Craig’s List Dating is Alive and Well and Living in Montreal

It started out as a typical kind of day for this self-employed crossdresser. Or should I say crossdressing contractor?

My wife was going to be out for the morning. She knows about ‘Linda’ and is comfortable around her but I still enjoy the private times when I get en femme. I don’t have her critical/ helpful eye there to see and advise on what I’m doing right or wrong. She is quick to offer advice whether I want it or not. Do you know the feeling? Also it’s a strange thing that even when I’m en femme I have trouble effecting a feminine voice and mannerisms when she is around. I’ll bet you know that feeling, too.

So I treasure my alone Linda time.

As the day went on I was sitting there working on a near-due report, dressed in one of my most recent purchases from Value Village (the Canadian equivalent of Goodwill). A few days earlier I had visited the store and picked out some finds I could not turn down — A Joseph Ribcoff mid-calf length casual dress and a thin-strap sun dress, brown with large white polka dots with the designer label removed by the previous owner. Ribcoff dresses usually sell in the $200 range. This one was $14.95. But I digress.

Pretty well as soon as my wife had left for the morning I had applied a little make-up, put on the summer dress, figured out how to use some two-sided tape to keep the dress straps in place over my bra straps and got busy doing the housework. I reminded myself of those TV housewives back in the 1950s — you know June Cleaver, Harriet Nelson and the like — always dressed ‘to the nines’ in those dresses with the flared skirts doing housework or getting dinner on the table. No leggings and baggy tees for them.

Having done the dishes, made the bed and tidied up the bedroom, living room and kitchen I had just made myself a cup of tea and sat down to go through the latest emails and check the on-line news then finally got to that report when I heard the door opening. No panic; my wife is used to coming home to see Linda at work or sitting there relaxing. Usually she would look around and say something like ‘Hi hon. I see you have been busy. Thanks. I owe you.” Not this time.

It was more like her taking one look at me and how I was dressed and saying, “Oh that’s appropriate. Here, there is a message for you,” as she dropped her cell phone in my lap.

Now, believe it or not I do not own a cell phone. Or at least we share one which turns out to 99% her share. I rarely need it anyway, preferring to do my business contacts by email and Skype. But I have to remember how I am dressed before accepting those Skype calls.

I was still somewhat taken aback by my wife’s curtness. Here is what had happened: her cell phone had rung while she was driving. She let it go to voice mail and then found a good spot to pull over to listen to the message. She had expected it was one of her children or perhaps a golf friend.

“Hello, I’m trying to reach Linda Jensen,” said the male-sounding message, “This is Fiona xxxx If this is the right number could you get her to call me at xxx-555-xxxx.

Who was Fiona? I thought the name was familiar. How had she got that number? After maybe several years what did she want with Linda?

The Fiona (a fabricated name of a fabricated name) I remembered would be someone I met several years ago. We had chatted a bit and found we had several things in common, not the least of which was that we both know how pleasing a man could be so pleasing for our egos. I don’t give out phone numbers but apparently I don’t hide them so well either as when Fiona wanted to reach me she just had to go back through her phone’s archives.

I was nervous, for sure. What did this Fiona want? How did she get this number? Was I about to be outed? There was only one thing to do: call her back.

“Do you mind if I talk to her privately?” I asked my wife.

“Go ahead but from the voice that was not much of a her,” she replied. My wife does not usually make disparaging comments about crossdressers. This was another way of her delivering a message to me that she does not like ‘Linda stuff’ coming across her phone. I did not see it as that much of a problem as I had made sure our names were not registered with the phone.

I took the phone upstairs to the bedroom I use as Linda’s closet and dialed Fiona’s number.

The call was picked up on the second ring. A male voice answered. “Is this Fiona?” I asked.

“Yes, she replied, her voice becoming softer but still a bit husky. “Is this Linda?”

“It is,” I replied, “but how did you get my number?”

“You had to call me once about three years ago. It was about a change of plans. It came through as ‘unknown caller’ but as soon as the call was finished I saved the number and added your name. You know I wouldn’t be phoning you but it has proven easier to find your number than your email address.”

“So what do you want? How can I help you?”

“Remember the discussion we had last year about Craig’s List and them closing down their Personals section?”

