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Oh my God! My life was changing at a breathtaking speed. Yesterday, there had been two momentous upheavals. The first was that I had handed in the keys to my own flat and taken up residence in Laura’s, sleeping for the first time on an airbed alongside her. This arrangement had its upsides—for a start, she had made a point of getting undressed for bed in front of me. When it suits her, she has no modesty. Obviously, she wouldn’t approve of me staring at her as she stripped off, but plenty of opportunities had presented themselves for furtive glances which had got me excited.
My penis, as always, of course, misunderstood the signs, and assumed it would soon be called upon to have with her. Persuading it that it was mistaken, and needed to return to his shrivelled state, was easier said than done, meaning I was lying awake long after she had drifted off to sleep.
But I gained some solace in listening to her gentle breathing, and inhaling her sweet perfume. I felt privileged to be in the same room as her, but I conceded that not many men would want the sleeping arrangement that had been imposed on me.
I mentioned there was a second upheaval yesterday. Laura had decided that if I was sharing her flat then I needed to wear clothes that were more “uni”. She justified this by saying that her landlord would tolerate a girl sharing with her but drew a line at boys. Moreover, she was going to buy me clothes that she considered would deceive her landlord into thinking there were two girls—uni clothes are what she called them, but it terrified me to wonder what she would purchase, as she clearly gets a kick from humiliating me.
Why do I put up with this, you may ask? It’s because I’m infatuated with her and almost everything she does, no matter how humiliating, turns me on in some way. Admittedly, she goes further than I would often wish, but I have to trust that she is not going to put me in mortal danger.
oooOOooo
I can’t say I got much restful sleep on that first night, and I was awake, up, showered and dressed before Laura. Fearing she might oversleep, and be late for lectures, I made her a cup of coffee and slice of toast and took it through to her.
“Oh, thank you, sweetie,” she said, through halfopened eyes. “I slept like a log, reassured you were close by, poppet. Did you sleep okay?”
“My first night was a little difficult, Miss, but I’m sure I will sleep better tonight,” I replied, not wanting to complain.
She gave me a coy smile, saying, “Who knows, I might have other ideas for tonight.”
My penis twitched on hearing that. She pushed back her duvet, revealing her bare breasts, uncontained by a bra or a nightie.
I was a little slow to avert my eyes. “Do you like what you see, poppet?” she asked.
“Yes, Miss,” I replied, feeling I couldn’t deny that I did.
I knew she could take offence on the blink of an eyelid but instead she said, “If you do it gently, you may suck my nipples, sweetie, while I eat my brekkie.”
Not for the first time, I was taken aback by her invitation, but I didn’t need asking twice. Being careful not to fall victim to hot coffee or toast crumbs, I manoeuvred myself and carefully encompassed a nipple with my lips, while using my tongue to stimulate it. As I did so, I felt it hardening—my penis as well—as signs that we were both being turned on.
I would have loved to have slid my arm down the bed to her crevasse and toyed with it using my fingers. I was certain she would be wet, and I imagined she would enjoy me stimulating her pussy along with her nipples, but I had learnt the hard way that if she wanted me to touch her with my fingers, then she would have to take the initiative.
As I caressed her breasts, I knew she was becoming more aroused. So much so that the chewing of toast and the sipping of coffee had come to a halt. It seemed that things might progress further but then, suddenly, she yelled, “Oh, hell! Look at the time. We need to stop!”
And that was it. Our game was over. She rushed through to the bathroom to grab a shower, while I wondered if the precum from my willy had penetrated through the satin of my panties and marked my trousers. I was relieved to see they were all right.
Showered and dressed, we drove off to university, she for a lecture and me for the library.
“See you lunchtime, Miss,” I said, as we parted company.
“No, poppet, I’ve got shopping to do. Remember?” How could I forget?
oooOOooo
At 5 PM, we met up in the car park for the journey back to her flat. My stomach sank when I saw her carrying two large shopping bags, emblazoned with the names of wellknown retailers of female clothing. As I had feared, she had gone shopping for the socalled uni clothing in women’s shops rather than, say, seeking out uni clothing in men’s shops. Undoubtedly, the bias was going to be on the feminine side of uni.
We said little in the car home, but I was anxious to discover what she had bought me. As I knew I had to, as soon as we got into her flat, I took off my upper layer of clothing and put a powder blue bra on, its colour matching the panties I had worn all day. Having practised doing up the clasp behind my back, I could now accomplish the task in under ten seconds.
I could see she was impressed, and she gave me a cute smile that made me blush. I went to put my shirt back on, but she stopped me. “No, poppet, you need to try these new clothes on first,” she said, pointing at the two bags on the floor. “Jeans and socks off!”
