looking for lite sissy dares

[pantyhimbo]

Hey,

I'm a 30+ yo male, straight, with a little sissy fetish. Therefore I'm looking for some nice and easy sissy dares. I don't want to be exposed completly as I'm still a little bit shy about this whole topic, so here is a list with some examples that are and aren't and are maybe ok for me:

Ok:

• buying female clothes, including panties and bras
• wearing female clothes in public that you can't see e.g. panties under opaque trousers or a bra under a coat
• wearing female clothes in public, that are not obviously for women, like normal jeans or normal shirts
• wearing obviously female clothes when I have a lot of control who will see it (little risk that it will be seen by other than the intended ones), e.g. flashing panties in controlled situations

Maybe:

• showing panties or wearing obviously female clothes in a little bit riskier situations, but only with a low risk that I could get caught by friends/co-workers
• buying anal toys or something like that (using them is more probably nothing I'm willing to do)

Not ok:

• wearing obviously female clothes in public, like walking around in a skirt
• wearing non-obvious female clothes at work or when meeting with friends etc.
• anything that involves photos or something similar

Maybe you have some nice ideas what I should do. As there is still a lot closed around here, I can't promise to do things soon. But I will report if I fulfill a dare.

So please give me dares, but please have some mercy on me

[grannyd16]

Buy yourself a skirt but before you buy it you need to do one of the following:
-go to the changing rooms and try them on
-Ask someone if it suits you
-Find some panties that match them style wise

[Marshmallow_Bitch]

buy and wear a g-string, it has to be visible above pants, but you can keep your shirt over it. "Accidentally" make them show at least 3 times throughout the day.

[pantyhimbo]

Originally Posted by grannyd16

Buy yourself a skirt but before you buy it you need to do one of the following:
-go to the changing rooms and try them on
-Ask someone if it suits you
-Find some panties that match them style wise

Ok, this is a tough one, but I will definitely try to fulfill it. I think I will go to another city to do it, so it could takes some time. Thank you for the dare!

Originally Posted by Marshmallow_Bitch

buy and wear a g-string, it has to be visible above pants, but you can keep your shirt over it. "Accidentally" make them show at least 3 times throughout the day.

This sounds interesting and I will do it soon. Does it have to be seen by others when I "accidentally" show it? And if so who? A single person or a group? Females or males? I think I would prefer to show it to women only if I it's my choice. Thank you for the dare!

[pantyhimbo]

Originally Posted by Marshmallow_Bitch

buy and wear a g-string, it has to be visible above pants, but you can keep your shirt over it. "Accidentally" make them show at least 3 times throughout the day.

As I had a free day today (I've a part time job right now as I'm still studying) I took the opportunity to do my first dare. So I went to a nice little clothing store and I was already very nervous when I left home. When I entered the store I directly went to the lingerie section. But then I saw a former school mate working there and she also recognized me. This made me to leave this store and I decided to drive to another city.

The store in the other city was almost empty (I saw just a few customers when I entered and two salesgirls) and I directly headed for the lingerie section again. While looking at all the panties one of the salesgirls approached me and asked if I needed some help. I just stumbled something like: "No thanks, I'm just looking".

Finally I found a nice string which is red and has some lace on it and I decided to buy that one. Probably it isn't exactly what is meant by a g-string, but it was the one that came the closest to a g-string. So i grabbed one in the size I thought would fit and went to the checkout. While going to the checkout I almost lost my courage and I kinda slowed down and thought about not doing it. But I said to myself, that I have to do it and finally I arrived at the checkout. The salesgirl already awaited me and the salesgirl, that asked if I need help went back to the checkout as well. The moment I arrived two women also came to the checkout and beeing a good gentleman I offered them to let them go first (the main reason was probably that I didn't want them to watch me how I buy female panties). I held the thong in way I was sure you could not really tell what I was holding, but it was obvious, that I didn't buy much things. One of them said, that it seems like I don't want to buy many items, so I could go first. But I insisted to let them go first and they did so. I was kinda reliefed cause I thought buying it in front of the two salesgirls is enough for the beginning.

When the two women had checked out, the salesgirl indicated that it was my turn now. But the two women still packed their stuff into their bags. So I just said: "Oh please, wait a second." and pretended like I wanted to have a look on some of the items near the checkout. After what felt like an eternity the women left and I stepped to the counter. Maybe I shouldn't have done it in the moment right after they left, as it probably made it very obvious, that I was embarrassed. When I put the thong on the counter the salesgirl said something like: "Well, now it's your turn." The way she emphasied the "now" I am sure she knows, that I waited till the other customers left. But no other comment was made and both of them just had a friendly smile on their faces.