“Yes, I remember. That was a tragedy for both of us, as I recall,” I replied.

Craig’s List is a large and dynamic world-wide on-line want ad service. It has sections devoted to for sale, housing, jobs, community services etc and for a while it had a huge section devoted to personal contacts. For a number of years among the services was a dating site that offered sections called ‘Strictly Platonic, ‘Dating/romance’ and Casual Encounters. Within each section people could post as M4W, M4M, and many other combinations including T4M, T4W, T4MM and a long list of other possibilities. The great thing about Craig’s List for Fiona and I who both travelled a lot was that their ads were sorted in to some 700 cities in 70 countries. If I was going to be in Denver or Stockholm, for instance, I could place a T4M ad specific to that area and within a short time, sometimes minutes, the replies would start coming in.

Fiona and I agreed that not all responses would be serious, quality responses but part of the fun of the process was separating the wheat from the chaff. Almost always the ads paid off as we both reported finding nice dates pretty well everywhere we went.

Not everything was perfect, though. It was clear as we posted our casual encounter ads that there were many others in many places were using that space to offer their paid sexual services. That had the potential of bringing Craig’s List afoul of a new law about to come into effect in the States where they could be held liable for damages incurred by a person responding to an ad on their site so a little over a year ago they closed down the Personals.

About that time Fiona and I had talked about the situation and how it drove a nail in to our social lives.

“Remember what you said at the time?” Fiona asked me over the phone, “You said ‘nature abhors a vacuum’ and that something would appear to take its place. You even told me that you would not be surprised if people started placing contact ads in their Missed Connections section.”

“Yes, I remember that. I still think it is true. I should check it out.”

Missed Connections was a part of the Craig’s List ads that was not shut down. It appears in their Community section and it is mostly designed for ads that might read something like this:

Arlington Subway Station

You were getting off the subway at 4:10 last Monday as I was getting on. You were wearing a flower print mini-dress. You smiled at me. I felt we had a connection but I was too shy to say anything. If you see this and would like to get together for a coffee please reply back.

I can’t imagine the odds of someone seeing and responding to such and ad but always there are people trying. But I can imagine people wanting to meet other people placing a similar ad. Perhaps it would read something like this:

Hot Young Stud

I have wanted to meet a hot young guy but since Craig’s List closed down their Personals I have nowhere to look. Write me back if you would like to get together.

“Well they are doing it,” Fiona interjected, “I’m going up to Montreal so I decided to check on Craig’s List’s Missed Connections. You should see it. From maybe three or four furtive posts in a month they are getting perhaps 30 a day. Besides the usual ‘I saw you at the bar’ ad many are clearly offering escort services and many are seeking some sort of kinky encounter. If there are so many are placing ads there must be a lot more responding to the ads. I took the plunge.”

“What do you mean you took the plunge?”

“I placed a Missed Connection ad on Montreal’s Craig’s List,” she said, “and the replies are coming in.”

“Really? What kind of replies?”

“Pretty well the same as the T4M ads would get. A lot of guys just want to show off their penises. Some I think just reply to see if they can get me interested in them but I’m confident I will have a good time in Montreal.”

By then my curiosity was totally aroused but I had to tone it down. My wife was close by. She knows about Linda and she knows that Linda plays around a bit. I’m lucky that we are both able to separate sex from romance and that she trusts me to keep myself safe and clean but she does not like to have Linda’s activity shoved in her face.

Of course I was curious to know how Fiona planned to carry it off but it was time to end the conversation. “Let me know how it all turns out,” I said to Fiona, “and be careful”, words my wife always tells me when I’m about to leave on another Linda adventure.

But already I had decided to look up Fiona’s ad on Montreal Craig’s List. She told me the date it was posted and that hers would not be hard to pick out.

Admirers: what do you think? Would you be able to find that ad? Would you be tempted to respond?

(Click the graphics below for a larger view.)

At this writing Fiona has been to and returned from Montreal. I’m anxious to hear how it went and anxious to tell you all about it, if she agrees. But remember a lot of what happens in Montreal stays in Montreal. C’est la vie!

Tags: crossdressing, featured, personal ads

Category: Transgender Fun & Entertainment