It was 8 months since the first time Mistress Hannah had ordered me to put on her panties. In that time I had become both more of a man and more of a sissy. When we went to the theater club on Sunday nights, I had a variety of dresses, wigs and shoes to choose from. My aerobic workouts had boosted my stamina and I had gotten good control over my premature ejaculations. I still occasionally used the breast and cock pump, but my cock had not achieved the 5" I had hoped for. It topped out at 4-3/4", so I could call it 5" and only my Hannah would know I was stretching it.
We continued to spend our weekends with me as her slave and our weeks with me as the he-man that my penis extension allowed me to be. To tell the truth, I was never macho or very independent during the week, but I was man enough to free Hannah from the burden of making all the decisions about what we did in the evenings.
Along with this independence came my opportunity for a fulfillment of one of my fantasies. Several times I had achieved a streak of two times when Hannah came before me as I made love to her with my strapon extension, but I hadn't yet managed the third consecutive success that would give me the opportunity to go to her promised land. She had told me that three consecutive successes would earn me the chance to fuck her tight little asshole.
On this evening I got another third try and Hannah was doing everything she could to drive me wild and test my mettle. Although I had sometimes been given the choice of when and how we would have sex, she did not offer me that choice on this occasion. She sat me in my comfy chair and started with a slow sexy striptease. She wore her sexiest dress and her sexiest lingerie and by the time she was finished stripping, she was wearing only her sexiest black thigh hugger-stockings as she knelt on a cushion on the floor in the doggy position and said, "Come get some, Big Boy."
Unfortunately for her, her strategy backfired, or maybe that was her plan. She was so turned on by her sexy dance and strip routine, which had included much self-fondling of her beautiful breasts and her ass and even her sensitive inner thighs that when I entered her wet waiting pussy with my rubber dong and reached around to fondle her breasts, I could tell that the race would be close but that I would win it by coming in last.
As her orgasm approached and she began to sense that I might finish further back, she pulled out every trick from her repertoire, but ended up only speeding herself closer to coming.
"Fuck my hot pussy," she demanded. "Fuck me hard. That's it. Oh, yes! You're the man! I love your cock! Fuck me! Fill me up! Ohh, harder! Faster! Oh, I'm coming you bastard! I'm coming! OHHHHHHHHHHHHHH! AHHHHHHHHHHHHH! Ohhhhhhh! Ohhhhhh! Ohhhhh!"
I maintained my control and somehow managed to avoid coming. When she asked me if I came, I just grinned and shook my head. I unstrapped my extension and pulled out my hard cock which continued to jut out in all its tiny glory. After dipping her finger into the extension to prove there was nothing but lubricant inside, Hannah smiled and hugged me and said, "You passed the test Champ. I'm so proud of you, Michael."
I don't know if it was her praise or the fact that she had called me by my male name for the first time during sex since she had given me the name Michelle, but I was so happy I almost came right then.
"I was hoping you would pass today so I gave myself an enema already. My ass is all yours now. You can open me with a finger if you would like. Or you could just put it in. Or if you want, you could open me with this present you didn't know you bought for me."
She pulled a small box from her purse and presented it to me. I opened it to find a small pink butt plug. The thickest part of the bulb was about 3/4" in diameter. I was very grateful that she was displaying such an eagerness to please me that I decided to do what she clearly wanted. I smiled and said, "I can hold off long enough to see this inside you."
She handed me the digital camera and it was then that I noticed the video camera was already perfectly positioned to catch her striptease and everything we'd been doing. It was great that she had actually recorded my success as a male to go along with our vast library of sissy-boy videos. I put a blob of gel on the butt plug and she put her elbows back on the floor and pointed her ass at me. I eased the point of the plug up to her wrinkled hole and circled gently around it, spreading the lubricant around. I added a little pressure and she tensed up. I increased the pressure a little and the tip slowly entered her tight hole. When the widest part got past her sphincter, she clamped down hard on the narrow shaft behind it.
"That's the biggest thing I've ever had up there and it feels huge!"
"Just relax, Sweetie." I twisted the butt plug back and forth until she relaxed a little and then smeared some more lube around it with a finger tip before pushing it in until the flange nestled between her ass cheeks.
"That's all of it."
"Thank the FSM," she said with a grin.
I snapped a few photos as she got used to the feel of it. Then I started to ease it slowly in and out in very short strokes until her asshole dilated. When the thickest part passed in and out of her without her tensing up, I knew she was ready, but I didn't want to fuck her in the doggy position, so I asked her to roll over and pull her knees up. This surprised her, but it seemed to please her. Maybe she liked the idea of facing me while I fucked her. I lifted her ass and pushed the cushion under it with my knee and then I snapped a few more photos.
Once again I started to ease the plug in and out until again she relaxed and her hole remained open. I added a little more lube to my hard little cock and pulled the plug out. As I slowly eased my cock into her it felt absolutely amazing. It was the tightest hole I had ever penetrated and it felt so warm and inviting.
