DIY Was Never Like This!

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Cal's reward is cross-dressing.
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Two weeks ago, I helped out a friend of a friend one Saturday morning. I was amazed to find myself involved in some fantastic and mind-blowing sexual activities that rather got in the way of completing the work I was expected to do. At the end of the day Fen, the lady of the house, had found herself in submission to her stepdaughter, which was a complete role reversal. She made it clear that when I return she would take absolute control, and that was going to include me!

I was greeted at the door by a very bright and smiling Fen, a glimmer already apparent in her eyes. Lucy, her stepdaughter, was nowhere to be seen and after the normal pleasantries and a cup of tea, I was set to work. There came a warning when Fen left the room - I was given only a couple of hours to complete the work then they would be coming to take over the rest of the day. I started and was soon working my way through the minor repairs to shelves, gutters and door locks. Time passes quickly doing this and it was with a start that I realised I was both thirsty and hungry and that almost 2 hours had passed. I barely had time to tidy up before I heard voices coming back into the house and Fen and Lucy walked into the room.

Lucy, a feisty 19 year old, was subdued and clearly back under Fen's control. What was most noticeable this morning was how similar in dress they were. Both seemed quite demure in their mid-thigh length skirts, loose fitting blouses, and low-heeled shoes. The only thing that set my mind thinking was the shiny, smooth nylon of their tights or stockings. Lucy, as before, was clearly deferring to Fen as they settled down in the lounge and Fen got straight into her role.

"I will be in charge of how we spend the rest of the day. We will be going out for some food, though what you will be wearing and whether or not you will enjoy it is yet to be sorted. After the planning you clearly both did last time I am going to make sure you are suitably chastised. However, I am going to make it more interesting."

Fen then turned to me and continued, "Cal, you will now be blindfolded. Lucy and I will either touch you, or ask you to touch us. Of course, it will only be a small part of us, and any attempt to move your hand further than we state will result in you losing. You see, what you have to do to win is simple - who is it? If you guess right, Lucy faces an extra forfeit. If you guess incorrectly, Lucy chooses an item of clothing. We will allow you to have eight of these pleasurable activities, and there are five forfeits available. If Lucy has not been allocated them all you will do the remainder. However, for every time you lose Lucy will specify an item of clothing, clothing you will wear to the meal. Assuming Lucy will not be choosing to keep you covered up I will select any remainder to ensure you are at least decent. Clear? Good, Lucy, blindfold please."

As Lucy placed me into darkness I realised why they were so similarly dressed - I had no chance to guess based on what they were wearing! Before I had time to think how this would work a mouth placed itself over mine and a tongue snaked its way between my lips. For a long while we kissed quite passionately, lips mashing together and tongues sliding around and fighting for space. Just as suddenly the mouth left me and I realised I hadn't thought about the challenge! Last time I had a passionate kiss with Lucy - was this the same?

"Well, who was teasing you," asked Fen. I thought it seemed an experienced mouth, one that knew how to arouse, so I had to go with Fen.

"Excellent, absolutely right, I do hope you enjoyed it," came the sultry reply. "Lucy, select one of the tasks and read it out."

"You will be bent over the back of a chair with your hands tied to the arms and spanked 25 times with ... with a ruler... on your bare cheeks."

"Good. Now a last reminder, no touching what you haven't been given permission to," and with that my hand was placed on to a calf. The nylon was so smooth, I slid my hand up and down the back of the calf, being careful not to reach too high or low. It felt delightfully slim and smooth, toned muscles under the shiny, sleek nylon and I was just getting into this when again the leg moved away.

"And your guess is?" came Fen's voice. She was clearly enjoying this, and by the rise in my trousers so was I.

It felt slim, I was sure Lucy was slimmer than her older stepmother so I guessed again, "Lucy."

"Oh dear Lucy, correct again, this is fun. Select another task."

Lucy did so and read out, "The remote control butterfly will be worn at all times when Fen asks, and of course she will have the control."

Before I had time to think about what this meant my hand was placed on a taut bum. The owner was bent over and I was allowed to roam my hand around the two firm cheeks. But who's? The material was no help, just a simple cotton skirt from what I had seen and could feel. The cheeks felt great, and there was the faintest hint of a panty line. I was again enjoying the sensation when they moved away and the familiar question from Fen. I was convinced this time it would be Fen, she would not allow Lucy all the fun so I guessed Fen.

