Has to delete and reup load because I had the wrong title 😅

I have pt 1 on my profile and some background of me and my roommate! This is the last story about this vacation! That you everyone for reading and for your kind and sexy PMs lol. Enjoy!!

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Up until now I hadn’t been out in public more than just riding in the car dressed up. But I felt like my makeup was cute, I had a scarf covering a lot of my face, and I had great curves from the gym. I was nervous but my roommate was very supportive.

After we had morning sex I got dressed. I still remember tingling from the sex as I pulled my leggings up and got ready to go out on the slopes totally dressed as a girl. Even as we sat on the ski lift I was still so turned on by that morning. Up to the top my roommate was holding onto my thigh and making me feel so protected by him. And as I laid my head on his shoulder for an instant I felt like I was really turning into a proper sissy femboy.

From my other stories of our sexcapades, we were really comfortable with the role playing. Down the slopes he would stay close to me. Occasionally I would fall and he would help me up and grab onto my hips as I balanced myself back up. But another thing that really had me turned on was that so many guys were nice to me. One guy helped me up and said “Most girls fall their first time. My girlfriend did.” And I would often catch glances at me. Maybe it was the color association with pink and my general outfit. But maybe I was catching their eyes because I was looking good and they would consider fucking me. Being out in public was an amazing feeling. And I am lucky to have done it.

The entire day was so fulfilling. Finally after getting back to our cabin we decided to make dinner instead of going back into town. I made an easy pasta recipe and we had some wine. Cliche romance lol. But it was really working on him. Throughout the whole night we would have random sessions of romance. He would slap my ass while I was cooking or reaching up to grab some plates from the cabinets. While we ate we had light conversation and my roommate would say little quick things like “I bet a lot of those guys were checking you out.” We watched a movie and I would give him a blowjob. He would make me stop before he came and just play with my ass while I laid my head in his lap. This happened a few times and by the end of the movie he was licking my asspussy and making me beg him to keep going.

After the movie I decided to clean up and my roommate said he was going to go to our room and wash up a bit. I was dripping through the front of my panties, my ass was tingling from the licking I just got, and I knew that once I was done with the dishes that I was about to go get absolutely railed lol. I tried to hurry but I wanted the dishes to be spotless. So I still took my time cleaning and building up the sexual tension in the air.

The dishes were clean and I halfway run and halfway skip to the bathroom in right passed my roommate laying on the bed with the TV on. I hop in the shower and give myself a quick wash. I’m thankful that he helped me wax before the trip because it is holding up absolutely perfect lol (more on that in another story if someone wants to message me and ask) and it is definitely a time saver from shaving. My clothes are already planned out by both of us. The memory of us laying in bed together picking out clothes for me to wear the night before one of our final exams and being extra tired the next day because we stayed up too late is still fresh in my mind. My outfit: wine red thigh highs, a matching garter belt, black lace boy shorts, heart pasties for my sensitive nipples to tease me until he licks them off, a wine red bra and new breast forms (birthday present), a black lace see through robe, a red wig that matches my lingerie, and his favorite color of lipstick. Just remembering how it felt slipping those thigh highs on and getting ready for him makes my heart flutter and gives me butterflies in my stomach. I get into my outfit and redo my makeup.

When I open the door to the bathroom my roommate glances over at me and says “wow.” I melt and walk over to the bed. I lay down next to him and start to caress the bulge in his boxers. He lets out a relaxing sigh and closes his eyes for a bit. I start to kiss his neck and he breathes deeply. He turns his head toward me and we begin to make out. It wasn’t everyday we would make out but when we did I knew things were about to get hot. He pulls me on top of him. I’m still grabbing his bulge and feeling it turn into a rock hard boner. His hands grab my ass and then starts to caress my skin. I moan right into his mouth with pleasure on top still kissing and licking each other’s tongues. His fingers explore my ass pussy still covered by my panties. The ultimate tease. He’s pressing gently into me and I can feel how thin the barrier is between me and pleasure from his fingers. He starts to sit up, picks me up with both his hands on my ass, and he scoots back to sit up against the wall. Ugh just being picked up by him and him holding me is enough to get me to do anything. We kiss more passionately as he spanks my ass.

