Cross Dressed Damsels

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"But if I had the full apron, and my hands were tied behind my back with the long streamers..."

"Oh. I suppose that would work, Anne."

"I'm sure it would. I'll demonstrate."

I went behind him, pulled his arms back. He didn't resist at all. I wrapped the streamers of the small waist apron around his wrists, tied them, and then made a bow over the knot.

"Try to get free from that, Derek."

He couldn't. As he wriggled his gloved hands the knot tightened.

"It works, Anne. I'm stuck."

"So you are."

I kissed him fiercely. He responded. The kiss went on and on. I was enjoying having a restrained cross-dressed Derek.

"But that isn't exactly how I should be," I said as the kiss ended. "Damsels in distress need more than that."

I went to the settee and picked up a long white scarf. I knotted it in the centre.

"Mouth open," I ordered.

I wasn't sure he would. He did. I gagged him lightly. If he had really wanted to he could have spoken through the gag.

"And..."

I put a deep poke bonnet on his head. It was the wrong period but when I pulled the veil down at the front, catching it in the ribbons around his chin, the gag was invisible.

"Now no one could see that the damsel is gagged. If I add a cape..."

The black cape buttoned down the front. It was knee length so Derek's bound hands were invisible.

"...no one knows that the damsel is restrained."

I was right. The thick veil was almost opaque looking from outside. Derek could see out with slightly blurred vision from inside the bonnet. I asked Derek to walk up and down while I took more pictures. No one could tell from the photos that it was a man inside that costume, nor that he was gagged and bound.

"That hoop petticoat is too large, Derek," I said. "It stretches the skirt and the hoops show as ridges. Please stand still while I get a smaller one."

He stood still while I went into my bedroom. I came back with a shorter hooped petticoat with a slightly smaller diameter.

"OK, Derek, I don't want to undress you and dress you again. I'll try dropping the hoop from inside."

I lifted the skirt and hoop. It was fairly dim under the heavy skirt but I could see enough to reach the ties on the hoop. I was just about to loosen them but I noticed that Derek was erect. The bulge was protruding between the legs of the pantaloons. I reached a hand to stroke the bulge. Above me Derek groaned through his gag.

"You need a reward, Derek," I said loudly, "and I can see what it should be."

I loosened the ties to the pantaloons and let them fall to his ankles. I slid his Y-fronts down before cradling his erection in a hand. I pushed my head upwards before opening my mouth to suck at the tip. Slowly I took more and more into my mouth. In that constricted position I couldn't take it all. Derek didn't seem to mind. In less than half a minute I was swallowing hard.

I wiped his tool clean with his Y-fronts as I pulled them back into position. I let the hooped petticoat fall and crawled out from under the skirt, dragging it with me. I asked Derek to lift a foot at a time as I removed the pantaloons.

Once I was outside the dress I took the cape off, removed the bonnet and gag.

"Did you enjoy that reward, Derek?" I asked unnecessarily.

He was looking at me as if he had won a lottery. He nodded.

It took several minutes for me to undress Derek. The apron ties had locked hard around his wrists. I almost thought I might have to cut them. He dressed himself in his normal clothes before we sat down with a cup of coffee. Somehow I had ended up sitting on Derek's lap, kissing him.

We stopped kissing long enough to drink the luke-warm coffee.

"Anne?" Derek asked. "That was wonderful but it's intended to be YOUR damsel in distress costume."

"Yes. It is. It seemed to work just as well on you, Derek."

"It did, Anne. It did. But YOU haven't been the damsel in distress, have you?"

Did he mean what I hoped he meant? He did. A quarter of an hour later I was buttoned into that dress, wearing elbow length gloves, my wrists restrained with an apron, a gag in my mouth underneath a veiled bonnet and a cape hiding my bondage. I was very warm between my legs and enjoying my predicament as a damsel in distress captured by Derek.

It was wonderful. It turned from wonderful to bliss when Derek burrowed inside the skirt and petticoats to use his tongue. I didn't know he could but he was an expert at arousing me. The heavy material covering him shook as I erupted into a series of shattering orgasms. I was squealing through my gag, wrestling with my bonds because I wanted to press Derek's head deeper, and lost in ecstasy. If what Derek had felt as my captive was anything like what I was experiencing? We had found a great relationship as alternating damsels.

+++

That was three years ago. We have been married for over two years, have become reasonably competent at sewing, and now live in what was Derek's house. One room is dedicated to our costumes. I go to re-enactment events in male costume, as does Derek. A few of our friends know that I take part in battle scenes as a man. Derek is never seen anywhere outside our house dressed in women's clothing. At home he enjoys being the damsel in distress as much as I do. We have a whole range of outfits which fit either of us.

Tomorrow is 1st April. Both of us have a few days off work. We were going to go away but the hotel we were going to has closed for urgent repairs after a flood. We'll be at home. No one will disturb us because our friends and family think we have gone away.

Derek doesn't know yet but I have planned something special for him. Tomorrow morning after breakfast he is going to be the restrained damsel in distress. We have more elaborate scenarios now. He wears breast forms and a female mask that is the front of a hood. I can fit a variety of wigs to the hood. Behind the mask he can be gagged loosely or tightly or left free to speak. As well as having his wrists tied behind his back with apron streamers he could have his gloved wrists restrained in folds of a skirt, or laced into a muff. However his hands are tied he is helpless as a damsel. So am I when it's my turn to be the victim.

Tomorrow? He will be the April Fool because once he is restrained, dressed as a Victorian woman, he is staying like that all day long. I will do everything for him including feeding him and taking him to the toilet. He will be my prisoner as a damsel in distress. I might take his erection in my mouth under his skirt, or I might flip his dress up to cover him from waist to above his head while I ride him.

Derek enjoys being my cross-dressed victim. Of course we agreed safety signals long ago if either of us really gets distressed but we have never needed them. He will willingly surrender to me, just as I will to him. I hope that on the second of April I will be the damsel in distress or we might take it in turns. We have several days for consensual sex playing.

In the morning Derek let me dress him up before restraining his arms. Unusually I had slid pantaloons up his legs. He soon found out that I had sewed the legs together, hobbling him. He could only take tiny steps. I gagged him effectively before fitting the face mask and wig. He couldn't speak, only grunt. Under the mask his eyes opened wide as I told him he was my prisoner for the whole day. I kept him gagged for about a quarter of an hour before I lifted the mask, loosened his gag and let him speak.

"I love you, Anne," He said when he could.

"I know you do, Derek, especially when you are my damsel in distress. I love you. Relax and enjoy today as my April Fool."

By the end of the day both of us were tired. We had nearly reached our record for the number of Derek's ejaculations in a day. We went to sleep wrapped in each other's arms, ready for more days of mutual enjoyment as damsels in distress.

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4 Comments
AnonymousAnonymous3 months ago

Something about a woman participating as a man doing WW2. The only role a woman could participate in doing a WW2 battle is Soviet. The Soviet Union had units made up entirely of women who were used in combat and snipers. Otherwise as Nurses off the field.

DianeRedfernDianeRedfern10 months ago

One of the sweetest and enjoyable stories ever. xoxo, Di

AnonymousAnonymousover 2 years ago

sweet and lovely thank you for a great fantasy

BrendaNWBrendaNWabout 6 years ago
hot and sexy

I would love to be the damsel in distress

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