Georgie's Road

Georgie always says that the way I lost my virginity made her like me.

Or at least, that's why she liked me to begin with.

I think she liked me later on for other reasons. Which are what this story is about.

***

It was our first year in college. We were, mostly, nearly 19. We were doing what students do: hang out, make friends.

There were about seven or eight of us, but I only had eyes for Georgie.

As soon as I saw her, she became my idea of the person I wanted to be with: smart, funny and no-nonsense. But she also appreciated other people being funny.

She was cute in a kinda sharp, librarianesque sort of way. She had short cropped red hair, glasses and a rather pointed nose, and a mouth that seemed to be almost perpetually about to smile, but didn't do so very often--so when she did smile, it was worth it. She always dressed in multiple layers, so it was hard for my lizard brain to tell what her general body shape was like, except that she flared slightly outwards at the hips, which I liked.

But enough about that. This is a story about Georgie's brain, and her heart, and how I learned about them.

***

Georgie was very feminist, and a fountain of sharp remarks about the idiocy of men. That was fine with me, because I think men are mostly idiots too.

Which is what made it so entertaining, that night in the pub, when we all started talking about how we lost our virginities.

Georgie's turn hadn't come yet, but she was very funny about all the guys who admitted that they'd only managed it under the influence of beer, and that it hadn't been very successful. One of the girls, Courtney, told a hilarious story about losing hers to another girl at camp, but most of the girls' stories were more or less hilariously awful--or at least the girls were determined to find them hilarious in the telling of them, that night.

'What about you,' Georgie said to me. 'What's your story?'

'Oh,' I said, 'not much to add. Little bit too much to drink, bad decisions were made, people did things they regretted. Not me so much, but yeah.'

'God, you're all so predictable,' she said, grinning. 'How many guys around this table have lost their virginities to girls that they should apologise to now.'

'Well,' I said, 'not me, actually.'

'Oh?' she said. 'Why shouldn't you?'

'I have nothing to apologise for,' I said.

'Do you think she'd say that?' Georgie said. 'Who was she?'

'A friend of my older brother's,' I said. Georgie raised her eyebrows.

'Ah,' she said. 'Well, that is a little unusual. What was her name?'

'Alan,' I said, smiling.

There was a pause, and then everyone burst into laughter. Georgie took slightly longer, but then she laughed too, covering her mouth with her hand.

'Oh shit,' she said, pulling a wry face. 'Well, ain't I the asshole. I'm sorry, I just assumed. I didn't know you're gay.'

'Oh, I'm not,' I said. 'I'm bi.'

'It just gets deeper and deeper, this hole, doesn't it,' Georgie 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 like it.'

'But it wouldn't bother you, not being able to, you know...'

Fuck me, was the unspoken phrase. I looked into her eyes.

'I'm sure there are plenty of other things we can do,' I said.

'Seriously?' Her smile widened.

'We're just going to have to be imaginative,' I said, smiling back.

She threw her arms around me and we kissed.

'One thing I don't want to have to imagine any more,' she murmured, 'is what you look like naked.'

I took my cue and got up. As I took off my socks and t-shirt, Georgie unbuttoned her blouse and removed it, then slid down her jeans. In bra and panties she watched me lower my own jeans and then slide my boxers down. Naked, I got back on the bed with her and she ran her hand up my leg, over my bare hip and along my side and ribs, stroking me.

I love being naked when my partner is clothed, or partially clothed. It makes me feel receptive and vulnerable.

'That's more like it,' Georgie purred. 'Get on your stomach.'

I obediently lay on my stomach, folded my arms and laid my head on them, looking at her. She stroked my bare ass.

'I've been fantasising about that ass ever since you told us that story about your eighteenth birthday,' she said.

'Oh yeah?'

'Mmmm. I was envious of your brother's friend.'

'Well,' I said, 'one of us likes being penetrated.'

'I thought so,' Georgie said. She got off the bed and walked over to a closet.

'Shut your eyes,' she said. I closed them and waited.

'Open them,' she said. I opened my eyes, and she had taken off her bra, and was wearing a strap-on dildo over her red panties.

'Are you ready to be my bitch?' she said, cocking an eyebrow.

'Would it make any difference if I said no?' I said, dry-mouthed.

'This is going to be fun,' she said, sauntering over to me. I parted my legs slightly, knowing she was looking at me, the naked young man prone and waiting on her bed.

She had a small bottle of lube in one hand and she squeezed some onto the dildo. I mentally thanked god that I was thoroughly clean, inside and out, a precaution I always take before a date.

'Have you done this before,' I said.

'Never with someone with your level of experience,' she said. She mounted my naked hips and pushed down on my back, and then she manoeuvred the head of the dildo until it was resting against my anus.

'This is for the sisters,' she said mockingly, and pushed. I gave a high-pitched moan as she penetrated me, and then I felt the pressure of the dildo filling my arse, and Georgie's weight on me, as she thrust her hips forwards and swivelled them back, buggering me.

