Gay Erotic Stories

My first male lover tells the story of a love affair with a much older man. The experienced gain from Bill would help shape me into the man I am today. The story shares my passion for older men, cigar smoke fetish, cross-dressing and numerous other kinks that helps satisfy my sexual lust for life.

Chapter one Introducing

My story begins not with a man, but with a woman, my then girlfriend to be exact. Little did I know but when Dawn decide to spice up our sex life by tying me to the bed with a couple of pairs of old stockings, I would end up in the arms of many men performing all manner of sex act with them.

I was twenty six at the time and Dawn had changed from her usual mild mannered self into some dominate sex queen in the time it took her to strip me naked and use her old stockings as very effective rope.

I remember being very aroused by it at the time; however when she pushed her dildo into my hole, a mixture of feelings erupted from within me. Leaving aside the fact she used no lube which of course made my toes curl, the feeling was so intense I shot my load over and over again that afternoon in her bedroom.

Driving back to mine that night I was in deep thought as to why I had found the experience so good, but one thing I did know I wanted to do it again. I expect like so many of us who have experienced this for the first time I started to question my sexuality, so after a couple of weeks I had decide I was bisexual and I wanted to take the next few steps to see if this was really the case.

I had always been a good looking guy, with a good body that I worked out hard in the gym and swimming pool. I stood about five feet eleven in bare feet, had broad shoulders, did not have a six pack, but was pleased with my 34 inch waste. I always kept my blonde hair short, a throw back to my old army days, so within reason I had no problems when it came to attracting woman.

After a few more times with Dawn in her more dominate role where she dressed up in all manner of sexy fetish gear with high heel shoes, sporting one of my huge cigars that I loved to see her smoke, I knew that even thought we shared this new fetish together, we would not stay together. So a month after the very first time together we split and I would never see Dawn again.

The next two years while I was at college as a mature student I watch just about every type of porn there was because I became addicted in what I called a nice way to fetish, kinky sex performed by men, groups of men dressed as glamour queens, leather men, rubber and PVC, you name it I watched it.

My favourites at the time became anything with cigar smoking a fetish I had since puberty, she-males and mature, older men that I was fast becoming so attracted to I had come to the conclusion it was time to meet.

The Internet had just started, but was still in the first stages, so after reading a headline in the personal column of the local free paper, selling UK contact mag’s for gay and bi guys I sent off along with a cheque for two magazines.

After a couple of weeks had past I thought I had been conned, however after giving up hope of ever seeing these magazines, they arrived in the morning post along with a letter saying they were sorry for the delay and I was now on there data base. I browsed through each magazine and was happy to see that there were so many guys out there just like me, who wanted to meet. There were not that many guys in my area, but I did note one advert from a guy over sixty who wanted to meet a younger man.

His advert made me aroused when he mentioned numerous kinks and fetish based interest’s, he was a retired man that had been a widower for over two years. I felt he would be perfect to meet, hopefully become close friends and act like a mentor too me. So I wrote a letter to this guy called Bill, telling him about my previous experience with my ex girlfriend that had helped start me down this road.

It was over a week before the reply to my letter came back via the box number I had set up so that my real address could be kept secret until I knew that any future contacts were real. The letter was a couple of pages long and I read it cover to cover; there were also a couple of photos of Bill, that I found myself looking at over and over again because he was a very good looking guy with a really nice hairless body. He was bald with blue eyes and I soon found myself shooting a load of his photo that shown his wonderful large pierced cock. All I had to do was send a couple of photos of me to show I was who I said I was and he would send back his phone number.

Again it took another week before finally I had Bills phone number with a lovely letter telling me I was a sexy young man. I called Bill within minutes of receiving his letter only to find that the answer machine cut in, so I put the phone down and rehearsed what I wanted to say. I called again and left a message saying who I was and left my phone number.

I had just made a cup of coffee when the phone rang, it was Bill thanking me for getting in touch, we talked for about a hour and when we had finished I was so hot I could not stop myself from rubbing my eight inch cock until I had shot more cum over one of his photos again.

Bill lived forty miles from me in the country, just outside a small village that I had heard of, so after looking at my road atlas I made a note of the place he had told me to meet him at the next day as it was Saturday. The place was a coffee shop in a town which was half way between our homes I could not stop thinking about it and I had a mixture of emotions from being nervous to a state of pleasure flex.

Chapter two The first date

I arrived in the car park ten minutes early for our first meeting, it was a lovely summer day and I felt on top of the world, but also wondered if I was doing the right thing, I suppose the old nerves were back, however I wanted to meet Bill so bad I sat and waited. After five minutes I watched a blue Volvo car pull up which I knew was Bill’s car from the description he had given me.

