• Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • Taking Donna's Dick

Taking Donna's Dick

123

Donna leant against me, her generous breasts warm against my arm, the contours of her nipples slightly visible even through her bra and soft white sweater. I could have pulled away, but I didn't want to. It just felt comfortable and sensuous. The others on the software integration rig didn't pay any real notice, she had always been a bit of a flirt and it wasn't unusual for her to try and lean against one of the men. Many would pull away, but I had always enjoyed it. The feel of her short full body warm against mine was always a welcome treat and often not even in an overtly sexual way.

Of course, that didn't stop my mind running away with itself afterwards.

Today though my imagination was already working overtime. My thoughts so distracted that I had lost track of where we were in the test procedure several times. Fortunately, I was only supervising, not actually running the test. Equally fortunate was that Donna's appearance on the rig had come late in the afternoon. My pretence of concentrating on the testing would need to survive only fifteen minutes or so.

Her presence, whilst distracting, had never had such a big impact on me before. Today was different though, not like before. That was because before I had never been wearing a pair of her red satin and lace panties under my work trousers.

* * *

"You're going to wear these for me today," she'd told me eight hours earlier. They were the bright red French knickers she kept in the second draw of her dresser and they looked gorgeous.

"What for?" I had stammered back, my eyes locked on those sexy panties, remembering how they had felt as I'd secretly tried them on when Donna had been away over the weekend.

"Because I'm telling you to honey. And, because tonight, when I get back from work, you will look like a little girlie slut as you strap my lovely hard dick on me and I fuck your pretty little backside," she smiled as she pushed the panties into my hands and gently patted my cheek. "And because we both know it's something you really want to do. That's why honey bun," and then she left me stood in the kitchen with her panties in my hands. She was smiling broadly as she left to go to work.

It's hard to clock in late when you're on flexi-time, but I had been thirty minutes later than normal. That must have been about the length of time I had stood in the kitchen wondering if my world was about to come crashing down in public embarrassment and humiliation. I had eventually decided that was not Donna's aim. There had been no sense of malice or threat in her voice, in fact her knowing smile had seemed to say just the opposite. Her words were a simple statement of fact. This was going to happen. Almost like I was already bent over with the dildo embedded deep inside me.

* * *

I had been in two minds about offering my spare bedroom to Donna when the relationship with her boyfriend had come to an acrimonious end seven weeks previously. I knew I was doing it for the wrong reasons, but after being single and living on my own for so long, the thought of having a vivacious flirty twenty something for company became irresistible.

Not that I really thought anything would come of it. Me being the wrong side of forty was the least of our differences. I thought it would be a refreshing change for a few months and the only downside I could see was the curtailment of my 'dressing' days. Not that I had stopped entirely. I still wore my own panties every day as I had for years. I still wore a nighty to bed each night, again as I had done for years, and with her hectic social life I still had some time alone in the house to smother my masculinity with pretty skirts, blouses, dresses and lingerie.

We had got on remarkably well for such different people, quickly settling into a joint routine that suited us both. We often shared breakfast and evening meals together, the conversation surprisingly easy and unforced.

Of course, it was only a matter of time before the temptation to invade the privacy of her wardrobe and lingerie draw became overwhelming. It started with a tentative opening of the wardrobe and cupboard draws. Looking but never touching. I discovered the pretty dresses she never seemed to wear and the smart sophisticated blouses that I always found so addictive.

Looking however, inevitably turned to delicate exploring. I found the items of her lingerie that tended to the intimate and sexy rather than the day to day comfort that I glimpsed in her laundry. Soon I was enjoying the wonderful, almost intoxicating feeling, of satin and nylon on bare skin. Even if it was only my fingers.

Then I was holding her things up to myself in the mirror. Trying to ignore how close to my size her things were. My eyes lingering on the delicate lace, the wonderful trim. All those beautiful details that make female underwear so pretty and effeminate compared to the drab utilitarianism of those for males.

Finally, my desires had grown too strong and I had stepped into a wonderful matching bra and panty set. In pink of course, with delightful small flowers on the lace trims.

