Dinner was pleasant. My wife and I were out at a nice Italian restaurant with my wife’s brother and our sister-in-law. The food was fantastic, the wine was delicious and the conversation was flowing; all of us sharing stories and laughing.
Well, most of us, anyway. Our sister-in-law, Jenny, isn’t quite as outgoing as the rest of the family. She has the occasional anecdote to share, but mainly her life revolved her children. She didn’t seem to have many of her own friends and she was a stay at home mom, so she only had so many stories to share. She realized that the average person, even relatives, could only listen to so many stories about her children, so she mainly remained quiet and listened to everyone else.
The conversation did turn back to Jenny’s preferred topic as the evening rolled on when my wife asked about their plans for a third child. It was no secret that Jenny desperately wanted to have at least one more child, while Jason wasn’t as keen on the idea. In his opinion, they had two beautiful children and they weren’t getting any younger, so why not just be happy with the family they had?
As the conversation continued, Jason decided to share a story with us that illustrated how badly Jenny wanted a third child. He began:
“Seriously you guys, she wants another kid so badly that she practically raped me!”
“Jason!” Jenny exclaimed, trying to keep her voice down, but obviously shocked at the story he was about to tell.
My wife and I had the same reaction, yelling, “WHAT?!”
“Yeah,” Jason continued, obviously not caring about Jenny’s objection, “I got home one night after work and was exhausted. I ate dinner, played with the kids for awhile, but I just couldn’t stay awake any longer so went to bed around 9:30.”
My wife and I were leaned in, listening quite intently. Jenny knew there was no way to stop Jason once he was in the middle of the story, so she just sat there blushing as he continued.
“All of a sudden in the middle of the night, I feel something moving on top of me. I opened my eyes, and there’s Jenny on top of me!”
“Like, trying to get you to wake up to have sex?” my wife asked.
“No!” Jason says, “We were having sex! She somehow got me hard while I was still asleep and she was having sex with me. That’s how badly she wants to have another kid! She doesn’t even care if I’m an active participant! She just wants my stuff!”
“So she was “milking” you!” I blurted out.
We were all roaring with laughter. Well, all of us except Jenny who just sort of chuckled, trying not to be a stick in the mud. You could tell she was pretty embarrassed, but I had to give her credit; she took the story like a champ. I know a lot of people who would have stormed out at that point or at least fumed for the rest of the meal. Not Jenny. She sat there and enjoyed the rest of the evening with us.
We changed subjects, had desert and after everyone had their fill, we paid our tab and left. On the way home my wife and I talked about the “milking” story. We just couldn’t believe Jenny would do such a thing; it was so out of character for the woman we knew. We laughed about it a bit more and the two of us occasionally took to calling Jenny “the Milker” in our private conversations.
But as with most things, time passed and the reference began to fade.
A few months later, Jason and I went out drinking with some friends. With the two little ones at home, Jason doesn’t get to go out with the guys very often, so when he does get the chance he likes to make the most of it. I’m not one to reign anyone in and I enjoy my nights away, as well, so our nights out often end in fun, a few foggy memories and a pounding headache the next morning.
This particular night was no exception. Beers were followed by shots, which were then followed by many more beers. At the end of the night, neither of us was in any shape to drive home, and since we were closer to Jason’s house we shared a cab back to his place where I was going to crash until the morning.
Jason set me up in their guest room and stumbled off to bed for the night. I passed out pretty much as soon as my head hit the pillow.
At some point in the night, I began to have a dream about sex. This is nothing new and it actually happens quite often when I have a lot to drink. You’re out in a bar, lots of pretty girls are around and the images stick with you through the night.
The dream was extremely vivid. I couldn’t see what the girl looked like, but the sex itself seemed so real. I could seem to actually feel my hard cock sliding in and out of a wet hole. I wished the dream was real, but knowing that it was just a dream I tried to keep my eyes closed and hope the dream would last. Since I was gaining consciousness I knew it would end any minute now and I would be disappointed to find myself in a bed by myself, but I tried to hold on to the dream as long as I could.
To my surprise, the dream wasn’t ending. In fact, it seemed to be getting more and more vivid. I could still feel my cock engulfed in a tight hole. I could hear the girl in my dream moaning as if she were right there. Maybe I had remembered the night’s events incorrectly? Did I somehow get home that night? Was I possibly in my own bed? Even possibly having sex with my wife?
I was afraid to risk waking up and ending the dream. On the other hand, I would have to miss out on actively having sex if this happened to be real. I decided to chance it and wake myself up.
I opened my eyes slowly, not sure if I was going to see my wife on top of me or an empty room. I shocked when I saw neither.
