OK so I was a little late to be a first timer at 59. Still I could have been dead and missed it all. Since retiring my sex life had virtually ended. My wife was no longer interested and in truth never had been. My girlfriend now lived 500 miles away. There were very few opportunities for a man my age and with my fetishes to get any sort of satisfaction. My girlfriend Darla & I used to tie each other up and tease each other for hours before allowing each other to come buckets in terrific orgasms. Eventually I made a strap on cock and she would fuck my face and ass with it while calling me her bitch. It was so sexy & wild. I can't get those images out of my head. Me bent double over the back of her sofa with my ankles tied to the outermost legs and my wrists tied to the front ones. She would stick her cock in my mouth and I'd get it very wet before she slid it up my ass while slapping my thighs.

I advertised on Craig's list for someone to take her place but got no takers. I began to fantasize about having a man actually fuck me. So I changed my ad. The title read "Submissive first timer" into cross dressing, anal and bondage.
That got some results and one of the first only lived 10 miles away. After emailing each other for a few weeks we got the opportunity and I got the courage to meet at his place one morning while his wife was out.
I shaved practically all of my pubic hair off and buzzed my legs & thighs. I took 3 enemas until I was clean as a whistle. I inserted my silicone butt plug and put a leather ring around my cock & balls. I placed my wardrobe in a shopping bag & drove to his house. It was all alone at the end of a long driveway out in the country. The door opened before I could knock and he let me in. He was a few years younger than me, a little more hairy and well proportioned. After some talk we decided we should try it to see what happened. He left to get dressed and I went to the bathroom to do the same. I put on a black snap thong and covered it with a garter belt and fishnet stockings. A chain with nipple clips went on top covered by a see through black camisole that just came to the top of my ass in back. Now the thong barely covered my hairless cock. I pulled on my black leather pants and zipped up my black leather jacket, and slipped into my high heels. I then placed a leather collar, and nylon bracelets & anklets on, each with a chrome ring fixed in it. and put on a pair of dark sunglasses. Stupid I know but my first time, right?
I asked through the door if he was ready and he said yes. I opened the door & stepped out to see him standing there in a pair of patterned panty hose and a silk blue top. "Looking good!" I said. He answered "so do you, what you got under there?"
I said "come over here & take a look." I slowly unzipped the jacket to let him see and he came forward to feel my chest & pulled lightly on the chain. I moaned in spite of myself. I removed the jacket & said the rest was up to him. He unbuttoned the fly of my leather pants & slid them down to my ankles. I had to kick off the shoes to get them off. He then told me to slowly turn around which I did as he said "Nice ass!"
"Thanks "I said- "Yours if you want it". I walked around him and caressed his ass through the panty hose and reached around to stroke his hard cock. His hands reached around to grab mine which responded instantly. We felt each other some more until I took the initiative and dropped to my knees in front of him. Slowly peeling down the panty hose I licked his shaft and then plunged his cut cock in my mouth and sucked hard. It became clear he would not last long so I asked what he wanted to do & where he wanted to come- in my mouth or ass- both if he could manage. He wanted my ass and god I wanted to feel a cock in it.

I reminded him it was my first time with a man and that I was very nervous in spite of appearances and that was what the ankle and wrist bands were for- in case I chickened out. I wanted & needed to be tied down. He had a kitchen table that would do nicely. I bent over it and handed him 2 pre-cut pieces of soft pliable nylon rope. He deftly fitted an end through the steel loop on my left wrist and around the top of the left table leg in front of me an pulled forcing my chest to the table top. Then the rope went around the right front table leg and through the right wrist loop and he pulled them tight before tying a firm slip knot. No turning back now, I was his. He followed the same procedure with my ankles until they were spread very far apart to the other 2 table legs. With my high heels on my ass was the perfect height for his bobbing cock, but first he wanted me to suck on it some more which I was perfectly prepared to do until he was almost ready to burst.
Then he came around behind me and unsnapped the thong. Noting that I was already occupied, he slipped his fingers around the base of the Butt plug and slowly slid it out of my ass.
"I wonder where this could go?" he said, and stuffed it in my mouth securing it wit a strip of duct tape. I felt him lube up my ass, inserting first one and then 2 fingers and heard the foil come off the condom we had agreed upon. I felt the head of his cock press against my puckered ass hole and he slowly pushed home until I could feel his pubic hair against the crack of my ass. He held it there in the heat and tightness for a moment and then began to rock back and forth. With each forward thrust my pubic bone ground against the table edge and I moaned around the plug in my mouth and my semi hard cock slapped against the table bottom. For those of you who do not know, it is nearly impossible to maintain an erection with a cock in your ass- there is just too much sensation to go around!
He grabbed my hips and thrust frantically a dozen times or more until I could feel his spasm and then he laid on my back breathing heavily. After a few minutes, he pulled out of me, slid off the condom and walked in front of me. He held me by the face and withdrew the butt plug from my mouth and replaced it with his sloppy cock which I sucked to erection in no time flat. He held my face with both hands and fucked my mouth until he came a second time. I swallowed it immediately- (swallow don't wallow) not as large a load as the one in my ass I was certain. Then he went into the kitchen and started to make coffee, leaving me spread eagled over his kitchen table panting and trying to get some stimulation on my cock.
"Hey man", I said "what about me, I'd like to come and these nipple clips are starting to hurt."
He turned and reinserted the silicone cock in my mouth, and secured it with a thick strip of duct tape. He said "What a great ass, he said, I think I'll keep it right here until I am ready to fuck it again- which won't be long!"put his coffee on the table in front of me and then began slapping my exposed ass.
He reached under the table and began to stroke my now hardening cock.
I began to hope that he really did have a wife who would be coming home soon since no one knew where I was.....I wondered if I would really prefer to have his wife return and see me tied over a table wearing nothing but fishnet stockings garter belt and high heels. I guess I would just have to wait and see how it worked out..