Chapter 4: Stephano’s Stepsisters

The next woman, Louise, arrived only an hour after Rebecca and her girls left. She had long blonde hair and massive breasts, even larger than Rebecca’s!

I helped her carry her suitcases into the blue guest house, and she got straight to the point. “I think this is basically a sex contest? You can do anything you want. Have fun with my body.”

We stripped and she laid on her back on the bed. I played with her gigantic tits quite a while, licking, squeezing, and sucking them. I slid my penis into her slit and started kissing her. The sex felt good, but she seemed preoccupied, and not into it. I came, but could tell she wasn’t even close.

I said, “I liked that a lot, but what’s going on with you? Don’t you like me?”

She told me, “If I lose the contest, I get to stay with my boyfriend Andre. I really love him. I like your dad too and give him some fun, but I miss Andre. You can do what you want, if it doesn’t hurt. But please don’t pick me.”

After dinner I played with her boobs some more, and licked and sucked her pussy, but she wasn’t really into it. I tried quite awhile, but she was nowhere near climax. She said, “It’s ok. Have some fun. If you like anal, you can do my butt.”

I told her, “Thanks, but it wouldn’t be much fun if you don’t want to. I’ll tell dad you were okay, but didn’t win. You can go home in the morning, if you want.”

“Thank you.”

Never in my wildest dreams had I imagined turning down anal sex. But that night it felt wrong.

I met the next lady in the parlor. She was a pretty brunette with an average body. She led in a young girl who looked like a miniature version of herself. Both wore conservative dresses, the mother in yellow, and the girl in light green.

“Hello, I’m Stephano.”

“Valery, and my daughter is Jasmine. Can we talk with you a little before the ... uh ... contest?”

“Sure.”

I asked a butler, “Jerry, could you bring us tea and cookies?”

He rolled his eyes. “Of course, sir. And I’m still Jonathan.”

Valery timidly asked, “I’m a little nervous. Is it okay if I smoke?”

My mother would never be back, and dad wouldn’t be back for at least several weeks. I didn’t care much anymore. “Sure. Just use a cup for an ashtray.”

I saw thin lines at the corners of her mouth and eyes. She wasn’t amazing, but better looking than average for over 35. I thought her pink lipstick and makeup were nice.

“My daughter Jasmine only looks 14, but she’s really 17. There were problems with her development, but she’s healthy. Do you mind if she smokes too?”

“Sure.”

We had tea and a few cookies quietly. I was waiting for them to tell me whatever they wanted to discuss.

Valery said, “We know this is some kind of sex contest. The one you like screwing best gets to marry your dad, something like that?”

“Well, the one I like best, and sex is a big part of it.”

“I love Heinrich so much! I need to win! For the last 10 years, he’s the only man I’ve loved. I want to stay true to him. Once we’re married, I want to honestly say I haven’t had sex with anybody but my husband since we met. But I’m supposed to sleep in your bed unless he’s home?

And he said something about another rule, the daughters stay with you, so you can be sure they don’t sleep with other guys? Jasmine went through a lot of abuse when she was little.”

At the mention of ‘abuse’, Jasmine stuck her thumb in her mouth and looked worried. Seeing a cigarette in her hand and a thumb in her mouth was totally dystopian, my mind couldn’t quite figure it out.

I said, “That’s a tricky situation. If you want to give up and go home, I understand.”

She said, “I love your dad so much! I think there’s a way, if you’ll hear me out?”

“Okay.”

“I actually like anal sex. I’ll do it for you every night, if you don’t touch my vagina. My pussy is only for your father.

Like I was saying, Jasmine went through a lot of bad things, and panics if anybody goes near her pussy or butt. She learned to do great blowjobs, in order to save her from doing anything else. She smokes a lot because she needs something in her mouth all the time, either a cigarette, her thumb, or a penis.

She’ll suck you as much as you want, and you can have my ass every night. Do you think that’s enough for you?”

Anal every night, and all the blowjobs I wanted?

I heard an orchestra and choir in my head:

“Gloria, in excelsis Deo! Halleluiah! Halleluiah! Halleluiah!”

I had to struggle with my gigantic smile to form the words, “I think that would be fine. Lunch isn’t for two hours. Let’s go get you settled into the guest house.”

As we walked there, I saw the top of Jasmine’s head was even with my shoulder. She didn’t look sexy at all, more like a teen just starting puberty. I couldn’t wrap my head around the idea she was that small, but several months older than I was. Or more astounding, that she would blow me!

In the guest house living room I sat in the middle of the couch. Valery sat on my left, and Jasmine stood by her mother hesitating. She said, “It’s ok, Jasmine, he’s nice. He’ll be your new brother. Sit by him.”

