Julie Goes to a Wedding Pt. 03

Story Info
A sissy dresses "pretty" for the first time.
3.6k words
4.18
3k
2
0

Part 3 of the 8 part series

Updated 04/27/2024
Created 03/21/2024
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

Hello Readers. I am starting a new series. This is a bit different in that my previous works are based on mostly real experiences. This series will be a mix of fact and fiction. It will have quite a bit of BDSM and "bodily functions." If that is not your thing, please read one of my other stories. Finally, everyone is 18+ and all activities were consensual.

My name is Julie, I am a sissy that has been living as a woman all my adult life. I live with 4 other genetic women, my wife, Nancy, my sister and her wife, Becca and Annie and finally our aunt, Aunt Patti. All of us are submissive except for my aunt who is the Domme of the family.

The other woman involved is Marsha. She is my boss at the library I work at. She is the only one that knows what is really between my legs. Everyone else is convinced I am a genetic woman.

In the last chapter we met a kinky female couple in a diner. The Domme of the couple (Judy) had just discovered I was a sissy and offered to help relieve me of my erection. Here is how the chapter ended.

Judy leaned over and took my clit in her mouth and started to suckle me. Between watching all that had happened so far and Judy's expert cock sucking, I knew I would not last long.

As I started to spurt into Judy's mouth, I suddenly felt extreme pain on my clit. As I was spurting in Judy's mouth, Judy was viciously biting on my clit and twisting on sissy balls. I was screaming, but the knickers in my mouth muffled the sound. The intense pain only added to my pleasure, and I continued to cum hard.

After I was finally done, Judy grabbed my hair and pulled my mouth to hers. First, she removed the filthy knickers from my mouth, then she pushed the cum from her mouth into mine. After all the cum was in my mouth, Judy broke the kiss and slapped my face hard and then spit on me.

Mistress Ursula watched it all and laughed, "Judy you are a woman after my own heart!"

I looked down and could see teeth marks on my tiny clit. I happened to look at Marsha, she was naked on her hands and knees scrubbing the floor. As she moved, her big tits jiggled and swayed. The scene was so erotic!

With my knickers still at my ankles, I helped Marsha finished cleaning and then we sprayed disinfectant on the floor.

I stood up and asked permission to pull my knickers up. Mistress Ursula nodded and then told Marsha to get dressed. Judy handed Marsha a towel so she could dry the piss on her face and tits before she got dressed. The scent of the piss on Marsha was still there. Mistress and Judy put there knickers back on and adjusted their dresses. In a moment we moved the table back to its location and took seats.

As the restaurant opened, everything looked normal. Molly returned and poured our coffee and we all smiled at each other sharing a secret kinky secret.

And now:

Mistress, Marsha and I sat there enjoying our morning coffee as if nothing had happened.

After a bit Mistress Ursula said, "Girls, aside from the wedding I am attending, there is another reason why I came to visit you. I have a dear friend that lives in the area. She lives with her nephew, because the boy's mom just passed recently. She has noticed her nephew has had problems adjusting sexually and asked if I could meet with her today. I would appreciate if you could come with me girls."

Both Marsha and I agreed and within the hour we were pulling up to a lovely home in a rural section of the state. The woman that greeted us at the door was quite lovely and invited us in. Her name was Rose, but everyone just called her "Ro."

After the introductions were done, Ro asked us to be seated. I noticed her skirt was quite short and showed off a great set of legs.

Ro said, "Ladies, I will get right to the point. My nephew's name is Greg and both my sister, and I noticed he is painfully shy around girls. On his 18th birthday my sister offered to let him fuck her, but when he tried, he was not able to get fully hard. Over the years, both my sister and I sucked him to completion, but he never really seemed to be into it."

"I think he is self-conscious about his body. He is not very big and what little hair he has on his body, he shaves off. Greg's father was a real piece of work and left my sister after he knocked her up. So, Greg has never had a male influence in his life."

"I know you girls are both whor...um I mean professional women and I was hoping you could help. I spoke with Greg about it and he is willing to try."

Mistress said, "Don't worry Ro, we are whores, and we are not offended by the term, but you were right. We are professionals. Julie and I have worked at in whore houses all our lives and we know how to help people enjoy sex. Julie and her family have been training Marsha for a few years to become a whore as well. You and Greg will be in good hands dear."

"I do need to ask some personal questions dear; I hope you do not mind."

