Force Cross Dressing (Page 2)

lion in purple thong
Front view of purple thong. I don’t want all our posts to show panty pictures, but this pair is incredibly comfortable to wear and very embarrassing to see on my body. From Mrs. Lion’s perspective, it’s perfection. [Click image to enlarge]
Yesterday morning, Mrs. Lion put a purple thong on the bed for me to wear. It was frilly like the one I showed the other day. I dutifully put it on and continued dressing. Actually, I looked at myself in the mirror first. Ridiculous! I was working at home but had a number of video conferences, so I got completely dressed. To my surprise, that silly thong was more comfortable than my boy underwear. It stayed up (most of my underwear tends to ride down) and felt great against my penis. Mrs. Lion has left me wild since we went on vacation.

I’ve read that some other guys like the way women’s underwear feels. My experience so far ranges from uncomfortable to acceptable. I’ve always been very happy to return to my Calvin Klein red boxer briefs. This time, I’m not so sure. For some reason, this thong stays up even when I am not wearing anything else. The front comfortably accommodates my genitals and the rear string sits comfortably as well. I won’t comment on the style. I like this thong much better when it is covered by pants. I’m definitely not a cross dresser. But, what can I say? This thong feels great.

Lion's butt with thong
Here is a rear view of the purple thong. I can’t really feel the string going through my crack. [Click image to enlarge]
For the record, I have some male thongs from Obviously. They are fine and fit well. But they do ride down in the back sometimes and the front is not as comfortable as this purple thong. Weird.

Anyway, I’m sure you are getting bored with my underwear adventures. Mrs. Lion has done a great job finding humiliating things for me to wear. Last night she had me model a lace bra. This number looked totally silly on me. There is no way I can rationalize wearing it. It is female-only underwear. Wearing a bra is way more embarrassing than wearing frilly panties.

She also had me try on — get this — a rosebud baby doll set that included a top that came down just below my belly button and a thong in a matching pattern. You can see it here. It looks a thousand times better on the model than it does on me. Holy shit! There are still a scary pile of undies I haven’t modeled yet.

Mrs. Lion is working out how she will integrate forced cross dressing into our daily lives. In the short time we have been doing it, she either lays out a panty or tells me to wear my regular male underwear. I’ve only worn the bra for a few seconds.

There’s no question that I’m embarrassed wearing this stuff. I think that Mrs. Lion is enjoying the shopping and perhaps is thinking of ways to use forced cross dressing to further humiliate me. It’s all harmless fun for her. I like the way having her make me wear things makes me feel.

More interesting, she seems to enjoy this. She’s having fun shopping for me and appears to get a kick out of seeing me wearing frilly things. She frowns when she doesn’t think the item works well for me; like the baby doll camisole. I think she is genuinely interested in creating a feminine wardrobe for me. I know for a fact that she is having more fun than I.

Lion''s Naughty Stool
This is my naughty stool. We bought it Saturday aand covered it with anti-skid tape to assure my freshly-spanked bottom will feel it. [Click image to enlarge]
[Sunday morning] I managed to get some olive oil on my shirt last night when we went out to dinner. That earned me more punishment. I had already racked one up for spilling the day before. I asked Mrs. Lion if she wanted to “bank” this punishment for a later date. She said that instead, if she wanted she could add a second punishment desert, like both corner time and mouth soaping. I shrugged.

During the day we did some shopping. We went to Walmart. Mrs. Lion took me to the Ladies underwear department. I had to stand there while she took a lot of time selecting panties for me. She would hold up a pair to show me. My reaction, I think, guided her purchases. I ended up with seven pairs of panties. Four of them are thongs. The rest, have very high legs designed to expose maximum cheek. They are a combination of pink, lace, or horrid patterns. She hasn’t revealed what I am going to do with all that lingerie,

We also bought a “punishment stool”. It’s a standard, high, wood stool. We went to Home Depot and bought a roll of anti-skid tape. This is very gritty tape designed to provide steady footing on ladder rungs. The tape is extra sticky and extra gritting. When we got home, we cut the tape to completely cover the top of the stool.

After dinner, Mrs. Lion brought out a large wooden spoon. The back, hitting surface has a patch of the anti-skid tape on it. We tried over-the-knee spanking again. This time she sat on one end of the couch and I lay over her lap with my chest on the couch. It worked!

After a thorough spanking; it was at least 300 swats, Mrs. Lion put the punishment stool in the corner and told me to sit on it. I did. It bit into my tender butt. She went into the bathroom. I heard the water running. She came out. Her hands were soapy and she had her bar of bath soap. She rubbed her soapy hands through my mouth and then inserted the bar of soap. I bit down on it.

