Have You Ever Crushed On Your Old Sitter?

One of my callers has been telling me about his sexual experiences with his old sitter.

Many times the old sitter is ten to twenty years older than them. You’d feel surprised how many told me they fucked them. Usually doesn’t visit them much, sees them sporadically as they are growing up. Then one day, things go to a whole other level of acquaintedness for them. Often, they share how they don’t have a girlfriend or are shy and awkward around girls their own age. Then she turns them from a boy to a man. So many have spoken fondly of their old sitter when she was the one that was their first. They were of course deathly afraid their parents would find out.

Many times they went over to her house and were there under the pretense of helping her with something. However, it was in fact the old sitter that was helping him. One the other day was saying how licking pussy is his favorite thing in the whole world. His auntie taught him how to do it. Pleasuring a woman is what gets him off more than anything. Going down on her and learning how to kiss and suck a clit. Getting her off multiple times per session, made him feel like a man for the first time. She gave him his first hand job, blow job, fucking. Like a doctor kink. He learned it all from her, and she was a patient, thorough teacher.

When his parents went away on a cruise, his old sitter stayed to keep an eye on him.

Little did his parents know of course they were fucking in their king-sized bed every night. She was horny, divorced, and had no boyfriend. He was young, horny, and eager to learn everything. It felt like a match made in heaven for them both. Other than the fact they had to keep it a secret from everyone. They nearly wound up caught once, he stated. She stopped by unexpectedly when he was over there after school. He heard her call and came up and dove under the bed. His old sitter acted like she was in bed taking a nap. It was a close call, but after she left, they went at it like crazy, he said.

His cock was getting more experienced by the week. By the time he obtained his first college girlfriend, she felt amazed at how skilled of a lover he became. Older women can definitely teach men the finer arts of lovemaking, unlike girls. The patience and experience of an older woman is the best thing a young man can have. His old sitter was a beautiful lady, he said. He couldn’t wait to go after school for fun. He loved it when she’d be in charge. It was pretty much non-stop sex from the time they left until they returned. He said she was always impressed by how long he could stay hard for.

Even when he’d cum, he’d be hard again a few minutes later.

He said his old sitter was his favorite lover he’s ever had. He’s married now and had a few girlfriends after his sitter. He never spoke to his wife about this, of course. She wouldn’t understand. Not many women would. He still jerks off thinking about all the hot times they used to have. He mentioned me as the only one he ever discussed that relationship with. She passed away a few years ago, and he hadn’t seen her in many years. He still holds those fond memories though of her teaching him in his youth. He’s glad his parents never found out, since they’d have been mad at her and him.

He loved sinking his dick into her for the very first time. His young, virgin cock, slipping into his old sitter. Pumping and pumping until he exploded inside of her. She knew he’d cum quickly at the beginning, but she taught him how to last. Then, he said the great control he attributes to this day her patience and skill. He felt lucky to experience her for his teacher in the bedroom. He fantasizes about their many encounters all these decades later. It can have a lifelong effect on someone when you have a relationship like this.

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