New York and new sex

Before I went to university in the UK I spent a year traveling, mainly in the US and Canada. I met loads of interesting people and saw lots of great places but most of all I discovered more about me. I had been confused about my sexuality at school. I had lots of girl friends but also knew that I could feel something different when I looked at my fellow male students and at some of the teachers too.

I found myself watching some of them dressing and undressing in the changing rooms and enjoying the experience. For some reason seeing guys in their underwear was something of a turn-on.

I had never done anything about these feelings apart from masturbation. This was before images were so accessible on the internet so the occasional catalogue or magazine was the best I could find.

So when I set off on my travels I decided that I would find out once and for all what it was all about – away from friends and family and the risk of being discovered. I spent several days in New York at the beginning of my stay and booked into a hostel. I had heard stories about what went on there and thought it was the best place to start.

I had a room to myself but guys seemed to gather in the corridors and by the stairs and I definitely felt as though I was being checked out as I moved about the place. The toilet cubicles didn’t have doors on so everything was very public in there!

I spent my first full day visiting places I had seen on TV and soaking up the atmosphere of the city. The height and closeness of the buildings was very strange and claustrophobic at first but I soon got used to it. When I got back to the hostel in the early evening the guys were in the corridor as usual and for some reason I noticed one in particular.

He was quite short with cropped hair but, unlike the others he was wearing a suit and tie. I guessed he was in his late twenties. I found myself staring at him and he obviously noticed because he gave me a friendly smile and said hello.

I responded and he moved away from the others and we got into conversation. We asked each other about ourselves and he said that he was on a training course for a week and decided it would be more fun to stay in the hostel than in a hotel. I wasn’t totally sure what that meant but I thought, and had begun to hope, it meant he was looking for company!

After a while he asked if I was doing anything during the evening and, when I said I had no plans, he offered to show me around. He said his name was Greg and told me his room number. We agreed we would meet there at 8.00.

I went back to my room and then washed and changed, choosing my best pair of white briefs and a clean blue shirt. I was getting more and more nervous but excited too but had no idea what to expect. I knocked on his door at exactly 8.00 and he shouted come in. He had changed out of his suit but was still wearing a smart dress shirt neatly tucked into his trousers. I also noticed as he was bending over his locker some visible brief lines and a glimpse of the waistband of his briefs above his trousers.

I have explained that I love seeing guys in underwear and for some reason the sight of a waistband with a shirt tucked in is a huge turn-on. Several of my school friends had tucked their shirts in their underwear and those few minutes in the changing rooms each week were always special. Some of them sometimes showed their waistbands during the rest of the day too, and I was never sure whether it was intentional or not. Although I tucked too sometimes I never consciously showed mine.

I was now ready for anything with this guy and yet I didn’t know how to show him. I just hoped I had read the signs right and he was up for it. One way of showing him of course was the fact that I was feeling so horny that after a few minutes my cock was starting to bulge in my trousers. We were standing chatting and I could see his eyes kept looking down at my crotch.

I moved around to try and stay relaxed and looked for any sign that he was getting hard too. His trousers was not very tight so it wasn’t easy to see but he saw me looking and put his thumbs in this waistband and eased them down a bit, revealing his briefs at the front now as well as the back.

Quite spontaneously I said that I noticed he was wearing jockey briefs and that I had some like them. He asked if I was wearing them now but I said I had some store brand ones on today and without thinking I put my hands inside my trousers and pulled the waistband of the briefs up.

He said they looked smart and how it was good to see another guy who tucked his shirt in his undies. None of his friends seemed to do it any more. I said that several of us did it at school but I had noticed it was less popular these days. Then he said that he found it a bit of a turn on, to which I hurriedly agreed and said that I didn’t know anyone else who felt the same. He assured me there were others in the States and he was sure there would be in the UK. I wasn’t sure how he knew but didn’t ask.

By this time we were both showing our bulges and he suggested we got rid of the trousers so we could see the full package. Not only was I getting hard now I could feel precum leaking into my briefs and sure enough, when I took my trousers off there was a damp patch on the front.

He took a good look and said how nice it looked and then started to rub his own bulge through his jockeys. This was too much. I started rubbing too but muttered something about being very inexperienced at this sort of thing. He asked what I liked and I said I was up for anything if he didn’t mind me being so new at it. He said it made it even better for him and he would enjoy showing me a great time.

Then he moved over to me and took me in his arms and gently kissed me on the lips. It felt strange to be kissed by a guy but also really good and I kissed him back and we held each other close as he pushed his tongue inside my mouth. I let my body rest against his and felt his bulging briefs starting to rub mine.

This was what I had been waiting for – it seemed so natural – and I loved the feel of his hands as they started to explore my body, playing with my waistband and stroking my cheeks through the briefs. Then he stopped kissing my lips and started to move downwards, finding my nipples through the shirt and then resting on the waistband and the front of the briefs.

As his tongue reached my bulging shaft I thought I was going to cum there and then but held off and tried to relax and enjoy the great feeling of his tongue moving up and down on me. Then he moved in with his lips and took me into his mouth and I knew this is what I had been waiting for – a guy who loved both cock and underwear.

I couldn’t believe my luck at finding him so soon on arriving in the States. By now he was sucking hard and I pulled away saying I didn’t want to cum yet and could I return the favour.

He was very happy for me to do so and so I got to kiss and lick and suck my first cock – still only through the fabric of the briefs. But after a while, during which Greg was moaning with pleasure, he pulled his cock out through the leg of the briefs. There it was, at least 6 or 7 inches of heaven, cut and waiting just for me.

I slowly repeated what I had done when it was in the briefs and finally put it in my mouth and started sucking. He was gentle with me but as he got more excited he started to push his cock in further and I was almost gagging on it. But I refused to stop and kept going till he let a torrent of words about sucking his fucking cock and cumming. Then he shot his cum into my mouth. I didn’t know what to expect but it felt great. He lifted me up and kissed me letting his tongue take back some of his creamy spunk.

By this time I was again ready to shoot my load and he quickly went down on me, pulled my cock out of the leg – I’m about 6” uncut – and started to suck. Very quickly I exploded with huge jets of cum pouring into his mouth. He took it all and swallowed it then licked me clean. We collapsed on to his bed in each other’s arms, still wearing our shirts tucked in our briefs and with our now limp cocks hanging through the leg holes.

I told him how fantastic it had been and we kissed again. Then he said there was a lot more we could do when I was ready, assuming I was up for it. I told him I would be happy to do anything with him and I was so glad he was here for the whole week.

We lay there for a while happily in cuddling and kissing but finally decided to go out and eat. So we rather reluctantly pulled on our trousers again both taking care to show a little waistband. This was probably not the best idea because I started to get hard again, but we were both hungry so we went to a nearby restaurant and I concealed my erection behind the table cloth!

After the meal he asked if I wanted to go and see the sights or go back to the hostel. I said I could see the sights in the daytime when he was at work and I’d much rather spend the evening in his room. And so we went back for my second sexual experience with a guy – but I’ll tell you more about that next time!!