Jenny's Date

Note to the reader: My wife has a date coming up soon with a new lover and I thought I'd put down a hypothetical account of how it might go. It's not intended as a script for her, just a short story that might amuse her (and I might as well amuse you all while I'm at it).
Some of the things described herein have already happened with one of her lovers and some haven't happened just yet, although I expect they will in short order.



Jenny's Date

Mike arrived about seven thirty in the evening.

Jenny met him at the door and immediately pulled him inside, showing her enthusiasm for his arrival by throwing her arms around him and locking her lips against his in a passionate embrace. I watched in silence, feeling awkward and out of place as my wife of thirteen years amorously French kissed this stranger with wild abandon. I couldn't have been more a contrast with him. I was wearing my usual sissy outfit; a feminine apron over my white Cinderella dress, pink polka dot panties, anklets, and shiny black Mary Janes.

I watched the two of them making out with an inexplicable curiosity, my eyes riveted on them as Mike's hands roamed freely over Jenny's curvaceous body. She was dressed very enticingly for him tonight, indeed, she had picked these clothes specifically to impress her date and make it clear that she wanted him to have sex with her. She wore a tight, low cut white top that her big breasts were literally spilling out of, a short clinging skirt, and white stiletto heels. My penis strained within its cage as I looked at her profile, and I reflected, not for the first time, how I wished that I was able to have such free access to her body as her date was tonight. But that was not to be. Jenny forbade me from so much as a touching her when she was in a relationship with a lover, so it had been many weeks since I had had the honor of stroking her lovely, soft skin.

Now, more than ever, I wanted to do just that. Her big, luscious boobs screamed out to be squeezed and fondled, and yet, all I could do was watch helplessly as her new boyfriend did just that, a simple act that I was denied. I watched for seal moments in frustration, my caged penis throbbing madly and impotently, unable to get hard or be touched.
With a heavy sigh, I returned to my chores in the kitchen. Alas, a sissy's chores are never done. I resumed my hand washing of Jenny's panties while my ears strained to hear what was going on in the other room.

"Bobby?" she called out to me, "Get us some wine."
"Yes, Ma'am," I responded promptly.

I went about my business briskly, pouring chilled champagne for Jenny and red wine for her boyfriend into separate glasses. Setting them on a tray, I brought them out just in time to catch Jenny stroking Mike's hardening cock within his pants.
"See this Bobby? This is why I have to get my sex from someone else--he has a REAL cock, not a little sissy penis like you do," Jenny taunted me.
"Yes, Ma'am," I acknowledged her submissively.

She stroked him softly and I could see the massive erection forming in his pants as he stared lustfully at Jenny's deep cleavage.
"Just look at you," she said disdainfully, "You're a sissy that wears panties and dresses. Why would I want that when I can have this?"
I shrugged my shoulders in embarrassment as she reached up to take her champagne glass from my tray. As she bent forward, I couldn't help but be distracted by her full bosom and the tray carrying Mike's glass became momentarily unbalanced. As if in slow motion, I gasped as I saw it tip over and land upside down on his lap, splashing red wine all over his crotch.
"You clumsy idiot!" he barked angrily.

My mouth gaped open in shock and dismay.
"I'm so sorry, Sir," I quickly apologized, "let me just get something to clean that up with."
He stood up and rudely pushed me aside as Jenny glared up at me.
"Oh no you don't," she told me, "you go get the paddle this instant," she snapped.
I whimpered in fear but the fire in her eyes told me that hesitation wasn't an option. Moving quickly to my nursery, I fidgeted as I grabbed the first paddle I saw, the small oval one with the holes, and returned to where Jenny had already set up a straight backed chair in the living room. Mike had returned to the couch where he was wiping the front of his pants with a wet wash cloth.

"Make sure you spank him hard," he growled ominously.
"Oh believe me--I will," she promised him.

