A Well Groomed Sissy Boy Pt. 02

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A sissy boy discovers his true calling.
2.9k words
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Part 2 of the 2 part series

Updated 06/09/2023
Created 05/10/2018
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keptsissy
keptsissy
2,210 Followers

I was scared to death. I think I was visibly shaking, at least it felt like it. I was at the door as soon as my doorbell rang dressed as my boyfriend told me to dress—to kill. I had on a micro-mini soft pink flexible tight rubber skirt. It was so short you could see the soft little head of my penis if you looked just below the bottom of it. My butt was lubricated but not sloppy, just real accessible. I wore a ruffled neck off-shoulder blouse with large ruffle long flair sleeves. I had on 3" spike heel pink ankle boots with pink ruffle sissy sox, big bows on the back of each. I was baby smooth and my bare legs showed off my girly-like smooth soft skin. My hair was up high, big hair in the back and bangs down almost to the centers of my eyes, my ears exposed with huge pink plastic hoop earrings set that all off. I was gorgeous. I knew my man would think so. My makeup was huge too, way dark cat-like eye makeup and big false eyelashes. Pink lip gloss and darker pink lip liner would make any man want to shove himself into my mouth. That was my intention.

"Hello, Daddy."

I felt my face turn red as he passed me quickly at my door and walked into my house. He ignored me. He looked all around the room quickly, somewhat nervously. He was inspecting. I could tell he thought maybe he was being watched, videoed. I shut the door and walked to the edge of my hall. After he seemed satisfied he was not being watched he turned and took me by my arm. He turned me around in a short tight circle, looking me over, inspecting me just as he did my living room. I felt his hand on my back and then on my rear end. He said nothing.

"I hope you like me."

I smiled back over my shoulder at him.

He ignored me, dragging me into the room, he took my arm and bent me over the back of my living room couch. I felt him push me to the cushions, my butt over the couch-back, him behind me. I felt fear. I felt like bolting, running. I knew better than that. My boyfriend would not send a man to my house that was dangerous but I still felt scared. I felt like crying. I fought that back as he slipped my rubber skirt up over my butt. I felt my naked rear end up high and exposed as he cupped my cheeks and spread them slightly. I felt him take his hands off of me and then heard him undoing his pants, taking them down to his knees. I could see him in a mirror across the room. He was rock hard. His cock bobbed as he stood back up straight after lowering his pants and underwear. I felt the slippery wet head of it brush up against the back of my right thigh just under my cheek. Without a word he was in me. All the way, he pushed himself deep up inside of me with his hard cock. He said nothing, made no sound. He started to fuck.

"Uhh...uhhh...uhhhh...ooo..."

I moaned, whimpered, felt like I was being impaled. I was. I steadied myself with my arms on the couch cushions as he used me like that. After fucking me like that, all the way in me, he started 'playing' with my rear for his pleasure. Long full deep strokes, he'd pull out to the head of his erection and then plunge back in all the way, over and over, sometimes toying with just the head of it at the rim of my tight little hole.

All of it started in less than three minutes after he came through my front door. I felt him fondle my skirt, pet and fondle the ruffles of my blouse. I thought that he must like my sexy little outfit. He fucked me for over an hour. He took forever, or so it seemed. And when he was ready to cum I felt him take my cheeks in his strong hands and spread them as wide as they would go. I cried out. He ignored me, fucked me deep and came so hard it poured, ran from my tight little hole all over my tiny balls and soft penis, down my legs and onto the floor. He said nothing the entire time. He just made the noises real men make when they are about to cum, fucking for their amusement, enjoyment and satisfaction. And then he pulled out of me. I gushed.

I stayed bent over the couch, afraid to move. I felt him pull me up by my arm and pushed me down in front of him. Again, he said nothing. I knew what he wanted. I took him in my mouth and started to suck him. I could taste my rear end all over him. I never complain about that. I just do what men expect me to do after they've had me. No man would ever know that I hate that taste.

"Make me hard again. Do it! Make it hard!"

I felt afraid when he snapped at me. I concentrated on doing as told. He stood with his pants and underwear down around his ankles, me working hard to make him fully erect again. I sucked him, pumping as fast as I could, licking, pushing my tongue into the hole of his cock. And when he finally went fully rock hard erect again, he took my arm and pulled me up roughly and pushed me back over the couch. If felt him plunge himself into me again for the second time.

