My first time with Bobby

I stayed on at school an extra couple of years to do my A levels but my heart wasn't in it and I failed them. I took a job in the local supermarket stacking shelves. It was unfulfilling work and after a few years I decided to go back to college to get my A levels. The course work was hard and I had no time for girls but I didn't really think I was missing out.

I was lucky in that my best friends brother Bobby had done the course and passed a few years before. I'd known Bobby all my life, but being 2 years older than me I didn't have a lot to do with him. When he heard I'd gone back to college he offered to help me with the course.

Bobby was a confident guy he was head boy at school. The guys admired him because of his sporting prowess and the girls loved him because he was such a hunk.

Bobby had a demanding job and a different girl on his arm every time I saw him but he still found time to help me with my work. We spent a lot time together and I found myself more and more attracted to him.

I completely understood why he was so popular. Not only was he charming but he was incredibly good looking and well endowed too. He had blonde hair, blue eyes and a dark Mediterranean type complexation. He played a lot of sports and had a muscular body. At first I found him quite big headed and arrogant. He would often just wear a vest and a pair of shorts to show off his muscles and his big cock.

As I got to know him he began to show me a more sensitive side. I got to thinking that his arrogance was all a show and deep down he was more vulnerable than he would let on. I don't know why but I got the idea he was hiding something. Perhaps he wasn't as straight as he liked to make out. I didn't have any proof it was just a feeling I had.

My sexuality was also in question. I fancied girls but they do nothing for me sexually. Twice now I've been out with some pretty girls. They tried hard to arouse me but they couldn't. It was very embarrassing, I think word got around about me because girls would often snigger when I walked into a room.

I don't really fancy men although Bobby is the exception. I am however fascinated by men's cocks. I find myself checking men out. I'm always looking at a man's groin to see if his cock or balls are poking out through his clothes. When I have a wank I always imagine some hairy hunk of a man fucking me.

Bobby was always talking about girls and what he'd done with them. To be honest I got fed up hearing about it, it was like he had something to prove. One afternoon we were working away in the front room when three girls stopped outside to wait for the bus. It was summer and the windows were open and we could hear them giggling. I went up to the window to check them out. Bobby came and stood right behind me. We were both admiring the girls commenting on their tiny shorts and the way their ass cheeks poked out from underneath them.

Suddenly Bobby grabbed my thighs with both hands. He pulled my ass back into his groin and pretended to fuck me.

He whispered in my ear, "If you were one of those girls I'd fuck you like this".

I could feel his hard cock banging against my ass. It only lasted a few seconds but I was so excited I came in my pants instantly. My cock wasn't even hard but cum just flooded out wetting my briefs.

I turned around to face Bobby, there was a brief pause as we looked at each other then he kissed me full on the lips. Wow! It was all too much to take in.

Straight away he sat back down on the sofa and apologised.

I sat down beside him and told him that's he'd made me cum.

"What, just with a kiss?", he asked.

I explained that the kiss was lovely but it was the feel of his hard cock against my bum that tipped me over the edge.

Bobby stared at the wet patch in my jeans.

I went bright red with embarrassment.

Bobby ran his hand over my groin.

"Wow! Your jeans are soaked in cum".

I didn't know what to say I was so embarrassed, but then  Bobby knelt down on the floor in front of me.

"What are you doing?", I asked.

He didn't say anything, he just opened my legs and rubbed his face into my cum soaked jeans.

He looked up at me, his eyes were full of lust, his cheeks pink with excitement.

"Oh wow, I love it".

I couldn't quite believe what was happening it was all happening so fast.

He  undid my belt and zip and pulled my jeans down around my ankles. He peeled my wet briefs down and gasped when he saw how much thick cum was still clinging to my cock and balls.

"Mmm, I love it", he said, as he proceeded to lick up every last bit of cum from my groin.

Then he drew back my foreskin and squeezed the last drops of cum from my cock. 

He got up off his knees and sat next to me.

"This is our secret right?", he asked.

Blushing and in a daze  I replied. "Of course, I'm not planning on telling anyone".

"Do you like kissing?" he asked.

