Making Life Fun: Duration

Well sadly both of my parents are back so I have to be more reserved in the part of my life that has been able to be unleashed on getdare and when my parents are gone. I have to be more reserved and in sexual tension since my parents are very vanilla. However, I did do some things that were pretty tame while my parents were gone after playing Rock Band with no pants or underwear on. One night I went to let our dog outside. We have an outside deck that is enclosed because of mosquitoes and we have a hot tub which I enjoy going skinny dipping in from time to time. However, with the heat as it is, it's too hot to go in the hot tub. Anyway, since my dad was upstairs, and the deck door is on the middle floor I decided to do just a little something. Before I let Maggie (our dog) out onto the deck I shed the bottom half of my clothes so all I had on were my glasses and two tee shirts. I went out onto the deck in just these two shirts anyone able to see my dick, because there was no way possible to bend my body so that the shirts would cover my dick. They just wen above my waist. So a little something there.
Also when my friend came over on Thursday I wore boy shorts the whole time he was over. I also wore my jean shorts which are really loose and when putting some weight in the pockets they sag down. I had weight in my pockets...So at any time he could look and see the black fabric of the boy shorts poke out from the top of my jeans. If I wasn't so scared of freaking him out I would've slipped my shorts down more. However, later in the evening they began to crush my balls and it hurt. After he left I took them off. That's something I don't understand if they're called boy shorts how come they're meant for girls? That week I had also wore a sky blue thong I own. Yes it is intended for women it's not a "man thong" in fact I don't own any "man thongs."
Anyway, despite my parents being back there is one dare I am going to be giving myself, that at first glance doesn't seem too difficult. However, in certain situations it can be. As I have said on some of my truths on here, sometimes I do sleep naked. I have no problem with it especially in the summer time when it's really hot. I sleep with two covers a sheet and a comforter and I always have my ceiling fan on full blast whether it's winter or summer. Starting the day of my 26th birthday which is in September, I am going to attempt sleeping naked every day for a full year. Now I can't take naps, my physiology for some reason doesn't allow it, unless I'm sick but if I do take a nap the rule applies then too. Also, if I have to go to the bathroom in the middle of the night, I'm not putting clothes on. Now like I said this may not seem too difficult at first glance but take this into account. What if I have to share a hotel room with my parents? What if my family comes over and I have to share a bed with a cousin? What if I'm on a camping trip with my friends? Whole lot of things that could be taken into account here. But to make this even more exciting, hopefully, I'm going to try and attempt to do something unique for every day sleeping naked. Like one day I may try to orgasm using my less dominant hands, other nights I may edge x amount of times giving myself no relase for that night. But seeing as I don't have the creative skills I want, I will probably be turning to the gd community for rituals to perform before I fall asleep that will heighten the experience. I will be posting this suggestion shortly before I undergo this experience and hopefully I'll get some feedback. Also if you have any ideas right now you can comment on here. I do have limits, but not a lot of them are sexual in nature so I'm pretty open minded.