Chapter 3: Stephano Selects a Stepmother

My father was at his castle in Germany and did a video call with me. I saw he was wearing a tailored suit in a plushly furnished and well decorated room, similar to the parlor at home. Behind him were five women sitting on a pair of sofas. All of them were a little younger than my mother, and beautiful. They all looked nervous and uncomfortable. As usual, my father preferred blondes. There was only one redhead and a single brunette.

“Son, I’ve decided to be home more, maybe a week or two every month. We can spend a lot more time together.”

“That would be great, Dad!”

“I need you to do me a big favor and choose which of my girlfriends I’ll marry. If you pick, the others won’t be mad that I favored her over them. They all agreed, whoever I marry won’t complain about the others, because I’ll be with her a lot more often. All of them have children and had surgery or long-term birth control, so they can’t get pregnant again.

You’ll be in charge of the kids at home, but don’t worry about them for now. I still have Gretta’s number if any of them are too much to handle.”

I thought aloud, “OH MY GOD! I’d never inflict GRETTA on anybody! Even terrorists probably don’t deserve her!”

Dad chuckled. “You might be right! I want you to pick the woman you get along with best as your new stepmother, because she’ll be in the house with you all the time.”

“Cool! That’s really nice of you dad. It would be great to have somebody here I can really talk to.”

He got a strange look in his eyes as he said, “I think I solved the cheating problem, too. My girlfriends that live in Europe will all choose one of the servants as their favorite, to spend the night with them when I’m not around and make sure they don’t sleep with anybody else. I want you to do the same with your new stepmother. Any time I’m not home, I want her in your bed so you can keep an eye on her.”

Instead of preventing cheating, he was guaranteeing all of them would cheat all the time! Unless sleeping with somebody he approved of wasn’t cheating? Maybe? I had no clue where he got his crazy idea, but if it would get me lots of sex with a pretty woman I wasn’t going to argue!

Dad concluded with, “Each of the ladies will spend a week with you, so you can get to know them. Annalise will be there tomorrow.” A skinny blonde, the one with the smallest boobs, waved to me and smiled.

He continued, “Their kids will visit for a few days too. Thanks for doing this for me, son. I appreciate it.”

He ended the call before I could thank him thousands of times. I did say “Thank you” to the blank screen for half a minute.

I had a devious plan to blackmail the women into sex. I’d tell the them if they wanted to win they needed to screw me. I couldn’t wait to put my evil plan into action. Later I discovered my plan wasn’t clever at all. The situation was obvious enough that most of them offered me sex before I could ask!

As I was finishing my morning workout the next day, one of the butlers told me Annalise had arrived, and was waiting for me at the yellow guest house. That was the one usually provided for guests who smoked. I wasn’t looking forward to smelling a stinky smoker, but I’d put up with it if I got some sex.

“Tell her I’ll be there for dinner at six, Jerry.”

He sounded annoyed, “I’m still Jonathan, sir. And she sent you something.” He handed me a gift-wrapped package, pink crepe paper wrapped in white ribbon. “She said you should open it in private, sir.” He handed me a pair of scissors and left the room.

I cut the ribbon and tore open one end of the pink paper. Inside was a plastic bag with something else pink in it. I opened the bag and smelled something very sexy. There was an aroma of a French perfume, and something ... quite arousing. I looked in the bag and found a photo and a pair of soiled pink panties. The photo showed a vagina being held open by two fingers with long pink fingernails. Written on the back was, “I can’t wait to meet you.”

I sniffed the panties and quickly started getting erect. I closed the bag and ran the way Jerry had gone. When I saw him I said, “Change of plans, tell her I’ll be there in five minutes.”

I was wearing a sweaty t-shirt and gym shorts, but from her obscene gift I knew I wouldn’t have them on for long. I usually showered right after my workout, but I could fix that with a dip in the pool, or maybe better, a shower with her.

When I got to the yellow house I saw her unpacking a suitcase, wearing only pink high heels and a pink bikini. I could see the shape of her nipples through the thin fabric of her top.

