Cherry Pop

Story so far : I have moved to a new country and met a 44 year old desi guy through Social Media. We had a casual and our liking was mutual. He conveyed his wish he would be a lucky guy if he can pop my cherry and I said okay to him. 

Date was set and anxiety set in immediately. For the next 10 days I have read about everything I find on the internet and it made me more anxious. 

Finally D-day arrived. Shaved, took bath and met him and quickly checked into our room. I had no clue or whatsoever what to do so I froze in place.

"Farzin, come and sit next to me" he said.

I just sat next to him "Oh my God, you are so beautiful" he said. 

"Thanks" I said. 

He knew I was nervous from my reaction so he wanted to calm me. "Dont be nervous, I am not going to bite you or do anything against your will. It will be best for both of us if you can communicate. Can you do that for me Farzin" he said. 

I nodded. 

He just gave a peck on my cheeks and said "Good girl". For the first time someone said that I am a girl so i blushed and my cheeks turned red. 

"You know, you look stunning when you blush"

I blushed again. 

"We should get comfortable. Do you want to change the dress" he asked.

"I didn't bring anything" I said. 

"I have brought something for you" he opened his bag and gave me a red babydoll dress. It was not fancy or anything, just a plain cotton babydoll. I was hesitant but I went to bathroom and changed to it quickly. It was short dress which covered till my thigh. 

When I went back and he was in his Boxers already. He was a total Daddy. He had graying hair and a beard, but also that look. It's indescribable, but he was a Daddy. He exuded Daddiness. He called me to sit near him when I sat he held my cheeks and turned towards him and started giving me a romantic kiss. His breath was good and the kiss was too good. That kiss calmed my nerves to be honest made me little horny. I could sense that he is horny too from his growing bulge. He pushed me to bed and was all over my body.

I have sensitive nipples when he pulled my babydoll and started sucking it I lost it. "Aaaaah" I moaned loudly. 

"Do you like it Farzin"

"Yes Daddy"

I used to call him Daddy on chats but never in real. So when I called him Daddy he lost it too. He become passionate and started exploring my sissy body. When he was done with my body bottom side of my babydoll is soaked with my precum. He removed his boxers and his dick is fully erect. I dont know the exact size but it is massive. 

I thought he will ask me to suck but he had other plans he turned me and asked me to lift my bum and he was going to fuck me. "Yes I will become a women" I thought. 

He put a condom and applied lube and inserted his index finger with lube. Even that was too tight. 

"Shit you are too tight. Try to relax" 

I tried my best to relax and he fingered my hole and I could feel it loosen up little bit. He removed his finger and I could feel his cock at the tip of my ass. 

"Farzin take deep breaths and relax"

"Yes daddy just take it slow"

"Yes I will" he lined up his cock with my cherry hole. He pushed little bit his tip was inside because it was well lubed. I gasped for air. 

"I am going to push a little more" he said and he further pushed. 

I am not sure how far it went by I could feel pain in my ass. "Daddy stop, its paining". He stopped and tried to go little deeper. He was so patient but after one point he couldn't so he asked me to relax and just pushed it deep. Pain was excruciating and I moved away from him and started crying. 

"Sorry, sorry you were too scared that's why I had to push it all in"

"Does it hurt"

"Yes, its paining"

"Come let me check he said" 

He checked and made sure I wasn't bleeding. "Its okay Farzin, your Cherry is popped, it will be painful for a little while then it will go away. We could take rest for a while and we can go away"

"I am sorry Daddy"

"Don't be I was expecting this. I am lucky that I get to pop your cherry" 

I blushed. "Daddy can I suck you"

"Sure why not"

He was sitting on the corner of the bed and I kneeled down his erect dick was close to my mouth. I kissed its head and grabbed it.  It reacted to my touch. I giggled involuntarily. Like an excited school girl, I tried to remember all the BJ videos I have seen and fed the head into my mouth. I started sucking him like a excited girl and when he gave out a moan I knew I was doing an okay job. I started looking into his eye and started sucking with more involvement and he started moaning more. That made my try to suck deep but gag reflex was bad so I started coughing. I took a break and started stroking him and then sucked the top half of it while massaging the bottom with my hand. After a while my mouth started to hurt a little be started giving deep moans and ejaculated thick cum into my face. 

I drank as much as I can and spitted out the rest. 

"Did you enjoy it daddy" I asked him.

"Yes Farzin. You?"

"I too daddy"

After cleaning up we hugged each other and his dick started growing again, I blew him 2 more times, once again he cummed in my mouth and the last one on my face. We parted our ways while I was coming back in tube even thought the day didn't go as planned It was a one to remember. Even though I didn't have a full fledged sex my cherry was popped that. After realizing the fact I laughed. Tube came out of underground tunnels and my cell go reception I received a text from Daddy. 

"Don't worry too much about the things that didn't go well. I fully enjoyed our time together and hoping to see you soon again when your ass is cured. This time I want you to come with a little more training"

"What training" I immediately responded. 

"I will tell you tomorrow" 

I was excited and scared about the training the following day.