I love to be ass-fucked. But I had never had it from a girl, and it was intoxicating, knowing that this smart, educated, together young woman was getting visceral pleasure from shoving a dildo deep into my arsehole and seeing me squirm with arousal and ecstasy.

'That's it,' she panted, 'take me, take my cock up your ass.'

'Oh god,' I whimpered.

'Can you feel me inside you?'

'Yes...'

'You look so hot, lying there with me fucking you. You like being fucked by a girl?'

'Oh please...'

'That's it, slut,' she gasped, 'take me. Take me inside you.'

Georgie well and truly fucked my brains out, that night. We lasted a long time, and she was very good: merciless but thorough. She leaned over me and kissed me while she sodomised me and I gasped and whimpered.

By the end, I was on my back, my legs were back over my head and she was crouching over me, fucking downwards and jerking me off, and as I made incoherent whimpers I came over my own face.

She wouldn't let me wipe it off, but she took off the strap-on and lay next to me and we cuddled. My eyes were closed so that my cum wouldn't get into them.

'You didn't cum,' I said.

'You did.'

'But you didn't?'

'I don't, really,' she murmured. 'It's cool. I still love doing it. I love this part. And I love putting you through that and hearing the noises you make.'

'I wish I could make you cum,' I said.

'No one ever has,' she said, and patted me fondly.

***

For the next six months it was like that.

We did do other things. We took baths together. We tried face-sitting, and 69ing, but she didn't like my tongue being too near her vagina.

We did a lot of mutual masturbation. One big day was the first time Georgie got naked with me, for my birthday. I tried to see any scars which were normally covered by underwear, but I couldn't. Whatever scars she had were evidently internal: in her mind and maybe inside her body.

I was happy. I loved her, and she seemed to love me.

But, over time, things began to get less blissful.

Sex seemed to be something she was less and less interested in having. I thought she might be going off me but she swore that she really liked me and I needn't worry.

But then, one night, after she'd fucked my arse again and made me cum as always, we were lying there afterwards, unusually silent.

'What's wrong,' I said finally.

'Nothing's wrong.'

'You seem sad.'

Georgie was silent for a long time, and then rolled over and looked at me. I was naked; she was in her bra and panties.

'Something's not right,' she said quietly. 'I really like you. I think maybe I love you. But I can't figure out why I can't come with you.'

'We'll figure it out,' I said.

'I've been trying to figure it out,' she said. 'That's not the problem. I think maybe...'

She paused, and bit her lip. Her eyes were wet. I began to feel like I didn't want to hear what was coming.

'I think maybe it's that it's not you,' she said. 'Maybe it's guys. Maybe I'm bi.'

'Do you fancy women?'

'I've always thought women are more sexy,' she said.

So that was it. I felt my throat tighten and my own eyes prickling.

'You don't fancy me, then?'

'I do fancy you, I love fucking you, it's not that. I mean, I really do love seeing you in ecstasy. It's so hot. But you know it doesn't make me come. I don't understand it and I have to figure it out.'

'So you think maybe we should... break up,' I said. Georgie closed her eyes and a single tear rolled down her cheek. Then she opened them again.

'I think maybe we should. I'm so sorry.'

I took her hands.

'I think you should do whatever you have to do to be happy,' I said. 'I still want to be your friend, if you want me as that.'

'Oh god, I'm so glad you said that,' she said, and put her arms around my neck and hugged me. We lay there, for a while, weeping a little.

'I'm so fucked up,' Georgie sobbed into my shoulder.

'You'll figure it out,' I said. 'I'll be there if you want to talk.'

'Thank you,' she whispered.

We parted, and I put my boxers back on. Now that we had broken up, there was no point in being naked.

We slept that night, and parted the next day. Was I as upset as fuck?

What do you think?

***

Over the next few weeks, I watched with mixed feelings as Georgie set about finding a girlfriend.

On the one hand, I was glad that she seemed to be on the right track towards happiness. And we did remain friends, and saw plenty of each other.

On the other hand, I missed her. Badly. I missed her company, most of all, but I also sleeping with her, and waking up next to her, and her lithe body on mine, doing things to me. I missed that I had never managed to make her have an orgasm, and I was depressed that it would be someone else who did that.

Being a bi guy who isn't totally terrible-looking, I didn't have much trouble finding partners for casual sex. But I got bored of the guys who just wanted to fuck another guy, not share a life with him, and I had to admit that I wasn't sure I wanted to be in a steady relationship with a guy anyway.

And most of the guys I had a thing with couldn't make me cum, either. It was a brief but steady succession of either gay guys, or clumsy bi-curious guys who wanted to try fucking another guy up his ass. Quite a few of the latter met me online and never met in real life, but described in great deal what they wanted to do to me (probably jerking off the entire time) and then never arranged to meet.

When Georgie did finally get together with another girl, it was doubly dispiriting, because she was a friend of mine: Louise, a plump and cheerful lesbian I'd known since school. I should have been happy for both of them, but I was only able to be through a great effort of will. Now they were both with each other, so I saw even less of both.

