My Journey into Cuckolding

analystguy27

Well-Known Member
Cuckolding for me was an accidental discovery.

I lost my virginity to my girlfriend at 16 but I was no stranger to sex before that.

My best friend, Riya, is a really hot girl. We ended up growing together as her mom and my mom were the best of friends and we were neighbours. We became lovers and are best friends and lovers till date.

The trouble with having a hot girl as a best friend is that most of your friends think she is hot but you do not see it even if she is usually around you in really skimpy clothes.

That was my case too. We had known each other since childhood and she was 2 years older than me and though we had seen each other nude, we never really had any sexual intent.

We enjoyed our time together and we both had a love for physical sports.

We discovered we could be friends and also fuck each other when she was 18 and I was 16. We were playing a game of tennis and she was all over the place. That was highly unlike her. Being a guy and her best friend, I knew all about her boyfriends and dates and she knew about mine and we would rib each other when we were by ourselves. I was no different today.

Me: Why the hell are you so frustrated today? Boyfriend not giving it to you good?

Riya: Fuck you!! He leaves me hanging and cums quickly.

Me: Ask him to eat you out to an orgasm or ask him to use his fingers

Riya: You are a know-it-all!! You eat your girlfriend?

Me: Sometimes when I am not up to the task, I use my tongue to get her over the edge. Don't you guys 69?

Riya: He does not like it.

Me: Dump him and find someone who will eat you anytime you ask.

Riya: I will fuck his brains over it. How does it feel to be eaten?

Me: How am I supposed to know that? When I get a blow job, I cum in her mouth or on her and I like it a lot. I also like hearing her cum and beg for more when I eat her.

Riya: That does sound hot!!!

Me: Do you want me to eat you to give you a taste?

Riya: I don't think you have it in you to please a woman.

Me: I think you are just scared you will like it too much and then get addicted to it.

Riya: Fuck you!!!! Let's go home and you can show me.

We went home and being all sweaty her skin glistened and tasted a bit salty and the smell of her sex with sweat was very appealing. Our parents were out, she stripped and pushed her pussy towards me and I went to work.

Her slow moans turned into fervent pleas and her legs were in the air and her hands pushing my head into her pussy and she moaned and came all over my face.

All this while I was fully clothed but hard as a rock.

She caught her breathe and said she loved it and I said that she should get her boyfriend to eat her pussy after we had sex and went down on her again. She was trying to catch her breath and came again. We then 69 where I was tenderly loving her pussy while she gave me a blowjob.

The next day Riya called me to her place and opened the door in a tube top and hot pants and had a 2 word statement, "Let's fuck."

We fucked fast and hard and I came in her and she then rushed me to her closet as the bell rang and cleaned up a bit and went to the door and got her boyfriend into the room and forced him to go down on her.

He resisted but then gave in as she gave him an ultimatum and he ate her to 2 orgasms as she wrapped her legs around her boyfriend's head. It was hot watching him eat my cum out of her as she moaned and told him she wanted more of his tongue. She held his head as she grinded away and came. I watched the whole thing from her closet and got real hard.

Riya hurried him out by telling her parents will be back soon.

She came back and I was out of the closet and eager to fuck and she wanted more. We enjoyed the sex but were also seeing other people.

She wanted to experience having sex with another woman but was unaware how to go about it. I set it up where she walked in on me and my girlfriend having sex and then proceeding to fuck her.

Being best of friends and neighbours with busy parents really helped us play our sex games and explore the fun part of sex.

She walked in on me and my girlfriend having sex and just pushed me off the bed and proceeded to fuck my girlfriend. They grinded, 69ed and the moans really got me going. They had a small break where I walked up to my girlfriend and fucked her. I lasted less than a minute. I was so hard I could cut glass with my dick.

Riya dived right back into my girlfriend’s pussy and they 69ed again. Riya left my girlfriend moaning and satisfied and walked away.

My girlfriend and I then 69ed and relieved every moment of it and my then girlfriend left a very satisfied woman.

I went to Riya’s home and thanked her by eating her ever so slowly, making her cum again and again while she held my head and pulling it in and moaning.

This fuck buddy arrangement where I had sex with Riya before she got her boyfriend to eat her with me watching from the closet continued for a year. My then girlfriend and Riya got together a few more times and let me watch but me and Riya never hooked up in front of my girlfriend.

I eventually moved to another city for my college but Riya is still a part of my life till date.

Unwittingly, I helped Riya cuckold her boyfriend even if it was her cheating on her boyfriend.

I learnt about cuckolding and the terms 6 months into my college.

That is a story for another time.