My first Anal
Story by bigears on 12 May 2010
I had bought a digital camera for our holiday in Florida. One hot afternoon my wife was sunbathing by the pool. I was upstairs in the master bedroom .On a whim, I stepped out of my shorts and stood there naked. I set the timer and started to take pictures of my body and , especially, my penis which quickly stiffened into a full erection. I have always enjoyed being naked and the pictures were a great souvenir .When we got home I enjoyed editing the images -choosing the best ones ,zooming in and cropping etc. Looking at naked pictures of myself in compromising positions was a real turn - on. Whenever I was bored ,but horny, and alone I would take more pictures and select the best for my collection. I especially enjoyed pictures taken outdoors. Being naked with the breeze whispering over my erect cock was a wonderful sensation and I half hoped that someone might suddenly catch a sight of me.
When I bought the video camera it was only a short time before I recorded myself masturbating. I enjoyed editing the video to produce a good 3 or 4 minute clip. I could masturbate while watching myself masturbate!
When I discovered websites that encouraged posting pictures and videos I fantasised about complete strangers watching me and ,perhaps ,being aroused by what they saw. I finally plucked up the courage to start posting pictures from my collection. I chose ones that did not show my head but revealed everything else as I was worried that I might be recognised by someone who knew me but I would have liked to show my face. I would log on to see how many people had viewed my pictures. I was pleased when they got flattering remarks and annoyed when they got low votes but it was still exciting to think of my exposed body being enjoyed by hundreds or even thousands of strangers.
After a few weeks the desire to be seen fully naked became too much and I posted my first full frontal pictures and wanking videos. The number of hits and flattering comments increased enormously. I enjoyed the extra thrill of possible recognition but was still worried about the chance of my 'private little vice' being discovered by my friends.
More and more responses to my pictures and ,especially, the videos wanted to know if I had a webcam or if I would meet them. The thought of meeting a stranger was much too risky for me but I decided to buy a webcam. One evening I clicked the video link with a guy I was having an instant message session with. His erect penis appeared in the video window. I got the request to show my video feed and ,with a tingle in my groin, I accepted. My camera was focussed on my upper body. He complimented me on my appearance as I watched his hand massaging his cock. After a bit more chat he asked me to show him my cock which was ,by now, thickening inside my pants. I was a little reluctant because my wife was around downstairs but after a slight hesitation I slid my pants down and adjusted the camera to let him see my fully stiffened cock sticking out. He made some flattering comments and as I watched his hand stroking his cock I got a raging hard on and with only a few more strokes I shot a thick stream of spunk down my leg. He came shortly afterwards.
We had several sessions after that. If my wife was out I would strip naked for him and let him have close ups of my cock and arse whenever he requested. He particularly enjoyed my bending over and separating my buttocks so he had a good view of my still virgin anus.
I had a few c2c sessions with a few other guys and enjoyed mutual masturbation but it began to get a little bit boring after a while. I wanted real sex with a real man but I was afraid of taking that next step and didn't say how it could be safely arranged. I am retired and although I play a little golf I was hardly ever away from my wife. If I wanted a sex session it would have to be local because I was never away for more than a few hours playing golf and I couldn't explain an overnight stay to my wife without risk of discovery. I was also worried about stories of people being mugged or blackmailed by someone they met and there was always the question of wearing protection during sex which ,for me, would have been a must.
I then started chatting with a guy called Steve. I'm sure it wasn't his real name just as I never used mine in chatroom sessions. However, he seemed to have similar views to mine. He was never worried about showing his face on camera and he had an attractive body. I am quite slim and have always trimmed my pubic hair and prefer similar body types. Steve was better built than I and about 15 years younger but we got on well. We had the usual discussions about life, our experiences , our fantasies etc. Many of the people I chatted to seemed to claim they were as inexperienced as I but the way they spoke made me suspect they might simply be on the look out for new conquests. Steve seemed different and we discussed the problems of first meetings without really intending to follow through.
