Being a widower for 3 years and no kids around makes a guy lonely. I am a young 58 year old. Most people think I am in my mid 40's. Good genes I guess. I have always had a strong sex life. But the last 3 years I also missed companionship. I tried a few escorts. They put on a good act but bottom line, they want your money.
This led me to Craigslist. Not sure why but I clicked on MW4M. One ad seemed to stand out. They actually seemed like normal people. A couple in in their late 40's looking for an ongoing relationship with a professional straight man that can be discreet. Age between 45 and 55. Must be well endowed and have stamina.
I met everything with the exception of the age. I figured let see what they say. I sent them an email telling them I am what they are looking for except I am 58. I got a reply asking for a picture. I found a nice picture of me and sent it.
Ten minutes later I get a reply back saying I am handsome. Now they want proof I am hung. Well I am a grower not a shower. I am trying to get myself hard and take a picture. The angle doesn't look like I am very big. I find myself now naked in front of the bathroom mirror trying to take a picture of my hard cock and not have my face in the picture. Fourth attempt I get it right. Off I send it.
Two days later I get an email from them. I had forgotten about it. I figured it must have been somebody who liked to get dick pics. They want to meet up for drinks first. I ask for a picture and they send a nice G rated picture. Both seem nice and attractive people.
Steve looks 49 or 50 with an athletic build. Blonde hair and a nice smile. Cyndi looks 45ish. Brown hair shoulder length. Cute face. I would guess she looked 5'6" and 135 lbs.
We set up to meet at a bar between us. I get there and I recognize them from the picture. They are sitting in the back of the bar in a booth. Steve waives at me.
I get to the table and we shake hands with each other. Steve motions for me to sit next to Cyndi. Cyndi is much better looking than her pictures and I tell her so. She had a big smile with full kissable lips. She wore a short skirt that showed of her long toned legs. Her blouse was tight that showed off her C cup breast and a white lacy bra underneath.
Steve and Cyndi already had their drinks so I ordered a rum and coke. We had several drinks and the conversation was easy. We talked about our jobs, kids, vacation destinations and a little politics.
On my third drink I felt Cyndi put her hand on my thigh. Her hand moved up to my cock. She played with it until I was fully hard.
I put my hand on her thigh and moved my hand under her skirt and found she was not wearing panties. Her pussy was clean shaven. I stroked her lips with one finger then started to insert my finger. She was already wet. I hooked my finger and started to stroke her G spot with my middle finger and rubbed her clit with my thumb.
"Well he didn't lie about being well hung." Cyndi said.
"Are you feeling his cock right now?" Steve asked.
"Yes I am. It's long, thick with a big swollen head. He will fill my pussy nicely. He also knows his way around a pussy. I am almost about to come."
Steve looked at me and asked, "Are you finger fucking my wife right now?" I nodded yes.
"Tell me what you are doing to her."
"I have my middle finger rubbing her G spot. She is really wet. My thumb is rubbing her clit. I can tell she is getting closer as she is squeezing my cock harder and harder."
Steve looked at his wife and said, "I want to see you come."
I continued on. I didn't slow down as the waitress brought us new drinks. We were well hidden by the table. Cyndi closed her eyes and was squeezing my cock really hard. I could feel her fingernails digging into me. She came hard. She released my cock. Her face was flushed.
"Tell me, how does she taste?
I put my finger in my mouth and sucked it. I winked at Steve and said, "Like candy."
"We have a hotel room a block from here. Want to join us?"
"I sure do. Thank you for inviting me."
We walked down the street talking like friends. There didn't seem to be a care to the world to Steve that I was about to fuck his hot wife.
As we approached the room Steve casually said, "Cyndi likes it rough. She likes to talk dirty and have her ass slapped."
This surprised me but I was game.
We entered the room and Steve said, "I will watch from over here in this chair. You two have fun."
Cyndi walked up to me and gave me a deep passionate kiss. Our tongues darted around each other. While we kissed she undid my pants and they dropped to the floor. I stepped out of them then helped her out of her blouse and bra.
My hard cock was busting to get out of my boxers. But I was in awe of Cyndi's beautiful breasts. Perfect C cup for sure. A slight tan line. Dark nipples the size of a quarter and they were hard beginning to be sucked.
As I sucked her nipples and massaged her breasts she was able to work my boxers off and now I was completely naked with a big erection.
She turned her back to me and said, "Can you undo my zipper for me."
I lowered the zipper on her skirt and it fell to the floor. She walked over to the bed and leaned over it and said, "Get over here and fuck my wet pussy."
No foreplay was needed. She was soaking wet. I guided the head of my cock into her pussy. Then in one big hard thrust I was deep inside her and pumping away.