I hop off of him and turn around with my ass facing him. He spanks me some more and then pulls my ass down to sit on his hard bulge. I start rubbing against it with my ass and he’s saying “ooh fuck.” He loves it and I don’t even need to ask. I turn back around facing him and stick my ass up in the air with my face in his crotch. His cock is still in his boxers and the precum is soaking through his boxers. I reach up his legs though his boxers and with one hand I caress his balls, with the other I gently stroke the tip of his cock. He tells me “what a girl little femboy sissy. That feels so good.” My mouth is kissing around his cock in his boxers. Finally I pull down his boxers and his dick flops out. One of my favorite things to see. His balls are hanging low. I lick starting right between his balls. Slowly up his shaft to the head of his dick and start sucking. The sound of his moaning and deep breathing I could finger myself to for hours. He says “baby” and “fuck” and “good girl you’re sucking it so good.” His dick is so good in my mouth. I knew it well and knew exactly what he wanted and how he liked it. I did everything. From sucking just the tip, to letting him poke the back of my throat, to having both of his balls in my mouth and jerking him off at the same time. I also knew when to slow down lol.

He grab any arms after some time and brings me back up to kiss me. I sit back on his lap facing him and holding his dick with one hand against my cheeks. He whispers to me “get on your tummy and stick that ass up.” I giggled involuntarily feminine and laid down. He spanked me and caressed and switched to kissing my ass and shoving his face in it for about 5 minutes. He really took his time watching my ass jiggle for him. He was admiring his work from encouraging me and giving me different butt exercises to do at the gym all year. Then he began licking me. Oh that amazing feeling of getting licked deep. And his fingers giving me that little warm up I needed for him to fully penetrate me. I don’t know how long he did it for but it was enough to make me beg him multiple times to please get inside me.

We always started missionary position. And he always grabbed my hips and held my hard clit straight up the middle with his thumbs. He didn’t need to guide his dick in me. He knew exactly how to penetrate me. Gently he slid the head of his cock in and he knew when it was in from my moans. Slowly he worked his way in and out of me. He would go in an inch and slide back out to where just the head was In. Then he would go a little further until he was all the way inside me. When I finally made it to the base of his cock he leaned over and started kissing me while thrusting inside me. It’s so passionate this way. His balls slapping against my skin, his tongue and lips muffling my moans, and his hard dick deep inside me. He pulls out and asks me if I want more. Of course I say yes and he goes back to kissing me then shoved his dick back in me. I tell him I want to ride him and he lays down. I get on too reverse cowgirl so he can have a great view. I ride him. He’s moaning and calling me “baby” and “good girl.” It pleases me that I’m pleasing him. He tells me to get on my hands and knees so he can pound me from behind. I eagerly oblige.

He gets up from the bed and stands at the edge. I slowly back up and tease his cock. I just slide it up and down between my cheeks. Then I grab his dick and guide him inside me. He starts pounding me. I can feel his balls slapping against me as he grabs onto my hips and pulls me harder every thrust. Suddenly I feel a tingling sensation on my femboy clit. I don’t get it, I feel like cumming and I’m not even grabbing onto myself to help. Without warning I feel a quick buildup from my toes to the top of my head and I start to cum! I’m cunning and whimpering like a good girl. So much intense pleasure I’m just involuntary making little fem noises. He’s pounding me still forcing cum out of me and I’m vibrating all over. I can feel him throbbing inside me and going faster. I know he’s about to cum in me. I beg him to cum in me. To give me his seed and make me his little femboy girl. Finally he releases inside me. Full warm thick cum just exploding into my guts impregnating me. I pull his dick out carefully squeezing my ass pussy so no cum comes out. I turn around and sit on the spot where I made a mess. Softly I kiss his dick. Then I start to suck and taste myself. Delicious. His cum and my ass pussy. I take out every drop I can.

What an incredible night.