Sissy Roommate -- Part 6 -- Sissy Doubts

Tank has been giving me money almost every week to buy more outfits.  I think it gets him very excited to send me off to the mall with the assignment of buying clothes to wear that will make me look pretty for him.                                                                                    Here's a cute little outfit I bought on my shopping trip last week.  I love this little denim top.  I think it really shows off how skinny I've become since I started dieting extra hard.  I think my arms look so pretty and feminine in this photo.  And of course I bought another short skirt.  I love how this one is just a little bit flouncy and how it moves and swings as I walk.  But it is so short! If I sit or bend over, my lacy panties are on full display for all to see.   

Tank has been sending me out in public dressed as a girl more frequently.  Tank took these pictures of me outside our dorm building before telling me to go to the Student Union to buy some snacks for him.  At first I was super nervous about walking around campus looking this way. But I was really surprised to discover that nobody recognized me.  I guess that's partly because I was always sort of a loner and didn't have any real friends on campus when I was living as a boy.  But I also like to think it's because I look really cute as a girl.  I certainly get some admiring looks and sometimes comments from the boys I pass as I walk around campus.

I think Tank really likes me and that makes me very happy.  He certainly gets excited and wants to have sex with me a lot. But I guess I should tell you that Tank sometimes brings girls -- especially cheerleaders -- back to our room. He says he needs to keep up his image and that people would think it was really strange if he wasn't sleeping with a bunch of girls.  Anyway, the hardest part is when he texts me that he's bringing a girl over and I have to clear out of the dorm room immediately.  And sometimes I'm all dolled up because I was expecting to spend the evening with Tank.  So I have to quickly clean off my make-up and change back into my boy clothes and plan on spending the night sleeping on the couch in the TV room downstairs.  I guess I get a little jealous when Tank is sleeping with girls and sometimes it's hard for me to fall asleep on the couch thinking about him being in bed with them.  But I believe that Tank really loves me -- in his own way -- and that this is just one more way I need to be a good sissy and to be supportive of my man.

As much as I enjoy making Tank happy -- and as natural as it has become for me to dress and act like a girlish sissy -- sometimes I wonder if I am doing the right thing.  Each day I feel a little part of the person I was before I met Tank disappear.  Sometimes I even get confused if I'm even really a boy any more.  Where will all this lead?                                                                      Anyway, tomorrow I'm going ride the bus back to the mall to buy some more clothes. And this time I am going to go dressed as a girl. That way I can try on things in the ladies dressing room and people won't look at me funny when I'm shopping for bras and underwear. I don't think anyone will guess that I'm not really a girl.  Do you?

Sissy Roommate - part 5 -- Some New Clothes

Well, my trip to the mall was quite an adventure.  I had made a list of the things I thought I would need.  More sexy underwear, some sexy tops and some short short skirts were definitely on the list.  I also planned to buy some more make-up and some brushes and sprays to make my hair look nicer.  And I hoped I would have enough money left over for some perfume -- I thought that Tank would really enjoy that.                                                                             But one thing made me extra nervous about my shopping adventure: Tank had also told me to get some clothes to wear outside.  He was going to make me go outside fully dressed as a girl! So I needed to be smart about what I bought since this wasn't just for sissy dress-up games in our dorm room.

Here's one of the outfits I bought for myself on that first trip to the mall.  Don't you like this cute little top?  I didn't realize when I bought it that it wouldn't even cover my tummy!  But I think it looks super cute.  And I think it looks nice with the short plaid skirt I bought.  I also bought some shoes and a bag that I could take outside with me.

Here's a close-up of my face.  I think you can see that I've gotten a lot better with my make-up.  I think I look very pretty in this photo.                                                                                         Maybe you can tell that I have plucked my eyebrows into a pretty arch shape.  That, along with some eyeliner and mascara, helps make my eyes look extra big and pretty.                                                                                             And Tank really likes it when I wear lipstick.  With some practice, I've gotten really good at putting it on. I spent a little more to get extra long wearing lipstick because regular lipstick doesn't stay on for very long since Tank likes kissing me so much.

And as you can see, Tank was true to his word.  He made me go outside behind our dorm to take these photos.  I was so scared that someone would see me as we went out the back stairs.  But the sensation of being outside dressed as a girl was so exciting!  I loved the feeling of the cool fall air on my exposed skin.  I loved posing for my man as he took dozens of photos of me.                                                                                                And I could tell that Tank was getting excited by taking me outside and making pose for photos.  Because when he was done taking pictures, he grabbed me by the wrist and rushed me back upstairs to our dorm room.  "All fours!  Now!" he growled. I quickly did as I was ordered and positioned myself on my hands and knees on the floor.  Tank pulled down his pants and approached me from behind, lifting up my skirt and pulling down my lacy panties.  Tank loves to fuck me in all sorts of different positions -- but I think he likes it best when I'm on my hands and knees.  I love it when he spanks my bottom while his dick is pumping in and out of me.  It gets me so excited when Tank says how tight my "pussy" is while he's fucking me.  I have to admit that it's pretty painful when Tank fucks me because his cock is so enormous. Sometimes it hurts so much that I cry while Tank is pounding away at me.  But it also makes me feel so happy and fulfilled to be pleasing Tank and to submit to him so completely.