My roommate caught me dressed up. He said it was okay with him inside our apartment. I gave him a blowjob when all the blood from his brain was in his morning wood. A few weeks later I gave him the first ass job and he came on my back. Few weeks after that we were having sex and sleeping in the same bed. The perfect set up. And we both knew what it was. No emotional attachment (although I promised to only take his dick and I did get jealous when he would stay the night at a girl’s place). Just sexual satisfaction for him. And my sissy desires fulfilled. And yet, later on, we had agreed on a “permanent role play” when we’re in our apartment. I was to be a girl and only wear girl clothes. And we were college boyfriend and girlfriend living together.

We had a role play Christmas. Where I ordered red lingerie, a bow for my hair, and wrapped my body in Christmas lights. He had gifted me a vibrator and I gifted him several pairs of thin pajama shorts for him to wear when we sleep together (if we weren’t already naked). His birthday came shortly after Christmas break was over and when we returned to classes I gave him a birthday blowjob with icing on his cock. I literally let him put a candle between my cheeks and then blow it out. Then he licked icing off my ass.

Valentine’s day came. We planned to go to the gym from class and then have a “date night” of me dressing up in lingerie and sex. I got to the gym later than he did, so he went home first to shower and I asked him to draw a bath for me with my lavender bubbles. The gym wasn’t very packed. I assumed that all the girls I normally see were already getting ready for their boyfriends like I will be later. After my workout I stopped by our apartment office to grab my Valentine’s Day outfit. It came in the mail a few days before but I hadn’t picked it up yet. I was so nervous grabbing the box from the front office girl. She was very cute and I absolutely envied her body. But I knew being dressed up in lingerie for my roommate, he would pick me over any girl. So I hurried the rest of the way to our place.

I opened the door and heard my roommate’s shower going. The kitchen was cleaned and some of the pots and pans for dinner were out. Part of tonight’s role play was a cooking date too. After I started sleeping with my roommate, I only used my own bedroom and bathroom for my clothes and when I’m changing into girl mode. We shared his shower because it was slightly bigger and it had a seat cutout made for blowjobs obviously lol. When I step into my room, my jaw drops! My roommate had hung sparkling lights on the ceiling above my bed. The sheets were changed to a deep red. On the bed were rose petals. There were several candles around the room not lit yet. And in the middle of the bed was a brand new bottle of lube that I jokingly showed him at Walmart one time (jokingly in public but he recognized the look in my eye). I was soooo excited. Maybe it’s a corny set up. Especially with the many cliches. But this was incredibly unexpected. I giddily skipped into my bathroom. There was a box on the counter. I opened it and found a brand new Xbox controller, red lipstick, bottles of all of the makeup I use, and a pink glass wand with a heart on the end of it. Already my dick was just a thick leaking clit. There was no hope left for any boy thoughts inside me. I stood there looked in the mirror and saw a sissy.

I was in the bathroom for a while. Maybe an hour even. I scrubbed every inch of my body with my lavender bath water and rose dove soap. I shaved my body from face to toe even though I had done so that morning already. I drained the water in the tub and hopped out. In my package that I had ordered, there was black lingerie with red hearts print, red thigh highs, and a brand new red wig. I applied lotion to my entire body. A scent he liked from bath and body works. And the cherries on top were breast inserts that I took time to tape and fasten to my body. To hide my lingerie, I put on white silky pajama pants that were thin enough to see my panties and a crop top with our university logo.

In the kitchen my roommate is wearing a pair of the shorts I bought him for Christmas. Clearly not wearing boxers. The exact reason I bought them. He sees me and I go over to him and give him a sensual hug. I press my breasts against him. He gropes one and chuckles. “Thank you for my controller. I needed one bad.” And I hug him tighter. He slips a hand in my pants and cusps my cheek and says, “you’re welcome.” Then we start on dinner. It’s a playful dinner. We talk about school and our exams from last semester. We drank some whisky. After a little bit of a buzz came on we started talking about the toy he got and how he wanted to use it on me. I was on my knees sucking his dick when the timer beeped to remove our food from the oven. We had a good dinner. It was actually rather light and quick. I think we were both just ready to go back to my bedroom where he prepared the bed for us.

