I have been crossdressing for some time now, and have just recently taken to venturing outside dressed. Up to now, I have only been to places where I was pretty sure I wouldn’t bump into anybody.
I love the feeling of silky underwear underneath my skirts and dresses. I always keep my legs shaved smooth as well as the rest of my body and keep my balls shaved and my pubic hair trimmed short. I love wearing really feminine clothes; the feeling next to my smooth skin really makes me horny.
This one day I had put on a nice blue patterned dress, pink panties, and a matching bra, and went for a walk along the seashore. The top of the beach is lined with woods. I had been walking for about ten minutes when I realized this guy was following me about fifty feet away.
After a short time, I decided to head off the beach to see what would happen. I headed up into the woods and down into a dip and waited to let him walk on by or maybe follow me. My heart was pounding as I waited then he suddenly appeared and stood there looking at me grinning. I nervously smiled back as he came closer until he was just a couple of feet away from me.
I didn’t know what to do, my mouth was dry and my heart was racing even harder, some with fear and some with excitement. He never said a word, he just began to rub his groin while looking me up and down.
Even though I took great care in dressing and looking the part, I just used a scarf to cover my head. He stepped closer and in a flash thrust his hand up my dress and squeezed my cock through my panties. He looked at me and smiled, and still without a word being said, he pulled down his zip and pulled out his cock. I looked down at it sticking out hard with a big fat purple knob, about 7”. I must admit I found it exciting as my own cock began to stir with his fondling.
I had never been this close to another cock except when I showered at the gym and sometimes stole a quick glance in the toilets. He gestured with his head and eyes to direct me to his cock, but eventually took a hold of my hand and placed it on his cock. I gently wrapped my hand round it and gave it a squeeze it felt so warm and hard. This was the first time I had ever touched a cock apart from my own and I was enjoying it.
He now dropped his jeans, showing me a thick dark mass of pubic hair. Then he hoisted up my skirt and tugged my panties down and pressed himself against me so his cock was pressed against mine and began to rub himself against me.
By now I was rock hard, and he grabbed my ass cheeks and rubbed hard against me. I felt his finger press against the ass hole I had often put a couple of fingers inside myself while jerking off, but this someone else’s and liked it. I opened my legs a bit and felt a finger push inside me, followed quickly by another. He worked them deep inside me. I began to moan loudly, then came noisily coating both our cocks in cum. Not long after, he too starting shooting, spraying us both with even more hot cum.
He held me against him for a few minutes then slipped his fingers from my ass and released me. My dress fell down and I looked down at his cock covered in dripping cum. It looked so hot. He grabbed my shoulders and pushed me onto my knees on the soft grass. He thrust himself close to my face and I knew what he wanted. As I looked at his cock, he grabbed my head and rubbed it all over my face covering me with cum. Then he held it to my lips, which I parted, and took him into my mouth.
I had tasted my own come before, but this was new. It was covered in cum, both mine and his, and I liked the taste and quickly began to suck it and lick it clean. Even sucking it out of his mass of pubic hair which tasted a little salty from his sweat.
He soon got rock hard and pushed it into my mouth. He fucked my mouth holding my head as I sucked noisily. He lasted for a long time before his body started jerking. He pushed his cock deep into my mouth and came down my throat, filling my mouth with hot salty cum.
When he was finished he pulled his jeans up, and now spoke for the first time looking me straight in the eyes “Be here tomorrow, same time, for a bit more fun, OK?” He spoke with such authority I just answered yes.
Then off he went leaving me still kneeling there with cum now drying on my face. At the top of the hollow, he called back “Be here tomorrow!” Then he winked, turned, and left disappearing over the hill. I now stood up pulled my panties back tucking my cum soaked cock in.