Restructuring Pt. 03

Story Info
A restructured Regina has a date...with a man.
2.4k words
4.47
21.9k
15

Part 3 of the 3 part series

Updated 06/09/2023
Created 01/17/2020
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

My wife said, "Well now it's just us girls. Leland is going to a bar to watch the football game with some pals. But it's only 4 pm."

Looking at Diane she continued, "It's so great to have you here, Diane, after so much time. It's great that we are re-connecting...and that our husbands get along so well. Ha Ha."

"Yes," Diane agreed. "There is some good chemistry there." She said, laughing heartily.

Meg asked, Shall I have our little vixen prepare a nice dinner or should we go out?"

Diane answered, "I would love to go out but it would be a shame to have to leave gorgeous Gina behind. That would be like the mean sisters and Cinderella."

They both laughed when Meg added, "I would love to bring her. Maybe she will meet her prince."

Diane pleaded, "Oh let's, Meg. Please. She might meet Mr. Right and get asked on a date. After all, we would be with her to keep things under control and protect her from any embarrassment."

After a good amount of flattery about my looks. ("Oh, what a fox you are, Gina!" "You rock that little black dress." "My little sex kitten." Those lips are the lips of a sultry seductress." etc.) a lot of urging, coaxing, and persuading, I finally agreed to go out with them provided they would bring me home if it got uncomfortable for me.

They both got ready to go out and in a while descended into the living room looking hot to trot. Meg was in a silver tube top and black spandex skin-tight pants with stiletto ankle boots. Diane in a light pink sheer blouse (through which could be seen a sexy black bra) and a charcoal gray mini skirt, black nylons, and black high heels. I had on my little black dress, sheer toe black stockings attached to my garter belt, open-toed stiletto pumps.

After they spritzed me with perfume, checked my make-up, and pinched my cheeks (all 4) we drove downtown. They discussed where to go. Diane suggested a place. It was a pub type restaurant bar and grill.

As the three hot babes walked in we got quite a few looks. There were a lot of guys watching football on the screens and there were tables for diners. The cheerleader hostess walked us to our seats and said, "Enjoy your dinner, ladies."

Meg said, "See Gina. Nobody here thinks you're anything but a girl. Remember all I taught you. Cross your legs or keep your knees together."

I said, "I know what you mean. Some guy grabbed my ass when we walked in."

We chatted and dinner was uneventful. When all the hoopla died down from the football game a lot of the guys there started drifting out. That's when we noticed Leland and two guys drinking at the bar. Leland noticed us and brought over his two friends to meet us. I was very nervous, and decided to smile a lot and be quiet so as not to reveal my voice too much. He introduced his friends Antonio and Jack. They were two very good looking guys but I knew that Meg and Diane would protect me if either one made a pass. What I didn't know was that they thought Antonio would be great for my first date with a man.

I stared into their eyes and smiled at them when they spoke, just as Meg and Diane had told me because men like to talk and expect girls to listen...intently.

After a polite five minutes they left.

Meg said, "Wow, what duds! They didn't flirt or come on to us at all. Unbelievable with the three of us looking so good! All the other guys in this place were fucking me with their eyes. "

Diane started to laugh uncontrollably and we couldn't get her to stop spitting her drink. When she calmed down she said,

"They didn't come on to you two because they're both gay. They're hairdressers in my salon and Leland knows them because he's our accountant."

"That means they both thought Gina was a real girl!" Meg exclaimed (a little too loudly for my liking.)

Diane replied, "Yes. But Leland, I'm sure, will straighten that out."

I was shocked to hear that and said, "You mean Leland knows I'm a guy?"

Diane answered, "Yes, after that hot blow job you gave him, I had to tell him. He thought you were a girl when you were doing it. I didn't want him to get any ideas about you. You did look hot and seductive... and men are men... at least most of them."

We ordered dessert and then asked for the bill. Just then, Antonio walked back into the pub. He waved and walked over to us and said, "I forgot my credit card. I hope the same bartender is still on duty." All the while he was looking at me and definitely was flirting. He walked to the bar and retrieved his card. Meg and Diane got giggly and whispered, "He likes you, Gina. No doubt about it. Leland must have told him you are a guy. Why else do you think he came back?"

