She knew all this before we married, but, because we love each other, we found a way around my inadequacies. I made love to her with my mouth and my hands and after she came, I put my puny cock inside her. In usually less than a minute, my three inch little wiener pumped out a few dribbles and I was done for the next day or so. I used to last a little longer when we were younger, but when our sex life dwindled to about once a week, sometimes I only lasted about 15 seconds and it wasn’t very satisfying. But a big change happened about a year ago. For the prior few months, we’d only made love twice. I was contemplating letting her know that I wouldn’t get in the way if she wanted a divorce so she could find a real man. I had settled into a deep despair for about three weeks, while I tried to find the courage to let go.
Hannah is a very beautiful woman with an anomaly that I found very sexy. It entranced me the moment I discovered it. She has a larger than normal clitoris and it swells much larger than normal when she is aroused. It looks much like a penis tip but without the pee hole. The first time we had sex, she was worried that it would freak me out. I got the impression that she had been teased about it when others had seen it. For a while she was angry at her parents for not fixing the problem when she was little, but later she learned that fixing the problem meant she would not enjoy sex as much so she just needed an understanding lover.
I was not the least bit put off by it. In fact, it was so sexy, it may have made me set a new record for coming too soon, which, along with my tiny cock, had clearly disappointed her. Somehow, she continued to date and have sex with me and we grew to love each other. I was the happiest man on the planet when she agreed to marry me. That made it so hard to stay together when it was clear that our marital problems were very deep. I knew that I was sexually disappointing to her, except when I lavished attention on her clitoris with my lips and tongue, but my manly pride required me to insist on trying to please her with my minuscule cock. My attempts often ended up with her being bored and me being angry because she wasn’t hiding it.
As I finished drying and stepped out of the shower on a fateful Sunday, I was surprised to find Hannah standing there holding one of her pairs of panties. It was a sexy pink pair that was one of my favorites. “Put these on.” she commanded. I was so shocked that you could have knocked me over with a strong blink. I had actually worn those panties in secret before and I had fantasized about wearing them in humiliation for her, but I had carefully kept my fantasies from her out of fear that whe would leave me. But one of them had included a confrontation just like this. As I stumbled over how to respond, she said words that sent a shiver of dread through me. “I found your pornography stash.”
Oh, hell!
“I saw the pictures of you wearing these.”
Oh, no!
“I saw the video of you with a banana up your ass.”
Oh, crap!
“I read your fantasies.”
Oh-oh!
“I made copies of it all and I’ve hidden them.”
I’m a dead man!
“Things are going to be different between us, but you are going to put these on!”
I hung up my towel and took the panties from her, but then I rushed out of the room and locked myself in the bedroom. I crawled under the covers on our bed and curled up in a ball. I needed time to think. She couldn’t be lying. She could have just left me and filed for divorce, so she must want something from me. The answer must be in the files she found on my computer. Why would she want me to put her panties on? She already had me by the balls. She knew my most embarassing secrets. What more did she want?
I heard the latch on the door as she opened it with the safety key. She crawled into bed behind me and started rubbing my ass.
“I know this must be a big shock,” she said, “but this will be good for us. I found it all a few months ago and I was devastated. I saw all the other women you’ve been looking at, and I felt inadequate when I saw how sexy they are – so many redheads and so many shaved pussies and so much anal sex. But I also saw the pictures of other women with big clitties. I felt violated when I saw you in my undies. I felt like I had failed to please you when I saw what you did to yourself in the videos. I even felt a little disgusted when I saw all the videos of women with strapon rubber cocks fucking men. But as I read your stories, it was clear that you really love me.
You’ve got a teeny little weeny and you have no control over how quickly you cum and you’re not the big he-man that can fuck for hours in all kinds of gymnastic positions.
Her words were like punches to my self-esteem. She had never specifically mentioned the inadequacies of my cock before, but I knew that she had read my stories and now she knew how aware of them I am. She also knew from my stories one of my truly deepest secrets, that humiliation turned me on. Now she was rubbing my ass. That was another thing she learned from my stories. My ass is sexually sensitive, I think because of my low sense of self-worth. She was letting me know that she would take that into account. I didn’t see any way out that wasn’t too drastic to consider, so, with a sigh of despair, I uncurled enough to pull the panties on. I thought maybe she would laugh at me or shun me now that she had achieved her triumph and so I started to sob. She kept rubbing my ass, now through the satiny cloth of her panties. “Shhhhhhhh,” she soothed. “It’s okay. We’ll make it better now. You’re my little sissy boy. Now say it, say you’re my little sissy boy.”
“I’m your little sissy boy,” I sobbed. She slowly pulled me over onto my back and then she leaned over and started licking and sucking on one of my nipples. Her hand shifted from my ass to my panty covered crotch. My cock was hard and fully extended like a tent pole under the fabric.
“I want you to understand this,” she said, “You are pathetic. What are you? Say it.”
I knew it was true and I knew that I would lose her if I didn’t comply, so I said, “I am pathetic.”
She repeated the question several times and I repeated the answer each time. In the meantime, she gently rubbed my ass and and my teeny cock and the feel of the soft feminine fabric was very sexy. She followed my pathetic admission with the second question that put me in my place. “But what aren’t you my sweet little sissy boy? You aren’t useless. I will use you, so when I ask ‘What aren’t you?’, you will answer with ‘I am not useless’. Now say it. What aren’t you?”
“I am not useless.” She stroked my teeny shaft and my humiliation was complete as a I soon pumped my cum into the panties.
“Now, that wasn’t so bad was it? Stand up and let me look at you.” I got out of the bed and turned around and immediately her digital camera flashed. I looked down and the panties were clearly and obviously wet from my cum. How embarassing. “Get used to the camera,” she said. “I want lots of pics of my little sissy boy doing my bidding. Keep those panties on for now and go get what you need to shave my pussy.”
I got the supplies and after carefully trimming her chestnut-brown pubic hairs with scissors, I revealed what I had been curious about since we had first met. The actual appearance of the delicate folds and curves of her pussy was more beautiful than I had imagined. As I worked, she occasionally took photos. I completely removed the hair, even the few curly hairs around her wrinkled asshole. After the smoothest shave I could accomplish, she inspected herself with a mirror and she seemed pleased. I washed away all traces of the shaving cream and then she had me kneel on the floor beside the bed. She sat on the edge of the bed with my head between her thighs and took another photo of my face poised to begin her pleasure. Then she asked me again if I was her little sissy boy.
“Yes Mistress, I’m your little sissy boy.” Then she asked what I am.
“I am pathetic.” Then she asked what I’m not.
“I am not useless.”
“Then lick my pussy, slave.” I gladly complied. All the tears were gone and I was comfortably doing what I wanted to do. It was very strange kneeling at her behest in my little pink cum-soaked panties, but I was at peace and I soon had her moaning and gasping in pleasure as I brought her to a series of orgasms. When she was spent, my cock was hard again. She saw it when I stood up and she pulled me to her.
“Fuck me little boy,” she said as she pulled the panties down just far enough for my little pole to pop out. I was able to kneel on a small footstool next to the bed and it was just the right height for pentration. I entered her spread pussy lips and to my surprise, I lasted over two minutes before pumping my load into her.
When I crawled into bed beside her, Hannah told me that we would spend our weekends with me as her little sissy boy and that she might have me do things during the week to prepare for the weekends, “Like keeping my pussy smooth,” she said with a smile. I looked forward to it.
