We walk into the hotel bar, and she sends me to get drinks while she finds us a booth with a people watching view. I have the same cocktail she’s ordered, and join her at a seat with a view of almost the whole bar.
I sit opposite, but it’s small enough that we can lean close together and whisper about the other patrons. It’s also small enough that she can easily stretch out a leg and brush my chastity cage with her toe. I know that because it’s what she immediately does when I take my place.
The cage is covered in her black lace knickers, the ones she wore most of the day and threw at me when we were getting dressed for the evening. I was allowed a sniff before putting them on, and as always, her delicate aroma made my head spin with desire.
On top of that, I’m perfectly respectable in a dark suit, with a tie that matches her burgundy dress. We look conservative and normal. Not out of place or drawing attention, just background to the other drinkers. You’d walk right past us without a second thought. It’s possible that you have.
Around her neck is a thin gold chain, with a key hanging an inch or two above her cleavage. Nothing ostentatious, but a subtle clue to any suitably kinky passers-by.
We’re here because she’s decided we should be, and it’s not my place to question that. Not when I’m caged, anyway.
She’s typing something on her phone, and I wait patiently for her attention. The full force of her attention is a powerful and addictive thing, and can instantly silence me or make me feel like a king. When she does turn her gaze on me, I can tell she has a surprise for me.
She raises her glass, “To an evening of excitement and new experiences,” she says with a grin. I’m sure my face registers some query, but she chooses to ignore it. My patience will be rewarded, I have no doubt.
We turn our shared attention to the other customers, quietly speculating about their relationships and plans for the evening. Always with a filthy and kinky twist, of course. The couple with the age gap in the corner; is she going to let him fuck her ass tonight? The lone woman at the bar, is she a business woman or a prostitute? The two men halfway down their second bottle of red and in an animated discussion, friends or lovers?
And so it goes on, jointly wondering about the private lives of others, sipping our drinks and enjoying our freedom.
Another man comes in, slightly taller and leaner than myself, and takes a seat at the bar. Immediately she asks me how big I think his cock is. Not an unusual question between us, but there’s something in the way she says it.
I fumble for an answer, as she fiddles with her handbag, pulling out a folded piece of her nicest paper. The thick, crisp cream coloured pad she saves for writing the most intimate of notes.
“Slightly bigger than mine,” I put forward. “He seems taller, it would make sense perhaps…”
She hands me the folded paper, “Let’s find out, shall we? Go and hand him this note, and we’ll head upstairs.”
With growing curiosity, I do as she says. I cross the room and approach him. He smells clean and masculine when I get close, and I hesitate for a moment. He turns as I open my mouth to speak, and I trip over my words slightly, “This is from my, er… This is for you. From my wife.” And I hand him the note.
He takes it between thumb and forefinger, and leans back on his stool, crossing his legs as he looks me up and down. I feel scrutinised, and feel my cheeks get hot.
He looks down and unfolds the paper, smiles a lop-sided smile and tucks it into the pocket of his jacket. Then he looks me in the eye and licks his lips. “Tell your wife I’d be delighted.”
She’s waiting at the door to lead me to the lift. I had no idea we had a room booked, but she’s confident and calm. As the door to the lift closes, she turns to me. ”His name is Barry, and I’ve decided he’s going to be the first man you have sex with. I’ve started a grindr profile for you, and I’ve been chatting with him for a couple of weeks. He’s fully aware of our situation, your lack of same sex experience and your not-so-secret desire to suck cock.”
“If you don’t want to do this, we will have a wonderful time by ourselves, and Barry will slip away into the night. The choice is absolutely yours.”
My heart races, and she squeezes my hand then pulls me in for a kiss. We’ve discussed and fantasised about this for a long, long time. We both want it, and the tightness of my little cage tells me my body is ready.
“By the way, his cock looks almost identical to yours in the pictures he sent me,” she whispers into my mouth. Then she grabs my balls. “So, what’s it going to be?”
The lift stops at the sixth floor, and she takes my tie in her hand, towing me behind her. She stops at room 619.
“Decision time, my slut. Is this the room you fuck a man for the first time?”
My mouth feels dry, but I nod with conviction. “Yes Miss. Yes please.”
“Good boy,” she taps my cheek playfully, “you won’t regret it, and I’ll be right here the whole time.”
A few minutes later, she’s made herself comfortable on an armchair in the corner. She has a view of the whole room, as well as the full-length mirror that covers the wall next to the bed. She doesn’t want to miss any angle, it seems.
Then there are two sharp raps on the door, and I freeze and look at her. She rests her chin on her hand and reads my mind, “I’ll be right here watching every move, and you can stop it all at any moment. Now don’t keep him waiting too long…”
I nod and stride to the door, stepping back to let him enter. He turns to slide past me face to face, and his scent fills my nostrils again. In that moment I realise it’s going to be planted in my memory for a long, long time. He’s an inch or two taller, a few kilos lighter and to my eyes better looking than myself. I feel self-conscious, but he places a hand on my chest and smiles at me.
The he turns his head and addresses her, “You were right, he’s beautiful.”
Source: reddit.com/r/eroticliterature/comments/109a4u8/first_time_experiences_are_rare_and_should_be
More please, my panties are straining with my cock already