Helping Henry
Chapter 1
by The Pen Is Mightier
Everything that night was a blur. I remember screaming into the phone that I needed an ambulance. Then I found myself standing against the wall in the emergency room as they carted him off to surgery. Then I was pacing the floor in the waiting room. The first thing I remember clearly was when the surgeon came out to talk to me.
“Henry suffered what’s called a brain aneurysm,” he explained. “He’s very lucky to be alive. Another minute or two and there would have been nothing we could have done.”
I nearly collapsed to the floor when I heard those words. Henry. My Henry, so close to being taken from me. I listened as best I could as the doctor explained the next steps. New medications, a stay in the hospital, and tests—lots and lots of tests. We’d be in the hospital a week or two, maybe more if they find anything else. Of course, I agreed to everything they suggested during his stay, including the experimental medicines offered as part of a research study on aneurysm survivors. I was just thankful that I didn’t lose my boy.
Honestly, “boy” wasn’t the best term to describe Henry. At eighteen, he was more of a man than any of the guys who regularly hit on me at the bar or gym. He was strong, a hard worker, and brilliant. I’ve heard some single parents say that raising a son was challenging, but for me, it always felt like a breeze. I was lucky to have him. He truly was my happy accident.
I’d never actually meant to get pregnant. I hadn’t even planned on having sex that night, but I let myself get carried away. I was a horny teenager, and he was a wealthy man in his forties. We met in an online chat room, and almost immediately he asked me if I wanted to meet. One thing led to another, and a couple of nights later I found myself in a hotel room bed, naked and moaning as he filled me with his seed.
After that night, he tried to avoid me online, but after some morning sickness led to a positive pregnancy test a few weeks later, he agreed to meet and have lunch with me. I knew I had to keep the baby, and I told him as much. He wanted nothing more than to make the situation go away. It turned out that he was married and in a position where an affair resulting in a pregnancy would ruin him.
In exchange for my silence, he offered to set up a shell company that he would divert funds into from his other business ventures. This shell company would ensure that my child and I could have a comfortable life. He even offered to pay my legal fees if I wanted to hire a lawyer to verify that this was all on the level. Long story short, I took the deal, signed his NDA, and a couple of weeks later, the first check came in. The result was that Henry got a great education, and I was able to be a stay-at-home mom, despite being a single parent.
After the stay at the hospital, the doctors wanted Henry to take it easy for a while and ease back into his routine. Honestly, the timing was pretty good. He’d just graduated high school a few weeks prior to the incident, and he hadn’t started at his summer job yet. We decided that he should take the summer off from work, and we’d play the following autumn by ear. Henry didn’t complain, and after getting a few final instructions, we were packed up and heading home.
About a week after Henry came home from the hospital, I started getting these strange feelings. It was almost as if I was being watched, even if I was all alone. At first, it really bothered me. I’d spin around suddenly, expecting someone to be standing there, but the room was empty. It felt almost like someone could see and hear everything I was doing and thinking, if that even makes sense. Ultimately I wrote it off as stress, a combination of Henry’s incident along with the fact that it had been months since I’d so much as been on a date. After about a week of this, the feeling seemed to fade into the background noise. It didn’t go away per se; it just seemed not to bother me anymore. It was about that time when I first had the thought.
I should help Henry.
I’d been standing in the middle of the kitchen when it came to me. I should help Henry. When the thought first occurred to me, I scrunched up my face a bit and tried to figure out where it came from.
I should help Henry.
I mean, for the last couple of weeks, I had been helping Henry. He wasn’t on bed rest, but the surgery and subsequent tests definitely took a lot out of him. Because of that, I spent a lot of time checking up on him and making sure he was okay. So why was I suddenly overcome with a feeling that I needed to go help Henry?
I should help Henry.
Part of me worried that it was some sort of premonition. You know, like “mother’s intuition” or something like that? Maybe Henry was hurt, and something in my subconscious was alerting me to it. I immediately thought of his aneurysm and started to panic, wondering if he was having a similar emergency. I took a breath, trying to calm my nerves. Hoping that it was nothing, I walked out of the kitchen, through the dining room, and into the living room, where Henry was lying on the sofa with his eyes scrunched closed. The expression on his face looked almost like he was concentrating. Or maybe he had a bad headache.
Or maybe his brain was bleeding again.
“Henry!” I said a bit too loudly, trying to keep calm despite a slight panic beginning to build. “Henry. Are you alright?”
Almost immediately, Henry opened his eyes and sat up. He stared at me, giving me this sort of inquisitive look, as though he was trying to figure out why I was so upset.
“Yeah, Mom,” he began. “I’m just fine. Why? What’s wrong?”
I let out a heavy sigh. “Sorry, dear, I guess it was nothing. I was just cleaning in the kitchen when I got this weird feeling that you needed my help, and then I came out here and found you on the sofa, looking kind of like you did before… you know, before the incident.”
