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Santa's Helper Chapter 3

"Jimmy and Debbie discuss the future."

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Christmas was officially in the books, and what a Christmas it was. For the first time, I didn't mind sharing my birthday with Santa and his minions. My stepmom more than made up for all those birthdays that took second fiddle to the excitement of Christmas.

After Dad was killed in a horrible traffic accident, his young wife, Debbie, and I had grown closer. Misery loves company, I guess, but it was more than that. Dad and I were never close and my real mom rarely contacted me. She and my sister were in another city, but they may as well have been on another planet. After my parents divorced, my dad wasted no time finding another woman to screw. It turned out she worked in a strip club as a bartender after moving up from dancing with a pole for a partner. Regardless of her questionable background, she was a babe. Not only was she gorgeous with blonde hair and blue eyes, but her compact frame sported a set of double D's–34DD to be exact.

At first, I was naturally suspicious why such a gorgeous woman would have anything to do with my asshole father. She confided in me that my father was a real gentleman with her and I was too harsh on him.

Whatever. I accepted that explanation mainly because I loved that she was living with us. Their whirlwind romance resulted in a quick marriage. And just like that, she was my stepmom.

But as I got to know her, I bonded with her. Of course, I had sexual fantasies that were at the heart of my feelings and eventually kept a pair of her panties close by for frequent masturbation sessions. Regardless, she was personable and smart on top of being this teenager's version of the perfect woman.

So when she quietly entered my bedroom in the wee hours of Christmas morning, all my dreams came true. Debbie took pity on me as an eighteen-year-old virgin. I think there was also some selfishness on her part as well. She confided that having no sex since Dad died had been difficult. She was used to getting it regularly. Later, I found out she and Dad had sex almost every night. And I could see why.

So Christmas night I awoke to find her crawling onto my bed. She shushed me and then promptly gave me my first blowjob, followed by my first intercourse. If that wasn't enough, the next morning I was rewarded with a kitchen lap dance, only with my cock buried in her. We ended the morning with a shared shower and a handjob where she let me come all over her tits.

We were both spent at that point. I actually could not fuck another stroke. My balls were drained and my cock needed a rest. Keeping up with my stepmom was no small task.

We took the next day off from sex and the following day we just snuggled. We slept in separate beds even though I had hoped we could spend a night together. But Debbie was in control, and who was I to argue?

As New Year's Eve approached, I wondered where all this was heading. Was this a once in a lifetime tryst or something more? Would guilt override passion? I waited for the ball to drop.

I didn't have to wait long. A few days after Christmas, Debbie indicated we needed to "talk." That sounded bad. I prepared for the worst.

I was in my room playing a video game and Debbie knocked and opened the door a crack.

"Okay to come in, Jimmy?"

I put the console away and invited her in. She had been doing house chores and her hair was tied back in a cute ponytail. She was wearing yoga pants and a loose T of my dad's. It was obvious she was not wearing a bra. Her large nipples announced their presence and her boobs jiggled with each step. My cock hardened automatically.

"We need to talk, Honey."

Here it comes–the oral version of the Dear John letter.

But to my amazement, it wasn't that.

"Honey, since your father died I've been a roller coaster of emotions. I'm not even thirty, and I'm a widow with an eighteen-year-old son still in high school. I thought about moving out of state and starting over, but I can't leave you. I know you are essentially an adult, but you are still technically a teenager. So here's what I'm thinking."

She outlined a plan to return to work, but not at a strip club or bartending. She had an offer from an old friend who owned a high-end ladies-wear shop. She had offered Debbie a job as a salesperson with an option to buy into the business if it worked out.

"This would keep us together and between my income and your dad's insurance settlement, we should be fine. We probably even have enough money for a college fund for you. And besides, I've developed quite a relationship with you. I know I'm an old lady compared to the girls you are used to, but I've developed feelings for you, Jimmy. This is not exactly a traditional mom/son relationship. And truthfully, I don't want to be looking for a husband at any time soon. Any needs I have can be taken care of quite nicely by my hung stepson. What do you think?"

"Oh my god, Debbie. That sounds wonderful. Yes, of course! I'm all for it. i have only a semester of school left, and then I could get a job as well. We'll be fine. I'm not sure I want to attend college, but I know I want to stay close to you.

"Sweetie, you are a teenager with raging hormones fucking a big-titted MILF. Your penis is doing all the talking. You may get tired of me in short order, but we can try this and see how it goes. And speaking of your penis, is it trying to say something right now?"

