This is my first posting to the Transgender & Crossdressers. I have used Fetish as the all-encompassing bucket for my varied tastes, but I think this story is better here.
This Chapter does not contain a lot of sex, but it helps set the stage for those that do.
This chapter contains elements of cross dressing, homosexuality, cuckolding, femdom and will likely progress into a wider variety of pleasures. If you don’t like these topics, please save yourself the aggravation.
For everyone else, as always, I really appreciate your comments.
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Finally, after a brutally long winter and the fleeting yet unstable spring, summer had finally settled in. Living in Canada where we do, seasons are distinct and the changes in season involve activities geared to the weather.
We both love the outdoors and recognize that in our mid-30s we are not expected to compete with the 20-year-old crowd. I admit to hating when I lose a challenge to Anna outdoors, but she is the better athlete. I try to keep up, to a great deal because I relish is watching her ass ahead of me in her lycra shorts, I love watching her muscles move and flex when she exerts herself, and the strong shoulders and core keeps a tone within her large breasts that I, and most men I have noticed, appreciate. At 5’1″ with fiery red hair, she is stunning. I am fit, 5’8″, but lack the muscle definition to hold a candle to Anna.
Once the summer returns, the skis and snowshoes are away, the outdoors becomes a different environment. For us, canoe camping and hiking are getaway essentials. We also try to spend a couple of weeks at a cottage. Relaxation, reading, swimming, sharing. I love our time.
If we are going to cottage, we plan and research, review and settle on a cottage together for a two week stretch. Normally I am the one to present the alternatives to my wife for discussion. Of course, the final selection is always hers. This year, however, Anna surprised me with a one-week cottage getaway. In fact, I knew nothing about it. Anna was completely responsible the selection, and I was not asked to place an opinion of any kind.
It sounded wonderful and the surprise was a gift. It sounded lovely. As always, our preference is on the water, a master with ensuite, a quality kitchen, fireplaces, and a luxurious bathtub. The fireplace for those cold yet romantic evenings that do occur, and the bathtub is an essential need of my lovely wife.
Driving up to the cottage was the beginning of destressing. The pressures of the past months began to melt away once we are on the road. Driving through cottage country with the abundance of lakes around us hurried the melt just a little. Anna chatted excitedly about the week to come and started to let me in a little bit about the cottage. It certainly seemed her choice was going to be spectacular. Waterfront with a small beach, two fireplaces including a gas one in the master. Three bedrooms including two with an ensuite and the master bedroom had a jacuzzi overlooking the lake. Oh, and our hosts who lived in a home beside us had a boat that we were invited on.
Sounded heavenly and much bigger than we normally get. This certainly exceeded our criteria, and I wondered about how much it exceeded our budget by.
The house was certainly not to disappoint. Pulling down the long driveway I could see the roof of the home with the lake in the backdrop, and it was stunning. Looking to either side I could not even see any homes around us. We phoned ahead of our arrival and Mark and Lynn, our hosts, met us moments after opening our car doors and stepping out to take a breath.
We had not even seen them when we heard “Pretty nice, eh?” as they entered through a path in the woods. Mark beamed brightly as he made the comment, Lynn at his side holding his hand just waved.
Approaching us, both extended their hands in greeting. Mark was about 50 or 55, perhaps 6’3″ with a full head of sandy curls and appeared to be very fit. Lynn stood approximately 5’6″ and matched her husband in the healthy, fit look. Her hair was light brown, almost blonde, and she absolutely killed the short shorts she was wearing and the crop top. I figured she might be late 40s but had the physique of a 30-year-old athlete.
After the standard greetings and handshakes, it was time to enter our new lodgings. Everyone grabbed a bag or two and we walked into the house. I immediately knew just how right Anna was about this place as we entered.
It was stunning. A fireplace with a copper dome top stood in a brick wall between the kitchen and the living room. The back wall of the family room was all glass providing a panoramic view of the lake.
I quickly moved our coolers into the kitchen and assisted in moving the bags to the bedrooms. With four of us it was over in no time. Mark grabbed a bottle of wine from the fridge and Lynn pulled glasses from the cabinet as they offered a verbal tour while we sat on the deck. The sun had not yet set, and the air was still warm making for a beautiful setting for our introductory drinks. Mark pointed out his 42′ craft with a flying bridge moored at the next dock. We eagerly accepted his invitation for a cruise. Commenting on the parties they had enjoyed on their boat and the small islands in the area, it really sounds like heaven.