Other illicit explorations and impromptu fashion shows in the bedroom mirrors had followed. I was model, audience and press rolled into one as I posed and admired and snapped pictures on my camera. Later reviewing and reliving the experiences through the captured images. Invariably leading to very noticeable stains in my own pretty panties or nylon slip before the separate SD card I used for those activities was safely hidden away once more.

My final indiscretion just a few days ago had been those red panties and their matching underwire bra. The side lace panels framing the smooth satin that revealed both the nipples of my breast forms and the bulge of my erection.

Naturally I had always been incredibly careful. Her clothes whilst not carelessly strewn around the room had not been particularly well sorted or ordered or folded. And I had not indulged myself enough to introduce any obvious new crinkles and certainly no stains.

* * *

As I stood in the kitchen with her gorgeous satin and lace panties in my hand I was at a loss to understand how she had discovered I had been wearing her things. Had I been careless in replacing them? It seemed unlikely. I had been so very careful and her draws and wardrobe were not that organised. Had she arrived back without me knowing and heard the floor creaking in her room? Had she hacked my computer, found my browsing history? Did she have hidden cameras? Or had she simply been looking through my room as I had hers?

I slowly decided I needed to concentrate on the future not the past. How she knew was clearly not really relevant right now, but confused panicky thoughts continued to chase themselves around my head as I tried to comprehend the implications of Donna knowing the secret I had carefully guarded for so many years.

Then gradually I managed to calm my thoughts a little. Realising her attitude when she had handed me the panties and told me she was going to take me was one of amused acceptance, not one of anger or outrage. Yes, she had definitely been amused. There had been no trace of malice or hatred or mention of revealing the secret to anyone else.

I could of course just not wear the panties. Just tell her I had no idea what she was talking about. She had already found a flat and had a provisional date for moving just five weeks away. Even if she told people I could just deny all knowledge.

Some people might wonder though. The rumours would spread. I would be a laughing stock. Or worse. Could I really take the risk?

Or ... or I could do as I was told. Wear her panties. Try out the fantasy that I had wondered about for years. I wondered if the attractions of that option had more to do with my desires or my fears.

In the end it was the smile that decided it. The final smile she had given me as she stepped through the door to leave me in the kitchen with her panties in my hands. The smile that I told myself was all about amused indulgence and a hint of conspiracy. So, I had gone to work wearing the red satin panties that Donna had told me to wear.

* * *

A few minutes later with the last test of the series completed the warmth from her body faded as we stood up to help the team tidy up and shutdown the test rig for the day. Then I went to leave with the others, trying hard not to look at Donna too conspicuously.

"Oh Chris, can I borrow you for a few minutes to check these disks off?" Donna asked out loud as we were almost to the door. Her face usually had a bright smile to it, but today the smile held something more once again. It was the same smile she'd had this morning holding her panties out to me. I told the others I'd catch them up, trying hard to feign impatience at being delayed.

I knew she had no real need to inventory the disks now, but the small storage room was likely to be empty and it would give her the chance to be alone with the man who was wearing her panties at work. Her panty slut.

As we wondered out with the portable hard drives my cock was already hardening in the sexy red knickers my work trousers hid. I tried to concentrate on the things she was saying, to maintain the pretence that we had an interest in work right then. My eyes concentrated instead on her nipples poking through her bra and white sweater. My mind idly wondering if she would get me to take it off before she slid her strap-on dick into me.

The disk storage room was empty and her hand was suddenly on my behind as she followed me through the door. It was secluded but had several windows on to the corridor and any people passing by could still see in. There was no guarantee that we would be alone for long.

"Open the cupboard," she said her hand still roaming, her fingers tracing the edge of the panties through my plain dark trousers. My hands were fumbling with the key to the locked four draw filing cabinet. I could feel a tension in my movements and there was an obvious hardness in her panties. Her fingers traced up between my ass cheeks, forcing the unseen red satin between them.

Donna chuckled as she watched me scrabbling to get the key in to the lock. "Are you nervous honey. Or is it the excitement of wearing a pair of my knickers." I finally got the lock undone and opened the top draw in case anyone looked in. Donna seemed not to care, her hand was now exploring the front of my trousers, sliding over my thighs, between my legs and rubbing gently over my bulge.