Antonio came back to our table and offered us all a drink. From that point on he was charming, Most of the time he was looking at me and I was blushing, I'm sure. As we readied to leave he put his hand on my knee. I thrilled at the touch of his big hand on my ultra sheer stocking. He looked me in the eye and said, "Can I have your phone number?" I didn't know what to say or do.

Meg said, "Gina is staying with me at my home. Here is our number."

We all left and Antonio went his own way.

Diane looked at Meg and said, "He's a dreamboat and he likes Gina. I bet he will call."

The next day, sure enough, Antonio called and invited me to dinner that night. Since Meg had already told me to accept, I told Antonio, "That's sounds lovely, Antonio. I would love to have dinner with you. OK, I'll see you at eight o'clock."

Meg was very excited about my upcoming date and said we should go to Diane's house and tell her the news. When we got there I knew they both would have all kinds of tips and suggestions for me on how to act, what to wear, etc. As we entered the house I saw Leland's car in the driveway and was feeling apprehensive and a bit intimidated and was hoping that Leland wouldn't spank me again. Antonio had said that we were going to Chez Brigitte on our date which is a dimly lit, romantic French restaurant and both Diane and Meg knew of it. Diane said, "That is one of our favorite restaurants. Leland loves it."

Then, Leland, who was upstairs, came down into the room and said hello to us all and continued,

"So how is my favorite little cocksucker today? Meg, Did you bring her here for a second date so I can fuck her little faggot ass?"

I was not in the mood for this taunting and said,

"i'm no faggot."

Leland laughed and the women looked at me with raised eyebrows.

Leland continued to mock me.

"C'mon girl, I know you were very busy at the time but you should have seen the way you so slavishly swirled your tongue on my cock, slurping, sloshing, and slobbering on my snake as it slithered in and out of your slutty mouth. C'mon girl tell me you don't want me to slam it up your tranny slit."

Diane stopped him when she said,

"Stop it Leland. Regina is our guest. Stop talking like some brutish gay basher.

Leland departed and the girls began discussing what I should wear that evening. When they had decided, Diane gave me a manicure and pedicure and , later, we returned home.

Antonio picked me up at eight and we left together.

Shortly after being seated at a quiet little table in the corner, Antonio recognized someone who walked in and waved. My back was turned and I didn't notice the person. Antonio said,

"Hey it's my friend Jack. You met him last night. Hey Jack, what are you doing here?"

Jack said hi to me and responded to Antonio,

"I have a date meeting me here at 8:30."

Antonio said,

"We can wait. Why don't you two join us for dinner? We just arrived. Have a drink with us."

Jack sat down. We were served cocktails. Since I knew that Jack was gay I expected his "date" would be some guy. Five minutes later, Jack stood up and waved to someone at the door. It was a good looking blonde in a fabulous red dress and red spike heels. She waved and came towards our table.

As she approached I thought she looked familiar but couldn't really place her.

She kissed Jack and Antonio and before I could say anything the blonde said,

"Oh, it's Regina! So great to see you again."

She knew me! I was startled and speechless because I didn't think I knew the woman, and then it dawned on me.

I said,

"Leland?!!

She winked and whispered,

"Yes sweetheart, I'm Leland but when I'm dressed for play my name is Leanne."

She sat down with us. I was still in shock that the guy who spanked me, called me a faggot, and talked to me so dirty, was actually a sissy himself.

She put her hand on my knee, caressed it under the table and said,

"Come with me , Gina, let's go to the Ladies room."

As I got up I heard Jack say,

"Sissies are just like women. They always go to the Ladies room together."

I had never been to a Ladies room and was very glad that Leanne accompanied me.

My conversation with Leanne in the Ladies room was mind-blowing.

As we stood in front of the mirror putting on more mascara and touching up our lipstick she told me the real story.

She said, "As you might imagine, all of the events of the past few days were arranged by Diane and your wife. They hadn't seen each other since college and Diane gave Meg the idea of restructuring you. When they met again at your house and rekindled their lesbian relationship they asked me to help bring you out into femininity. Since I'm a sissy too, I knew that treating you and talking to you dirty like that would have the desired effect. I know it does with me."