After several months he suggested we could meet. He offered to arrange everything as we had discussed. The thought of real sex was fantastic but I was till worried. He knew the area in which I lived but not my real address. When he said he was due to visit a small town about ten miles from my home on business in a few weeks time I began to think, for the first time, how I might meet someone safely. The nest day I sent him a private message to ask him how serious he was about a meet.' I usually stop overnight at a Hotel in the town' he wrote.' I'll give you the room number and leave it up to you if we are to meet. I'll pack the necessaries in my case. All you need to do is turn up!' I said I would think about it but I was already having an erection just thinking about what we might do together. I asked him what date he would be in town. It was next Thursday - my usual golf day. A plan sprang to mind. I'd tell the wife I was having an away Golf day with the usual Thursday set. I usually took a small case with a change of clothes for if it rained so that would not be a problem. I decided to go for it !
On The Thursday morning I put my clubs in the car and my travelling case. I told Steve I would be there about mid day. I left my wallet and credit cards at home as I was still a little worried about being ripped off. I had a little money with me and that was it. I had found out where the Hotel was and parked my car in a long stay car park some distance away and walked the last mile or so to the hotel. I got more and more nervous as I got closer and thought about abandoning the whole idea but the warm feeling in my groin persuaded me to continue. I finally reached the hotel. How could I get to his room inconspicuously? I plucked up courage to go to the desk and asked if 'Mr.Simpson' had checked in. The clerk told me he had and asked I wanted him to tell him he had a visitor in the lobby. I said I was expected and went to the lift. I was sure the clerk was watching me suspiciously but I told myself not to be paranoid. When I arrived at the door ,I quickly knocked and waited. My heart was pounding and I actually could feel my knees shaking! There were footsteps , the door opened and I was inside.
We looked at each other and shook hands like two colleagues at a meeting. He was barefoot but dressed in casual trousers and an open necked shirt. I had arrived in a jacket and tie to look like a businessman.' Glad you came' he said. I was surprised, he had Geordie accent. He looked pretty much like on the webcam but he was as tall as I,I am just over 6 foot, and he looked a little younger than I had thought. He smelt of aftershave. The room was a large double room with a chair, a small sofa and a writing desk. There was the usual en-suite bathroom.' Do you want to take your coat off?' he said. I took it off and hung it in the wardrobe. 'Would you like a drink?' he asked .I said a coffee would be fine and he brewed two cups from the room kettle. We sat facing each other sipping coffee. It was quite awkward because neither of us seemed to know what to do next. This made me less anxious as it looked like we were both genuine. Eventually, I asked 'How should we start?' He laughed. 'I suppose it would help if we undressed! Do you want to use the bathroom?' I'm fine' I replied.' O.K' he said and stood up, unbuttoned his shirt and took it off. At the same time I slipped off my shoes and socks. I took off my shirt and slipped out of my trousers. We both stood there in our underpants. We looked at each other trying not to stare at each other's crotch. Then he shrugged and pulled his pants down. I had seen his cock before but it was much more impressive in the flesh! He had a good hard on and his cock jutted up from its little nest of pubic hair. I stepped out of my pants and faced him.' You look great' I said. ' So do you' he replied. He walked across and took my cock in his hand and squeezed it gently. I did the same to him and we both stood there enjoying the sensation of handling another man's cock. His felt warm and stiff and I could feel it throbbing in my hand. I knew mine was throbbing wildly. His other hand stroked my back and buttocks and I enjoyed the sensation of that and the feel of his buttocks in my hand. We were both panting a little already and our hands began to move up and down each other's cock with increasing strength and speed. Soon we were both dribbling pre cum and this acted as a natural lubricant. I had never been wanked off by a man before and the sensation was incredible.' I'm coming' I gasped.' 'Me too. Don't stop!' We stood looking at each other's rigid cock as our hands moved back and forth. Who would come first?! His cock jerked in my hand and several jets spurted out. Seconds later my prick was pulsing and cum squirted out. We stood for few moments enjoying the afterglow and then laughed and got some tissues to clean ourselves ,and the room ,up.
'That was short but sweet' I said. 'Never mind we've got a long afternoon ahead' he replied. We sat naked alongside each other and just chatted about nothing in particular. After another coffee Steve said he'd brought a few DVDs along. 'Perhaps they might give us a few ideas' he grinned. 'Good idea' I replied. 'Any preferences?' he asked.' 'No. You chose' The DVD started and we watched the usual lead up to the action. It was set in a garage and soon the mechanics were stripped off and sucking each other's cocks. As I watched I felt my cock stiffen and when I glanced across at Steve he was looking at mine and his cock was well on the way to full size! 'Seems to be working' he joked and put his hand on my knee. My cock stiffened further as I reached across and stroked his. 'Do you want me to suck you off?' he said. I gulped. 'Actually' I said 'I'd like to go one better' 'Wow, very daring for a first meeting' he said ' but I think that would be an excellent idea!'
