Where Went ‘The Road Not Taken’?

I shall be telling this with a sigh

Somewhere ages and ages hence:

Two roads diverged in a wood, and I—

I took the one less traveled by,

And that has made all the difference.

Robert Frost

As with most students in the 1960s we came across this poem in English Lit classes in high school and university. We read it, analyzed the meaning and probably forgot it.

Yet now it is ‘ages and ages hence’. The poem has become fresh in Sally’s mind as she considered her own ‘road not taken’.

I had been invited to speak at a local support group. I was going to do a presentation on dating but as I considered my potential audience I realized that some of them had a lot more experience in the world of TG dating than did I. ‘Preaching to the converted’, I think the phrase goes. ‘I guess I’ll have to wing it,’ I thought as I drove to the meeting. ‘Perhaps I’ll ask the girls to share their views on using ladies restrooms,’ I decided. Yuck. No drama there. Not unless you are in Georgia or South Carolina or some state like that.

Then fate intervened. On the NPR radio station there happened a discussion about the poet Robert Frost and the panelists’ favorite works of his. One chose and explained The Road Not Taken. That’s it I exclaimed to myself. We are all TG’s. We all probably have dozens of ‘roads not taken’. I sure do. I decided to initiate a discussion of what would have happened to each of us if we had taken a different path at some point in life. I had not prepped anyone. I could only hope that someone would have an interesting story. I didn’t want to have to tell mine.

Well, you know how these meetings go. The long-time president starts the evening asking the newcomers to introduce themselves. The wives/SO group then heads to another room to share their monthly gossip. Announcements are made and finally the guest speaker is introduced. That’s my cue.

Have you ever stood in front of some 20 ‘sisters’? The blank looks on so many of their faces can be intimidating. What are they thinking? I always feel that some are assessing what I am wearing or the makeup job I have done. What I am saying might not be registering at all. That’s no different from any audience anywhere. The standard procedure to bring them in is to tell a joke. I told the one about the priest, the rabbi and the crossdresser. That got their attention.

It also allowed me to segue into talking about Robert Frost’s poem and our personal ‘roads not taken’.

Not surprisingly, most who spoke told of how becoming a crossdresser/transsexual they had chosen the road less traveled and described how being on that road was interesting, exciting or daring for them. Ho hum! I was beginning to worry that I might have to spin out my story. That is, I was worried until Melissa started her tale.

Melissa was a t-girl ‘of a certain age’ as they say. She was probably old like me but also like me she was managing to keep a younger appearance when dressing en femme. (At least admirers would tell us so.)

Melissa’s road junction happened back in her college days. It was summer. She had just received her undergraduate degree and had decided to enroll in a special program where she could take summer courses for the next two years and correspondence courses during her working months to qualify for a Masters degree. She was going to be a teacher. She ended up being a successful and prize-winning educator but that was not Melissa’s ‘Road not taken’.

Classes and practical exercises kept Melissa and her colleagues quite busy Monday to Friday but on Friday evening most left for home. Melissa preferred to stay around the college town. During the evenings she would head up the road 25 miles to the small state’s big city. In case you didn’t know at that point of her life Melissa was known as Melvin or Mel, an athlete and small-time student leader, member of a fraternity, had numerous female bed partners and was the father of one child that he knew. He and the mother had plans to marry as soon as he got established teaching and she finished her RNA program that the state was funding due to her single parent status.

Listening to Melissa. we all took it as a ‘red flag’ that she was heading the 25 miles to the big city rather than the 200 miles home to visit her family.

Her story continued. I will shorten it a bit. While walking to the station to catch the regional train back to the college town Mel caught a glimpse of what he saw as two gorgeous, well-dressed ladies walking into a club. Plans changed. Mel followed the ladies and found himself inside a gay bar. But what were the ladies doing there? Turns out, of course, they were part of the show. Young stud Mel figured they were drag queens but he couldn’t help but be attracted to one of the girls.

“On stage she was calling herself Ineeda Mann but off stage she was Stephanie and of course her birth name was Steven,” explained Melissa. “I don’t know where I got the nerve to ask her to join me for a drink but I did and she did.”

“Is this the start of the road not taken?” one of the audience asked.

“No, but I’m getting there,” replied Melissa. “To say we hit it off would be an understatement,” she continued. “We talked all evening except for the two more numbers and her tip-seeking tours of the lounge. She told me how her fair features helped make her successful at feminization and when you are good at something you want to do it more and more. You seek the attention it brings.”

“You mean you don’t feel that you should have been born female?” Mel had asked.

“Not really. But I was born with features that helped me feel I could be comfortable as a female and I was right,” Stephanie replied.

