The Date

It had been six months now, since Bobby had enjoyed the pleasure of an ordinary orgasm. And to my suprise, I found that depriving him of such a basic function had caused him to become even more submissive to me, making him more pliable and obediant to my whims. It would seem that when a male is prevented from that most basic of manly functions, being able to get an erection, it tends to have a feminizing effect on him, making him more prissy and less argumentative. I took full advantage of the situation and expanded my domination over him, forcing more concessions from him and restricting his freedom even further.

For one thing, I was openly dating other men now, while I left him home in his diapers to be watched by the babysitter of my choice. And just to rub salt in the wound, I insisted that he help me get prepared for my dates, running my bath, styling my hair, and selecting my hottest lingerie for my liasons. I required him to pick out my clothes, with the knowledge that if they weren't sexy and provacative enough, he could expect a trip over my knee before I left. Thus, poor Bobby had to endure the frustration of picking out my lowest cut tops and skirts, then watching as I put them on in the most teasing manner possible, all with the knowledge that my date would be the one enjoying the view later on while he spent another night, alone, horny and frustrated.

I intended for this evening to be similiar, but I also had a wicked idea up my sleeve. Informing Bobby of my evening's plans, I told him to meet me in my bedroom.

He came in, wearing one of his prissy, flouncy dresses, one with a lot of layered petticoats that fluffed it up, but that still showed off his fat, embarrassing diapers. I, on the other hand, was only dressed in my sheer push-up bra and panties. Sitting on the edge of the bed, I commanded him to pick out some lingerie and an appropriate outfit for me to wear.

Bobby was clearly in a state of angst and agitation; beads of sweat appeared at his brow and he kept wrestling with the front of his diapers, obviously trying to relieve the painful strain he was feeling from his poor, throbbing penis, struggling within his chastity tube to get hard. He stared hungrily at my smooth breasts, the naked lust in his eyes plainly apparent. Being completely consumed with his horny impulses, he eventually selected a shimmery black corset that I knew drove him wild with desire. It added to my already hourglass shape but it also plumped my big breasts into two impressive feminine mounds. It wasn't uncommon for Bobby to start begging me for relief during these times and I couldn't really blame him--his shortness of breath and figeting showed me just how frantically desperate he was to cum.

"I have good news for you, Bobby," I told him as I carefully pulled one of my silky charcoal stockings up my toned legs.

"Tonight, you'll have a date just like me."

Bobby's face registered his shock at such an unexpected event and at first, he was at a loss for words.

"You-you mean I'm...I'm going out on a date too?" he asked incredulously.

"That's right Sissy, we're going to a private party and you'll be meeting my friend Dahlia."

What I didn't tell him was that it Mistress Dahlia, a very strict dom that was known for crushing sissies like flies.

"Oh, thank you Mommy!" he gushed, "Thank you for letting me come with you tonight."

I'm sure he thought there would be an opportunity for him to be released from his chastity but he knew better than to ask for it directly.

"Now, now, don't get too excited," I giggled, "help me get dressed first so we're not late."

He responded enthusiastically and picked out a plunging, low cut top and a nice short skirt to show off my long legs. Lastly, I had him put my high heeled sandals on, and he buckled the tiny straps that went around my ankles.

After making some small changes to his own outfit and picking out some shiny Mary Janes, I sprayed him liberally with his sissy perfume, a little thing I picked up from MommyScents that makes him smell just like a baby's nursery. Now, even a blind man would know what an absolute sissy he was from the sweet, pungent scent he was bathed in.

After a short drive, we arrived at Dahlia's substantial house. I informed Bobby that my date would be along shortly and after being invited inside, we made our introduction to the party's host, a cute woman named Laura.

What followed next, I can barely describe without falling over laughing.

Mistress Dahlia walked into the room next, strutting regally like a queen in her black leather bustier, panties, and thigh high boots. She had such a commanding presence that even I drew in my breath in appreciation. She was quite a striking woman, with long, jet black hair and dark, piercing eyes. Seeing the haughty, imperious expression on her beautiful face, almost made me feel sorry for Bobby.

Bobby greeted her with friendly niavete--which she ignored, staring down at him contemptuously only long enough to be satisfied that here was a sissy who needed to be shown his place. Reaching down, she snatched his wrist roughly and jerked him forward, simoultaneously slapping his fat, diapered bottom with a resounding thud.

"Come along you little sissy," she snarled, yanking him into an adjoining room with her.

Bobby squealed in despair but was forced to stumble after her, to receive god only knew what might be waiting for him inside. The laughter of everyone present filled the room as we watched his retreating form being led firmly and purposefully by Mistress Dahlia to his fate.

While my host gave me a glass of wine, we listened for a moment, hearing Bobby's plaintive pleading, followed by what sounded like a hard slap being delivered to his face. More pathetic whining and pleading followed as my host and I shared knowing looks and giggles. A moment later, we could clearly hear the distinctive sounds of a sissy's bottom being soundly paddled. This was confirmed by Bobby's loud sobbing and wailing as Mistress Dahlia proceeded to blister his bare bottom with a vengeance.

I'm quite sure this wasn't the "date" he was expecting!

