Ladies who Lunch - At the Gloryhole

Author's Note: Hi, just a quick little story to finish out the summer. Three older crosssdressers have a little more excitement than they are used to after lunch. I hope YOU like it...

***

The Boynton Tavern

So we did lunch, it was a thing we did. I had to admit it was one of the things I did that I liked the best.

"Hi ladies, what will it be today? Sabrina?"

"Ceasar salad please." That was my go-to, I was easy, I needed something light. I was wearing the tightest corset, I couldn't eat much anyway. Lunch wasn't about eating for me.

"The Cowboy cut with roasted potatoes, you can give me some vegetables if you like, give some color to my plate." Brenda went for steak, she said she never had it at home, never even turned on her grill anymore, ever.

"And for you Sarah?"

"Mmm, I'll have, um," Sarah was always last, she would change her mind a couple of times, she would read the menu like a Jane Austen novel. "How about the salmon?"

"Are you sure?" We would giggle, I loved watching Sarah decide anything. Her fingers would tap on her chin, her long nails would be glowing.

"Ooh no, the catfish, yes, and lots of vegetables. Ooh and lemon on the side, or lime, no lemon." She checked with us, we all gave her a high approval rating. "Thank you." She was eating healthier, she was worried about her cholesterol levels. She really wanted a hamburger. "Ooh, no give me the avocado toast." She made an embarrassed grimace. "Whew."

"Of course. Okay, ladies, I will bring some sangria, lunch will be ready in no time." She winked, she smiled, Trudi was our favorite waitress. Three times we took her on our traipses after lunch, we once invited her and her boyfriend out to dinner for Brenda's birthday. Well, before she broke up with him. Sangria was always on the house.

Once the pitcher came, we poured, we drank. The other two said they needed a little alcohol to take the edge off. I didn't really know what they meant, I never felt an edge, I only liked the taste, the fruit. Actually, I would drink whatever Trudi brought us, whatever they were making special that day, sometimes the owner would come over and buy us a round of drinks. He also called us ladies, it was nice.

The two other ladies were sucking their straws, they were always relaxed at lunch. Me? I was always excited, I would be rubbing my nylons and constantly recrossing my legs. Personally, I was looking to put an extra edge on, being with the other two girls did something massive to my confidence, my libido, and I was waiting for a little adventure, but the other two, well, they just wanted lunch.

***

"Come in, come in, come in..."

The three of us started these lunches three years before. We all went to the same salon. I always thought it was funny that the salon wasn't in, or even near where we lived. We lived in Worchester, Massachusetts and the salon was forty minutes away in Framingham. The woman, Marilyn, who worked on our wigs and nails and curves got us together. She said it was quite coincidental that we had so much in common. We lived in the same city, we were almost the same age, we were all retired, and we were all beautiful crossdressers, well, that was her words. Oh, and we were all married.

"Hello, Ladies,"

Even Marilyn called us ladies, right from the start, as soon as the three of us had gotten together. We were in one of the side rooms, the ones for waxing and shaving and other things which led to clothes being taken off, you know a little nakedness. It was very private.

Marilyn introduced us, she gave us wine, we had a nice afternoon. It was the longest I had been out of the house in a dress in years since I was in my twenties. I told my quick little story, I was so embarrassed.

"I have been um, dressing up since I was young, real young. I went a little crazy with it when I was a teenager and in my early twenties and then I got married. That was twenty-five years ago, I'm fifty-one, have two kids that are out of the house, and a bored wife that doesn't know I still wear heels. She thought I gave it up on our tenth anniversary. She doesn't realize it's all I think about. I'm also a little obsessed with makeup I could spend hours if I have the time, trying different looks." I scrunched my face, I swallowed, I was going to be judged, I think I was blushing.

"Oh my god, I could say the same exact thing."

Brenda was the tallest and definitely the most full-figured of the three of us. She was a retired Worchester cop, eight years off the force, she was African American and she was very pretty. She wore a light brown wig that reached her shoulders, and she loved sleeveless dresses to show off her arms. They were surprisingly feminine.

