Caroline 06 Damsel in Distress


Caroline 06: Damsel in Distress

Copyright Oggbashan July 2020

The author asserts the moral right to be identified as the author of this work.

This is a work of fiction. The events described here are imaginary; the settings and characters are fictitious and are not intended to represent specific places or living persons.


Tom and I were on adjacent beds, our heads resting on the laps of Angela and Caroline, unable to move off or to object as they stroked our erections hidden under our confining clothing.

About two weeks ago, shortly after Caroline’s latest work, Cleopatra, had been installed in Jerry’s club, Caroline made an appeal to the club’s members for laddered stockings and tights and any clean used panties. She now had a large collection ready for use by her latest experimental creations.

These, and she had made two simultaneously, were simplified versions of the complex Cleopatra. They were as large, standing nine feet tall and dressed as medieval serving wenches with low cut dresses and prominent cleavages. Their apparent use was as dancing partners. A man had to approach one, bow, and then ask for a dance. She would open her arms and hug the man, almost smothering him in her cleavage, as they executed a basic waltz. She had to lead because the man couldn’t see beyond her. In fact with his head held tightly in her cleavage he couldn’t see at all, but as with all Caroline’s recent productions, despite apparently being trapped between her breasts he could breathe freely. But the air he was breathing was slightly scented and had a relaxing and soporific effect.

At the end of the dance, the wench wouldn’t let her partner go. She would use some of the donated stockings and pantyhose to secure his legs together at ankles, knees and thighs before tying his hands and arms to his sides. When he was completely immobile she would strap breast forms to his chest and stuff his mouth with a pair of panties, tying them in place with pantyhose wrapped around his head.

Then she would pull a tight floor length dress over his head and down to his feet. It had short sleeves that flapped uselessly because his arms were already secured by pantyhose and were now tightly wrapped in the dress. She would put a hood on his head. The hood had a basic female face and shoulder-length blonde hair but over the mouth the woman’s face was apparently gagged with a scarf. Her last actions were to wrap rope around the dress below the bust, around the waist and at the knees.

Her former dance partner now looked like a damsel in distress, gagged and tied with rope. But the gag and rope weren’t the real restraints hidden under the dress and hood. She would take her victim and put him down on a bed where he might struggle but be totally unable to be more than a cruelly restrained damsel in distress. Unlike Cleopatra she wasn’t programmed to release her victim. He would stay on that bed until someone took pity on him. The safety ring would work at any point until he was put on the bed. Then it was too late. Anyone who did try to extricate him would have a hard time removing the clinging dress and untying the knots in the stockings and pantyhose that had locked as the victim struggled.

That was how the dancing partners were supposed to work. But before they could, Tom and I had to be the test pilots for all the various stages.

Caroline wanted me to try the first stage, the dancing. She had to adjust straightaway. I bowed and asked for a dance — no reaction at all. The microphone that would detect my request wasn’t connected. Once that was plugged in, I tried again. The wench hauled me against her bust and into her cleavage as we started to dance. Another disaster. Caroline had put too much of the soporific gas into the air supply. In the first minute I slumped in my partner’s arms as I slipped into unconsciousness. She held me upright even as my feet just dragged across the floor.

It took me half an hour to recover before I tried again. I don’t know Muğla Escort whether it was the effect of the previous dose or whether Caroline hadn’t reduced the amount enough. This time I lasted three minutes before collapse. For the third time Caroline put no gas in at all. I survived the five minutes before the wench just stopped. Caroline had to press a switch before the wench would release me from the strong hug into her cleavage.

Angela worked on the programming for the safety ring and used Tom for that series of tests. The safety ring worked for the first four minutes of the dance but during the last minute the wench would just stop, keeping Tom trapped. It took three more tries, and three times Tom had his head buried in the wench’s cleavage before Angela had successfully modified that part of the program.

Because Caroline was making two copies of the serving wenches, Tom and I had to repeat our tests twice before both devices were declared satisfactory for that stage of their operation.

The next step was to be secured with stockings and pantyhose. The first time I tried, the wench tightened my bonds too much. Yes, I was secured and helpless, but the ties were cutting into me painfully. They couldn’t be unknotted. Caroline had to cut me loose with a knife. She adjusted the settings.

This time they were too loose. I could wriggle my hands out and push down the bonds around my legs. I might have been able to push the pantyhose around my waist and chest upwards but not off because my head was still held in the wench’s cleavage.

