[MM] – Losing my virginity – story of my first summer away [Long]

I was 19 at the time – working for the summer in a small town that I used to live in. It was summer break and things were good – the job was easy and I had lots of free time both in and out of the office. As most teenagers with new access to wifi do I used lots of that time to look at porn. I had started getting into trans, bi and gay porn a little at that time as well.

But let me back up a bit – I was raised very conservatively. Church, private school, abstinence, all that stuff. I had been with girls and done most everything but actual sex to that point. I had also played around with boys, once or twice, mostly when I was younger. I was still a virgin, naively saving myself for marriage or someone special.

So most of the people I worked with were older and I hung out with them. It was fun, they normally shared drinks with me and I got to hang out and do what they were doing. One night I was at someones house with some co-workers and someone was talking about tattoos and piercings when one of my co-workers piped up (let’s call him Bill) and said he had a prince albert piercing!! One of the wives or girlfriends of one of my co-workers said she didn’t believe him and he offered to show it. Next thing you know he’s got his cock out and sure enough, he’s got a prince albert!

I was mesmerized – I had never seen that before, let alone knew it existed. Plus this was one of the bigger cocks I had ever seen AND it was uncut! Looking back on it I think he was around 7″ long and decently thick but at that time, not having seen many of them, I thought it was huge!! Everyone there was mildly impressed at best but I was blown away, and Bill noticed how I felt. He could tell I had never seen anything like it and I was interested.

Let’s talk about Bill a bit. He was older than I was, much older, likely in his middle 50’s. He was bald with a goatee and 1 earring. He had tattoos and had a motorcycle and was divorced. He constantly told stories about having sex with her and strangers, swinging and the like. Anyways, back to the story.

About a week later I was at work, eating lunch, when a few people get up from the table and only Bill and I are left. We start talking a bit and get into the subject of porn and what we like to watch. I told him I loved redheads, especially hairy ones and that I had been into trans lately as well. Nothing much came of the conversation then but apparently he took note.

Bill was very good friends with the people I was staying with. I was staying in the basement of their main house and I had the whole basement to myself. Bill was a janitor and handyman at work so he did some of that work in his spare time. He had done some work on the basement before I moved in, getting it ready for me to stay there.

So one day, the weekend after Bill and I talked at lunch, I was downstairs watching porn. IIRC I was watching trans or crossdresser porn. I had headphones in and couldn’t hear anything but Bill came over and came downstairs to get some tools he had left there. Well obviously he comes downstairs and I’m sitting there naked jacking off! I notice him and I immediately try and pause the video and cover up. He tells me that it’s ok, I’ve seen his and now he’s seen mine and he asks what I’m watching. Sheepishly I show him and he says it looks cool and asks if he can pull his out and jack with me! I was super excited at this prospect, seeing his cock again so I said sure.

He pulls down his pants and he’s not wearing underwear. I’m still rock hard but he’s got a semi that’s bigger than mine when it’s hard. I start the video and we start jacking. I tell him I’ve never seen a man cum and I’d like to see him do it – he says he takes a while and that I can just cum whenever but to tell him when so he can watch it. So we start jacking and honestly I’m looking at his dick more than the porn and he’s glancing at mine quite often – eventually I tell him I’m about to cum and without saying anything he quickly bends over and sticks my cock in his mouth! I wasn’t ready for it and I blew a huge load, mostly into his mouth but also kinda on his face.

I wasn’t sure what to do – I knew that I liked what happened but I still felt like it was wrong. I wasn’t ok with my sexuality and I feel like he should have asked first. So I got a little mad and told him I was upset and asked him to leave. He did but it wouldn’t be the last time I saw him that weekend.