“Hello, I’m Stephano. Can I help you with that?”

She closed the suitcase. “I’m Annalise. The luggage can wait. I’m supposed to get to know you. I’m not so great at talking, so can we talk when you’re too tired for any more sex?” She put a hand on my groin and squeezed a little.

“Sure! Sure!”

She sat in a chair and had me stand in front of her. “I love having something in my mouth. That’s why I like smoking and sucking cock.”

She sniffed my shorts before she slid them down. “Mmmm! You smell like your father! Nice!” She licked and sucked me like a champ, as I held her shoulders to keep my balance. I squirted two loads into her mouth before I needed to rest.

“You taste great! Just like your dad! And your cock is nearly as big as his. I love to fuck him so much! His big dick makes me feel so full! Do you want to fuck me? I can’t get pregnant, so you don’t need condoms.”

“Just a minute, let me get some water.” I went to the kitchen and drank a glass.

By the time I got back, she had her bikini bottoms off and was leaning over the arm of the couch. In her high heels, she was the perfect height. I easily slid into her as she lit a cigarette. It was the first time I’d been inside a pussy bareback. Without a rubber membrane between us, it felt so much better! I never wanted to use condoms again.

The sucking motions of her mouth reminded me a lot of the great blowjobs she’d just given me. I slowly slid in and out of her, as I watched her puffing on the cigarette. Some of the smoke rose in spirals, matching the spirals of her curly blonde hair. Seeing her tap it with her long pink fingernail to knock the ash off looked feminine and flirty. I thrust into her over and over, picking up speed gradually. She had a small orgasm. “Oooh! Yeah! Uh! So good!”

After another dozen thrusts or so, she asked, “Do you want to try my ass too? I kind of like it in my butt.” She handed me a small bottle of lube, took a big puff, and the sucking motion aroused me even further.

I drizzled some of the lube between her butt cheeks, then pulled out of her snatch and pushed her butt down slightly. It was freakin’ AMAZING when I slowly pushed my cock into her little asshole! It squeezed me SO TIGHTLY! Without a condom it felt almost unbelievably great! I only lasted a few dozen strokes in her rectum and squirted deep into her. “AAAAHHH! YEAH! UH! UH! AAAAAHHH! SO GREAT! Thank you!” I laid on top of her a while, resting and watching her suck on her cigarette. I didn’t care so much about the smell anymore.

When it was finished, she crushed it out in the ashtray and said, “Let’s get a shower and wash my shit off you, so you can fuck my mouth again.” Her crude language was a little jarring, but I thought that was an excellent plan. In the shower I washed her boobs first. They were small but suited her slender frame. She washed my penis well but I only got halfway erect, after three climaxes in an hour.

We dried each other then sat on the sofa nude. She said, “You fucked me almost as good as your father does. That was nice. You should use more lube for my ass though, it hurt a little at the start. Your Dad always uses plenty of lube. And maybe you could play with my hair during sex, like he does? And I love it when he kisses my ears!”

I made my decision about her after only two hours. Sex with her felt great, but it bothered me a lot when she compared me to my dad, usually unfavorably. For the next four days, I spent as much time as possible with my cock in her mouth, to avoid her talking about my dad.

On the fifth day her seven-year-old son arrived. We played in the pool with him and I showed him some video games I liked. She sealed her fate just before they left. She said, “I had a nice time with you, but I really hope I get to marry your dad! I love fucking him SO MUCH!”

The next candidate was Rebecca, a redhead with big boobs, a well-rounded butt, and long legs. She was almost my height, and with her high heels on she was taller than I was.

When I met her at the blue guest house, the first thing she said to me was, “I can’t wait to be your new mommy. I have two girls, but I always wanted a boy. Come give mommy a kiss.”

I was emotionally conflicted and a little confused. Her height reminded me a little of being with my real Mom when I was younger, but her great body and red hair reminded me of the first girl I saw naked, my shower assistant Kerry. I was nearly a grown man, but she was talking to me like I was four. For some reason I liked it.

