Encounter on 34th Street

| Mar 7, 2011
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“Hey Linda, did you see Ronnie’s ‘TWIT of the Week’?” It was my friend Samantha asking. She is a relatively new reader to TGForum. By far her favorite column (next to mine) is This Week in Transgenderism where Ronnie Rho culls together news stories from around the world highlighting both positive and negative aspects in the lives of crossdressers, transsexuals and others in the transgender spectrum. Her favorite part of the column is TWIT of the Week where Ronnie picks a transgender person who has made the news by doing something incredibly stupid.

Samantha knows that a particular pet peeve of mine is the person who gets dressed en femme, goes in to a department store and decides to shoplift some items such as lingerie or cosmetics. Theft is wrong, plain and simple but to get dressed in a way that is going to bring oneself attention and then try to shoplift is just stupid, and is an open invitation for trouble. I suspect Ronnie feels the same way. Her TWIT is more often than not a “shoplifter in drag.”  Sure enough as Samantha pointed out that week was no different.

“What was that person thinking? Does a guy think that by putting on a dress and wig that he becomes invisible? Does he plan a defense that ‘the devil made me do it?’”  I asked.

Samantha just nodded her agreement. “Have you ever been tempted to shoplift?” I asked Samantha.

“Not since I was very young. I was caught by my mother and the consequences were not pleasant. I was scarred for life. I must admit that when I was coming out to myself about Samantha I would go in to stores dressed in drab and see something I would really like but was too shy to buy. I was really tempted to slip things under my coat.”

“Did you ever do it?” I asked.

“No way,” Samantha replied, “you know I have a professional career. I would have been ruined if I’d been exposed as a shoplifter, let alone someone shoplifting women’s clothes.”

That got me thinking of an event in my past that had taken a weird twist. “I had a close call once,” I told Samantha, “It was quite a few years ago. I was in Manhattan. It was a beautiful spring Saturday morning. Even though I had been out the night before at the old Club Edelweiss I was anxious to be on the go. I dressed in a skirt, blouse and jacket, low shoes and relatively conservative make-up and decided to walk down to the big Macy’s on 34th St.”

“You go girl. That’s the center of the universe. You must have brought a lot of attention on yourself.”

“Not really. Early on a Saturday morning both Manhattan and Macy’s were relatively quiet. I was able to try on dresses and browse the other racks virtually by myself. I worked my way up to the top floor where I knew they had a sort of outlet where fashions and other items were on sale at big discounts.  I made a few bargain purchases. Then perhaps because it was so quiet I was able to spot this guy who seemed to be keeping a close eye on me.  I first picked him out when I held a dress up to the mirror to see how it looked. In the background was a tall black man, good-looking, well dressed but wearing a turtle neck sweater and jacket on a warm day. When I moved to the lingerie area he was still in the background.”

“What did you think?” Samantha asked.

“I wasn’t sure what to think but I thought there was a good chance he was a store detective. I didn’t have anything I hadn’t paid for but I didn’t want to be tailed by this guy for the rest of the day so I decided to leave the store. My other thought was that he was a stalker and worried about what he might do out on the street. I was prepared to run! However all that meant going down five or six flights of escalator. As I descended my shadow followed but not too close. I stopped on one floor to look at some merchandise but mostly to see what he would do.  I wasn’t sure he knew I knew he was following.”  I paused in my description of the events.

“Well what did he do?”

“Just as I suspected he stopped at the same floor but turned in the opposite direction and kept his distance. I wondered why he was following me. The way I was dressed I couldn’t have slipped anything under my clothes.”

“What would you have done if he was stalking you?” asked Samantha.

“I don’t think that occurred to me too seriously. I was mostly thinking, probably because of the way he was dressed, he was store security. Anyway when I started back down he followed. The same thing happened on the next floor which had the jewelry and cosmetics counters.  I did a circuit among the counters and each time I turned I caught a glimpse of my pursuer.  He was there but he never came too close.  That was also the ground floor.  I was just about to the exit when suddenly he was right by my side. I couldn’t believe how quickly he had caught up to me.”

“We’re you scared?”

“It was so strange. I had done nothing wrong but there was this tall man, probably 6’ 4”, athletic and imposing quietly identifying himself as working for Macy’s and asking if he could check my packages. Despite his calm demeanor and gentle voice he was very intimidating. I may not have been scared but I certainly was nervous. I had heard stories where items had been planted on a customer to get an arrest.”

“What happened?”

“Well there was a man and woman coming by. I asked them to be witnesses while this man searched my packages. Happily, they were not your typical ‘don’t get involved New Yorkers.’ They probably weren’t from New York at all. They patiently stood by as my bag was searched and they didn’t seem to read me at all.  After looking in the bag my accoster glanced at the receipt and handed it back to me and said thank you and that he was sorry that he had to search me. He even thanked the strangers. They moved on and I resisted the temptation to give the detective a lesson on profiling. That’s when things took a strange twist.”