“Really?” Henry’s voice was full of wonder, as though I’d told him I saw into the future or something.
“Yeah. It was weird. Anyway, was there anything you needed while I’m here?”
“Actually,” he said, a slight grin tugging at the corner of his lips, “I could really go for a sandwich, if you’re headed back to the kitchen anyway.”
I should help Henry.
“Of course,” I replied, happy to help. I went and made him a sandwich and sat with him as we talked for a bit.
About a week later, Henry and I were snuggling up on the sofa getting ready to watch a movie. This wasn’t anything unusual for us. It definitely wasn’t anything sexual.
Or so I thought.
While we were curled up together watching the film, a fairly steamy sex scene came on. I had been pressed up against Henry at the moment, and I didn’t really think much of it at first. Henry was eighteen. He’d watched movies with sex scenes in them before in my presence. Hell, for that matter, as a single parent, I was the one who had to give him the “birds and the bees” talk earlier in his life. We were pretty comfortable about the topic, to the point that we’d had multiple conversations about sex before, especially when he was old enough to start dating.
Still, that night, something was different. As the scene played, I felt Henry stiffen up beside me. After his incident, I felt like I was always on high alert, and tonight was no different. I asked if he was okay, and at first he just nodded a little. I still felt something was off, so I prodded him to tell me what was going on. He hesitated, giving me a look as if he was trying to muster up the courage to say something. I reminded him that I was his mother and he could tell me anything, and that was when he said it.
“I just… I’m just a bit, um, aroused,” he admitted.
I should help Henry.
I have to admit, I was a little surprised by the comment. Sure, the scene in the movie was pretty steamy, but most teens his age would keep information like that to themselves and just go beat off later. Instead, Henry was here, sharing it openly with his mother. He assured me that it had nothing to do with me and that it was just the physical contact in connection with the hot sex scene. I told him that it was perfectly understandable and not to worry about it.
I should help Henry.
It seemed like he wanted to say something else, so I told him to go on. He really opened up after that, explaining how sexually frustrated he’d been lately and how good it felt to be close to someone. He hadn’t had a girlfriend in months, long before his hospitalization, and nothing ever felt as good as being with someone. When the scene came on in the movie, he had felt my body against his, and he admitted that it made him hard. Very hard, apparently. I was a little embarrassed to hear this from the mouth of my own son, but I told him it’s okay, and it’s totally normal to have those feelings. I pointed out that I hadn’t been out with a guy in a while myself, and I definitely had struggles with that at times.
Then Henry asked something I’d have never predicted in a thousand years.
“Well, don’t take this the wrong way, but do you think you could maybe… help me?” Henry asked.
I should help Henry.
I looked at him, my eyes going wide. Surely he didn’t mean what I thought he did. “What are you saying?” I asked him with a tone of concern.
“You know. Maybe you could, like, give me a handjob.”
I should help Henry.
“Henry,” I said, my mouth falling agape after I said his name as I tried to formulate the proper words. “I’m your mother.”
I should help Henry.
“I know. It’s just, it’s really hard, and it’ll be uncomfortable if it doesn’t get dealt with.”
The way Henry was casually talking about his mother getting him off totally caught me off guard. He was almost acting like he was asking for a foot rub. I couldn’t be upset with him over it; after all, I did goad him into the conversation. Still, I was flustered as hell. We sat there, staring at each other in awkward silence for a bit, and finally I told him that I loved him, but touching him like that wasn’t appropriate. I made it clear that he should be having those kinds of interactions with other people his age. Then I suggested that if it was really bothering him, he should go up to his room and deal with it.
He agreed and got up to leave the living room. Some time later, he returned to his spot on the sofa. I kept a little gap between us this time, not wanting to get him excited all over again, and we tried to move on, watching the rest of the movie in a slightly awkward silence. Henry didn’t ask me to get him off again, and that was where we left things.
For the next several days, life seemed to get back to normal. Or at least some kind of normal. Henry and I still had a good time together. We went to the park one day and hit the pool another. We chatted, laughed, and acted as if he’d never asked me what he had. On the surface, it looked like everything was just as it always had been.
Except it wasn’t.
Over those several days, I couldn’t get that moment during the movie off my mind. It just replayed continually on a never-ending loop. My son got hard from my contact, then asked me to touch him sexually. I heard his voice, again and again, asking me for that handjob. And every time the thought came up, it was followed by another thought.
I should help Henry.
To this day, I couldn’t tell you how I talked myself into it. Maybe I felt bad for him. Maybe I thought it would help him in the wake of his hospitalization. Hell, maybe I subconsciously wanted it myself. Whatever the reason, I found myself feeling more and more like Henry’s request wasn’t as awful as I first thought. Really, it was almost like a medical procedure. I’d given Henry several back massages since he was released from the hospital. This was just another kind of massage. If I kept things in that light, it almost felt bad not to fulfill his request. After all, he was my son, and he was simply asking for help. And I should help Henry.
