I’m going to apologize in advance if this story makes anyone uncomfortable. To be honest, the whole situation makes me just as uncomfortable as it does turn me on. So a little backstory first. I had my son when I was 31, so this story starts when I was 46. I’ve been a single mother since my son was a little over a year old. I did date several men in those years but nothing where anyone was ever living with us.
Ok. So when I was in high school I was fairly popular. I’m tall, blonde, green eyed, and very skinny. I was a cheerleader, I was on the tennis team, and I was always invited to most of the parties. I had a really great high school experience and I had always hoped the same for my son. By the time he was 14 though I could see that he and I were having two very different school experiences. My son, though I love him dearly, is quite the nerd. He’s a good looking kid, but he never went outside, he never hung out with friends, he just stayed at home playing video games. He was rarely invited to parties, and when he was, it was because the whole class was invited. He was picked on and bullied at school, so much so that a few times he even cried at school.
I did what I could for him over the next few years, encouraging him to go out, trying to get him interested in some type of group activity, anything. But nothing seemed to change. Once in high school he did get some friends, but they were all girls, and it was clear that it was just that, friends. Eventually though he became real depressed as one by one the girls stopped hanging out with him because they got boyfriends. I tried to use that to encourage him to get a girlfriend, like I said, he’s not bad looking at all, he’s just nerdy. But he never asked anyone out.
One night, it was after he turned 16, we were eating dinner in the living room on the couch and he explained to me how one of his friend, one of the girls, had just had sex for the first time. I could tell that he was bummed out. Over the next few months he told me about a few more of the girls having sex for the first time. I could tell it was really bothering him, we both knew that he wasn’t getting laid any time soon. I didn’t know what to do, I wanted him to have a good experience so much, to have something like what I had, and finally, I had an idea. Looking back it was nuts, I know, but I just didn’t have any idea what to do and it was really just out of desperation.
One night while we were watching TV I slid off the couch to kneel in front of him, he looked at me like I was crazy, and I’ll tell you, my heart was in my throat. I was so nervous. I was worried about how he’d react, worried if this was the right thing for him.
I slid my hand up his leg until I found his cock, then I started to rub until I could feel him getting hard. He squirmed a little at first, but then relaxed, though he didn’t look down, he just stared, red faced, at the TV. After a few moments of rubbing I unzipped his pants and pulled them down to his ankles. He helped, lifting a little so that I could pull them down, but he still never looked at me. His cock is average, four, maybe five inches, but damn he could use a trim. I kissed the head, then kissed down the shaft and back up, cupping his balls in my hand and massaging them as I took him in my mouth. It didn’t take long before I felt his cock got harder and his body tensed, his cock twitched in my mouth and I swallowed spurt after spurt of his cum. Once I felt him start to get soft I took him out of my mouth but kept stroking, milking every last drop.
I got up off the floor and sat back down on the couch. He pulled his pants back up and sat stiffly watching TV until the show was over, then went right to his room, only saying goodnight once his back was to me.
The next morning was awkward, and god know that I was worried about the police showing up to my job to arrest me, but that never happened. Once I came home from work, he came out of his room to talk to me as if nothing had happened. I knew then that we were ok and I knew what I’d be doing that night.
After dinner as we sat on the couch, I got up, went to my bathroom and came back with a razor, a small bowl of water, and a pair of scissors. Like the night before, I pulled his pants down, his cock popping out, hard already. I trimmed with the scissors first until the hair was closely cut, then I shaved his balls and at the base of his shaft. I could see that it was still awkward for him, he still didn’t look at me, but at least he wasn’t beet red like that last time. Once he was all trimmed and shaved I cleaned him with a warm washcloth and gave him another blowjob. Afterward I cuddled up next to him. We kissed goodnight, a normal peck on the cheek.
It went on like this for a few more nights until I started to give him some instructions. Hold my hair, thrust a little into my mouth, that type of thing. I also started to lick his balls and play with his ass. And after time I could see that he was not just into it, he was looking forward to it. I started to take my top off when I’d go down on him, and then, eventually, I’d get completely naked. Soon we would cuddle on the couch naked together afterward.
It was more than a month later, but one night, going down on him, I stopped and straddled him, guiding him into me then resting my hands on his shoulders and rode him until he came in me (I’m on birth control.) After that night he really woke up. Each night we tried multiple positions, he became a little more aggressive, smacking my ass when he was behind me and pulling my hair. I let him cum on my face and tits. Once we even tried anal – I’m not a fan and so I’ve only ever done it a handful of times.
Soon he wasn’t even waiting for our normal time after dinner. He would come up behind me while I was making dinner and grab me, he’d come down to my bad at different hours in the night, he’d even play with me in the car when we were driving somewhere or put my hand on his cock.
This is the end of his senior year at high school, he’s staying in the state, but the school is still several hours away. He’s been more confident ever since we started having our little tryst, something I tried finally worked. But since his decision to go away for college he’s been even more aggressive, we’re having sex two to three times a day. When I’m on my period I’m giving him head. It’s exhausting and exhilarating. We have sex everywhere now, in bed, on the couch, in the kitchen, on the washer, in the car, etc… I’ll miss him when he goes away, and god knows I’ll look forward to when he comes home for breaks.
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