The Making of a Sissy Pt. 07

Story Info
Charlene and John set sail for the weekend.
2.2k words
4.56
5.8k
6
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

*recap*

Opa put a chastity lock on Charlene in the woods. It's finally the weekend.

*Part 7 starts here*

It was still Friday night. As we finished dinner John called in and Opa answered.

"Ok. I will tell him. Thanks for calling John." he said on the phone.

"Eddy, John called to ask you to meet him at his place at 7:30 in the morning. Make sure you pack everything you need, ok?" he came in the study and told me.

"Ok Opa! Thank you!" I replied.

He saw the big smile on my face and gave me a wink before he left.

I had to find an excuse to pack my girly things in the garage. Just as I was thinking i heard Opa shout from the living room "Eddy, can you help me find my working boots in the garage?"

I immediately jumped up. I knew this was his way of getting me to pack my girly things.

"Ok Opa" I said as I walked in the living room.

"It's in one of the boxes in the garage, I forgot which one, but you might have to go through them" he explained "and be careful moving the boxes from the top. take your time kiddo don't get hurt."

"Big day for you tomorrow, Ed, be careful" Oma added.

I walked in the garage and turned on the lights and immediately saw his boots resting in the far corner. This is why I love Opa. He's a smart man who plans ahead.

I grabbed my carryon luggage in the garage and laid it on the ground. I carefully took out the box containing all my clothes. I picked out everything we bought today along with pink lingerie and thong and my fishnet stockings. I saw the bottle of lube and dildo and decided to bring them also. I giggled as I fondled the dildo. Finally, I put my makeup box in the luggage.

I went back inside with my carryon luggage and the boots. I laid the boots on the side and walked to my room while they watched TV.

I then put in 2 t-shirts, black and white, a pair of briefs and socks. Finally, I zipped it up and locked it.

Later on, when we got in bed Opa set an alarm for 7:15. We hugged and kissed before we slept. I was so excited.

The alarm rang the next day, me and Opa both got up. I quickly brushed my teeth and put on some casual clothes then he walked me to John's house.

"Just relax and have fun ok sweetie? John is a good guy, and he won't hurt you or put you in any danger." Opa said as we approached John's front door.

"I know Opa." I smiled at him "Thank you again."

Opa rang the doorbell. John swiftly answered as I'm sure he was waiting already.

"Morning John! Here's our boy. Take good care of him, ok?" Opa said with a laughter.

"Morning Turner! Morning Eddy!" John replied, "You know we're going to have nothing but a good time."

"I'll get going now and leave you two to it." he said as he hugged me and kissed me passionately in front of John.

"See you soon Opa" I said as I made my way inside John's house. He was wearing a white t-shirt and beach shorts with flip flops on.

"I figured you'd need time to get dressed up and ready Eddy that's why I want you over this early" John explained "Breakfast? We don't leave until 8:30."

"Aw thank you John. And yes please." I giggled.

"You can use the bathroom in my bedroom if you'd like" he said as he walked towards the kitchen "breakfast will be ready when you are Ed."

I pulled my luggage into his bedroom and took out my makeup box, my wig, my lingerie, my denim shorts, a white t-shirt and my wedges and headed for the bathroom.

John's bathroom was BIG. A long mirror with a big countertop, a big bathtub and a glass shower. "How much does this guy make?" I giggled in my head.

I quickly had a shower. I walked out and took the butt plug and lube out of my luggage and returned to the bathroom to put it in place. Next, I put on my lingerie and put some socks in my bra again to make my cleavage bigger. I started applying makeup on and I realized there was a small box with and a bottle I haven't seen before in there. Must have been something Opa bought me.

It was a pair of fake eyelashes in the box and the bottle was the glue for it.

I quickly put on everything, and I have to say the fake eyelashes made a huge difference. I look even more feminine now.

I finished my makeup and began putting on my shorts. I pulled my thong up more to reveal that I was wearing a thong. It made me feel sexy. I put on the white shirt and tied a knot at the bottom to reveal my tummy. Put on my heels and wig and walked out.

John must have heard the sound from my heels hitting the wooden floor.

"Breakfast is ready" He shouted.

I grabbed the tramp stamp tattoo sticker and slowly made my way into the kitchen.

"You look stunning!" he said as I walked in "Just wow look at you!"

I turned around and gave him a pose, revealing the backside of my ass. I held up the tattoo sticker and asked, "Will you do the honor of putting this on my lower back John?"

I handed him the sticker and pulled my thong and shorts a little lower. He quickly damped the sticker and applied the sticker on the right spot.

"Let's eat while it sets" he says.

We chatted through breakfast. "We'll be traveling West today. I found a small island that nobody goes to. The trip will be about 30 minutes. We can chill and have fun there" he walked me through the trip he has planned "I have plenty of beer, spirits and food on the yacht, so you know you're in for a good time."

"Sounds perfect John! I can't wait" I replied joyfully.

We finished eating and he peeled off the wrapping on the sticker and said "It looks perfect! Pull your thong back up for me girl I want to see how it looks."

I turned and slowly pulled up the strings.

"Perfect!" he said exaggeratedly.

Clock hits 8:30. John put my luggage in the back of his Range Rover along with his duffle bag. Our trip finally began. The view on the way was stunning. We chatted as the music on the radio blasted. I was fully enjoying myself. An hour later we got to the marina. He checked in with the details at the counter and came back with papers.

"We're good to go." he said.

He carried his bag in one hand and my pulled my luggage on the other. I followed behind him to his yacht. There were other people at the marina already all waiting to set sail. John knew some of them and they jokingly asked as we walked past.

