Dear Lucy — Secret X Dresser

Letter of the Week

Am I still straight?

Dear Lucy,

I’ve never written in before but I can’t stop thinking about what happened and I need to get it off my chest.

I’m 34, married (sort of), and until three weeks ago I thought I was completely straight. Then I met her.

I was staying in a hotel for work. Thin walls. I heard a woman moaning next door — properly enjoying herself. When it went quiet I did something stupid and knocked. She opened the door in a bathrobe, tall, dark hair, full lips, the lot. She let the robe fall open and… she had a cock. A proper thick one, already hard.

I should have left. Instead I stayed.

I ended up on my knees sucking her off while she held my hair. Then I fucked her arse while I wanked her. She came over her own stomach and I came inside her. We went at it most of the night. By the morning I was licking my own cum out of her while she sat on my face.

I’ve been back to that hotel twice since. Same room. Same girl. Every time I tell myself it’s the last time, and every time I end up with her cock in my mouth again.

I can’t stop. I think about her at work. I get hard on the train. My wife knows something’s different but she hasn’t asked yet.

Am I gay now? Bi? Or just a bloke who found something he didn’t know he needed?

I don’t even know what I’m asking you. I just needed to tell someone.

From
James (not my real name)

Lucy replies:

James,

You’re not “gay now.” You’re a man who discovered he likes a beautiful woman who happens to have a cock. That’s far more common than the magazines usually admit.

The fact you keep going back tells me everything. You’re not confused — you’re hooked. And from the way you write, she knows exactly what she’s doing to you.

My advice? Stop trying to label it and just enjoy the fact that you’ve found something that turns you inside out. Most men never get that lucky.

If she invites you back for a fourth time… go.

Lucy x

From a regular reader

My wife’s secret

Dear Lucy,

My wife Claire has been crossdressing properly for six years. What started as a bit of fun on weekends is now basically full-time when we’re alone.

She’s 5'10", long legs, soft tits, and a thick cock that she keeps waxed smooth. Last Saturday she came downstairs in a tight red dress, stockings and heels. She looked better than most of the real wives in the old magazines.

She rode me while I stroked her. She came across my chest while I was still inside her. Afterwards she stayed on my lap, full of my cum, and told me to write in and tell people what my wife really is.

So here I am. My wife is a crossdresser. She fucks like she was born for it. And I’m the luckiest bastard I know.

Mark

Lucy replies:

Mark,

You’re not just lucky — you’re honest about it. Most men in your position keep it buried. The fact that Claire wanted you to write in says a lot about how comfortable she is in her own skin (and in that red dress).

Keep treating her like the wife she is. The rest of us will be quietly jealous.

Lucy x

First time nerves

I nearly bottled it

Dear Lucy,

Met a crossdresser through an ad. We arranged a hotel. I was so nervous I almost turned around in the car park.

She opened the door in a black slip and hold-ups. No knickers. Hard cock already sticking out. I froze. She just smiled, took my hand, and pulled me inside.

Twenty minutes later I had her in my mouth and my fingers in her arse. An hour after that I was bent over the end of the bed while she fucked me slow and deep, whispering what a good boy I was.

I’ve never come so hard in my life.

I thought I was going to feel ashamed afterwards. Instead I just felt calm. Is that normal?

Dave

Lucy replies:

Dave,

Yes. That’s normal. The shame a lot of men expect often doesn’t turn up when the person on the other side of it is patient and confident.

You didn’t bottle it. You walked through the door. That’s the hard part. Everything after that was just two people enjoying themselves.

Go back if she offers.

Lucy x

Office encounter

She was in the stationery cupboard

Dear Lucy,

I work in a big open-plan office. There’s a girl on the third floor I’ve always fancied from a distance — tall, quiet, always immaculately dressed. Last Thursday I went to the stationery cupboard for printer paper and found her already in there.

She was adjusting her stockings. The door clicked shut behind me. She looked up, smiled, and said, “Are you going to stand there or are you going to help?”

I helped. One thing led to another and five minutes later I had her bent over the paper shelves with her skirt around her waist. That’s when I felt it. Hard, hot, and pressed against my thigh.

I froze. She just reached back, took my hand, and put it on her cock.

“Still want to help?” she asked.

I did. I ended up on my knees in that cupboard sucking her off while she bit her lip to stay quiet. She came in my mouth and I swallowed it like a good boy. Then she straightened her skirt, kissed me on the cheek, and walked out with a ream of paper under her arm.

We’ve done it twice more since. Always in the cupboard. Always quick and filthy.

I think I’m in trouble.

Tom

Lucy replies:

Tom,

You are in trouble. The good kind.

Stationery cupboards have launched more secret affairs than hotels. The fact she keeps coming back means she’s enjoying the risk as much as you are.

Just try not to get caught with toner on your knees.

Lucy x

Long-term arrangement

We’ve been doing this for two years

Dear Lucy,

My girlfriend (let’s call her Sophie) started crossdressing a couple of years ago. At first it was just underwear at home. Then full outfits. Then she started going out like that.

Now she lives as a woman most of the time when we’re together. She has beautiful tits, a smooth body, and a cock I can’t leave alone. I fuck her, she fucks me, we take turns, and somehow it never gets old.

Last weekend she made me wear her knickers under my jeans while we went out for dinner. All night I could feel the lace. When we got home she bent me over the kitchen counter and took her time with me while I was still wearing them.

I used to worry what it said about me. Now I just worry we won’t have enough nights in the week.

Is there a point where this stops feeling new?

Chris

Lucy replies:

Chris,

From the sound of it, no.

Two years in and you’re still getting hard over lace under jeans. That’s not a phase — that’s a very happy arrangement. Most couples would kill for that kind of heat after two years.

Keep the knickers. Keep the kitchen counter. You’re doing fine.

Lucy x

Confession

I paid for it and I don’t regret it

Dear Lucy,

I’ve always been curious but never had the bottle to do anything about it. Last month I finally answered an ad.

She was stunning. Proper model looks, soft voice, expensive perfume. We met in a nice hotel. I was shaking when I walked in.

She sat me down, poured a drink, and just talked for a while. Then she stood up, let her dress fall, and I saw everything. I must have stared for a full ten seconds.

She laughed gently and said, “You can touch if you want.”

I wanted. I touched, I kissed, I ended up with her cock in my mouth and my own arse full of her. She was patient and filthy at the same time. When I came she held me and told me I’d done well.

I paid her. I know some people look down on that. I don’t care. It was the best night of my life and I’ve already booked her again.

Does that make me pathetic?

Anonymous

Lucy replies:

Anonymous,

No. It makes you someone who finally stopped waiting for permission.

You were treated well, you enjoyed yourself, and you’re going back. That’s not pathetic — that’s honest. Plenty of men spend years wishing they’d done exactly what you did.

Book the next one. Tip her properly. And stop apologising for getting what you wanted.

Lucy x