πŸ“š a stepmother's final lessons Part 4 of 6
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A Stepmothers Final Lessons Ch 04

A Stepmothers Final Lessons Ch 04

by onlyhappyendings
18 min read
4.41 (13800 views)
adultfiction
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(Part 4 of 6)

Author's note: I put a content warning in the tagline and I will elaborate here. This story includes male masturbation and girl-on-guy strapon action. If you can't tolerate that, please back out now and I invite you to rejoin me for chapters five and six. But I do hope you give me the benefit of doubt and read on. Thanks.

*****

I couldn't have asked for a better summer. The weather was mild so I took on a lot of hours at my temporary job with the occasional day off for rain. Staying with my stepmother meant that money was flowing back into my depleted bank account. I had more than enough for partying with my friends, many of whom, like me, were home from their first year of college. And going to parties got me introduced to plenty of nice ladies.

I didn't have to chase the ladies though since Heidi, my stepmother, volunteered to be my temporary girlfriend, which I don't have to tell you was the best part of my summer. She had been like a mother to me since my real mother passed away when I was nine. Only recently did she reveal that the only reason she was with my father at all was to raise me and to keep me from turning out like him. That answered a lot of questions I had growing up.

Now my father was out of the picture which suited me fine. Over the years I had problems getting along with Mom, as I was accustomed to think of her. But my relationship with Dad was a lost cause for a long time. Not that he gives a crap about me or anyone else. Now that it was just her and me, and me a grown man, Mom and I got along great. And every day that summer I got to know her better... as a person and as a woman.

If you've read my earlier stories you know just how well I got to know her. I learned that she liked to read dirty magazines, Hothouse magazine in particular. She especially liked the letters to the editor, in which readers purport to share their wild sexual experiences. Of course they are totally fake. But the stories are sexy and maybe even sexier if you persuade yourself they might really have happened.

Well, it was while we were reading those stories together that she seduced me, which led to a night of excitement that rivaled the most outrageous stories you could find in the pages of that infamous magazine. My stepmother, the woman who raised me, a stern, no-nonsense woman, became in an evening the sweetest, hottest lover that ever took a man all the way. And when I say all the way, I mean it.

But as the summer wore on our physical relationship started to taper off. At the same time, we came together in other ways, learning more than we ever had about each other's interests and habits and tastes. That was to be expected, Mom explained.

"Physical considerations bring two people together. But it doesn't last," she explained. "They are attracted by appearance and scents. They touch, they kiss, they make love. In doing so they form a bond. They can make the effort to keep the flame alive, and they should. But rarely will it burn as brightly as it does during their honeymoon phase.

"But as passion gives way to familiarity, their bond grows in other ways... emotionally, intellectually. Mature people accept this and take their relationships to the next level. Shallow people crave novelty so they flit from partner to partner. Men tend to do this, I think, but some women too.

"Some people want it both ways. They want the comfort and safety of a long-term relationship and still look for novelty outside of that bond. I imagine that is more of a woman thing but again, men do this too, men like your father. Don't be that way, Trey, please? I hope you find someone, the right one. But if you're with a girl and it isn't working out, just be a man and tell her so."

I wanted to tell her that I did find someone who I thought was the right one. But I knew it wasn't true. And some time this summer Mom was going to tell me it was over. And I had promised when that time came I would accept it and not get weird or possessive. But damn, if only there was a way I could change her mind.

As our time together was growing short, my sexual requests got kinkier. She didn't mind. She encouraged me to use my imagination and assured me that if I could think of it, she'd probably already done it. One thing I had to keep in mind though was her frequent insistence on reciprocity. That is, if I wanted her to do something she would want me to do the same in return. The first time I sucked on her toes, for instance, she insisted on sucking on mine. When I wanted to watch her masturbate, I had to play with myself as well. And when I stuck my finger up her butt, guess what. She said this would teach me empathy.