I stood dumbly before her as she snatched the paddle from my hands and grabbed my wrist with a steely grip. I put my hands up to stop her but she easily yanked me over her lap and flipped the back up my dress up, exposing my panty covered bottom.
"Please don't spank me hard--please?" I pleaded with her.
"This will teach you a lesson in manners," she replied as she jerked my silky panties down my thighs and past my knees.
Before I could launch into a spirited defense of my actions, Jenny brought the paddle down hard with a cruel slap against my bare, defenseless cheeks.

"OWWWW!" I howled in shock and pain.
SMACK!!! SMACK!!! SMACKKKK!!!
I kicked my feet and slapped the floor with my hands as she peppered my bottom with her paddle.
SMACK!!! SMACK!!! SMACK!!!

This was a lot worse than her normal spankings and I could tell she was truly upset with me. Keeping up a constant rhythm with the paddle, she swatted my buns mercilessly and I was quickly approaching my threshold of pain and dignity. At last, I could no longer take it. I burst into tears and sobbed as she spanked me with a vengeance, delivering blistering swats to each blazing cheek.
Mike watched me humiliate myself with immense satisfaction as I cried like a baby and sank to a new low of shame.
At last, the spanking was over and I rose shakily, on wobbly legs to stand before Jenny.
"I want you to apologize to Mike for your sloppy behavior," she ordered me tersely.
"I-I'm sorry I spilled that wine on you, Sir," I sobbed as I wiped the tears from my flushed and wet face.
Mike regarded me with amusement as he shook his head dismissively.

"I want you to stand in the corner and you better not move so much as an inch--and keep your panties down, I want that sissy red bottom on display."
"Yes, Ma'am," I replied tearfully.
Shuffling over, I put my nose in the far corner and struggled to keep from rubbing my hot, stinging buns. It was all I could do not to assuage the pain because they stung like nobody's business. I shifted my feet and fidgeted, hoping to will away the blazing fire still raging behind me.

As my breathing became more subdued, I listened to the sounds of the room behind me. I could hear Jenny saying something in a low, sultry voice and the sounds of someone shuffling around. For a moment, everything was quiet until I heard Mike breathing deeply and the slurping sound of Jenny sucking on his big, thick cock. I could well imagine the scene taking place not ten feet away behind me but I didn't dare take a peek for fear of more retribution.
Mike was moaning now, and commending Jenny for taking his cock so deep into her throat. A strong surge of jealously ran through me as I pictured her paying oral homage to his manly tool. Risking their wrath, I turned my head just far enough to look at my wife's head, bobbing up and down the long, slick shaft of Mike's cock. He was oblivious to my attention with his eyes half closed in ecstasy, fully enjoying Jenny's magnificent fellatio skills.

"Look up at me," he said in a husky voice filled with lust, "I want to look you in the eyes when I cum in your mouth."
Jenny's response was garbled by the massive cock filling her mouth but a moment later, he moaned loudly and began coming in uncontrollable spasms.
"Oh My God!" he yelled as his eyes crossed and his head rolled backward.
Jenny gagged and struggled but amazingly, she managed to keep from choking. I returned my nose to the corner as if I hadn't seen anything but almost immediately, I felt my shoulder being turned to face Jenny. She bent forward and kissed me fully, opening her mouth to empty the contents into my own. I was shocked to taste the warm, creamy semen of her lover as she used her tongue to make sure I took the entire load. I squealed helplessly, feeling my mouth being filled with his seed but I obediently accepted her "gift", only swallowing the salty goo reluctantly.

Jenny smiled at me, a look of smug superiority on her face.
"How does it feel to swallow another man's cum?" she taunted me.
I blushed furiously and stared at the floor in shame.
Taking her finger, she raised my chin, forcing me to look into her eyes.
"Maybe next time, Mike will let you get it straight from the source."

My face only reddened further and I looked to see the object of her statement shaking his head at my sissyish display.
"Can I pull my panties back up now, please?" I asked pathetically.
"Yes you may," she replied, "And then it's bedtime for you. Go brush your teeth and then I'll tuck you in."
"Bu-but it's only 8:30," I complained bitterly.
"That's right, Bobby, and sissies like you aren't entitled to stay up late. Now get going before I put you over my knee again," she warned me.

