All Caged Up Pt. 01

"Ohhhh, ouoououhhh!!" Tammy moaned.

I had been eating her delicious pussy for at least 30 minutes. Her nails dug in harder and harder into my scalp as her entire crotch spasmed. With my right pointer and middle finger rubbing her g-spot I almost wanted to lift her up and smack Tammy's ass with my left hand. But I just stayed and worked that stop with my lips, tongue, and fingers.

"Damn!!" Tammy cried at the final climax a few minutes later.

I looked up and smiled. I then crawled up to Tammy and squeezed her as I rested my head against her right breast.

"Sissy..." she panted. "you're incredible. Who taught you how to do that? Not even my ex-girlfriends ate pussy like that."

I held Tammy for a few minutes and just enjoyed the moment but I had some questions.

About an hour later we woke up and started cleaning up. I joined Tammy in the kitchen after my shower.

I pulled her close from behind as she drank her coffee.

"Morning Mistress"

"Morning Sissy."

"I have a question, Mistress."

"Yes, Sissy?"

"You said I eat pussy like one of your ex-girlfriends."

"No, better," she replied.

"I didn't know you had a girlfriend. Are you bisexual or gay?"

"Yes, Sissy. I am bisexual. I have had girlfriends and yes threesomes. Is that what you want to know?"

"No, I was just curious."

"You men love your threesomes."

"I have never had one and would only want one if we both agreed."

"No."

"What?"

"Sissy, you mean Sissy would only want one if Mistress told him to. That's what you meant, right?"

"Yes, Mistress."

"Sissy, you trust me, don't you?"

"Of course, Mistress. What's up."

Mistress went around me and pulled me close. She dropped my pants and panties.

"Put this on," Tammy said as she handed me what looked like twisted hard plastic.

"What is it Mistress?"

"It's a chastity cage."

Before I knew it, she had slipped on me and locked it. I tried to get it off and she laughed.

"Sissy you can't get it off. Mistress has the key," she said as she swirled the key around her pointer finger. "Now Sissy, Mistress is going out to watch her beloved Michigan State Spartans football team. Sissy is to go home and play with his toy. Work your way up to at least four beads for next weekend and keep his cage on. That is your homework. I know Sissy always does his homework, doesn't he?"

"Mistress, I am confused."

"Yes Sissy."

"Won't this make it harder for me to get hard? And if I get hard using my toy won't it hurt?"

"Sissy, does that matter? Aren't you going to save that big sissy dick for your Mistress?"

Then she turned around and swiveled her ass into my crotch. Ouch. It fucken hurt.

"Of course, Mistress."

"Then you will be fine until Mistress lets you unleash that big, hard dick on my delicious pussy. Mistress told Sissy she is in control. Doesn't Sissy like that?"

I nodded yes.

"Isn't he happy when Mistress puts him in stockings, lets him eat her pussy and worship her feet, and of course my Mistress takes over and fucks him like the slutty little Sissy he is?"

I continued nodding.

"Mistress knows he likes it because he comes like a firehose. So, trust Mistress. We are on a journey together, but Mistress is in control, and she would never do anything to hurt Sissy."

"Yes, Mistress."

"Mistress has to go."

With that, I gathered my stuff and went home. The rest of the weekend I spent playing with my toy and slowly getting more familiar with the moment of the beads in and out of my ass. It flushed me with pleasure but then my dick would throb against the cage and hurt. I Googled pegging and was blown away. Several April Olsen videos later I was like a rabid dog.

Monday came and I was at my desk. A text came through, "Sissy, the same rules as last week. Be a good boy and you'll get something sweet on Saturday. Hope you like your new friend."

"Saturday?" I texted back.

"Saturday. Don't challenge your Mistress. Be a good Sissy boy and do what your Mistress says. End of conversation."

I put my phone down and went back to work. My dick hurt but I tried to focus on anything else. A few minutes later. I overheard Tammy.

"Sorry about that, I sometimes get annoying texts. Let me continue our tour," Tammy said.

Then she knocked on my opened door and walked into my office.

"Anna, this is Mike," Tammy as she waved her hand across my office. "Mike, Anna is a temp here for the week and covering the front desk while Janet is out for jury duty."

I turned and saw a short, petite blond with blue eyes, a bob haircut, a sky-blue blouse, and a matching skirt that went to her knees but could not hide her lovely legs that ended with little ankles, open-toed heels, and cute feet. Even before she turned around, I could tell she had a tight little ass, just like a cherry. Gorgeous.

She was a contrast to Tammy's tall, curvy body which featured full breasts, a juicy round ass, and flowing black hair. Fuck I wanted them both. My dick throbbed and instantly hurt. Fucking cage.

"Mike... Mike," Tammy said and motioned at Anna's hand. I spaced out for a second and quickly shook her.

"Please excuse his messy office and spacey demeanor," Tammy said.

"Mike, is that a Jets sticker?" Anna asked.

"Yup," I responded. "They are 2 and 2. Big game against Miami coming up."

"Cool, my family is from Mineola. So, I know all about the J-E-T-S!" Anna started to say. "I love the games on a three-day weekend. Do you guys get Columbus Day off?"

"Yeah, one of our founders was a big supporter of Italian-American culture," I responded.

"You'll have to make it a really special day then since you get to rest Monday," she said.

"True."

"Ok, well let's wrap this up. Anna has other people to meet. You two can talk J-E-T-S some other time," Tammy interjected.

"Great to meet you."

Tammy was annoyed and quickly took Anna away. I watched their two asses leave and thought what a delicious contrast. The rest of the day passed, and I went home to play with my toy.

On Tuesday afternoon, I headed out for lunch and passed Anna at the front desk.

