A dare to a new level

My name is Anthony, and this is the story of how I was introduced to a whole new world of pleasure. It all started with a game, a game of truth or dare. Jess, a friend of mine, and I were bored one evening, and we were texting as I was on the train on the way home from work. She suggested that we play truth or dare, and gave me the first go, as she had suggested the game. I wasn't much one for telling the truth, as she knew, but I went along with it anyway. She asked for a truth question and I decided to start off easy, as she was only a friend, and I figured this was just some light entertainment to pass the time.

Anthony - Have you ever ...

Jess - No, truth or dare?

Anthony - Truth

She seemed to have her question locked and ready to go as she came straight back to me.

Jess - What are you most jealous about women for been able to do that men can't?

Anthony - I suppose been able to dress up in such a variety of ways to be sexy.

Given what she had said, when she asked for another truth I asked her to tell me what she was wearing.

Jess - I'm in holdups and a skirt, with a pair of lace French cut knickers on. I have my bra and a blue blouse.

Anthony - See this is what I mean! Men have boxers or briefs, and nothing like holdups at all. The ability to dress to impress is definitely a female power.

Jess - I don't know, there are things a man can do. Anyway, truth or dare?

Anthony - My train has just arrived, a truth for later please?

This went on for a few days, us learning more about each other. I found out the most men she had been with in a night was four, she found out about the time I had sex with my girlfriend in the swimming pool changing rooms when I was 17. I found out that she had been with a woman before, and she got told about the time I shaved it all bare for a woman I was seeing. To this point the dares were very tame - things like chugging a drink in the evening. However she then asked a question that I had no intention of answering

Jess - Have you ever been with another man?

(The answer was only partially. While I was growing up a gay friend of mine had a crush on me. At his urging, one night I snuck out of my parents house and met him in a field nearby. We kissed for five minutes, and then he gave me a blowjob, but didn't ask me to reciprocate. After he left, and neither of us ever brought it up again)

Anthony - I think I'm going to change my request to dare here. 

Jess - You can't do that! I've already asked you my question!

Anthony - There isn't anything in the rules that says I can't change. Come on, just give me a dare

Jess - Fine, but you brought this on yourself! 😉 On your way home go into tesco, and buy yourself a thong that would fit you. If you need help with the size ask the shop assistant. You can tell her whatever you want, as long as you start by saying it's for a big weekend.

I was shocked, this was well outside of our normal dares! I went red just thinking about it, although as I did a quick frission of excitement went through me. I knew better than to argue back, she'd let me win once, there was no way I'd change her mind this time. I went to the women's section, and found the brightest pink thong they had. As I picked it up, I felt the same sense of excitement, as if I was doing something naughty and getting away with it. I suddenly noticed I was achingly hard, pressing against the front of my suit trousers. It was a cold day so I had a long coat, which I rearranged over me to hide the evidence. I avoided the shop assistant, used the self service till and ran for my car.

Anthony - I got one!

Jess - Prove it, let's see a picture 

I sent her a picture of the thong lying next to me on the car seat

Jess - So, what did the assistant say?

Anthony - I didn't speak to one, I'm sure they fit.

Jess - Well you have to prove that too, put them on and send me a picture

Anthony - Here? I'm in public, I can't take my trousers off!!

Jess - I guess, put them on over your trousers, then stand up outside and take your picture, so I know they fit properly.

I looked all over the car park, but it seemed empty. I pulled them on standing with the door covering me, had one last look around. As I did a car headlights flashed round the corner, pinning me in place, but they drove off around the far side of the shop. My face burning, and my prick aching, I stepped away from the door and took the picture quickly. I jumped back in the car, and before I could do anything else I got another text.

Jess - Once you've got the picture don't take them off

I sent through the picture, hoping that this was over, or just beginning. My brain and my body seemed to be thinking two different things.

Jess - That's quite the look on you 😉. And look how you fill them out 😜. This dare can be over now, or you can come pick me up now, exactly like that, if your up for it?

Anthony - I'll be there in five

Jess was standing on her street corner as I pulled up. She jumped in the car, smiled at me, and told me to drive to a local spot nearby, a car park that was nearly always empty this time of night. As I drove away, she asked me how I felt. I was just about to answer when suddenly she started rubbing her hand over my new thong, pressing on my hard cock underneath. Words were beyond me and I just groaned.

She smiled again and said "My, you're going to need better control than that if we keep this up". She then dragged a finger nail down my cheek, lightly scratching me, sending a flair of pain which combined with the aching coming from my crotch. It was only a few minutes to the car park, so I arrived before anything else happened and pulled into a space facing the wall, and turned the car off. 

I reached over to kiss her, but as I did she grabbed my cock through the new underwear and my trousers and squeezed. "Nuhuh" she breathed in my ear, "This is my fun, not yours". I was so turned on at this point I think I would've agreed to anything. She told me to take the thong off standing outside the car, and to hand it to her. At this point I barely cared about been seen, so jumped out and whipped them off before sliding back in. As I seated myself she pulled down my fly, and threaded my cock out, revealing its full length. She chuckled in my ear "Is this for me, or your new purchase?" before nibbling on my ear. She took the thong and tied it round the base of my cock, and said "If you cum before I say so you'll have to lick it all up." She then took my hand, and fed it under her skirt. I could feel her panties, also a thong, were soaked. She told me to take them off and give them to her, while she continued to stroke my cock with the lace part of the thong tied around it. I was in heaven from the feeling, but trying my best to hold it in - I figured she might tease me for a while. She took her thong off me, and then told me to hold the steering wheel with both hands. Suddenly my mouth was full of the taste of her, and she pushed her soaked thong in my mouth. While she did that the attack on my prick went from 2 to 10, as she pulled and tugged at me, before running her nails over my sensitive mushroom head. 

I couldn't stand it anymore - all the new sensations, the taste of her, the fantastic hand job, it was all too much, and I groaned into my gag and I erupted over her hand, and my new underwear. "Oh no" she beamed, "guess this is for you then" as she brought her hand to my lips. She allowed me to spit out the thong in my mouth, and fed my cum to me drop by drop. It was salty, warm, but not awful - to be honest I'd expected worse from what I'd heard. 

"If you want a chance to get another dare in the bank, I've got one for you now" she whispered in my ear. I figured at this point why not, I was feeling so good from my experience. I agreed, and she told me to get dressed in my new thong again, but as my only bottoms this time. My concerns from before were blown away in my ejaculation, so I quickly stripped and redressed. She then told me to come around the car to her door. I quickly ran round, looking out for lights, and opened her door. She said "Kneel out there, and lick me until I cum too", pushing one leg out on the door, the other over my shoulder. I don't believe anyone saw me, but what a sight it would've been - a man in work shoes kneeling in the road, dressed in a shirt and a pink thong, with a girls legs around his ears, her face closed tight as she moaned out her orgasm.

That was her first two big dares - but now I owed her two back!!

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