Note to the reader: In this diary I will tell the true stories of my sexual encounters that have come about thanks to the Internet. Some more precise details such as names and places will be left out to protect other’s privacy, and mine, and also because they don’t matter, but otherwise I will try to be as accurate and truthful as possible.
After my first experience with Ed, I took a break from looking for meetings through the Internet, mainly because I moved to a different country for a year. For a while I did amuse myself by creating a new account on the site pretending to be a girl, complete with a photo of me from the back dressed in some of my sister’s clothes. Unsurprisingly this profile got a lot more responses than my male one, from men of all different ages, so if you’re a woman finding someone to have sex with through the internet is a lot easier than for guys. The trick would be in finding someone who isn’t a weirdo, and finding the meets that would be worthwhile amongst the dozens of replies you’d get.
Once I was back in the UK I decided that a year without sex was far too long, so I started working on my real profile again, concentrating on getting some guys to begin with. Fairly soon I started getting some replies, but despite the fact that I was quite clear in my profile that I couldn’t accommodate, people still kept assuming that I could. One who didn’t though, Jason, lived in a city not far from my university city, so I told him when I would be back there so we could arrange a meeting. He was 30, so a nearly ten years older than my 21, but from his pictures he looked pretty attractive, and was straight forward in his messages. We exchanged phone numbers, but then for a whole month after I was back within easy reach of him, and several explicit text messages in which he told me he wanted to fuck my tight arse, we still failed to meet.
Finally though, we agreed on a Wednesday morning when I didn’t have class and he didn’t have work. Unfortunately it meant that I had to get up at 7.30 in the morning, but I managed it, taking a shower, dressing in jeans and a jumper rather than my more usual hooded top. I then waiting in my room rather than having breakfast as I didn’t feel like explaining to my housemate, who I could hear moving around, why I was up so early on a day without lectures.
I left the house and went to catch the train, which took about an hour, during which I slept and fantasised about what we would be doing together soon, trying to get myself aroused enough to overcome the butterflies in my stomach at meeting someone new again. Once at my destination, I sent Jason a text to ask him where he was, half-hoping he wouldn’t be there, and considering just getting back on the train and going home, but he sent one back straight away saying he was in a silver Clio opposite the station, facing me in fact. Taking a deep breath, I went over to it and got in.
“Hi, I’m Jack,” I said, greeting him.
“Nice to meet you finally,” he replied. “It’s been what, about a month we’ve been meaning to do this?” We started making small talk, about the journey up, our two cities, going out, his job (air steward – really!) that sort of thing, and I was checking him out, noticing that he was very good-looking, a well toned body, nicely dressed, unlike my very casual gear, even wearing shades.
“You want to go back to my place then, yeah?” Jason asked suddenly in the middle of the conversation, maybe because I seemed nervous, which was reassuring to me, as he was clearly far more experienced than me, so he could have just taken it for granted that I would do what we agreed.
“Yeah, sure,” I replied, sealing my fate.
He continued driving, finally pulling into a fairly nice estate of semi-detached houses, hardly a car to be seen, and pulling into a drive at the end.
“There’s no one about is there?” he remarked getting out. I followed him quietly as he opened the door and punched in the code for the alarm, then into the kitchen. “Would you like something to drink?”
“Some water would be fine,” I replied, my mouth bone dry as the nervousness, which had been ebbing away, came back full force. He passed me a glass of water, pouring one for himself, and I drank a couple of mouthfuls.
“So what do you want to do?” he asked. This was exactly what I didn’t want him to ask. I was fine telling people my desires on the Internet, but saying them out loud seemed kind of corny. I took another sip of water before replying.
“Well, you know, we’ll see how it goes,” I mumbled.
“Do you want to start down here, or go upstairs?”
“Probably best to go upstairs, I think.”
I turned and climbed the stairs, feeling him close behind me, and followed his directions into the first room on the left. It was full of stuff, only a small area of floor free from clutter, and several big mirrors arranged around the place, behind the double bed and next to the door. A little taller than me, he came closer, and not saying a word more, began kissing me, his arms pulling my closer. I put my arms around him, mimicking his moves a bit, squeezing his buttocks and doing my best to tongue him back and return the kiss against his stubble. I began to relax, and decided it was time to take my jumper off. He did the same, and then we resumed kissing, the only sound we made the rustle of our hands over each others clothing, our breath and the occasional wet smack of our lips.
Jason began pulling my buttocks harder, grinding my groin into his, and then reached down to cup it. I also wanted things to progress, so I took off my T-shirt, and once again he copied me, so now I could feel his strong muscular chest while he felt me up. Grinding into his hand a little, I decided to see what his package was like, as the pictures he’d sent me months before had been automatically deleted and I couldn’t remember what kind of size he had. To my surprise it felt pretty big, and I began to think that finally I was going to be properly filled by a real cock!
Trousers were the next to come off and without the denim in the way, my estimate of the size was proved to be correct by the feel through the fabric of his boxers. Eager to see it for real, I knelt down and pulled his underwear off, releasing a beautiful shaven cock, only semi-erect for the moment, but clearly not much less than two inches thick and a little more than six inches long. To begin with I licked at his smooth balls, taking each in my mouth to suck gently, tracing the shape with my tongue, tasting his skin, but moving my attentions quickly on to his shaft, feeling it harden, circling the head a few times before taking it into my mouth.
I actually had difficulty fitting it in without my teeth touching his skin, but I began sucking and pushing forwards, trying to use my tongue at the same time. Jason put his hand on the back of my head and began pushing me down more which helped, although it meant some silly sounds got made as air escaped between my lips and his cock, and I could soon tell that his cock was fully erect. Glancing to the side, I could see myself sucking his dick in the mirror, which turned out to be a real turn on. He began thrusting harder, pushing further into my throat so I could no longer really suck and just kept my mouth open, trying not to choke.
