All the stories I will tell are 100% true. I got extremely lucky in life and got to fulfill my inner cd/sissy/femboy desires all the way from high school through college. It turns me on to retell my stories and I’m so glad I found a subreddit to do it. Please enjoy and you can ask me any questions in PMs or in comments 🥰 enjoy!

About a month and a half after my roommate caught me dressed up and after the first blowjob I gave him, we made plans to go to New Mexico together for spring break. We planned to go to the mountains in the northern part where there was still snow. The plan was to ski and snowboard for a week. We wanted to enjoy a change of scenery from our everyday college lives and routines.

At this point, I was dressing up daily as soon as I got home to our apartment and I was doing everything in girl mode. My roommate was used to it and would even come home and spank my ass hello. Sometime he would even ask me to stand up so he could give my ass a slap if I was sitting down when he arrived. We weren’t always having sex daily but we would at least three to four times a week and occasionally we would have one to two weeks of non stop sexual gratification. Blowjob, ass eating, fucking, hand jobs in bed, making out, etc. But still every night I was getting in bed with him and he would settle his cock between my ass cheeks and I would grind on him until he got hard. Then we would fall asleep.

So we planned out our vacation for spring break and decided to leave from college the Thursday of our last midterm exams. Of course I packed all of my lingerie, girl clothes, and crossdresser accessories. We were going to be alone where nobody could bother us and obviously I’m trying to get railed lol. One of the sexiest things we had been doing lately is asking him to “get me pregnant” while we fuck. Something about it idk. Maybe other crossdressers know what I mean.

We start off driving. In his truck I’m wearing a short skirt, some over the knee socks, a cute thong, a t shirt, and to top it off a new buttplug that may roommate bought for me. I hadn’t used it yet but I wanted to surprise him cause he had been asking me when I was going to try it out. It was a glass buttplug with a flower at the end of it. Y’all may have seen it before in a few other sexy CDs in this sub. I wasn’t wearing a wig or makeup of any kind just in case I needed to get off on our road trip. I had some sweats to slip on quickly if I needed to. The trip was going to be a total of 10 hours driving.

About three hours into it my roommate is driving and asks if he can play with my ass a little. I tell him of course he can and I lean over a bit and pick up my skirt so one cheek is exposed. He’s grabbing my hip and my ass. Spanking the side of my ass and squeezing my smooth thigh. His grip makes me squeal and giggle. He moves his hand under my ass and pulls my thong to the side. I know he wants to finger my ass pussy cause he loves doing that anytime he touches my ass. He feels my butt plug and I see the look of excitement on his face when he asks, “Are you wearing the buttplug I bought you finally?! Can I see it?” I happily obliged and got up on the seat on my knees and faced the passenger window so he could see my ass. I lift up my skirt for him and he sees the toy he bought me inserted in my ass. He caresses my soft smooth sissy balls and pulls my throbbing girly stick back between my legs. I’m moaning lightly. It feels so good. I know he’s getting hard too and I can’t wait to feel his cock through his gym shorts that he wore. He grabs the head of my buttplug and slowly gently pulls on it. He pulls it out some and pushes it back in. Then he pulls it out all the way. He teases my hole with it a little bit. Then he puts it in the cupholder. I feel his fingers caressing my balls again and working their way up to my hole. By this point my sissy cock is leaking and twitching. I can feel my precum dripping on my thighs. He rubs the tip of my sissy cock and lubes his thumb with my precum before pushing it inside me. It feels so good feeling his fingers in me. He switches to his pointer finger, then adds his middle finger, and then finally puts three fingers inside me. That is the most fingers he had put inside me at that point. It felt amazing. He instructs me to spank myself. I spank my ass for him every time he says “again”. My ass is red and burning. I love how it feels. He spanks me a few times as well. Then he grabs my plug and places it back inside me. I sit back down and he says “good girl”. He knows I love that. I adjust my thong and my skirt back then sit there quietly, horny, wanting to suck his hard dick while he drives.

A few minutes later I can’t take it anymore. I reach over and feel his cock. I had been glancing at it several times. But I wanted him to ask me to suck it. He smiles when I grab it and says “good girl.” That sends me over the top. I reach into his shorts and gently play with his balls. His cock is wet too from his precum. Something he always had a lot of. I was thankful for that because in the heat of the moment we wouldn’t even need lube. He could just stick his cock in me. Plus I absolutely loved licking up his precum. So I jerk him off for a while. Then I ask him, “Can I please suck your cock sir?” He says “Yes baby. Be a good girl.” I love how he talks to me. I get on my knees on the passenger seat and bend over to suck his dick. He warns me that truckers might be able to see my ass. And I tell him to let them see it so I can practice being a girl in public lol. It wasn’t very long before I hear a horn from a truck next to us. My roommate slows the truck down and gets behind the eighteen wheeler. I ask him if the driver saw it and he said yes but decided to moved behind him on purpose just so the eighteen wheeler wasn’t driving recklessly. As if we weren’t doing something reckless ourselves lol. I sucked his cock and maybe three more times truckers honked at us and my roommate pulled the same move getting behind them. In my mind though I was imagining him actually feeling jealous because I am his girlfriend and he doesn’t want guys looking at me. It makes me suck his cock with more passion. I want to please him and for him to think I’m better than any girlfriend he could have. He had said it to me multiple times but I wanted to actually show it. I’m sucking his cock and he’s playing with my buttplug all while driving with one hand. Finally he cums in my mouth. I swallow every drop that comes out and I continue sucking his dick until I get every last bit of cum. Then I gently grab his balls and star kissing them. His dick stays hard the whole time I’m kissing his balls so I go back up and suck his dick some more. After a few minutes I sit back down and he says, “What a good girl. I’m going to pound your ass as soon as we get there and I’m going to impregnate you.” I squeeze my butt plug with my ass pussy and I fix my skirt a little bit then say, “Yes please sir.”