Rosie Finally Meets Jessica

It was cold. Bitter cold. January always brought negative temperatures and more snow than I care to see. It's the kind of cold that gets into your bones and you can feel it for hours after being in a warm place. Not even a hot shower can soothe the chill you have inside. Short days and long nights made the month long and depressing. My only respite from the harsh environment was warm house where my wife waited to warm me up with hot meal.

On certain days, we'd crawl under a blanket on the couch or in bed and hold each other while we watched our shows. Today happened to be one of those days, so I was excited to get in the house after being in the cold for 8 hours. It was already dark out and from the car, I could see the lights on in the kitchen. I trampled hurriedly through the foot of snow and made my way through front door. My nose was inundated with the smell of my wife's latest concoction.

As I sat on the steps removing my boots, I tried to guess what she was making tonight. It was never easy to guess since she was always trying something new, but I took it as a challenge. Apple glazed pork chops? Lemon Pepper Chicken? I couldn't tell, but my mouth was watering.

"Rosie?" I called out.

"In here." Her voice echoed from the bathroom. "I'll be out in a minute. Dinner is almost done." Her voice was always a turn on to me, even though she thought it was too deep and masculine. It wasn't. It was sultry. It had a tiny bit of rasp and was deeper than most women's voices but she didn't sound masculine. It reminds of the singer, Pink.

A minute later, Rosie emerged from the bathroom door. Rosie is 5'4", 140 pounds with an olive complexion. She dyes her hair a few times a year. Currently, it's shoulder length and a deep red which clashes with her green/hazel eyes, full lips and high cheek bones in the most beautiful way. It's like looking at red bolts of lightning strike a lush island in the middle of an ocean.

Her shape is distinguished. A former dancer, her legs and core are thick and strong while maintaining a feminine physique. Her chest after kids has grown to D cups, giving her an hourglass figure that makes men stare. She doesn't see it, but I watch them turn around inconspicuously to take a glance at her ass. I watch their eyes follow her through the mall or wherever we might be. She's an exotic powerhouse that's generally outgoing and friendly, but she has a temper like her build, short and powerful.

"Hi Baby," she cooed in that sultry voice as she wrapped her arms around my neck, "I missed you!" It's always been a bit awkward hugging Rosie as we're complete opposite builds. I'm 6'1", 180 pounds which lends to a tall and skinny frame. I have blue green eyes with short light brown hair. If I have an ass at all, it's not worth mentioning since there's barely enough cheek to make sitting comfortable.

It was the "tall and skinny" frame that interested Rosie when we first met because in her opinion, "They all have big dicks." Combine that with a trimmed goatee, a tan, and few tattoos and she was hooked. "I missed you too, beautiful!" I replied as I squeezed her back with a kiss and her feet started lifting off the floor. I could feel her nipples against my ribs as we held each other and I felt the commotion it was starting in my groin.

"So, what's for dinner?" I asked.

"OH! You're going to love it! It this new recipe I found online, but I changed it up a little bit. It's bacon wrapped pesto pork tenderloin." she beamed!

"I can't wait! It smells and sounds delicious, but I need a hot shower first. Do I have time before dinner?" I asked as I made a hand gesture to the clock on the wall.

"Sure, but I have a surprise for you, so take your time and keep your phone on the sink. I'll be texting you instructions and you're NOT allowed to ask any questions from here on." she instructed.

"Oh ok," I replied.

My mind was racing. Rosie had very rarely taken control or made surprise plans, especially when it came to sex. It was always very spontaneous and passionate, so the change of pace was exciting and nerve wracking at the same time.

Of course, we've made mutual plans on weekends without the kids or on vacation to have a fun filled night of exploration and passion. We've bought all the furniture from wedges to swings and all the toys from bullets and strap on dildos to pumps, plugs and cages.

Our sex life is anything but boring, especially with me coming out to her early on that I was bisexual. It bothered her at the time that I would "leave her for a guy" but over the years, she's grown comfortable with occasional strap on sex and puts a finger in my mouth here or there, teasingly of course.

For me, my bisexual nature is in my duality as a person. I am the alpha and the omega. I am masculine with a feminine side. I will wear boots, ripped jeans and heavy metal t-shirt with a pair of pink frilly panties. I can watch a love story followed by a war movie. It's natural me to and many times I feel like I cannot be defined by society's labels.