He fucked me for half an hour. He took what seemed like forever again to cum in me a second time. This time when he came in me he collapsed onto my back pinning me to the back of the couch so tightly it hurt. I felt his hands hold my arms tight to the couch cushions as he pumped to cum inside of me. His grunting, moaning, shouting the word 'fuck', the only sound in the room, I felt his cum gush out of me once more.

When he finished with me he stood and wiped himself on my bare butt. I felt him slap my rear so hard it made me cry out.

"Good, very good. He was right. You are a sexy little bitch. And my wife never wears anything remotely as hot as what you are wearing. I like this. I do. You'll do just fine."

He was talking almost to himself as he pulled his pants back up. I stayed over the back of the couch, my face pressed to the cushions. I felt myself start to drip his cum heavily, felt it pouring out of me. It ran down my inner thighs to the tops of my ankle sox on both legs. I felt him take my arm and pull me up off the back of the couch and turn me to face him. I looked to the floor.

"He told me you'd be hotter than any woman I've ever fucked and I think he may have been right. I've never had a sissy boy ass before. He told me to think of you as a 'third sex'."

He laughed loud when he said that.

I felt my face go red. I looked up at him, saw him smile.

"Uh, uh, uh. Don't you look at me, you little whore. You did it right the first time. You look down when I have you."

He slapped my face. I felt tears come to my eyes.

"And when I come back next time you say nothing to me. You just be at the door looking at the floor as cute as you are now or cuter. I know you don't want me to complain about you. I know that. He told me you'd work hard to not have that happen."

He laughed hard, took his hand off of my arm and walked to my door ignoring me.

"I'll probably be seeing you at least once a week. That ass is too sweet not to use. Your boyfriend has good taste in faggot bitches."

He laughed as he left my house.

I stood with my skirt up over my butt, dripping his cum for at least ten minutes, staring at myself in my hall mirror. I could not think of anything I'd ever done that was hotter than what had just happened to me. I knew I could not masturbate but wanted to desperately. I knew another man would be at my door in just a little over two hours, per my boyfriend's 'scheduling' instructions. I hurried up to my girly girl prep room and started getting ready for my next 'guest', as he referred to them. The first two men my boyfriend said he was sending to my house, sending for me to please, no questions asked. I was going to make my next guest very happy, I thought to myself as I stripped and hurried to the shower to clean myself.

When my next visitor pulled into my drive I was made up much the same but did a completely different look for him. I had on 3" spike heel ankle strap open-toe shoes showing off my pink toenail polish, thigh high fishnet lace top stockings, a black ribbon tied in a bow up around my tiny balls tight, big bow on top pushing my soft penis and balls out and up. All of it showing off my little thing and highlighting me for the sissy I am. I had on a sheer lace-top bustier with a lace neck choker. I had deep bright red lipstick and black lip liner to accent my Cleopatra-like pointy mascara eye makeup. My hair was down over one eye, pulled to the side with a big black bow in my hair at the back.

When he rang my bell I felt my soft little thing bounce under the bow on top as I minced to the door to open it I could feel my butt throb from my last guest. I liked that.

"Well, well."

He spoke before I could say anything.

"You're beyond hot. He was right. Wow. Adorable, actually."

He came right up to me as I closed the door behind him and pinned me to the wall. He was an inch from my face.

"I think this is going to be better than I thought it would be."

I felt his hand go to my penis. He cupped my balls and little thing in one hand. I felt his other hand cup my left butt cheek. He leaned forward and French kissed me. And did he ever French kiss me! He was one of the best kissers I've ever had! I felt myself go erect in his hand almost instantly. My little erection sticking straight up in his hand, I could feel the end of it start to drip. He kissed me and kept his hand on me. He worked me, made me want that to never stop. I felt the fingers of his other hand probe up between my cheeks in back. I melted for him. I was instantly addicted to this man and the way he touched and kissed me. He pulled his lips off of me. He whispered an inch from my face.

"You are a very sexy little boy. I like that. This is going to be better than I thought it could be."

I was breathing so deeply, stammering, I could hardly talk.

"You can do anything you want with me. Anything."

I kissed his cheek. He laughed and took me by my hand.

"Take me to your bedroom."

I did. And for the next two hours he made actual real live love to me, treated like a man would treat a woman in bed. I went down on him and did not want to stop. He fucked me in every position imaginable and when he finally came in me he was between my legs on top of me in the missionary position with his tongue pushed deep down my throat.