"I just turned fifty-three, I'm six-five in three-inch heels, and my wife knows. I told her when I retired, she doesn't feel too great, she has a history of heart problems. I love her, she is the best thing that has ever happened to me, she doesn't mind me getting dressed up as long as she doesn't have to witness it, hehe. Like I would ever show her, like I would ever show the kids." We all laughed, it was nice, it was nice sharing our stories, sharing our almost one hundered and fifty combined years of crossdressing. Unfortunately, Brenda's wife died a year and a half later. It was hard on her, it was hard on all of us even though we never met her. We didn't want to have to explain who we were, we went to the wake and funeral and sat in a corner.

Sometimes Marilyn had to get up, meet with a client, and instruct one of the other workers, she left us alone. That first time we were all in short dresses, heels, full makeup, we wanted to make a good impression, wanted to show off our feminine sides to the max. We wanted to show off our jewelry and hand gestures. We were quiet, we were getting used to each other. I was just getting used to talking to someone while in femme mode again, it was so much easier when the people you were talking to were in the same situation. We smiled, we played with our hair, we checked our long nails, our bags, I finished my wine.

"So getting to know each other a little better?" Marilyn was back, we smiled, we all shook our heads.

"Yes." We all lied.

"Good. Sarah, tell us all a little bit about yourself."

Sarah looked at us each in turn, took a long deep breath. "Well, where would I even start?" I could tell she would have liked to of cried.

She was the oldest and definitely the most passable. She had long gray, white hair which landed somewhere around her bra strap. She was constantly playing with it and sometimes even braiding it. We all told her she was stunning, gorgeous, she had the best eyebrows, best cheeks, we were all jealous. She was also the timidest, she was the one that had trouble leaving through the front door of the salon, leaving the car, or going anywhere that might have men in the vicinity. She never gave anyone eye contact.

"Mmm, I am fifty-eight, my wife kind of knows. She doesn't approve. I have been cross-dressing for ever. I go away a couple of times a year to dress up, to become myself again, and, um, I want to do it more now that I have time. I would like to experience life as a 'female' before I die." She took another deep breath, "I would like to get more comfortable talking to people."

"Marilyn, touched her hand, "You will. Now that the three of you are together. You will all have more confidence, more of an 'I don't care' attitude. There is power in numbers and you three are ready for some fun, you deserve it." She poured more wine and we talked some more, even when she left the room, it was nice, I learned a lot. I learned I wasn't the only one in Worchester like me. Maybe there were even more 'women' like me in this world.

***

After that first time with the other two ladies we opened up a little more, we told more stories, much more personal remembrances and we got together so much more. We started to discover each other's personalities. Sarah was the smart one, the quietest, she was less likely to do anything out of the ordinary. She could take weeks to decide on things, new dresses, new shoes, new hairstyles. She was the opposite of the words, impulsive and rambunctious. While Brenda was the chatty one, the loudest and the biggest. She didn't really care if others knew she was a male in a dress, she was out to have fun, especially after her wife had passed. We also let her make most of the plans, she was the one that introduced us to Trudi at 'Boynton Tavern,' and she was the one that had been going to visit Marilyn at the salon the longest. She also made us get every bit of our hair removed from our bodies. My wife was suspicious.

"Why do your legs look so smooth?" She asked me three weeks after my last esthetician visit.

"I don't know, maybe 'cause I'm getting old." I shrugged, I told her I had to go, had to get the car tuned or fixed or something. Whatever people did with a car. She never asked again, I wore sweatpants now instead of shorts. I was a really bad liar.

I felt I was the most different of the three of us. I was the youngest by only two years, but I was the youngest in my way of thinking. I wanted to dress like I was in my early twenties, I wanted to wear the highest heels, I wanted to flirt while we were at the restaurant. Maybe I even wanted people to think of me as a MILF, since I did have the largest breast forms. Double D by the way. I was also the shortest, I was 5'8". When I wore my six-inch heels I was still only 6'1", the other two had at least three to five inches on me. They called me petite, it made me giggle. I was also the one that made them nervous the most, I was the one that would walk out of the dressing room partly naked to ask opinions, I was the one that had my ears pierced, the longest nail tips, my teeth whitened, my nose fixed. I even had Marilyn make a little strip of hair in my panties, my wife would never see it, and I wanted to feel more feminine. I was also the one that would initiate conversations with men.