I sat there a long time. Drool dripped al the way down the front of my chest. I hated every minute of it. When it was done, Mrs. Lion said I had been in the corner for twenty minutes It was the longest twenty minutes of my life. I felt and tasted the effects for hours.

Surprisingly, the spoon turned out to be one of the milder spanking implements that Mrs. Lion uses. Don’t get me wrong, it hurt. It just didn’t hurt as much as many of her other toys. I suggested that her hairbrush-shaped paddle is the most severe paddle for OTK. Her long-handled, bloodwood paddle — it has a tiny 3-inch spanking end — is beyond doubt the meanest tools in her bag. I hate even seeing it.

After I did the best job I could rinsing out my mouth and taking a shower to get the droll washed off we relaxed and watched a movie. After the movie, we went to bed. Mrs. Lion snuggled and then got out the Magic Wand. She gave me a great orgasm. I went to sleep smiling.

We’re on our way out now. I asked her what I should wear. Would it be a thong? Maybe the yucky lace? Nope. she wants me to wear my regular underwear with the training collar. Go figure.

Spanking shirt
My naughty shirt arrived yesterday along with some girly stuff. Poor Lion [Click image to enlarge.]
Yesterday, I got a comment from Julie of Strict Jule Spanks. She’s become an informal mentor to us both. We’ve only exchanged a couple of emails, but that correspondence, her comments, and her blog have been very helpful in how Mrs. Lion spanks and now forced cross dressing.

Her latest comment really turns up the embarrassment in dressing me in women’s clothes. Mrs. Lion has been shopping online for things for me to wear. She likes shopping online; so do I. It’s painless for me when Mrs. Lion shows me something she might purchase. I make a face and then she goes on with her iPad. What UPS will bring is going to be a surprise for me.

Julie suggested that it’s a mistake to buy online. She says it is more fun to take me underwear shopping and hold panties up against me while Mrs. Lion makes her purchase decisions. When she’s done, I have to bring the items to the cashier and pay for them. Hoo boy!

That will certainly embarrass me. One benefit of being locked into a chastity device is that if I get aroused, no visible erection will  be produced. This is the first case where I find a real benefit in being caged. It turns out that it may be more embarrassing to buy panties than to actually wear them.

On Wednesday night, we had do-it-yourself hot fudge sundaes. I dripped a bit of hot fudge on my shirt. One of my rules is not to get food on my clothing. I figured that I would be punished on Thursday night, our regular punishment day.

Nope. After we finished eating and got the bowls into the dishwasher, Mrs. Lion went to her behind-the-door paddle collection, selected the paddle with points on one side (the Tenderizer) and told me to lie face-down on the bed. She then gave me a very thorough spanking with at least 200 swats. There were some drops of blood where the tenderizer’s pointed side hit me. She only used it for a few swats.

When she was done, my butt was burning. She then pointed to the corner and told me to stand in it. I have no idea how long she put me there. It was very difficult to think about anything other than the pain in my bottom. Corner time is definitely a spanking magnifier. She kept me there long enough for my legs to get tired (a good thing from a punishment point of view). When I was finally released, I gratefully got back on the bed.

She asked me about my corner time. I told her about feeling the pain of the spanking. She said, “Good.” I told her my legs were getting tired. She said that maybe we could get a stool for me to sit on. We have a board with rough, gritty non-slip floor tape on it. She said that would help me feel my spanking.

Ever helpful, I suggested she could line the seat of the stool with the tape. We still have a supply of it. She said we would have to figure out what we want to get and  where we could store it when not in use. I suppose it could go in the garage and could fetch it, and return it when we are done.

We’re still struggling with over-the-knee spanking. Our recent attempt felt a great deal different to me from when I lie on the bed for my beating. We haven’t found a comfortable way for Mrs. Lion to do this. I hope we can figure this out. I imagine that the spanking will be much more meaningful and severe if I am across her lap.

We keep learning. Even though we are in our fourth year of enforced chastity and our second in domestic discipline, progress is slow. My knowledge as a top and educator is surprisingly unhelpful. I’m the bottom and I can’t really teach my top. I also admit that we are doing things I’ve never tried when I was a top. I never gave OTK spankings. My victim was generally tied to equipment.

That’s why advice from a practicing female disciplinarian is so helpful. So far, thanks to Julie, Mrs. Lion’s spankings have become much longer and effective. If she follows Julie’s advice on cross dressing, we will benefit from her experience. Maybe “benefit” isn’t the right word from my perspective. No, not from my position.