“We enjoy the privacy of our homes,” Mark explained “and our focus is on private. It is important for everyone to be able to be themselves without having to worry about the neighbours of which there are very few!”
“Well” Lynn interjected “YOU might have to worry about your neighbours!” We all laughed, and Anna smiled at me with a twinkle in her eyes. Not sure exactly what, but there was something more to that look.
Finishing our wine, we returned to the home to settle in, and Mark and Lynn made their way home.
Anna was quite excited about our cottage and our hosts. I was peppered with questions about what I thought about Mark and Lynn. Did I think they were sexy? Isn’t the boat gorgeous? Did I like Lynn’s shorts? In short order we had finished the unpacking and started to settle in for our first evening.
I had not noticed my laptop open on the table until that moment. Strange. I did not remember setting it up. I moved my finger over the mousepad, and it opened right up.
I stood staring at the screen. A photo of a Sissy in a maid’s outfit, the skirt short enough to show the cage protruding from the filly crotchless panties, fishnet stockings and stilettos glowed before me. I touched the spacebar, and another photo came up of a Sissy in a schoolgirl outfit. Then one in a little black dress. It was kind of my ‘best of’ of my collection of Sissy pics. All very cliché. Then the photos got more graphic. Sissies being pegged, sucking cocks, being fucked. Some of my favourites of Sissies joining in while being cuckolded. These were from my secret folders that I shared with no one.
“I thought you might notice your laptop eventually”
I turned with a start, Anna stood behind me with her arms crossed, almost a wicked smile on her face.
“You really should do better with your passwords, baby. You made it so easy when I needed to jump onto some banking a couple of months ago. The file name Sissy Dreams enticed me, and the rest is, well, obvious.”
“Darling, let me…” I started with a dry mouth, but her raised hand stopped me.
“I think a drink on the back deck is appropriate,” she interjected. “White wine, please, chilled” and she turned and walked out onto the deck.
I was stunned. My fantasy had always involved being caught. My fear was being caught. I returned with two glasses and wine in a bucket of ice, unsure of what to expect. I felt the wine was a good indicator of not being too firmly dealt with.
“Sit” was the only instruction I received upon returning to the table with the wine and pouring two glasses.
We sat in silence for a little while. My anxiety rising the whole time.
“I have known about your interest in panties, of course,” she began, “and I found it cute that you thought you could hide it. What I had not imagined was the full extent of your preferences. Kept from me. Most disrespectful to your wife.”
I sat and listened, watching her face, wondering where this was headed. I sipped my wine, trying to keep my hands from shaking.
“My dear,” I began, “I just enjoyed looking at some pictures and”
“When I want to you to speak, I will ask for you to speak,” she stopped me mid-sentence, although I truly did not know how long I would have blathered on and on without any point in my head.
“You did far more than look at pictures. My God, they are categorized into folders and dated quite a way back. Indeed, these have never been shared with me, nor have you been honest about your twisted ideas.”
I could not speak. Suddenly I had a fear that I had gone too far. I could feel myself trembling.
“Oh, don’t you look delightfully scared. Like a little boy who got caught with his hand in a cookie jar. How appropriate. Stand up little boy.”
I slowly stood up in front of her.
“Drop your pants little boy.”
I grasped the waistband of my panties with my jeans. Anna would think I went commando.
“Pants only. I want to see what panties you selected.” Anna corrected me.
As my pants crumpled around my ankles, she motioned to step out of them. She smiled that I had selected pink frilly thong panties today and motioned for me to turn around. She then motioned for their removal. Standing in front of her, my five inches (on a good day) started to grow, and I covered up with my hands and tried to will it away.
“Drop your hands. I have some questions for you. Answer only yes or no.”
My hands to my side, my cock was continuing to harden.
“All your files were categorized and titled. A lot of them referenced the word ‘sissy’. So, I will go with that.”
“Do you want to dress like a sissy for me?”
Knowing what she had seen, and my panties on the floor in front of me, I really could not deny anything.
