Coming out to a Friend

This is a true story about how I told my friend I am a cross dressers.

I arrive at his house and he greets me at the door.

We are both nudists and since he is single we hang out naked at his house and have a few beers.

About 9 months ago while sitting on his couch naked and a few beers I finally asked him what I had been wanting to for awhile.

"So, how do you feel about cross dressers?"

He seemed kind of shocked and at a lose for words. He said he never really thought much about it.

I have always suspected him as at least bi although he has never tried to hit on me. Although I have noticed him looking at my cock often.

He seems to have all male friends and has never really brought up women except that he was married along time ago but if just didn't work out.

He asked my why I asked him about that and just told him I like to dress.

He wanted to see me dressed up so I told him I have my clothes in my car if he really wanted to see. He said sure go get them.

I put on my man clothes and get my bag out of the car. He wanted me to change in front of him so I did.

I have always tried to hide my hard on from him but as I got dressed there was no hiding it.

We decided on fishnet thigh highs, panties, a mini skirt, bra with my falsies, a blouse and my long wig.

So sit next to him on the couch and he complements on my legs. I have little hair on my legs but I wasn't shaved at the time.

I did get up to piss and walked across the living room in my heels and skirt. After awhile I told him I was hot and took off my skirt and blouse.

I sat there in my stockings, heels, panties, bra and wig.

We sat and talked for about an hour before I told him I should be going.

We both stood up and I thanked him for letting me express myself like this.

We hugged, a long hug and I just decided to feel his cock.

He had ED so he can't get hard, He always says he wish's his cock was bigger.

I was hard and he started stoking me though my panties.

I asked him if he wanted to suck me and he got down on his knees and took me in his mouth.

Somehow we ended up on the couch, my panties now off and both sucking each other.

I have sucked men before but never a guy with ED.

He didn't have me cum in his mouth but jerked me off until I shot all over my chest.

We continued to meet to and get naked but never brought up the that day again until one day we were hanging out and I just had to ask him about how be felt about that day.

We told me he was fine with me dressing if that is what I wanted to do.

I told him a do this from time to time but there were also times I just didn't feel like dressing as a woman.

I told him how lately I have been dressing, sometimes it's just panties and a bra when I get home from work and want to relax.

I had my bra and panties in the car and asked if it was ok if I wore them today, he said sure by all means go get them.

So I put on just the black bra and black lacy panties and we just hung out, he was nude as I was before I brought up the cross dressing episode.

We talked about how we had played with other guys, how that all started for both of us. What we have done and what we haven't done.

I told him sometimes the desire to cross dress is so overwhelming. How I want to shave my legs and go out in at least semi public as a woman.

I also told him I would like to come over completely dressed again and he said that would be fine.

Again it was time for me to get dressed and head home. I got up from the couch and kind of teased him with my pantied crotch in front of his face.

We laughed about this after I was back in my man clothes and I told him at least I didn't stick my cock in his face.

He said "Go for it" so I did. Of course I was hard and again he took me in his mouth.

We moved to the couch where I sat down and he got on his knees and continued to suck me.

This time I jerked myself off as he watched. I then got dressed and left with hope that I will completely dress the next time we are together.

A few weeks later I texted him and told him I'd be taking some much needed time off next week and we should get together.

We planned on Monday morning. He asked what I wanted to do and I told him I was just happy hanging out.

Since we are nudist and I had already told him I would like to completely dress for him again, I told him 'I can be nude or dressed wink wink'.

Then I texted emoticons of bra and panties, a dress. high heels, and lipstick.

It took him awhile to text back but he told me I was a mess.

I told him I know it's not normal but I want to spend an entire day like that and to let me know if he would rather I didn't.

He told me it's my day off and he wasn't offended by it, dress or be naked He's fine and I'll be safe with him.

I told him I want to but do I dress here or dress at his place. He told me either is fine but might be safer dressing there.

I told him how the thrill of it all was driving and arriving dressed up. He was worried about me getting pulled over or a flat tire dressed as a woman.

The day arrives for us to meet again. I wake up early and paint my toenails a nice bright red.

I shower and shave before I leave my house. I also shave my legs, something I have been doing lately and love the feel.

I drive to his house wearing a bra and my small breast forms, I am also wearing panties and knee highs and my girly sneakers.

When I arrive at his house I bring in my bag with all my woman clothes.

I get there I take off my shoes and we both sit on the couch and talk since it's been awhile since we last met. We have a beer to loosing up some.

He finally asked about my toenails, asking me when did you paint them?