"Oh dear, this time you are wrong, Lucy will have the joy of selecting at least one item for you to wear later."

My hand was then taken and placed on what felt like a very shapely ankle. I slid my fingers slowly over the slinky nylon covering the fine shape, and moved up and down to the limit of what I thought I could go. Roaming around both the inner and outer parts, sliding on to the top of the foot and up towards the start of the calf, all the time the nylon feeling sexy beneath my finger tips. My fingers were guided towards the foot and I was allowed to fondle the toes encased in their nylon sheath before my hand was taken away. This was a slim, young foot was my thought and I announced, "Lucy", very confidently. Lucy gave a small intake of breath as Fen confirmed I was right and she selected another task to be done later.

"Your clothing will be filled with cream or other foodstuffs before they are put back on. You will wear them to serve Fen until the cream runs out and Fen orders you to clean up." Lucy's tone of voice changed as she read this out, clearly getting 'messy' was not among her favourite occupations!

The game continued, four items down, four to go I thought as my hand was lifted yet again and placed on a blouse covered breast. It felt full and heavy, wonderful to touch with no visual stimulation to distract me. Rolling an already growing nipple between my fingers through the silky material of blouse and bra I received a warning tap on the hand preventing me from arousing whoever it was any further. I held the whole breast in one hand, lifting it and sliding my palm around the fullness of it, knowing this could only be Fen. Even the lace of the cup through the fine material couldn't detract from a very prominent and firm breast so when my hand was removed I again announced very confidently, "Fen", and waited to find out what Lucy would be doing next.

"Unfortunately not, can you not remember Lucy from your pleasures last time? Shame on you, I am sure she will select your second item with care," was Fen's laughing response.

Dam, I thought, better pay more attention now; this could be embarrassing if I lose too many more.

I heard the sound of material against nylon and then felt my hand picked up and placed on a nylon-clad thigh. The sound had been a skirt being raised and I was starting to get very aroused as I teased my way to the top of a stocking and found smooth bare flesh beyond. I played around the top of the stocking, teasing and catching the straps from the suspender belt whoever it was wearing. The flesh was warm and smooth, feeling firm to my gentle touch, but I really had no idea. I was not allowed to roam too far so I didn't know whether it was the slim thighs of Lucy or the firm but rounder thigh of Fen. As my hand was taken away, my cock was raging as I thought of how close I had been to somebody's warm and no doubt wet pussy. I had to guess, and chose Lucy.

"Well, things are getting equal now, another item for her to choose from, but I suppose I didn't really allow you chance to get to know my thighs very well last week did I? Now, we must adjust your position for a moment. Lie down with your hands at your side."

Two sets of hands helped me lie down flat on the floor. A cushion was placed under my head for a little comfort (or so I thought) and the hands went away. I could hear slight movements, clothing rustling and I felt someone approach. I heard rather than felt them stand above me and suddenly I felt the smooth nylon of stocking tops again, but this time on my cheeks as whoever it was knelt down. A skirt was lifted over my head, the light, silky material resting on my forehead as the two thighs settled either side of my head. I could smell the arousal of a wet pussy getting closer before it was rested onto my face. My lips were pressed against two engorged, dripping lips as whoever it was rubbed them across my face.

The taste was extraordinary, juices running freely as they used my face for pleasure. I stuck out my tongue and slid it into the folds of flesh, tasting again the honey that was running free. I had no thoughts as to who this was, I didn't care! I could feel my cock straining even more at the thought of this astonishing situation - blindfolded and lying flat on my back with a gorgeous woman on top using my face for fun and having no control over what was happening. I tried to use my tongue to arouse her even more, perhaps to get some indication of who it was from a noise. The pubis was slid over my mouth, hairless and smooth - and then it was taken away and whoever it was stood up. It had to be Fen, she wouldn't let Lucy enjoy a sensation like that?

"Well, we are waiting, and you really wouldn't like to keep me waiting long!"

I licked the remaining juices slowly from my lips and said, "Fen," and was rewarded with a squeal from Lucy.

"Indeed correct, you were getting into it, as was I. We might return to that position later but in the meantime Lucy, read out the next punishment."

