Femdom Vacation

As per her instructions, I sent her a photo of me wearing the chastity cage. The work week was difficult. I was so excited, yet nervous about meeting her. I wasn't able to get an erection because she had the key to my cock, or hopefully it arrived in the mail to her. I had to avoid being naked around my wife, but that wasn't too big of a deal. My flight to San Diego was set for Friday.

Friday morning when I was parking at O'Hare, I received another text. Mistress A informed me that our beach house wouldn't be ready until Monday. She was headed north and would meet me at the San Diego airport that afternoon.

My heart started racing. This was becoming a reality.

I checked my baggage, went through security and noticed a few smirks as a few dildos appeared in my bags through the xray machine.

Being a chronic masterbater, I normally rub one out in the bathroom on flights. This was not an option, which made the flight seem even longer.

The flight landed, I retrieved my bags, and headed towards transportation. From a distance I saw a beautiful woman wearing tights, red high heels and a loose fitting t-shirt. She had a big smile, long brown hair and a sign that read, "Bitchboy Bobby."

My cock tried with so much effort to get hard. It was useless. My heart sank, I gave her a big smile and walked towards her.

"Mistress Alana, I presume"

"You are cuter than I expected. We're going to have some fun."

I smiled.

"I've been on my feet for too long. Let's have a seat over there."

We sat on some comfy benches in the airport lobby. She put her foot on my lap and looked me in the eyes.

I removed her sexy high heel, revealing her soft, delicate, well cared for foot. I rubbed the bottom of her foot, giving her a deep massage. Then the other foot. She was so easy to look at. She took her two feet together and pinched my caged cock. Her toe nails were painted red. Her feet were wonderful.

"Good. I see you are still under my control. I'm sure you know that the mail system in Mexico is a disaster. That's why I had you mail the key to my friend here in San Diego. She confirmed that she received it. We can stop by her work place tonight. Let's go check into our hotel room."

Our room. It sounded so nice.

When we picked up a rental car, Mistress A asked them to upgrade us to a mini van instead of a sedan. I obliged and we drove to our hotel. It was a 4 star hotel, clean nice and good service.

We arrived to the room and she said, "Stop. The first rule for this room is that you are not allowed on any furniture without my permission. You are also to be on your knees anytime we are in here. "

"Yes, Mistress."

"Good boy."

I crawled into the room, pushing my bag from behind. She sat on the bed with her heels dangling.

Without looking at me, she demanded that I take my clothes off and gave me permission to stand up.

I did and she started laughing. "Your poor little helpless useless dicklet. You seem pretty sexy except for that thing. Now back down on your hands and knees. Go unpack your things. Please put all of the sex toys on the table opposite the door near the window."

I complied and it took me a while not being able to walk.

While I did this, she called to the front desk to ask for a few extra towels.

There was a knock at the door and Mistress A ordered me to kneel at the edge of the bed. She got up and opened the door. I heard a deep voice and she was being extra flirty with him. She said, "you can just put them on the table over there by the window. "

The man walked past me as I was kneeling and naked. He put the towels on the table amongst the dildos, harnesses, straps, panties, lube, ball gag, clothes pins. He was average looking, in his 20's and tall. He seemed a bit uncomfortable, but has probably seen a lot working at a hotel.

As he was leaving, she said, "Don't mind my bitch. he's just here to watch." She gave him a tip and he left.

Watch what, I thought?

"Ok bitchboy, go shower, put on some nice clothes. We are going out tonight. Dress nicely, we have some fun planned."

We drove a few neighborhoods over to meet up with her friend, Jana. We went up to her apartment and Mistress A had me get naked the second we entered Jana's apartment. I stood there humiliated as Jana appeared in the living room covered in sweat. She had shoulder length blonde hair with bangs, 5'8, covered in tattoos and large breasts. She was thick in the most perfect ways.

"Sorry, I was just finishing working out. I still need to get ready."

Mistress Alana asked her if she needed any help.

She looked at me and said, "Yes, I do" as she smiled in a cunning manner.

I crawled behind her looking at her nice round ass. She was wearing yoga pants and it was a really pleasant view.

"You are allowed to climb up onto my bed. Get up there."

I laid on my back on her bed and she stood in front of me, taking off her sports bra and exposing her tits. They were likely 36D or 36DD.

"I bet your worthless little cock wants to rub all over these babies, doesn't it?"

I didn't answer because I was too mesmerized. She climbed closer to me and lowered her tits towards my face.

"Do you want to get hard?"

"Yes Ma'am."

"You know I have the key to your cock, right?"

She had a cruel laugh. One like a witch, but it was so sexy. I wanted nothing more than to beat my cock looking at her tits.

She stood up and then lowered her body so she was sitting on my face. I could tell she had a good workout. I could smell it through her yoga pants. She sat there for a minute or two before standing up and taking her pants off. She had a thong on and took it of. She put it in my mouth and started pinching my nipples. Her pinch became harder and harder until I started making noises and squirming.

She let go, pulled the panties out of my mouth and leaned to my ear, lightly nibbling on it.

She whispered into my ear, "Your are our bitch tonight. This is just the beginning."

She stood up, sat down on my face and smothered my mouth and nose with her hairless wet pussy. She rode my face while I licked her hole and clit until she came.

She stood up and walked out of the room to take a shower. I looked over and Mistress Alana was sitting on the chair watching.

"Very well done. You'll be eating a lot of pussy this week so be ready. Put those panties on and get dressed. We have a fun night planned for you."

She held up the key to my chastity device and walked out of the room.