A Weekend Adventure Part II

ADVENTURE #4

Having had a good night’s sleep (without rolling over on her boobs) my friend was up bright and early that Sunday. She decided to go down to the motel lobby to grab a coffee and one of their ‘free breakfast’ packaged muffins.  ‘Should I shave and freshen my makeup or go drab?’ she mused for a second before washing off what remained of her makeup. She had no plans for the day except to eventually get back en femme and do some dress try-ons. After all, there was a plaza with Ross, Marshalls and Beals stores nearby, the trifecta of bargain shopping. A Goodwill store down the road made it a grand slam. She could hope that some estate had recently cleared out their late grandma’s collection of clip earrings.

A taxi was waiting at the curb, apparently waiting for a recent customer to arrange payment.  A woman probably in her fifties was in some distress. It seems the hotel clerk had just told her there were no rooms available. She was in animated discussion with the taxi driver. She apparently was running out of options for hotels and shelters and of money to pay the driver. She looked up and sized up my friend who was by then watching from the second-floor balcony. My friend didn’t know it but her plans for the day were about to be dramatically altered.

No sooner had my friend walked down the external stairway when the woman in distress approached ‘him’ pleading for help. The story in a nutshell: after her marital breakdown the woman had been staying with someone who sometime around midnight told her to pack up and leave. It seems even before ‘he’ got the coffee, my friend got the whole story. It was not a pretty story. Two women who neither had seen the better parts of life were living together. There had been an argument and the one who controlled the house kicked the other one out bags, baggage and all.  The evicted had spent most of the night riding in taxis looking for a woman’s shelter, a cheap hotel—anywhere she could spend the night and get reorganized. My friend just happened to be in her path. What would you do?

“Sir, my friend kicked me out. I just need a place to stay for a few hours so I can get organized and make some calls. I don’t do drugs,” pleaded the newly homeless woman.

“Don’t tell me you took her in?” I asked my friend. “That was Florida. You know things can go horribly wrong. She could have had an accomplice waiting to mug you!”

“This was some dirt-cheap Econolodge, not a Holiday Inn. If she was looking to mug some rich guy she was parked at the wrong property. Besides I was influenced by her mascara. She had gobs of it streaming from her eyelids. She had not just started crying and she needed help.”

The woman in distress said her name was Rhonda and apparently, she said she didn’t do drugs so many times that my friend was convinced she did drugs. “We got her things into the room, and I relaxed on the bed and suggested she take a chair and unwind. She sat but there was no unwinding. I guess in her situation I would have been the same. Well maybe not. Right off she told me she would put out for me for a couple of hundred dollars. ‘I need the money,’ she said. I turned her down.  Later, when I had decided I was going to go en femme anyway I suggested to her that asking me for money in return for sex was useless because we were sort of in the same line of work. I pointed to the makeup and femme clothes spread around the room and told her they were mine.

“How did she take that news?” I asked.

“It didn’t seem to faze her. She said she’d been wondering about the makeup. I told her again to relax but there was no relaxing in her. So, I was not going to be relaxing much.”

I took a guess: “I’m figuring your femme side enters into this story somehow.”

“Right you are. After a bit more chitchat and trying to get her to unwind I decided to go for it. First, I told her I wanted to shower and shave. She stepped out to have a cigarette. I skipped the shower and just shaved. She came back in as I was starting to apply my makeup. She just busied herself with rearranging all her belongings which were in two suitcases and a few paper bags. In different parts of the room we were busy doing our own thing. When I was finished, I was wearing the same dress as the night before and sitting up on the bed. She had no reaction to seeing her ‘savior’, her potential sugar-daddy in drag. I thought I had done a good job on my makeup and she had no compliments or criticism. It felt as if she was very comfortable with me presenting as a woman. At least it stopped her from again offering sex for money.”

“You know the way you describe her there is probably nothing in life that hasn’t already touched her,” I mused.

“For what seemed like a long while I just sat propped up against the headboard while Rhonda busied herself rearranging her luggage. She shared bits of her story and it wasn’t the story of an easy life,” my friend explained, “There was so much adversity and hardship that I cannot remember it all. But I’m pretty sure failed marriages, years of strip club work, escort work and straight hooking entered in there all culminating in the previous night’s fight with her landlady, expulsion from her room, baggage and all, and a fruitless taxi ride around part of Clearwater looking for a shelter or cheap hotel room.

