Tale of losing my anal virginity

Hi readers. This is Vinod again. I have decided to share more of my sexual journey with you. Continuing from my earlier post. It was an eventful day with Srikanth in his room.

I should say I have been a changed person since then. All my idle time was consumed by his thoughts. The feeling of his hands all over my body. The feeling of my hands playing with his thick, hard cock.

Since that day, we used to meet whenever we had time and a place. We never wasted any chance to meet up and have fun. I always used to look forward to sliding my hands into his shorts and holding his cock.

It’s been about 2 months, and we used to meet 2 or 3 times a week. I used to suck him and drink his cum. Take it all over my face and body and lick it and his balls clean. I used to enjoy every bit of these, unlike the earlier days when he used to insist on my drinking his cum.

The best part used to be the way we maintain eye contact during these acts. It made me feel like a real slut.  The days passed like that, and then came Dussehra. All my flatmates planned trips to their respective hometowns.

I felt it was going to be a good opportunity to be all alone in the 2BHK flat for 5 days if I skipped going to my hometown. So, I decided to skip it, and I told Srikanth that I’m going to have the flat for myself for 5 days. He too decided to skip going to his hometown.

I was super excited to have him with me in my flat for 5 full days. The day has finally arrived. All my roommates were supposed to leave the room by 9 pm to catch their respective buses. I told Srikanth to come by 10 pm. Travel time from his room to mine is about 10 minutes.

I told him to give me a call when he starts. I wanted to get naughty by the time he comes. I bought myself a tight white t-shirt. I chose a notch smaller than my regular size and paired it with white underwear. The t-shirt was already hugging my body tightly.

I then drenched myself in water while wearing them. I looked at myself in the mirror. The wet white body-hugging t-shirt was showing out every curve of my body and nipples through it. I was eager to show myself to him like that.

The doorbell rang, and I drenched myself in an extra mug of water and opened the door. I could see his eyes widen as he saw me. I told him to come inside soon. I quickly closed the door. He pulled me closer and spanked one on my waist and one on my ass.

I asked him, ‘Did you like your bitch?’ He spanked my ass again harder and said, ‘Yes, you bitch.’ He bent over a little and started biting my nipple from over my t-shirt. He kept squeezing and biting me whenever he could.

I was moaning in pleasure. As he kept playing with my body at will. I slid my hand into his shorts and got hold of his rock-hard cock. I started playing with it by pulling his skin back. I was getting horny and badly wanted his cock in my mouth.

I pulled down his shorts. He took off my wet t-shirt and later his t-shirt and my underwear. We were fully naked, and I got to my knees and started licking the tip of his cock with my tongue, looking into his eyes and smiling. He likes it a lot and was moaning with pleasure.

After a while, I took it in fully and started deep throating. When he wanted a pause. I stopped sucking his cock and focused on his balls. He loves to rest his cock on my face as I suck his balls. I, too, get a kinky pleasure of bearing his cock’s weight on my face when sucking his balls.

I sucked him for a while, kneeling in front of him. After a while, he made me lie on the bed and sat on my chest. He put a pillow under my head and fucked my mouth. Then he told me to play with my tongue on his tip. I put my lips around the tip of his cock.

I started rimming his cock around the diameter of the tip and occasionally applying pressure on his pee hole with my tongue. He then shot out his cum. Some of it over my tongue and the rest over my face. Whatever cum fell on my face, he used his cock to rub it all over my face.

He moved away from my chest, pinched my nipple hard, slapped my boob, and lay down beside me and relaxed for a while. After some time, he said, ‘I’m feeling very tired. Let’s have a hot shower.’

I said ok and switched on the geyser after a few minutes. We both went in and had a romantic shower together. He bathed me, and I bathed him. The hands of one person running over the other person’s body with the slipperiness of the soap felt very romantic.

At one point, he was hugging me from behind and trying to press my boobs as he rubbed them with lather. His cock became fully erect, and it was poking my ass crack. He then positioned it in a way that it gets stuck in my ass crack and pushed it in like he’s fucking my ass.

It got further stuck in the crack, and he gave a couple of more thrusts. We both instantly burst into laughter. We continued our romance under the shower, and he was kissing my shoulder from behind.

He said, ‘I want to fuck you.’ I said, ‘I am all yours. We finished the shower and went out to have dinner. It was almost 11.30 then, and we ate fried rice and returned to our room by 12.30 or so.

We relaxed for a while, and then he asked me ‘So are you ready?’ I said ‘Of course I am. Why are you asking like that?’ He said, ‘I am talking about breaking your virginity.’ I said, ‘Are you serious?’

He said, ‘Yes, Namitha darling. I want to fuck you.’ He started pressing my boobs. I can’t say no to anything he asks me when his hands are on my boobs. That’s kind of a soft spot for me. I said,’ Yes, I am all yours. ‘ He then told me to get oil. I brought it.

