Donna and Deb — A Couple in a Million

They walked in the room and looked around. More than a few sets of eyes looked back at them. My first impression was that they were sisters. Or they could have been two girlfriends who liked to dress in similar styles. Both were tall, slim and athletic-looking women. They were probably in their mid forties but in that light it was a little hard to tell. The setting was a little unusual to see two such pretty ladies in low-cut summer dresses and light make-up.

I was in one of the bars at the Parliament House resort. The Parliament House is a large gay-oriented motel and nightclub complex not far from downtown Orlando. With several bars, a large dance floor, a cabaret for one of the world’s best drag shows and a swimming pool used more for lounging, tanning and cruising the Parliament House is definitely not part of the nearby Disney complex of family oriented theme parks.

At the Parliament House you will find gay men and lesbians, so-called straight guys taking their ‘walk on the wild side’ a number of crossdressers but rarely would you find two such ladies as these. They looked lovely; they looked, in a word, normal.

I was sitting at the bar as they walked in. I was dressed as Linda. It was the first evening of an Orlando vacation after a flight from Toronto. I had spent the first half hour at the PH wandering around, taking in the sights and getting oriented. Of course I wanted to let any potential tranny-chasers in the crowd know that I was there. Then I settled in on a bar stool to see what would happen. Donna and Deb are what happened.

Le Club Disco at Parliament House

As I sat at the bar admiring the two newcomers I noticed they kept looking over to me as if they were sizing me up. I smiled at them. They came over to ask if they could join me. Of course they could but I couldn’t help but wonder why. Did they think I was another on a ‘girl’s night out’? Did they think this single girl needed some company for protection? Were they ‘lipstick lesbians’ who were looking for extra company? Had they read me?

We struck up a conversation. I was pretty sure they would read me once I started speaking but they did not skip a beat. However that was when I started to pay a little more attention to Donna. Her voice was huskier than the normal woman’s range. She also had pretty big hands and her shoulders had seemed a bit wider than normal. Then it hit me. Donna was not Deb’s sister; she was part on my ‘sisterhood’.

I did not let on I knew but they knew I knew. Soon we were talking of topics of interest to crossdressing tourists. I told them how I had enjoyed visiting the Queen Mary in Los Angeles.

“We loved the Queen Mary!” exclaimed Deb. “That is where we met.”

They told me how Deb had been part of a going-away stagette evening for one of the girls in her office. The party had ended up at the Queen Mary Show Lounge laughing along with Butch and the girls and having a great time. Deb and one of the others had become curious about the back bar so after the show as their party was breaking up they moved to the back room.

They went in to a lot of details but the short version is that she met Donna, danced with her, talked with her and they became interested in each other. Deb worked in a real estate office in the San Fernando Valley. Donna was a visiting businessman from North Carolina. When the businessman travelled an extra suitcase for Donna went along.

Donna said, “It took a lot of nerve for me to do it but at the end of the evening I asked Deb if she would like to go out to dinner with me the next evening. It was going to be a Sunday and my last day in L.A.”

“I agreed,” said Deb, “she was such an interesting person. But to my surprise when we met at the restaurant I did not recognize her. Donna wasn’t there. She had come as David and he was gorgeous! I had a hard time realizing it was the same person.

Donna added, “I had originally intended to go as Donna and I knew she would accept me but overnight I had decided I really liked this woman. I wanted her to know the other part of my personality.”

“It was love at the first two sights,” quipped Deb. They finished the night making love at Donna’s hotel room before having breakfast at Deb’s apartment.

An intense transcontinental romance ensued. They met each other’s families and they learned about each other’s pasts. While both were single they both had been married, had children now in their twenties and they both were fairly open sexually and were comfortable with what they learned of each others’ bisexual side.

They told me of one of their pre-marital adventures.

Deb started, “I guess it was the final test before we married. I had already given up my job in LA and moved to Charlotte. Donna and I decided to take a vacation where she would be Donna 24/7. I was certainly okay with that.

“We came here to Orlando. We had a great time playing golf, shopping and of course visiting the theme parks.

“Then it came the night we were to come here to Parliament House.”

“So far I had been dressing down to fit in with the straight crowds,” added Donna,

“This was to be our night to ‘glam it up’ a bit.”

“We put on our sexiest little black dresses and really did up the make-up.”

“When you come to the Parliament House you never know what you are going to get,” said Deb, sounding more like an experienced visitor than like Forrest Gump.