"Lucy - you will wear nipple rings, linked by string with a weight suspended from the middle. You will be taken .. ah.. from behind in whatever position Fen chooses but with nothing worn above the waist." As she read this out Lucy's voice trembled at the thought of it, though I couldn't work out whether this was in anticipation or dread. I was trying to picture the scene when Fen reminded me there was one more to go.

"This one is crucial to you as if you get it wrong Lucy will be choosing one more item AND you will be subject to the last punishment. So, think very carefully."

I felt a pair of hands undoing my belt and unzipping. I was asked to lift my hips, did so and my chinos were slid from me, taking my boxers with them. A rush of cooler air came around my hot and very aroused cock as it sprang free. Someone started to blow gently on the end of my cock before a tongue licked lightly at the end, perhaps taking in the pre-cum that would no doubt be leaking out by now. Gently a pair of lips wrapped themselves around the head of my cock and took it inside a warm, soft mouth. The lips continued to slide down my shaft, more of my cock going into the waiting mouth as the tongue licked and teased the side of my erect flesh. I was absolutely rock hard, my raging erection being given the full treatment by one of two sexy women, who I couldn't even see or touch. The mouth stopped as my cock hit the back of the throat, and whoever it was paused before slowly continuing and easing my cock into her throat. I was so close to cumming, a deep throat experience in the dark. Finally the lips nestled into my pubic area as the whole of my cock was now swallowed by the fantastic person on top of me. Without too much warning the mouth slowly slid back off, tongue flicking away at the sides and head of my cock as it made the return journey and was finally left free, hard, erect and throbbing, desperate for relief. I was breathing hard and had completely forgotten what this was about, concentrating as I was on the amazing sensations. Fen brought me back to earth.

"You are keeping us waiting again, this does not bode well for you later. Who's mouth has just been giving you the best sensation you have had for a while?"

Quick thinking, Lucy did a very good job last time on accommodating my cock, so it really must be her. But would Fen have done this knowing I would think it Lucy? Could Fen also completely swallow a cock like this? I decided it was a bluff, and guessed, "Lucy," confident Fen would not have this skill. How wrong can you be!

Fen seemed to enjoy this, as there was sense of anticipation as she reeled out my fate.

"Lucy told me about her exploits as I asked her to describe in every last detail what you had been up to last time, so I thought I would have a go myself. Its quite a feat, and clearly effective, but you now have Lucy selecting four items for your dinner date. In addition, of course, the punishment. The punishment might be something to test your resolve. I had a different one in mind for each of you and this is yours. I will instruct Lucy to decide what you will wear for this task but I do not expect it to contain any of your own clothing. She will 'help' you to your orgasm, but with a difference. You will cum onto your own face and into your mouth, swallow some of it and share the rest with Lucy."

I gasped at that as I really hadn't seen that one coming. I was about to query this when I realised two things - querying it would end the day straight away, and I was looking forward to such a lot, and that the thought of this last punishment actually had me aroused. I pushed the latter thought aside as Fen sent Lucy to collect items she wanted me to wear.

Lucy returned quite quickly, and I suspected she had been hoping or even preparing for this. In the interim Fen had removed my blindfold and allowed me to sit back up. I had not been able to hide my growing erection, which was still on show when Lucy returned. She handed Fen the four items she had selected which Fen held up and then passed to me one by one. The first was a silky stocking, black and shiny, opaque and very sensuous. The thought of wearing these was intriguing and my cock twitched when it was handed to me. The next was not another stocking but a black, calf length heeled boot in soft leather. I drew my breath in - how would I get this on? How would I hide the fact that I am wearing it, as we are going into a very public place? Still, I thought these four items were not too bad and I could at least wear something on top. I was about to discover that Lucy wasn't letting me off so easily.

Fen smiled and handed me the next item and I was surprised it wasn't the matching stocking or boot, but a black, silk camisole top. It shone as only pure silk can and felt sexy to the touch, but how was I going to wear the first two? Before I could consider this further the last item was handed over, and it was something I had seen before - the black latex knickers Lucy had been wearing when we first started this game the last time we met. This did not make sense, how could I wear such items.

"Are you sure? Surely I can't have just these, it doesn't make sense," I started to protest but stopped when I saw the gleam in Fen's eye.

"You now have an extra punishment for speaking out of turn and questioning when you should not be doing. So, it would be a shame for you not to experience the full sensual nature of nylon stockings, so we will have to make your legs hairless. I think the depilatory cream will work just fine."