When Ro nodded, Mistress asked, "Are you and Greg casual about nudity?"

Ro answered, "Oh yes, it's not unusual to see one or both of us walking around in just our underwear or completely naked. My sister was the same way."

Mistress nodded, "Good, now would you please take off your clothes?"

Ro looked confused, "I want to see your body to see if there is a reason why Greg does not get hard when he sees you naked."

Ro still seemed embarrassed, so Mistress told us, "Take off your clothes girls. That should help Ro."

It was obvious that Ro did not expect to see a clit and sissy balls between my legs but was polite enough not to say anything.

Marsha and I got naked quickly as did Mistress. That seemed to ease Ro's embarrassment and soon we were all naked. With her clothes off, the scent of the dried piss on Marsha's body was evident now.

Mistress explained, "Before we got here, we had a rather kinky session at a diner where Marsha got pissed on. I hope the scent is not offensive."

Ro was gracious, "Not at all, in fact I find the scent exciting. My sister and I used to engage in piss play and even scat play as well. We have always been lovers. In fact, Greg has caught us fucking a few times."

Mistress said, "Stand up Ro, hands on your head, thighs spread wide." Ro blushed as she obeyed and the 3 of us examined her like she was a prized cow at an auction.

After a bit, Mistress nodded, and Marsha and I got on our knees. I moved behind her and Marsha in front of her and we started to lick Ro's ass and pussy. In time, Ro started to moan and orgasmed. Once she settled down, we all sat.

Mistress asked Marsha and I, "Did you notice anything ladies?"

Marsha said, "Her pussy has a lovely scent, and she obviously keeps herself clean. That should not have been a turn off for her nephew."

When Mistress asked me, I answered honestly. "I did notice he had not wiped her ass very well and her shit did have a stronger scent than I am used to."

Ro started to blush and seemed to be on the verge of tears.

Mistress held her hand and gently explained, "Sweetie, all of us here are into scat play and love it, so please do not feel embarrassed. But we are also quite aware that shit smells. Because of that, we rarely use spices and eat lots of fruit, By doing this our shit does not have a nasty smell and tastes sweeter that way."

Ro apologized to me and said, "While my sister and I always did scat play with each other, we never involved Greg and Greg never did anal on either of us, so I doubt that is the issue."

Then Mistress explained to Ro, "Julie is a whore dear, but she has also been a teacher as well. I mention that only because that gives Julie a great insight into how young people think and act."

Ro looked at Julie, "I was shocked when I noticed your genitalia, I never would have suspected. You are beautiful. Any insight you have about my nephew would be so helpful."

Mistress said, "Let's do this. Suppose you come to Julie's place in a few hours with Greg and we will see how things work out. Just warn him ahead of time that things may get sexual. Okay?"

After Ro nodded, I added, "Do not tell Greg about my secret Ro. I think I may have hit upon what Greg's issue might be."

Ro and her nephew, Greg, got there at 2 PM. Introductions were made. Marsha and I curtsied submissively to both Ro and her nephew Greg. That confused Greg and Mistress explained that we are in a very kinky lifestyle and that Marsha, and I were slaves. Greg seemed to be disinterested but was polite.

Mistress explained, "We are also whores Greg and would like to help you. Mistress nodded to Marsha who took Greg by the hand and said, "If it pleases you Sir, I would like to take you into the barn and fuck you."

The word "fuck" seemed to catch him by surprise, but other than that, Greg was not overly interested.

As they went into the barn, Mistress and I brought Ro to the sitting area and put the television on. In a minute, Marsha and Greg came on the screen. Mistress explained to Ro that every inch of the house and barn is on CCTV. We could watch everything that was happening.

We watched as Marsha took off her clothes and then undressed Greg. Greg's cock was semi hard, and Marsha worked to make him harder. Though she was new as a whore, she was talented and used her skills well. Unfortunately, she could not get Greg passed the semi hard stage and after a while she asked Greg to stay in the barn as she came back into the house.

Ro said, "This is what happens with me and my sister. He seems to enjoy it and given enough time, he will cum in our mouths, but will never get fully hard."

I looked to Mistress and said, "I had expected as much, with your permission Mistress, I think I can get him hard." Mistress nodded and I went into the barn.

Greg was still naked, and I got a good look at his body. He was smooth all over, other then his head, and a patch of pubic hair.