I locked my old Mini and walked over to the Volvo as Bill was locking the car door, he turned and said, “Good morning William, what a lovely day.” He shook my hand with a firm grip and put me at ease by saying, “Don’t worry, I won’t kiss you in public.” We both laughed at this and any nerves that I had felt had gone in seconds.

We walked outside to a table in the corner of the patio, there was no one else outside, but a few people in the shop. The waitress brought our coffee and Bill offered me a medium sized cigar saying he was pleased that I enjoy cigars as much as him, he winked at me when he said this, which had a nice effect on my cock.

Bill opened the conversation about why would a good looking young guy like me want to meet with an old guy like him, I told him I wanted to learn and experience the pleasure I had seen many others performing on my porn videos, he smiled at this and said, “If you are sure that’s what you want, I will take you on a voyage of discovery that will blow your mind.” He said that he would like me to follow him back to his home if I wanted, because it was a little difficult to talk where we were; a couple of families had just sat at the next table and there kids were running all over the place.

I agreed and said I would like that, so in thirty minutes we were driving down an old dirt track to Bill’s home. Bill was not short of money, because his house was huge and set in a secluded spot that had once be a farm. I followed him into a large lounge, where Bill poured a couple of brandies saying it was early but it would help relax me.

He went up stairs and changed into some shorts and a lose fitting short, when he returned I could see that he still had a fantastic body and that both his nipples were sporting rings, he smiled as I looked at him, “You like?” he asked.

“Yes,” I said, “they look great!”

‘Good,” he said, “I do love the feeling they give me.”

The brandy was doing wonders for my nerves, so when Bill put his arms round me for the first time, I wanted to feel his lips on mine as we kissed for what seemed an age as our tongues explored each other’s mouths. “Well, well…” he said, “now that’s what I call a kiss young man!”

We were both hard, so Bill took me by the hand and we walked upstairs to a bedroom, he said it was his playroom as he told me to strip off my clothes. I sat on the bed naked as Bill searched one of his wardrobes for some fetish gear.

“I seem to remember from your letter you like these am I right?” he said as he waved some stockings in my direction.

“Yes.” I said, and we both pulled our stockings over our hairless legs, he helped me with my suspender belt and could not resist touching my cock with his skilled hands.

“My, my, you are a big boy.” he said, but Bill was bigger; he must have been an inch longer and thicker than my cock, it looked so good seeing it so hard with the large cock ring in the helmet.

Bill offered me the biggest cigar I have ever seen, saying, “I seem to remember you like these as well.”

“Yes,” I said as my hand was shaking as I took the cigar and went to work on it.. Within a few minutes we were both performing open mouth inhales with our large Cuban cigars whilst Bill went to work on my arse pussy with a small dildo. He talked me through everything he was doing and I felt strangely at ease with the camera that was filming our ever move.

Bill had d a tight ring around my balls saying he did not want me to cum straight away as he was going to stretch my pussy until he was happy I could take all his nine inches. I loved watching him push bigger and bigger toys up my pussy as he smoked his huge cigar, I felt pleasure I had never felt before because Bill explained everything in his throaty voice that he was doing to me.

After an hour of probing with the toys, he said I was ready for my first large cock; he removed the ring from his helmet and pulled a condom over his massive love weapon. I was so aroused I wanted to feel that big cock inside me so bad, he gently pushed the tip of his cock into my pussy, the toys had done there job so well and my pussy was soaked with lube. Inch after inch he pushed, it felt great but my anal muscles tried to push the intruder out, he told me to inhale my cigar to help with my breathing, this did the trick and finally I could feel his balls against my arse cheeks because my anal muscles finally admitted defeat to his monster weapon.

He slowly started to push his cock in and out of me until he was fucking me quite fast, he shouted at me to hold my legs tightly around his back, the feeling of my stockings on my legs made me feel so good that even with the cock ring I doubted I could hold my cum any longer,.

Bills cock was fucking me so hard I could not stop my cock shooting my cum in time with his thrust, he said, “Tthat’s a good boy; daddy is very pleased with you.” Then he shot his own load into the condom, his body was like mine, tense and so full of pleasure it took us a few minutes to gain our composure.

We laid there together holding each other kissing and caressing until Bill said we ought to get showered and changed, he had a party to go to that night and time was getting away.

I kissed Bill goodbye outside his house, we had made another date for next week and he promised me that I could stay the night next time. I said of course I would and if it had not of been for his party I would have stayed this time.

I drove back to my home with a smile on my face, my pussy felt great, but a little sore, Bill had given me a couple of large toys to take away with me and some cream for the soreness that he said always helped him.

I arrived home to find a message on my answer machine that said, “William thank you very much, I look forward to our next meeting.” Bill was being discrete like he said he would, and I was starting to count the days until our next meeting.

I looked into the mirror to see a very satisfied face looking back, I thought of Dawn and wondered if she had any idea what she had helped create the day she introduced me to her dildo.