'Have you got the supplies' I choked. My mouth was dry. I could hardly believe what I was about to do and to allow him to do to me!
'Sure have' he said and reached into the drawer beside the bed. He took out a small bottle of lubricant and two condoms.' Want to go first?' he smiled. 'Yes please!' I managed to grunt through my dry lips. I'd seen fucking on DVD so I thought I knew what to do but actually fucking another guy in the arse was my ultimate fantasy.' How do you want me?' he said.' 'Bend over the Chair' I said. He obeyed and leaned forward to offer his arse to me. The tight little puckered brown ring inviting me to enter .My cock was absolutely rigid and the veins stood out as it throbbed before me. I slipped a condom on with trembling hands. 'Don't forget the lube' he said. I squeezed a little onto the brown ring and tried to work it in. 'Nice' grunted Steve.' 'Let's be having you!' With trembling hands I placed the swollen tip of my cock against his anal sphincter and began to push. There was a moment of resistance and then it slid deliciously in. I was inside him! I savoured the moment. I could feel the warmth of his body and the tight grip of the sphincter against the base of my cock. I was pushed as deep inside him as I could get. ' Go for it' said Steve. I needed no more encouragement. I began to pump away wildly. As I worked him I stroked his buttocks and back. The excitement was too intense .In only a few moments I felt an overwhelming urge to shoot and with a loud gasp I came. The orgasm felt as though it would last for hours as my pricked jerked away inside him but, obviously, it was over in seconds. I enjoyed a few more seconds of the sensation of being inside him before I ,regretfully, pulled out. My cock was absolutely scarlet and the condom seemed to be brimming over with milky cum. I cleaned myself up as my racing heart gradually slowed to normal. Steve turned to me with a broad grin on his face. 'I think you enjoyed that! I hope Reception doesn't get any complaints about the noise!' I smiled ,I was a little embarrassed. 'Sorry about that but I couldn't help myself. Thanks. that was wonderful' ' Don't worry, you can show your appreciation in a much better way. My turn!' he said. My prick gave another little jerk at the thought.
He bent me forward over the back of the chair.' Just spread your legs a little more' he said. I could imagine my own little brown ring exposed before his eyes. I was half anticipating and half dreading what was to come.' Here comes the lube' he said. I felt a trickle of cold liquid in the cleft between my buttocks.' I'll just work it in' he said and I felt first one and then two fingers pushing through my sphincter which tried to close to resist their entry but was overwhelmed. 'Just relax' he said as he moved his fingers in a circular motion inside my anus. 'The first time is always a bit of a struggle' I heard him tear the condom packet and when I looked back over my shoulder at him he could see he had the biggest erection - ever. I wondered how it would possible get into me. 'Ready?' he said thickly. I nodded and waited. I felt one hand on my hip and felt the tip of his cock against my sphincter. Once again it tried to shut down.' 'Just relax' he said .I felt him begin to push .He couldn't get in. He increased the pressure. I wanted to help him. I strained as if I wanted to go to the toilet. I had read that can help. The sphincter relaxed a little and with a triumphant grunt he penetrated me.' Jesus Christ - that feels so good!' he said.' ' You OK?' I felt I was being split but I grunted 'OK' He paused for a few moments and I began to feel more comfortable. I could feel his pubic hair tickling my buttocks and the throb of his gigantic cock inside me. He grasped me firmly by the hips and began slow movements, In and Out. I began to feel more comfortable as the moments passed.' Don't hold back ' I gasped. He didn't need any more encouragement and began to pound away. He was gasping for breath and I felt drops of sweat fall onto my back .My anus was a mixture of pain and pleasure as he worked away more and more wildly. I could feel his balls banging against me. ' Jeeeesus!!' he cried and I felt his cock pulse inside me. I could almost imagine feeling his cum splattering into the condom. He enjoyed the moment, as I had for a few more moments and then pulled out.
We cleaned up. Had another coffee and then I left. When I got home the wife asked if I had played well.' Best ever!!' I said.