Chapter 1

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.

I am 6’5” and lightly muscled - neither brawny enough to be a

“hard guy” or skinny enough to have the thin look down. I’ve always thought of myself as exceptionally normal looking, and have the success rate with women to back up that rating. Jess was clearly moving this in a gendered direction, so 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?

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.