Not long after I made up my mind, I called Henry into the living room and sat him down for a talk. I asked him if he remembered what he’d asked for.
“You mean during the movie?” I could hear concern in his voice.
“Yes,” I replied, “during the movie. Don’t worry, you’re not in any trouble. I just want to talk.”
As soon as I said that, he visibly calmed down and gave me a sheepish smile. It was honestly adorable how timid he seemed. I told him that I’d given his request some thought, and I changed my mind. You could see his eyes light up as I said those words, and his grin told me that he was excited, to say the least.
“Hang on,” I said firmly, drawing his eyes to mine. “I want to make something clear. This is a one-time thing, and only because you haven’t had a girlfriend in a while. I still think you need to find a girl your age for… these things. Understand, mister?”
Henry nodded enthusiastically, and a moment later he was racing off to his room as I headed into the bathroom to gather up the necessary supplies. My head was absolutely swimming as I dug through the bathroom closet for my latex gloves and lotion. What had I just agreed to? I just offered to give my son a handjob. I told him that I, his mother, was going to jerk him off. What would people think if they ever found out?
“I should help Henry,” I told myself again and again, echoing the thought reverberating in my head. “I should help Henry.”
After I had everything gathered, I found myself standing in his doorway. He’d turned off the lights, and there was this kind of intense silence as I looked at him lying there under the sheet. “He’s naked under that sheet,” I thought as I wordlessly entered his room. It hadn’t been a sexual thought in the least, just an observation.
I took a seat on the bed next to Henry. Without saying a word to him, I slipped on my latex glove and squirted a little bit of the lotion into my palm. My heart was racing. I couldn’t believe it. I was really going to do this. For what felt like an eternity, I stared at my gloved hand with a gob of lotion resting in it. Then slowly, my eyes lifted, turning to meet Henry’s.
“Are you sure you want this?” I asked. In response, Henry just nodded.
I pulled back the sheet, exposing Henry’s erection. “It’s just like a medical procedure,” I told myself. As clinically as I possibly could, I reached out, wrapping my hand around him. Even through the glove, I could feel his warmth as I began to slowly stroke him. I diverted my eyes, doing my best to focus on a point in the far corner of the room. I didn’t want to see Henry’s eyes. I definitely didn’t want to see his erection. I was performing a procedure to give him some relief; that was it.
After a few minutes, I heard his breathing intensify. I was still looking away, telling myself this was like a back massage. As his breathing quickened, I found my strokes coming more quickly as well. Soon, Henry let out a little moan.
“Oh, fuck, Mom,” he groaned.
For a moment after he said those words, I couldn’t breathe. Suddenly, I was hit with the full weight of what I was doing. I was jacking off my son. I was doing something no mother should ever do.
An instant later, I felt his cock begin to pulsate in my gloved hand as he started to come. Acting quickly, I grabbed the neatly folded paper towel I’d brought in with me, putting it at the head of his cock to catch his cum. As he filled up the paper towel with his load, I started to feel sick to my stomach. This was not a back massage. This was disgusting. This was wrong.
I should help Henry.
I barely slept a wink that night. For the next two days, I was an absolute train wreck. I hardly came out of my room, and I barely spoke to Henry the few times we saw each other. I felt like the worst mother ever. I felt like I’d ruined him forever, along with myself.
Three days after giving him the handjob, Henry broke the painful silence. He said he noticed how distant I’d become. He told me he was worried that it was because of what we’d done. He tried to reassure me, telling me again and again how much he’d enjoyed it. I found myself crying, saying that I was so afraid I’d hurt him. Henry held me in a tight embrace, assuring me that I’d helped him so much.
“Honestly, Mom,” he told me, “it was the best experience of my life. If you’d be open to it, I’d like to do it again.”
I should help Henry.
“Honey, I’m your mother.” I said. “It's just… mothers don’t do those things with their sons.”
“But Mom,” he gently protested, “it helped me so much. Don’t you want to help me like that again?”
I should help Henry.
“I just,” I began.
I should help Henry.
“We’re just…”
I should help Henry.
“Henry, I don’t know if we…”
I should help Henry.
“Let me think about it, okay?” I asked as quickly as I could before turning and running to my room.
Somehow, despite my emotions, that night I found myself in Henry’s room. Just like the time before, I slipped on my latex glove. Just like the time before, I squirted lotion in my hand. Just like the time before, I pulled back his sheet. Just like the time before, I looked away. And just like the time before, I stroked his cock until he erupted, filling my neatly folded paper towel.
“Fuck, Mom,” he groaned as I wiped him up and pulled his sheet back over his erection. “It’d be so helpful if we did this more often.”
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