I’m James, just seventeen and pretty fit as I like working out in the gym. My friend Tiffany is two months older than me and hates the gym but she is very fit due to her cross country running, which I hate. Tiffany is gorgeous, with long, chestnut coloured hair and Mediterranean olive skin. She has an amazingly beautiful body with slim hips and such firm tits.

Anyway, we’ve known each other for about six years and started to dare each other a couple of years ago. It started as fairly mild stuff, like Tiffany had to walk through the village with no bra and no knickers. She made me take off my swimming trunks in our local pool when there were loads of people around. Whenever either of us came up with a dare there was always a consequence and punishment if we didn’t do it or got caught. 

Yesterday Tiffany and I were meeting in our local park. I was waiting on a wall when I saw her jogging towards me. She was always jogging and I loved the way it made her tits bounce. She seemed full of herself and couldn’t stop grinning as she leapt up to sit next to me.

“What?” I asked. “Come on, tell me.”

“I’ve thought of a new dare for you,” she giggled, “but I don’t think you’ll be man enough to do it.”

She’s a crafty mare, I thought, knowing that this would pique my interest. 

“Go on then, I’m game,” I told her.

“Without knowing what the dare is?”

“No, I’m not agreeing to it until I hear more. Tell me.”

“You have to run 2k cross country,” she said.

“Is that it? I hate running but I can do 2k.”

“Er, not quite, you have to do it in under thirty minutes.”

“That’s easy, even for me.”

“Normally you should be able to do it in twenty-two minutes, eleven minutes per kilometre, but you have to collect a few things on the way. And there are some consequences if you don’t.”

“What consequences?”

“No, that’s all you get until you accept the challenge or chicken out.”

I could tell she was up to something but I was curious. She’d used a strap on my bum in the past as a consequence. Come to think of it she’d used a plastic ruler on my cock when I gave up on a dare. I actually enjoyed that.

“Oh, go on, I’m going to do your dare,” I told her, “I’m not having you say I was too scared to try.”

“Right, here’s the route,” she showed me a map with a thick line across the country park near us. There were red crosses along the route.

“What are the red crosses,” I asked

She unfolded a sheet of paper detailing what I had to do at each cross and the consequences if I failed at any of them. Now I could see why she was so full of it. I was to start off wearing just six items of clothing, including shoes and socks and a hoodie top. 

“So, T-shirt, shorts, underpants, shoes and socks, but why the hoodie top?”

“Because, everything you take off you have to carry for the rest of your run, and the hoodie will be awkward to carry and if you drop anything you have to take another item off.”

I was starting to feel both nervous and excited at the same time. My cock was growing in anticipation. “What happens if I have to take everything off before the end?”

“You carry on regardless, even if you see other people in the park. Also, if you don’t get to the end in thrity minutes I’ll be using a cane on your backside.”

So now I knew how risky this was but I couldn’t back out now. “See you at the park tomorrow,” I added, as I set off home.

The following day was a scorcher so I didn’t put on my hoodie until the last moment. 

“I’ll be jogging along a little distance back so I’ll know if you fail to complete any of the tasks or drop anything,” Tiffany said, then without further ado, “Okay, go.”

I’d studied the list so I knew what I had to do and where. I needed to get rid of the hoodie as quickly as possible, I was roasting. 

I came to the first cross on the map, If someone is within 15 feet on the path you are crossing, remove one item of clothing. A lady and her dog were right there so I removed my hoodie before crossing the path. Tiffany was right, it was awkward to carry.

At the next cross Clamber up into the oak tree to retrieve the tennis ball. I could see it, ten or eleven feet up, so I wrapped the hoodie round my waist and clambered up. There it was wedged into where the next branch up met the trunk. I reached out as far as I could but only succeeded in knocking the ball clear. I watched in frustration as it fell to the ground. I got back down and realised Tiffany was watching so I had no choice but to remove my T-shirt. 

I was now carrying both hoodie, T-shirt, and tennis ball and underlined on the list was the instruction do not put the ball in a pocket, you must carry it.

I set off again, checking my watch as I went. Damn, I was behind schedule already. I picked up my pace and reached the next cross on the map, a five-bar gate. Climb over the gate while holding your clothes and tennis ball, then continue. I put the ball in my left hand and my hoodie and T-shirt over my left arm and got over reasonably well. As I moved away my hoodie caught on the gate catch and in my effort to stop it falling I lost the ball on the wrong side of the gate. I reached through and retrieved it but saw Tiffany watching. I took off my shorts and felt my cock responding to the knowledge that I was close to being spanked by Tiffany.

I set off again, holding T-shirt, shorts and hoodie plus tennis ball. At the next cross on the map I came to a narrow stream, Jump over the stream and continue. 

I took a run and sailed over, landing a good two feet on the other side but I fell as I landed and dropped my shorts and the bloody tennis ball. I glanced round and sure enough, there she was, noting my failure.

Shoes or underpants to come off? Neither was ideal but there were people walking everywhere so I took my shoes off. I hadn’t really thought this through because carrying a pair of trainers along with all the other gear proved very tricky and seconds later I dropped one of them. I sat on the grass and tied the two trainers together then removed my socks and stuffed them in the trainers.

I glanced at my watch, I had just two minutes left and I could see the destination in the distance, a small wooded copse, at the end of the rough sandy pathway marked on my map. The pathway was located on a raised section, some three feet above the rest of the park but luckily there were a couple of footholes dug into the side so, without losing any more time I quickly jumped onto the first and my bare foot found a stone making me drop almost all my stuff. Despite my predicament my cock began to swell at the thought of completing my dare totally naked.

