It all started a few months ago where i thought to myself i had to have a gay experience after fantasizing about it for along time, i have been curious for a few years but turned 18 last summer so havent thought about actually doing the act as i felt too young, but wanted to do it before going to college.
I read a lot on forums about being bi or curious and about peoples first times. I read a lot of erotic fiction and spent hours at night reading, then started to look at gay personals on websites and craigslist and got extremely turned on by them.
Last week i decided to make my own ad on a popular site it read.
“19 looking for first time” “looking for older guy to experiment with, needs to be discreet and patient”
I nervously went to bed after putting the ad online.
In the morning i checked my email and was surprised to find 13 emails, about half were just small 1 liners saying how they thought my ad was hot or good luck shame you are too far away.
Then i came across one that i really liked, it was from a 47 year old married man named jay who was local and was looking for young guys to show them “the joys of sex with a man” he talked about how he would be patient and to just mail him for a chat nothing more. So i did, i replied to his email and talked for 4 days over email, i was growing very attracted to him he seemed very wise and giving me advice.
The conversation soon talked about real life and whether i was ready to be with a guy, i knew i was ready and knew that i wanted to be with him he suggested we meet somewhere in public just to assure me he was genuine.
We decided to meet at the cafe in town and he sent me a picture of him so i could identify him. On saturday i went to the cafe and nervously sat for a while, i then noticed jay walking in and ordering a coffee, he sat down at a table and started reading a newspaper. I had to pluck up the courage to walk over and sit next to him which im glad to say i did, i was sweating with nerves as i sat down and he looked up and said “you must be john” and i nodded, we chatted for a while and he made me feel really comfortable. He suggested we leave the cafe and go for a walk, it was a beautiful day and we walked around the park, again the conversation came onto sex and he was suggesting private places we could go; toilets, his car, his house or in a hidden area in the trees. I said i would like to just masturbate to start with and he nodded and suggested we go to the trees; we walked for about 5 minutes into quite dense bush and trees and then stopped.
After an awkward silence he asked whether it was ok for him to lower his pants, i nodded and he did revealing his beautiful long, thick and extremely hard cock. I decided to lower my pants too exposing by not so impressive cock he reached over and started to run his fingers along my shaft and over my balls and stepped closer, i looked up at his face closed my eyes and kissed him on the lips, he slowly started to stroke my penis while locked in a slow kiss, his tongue rolled in and out of my mouth and it felt great. I then reached for his cock and started to run my hand up and down the long shaft, after a few minutes of kissing and jerking each other off i broke the kiss and smiled at him. I slowly sank to my knees and came face to face with the purple head of his throbbing cock, i wrapped my hand around it and stroked it a few times then stuck my tongue out and licked the tip, it was warm and moist with a musky taste and smell it was beautiful. I opened my mouth and took the head in, i slowly massaged it with my tongue and to my joy i hear him breathe deeply, i look up and make eye contact with him, he smiles and gently rests his hand on the back of my head. I start to take more of his cock into my mouth i get about half way down to shaft until i feel i cant take anymore then i slowly withdraw till the tip is between my lips then draw my hand up the shaft in unison my hand and mouth work up and down his cock, i do this for about 5 minutes slowly picking up the pace.
I can see and feel that he is getting close to climax, i look into his eyes again with his cock in my mount and my hand around his shaft and my other hand around my cock and start to go faster and faster, he runs his hands through my hair and groans, i feel his cock grow his abs tighten and his balls pull up. He then firmly grabs my head and pulls me into him and i feel a rush as his semen jets out onto the roof and back of my mouth, i use my hand to squeeze his cock to make sure i have it all and then swallow, he removes his cock from my mouth and praised me on how good i was for a first timer, little did he know that i practiced on a dildo and watched a lot of porn.
I was still hard and was slowly jerking myself off and he tells me to leave it and to pull my pants up, i do so and we walk back into the main park, we finish our walk and he walks to his car with me, he then turns and asks whether i will be coming home with him or whether i am satisfied with my gay experience. I was too horny to answer and just opened the door and sat in his car, he got in and we drove off, while driving he unzipped my pants with his free and got my cock out and stared playing with it, i was incredibly turned on as i hadnt had a release since last night.