I told him I did this morning and did you just notice them? He said he did right away. He also said he noticed my breasts.

I asked him it was ok if I changed and he said of course. I asked to use a bedroom and told him I'll be awhile so get comfortable.

I go up to his bedroom I start by getting naked, which I love about as much as I do cross dressing. Especially being naked someplace I have never been naked at before.

I start with my bra and falsies. Next is my blouse. I need to put these on before I do my makeup. My friend has never seen me in makeup yet.

Now for my makeup, I start with concealer to hide my beard stubble. Next is the foundation that goes over my entire face.

When I am satisfied with my facial skin so far. I work on eye shadow and eye liner. Then comes mascara and blush.

The final touch is lipstick. I use a nice pink what has some sparkles in it.

I remember one time I had my lipstick on and had a cup of coffee from the store with one of those white lids on it and leaving a pink lip mark on the coffee lid. I loved that.

Next is a nice pair of thigh high stockings. I choose tan since I know my friend has commented on how he likes sexy legs.

The other time I dressed fully for him I wore fishnets but had not shaved. The tan pair looked great with my shaved legs.

Next is a pair of panties and a mini skirt and heels.

I put on my wig, comb it out and give myself one last look before I walk down the stairs as Sara.

I'm ready and open the bedroom door and head for the stairs. My heels clicking on the floor as I walk.

Down the stairs I meet my friend relaxing naked on the couch with a big smile as he sees me.

He tells me how good I look, the makeup and the shorter wig look good on me. I ask him if he thinks I could go out in public like this and he agrees I could.

I sit on the couch with him. I love to walk around in heels so I follow him into the kitchen when he suggest we have a beer another beer and some lunch.

We stand around in the kitchen drinking our beers and making sandwiches, him naked and me dressed like a girl.

I told him a really would like to go to a park or some place semi public dressed sometime. Maybe not in a mini skirt and heels but I have legging and would he like to see them.

He said yes to I go upstairs and take off the mini skirt and put on the leggings. I love the look of the black leggings and heels so I put my heels back on.

I also put on a sweater that is open in the front and longer in the back. I think it's a sexy look.

He says 'Oh that's nice'. I said I would wear my sneakers not my heels and swap shoes for him.

So now I am wearing all black, leggings, blouse and sweater and ask him if it's too much black I have a white blouse.

He said he thought maybe it was and I suggest I try on the other blouse. He said ' Wow I didn't know I would get a fashion show'

So back upstairs I go again and put on the white blouse and come back down. I agrees it looks much better.

We talk about sometime we could go for a walk, I am very excited to do this.

We finish out lunch and I tell him I'll go change again. I decide it's time for a different look so I take off the leggings and change back to the black blouse.

I also remove my panties and think this is a good look, wig, makeup, blouse and bra with falsies, tan thigh highs and heels. No panties or skirt.

So back down the stairs I go again and sit next to him on the couch.

I sit as ladylike as I can, legs crossed with my feet with painted toenails and heels dangling.

Time to step it up again and show off my toenails even more so I slip off my heels and remove my stockings.

I am enjoying my time dressed as Sara, but it's getting time to leave. I ask if I could use his room again and get ready to go.

I go upstairs and get naked and remove my makeup and wig. I pack everything back in my bag and walk down naked.

We sit on the couch and talk about how he is fine me doing this whenever I want, this is a safe place for me to express myself.

I tell him how it's hard to explain why I do this. I can be fine not dressing for weeks but when I get that desire it is so overwhelming, It becomes an obsession.

We talk about the clothes I have and I try on a few other panties I brought.

We also talk about how he felt bad that he sucked my cock twice. I guess he thought I thought that was a bad thing.

I told him it isn't my goal to have sex but if it happens it happens. We just enjoy each others company and being naked. I also enjoy being Sara.

It is so nice to dress for someone, doing it alone was a thrill at first but it does get a little boring after awhile.

The next time we meet he picks me up after dropping my vehicle at the shop for service and as I get in his car he asks "Where is all your stuff?"

I tell him we can talk about it later. He finally asks later about him and I explain that I stopped for awhile but I'm sure I'll do it again.

We discussed me dressing and again he tells me he is fine with it. I asked him if he was disappointed I didn't dress and he said he was fine either way.

We did joke about me dressing and he told me when I came down the stairs in bra, blouse, stockings and heels it was hot.

I had no panties or skirt on and had a hard on. I'll have to remember he likes this.

This the beginning of my story, there will more more to follow. Thanks for reading.