Glory Hole Pt. 02

Story Info
Entertaining a group to get to be in the glory hole.
6.5k words
4.66
10.1k
8

Part 2 of the 3 part series

Updated 06/11/2023
Created 10/30/2021
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Hi, I am Leigh, a Crossdresser (CD), Caucasian, 68" tall, women's size 8 or 10 depending on the brand, green eyes, and shoulder length hair. I have always had soft facial features. My stories are more of a diary entry than a novel. They actually happened but I changed the places and names.

This all started as a curiosity after reading several stories about the thrill of the glory hole then catching a few videos. I also found two local stories where women had to have their stomachs pumped at the ER after swallowing 50 loads of cum in one day. Wholly crap 50 loads, that's like blowing a sperm whale. I was pretty turned on and wanted to satisfy my curiosity, but I didn't want to blow 50 guys.

Where could I go for answers, why the internet of course. That's where I met BobOhio and after weeks of chatting he recruited me to try out to be a "host" at the adult book store.

I can understand the need to be careful, if the cops sent in an undercover to the adult bookstore it would have cost the owners a lot of money, but if the bookstore was attracting clients by having a host in the corner booth for guests to enjoy so I can't blame them.

The more I chat with Bob the more I understand this is some form of membership, the hosts have to prove themselves and the guests have to apply for membership. Bob keeps saying "you have to be careful" and "you have to keep secrets". I get it.

In part 1 I had to audition at Ryan's House to show I was real and not a cop or some low life lurking on the web.

I received a new set of instructions on the drive home from Ryan's place, where to go, times, and even where to park. The instructions also provided outfit suggestions and a note that my expenses would be reimbursed. These were more of a men's fantasy thing, playboy bunny, magician's assistant, sexy mermaid, the list was everything I never dressed as. I needed help with the outfit so I phoned a friend who I knew would be too eager to help.

It only took me two hours to get ready to go shopping, all because Lin said No Jeans and No yoga pants, so I had to come up with something different. I picked a pair of dark tights, Red and black plaid skirt and black long sleeved top and black knee-high boots (I love fall) and I painted my nails red to match the skirt. Eye shadow and liner had to be a smoky. My hair was styled in very loose curls over my shoulders.

Lin pulled into my driveway, yelling hello as she let herself in the side door. I was just checking myself over in the mirror one last time. She was the thrift shop queen of the town, she walked in wearing a 70's mini-skirt with a loose top and mid-calf boots with heels.

"OMG you have boobs?" I said.

"Yes and you should do the same thing gurl, you'll love them." She said proudly pulling up her top.

Her chest was still wrapped in an ace bandage but you could tell she was going to be a c-cup or maybe a d-cup when it came off. It's the one thing I've been working on, I was pretty proud of my B-cup, if I added a water bra I could pass as a C-cup. But for now I'll just hate my body and not stand too close to Lin.

"Come on gurl, it's only a car payment for like 3 years and you get perky boobs!" Lin bragged.

"Yea but you don't have a choice ass like this." I said as I pulled up my dress to show off my assets. This was a lot of work, 8-10 hours a week on the elliptical and walking 3-miles a day gave me a nice ass even if I do say so myself.

Giggling Lin said "We should stop at the restaurant, my brother would love to see you again."

"That asshole? He treats me like shit every time I see him!" I said.

"He likes you, he has a crush on you." She confessed.

Lin's brother is an ass. He treats me like shit and I don't know if that's the custom in China but he needs to unfuck himself, he's in the US now and he needs to treat people with a little respect. I didn't say anymore I didn't want to upset her, it is her brother. Her family disowned her when she came out, her brother was the only one that would help her out and he gave her half the business so she had some stability in her life.

"I'm so glad you're going with me, I could never do this alone." I confessed to her.

As we got into her car she asked what I was looking for.

"I need something cute, that includes nylons, a short dress, and would fulfil any guys' fantasy" I said.

Then I had to explain what was going on and what I was doing.

We drove the short distance to "The Second Chance Shoppe" a thrift store at the end of the main street in town. This is something I could never do dressed; but Lin was fearless. Lin was also 100% passable. The parking lot was around the corner and shared the building with a Yoga studio and a bagel shop. I was disappointed the rear entrance was closed. The less time on the street the better.