Fen clearly noticed the look of astonishment appearing on my face, and raised her eyebrows as if waiting for me to answer back again. I bit my tongue and contemplated my fate. As I did so I realised Fen had used the plural - stockings. I carefully phrased a question as I didn't want to get further into trouble, and I was still rather enjoying the whole day. "You mentioned stockings, but I can only see one. Have you decided what else I am to wear, as you said you would be doing?"

"You noticed, and yes, I have. Lucy, fetch the other stocking, boot and a suspender belt that will fit Cal, we cannot have the stockings showing as they fall around his ankles. Cal, take the remainder of your clothes off as we are going to make your legs so smooth you will really appreciate the feelings we are about to give you."

The next 20 minutes were surreal, but incredibly arousing, and my cock was standing erect for much of the time. I felt I wanted to go along with the game so followed Fen to the shower where she produced the appropriate cream. Lucy was instructed to wet my legs and the cream was sprayed on from thigh top to ankle. I must have looked an odd sight at first as the cream got to work but when Lucy set the shower going and cleaned off my legs the hairs went with the cream and the skin was bare. What an odd but amazingly erotic sensation! The air moving around my bare flesh seemed much more apparent, I felt extremely naked. Lucy reached forward and started to rub some moisturising cream into my clean 'shaven' skin and my cock sprung further into life again. The sight of a slim, attractive young woman bent down applying cream and rubbing my legs, and the silky sensations that go with it were almost too much. I was already close to orgasm, but I just got this feeling I would not be allowed to cum for some time yet.

Lucy completed the smoothing of my legs and Fen handed me the clothes I had to wear for lunch. Fen suggested I started with the suspender belt and even wrapping this around my waist felt distinctly kinky and daring. With the straps hanging ready, I was handed the first stocking. Rolling it slowly up my right leg the sensation was quite unlike anything I had experienced before. The soft, shiny lycra and nylon hugged my flesh and with the smooth skin, the sensation was electric. I reached the top of my thigh and clipped the stocking into place, relishing the feel of it on my inner thigh, close to my balls. Wow, my cock was standing proud and clearly demonstrating how much this was exciting me. The second stocking was as gloriously smooth as the first and I was really beginning to get into this. I was almost oblivious to the others until Fen said, "Lucy, whilst Cal finishes you should go and get ready. Sheath dress, hold-ups, boots and butterfly, now."

Lucy left and I was encouraged to continue. Fen handed me the camisole top, which slid over my head and settled into place - now that really felt odd. The garment was very feminine and the silk slid over my flesh causing ripples of excitement and a tingle in my tight balls. Fen reached forward and teased my nipple through the silk and I gasped at the electric sensation. She then handed me the latex knickers and I stood shakily on each leg as I slipped them on. Just moving them up over my stockings felt so erotic but settling their tight confines around my raging erection was again almost too much. I had difficulty getting the purple head of my cock inside, but managed to pull the shiny fabric over the end. Fen handed me my own trousers and suggested I put them, and my shirt, on before I tried the boots. As I did this Lucy returned to the room... and I stared in disbelief at what Fen expected her to go out in.

Lucy was wearing a black dress that was so clingy, so sheer that it showed off every curve of her lithe young body. Her nipples and aureole were clearly aroused and visible, aroused and erect. The outline of her stocking tops were showing, clearly indicating these hold-ups were all the clothing she had on - there appeared to be no other lines. The hem of her dress ended midway between thigh and knee, so a careful movement was needed. To cap the outfit she wore high heeled leather boots, shiny and black and at least 4" of heel to make her slim frame seem ever more lissom. I was instructed to put my on boots on, and was amazed that they fitted. My toes made it to the end and I zipped each boot up carefully, not wanting to catch my stocking. I stood up and allowed my trousers to fall back into place, and was relieved to see that whilst they were clearly visible, they could pass for cowboy boots at a pinch. I was so aroused I knew I would be leaking inside the latex pants, but when Fen waved a remote control under my nose and then turned it on I knew I had the easy bit. The butterfly I later found out was strapped around Lucy's waist and held in place by thin, clear rubber straps over her bare mound, focussing right on her clit. The remote controlled the vibrating speed and intensity of it, and was already clearly causing Lucy some pleasure as she moaned and closed her eyes when Fen hit the button.