I told him I didn't know, but I liked the kiss he gave me earlier.

He moved in towards me and kissed me gently on the lips. I opened my mouth and we kissed more passionately with tongues and everything.

I could taste my cum on his lips and this gave me a huge hard-on.

Bobby took my hand and placed it between his legs. I'd often wondered what it would be like to touch Bobby's cock and now I was stroking it through his trousers. It felt hard and powerful and I wondered what it would feel like inside me.

Bobby helped me undue his button and zip and soon I had his hot cock in my hand. It felt amazing so much fatter than my own. I watched as I slowly wanked him wondering if I dare suck it.

"Do you want to suck it?", he asked.

I nodded my approval and went down on his cock.

The texture in my mouth was all new to me and I wanted to savour every second. Straight away I could taste his masculinity. His glans were peeping out from under his foreskin which I pulled back to reveal his sticky knob. I set to work sucking and licking on his cock.

"Is that ok?",  I asked looking up at him.

"Fuck you're good", he said, "Better than any girl I've been with".

I was flattered with what he said especially as I'd never sucked a cock before.

I sucked on his glans tickling his frenulum with my tongue, then I mouthed the side of his cock wanking him with my lips. I tried to take him balls deep but I kept gagging but that didn't stop me from trying.

Bobby kept pushing my head down, I kept choking but it turned me on so much I kept doing it.

"Fuck Stuart", he said, "You're a natural"

I carried on sucking and licking, trying to take him balls deep.

Bobby took my hand and guided it down over his balls between his legs.

I started playing with his balls but he moved my hand down further and whispered.

"Finger me"

I must admit it was not something I thought Bobby would like but as I circled his rosebud with my finger I could feel him getting harder in my mouth.

"Spit on your fingers and finger fuck me".

I did as I was told and worked a finger inside him.

His ass felt hot and moist and slowly it loosened up. I easily got two then three then four fingers inside him. I was now finger fucking him with four fingers as he got wetter and wetter.

By now Bobby was shaking and I knew he was about to cum.

"Quick, I'm going to cum"

He gave me a warning expecting me to let him slip from my mouth but I wanted to know what it felt like to have a man cum in my mouth.

Then with a huge grunt and a groan he exploded in my mouth his legs trembling uncontrollably.

Oh wow!

The taste of his cum was so strong and intense and the texture so think and gooey. I swallowed a good couple of mouthfuls but he was still spurting like a fountain. It was all over my face in my hair and dripping down my chin onto my t-shirt. The taste began to subside but I was so fucking horny I wanted more cum. If there was another guy with us I would have gladly sucked him off too!

I sat back on the sofa  swirling Bobby's cum around my mouth. His eyes were closed, his thumbs gently brushing his nipples. His whole body was still shaking. He opened his eyes and looked over at me shaking his head.

"Man, that was fucking fantastic, you're an amazing cocksucker. Better than any girl I've been with".

Again I was flattered, I knew he'd been with lots of girls so that was indeed a compliment.

Bobby avoided me for the next couple of days and when he did finally call around to help me with my college work things were a little awkward between us.

At one point I turned to Bobby and said lets talk about what happened.

He was reluctant to talk at first but eventually he opened up to me.

He told me all about his feelings. He explained that the macho thing was all and act and that deep down he knew he was gay.

He told me he liked much older men and had been chatting with two men on the internet who were in their fifties. I asked him if he had met them. He said no, they were both dominant tops looking for a sub and he was too scared to meet them. He said he'd cammed with them both and fancied them but didn't have the nerve to go further.

I wasn't that familiar with all the gay lingo, tops, bottoms, subs, doms etc so I asked him to explain. I told him that I'd viewed straight porn but was too scared to look at gay porn just in case anyone found out. He explained all the terms to me and told me he understood my reluctance to look at gay porn but he just had to give in to his desires.

He asked me if I liked older men and if I thought I was a bottom or a top. I told him I was a bottom. I wasn't sure about older men although I did like hairy men with big broad chests.

He suggested I come over to his flat were we could watch some gay porn together and possibly chat with the two older men. I agreed and we arranged an evening for me to call around.