Trip To The Races Ends In My First Anal Sex

When I was at university I had a preppie boyfriend who worked for a merchant bank in London. His firm laid on lavish hospitality at the Royal Ascot races for employees and clients. He invited me as his guest, and I wore a designer dress and hat for the event. I looked very sophisticated – little did I know I’d be experiencing my first anal sex just hours later!

At the races, we got stuck into the champagne and studied the form. I don’t really know much about horses. I’ll usually just bet if I like the horse’s name.  There was a powerful-looking stallion called Poppy’s Delight. I’m always an admirer of a well-hung male, so I decided to place a bet. My boyfriend laughed and said that the horse was a rank outsider and had no chance over the short course. I stubbornly told him it would win and that I was betting £100. He laughed again in a way that really annoyed me. He said that if I was so sure, I should make a bet with him…

Betting Away My Anal Virginity

The deal was that he’d take my bet at 7:1  – if my horse won he’d give me £700. If it lost, I had to have my first anal sex experience with him that night. Another first… just like my shocking first threesome!  I’d always been nervous about anal and refused every time he asked. The closest I’d got was pushing a well-lubricated finger in my arse while using my vibe. Now he’d injured my pride and I impulsively agreed to the bet.

I watched the race with nervous excitement, suddenly stunned when my horse came in second to last. Smirking and gloating all afternoon my boyfriend was stroking my arse like it was his private property. I wanted to slap him, but I’d lost the bet and couldn’t do a thing about it. I kept wondering what it was going to feel like to get fucked in my arse, and whether it would hurt.

Back in our hotel room, he ordered me to undress and get on the bed in the doggy position. He handed me a tube of lubricant and ordered me to start working it into my arse. I’ve always had a secret submissive streak and I felt my heart beating faster. He watched as I fingered my own arsehole, working the lube deeper. Walking around to the other side of the bed, he grabbed my hair and pulled my mouth to his cock.

Losing The Bet And My Anal Cherry

I sucked him clumsily, trying to support myself on one hand, as the other fingered my arse. Fully erect he pulled out of my mouth and told me to work the lube into his cock. I massaged the wet gel onto his dick while trying to wank him. Very unsure about having him in my arse, I wanted him almost ready to cum. He had other ideas! Slapping my arse cheeks hard, he pushed me down, raising my arse upwards.

I felt his glans press insistently against my arsehole. Even though I’d just had a finger inside, I was very tight. In fact, I still am! Anyway, he worked his cock inside me, pushing a millimetre at a time. I’d never felt so submissive and so completely penetrated. It was a strange feeling, but not as painful as I’d expected. As he pushed deeper, he dripped more lube over his dick and thrust a little bit faster.

I reached between my legs and started to rub my clit, moaning with pleasure. Then I pushed two fingers into my pussy. The feeling of a hard cock in my arse and two fingers in my cunt was intense. I’d never experienced that kind of sensation before. It was like I was completely filled up and losing all my self-control. He fucked me harder, causing me some pain, but also incredible excitement.  I came seconds after he did and slumped face down on the bed, utterly exhausted but with a sly smile on my face…

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First Anal Sex