Sissy Boyfriend Cuckolded When Girlfriend Fucked

Hello guys, all the characters in this story are real but their names have been changed. This is a fictional story, however, I want this to happen to me in my real life. So let’s get to the story.

I am Aayan from Surat, Gujarat. I am 5’4 and not that well-built. I have a sissy cock which when fully erected is about 3.5 inch or 4 inches.

I have always had a crush on this girl named Amrita. She was a family friend of mine. She was really good looking and looks like a sex goddess in real life. Her figure is 32-28-34. People could easily get a boner just by looking at her even in photos!

One day I finally gathered a great amount of courage and asked her to be my girlfriend. To my luck, she agreed. I was so happy.

We dated for about 5 weeks during which we had a lot of intimate moments. We used to kiss a lot and smooch each other damn hard. Her lips…Ufff!!! Those were the perfect lips I had ever seen. However, Amrita wasn’t ready for sex yet. But somehow, I convinced her to have sex.

One day, she invited me to her house as she was all alone and her parents had gone out of town that night for 3-4 days. I was very excited about losing my virginity. I bought one packet of condoms. I had decided thinking I would satisfy her and I will be the only male who would rock her world on the bed!

I reached there we had dinner. And finally, it was fun time. We were sitting on the sofa and started making out.

It was an intense make-out session for nearly 10 minutes. Damn, my girlfriend smelled so nice that night! Then I took her t-shirt off and to my surprise, she wasn’t wearing a bra. Fuck, my sissy dick almost came seeing her body.

Then she went and dimmed the lights. I made her lie down on the sofa, took off her pants and then started licking her pussy.

Amrita’s juices started flowing on my tongue. God, they were so tasty. I slowly started fingering my girlfriend’s pussy. Amrita started moaning hard. It was the time I thought I should make my dick enter her pussy.

I took my dick out and started wearing a condom, but it didn’t fit well. It was hanging out a bit. I thought to myself that I should have bought a bigger size. Anyway, I continued and was ready to insert my dick.

So, I inserted my dick inside my girlfriend’s pussy and started fucking her. Unfortunately, I came after 4-5 strokes. Amrita didn’t feel anything. I was so embarrassed that I immediately grabbed my pants and ran from there. My girlfriend called me but I didn’t reply for days.

Then I thought that I would take her to Bangalore to make up for this since I loved her so very much, but never did I know that this would be such a huge turning point in my life.

I contacted a friend of mine who was in Bangalore. His name was Sameer. I met him through ISS site. He was a very good friend of mine and I trusted him more than anyone else in my life.

So I told him all of my problems and what happened. He consoled me and said not to worry and he has a solution for this. In fact, it was his idea to take Amrita to this trip. Little did I know about his evil plans!!

We went to Bangalore. It was a trip for 5 nights and 6 days. I booked a 5-star hotel near Sameer’s residency area. The first night we went out for sightseeing and then came back to relax.

The next day we planned to met Sameer at a cafe at 2:00 in the afternoon. She was wearing a short green coloured dress which was quite tight and suited her figure very well. She was looking a total sophisticated slut bomb.

We all met, had fun and ate and left by 3:30. During this time we met, I thought Sameer was literally flirting with my girlfriend and she too responded to him very well. Sameer being a well-built attractive 5’9 man was proving his sexiness.

I didn’t mind it and took it lightly. The same night Sameer texted me that it was lovely meeting us and that Amrita was a beautiful person and she deserves all the happiness. Soon things accelerated and out of the blue, Sameer said:

“I have a solution to your problems”. I knew he referred to my sexual problems.

I asked out of curiosity, “What solution?”

He replied, “I can fuck Amrita and satisfy her!!”

I was damn furious but I don’t know what struck me after talking for 5 minutes. I easily surrendered to him, maybe it was my innermost fantasy to be sissified and be cuckolded and see my sexy gf being fucked real hard by a big dick.