Georgie and Louise were an item. They seemed very happy.

Then, after six months (again!), something happened.

***

It was Louise who called me, oddly enough.

She sounded upset and I suggested we meet for a drink. That evening, I waited in the pub for her and she came in. Her eyes were red.

'Georgie's broken up with me,' she said.

I was less than prepared for this. Louise was a sweetheart, and she was also experienced enough to be confident about her sexuality. I was sure that if anyone could make Georgie melt, it would have been her.

We talked about it, and it emerged that they'd indeed been very happy except for one thing: Georgie never had an orgasm when they made love. Louise was the sort of person who could have an orgasm just by thinking hard about Dua Lipa.

'I don't understand,' Louise said. 'I mean, I tried everything. I think. I thought maybe she's ace, but I don't think so. It's just some intimacy thing.'

She sipped her vodka and coke and looked miserable.

'She never had one with me, either,' I said.

'Never?' Louise said. 'God. She didn't tell me that.'

At that point, my phone rang. It was Georgie. I went outside.

'Hi,' I said, 'what's up.'

'I broke up with Louise,' came Georgie's voice, sounding hoarse.

'I know,' I said, 'I'm in the pub with her.'

'Oh fuck,' she said. 'I wanted to come and see you.'

'Maybe tomorrow?' I said.

'Okay.'

'How are you?'

'Miserable. It didn't happen with her. I feel like shit because she's so great, but... I just don't think I really fancy girls.'

'Well, I won't tell her that.'

'Please don't.'

'Okay,' I said, 'look after yourself, okay? I'll see you tomorrow.'

I went back in to Louise.

***

The next day, I skipped a lecture and went to see Georgie.

She answered the door in her pyjamas. Her face was red. She invited me in and put the kettle on.

'It's so humiliating,' she said. 'Poor Louise.'

'What are you gonna do,' I said.

'I don't know,' George said absently, staring at the floor, nursing her cup of tea.

None of the usual phrases seemed up to the job. The idea of telling her to not worry about it seemed insensitive. Going to a sex therapist would cost money.

The girl I liked most in the world, and who I most lusted after, and whose opinion I cared about the most, was sitting opposite me, dejected that her ex-girlfriend couldn't satisfy her.

There is no manual for what you do, at these moments. I envisaged many cups of tea, many cupcakes. If that was what Georgie and I were about from now on, well, so be it. I didn't know what else to do.

Then, Georgie looked up at me.

'Can we get back together?' she said suddenly.

'Who?'

'You and me.'

My heart leaped, but at the same time it felt like a betrayal of Louise. And I couldn't help wondering if this time Georgie would get tired of me after three months, and decide that she just needed a better boyfriend.

'Isn't it a bit soon to be on the rebound with someone?' I said.

'Don't you want to?'

'Of course I do,' I said, 'but you literally just broke up with Louise.'

'I just want to feel something other than this,' she said, miserably.

'Yes,' I said, finally. 'We can get back together. But whatever's making you not able to come, you have to let me help you find the solution.'

'Okay,' Georgie said.

She looked at me for a long moment, then got up and headed for the door.

'I'll be back in a moment,' she said. 'Stay there.'

She left the room, and I sat in the armchair, waiting.

After a few minutes, I heard her come back in. She walked around the armchair to where I could see her.

Georgie was naked. She blushed at my stare. In one hand, she held a black sleep mask.

She came up to me and nudged my knees with her foot. I parted them. She knelt between my legs and unzipped my jeans, then took out my cock, which was growing hard.

She looked up at me and then slipped the mask over her eyes, and bent over my cock.

I watched as she sucked me off, and watching Georgie kneeling naked and blindfold before me, sucking my cock, was extraordinarily arousing, even though I don't normally like being given head.

I moved my hips and she grasped them and sucked harder, and I shut my eyes and whimpered, knowing that she was doing this to show her gratitude, and I felt powerful and manly and dominant, and then I felt guilty about feeling like that, and then I couldn't help it, I felt myself coming.

She took her mouth off my cock as I came, and I opened my eyes to see her kneeling there, her lips slightly parted, gasping as I came over her mouth and nose and the mask. She lifted the mask and closed her eyes as the last of my spurts of semen splashed over them.

Then she was kneeling there, her hands in her lap, naked, her face covered in my cum, her bare chest rising and falling.

I reached down and pulled her up to me and kissed her, rubbing our faces together. She gave a low chuckle in her throat.

I put my arms around Georgie and held her naked body.

For once, I was clothed, and she seemed like the vulnerable one.

***

After that, we were back like before. But now we had a bit of a shared purpose.

We tried exploring pornography together, but it was pretty predictable. We talked about having a threesome with another guy, but our hearts weren't really in it, and we couldn't find a guy who fancied both of us and who we both wanted to have one with.

We did become more intimate. Georgie used a prostate massager on me, and I masturbated her. We talked about fisting, but it raised all her anxieties and while we got ready to try it, she always got too nervous and called it off.