“Yes” I whispered, my head lowered, but my cock rose a little further, much to my embarrassment.
“Lift your head and give your responses clearly.”
“Do you want to dress like a sissy for me?”
“Yes,” I responded more clearly,
“Do you want to be fucked with a strap-on? I believe you called it pegging? ”
As my cock twitched, she just smiled.
“Yes.”
“Does my little man, or should I say Sissy, want to suck a cock?”
“Oh, no, Darling!” I stated quickly.
“Liar! Your cock is getting harder, you cannot lie” she responded, “and I said yes, or no, only!”
“Would you like to suck a cock before he slides it into me?”
I knew I was holding my breath. I was afraid I would moan out loud, or worse, whimper.
“I saw a lot of slutty pictures you saved with the wives getting fucked while the cuckold sissy helped. Is that what you want? Do you want to be my little sissy cuckold? Do you want me to dress sexy for another man, and have you suck his cock dressed like those pictures?”
I started to shake my head no, but my cock was bobbing, I could feel precum forming at its tip, starting to ooze into a drip. Anna reached forward and ran her finger up my slit, drawing out the precum, then lifted it to my mouth. I sucked her finger into my mouth.
“Would you like to watch a big cock take your wife, wet from your mouth?”
I could not answer, my eyes were closed, but I could no longer stifle the moan that emerged. She left her finger there while I sucked on it.
“Most interesting.”
“I bought you something to wear” she responded removing her finger and pushing a box over to me.
I accepted the box nervously. It was heavy. Opening it I looked at a steel cage. A small steel cage
“Judging my how hard your little cock is, I would say I found the right gift for you. I jut hope it is not too large. Go on. Pick it up.”
Lifting out the cage, I smiled awkwardly. “Actually darling, it is probably too small” I said, waving proudly to my now rigid 5 inches.
“Come forward,” she instructed. Grasping my cock in one hand she removed the wine bottle from the bucket, and to my horror brought it down in front of me, tipping it forward and forcing my cock into the icy water. I screamed out in shock.
“Do not move until I let you.”
God it was cold, painful even. The pain stopped once my cock and balls were numb and shriveled to a tiny nub.
Lifting it out, she grabbed the cage and snapped the ring around my testicles and scrotum. The cage fit easily over my cock, and she locked in in place with no difficulty. I felt nothing. Worse, the tiny cage had space unfilled.
“We have so much to learn about each other still. Let me rephrase that, I already learned a lot about you. It is you that have a lot to learn about me.” She smiled. “You understand that after seeing your laptop, then seeing your responses just now, that the man I married is no longer here, at the very least for our trip, if not forever. What I have now is a fulltime sissy.”
She paused to allow that to sink in. I have no idea if my face showed the fear and excitement that I felt down to the soles of my feet. I knew my face was red with humiliation.
“You will refer to me as Mistress from this moment forward. You will find I intend on enjoying myself here. I saw your fantasy pictures and as of now you will accept any, and all, instructions. I found your girlie clothing. I brought them here. They are in the pink guest room. I added where I thought appropriate. I also improved your poor choices in make-up. I believe I have told you everything you need to know for the time-being. I expect you properly dressed, with a proper attitude, when you return.”
I stared at her for a moment, but her eyes told me not to say a word. The conversation was over for now.
“Yes, Mistress, thank you Mistress” was all I could think to say as I walked away, still in shock. I was excited yet my cock was numb. I could feel the weight of the cage swinging as I walked. I hurried into the guest room. The entire room was decorated for a girl, with pink walls and bedding with frilly pillows. One of Anna’s suitcases and a box sat on the bed.
Opening the large case, I gasped as I lifted out beautiful lingerie on the top. Lacy bralette/panty sets, garters and packages of nylons were soon spread out over the bed. My heart was pounding as I lifted out a variety of tiny dresses and skirts. My panties, and my treasures like the French maid outfit and a long gown with slits to the hip, were at the bottom.
I opened the box and my pair of ‘secret’ shoes were there with three brand new pairs in my size. A pink make-up kit sat beside the shoes. My cock had warmed up and I realized just how tiny the cage was.
I found incredible pleasure holding up the dresses and lingerie. I chose my outfit for my return and realized just how long I had been ‘playing’ with my clothes.
