My first time

So to make a long story short - On Sunday I lost my virginity.

As the weekend rolled closer, arguments with my girlfriend became more frequent. The pettiness of comments and actions on both sides meant that by Thursday, all contact was cut.

What was I to do about my Disneyworld tickets? I’d already booked the hotel and tickets as a surprise, but hadn’t gotten around to asking her. With nothing to lose, I thought I’d head out of town for a weekend of ‘me’ time.

My definition of ‘me’ time might be a little different to most 22 year olds.

Since I was a youngster, I always loved trotting around in my mothers high heels. This eventually lead me to my sisters underwear draw, by means of terrible directions to find an iPhone charger. By the time I was a tween, you’d find me sneaking off to wear dresses, lipstick, underwear, whatever I could get my hands on.

Usually university is where people find themselves, but aside from buying my own stash of lingerie, I carried on pretending to be a heterosexual male.

So here I am, alone in a hotel room, shaved head to toe, moisturised and perfumed, and dressed in the sexiest black leather miniskirt, white ruffled top, and 4inch nude heels which I acquired via a shopping trip on the way here, when I decide, for the first time in my life, to enter the outside world not as Matty, but as Macy.

I headed to the hotel bar and ordered myself a mojito. After a few chats, a few drinks, and a few laughs I headed back to my room alone, proud of myself for getting out as the person I know I am inside, but now crippling horny.

I set about my usual routine. I start by locking my penis away in a micro pink chastity cage. Then I lay down a towel and prepare my 8.5 inch BWC dildo with lube, and go to town. I try every position, from doggy to missionary, with some cowgirl in between. I’ve not managed to cum this way yet, but it feels good.

After a while I call it quits. I tidy up and place a butt plug in my hole. I install Grindr and create a profile, before I drift off to sleep.

When I wake up my phone has gone through the roof with notifications! I work my way through them, deleting the creeps and blank profiles asking for nudes. Finally I come across an older gentlemen. Rough looking, but with a hairy chest and he’s much taller than me. In a desperate move, I agree to meet him. He’s a trucker, and would meet me at a lay-by 30 mins away. I drove there like a bitch in heat. I was wearing my white bridal lingerie - fitting for my first time, and a torn maids dress that barely covered my ass. My chastity had drove me crazy. I was desperate for cock simply because I couldn’t cum.

He greeted me in the truck. He was kind. I fell to my knees. I sucked his wonderful cock and revelled in the taste, the smell, the excitement. I assumed doggy on his bed. His tongue licked my bulging, cold balls as he flicked my. little cage. After he moved his tongue to my hole, his fingers crept not far behind. It didn’t take long before I said the words I never thought I’d hear myself say - “fill me up daddy”.

I let a complete stranger fuck my hole, and I meaner and enjoyed every second of it!