author: Baloardo Gratiano
[Author's note: a collection of my writings on cross-dressing and erotic humiliation are available on Amazon, under the title: "A Treatise on the Sissy." -- Baloardo Gratiano.]
Economic considerations required me to rent a room in an apartment rather than get a place of my own. After visiting many locations I finally found a well-kept middle-class home in a nice building, owned by a very intelligent --and not unattractive--woman in her fifties. I was twenty-three at the time. Mrs. Morfydd (there didn't seem to be any Mr. Morfydd) was direct and a little commanding in her inquiries about me. But her expectations of my conduct were reasonable, and I was glad to have the terms of our arrangement made so clear from the very start. I would have kitchen privileges, would help with the house cleaning and maintenance, could come and go as I pleased, but might not have overnight guests.
I liked Mrs. M. at once. I have always been somewhat shy, particularly around women, so I was glad to have her take the lead. I soon moved in my effects, mostly books, and a routine developed.
In the course of our first weeks together she asked a few questions. Did I have a girlfriend? The answer was negative. Had I had a girlfriend? Yes, I replied, not entirely candidly. I had had crushes, and once a girl had, apparently on a whim, bedded me, but lost all interest in me after that first time, when I came quite prematurely. I was so overexcited by our several inconclusive dates that when she finally let me have her I didn't last long. "You came already?" she asked, or perhaps announced, and pushed me off and put her jeans back on. That was that.
I had had a few encounters with guys. These did not, and were not meant to, develop into relationships. They took the edge off my horniness, and were better than abjectly courting uninterested girls. I generally took a submissive role.
I liked wearing panties. My dick isn't very big, only five inches when hard. I am well proportioned: thin, five foot seven, and I like to think it's all to scale, but in fact my cock is a good inch smaller than average. Panties fit me, I don't really need briefs, and I like the patterns and materials better, Anyhow, men's briefs are designed nowadays so they pretty much look like panties, except they have that little pouch which I don't really need.
Mrs. M. came into my room one day to speak to me about some household matter, and I hadn't put away all the neatly folded clothing I had brought up with me from the building's laundry room. She only glanced at what were obviously a pile of girl's panties, and said nothing. But from that moment she seemed warmer, more sympathetic towards me. In the coming weeks she stood closer to me when we talked, and spoke in deeper, more intimate tones. Sometimes she would touch my shoulder when explaining something, or hold my arm when we went together to the kitchen. One day she told me I was such a nice boy, she wondered that I didn't have a girlfriend. She stroked my hair when she said this. I sighed.
"Do you like women?" she asked, her hands on my shoulders now. "I saw your panties, and I wondered. It's OK with me, whatever your preferences are."
"I like women," I said. "They don't seem to much like me."
"Well I like boys," said Mrs. M., "especially sensitive boys like you. I think it's so sweet that you wear panties. But aren't they a little tight on you?"
"No they fit fine. I'm , uh, not that big."
"I like that. I don't like men who are big, like animals. I like smooth thin boys like you. Boys like you can better please a woman who knows what she wants."
Here she kissed me. My little thing instantly got terribly hard in my pants. I didn't know what to do. I somehow didn't dare to take hold of her. She reached behind me and stroked my ass with her hands, pressing me against her while she kissed me.
In her bedroom we undressed. She was wearing just her bra and panties--black lacy ones. I was wearing my pink floral panties. I felt like a flat-chested girl next to her. I was so excited! She reached down and felt my small stiff penis, and said,
"You know you won't be able to get me wet with this little thing. Have you ever gone down on a woman?"
I said nothing.
She took off her panties and sat on the edge of the bed. I got on my knees before her.
He pussy was quite hairy. She had a magnificent bush and her labia were large.
"That's what pussy really looks like, Damian," she said. Have you ever looked at one up close like this?"
I shook my head no.
"Give it a kiss."
I did, a slow kiss on the amazing wrinkly cunt lips. I smelled the faint thrilling scent of her piss.
She pulled my face in.
"Kiss it nicely. Kiss my pussy for me, show me how much you love it."
I kissed her pussy up and down, slowly, adoringly..
"Now lick it for me. Lick it like a good boy."
I licked and licked, slowly, and deeply. I tasted her cunt. I smelled the wonderful smell of a pussy as it gets wet.
"Now put your hands under my ass, so you care really pull your face into it."
I did so, licking deeply , concentrating on her clit. Sometimes I thrust my tongue into her, using it like a wet thick penis, but mostly I rubbed her clit with my tongue, in a circular motion. The one girl I had slept with let me watch her masturbate once, to tease me. I imitated with my tongue what I'd seen her do with her finger.
"Good boy. You don't need to touch your little thing. Just hold my ass and keep your face in my nice pussy."
She was getting really wet. I could almost have cum in my panties just from licking her.
She pushed my face away.
"Now take off your panties, sissy."
I obeyed her. I wasn't sure about her calling me a sissy, but with my pink panties I couldn't well argue.
"Let me see your little thing. It's so cute and small! Let's see what it feels like."
She guided me in. The wet warm cunt felt so good I could scarcely believe it. Hotter, more thrilling than any blowjob!
"Now don't cum without my permission. Guys with little dicks often cum prematurely. They get so excited. Are you in me yet?"
I had been all the way in for a while.
She held my ass and pulled me close.
"Hump me with your little dickie. You like how that feels, don't you? Hump my pussy with your little panty-boy cock, but don't cum."
It was all I could do not to cum, feeling her hot pussy and being told how small my dick was.
"If you cum in my pussy before I'm ready, I will make you lick it up and finish me with your mouth. You don't want to have to lick up your little mess, do you? On your knees licking sperm from a pussy you were too little to fuck? I don't know, guys like you with tiny dicks usually can't help themselves. Maybe you really do belong in panties, your dick is too small to be a man's. You can't really fuck, can you? Just rub your little clit against mine like a girl. If that makes you cum, you can finish me like a girl, with your mouth. Maybe you'd like that better."
I couldn't help myself. I came. My little stiffy squirted helplessly in her hot cunt.
"You came, you little sissy, didn't you?"
I nodded my head in shame.
"Get out, get out," she said pushing me off her.
"Now clean me."
She pushed my face into her cunt, dripping a little with my sperm. I lapped it, to keep it from getting onto the bed sheets.
"Now finish me with that talented tongue of yours. Lick me like a girl."
I was already hard again from her words and the way she forced me to do what she wanted. I licked into her cunt eagerly, tasting the last of my salty liquid, and then it was nothing by the taste of wet pussy.
I went to work on her clit, rubbing it with my tongue in a circular motion, from time to time thickening my tongue to penetrate her. She held me by the back of the head, keeping my face in place, pushing it into her. Finally she started bucking and her cunt contracted and stayed tight as she came in my mouth.
When she was done fucking my face she put her palm to my forehead and pushed me off.
"Good girl.
"That worked out very well for me, and I think you liked it too."
I nodded. It had been the most exciting sexual experience of my life.
"And don't worry about your little thing. I don't really like hung men, I don't enjoy being gouged by a big cock. Some women do -- masochistic women if you ask me. I prefer a guy with a little inadequate dick like yours. A dick I can just ignore. And I really love being licked. You have a very good tongue."
She paused to reflect.
"I don't really like sucking a cock. I hope that isn't important for you, because I don't do it. I don't let men cum in my mouth. But you don't really care about that do you?"
I shook my head.
"I didn't think so., You'd rather be the one on your knees, wouldn't you?"
I nodded, embarrassed but excited.
"Oh we are going to get along very well indeed."