I asked him, “How will you convince Amrita though?”. He replied, “No need to worry about her, she has already agreed to meet me tomorrow morning.”

I was shocked to hear that. My own gf was thinking of cheating on me and that too with a guy whom she just met once. Sameer then explained to me that she might be desperate to lose her virginity and get a real cock and that she was a woman after all and would be really horny!

The next day I confronted my girlfriend and she explained to me and was really sorry how she felt. But she told me that she too had needs and whom else could she use rather than such a close friend of mine. I understood and told her that it’s ok.

I asked Sameer to come and meet at the hotel room at 9:00 pm that night. He arrived at sharp 9:00. Of course, who wouldn’t if one is getting an opportunity to fuck such a beauty. I was terrified as well as excited. As soon as he entered, we ordered dinner. Amrita and Sameer had some wine too. I don’t drink so I just had some red bull.

We were sitting on the bed and soon, Sameer initiated and engaged in a deep lip lock with Amrita. She too started vigorously responding back.

Sameer then started caressing her boobs and ass. Soon both of them removed their shirts and pants. Amrita was really shocked seeing that monster 8-inch rod. Even I was embarrassed and felt ashamed of myself.

And suddenly, I don’t know what happened to my girlfriend, she came near me and whispered in my ears, “From this moment, don’t take anything seriously. It’s all for fun, babes!!” and gave me a tight slap. I was feeling humiliated but also kind of enjoyed it.

She started abusing me and my small dick and said that I wasn’t a real man and cannot satisfy or even fuck a woman normally. Sameer was laughing and he pulled my girlfriend by her hair and made her suck his dick. She couldn’t handle his big dick all at once but still, he continued and deepthroated his dick.

My girlfriend was feeling so good. They ordered me to strip down and started abusing me and told me to watch and learn how a real man fucks and satisfies a woman!

Then, Sameer fingered my girlfriend and she had already come twice. It was climax time. Sameer took his 8-inch monster and inserted in my girlfriend Amrita’s pussy slowly.

It had only reached half her pussy and she started screaming and moaning. It seemed that her cherry wasn’t even popped yet. Sameer was laughing at me and said, “You miserable sissy, you couldn’t even reach her hymen to break it properly!!”

I was utterly humiliated at my cock and myself. Sameer calmed down my virgin girlfriend and started stroking her slowly. Amrita too was liking it as she had never experienced such a huge cock inside her pussy, stretching her walls so good.

She was moaning really loudly, “AAAAHHHHHHHH…UFFFFFFFF…FUCK ME HARDER SAMEER. SHOW THIS SISSY HOW IT IS DONEEEEEEEE”, and she reached her climax only in 5-6 strokes. Meanwhile, Sameer hadn’t even broken a sweat. I knew it very well that this was going to be a long night.

This continued and soon Sameer turned my girlfriend in doggy style and spanked her ass. Then he inserted his rod once again and fucked her for nearly an hour. I could hear all types of screams and moans, “OHHHHHHHHH, DEPPEEERR SAMEER MORE FASTERRRRR…SHOW THIS SISSY BITCH HOW IT’S DONE”.

Listening to all this, Sameer got more furious and held Amrita’s hair and fucked her like a fucking demon. It was so fast that Amrita couldn’t stop screaming and moaning out of pleasure.


They were both drenched in sweat. They hugged each other and kissed for the next 10 minutes. Then Sameer got dressed and winked at me and left saying, “I am the master of your sex life now, bitch!!”

I didn’t know what that meant but I certainly knew it wasn’t going to be good for my manliness and manhood. Amrita was still recovering from that wonderful beastly sex. I just went to the bathroom, masturbated and slept wondering what was going to happen in my life next.


I hope you liked this story and it certainly doesn’t end here. There are more parts to come. As I said, all the characters are real.

So, if you want to meet my master or want to meet me the sissy and take my anal virginity or anyone who wants to see amrita or her mom or my mom and sister, please message me at [email protected]

Stay tuned. Thank you.

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