"Yes, Ma'am," I responded.
Going back to the bathroom, I brushed my teeth and got ready for bed, knowing that the evening was only beginning for Jenny and her well-endowed boyfriend.
Walking across the hall, I went into my nursery, removed my apron and pinned my nighttime diapers on, waiting for Jenny to come in and finish dressing me. It was only a moment later that the door opened and she came inside. She went across the room and selected a pink diaper cover with a Care Bears type of pattern on it.

"This is right where you belong, Bobby--in a pair of thick diapers and a sissy top while a real man satisfies your wife."
I bit my lip uncomfortably but didn't contradict her. Seeing her new boyfriend with his big eight inch cock, it was hard to imagine how I could measure up to him as a man or lover.

Taking a pair of clear plastic panties, Jenny had me step into them while she pulled them up my legs.
"Just look at you," she said disdainfully, "a grown man wearing sissy diapers and about to be put into his crib for the night like a little baby. And meanwhile, I'll be in the next room over, spreading my legs for my new boyfriend and his nice, big cock."
"Yes, Mommy," I responded submissively.
"I should have done this a long time ago," she said as she removed my dress and picked out a fleece diaper shirt from my drawer that said 'Bedwetter in Training'.

"Oh, and by the way, I've decided I'm going to keep seeing other men, whether you like it or not. I know we had originally said it would be a mutual decision, but I've decided to change the rules. Since you like diapers and dresses so much, you can wear them all you like, but from now on, I'm going to be getting all my sex from real men like Mike, not from a sissy like you."
I whimpered in protest as she pulled the fuzzy soft top over my head, realizing the futility of arguing with my wife, once she'd made her mind up.
"Do you understand me?" she pushed me.

"Yes, Mommy," I replied, once more bending to her superior will.
"And since you are incapable of satisfying my sexual needs, I don't see any reason why I should satisfy yours. I've decided to make your chastity permanent."
"No Mommy--please don't do that!" I protested vehemently.

Without a word, she scooped up the pacifier next my crib and pushed it into my pouting mouth, effectively ending the discussion. I stared into her firm, unyielding eyes, feeling helpless and inferior. At the same time, I couldn't help the intense arousal I felt--between her bossy attitude and sexy curves, I was beside myself with desire and lust. But for some reason, the combination of my sissy outfit and the chastity restraining my penis drove me to an even greater level of submission.
Turning me around, she sent me to my crib by slapping the thick seat of my diapered bottom with a muffled thud.
"Bedtime, Sissy," she ordered me.

Wordlessly, I crawled into my crib and Jenny closed the side of it behind me.
"And if I catch you out of bed tonight, your spanking will be from Mike, not me," she warned me.
I shuddered at the thought of that and hugged my teddy bear for comfort.

Turning the light out, she closed the door behind her and I heard her moving down the hallway. With little else to do, I strained my ears once more to hear what was going on in the living room. It wasn't long before I heard the unmistakable sounds of Jenny moaning, her cries of joy and fulfillment filling every corner of the house. I could easily imagine her, straddling her boyfriend's lap, rising up and down rhythmically as his tremendous cock plunged in and out of her dripping wet pussy. Her hands would be on his shoulders as she steadied herself, enjoying the wonderful fullness of him inside her.

Her cries started gradually, as little more than a whimper, but rising more and more in a crescendo as the passion took her. Finally, she began to moan with delirious abandon, louder and louder until she began to orgasm. Shrieking with pleasure, Jenny came in wave after wave, reveling in the indescribable pleasure washing over her.
There in my crib, I stared up at the ceiling, my penis throbbing in its cage and my heart beating wildly in my chest, indirect witness to my wife's ravishment at the hands of another man.

And the night was still young.

 

You are very kind, Mistress Brenda.