My Entry into Anal

My anal story begins with me joining a website for mature bisexual and gay men. At first I was only interested in meeting men for mutual cocksucking, but it intensified to more.

First some background on me. I'm a married senior citizen whose wife had always refused to suck my cock. By means of the internet I was able to find guys willing to suck my cock, which I thoroughly enjoyed. This activity eventually led to me try cocksucking and I found I like it. One of my fellow cocksuckers turned me on to the website I joined the site and quickly found fellow members that lived nearby. My circle of cocksucker friends suddenly expanded. But my ability to meet was limited by the fact I'm married and cannot host. Many of my new found friends were in the same situation. I was amazed how many married men are involved in cocksucking.

One of the guys I met online did massages on the side to supplement his retirement income. He has a web site and after I visited the site I became interested in possibly trying his services. He promised excellent massage with a happy ending which intrigued me. The problem was he lived about 100 miles from me so getting away long enough to meet was going to be difficult.

One day my wife announced she was going away for 3 days. I couldn't wait to get on the Massage website and make an appointment. I also left the masseur my messenger address so we could chat. We began chatting and discussing my forthcoming visit to get an erotic massage with a happy ending. The anticipation on my part was great and the time dragged waiting for my wife to leave.

The day finally arrived and as soon as she left, I messaged my friend and said I could leave and it would take me about 2 hours to get to his place. He gave me his address and I programmed it into my GPS and headed his way. Since I had never had a massage, I was a bit nervous with anticipation.

Upon arrival, after introductions, he ushered me into a back bedroom that had lights dimmed and classical music playing in the background. There was a prepared massage table set up and the atmosphere was very serene. The masseur told me to undress to my level of comfort and I told him getting totally nude was fine with me. He then asked me if I wanted him nude as well and I answered yes.

He told me to lie on my back and to relax and he would make the massage as enjoyable as possible. Once on the table I closed my eyes to experience the full effect of an erotic massage. I felt his hands on my shoulders as he started applying a non scented massage oil. The massage was very relaxing and felt good and I shivered when I felt his cock touch my body as he worked his magic. I reached out and took his cock in my hand and slowly stroked it as he continued with the massage. His cock was not big probably 5" and normal thickness. He continues the massage as I held his cock. As he worked his way down my body, I felt his moist lips and mouth around my cock, which had harden. I turned my head and took his cock in my mouth. We continued with the sucking for a while and then he said it is time to turn you over. I turned over and he went to work massaging my back, and arms. As he worked down my back he started massaging my buttocks and wiping across my anus. He asked if I had ever been fucked and I said no. He then asked if I had ever experienced a dildo and again I said no. He said he had a vibrating dildo and wanted to know if I wanted to try it. I was so turned on I answered yes.

After apply lube to my backdoor, he began working the vibrator up and down my crack letting me feel the vibrating sensations. After a while he started inserting the vibrating dildo very slowly and very gently until it was deep in my rectum. The feeling was awesome and when the vibrator hit my prostate I could feel precum leaking from my cock. He continues by fucking me with the dildo as I began to moan. The feeling was exquisite. It is hard to describe, but awesome. I did not achieve an orgasm but I know I leaked a lot of cum. After the session was complete, he told me the dildo was 7.5" and that I had taken it all without any difficulty. I was shocked when he said 7.5" and asked to see it. I was amazed that I had taken that whole thing with virtually no pain. I knew I wanted to come back and repeat what I had just experienced, which I did at a later date. We have met twice but due to the distance and amount of time involved, I don't know when I will be able to visit him again.

My second anal experience and first with a real cock was again with a guy I met online. We would chat on messenger and he explained to me he traveled my state on business and was in my area several times a year. One day I got a message from him saying he would be in my area and would I like to meet him in his motel. I answered yes if it would be on a Tuesday or Thursday morning. I normally play golf those days and use the golf as cover for my meets with men. He responded that would work as he could be in my area on a Monday night and we could meet in his room the following morning. He would leave me a message with his room number after he had checked in.

When the agreed on Tuesday morning arrived, I got up showered and took an enema to ensure I would be very clean. I put my golf clubs in my truck and left at my normal time for golf, i.e. 7:30 AM. I arrived at the motel shortly before 8:00 AM and proceeded to his room. He answered the door in a bathrobe and after concluding introductions, as this was our first face to face meeting, I continued to get undressed as he removed his bathrobe.