It's not a cover up or that I haven't "come out" yet. I've had sex with a guy in my teenage years, so I know I couldn't kiss a guy or be in love with a man. I just don't have feelings like that towards men, but it sure is fun to have sex with a man.

That doesn't make sense to Rosie because sex is always meaningful to her. She can't have sex with anyone if she doesn't have feelings for them. In the past, I've tried getting her to open up to the idea of a threesome or foursome, but she's always uneasy about those things because she needs feelings involved, so I stopped talking about it years ago.

Now standing at the sink, I begin my habitual work on myself. I start with my face. A close shave and trim before stripping and getting in the shower. I was just about finished when my text notification goes off.

"Shave EVERYTHING from the nose down! XOXO - Rosie"

EVERYTHING?!?! I panicked to myself. I haven't shaved my goatee in years and the last time I shaved my legs, I used my razor. The result was legs that looked like a pack of Chihuahuas attacked me. She obviously wants me smooth and feminine. How was I supposed to look like that with nicks and cuts all over my legs? My notification goes off again.

"Use my razor and shave cream for everything below the waist, so you don't cut yourself again. XOXO -Rosie"

She was in my head already and had thought this through. My anxiety started kicking in. She's remembering the details, so this must be pretty important to her.

Nervously, I pick up my razor and begin shaving my goatee. First the chin, then the mustache. It feels weird. I haven't felt or seen these parts in years without hair. It takes 10 years off my age and I'm pretty uncomfortable with my appearance now, but part 1 of my habitual process is completed.

I turn the shower on and adjust the temperature. As I strip, my notification goes off again. She must have heard the shower start.

"After you're done shaving, use the enema under the sink and make sure you're very clean. You'll thank me later! XOXO - Rosie"

Okay, I see where this is going. She wants a girl on gurl night. We've played this way a couple times before but never this in depth. She's never wanted me to shave everything for girl on gurl playtime. The enema has been used before too, but just lightly. I've never had to be "very clean". In the past, we would dress up in lingerie and she would lock me in a chastity cage so we could both be as feminine as possible. We'd make out and perform oral on each other until she wanted the strap on for one of us. It was always a nice change of pace to be soft and sensual instead of being the aggressor.

"I'll just play along," I thought to myself. My anxiety eased and got on with the tasks at hand.

Once I was completely shaved and very clean, I wrapped a towel around my waist and made my way to the kitchen for the habitual inspection. Whether she shaved or I did, we always looked to each other for approval, just to make sure we didn't miss anything.

"Well, what do you think?" I held my towel out enough to fit her hand inside the towel. She reached her hand into the edge of the towel.

"That's very nice, but...," she tore the towel off spinning me around, "I can't check EVERYTHING with this on!" Her hand pushed the top of my back bending me over the kitchen island. My feet were still damp so when she kicked at the inside of my feet, my legs split and my chest hit the countertop. She kneeled behind me running her hands down my back, over my ass and along the outside of my freshly shaved legs. On her way back up, she switched to the inside as she whispered deeply, "Mmmhmmm, very nice!"

Her hands parted my cheeks as her breathe passed over my sensitive skin. Her warm breathe gave way to her hot tongue sliding gently over my asshole. I tensed momentarily at the surprise. Then all sudden, she stopped. She stood admiring for a moment before she gave her final approval. "Very good, darling. Now...take yourself upstairs and put on everything I've laid out for you before dinner." she commanded in that sultry voice.

With that, I stood and found my towel. As I reached to the floor, she grabbed a silicone covered spatula and laid a welt across my left ass cheek. "Owww," I howled.

"Leave it! Now do as you were told!" she barked.

"Yes, ma'am," I replied sarcastically, walking away thinking she was still playing the role.

*CRACK* I howled again as she welted the right cheek this time. "Any more attitude out of you and I'll make sure you regret every word." she scolded.

I was confused. I was in shock. I had no response. I walked towards the stairs, as I was told, not sure what had just happened. She had never been this aggressive before. My mind raced at what was going on. This wasn't the pseudo lesbian play time I was expecting. This was something different. Something much more dominant. We've had conversations about dominant/submissive roles before, but we came to the conclusion that she's too sympathetic and doesn't enjoy pain, so it would be hard for her to play either role.

