Annie, Jenny, and Me
Copyright© 2022 by Master Jonathan
Chapter 2
Romantic Sex Story: Chapter 2 - This story is about a guy new to the apartment building who befriends and ends up having sex with a divorced woman across the hall. When her daughter comes to town, she introduces him and he has sex with her as well. Although there are three characters in this story, two of whom are mother and daughter, there is NO incest – he has sex with each one individually. So all those who dislike the idea of incest can read this story without worry.
Caution: This Romantic Sex Story contains strong sexual content, including Mult Consensual Heterosexual Fiction Sharing Anal Sex Analingus Masturbation Oral Sex
“Jenny! What the hell?” I said quickly covering my eyes. She stood up quick and whirled around. covering herself as best she could with her hands.
I heard her coming closer. “James, I’m sorry. I probably should have warned you – I like to sunbathe in the nude. I hate tan lines. Back in Denver, we have tanning beds that you can do that in but I don’t know about here in Houston. I’ll go put my robe on.”
“That would probably be a good idea,” I said. When I thought it was safe enough, I uncovered my eyes. But I did get a good glance at Jenny’s ass as she walked to get her robe.
Once Jenny had gotten dressed again enough for my comfort if not hers, I took her over to the sofa and gave her the soda. “Jenny hon, I think we need to talk. You know that your mom and I are kinda seeing each other right? Well, I don’t know how she would feel about your flirting with me and I don’t want to do anything to spoil what she and I have.”
“Oh, it’s okay, James. Yes, I know that you and my mom are having sex. That’s cool. But you see, I don’t know anyone out here ... all my friends are back in Denver. And, well, I get horny. I am a teen-aged girl you know. And I am over sixteen, so I’m legal if you are worried about that. I’m also on the pill and have been for a few years now. All I want is to have a little fun. Don’t you like me, James?” she said.
“Sure, I like you Jenny, but...”
Then I saw Jenny stand up and open her robe, letting it slip down her arms until it gathered at her wrists. My God, did she have a killer body!
Before my mind could formulate a thought, she straddled my legs and sat down on my lap facing me. She took my face in her hands and kissed me ... hard and passionately. Like she meant it. Her mother sure taught her well because as much as my common sense, wisdom, and experience told me this was wrong and I was going to get caught, my body was telling my mind to shut up and enjoy it!
My hands found their way on their own to her slim waist and wrapped around her, holding her. Her 34C tits, large for her age and size, pressed against my chest and I could feel the diamond-hard points trying to poke into my chest.
Our kissing continued getting more passionate, more urgent. I could feel my cock growing and straining wanting to get out and get into the action too. And I could tell Jenny felt it rubbing against her naked, and to my surprise shaved, pussy because she began to moan and grind against me, further arousing us both.
Just as I felt myself giving in and losing what little control remaining, better judgment stepped in and just in time. “Jenny wait!” I said. I pushed her off my lap and stood up. “Jenny I like you and Lord knows you are hot enough to melt my zipper, but I can’t do this.
“Your mom means a lot to me and while a romp in the sack with you would be loads of fun I’m sure, you are going to be gone in a few months, and I will still be here. And living across from your mother with her angry that I fucked her daughter would be unbearable.
“Now I know it’s hard to go without sex – believe me I know. But it’s only for a short time and then you will go back to Denver and back to your friends. But your Mom and I ... well all we really have is each other and if we have a falling out over a summer fling, it would crush us both.”
Jenny didn’t say anything. She just quietly turned and got her bathing suit and towel and left my apartment without even looking back. I knew I had probably hurt her even though I didn’t mean to, but I also knew that I did what’s best for everyone.
If we had been caught, especially with her naked on my lap, Annie would have been beyond furious with me. We probably would never speak to each other. And if Jenny and I had developed something between us, it would hurt her to have to leave again. It was just better all around this way.
Things quieted down again for a while. Annie and I continued our relationship, but I didn’t see much of Jenny. When I did pass her in the hallway it was a polite but short “hi” and even that was few and far between. I knew that I had upset her but what could I do?
Her cold aloofness would come to an end in a most surprising and shocking way. I had just come home from work and saw that Annie’s apartment door was open. Annie was inside making dinner for her and Jenny and I waved to her. She smiled and waved back and then I went into my apartment.
I wanted to take a shower and relax after work and before thinking about my own dinner. I had just stepped in the shower when I thought I heard the bathroom door open. It must be something else, I’m all alone in here I thought and dismissed it. That is until I heard the shower door open!
Standing there once again in all her glory was Jenny. But this time she wasn’t going to take no for an answer! Before I could object, she got in the shower with me and pulled me down into a protest snuffing kiss. Her hand went straight for my cock and it didn’t take long at all before she had me hard as a railroad spike!
“Mmm, that’s the James Mom told me about! Now don’t you worry, Mom is fine with this – we have shared boyfriend’s before, both hers and mine. So this isn’t going to get you in trouble or cause you and Mom to break up. Hell, she’s glad that I find you attractive – it keeps me from bringing home something off the streets!
“And she knows that this is only a summer fling. I’m going to be leaving in a couple of months to go back and finish my senior year at high school in Denver. But I’ll be back. Like Mom, I don’t like the weather in Denver ... I’m a sunshine girl. What happens when I come back is anyone’s guess. I just want to have a little fun while I’m here. You ‘up’ for it there, big guy?” she asked.