Soon we were at his home and we went inside, he asked whether i wanted a drink i looked at him in silence, he smiled and suggested we go to his room instead, he takes me by my hand and we walk upstairs and into his room. We stood facing each other by the side of the bed and we kiss each other again. Soon his hands were all over my body and starting to take my clothes off. I decide to do the same to him and soon we are in our underwear. He then lays me down on the bed with my legs dangling over the edge, he leans over me and kisses me again running his hands over my chest and stomach and then under the elastic of my underwear and starts playing with my cock again, he starts kissing my cheek and moves to my neck, kissing and gently licking his way to my nipples, i feel his hot breath on my stomach as he moves down to my crotch, he slowly takes my under wear off and exposes my rock hard cock, he uses his hand to guide it into his mouth and he expertly takes it all into his mouth, his nose buried in my short pubic hair i feel his tongue moving around my penis and i roll my eyes back in ecstasy. He expertly uses his mouth, hand and tongue and brought me to climax, we kissed again and i could taste myself in his mouth we kissed for a while and i was hard again he then broke the kiss and stood up, walked over to his bed side table and brought back a small bottle of lubricant.
My heart started to race as i knew what was coming, he asked whether i was ready and i just nodded, still lying my back he told me to bring my knees to my chest, i did so and he bent down and slowly licked my balls and moved towards my ass hole, i feel his tongue probing my tight virgin hole the warm wetness sends shivers around my groin and then a lubed finger slowly penetrates me. He adds more lube and inserts his finger again this time with more ease, he swirls his finger around and i start to relax, my muscles relax and i breathe deeply and slowly. He stands up and gets into position he looks at me and i look at him as he smiles at me as i feel the tip of his cock at the entrance to my lubes hole. He runs it up and down between my cheeks then starts putting pressure on, i relax and slowly feel his cock sliding into me, the big purple head pops in and past the tight muscles around the entrance, i let out a long pleasurable moan as he slowly he pushes his thick shaft into me, stretching my tight virgin ass around his big cock. It seems an eternity until i feel his balls touching me, i feel very full, i can feel his cock deep inside me, he holds himself inside me for a while to let me adjust to the fact i have just lost my anal virginity, then slowly he withdraws until just the tip is inside me making me feel very empty inside. “please, fuck me.” i say in a soft voice.
He thrusts into me hard and fast the second time and must have hit me in a special spot as i felt a wave of pleasure. He starts to fuck me in long smooth strokes making sure all of his cock goes into me, he was rubbing the right spots as i felt a wave of pleasure every stroke. I reach out and touch his chest and rub my hands over his body i clamp my legs around him as i feel my climax building, i grab his ass and pull him into me and he picks up the pace and pumps into me hard and fast. Sweat forms on his brow and he lets out loud groans and moans of pleasure as he continues to pound into me. It was too much for me and i soon have another climax my body tenses, my cock throbs with no stimulation and my ass tighten as i unload onto my stomach and chest. The sight of my orgasm sent jay over the edge and with a deep thrust i feel his trembling cock swell and unload his seed deep inside me. He falls forward and breathes heavily over me and we kiss patiently until his cock softens and slides out of me. In the afterglow of my climax i feel so alive so pleased with myself so happy that i did this.
We had made quite a mess and so jay told me to jump in the shower, i stood up and walked to the bathroom. I felt his eyes on me, my ass and his cum running down my legs the sight must have made him incredibly turn on. As soon after i got into the shower he was in the shower with me. Running his soapy hands over my body i again submit to him and i bent over ready for my second fucking, his hard cock was quickly buried inside me, thrusting in explosive passion. The hot water on my back, my head down and my hand pumping my cock caused me to feel feint and light headed. On the verge of blacking out i am engulfed in pleasure as i have another orgasm and soon after i feel jay unloading inside me again. I collapse but jay holds me firmly he washes me and himself and then lays me on his bed. I must have dozed off as i woke a hour later to a empty room, i get up and smell cooking i walk down stairs into the kitchen to see jay cooking his dinner, i see the time is 7pm and i tell him i should be getting home but he insists on feeding me first. I agree and have dinner with him. After dinner jay drives me into town. He stops the car in the car park and asks whether i had a good time, i, of course said yes and we said our goodbyes.