It took two more attempts until the bonds secured me helpless but were not too tight. Meanwhile Angela was using Tom to test a new setting of soporific gas. Eventually he was able to say that although he felt slightly sleepy, he also seemed to be enjoying the massive cleavage of a real woman, not one of Caroline’s creations.

The next operation was the gag with panties. Caroline had changed the idea slightly. The wench would stop and hold out a hand for about twenty seconds. During that time, the victim’s girlfriend could put her own panties into the wench’s hand to be used to gag her boyfriend. If the girlfriend knew that was going to happen, she had the five minutes of the dance, and the twenty seconds to take off her own panties for the wench to use. At the end of the twenty seconds, if no panties had been put in the outstretched hand, the wench would use one of the donated pairs of panties.

Tom and I were gagged several times with the donated panties and at least twice each with Angela’s panties for Tom and Caroline’s for me. Both of us found the real woman’s panties far more arousing than the generic ones. They were warm, damp and had our girlfriend’s perfume on them. Once those panties had been secured with more pantyhose we couldn’t speak.

With the female mask or hood over our heads we could breathe and see through the painted eyes. The tight dress reinforced our restraint and the breast forms made our bodies look feminine. The rope added as a final touch was more symbolic than a real constraint. They made us look like damsels in distress but the bonds hidden under the tight dress really made us helpless.

Caroline and Angela teased us. Whenever we were put on the bed they would remove the hood, untie the pantyhose and pull out the panties but leave us restrained. They would pull our head on to a lap and smother us with breasts while checking through our bondage for how erect we were. Caroline knew how frustrated I was. It was an hour before she dragged me into our bedroom for some unrestrained sex. This time, having been the wench’s victim for so long, I wanted to be in control. Caroline squealed as I thrust into her hard and often. It took a long time, for me, before I was close to ejaculation. Both of us enjoyed that.

Perhaps that is why I ended up as the wench’s victim more often than was strictly necessary. Caroline knew I would want revenge by making love to her until I exhausted Muğla Escort Bayan myself.


Caroline wasn’t wholly happy with her two wenches. Yes, the man was turned into a damsel in distress but the hood over his head concealed his embarrassment. She wanted the victim to be in an embarrassing situation and to be seen to be embarrassed. She decided to change one of the wenches into a many-armed Hindu goddess that she called Durga.

The start would be them same — ask Durga for a dance, But the victim, hauled into Durga’s cleavage, would be given a large dose of the soporific gas. Durga’s victims would remain conscious for at most a minute. Once they were unconscious, Durga’s many arms would strip him down to his boxers or y-fronts. Durga would pull hold-up stockings up his legs, fit a bra filled with large and heavy breast forms, pull a knee-length full slip down his body, before adding a satin blouse and a below-knee pencil skirt.

Durga would then use rope to tie his legs above his knees, concealed by the skirt, around his ankles, around his waist securing the wrists, and finally below the bust line to tie the elbows.

Two of Durga’s hands would hold his head still, two more would be posed to restrain him if he woke up which very few did, and Durga would assess whether he needed a shave. If so, that would be done carefully with an electric razor. Shaved or not, his face would be anointed with moisturiser then foundation and blusher. Lipstick would be applied to his lips, eye shadow and eyebrow liner added and then a knotted scarf would be forced between his lips and knotted at the back of his head. The knotted scarf would not be an effective gag. He could still breathe around it and make some sounds, but his lipstick-covered lips would be obvious. The last image change would be to put a short but obviously feminine wig on his head, secured with double-sided tape.

Durga would pick the bound man up and place him in an armchair where he would be secured by rope around his ankles to the chair’s legs, and around his chest to lash him to the chair back. White high-heeled shoes would be strapped to his feet. A full length mirror would be stood in front of the chair.

When the victim came to, he would see himself as a damsel in distress, a feminised version of himself, bound and gagged in women’s clothing and wearing makeup. Although he might be able to make a sound, or perhaps even say some understandable words, he would be unable to escape from that bondage. Caroline made it possible for the girlfriend, if she had clothes of the right size, to provide her clothes for the bondage. Caroline had to obtain the white high-heeled shoes in quantity from a specialised theatrical costumier because most men’s feet were too large for their girlfriend’s shoes.

