After our run in the park, I didn't hear from Ryan for almost two weeks.
We had walked out of the park together with Dick's arm around my waist. He had tucked his hand into the back pocket of my opposite cheek. The pocket wasn't meant to be functional, of course, the pants being as tight as they were. So Dick's large hand was clearly outline as he pinched and fondled my ass while I giggled and leaned into him. I knew because he told me about it, asking me how I felt that others could see him doing this to me. I had blushed and said "Okay, I guess." Secretly I was very pleased, proud that this teen stud was claiming me as his for the world to see.
He dropped me at my car and leaned up and into him on my tip toes to thank him for the run. We had kissed and when it broke I had asked whether I would see him at the gym in a couple days. He said that, respectful to my wishes, he would give me some space. He'd be in touch though. He gave my ass a slap and went off.
I was dumbfounded. In the whirlwind of that day I'd all but forgotten about my resolution to bring our relationship under control. I drove home and snuck in the house as the reality of the situation washed over me. I had hooked up with a teenage kid. A MALE teenage kid. And I had practically been dressed as a girl the whole time. All the while my beautiful and loving wife slept at home. Shit. What the fuck was I doing?
I knew I should be thankful that Ryan had taken my request seriously and was giving me space to short out our relationship. I knew I should take advantage of that time to connect with Carlie. Initially, as the days of radio silence from Ryan went by my mind was incredibly preoccupied with him. I kept flashing back to being between his legs, staring up at his hard body and glorious cock. In the showers I groped my ass with my own hands, imagining they were Ryan's. However as the days progressed beyond a week, my obsession waned. I continued to go to the gym and being disappointed each time I didn't see him there, but my raw feelings towards him dulled a little. I still thought about Ryan constantly - his strong body, handsome boyish face, deep blue eyes, long hard cock - but, trying as I was to accept the situation, it began to develop into more of a fond memory, rather than regret.
I felt I was making progress, so when I finally received a text from Ryan, I was relieved about what he was asking. He had a school dance coming up - the halloween dance. He said that, even though it was against school policies, he was going to drink. Aware of this reality, the school encouraged the students to arrange for parent or adult escorts to the dance, so that the surpervising adult could generally keep an eye on things and drive home, if necessary.
Ryan's parents were out of town and so he wondered whether I would escort him and one or two of his friends. This seemed like a step in the right direction, even if I felt a tang of disappointment that this was the reason for his reaching out to me.
Ryan gave me his address, and told me to come over at 6 the following evening - a Friday. As usual, Carlie would be at work so I agreed.
--
The next night came around and I drove through the expensive neighborhood and arrived at a large gate, as if the entrance to a museum. I saw a buzzer and tried it. "Hello?" a familiar voice asked. "Ryan it's me! Jerry."
"Hey babe, come on in. I'm just about to hop in the shower but someone will let you in."
With that the doors swung open slowly and I slowly drove in. I drove down a winding road through trees and coming to a clearing where finally I spotted Ryan's house, or should I say mansion. This place was huge! I had suspected Ryan was wealthy but this was another level.
As I pulled up to the house I spotted a young woman with brown hair who appeared to be waiting at the front door. I parked the call and walked over. "You waiting for me?" I asked.
She rolled her eyes slightly and, impatiently, said "follow me." She turned on her heel and began walking into the house. I picked up my pace to keep up with her, staring at the large house all around me. You could fit dozens of my small apartment into this place, I thought.
I looked ahead again and realized I was falling behind. I focused again on the girl and tried to catch up. I noticed she had a really great body. Thin and lithe, she stepped in long graceful strides. I felt clumsy trying to keep up. I wore a suit for the occasion, which seemed to further limit my mobility, as it was getting tight around my ass.
We finally arrived at a door to a room. I collected myself, thinking I would be seeing Ryan again after around a week and a half. Even though I knew I was there only to provide a simple favor, I was nevertheless excited to see him.
But when the girl opened the door, we stepped into what was clearly a girl's bedroom. The walls were light purple and the four poster bed had curtains and lace hanging down from the top.
I stepped in after the girl, confused. "Ryan says you need to get dressed into your costume." she said, her voice had a slight edge to it.
"My...costume?" I asked. "I didn't bring a costume."
"There's a costume here for you." She responded, simply. She pointed to the bed. I walked over and saw on the bed a rather small thin dress with wide horizontal stripes alternating in color between yellow and black. Next to the dress was a pair of long stockings and white wings with gold trim that appeared to loop around your arms.
"You're kidding, I assume." I said.
"Ryan said you need to wear this, given that you're taking him to a halloween dance." She replied.
"I'm going as a supervising adult, I don't need a costume." I replied.
"Listen." She said, impatient. "I'm sure Ryan is aware of all these things, so lets get going there's a bunch of work to do here." Her gaze traveled up and down my body as she said these last words.
Now that I got a good look at her I gauged her age at low-mid twenties. She had piercing green eyes and her body was as impressive from the front as it had been from the back.
"Um...okay, I guess." I said. Unsure of what I was agreeing to.
The girl sat me down and brought over what looked like a foot stool. Shockingly, she proceeded to take off my socks and began to work at my toes with clippers and a nail file.
"What are you doing!?" I asked.
"Do you really need to ask? Obviously I'm giving you a pedicure. The manicure is next."
I stared, confused about what was happening. The girl was efficient though and had finished up my feet, including a layer of light pink nail polish, and moved onto my hands in only 10 minutes. She made fast progress there too and this time applied a soft yellow, very subtle. I had to admit my hands and feet looked and felt great after this.
Next she brought over a make up kit and pulled set a seat in front of me so that she face me.
"Whoa. The makeup's not really necessary, right? It's just a costume." I said.
"You already got the mani/pedi and now you're saying the makeup is a step too far?" She asked. It was a fair point. "Besides, costume will look dumb without it."