Could this finally be happening? I've had fantasies about being dominated and she knows about them. I've been satisfying my fantasies lately vicariously through my favorite story website and a new niche website designed for BDSM fans to make their own pages to share pics, videos and stories. Had she found my internet history? I didn't try to hide it, but I didn't tell her about it either.

I began feeling anxious again as I made it to our bedroom. Laid out on the bed was the smallest chastity cage we own. Being an average sized 8" and a "grower", not a "shower", it barely fits me at my smallest.

Under the cage was a full lingerie set. It was a pink and white silk and see through floral lace corset. It had four pink silk bows at the garter straps and one between the breasts. The stockings were pink as well with white lace flowers running down the rear seams. The panties were the same color and materials but were like a jock strap with no pouch in the front. "Those are really going to lift my cheeks and push my ass out." I giggled at the thought.

My mind couldn't comprehend what was happening. All the signs pointed to a "girl's night", but her demeanor was the complete opposite of the sensuality I'm used to when we play like this. I continued sorting through the items on the bed. As I picked up the corset and stockings to move them aside, my mouth dropped open. Panic ensued.

She had bought breast forms, large ones at that and a blonde wig. We had never gone this far before. This was too much. I don't want to be a girl, I just enjoy the look and feeling of the silks, laces and all the materials that guys don't get.

I picked up a breast form and guessed they were C or D cups. My hands shook in fear causing the form to giggle. These were expensive, lifelike silicone. They moved and felt real. I dropped it on the bed and picked up the wig. It was long and had loose waves and curls. It also looked and felt real. She really went all out this time, but why?

I dropped the wig and continued. A large butt plug, pink obviously, stood where the wig was. It was blunt and not very long, but the width was thicker than Coke can. I had taken thick objects in the past so she knew I could, but never for very long and nothing this thick. I wasn't sure if would even fit. My notification went off.

"Dinner in 15 minutes. Finish putting everything on and get your ass down here! Oh, don't forget to put the shoes on too. I put them under the bed where the lingerie was. XOXO - Rosie"

Again my anxiety and panic set in. "Shoes!?!" I thought to myself. I scurried to the floor and pull out the box. They were pink glitter 4 inch strap heels with white rhinestones and they were the correct size. "She's gone too far." I whispered to myself. I've never worn anything but men's shoes. I was going to break my ankle or worse falling down the steps. I remembered her spatula and 15 minute time reminder text.

Without a second thought, I grabbed the stockings hurriedly began pulling up them up. They felt and looked great on my bare legs and I felt my cock begin to rise. I grabbed the chastity cage and got it on before it became impossible.

Next, I grabbed the corset since it would take the most time. I slid it over my head with all but 3 eyelets laced. I laced them up, pulled it tight as it would go and tied it in a nice bow to match the bows elsewhere. I spun it around and began attaching the garter straps.

Once finished, I grab the breast forms and placed them inside the corset cups. They barely fit but I did get them in and I could feel the backs almost suction over my shaved nipples. I won't lie. It aroused me to feel the suction and look down at breasts and cleavage. I took a moment to bounce a little bit and watch them giggle. Beyond the form line being visible because of the skin tone difference, I couldn't tell if they were fake or not.

I grabbed the jock style panties and pulled them up over my ass and locked cock. I felt my cheeks squeeze together and raise up to the bottom of the corset. This pulled the cage tightly against my pelvis and put a gentle squeeze on my balls.

3 minutes left.

I shook the wig out and pulled it over my head. I teased the hair a bit with my fingers and straightened it to my hairline. Only the shoes left. I sat on the bed and fit them over my stocking covered feet. They fit great and I tightened the straps so they wouldn't move, just like I would with ice skates.

I moved towards the door slowly and realized I had forgot the butt plug. I panicked. I grabbed the lube from our dresser, placed a glob at my hole and pushed a finger in. I shuddered. Knowing I had little time to work with I sat the plug on the bed, lubed it up and eased myself back onto it. It began stretching me and I pulled up to reset. As I lowered the second time, my heels twisted on the carpet and I fell back onto the plug, burying it to the base. I gasped and cried out. I could barely catch my breathe due to the girth of the plug. I felt like I had been ripped in two.

