Written by Xdresser_Alexa

06 Mar 2014

I think it was on our third date that I first learnt of Greg's 'preferences'. We were sitting in the cafe, having just seen the latest Woody Allen film, discussing whether it was funny or not. [I thought it wasn't. He loved it.] There was a few seconds' silence, save for the sound of the other people chatting, and the radio up at the counter. Tegan and Sara were singing "You Wouldn't Like Me."

"Here's an idea", Greg said. "We'll play 'You Wouldn't Like Me'. Right now, right here, we get to confess, one at a time, stuff you're insecure about in yourself; things we think 'hey, if it gets out, this date is history'. That way, we bring it out into the open and we don't have to sit here worrying about it."

I was a bit reluctant at first, but there was something about him that made me play along. Maybe, I thought, he's got something big to say, and this is his way of leading up to it.

He revealed his love for German Krautrock. I [quietly] revealed my silly teenage girl love for East 17. He revealed that he has his laundry done professionally because he doesn't know how to work the washing machine. I told him how I actually thought Woody Allen had sucked for the past two decades. He told me how he can't eat strawberries without spending a day on the john. I told him, giggling, how seafood gives me flatulence. We laughed together.

Then he grew more serious. "Jayne, I've got to tell you this next one. And if you put your coffee down, walk out, and delete me from your life, I won't blame you." He looked around to make sure nobody was eavesdropping. "I'm a... transvestite."


"Y'know." He mouthed the next words quietly. "Women's clothes. Underwear."

I raised my eyebrows at him. "...what *sort* of women's clothes?"


"Say... a night out on the town, a day out in the country or a night in with someone special?"

"Ummm... ahhhh..." he stuttered; I think he'd expected me to be angry or dismissive, but certainly not curious.

"You've got pictures, right?" I said, cutting across his - undeniably cute! - uneasiness and hesitation. "I'm sure you do. Most do have."

"Well, yes...." His cheeks were turning bright pink.

I smiled at him. "It's okay, you're not the first man to confess it to me. And it's not something I'm scared of." I whipped out my Blackberry. "Are they online?"

We had to leave the cafe to get a signal, so we found a seat down the street. In seconds I was on his second "secret" Facebook account, seeing him - her! - as 'Bethany', both clothed and half-clothed. Most of them were obviously self-taken, in mirrors, though there were a few in a maid's, a nurse's and a WPC's outfits that looked more professional. I had to try a little harder to prise the details of those out of him. "Not proud of this, but... I went to see a, *ahem*, 'working girl' - I saw on Facebook that she specialized in it. She didn't do anything to me; just provided the gear and took the photos."

He shook his head, as if to get rid of the stress. "Look, I confessed four things, you only confessed three. I need one more from you - the big one, whatever that is."

I leant over to him and whispered in his ear. "I love trannies."


Well, that was how we started. And that was the evening we started. He had a few suitable garments back at his place, but not very many - apparently his previous partner, who wasn't positive about these things, had thrown far too much out. He told me how liberated - and how exhilarated - he felt at having told me his secret almost straight away.

We started to explore each other. He got to know straight away, for example, how I cum much easier and quicker to someone's tongue than to cock. Like all men, he thought he was brilliant at it. Well - he was pretty good, certainly better than some, but needed a little encouragement to get it just right...

And I had to adjust too. It had been Dave/Daria, about six or seven boyfriends ago, who had taught me how some men enjoy crossing over - but he/she had wanted me to dominate her, to whip her, to humiliate her. I enjoyed that - it was great when he was Daria, although not so good as Dave.... When I tried that kind of thing with Greg as Bethany, he stopped me straight away. "No, it's not like that. I'm not into that stuff - I don't want to be your bitch."

"Then what is it like?"

"More... your girlfriend. Your... *ahem*... lesbian girlfriend." And he blushed. I knew I'd found one of his hot spots.

So, over the next few weeks, I decided I'd run with it. I'd say "hey, girlfriend!" when I answered his phone calls. I left copies of "Diva" around my flat when he came over. I teased him by leaving links to harnesses and double toys on his alternate profile. Okay, it's nothing deep, but I know that the little things pressed his buttons.

Before I knew it, we'd been going out for three months, and we agreed to buy each other little presents to celebrate.

He'd been away with work for a week, so I was fairly hungry for him - and her - that evening. But he'd got back in time to prepare us some delicious pasta - I was all for encouraging his rapidly improving cooking, too! - by candlelight, after which we were soon canoodling on his sofa to some soppy movie. His skin was soft - and wonderfully smooth, with the tips I'd given him - as we caressed each other and kissed. Knowing what I'd got for him was making me moisten too...

I unbuttoned his shirt, pulled it off him, and pushed him onto his back. Straddling him, I circled my fingers around his hardening hairless nipples. "Sweetheart! I do like your boobies..."

"Not as much as I like yours...." He tried to reach up to mine, but I patted his arms back down.

Using my fingernails on the tips of his nipples, I teased him further. "You'd love to just have our breasts bouncing together, hey?... Have your own pair all the time to cup and to hold?..."

"God, yes!"

"I know you. If you had your own titties you'd never leave the shower." I giggled as I dug a nail in his left nipple and twisted it slightly. Yes, he's not into pain or humiliation, but it doesn't hurt to establish who's in charge...

"Ow! Guilty as charged!"

I raised myself off him slightly. "Turn over, sweetheart." He rolled onto his front, stretching his legs off the end of the sofa. "And close your eyes."

I reached underneath where his feet stuck out, where I'd left the bag I'd brought with me. And silently prayed that I'd got the measurements right...



