A Natural Sissy Ch. 07

Story Info
Stacy has a bad? morning.
1.6k words
4.25
62.4k
8

Part 7 of the 8 part series

Updated 10/30/2022
Created 06/01/2007
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
harv069
harv069
102 Followers

Author's note: This is a story about a young woman turning an older man into a compliant, sissified plaything. If that idea doesn't appeal to you, don't read the story. If you don't like this kind of story, but read it anyway, please don't bomb me. I warned you to go away. If you like the idea, read on, and don't forget to vote and leave a comment. More will be added if comments from readers justifies it. Sorry about the delay in getting this chapter up. Real life gets in the way at times.

Ch. 07 Stacy has a bad? morning

The next morning I slept in a bit. Stacy woke me by climbing onto the bed and spreading my legs as was the method prescribed for such times. Stacy was a world-class pussy eater, and I guess I have his sisters to thank for that. When my orgasm came I opened my eyes to see Stacy's face right in mine. He was grinning broadly, I guess with pride.

: Breakfast is ready, Miss Gail." He said. :"Or shall I keep it warm until later?"

"No, now is fine, Stacy. Set a place at table for yourself, too. We have something to talk about before we start the day."

"Yes, ma'am." Stacy was off the bed and out of the room before I could muster a reply.

When I got to the breakfast nook, the table was ready, and it was a heavy breakfast for us both. Stacy had prepared a dozen eggs, biscuits and gravy, sausage and bacon, orange juice, fresh fruit, and best of all, hot coffee.

As we ate, Stacy kept watching me, waiting for me to begin listing his assignments for the day. Well, I guess it's time to tell him. "When we finish breakfast just throw the dirty dishes in the sink, and go get dressed. We're going to visit Heather this morning. You remember my friend Heather, don't you Stacy?"

Stacy frowned. I knew he didn't like Heather. She was kind of uppity, I guess, but I still counted her as one of my best friends. Stacy was silent.

"Don't worry, sweetie, I'll not let her rape you again like the last time you saw her. We just need to set up an appointment with her for this afternoon. Now, let's get the show on the road, shall we?" I smiled at my boi toy in my most charming way. That always melted Stacy, and he would do anything to keep getting those smiles. "I have already laid out what you will wear to the meeting. We need to be ready to go in half an hour."

"Yes, Miss Gail. I'll start right away," answered the poor sissy as he rose to go dress. He wasn't aware of what I had set out for him, but I didn't expect any backtalk. He was too well trained now for that.

He would be wearing a modified male suit over lingerie. Matching red lingerie. Bra, garter belt with silk stockings, panties with an open crotch, and red patent leather high heel pumps. He would likely not like the blouse I had put out, but he would wear it. There was no doubt about that. It was a sheer white frilly thing that offered no concealment at all. His red bra would be quite visible. His "manly" tie would match his lingerie perfectly. It was solid red except for the design at the bottom, which read, "I give great head" in French script. Of course, he'd round out his ensemble with dangling gold earrings that brushed his shoulders when he wore them. His suit coat was unmodified, but the trousers were. I'd had a tailor fit then to his measurements in a way that made them skin tight. His cute butt would stretch the trousers to the point of slutty, and the legs would hug his thighs like he was poured into them. They were shortened to end at a cuff three inches above his ankles, so his stockings and high heel pumps would be very obvious. I had not put out a wig, so he's be wearing his natural male cut hair. Subtle pink makeup would round out his persona for the trip to the tattoo parlor that Heather owned and operated.

No, the tattoos would not be done in the parlor. Heather would come to the house, a much more relaxed atmosphere for us ladies. Not so sure about the sissy, though. He had mentioned that he'd like a feminine tattoo on his breast, and that's what he will think he's getting. He'll be right about that, but there would be moiré that he doesn't know about. I'll tell you about that later. Stacy's on his way down now, and we need to get going.

"Oh, there you are, sweetie. With just enough time to spare to take your Viagra before we leave. Hurry now, darling. Heather doesn't like people to be late for appointments."

We arrived at the strip mall where Heather's parlor was located at just the right time. All the stores were opening and customers abounded. I chose a parking place as far from the parlor as I could.

"Why... why... did you park so far away, Miss Gail?"

"Oh, because I have a cramp in my leg, and I need to walk it off. Come along now. We need to hurry."