"Undo your fly and tell me how wearing my satin knickers to work makes you feel," she directed. The fingers of her left hand were down the back of my trousers, fiddling with the waistband of her panties, her other was aiding and abetting mine as I struggled with the zip.

"Excited," I admitted. "I can't stop thinking of ... tonight."

She smiled as her fingers explored inside my trousers. Her hands were always warm and I could feel them on my hard cock through the smooth fabric. "I've been thinking of that all morning too," she almost whispered. Her hand was steadily stroking my satin covered dick now. My breathing was becoming more erratic.

"Tonight when I get home you will be wearing the bra and stockings to go with these knickers." Once again, a simple statement of fact. There seemed to be no doubt in her mind I would do it. "They're on my bed along with the thin white blouse and that short-flared skirt of yours." My eyes left her nipples and met her eyes. She had obviously been through my room too, picking her way through all my girls clothes hung in the wardrobe. "What, you can rifle through my things, but I can't go through yours?" There was a disarming smile on her face and her hand suddenly squeezed my hard cock. I felt another noticeable shift in the dynamics of our relationship.

"It's that thin white short sleeved blouse, the red bra I left for you should be quite visible through it. And you will not have to bend over too far for me to see the knickers I made you wear all day."

I looked back at her. Noting the more determined tone to her voice. Feeling her hands on me. Her eyes showing the expectation that I would acquiesce to her touch. I was acutely aware of her fingers very slowly stroking my hardness through the smooth satin. A touch she knew I was powerless to stop because she understood my desires too well.

"OK," I replied nervously.

"And a little slut like you are going to be wouldn't be complete without some bright red lipstick sweetie," she said in a softer tone. I looked steadily at her, but I couldn't help pressing my lips together and thinking of how the lipstick would feel and how it would help my transformation to a slutty tart for her.

* * *

Two hours later I was stood in her bedroom once again. The clothes to turn me into a slutty panty boy were on her bed. The red bra, to match the panties she'd told me to wear, I had already discovered in her draws. A suspender belt and red fishnet stockings I had not found on my surreptitious explorations of her room. I could also see that she had been through my things.

The white short sleeved blouse, quite thin, the contrasting red bra would be very visible through it, especially when it was stretched tight. There was the short-flared skirt with a pinkish rose pattern. It had always felt light and airy when I had worn it before and I knew from experience it would ride up very easily any time I bent over. Of course, this was the first time that anyone would be there to see the tops of my stockings exposed. Next to them was a bright red lipstick and the larger of my two sets of latex breast forms. Dressed in these things I really was going to look like a slutty whore for her, and that made my hardness twitch of its own accord.

Also on the bed were some things of mine she had not mentioned in the disk storage room. It proved just how thoroughly she had been going through all of my things. First were the leather wrist cuffs complete with the two quick snap connectors. And one of my anal dildos with its T-bar protection. Not too big but enough to feel wonderful sliding into my ass. And finally, a note in Donna's usual neat curvy handwriting.

My little panty slut,

Once you're dressed up all pretty with your lipstick on you will get yourself ready for me. Your pretty little backside needs to be filled up so it's ready to take my dick as soon as I get home. Also you will have the cuffs on your wrists and fastened behind your back. I don't want my little whore thinking he can use his hands to stop me sliding my dildo right inside his panty covered backside now do I?

Luv,

Donna

I slowly stripped off my clothes until I was stood in nothing but Donna's red panties. The red panties I had worn all day at work and that bulged with my obvious erection. I rubbed myself gently through the shiny material for a few minutes, then, half reluctant, half excited I stopped and set about getting ready for Donna's return home.

I put the red bra on first. It matched the panties, using the same combination of smooth shiny red satin and red lacy trim. The straps felt wonderful around my chest and over my shoulders. It was a little tight, reminding me of its presence at every movement. A feeling that became even more apparent as I filled the cups with my breast forms. I spent a moment cupping my tits and admiring myself in the mirror. The sight of my full bra cups making my cock twitch inside its restraining panties once more. My tits, though substantial were still not as big as Donna's and my mind wondered idly at the thought of touching and squeezing hers like I was with my own. A pleasure I hoped she would allow me later.

