My Daughters First Time

My name is Lisa. I have always wanted the best for my daughter as all parents do. When it comes to sex, that is especially true.

My husband Tom and I have raised our 20 year old daughter Jessica (Jess) to enjoy life and it's treasures, sex being one of them. Tom and I have never shied away from discussing sex with her. On more than one occasion she has seen us naked and even fucking.

As her 21st birthday was approaching we wanted to something special for her. We decided on giving her a special present, a weekend at a resort with one of our best friends, Dana, a trans female. This would be her first time with a trans woman.

Now, Jess knows Dana but she doesn't know that Dana is trans. They have always gotten along fine and we thought this would be good for Jess.

We picked a weekend when Jess had no school. I called Dana to see if she would be not only interested but also available.

"Dana, high this is Lisa. How have you and Sammi been?"

"Hi Lisa, we have been fine. What's going on?"

"Our daughter's 21st birthday is coming up and we wanted to give her something very special and I was thinking of a weekend with you. Interested?"

"Hmmm. That does sound interesting. When would it be?"

"I was thinking at the end of the month. Would that work for you?"

"Yes, that's fine. But would Jess be ok with this surprise?"

"Tom and I discussed it and we think she is ready. If nothing else, you will get a quiet weekend at a nice resort."

"I guess I could do it. Ok, I'm in. Get me all the details."

"Thanks Dana, I owe you."

"You sure do. Bye Lisa."

"Bye Dana."

I told Tom and I started to make the arrangements.

By the end of the day, everything was set. That night Tom and I took Jess out for a lovely dinner. As we ate Tom told Jess what we had planned for her birthday and she was very happy and looked forward to going to the resort. She was equally happy that Dana was going to be with her.

"You know mom, I like Dana. She is smart, pretty and not a stuck in the mud. She is kind of hip for her age."

"We are glad you're happy. We made all the arrangements and Dana will come here and we will take you two to the airport."

"I'm looking forward to it. Thanks Mom and Dad."

Finally, the day arrived. Dana already was here and Jess finished packing and Tom and I took them to the airport. We stayed with them as long as possible before they disappeared down the ramp to the gate.

From here on, Dana is continuing with the story.....

Jess and I boarded the plane and after a two hour flight we arrived at the beautiful island and took a cab to the resort.

We checked in and were taken to our private chalet on the beach. The only problem was that there was only one bedroom with a king sized bed. We called the office and told them we needed two bedrooms but they said the reservation called for only one bedroom. Dana said, "It's ok Jess. If you are ok with sharing a bed, so am I. We unpacked and got ready to go outside.

I wore shorts and a tank top without a bra and Jess did the same. We walked around the resort and got familiar with all it had to offer. The place was beautiful. By the time we got back, it was time to get ready for dinner. Jess showered and as she was getting ready, I showered and then got dressed. We then headed to one of their dining rooms where we feasted on roasted duck and plenty of wine, things we don't get at home.

We spent almost two hours at the restaurant and after dinner we continued walking on the beach under the moonlight and gentle breeze.

It was getting late so we headed back to our room. Jess undressed first. "Dana, is it ok if I sleep naked?"

"Sure Jess. It's ok with me. I'm going to keep my thong on. Ok?"

"Sure Dana. Not a problem."

We got into bed and we kissed goodnight.

At some point at night our bodies pressed together. My cock was hard as our bodies touched as we faced each other. Then I felt Jess's hand moving down. It rested on my thong and hard cock. Suddenly Jess jumped up, "Dana, you have a cock "

"Yes, Jess. I am a trans female. Is that ok?"

"I guess so. I didn't know. Can I see?"

"Sure Jess." And I removed my thong and my cock popped out.

Jess reached down and touched my cock and balls as I turned on the light.

"Your cock is beautiful Dana. It's bigger than my father's. Is it ok if I play with it?"

"Sure Jess."

Then Jess moved her face down to my cock and she started sucking it. I threw over the sheet so she had complete access to my cock and balls.

As she sucked my cock I played with her tits. Soon we were missing and sucking on each other's nipples.

"This is Amazing Dana. You are beautiful. Does Mom and Dad know?"

"Yes Jess. They wanted me to come with you so I could fuck you. Is that ok?"

"Oh yes Dana. I want you to fuck me."

I moved Dana on her back and mounted her. I slipped my cock into her cunt and started fucking her. "Jess are you safe?"

"Yes Dana. You can cum in me."

I started fucking her harder and faster as she met my thrusts and soon I started cumming. I came so much that my cum oozed out her unt with my cock still in her.

We kissed as my limp cock slipped out of her cunt.

"That was amazing Dana."

"I'm glad you enjoyed it Jess."

For the rest of the night we fucked often until we fell asleep naked and cuddled together.

The next morning I was awoken by Jess sucking my cock. As my eyes opened, I felt my cum shooting into her mouth. She had a big smile on her face and my cum oozing from her lips.

We got up and showered together. My cock constantly hard and erect. We had breakfast in the room, both of us naked and as soon as we finished, we went back to fucking.

Right before lunch my cell phone rang.

"Hi Dana, Lisa here. How is everything?"

"It's your mom Jess."

"Everything is fine Lisa. Jess and I fucked last night and are going to fuck again in a little while."

Jess jumped up, "Hi mom. Dana is terrific. Thanks for you guys for arranging this."

"Glad you two are having fun."

I got back on the phone, "Lisa, Jess is amazing. I'm glad it worked out. Got to go, Jess is on the bed already wanting to fuck some more."

"Ok Dana. Enjoy her. Bye."

I hung up and said to Jess, "Your mom said to enjoy. Ready for more fucking?"

"You bet I am."

We fucked for most of the day. Eventually going outside to stretch our legs and enjoy the scenery.

That night and the next day was more of the same. Jess was insatiable and just wanted me to fuck her in both of her holes.

Unfortunately, we had to get ready to leave and we packed our stuff and took a cab to the airport and headed home.

Lisa and Tom picked us up and headed to the house.

Lisa said, "Thank you Dana for going with Jess. We owe you."

Jess said, "Yes, Dana thank you. I'll never forget you."

Then I replied, "Thanks to your mom and dad and you too Jess. You are an amazing woman. I hope you visit me an Sammi sometime."

Jess looked at ma and said, "Mom can I visit them?"

"Sure you can. Dana and I will arrange it. Ok baby?"

"Yes mom. Thanks."

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