We got into a 69 position on the bed and sucked each other. His cock was about 5.5" and thin and smaller than I expected from his profile picture on SD. After we sucked for a while, I asked him if he wanted to fuck me, which he had indicated that he wanted to do in previous conversations. He responded in the affirmative, got up and put on a condom. After lubing his cock and my ass, I got on my knees on the bed and he started to work his cock into my ass. He was able to gain entry without much difficulty and then continued to fuck me. I did enjoy the fucking, but was not getting same sensations I got from the vibrating dido used on me by the masseur. It must have been due too the size of his cock. He continued fucking me and began to pound me hard until he blew his load into the condom. Although it was felt good, I was a little let down.

My next experience getting fucked was administered by, a 43 year old, Navy Doctor who was assigned to a Marine base about 100 miles from me. Like my previous sex partners we met online and carried on a chatting relationship for about 6 months hoping to make a meet happen without success. He talked about his wish to fuck a silver daddy like me and to enjoy mutual sucking.

One day out of the blue I received a message saying he was traveling back to the Marine base from a trip home and he could make a slight adjustment in his travel plans. He asked if I could arrange to meet him in a motel nearby to where I live. It would make possible the meeting we had so often discussed when chatting online. I quickly agreed. He asked for some motel information near me and I responded with info on two motels that were nice but not high priced. He said he would message me when he got near the motel and gave me his cell number so I could call and get the room number.

I received a message saying he was about 15 minutes from the motel. I waited the 15 minutes and then started driving to the motel. When I got to the motel parking lot, I called his cell phone to get the phone number. With great anticipation, I made my way to his room and knocked. The door opened and I saw a very handsome 6'3" man. After exchanging pleasantries, I started removing my clothes and he followed suit. I was taken back when I saw his cock. It was much bigger than I expected from the picture on his SD profile. In most pictures the cock appears bigger than it really is. I commented on that and he said it was 7". It was a very thick 7" and cut with a big mushroom head. I wanted to suck that cock.

We got on the bed and maneuvered into a 69 position and began sucking each other. His cock immediately leaked sweet tasting precum. After we sucked for a few minutes he asked me to stop saying he was going to cum. He continued sucking me, and doing a very good job of it. It was obvious that he knew what he was doing and he brought me to the point of orgasm and I warned him I was about to cum. He suggested that I should cum and I blew my load in his mouth as I experienced an awesome orgasm. After I came down from my high, I asked if he wanted to fuck me, and he said yes and that is why he didn't want to cum when I was sucking him. I told him I had brought an enema prep to clean myself, just in case. I ask him to insert the enema and after the cleansing process was over, I climbed into the shower to complete my cleaning. He followed me and took a quick shower. We were both very clean and ready.

He put on a condom and applied lots of lube to his cock and my ass. I was a bit nervous because of the size of his cock. Not so much the length, as I had experienced a 7.5" dildo but at the girth. It was very thick. He asked what position I would like and I said on my back so I could watch his face as he fucked me.

I go on the bed on my back and he raised my legs over his shoulders. He then maneuvered me onto my side to get a better angle to access to my ass. This was necessary as he is 6'3" tall and I'm 5'8". After some jockeying to get in the proper position, his cock was at the entrance to my ass. He worked very slowly and gently and pushed till the mushroom head of his cock had gained entry. The pain was slight and he was very concerned that he not hurt me. He continued on going slow till I could feel him deep in me and I asked if he was all they way in and replied yes. He kept asking if I was okay and if it hurt. I answered no I was all right and he proceeded to slowly fuck me. The feeling was exquisite. This was how being fucked should feel. He was making lots of contact with my prostate and I felt cum leaking from my cock. He picked up the pace till he was pounding me very hard. I watched the expressions on his face as I was being thoroughly fucked. He came with a big groan and expression that I will never forget. I loved being fucked by him it was better than I had anticipated.

After we got up we both showered again and then got dressed. He told me he had to be back to the Marine base by 8 PM and that is was a 2.5hour drive. So he needed to leave. As we walked to the parking lot, I told him I hoped we could do it again. He said he hoped so too, but then he dropped a bombshell. He told me he was being deployed to Afghanistan and did not know where he would be sent on his return. I was stunned and wished him well and told him to be safe and to keep in touch. I'm not normally into kissing men, but I kissed him.

After I got home, I sent him a message and told him I could not stop thinking about him fucking me and again wished him well and to be safe.

That is my story on getting fucked. I'm now not only into mutual cocksucking but a bottom as well.