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I wore a pair of nylon running shorts and hadn't bothered with underwear. My cock head was sticking out of the leg of my shorts and struggling for air. The bulbous head looked huge as it almost reached my knee.

Debbie smiled and sat on the edge of the bed before patting it with her hand.

"Come here, Honey. Let me take care of that for you before you pass out from a blood rush to your cock. That's a major vein you got there."

I rose from my chair and before I sat on the bed, Debbie reached over and slid my shorts to the floor. My cock rebounded and nearly hit her in the face.

"Hello," she said as if talking to my cock. "Nice to meet you again."

She reached over and grabbed it in her small hand and stroked it.

"How about a little kiss? I bet your owner would like that."

She kissed the tip and then extended her tongue and licked all around the crown before opening her mouth and stretching her lips over the end. I watched as her lips tried to take in as much of me as possible, her mouth and tongue working in unison until almost half of my cock was in her mouth. She sealed her lips around me and sucked so hard that her cheeks hollowed while she backed off of the shaft and kept only the helmet in her mouth. She continued in this way for several strokes and I thought I was going to cum immediately. It felt like a Hoover vacuum was on the end of my cock.

"Oh, fuck, Debbie. That feels so good. You suck so good. I don't think I can hold it."

Standing there with a bird's-eye view of my stepmother sucking my cock was about as exciting as anything I had ever seen. She slipped me out of her mouth to speak, saliva dripping off her lower lip and onto her chin and chest.

"God, I still can't believe how big you are. It's hard to keep from choking on you. If you have to cum, Honey, that's the whole point. Get it out of these big, hairy balls and into my mouth. I love the taste of your cum, but I have ways to prolong it as well. I'll give you a motherly squeeze when I think you are going to cum and let's see how long you can hold it. Hmmm? This is good practice for you to keep from cumming prematurely."

She stared up at me with those big blue eyes and recommenced fellating me. As her lips obscenely returned to my cock, her hand stroked me, occasionally stopping to squeeze the base of my shaft when she felt I was going to lose control. She continued in this way making loud sucking noises and using lots of saliva to lubricate me in the process.

With a free hand, she raised her T-shirt above her breasts and placed my hand on a firm tit to fondle. That was it. I couldn't hold it any longer and my cock began to throb. Debbie squeezed me tightly with her stroking hand and then massaged my testicles with her free hand. My cock jerked once, twice, and then she released the stranglehold with her fingers at the base. A huge load shot up the large channel on the bottom of my shaft and my piss hole.

Debbie had only the head in her mouth when the first blast erupted. She continued sucking and swallowing as much as she could but quickly fell behind the volume entering her mouth. Milky sperm began leaking out the sides of her mouth and onto her hand and wrist before dripping onto her large breasts. I had not jacked off for several days, saving myself for the possibility of something like this. The result was a huge load that could not be contained by Debbie's mouth despite a notable effort to swallow it all.

When my orgasm had finally subsided, she was nearly out of breath. She supported my flaccid cock with her hand while she licked and sucked my cock head clean. When she was finally satisfied there was no more, she let my cock fall limply to my thigh and looked up at me with a cum plastered grin.

"Holy shit, Honey. That was a meal-and-a-half, When you cum, you don't hold back."

She had shiny goo all over her face from a good-sized blast that caught her as she was catching her breath. Even her eyelashes had sperm on them. She wiped her lips with a finger and sucked it clean between her pursed lips.

"Sorry, Debbie. I couldn't help myself. That was unbelievable. Let me get a washcloth for you."

"No worries, Sweetheart. Gimme a kiss and I'll forgive you. Come here, you big stud."

She opened her arms to me and I sat down and embraced her. I kissed her lips and sampled the taste of my sperm. Following suit, I wiped her cheeks with my finger and sucked it clean.

We lay back on the bed and kissed.

"Debbie, you are wonderful. I am so lucky my dad found you. You have made me the happiest guy on earth, I swear. What could be better than this?"

"You mean better than your stepmom giving you a blowjob. I can think of things just as nice, but we'll talk about that later. I'd better wash up in case someone drops by and wonders how I got jizz all over my face. But later tonight, I'll let you pay me back. One good turn deserves another. I love oral sex from both sides: giving and receiving. You're a good student so I'm looking forward to a nice, slow, evening session.

She kissed me again, straightened her T-shirt, and walked to the door. She turned and winked at me.

"Better get some rest. You're going to need it, Honey."

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Written by johndoe7
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