Georgie's Road - Sex Stories

Georgie's Road

... said.

'It's fine,' I said. 'He's the one that has regrets.'

'Why?'

'He cheated on his girlfriend with me,' I said. 'At the end of my eighteenth birthday night out.'

Georgie sat back and let her jaw drop. The others were all laughing.

'So there is at least one total dickhead in this story,' she said.

'Well, they're still together,' I said. 'I was just a fling he had.'

'And you went all the way?'

'I was staying over at his place,' I said. 'He knows I've been bi since forever. He was giving me funny looks all night and buying me drinks. It was the end of the night and I decided I'd have a shower. While I was in there, he.... got in with me and started kissing me.'

'You let him?'

'Well, he's sexy as fuck,' I said. 'To him I was just Mike's cute bi little brother. I was flattered and he was horny and I realised I was about to get laid. He soaped me up and, um...'

I smiled and blushed. There were whoops from around the table. Georgie looked at me with, I thought, new respect.

'Standing up?' she said.

'Standing up,' I confirmed.

'Cool,' she said.

***

I'll skip how Georgie and I got together, because that's not really what this story is about, and it's not as interesting.

We were attracted to each other, we went on a couple of dates, we hung out, and pretty soon we were in her room, making out, and we were very much in the mood for, well, the main event to happen.

In mid-kiss, Georgie broke away from me, sat back and blinked and ...

... looked down.

'Is something wrong?' I said.

'No,' she said. 'No, no. I like you. I want to... you know.'

I thought perhaps she was having her period, and wanted to postpone. I wondered if I would mind having sex with a woman who was having her period. Or perhaps she had bad cramps.

'There's something you need to know about me,' she said.

I thought that she might be trans, and immediately decided that it didn't matter. She was still a hot nerdy librarian type. I had no interest whatever in the specific configuration of her genitalia. I liked her.

'It's about my... past,' she said, haltingly. I thought, Definitely trans.

'It's caused problems with guys I've been with before,' she said.

'Okay.'

'I want to have sex with you,' she said, and swallowed. 'But... I'm up for most kinds of sexy stuff, except... I have intimacy issues.'

'Okay,' I said, puzzled.

'Basically,' she said, looking up at me, 'I really don't like to be penetrated.'

'Ah,' I said after a pause.

'So you can see why that's a problem.'

'I suppose it would be,' I said, nodding.

'So if that's a deal-breaker,' she said, looking uncomfortable and a little sad, 'I understand.'

'I see.'

'It's cause of bad experiences,' she said. 'I'll tell you about them later, if you still want to be around.'

'I do,' I said.

Georgie smiled tentatively.

'You do?'

'Some gay guys don't like to be penetrated,' I said, shrugging. 'I don't see why it should be obligatory for women to ...