Seconds later, I was standing there in just panties and bra, while she eyed me up and down. Then, delving into the bag, she pulled out a pair of blue denim jeans and told me to put them on. At first sight, they didn’t appear too different to men’s jeans, but I soon discovered they finished midcalf, revealing my lower leg. And, having put them on, I could tell from peering in the mirror that they had been tailored for the female figure—I felt embarrassed just thinking about wearing them outside the flat.
“Hmmm,” she said, suppressing a smile. “They look good!” I wasn’t convinced, and I’m not sure she was either, but there was a sparkle in her eyes that told me she was being turned on by my feminised appearance.
I then tried on a pair of trousers, these being pale pink, not a colour I would have chosen. These had a similar short leg to the jeans, and with embroidered motifs at the base of each leg, something seldom seen on male attire. I was very uncomfortable wearing them. Then, worse still, she showed me a pair of very baggy, beige, harem trousers with elastic around the bottom of the legs—they were unmistakably intended for a girl to wear, and the material was so thin that I was alarmed that my panties might show through.
She sensed my concern, saying, “Just be careful when you bend over, muffin. You’ll be okay.” Her facial expression said otherwise.
I was getting increasingly nervous, and starting to sweat, but worse was to follow when she produced tops. There were several Tshirts, in pastel colours, and evidently designed for someone with a bosom, which I didn’t have, unless wearing a bra. But what was as bad were the necklines. It had never occurred to me before that women’s Tshirts often have necklines very different to those found on men’s shirts. One top, in particular, was low cut, intended to reveal cleavage, another had barely any arms, and a third was no more than a vest top. As well as these, there were also a couple of formal shirts, which looked nothing like uni, not helped by the buttons being on the “wrong” side.
“I’m… I’m not sure about any of this, Miss,” I ventured, knowing I had to be careful how I worded my concerns.
“Why not?”
“Well… they look very girly, Miss.”
“Rubbish! You look great! They’re not girly, they’re uni. This is girly, poppet!” She tapped the skimpy top she was wearing. Sure enough, it was more girly than what she expected me to wear—it was so flimsy that it didn’t cover the shoulder straps of her black bra and so diaphanous that I could clearly see the cups of the bra through the thin fabric.
“Yes, but even so, Miss, these clothes you’ve bought me look too feminine.”
She let out a gasp of exasperation. “I’ve told you why we can’t have masculine clothes lying around the flat. Don’t you want to share a flat with me?”
“Yes, of course I do, Miss, but…”
“We’re in the twentyfirst century when anything goes, at least at university. There’s a boy on my course who wears a skirt every day, and no one bats an eyelid. He’s even got a beard! Do you want to wear a skirt, poppet?”
The idea caused my penis to twitch, but I most certainly didn’t want to wear one outside the flat. And then a thought occurred to me. “Could he be Scottish and wearing a kilt, Miss?”
“No, it’s not a damn kilt, you idiot! It’s a bloody skirt he wears. I’m getting tired of your whinging. If the trousers and tops I’ve bought you aren’t to your liking, then you can go out and buy yourself some skirts and dresses that are to your liking. Your decision, Stevie! Tops and trousers, or skirts and dresses?”
She was losing her temper with me, and it was time for me to back down. “I’ll wear these, Miss. Thank you.” I resigned myself to my fate as she emptied out the remaining contents from the shopping bags. There were white ankle socks with pink trim, pink socks with mauve trim, and several other colour combinations, all clearly intended for women. Moreover, there was also a pink fleece, more panties and bras to add to my collection, and even tights and a camisole.
Worse of all, maybe, was something she pulled out of a package that had been delivered that day—breast inserts!
“These will give you a better shape,” she explained, purposefully ignoring my alarmed expression. She didn’t explain what her landlord might make of them, should he find them, and I had no intention of aggravating her further by asking.
Dressed en femme—or androgynously, as she might put it—I followed her into the bedroom where she emptied all my male clothes into the two empty shopping bags. “You can store these in the boot of your car, Stevie. They have no place in the flat,” she said, in a firm tone, not to be argued with.
“Oh, and by the way,” she added, “don’t even think about getting your hair cut. Understood?”
“Yes, Miss,” I concurred, wondering what that was about.
oooOOooo
As I expected, wearing my uni outfits outside the flat was challenging, but I consoled myself that at least I was still at university. Laura was right that almost any outfit was to be seen there, a place where dressing normal was almost considered abnormal. Certainly, I received some strange looks, but no one laughed, at least not to my face.
But another problem had started to occupy my mind. It was now more than two weeks since Laura had given me a hand job to provide release. My frustration was growing by the day, not helped by me wearing panties and by Laura teasing and exciting me at every opportunity. I had been called upon to satisfy her with my mouth many times, yet had not been rewarded, despite her climaxing numerous times.