With that in mind, I should have anticipated what would happen when I left the Hothouse magazine out for her to find, open to a certain page. I had been reading what would become my favorite issue when I ran across a letter from a girl who described how she preserved her virginity and still kept her boyfriend happy by giving him frequent blowjobs. I liked this concept and the story was very hot. I liked it even better when her boyfriend persuaded her to give up the butt.

That got me thinking about Mom's hot little ass and the time she let me have it, our first night together. I couldn't forget how she casually told me about the glob of vaseline she put on her butthole, or the look in her eyes when I squeezed into her, or how she informed me that by claiming her ass I had gotten farther with her than my father ever did.

So, her ass wasn't off limits and yet we hadn't done it again since then. I doubted she would refuse me if I asked. But I was too embarrassed to bring it up. Then it hit me. Here was a way I could ask her for a repeat performance. I would leave the magazine out for her as we would sometimes do. Then it would be up to her whether we did it or not.

The way she slyly smiled when she brought the magazine to my room made me think I was in luck.

"I've been expecting you to bring this up. Surprised it's taken you this long." She paused and looked at me kindly. "We'll do this if you want... but not in the way you're thinking."

"What do you mean?"

"Trey, something I've tried to impress on you is how much preparation good sex can take."

"Yes, of course."

"And, ah, you understand how much of the burden of preparation falls on the woman?"

"Well, yeah. And I appreciate it, really."

"I'm not complaining, mind you. I actually love that about a guy... how he can be ready for love with a shower and a shave. And sometimes not even that."

I didn't know what to say. I kept myself pretty well groomed and dressed for her. But I had to admit her grooming rituals, her elaborate garments, her bedroom tricks were a testament to the effort she put into our lovemaking.

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"Maybe we girls make things more difficult than they need to be. I'm sure you wouldn't reject me if my legs were a little hairy or my breath smelled like garlic. But one thing I can guarantee. I wouldn't let you anywhere near my butt unless it was clean enough to eat off of. And I wouldn't let you put your dick in it unless I was certain of success."

"What are you saying?"

Mom pursed her lips and looked out my bedroom window. "That time I let you do that... it was unexpected, spontaneous... for you. I loved giving you that experience. It turned me on. Still does, just thinking about it. But I was getting myself ready for it long before that night. I didn't even know if we would go that far. But I was ready, just in case."

"Hmm, I'm thinking that you want me to reciprocate."

"You're very perceptive, Trey. It's called pegging and I know it's not something a guy wants to do. But I really think you would benefit from an advanced lesson in empathy."

"Yeah, not something I would want to do. But I'll do it, if that's what you want."

"It's not that I want it, to be honest, because I don't. Very few women would. If I were you, I wouldn't be the first to bring it up. And don't act too eager for it if she does. But the fact that you're willing to do it to please me makes me very happy."

So that's how I found myself at the adult bookstore, shopping for dildoes, quite an embarrassing experience. She said I needed two of them, each as big as my own package or bigger, and one of them should look like a real penis with balls and all. She also suggested I use condoms with them and water-based lube. Everything else I would have to figure out on my own.

A couple walked into the store just as I got to the counter with my items. The guy looked like a biker and the girl like a stripper. He whispered something to her when they saw what I was buying and her face lit up with amusement. I blushed all the way down to my shoulders but I went ahead with the purchase. It would have been even more awkward to back out.

As I mentioned, Mom and I had engaged in some ass play over the summer so I wasn't starting from scratch. Even so, it took me three days to manage penetrating myself. Once I got past the gate, though, I was able to push it all the way in. It felt weird but good, not going to lie. Not good sexually. It didn't make me hard. Just the opposite, in fact.

It felt good like stretching out sore muscles feels good. I also had some satisfaction of accomplishment like I passed a difficult test or achieved a training goal. I had found it frustrating that I couldn't do something that my stepmother easily could. I felt bad for asking her to take it when I couldn't. You'll probably laugh, but I felt proud of myself when I finally managed to sit on all six inches, right down to the flared base.