The shop owner was great but nothing that could be used to make a sexy costume so it was off to the next shop. We stopped at this Unique Thrift Shop in the next town. Racks and racks of clothes and costumes, better yet, almost nobody in the store. After a half-hour of browsing Lin stops and looks at me.

"What are we looking for exactly?" Lin asked.

"Sexy costume that includes spandex and a short dress." I said.

"I know where need to look." Lin proclaimed.

"Where?" I asked.

"The magic shop." Lin said in a matter of fact voice, as if that was so obvious.

The trip to the Unique Gift Shop wasn't a total bust, we each found a couple of swimsuits, new with tags and liners that fit us.

The Magic Shop, an easily missed little store nestled between a State Bureau of Motor Vehicles Office, a State Liquor Store and a Quick Stop Convenience Store.

We walked in to the dimly lit little store with the old fashioned doorbell announcing our arrival. A tall gaunt figure appeared from behind a curtain in the back of the shop.

"May I help you?" He asked as if he was Lurch's younger brother or something.

I was speechless but the brave Miss Lin just blurted out: "She needs a pixie outfit for a party."

Pixie? I hadn't thought of it but it seemed Lin had an idea. Without batting an eye the curator asked if I wanted to be a scary pixie or a cute pixie in his very own creepy flat tone. Really? Is this guys an undertaker or magician? I'm voting for an undertaker...

Lurch my new pet name for him, brought out a book and offered us to look through the over 30 different pixie/fairy costumes before disappearing into the back. Lin was beside herself, you would have thought she was shopping for herself she was so into this. Lurch came out from the back with six complete outfits.

I immediately dismissed the two from the "mouse house" I wanted this to be an adult outfit. That left us with two that looked about the right size.

"I have a changing room in the back if you would like to try them on." Lurch offered.

Lin drug me to the back by one arm and literally snatched the two costumes from the counter. They were both ok, the one the hips and waist fit me well but there was a lot of room in the cups and the other the cups fit better but it was a little snug in the hips. Lurch offered his expert opinion with each outfit and said if I chose the yellow and green one he would throw in a couple accessories.

Lin and I figured if we shortened the shoulder straps the top would fit fine but the dress was almost two hundred dollars but it was a light green leaf print high hip maillot corset/swimsuit made of a heavy weight satin with a green satin mini skirt layered with yellow lacy panels. The sleeves were Genie material, green and yellow mesh. This was not a cheap Halloween costume, the tags claimed it was made by a ballet supply company in Chicago.

We looked around the back and found rhinestone fishnet stockings and fairy ear appliances, the total bill was just under three hundred for everything and a cheap garment bag to keep everything clean. Who would have thought to go to a magic shop? Actually the shop had several costumes in the back all nicely hung up on wheeled garment racks.

Leaving the magic shop Lin and I were like a couple of Vikings leaving the burning village with all our loot Then I froze in my tracks, I had a text from Ryan on my phone. Two hearts and it said "thinking of you." I showed Lin. "He missing dat ass." Lin said and we both laughed.

Lin pulled the car out of the lot and headed south towards the expressway but she drove past it.

"Where are we going?" I asked.

"We've had a rough day I think we deserve lunch before we shop for shoes." Lin said. It was a good idea, I forgot how hungry I was. We pulled into the downtown of another small town. It was like the set of a movie with all the brick buildings all in a row. This town was the center for the trolley system back in the day. Matter of fact the café we were at, was part of the original trolley barn.

Shoes was going to be an issue, we needed the right shade of green or yellow and they had to fit. I didn't exactly have ballerina feet. After complaining to Lin about my shoe dilemma Lin shared a story about her great- grandmother who had bounded feet. I felt small for complaining after that.

"You know I wish I could be more like you." Lin said thoughtfully. After a sip of her iced coffee she continued: "I wish I was more daring like you. Joining a Glory hole as the host. It's so wild."

"Why don't you come too? I'm sure we can get you a costume." I said.

"I have a costume from the dance class I took last year, remember?" Lin asked.

"I'll text Bob and ask him if you really want me too." I said.

"Good, and then I get to suck your boyfriends cock, maybe he'll like me better!" Lin laughed.