I smiled and curtsied and said, "Sir, with your permission, I would like to undress. Would you like that Sir?"

Greg seemed to be embarrassed at his inability to get hard and said in a curt tone, "Look, this is not going to work. Let's just forget this and my aunt and I will go home."

I touched his cock and said, "Please Sir, let me try and if it does not work, we can forget it ever happened."

He shrugged and I started to take off my clothes. I slipped my sun dress over my head and stood there in my bra, knickers, garters and stockings. He smiled politely, but his cock did not change.

I turned around and asked him to unhook my bra. He did so and I turned so he could see my tits. I started to rub my tits in front of him and pulled at my nipples. "I love doing this to myself Sir."

His cock seemed to get a bit harder, but he still was not overly excited. "Would you like me to take off my knickers Sir?"

He responded, "Sure why not. I have seen cunts before, my mom, my aunt, that girl Marsha. I mean they look nice, but don't do much for me."

I smiled, "I think you like what you see Sir." With that I slipped my knickers off and exposed my clit and sissy balls. That got his attention!

"Holy shit, you are really a dude!"

I smiled, "Does that disappoint you Sir? I am a sissy. I have lived my entire life as a woman.

I cupped my tits again and jiggled them. "My breasts are real Sir. I have been on hormones my whole entire adult life. They give me nice 36D tits but have made my clit small Sir. Do you like how I look Sir?"

For the first time, Greg looked interested, and I noticed his cock was starting to stir. He said, "May I touch them please?"

I smiled and offered them to him, "Do whatever you want to me Sir."

Greg started to fondle my tits. As he did, I played with his cock and balls, and he finally got hard. I leaned in and kissed him hard and continued to fondle him. He started to moan. I gently pushed his down to his knees, so he was at eye level with my hard clit.

My voice was a bit more demanding, "Take it in your mouth Sir and suck me." He looked in my eyes as he took my hard clit in his mouth and started to suckle me.

In the house, Ro was shocked. "I never suspected he was gay."

Mistress explained, "He is not gay in the traditional sense dear. He likes the idea of a beautiful woman like Julie that has a 'little extra' in her panties."

I stroked his hair as he continued to suckle my clit. "Have you ever sucked a cock before Greg?"

He never stopped sucking me as he shook his head "no."

I knew I had figured him out. "You are smooth and feminine looking Sir, would you like me to teach you how to be a sissy?"

I thought he was going to cry and when he sucked me harder, I knew I had hit a nerve. I held his head still and started to move my hips as I fucked his face.

As I got closer, I said, "I am going to cum in your mouth, and you are going to swallow every drop. Understand girl?"

He never had a chance to respond as I came hard in his mouth. As instructed, he swallowed every drop. After I had finished cumming, I had him stand up and we hugged and kissed hard. I could feel his hard cock pressing into my clit as we kissed.

The he said, "Why did you call me a girl?"

I smiled and explained, "From this point on, you are a girl dear. Instead of Greg, your sissy name will be Jane."

I brought "Jane" her stockings and helped her put them on and then she stepped into her garter, and I attached the stockings. I took Jane by her cock and walked her to a full-length mirror so she could see herself. With her cock in my had I explained, "From this point on, this will be your clit dear. I cupped her balls; these will be your sissy balls."

I looked into the camera and said, "Marsha, please get our shaving supplies and false tits please dear. Then would all of you, please come into the barn?"

As we waited, I handed Jane my knickers and told her to put them one. As she did, her clit poked through the top and I smiled, "We will tend to your hard clit in a bit dear."

The other women came into the barn and Ro hugged her new niece tightly. "Oh Jane, I am so happy for you!"

I slipped her knickers down and quickly shaved off her pubic hair and slipped them back on.

I helped Jane into her bra and then slipped a pair of 36D silicone tits into the cups. I smiled, "Before my sister, Becca, started to develop tits, she would put these silicone tits into the cups of her bra. Before the hormones I had started to take, I used these 'tits' too. Now I am giving them to you Jane."

I saw a tear drop from Jane's eye and I kissed it away. Finally, we helped Jane into the sun dress and let her twirl around. Jane was thrilled! Finally, we put a blond wig on her head, and she looked in the mirror. She cried out, "Aunt Ro, I am a girl!"

Ro chuckled, "You are dear, but we will have to do something about that hard cock!"