After buying it I went back to my car and drove to a quiet place. There I took of my boxers and changed into the thong. I especially put a big towel in my car, so I could cover myself while changing, but no one came near my car, so probably no one would have seen it anyways. But I have to say that it was still very embarrassing to put it on. I think getting dared to put it on made it even more embarrassing. (It doesn't fit well, by the way.) Then I drove to a mall and went for a little walk through it. I made sure, that my thong was above my waistband as you dared me to. Knowing that only my shirt covered the thong made me nervous as hell and my heart was pounding like mad. I checked if my shirt was still low enough about every five seconds.

After walking around for almost an hour, I felt like the nervousness settled down a bit and I remembered, that I still had to show the thong 3 times. So I went into a big grocery. Inside I searched for an empty aisle, made sure no one was around and did some tests like bending over. I recognized that reaching for an higher shelf would raise up my shirt just enough to show a bit of my thong but only so little that the chance was high it won't get spotted. But bending over or down to look on one of the button shelfs would put my thong on full display, so it would be hard to miss. So I decided to go with the reaching up for the first try. And I saw that there were some kind of transparent plastic covers at the edges of the shelfes to put labels behind them. This plastic was a little bit reflective and therefore allows you to have a slightly view what's going on behind you. After some strolling around I found a long aisle with only one woman (maybe in her mid-forties) inside. I entered the aisle too, walked slowly toward the woman and than waited on a spot pretending to look at items. While the woman kept comming closer (she took her time, so it felt like an eternity) I changed my mind back and forth if I should reach up or not. When she was almost at my level I decided to summon up all my courage and do it. So I reached up to a higher shelf, but the reflection told me, that she wasn't even paying attention. I was a little bit disappointed on one hand, but it was a huge relief on the other hand. Even that she probably didn't see it, I count that as showing it one time.

After a short time of searching I found another opportunity. A woman (I would guess that she was about my age) just entered an empty aisle form the other side, so I entered it as well. This woman was faster than the first so I didn't have time to hesitate that much. Just before she came to my level I reached up again and felt how my shirt slided up. But she just looked at items on the other side and didn't pay any attention to me. A few steps after she passed me she stopped to look at something and I reached up a few more times, but she did not look. Spontaneously I decided to go a step further and bend down. I immediately felt how my shirt raised up and I knew that my thong was on full view now. But she never turned her head to my direction, so I'm very sure she didn't recognize it. Probably it lasted only a few seconds before she went on, but it felt soooo long again. After she proceeded I saw a man entering the aisle on the other side and I decided to stand up quickly.

So just one more time to go to fulfill this dare. After some searching I found a group of young people (probably in their early-twenties, 2 boys and 3 girls). As I said before I would prefer showing my thong only to females (I don't know why but it would be way more embarrassing to me if a man found out my "secret") and of course I think a single person is less embarrassing than a group. But I got away very cheap the first two times and so I decided that I have to flash my thong in front of this group to fulfill this dare. The group was quite far on their way to the other end of the aisle. This aisle and the next one are full of sweets, so I thought they might go into the next one too and went to the next one directly. I rushed to the end of it and waited. I could hear them talking and so I knew, that they were about to leave the aisle and come around the corner and I was ready to reach up in this moment. I don't know what happened in this second, but something turned a switch in my mind and out of a sudden I decided to bend down and so I did. So I was bending down with my back facing the side they could come around any second and with my thong on full display. From the corner of my eyes I could tell, that they didn't come around the corner yet. But I could see some shadows, so I knew they were already standing next to my aisle. But then something changed my mind again completly and I really chickened out. I stood up straightaway and just a second later they came around the corner. I quickly leaved the store, pulled up my pants, so the thong was below my waistband and rushed to my car. I drove away a bit, changed back to my boxers and drove back home.

It took some time after coming home to find the courage to write it down. I think I was really brave today and tried to fulfill this dare. But to be strictly accurate I did not every part of the dare. So if you think that I did not enough to fulfill this dare, you could tell me some sort of a punishment I have to do.

[nya]

Two easy ones. Sit down to pee, always no excuses.
Start watching makeup tutorials on youtube or tictok.

[pantyhimbo]

Originally Posted by grannyd16

Buy yourself a skirt but before you buy it you need to do one of the following:
-go to the changing rooms and try them on
-Ask someone if it suits you
-Find some panties that match them style wise

When I read this dare for the first time, I thought I have to "do all of the following" and not just one. This makes it much easier of course and I decided to give it a try today.

Originally Posted by nya

Two easy ones. Sit down to pee, always no excuses.
Start watching makeup tutorials on youtube or tictok.

I promise to sit down more often to pee, but not always especially not in public restrooms. They are gross. And I will do the other one. Thanks for the dares!