“At one point we got back to the subject of sex work. She was quite underweight and gaunt, probably from too much drug use but now that we were two girls she was anxious to show me her boobs. They were no longer a commercial quantity.  They were also an extremely nice, firm set.

“Are those implants,” my friend asked Rhonda.

“Yes and I had to have them re-done a few years ago,” came the reply.

“I thought a boob job had a life-time guarantee,” I interjected.

“So did I but Rhonda claimed the were only good for ten years or so.”

“Just like artificial knees,” I quipped.

“What did you end up doing?” I asked my friend. I imagined she was going to shell out several hundred dollars to get Rhonda settled and out of her hair.

“When it became clear I wasn’t going to become her latest sugar momma/daddy Rhonda straightened up a bit. She had lost her phone in the previous night’s activity. I let her borrow mine to make a call. The good news was that her ex-husband arranged for her to get a hotel room close to a club where she was confident she could work as a dancer. I thought well maybe a skinny little 50-something, maybe 60-year-old with rock solid boobs could make some money dancing but I was skeptical. But by that time, I was anxious for her to move on and for me to make moves toward my next destination. So, I encouraged her to go for it.” My friend sounded a bit more frustrated and a little less charitable toward her new companion.

“By check-out time we were both packed up, makeup freshened up and we were ready to hit the road to a town called New Port Richey, not exactly the direction I expected to be heading as my next stop was to be in Sarasota. We made some stops along the way. She wanted to look for her phone where she had been dropped off. That proved to be fruitless except Rhonda ended up telling her story to a stranger who pulled out and gave her a $10 bill to help her along her way. That girl had some survival talents. Next, we stopped at a restaurant for a meal which she devoured quickly. So did I. We were both hungry and tired.

I just grinned.

“You know what,” my friend continued, “once she had something to eat and we were back on the road she dropped off to sleep like a baby. Sitting in the passenger seat she fell forward against the seatbelt and her head flopped further forward. I was seriously worried that she might have died.”

“Had she,” I asked part seriously.

“Thankfully no. And just after we passed her hotel destination she woke up, recognized where we were and directed me to turn around. She was a bit more on the ball than I had suspected.

“We arrived at the hotel and she told me to stay in the car while she checked in. About five minutes later she came back to tell me she had the money for the room but because it was cash they needed a $100 deposit which she didn’t have.”

“So you forked it over,” I guessed.

“Damn right I did. I put it on my credit card and made sure the deposit was limited to $100. To this day I don’t know if I did it out of a generous spirit or because I wanted so badly to wrap up my good Samaritan stint.”

“Perhaps there was no deposit required. Perhaps she and the clerk had just worked up a little scam.”

“That is possible or perhaps she was going to overstay her one night but one way or another I was sure I would never see that $100 again.

“Didn’t that bother you?”

“Look,” my friend replied. “That woman was in bad shape, physically, emotionally and socially. She needed help. $100? If I hadn’t been there with her, I would have been spending that on clothes and jewelry and if I hadn’t been doing that it would have been a game of golf with friends all the while wishing I could be off somewhere getting all dolled up. Helping Rhonda was my Sunday recreation and I could do it en femme.

“Besides we talk about society helping those less fortunate among us, about giving to shelters for the homeless and for abused women but sometimes we can’t send ‘just $19.50 a month.’ We will be called on to act one-on-one. That was one time I just had to do my bit.”

“How did she make out after you left?” I asked.

“I have no idea. The last I saw of her she was talking to the guy in the room next to hers. I assumed if she needed a room after that night she would get herself hooked up with him,” my friend said reflectively.

“What a life!” I said quietly.

“Yes, what a life.”

“Did you ever get that deposit back on your credit card?”

“Nope! But she did give me one gift. During her repacking she came across a bra that she said was too big for her and I could have it. It was a pink 38 C demi cup. When I got back home I could not wait to try it on with my breast plate. ‘That suits you well,’ my wife said with some sarcasm. I think she didn’t fully believe my story. Do you?”

Tags: crossdressing, featured

Category: crossdressing