"Lucky guy John" "Who is the cutie, John?" "Wanna check out my yacht cutie?"

"Haha you guys. This is my girlfriend, Charlene. Be nice" he replied while laughing.

I was so shy, but I loved how he introduced me as his "girlfriend."

John's yacht was at the end of the dock. It was bigger than the other yachts and had a big deck with wooden flooring. An L shape couch with pillows on it and a big roof on top. I was in awe.

"Nice, isn't she?" John laughed and guided me into the cabin.

"This is amazing John" I said as I entered the cabin.

The saloon was spacious. There's a minibar in the corner next to a door. Long couch across the wall and a big TV with surround sound system. John led the way and opened the door next to the minibar. It was a big cabin with a king bed in the middle, a small closet with enough room for a walkway which leads to the bathroom in the back. Both sides of the cabin were glass walls with blindfolds. John put our luggage down and said, "Let's get going shall me?" with a big smile and his hand resting on my shoulders as he stood behind me. I nodded and he led me to the cockpit.

The trip has started. We took off. The weather was perfect, and the smell of the ocean was fresh as ever.

"Why don't you go get changed into your swimsuit?" John said, "We'll be at the island soon."

"Okie!" I said as I pinched his butt softly and skipped into the cabin to get change.

I quickly undressed and opened my luggage. I decided to wear my teal bikini today. I put them on and thought something was missing.

"Ah, nail polish. Silly me." I thought to myself.

I took out my white nail polish and carefully applied them on all my nails. I waited 15 minutes for them to dry and put on my wedges again and went back to the cockpit to meet him.

"Great view!" John exclaimed.

"Definitely!" I replied as I sat down next to him.

"No darling I was talking about you" he looked at me and said with a big smile.

I looked back at him and said, "I know." with a wink.

We both laughed as we approach the island. It really was a small island. I could see the other side from the cockpit. The water was as blue as a sapphire with nobody in site but us!

"So, what's the plan John?" I asked.

"I'm going to go get changed really quick. Why don't you get comfortable on the deck. I'll join you with drinks in a minute." he said as he got up, pointing to the couch on the deck.

"Beer or martini for my lady?" he asked.

"Martini please dear" I replied giggling.

I quickly grabbed my sunscreen from the bedroom and made my way to the deck. As I was going through the cabinets under the couch, I found a big white brim hat and orange Rayban's. Obviously, they belonged to a woman. I took them out and put them on as I sat and enjoyed the view in front of me.

5 minutes later John came with two martinis with olives in his hands. He was wearing a speedo and he made sure the bulge was as obvious as he could get it.

"Those were my ex-wife's" he explained as he sat next to me. "They look beautiful on you. Glad I didn't toss them away" he laughed.

"Martini for my lady" he said as he handed me the drink.

"Cheers" we both said and took a sip.

"I didn't know you were a fine bartender John" I joked.

"Well, a man's got to find a hobby, doesn't he?" he laughed as he eyed me up and down.

I loved the vibe. The attention. Everything was perfect.

He took out a small speaker with an iPod connected to it and started playing music. We quickly finished our drinks. I wanted to get in the sun and John pulled out a blue beach mat. I quickly put it down at the nose of the deck and laid down on my stomach. John's eyes never left my body.

"Can you do my back dear?" I got up and asked John as I pointed at the sunscreen.

"The pleasure is all mine darling" he replied.

He approached me and sat softly on my butt. He then untied my bikini top and started applying sunscreen on my body. The feeling of his hands rubbing on my body turned me on. I started to rub my butt against his lower body. He pulled my bikini bottom up and it turned into a thong-kini.

"Don't forget these beautiful peaches" he laughed as he applied sunscreen on my butt.

He stood up and asked, "another Martini dear?"

"Whatever floats your boat baby" I replied. I was in heat.

He went back inside to make the drinks and soon returned. I got up to get the drink from him and saw he had a SONY video camera hanging on his neck.

"Why don't we take some videos? I never want to forget his beautiful day with the perfect girl" he said as he handed me the drink.

I didn't say anything and started posing. He knew I'm okay with it. He put down his drink and starting shooting.

We laughed and chatted as I posed like a swimsuit model. It was so much fun and to think I can relive this moment in the future made me the happiest girl.

"Why don't you film us while I suck your cock, John?" I walked towards him and asked, with my fingers on his chest.

He paused for a second and ran to the table to setup the camera. He changed the music to sexy RnB and returned standing in front of me.

*End of part 7*

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
5 Comments
Jane_dkJane_dkabout 1 month ago

Lovely story, I loved the whole story and do hope there will be some continuation soon

Jane

AnonymousAnonymousabout 2 months ago

Please post the next one! Omg!

AnonymousAnonymousabout 2 months ago

I check every day for the next one. Please post the next one. Please!

AnonymousAnonymous4 months ago

please post the next one

AnonymousAnonymous4 months ago

this is so good

Share this Story

Similar Stories

The Making of a Sissy Pt. 02 The journey continues as Opa and C got closer.in Transgender & Crossdressers
Pleasing Mr. Wilson A summer job at the cottage leads to unexpected duties.in Transgender & Crossdressers
Daddy Party A young CD accompanies his Daddy to a naughty get together.in Transgender & Crossdressers
My BBC Neighbor An anonymous hook-up leads to a pleasant surprise for sissy.in Transgender & Crossdressers
The Man That Converted Me A young man is snowed in & turned out on a mountain getaway.in Transgender & Crossdressers
More Stories