[aralius]

Go back to the store your bought the gstring.

Look in the lingeree section until someone comes to help you. When they ask you must accept their help and tell them you want a matching bra and panty set and that you need help with the sizes.

Tell the assistant your budget and that she can choose anything within that budget in the correct size for you.

You must try it on if she asks if you want to try it for size.

[Paladintwk]

I modified these from my PM Dare list to hopefully make them lite enough for you. If you ever want ideas more challenging check my PM Dare List.

PANTY JACK GET DARE: Jack off in panties while playing Get Dare and leave them on soaked in my cum while I am online playing. I have to post on my signature or in the chat room that I have done this dare and that I am currently wearing the cum soaked panties while I am online until someone gives me permission to take them off. If no one gives me permission I have to wear them until morning.


PANTY JACK COCK HERO GAME: I will play what ever Cock Hero Video you send for 20 minutes stroking to the beats without stopping wearing only panties or a thong. If I cum I will have to lock myself in a chastity cage immediately wearing only my cum soaked panties or thong and stay locked for X hours based on the roll of a pair of dice (2 to 12 hours) A detail report will be provided on request.

[grannyd16]

Originally Posted by pantyhimbo

When I read this dare for the first time, I thought I have to "do all of the following" and not just one. This makes it much easier of course and I decided to give it a try today.

While I did intend for you to do one if you wish to do more than 1 its up to you

[pantyhimbo]

Originally Posted by grannyd16

Buy yourself a skirt but before you buy it you need to do one of the following:
-go to the changing rooms and try them on
-Ask someone if it suits you
-Find some panties that match them style wise

Originally Posted by grannyd16

While I did intend for you to do one if you wish to do more than 1 its up to you

As I told before I tried to do this dare today. The stores were much more crowded than yesterday. But I told myself that I wasn't allowed to cop out again. (I think, I would have never done something like this by myself, but the dares put some pressure on me. So I'm glad and a little bit proud that I finally picked up the courage to join this forum and ask for dares. But I'm also afraid of what else is going to come and where all of this will lead to.)

I went to a store and looked at several skirts and I felt less nervous than yesterday looking at the panties. Finally I found a skirt that seems to have the correct size and wasn't that expensive. It was a black one out of viscose with lot of flowers on it. So it was time to decide which of the extra tasks I should do. Asking some one if it suits me wasn't an option for me. There were many people around the fitting rooms and I didn't want them to see me going to try on a skirt, so I thought about looking for matching panties. But then I had the idea to grab some other items and hold them in a way you can't see the skirt (this wasn't forbidden in the dare).

I grabbed some male pants and went to the area with the fitting rooms. There I had to wait because all rooms were occupied and a few other people waited too. While standing there I was nervous as hell and checked all the time if the skirt was really hidden under the pants. And I recognized two things while waiting: 1. You really have to close the curtain properly to prevent any gaps. 2. The curtain was long enough to hide most of your legs, but if you don't pay attention how you put on things, they could be spotted from the outside under the curtain. When it was up to me, I had the "luck" that it was a room directly facing all the waiting people. This made me getting even more nervous. In the dressing room I decided to start trying on the pants. After I've tried on the three pants it was time for the skirt. I double checked the whole curtain, sat down on the chair, hold my legs up above the lower edge of the curtain (to ensure no one could see what I was trying on) and put on the skirt. It looked really silly on me and I felt very embarrassed. But it also turned out, that the skirt was at least one size to big, cause it kept sliding down.

I think the whole sense of trying it on was to find a fitting one, so I had to do the whole procedure again. I grabbed the same skirt just two sizes smaller, took some male pants and went to the fitting rooms again. This time I had more luck, as I got a room in the corner. For a short moment I thought about not sitting down on the chair to put the skirt on or even leaving a small gap in the curtain, but I discarded this idea right away. This time the skirt fitted perfectly, but it also looked even silier. Although I forced myself to keep it on for at least a short moment and turn around and watching me in the mirror.

I had luck at the checkout this time, as it was all empty when I got there. This salesgirl weared a facemask, but I think she showed no reaction. I don't know why, but buying the skirt was less embarrassing than buying the panties. The most embarrassing part was to try it on.

I indeed took an easy exit (hiding the skirt under other items), but this was not forbidden. So I would say, I managed to fulfill this dare and therefore I fulfilled my first dare (I think I'm not allowed to count the other one from yesterday) and I have to admit, that it makes me a little bit proud

[grannyd16]

Good report, fair enough I didn't specify in the dare which is my fault, however, that means the next one will be even more exact and less lax on the rules. So I hope you look forward to that.

[pantyhimbo]

Originally Posted by aralius

Go back to the store your bought the gstring.