As we made out way across the parking lot, Stacy was on full display to hundreds of mall shoppers coming and going. His high heels clicking on the pavement brought attention to the sissy, and his cock was plainly outlined by the skintight trousers he wore. I stopped him when he tried to button the suit coat, and of course his red bra was obvious to any who chose to look.

Finally, we were at the door to Heather's parlor, and she came out to welcome us. She and I hugged, like the dear friends we were, and then she looked at Stacy, her hands on her hips, her legs spread, stretching her mini skirt to the limit.

"Stacy, aren't you going to give me a nice manly kiss like last time we met? I'm sure Gail will time it for you."

"Uh... here, Miss Heather? Out here on the sidewalk?"

"Of course, right here, darling. Why would you think not?"

"There's a lot of people here. Inside wouldn't be so crowded."

"Crowds don't bother me. Are you going to kiss me, or not?"

I was almost ready to burst out laughing, I was so amused at Heather's antics. Stacy was really getting nervous now, I could tell. He was looking around to see how many people were nearby, and there were a lot of them.

"Er... um..."

"Come on, Stacy. Wrap your arms around me and give me one of your alpha type kisses, you delicious hunk of masculinity."

Talk about sarcasm, I thought.

Finally, Stacy decided that he was not going to get out of this predicament, so he knelt on the sidewalk, raised Heather's mini skirt, exposing her naked pussy, wrapped his arms around her luscious thighs, and began his kiss. Her pussy, of course. I understood that it was to be a three-minute French kiss so I timed it for them.

When it was over, a crowd had gathered, and applauded with gusto.

"Here, here!"

" Bravo."

" Good job, my man."

" Would you like to kiss me, too?"

Poor Stacy. He was beet red. Heather was quite calm. She unceremoniously grabbed Stacy's tie and pulled him along on his knees into her parlor. I followed quietly. This was Heather's show.

The actual discussion about the appointment was brief. Heather and I had already made all the necessary arrangements by telephone. This visit was just to humiliate Stacy. Every sissy needs that as often as can be arranged. Heather escorted us out of the parlor five minutes after we arrived, and demanded a goodbye kiss from Stacy. She also stipulated that she needed to see how Stacy reacted to the kiss, so he was to extract his clitoris (cock) and leave it exposed during the kiss. This was no small feat for a rock hard nine inch cock confined by skin tight trousers, and it too the poor sissy a good three minutes just to do that. He had to pull his ovaries (balls) out, too if he was to have any comfort at all.

The goodbye kiss lasted five minutes, long enough for Stacy to ejaculate just from the thrill of his embarrassment. I told you he was a natural, didn't I?

Before he could stuff his still hard cock back in his trousers, I grabbed it and led him, using his cock as a leash, across the parking lot to my car at the far end. Stacy said not a word the entire ride home.

Amanda called just as we entered the house. I sent Stacy to change clothes while I invited Amanda to visit during the afternoon while Heather was doing her chosen line of work in the recreation room downstairs. We'd use Jolle as our entertainment.

When Stacy was back downstairs, I asked, "Did you enjoy our little outing this morning, dear?"

"No!. Not one bit, and you know it." He was livid. He was wearing his usual lingerie with no outerwear.

"Oh, come on, Stacy. Your body said otherwise. I've never seen your cock any harder that when you were sergvicing Heather on the sidewalk in public."

"Well, I..."

"Well, you did enjoy it. I could see."

"I... I guess it was okay," the sissy conceded.

"Right on. Now get us some lunch ready, sweetheart. It's going to be busy around here this afternoon." I gently squeezed his rising cock, dismissing him to his chore.

After lunch, I sent him to the recreation room to get it ready as a makeshift tattoo parlor.

Just what would our sissy have to endure this afternoon, dear reader? Stay tuned. It's coming next

harv069
harv069
102 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
1 Comments
AnonymousAnonymousover 16 years ago
panty boy loved this story

I came in my panties so hard . Great story more please. I hope Stacy gets fucked soon.

Share this Story

story TAGS

READ MORE OF THIS SERIES

Similar Stories

A Slut is Born Young man forced to be a womanin Transgender & Crossdressers
Joel Gets Caught by His Wife Joelle is caught and dominated by his wife.in Transgender & Crossdressers
Feminized by My Girlfriend The start of how she changed my life.in Transgender & Crossdressers
My Girlfriend Made Me a Sissy A guy is transformed into a sissy slut.in Transgender & Crossdressers
Discovering Amber My boyfriend gets caught in my lingerie, changes must happen.in Transgender & Crossdressers
More Stories