He put it aside and told me to start sucking. We became nude and he sat on the bed edge. I was kneeling in front of him and started sucking. It was fully hard in no time. He told me to bend over in doggy position and applied oil to my asshole and his dick.

He did some fingering of my hole for a while. He then tried to insert it, and it was slipping away initially. I then helped a bit by holding and spreading my ass cheeks for easier access. He then tried inserting, with hardly any success, during all this struggle.

He lost his erection and felt tired. Both fell on the bed and laughed, thinking it’s not as easy as we think after a while. He told me to suck it and make it hard. I said I am not going to suck that coconut oil. I can do a hand job. He said ok and I started rubbing his cock, which had oil on it.

Once it’s hard, I set myself in doggy position and hold open my ass cheeks. He again applied a lot of oil to his cock. My ass hole and his fingers. He did vigorous fingering with 2 fingers. It was slightly painful and uncomfortable at first, but soon there was pleasure.

He again started his struggle of trying to insert, and again, many times it slipped away. He finally got lucky, and a bit went in, but there was sharp pain. I screamed and crawled away from him as an impulsive action. He tried to hold me, but I moved quickly away from him.

He lost his erection, and he came to me. Pulled my hair and slapped my face. ‘I managed to enter somehow, and you spoiled it all, ‘ he said. I said, ‘Let’s relax a while and try again.’ We relaxed again for a while. During the process, we wondered how anal sex is actually done as shown in porn.

Is it really possible? Etc. After a while. We decided to make another attempt. I again gave him a hand job and once hard. We decided to try. This time he said, ” Let’s try missionary. He made me lie on my back. Raised both my legs. Put a couple of pillows under my bum and again applied oil and did a bit of fingering.

He then started to insert and told me not to move or disturb this time. He put his dick on my asshole and put all his weight on me. Maybe it gave an advantage. It started going in. I could feel my ass hole opening up with a lot of difficulty for his cock to make its way in.

The pain was sharp and unbearable, and I was not left with any space to move away. The only way was to push him away, but maybe because of the pain, I couldn’t feel any strength to do so. I was feeling torn apart and screaming, and tears were rolling down my face.

He could see it, but he was hell bent on fucking me that night. He used all his strength and willpower and slowly pushed his whole cock inside. The pain was horrible beyond explanation, and I felt I was going to die that day.

He then slowly pulled it back, and the feeling of hollowness as he was pulling was amazing as he pulled it out to the tip. He suddenly pushed it back again. Every time he pushed in.

It was like hell, and I was literally crying, but he kept going on and increased his speed. In a couple of minutes, he shot all his load in my ass.  He pulled out his cock and closed my legs, turned aside and was crying.

He then called me and showed his finger. I could see blood on it. It scared me. I could still feel the pain and burning sensation in my ass, and it felt uncomfortable for me to sleep in any position. I then decided to wash it off as I was feeling all sticky there.

I found it hard to get up. My whole body was trembling because of pain, and I wasn’t even able to walk properly. He helped me to the bathroom, and I washed it all off, and I saw blood coming because of the rupture of ass walls. I washed off and came back to bed.

I told him to put a couple of tissues in my ass crack so it would absorb any blood drops that might still come. He was trying to comfort me, telling me to sleep and that it would all be fine by morning. It took a while, and I didn’t know when I slept.

The next day, I woke up to horrible pain and a burning sensation. I saw that Srikanth had already woken up and brought breakfast. The pain lasted about a week as it slowly faded away. It took me 2 days to walk properly. Almost 4 days of horrible burning sensation when shitting.

Because of this, I only ate bland food till the burning sensation subsided. The next 5 days, I only sucked his cock, and there was no anal. This kind of torturous pain was there for the first 5 or 6 times. We deliberately gave a gap of 1 week to 10 days between two fucking sessions.

After about those 5 or 6 sessions, the pain was bearable, and we started doing it 2 or 3 times a week, depending on the time and place availability. Slowly, the pain was more and more manageable. I started to enjoy the pleasure of it to the extent that I started encouraging him to bang harder and harder.

The relation with Srikant lasted for about 2 years until his marriage was fixed. He moved away to his hometown, after which we lost contact.

So, guys. This is how I lost my virginity. I want to mention many stories where anal sex is described as a casual and enjoyable thing. No, it is not. Especially the first few times. It is going to be a hell of a lot of pain, and you can enjoy it at a later stage only once you pass this phase.

So don’t be under the misconception because of what you see in porn or what some stories describe with added masala. The truth is, it is going to be very, very painful beyond what I can describe in words.

You can share your feedback on [email protected] and based on the feedback I can share further experiences.

 

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