The next day I got a text from him, apologizing for what he had done and asking me if he could take me out to lunch to make up for it. I was having a pretty shitty day (unrelated to what happened) so i took him up on it. He came over to get me to take me to Denny’s and we started talking a bit before we left. He again apologized for what happened the day before – I told him it was ok. I liked it but I wanted to know he was gonna do it. And I would have liked it more had he sucked it the whole time rather than just the end. So then he asked about what I was watching and if I liked guys in panties and trans porn and I told him I did. We talked some more and then we hugged – for a long time actually. I noticed that he was getting hard and his hand was working his way up my leg into my shorts. I had time to think this time and I spread my legs for him, giving him access inside my shorts to my dick. He slowly slid his hand up and grabbed it and started caressing it. This time he asked if it was ok if he sucked it and I told him yes, I would love that. Bill slowly pulled my pants down and put his mouth around my hard cock. It felt amazing! I had gotten a bj before but never from a guy – he knew exactly what to do and within a few seconds (honestly, like 30 seconds) I blew a huge load into his mouth. To my amazement he swallowed it all! I had only been with spitters up until then.

He thanked me and I thanked him and asked him if he wanted me to play with his – secretly I wanted him to say yes as I wanted to see his cock again, stroke it, maybe suck it and I wanted to see another man cum. He told me he was fine but maybe we can try it soon. I agreed and he asked me if I was ready for lunch – I said that I was but he told me that I wasn’t quite ready. With a puzzled look on my face I asked what he meant. He told me to sit on the couch and he’d be right back.

He went into the master bedroom – of the house I was staying in – and came back with some lingerie from the homeowners wife!! It was a pair of stockings with a garter belt and matching panties and bustier! He told me I had to wear these under my clothes for him – since I liked watching other guys wear it that much. Secretly I had always had a panty fetish – I would wear or sniff them or jack in them any chance I got. So I did as he asked and I put them on under my pants and t-shirt. It was pretty obvious that I was wearing them, you could see the top under my white t-shirt and the belts from the stockings to the garter belt showed through my pants. It didn’t matter, I was in heaven. Lunch was uneventful although I did notice Bill trying to sneak peeks at my panties every time I bent over or leaned forward.

Fast forward a few more days – things had been pretty normal at work and with Bill. One night after work he texted, told me he had a really sweet porn with a super hairy redhead and wanted to know if I wanted to watch it with him. He also said he had some beer and pizza. That was all I needed to hear, I was on my way over! I got there and he was shirtless, wearing only some thin shorts. The movie was already on, paused with a huge hairy red bush on the screen. I hugged him when I got there and he squeezed my dick during the hug and said something like “Looks like you’re already ready!!”. I told him I was and that I was excited to be with him again. We sat down, he grabbed me a beer and started the movie.

I’m sure this is where you expect it to get all hot and heavy and for all the action to happen but it really didn’t. We sat on the couch watching at first. Then we started rubbing our own dicks through our shorts – eventually both of us were completely naked on the couch jacking off. He asked me if I wanted another blow job and I told him I did but I also told him I wanted to play with his this time. He said that I could but that it was for later – right now was about me. I agreed and he laid me down on the couch and spread my legs. He was sucking me and i was lasting pretty long this time. I had my head back and he asked me if anyone had ever played with my ass before. I told him no but i’ve put things in there before – a small dildo, tampons, etc. He asked if he could I and told him yes. Before I knew it he had moved his mouth from my dick to my asshole and was rimming me! I had never had this happen but I loved it! He would circle around my hole, every now and then moaning or gently sticking his tounge in my hole. After a while i was good and wet down there and he stuck a finger in my asshole. It felt amazing!! He was gently moving it in and out, trying to massage my prostate as he sucked me off. Needless to say it didn’t take long and I blew a HUGE fat load into his mouth. I must have came for 10 seconds straight. He came up and told me that I tasted great and asked me if I liked all that. I told him I did, that I loved it and I couldn’t wait to play with his! He told me I could – but that it would have to wait for later. Little did I know what awaited me later that night – and it wasn’t just the pizza and beer.

This story is 100% true – names have been changed as needed. I will continue this story with part 2 if people like what I wrote so far. Thanks!!

Source: reddit.com/r/gonewildstories/comments/8ubl4l/mm_losing_my_virginity_story_of_my_first_summer