Look in the lingeree section until someone comes to help you. When they ask you must accept their help and tell them you want a matching bra and panty set and that you need help with the sizes.

Tell the assistant your budget and that she can choose anything within that budget in the correct size for you.

You must try it on if she asks if you want to try it for size.

Oh I think I'm not a good sissy, as it turned out that I have much more problems with even the easier dares than I thought I would. Thinking about doing stuff like that feels way easier than really doing it. I noticed that I'm quite uncomfortable with someone knowing I was buying female clothing for myself or even wearing them. When I opened this thread I was aware, that it could bring me to the boundaries of my comfort zone, but I decided to do this step although. But I didn't knew I had to leave my comfort zone entirely so soon. However I'm willing to get better and braver and so I think I have to at least consider doing this dare. I promise to consider it and thanks for the dare!

Originally Posted by Paladintwk

I modified these from my PM Dare list to hopefully make them lite enough for you. If you ever want ideas more challenging check my PM Dare List.

PANTY JACK GET DARE: Jack off in panties while playing Get Dare and leave them on soaked in my cum while I am online playing. I have to post on my signature or in the chat room that I have done this dare and that I am currently wearing the cum soaked panties while I am online until someone gives me permission to take them off. If no one gives me permission I have to wear them until morning.


PANTY JACK COCK HERO GAME: I will play what ever Cock Hero Video you send for 20 minutes stroking to the beats without stopping wearing only panties or a thong. If I cum I will have to lock myself in a chastity cage immediately wearing only my cum soaked panties or thong and stay locked for X hours based on the roll of a pair of dice (2 to 12 hours) A detail report will be provided on request.

I promise to do the first one and think about the second one. But I can't promise anything for that as I never really thought about chastity or things like that. Thank you for the dares!

Originally Posted by grannyd16

Good report, fair enough I didn't specify in the dare which is my fault, however, that means the next one will be even more exact and less lax on the rules. So I hope you look forward to that.

I'm afraid to be honest!

[pantyhimbo]

Originally Posted by nya

Two easy ones. Sit down to pee, always no excuses.

As I said before I'm willing to obey this rule, but I don't want to do it forever. Therefore I decided to sit down to pee where it is possible for me (I'm disgusted by toilet seats in public restrooms, so I won't do it there) for one week until next saturday.

Today I took a ride with the bike (I cycle quite often) and on the way I felt that I had to pee. So I stopped near a tree and got off the bike. I was up to stand next to the tree and pee, when this dare came back to my mind. I wasn't sure, but I think this dare includes peeing like a girl outdoors too (correct me if I'm wrong). As I didn't need to pee badly and this lonely tree didn't provide much cover, I decided to proceed until I would come to the next wood. I've never seen anybody else on this way, so I thought that this should be a much safer space to do it.

I rode my bike midway through the wood and stopped again. I didn't want to leave my bike behind and the covert is quite dense in this wood, so I wasn't able to go very deep into the forest. There was a thick tree near the way and I determined it as the best spot to have the most cover and I went behind it. With the hope to spot upcomming people quick enough I stood there facing the way, took a deep breath and pulled down my bike shorts (was very glad, that I didn't wear bib shorts today) and my boxers to my knees. And then it was time to squat down. I peed sitting down before for a few times and I think it is impractical and annoying, but not too humilating. But squatting down to pee outdoors like a girl instead of just standing there like a man, felt so weird and I was pretty humilated and embarrassed. And this must be an embarrassing position even for a woman. Watching a woman peeing outdoors is a big fantasy of mine and I once managed to catch one "accidentally". She was really upset about this situation and my today's experience made me feel a bit guilty for provoking to catch her back then.

After squatting down I tried to pee, but I was so nervous and humilated that I wasn't able to pee. Felt like being in a public restroom with other guys. I'm often not able to pee in this situations too. And probably the need wasn't big enough in this moment. Another problem for me was to find a position in which I could hold the balance and didn't need to worry about peeing myself. The bike shorts are quite tight and prevented me from spreading my legs far enough and pulling them down to my ankles even made it worse. I noticed that the best options could maybe be to either lean my back to another tree or squat down quite deep (with my butt almost touching the ground). Finally I surrendered (My log showed me that I tried it for more than 10 minutes.) and decided to go on as the need wasn't too big and pee standing up felt like rule-breaking.

Just squatting down was soooo embarrassing even without peeing and I guess it would be even more embarrassing with peeing as it would put me into a very helpless situation till I finished. However I promise to try it again if I had to pee again while riding the bike in the upcomming week. Probably I should think about a good way to pee like a girl but while writing this I notice how weird it feels to just think about this question.

[littlejoanne]

it sounds like you have bought some women jeans. am I right ?