I left it in there for a while to get used to the feeling of fullness. I put on my jeans and walked around with it in my ass. I even went out to get the mail, trying not to walk too funny. I was so distracted I nearly didn't notice the letter for Heidi mixed in with the junk mail. It caught my eye because the return address was for the town where I went to college. Mom went to school there too. I guessed she still had friends there. Mike Charles... why did that name seem familiar?

Later, when I went to take the dildo out I tried pushing it in and out a couple times, expelling an involuntary 'unnnhhhh' each time. It wasn't enough that I could take it and hold it. I had to be able to get as well as I gave. With that goal, I had a long way to go. The next time I tried, though, it went a lot easier.

The realistic dildo was not for my ass. It was for my mouth. Mom wanted me to demonstrate oral skills as well, just like the girl in the Hothouse story. I found this even more humiliating than taking it the other way. I mean, yeah, taking a rubber dick in the pooper was bad. But it's a passive act. Sucking a rubber dick? That's active. I had to open my mouth, right there in the middle of my face, and wrap my lips around it. I had to lick it and trap it against my palate and to be careful not to touch it with my teeth.

I couldn't help but imagine what it would be like to do that with a real penis. The better job I did, the sooner it would be over. But that meant I would be good at sucking dick, not something I aspired to. Still, I wanted to do a good job for Mom. I could take it a little over half way before hitting my gag reflex. She never took me deeper than that. But girls in pornos took them right down to the root, big ones. I became curious about deep throating but was afraid of injuring myself. Imagine if I choked to death on a plastic penis and the paramedics found me that way.

I eventually visited the library and consulted several books on sexual health. I familiarized myself with the anatomy of the mouth and pharynx. I also learned a few things about the anal canal that would have saved me some trouble earlier. Armed with this knowledge I devoted myself to mastering some new skills. It took me two weeks to figure things out. But I figured them out.

Heidi never asked me how I was getting along. I guess she assumed I would be ready eventually or I would stop asking. I'm not sure I liked the way her eyes glittered when I told her I was ready.

She was sitting at the edge of the bed when I went into her bedroom, hunched forward with her elbows on her thighs. She sat up when I came in and her nightie parted, revealing a large flesh-colored phallus jutting up from between her legs.

"What do you think?" She asked, showing off her silicone penis proudly.

"It's big," I said, trying not to sound too happy or too sad about it. I was actually quite intimidated.

"It's called a FeelDoe. And this is the smallest one they sell, really. Touch it."

I sat down next to her and gingerly ran my finger from the tip to the base. It wasn't held on by a belt or harness but appeared to go up inside her vagina at a roughly ninety-degree angle. I brought my fingers back to the tip and pressed downward. It sprang upright again when I released it, causing her to gasp and swivel her hips slightly.

"The pony end fills me up pretty well and this part here rubs me in the right places. It's supposed to make me feel like you do when you fuck me. So I guess we'll both be having some new sensations tonight."

I wrapped my hand around it and stroked it gently. Her eyelids half closed as I did this and she practically purred.

"That feels good. But you're not getting off that easy. Or I'm not, I should say."

I crossed my legs and leaned into her lap, the tip of her fake dick hovering in mid air just centimeters from my lips. I knew from limited experience that this wasn't the ideal position for sucking a cock but this is how the girl in the story did it. Plus, it felt less submissive than being on my knees or lying on my back. I took a deep breath to get past the shame that washed over me and accepted the thing into my mouth.

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"Oh, that's it," Mom moaned and she ran her fingers through my hair and massaged my neck.

I started bobbing on the first couple of inches. I let my tongue swirl around the molded silicone head a couple of times but it quickly dawned on me that paying attention to the head was not going to help me. Her pleasure was to be found mainly in the base of the shaft. I switched to a strategy of pressing myself down on it as far as I could go without choking, then applying some suction on the way up.

