Chapter 1 – An Unexpected Thrill

Tuesday 7th June 2016

Bearsden

Glasgow

It was a lovely warm morning, so after my wife left for work, I went for a walk through the local woods. I’d been doing it for a few weeks, but most recently, doing more than walking. One morning, three weeks earlier, probably due to sexual frustration, my imagination had been running riot, and I wanted to do something kinky.

I had wandered off the narrow path to find a clearing where I could drop my pants and give myself a good time in the open air. That first time, I’d stood there with my jogging pants and boxers down around my ankles and found it exhilarating, wanking in the woods. I shot my load really quick, and I knew it was something I’d do again and again.

That was how it started, and here I was again, but feeling I needed more. I wore a long T-shirt and jogging pants as normal, but instead of boxers, I was wearing a pair of my wife’s panties. They were white lace and felt snug and sexy, holding my package firmly in place. By the time I got to my little clearing, I didn’t need any slow build-up like normal. I already had a hard-on.

As usual, I stood for a moment listening, just to make sure there was nobody else around, but the clearing was in a dense part of the woods, so I felt safe. It was an almost circular area with thick grass, and a fallen tree was off to one side of me. I’d sat on the tree once to stroke my cock, but I preferred dropping my pants and kneeling on the grass. I took off my T-shirt and dropped it.

I removed the elastic scrunchie that held my long blonde ponytail in place and leaned my head back. I felt my hair on my back and dropped my jogging pants to my ankles. When I looked down at my sexy panties and the bulge within, I sighed, and my breathing became deeper and faster.

I knelt down and moved my knees apart, and because of the panties, I felt this session was going to be special. I reached back to caress my long hair with one hand and caressed my lace panties with the other hand. When I felt the throbbing bulge of my hard-on, I rubbed it within the soft material and sighed. It wasn’t long before I was using both hands to caress the bulge of my aching cock. I held it firmly in the lace and stroked slowly a few times, and after briefly gazing at the panties, I closed my eyes. I knelt there, stroking slowly in ecstasy, not sure why wearing panties was helping. I eased my free hand inside the material and under my ball sack. As I caressed and squeezed my balls with one hand, I wanked myself off with the other.

“I’m just a kinky sod,” I whispered as I continued to stroke my cock in the lace.

“You really are a kinky sod,” a nearby male voice said.

I opened my eyes and stopped what I was doing. My lips trembled as I stared up at the guy stepping from my right side to stop in front of me. He was wearing a T-shirt and jogging pants, just like me, but he was still dressed. He was also clean-shaven, like me, but a major difference was that he was tall, well-built, and much bigger. I moved both hands to cover the front of my panties, but a strong hand landed on my shoulder.

“Take your hands away from your panties, but stay on your knees.”

“Please,” I whimpered. “I’m … I’m not … I’m not a—”

“You’re not a girl, so you must be a fetishist or a sissy.” The hand stayed on my shoulder. “Either way, I’d like you to continue pleasuring yourself.”

“I’m not a sissy—”

“Maybe not yet. Now, push your panties down, and stroke your clitty cock.”

My clitty cock?

“I’ve lost my arousal, and—” My mouth went dry when he let go of my shoulder and pushed his jogging pants off his hips.

His pants fell to his ankles, and then he eased his red boxers over the sizeable package within to let them fall and rest on his pants. His cock was soft but was already longer and thicker than mine. The shining, circumcised head was strangely sexy. His big ball sack hung there, prominent behind his shaft. There wasn’t a hair or a bristle anywhere because he was shaved totally smooth.

He said, “Stroke mine and see if it helps to get you aroused again, sissy.”

“I’m not a—”

“Stroke my cock, you kinky girly-boi.” He held my head in both of his strong hands. “Mm, such a smooth face. If you don’t stroke my cock for me, I may have to force you to do something else.”

“I’ll … I’ll stroke it.” I stared at the veins in his big shaft and reached out with my right hand to touch it. It felt strange to touch another man’s cock for the first time. Once I had a loose grip, I remembered what the other option was, so I slowly stroked it in a downward motion, like milking. Since it was soft, I continued to tug on it instead of holding it upright, but I soon felt it filling out. By the time I’d stroked a few times, it was becoming stiff. I held it upright and continued.

He sighed and took one hand from my face but left the other resting on my head. “Good girl.”

Why is he calling me a girl now?

I was mesmerised by the sight of such a big cock, and the sensation of giving a handjob to someone else. I wasn’t sure why, but it felt natural to reach up with my other hand and cup his balls, which brought another sigh from above me.

“You’re good at that, sissy, and now, look at your clitty cock.”

I paused briefly and looked down. The pink head glistened, and the shock made me look up at the stranger.

How can doing this for him possibly be arousing me?

He smiled down at me. “Go on, princess, I’m not selfish. Use one hand for me and one for you.”

