This is a 100% true story about my first gay experience.
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Chubby Gay First Time With Older Man (True Story -
Sorry for the long story!!
Five years ago, I was 21 and in a boring relationship with a girl and my sex life was stuck at missionary once a week.
I always liked kinky sex and fantasied about everything. If it was weird and different then I was turned on. Nothing 'normal' got me excited.
Having had urges about sucking a cock since I was in school, I wanted to try and find someone who was up for some discrete fun. I ended up placing an ad on Gumtree and as I was filling out my ad, my cock was pressing against my jeans, I knew this is what I wanted. Once I had submitted it, I had more precum than I ever had before.
Being 18 stone and very hairy, I didn't have much self confidence and I thought the response would be small but to my suprise I had well over 10 replies asking to meet me. Mostly from older guys and that made me even more turned on.
To my regret, I didn't contact anyone. I just read their messages and instantly my cock would throb, I was begging myself to be allowed to do something about it.
A couple months later, I had a reply from that old advert from a 40 year old guy and he said he liked everything I described and wondered if I would be up for meeting him.
This was perfect timing. I was at an all time low in my relationship and I was gagging more than ever to have my first taste of cock. I messaged him back asking if he had MSN and so we started chatting...
He lived about 8 miles away and said he could drive to meet me that night. As soon as I read those words my cock nearly burst with excitement, it was almost like my cock was on its knees begging me to meet him. In a couple seconds of pure excitement and panic, I said yes.
I arranged to meet him in 30 minutes. I rushed into the shower and gave myself a good clean mostly around my asshole area. I had so little time to get ready I didn't have time to think about not meeting him. I left my house with a mixture of nervousness and excitement and it hit me right then that I was going to do something that felt so wrong but something that I had wanked over for years, it was finally coming true.
I was waiting at a bus stop and I didn't have a clue what he looked like and I didn't know what we were going to do to each other. All I knew was that I was going to see and feel a cock for the first time and that's all that mattered.
He phoned me to make sure I was there and I said yes. He said he would be 5 minutes and told me what car he had, so I could look out for him.
He pulled into the bus stop and waved me in. I sat in and I could see he was in quite a good shape and with a shaved head. His looks didn't matter as much as what he had in his pants.
We got talking and I suddenly realised that I wasn't turned on anymore, I tried to get hard but it wasn't working, I was panicking, realising that I might have to tell him I couldn't go through with it.
He said he knew of a country lane that he had used before, so he started to drive towards the countryside. With it getting close to midnight, he said no-one would see what we were doing.
He then said it wasn't far and I still couldn't get hard. So then I thought 'fuck it' and I pulled my trousers and boxers down so my unerect cock was exposed in front of a man I had only met minutes earlier. He was still driving and I noticed a bulge in his trousers, he smiled and reached his hand over to me and started rubbing his rough hands over my floppy foreskin. The excitement was back. From that point on, I had never been more erect in my life and the feel of his rough hands rolling around my foreskin made me want to scream in delight.
We got to the country lane and he turned off the engine. He leaned over and started kissing me. I thought I wasn't ready for kissing but I went with it as I was so turned on. His fingers were running around the head of my cock with my balls cupped in his other hand.
He asked if I had ever had someone touch my asshole before and I told him I hadn't. One of his fingers then slid down past my balls and I could feel some pressure against my bum, he then started massaging my hole with his finger, I let out a whimper as I had never felt pleasure like it. I couldn't get it out of my head that a fully grown man was playing with my cock and rubbing my ass with his finger.
He then pulled my t-shirt off so I was completely naked and started sucking my nipples while still rubbing my ass. He then pushed his finger into my hole a little bit and I told him that it felt really good. He started wiggling his finger around but didn't go any deeper, which was a great feeling.
I still hadn't got a look at his cock, let alone touch or play with it, so I reached my hand over but before I got too close, he pulled my hand back and told me to wait. I had never been dominated before and it felt great not to have any control as this older man was doing what he wanted to me.
With his finger still exploring my hole, he started to lick the tip of my cock and as he pulled his head back he had a line of precum going from my cock hole to his lips. He said I have a thick cock and that made my cock pulse with excitement, I could nearly see my cock veins pulsing in pure delight.
He then planted his face down to the base of my cock, without thinking I widened my legs so his finger could get deeper into my bum. He was bobbing up and down on my cock and with his finger still exploring me I felt like I was in heaven. I think he could sense I was close to cumming and he pulled away and told me to open the car door and bend over. I told him I wasn't sure that I wanted a cock in there yet and he said don't worry that's not what I've got planned.
So I bent over naked on the seat and he opened the car door, my bum fully exposed to this older man and not knowing what he was going to do next.
I could feel his rough hands grab each bum cheek and spread them wide open, the cold countryside air running across my open asshole, I was excited and nervous about what he had planned. I could feel him breathing on me, he was smelling my arse and he told me it was beautiful. My cock was swinging underneath me, I could feel my precum against the car seat. At that point I would've let him fuck me, but that's not what he did.
Suddenly I felt something on my asshole, it felt like nothing I've experienced before, his tongue was running around the ring of my hole and then he started probing my bum with his tongue, he stretched my cheeks wider and I could feel he was trying to open my hole as wide as he could so he could get his tongue in deeper. I relaxed and felt some more pressure as his tongue was desperately trying to taste the inside of my arse.
So, did I get to play with his cock?!