The Return of Craig’s List Dating? Part 2

[Part 1] [Part 2]

I was very anxious to hear how Fiona’s trip to Montreal had gone. I assumed she had gone for business purposes but her ad on Craig’s List Missed Connections made it seem as if she was going there for nothing but play.

It turns out that she was to be in Montreal for a weekend convention which she would be attending in drab but had decided to go a few days early for some Fiona play. It was some time before we could get together to talk about her Missed Connections experiment but when we did get together she spared no details. (Unfortunately Angela, our editor, has high standards and will cause me to spare you some of the details).

“So how was Montreal?” I asked Fiona as we settled in to our corner table at the Chateau Laurier Hotel’s lounge. We were in Ottawa, Canada.

“Montreal is Montreal,” said Fiona, “it’s lively, vibrant, the restaurants are great and the people have a ‘joie de vivre’ about them. The convention was interesting and I got to meet many of the stars of the business. I also made some money at the casino,” she said with a grin.

“Two chardonnay, please,” I said to the server who had arrived to take our order. I usually don’t drink alcohol but I know Fiona’s lounge drink of choice. She said that when men see her with a glass of wine they see her more as open to advances and more than a few dates have started when someone has sent the server over with a ‘glass of the same.’

Fiona knew the information I was after but she was going to make me dig a bit for it. That’s okay I was not above begging. Fiona had gone to Montreal and she knew I wanted to know about the results from her Craig’s List Missed Connections ad. She hadn’t missed connecting with anyone. She just didn’t want to miss any while she was there.

“You know what I mean,” I pretended to plead, “how did your Craig’s List thing go? Did you get any bites, land any fish?” I asked referring to an analogy we had concocted where Internet dating was a lot like fishing. We were not always going to land ‘the big one’ or even make a catch but for sure if we did not put our lines in the water we were not going to catch anything at all.

“Oh that,” she replied innocently, “yes it went okay.” I could see by her smirk that things had gone better than okay.

The server had returned with our drinks.

“Cheers!” I said as raised my glass to Fiona’s. “Are you really going to make me work to get the information out of you? You know you are dying to tell me.”

“Okay, I’ll tell you but promise that when you write about it you won’t make me out to be a slut.”

“You mean the slut that you are?” This time it was my turn to smile and smirk.

Fiona winked and smiled back. She knew we both meant that term in the best possible way.

“In a lot of ways it was just like the old T4M ads where we used to get so many bites but only a small percentage of real action. I placed the ad a few days before I was to be in Montreal. I agreed to their terms of service and left it for a while as the ad got vetted and posted and I waited for the replies to start coming in.

“When I checked my Inbox a few hours later I already had several replies. They were not very promising. It seems there must be dozens of guys who lurk on the Internet ready to send out photos of their or someone else’s penis. They usually don’t write much, just send the photo. I don’t know if they want or expect a reply but they all got one from me.” Again she winked.

“Yes, I know that kind, exhibitionists. I think they are just too lazy to get up off their asses, go to the park and expose themselves,” I laughed. “But did you get any quality responses?”

“Eventually I did. There were several in fact. These guys had taken the time to read and understand my ad. They felt I had something that interested them. Now you know of that group there were those who just wanted to see if they could get a reply from me but didn’t intend to meet. There were those who just wanted to get a personal photo from me, preferably erotic. And then there were those few who genuinely wanted to hook up.”

“So it wasn’t much different from the old T4M days?” I asked, “What did you do?”

“Not really different at all,” continued Fiona, “so I drafted up and sent out two stock replies. One for the exhibitionists saying thanks but no thanks.”

“Did you compliment them on their junk?” I laughed.

“You know I didn’t. I felt like saying something like ‘don’t worry, with exercise it will get bigger’ but I didn’t even do that.

“For the others I sent a stock reply telling more about myself, including a photo because the Missed Connections do not include photos, also seeking out more information and laying out a few conditions if we were to meet.”

“Don’t tell me,” I interjected, “you told them that if they wanted to get you in to bed they were going to have to take you out on a date first.”

“Close,” Fiona replied, “I didn’t quite put it that way. I wrote that I was hoping to meet a sensual man who would enjoy taking me to a nice dinner or to a show and then we go back to my hotel room to cozy up. Then I gave them Plan B”

“Plan B?” I asked.

“Yes and don’t play dumb with me. You are the one that told me about the need to feel valued and know that the date is not just using you. He must contribute to the relationship.”

“The hotel room?”

“Yes, I put in the note that if he was not able to take me out then I’d ask that he contributes something to the cost of the room.”

Fiona had a point there. It’s amazing how many men we come across that think it’s fair that we girls get and pay for a hotel room and then they come over for a while, get their rocks off and leave without any kind of a commitment. For me I prefer to be taken out on a date and then I’ll be very nice with him. I think Fiona prefers the hotel room contribution. I think she is an escort at heart.

However we both are very concerned about falling into a police trap so we never ask for more than ‘half the cost’ of the hotel room and never suggest the money be paid in advance.

I changed the subject. “So what were the numbers? How did the replies break down?”

“This is only approximate but close,” said Fiona, “I probably had some 20 replies, most with photos of some kind. Let’s say that I sent the ‘thanks but no thanks’ reply to about half of them, the ones who sent no message with their photo or the message was something like ‘Hey, Wazzzup!?’ That means there were about ten who I wrote to saying that yes we should meet and laying out my conditions. Of those I did not hear again from probably four or five of them. Another confessed that he was from eastern Canada and would not be in Montreal while I was there and another actually was from here in Ottawa. He told me he was married but had a growing fascination with being with a t-girl. I offered to set him up with the local transgender support group.”

