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Fantasy to Reality
25/07/2026
Every since I started jerking off to penthouse letters. I became addicted to being a cuck way before I had my first girlfriend.

We met on a Friday night while cruising main Street in our small town. I didn't know her because I was new to the school. Her name was Jan and she was a senior and I was a junior. She was a tall thin brunette with a rocking body. My best friend Mark and I were riding together the night I met Jan.

She was the aggressor and me being the shy one was intimidated with her beauty. She asked if I wanted to ride with her and I said sure. We met in a parking lot and I got in her car. She was driving and I couldn't believe this was happening.

She didn't go back to main Street but just drove around as we talked. It was mostly her asking me a ton of questions. Then she takes me to this small private lake near town I didn't know existed. We parked and it was very dark with no lighting around. She kissed me and before I knew it, she was on top of me and grinding against my hard dick. We still had our clothes on.

I was a virgin and had only kissed a girl once before. I felt like this was total role reversal and wasn't in control, though I didn't know what to do anyway. She began groping my hard dick and then asked me to squeeze her tits. My first time playing with tits was mind blowing.

I slipped my hand inside her blouse and under her bra. She had a full set of C cups and boy they felt good. She had small dark nipples that were erect about an inch long. She asked if I had a condom and I said no. She asked if I had ever fucked before, again it was no. That seemed to fuel her fire and she said she was going to take my virginity.

I was just along for the ride. She asked me to remove my pants as she got naked. We also got in the back seat. She climbed back on top of me and started rubbing her wet pussy on my dick. I was on the brink of shooting my load and was trying to hold it back. She asked me to suck her nipples and I did as she grabbed my dick and began lowering her very wet warm pussy onto it.

Once I was all in she told me to suck her nipples as she started slowly riding me. Looking up through her big tits and seeing her face looking down at me was all I could take.i announced I was going to cum but she kept going. I grabbed her hips as I unloaded inside her and she picked up her speed and rode me harder.

My dick was very sensitive after cumming and I grabbed her ass trying to stop her because I couldn't handle it. She eventually started to orgasm and screamed out very loudly while doing so. Kinda scared me and I asked if she was ok after she collapsed on top of me. We just lay there with our naked hot sweaty bodies against each other. No words spoken for a few minutes.

I couldn't wait to tell mark what had just happened. She began kissing me again and eventually asked if I enjoyed it. I said it was better than anything that has ever happened to me. She was happy she took my virginity. She then asked if I knew what this meant. I said no, and she simply said that I was now her boyfriend and I belonged to her, understand? I agreed.

I'll admit I was worried that she would get pregnant but she didn't seem to worry about it. She kept complimenting me on my nice hot body and cute looks. She said she was surprised I haven't already been taken. I was new to the school. I knew girls were attracted to me because they would make comments but I guess I was naive.

I told her I was surprised she was single, and she said she had just got out of a long relationship with a older guy in college. He broke up with her because of another girl. I didn't care that she was well versed in fucking and she was my teacher. I was in love and wanted to marry this girl.

When I told my buddy Mark what took place, he said I was lucky because she is out of my league, I agreed. He then teased me saying she must like small dick. I'm only six inches which is average I reminded of. He likes to always throw it in my face that his dick is much bigger, nine and a half to be exact, so he says.

I have seen it on occasion and I'll admit, it's impressive. Me and Jan had been going together through the summer and into the school year. We were fucking at least twice a day sometimes more on weekends. She had put herself on the pill so we didn't worry about anything.
It was in the winter months when we had a double date with Mark and his girlfriend Melinda.

She was a sophomore and also very hot. Mark constantly bragged about destroying her pussy and saying he feels sorry for the next guy. Not only was his dick long, it was extremely thick. I thought it was unusual since I had the bigger body frame. I made a comment to Jan about Mark resizing Melinda's pussy. She asked what I meant. I told her that he was hung, bigger than me.

She replied, you're not that big with a smirk. Then she asked, just how big is he. When I told her she didn't believe me. That's when she began asking more questions and giving Mark more attention in my presence. I became a little jealous and again felt like I was the girl in the relationship. I was along for the ride. It was spring and the weather was warm so she asked if Mark would like to go to the lake and go swimming with us.

I told her I would ask but never did. Then he stops by the house asking what time are we leaving. She had asked him herself. Saturday came and the three of us went to a popular lake. Jan was driving and we went to a secluded area. We got out and unloaded the car spreading a large blanket. Jan then removes her T-shirt and shorts.

My jaw dropped and so did Mark's. She is a sun worshiper and her dark tan and her rocking hard body was a sight to behold. Also she had on the smallest bikini she could fit in and there wasn't much left to anybody's imagination. She said she was going to lay in the sun and for us to go swimming. We removed our shirts and headed to the water. Walking down Mark makes a joke about destroying her pussy. I laughed it off and said dream on, she's mine.

We swam and frolicked in the water and after a bit Mark said he'll be right back and heads to the car. Several minutes go by and I don't see him by the car. The car was blocking the view where Jan was laying. So I proceeded up to the car only to find Jan lying without her top on and Mark applying sun lotion to her back. I stood and watched with no words. She then asked him to apply it to her legs. She then spread them giving him more access.

She didn't know I was standing by the car intently watching. Mark looked at me and winked with a smile. He worked his way up her thighs towards her crotch and I felt my dick get hard as a rock and push against my thin swim trunks. He was deep in her crotch with his hand clearly rubbing her pussy. She was beginning to squirm and moving her hips to meet his hand.

She the said you you to get the front side. He stood and there it was, his huge cock running down the length of his leg. She rolls over and her top is left on the blanket exposing her beautiful tits that were tanned also. She glanced at me but noticed his huge cock and couldn't take her eyes off of it. Not even giving me recognition, she asked him to apply lotion to her front side.

She laid on her back as he began at her shoulder and moved to her tits. He was squeezing them and rolling her long nipples as her breathing became heavy and louder. After covering both tits he moves down towards her crotch. That's when I noticed her hand up his trunks leg playing with his cock. Without hesitation she instructed me to pull off her bottoms to give Mark access to her. I hesitated and she asked in a firmer choice.

Knowing now what was going to happen I did as she instructed and sat back. Mark began rubbing her clit and she spread wide for him as his fingers disappeared deep inside her. Before I realized it, I had my hard dick exposed watching silently stroking myself. I hear her say something and Mark stands and drops his shorts. She sits up to watch and sees me stroking myself. She smiled a me as she grabs his cock and pulled it towards her mouth. She sucked him for a few minutes and asked him to destroy her pussy.

He knelt between her legs looks at me and says, I told you as he pressed inside her. She let out a scream as he proceeded to destroy her. It wasn't long before I came and just saw quietly watching. The to of them fucked two more times before we headed home. I never said a word knowing my best friend just stole my love of my life and fucked her hard.

We didn't break up for at least a year afterwards. They were constantly fucking and I only watched jerking off. After that period I was forever changed as a man and realized I'm less than a man and a destined submissive cuck.

I eventually married years later and confessed to my wife about my sexuality. She was ok with it and eventually started fucking another man from work. They have been having an affair for years now. I'm ok with it but he's married and his wife doesn't know. It'll be interesting when she finds out.


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