[M/M]y First Time | 2016

Edited for Paragraphs Sorry for the length, I started writing and couldn’t stop. I know the mark of a good writer is editing, but I am not a good writer. Sex starts about half way down for the inpatient.

I was 28 at the time in a LDR with a girl that was just starting its inevitable spiral towards ending. I had recently lost 20kg and had been spending a few nights a week at the gym and my body confidence was at an all-time high. I had never been sporty, a bit more a geek, but I was 6'3" and naturally broad and strong, which was only improving with the last 5 months in the gym.

The sometimes long nights in the 24hour gym after work had sparked a few friendships, nodding terms anyway, with the local regulars and I had started to get turned on by their bodies, shirtless and sweaty, posing in the mirrors, and showering after. I had to hide my erections every time I came out of the shower. If it had been that type of place I might have been keen to engage in a bit of fun there, but the gym was pretty strict on that, and there were even signs up in the changing rooms warning against.

I had downloaded Grindr just to see what it was like, but after sitting in work and spotting a guy on my floor messaging me, asking if I worked at the company (I didn't have a face pic) I stopped using it for a while. I wasn't keen on people knowing yet, I was still in a relationship and wasn't even sure my own sexuality, so I left it for a few weeks and went back to admiring from afar.

I had a conference in the next city, it wasn't far but the budget allowed for a hotel room, so I took advantage of it as it allowed me to go out for dinner with the organisers after and have a few beers. As soon as I checked in I thought of Grindr and I logged in. In a moment of courage I even took a face-pic just out the shower and uploaded it. It took a while to validate and I forgot about it while I got ready and started walking up to the restaurant.

As soon as I sat down my phone started going crazy, I had one or two pings while I was walking but obviously my photo had cleared. I am not a model, far from it, but I've been told by different people I am attractive, in an unassuming way, I have a pretty square jaw, dark eyes and had, after my rise in body confidence, started to take more care about my grooming, my hair and my beard. I apologised as I took my phone out and switched it to silent, there were around 25 of us at the table and I wasn't missed as I scanned through the messages.

I have nothing against older guys and always appreciate a bit of experience, but I had to discount them as I wanted my first time to be with someone my own age which left 5 guys who were pretty cute, two were only 19, students at the local university my hotel was near and three were my age or a little younger. Ever since I was a teenager I had liked skater guys, cute skinny ass hanging out, 10 years later skater guys are no more but the cute skinny ass hanging out guys still exist and that was my type. I had looked at these muscled guys at the gym but I wanted someone different. Over dinner I exchanged a few messages, politely declined sending any more pictures, I couldn’t for a start as it wasn’t the crowd to take a selfie infront of, and three of the guys left the conversations leaving me chatting to one of the 19yr olds and the late twenties.

After dinner I went back to hotel before I went to the pub to meet the rest of them, and spent an hour chatting back and forth to these two, the student was working at the local student union and was a bit slower at replying so I was getting on better with the other guy and we had exchanged a few more photos and I was hard as a rock, he sent a few topless photos, smooth and skinny, bit of a six pack that comes more from lack of far than any amount of muscle, and I started to jerk off, took my shirt off and suit trousers and sent him a few of me, I am still carrying a few extra pounds but the gym definitely was starting to show, and he saw how big a bulge I had. I’m not too big down there but I have pretty big balls and they make a large package. The next photo he sent was his cock and I almost blew then. It was about 8inches long judging my hand around it, and like him, pretty skinny. I thought that would be perfect for my first, and told him, we were telling each other what we would like to do to the other and I had to stop wanking as I needed to get back out, I had been gone an hour and a half by now.

All of a sudden however this guy just stopped messaging. We were on WhatsApp at this point and I could see the messages weren’t even reaching his phone. I was incredibly frustrated and now the other guy told me this was the busy time of the evening and he was talk later. I went from having two possible guys to none…

I went out and met the others, two of the sales reps had their expenses accounts running at the bar so it was free all night. Frustrated I ordered a few pints before starting on the whisky, I even got talking to a pretty attractive group of girls from the university and one was definitely interested but I blew them off and started to walk back a little worse for wear. I was pretty drunk and my Grindr was pinging on and off and I was chatting with guys I wouldn’t have spoken with previously but now I just wanted a cock. I had psyched myself up for this and wanted to fuck and be fucked. One guy was 20miles away and said he’d drive to meet me, another was local and wanted me to come to his, one was out and knew a place we could go in a park. None of these appealed and I had resigned myself to going back to my hotel room, finishing wanking over the pic I was sent and going to sleep.

Just as I arrived back at my hotel my WhatsApp pinged and it was the student. He was off work and wanted to know if he should come round. I instantly said yes and jumped in the shower, I washed all over, got out and dried off, put on new boxers, casual clothes and brushed my hair back quickly. I was messaged to say he was outside and I went down to reception to meet him.

I hadn’t received any pics of him but he was just my type, so cute, slim, skinny jeans, shirt with top two buttons undone and a light jacket, his hair was brushed to the side and was shaved to a high fade at the sides, and was clean shaven. He looked as if he couldn’t even grow a beard he was so smooth, I was instantly aware how young he was, 10 years younger but as soon as he looked at me I knew he was experienced and I was the virgin, he smiled, looked me up and down and told me to lead on. In the elevator we were only going two floors but I felt so awkward, he was just eye fucking me from across the lift and I felt myself getting harder and harder.

