THE ROMANTIC TRANNYCHASER SERVES THE COCK OF HIS BELOVED!

[squirtsilly]

THE ROMANTIC TRANNYCHASER

Here is a three-part piece of fiction, complete in three sections, one posted right after the other, broken up for easier reading. It was inspired by the accompanying pictures by Captain Outrageous of this awesomely sexy, yet demure, gal. I hope you enjoy it, and as always, any comments are greatly appreciated!

THE ROMANTIC TRANNYCHASER by Squirtsilly
Part 1: Dry-Humping and French-Kissing

I’ve always wanted a t-girlfriend, and now I have one. Her name is Penny. Actually I met her in the library one day, when I was browsing through the new books. She was on her lunch hour from her secretarial job, and we got to talking. Although she was very pretty and passable, dressed conservatively but attractively, I immediately knew she was transgender. I had hung out at t-girl bars in the past, known and dated t-girl escorts, and I could read them pretty well. Still, I think she had some anxiety about what I actually did or didn’t know, so when I asked her for her phone number, she told me bluntly that she was a pre-op. “I just don’t want to have any misunderstandings down the line,” she said. “Me neither,” I replied, and gave her my number too.

I’ve been with genetic girls and t-girls, and although I like them both, I find t-girls the most attractive. I love the femininity, and I love the cock. I am also sexually submissive, both to women and t-girls, and a girl with a cock brings out my most enjoyable feeling of surrender.

Penny was perfect for me. She was thoughtful, considerate, and we shared interests like movies, museums, and reading. She loved Italian food and we explored different restaurants. As we dated over a period of weeks we took things slow sexually, which added to my excitement. We sat on her living room couch for hours, kissing and fondling each other; but we didn’t get out of our clothes. We would be French kissing and we would rub each other, building up the pressure but not letting it go. She didn’t let me stay over and I always went home with blue balls, but that was okay; I told myself I was saving it up for something that would be really special. I didn’t feel Penny would let me down, or herself. This was going to be not only a warm relationship, but a thrilling one.

Penny gave me a sneak preview of her sexual nature one night when we were on her couch making out. She was wearing jeans and a top, and although she didn’t let me touch her breasts yet, I could feel the hardness of her nipples against me. I also could feel her cock in the front of her jeans pressing against mine in my own jeans. We got more and more turned on as we dry-humped, and were getting closer and closer to cumming, but then suddenly Penny told me with a sweet smile that she wanted me to hold my orgasm in, while she let her own cum out. I almost couldn’t take it anymore but she said she wanted to see how well I could control myself, and that if I respected her I would do as she asked. She had such a sweet smile, how could I disobey? So taking a deep breath I lay there while she dry-humped against my hip and then suddenly I could feel her cock spasming in her jeans. Looking at her pretty face all scrunched up in ecstasy as she shot her load in her panties and tight jeans was one of the greatest things I had ever witnessed. It took all my concentration to try to hold my load back, but I failed and began unloading in my own pants from the sheer thrill of the spectacle. But Penny forgave me. She lay on top of me, squishing my cream against me in my underpants as she ground her denim crotch against mine, kissing me and telling me it was okay, she still believed I respected her even if I couldn’t control my orgasms. She said she knew she’d been strict with me, but soon I was going to get my reward.

Part 2, "Housecleaning, Spanking, and Cummy Towels," follows immediately!

[squirtsilly]

THE ROMANTIC TRANNYCHASER by Squirtsilly
Part 2: Housecleaning, Spanking, and Cummy Towels

A couple of days later Penny called me up in the morning just as I was getting ready to go to work. “This is the day,” she said, “the day we’ve both been waiting for. Can you come over to my apartment right now?”

I explained that I was about to leave for the office but Penny said, “Can’t you take a day off? This will be so much fun for both of us. Please?”

Just the sound of her girlish voice over the phone called to mind all the things I loved about her: her gentle smile, her soft perfume, even the sound of her pantyhose rubbing together as she walked. I told her I’d call my office and tell them I needed a day off. Since I had nothing urgent on my schedule, it wouldn’t be a problem.

However, when I got over to Penny’s, she herself was getting ready for work. She was dressed in a jacket and skirt, blouse, and medium-heeled pumps. “I don’t get it,” I said. “I thought we were taking the day off together.”

She came up close and began to undo my shirt. “Well, only you are taking the day off, but in a way we’ll be spending it together. We’ll be playing a game, with me in the office and you here in my apartment.” She took off my shirt and then my shoes and socks and trousers. “Ooh, you wear tighty-whities,” she said. “They make you look cute.” But then she hooked her fingers into the waistband and pulled them off. “Oh, your thing is kind of small, even when you’re hard,” she said. “But it makes a good handle.” And she led me by my cock, naked, into her bathroom. She lifted up the toilet seat and positioned my cock over the bowl and began to stroke me.

“This isn’t how I imagined our first time together,” I said. “Which isn’t to say I don’t appreciate its novelty...”

“This is what you’re going to do today,” she began. “First you’re going to cum, so you won’t have naughty thoughts distracting you, and then you’re going to clean my apartment. And then when I come home for lunch...”