"I don't have a boyfriend, you mean Ryan? I asked.

"He texted you and said he missed you. That's boyfriend material girl!" Lin joked.

As we drove to the mall I texted Bob about Lin. The whole day had been perfect. I had my doubt but nobody said anything to us and nobody treated us like we were lepers or anything. I honestly still had my fears since I'm not 100% passable, but I try my best and I'm not doing this for fun, this is me, and this is who I am. I wish I was more like Lin, you would be hard pressed to say she still had boy parts. I wasn't worried about the mall the shoe store was only a few feet inside the building and Lin was already pulling up to the mall entrance close to the shoe store.

We walked what seemed to be an eternity to get to the doors, the mall was packed or everyone was parking at the most unreasonable mall entrance, unless you wanted women's shoes that is. We enter the mall and a nice man with a family held the door for his wife and kids and held it for us, I was very impressed. Lin thanked the man, I nodded my head because the words wouldn't come out.

We walked down the hall past the nail place and the island of gumball machines to the mall concourse and made a left, the shoe store was two stores on the left. We get to the store and find everything is 40% off, the store is going out of business and it's packed with crazy women. It's like shark week, the sharks are all in a frenzy, and everyone is there looking for a good deal. The store attendants are running back and forth trying to keep inventory under control, kids that were dragged in to this tempest are either crying or too scared to cry. It is something right out of Dante's Inferno. In the middle of the tempest I spotted two of the girls from our Girls night out (GNO) Bevy.

Lin and I worked our way to meet them, it was Jessica and Jeri both very close to passable girls but they were looked down upon by the GNO Club because they used "false names". You are supposed to feminize your real first name and ad your last initial to form your screen name and email for the club's site. Scandalous to some, I say it's your name, make it what you want but neither girl looked like Jessica Simpson or Jeri Ryan, their "namesakes".

One of the clerks asked if she could help us, and I told her what I needed and Lin chimed in. Again Lin was too perfect, she had "normal sized feet for a woman" and I had ugly men's feet. I hate my feet.

I was getting paranoid in such a large group of people, especially young bored kids that were here with their parents. Kids had no filter and I was waiting for one of them to say something. Surprisingly they never did.

The clerk came back with 4 boxes from the back, all of them excellent colors. I tried them on one at a time and discovered why I should have worn pants. It was hard to keep knees together and be modest in the outfit I chose. Success was made, 2 pairs fit, I kept the yellow opal and the black pair the clerk brought out. Lin finally found a pair of knee high boots and some pumps. I offered to pay for hers also since she was driving us all over today. It was a really good sale!

"Jessica want's in." Lin said.

"In what?" I asked.

"Jessica wants in on the GH club" Lin said over emphasizing the "GH" and winking with the wrong eye at the same time.

"Dude, you can't tell everyone about the secret club, that's why it's a secret" I scolded.

"They...I mean Jessica is not in!" I scolded.

Lin wanted to walk through Hot Topic and Spencer's since we were here, I didn't want to walk through the mall but I wasn't driving. Jessica and Jeri were cool, most of the time. Jessica is a high class girl when she gets dressed up, very impressive when we go out on the town. Lin and I looked over the earring case at Spencer's and got a good laugh out of the novelty stuff they had. Lin loaded up on earrings, maybe 10 pair. She was worried I was out of money and I confessed that I never got my ears pierced. Shocked, after I paid for her stuff and took me by the arm and walked me out of Spencer's and to the center of the mall, near the food court.

There it was the rite of passage for every little girl; the Piercing Pagoda. We got to the counter and the attendant no more than greeted us and Lin proudly offered me as the next sacrifice to the pagoda.

The woman working the booth was very nice and went over all the options as well as the aftercare instructions. Simple ball earrings were the starter. I already had my tongue pierced, how bad could this hurt. I obviously underestimated the pagodas ability to inflict temporary and direct pain.

"Relax, I have an Australian piercing, this is nothing sweetie." The pagoda woman whispered in my ear.

While my brain was processing what that meant the gun pierced my other ear and the deed was done. Lin paid for the event while I marveled at the studs in my ear lobes. I did finally pick out some different earrings, for when everything healed. Then we headed to the food court with our bags in tow. Not to eat but to spy on the Chinese restaurant in the corner.