With my cock rubbing against the satin panties and my bra tight around my chest I set about the stockings and suspender belt next. The suspender belt was white, but the red fishnets matched and soon had me looking closer to the slut that Donna had told me to become. Knowing that time was now pressing on, that Donna would soon be back and anxious to please her, I paused only briefly to admire myself in the mirror before reaching for the bright red lipstick she wanted me to wear.

Next came the blouse. A short sleeved white one that was see through enough that she would be able to see her red bra around my chest. Down the front it also had two vertical rows of lacy details with small holes that would easily allow the contrast between colourful bra and pale skin to be seen.

Finally, I stepped into the skirt, holding the tight elasticated waist band apart as I slid it up my fishnet covered legs, and settled it around my waist. My blouse was not too long and didn't really need to be tucked in, but by doing so it pulled down tight over my breasts. What is the point of being a sissy boy if you can't have a ladies' eyes watching your bra through your thin blouse?

I looked at the panty boy in the mirror, his red bra beneath his white blouse, the short-flared skirt that barely hid the top of his fishnet covered legs, the rich red lipstick covering his lips and I could feel, but not see the huge erection filling his matching red panties. All that remained to be ready for Donna was a nicely filled backside to prepare the way for her own strap-on erection.

She had left out the largest of my two butt plugs and the KY lubricant that had been hidden with them. Carefully I applied the lubricant, smoothing the slippery liquid around the anal plug with my fingers. Then, carefully I knelt on the bed and dropped forwards onto all fours while hitching up my skirt. As I eased aside my panties I wondered if Donna would be making me do the same thing very soon. The thought made my cock strain against her panties yet again as I reached back and placed the butt plug between my cheeks. The tip resting on the rim of my anus, the touch of it setting off another twitch to my bulging panties. Then slowly and carefully, relaxing as much as I could, one hand holding my cheeks apart, the other started pushing it up my backside. Moaning as I felt it penetrating my passage and then with a final grunt the widest portion slipped inside the rim and the pleasant feeling of being filled enveloped me.

I stayed on all fours for a minute or so, knees spread wide, enjoying the sensations. The butt plug filling me, the stockings on my legs, the bra straps around my chest, the lipstick covering my lips. Then with Donna due to fuck my sissy backside in less than twenty minutes I got up and washed the lubricant from my fingers.

Donna's final instruction had been for her sissy boys hands to be secured behind his back. To this end she had left the wrist cuffs and the two quick snap clasps on the bed for me. Soon I had the cuffs on my wrists and after fumbling for a little while I managed to clip one to the other behind my back.

I was ready to be taken by my mistress now, a man fully dressed as a pretty girl, slutty red bra around my chest, panties holding back my manhood, stockings enveloping my legs, bright creamy lipstick covering my lips, a pretty skirt and dainty feminine blouse pulled tight against my breasts, wrists locked behind my back and my back passage comfortably stretched by a plastic dildo. I was ready to be fucked, ready to take Donna's dick all the way up my backside.

I went downstairs to wait in the lounge for Donna to arrive home. The stairs surprisingly difficult with my hands behind my back. The feel of my skirt, stockings and bra constantly reminded me that I was dressed like a sissy slut, with a bulging cock filling her panties. I longed to rub it but my hands were now restrained behind me. Eventually I needed relief so badly I resorted to rubbing myself against the arm of the couch.

I was so engrossed by the sensations aroused in my dick that I didn't hear Donna arrive and had no idea how long she stood there watching me with my legs spread, knees bent desperately rubbing my bulging knickers to satisfy my sexual urgings. I was grunting in time to my thrusts and telling myself I couldn't cum until Donna said so when I finally became aware of her stood watching me. I froze, no longer thrusting but still squatting down, legs spread apart.

123
  • Index
  • /
  • Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • Taking Donna's Dick

All contents © Copyright 1996-2023. Literotica is a registered trademark.

Desktop versionT.O.S.PrivacyReport a ProblemSupport

Version ⁨1.0.2+795cd7d.adb84bd⁩

We are testing a new version of this page. It was made in 10 milliseconds