Hen Night Captive

I knew you were the one I was looking for the moment I saw you in the club.

You looked ill at ease as you danced with your friends while dressed in what could only have been stag night attire. Some people just don't feel comfortable in drag, I suppose.

I danced up to you and looked you in the eye before leaning in to talk into your ear.

"Snap," I said, just audible above the sound of the music.

You looked confused, so I gestured to your dress, then to mine. They weren't identical, but they were close enough. Leopard-print mini-dresses in stretch satin with see-through black panels from bust to neckline. Mine had a lace panel with cap sleeves while yours had a mesh one with long sleeves, but neither scored any points for modesty.

I'm a big woman, tall and broad-shouldered, and I wasn't surprised when you took my invitation to compare our dresses as a chance to stare at my chest. I wagged my finger at you. Naughty boy.

I took your hand and led you away from the group so I could talk to you somewhere quieter. I ushered you into an empty booth and put down the two bottles of alcopops I had in my hand.

I clinked my bottle against yours and you took a sip. This was going to be easy, I thought.

I let you do the talking. You chattered nervously about why you were wearing the dress, as if you needed somehow to justify it. It was your friend's stag do, of course, and you had met the rest of the men at the best man's house before coming out. You were a stranger to the city and didn't know the best man, but learnt quickly that he was a cocksure type, a medical graduate who knew the groom through their local rugby club. He explained that there were rules. The groom was to be in drag and everyone else had to back him up on his "last night of freedom".

The best man's girlfriend, a forthright woman with a fondness for leopard print herself, distributed the clothes. She sized you up carefully before handing you your dress and a piece of shiny black underwear that looked at first like cycling shorts. She was particular about you wearing them, and sent you back to the bathroom when you reappeared with only your boxer shorts beneath the dress.

"See how much better it is now?" she asked when you reappeared. She lifted the hem of the dress to demonstrate how the underwear, with its deep lace trim around the leg holes, better protected your decency. She said that she had bought most of the clothes from a charity shop, but you wondered from the possessive way she adjusted your new outfit whether she had chosen yours from her own wardrobe.

I told you that you looked divine and that you would fit in perfectly with the hen party I was with tonight. You glanced anxiously towards the dance floor, explaining that you didn't want to lose track of your friends because you didn't know the way back to the best man's house. Your phone, you said, was in a bag with everyone else's because your dress had no pockets.

"Now you know what it's like to be a woman," I said, thinking that you had a lot more to learn. Bit by bit I slid closer to you, intent on your chatter, pressing you further into the booth.

I ignored your hints that you wanted to leave. Even when you said so outright I refused unless you agreed to a kiss. I kept you in my embrace for several minutes, stroking your back and bottom through the soft material of your dress and placing your hands upon mine.

By the time you escaped your friends were gone. I had seen them go minutes earlier but I let you search for them for a while before offering to help.

When we had investigated every corner I told you that my fellow hens had left too, but you could come back with me to the bride's house. I needed someone to walk me there anyway, I said.

You got plenty of catcalls on the way, which I encouraged, and you were nicely shy by the time we reached my friend's front door.

It opened with an enthusiastic greeting from the hen party, who were in their element inside. Helen, still wearing her bridal veil and crown, escorted you into the sitting room with the playful introduction: "The entertainment has arrived."

With a chorus of cheers and whistles you were enveloped into the group. We drank together and resumed a game of spin the bottle. After a few more drinks you began to laugh with us. "Truth or dare," I said to Helen when the bottle pointed at her. "Which one of us would you most like to fuck?"

"I can't choose!" she declared, and the girls chanted, "Dare, dare, dare..." You did too. I announced that Helen's forfeit was to wear an item of my choice from the sex toys we had unwrapped earlier from a naughty lucky dip. I selected a strap-on dildo, pink and glittery, which Helen allowed me to fasten onto her.

Helen spun the bottle this time and this time the winner was unquestionably you. "Alright," she said. "Which one of us would you like to be fucked by?"

You tried to deflect the question, leading to squeals of delight as Helen prepared the dare. "On your hands and knees then, darling," she said. "What do you think, girls? A little light spanking? Or something more... generous?"

You had been tugging your dress down all evening to hide your knickers, but there was no concealing them as you gingerly got on all fours to take your punishment with good grace. Helen slipped her fingertips underneath the hem of your skirt and pushed it so that it rode up to your waist. "Dare, dare, dare..." the women called. I bent over to hold down your wrists, playfully wiggling my chest in your face. Others, out of your view, braced your ankles.

Helen gently teased down your knickers and pressed on the small of your back so that you presented your bottom to her.

You don't know who it was who squirted something wet and cool onto your bottom or who began kneading it into you, but this was when you started to panic. The chanting of "dare, dare, dare" drowned out any protest from you as Helen eased the tip of her strap-on inside. It continued as she worked her way slowly deeper.

The only thing you could hear over the noise was my voice by your ear congratulating you on becoming one of the girls. "I knew you could do it," I told you. "I knew as soon as I saw you, you'd be perfect for us."

The chanting subsided and was replaced by chatter. "I can't believe you actually did it," Helen said to me. "Someone look at his face. Is he enjoying it?"

"Not yet," I said. "Maybe if you go deeper?"

You hadn't yet learnt to let go, but muscle relaxants in the lubricant were starting to loosen you up. You could feel stretching and sliding as your resistance faded. Helen slipped further inside and smiled. "Thank you," she said, and kissed me while pushing steadily into you till the dildo was buried to its base.

She rocked you gently, withdrawing only slightly at first before pushing back in. We heard your first little sigh. It was so beautiful. We wanted more.

Helen grew bolder, increasing the length and speed of her thrusts while you obliged her with feverish groans.

Carrie, the maid of honour, asked to have a turn. Her strap-on looked even bigger. Helen conceded that it was only fair that we should all have a go. One by one we broke you in till it was my turn, for which we laid you on your back and teased your cock to attention with caresses. You felt their lips around you as their heads bobbed. Your cries, which had turned to whimpers, rose again in volume and pitch until you could take no more. The spasms overtook you and we marvelled at your total surrender to pleasure.

As your climax subsided we stared at our guilty secret. What should we do with you now? Some wondered whether to send you back out into the street. Helen offered me the choice. "I think I'll keep him," I said.