Logan's Embarrassing Situations

Surprise Gift

Things just felt so right, now that Phillip filled the empty space in my dull humiliation free life. Ever since that wonderful day in the mr. Johnson's backyard, things have been rough and fun. Phillip moved into my apartment and had completely made himself at home. He wasn't the neatest guy, but his beautiful eyes and dominating personality made up for that. Since moving in he hasn't wasted any time making me into his personal humiliation slut. I had a set of chores that consisted of; keeping the place nice and tidy, cooking breakfast, lunch & dinner, helping Phillip release his pent up stress with blow jobs any time he wanted, getting daily wedgies, grocery shopping, etc. I didn't mind doing these things because it was fun, but at times it could be very embarrassing. When we have guests over, which is usually his hometown friends. I am only allowed to wear a pair of running shorts, a thong or Tighty whities, a t-shirt and a chain necklace with a lock on it. Wearing that necklace symbolized that I was taken and he was in charge.

~Friday morning~

I woke up to a quiet home as the sunlight bathed over my smooth milky skin. I looked over at the clock and was surprised that I had slept in until noon. Usually Phillip would wake me up with a major frontal wedgie, which most of the time led to me giving him a blow job. That's when I realized that my undies weren't being stretched and there wasn't a gigantic piece of meat in my face! I didn't know where Phillip was, so I got up and checked his room. I knocked on the door and there wasn't any response, so I proceeded to creep inside and noticed he wasn't there. Where could Phillip have gone? Did he have a meeting or something? Maybe he just had to run over to his grandfather's next door? I made my way to the kitchen and stumbled upon a letter on the counter. It was from PHILLIP!

" Yo little man, took a trip with the boys, we are taking an end of summer road trip and probably going to the beach. I'll be on vacation and gone for the next couple of weeks. Keep up your routine and enjoy your free time, maybe you should take the time to hang out with your friend. Take a trip or something, don't sit around the house all summer. Also cheek on our nosy neighbor and help him out from time to time. I know he's annoying, but he loves the teasing you do so well. Also make sure to keep your phone on because I'll be sending you tasks from time to time. You'll have to record it and send it back of course, but failure to complete any task will result in your little cock getting caged when I'm back. Have fun dork!"

So Phillip was gone and I was left on my own. At least I could relax and enjoy not having my undies invading my ass every second of the day. As I contemplated my new freedom, I decided to take a long hot shower. The water felt amazing running down my body and over my most intimate parts. Ever since Phillip had me get my nipples pierced, they stayed hard and we're super sensitive. The water jetting out onto them always made me horny and rock hard. This of course made me wrap my soap covered hand around my rod and stroke, but before I could get into a rhythm, I heard my phone alert me with a text.

"Phillip: Hey nerd, time for your first task. Shave all your body hair off. Before I left I noticed some stubble coming back and I want you to be as smooth as butter. Once you're finished make your way to your bedroom and look in the bottom drawer. Inside you'll find a big box, take it to the living room and open the blinds. Make sure to record your reaction and do what the note says inside. If you do well, then I won't have to punish you."

Phillip really knew how to worry me with all these surprises he likes to do. Part of me felt like his grandfather taught him all of this, but who knows. The man was only 65 and definitely built like a bodybuilder in his 30's. He was definitely in the category of a D.I.L.F! That aside, I wrapped a towel around my waist and made my way to my bedroom. I opened the bottom drawer and inside was an all black box with a white bow wrapped around it. It wasn't very heavy, but it definitely was wide. I sat the box down on the coffee table and opened the blinds. The sun lit up the entire room. I felt a little exposed with the blinds completely open and me only in a small towel. I quickly sat down and opened the box and inside was at least two dozen pairs of underwear and all of them were briefs! They were so cute and colorful and all different sizes!  I had to call Phillip and thank him for the wonderful gift.