"Nice day for a walk, and I love your suit." I would squint my eyes, I was trying to be cute, I didn't know if I actually was or not.

"Oh thank you, you ladies all look lovely today too." Brenda and I would smile, Sarah would check her watch, her phone.

"Sabrina," After they moved on Sarah would scold me, "Those men were so young, they are going to assume we were interested in them. Maybe even interested in their suits."

"Ha, well aren't we?"

Yes, I was the one that was most interested in men. I could tell the ladies loved it when the guys spoke to us, complimented us, checked out our legs when we left almost any space. Three pairs of legs in short dresses and high heels made us popular at the malls, museums, getting out of cars. They acted like they didn't approve, but it was an act, they did nothing but talk about men when we were at lunch. Even though they were very quiet about it. Brenda had a thing for her tall muscled mechanic, she would tells us how sweaty he got as he bent and worked on her engine. Sarah loved romantic comedies, imagining she was the starlet running away, getting married, or falling in love with her best friend from high school. Me? I would sit in the restaurant and look for the most handsome men, even some much younger ones, I wanted to wink, make eye contact, make sure they knew the three of us were there. Make sure they assumed we were interested. Make sure they knew we were ladies.

***

The Boynton Tavern

again

"So, the zoo, the brewery, the Historical Museums? What should we do this afternoon?" Sarah was ready, she was looking into her compact fluffing her forehead, the men heading to the table next to us smiled and said good afternoon as they sat down, she was ready to leave.

"No more Historical Museums." That was the last place I wanted to go, "We have hit every single one in a hundred-mile radius, they are always empty." The Worcester Historical Museum was four blocks away from my house, I had never been so nervous before. I was so afraid I was going to run into someone I knew, like the wife. Now I wanted to go someplace I have been fantasising about for quite a while, someplace perfect for three ladies in heels. "I have an idea, but don't shoot it down right away, okay?"

The two of them looked at me nervously, Sarah then snuck another glance at the four men behind her, through her little compact mirror, they would be listening, they wanted to know what hot 'middle-aged women' did on an afternoon off.

"I was thinking," I had a sly grin on my face, I just finished fixing my red lipstick. I looked around, I then whispered the next bit. "How about that adult video store on Highland?"

Sarah dropped her wine glass, the two of them got distracted, Trudi came over to help clean up.

Brenda looked around again. "Why the adult store, can't we go to the movies or something? We can see a PG-13, an R."

"There is also a home decorating show today at the conference center. I could use some curtain rods." Sarah was hopeful, she suddenly had another glass of wine. She started biting her nails.

"I think we need to get out of our comfort zone, I want to go someplace salacious, naughty, I am so ready to take it up a notch."

"I'm not, I want to bring it down a couple." Sarah was still looking around, even at the men next to us, she didn't want anyone to hear my idea. The two of them very rarely did what I wanted to do, I knew they were always skeptical, but today I really wanted to go someplace to meet people, to meet men. "Please, just a quick walk around, then we can go to the movies or the decor show. I will treat both of you wherever we go, whatever you want."

"Someone's going to see the car in the lot." Being an ex-cop Brenda was always worried she was being followed, being spied on.

"That's okay I'm driving. I don't mind." I giggled again, I gave them my brightest smile, I was trying to stay positive. "Please, we are all dressed up so nice today, we had our nails lengthened, painted, we all got so many compliments at the salon."

Brenda was in a black and white patterned dress showing off her knees and her two-inch high sandals. She was wearing her wife's ankle bracelet, gold Swiss watch, and gold bangles. Her boobs looked amazing. She was the only one that didn't wear falsies or a breastplate, she filled up a B-cup quite nicely. Her wig of course was perfect, Marilyn made sure of it, it always looked natural and it softened all of her features. It just barely hid her long dangling earrings. She had dark pink lipstick matching her nails. She would be the only one keeping on the nail color for at least a week.

Brenda had a finger on her lips, she was thinking. "Mmm, I haven't been to one in a long time, I wouldn't even know what to expect."