I answered her question by squatting down and bit and putting her arms around my neck. My hands moved down to support her under her ass. I stood up, lifting her with me and she wrapped her legs around my waist.
She settled at the perfect height for me to return her passionate kisses as my cock tickled her pussy from beneath. Between her wriggling in my arms and my own moving around, my cock did a pretty good job of teasing that tight little snatch and she moaned urgently into my mouth.
“Oh James!” she gasped “Please fuck me! Please show me what Mom has been raving about to me!”
I looked into her soft hazel eyes. “Can I assume that you aren’t a virgin anymore, Jenny?” I asked, “Because if so I will have to take it slow with you.”
Jenny giggled, “No, I’m afraid that ship left port and is out of sight by now! I’ve actually been with four boys – a couple of seniors, a boy my age, and one college guy,” she said.
“Well, I will still go slow with you ... I doubt very seriously you have had anyone my size before and I don’t want to hurt you.”
I lowered her down a little until my cock began parting her pussy lips. Then I lowered her another inch until my cock had nestled and sealed her entrance. I hadn’t started spreading her quite yet, but I was about to.
“Okay, Jenny are you ready?” I asked her. She looked at me biting her lower lip and nodded.
I lowered her further, slowly, inch by inch and watched her expression change from nervous anticipation to surprise then to shock as she realized that she wasn’t with one of her schoolmates this time. She wasn’t with some college guy. She was being fucked by a man – and all bragging and boasting aside, I was appreciably bigger than average on top of that.
Her eyes were wide and her mouth dropped open to form a perfect “O” shape as she became aware of what was happening to her.
“Oh my God, James! Oh, fuck! You are splitting me wide open! Oh God, I don’t ... I don’t know if I can take it!” she said.
“Just relax, Jenny. I will take it slow with you. Remember babies come out of there and I’m nowhere near the size of a baby’s head. But if it gets to be too much, you just tell me and I will stop right away okay?” I told her. Jenny nodded that she understood then she planted her face in my shoulder and I continued lowering her onto my hard thick cock.
“Oh God, Oh God, Oh God,” she chanted as she felt me burrow deeper and deeper in her tight pussy. Jenny was indeed tight – probably the tightest pussy I have had in a very long time. But I also knew she’d had others in there so I wasn’t breaking new ground ... just yet.
But soon I was. “Oh, God James! Oh, Fuck! Oh, no one ... no one has ever been this deep before! Oh how much ... more is there?”
“Jenny honey there is still a couple more inches left to go if I don’t bottom out in you first,” I said.
“Ohhh Gaaawd!” she moaned, burying her head in my shoulder again.
I lowered Jenny the last couple of inches until I felt her ass against my cock. I knew I was as far in her as I could get now and I was a bit surprised that I got my entire length in her, considering her tender age and my large size. But I was glad that I was able to fit my full length in her because it meant I wouldn’t have to worry about going too deep and hurting her.
“Oh, James! Oh, I’ve never felt anything so amazing! Your cock ... so deep inside me. Oh, it’s wonderful! Now I know what Mom meant when she told me about you!” she said.
“Did she also tell you that the first time I fucked her, she could barely walk afterward ... I had her spend the night with me so I could look after her!” I said.
“Ohhh...” she moaned.
“Of course I won’t be able to fuck you like that, your Mom is older than you and I know she can take it. Don’t tell her I said this, but she really likes it rough and so do I! Your Mom has a slutty side that I really love!”
“I am a slut too, James! I like it rough just like Mom! Please, please fuck me like that! Oh, please – I have only had the boys at school until now! Please, I want to feel a man’s cock! I want to feel your cock! Pound away at my tight pussy, James, I promise I will love it! Please!” she cried.
“I don’t know Jenny. I mean I can get pretty wild. Your Mom has had a number of men and she had trouble walking after I finished. Of course, it had been a while since she last got a good fucking, but...”
“James, I will do whatever you want, any way you want it. I want to show you that I can take the rough stuff too. I want to show you that I’m not some little girl or some china doll that will break if handled too rough. I can take anything you give me and I would love being a slut for you. Just give me a chance to prove it!” she said.
I looked into this young woman’s eyes and I saw she was serious. She really wanted to prove herself to me and she wanted me to show her what it was like to be fucked by a man. I had to feel for her – I remembered the days when I was just a pup trying to make a name for myself as well.
“I’ll tell you what, Jenny. I will think about it. I know what you are telling me and what you want to prove to me. And truthfully, I hope you can. If, as you say, it’s okay with your mother, then I would love to have both mother and daughter as my playthings!
“But let me think about it for a couple of days. Besides, when I came home your Mom was cooking dinner for you two – she’s probably wondering where you got off to right now. At least we found out that you can take me all the way in and I won’t have to worry about fucking you too deep and hurting you.” I said.
I could tell Jenny was disappointed that we didn’t have sex right there in the shower and I was thinking twice about my decision too after she got dressed and left. But I knew I had done the right thing. I didn’t flat turn her down so she still had hopes, but I wanted some time to think with my big head on this one!
The next day as soon as I got to work I called Annie up and her office. “Hi Annie, it’s James. Hey, would you like to go to lunch with me today? I have something I need to talk to you about and it’s pretty important,” I said.
“Sure, I go to lunch at 1:00 after some of the other girls get back from their lunches. That way the phones are always manned. Is that okay with you?”
“That will be fine.” So that afternoon I met with Annie at a small diner that was about halfway between our work offices.
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