I pushed myself to standing with my arms and felt my legs wobbling. I shuffled my way to the door and slowly crept down the steps. My heels clicked across the hardwood to the kitchen where Rosie waited.

I stood in the door with my head down, embarrassed slightly and still shaky from the large plug destroying my asshole. My cock was leaking through the cage and I can only assume the massive amount of pressure from the plug was pushing on prostate and causing me to leak profusely. Rosie pulled dinner off the stove and turned to get a look at me.

"WOW, Baby! You look sexy! Put your head up so I can see your face." she said proudly as she approached me putting her hand under my chin. She pushed my head left then right.

"Well, you've come this far. You may as well let me finish you up with my make up." she stated matter of factly.

"But wh..," I began and she put a finger over my lips.

"Shhh...you've been such a good...gurl...so far, don't go ruining it by starting to complain now. Besides, if you had a problem with any of this, you would have been bitching long before I wanted to put makeup on you."

She was right even if I didn't want to admit it. I've always been curious what I'd look like as a woman if given the opportunity. I guess I was about to find out.

"Take a seat. Our dinner is done." she said as she turned away to prepare our plates. I shuffled towards the table half trying not to fall and half trying to maneuver with this giant plug in my ass. I got to the chair and slowly sat down so I could adjust to the pressure of the plug pushing further in.

"Dinner is served. Bacon wrapped pesto pork tenderloin!! What do you think?" she asked knowing that I never turn down her meals even if they burned.

"Delicious, baby! Thank you!" I said with a mouthful.

"Good. I'm glad you're enjoying it, but don't eat too much. We're having dessert too!" She exclaimed with a twinkle in her eye. She's used that line before, but this time seemed different.

When we'd finished eating, I eased out of my chair and shuffled around to clear the table and start the dishwasher. Rose cooked, so I cleaned up. It's that way everyday.

As I set the dishwasher and closed it, I felt Rose stalking me from behind. "You ready, darling? Let's put the finishing touches on you and bring out the sissy you've been hiding all these years." she whispered.

My cage and prostate throbbed in rythm with my heart. "Sissy?!?" my ears echoed. Has she put 2 and 2 together? Or did she find something I was reading or looking at? I didn't know the answer. All I knew was that that word echoed out of her lips through my ear and into my pink soul.

She steadied my walk through the hall to the bathroom. She held the door for me and let me pass so she could give my ass a "love tap" and had me sit on the toilet seat. I plopped forgetting the plug and let out a whimper as it pounded deeper. She noticed and smirked, but made no comment. Facing me, she held my chin up and began working her fingers and brushes over my face, neck and breast forms. 30 minutes later and she stepped back to admire her work.

"Daaamn! I'm good!" she boasted. "All traces of manhood are gone! Now that you're a woman, you need a women's name. How about Jasmine? No, too strippery. How about Carmen? No, too exotic. I got it!! Jessica! Blonde, American, Bimbo!! It's perfect!" she proudly shouted.

"But, why do I need a new name? It's only us here and I won't remember to answer to Jessica, plus...," I started half complaining and half whining.

"Enough! This is a girl's night and since you're locked up, you'll do as I say or I'll leave you locked up until your cock...wait you're a woman now...until your clit shrivels up and dies. Now, Jessica, go put on my black mini skirt and that pink deep v-neck halter top. We're going clubbing!" she commanded as she shook her hips.

I knew I couldn't disobey her. Even if I was small enough to pull out of the chastity cage, the cage had an anti pull out ring that would rip me to shreds if I had tried. I was defeated and put my head down as walked towards the stairs.

"You look great and this is supposed to be fun, so try to get out of your mood please!" she said with another tap on my ass as I passed her.

Once upstairs, I found the skirt and halter and slipped them on easily. I headed for the stairs again, stopping to check myself out in the full length mirror. I really was unrecognizable. Sexy too, I might add. Hell, I'd fuck me. I giggled at the thought and continued downstairs.

Rosie was in the bathroom and had heard my heels on the hardwood floor. She yelled through the door for me to go start the car and wait for her to finish getting ready. I grabbed one of her oversized leather and fur winter jackets and headed for the car.