We left our plates on the table. He follows me to the room slapping my ass on the way. I go into the bathroom to check my makeup. My lipstick is smeared from the kitchen blowjob and I ask my roommate why he didn’t tell me! He said that he thought it looked hot. On the bed my roommate was laying down and had put on a movie for some background noise. I hop on the bed and in my hands I have a bag with a gift for him. It’s a pair of shoes he said he wanted and some shirts for working out. He hugged me on the bed and groped my ass while he said thank you. I told him to lay down and I straddled him reverse cowgirl. I give him a lap dance feeling his dick get hard. He pulled my pajama pants down exposing my ass filling a pair of black lace cheeky panties with red hearts. I ask him to spank me which he does. And when I feel my ass is red and warm I turn around and suck his dick. I pull my pants all the way off and stick my ass in the air while I lick his balls. He’s moaning so loud. I bet our neighbors think a girl is giving him the best blowjob of his life. My cock is a rock hard clit barely contained by my panties while I passionately suck his dick. My lingerie. My hair. My makeup. My red painted nails. I have given in completely as I always do inside our apartment.

While we had dinner, my roommate described exactly how he would like to use the glass wand on me. he wanted to lay back. I straddle his torso reverse cowgirl with my ass almost in his face. Then I lean forward and he pleases me. Our conversation flashed in my mind as I lean forward on top of him. I feel the lube cover my ass. He spreads it all over my cheeks and spanks me. I moan and whimper in my best girl voice. Almost natural by then. Then I feel the cool tip of the glass rub between my cheeks. He teases me. And to my surprise he begins fingering me. I love it. I can’t help but enjoy it. It doesn’t even feel gay in anyway. I just feel like he’s fingering my pussy so good and I’m being a good girl for him. Then the wand penetrates me. It feels amazing inside me. He uses it on my ass fast and slow. He wiggles it around inside me. My roommate puts it all the way inside me to the base and spanks me more. My hard clit is just leaking all over his stomach between our bodies.

I turn around on top of him to face him and press my hard clit against his hard dick. We kiss. Something we had started to do while fucking. But it was still new. And it was really good. Then I slip him inside me. I lean back to give him full view of me bouncing on top of him. He grabbed my sissy dick and I ride him. Moaning and whimpering as loud as I could. We didn’t even try to be quiet. It was Valentine’s Day after all.

The next day was business as usual. I woke up with his loads still inside me and a butt plug for extra measure to encourage impregnation of course. I got up before him and went to the bathroom to change into panties that didn’t have lube and cum on them. I washed my face of my makeup (never fall asleep with makeup on. Rookie 101). Then I went to the kitchen and made some breakfast while I cleaned up some of the mess from the night before. My roommate came out just as I was making our plates. We sat and had breakfast and talked about last night. He really enjoyed when I rode him cowgirl and came on myself. One of the few times that I came before he did and he loved to bring it up to get me squirming in random public places. I told him that I liked when he licked me from behind in doggystyle before pounding me to his first orgasm. We joked about recovery time being so quick. He said I looked amazing and it turned him on so much. Then we both agreed that our neighbors could likely hear us lol. My roommate was amazed to have came three times in a row last night. The last one took so long to get to. We probably tried ten different positions over thirty minutes and when he shot into my mouth it was barely a mouthful. I came the first time before any of his. But from beginning to end it felt like one long continuous orgasm.

We shower together after breakfast. To which he received a blowjob in the shower after I requested to wash his dick for him and he got hard in my hands and soap. I jerked on my own cock and came right in the middle of the blowjob without missing a beat deep throating him. After the shower we got dressed in boy clothes and went to campus to attend a seminar for extra credit. On the way back, my roommate said he had a date with a girl from class. I felt the jolt of jealousy, but I just said okay. The rest of the day I settled in and played video games in panties. I played with my dildos on my roommate’s bed smelling him in the sheets. That night I woke up to him spooning me naked in his bed. His dick rock hard poking my shorts. I took off my shorts but kept my thong on. Without saying anything he goes down to my ass and begins kissing my cheeks and licking my hole. I’m still slightly jealous of whoever he was with but I was beginning not to care. After all it was just a game of role play. No attachments. Then he spoon fucked me with my thong to the side. He came inside me and we fell asleep together after he put my butt plug in me.