In my room we stood looking at each other for a moment, I offered him a drink, but I only had water or coffee, he declined and just walked towards me unbuttoning his shirt. He grabbed the back of my head and pulled me to his lips, we kissed aggressively. Our tongues were in each other’s mouths, my hands replaced grabbed his head and he continued to unbutton his shirt and then mine. His hands were on my chest and stomach and round to my back sliding down to my arse where he grabbed me and pulled me into him. I could feel his cock through his skinny jeans and he must have been able to feel mine, I was straining my jeans, he pulled his hands back up my back and slid me shirt off, kissing my neck and chest, sucking and licking my nipples caused me to moan and he continued down my chest to my waist band. My stomach jumped, it felt like I was going to faint as his fingers started to unbutton my jeans, revealing my tight bulging boxers, he looked up at me with a smile and said he was impressed, he had also not seen any pictures but he told me he was looking forward to this. Pausing an unbearable amount of time to ask if this was really my first time, I confirmed it was and I was pretty nervous. He just laughed and said I was in good hands.

I found out quickly how good they were, he pulled down my boxers to my ankles and my cock hit him on his chin as it sprang up, he laughed and then devoured it. I almost collapsed at the knees, he was good. I let me cock fall from his mouth and told me what amazing balls I had as he started to stroke my cock and tried to suck on them. He fit on in his mouth and was pumping me cock with his hand. Even in my drunken state he was just about to make me cum, and I told him to stop, I wouldn’t manage two in a night when I had drunk this much. He had unbuttoned his jeans and as he stood up he unzipped and slid them down to his thighs. As he sat on the bed I pushed him backwards and grabbing his waist band slid them over his legs and threw them onto the sofa. He was just lying there propped up on his elbows with that constant grin, and my eyes traced his body down to his underwear. It was the first time I’d see jockstrap style underwear and it was hot, I almost shot my load there, but I collapsed to me knees and slid them slowly down his legs and they joined his jeans.

His cock wasn’t too big, about my size but he was cut, which was new on me as well. I told him I didn’t know what I was doing but I was enthusiastic and started licking up and down his hard cock. I wrapped my hand round the base and started jerking it with the head just in my mouth, he moaned his appreciation and he collapsed onto the bed, I tried going deeper and gagged a bit, but kept going and had about 2/3 of his dick in my mouth before my reflex told me no further. I bobbed up and down on it, occasionally stopping to lend more of a hand as I licked the head. I heard him moan I was a natural which made me almost cum for the third time. After a few minutes his legs tensed and he said he was about to cum, less than a second later he did and hard. The first load hit the back of my throat and I gagged and pulled away and the second and third hit my face and neck respectively. I was laughing and coughing and I started to lick my lips clean, his cum tasted good, much nicer than my own and I was getting into it.

As he lay there, his cock wasn’t going down, it stayed hard. He was breathing heavily and pulled me up to his lips and kissed me, his hand on my cock. He licked his cum off my neck and kissed me again, and for the fourth time I almost came. As he lay there stroking my cock he told me he only topped, we hadn’t discussed it before but he could see I was disappointed but told me he would give me the best head of my life if he let me fuck him. I wasn’t going to say no either way, I wanted to be fucked and just sprang onto my knees, almost too keen. He went over to his jeans and pulled out a condom and a pack of lube. Rolling on the condom he smeared some lube on my ass and started working his fingers into me. He went in easily and again asked if this was my first time, I said it was but maybe the alcohol has relaxed me, the next thing I felt was his cock head rubbing on my ass.

Telling me he’d go slow he slipped the tip inside, as soon as this happened though I pushed back and took the whole length, we both grunted in shock, but I felt no pain, it went right in, but all he said was fuck I was tight. The feeling for me was amazing I felt every inch of him, and responding to my initial push, he took that as his cue to go all out, he fucked my virgin ass like he hated me, and I loved it, I was rock hard again. He slipped out my ass at one point and went straight back in, im sure reception head how loud I moaned at that, the second time he did that he told me to get on my back up the bed and pulled me legs over his shoulders and started going again, this time deeper, he grabbed my cock and started jerking me, a pool of precum was forming on my stomach, and then suddenly his thrusts got harder and longer and knowing that reaction, I knew he was cumming, I wished it was without the condom so I could have felt him inside, I know that would have sent me over the edge. He collapsed between my legs kissing me, he slipped out of my ass and I was left feeling empty, missing something. He started grinding on me his cock was out of the condom, I don’t know where it went, but his cock was mixing with my precum and was rubbing against my raging hardon.

He dropped down the bed and started sucking again, this time his fingers were inside me, deep inside, two or three as his head bobbed up and down, he never broke eye contact, his fingers found every sensitive part and just as he took all of my cock down his throat I started to cum, he took the first load like the pro he was, and took the next 4 over his cute lips and nose, his hair had broken free from his gel and was hanging over his eye. I just about came again when I saw him, it was the hottest image I have ever seen, this cute 19yr old covered in my cum, still sucking the last drop out of my cock and cleaning me up. I pulled him up and kissed him again, tasting my own cum this time. So much sweeter from his lips. We lay there for 20 minutes discussing the last hour. I told him I couldn’t have had a better first time, I kissed him one more time, and he jumped into the shower, he said he had to go. I retrieved his clothes and found the condom on the TV. I wrapped it in tissue and flushed it when he came out of the bathroom. Getting dressed we exchanged numbers politely, I was back to full mast as he kissed me goodbye and closed the door behind him. I sat down on the bed and found his jock strap beside me on the bed. I wanked twice more that night at the thought of that night and I’ve started only wearing jockstrap underwear.