It took a long time for Durga to be tested and adjusted up to the stage when the man was placed on a bench and stripped. Caroline didn’t use any soporific gas for these tests. I was completely aware and able to object if something went wrong. The stripping was initially the most complex operation because the victim could be wearing a variety of clothes and Durga had to act differently depending on how he was dressed. I might wear a sweater, shirt and trousers, or a T-shirt and jeans. My shoes were either formal lace-ups or Velcro secured trainers. Caroline and Angela were often swearing as they tried to get the programming and actions to fit the clothing.

A few times my boxers came off with my trousers. It was a week and many boring tests before they were satisfied up to that stage.

Dressing the man in women’s clothes was also complex. Durga had to assess the man’s size and select which clothes she had that were suitable. For the first attempt Caroline provided some clothes that she had worn when she was in the early stages of pregnancy and larger than she is now. The satin blouse was tight, straining against the breast forms but acceptable. The pencil skirt was too tight around Escort Muğla my legs. Durga had problems tying the rope over my knees because the skirt was already forcing my thighs together. When she closed the zip the waistband was cutting in to me. Caroline had to change that skirt for a slightly larger one from a charity shop.

Durga’s hands as she put stockings on my legs and dressed me were surprisingly gentle. I could imagine that she was my girlfriend dressing me up as part of bedroom play. But when she added the ropes, I was helplessly restrained. They were tight, not excessively so after a few adjustments, but inescapable.

Caroline and Angela tested Durga’s reaction to the safety ring at all stages up to when I was fully dressed and tied up. Initially there were a few blank spots when Durga would not react but soon they were satisfied that Durga would stop and release her victim at any stage up to the finished tying — not that they expected the victim to be able to press the ring during that time as he would be unconscious — but just in case he wasn’t, the ring would set him free.

Caroline and Angela could have made Durga give a wet shave but they thought no one would trust a robot to do that. Durga had to distinguish between stubble and a beard with or without moustache. Caroline asked me not to shave for 24 hours before the test. Durga’s shave was gentle, professional and very effective.

I felt gently pampered as she applied the moisturiser, foundation and other make-up. I was surprised to watch the transformation in the mirror. Once the wig was added I barely recognised myself. I was still obviously male, but dressed and made-up as a woman. Once the wig was fitted I doubt anyone would have recognised me. Caroline had provided one of her scarves for me to be gagged with. I was aware of her scent as it was tightened around my head.

Caroline asked me to try to speak. She could understand some words but not a coherent sentence.

Finally Durga tied me to the armchair before moving away. As Caroline had hoped I was embarrassed to be tied up as a damsel in distress. I ought to be used to it, but all the testing had been recorded on video, showing the transformation from Nick to whom? Nicola, perhaps?

After more tests to make sure the safety ring worked, Caroline and Angela untied me from the chair, removed the ropes around my ankles and legs and helped me to walk in to the bedroom where they put me down on the bed. My arms were still tied. The scarf gag was still in my mouth. Caroline took the skirt off, flipped up the slip, pulled down my boxers and rode my erection despite my ineffectual protests around the gag.

Caroline kept me tied and dressed as Nicola for the rest of the day, only releasing me in the evening. I went into the bathroom and removed the make-up. When I got back to the bedroom, I picked Caroline up, threw her on the bed and thrust into her again and again to show that I was Nick, not Nicola. She was squealing in enjoyment as I tried to take my revenge. As revenge it was unsatisfactory. Caroline was enjoying it too much. Because she was, so was I.

Once installed in the club, the wench and Durga were popular. Unlike Cleopatra, there were no unwilling or unsuspecting victims. They had to start the process by asking for a dance. If they didn’t, they were safe. Many girlfriends persuaded their boyfriends to ask, mainly Durga, for a dance. They liked the idea that their man could be feminised, tied up in their girlfriends clothes — if she had any large enough — and left for the girlfriend to decide what to do with their new girlfriend. Many men left the club still tied and dressed as a woman. As before, despite the extensive testing that I and Tom had done for the operation of the safety ring, very few club members actually wore one.

The wench and Durga had required many weeks’ of testing. Tom and I were rewarded for our endurance but often we had been unable to resume being our male selves until our girlfriends relented. They seemed to like making love to damsels in distress.

I am writhing on the bed, dressed and made-up as Nicola, while Caroline jumps on me again. I wonder what creation she will think of next. Whatever it is, I know Tom and I will be its test victims.