“Let’s see. That only leaves you with two or three. Did you get any action at all?”

“Three actually but one confessed that he was not quite ready to be intimate with a t-girl. So. . . then there were two.

“How did that work out?’

“Well they both confirmed that it is indeed worth sifting through the replies to find the nuggets. Didn’t you once say it was like panning for gold?”

“Yes, a lot of sand and silt is going to wash out of the pan before you get down to the nuggets,” I recalled saying.

“My first night I stayed at the Auberge des Gouverneurs right downtown on the edge of the gay district. It’s a lively part of town with a traffic free street and a park right across the street from the hotel. I knew that if the date didn’t pan out I could always head over to Cabaret Mado and catch a great drag show. It was just two blocks away.”

“And?” I asked impatiently.

“Anthony was a relatively young man, probably early 30s and originally from Jamaica but he’d grown up mostly in Toronto but was now working in Montreal. We met in the park across the street. I liked that he was there waiting for me and we both picked each other out from the descriptions we’d given each other. Frankly I was probably the only ‘almost 6 feet tall platinum blonde within 300 miles of there.”

“Ha! I know that feeling. And then. . . .”

“We chatted for maybe half an hour. He was really easy to talk with and interesting. At first we talked about his life in Montreal and how he’d like to get back to Toronto. As cosmopolitan as Montreal is and the old animosity by Francophones towards the English is mostly gone it must be difficult living in a city where you are cut off from communicating with so much of the population.”

“Yes, and remember all the signs in public places are in French only. Well that doesn’t bother me. I love the chance to speak French,” I said.

“Me too,” replied Fiona, “but for Anthony who came to Montreal with absolutely no background in a second language it was a struggle. So anyway after a while I felt comfortable enough to invite him back to my room.”

“Was he. .  .?” I paused.

“Yes he was quite okay down there and very clean. We had a good time.” Fiona went in to a bit more detail but you get the picture. “He stayed for about two hours before he had to leave.” Continued Fiona, “I was still wide awake and a bit hungry so I decided to re-do my makeup and head over to Cabaret Mado. On the way I stopped at a donair shop where the server, probably the owner, was really nice and complimentary to me. I thought of trying to see if I could seduce him but there were other customers around.

“The show at Mado was really good, fast paced with lots of jokes. They were doing a ‘Christmas in July’ theme and the crowd loved it. And do you know what I like about their show: the girls perform right through the song. It’s not like in the States where they do a bit of a number and then work their way through the crowd soliciting tips. That’s so demeaning. I’d rather pay the cover charge up front and be done with it. Besides in Canada the smallest bill is $5, eh, so the performers would be weighed down with hands full of loonies.

“After the show I went back to the donair place but my friend seemed to be gone. I called it a night.”

The next day despite the late night before Fiona was up early and dressed. She visited a gay district restaurant for breakfast and then did some shopping for fresh cosmetics before heading back to the hotel to pack and move out.

“Hey, you know what,” recalled Fiona suddenly, “We’re not alone.” As I was checking out the window menu for one restaurant I could see reflections in the restaurant window and there was another t-girl checking me out.”

“How could you tell?” I asked.

“She was looking right at me.”

“I mean how could you tell she was one of us?”

“Tall, broad shoulders, wearing a dress in an area of town where the lesbians wear shorts and tank tops to show off their tats. She was one of us.”

“So did you introduce yourself?”

“I wanted to but by the time I was turned around and heading across the street she was moving on. The last I saw her she was heading up St. Catherine toward the shopping district. I let her go. She was the one that got away.”

“Perhaps you should have placed a Missed Connection ad?” I joked. Fiona laughed.

“But I had to check out as I’d be spending the next two nights in another part of town. This was another bold move. My next hotel reservation was in my male name but I stayed en femme. I had some time to kill before check in time so I made my way out to Ville d’Anjou via a few stores and a little trying but not much buying. I didn’t have any date lined up for that day so I could take my time and enjoy myself.”

“But you had to check in under a name that clearly would not match Fiona’s image. Weren’t you a bit worried about outing yourself?” I asked.

“Not really,” she replied, “what will be, will be. Fiona’s name was on the reservation as the second guest and hotel clerks have pretty well seen everything and if they haven’t seen it they have taken sensitivity training to accept it. Check in was a breeze. We got an upgraded room and as I was checking in I was handed a phone message for Fiona.

“So to make a long story short the message was from my date for the next day. I called him back and we set a time for us to meet at noon which would be during his lunch break. “

“All went well?” I asked.

“Sure it did. He was a very nice guy, not all that good looking but a nice guy and a great kisser. We got to know each other. We made love. He ‘chipped in for the room’ and left.”

“You make it sound so routine,” I commented.

“I guess it was in a way and I would not be bothering you with details except for the unusual way I met these guys,” Fiona replied.

“Will you be using Missed Connections again?” I asked.

Fiona said the she was pretty sure that she would. “I may get dates or I may not,” she concluded, “but for sure if I do not offer myself out there I won’t be hearing back from anyone.”

“Cheers to that,” I said just as our server arrived with two fresh glasses of chardonnay. “Compliments of the two gentlemen at the bar,” she said as she pointed to two nice looking guys looking our way and raising their glasses.

“Let the games begin,” Fiona declared.

“But Fiona,” I said quickly as I saw the gents smiling and coming our way, “have you ever looked at the Activities section on Craig’s List?”

“No,” she replied, “Tell me about it.”

“Some other time,” I whispered as the two gents pulled out the free chairs at our table.

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Tags: crossdressing, featured, opinion

Category: Transgender Fun & Entertainment