"Ohhh, that feels kinda good," she said with a very surprised tone. I placed her legs on my shoulders and reached around them to fondle her nipples. She slid one hand between her legs and slipped a finger into her pussy and started to caress her clit. I continued to use my techniques to postpone orgasm as she brought herself closer to orgasm, but even without thrusting into her, I almost came.
Soon, her clit was fully erect and I could tell she was very close to coming again so I started to fuck her tight ass. I was slamming into her with full strokes and looking deep into her eyes when she started to come and just then my cum splashed into her. She screamed with pleasure as wave after wave of orgasmic lust washed over both of us. Finally, I collapsed onto her as my shrinking cock slipped out of her ass and my cum oozed out onto the cushion.
"That was in-fuckin-credible!", she gasped. "We'll have to do that again sometime."
I couldn't think of a happier moment in my life. I was finally able to please her with just my cock and a little help from her hand. I considered it to be a new peak of happiness in our marriage. Of course, that's when, like a typical male, I said the wrong thing. "I guess Mistress Bella sure underestimated me."
Hannah tensed and got off the bed. She pointed to the floor and said, "On your knees here, NOW slave."
I immediately said, "Yes Mistress," as I jumped off the bed and complied. She went to her dresser and removed the old pair of pink panties from her top drawer. Then from the drawer beneath it, she pulled a riding crop. She ordered me to stand and put on the panties and then to bend over one-half. She gave each cheek a hard painful swat.
"You made two mistakes, Michelle. Never ever mention another woman just after making love to me! I can forgive you for that one, but you deserve to be punished for the other. Never ever say anything bad about any Mistress I've let control you, especially Bella! Understand?"
"Yes Mistress. I'm sorry, Mistress." Despite wearing panties and being submissive, I was not hard and was not feeling the least bit aroused or humiliated. More than anything, I felt scared, because Mistress looked genuinely angry.
"Mistress Bella is the reason we got together and the reason we are still together. She is a professional domme. She controls simple men with pain and intimidation and extortion. She did not underestimate you. She looked at two of your stories and told me that she could never hold a man like you. She said that you are too complex and that she simply didn't have the instincts required and that frankly you weren't worth the attempt because you don't have the meat she craves."
That statement brought a little jump to my little willy, but Mistress continued, "But she is a good judge of people and she told me *exactly* what was needed to keep you from giving up on us when you were resigned to chucking our marriage out the window. She told me exactly why I would be able to prevent that, and exactly why I would want to. Lay down on the floor."
I quickly complied and she straddled my face. She whipped my thigh and commanded, "Lick me, you cunt."
I started licking her pussy and she said, "This is the kind of treatment Mistress Bella's slaves get." She reached behind and grabbed my cock and said, "But this isn't responding to that treatment." I had to agree that being forcefully commanded was not appealing at the moment, but I kept licking her pussy. "Physical pain does not do it for you. Intimidation does not do it for you. Neither would extortion. I could threaten to drag you naked into a stadium full of people and show them your tiny cock and you would get hard, but we both know that would be senseless destruction of your career and it wouldn't stop you from leaving me if that's what you wanted."
She threw the riding crop away and continued, "We stay together because we get what we need from each other. You could leave and find another mistress, But would she let you fuck her with your compensator? You could find a woman who wouldn't mind your rubber dick, but would she dress you like a sissy and treat you like a wimp? Unhhhh, that's feeling really good. Yes, suck my big clittie. Unhhhhhh. Mistress Bella nailed both of our personalities and I've tested what she told me and learned that I'll be able to hold you without sacrificing too much because of your inadequacies. What are you?"
I replied with a garbled, "I'm pathetic, Mistress." and felt my cock stiffen.
"That's, right. You're pathetic, because you've got a tiny little cock and you only just barely have enough control over it to use it when it's wrapped in a rubber vault. Bella told me what I wanted and she told me I could get it from you and you've done nothing but prove that she was right. Unhhhhh, ahhhhhhhh, ahhhhhhhhh. Oooooh, I'm, ahh, coming, ahh, ahh, ohh, ahh. See now, you're hard, ahh, ahhh. ahhhhhhhhh."
For the second time ever, Mistress gushed as she came and I was practically drowning as I struggled to swallow it.
Mistress eventually crawled off my face, but to my surprise she kept talking. "Stroke your little dick, my sissy. Yes, I know what you want. You want acceptance for that pathetic little needle dick. You're a sissy whose meat can't fill a real pussy. It only barely filled my tight little virgin asshole. That's it. Stroke it. Come for me, sissy. Soil your panties with cum. That's a good little sissyboy. Look at all that cum. Now here, lick it off your fingers. Yes, that's a good little sissy. The next time we see Mistress Bella, you're going to thank her for all she's done for you. Maybe even up on stage. Oh!, that got a little more cum out of your teeny weinie. Here, lick that up, too. You are not useless."
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<a href="https://www.lushstories.com/stories/crossdressing/mistress-hannahs-pathetic-husband-part-5.aspx">Mistress Hannah's Pathetic Husband Part 7</a>