“What do you mean?”

“Well, after again apologizing for stopping me he started complimenting me on my appearance. He went on to say that they get all kinds coming in and he has to be careful. I think that if there had been shoplifting TWITs of the Week back in the 1990s he could have caught a few of them. It turns out he had a particular eye for us girls.

“He said his name was Randy.  He said his break was coming up and could he make it up to me by taking me for coffee. Needless to say I was feeling a lot better and he was very good looking. I agreed.

“I thought it was funny that he didn’t have to clock out. We left right away for a nearby café.”

“Are you serious?” asked Samantha, “the guy who you thought was going to arrest you was now buying you coffee?”

“Not just coffee; our conversation stretched in to lunch.  He felt like talking and I felt like listening and finding out more about this man. He was very well-spoken, had a university degree which he had earned while playing basketball on a scholarship. I didn’t know much about store detectives but he didn’t seem typical of the type. When I asked him how he came to be working at Macy’s he said it was a part-time thing but was otherwise pretty evasive about his work. Did I tell you he was very athletic and very good-looking?”


“We talked through the lunch hour about life, about families and about college sports.  And no we didn’t talk about the T-word.”

“T-word?” Samantha asked.

“Transgender and don’t play so innocent. I had assumed he knew but I wasn’t sure. I also was beginning to wonder why he didn’t have to get back to work. I had a hunch. I asked with a smile, ‘you don’t really work for Macy’s do you?’”


“At first he tried to protest but then he admitted that he didn’t, that he had been cruising through the store, spotted me and knew he had to meet me. He told me how much I turned him on and for the first time he reached under the table to squeeze my thigh. I put my hand on his and smiled an understanding smile.

“He told me how nervous he had been while he followed me, worrying that I might ask store security to hold this stalker.”

Samantha laughed. “That’s truly ironic,” she said.

“He described how he was afraid he’d lose me if I got out on to 34th Street so he quickly devised a plan to claim he was a store detective. The plan worked and after a few hours of chatting I knew he could have his way with me.”

“You didn’t?”

“Our conversation started to wind down so I asked the eternal question: ‘where do we go from here?’ He replied, ‘Your place or mine?’ and went on to explain that his place was an hour away out in Queen’s.  I explained that my hotel was up by Times Square.  In no time Randy had paid our bill and hustled us out to get a cab. I could see Samantha’s eyes literally grow wider as I described how Randy held me and kissed me in the elevator. I told her how nice it was to look up to a man to kiss him.

I went on to describe to Samantha how Randy had stood very close behind me as I poured us each a glass of wine thus allowing me to feel his growing excitement. Samantha clearly enjoyed the lurid details of how Randy and I had kissed and caressed each other while laying on the bed in no particular hurry, how I enjoyed rubbing my hands over his strong body and how I also enjoyed his hands on me. I spared no details. The more Samantha seemed to enjoy the description the more details I added.

At some point in the description Samantha threw in the pun that ‘Randy certainly was randy, wasn’t he?” I laughed in agreement.

I eventually concluded, “We spent a great afternoon together before he had to go home, probably to his wife.”

“Did you ever see or hear from him again?” asked Samantha.

“It was the days before the Internet so we couldn’t exchange email addresses or Facebook pages. I did give him my postal address but I never heard from him again. He was my ‘Miracle on 34th St.’ What a movie that would make! A stalker pretends to be a store detective to lure a girl who is more afraid of store detectives than stalkers but he wins her over and they live happily for a few hours after.”

Samantha was clearly aroused by my descriptions but she had one more question: “Linda, don’t jerk me around, did that really happen?”

“Yes and no,” I confessed with a smile, “everything that happened up until I left Macy’s is true. He did follow me. He did stop me and search my bag and purse. He did compliment me on my appearance but then we parted. He had to get back to work, I guess. The rest was just my wishful thinking embellished to satisfy your lustful mind. Besides I was a good girl back in those days.”

“You bitch!” were Samantha’s closing words on the subject.

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Category: Transgender Fun & Entertainment

Linda Jensen

About the Author ()

Canadian writer Linda Jensen is a long time contributor to TGForum. Before the days of the Internet Linda started her writing with the Transvestian newspaper. Her writing ranges from factual accounts of her adventures to fiction although frankly sometimes her real life adventures are stranger than the fiction. Linda is married to a loving partner who upon learning about Linda said, "she was part of you before I met you. Although I didn't know it she was part of the package I fell in love with. I don't want to mess up that package." "Does it get any better than that?" asks Linda.