Remembering how she would vary her movements to enhance my pleasure, I included nodding motions and side to side action in my routine. Then, when I sensed she was getting comfortable, I let her tip press against the back of my throat and forced myself down on it. I felt it push past my uvula and into my throat. Like with my anus, I found that once the dildo got past the gate, the rest of it could slide in easily.

"Oh fuck," Mom groaned as the lips of my mouth came in contact with the lips of her pussy. "How did you learn how to do that?"

I didn't answer, just felt the head of her dildo slide in my throat while I moved my face in little circles. I came up for air and masturbated her saliva-slick penis while I caught my breath. That was the turning point in my first and last blow job. Her hand on the back of my head became more insistent and controlling after that. At first I resented being treated that way. But then I recalled the times I did that to her and yeah, there was the lesson in empathy she was always trying to impart.

After she was satisfied with my mouth it was time for my ass. She had me roll a condom onto her penis while she pulled a latex glove onto her hand. I felt very weak and vulnerable on all fours with my ass sticking out. I shut my eyes and tried not to think about it as she lubed up my anus.

"I'm going to keep my fist wrapped around the base of it so that it doesn't go too deep in you."

"Thanks, Mom," I said.

"That will also keep it from tugging out of my you-know-what. It's not going to win a tug of war with your bunghole, you know."

"That's smart, Mom." I said, but I was wishing she would just get on with it.

"It will also protect me from cross contamination. We've talked about that, remember?"

"I remember. And I'm ready any time you are."

I suddenly felt the cold, greased up head at the entrance to my anus and before I could react it was squeezing past my sphincter muscles and into my ass.

"Oh shit!" I exclaimed but stayed stock still as inch after inch of silicone cock slid into me. I was so, so relieved when I felt the knuckles of Heidi's thumb and forefinger between my cheeks. I hung my head and breathed deeply to calm myself.

"You okay, sweetie?" She asked.

"Give me a moment and I'll be fine," I assured her, not sure of it myself. "Thank you for doing this for me."

"You are most welcome, Trey. Some girl is going to be so lucky to have you for a boyfriend."

Then she started moving, an inch at first, in and out. It kind of felt good. Doing this with a partner was a different experience, better in one way and worse in another. It was worse because I was extremely self-conscious being so utterly exposed this way in front of a loved one. But I did love her and it was a very loving act, so there was that. She started giving me two inches at a time, then three. Her pace started to pick up, too.

"I'm enjoying this more than I thought I would," she said as she fucked me from behind with casual thrusts of her hips. "I may have to try this with my uh..."

"With your what?" I asked, confused. It was hard to concentrate on anything except the silicone cock stretching me to capacity.

"Oh, nothing," she said and her free hand reached around and gave my dick a caressing stroke.

"Oh shit!" I cried out again. Her touch aroused me in a way I had not previously experienced while having my bottom abused. She wrapped her hand around it and it felt so good and very hard. The motion of her dildo in my ass caused my dick to move in her hand and I shut my eyes while I fucked and got fucked.

She was giving me as much of her stroke as the clenched fist on the base of her dick would allow. Her pace was vigorous, just on the edge of discomfort for me. I was close to coming. I wondered whether she would keep on going after I came. I would keep going, obviously, if I was fucking her and she came. I would keep going until I was done. I tried not to think about it lest I spoil an epic climax.

She did not keep going though, but slowed to a stop while I splurged into her hand. I lowered myself down to my elbows and savored the feeling of being full of her cock. To my surprise she reached forward and offered me her semen-covered fingers. I cringed away from them.

"It's a one-time only offer, Trey," she said, a hint of command in her voice.

I thought it over, thought about the times she had happily swallowed my seed right from the source. I opened my mouth. And while my mother slid her flesh-colored FeelDoe out of my ass I licked and sucked my essence off of her long slender fingers.

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