"Hi," I said.

"Hello," she responded with a little wave.

I passed by and grabbed the door to leave.

"Mike."

"Yes," I said as I turned around.

"Do you go to Planet Fitness on 4th and Montgomery?"

"Yes, I do."

"I thought I saw you on the treadmill last night. But I didn't want to bother you."

"No bother. What were you doing there?"

"I was at Pilates. I do that there Monday, and Thursday, and yoga on Wednesday and Saturday afternoon," she said as she pulled her dress up and I saw the top of her thigh-high stockings.

I instantly imagined her in a tight leotard and very sweaty. My dick got hard. Ouch. I took a deep breath.

"Everything ok Mike?" she asked. "Are you eating out?"

"I am fine. Just going for a walk. I bring my lunch every day but Wednesday. I go out to celebrate getting over the hump," I said and instantly felt like a lame ass. It didn't matter. I was sure she had a boyfriend who was jacked, looked like Ryan Gosling, and made three times my salary. Also, and much more importantly, I had Mistress.

Before I knew it, it was lunchtime on Wednesday, and I was leaving for my weekly lunch out. My stomach was growling so I bolted out of the elevator and quickly made my way through the building lobby. Then I bumped into Anna.

"Hi, Mike."

"Hey."

"Ready to eat out?"

"What?"

"You're eating out, right?"

Just the way she said eat out made me imagine having my face buried in her muff. I wonder if she fully shaves, does the landing strip, or goes full bush. God, it was hard to concentrate.

"Are you good at it?"

"What?"

"Are you good at it? Eating out. Most people, especially guys aren't."

What the fuck? Was this conversation actually happening I thought. I could chew through this fucking cage right now.

"It's really a skill, I think. You have to find the right place and take your time. Really get to enjoy and be willing to try new things. Most people just rush right in get what they can and rush out. They don't savior the opportunity. I've had some really tasty, satisfying meals because I was willing to take my time, find the right spot, and let myself enjoy. You know? Maybe sometimes we could eat out together?"

Fuck.

"Yeah... I know what you mean... That would be uh great..." I said but was not really sure what to do. Anna was looking down and blushing. Did my dick break through the cage?

"Well, I have to go. Tammy will be mad if I take too long."

"Ok," I said, thanking God I had a coat on that covered my crotch.

Anna walked away and her tight little ass wiggled just in rhythm. I could tell she was smiling.

Thursday I was running late and as I entered, ready to say hi to Anna, I was stunned. She was gone. I short, fat, wrinkled old woman sat at the at front desk.

"Do you work here? ID," she said.

"What? Yes, I work here."

"ID!!"

I fished for my ID and Tammy came out to the front desk. She had a smirk on her face.

"It's ok, Mike works," Tammy said. "Mike please find your ID next time."

I fished it out of my wallet and showed it. Then I headed to my office. Tammy was now following me.

"Who was that?" I asked.

"Dot."

"Dot?"

"Well, her name is Dorothy. But she wants to be called Dot. She is taking over for Anna. Apparently, Anna got a new job that starts on Tuesday. Are you going to miss her?"

"What? No."

"Oh come on. I saw how you stared at her. At least Dot won't cause any problems with your new friend."

"No, I didn't."

"I don't blame you. She had a great ass and is cute. Just my type."

"Well... I have work to do," I stammered and walked away.

The rest of the week went by. Friday night no message from Tammy. I was getting antsy. Finally, at 6:15 I got the following, "Nothing tonight Sissy. Get your beauty rest. Have fun with your cage and beads. Save your strength for tomorrow and Sunday."

Sunday? That was interesting. Two days with Tammy. I wondered what she had in mind. Reading save my strength was even more intriguing. So, I went home, played with my beads, and tried to sleep. I tossed and turned all night. Sleeping with the cage was not easy. Finally, I woke up at 11:00 a.m. to a buzzing phone. The message said, "Sissy be here at 3:30. Have your panties and stockings on. Don't bring a change of clothes. Mistress has everything taken care of for Sunday."

I got there just like she said and rang the doorbell. Mistress answered the door in a red silk robe and only a pair of black lace panties.

"Come in Sissy."

I walked in and asked, "Where is it?"

"What Sissy?"

"The key!"

"Oh this?" she pulled it out of her pocket and spun it around. I grabbed for it. She stepped back and laughed.

"Oh Sissy, Mistress wants you to earn this."

I chased after her.

"Oh, Sissy! This is a new side of you. So aggressive. Mistress is shocked."

I chased her onto her couch and grabbed her. I pulled off her robe.

"You want me to earn it?"

"Yes!!"

I started smacking her ass. I pounded it for a good two minutes.

"Oh, Sissy!!"

I then reached down and bit her thong and pulled it up. That snapped it off her body. She turned with her mouth open.

"You're a bad boy."

I then squeezed her ass and began kissing it. I rubbed it and then moved in to start licking her cheeks and around the rim. Then I moved down and licked her pussy.

"Ooohhh yes!! Sissy yes!!"

I rubbed, licked, and kissed her ass and clit until her moans filled the room. I then stood up and dropped my pants. She turned over. Tammy was flushed and smiling. She then unlocked me. She stood up and kissed me, sticking her tongue down my throat, and took me to the bedroom. My dick was now free and getting so hard.

She jumped on the bed and motioned for me to come over. She finished undressing me and I started to kiss and suck on her breasts.

"Damn!! With an ass like that I can see why you want to peg him," a voice said.

I turned around and it was Anna. She was standing in the doorway wearing a dark

blue negligee and high heels. I looked at Mistress and she smiled.

"Mistress told you there'd be a reward, Sissy."

To be continued...