Feeling her big boobs against me when we hugged was comforting, but sexy. Her lips on mine as we kissed reminded me of love and having somebody who cared about me, but her tongue licking my upper lip a bit as we finished the kiss started to turn me on.

“My daughters say I’m not very good, but I like video games. I got you some racing ones.” She handed me a small bag.

“I have that one already and it’s lots of fun. I heard about this one, do you want to try it in my room?”

“Sure. Let’s go.”

She held my hand as we walked and it was nice. I was conflicted about WHY it was nice. We sat on the sofa in my room playing games a long time. I gradually moved closer to her, and she moved closer to me. Soon we were happily leaning on each other. We played over three hours, but it only felt like a few minutes. I won more often than she did, but we both had a lot of fun. I liked her as a person and a friend. I totally forgot about sex.

Jerry brought us spaghetti for dinner and left. She bashfully blushed and asked, “Would you like to sit in mommy’s lap and let me feed you?”

To me it sounded like a nice idea but I’d be hugely embarrassed if anybody saw. I got up and closed the door as I said, “I think I’d like that.”

I sat across her lap with one of her big tits resting on my chest. Many thoughts about sex quickly returned.

I watched her patiently cut the spaghetti and pick it up with a spoon, then move it to my mouth. I looked into her pretty brown eyes as I took the spoon in my mouth and ate. She had the same loving smile I remembered on my mother’s face when she took care of me, far too long ago.

I ate another four or five spoonfuls before some spaghetti escaped my mouth and slid down my chin. Rebecca licked it off my face, then kissed me slowly. I licked her lips and she took my lower lip into her mouth, sucking on it. She pushed the food aside, and we French kissed for several minutes.

She started to unbutton my shirt saying, “Mommy loves you, baby. Would you like to make love to your new mommy?” I thought it sounded caring and wonderful, but strange and wrong.

I said the first thing that came to my mind, “Please, mommy? I love you.”

We kissed lovingly and kindly as we undressed each other. Before long, I was nude and laying atop her naked body, kissing her and squeezing her big breasts. I moved down a little and sucked her nipples.

“Yes, baby. Suck mommy. I wish I could give you milk, sweetie.” She played with my hair, as I joyfully tried to breastfeed. She reached down and squeezed my penis as I licked and sucked her nipple. I was already mostly erect, but got hard as a baseball bat as she stroked me slowly.

“Yeah! Put your nice dick in mommy! Make us feel great, baby!” She guided me into her vagina, and I slid in as far as I could go. I imagined climbing inside her, penis first. Her arms around me were reassuring and warm. I wanted my whole body to feel like that, comforted and protected inside my mommy.

“This feels so great, mommy! I love you!”

“Yes! Make love to mommy, baby! Mommy loves you so much!”

I kissed her neck as I started thrusting into her, lovingly and slowly at first, then building speed as we got closer and closer to cumming. She rocked her hips in time with me, moving her pussy upward as my cock descended into her. The hundreds of strokes made me more and more aroused and euphoric. I hugged her tightly, and I felt her arms wrap around me with more pressure, as we reached a simultaneous orgasm.

“AAAHHHH! YEAH! UH! UH! MOMMY!”

“YES BABY! AAAAUUUGGGHHHH!”

I felt like I was dying from a happiness overload. I laid atop her, struggling for oxygen, as she panted along with me. It was the best I’d ever felt! Even anal sex without a condom hadn’t made me as happy.

I rolled off her and felt something wet on my back. Spaghetti. We laughed together as I stood and removed the plate from the bed.

“Mommy will clean you up baby.” We had a shower together and I fingered her to another orgasm. She kissed me and jerked my rod until I squirted onto the shower floor.

As we were putting on bath robes, she said, “I’m sorry, sweetie, but mommy really needs a cigarette. Will you come outside with me?” Another smoker, I was a little disappointed. I opened the French doors and sat at the table on the balcony. She carried her purse and asked, “Can mommy sit in your lap, sweetie?”

“Please!”

I felt the weight of her on my legs and held my arms around her, supporting her breasts with my forearm.