To make a long story short when Mel told Stephanie that it was time for him to run to catch the last train back to the college town, she invited him to come home with her. She warned that they would have to share a bed. He accepted the invitation. He knew the sleeping arrangement would be a first for him. He expected she would want to give him oral sex but he didn’t know how far he would go.

Speaking to our audience, Melissa didn’t go into a lot of the details. After all, we were an audience of t-girls. Many of us had been down the same road where the first of our same-sex relationships had been with another t-girl. And it wasn’t unusual for many of us to have had our first sex with a t-girl before we ourselves even realized our own trans tendencies.

So it was with Mel. After a night of lovemaking that involved giving his first oral sex and anal penetration he fell deep to sleep only to wake up mid morning to the sound of Stephanie taking a shower. He looked around the room. He couldn’t help but notice Stephanie’s bra, panties and negligee on the floor. Curious to what they would feel like he tried them on. He and Stephanie were about the same size. He looked in the mirror. With his long hair and fit body Mel had to admit that he didn’t look half bad. He started to stroke his sudden erection.

That’s when he heard the shower water stop running. He had time to discard the negligee but not the bra or panties. Stephanie returned to find Mel in her underwear. “Oh cute,” was all she said. Then “would you like some breakfast? You can put the nightie back on if you would like.”

“Do you have something a little less revealing,” Mel replied while pointing to his erection.

“Well, I was going to take care of that,” cooed Stephanie, “but as you wish.” She handed him a pink frilly robe.

The erection was still evident. Stephanie let it be while she prepared some coffee, eggs and toast for the two of them.

“You look good,” Stephanie told Mel at one point. “Would you like to see what you look like when you go totally en femme – dress, heels, make up and a wig?”

“Why not. If it means I can spend more time with you let’s do it,” said Mel as he put aside plans to take the train back to college and to talk by phone with his girlfriend and child.

“Road Not taken?” chirped in one from the audience.

“Not yet!” exclaimed Melissa, “Stephanie well and truly gave me a crash course on being feminine. You know that song ‘I kissed a girl and I liked it’ well I became a girl and I LOVED it! It helped that we were the same sizes for everything 36 C bra, size 9 W heels, size 10 dresses and skirts, medium blouses. It helped that I already had long hair which she washed, dried and brushed out. I didn’t need that wig. I wasn’t sure about her cutting my bangs and that was something I later had to make a story about but at the time I loved the look.

“Stephanie showed me how to get a close shave and she did a great job with my eyes and showing me how to put on lipstick. It was like Drag Queen 101 but she was not going overboard with the makeup. It was as if we were two gals about to head out for Saturday lunch and that is what we did.”

“Are you serious? Your first time dressed and you are heading out to a restaurant?” asked one of the audience.

“I know,” replied Melissa, “I was nervous as hell but it helped that Steph was full of confidence and reassurance. She also told me that the restaurant was very gay friendly and she was well-known there.”

The lunch trip turned into a bit of a shopping trip and all went well for Mel, recently drag-named as Melissa. When they got back to Stephanie’s apartment Melissa mentioned more out of courtesy than desire that she should be getting back to the college.

“You will do no such thing,” ordered Stephanie. “We are going back to the club tonight but this time you are going as Melissa. But first we’ll need some beauty sleep.”

So it was that Stephanie and Melissa returned to bed wearing two of Stephanie’s sexiest nighties.

They were well into it when Stephanie asked Melissa, “Have you ever had a rim job?”

“I don’t think so. What is that?”

“Lie on your back. Put this pillow under your butt. Lift and spread your legs,” Stephanie ordered gently.

Melissa obeyed and soon Stephanie was down, using her tongue to give the most intense pleasure Melissa had ever had to that point. Melissa was half aware of Stephanie reaching for what turned out to be a tube of lubricant and a modestly sized vibrator. Melissa felt the sensation of the cool lubricant and of Stephanie’s finger being inserted in her anus. Melissa was familiar with the drill but always before it had been Mel’s lubricated finger going inside a nervous girlfriend’s vagina. She knew what would happen and sure enough her anal sphincter was soon relaxing and opening. Was Stephanie going to break role and f—k her? Melissa probably would have liked that. But no. It was the first of several sessions the two would have together with ever increasing sizes of vibrators.

After an hour or so of play the two were ready for their sleeps. Melissa was so surprised that even after a well-spent orgasm she hadn’t wanted to bolt out the door. She was so comfortable with Melissa.

At this point dear readers, I should tell you that I was getting concerned about how long it was taking Melissa to tell her tale and she still had not arrived at the road not taken. I looked around the room to see if she was holding her audience. No problem there. The girls would have listened all night if that’s how long it would have taken to tell the story.

Melissa continued and I will tell you the rest when and if Angela lets me continue.

Part II

Tags: crossdressing, featured

Category: Transgender Fun & Entertainment