A Sissy is Born Ch. 03

Story Info
You take me deeper into the sissy life.
2.4k words
4.32
52.6k
16

Part 3 of the 4 part series

Updated 10/19/2022
Created 12/12/2012
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

As the title indicates there are two previous chapters. They are quick reads and even if you've already read them a quick review will enhance the enjoyment of this installment!

*

When the reality of my situation became clear I began to panic. I was seated in a woman's car dressed as a whore and I had no idea where my regular clothes or car keys were! I began sobbing again. "What am I going to do?"

"There there, little girl." The woman tried to comfort me as she patted my stocking clad leg again. "Mama's going to take good care of you. Don't you worry your pretty little head!"

"Bu..bu..but. m..m..my c..car!" I stammered as I held my head in shame.

"First tings first, sweetie. Let's get you cleaned up and find some more presentable clothes then we'll worry about your car." She reassured me as we pulled into the drive of an old farm house. We were still in the city but the size of the lot and the numerous outbuildings gave witness to its former utility.

Distracted from the mess I was in for a moment I asked, "Where are we?"

"We're at my house, lover." She replied simply.

"Yes, Ma'am, but where exactly are we?"

"Not to worry, dear." She avoided giving me a direct answer. "We're only about a half mile from the hospital."

"But I've lived and worked here half my life and I've never seen this street or house before!"

"Why would you, honey. People with no business here seldom come up my street because it's dead end. My mail box is out on the main road; has been for over a hundred years. We sit so far back that the house is nearly invisible except during the winter months." She explained as she parked between the four car garage and the house. "You're safe back here, darlin'. The main road is two hundred yards down the hill, the Metro Parks surround us and the freeway is a good half mile behind us. There are forty thousand neighbors living within a three mile radius but for all practical purposes we are out in the country! You could be naked and no one would ever know. Fact is, during the summer I enjoy a little nude sun bathing myself but it's a little too cold now. Enough chit-chat, let's get you cleaned up and then we'll worry about your car!"

I followed her to the house. The back entrance was spacious, an all weather sun room, sort of. There was a bath tub on a raised platform on one end of the room. The wall next to the tub was lined with cupboards. There was a padded table over what looked like a seat-less toilet on the other end of the room. "This is different." I observed. "I don't think I've ever seen a bath tub on anyone's back porch before!"

"That's not my bath tub, sugar! My bath tub is upstairs in my bath room. I used to train Whippets and this is where I groomed them."

"Oh."

"You're going to get cleaned up here, though. Get out of those nasty things and get up here in the tub!" Her manner was calmly assertive as she began to draw the bath water. I hesitated momentarily. "Sweetheart, your penis and testicles aren't even covered by your panties any more! Just strip and get into the tub and let Mama give you a nice bath!"

I blushed as I realized how ridiculous I looked. I sat on the edge of the bathing platform and removed my shoes and stockings. She watched as I took off my wig and bustier. She smiled as I stepped out of the tiny panties. She offered me a hand. "Step up here and get in the tub. It's time for a nice relaxing bubble bath!"

I slipped beneath the warm water and under a cloud of fresh smelling bubbles. "Now tell Mama, doesn't that feel nice, sweet lips?"

I smiled. This woman was clearly young enough to be my daughter but she kept referring to herself as "Mama." It was odd but somehow appropriate. She was comfortingly maternal; pleasant and accepting. "Ah" I sighed as I closed my eyes and relaxed for the first time since I was left all alone at the medical offices.

"Isn't that better, lambikins, I'll be right back; I'm going to get some towels."

It was relaxing; the warm bath and the floral aroma of the bubble bath. I felt safe and secure even though I still had no idea of where my clothing and car keys were.

"Do you feel better, honey?" She asked sweetly as she re-entered the room carrying some large bath towels and some items I couldn't quite make out.

"Yes, Ma'am, I surely do."

She placed her load on the counter and walked to the end of the tub where I was reclining. She began massaging my neck and shoulders. I relaxed under her gentle touch. After a few minutes she said very softly, "Tell Mama how you got yourself into this mess."

"Well......" I hesitated, trying to figure out how much to say.

She moved to the side of the tub and began washing my chest with one of those spongy net things. "Look at me, little girl!" Her hand held my jaw. "I found you wearing ladies underwear and a wig in a public restroom. You had semen in your hair, on your face and clothing. I know you are a man who wants to suck cocks! I know you are a man who gets a thrill out of dressing as a woman. Don't be shy now, silly girl!"

"I don't know where to begin......"

"Why don't you start at the very beginning? The very first time you wore female clothing and then just go from there."

"Ok...but don't laugh."

"Oh, honey girl, Mama's not going to laugh....Mama just wants to get to know her new baby girl."

