Dare You?

You've gone away on business again, and, as we both like to do, I've given you a list of tasks. I love to dare you to do things. You'll usually manage at least one or two of them, and it's great for the inevitable phone sex or cyber sex later.

There are the usual mild ones, like "Film yourself nude, in bed, playing with yourself", or "Send me a photo of your vibrator inside you." There are some not so mild ones, "Forget your knickers to dinner", or "Photograph yourself nude next to the hotel bedroom window."

Then there's the last one.

The "do you dare?" option.

The most extreme one.

"Pick up a man in the hotel bar. Have him photograph you. Nude. In bed. With him."

We chat online during the evening. It's the usual flirting, and chatting about your day. It's been successful, apparently. You seem very cheerful, you won a very lucrative contract and you've enjoyed yourself. I receive a photo of you in a skirt, swinging a pair of your knickers on your finger as you head out for dinner. You're wearing a very cheeky, attractive grin, my favourite top of yours, the low cut one, and you're clearly having fun. I'm jealous I'm not there - I know that grin. Your vibrator is going to be busy tonight. Quite probably with your phone in your other hand, to let me hear you as you orgasm. This is shaping up to be a fun night for both of us. I resolve to get to bed early in preparation.

After you've eaten, messaging me to tell me how naughty you feel to be dining in public feeling the cool air on your bare pussy, you send me a note so say you're going for a quick drink before you head to your room.

Then you go quiet. It's unusual. Normally I'd receive a photo of a glass of something, and a cheeky note saying something along the lines of "look at what you're missing out on. And the wine, too!" You're probably just busy chatting.

Later on, I receive a vague text. "Having a good night. Hotel bar very fun. I'll try and message later. xx"

I wait, wondering what's going on.

40 minutes later I receive another message.

"I'm feeling brave. Remember I love you."

My heart pounds. What's going on? I message you back, but there's no reply and the text remains unread.

Finally, a photo message. It's a young man, early 20s. He's probably young enough to be your son. Dark hair, blue eyes, slim and handsome. He's in a selfie with you. You're both grinning. The caption is "You like? xx"

Really? You're really going to go through with it? I'm shocked. You like a challenge, but this one was meant to be something to joke about. It's always been a shared fantasy, but it was never really meant to happen. I mean, we've talked about it a lot, but it was always hypothetical. Now it's real. And very good looking. And apparently about to kiss you.

I take a deep breath and message you back with a nonchalant sounding, but braver than I feel, "oh yes! You go for it :) xx". It might sound positive, but I feel strange. It's really happening.

It all goes quiet again. I'm lying in bed, stroking myself. I'm excited but scared. What if you go through with the dare and you find you prefer him to me? He's half my age! But it's such a hot thought. I like it. And it's really turning me on.

Another message. What is it? I bet you've stepped back and are going to bed alone.

"If you're sure you want me to go through with this, I'm in room 324. If you don't hear from me in a couple of hours, call me. Love you always xxx"

Shit! You're really doing it. I'm hard as a rock. I can't bear to touch myself - I'll explode. I've fantasied about this, we both have. But fantasy and reality are very, very different beasts.

I reply. "Do it. Xxx". My finger shakes and my breathing hitches as I press send. But what courage my finger lacks, my erection makes up for in strength.

An hour later, my heart is still pounding. I'm sweating. I swing between anxiety and extreme arousal, and I'm hoping I've done the right thing. I can't help thinking of you, and what you might be doing. I want, dearly, for you to enjoy this. I'm checking my phone constantly. Then a notification appears.

Photographs. Six of them.

I open them, my heart in my mouth.

A rock hard, youthful cock. With what are unmistakably your lips around it.

A pussy with a very familiar landing strip of dark hair above it, that I distinctly remember shaving around earlier in the week. With a hard cock just parting the lips.

The same pussy. The same cock. Deep inside.

That same pussy again. Wet and open. Semen leaking out of your cunt.

Your face. Tired but very happy. Satisfied. With ribbons of pearlescent cum all over it.

You, lying on your back, in bed. With him. His head nuzzled into your nude breasts.

Then a message.

"Thank you, darling. That was amazing. I forgot how good the stamina of a twenty five year old can be. He's gone now. I still love you xxxx"

I ejaculate harder than I have in years, the cum hitting my chest and face. I cry out with the force of it.

My phone rings.

"I still love you. Don't be jealous. That was amazing. Thank you for making me do it. Thank you for making me do him. Want to play?"

Your vibrator buzzes, and I grin, my cock twitching.