When I really was starting to choke I stopped him and stood up, and he took that to mean that it was his turn to go down on me. Pulling my trousers and boxers off, he repeated the ritual, licking my shaft and then peeling back my foreskin. As he began sucking I closed my eyes and really started to relax, resting my fingers lightly on his tanned shoulders and feeling myself grow in his warm wet mouth. His hands pulled at my hips, getting me to thrust at his mouth, which I did, but not as enthusiastically as he had, leaving most of the work to him. It felt really good, but this wasn’t quite what I had been looking forward to for months, so I pushed him gently away and rummaged in my trouser pocket on the floor.
Meanwhile Jason had sat down on the side of the bed, where I passed him the condom I’d been searching for, and while he was putting that on I got out the tube of KY jelly I’d brought and began smearing it around my arse, before squeezing some into my palm and lubricating his rubber coated cock. Turning around, I was now standing between his legs facing the mirror with my back to him, then holding his hot shaft in my right hand and holding his legs with my left for balance, I bent my knees to lower myself down. I tried to relax my muscles, and guided his head to my rear entrance, pushing to my hips down to get him inside. At first, it stretched me too much, stinging a bit, so before it was all the way in I came up again, but gradually I relaxed more and admitted more of him inside, the slight ache soon eclipsed by the pleasant feeling of being filled.
In order to make things easier for me, Jason lay back, enabling me to bring my feet up on the bed so I was crouching over him and watching myself in the mirror as I bounced slowly up and down on his cock, holding my balls up out of the way so I could see better. Unfortunately, as I wasn’t used to being in this position, my thighs were not strong enough to keep going for long, so I had to get off.
Jason took the opportunity to get a little bottle of poppers out of the drawer next to his bed and take a sniff, offering me some but I refused. As he was still on his back, I decided to try kneeling over him so I could look down on his smooth chest decorated with tattoos while pushing my arse back to take him inside me again, doing my best to tighten my muscles now rather than relax them. We stayed in this position for a couple of minutes, but even with him thrusting up to meet me it was still going a little slow for what we were both in the mood for, and my attempts at giving him a tighter hole to fuck kept interrupting things each time it forced him out, so I got off once more.
“Let’s try it like this,” I suggested, getting on my hands in knees in the classic doggy position, and waited for him to get ready.
He entered me easily now, and it didn’t ache at all, although I could feel it all the way in, pushing against my insides and producing a fantastic sensation. His strong arms pulled my waist back to meet the thrusts of his hips, so I was able to just sink down on my elbows and enjoy him. But this position soon became frustrating as he couldn’t penetrate me as deeply, so once more it was time to change position.
This time Jason asked me to get on my back and move closer to the edge of the bed. He was still standing, and lifted my legs right up out of the way to push himself inside my arse again. Now he could really start pounding my arse, thrusting deeper and faster, and reaching down I could feel his rigid shaft sliding in and out between my fingers, then I cupped my balls with my hand.
As he continued to fuck me at that speed, the sensation began to change from just pleasant to fantastic, a hot feeling rising up into my chest so that I couldn’t help but gasp. Even though I was no longer erect it felt like I was about to cum, but the feeling stayed without anything further happening. Jason bent down over me, supporting himself on his muscular arms, and I arched my back up to meet his lips for a passionate kiss, mostly licking each other’s tongues.
“Let me know when you’re near,” I whispered.
“I want you to finish in my mouth,” I said, and grinned to myself that I’d actually said it, and that I’d be able to live out one of my fantasies at last.
He continued fucking me, and I tried to tighten my arse around him again, playing with my cock, and then wrapping my arms around his back, feeling his chest, moving my hands down his body as he kissed me and moved above me, until I spread my hands over both his taut firm buttocks, pulling him into me.
“Oh, I don’t want to cum yet!” he said suddenly, and pulled out for a breather.
I sat up, cupping and gently squeezing his balls until he was ready. When he was he didn’t lean over me again, remaining standing instead but thrusting even faster, sighing “yeah, yeah”, and then he pulled me right up so only my shoulders were still touching the bed, my legs straight out either side of his neck. He put me down again and started wanking me at the same time, my cock which had been semi-hard most of the time filling out again.
I closed my eyes and spread my arms out on the bed, moaning and gasping as his hand on the outside and cock on the inside brought me nearer to orgasm. My breathing suddenly quickened and I gasped loudly, a haze seeming to fill my brain as I came, Jason still pumping his hand on my dick and my hot spunk splattering all over my chest, engulfed in it for at least a minute.
I’d barely come out of it when he pulled out and took off the condom. I quickly sat up, taking his hard cock from his hand and putting it in my mouth. Sucking hard I played with my sticky cock with one hand whilst massaging the shaft of his with the other, bobbing my head as fast as possible in response to his gasps of pleasure. Soon I could taste another hot liquid join my saliva on my tongue, and I slowed but sucked harder, enjoying the sound of his moans and the strange sweet taste in my mouth until I noticed no more had come out for a few seconds. I swallowed and licked around the head, getting it nice and clean before I finally stopped and sat back. We looked at each other and smiled, both catching our breath.
“Just what the doctor ordered, I think!” Jason said finally, and we laughed.
Not saying anything else, we both cleaned up and got dressed, then he drove me back to the station, making small talk on the way once again. We said good bye and I got out quite quickly. It had been great, but I was feeling a little strange from our abrupt parting. As I was waiting for the train though, I received a text message from him saying: “Cheers m8 that was fantastic, well horny! Hope u enjoyed it 2?” I replied that I had, and since then our meetings became a semi-regular thing every two or three weeks.