Hi, my name is Sam and I am a 26-year-old, slim physic cross dresser. I am a fashion designer and have a thing for female clothing. Not only I love designing female clothes but I also enjoy dressing as a girl. Coming to my story, this incident took place some years back when I was around 20 years old and had cross dresser romance session with my real Aunt. With fair and curvy physic, I can look more girly than a girl with my cross dressed attire.
On one weekend, I went to my aunt’s place for a stay. To tell you, my aunt was a widow with no kids. As I was putting my stuff in the wardrobe of my aunt’s guestroom, I found a box that was untapped but had some things in it. As I opened it, I found a couple of fancy women clothing, sexy lingerie and wigs. I thought of trying it on. I dressed in a blue tulip dress, applied a red lipstick that I usually carried with myself and tried her pink curly wig. As I was admiring my girl look, my aunt entered the room. In excitement, I forgot to lock the door. Seeing her staring at me, I got embarrassed and then she left. I undressed and packed my bags and was leaving when she called me from behind. She asked me to sit with her. Shy and shamed, I sat next to her.
Me – “I am sorry Aunt Lisa”
Aunt – “Don’t be! I knew you are different from other guys. Do you like men?”
I nodded my head in reply.
Aunt – ” I am not going to disclose this to anyone if you agree to have a cross dresser romance session with me.”
I was surprised. She told me that after my uncle’s death she got lonely and the idea of getting physical with another man always cliched her. Thus, she decided to turn lesbian. She told me she always had a fantasy for a cross-dressing male. I agreed to her demands in order to keep my little secret away from my parents. She went into her room and brought a black baby doll night suit for me. She asked me to change in front of her as she wanted to enjoy every bit of the cross dresser romance session. I was hesitating so she forcefully undressed me and massaged me a bit on my already hard cock. She then made me wear that night suit. She then held my hand and took me inside the room.
As I sat on the corner of the bed, she opened her wardrobe and took out an 8-inch dildo and a pair of handcuffs. My dick started tingling imagining that dildo humping me inside my tight ass. Aunt then opened the side drawer and took out a jar of petroleum jelly. She then pushed me to the bed and then started removing her clothes. Her boobs were big and delicious. Then, she jumped on me and started kissing me and melting her tongue in mine. Then she made me suck her boobs. As I was sucking her nipples, she grabbed my hair and pushed me inside her chest, making loud moans.
Then she started pulling up my night suit and removed it. Then she went down and pulled my jockey down with the grip of her teeth. She then licked my balls and stroked my dick. It was getting hard. She then spat on it and spread it all over my dick with her saliva dipped tongue. Then, she told me to turn into the doggy position and stroke myself with one of my hand. While I was doing that, I felt some liquid getting dropped on my asshole. It was petroleum jelly. When I turned my head, I saw her adjusting the strap on dildo and applying petroleum jelly on it. Current went down through my veins on the idea of getting fucked in the ass. She then climbed up on me and inserted the dildo slowly inside me. At first, it pained a lot but then it was pleasurable. My aunt was fucking me hard with the dotted dildo, making me moan hard.
After 10 minutes of fucking me with the 8 inches strapon, she stopped for a moment and pressed a button on the strapon belt. It began vibrating. My hands stopped the stroking motion but she asked me to continue it. The pleasure and pain my aunt was giving me was enough to reach my apex. Soon I was about to cum. She then pulled out the dildo and turned me around and started sucking my penis.
Soon, I orgasmed inside her mouth and she swallowed it. Then I pushed her on the bed and lay next to her, finger-fucking her pussy. She then asked me to handcuff her on the bed and insert the vibrating dildo inside her. I obeyed. I handcuffed her on the bed, spread her legs, get hold of the vibrating dildo and inserted it inside her in one go and start pushing it in and then pulling it out. She was moaning loud and after some time, she squirted. I then removed her handcuff and she wiped herself with a tissue and went inside the washroom to take a bath.
We both enjoyed our time and had a wonderful cross dresser romance session. We continue doing that whenever we meet.