In Over My Head, Part 4: Fucking My New Step-Mom [mF][dark]

This is a work of fiction.

I'm writing this down because I don't know what else to do. My grades have gone down the tubes, my college plans are looking iffy, and I've started cutting myself. I want to tell someone but I'm too scared – it could destroy my family and leave us in a national media circus. I'm hoping that writing this down will help; I'll probably just burn it but at least I'll kinda get it out.

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“We’re getting married!”

Dad and Caroline told me at a holiday dinner, just the three of us. Dad beamed with joy, and Caroline put her arms around him and kissed him on the cheek.

“Congratulations,” I said, managing a beaming smile. “I’d been wondering when you’d get around to it, Dad.”

It had been six months since Caroline first cornered me in our garden shed, and in that time she’d worked her way thoroughly into my mind and my pants. I’d seen her less frequently since her fall classes had started up, but she made up for it by calling on nights when my Dad was on-call at the hospital, giving me detailed instructions for how to touch myself and where, arousing me then ordering me to stop, edging me for hours until finally giving me permission to cum. When she did visit to work the garden, she began to teach me how to eat her pussy, lick her feet and put my finger in her ass to make her orgasm. I had to help her, you see, since she was helping me to control my “sick urges” by getting me off with her hands, her breasts and her mouth.

I was 15. She was 21.

Afterwards, she would hold me in her lap and reassure me. She’d take care of me and make sure I didn’t hurt anyone. It would be our little secret, and Dad would never have to know how I’d violated his girlfriend.

And I was, outwardly at least, happy and well-adjusted. Sure, I never talked to any of my old friends anymore, but I had her. Sure, I’d dropped off the cross-country team because practices were taking too much of my time, she said, but that just let me spend more time with her. And yes, my grades had dropped because I couldn’t get all my homework done, but I still had a B average. I was her pleasure toy, and I loved it.

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The next escalation happened in late May, a few weeks before the wedding. Caroline was home for a week before her graduation and so I was unsurprised to see her waiting for me on the couch when I came home. “Up to your room,” she ordered, and obediently I followed. Once we got there, she sat me down on the bed, removed my shoes, and told me to take my pants off. This was standard procedure for our trysts – her manner would be brisk and businesslike until the sexual contact started. As I undressed she lifted her blouse over her shirt and laid it across my chair, then unhooked her front-clasp bra and shrugged it off, revealing her 36DD breasts. She came and sat next to me on the bed and kissed me, while I massaged her breasts with my hands.

As I grew hard she gently stroked my cock, running her hands lightly along the shaft, rubbing my precum over the tip. She moved my mouth to her nipples and I teased them as she’d taught me to do, running my tongue around the edge of her areolae, flicking her nipple, then sucking and gently biting each in turn.

At this point she usually took my cock in her mouth or had me fuck her tits, but today she stopped me, pulled off her shorts and panties, and pay down on my bed with a towel under her. Normally she wouldn’t remove her bottoms until she’d made me cum and even then only after I’d put my underwear and pants back on. Today, though, she simply said “I think I should be first today,” and pulled me down toward her open slit.

I kneeled on the floor beside the bed and lowered my mouth to her already-wet pussy. As she’d taught me to do, I began by working my tongue along her vulva, lingering at her clit to circle it with the tip of my tongue. She began to breathe heavily and play with her nipples as I worked first my tongue, then a finger, then two fingers into her pussy. Finally I had three fingers inside her, finger banging her as I teased and sucked her clit with my mouth. As I began working my hand in toward her g-spot, she stopped me and motioned me up onto the bed with her.

And then she reached down and pulled me inside of her.

This had been the big forbidden no-no; we were constantly having oral sex with each other, but she had always insisted one of us have pants on at all times. Excited to finally feel what it was like to penetrate a girl, I gasped as I slowly pushed all the way into her sopping wet cunt. I stopped there and shuddered a bit, then felt her squeezing my cock with her vaginal walls. She started to rock her hips toward me, then back again, and I quickly joined in, timing my motions to hers as I slowly thrusting.

She pulled my head down to her breasts and I began to suck and tease her nipples. She began to whine as my thrusts increased in tempo. I felt her tightening around my cock and…and came, thrusting deep inside of her and gasping, then giving two more smaller thrusts and collapsing on top of her.

I lay there for a moment, my cock still twitching inside of her, enjoying the feel of her skin against mine. But she quickly pushed me off and began rocking back and forth, curled in a ball and crying “Oh, David what have you done?”

If you’ve been reading along, you saw this coming. At the time, even I knew it was coming. As I’d worked my cock into her, I knew it was wrong, I knew it would end badly, I knew it would be my fault. She always turned the afterglow to ash, bitter remorse to replace the ecstasy.

And I did it anyway. That’s what I can never forgive myself for.

I held her, in a reversal of our previous sessions of mind-fucking that followed our sex. I told her I was sorry, that I’d never do it again – even then I knew that was a lie, and a lie that would be turned against me with bitter potency – and that I didn’t mean to hurt her.

Inside I felt disconnected, like this wasn’t happening to me at all, but to someone far away, and I didn’t care what happened to him.

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After the wedding Dad and Caroline went on a week-long cruise. I told myself that I would stop it, that it wouldn’t happen again.

I knew I was lying. I knew I had no control and no way to stop what would happen next.

Source: reddit.com/r/sexystories/comments/33ieo3/in_over_my_head_part_4_fucking_my_new_stepmom