Mistress said, "It is a woman's job to get fucked dear. Bend over the hay bale."

Jane never hesitated and bent over. I pushed her dress up and over her hips and pulled her knickers down. Then I reached for the lube Marsha brought in and started to finger her asshole. Her moaning told us how much she was loving this.

I positioned myself behind Jane and slipped my clit into her asshole. Ro knelt in front of Jane and said lovingly, "You are losing your virginity dear, you are becoming a real woman. I am so happy for you."

Ro and Jane started to kiss as I started to fuck Jane. I could feel my sissy balls slapping along her ass cheeks as I drove my clitty deep inside her asshole. When I came, I came hard. The hormones that make my clit small. Also make it possible for me to cum a lot and often.

After I was done cumming, I slipped my clit from Jane's asshole and Mistress nodded to Marsha. Marsha got behind Jane and licked her pretty asshole clean.

Mistress than said to Ro, "Lick Julie's clit clean dear, but when you do, take special notice to how her clit tastes.

My clit was covered in shit from fucking Jane's asshole. Ro got on her knees in front of me and licked my clit clean. Mistress explained, "Make it a point to remember that taste dear. In a bit you will see the difference."

After she was done, I smiled at Jane. "Your turn dear. Are you ready to cum for your first time as a woman?"

Mistress said to Jane, "Pull your panties down and lift your dress dear. Get behind Julie and give her a good fucking."

Still naked, I took Jane's hand and led her to bales of hay in the barn. I took the lube that Marsha brought with her and lewdly reached back to finger my asshole. I moaned softly and bent over wiggling my sexy ass.

Ro helped Jane guide her rock-hard clit into my asshole. Once I could feel her sissy balls on my ass cheeks, Jane started to fuck me hard and fast.

It seemed like years of frustration were coming to a head as she fucked me. When she came, she came hard and long. I could feel her cum dripping down my thighs as she fucked me. When she finally finished cumming, she leaned over me and I could feel her tits pressing into my back.

When Jane slipped her clit from my asshole, as expected it was covered in my shit.

Marsha got behind me and started to lick the cum from my asshole.

As Marsha licked me, Ro got one her knees and started to lick the shit from Jane's clit.

As she did Mistress asked, "Do you notice the difference in taste dear?"

With Jane's clit in her mouth, Ro answered, "It does not smell, and it actually has a sweet taste to it. I love how it tastes and smells Mistress."

Mistress explained, "That is the difference in diet dear. I have seen you eliminating spices by tomorrow, your shit shoe be just as nice."

All the time Ro was licking her niece's clit, she made loud nasty slurping sounds. Jane's clit never went down as she did.

Mistress looked at Jane's clit and smiled, "I think she should be able to fuck you dear. Why not get on your hands and knees and let Jane give you a good proper fucking."

Still wearing her sundress, Jane got behind her aunt and Mistress guided her clit into her aunt's wet cunt. Mistress got behind Jane and took Jane's hips in her hand and guided her so that she gyrated her hips as she drilled her clit into her aunt's wet pussy.

Like she did in the diner to Judy, Mistress reached down into Jane's sundress and tweaked her nipples. As she did, we watched as Ro's big tits jiggled and shook until she finally screamed and came all over Jane's clit.

That was too much for Jane and she emptied her sissy balls into her aunt's cunt. They both collapsed on the ground, trying to catch their breath while Jane's clit was still inside her aunt.

In time, Jane's clit went down, and she stood up, her clit was dripping cum down her stockings.

Ro finally rolled over on to her back, her cunt leaking as well, with her legs spread wide and said, "You like being a sissy Jane?"

Jane giggled like a little girl, "I love it Aunt Ro! Can I dress like this all the time?"

Mistress answered for Ro, "If you are a good girl, we will take you shopping and your new life as a sissy cane begin tomorrow."

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
Share this Story

Similar Stories

Cuckslave Begs to Serve Mistress frustrates her slave until he begs to serve.in Transgender & Crossdressers
Searching for a Black Master A young curious white couple discovers a very taboo website.in Interracial Love
Porn Star Mother -- Illustrated Busty mother uses body to help son's career.in Illustrated
Caught Wearing a Bra! Pt. 01 Will a simple pat on the back from the boss cause a problem?in Transgender & Crossdressers
Birthday Present Wife takes him to first swing party for his birthday.in Exhibitionist & Voyeur
More Stories