After he finished he kept his cock in me, just lay on top of me and petted my face, kissed my neck and nibbled at my ears, made me crazy for him. I had never been taken by a man like that before. My boyfriend takes me to bed but not like this man did.

"You are going to be a regular thing. I hope you like that. Your boyfriend told me I'd like you. I do. My wife doesn't do anything anymore. You could not be sexier to me."

He kissed me deeply. He was still in me and I felt his cock stir in my tight little hole. I felt him start to get hard again. Then I felt him start to fuck again.

The second time he fucked me it was hard. He slammed me into the bed. I thought he'd break it. And when he came, he pulled out and hurried up over my stomach and chest. He pushed himself into my mouth to finish. I took it all for him. He kept himself in my mouth and let me suck him clean.

After he was finished I laid on the bed with his cum dripping out of my rear end, just staring at him. I liked this man! As I watched him dress, he talked to me so sweetly. He told me this would be his 'escape', that he'd be seeing me at least once if not twice a week. He told me his wife used to what I just did but not anymore. She had no interest in him. I told him I found that hard to believe, he was so good in bed!! I told him I wanted to see him five nights a week. He laughed and said 'Maybe'.

I told him I wanted to do something for him before he left, before he pulled his pants up all the way. I said I wanted to give him something to think about on the way home.

I hurried to my knees behind him and licked his rear end, ran my tongue all around up and between his cheeks. I could hear him lose himself to it.

"I know she doesn't do this for you, probably never did, Daddy."

I purred as I ran my tongue up the full length of his butt. I pushed my tongue into him, French kissed his butt as I took his soft cock into my hand. I kissed him deeply and then ran my tongue up full length between his tight cheeks one last time. I fell back onto my rear, legs out for him to see, my makeup smeared all over my face, no doubt, the look of 'his whore' I thought to myself.

"You like?"

I smiled up at him.

"Like??? I love!!"

He stared down at me, his cum still running out of my rear onto the floor.

"I'm the dirtiest girl you'll ever know. I'll do whatever you want. Anything you think of, I'll do for you, Daddy. And I'm shock proof. Remember that when you think all the things I know you'll think about me later on."

I stood up and took his hand and led him to my front door. At the door, he put his hand on my penis again, cupped it. He hugged me, kissed my neck and cheeks. I felt myself get hard again in his hand.

"I'll be back. You can count on that."

He walked out my door. I stood there somewhat in shock. Did that man just make love to me? He did. I liked it. I liked it a lot.

I did what I always do after my boyfriend leaves after using me. I masturbated in front of my full length hallway mirror. I looked at the brand new 'call girl' slut looking back at me. I felt hotter than I'd ever been before. I could feel that deeply. When I came into my hand I watched the bitch in the mirror lick it clean, saw her hungry eyes. Then I masturbate again and cleaned it like the 'good girl' in the mirror knew was the proper thing to do, one more time.

I saw the cum on the floor of my living room, left from my first guest. I got down and sucked and licked up what I could, feeling the dirtiest shame as I did. I went to my bed room and did the same thing on my bedroom floor, and on my bed. I thought to myself as I collapsed onto my bed and onto the wet spot in the middle of it that I am the dirtiest whore I could possibly be. And as I turned out the light on my bedside table, still dressed like the whore I am, smeared makeup and cum all over my face, cum up deep inside of my sore and throbbing little butt, I smiled. I could not stop smiling. I like what I am. I like what I am a lot. Then I thought to myself, no. I love what I am.

My boyfriend did not call me that first night. He knew I'd be the perfect hostess, do as he expected me to do. He did not need 'a report'. And he knew I'd exceed his expectations. I did.

I drifted off to sleep.

keptsissy
keptsissy
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  • COMMENTS
3 Comments
tristantrotskytristantrotskyover 5 years ago
Sissy Heaven

I just love her little sissy cock all tied up with the ribbon on it...

sissygirl123sissygirl123almost 6 years ago
love it

I'm a follower of all your stories I just love the feel of women's clothing against my skin and the feeling of his arms around me treating me like a girl I am inside. when he enters me with his manhood I just melt against him

please continue writing about being a girl for our men

AlwaystabooAlwaystabooalmost 6 years ago
Beautiful

Aroused bi each word.

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