"It was the Halloween after I graduated from high school. There was a costume party at the Maxwell's down the street. I didn't have a clue what to go as and my mom suggested I go as an Indian girl. I half-heartedly objected but when I saw the sari she had in the back of her closet I knew it was going to be fun. Her sister helped with makeup and a wig. They shaved my legs from the knees down and gave me a pedicure. They darkened my skin, painted my nails and made up my face. I was wearing white cotton briefs. My aunt said that she thought I should wear panties. My mother said it wasn't necessary; no one was going to see my underwear. My aunt insisted saying that to go as a girl I had to feel like a girl and that meant wearing panties! It would help me play the part."

"So, did you wear the panties, sweet cheeks?"

"Yes, I did and it made me feel so sexy!"

"What happened at the party?"

"They told me to take very tiny steps when I walked and act as if I didn't understand English. It worked like a charm. None of my friends recognized me. When it came time to vote on best costume my mother nominated me. Everyone asked where I was. She said I had been there all night and brought me to the center of the room. She took off the wig and everyone gasped. I won hands down."

"How did that make you feel?"

"Wonderful, just wonderful!"

"Did you continue to dress up after that?"

"No, not for a long time. But I thought about it."

"So, when did you start dressing as a girl again?"

"Not until a few weeks ago when I met a guy on line."

"Do you meet lots of guys on line?"

"No, just the one."

By this time she was scrubbing my belly was the net thing. I was hard as a rock. I'm sure she knew. "Why would you look for a guy on line?"

"It just kind of happened. I bought lots of men's magazines and read lots of stories."

"You masturbated when you read them didn't you?"

I blushed. "It's OK, sweetie, everybody likes to play with themselves. It's the most natural thing in the world." She gently cupped my balls and squeezed. It took my breath away. "Do you like that?"

I nodded, unable to speak.

"Go on, lover, tell Mama everything."

"I read all kinds of stories but always seemed to like the ones about men who wore women's clothes."

"In some of the stories their wives or girl friends would make them dress up and then make love to them like they were a girl."

"How would they do that?"

"You know."

"Pretend I don't. Tell me what they did that excited you most." She was gently stroking my cock.

"Usually they would start by wearing a strap-on dildo and make the men suck it and then fuck them."

"Does your wife do that to you?"

"Heavens no! She doesn't know about this at all!"

"Would you like her to."?

"If she enjoyed it too."

"Do you think she wouldn't?"

"I think she'd hate me."

"That's too bad, Sugar. She doesn't know what she's missing. Continue, tell me how you ended up in that restroom sucking a cock."

"Almost all of the stories that I read were about sissy husbands who would suck their wife's lover's cock or eat their wife's lover's semen from her pussy after she had sex with them. Then I read about guys who looked for other men on line. I started to read ads like that and masturbate."

"And then you answered one?"

"Not just one! Twenty, thirty, I don't know how many."

"But you said this was your first time."

"It never worked out before. This was different. He said I had to prove I was a sissy."

"How did you prove to him that you were a sissy, honey buns?"

"He gave me a series of challenges and after each one I had to send him pictures. The first one was really simple; all I had to do was put on my wife's panties and bra and send him a picture."

"OK, what came next?"

"I had to buy lip stick and face powder and send him the receipts. The biggest challenge or hardest was to go into a lingerie shop and buy a bustier. Not just buy it but tell the clerk that it was for me to wear."

That was exciting, wasn't it, sugar?"

"I could feel my heart pounding in my chest almost the whole time. But she was so nice and polite that by the end I was very calm. I even bought thigh high stockings. Then I went to a party store and bought that cheap wig and a shoe store to get the high heeled sandals. My reward was to meet him at the medical building."

"Was it worth it?"

"All but being left by myself in that restroom!"

"So you'd do it again?"

"Maybe....well yes....if I had a little more control."

"Would you like Mama to help you look the part of a cock tease?"

"I'll never really look that sexy!"

"Maybe not but if you feel sexier you will be sexier."

"What do you think you could do?"

"For starters your eyebrows could use a little trim and those wild hairs in your ears and nose and if you're really serious I'd wax your back and chest and shave your armpits."

"That's a little too much! My wife would have a fit if she noticed."

"You're afraid your wife wouldn't approve?"

"Afraid? Not at all. I know for a fact she wouldn't approve. In fact, she'd be so mad that I'm sure she'd kick me out of the house."

"But you did it anyway, why?"

"I got carried away. It felt so sexy...so good."

"As good a sex with your wife?"

"We haven't had sex for a while."

"A long while?"

"A very long while, maybe twenty years."

"That's not right! Why do you stay?"

"The kids...the grand kids. Ninety-nine percent of our marriage is great."

