men just wanted to suck the dick. Sue stopped at one where the woman was telling the man that she knew he wanted to suck it so he should just do it. She asked me if I had any thoughts like that. I quietly said that I had wondered what it would be like. She asked if I had ever tasted my own cum and I had to say yes, once.

She was still slowly rubbing my dick through the panties and she asked if I would taste it again for her. She was intensifying her rubbing while she was asking and I hesitated but nodded my head and said if she really wanted me to I would. I would probably do just about anything for her and she knew it. I ejaculated into her panties for the second time tonight before I finished my sentence. She waited a minute for me to finish then with two fingers scooped up some of the cum that had come through the panty material and put it and her two fingers into my open mouth. I closed my mouth on her fingers and sucked the cum off of her fingers.

Over the next week or 2 we had sex more than ever and it was mixed with us both sitting at the computer looking at pictures, pictures with captions and stories of men being feminized or how they got involved with wearing panties or crossdressing. I was always wearing her panties and much of the time she was in her bra and panties. After a couple of times I noticed that she would intensify her stimulation of my dick through my panties as she was reading about a guy wearing panties sucking cock for the first time. She would almost always get me to cum in my panties just as the guy would cum in the crossdressed guy's mouth.

The sex also was evolving a bit. I noticed that I was orgasming before her no matter how much we tried to have her go first. After a while it seemed like she didn't want to orgasm while my dick was inside her. She wanted me to bring her off orally. I tried to bring her off orally before I entered her so I wouldn't have to do it right after I had filled her with my cum. Not that I minded tasting my own cum anymore. It was worth the sex. But now she seemed to want me to stop the oral stimulation and mount her just before I was about to make her cum orally which seemed odd. I just stopped questioning what was happening since the sex and her masturbating me in panties was so good. I would just cum inside her when I was ready and then slide down to bring her to orgasm while I also lapped up my cum as it oozed out of her.

Part 4 - Sue helps me buy my own panties and comes home with a toy