I got to the pathway, no-one near by so I slipped off my underpants releasing my growing erection. I also realised that it was highly likely that I wouldn’t get to my destination in the remaining minute. Knowing Tiffany I guessed she would be punishing me in the park to add to her fun.

I gathered all my stuff and set off painfully, hobbling along the sandy, stoney path.

Three minutes late I reached my destination, a small copse of trees but the final instruction on the notes told me continue into the middle of the copse where I would find the large trunk of a felled tree. Wait there for me, still holding all your things. 

This was hard work, holding on to my stuff, having to fight my way past low branches and nettles naked. I finally arrived at the tree trunk, scratched and stung, now 13 minutes late. With all the exertion my cock had softened, despite anticipating the punishment to come.

A few minutes later Tiffany appeared from the other side of the open area; but she was not alone. Two of her friends that I knew followed her out, Sarah and Carol. I lowered my bundle of clothes to hide my penis which began to grow again in their presence. Sarah was really beautiful, slim with long blond hair and a wicked smile which was directed towards me at the moment. Carol was an attractive red head with a slightly fuller figure than Sarah. My eyes locked onto her firm, braless breasts where her nipples were pushing hard against her T-shirt. She actually licked her lips as she studied my body and my erection continued to harden.

Tiffany took control of the situation, “James, you were late getting here, so I’m going to punish you.”

“You didn’t tell me Sarah and Carol were going to be with you,” I mumbled.

“Well, that was an extra element to the dare, so now we’re all going to punish you.”

Carol and Sarah obviously knew about this. Their eyes lit up and Carol eased her legs apart at the prospect.

“You were fourteen minutes late,” she began.

“Thirteen,” I corrected her.

She smiled, “Alright, thirteen, and how many items did you drop en route?”

“I don’t know, why? I added lamely, wondering where this was going.

“Didn’t you look on the other side of the notes? she asked.

I grabbed at the notes, dropping most of my clothes. I gave up trying to hide my erection and threw the rest down, enjoying the look of excitement on their faces and my cock responded.

“Read it out loud,” Tiffany told me.

“Punishment. One stroke of the cane across your bum for every minute late.”

“And the rest,” she added, “how many items did you drop?”

I continued, “Add to the minutes late, every item dropped, each time it was dropped. I don’t know how many times I dropped things.”

“Then it’s a good job I kept notes,” she smiled, looking at her little notebook. “All together you dropped twenty-five items so in total that is thirty-eight strokes of the cane.”

My face fell.

“Read the rest,” she added.

“Penis Punishment, one stroke of a leather strap for every count over twenty and if the number is greater than twelve the remaining strokes will be given with fresh nettles. Noo!”

“You agreed to the rules. Right, bend over the tree trunk.”

I had no option and saw Tiffany hand Carol a whippy-looking sappling she’d broken off. 

I tried not to cry out but each stroke stung like fury and twice I leapt up, my cock swinging from side to side. 13 Strokes later she ran her fingers along the tramlines on my bum.

Sarah took the sappling and stepped to one side before I heard the woosh and the pain went through me. Each time I heard the swish, I closed my eyes and waited for the sting. Sarah stopped twice to check her handiwork and on the second time I felt her fingers close around my cock, sliding the juices around the helmet.

“You are very fit,” Sarah murmured as she ran her hand across my chest, down over my abs and then circling my cock again.

Tiffany stepped in, “My turn.” She’d done this many times, though previously in private. Of course she ran her fingers along my cock and around the helmet as I knew she would. Then, without warning, she bent me over, swish, swish, swish. I lost count until she told me to stand up. 

Tiffany undid her leather belt and gave it to Sarah, “Four strokes from each of us, then two more with a bunch of nettles.”

Using my T-shirt she picked a good bunch of bright green nettles as Sarah prepared to spank my cock. She stroked it first, ensuring it was fully hard, then brought the strap down across the shaft four times. 

Each time Tiffany had done this in the past I’d had the same reaction, first the stab of pain followed by an incredible wave of pleasure down my cock. But then she carefully took the bundle of nettles and rested them across my cock as she had done with the strap. The nettle sting made me yell and pull back before again I got the wave of pleasure down my cock. Sarah brought the nettles down across the head twice and smiled as I cried out.

Carol took the strap. She eased my foreskin back to expose the helmet then delivered four strokes along the length of my nearly eight-inch erection. She’s seen Sarah resting the nettles on my penis but she decided to go one step further. She pushed the nettle bunch around the head. I cried out and moved back but Tiffany was there to keep me in place. Carol was enjoying this and weirdly, so was I. She lifted the bunch high and struck twice across the shaft.

I watched nervously as Tiffany picked a fresh bunch of nettles before coming over to collect the strap. She stroked me until I was rigid and my juices flowed, then, thwack, thwack, thwack, thwack. The girls giggled as my cock swung around. Tiffany had enjoyed my reaction to Sarah with the nettles on my penis so she pulled my foreskin clear of the helmet before pressing the nettles onto the tip of my cock.

“Aargh,” I cried, jumping back but Tiffany had not done yet and pushed the nettles past the head and along the shaft and onto my balls. 

“Ooow!” Then the wave of pleasure got to me and I groaned just as she delivered her two strokes of the nettle bunch along my shaft.

I was still rock hard and feeling so horny. Before I knew what was happening Sarah moved close behind me and began to slide her hand back and forth along my rigid member using the copious juices. The incredible sensations from the strap and nettles erupted and I shot my load across the tree trunk while the girls giggled at the sight. 

“Get dressed and we’ll walk back together,” Tiffany suggested.