I was seventeen when I tried on my first pair of panties, I was at a friend's house staying the night with a few people, both male and female. We had all been swimming and I was last to have a shower and change into dry clothes. Jumping out of the shower and drying off I realised one of the girls had left some panties on the floor, whether she didn’t wear them when she left or didn’t realise another pair fell out of her bag.

Curiosity got the better of me for who knows what reason and I tried them on, it was a mixed feeling of excitement and fear. I stood the for a few minutes feeling myself as my cock slowly grew, I quickly took it in hand, and being seventeen I blew my load to the most intense orgasm I had ever had. Quickly cleaning up, I put them back and got dressed, heading out to everyone for a night of relaxing, but the feeling and thought of those panties never left my mind.

The next few months, I slowly explored crossdressing more, trying on some of my mum's lingerie and dresses, but nothing seemed to give me the same feeling as that night. I soon turned eighteen and I decided I wanted to get some of my own clothes.

I looked online for a few days making quite a collection of items I wanted to buy, from dresses and lingerie to some leggings, tops, and shoes. Thankfully I was able to do click-and-collect orders and everything was ready to pick up a day later. I was so nervous walking into the shopping centre to pick up the items, the embarrassing feeling that every person there knew what I was doing and the thought of the employer knowing what I was there to get had me sweating.

Waiting at the desk for the clerk to bring out my order felt like an eternity, but with the last bag on the table, I quickly made my way out. I couldn’t wait to get home and try on my new clothes so I ducked into the men's rooms and dug through the bags at my new purchases, and I felt an overwhelming excitement hit me. I swapped my pair of briefs for a nude G-string and put my shorts back on. Walking back through the shop I felt so slutty. 

Getting home I sorted all my new items out, two pairs of matching lace lingerie, a white set and a green and black set, a short-sleeved green flower summer dress, a black mini dress, some black jeggings, a short skirt, Red long sleeve top, some stockings, a pair of black suede four-inch heel boots and some four-inch string stilettos. I tried it all on before hiding it all in the back of my dresser. I spent the following weeks dressing at every opportunity I had at home alone but knew I wanted a bit of a longer period in private to fully experience my few found love.

I booked an air BNB in a little coastal town about an hour away from home, somewhere I had been before and I knew I would have some spots to go outside and not have to worry about being caught. I'd also become slowly more explorational when dressed, from tasting my cum to butt play, I'd never thought I would enjoy it but while dressed it made me feel so sexy.

I made a trip to an adult store on the way to my weekend getaway and purchased a butt plug, dildo, and wig, and stopped by at another shop to get some basic makeup, just to see if I would be able to pull it all together. After checking in and getting my bags inside I wasted no time in getting in the shower and shaving my body smooth, I hopped out, dried off, and slowly inserted my new plug. It was by far the biggest thing I had used and took some time but felt so good once in place, I slipped on the white lingerie set and put on my homemade nipple clamps, followed by some homemade fake breasts.

I followed a tutorial online about making them from stockings and rice and weighed them out to be roughly B cups. I sat at the mirror watching YouTube and applied some basic makeup, and was pretty surprised with the outcome, I threw on the summer dress and stilettos and went out onto the balcony for a wine. 

I spent most of the Friday night just chilling out and polishing off a few glasses of wine, feeling quite frisky I decided to try out my new dildo, it was a seven-inch suction cap dong, and it was pretty thick and looked very realistic. Semi undressing I went to the back room and set it all up, slowly pulled out my plug, and lubed up my asshole and the dildo, I sunk to my knees and aimed the head and my opening, and slowly sat down. The first inch was hard. I had to take a few attempts and add more lube but soon the head popped past and I slid down the shaft.

The first feeling of a cock in my ass felt amazing, I bobbed up and down and soon had the whole thing working its way in me. Cupping my breasts the pinch of the nipple clamps through in an extra bonus of arousal, And within minutes I shot spurt after spurt of my hot cum all over the floor.

I sat there for a few minutes gathering back my breath before letting the dildo pop out from my ass, an empty feeling left me quickly lubricating the plug and putting it back in. I cleaned up and got changed back into my outfit before relaxing back on the balcony, Id never felt so happy and content with myself, it was a weird feeling. But knowing I still had another two days to go I knew my time out here would be one to remember.

Thanks for reading and the next parts of this story will hopefully be up soon.