“Yes?”

“You’ll get acquainted with my cock, just like I’m getting acquainted with yours. Oh yes, you’ll learn lots about my cock!” And at those words, I began to shoot my stuff. Penny angled my thing down so my goo all landed in the toilet bowl.

“Ooh, that was a big cum!” she said, tongue-kissing me. “You were horny.”

“I’m still horny.”

“But that load should keep you until I get home for lunch.”

She wiped me off with a piece of toilet paper and led me, now by my soft cock, into the living room. “I’m going to my office now, but I’m going to be getting very horny myself thinking about you in the nude, cleaning my apartment.” She let go of my cock and locked all my clothes in her hallway closet, saying “Just in case you have any ideas about covering up! I want you nude and doing housework.” And then she showed me what had to be done in the kitchen, the bathroom, the bedroom, and the living room. She showed me where her dust cloths were, and the furniture polish, and the broom and vacuum cleaner and so forth. I had my work cut out for me.

“Now get busy, and I’ll see you at lunch,” Penny said, kissing me on the lips. “Remember, no playing with that tiny thing!” But it was tiny, and I actually liked hearing her say so...

I tried to concentrate on my chores, but it wasn’t easy because my dick got stiff again almost as soon as Penny left. As I dusted and swept, I kept leaking. The idea of being a houseboy like this for my pretty t-girlfriend was fantastic. It was a much more exciting job than the office gig that paid my bills!

I was tempted to tug myself off while I stood at the kitchen sink scrubbing some pots and pans, but I decided against it. The more I abstained, the more excited I got.

Then the phone rang, and it was Penny. “How’s my little slave?” she said.

“Did you just call me ‘slave’? Wow, you’re full of surprises. Anyway, I’m fine.”

“I like to be in control of my boyfriends. It really comes out when we get down to sex. I hope you haven’t disobeyed me and squirted out any more cream?”

“No, Penny.”

“Good. Well, I’m going to be home for lunch soon, but it’s not food I’m going to want. I’m so turned on thinking of you following my orders, being naked in my apartment, and not even being able to get dressed if you wanted to! You really are not only my slave, but my prisoner! I’ll be home soon and I’ll want you to give me a blowjob. Don’t know how long I’ll last, though, because I’m soooo turned on at the thought of you doing it!”

My dick was leaking and I was cupping the tip so I wouldn’t stain the sofa where I was sitting. “I’ll do whatever you want, Penny. I’ll be waiting. Just bring yourself and...and your cock home! Soon!”

“Just make sure your chores are done.”

So I went back to finish the pots and pans.

Around twelve-thirty I could hear Penny’s key in the door. I stood naked in the middle of the living room, as she walked in and gave me one of her sweetest smiles. “Have you been a good boyfriend?” she asked. “My boyfriends must always do my housework. I don’t like to spring that on them until I know they really like me, as you do. Now let me take a tour and see how well you’ve performed. Just stay there.”

I caught a glimpse of myself in the mirror on the wall, my face blushing and my cock angled up—stiff but only about the size of a thumb. I looked truly naked and submissive. Sometimes, in my fantasies when I was masturbating, I thought that was actually my most natural state. Anyway, Penny took awhile with her inspection tour, and I could hear her making little criticisms out loud as she checked my work. When she came back into the living room, she was holding a small towel. She said, “You could have done a better job. Maybe you weren’t concentrating well. I think a spanking should teach you to work better.” She pulled up a chair and put the towel across her dark-skirted lap. Then she dragged me over her lap by my wrist and pressed my small but stiff cock against her lap, which was protected by the towel. Ohmigosh, I thought, I can feel her own cock through her skirt, pushing up at me. She had never felt so hard when we were just making out. I was going to be blowing that cock soon. It was going to fill my face...suddenly the first of many smacks came smashing down on my bare ass. I felt like I was in a dream. I began to cry, it hurt so much. I had never been spanked before, ever. But I was leaking all over her skirt too, close to orgasm. Penny was telling me I would have to be a better boyfriend in the future, and that meant learning to clean properly for her. My ass was stinging and sizzling. Her cock felt monstrous as it pushed against her skirt and the towel, right into my own crotch. What a wonderful position to be in...I couldn’t help myself. I tried not to cum, but it was useless. I began to twitch and squirt as she kept smacking my behind. She was telling me how bad I was, and how I’d have to be spanked often...bad boy, bad slave...it was the most wonderful experience I had ever had!

Finally she pushed me off her lap, tossed the now-cummy towel on the floor, and told me to kneel in front of her. She had that sweet, girlish smile again, and you’d never know she’d just been sadistically slapping the hell out of my butt. As I looked up at her, she said, “And now, boyfriend, I want my lunchtime treat before I send you back to your chores.”