I was getting desperate and, despite the risks it entailed, I decided I had to raise the matter with Laura. I knew it would be a difficult conversation, and it was after dinner one evening when I decided to speak up. “May I talk to you about something very delicate, Miss?” I enquired.
Her eyebrows shot up and an inquisitive smile broke out across her face. “Go on…” she urged, with unnecessary enthusiasm.
“Er… Men have needs, Miss.”
“Needs, poppet? What do you mean?” She looked bewildered, but I suspected it was an act she was putting on. “I’m feeding you, you’ve got a roof over your head, a bed to sleep in, new clothes to wear. Your needs seem well catered for, poppet. What more could you want?”
“Er…, there are other needs, Miss. There’s a buildup, Miss, which has to be released occasionally.”
“A buildup, muffin? I don’t follow,” she replied, looking comically baffled.
I was sure she was being deliberately obtuse, so I needed to be more explicit. “A buildup of… er… semen, Miss,” I hesitantly explained.
“Hmmm… I still don’t understand you,” she added, shaking her head.
“Men need to have ual release occasionally, to empty themselves out.”
“Hmm? Are you sure about that, sweetheart? I’m studying biology and I don’t think that’s been covered in the course. Would you like me to put you in touch with my professor of reproductive physiology? She can give you information, muffin. Or your mother might be able to advise.”
Neither option was on the table as far as I was concerned, but I knew she was baiting me. “No, I don’t need to talk to anyone, Miss! But it’s not healthy for it to accumulate. The pressure builds up.”
“What?! Do you think you might explode, poppet?” she asked, barely suppressing a grin.
“Not explode, no!” I retorted.
“Ahh! A wet dream though? You might have one of those?” She broke into a smile.
I had not had a nocturnal emission since I was in my midteens and the thought of having one now appalled me. I felt myself going crimson as she teased me.
“I hope not, Miss,” I replied sheepishly.
She paused to think before breaking the impasse with a more serious expression on her face. “I do understand what you’re saying, but I wonder how desperate you really are.” She held me in a long stare, and I found it impossible to maintain eye contact. “It’s only been about sixteen days, muffin.”
Only sixteen days!! I had gone from masturbating once or twice daily to sixteen days!
I didn’t know what to say, but luckily she continued. “I’ll tell you what. As you’ve been a good boy lately, and I’ve not needed to punish you, I’ll give you a choice. Option one is that I unlock you and give you another hand job—you liked the last one, didn’t you? Option two is that you don’t get the hand job, you remain locked up, but we spend the night together in my bed, with you free to explore every inch of my body with your hands. No part will be off limits, muffin.”
I was not expecting that. She was inviting me not just to touch her, but to examine her in the most intimate way, something I had long wanted to do.
It took me only an instant to reach a decision. “I would like the second option, please, Miss. Thank you, Miss.” I could barely talk with excitement.
“Whoa! So you aren’t that desperate to relieve this socalled buildup, poppet?” I did want relief, but I also wanted to touch her, like an ordinary boyfriend might touch his ordinary girlfriend.
She was smiling, and it was a friendly smile. “We’ll have an early night, sweetheart,” she assured me.
oooOOooo
At 9 PM we retired to the bedroom where we both stripped off everything—apart, of course, from my chastity cage, which remained locked in place.
“You can ogle me, sweetheart. Special rules apply tonight.”
I looked her up and down, taking in every detail of her svelte figure, honed from regular exercise. My penis was straining inside its cage but at that moment I was ignoring the pain. She was gorgeous, everything I ever wanted in a girl. I so wanted to penetrate her, but that wasn’t on offer, yet I was going to be allowed to explore the warm, soft contours of her flesh, every valley and every hillock.
She jumped into bed and patted the mattress alongside her. “Come on,” she urged. “I’m waiting.”
I joined her and soon we were embracing each other. Her warm skin was pressed against mine, her breasts and nipples pushing into my chest. Her lips made contact with mine, and soon her tongue burrowed its way into my mouth, where it met my tongue. Meanwhile, my hands began to explore her body. I stroked her back and then, with some manoeuvring of position, I fondled her firm breasts, cupping one in a hand and gently rubbing the nipple between finger and thumb, causing it to harden to my touch.
Next I slid my fingers down her abdomen, towards her pussy, encountering first her neatly trimmed bush. I gently stroked it, much like I would a kitten, and then I moved my hand down so my fingers rested on her mount of Venus. From there, it needed no more than a slight adjustment of position to probe the entrance to her crack, teasing her.
