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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. bursa escort “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.”
She began applying makeup, concentrating hard on my face as I stared back at her. It was a weird feeling. I had never worn makeup before. I became increasingly squeamish when she applied eyeliner, but managed to make it through without twitching so that she stabbed me in the eye.
Finally, she fastened hair extensions to my head. They integrated with my medium-length hair well and fell to my shoulders. I didn’t object, it seemed like less of an issue than the makeup.
But then she told me to strip. I began taking off my clothes but left my boxers on. “Down to your birthday suit.” She said.
“What? No fucking way.”
“How do you think this dress will look over your boxers? They’ll just be poking out the bottom. It’ll look ridiculous. Do you want to embarrass Ryan?”
She was right of course. “Put these on” she said, holding out a small piece of black fabric. “These are control briefs. They’re small enough that they won’t poke out anywhere but big enough to be…supportive.” She said this last piece with a half grin and I blushed, taking them from her.
I turned away and pulled down my boxers, embarrassed. As I pulled on the panties though I had to admit, they felt wonderful. Soft and smooth against my skin, they cupped my ass comfortably and gently.
“And here’s the bra” I hear the girl say. I spun around and saw she held a bra that appeared to have the tits built in. I was going to have to put on fake boobs? I thought.
“Is that really necessary?” I asked.
“The costume won’t even fit you without it.” She answered.
With trepidation, I reached out and took the bra from her. It was heavy. I pulled it around myself but wasn’t sure how to tighten it. Only two thin clear strip ran across the back, linking the sides of the bra together. The girl helped, pulling it tight from behind somehow and fastening it. As she did so the boobs contoured to my body and all the sudden I was looking down at my very own tits.
I couldn’t help but grinning. It was just so ridiculous. I guessed that was the point of the outfit, great for providing a good laugh.
“Alright,” the girl said, “put it all on.” At this point the girl had been working on me for over an hour so it was a relief to finally be past it. I pulled on the dress and it immediately contoured to my body, squeezing against my fake boobs, tight in at my waist, and wide again at the hips.
The girl glanced at me up and down. “Oh, lipstick.” She went to her purse and grabbed a tube of lipstick, applying it to my lips. “Press your lips together.” I did so.
“Okay, come look.” She beckoned me over to a mirror leaning against a wall and I walked over, extremely curious.
My mouth fell open. I stood in front of the mirror, amazed. görükle escort I barely recognized myself. I stared at the wonders this grumpy girl had preformed. My lips were full and pouty. Somehow they even looked moist, though they weren’t overloaded with lipstick or anything. My eyes were dark and…brooding Somehow, my eyelashes long. Even my cheekbones and chin seemed accentuated. My hair was lengthened with auburn extensions and fell wavy down to the top of my chest.
My chest – it stuck out gloriously. I felt the weight pulling me down in front and stood up taller, resisting. The yellow and black striped dress stuck to every curve and seemed to support and press together my voluptuous breasts, pushing out even more now with my upright posture. The dress was high-necked (as it had to be given that the cleavage would be fake) but low-backed. Apparently, I had a distinct hourglass figure now.
As I turned around to look from the back I sucked in a breath. I had always hated my shoulders, which were thin and bony. I now realized this was a perfect trait for a girl, making me look dainty and sexy. Tracing downwards I also realized I had developed a thin, toned, feminine back. To thin lines of muscle ran up either side of my spine, which itself was just slightly visible. The hair-removal cream I’d been using (once a week) also provided nutrients that had my skin looking the best it had ever had.
My pale, thin back sloped into the lovely round curves of my ass. Damn. My ass had continued to grow and develop under Ryan’s close tutelage. The dress hugged it hard, outlining each cheek in a sumptuous fashion. The hem ended just below my butt and unless I repeatedly pulled the dress down, the folds where my ass cheeks met my legs would keep peeking out. As the girl had predicted, the panties weren’t visible.
My legs too looks surprisingly good. It was another trait of my body I had never liked – no one wanted long legs on a guy. But in this costume they were long and shapely. The thin pale stockings reached high and ended just below the dress. Though sheer and pale most of the way up, the top of the stockings were lacy and sexy.
“Now put these on.” The girl held out a pair of dainty but high wedges. I sat down obediently and as I slipped them on I appreciated the necessity of the pedicure. My feet looked soft and dainty, encased now in these beautiful and sexy shoes.
I stood up, unsure of myself. But the shoes felt surprisingly comfortable. And they weren’t as high as I’d first thought, only 2-3 inches off the ground. As I walked around experimentally, I realized they felt quite natural. I looked at myself in the mirror again and saw that the shoes accentuated my legs and pushed up my butt further. I raised my eyebrows, appreciatively.
“Okay, lets go.” The girl said.
“Huh?, where?” I asked
“To show Ryan.” She answered shortly.
“Umm…do You think he’ll like it?” I asked nervously. Why did I ask that? Who cares? It was a costume. I should really change into something else more appropriate. “Actually, are there any other costumes I could wear?”
“Just follow me.” The girl answered impatiently. Ignoring my questions.
I hesitated only a moment more, then followed. I couldn’t shake the growing thought: God I hope he likes it.
Ryan was sitting in his desk chair facing his computer when I stepped into his room. He swiveled around to face me. His hair was wet and a towel hung around his neck, covering most of his body. He wore loose fitting grey sweatpants. His arms were on full display to his shoulders though, bulging with muscle and glistening with water from his shower. My eyes focused in on him intently and my heart hammered against my chest. After almost two weeks the rush of excitement at seeing him hit me all at once. “Hi Ryan.” I said softly, and in a higher pitch than normal. It just seemed to make more sense to use that voice when dressed up like this, for the sake of the costume of course.
