My name is Carol. I am currently fifty years old, and I am entering a new phase of life. My son has recently married and he has started his own life. His wife is now there to support him. But for the past few decades, I have been a loving mother to my son. I made sure he was always happy and content.
Tom would often bring friends over to hang out after school. One of Tom’s friends was Jake. Jake was a nice boy. I had known Jake since he and Tom were both twelve. They were friends from the first day of junior high. Jake was one of the few boys who was friendly towards Tom when he started junior high. Both had been quite shy and were drawn to each other. I had watched them grow into young men. However, Tom had since made a wide variety of other friends. Tom had come out of his shell since I started giving him a confidence boost. Tom was also showing an interest in girls.
Jake was extremely shy and nervous around girls. This is how Tom was before I taught him what to do with a lady. Tom had essentially left Jake behind. I felt a bit sorry for Jake, but I had my hands full with Tom. To his credit, Tom never ditched Jake. Tom is a very loyal person and he often invited Jake to our house on weekends for a sleepover.
Jake’s last sleepover was during the summer, just before starting his final year at senior high. We had dinner and watched a movie together. Tom and Jake then went to Tom’s bedroom to play the PS4. I went to bed to read a book, before falling asleep.
I woke up in the middle of the night for water. It was well after midnight. I decided to check on the boys. As I opened the bedroom door, I could see Tom in his bed. Jake was at the desk looking at his laptop. It was dark, but I could see Jake doing something as he was watching his laptop. The light from the laptop screen revealed a glimpse of his hand vigorously wanking his penis. He was obviously watching porn.
Tom was snoring. Jake had headphones on and he couldn't hear me. I tried to back out, but I was too far into the bedroom. Jake saw me from the corner of his eye. He got startled and frantically took evasive action. I didn't want to back out, as I had done with Tom when I had caught him masturbating years before. I slowly continued towards Jake.
Jake slammed the laptop shut and was attempting to cover himself. I put my hand on his shoulder and gently pushed his hands away, to reveal his still-erect penis. Without saying a word, I gripped it in my hand and slowly began to stroke Jake’s shaft. Jake sat up straight and began to enjoy it. His back was soon arching, as he felt his cum load building. I continued to slowly stroke his shaft. His penis went very hard and began to throb. A few more strokes, and Jake was ejaculating. His cum shot up into the air and back down onto the laptop.
I continued to stroke Jake as he went soft. Luckily, Tom was still snoring. I silently left the room. I returned to my bedroom with my hand covered in Jake’s cum. I rubbed it into my pussy as I masturbated. I had previously done this with Tom’s cum also. The next morning was a bit awkward, but Jake was more talkative. I didn't see Jake again for a few years. Both boys progressed to college. Tom went to WSU and Jake attended college at a local university.
I occasionally saw Jake out shopping and I’d ask how he was. He’d ask how Tom was. I missed Tom a lot. Tom would come home during his breaks and we’d have quality sex. But I missed him between those breaks. I also got very horny and my dildo could not fully satisfy me. I needed a real cock. The next time that I saw Jake, I invited him over to my place for lunch.
Jake arrived in sweatshorts and a t-shirt. Jake is slightly shorter and a bit skinnier than Tom. I chatted with Jake about his studies and college life. He still lived with his parents and said it was good to get out of the house. I asked him about girls. He laughed nervously and said, “What girls?” I asked him if any girl had held his penis like I had a few years before.
“You do remember, don't you, Jake?” I said.
Jake got embarrassed and answered, “No. Erm, Yes. I mean No, they haven't, and Yes, I do remember.”
I asked, “Do you still have to masturbate?”
Jake looked down, nodding his head in acknowledgement.
“Well we are going to have to do something about that,” I said.
“Would you like me to help you again Jake?” I asked.
Jake looked away and he didn't know what to say. I began to rub his crotch area. His cock began to grow in size rapidly. I softly stroked his shaft through the loose fabric.
“I think this wants me to,” I said in a seductive manner.
Jake was trying not to look down at what was happening. But looking up was of little comfort to him. We were in my open-plan kitchen and he was sitting on a bar stool beside the bench. Jake felt exposed. I felt exhilarated. I was about to see only my third cock in the flesh. I had only ever seen my ex-husband and my son, Tom.
I pulled Jake’s erect cock from his pants. Jake lay back in his chair slightly. I continued to slowly stroke his cock. I crouched down to eye level with it. Jake’s cock was rock hard. He was about an inch shorter than Tom, and he was circumcised. There were thick blue veins running up the shaft and around the base of the head. I had never seen a circumcised penis before. I needed to spit on my hand because there was no foreskin to stroke.