House Sitting Dare

Hello,

Katie here, John and I are both busy with finals so he's making me write our next post. First off we loved hearing all the wonderful responses from our first dare. I have always been self-conscious about my body so hearing all your lovely words was greatly appreciated. Our last email account was too full of spam, which is why we made this new one so I apologize if we did not respond to anyone’s. I am still a little nervous and don't feel comfortable taking/posting some pictures so apologize for the ones I don't post. Since this whole dare debacle started John and I have become very close and have done many things together. Being the generous person that I am, a lot of the stuff doesn’t require him to burn a dare, as long as no pictures are posted. While reading the dares that are sent to us I get very turned on and hope I can find the courage some day to attempt them. We do have quite a few pictures/videos however that I may be willing to share so I can start slow and become more open. For this post however there are 2 from the actual event and 1 that is not. I hope everyone enjoys and please feel free to respond. Sorry if my post is too long but I kind of get turned on by retelling it and like detail :)

For John's next dare I had to spend an entire day completely naked, with a few extras. I was house sitting for my aunt and was planning on being alone all weekend to study. I didn't know John was planning on using a dare over there so he tricked me into coming over. He lied and told me he needed a quiet place to study so I gave him the address. When he arrived I let him in the front door and he immediately said, "take off your clothes!" I said "hell no" I had a lot of studying to do and didn't have time to mess around. He replied by telling me that this was his next dare so I would have to study naked. Now knowing I had to do it, I reluctantly stripped down while the front door was still open. It wasn't until I was completely naked that he closed the door, which made me even more embarrassed.

Once naked he made me give him a tour of the house. Although he has seen me naked before I was still embarrassed and tried to cover up as much as possible. Walking naked though a house that isn't yours I have to admit was quite exciting however and I was wet the whole time. Judging from the tent in Johns shorts I could tell it was quite exciting for him as well. After showing him all three levels during my nude tour we finally sat down to study. It wasn't until then that he told me I had to stay naked for the next 24 hours straight. I was pissed and called him a jerk but also realized he could have given me a way harder dare so agreed. John got his books out then immediately left and said he had to go use the bathroom. To my surprise the dumbass accidentally left his phone on the table so I made sure to capitalize on that. I really didn't want him taking pictures the whole time so I set a passcode on his phone. This way he couldn’t access it unless I gave him the correct code. He may have his dares but I certainly have my tricks ;) With an iPhone you can still take pictures even when locked but John is technologically retarded so I was almost positive he didn't know about that. Luckily I was right. He was in the bathroom for a very long time so I can only imagine he was in there jerking off.

After finally getting back he instantly noticed his locked phone and became super pissed off. We argued for a while then he told me I had three options. 1) I could tell him the pass code 2) I didn't have to tell him but this dare wouldn't count and my next dare would be REALLY bad or 3) I didn't have to tell him until the 24 hours was up but he would add something to my current dare.

I really didn't want picture documentation of this and I didn't want a worse dare so I took my chances and went with option 3. With a smile he told me the extra part to the dare and I wished I would of just picked option 1 and told him the damn passcode. The add-on was that I now had to masturbate in every room of the house and if I didn't get to each one before the 24 hours was up the dare wouldn't count. This could be either masturbation with my hand, or masturbation with any item found in that room but the only regulation was I HAD to orgasm for the room to count. I was scared because my aunt and uncle have 4 kids so their house is very large. Normally I masturbate tops once a day so I told him there was no way I could orgasm that many times. He said if I couldn't or didn't want to masturbate in a room, I would have to make him cum with a blowjob or sex.

I could tell John was still pissed about me locking his phone because he made every closet, hallway, staircase, and even tub count as a separate room. The bastard even counted the back deck, front porch, garage, and the car in the garage as individual rooms. Each room could be a story in itself and I have already rambled long enough so I won't discuss them for this post. I will however try to post all that occurred in each room on the stories section of T or DP so in the mean time please don't hesitate to ask for the details.

After all was said and done we found that the house had 36 rooms, based on Johns rules of course. Over that 24-hour period I experienced 27 orgasms, gave 14 blowjobs(most of them being deepthroats), and had sex 6 times. The number of orgasms per room doesn’t add up, I know, that is because in some rooms we both came or I gave him head while fingering myself and came before he did. In addition to fingers I orgasmed/attempted to orgasm with a water bottle, a shampoo bottle, a shot glass, 5 pens, a cucumber, a soccer trophy, a baseball bat handle, a car shift knob, and other various items found in each room that I can't remember off the top of my head. Towards the end my pussy/clit hurt so bad that I even resorted to trying my butt. Often I hear that anal orgasms are better than vaginal ones so thought it was worth a try to give my swollen pussy a break. Everything that was put in my tight virgin ass left me with no orgasm and ended up hurting far more than my beat up pussy did. My poor virgin asshole was violated with a finger, a pen, a clothes hanger, a toothbrush handle, an Icy Freeze Pop, and worst of all, the head of John's fat dick. Even though he went slow and was super gentle, my ass was so tight that I screamed and experienced the worst pain of my life from just the head.

All in all we both had fun and I apologize again for the lack of pictures. John tried to convince me to reenact some by putting items in my pussy while he takes pictures but I said no. Like I said earlier I am new to posting pictures so am still a little nervous. The first 2 pictures I am posting are during the initial house tour where I was still super embarrassed about being naked. The third is a screen shot John took of me fingering myself over webcam. I thought I'd add it to make up for locking his phone (sorry about the quality). I told John I would also post some pictures of us having sex and me sucking his dick to make up for it also but at the last second I chicken out.

Once this dare was finally over I made a terrible mistake however and am petrified for my next dare. I told John that my pussy was so incredibly soar and begged him to be gentle on it for his next dare. I was horrified when he replied by saying, “ok that’s fine, I’ll give your pussy some time to recover and fuck your ass instead.” He also told me that if I don’t let him take pictures and post them he will make me suck his dick after it has been in my ass D: This is probably good news for the viewers but I am super scared from how much pain just the head of his dick caused last time. I think I will probably get torn apart if he puts the whole thing in me. He may be joking and was very gentle last time so I know I can trust him but am still dreading it. If anyone has advice on how to prepare for anal or just any tips in general please please PLEASE let me know. I look forward to hearing responses and stay tuned for our next post.

John - EMAIL ME!!
todp1992@yahoo.com