He saw me and looked me up and down slowly. I waited, embarrassed.
He gave a small smirk. “God damn, babe. Looking fucking good. Come here let me see you.”
I tried to keep my composure (though I had a difficult time suppressing the incredible pleasure that came with Ryan’s words).
“Ryan,” I said, a small shake in my voice, “I don’t know. Why do you want me to dress like this?”
I glanced over at the girl who had worked so hard, if unhappily, on my outfit and makeup. She had one eyebrow cocked, curious to see where this went.
“It’s a halloween dance, babe. You have to dress up!”
“But I’m just the supervising adult escort for you and a friend, right? Why do I need a costume?”
“A lot of the adults wear costumes too.”
Though I wanted to accept this, my discomfort with this costume forced me to persist. “But why a costume like this?”
“My slutty older sister here didn’t have anything else you could wear. Plus I thought you’d look good in it.”
Under bursa escort bayan other circumstances I may have asked why he only considered his sister’s costumes, but I was immediately distracted. His sister? I glanced over at the brunette and saw she was staring daggers back at Ryan.
“Fuck you” she said.
“Not right now, I don’t think. But soon enough, slut.” I was surprised by the aggressiveness of Ryan’s response. I’d never seen him like this.
Still looking at Ryan’s sister, I saw she colored and lost her composure a bit, but she continued to look at Ryan, disgruntled. Something else, though, as well. Hopeful?
“I don’t know why I agreed to do this for you, ass hole.”
“Oh I we both know why, Kasi, don’t we?”
So her name was Kasi. I thought I should extricate myself from this fight between family members. “Ryan, I’m gonna…”
Ryan interrupted. “Jesus girls, calm down won’t you?” Ryan stood up and took off his towel. My eyes immediately scanned him up and down, taking in his rock hard body, impossibly large and defined for a teenager. My mouth went dry and any further words died in my mouth. Somehow in the time I hadn’t seen him I’d forgotten just how impressive his body was. I noticed his sister, Kasi apparently, had also clammed up. I glanced over and saw that her gaze too was locked onto her younger brother’s body. Her face had gone slack, all traces of anger gone.`
He walked over to me so that he stood right in front of me. I looked up his chest, paused at his lips, then into his intense blue eyes. “Now, lets see you.” his hand reached past my face as he felt the luscious brown hair that his sister had secured. His fingers rand through the hair on top of my head then ran down to the side, sliding through the soft waves. “Very nice, Jerry.” I blushed. Though I thought-Jerry? He never called me that.
As if thinking the same thing, he said, still stroking my hair “Jerry isn’t really right when you’re like this, right? What should we call you? Hmmm…Janelle. That’s sexy right?”
I instantly liked the name, if only because Ryan had said it was sexy. Instead, though, I said “I don’t know, Ryan. This is just a costume. My name is…”
“Shhhh” he brought an index finger to my lips, silencing me. “You’ll get used to it, Janelle.” Ryan ran his finger along my lips slowly. I closed my eyes and was just opening my mouth when he removed his hand. Was I about to suck his finger? I asked myself.
His hands came to rest on my hips. He ran his hands up my sides, feeling with his firm hands my new, hard-earned curves and sending shivers through my body. As his hands reached the sides of the fake tits, he brought them forward and rested them on top. He smirked, his eyes again glancing at mine as he gave them a firm squeeze. I let out a slight sound, my breath catching as I suppressed a moan.
The bra was designed in such a way that the pressure applied apparently traveled through the fake boobs almost unimpeded so that I felt it directly on my own chest. Seeing him squeeze the breasts and feeling his touch at the same time was an effective mind trick. Even knowing what I knew, the sensation was that these large tits were really my own.
“These are fucking perfect.” Ryan said, kneading and pinching. I stared down at Ryan’s large hands squeezing my large perky breasts, then looked up again at Ryan’s handsome face. I was illogically pleased with his reaction to my large tits. My eyes fluttered closed and open again.
One of his hands left my chest and I he turned me by the arm so that I faced his sister. She was staring at us intently, her eyebrows arched almost pleadingly – high on the inside low on the outside. She was biting her bottom lip with her chin slightly raised.
I felt Ryan’s strong hand trace down my bare back and I automatically arched my back in surprise. I didn’t move, though. Ryan’s other hand was still on my left breast.
His hand continued its path down my back and came to the top of my ass, now pressed out with my back arched. He slowly ran it over my ass, cupping from the bottom and squeezing.
My eyes closed and I couldn’t help but moan audibly now. “UUuuuhhhh”
Mine wasn’t the only moan though. I opened my eyes and realized that Kasi had moaned at that moment as well. She was clasping her hands tightly to one another, her knees pressed together, like she was trying to fight something.
I felt Ryan’s hands pause. Then I hear a low chuckle.
“Kasi? What’s wrong?” I could hear the smirk in his voice.
Apparently Kasi did too and she momentarily stood up taller, bringing her hands down to her side, looking over my shoulder at Ryan defiantly.
“Ass hole.” She said.
Ryan ignored her. “What I’d like you to do, big sister, is to look at how I touch Janelle’s sexy body here, and imagine I’m touching you this way. Just like you wished I would.”
Her eyes arched, surprised. Then they lowered again. “Go fuck yourself.”
Again Ryan ignored her. Gently, he repositioned me so that he stood directly behind me. I felt his huge hard body press up against me. I faced Kasi directly now, about 10 feet away now. I felt Ryan’s giant cock pressing into me, starting at the top of my ass and hang down past the bottom.
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