I grabbed his right arm from underneath him, and looped the material over it and up to his shoulder.

"Wha....?" He already knew what it was. I passed it underneath him, and bent his left arm into the other loop.

I adjusted it so it sat right on him, then leant forward to whisper in his ear. "Sweetheart Bethany, I've bought you your first bra. Will you be my lesbian lover whenever you wear it for me?"

"Yes! Yes! You know I will!"

"You want me to do you up at the back?"

"Please, Jayne, please!"

"Keep those eyes firmly shut!..." I hooked the eyes on the bra, and pushed my finger underneath and passed it around to make sure it wasn't too tight. A perfect fit: I was rather pleased with my work!

"Turn over." When he did, I caressed his nipples through the cups - "A" was just about right for him, though a few years on he might go up to a "B" - then reached down to undo his trousers. As I'd suspected - and hoped - he'd worn satin panties, just full enough to keep his cock inside. I ran my hand briefly over the material, and his obvious excitement.

"Okay, in a minute you can open your eyes. But know this. When you wear the bra, you are Bethany. You will be my girlfriend, my woman, my lesbian lover. You'll finally be 'she'. Understand?"

"I understand." His - no, that's wrong, now it was appropriate to say 'her' - voice was croaking with excitement.


She blinked at the light, then looked down, to see the red lace bra over her chest. I ran my fingers under her straps, then adjusted the right one to give her shoulder a little more room.


"What do you think?"

"I.... I..." She was speechless.

"The black panties don't really match - we'll have to sort that out another time. Now, how does that feel? Comfortable?"

"Ah.... Not too tight. Can you do the other strap too?" I reached down to adjust it. "And these..." Her right hand pulled up to her breast; her eyes glazed - both with joy and, yes, moisture. Something deep within her had been touched, and the energy was about to pour out of her.

"Now, don't get all soppy on me" I scolded, grabbing a tissue for her to wipe her eyes. "Take the rest of those clothes off - you're no female cross-dresser, are you?"

I got up off her and let her remove the trousers and socks. I bent down to feel her legs - newly shaved - and kissed her on her knee. Then I took off my own top - to reveal my own red bra. Just like hers, only a "C" cup, and uplifted to make the most of what I have.

She was shaking slightly as I pulled her up from the sofa. Reaching out to take both her hands, I led her into the hallway and in front of the full-length mirror. "There! Aren't you beautiful?" I stood behind her and put my hands either side of her waist: her own hands were up on her chest, feeling all around on the new sensations of wearing a brassiere.

"It's... it's gorgeous. How can I ever thank you?"

I kissed the back of her neck, and ran my hands down to her hips. "We'll find a way." My right hand crept into her panties, and found her hardness. I squeezed it gently and ran my fingers down it to the tip. Already there were a few drops at the end of the skin. I decided to let her go as fast as she wanted to.

"Just look at yourself!" I whispered in her ear. "A slutty lesbian, having been stripped by her friend." I wrapped my fingers around her hardness. "Being frigged in just her bra and panties!"

"Jayne! Ah...."

"We'll let your hair grow long, and get you some red high heels to show off your legs. Then you can be Bethany with me whenever you want to be. The woman you've always dreamt of being."

Now I was pulling her back and forth slowly. Her breathing grew heavy; I knew she was getting close.

"Cum for me in your panties, sweetheart. Show me how much you want this. Show me what being my girlfriend in your bra means to you." My left hand entwined with hers, on her chest, over her nipple. She threw her head back and I made a lovebite on her neck.

"I'm going to..."

"Yes, you dirty lesbian! All in your panties! Ooze your cum out for me!"

I squeezed her head one more time, and she shot her load into my fingers. Straight away I pulled them up to her mouth so she could taste herself whilst the rest of her cream went into her panties. I had to hold her up because she was shaking so much: I leant her against the wall and kissed her deeply, sharing the last few drops of her cum.

I let her get some breath back before pulling her back to the back of the sofa. Bending her over, I told her to pull her knickers down whilst I crouched down and pulled my own panties down from under my skirt. Stepping out of them, I pulled her satin panties off and replaced them with my black cotton ones - telling her to feel where they were warm with juice at the gusset - and then put my legs into her cum-stained ones and pulled them up around myself.

I kissed her left bottom cheek: "Sharing things is one of the best bits about being girl-on-girl-friends..."


Later on, once she'd licked the cream off from all around my crotch and had her face pressed up against my pussy, I teased his - her - penchant some more.

"Ooooh... sweetheart... it's true what they say, a woman does do it better...." She was definitely improving, even more than with her cooking. "Lick it, Bethany! Up there and up to the front... hooooh... you're the first girl I've had do this since college..." That spurred her on even more!

And then, once I'd creamed on her tongue and her lips, and pulled her up to share the juices once more, we kissed deeply as I undid the hooks round her back, then pulled the straps from her shoulders. "I'll keep this. Ready for you any time to ask me for it, whenever you want to be my girlfriend."

"Thank you, Jayne. Thank you... I can't say it enough." He - now the bra was off he was definitely back to a "he" - was smiling from ear to ear, looking deep into my eyes.

He blinked a couple of times, then suddenly got up to open a drawer across the room. He still had my black panties on; I giggled as he shook his behind at me as he bent down.

And then he was on his knees in front of me. In his right hand, up towards me, was a small red box. "This is my gift for you tonight."

I opened it and found a beautiful gold and diamond ring. "Marry me. Or... well... 'civil partnership' me. Whichever you want."

My mouth fell open. I heard myself say "Yes."