"Come with me," my host offered conspiratorily, "We have a special viewing room where we can watch as things get even more interesting."

Thoroughly intrigued, I followed her to the room next door, which had a large window into which we could view what was taking place between Bobby and Mistress Dahlia. It was explained that we were looking through a one way mirror and my sissy husband would be unaware of our watching him.

When we came in, I could see that his diapers had now been haphazardly pulled back up and Bobby was on his knees, kneeling submissively before Dahlia. She was wearing a sturdy strap-on with a thick, flesh colored dildo, driving it deep into Bobby's stretched mouth as he whimpered helplessly, the tears still spilling down his cheeks. She was holding his head firmly as she rammed the huge object as far as it would go down his throat, causing him to squeal like a defenseless little girl.

Then, from the other side of the room, I saw a big, rough looking biker come in, dressed in black leather and a jacket, his bare, barrel shaped chest, thick with hair. Coming over next to Bobby, the biker unzipped his pants, revealing a growing hard-on that was amazing in it's tremendous size. Pulling Bobby off the dildo that was nearly choking him, he immediately shoved his own erection into the sissy's mouth, hardly giving him a chance to catch his breath before forcing him to suck on his massive, meaty tool. Bobby squealed again, but before long, his head was dutifully bobbing up and down while the biker guided him with his big hands behind the sissy's head.

We watched with glee as Dahlia lubed up her strap-on and then got down on her knees behind Bobby. Yanking his diapers back down, she positioned the blunt head of her dildo at Bobby's puckering back hole.

"Open wide, Bobby," she declared, "'cause I'm coming in!"

She pushed it forcefully against his sphincter, but the huge size and Bobby's desperate squirming combined to frustrate her efforts. His Mary Janes were twitching and we watched as he tried frantically to pinch his cherry red cheeks together to deny her access.

Bobby squealed and carried on but with his mouth full of the big biker's cock, he was hardly in a position to resist. Dahlia slapped his blazing buns viciously, making him buck and squeal anew. I saw a fresh set of tears trickle down his cheeks as he fought a losing battle with her determined, slippery dildo. Finally, she managed to push the fat head of her strap-on past his defeated sphincter and she rammed it home without mercy. Shoving it in until it bottomed out, she gripped his hips tightly and held it in place, forcing him to take every rubbery inch, a wicked grin on her face. Her long nails dug into his soft hips and as she looked our way, she gave us a smug wink. Bobby's eyes went wide in angst but now he was getting drilled from both ends and there was no escape for the weak-willed sissy.

Just when I thought it couldn't get any better, a second big biker came into the room.

The guy who was jack hammering Bobby's mouth, soon climaxed in a mighty roar that filled the room, to say nothing of the creamy load that was pumped down poor Bobby's throat. It took several desperate attempts to swallow the huge quantity of sticky semen that was being forced into his mouth but at last, with cum dribbling down his chin, the biker seemed to be satiated. When he finally pulled his tool out, my sissy husband was gasping for breath and gooey semen was seeping down his chin.

Nevertheless, he was still being raped forcefully by Dahlia who wasn't about to let the sissy get away. With his legs spread wide to accomodate the monster dildo being shoved inside of him, he moaned plaintively as he struggled to keep his place on the ground.

Not giving him a moment to rest, the second biker gave his boner a few taunting pumps in front of Bobby's cum-smeared lips.

"Ready for your second helping?"" he jeered down at the hapless sissy.

"No-no-please---" Bobby wailed, his one hand raised in protest, but to no avail.

Without waiting, the grinning biker shoved his hard, eager cock deep into Bobby's gasping mouth, choking him as he gripped his longish hair to prevent his escape. I watched in amazement as Bobby's cheeks were stretched wide to try and accept the gargantuan erection being thrust down his throat. I barely noticed as a third man entered the room and began coating the tip of his hard-on with KY. At a signal from Dahlia, she pulled her strap-on out and the third biker knelt down to take her place.

Bobby was only periferally aware of what was going on behind him, but he soon learned their plans as Dahlia stood over him gloating and the biker thrust his fat, hard cock deep into Bobby's pouting rectum.

Now he was being pounded by two big strong men and there wasn't a thing he could do to stop them. I watched in captivation as I saw his little caged, captive penis swinging rythmically and impotently with each pounding thrust he received from behind. Occasionally, a thin string of useless pre-cum would dribble down, swinging like a pendulum until it stuck against his leg, leaving him a little more drained but no more satisfied. I could only imagine what it must be like for him, getting banged silly by two big men with no means of getting any relief for himself. Nevertheless, this is exactly what Bobby needed.

It was at that point that I decided on permenant chastity for Bobby. With a simple piercing and the right chastity device, Bobby would never be able to cum again. I would limit his sexual experiences to satisfying others, much as he was doing right now. Of course, it goes without saying that I would make sure it was only men he would be satisfying the needs of. It seemed to me that this was the perfect solution for a sissy like Bobby--to keep him perpetually denied while forcing him to service real men.

And just then, my date arrived and I had to leave the party. Much as I would have liked to stay, I had my own hunky man waiting for me and besides....I knew Bobby was in good hands.