My First Time As A Gay Bottom – Part 2

Hello ISS readers, my name is Shri. I am 29 years old bisexual guy from Chennai. I come from a well-to-do family who gave me all the freedom to do whatever I liked. I have had my fair share of experiences. I would love to share them with you all, starting with my first sexual experience.

Please read the first part to know the story from the beginning.

My friend’s mom knocked on us after our encounter was disturbed halfway through, calling us out for dinner. We cleaned up and went out to have dinner. We had dinner and watched some sitcoms on TV. After his parents went to bed, we also got into our room.

Vishal said he had got a plan and went upstairs to his sister’s room. His sister was pursuing her masters abroad. So her room was a typical girl’s room with all girls’ stuff. Vishal came back after a while with a bag in his hand, and he said that they wanted me as Pooja.

I did not understand at that moment. But when he handed me the bag, I was shocked. I saw pretty pink panties, a matching bra, his sister’s school uniform, and some makeup items when I opened it. At first, I was unsure, but they again started to melt my brain, and I accepted.

They stripped me off and made me wear the pretty pink pantie, which fit snugly on my bubble ass. They tucked my tiny cock in between my thighs to make it disappear. Next came the pink bra, a 32b cup with pad support. They made me wear it and clasped it from behind.

It felt so good that the fabric of the pantie rubbed around my crotch. The tight bra that held my boobs gave it more shape and formed a sexy cleavage. Arjun and Vishal were so hard seeing me.

I could see their hard-ons over their shorts. It got me excited, too, and my little clitty was leaking and struggling to get hard between my thighs. I was able to feel the wetness.

I then wore the shirt, skirt and the pinafore and applied a little makeup, just kajal and lipstick. I couldn’t believe myself when I looked into the mirror. I saw a cute schoolgirl with a boy cut. The guys didn’t wait for me to get in enough of how cute I looked.

Arjun pinned me to the wall and started making out with me. I was so turned on and reciprocated back with the same force. We were kissing like long-lost lovers, and my lipstick was smudged and made me look slutty.

Vishal now pulled me from Arjun and made me stand in front of the mirror. He started caressing my body from behind. I was able to feel his cock poking over my skirt. I pushed back, lodging his cock between my asscheeks, and he moaned, “Ah Pooja! You bitch, I’ve wanted to fuck you for a long time.”

I was so turned on by his words. I replied, saying I was all his and he could do anything he wanted. He then slowly started kneading my boobs over the uniform. The feeling of being groped over my bra sent shivers and chills throughout my body.

Arjun came in front of me and started making circles with his tongue on my neck. I was in another world with Arjun in front and Vishal behind me. Arjun started to strip me off slowly and seductively, kissing me. I was standing in my pink lingerie and slutty smudged makeup in no time.

The guys also got naked, and I fell on my knees like a good sissy slut. I started to blow both of them one at a time. I made sure they both got super turned on by using a lot of salivae and giving them a sloppy blowjob.

While I was sucking Arjun like a hypnotized bimbo, I felt something cold on my asshole. I felt a finger poking through my tight ass. It pained a little, but Vishal made sure he used enough lotion as lube.

Sometimes I had Vishal fingering me with 2 fingers. I was experiencing pain and pleasure. I was still sucking Arjun and was moaning with his cock in my mouth.

After opening my hole enough, Vishal moved the pantie aside. He placed his thick cock on my entrance and gave it a slow push.  Though there was a lot of lube, the pain was unbearable, and tears started welling up in my eyes.

He pushed in slowly and let me adjust to his size, and in 5 minutes, the pain was gone. Vishal gave me slow strokes, hitting the right spots. My little clitty was leaking precum like a water hose. I was experiencing a whole new level of pleasure.

He turned me around, placed a pillow below my hip and entered me into the missionary position. I was lost in pleasure. I felt I was a girl getting fucked by her boyfriend. My little cock was tightly held by the pink panties, which had a huge wet spot.

Vishal laughed, looking at it. After fucking me in that position for 10 minutes. He was close to cumming, and he increased his pace. He was hitting my prostate with every push. I was at the peak and edging.

He gave me a few more hard thrusts and came inside me. At the same time, I also cum in the panties without even touching my clitty. The orgasm lasted for a while. I was sweating and felt his warm cum inside my ass.

He slowly took out his cock, and his cum came out, gushing out of my not virgin any more boi pussy. I was tired, and luckily Arjun was not into anal sex. I finished him off with a sloppy blowjob where he came all over my face and mouth again.

We were all tired. They took me to the washroom and cleaned me up. They made me wear a fresh pair of bra and pantie, and we went to sleep. I was sandwiched between my two friends or lovers or whatever we would call this. And we were all so satisfied.

This is my first gay sexual encounter. I hope you guys enjoyed it. Please do write in your feedback to [email protected]. Based on your feedback, I will continue to post my other experiences.