I stared as she took off her skirt and pulled down her pantyhose and lacy white panties to reveal a cock that was thick and dark and powerful looking. It didn’t seem to go with her ultra-feminine, ladylike appearance, but there it was: thick, uncut, almost menacing. She held it in her hand as if it were loaded with something that could be set off with a mere jostling, like nitrogylcerin. That was my girlfriend’s cock. Just by seeing it, I was surrendering to it. The aroma of her flowery perfume mixed with the musk of her crotch. “Look how hard I am!” she said. “Look how much it needs to be sucked. Bring your mouth closer, darling.”

I was ready to do whatever she asked...

The conclusion, Part 3, “My Beloved’s Beautiful Load,” follows immediately!

[squirtsilly]

THE ROMANTIC TRANNYCHASER by Squirtsilly
Part 3: My Beloved’s Beautiful Load

Penny took off the rest of her clothes and sat down on a chair in the middle of the room. Her cock, however, seemed like the center of gravity for me, sucking in all the energy in the room, all the air, even as I shuffled over on my knees to get close to it. There was a drop of pre-cum on the chair. Penny was obviously hot from everything we’d been doing. I think she’d gotten excited not just from giving me the spanking, but from walking around her apartment and criticizing my housework. After all, Penny had been waiting for this uninhibited encounter as much as I had.

She was sweet, but had a sadistic sexual side that was well matched with my obsession to serve the whims of a female.

I took my girlfriend’s dick in my hand—I love that phrase, my girlfriend’s dick—and felt its hotness, and the satiny tautness of it, and the bulky, almost obscene weight of it, and the sweat of it from where it had been encased in her lacy panties and pantyhose only a few minutes before. Penny smiled and told me to be a good boyfriend and do what I was told. “Suck my dick!” she said firmly but girlishly. “You know you want it bad.” I opened my mouth. I could barely fit the beautiful thing in my face, but I tried. I opened wide and felt it move down my tongue and then I clamped my lips over it. My lips were stretched wide and were snug against her meat. I gently held her balls and sucked with a soft squishing sound.

I looked up at Penny and she wasn’t smiling now. Her face was scrunched up in that look of arousal and ecstasy that I had seen the other night. That got me so turned on I had to rub myself, even though I had just cum a few minutes before. Meanwhile, my ass stung from her smacking hand. What a sissy that made me feel like. I had been spanked, and I had cried, and I had cum on top of it all.

But I would be Penny’s sissy...

Her dick was so thick I couldn’t suck it up and down, but just kept it in my mouth and suctioned. I could only imagine what it would feel like if she put it in my ass, as I had a feeling she would, sooner or later...

The only sounds in the room were my mouth and her moans. It didn’t take long, Penny was all pent-up with waiting just as I had been, and then suddenly she could take it no more. “Move back,” she said, “I want you to watch me cum, and I want to see it too!”

I slid my lips off her cock, strings of drool and pre-cum only breaking off when I was more than a foot away. Penny was trembling as she looked at me, deadly serious now, and took her meat in her hand. She was shaking right down to the tips of her well-manicured fingers. “You’ve been a good boyfriend,” she said. “You cleaned my apartment, and you sucked me so well, so nice. I think I’m going to keep you...as my cocksucking sissy slave. Oh yes, that’s what you’ll be and you’ll love it for me!” And at those words her juice burst out, and Penny moaned and almost cried as she arched her back and pressed her cock against herself as if she were afraid it would fly off in the explosion of her relief. I stared, watching the cum pulse up and down her crotch, puddling like a lake of cream in her pubic hair. How beautiful it looked, all the cum on her tummy, all the cum on her tip, all the cum in puddles on her chair...

Words were unnecessary now. I pressed my face against Penny’s warm bare thigh and stared at her dick. She stroked my hair. Soon lunchtime would be over, and she would send me back to my chores, to correct the mistakes I had made. Would she come home after her day’s work and want to fuck my ass after checking on my housekeeping progress? Well, whatever she wanted, I was ready to receive.

I guess you might say I’m romantic that way.


--The End of a Happy Beginning!--

[spolverone]

nice dream, nice story!!!

it's my dream

ciao

[squirtsilly]

Glad you liked it, spolverone. Thanks for commenting!

[KimmyFur]

I enjoyed that.
Hopefully you'll continue the story!

[squirtsilly]

I enjoyed that.
Hopefully you'll continue the story!

Thanks, KimmyFur. I don't know if I'm going to keep going with this one, but there will definitely be more stories that I hope you will like!

[Jeffrey_L]

really great story

Squirt silly I sent you a PM. Please take a look at it when you have a moment

[squirtsilly]

Just thought I'd bump this thread up. Wrote this story few years ago, but I think it still reads pretty well. Hope you enjoy it!

[squirtsilly]

Since I bumped this story a week ago, it's gotten over 330 views, which is nice; but since there have been no comments, I wonder what the reactions are, if any. Do people read the story, or just look at the pix and then move along?

If you read the story and it evokes any reaction in you, good or bad, please leave a brief comment if you can spare the time. Even a single sentence is fine. I would really appreciate it. I like writing these kinds of stories and am thinking of writing more, but it's hard to write without any sense that I am communicating and reaching readers. Maybe I'm not...maybe the story sucks...although I don't think myself. I wouldn't have put it up if I didn't think it was readable and entertaining.