This happened during college ( a few years ago) and nothing could have prepared me for that moment. Now I feel like I should share my story with other crossdressers like me. Since an early age, I was fascinated by girls clothes, especially skirts and stockings. One time, when no one was home, I sneaked into my sister’s room and wore her grey pleated skirt and white stockings.
Since then I was pretty hooked to dress up as a girl. Anytime I was alone in the house, I would secretly wear my older sister’s clothes. Long story short, I started searching the internet and found out about crossdressing, and with time, my desire to dress feminine grew more and more.
When I joined college, I had less time to dress up and having a roommate made it even more difficult. I used to share an apartment with a guy named Jake, he was pretty cool, liked sports and was very athletic. We used to get along pretty well. I was kinda introvert, had few friends while my roommate, Jake was pretty opposite of me. He had a lot of friends and loved hanging outdoor or go to clubs with his friends. Whenever I knew Jake was going to be out for a long time, I would plan to get dressed and enjoy my feminine time. I had a small stash of feminine stuff hidden safely in one of my suitcase.
One day, Jake told me he was going on a hiking trip with his friends that weekend and I was pretty excited to have some alone time to dress up. Jake left early in the morning and as soon as he left, I began to get myself ready. First, I took a shower and shaved off my facial hair. Next, I got out the outfit I would be wearing, a white padded bra and panty set, a black mini skirt, white sleeveless blouse, thigh high stockings, and a pair of black high heels.
I put on the undergarments first and then the outfit. Now, I needed to do my makeup and hair. I put on my long wavy brown hair-wig that I just brought recently and when I looked at the mirror, I felt pretty cute and girly. I went to the bathroom to do my makeup. I put on some music. It took me around 30 minutes to do my makeup and I was pretty happy with how I looked. Next, I put on my heels and my transformation was completely. After posing in-front of the mirror for sometime, I decided to take some phots and videos of myself.
Unknown to me, Jake’s hiking trip was cancelled because one of his friend didn’t feel well all of a sudden and he was returning back to the apartment. I had no idea and I was completely submerged in my crossdressing. I was busy taking photos and with the music being played, I didn’t even hear Jake opening the door and coming inside the apartment.
I was in my room and the door to my room was open. I was sitting in the couch in a very slutty pose and taking naughty photos when all of sudden I saw Jake looking at me in shock. I felt like my heart stopped when I saw him. I couldn’t believe I was caught and I had no idea how I was going to explain it to him. I was so embarrassed and I didn’t know what to do next.
“Oh my god.. Sam? is that you?” Jake screamed at me, looking pretty shocked.
“Yes, sorry Jake.. I can explain..”. I uttered as I stood up.
” Wow, I can’t believe it. I really thought you were a chick at first. Why are you dressed like this?” Jake asked with curiosity in his eyes.
I didn’t know how to respond to his questions. I was still in shock that Jake caught me dressed like that. Finally, I managed to ask him why he was back so soon. Jake told me all about how his trip got cancelled at the last minute and it was pretty awkward standing there listening to him while I was dressed like a girl. At that moment, I didn’t even realize to change back to my guy clothes first before having a conversation.
After Jake was done speaking about his trip being cancelled, it was my turn to explain it to him why I was dressed like that but I just couldn’t understand at that moment how to explain it to him. I guess Jake must have sensed the awkwardness between us and asked me if I would be comfortable if we just sit down and talked about it. I nodded and we sat down on the couch.
“Are you gay?”. Jake asked me.
“No. I just like to dress up sometimes. I don’t know why but since I was a kid I enjoy wearing feminine clothes. Do you know what a crossdresser is? I asked him.
He nodded and asked how long I have been crossdressing. I told him about my crossdressing journey and he listened to me patiently.
“Thanks for not freaking out and sorry.. you had to see me like this. I won’t crossdress in the apartment again.” I told Jake.
” No worries. I was just shocked when I saw you like this before because I had no idea you enjoyed crossdressing. I have no problem with it. You can totally dress up whenever you like. And its crazy that you look so different as a girl, you look pretty hot!” Jake winked at me.
I blushed hearing his comment.
“So are you into guys or girls?? or both?” Jake asked.
” Well, I am not very sure.. I have dated girls but haven’t really thought about being with a guy.”. I replied.
” Would you like to try?” Jake asked.
I was confused and asked him what he meant by that. Then all of sudden, Jake leaned towards me and kissed me on my lips. I don’t know why but I didn’t stop him from making a move on me. I kissed him back, may be it was the heat of the moment that we both were feeling at that time. We kissed for a few minutes and Jake pulled me closer towards him.
He made me sit on his lap and started to caress my legs, slowly pulling my skirt upwards, revealing a tiny bulge in my panties. I was completely under his spell. I had never been made love to like a girl and I didn’t want to resist him at all.
Jake ushered me to move to the bed and I asked him if he really wanted to do this. He nodded and carried me to the bed. Then we kissed for sometime, took of each other’s clothes and made love to each other passionately. It was the best sensation I have ever experienced. It just felt so right at that moment.
After we were done, Jake got up and told me he was lucky he caught me crossdressing, otherwise he would’ve never known. I told him I felt the same way too. After that moment, I cross-dressed more frequently inside the apartment and we made love to each other countless time until Jake moved out to pursue his career. I really cherish those moments that we got to spend together.
Submitted by Samantha