She was dripping wet. Somuchso, I suspected the bedclothes would be stained. My fingers sensuously played with her labia, her clit and then edged into her love tunnel before venturing deeper. All the time, her tongue was in my mouth, desperately engaging with mine and sometimes almost touching my tonsils. As my fingers toyed with her, she started squirming and wriggling and moaning. She was grabbing me, pulling me tighter to her. Then suddenly, with my fingers still inside her vagina, she came and a thunderous climax wracked her body. I did all I could to enhance her orgasm, thrusting with my fingers, while wishing it was my penis doing the pumping.
It seemed to take ages for her to come down from her high point, and she was gasping for breath. “Whoa! That was so good, poppet! You were fantastic.”
I embraced her again, we kissed and then she turned over. Seconds later she was zonked out, softly snoring as I cuddled her in a spoon position. Only then did I become aware of the throbbing pain from my cage. I needed a cold shower, but no way was I going to give up my tight embrace on Laura, even though it was fuelling the furtherance of my attempted stiffy.
After a long time, I drifted off to sleep, only to wake up at some unearthly hour to find that Laura wanted further attention. She flung back the duvet and pushed my head and shoulders down towards her pussy. Despite me being only semiawake, I knew I had a duty to fulfil and using my lips and tongue, I soon brought her to another powerful climax. Her appetite for was insatiable.
She thanked me, kissed me, and then immediately fell asleep again, leaving me, once more, with an agonising pain from my engorged manhood. Eventually, I drifted back to sleep again, and then, at 7:30 AM, the alarm went off. Laura was quick to wake up and was full of enthusiasm.
“You were bloody magnificent, poppet,” she remarked. “What a night that was!”
It certainly was! Despite the pain from my encaged penis, I had enjoyed myself. Being able to touch Laura, and explore her most private regions, with her full consent, more than compensated for my discomfort and disturbed sleep. Yet my buildup was still there. How long could I last? Would I have a wet dream?
And then she surprised me. “You were brilliant, sweetheart, and to show you my appreciation, I’m going to allow you to empty yourself, as you put it.” She smiled warmly at me.
“Really?” I asked, not believing my ears.
“Yes, poppet. I’m going to allow you to spend five minutes in the bathroom, with your cage off. You can do what boys do in the bathroom.” Grinning, she reached into her bedside cabinet drawer and took out the key. Quickly, she opened the padlock and pulled the cage off. Immediately, my penis popped up, like a jackinthebox.
She passed me a condom. “Put this on when you get into the bathroom. I expect you to come back with it full, sweetie. Do you understand me? I think you know what needs to happen to the contents. Eh?”
Yes, I did. The thought appalled me, but I was desperate for release, so I had to agree. “Thank you, Miss, I understand.”
“I’m trusting you to be well behaved and not to make a fuss when I have to lock you up again afterwards. All right?”
“Yes, Miss. I won’t complain or cause trouble. Thank you for trusting me. I won’t let you down.”
She picked up her phone and pulled up the clock app. “Your five minutes starts now. Off you go!”
Wasting not a moment, I went into the bathroom, put on the condom, and began masturbating. It was only later, on reflection, that I thought how debasing this experience was—I had been ordered by my girlfriend to jack off, on my own, in doublequick time. There was no mutual pleasure between us. What I was told to do was no more than a cold, clinical procedure, to be conducted quickly and efficiently. However, this proved easy, and just thinking of the night that I had had with Laura meant that it took only a few strokes for me to ejaculate.
Coming down from my climax took longer than reaching it but once I had stopped trembling I carefully removed the full condom, wiped my dripping penis with toilet tissue, and then went back into the bedroom.
Laura was sitting up in bed. “Was that fun, poppet?” she asked.
“Yes, Miss, thank you, Miss,” I replied. It was unwise of me to add that it was nowhere near as much fun as releasing my load into her, or receiving a hand job from her. But it had provided me with much needed release.
However, my libido had crashed following my spurting. Before masturbating I had felt uncomfortable with the thought of consuming my jism, now I was nauseous. She could tell, so said, “You did promise, so you need to keep your side of the bargain.”
“Yes, Miss, I understand,” I replied after a few moments’ hesitation.
“Open wide and head back. Don’t swallow until I tell you,” she instructed. I obeyed, and she drained the contents of the condom into my mouth.
“Swirl it around, but don’t swallow.”
I struggled not to gag as the gelatinous bolus of spunk moved around my mouth. The taste was awful, but the slimy consistency was far worse.
“Show me,” she ordered.
I opened my mouth so she could see I had not swallowed.
“Gooood boy,” she said, adding further to my humiliation. “Now swallow it!”
I did so, and Laura gave me a zealous smile of satisfaction. Her nipples were once more enlarged and protruding—she was getting worked up again!