Jasmine sat on my right, squeezing against the arm of the sofa, to be as far from me as possible. She sucked her thumb, and I imagined it was my penis.

“I love your dad, and I want to be a good mom for you, too. If you ever want to talk to me about something, if you ever need a hug, anything, you can come to me, and I’ll do my best to help.”

“Well ... uh ... mom. I’d really like a hug. A naked hug.”

“I can do that. Anything for my kids, other than sex. Kissing, playing with bodies, and anal aren’t sex. Whatever you want, if you leave my kitty for your father. I’m willing to do blowjobs sometimes, but she loves them.”

I smiled. “I think I love you two already, mom.”

Valery led us to the bedroom, and her and I slowly stripped. She laid on her back on the bed, and I cuddled up next to her.

“Your boobs are nice. Just the right size to fit my hands. Can I kiss ‘em?”

“Good mommies breastfeed their babies, so go ahead, son.”

I licked and sucked her nipple and before long, I saw Jasmine sucking the other one. Valery played with our hair as we sucked.

I felt and cuddled with Valery’s body a long time, as I sucked her tit and watched Jasmine do the same.

Valery told her, “If you want to suck your new brother, that’s fine. I think he’d like it.”

Jasmine moved over and started sucking on the head of my cock!

I came quickly the first time, and sprayed semen into her little mouth. The second time took a lot longer. After her second serving of cum, she kept the end of my penis in her mouth, just holding it there, while my new mother French kissed me.

After half an hour or so, we stopped so they could have cigarettes. Jasmine took off her clothes too, and I sat between them on the sofa nude. They leaned toward me, and I wrapped my arms over their shoulders, watching them suck on their cigarettes. When they finished, Valery talked to me about school and college. Jasmine was half my weight, but would be ready for college at the same time.

My new sister leaned over and took me in her mouth again. By supper time, they had smoked 8 cigarettes each, and my cock returned to Jasmine’s mouth after each one.

When we returned to the guest house after dinner, she wanted to suck me again.

I asked, “How about I kiss you? Would you like to suck on my lips?”

“Okay.”

She sat sideways in my lap and French kissed with me a long time, as her mother rested her arm on us.

Jasmine cuddled in my lap and Valery leaned on me as we watched a funny movie, then we went to bed. Valery laid on her back with a pillow under her hips, to make it easier for me to enter her anus, once I put lube on myself and her ass. She reminded me, “Be careful with your aim, make sure it goes in my butt.”

I climbed on top of her, and slowly entered her tight ass. She smiled and said, “Start slow, but I like it. It feels strangely good.”

I slid most of the way in and held it there, as I licked her lips. “So good, mom! Oooh! So good!”

Jasmine held my hand as I carefully started fucking our “mom’s” ass. I sped up gradually, looking into Valery’s eyes. I kissed her lips as I started to cum, feeling my cock pulse and squeeze a stream of sperm into her colon. “UH! UH! YEAH! MOMMY! SO GOOD, MOMMY!”

“Mmmm! I like that, Stephano. Thank you for being careful, so it didn’t hurt. Would you like to do it again?”

“I wish I could! That was GREAT! But I’m SO TIRED.”

“Okay. Let’s get a shower and clean up before we go to sleep.”

The three of us happily washed each other and played with each other’s bodies, until I touched Jasmine’s hip. She screamed and ran out. “EEEEH! NOOOO!”

Valery explained, “It’s memories of the abuse. She was hurt badly when she was young and won’t let anybody touch her between her knees and her navel. The doctor has to give her a sedative before they can check her. Please, please don’t touch her there again.”

“I’m really sorry. I would never hurt anybody.”

Valery got her calmed down, and when the three of us climbed in bed, Jasmine’s mouth was back on my cock immediately.

I paced myself the next day, and was able to do Valery’s wonderful ass twice that night. I had five more nights of excellent anal sex, and more blowjobs than I could handle.

In between our many sex sessions, we watched movies, rode bikes, and swam in the pool. I loved the two of them dearly.

But did I love them, or Rebecca and her girls more? How do you compare infinity to infinity?

The final contestant was Cathy, a pretty blonde with two boys 9 and 12 years old. She had a nice body and face. She was very flirty with me, and good in bed. I liked her, but she couldn’t compare to Valery or Rebecca.

I spent three days debating with myself and didn’t have any sex.

( SHOCK! HORROR! )

I thought Gina down the hall would probably be willing, but I didn’t even jerk off.

On the fourth morning, Gina woke me when she started to clean my room. I sleepily said, “Hi Gina. How’s it going?”

I climbed out of bed, and she said, “Uh, I can help you with that, if you want? Unless you just want to put it away?” She was pointing at my ‘morning wood’.