She was still idly stroking my swollen cock and rubbing my balls. "I see." She sighed. "It's a shame; she could be having so much fun, too bad. Maybe I should tell her a thing or two."

"Don't you dare?" I blurted.

"Don't worry, sweetheart, Mama won't get you in trouble." With that she started draining the bath. She attached a rubber hose to the faucet. "Let's get you rinsed off." The water played over my chest and belly then my arms and shoulders. "On your knees, darlin, drop your head, dear." She rinsed my hair and back and then my butt. As the water ran between my cheeks her free hand was busy playing with my balls as her thumb massaged my anus. "Looks like your pussy needs a shave, gorgeous!" I blushed at the thought. "Straighten up, dear. I don't want any soap irritating your legs!" The warm water played over my legs and her free hand continued to stroke my skin. She cupped my balls and focused the water between my legs. "Stand up, lover!"

When the last of the soapy water was rinsed from my legs and feet she turned the water off. "Hold still now sexy, I'll get a towel." She went to the cupboard and pulled out a large soft bath towel and began patting me dry. When my legs and feet were done she helped me out of the tub and dried my torso and arms. My face and neck and hair were last. "Doesn't that feel better?"

I nodded my approval.

She got a hair brush and pointed to a chair. "Sit down, handsome, let me fix your hair."

How could I object? Being pampered and fussed over was something I wasn't used to. When she was satisfied she held out her hand. "I've got a fire going in the great room. Let's go in there and relax."

"But what about my clothes?"

She led me into the house. "All in good time, big boy."

"As we entered the great room a male voice called out. "I'm having scotch neat, what can I get you?" It was you standing naked at the bar!

The woman held my hand even tighter and pulled me towards the bar. "You two need to get acquainted. I'm going to freshen up."

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
3 Comments
cdCindy1cdCindy1about 6 years ago
just like my life (it was me)

The previous comment was from me (a few years ago). I wrote then:

"The situation in this story is very similar to my life - and the status of my marriage. My wife and I have a good life and almost everything is great - except sex, because we don't have any. Over the past couple of years I've turned to cross-dressing and I've had sex with quite a few men. I've sucked a lot of cocks, french-kissed a few men, and just recently I started to get fucked (only 4 times so far, but I want it more - so badly I want to get fucked a lot more times). Just like in your story, I wish I could tell me wife but I suspect our marriage would be over. I would love for her to get dressed in a hot black outfit with a big strap-on -- and then dominate me !!! I would love it if she fucked me hard and then watched me suck other cocks while she played with herself. I would love to be her bitch. Please continue this story."

The update since then is that I have continued to have hot gay sex with many men - sometimes I dress up (I'm an avid sissy CD) but sometimes it's just he and me both naked in bed. I've become a total bottom and my wife still doesn't know. I still wish she would dominate me with a big strap-on and I'd love it if she included her female (and male) friends from work. It would be hot and such a turn on to be the faggot slutty bitch for everyone. Please tell more stories like this one. It turned me on so much and I can't wait to read the next chapter.

sally_spandexcdsally_spandexcdover 11 years ago
Damn good story

Well part 3 was just as hot as the others but oh how I want part 4 now that our lil sissy is about to meet a new lover and yes I still hope our new lady friend turns out to have a big hard cock in her panties I really love the story line so HURRY as my pantyhose are wet for more.

AnonymousAnonymousover 11 years ago
Just like my life

The situation in this story is very similar to my life - and the status of my marriage. My wife and I have a good life and almost everything is great - except sex, because we don't have any. Over the past couple of years I've turned to cross-dressing and I've had sex with quite a few men. I've sucked a lot of cocks, french-kissed a few men, and just recently I started to get fucked (only 4 times so far, but I want it more - so badly I want to get fucked a lot more times). Just like in your story, I wish I could tell me wife but I suspect our marriage would be over. I would love for her to get dressed in a hot black outfit with a big strap-on -- and then dominate me !!! I would love it if she fucked me hard and then watched me suck other cocks while she played with herself. I would love to be her bitch. Please continue this story.

Share this Story

READ MORE OF THIS SERIES

Similar Stories

Being a Sissy for Viv Ch. 01 Pretty panties is all it takes.in Transgender & Crossdressers
A Sissy's New Daddy Billie is forced to be a sub-sissy.in Transgender & Crossdressers
Busted Wearing Panties Ch. 01 He's caught by his stepdaughter wearing her panties.in Transgender & Crossdressers
My Husband’s Birthday Sexual humiliation for his birthday gift.in Transgender & Crossdressers
Girl for Charlie Unexpected gay visitor gives him a chance to dress up.in Transgender & Crossdressers
More Stories