I forgot I was wearing a dress and that I was just being me. All these years I had been resentfully acting like something I wasn't, this was the real me and I didn't want today to end.

We did a half circle in the food court and ended up getting a small order of chicken with Chinese vegetables over rice. There was an Amish family over by the restrooms, the male without a beard kept looking my way. Every time I looked towards him he was looking at me, then looked away. I don't know if he was trying to decide what I was or if he was going to say anything. I think I was just paranoid.

Leaving the food court there was a group of high school aged guys, not particularly well dressed that started to follow us. You know, the stoners. Every school had them. You could hear them quietly cat calling us. Kids, we were NEVER like that in High School. Lin and I turned into Hot Topic to look around and hopefully the guys found a new target.

Lin scooped up this lotus flower high waist bikini that was on sale. "I could never wear that, but it would look great on you." I said. Lin had the perfect body for transition, she already had the boob job and there was no reason for feminization surgery, she just needed her boy-parts removed and she would be complete.

The sales woman asked us if we needed any help, I told her no, we were just looking but Lin pulled a black one piece with a lotus flower on it and told the woman that I wanted to try this on.

"Sure follow me" the sales woman said with a smile, almost skipping to the changing room. Lin wanted to try hers on also. I was afraid of stretching it in the wrong places but I guess I was the only one worried. It did fit and it looked nice, even if I left my tights on under the swimsuit.

"I guess it fits." I said from inside the booth.

"No, you have to come out so we can see!" Lin exclaimed.

The sales woman looked me over and asked me to turn around. She tugged on the shoulder straps and brushed my ass with her hand. "I think that's a great fit." The sales woman declared. Lin thought so too. The real winner of our mini Miss Tropicana was Lin, she had to get a larger top, but was very happy with how the bottom fit. Our tormentors were doing laps but we managed to give them the slip at the gumball machines.

"We did everything except nails" Lin exclaimed as she pointed to the Asian spa.

"I can't do those, they are permanent until your nail grows out! I explained.

"No they have temporary sets, come on." Lin insisted. We were having a full blown girl's day if it killed me. I might survive but I was starting to feel sorry for my credit card. Reluctantly I conceded.

I did get temporary nails and a pedicure. The nails were green with a yellow diamond to match my pixie outfit.

I had time for a couple hour nap before I got dressed for the party. I found a green t-back gaff and shiny skin tone nylons to wear under the silver fishnet nylons that had the rhinestones that radiate from the ankle almost like a starry night. Over that went the green leaf leotard then the mini skirt. Makeup took the longest, I actually had practiced something like this before but I drew out the eye liner to make it look like ivy sprouted from the corner of my eye and wandered down a little way. My hand drawn green leaves were a little off but I wasn't worried. The leotard had an adjustable band inside like a corset that helped give me a little squeeze to show off more of an hour glass look.

I pulled on the pumps we picked out at the mall and walked to and from the mirror to get a feel of the outfit. I don't like the label "sissy" I've always thought of it as a demoralizing term but looking at me in a pixie outfit I couldn't think of a more appropriate term right now. However I did feel more sexual in this outfit, even more than a mini skirt or night wear.

It was dark and it just started to rain a little when I got off the expressway to the airport exit but passed the ramp to short term parking and got in the left lane to go into the little collage suburb. I was making good time and expected to be at the audition with 5 minutes to spare. The left turn light changed to green and I made it across the intersection only to get stopped by two different trains. I was now officially late. I made the left and drove past the restaurant that use to be the train station and followed the road to the left and turned into the abandoned machine shop on the right. As if my heart wasn't pounding enough a train went by. The tracks were just the other side of the machine shop and at first it looked like the train was coming right at me.

The machine shop parking lot was lined with bushes that had grown taller than a person but some lawn care service was still shaping them into upright rectangles making it difficult to see the house or even the street. Walking past several other cars I took the sidewalk across the street to the front of the house I was directed to. It was an abandoned store of sorts, maybe from the late 1800's. I didn't know what to do so I started walking around the house. The front of the house still had the original store windows in the front on either side of the door but inside was a dining room table and wood stacked up against the walls. There was a side door with light coming from the window so I knocked.

12