I was still in shock, especially when thinking that my wife was a lesbo bitch.

Giggling Leanne said,

"Let's go. Our dates are waiting."

Now back at the table, I was relaxed and feeling at ease that I was out in public dressed as a sissy and was successfully passing as a woman. I flirted with Antonio. He was such a nice guy and after learning the news about my wife Meg's being a lesbian, I had had more motivation to please Antonio. He placed his hand on my knee and I let him. A short while later he did it again, only a bit higher up my thigh, caressing my leg through my sheer nylon stocking. After he refilled my wine glass, I decided to push things along and I placed my hand on his crotch until I located his cock, and I squeezed it tenderly. He smiled and placed his hand on my thigh and caressed the area just above my stocking top. I was being felt up and I loved the sensation. Antonio stopped when the waitress appeared to ask us if we wanted anything else.

Antonio said, "No thanks, we have to be going." Leanne and Jack were oblivious to us as they were playing kissy-face with each other. We said good-bye to them, Leanne winked knowingly at me and Antonio accompanied me to the parking lot while holding my hand. I put my head on his shoulder and he put his arm around me when we walked. I felt like his girlfriend and was really enjoying all the attention. He opened the passenger side car door but before i could get in he embraced me a gave me a long lingering, wet kiss. I responded enthusiastically to his advance and our tongues dueled for a few minutes. I got into the car and as he walked around to get in the driver's side, I leaned over and unlocked the door to show him that I wasn't a selfish bitch but really, I couldn't wait to be alone with him in the car in that almost empty, dark parking lot.

We began kissing again and I groped his crotch and felt his cock which was as hard as an iron pipe. This was the moment. It was now that I would try to please my date. I opened his belt, unzipped him and exposed his rock hard member to my kisses. I couldn't wait to suck that cock and got to work licking and sucking it until he came in my hot mouth. I knew I had to swallow it all or else I would ruin my makeup or stain my dress. I swallowed every drop as he caressed my cheeks.

We drove back to the house mostly in silence. I stared out the window dreaming about what I had just done and dreaming about the whole evening.

When we arrived in front of the house, he kissed me goodnight. We were still in the car kissing as I felt him grabbing my ass very firmly. My legs were not together and I was flashing my stocking tops and garters. That's when he slid his finger into my sheer nylon panties and probed my boi pussy with his finger. I let him. It felt so nice.

I was being finger fucked by a guy. In my mind my masculinity was only a distant memory. I felt so hot and disgraceful but I loved it. I couldn't let it go any further as there were lights on in the house and I knew that Meg was still awake.

We said good-night and Antonio said,

"Let's do this again soon."

I blew him a kiss as I sashayed towards the front door accompanied by the sound of my stiletto heels on the pavement.

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
AnonymousAnonymous6 months ago

The wife said she would not put him out and she did that's not right not right at all I know it's just a story but still the wife should not ever have done that

cdCindy1cdCindy1about 4 years ago
wonderful story

This really turned me on and hit me hard because this is truly my dream. I fantasize all the time about going out on a real date in public with a man who treats me all evening like the sexy sissy feminine slut that I am. Then, finding out that my wife is a lesbian would be the ultimate high.

Please tell us the next few chapters. I can't wait.

BrendaNWBrendaNWabout 4 years ago
exciting story

Thank you for a loving the story and part 3 continues it well. Please write more if you have time and desire. TG Tiffany

Share this Story

READ MORE OF THIS SERIES

Similar Stories

Substituting for My Wife I substitute for my wife with her boyfriend when she's away.in Transgender & Crossdressers
The Deal Freddy's wife convinces him to dress up and go clubbing.in Transgender & Crossdressers
A Harmless Favor A young wife assists her young husband to become a sissy.in Transgender & Crossdressers
The Babysitter Babysitter guy becomes babysitter girl.in Transgender & Crossdressers
A Husband Named Cathy A husband's dream comes true. He becomes Cathy.in Transgender & Crossdressers
More Stories