“We had already discussed what would happen if one of us were to get hit on. We were going to play along but under no circumstances was one to leave the other alone.”

“It turns out we didn’t have to worry about that,” said Donna. “We met two guys from Canada, like you. They were down here on a golf holiday and had decided to slip away from their group for a little fun.

“They bought us drinks and stayed with us all evening. We went in to watch the show and we danced together a bit. However, they weren’t much in to dancing.”

“Things were progressing so Deb and I had to talk. We excused ourselves to go to the ladies’ room,” said Donna. “Deb asked me if I liked my guy. I was non-committal. When I asked the same of Deb she said ‘yes, but he is no David’.

“What do you think they think of us,” Deb had asked Donna.

“I think they like us.”

“Yes, but do you think they think we are two crossdressers or two women or what?’

“Surely they have read us.”

“We’ll see when we get back. Maybe they’ll be gone.”

When Deb and Donna returned to the table the two Canadians were still there. They had ordered fresh drinks.

Apparently it didn’t take long for the guys to suggest that they all go back to their suite. Deb and Donna exchanged looks that meant ‘let’s go for it.’

“What a night that turned out to be. The boys admitted they were both married but they wanted to experience a little ‘adventure’.”

“It was kind of strange watching each other kissing other men but frankly it was also a turn-on for me,” said Deb.

“Me too. We knew they knew I was en femme but we weren’t sure what they thought of Deb,” added Donna.

As they recounted their story I found myself getting aroused.

“Well we’re not sure if they ever found out. Before they suggested that we all get naked Deb asked them to help settle a dispute we were supposed to be having. She said we were trying to settle which of us gave the better oral sex so she wanted a contest to settle it. I don’t know where that idea came from but it was brilliant.

“It didn’t take long for her to lay out the ground rules for the contest. The guys were to strip below the waist, wash themselves well and then sit back. Each girl would have five minutes with one man and then five with the other. The men would be the judge. All agreed. Then Deb threw in one more rule. If it didn’t go to the time limit the first girl to make a man come would be declared the winner. All agreed but I hoped that wouldn’t happen as I knew that would also mean the end of our evening and I was looking forward to seeing another man inside Deb.”

“We got through the first five minutes and the guys were really enjoying it. We suspect that their wives were not too enthusiastic about that aspect of their sex lives. However the changeover was way too much for the guys. First one and then the other couldn’t hold back.”

“Of course Deb was the winner but that was because I’d done all the prep work on her guy,” Donna said with a grin. “Needless to say they both suddenly got very tired and remembered their early tee time. That was our cue to leave. We laughed a large part of the way home.

“Needless to say when we got back to our hotel we couldn’t hold back. Seeing each other with someone else sparked arousal rather than jealousy.”

“Why was that?” I asked.

“I think it is because we are so emotionally committed to each other,” said Deb “we don’t feel jealous or threatened because we know each is always going to be there for the other. We had talked about it before and had agreed that we could separate love and commitment from sex for the sake of sex.”

The couple returned from their vacation, married (as Deb and Doug) and started a happy life ever after. Donna doesn’t go out much in Charlotte and they don’t hang around with the local swingers’ scene. When the urge to play strikes they will use a dating web site or hop on a cheap flight to Orlando check in to a hotel and try their luck at the Parliament House.

“Wow!” was all I could say.

“Let us ask you something,” Deb said to me. “If you were to come back to our hotel which one of us would you prefer to be with?”

I thought a while. I looked at both of them. Was there a right answer? I even thought of that old story of the lady or the tiger.

“Both,” I finally replied.

“Good answer,” they said in unison. “Any time you would like to go we’re ready,” Deb added as she squeezed my thigh. It was the first physical contact I’d had with either of them.

I must admit I hesitated for a moment but then I replied, “I can’t think of anything I’d rather do this evening than be with you. However, my wife is waiting for me back at our hotel. She knows that I have a wild side but this is our first night in Orlando. The deal was that I would just go out for a little while and come straight back.”

“Why don’t you call her?”

“Maybe we could join her?”

It hurt me to do it but I had to turn them down. Then I had to leave. Deb and Donna were left to look for new friends. We kissed our good-byes. Sadly, we didn’t exchange e-mail addresses. I have never seen them again but every time I get to Parliament House I find myself looking for them.

Category: Transgender Fun & Entertainment