I needed to get ready fast. I felt incredibly restricted as my cock tried to harden in the cage.
I chose a short black dress that had caught my eye. Tiny straps and open back, tight string panty to hold the cage in place, black thigh-highs, and new 4″ stilettos. I kept my make-up light and fixed my relatively long hair to be presentable and quick.
I looked in the mirror, and the image before me was not what I expected. I looked slutty, but I was not passable as a woman. I was a sissy with lousy make-up. I swallowed, tried to smile sexily, and went to see what my response would be.
“Hmmm. Much better” my Mistress offered as I returned. “Give me a twirl, gurl,” she laughed.
I did, noticing that my cage hung just below the hem of this dress.
“You need work on your make-up dear, and perhaps your hair done a little nicer, but pretty good for a start, sissy.”
We enjoyed a couple of glasses of wine, and laughed, enjoying the solitude on the water. I could not help but enjoy the breeze on my nylons.
My Mistress turned towards me and motioned for me to come forward in front of her.
I stood and moved towards my Mistress. Standing in front of her she smiled and stretched out her hand, palm up and grasped my cage.
“I love you, Kris. I wish you had been honest with me about these things. But now I especially love that you will be Krissi my sissy, for the entire week. I caged you just to be clear on that. I have noticed that you seem more attentive since I put it on you. I like that and am going to enjoy those facts fully over the next two weeks.” Releasing the cage, she sat back and spread her legs pointing to the floor in front of her.
“I would like you to gently take special care of my pussy. No rush. This is just the beginning.”
Spreading her legs, I knelt between her knees and lifted her dress. Gently sucking each lip into my mouth as I started, my Mistress rubbed my head, pulling and directing as she felt.
“I think our hosts are pretty hot, baby. Don’t you?” she purred, running her fingers through my hair.
I could only hum my response as my tongue was occupied.
“I wonder what they would say if they saw you in your attire right now, sissy” she moaned. “Would you like that, baby?”
She seemed to fully tie into my sissy persona, making me squirm when I answered these questions affirmatively. My humiliation trigger was so strong.
I licked slowly around her beautiful pussy, watching the fluid drip between her lips untouched. Flicking her clitoris with my tongue, her legs tightened around my head.
I think you wanted to get caught, didn’t you, sissy?” she moaned faster. “You wanted me to find out how much of a fucking sissy you really are, didn’t you?” she egged me on.
“I think you want to be caught again, don’t you sissy?” My cage was stretched to its max, my balls paid the price as my cock tried to push the cage away.
I slid my tongue down her lips, and slid it in at the base, extending all the way in and releasing a flow of liquid into my mouth.
“I think you would like to be dressed like a little sissy while a large cock fucks me. I think you might want to help a big man fuck me, wouldn’t you. Yeah baby, hmmmmm. You like that idea. I can feel your tongue get harder when I talk about helping a man fuck your wife…hmmmmm”
“I might arrange something, baby…hmmm, you’d like that, hmm, yes baby. I so look forward to having my sissy Krissi and pushing her boundaries,” my Mistress moaned, squeezing her thighs around my head. “Maybe I will have you suck a cock, or two, while we are here. Hmmmm. But now this is for me, baby. I want you to pleasure my little rod and suck me off, sissy.”
I slid my tongue upwards, deep inside her, smothering my face in her juices and moving the liquid up over her tiny rod.
Sucking her clitoris into my mouth, flicking its tip, I felt her tense. Running my tongue from the base, slowly up, sliding tip of my tongue over the tip, flicking it again, and lightly pressing it against my teeth. A moan started deep within her, and I pulled her clitoris into my lips, sliding my mouth up and down like a tiny cock. Her pelvis started to move, pressing herself against my face. The pressure on the back and sides of my head intensified, and with a guttural moan she exploded into my mouth.
Waves of fluid flooded me, her pussy pulsing, then slowly subsided. She held my head between her thighs, finally letting me fall back onto my knees.
“Oh fuck I needed that!” she laughed.
Patting me on the head, she started to rise. “That was wonderful Krissi. I am going to rather enjoy myself this week. I hope you enjoy me enjoying myself, too!” she kissed me on the top of my head.
“I am going to get ready for bed now. Please clean up, lock the doors, and shut the lights off, sissy.”