I continued to stroke his big shaft with my right hand and simultaneously used my left hand to stroke my average cock. I mainly looked at his impressive shaft, but I occasionally glanced down at mine, enjoying the sight of the lace panties snug around my balls. I didn’t know if it was the panties or the unexpected task of wanking off a stranger, but I was experiencing a greater thrill than I could have hoped for.

He panted. “What’s your … girly name … when you … wear lingerie?”

“I don’t have one,” I said and panted as I stroked him a little bit faster. It wasn’t intentional, but I realised that I was stroking myself faster, too.

He continued, “You should have … a nice girly name … for when you … dress up.”

“This is the first time I’ve ever worn panties.”

“It’s not your … first time … wanking … in the woods … is it?”

“No, I’ve done that a couple of times.”

“Cindy.”

“What?” I said and glanced up.

He was panting heavier. “I’ll call you … Cindy … Cindy … the Sissy.”

“But I’m not ….” I imagined what we’d look like to anyone else, and it aroused me more. “Oh my … oh … I’m gonna come … I’m—” I shot my load and stroked myself for a moment longer.

“Oh Cindy, your first spurt of cream shot between my legs. ”

“I … I know.” I eased off what I was doing for him.

“You have to … keep going … Cindy … or you know … what I’ll expect … my sweet sissy.” He placed both hands on my head and held me steady. “Use both hands … like you did before.”

I continued wanking him off and cupped his balls with my other hand. I couldn’t take my eyes off his big cock, and I wondered what it would feel like if he carried out his threat.

Can I get a couple of inches of that thing in my mouth?

“I can see you … looking at my cock … Cindy. I think maybe … you’d like to … suck it.”

“No … no, I just … want to … do this right … for you.” I changed hands because my right arm was getting tired, and he was lasting much longer than me. I felt like I’d been wanking him off for ages and changed hands again. He had a lot of stamina.

“Lift your head up … Cindy … and look at me.”

I glanced up. “Why do you want—?”

“I want to … come on your face … or over … your body.”

Oh my god, I hope he doesn’t come on my face.

I kept stroking him and tilted my head to look up as he’d suggested. 

“That’s good … that’s a good girl … Cindy … I’m gonna come … I’m coming … I’m coming … oh yes … yess—” He gripped my head with both hands, and I felt his cream hit my face close to my lips. I glanced at his cock as I continued stroking, but more gently. He jerked his hips and kept coming in spurts, so his cum was going all over my chest and running down my body.

As I stared at his cock, I slowed down the speed of my arm. I felt a tickle at the side of my mouth, so I instinctively licked and swallowed. It was a strange taste but not unpleasant.

Oh fuck, I’ve just swallowed some of his cum.

I glanced up at his face and hoped he didn’t see me swallowing his cream. I tried to keep my gaze on his cock and continued to stroke it but slower until he stopped coming.

“Oh, Cindy … that was … nice. I think I’ll need you … to do it again … sometime.”

“We might not … see each other again.”

“I think we will … princess. I bet you wander in here regularly … about this time, don’t you?”

“Yes … yes, I come here … on a Tuesday … and a ….”

“Go on … kinky … sexy … sissy … what other day?”

“A Friday,” I confessed.

“At the same time on both days?”

I swallowed so loud I heard it. “Yes.”

“The weather will be like this all week.” He inhaled deeply. “I’ll see you here on Friday.” He squatted to pull up his underwear and jogging pants and looked into my eyes. “Okay, Cindy?”

I bit my lip and nodded. “Yes … yes, okay.” With his short brown hair and clean-shaven face, I considered for a moment that he was maybe forty and an attractive man.

He smiled and raised a finger to wipe the cum still on my face, but instead of removing it, he moved his finger to my mouth and slipped it inside. “Go on, princess.”

I sucked his finger and swallowed the cum he’d fed me.

“Good girl, Cindy, and that was so sexy. I think we’re going to have a lot of fun together.” He touched his own lips with his forefinger and then touched it to mine. “Next time, I’d like you to wear a bra and matching panties.”

“I … I—”

He smiled. “A matching bra and panties.” He gazed into my eyes. “You already have a nice smooth face and lovely long hair like a girl.”

“Thank you.”

What am I doing, thanking him for a compliment about how girly he thinks I am?

He gazed into my eyes for a moment and whispered, “Cindy, the pretty sissy.”

“What do I call you?”

“Roger.” He caressed my lips with a fingertip. “I’ll see you on Friday, Cindy.” He stood and turned to go but paused and looked back. “When you shower, do you clean your bum hole?”

 “I … I sometimes rub it with a fingertip to ensure it’s clean.” I shook my head, confused. “Why did you want to know that?”

“I might want to tease your bum with a finger, so I’d like it to be really clean in there.”

“Okay … I’ll … I’ll clean it well—”

“Good girl.” He turned and walked out of the clearing through the heavy undergrowth between the trees.

What am I thinking, telling him I’ll clean my bum hole well?

I remained on my knees and used a hanky to wipe my face and chest before putting on my T-shirt. I stood and pulled up my panties and jogging pants.

***