Sarah was looking into her mirror again. She was in a black shirtwaist dress, showing off her legs and her chest, but no cleavage, she never showed any, even though the V-neck was cut quite low. Sarah always wore her wife's old work clothes, when she was working at a bank. She always looked professional, always ready for a meeting. She was quite thin and had a nice figure, everyone assumed she was a woman already, she had that gleam in her eye that every crossdresser dreamed of. Her natural grey hair was blown back showing off her gold, thick and heavy earrings, matching her many bracelets. She was always jingling, we always knew she was in the vicinity. She was carrying a sexy leopard clutch and matching pumps. I could tell she was ready to show off, she was just acting shy. I knew she had a wild side bottled up inside of her, I wanted her to let that wild side out. I wanted to be the one that helped her do it.

"What happens if someone sees us walking in?" Sarah was still worried, the conversation was too nerve-wracking for her. Brenda had to scold her to stop her from biting her long beige nails.

"Well if they see our asses in our new outfits, the place will get mighty crowded... quick." I giggled but they didn't. "Who is going to see us that we know, let's not worry about things we shouldn't be worried about. Let's just have fun." And I was so ready to have fun, I was wearing the shortest light blue dress with white polka dots. It was hiding my Maidenform bra and tiny white bikini panties. I was nice and thin with a corset and nice and round with hip pads, I was quite curvy for a 'woman' in her fifties, I went to the gym three times a week. I loved showing off my legs, encased in sheer nude pantyhose, they were visible from the top of my thighs down. I had on five-inch black sandals with a sexy ankle strap and showcased my red toenails matching my red fingernails. My blonde hair was long, it was a wig and it was expensive and straight, it went straight down to below my double Ds. I was also showing plenty of cleavage. I had on the new breast forms that I got from Europe, Marilyn ordered them for me, they were perfect, they matched my coloring, they made me look so busty, of course. The seam was covered by a black collar around my neck, it said 'SMILE!' of all things. I was also wearing my biggest hoops, they lightly touched my shoulder, I loved how they looked peeking through my hair.

"Please, pretty please," I begged some more, and I felt them melt, I felt them change their minds. I felt them want to do something for me, with me.

I studied them, the two of them were so beautiful. I loved them so much. In the last three years we have become inseparable and had risen completely out of our shells, Marilyn was so right. She knew dressing in public would be easier with friends. Shopping, visiting, and flirting would be more fun with an accomplice, another girl who felt the same, had the same desires and fetishes. And look at our makeup, we were stunning, we all had on false eyelashes, lots of mascara, dark shadow. We all had perfect eyebrows, plump lips, and straight eyeliner. We were definitely ready to at least talk to some men. We were ready to shop at an adult store, I think we were ready to act like adults.

"Okay, let's do it. We can be quick, then let's go to the zoo." Brenda seemed kind of ready, so we all got up and said goodbye to the four men. We said goodbye to Trudi, I even asked her to come, she had just broken up with her boyfriend and I knew she would love a good distraction.

"I wish, I'm going to be here a while, but you three ladies have fun." And she waved us out of the restaurant.

*

Highland Video

I didn't really know what an adult store consisted of, I didn't understand the logistics of it, I had never been to one before. And why was there always Video in the title, what was it still the nineties inside these types of places? We parked towards the back, Brenda was making me hide the car, which meant we had to walk all around the entire building. We took in the whole perimeter in our heels, clicking on the concrete. The store itself was lonely on the quiet block, just two empty lots, an office building, and the adult store, with the huge parking lot. There were quite a few cars here.

Me, Brenda, then Sarah walked in, we went from nonchalant to nervous as we went through the big tinted glass doors. Right away we were greeted by a huge man with a booming voice. "Ladies, welcome. Are you interested in anything special?"

Of course, he was looking at me, I was in front, he was looking down my dress, he wanted an answer.

"No just looking, thank you." I smiled sheepishly, I used my perfect femme voice. The man then glanced down at my legs, he approved. He then looked over the other two as they made their way passed him, smelling their perfume.

The place was quite big, it was deceiving on the outside. It was filled with shelves and shelves of sex aids and toys all behind locked glass doors. There were free-standing racks of anal beads, massagers, and jewelry, there were racks of bodysuits, pole wear, and costumes, there were glass counters filled with dildos, rabbits, and chastity devices. The only thing missing were men, well anyone. We were the only three walking around on a quiet Thursday afternoon. We were the only ones in this bright fluorescent fantasy of ours.