Directly in front of me was a pair of unknown, but quite large, milky-white breasts. I looked down the silky smooth stomach and watched as the woman’s hips straddled my own and moved rhythmically back and forth over my pelvis; my penis buried deep in the woman’s womb. I looked back up the body. Her arms were extended with her hands in the middle of my chest for support. Her back was arched slightly, breasts protruding forward and her neck was tilted backward with her eyes closed; enjoying the ride. My sister-in-law, Jenny, was fucking me as I slept. To use the expression we had developed, she was “milking” me.
At this point I was left questioning what to do. On the one hand, I was at that moment cheating on my wife. Plus, I really liked my brother-in-law and, even though I had no idea what had been happening up until this point, this was still his wife that I was having sex with. On the other hand, neither my wife nor Jason would probably care – or possibly even believe – how I came to have my dick buried deep inside of Jenny. And being inside of her felt so good and her tits looked so wonderful bouncing on the chest above me. Do I just close my eyes and enjoy this, let Jenny leave when it’s finished and act like nothing happened?
I didn’t have time to make a decision. As I was debating this in my head, I saw Jenny open her eyes and look at me. She could tell I was about to say something and simply whispered, “Shush, shuuush.”
Jenny leaned forward until her face was a few inches from mine. I could feel her dangling breasts rubbing against my chest. She began to talk quietly as she continued humping her hips on my shaft.
“Just relax,” she tried to reassure me, “just relax. No one will ever find out about this. Just enjoy it.”
“Jenny, what about Jason? What about the kids? What if someone wakes up and comes in here?”
“Wakes up?” she replied, “Oh, you still think it’s the middle of the night. It’s actually 9 in the morning. Jason got called into work and will be gone all day. Saturdays the kids spend with their grandfather so they’ll be gone all day, too.”
She kept sliding slowly up and down my shaft. She was obviously enjoying this immensely. I was too, it felt great! But it was wrong, too.
“Jenny, we shouldn’t be doing this,” I began to protest, but she cut me off.
“Relax,” she said again, “I just want your cum and then we can be done with this if you’d like. Mmmm, if feels so good though. Doesn’t it?”
She just wanted my cum? What? I knew she wanted another child, but this was crazy! How would she explain it if I knocked her up?
I tried to explain that point of view.
“Jenny, I know you want a third kid, but …”
Again, she cut me off. “I’m not trying to get pregnant. I’m not stupid!” she said. “You can only get pregnant at certain times of the month and this isn’t one of them for me. I couldn’t get pregnant if I wanted to right now. Like I said, I just want your cum.”
“What?” was the only reply I could come up with; not exactly witty or anything, I know!
“Jason wasn’t lying about the story when he woke up with me having sex with him, but he was wrong about the reason,” she explained. “I’d love to have another child, but getting pregnant wasn’t my plan that night. And it wasn’t my motivation the other nights I’ve screwed him while he slept and never woke up to notice.”
She had me puzzled.
She continued, “I just love cum. Sperm. Jizz. Whatever you want to call it. I just love it. I need it. I always have. I love to feel it fill my insides. I love to feel it coat my tongue as a guy cums in my mouth. I love to feel it shot all over my body.”
“So Jason won’t give it to you?”
“He will, and does. But he has to work so much that he’s exhausted when he gets home and is asleep by the time we could have some “alone time” from the kids. And when I get a craving for some cum, I NEED to have it. I planned on getting some, lots in fact, today, but then he was called in to work. And then I remembered you were here and I couldn’t help myself.”
Holy crap that was hot! Jenny, timid, shy Jenny, just confessed her cum addiction to me. She was still riding my cock. She was taking it in longer strokes now. She would pull her hips up until just the head of my cock was left inside of her and then she would slide slowly down until my balls were pressed against her ass.
“So?” she asked. “Can I have your cum? Can I feel it shoot inside of me? We can stop after that, if you’d like, but I would love to feel your cum all over me today. You can shoot it wherever you want.”
I knew this was wrong. I knew we should stop. But I hadn’t stopped it when I first knew what was happening, so I was already cheating with my sister-in-law. We had been screwing for awhile now and I was getting fairly close to cumming anyway, so I might as well finish I thought.
I had been a passive participant the whole time up until the moment. I had kept my arms at my side letting Jenny do all the work. Now I was going to join in. I reach around and grabbed her ass and squeezed, pulling her down onto my member until I bottomed out in her.
I looked her in the eyes and asked, “Wherever I want?”
Her eyes twinkled as I asked that question. Jenny knew she had me. She knew she was going to get what she wanted so badly – cum! And she knew she was going to get more than one load from me.
She smiled and replied in a sultry voice, “Wherever you want. In my pussy; on my face; in my mouth; you can even explode all over my big tits and I’ll lick it off of them for you.”
Fuck, so hot! Whoever knew Jenny would be such a cum slut!
There was one place I most definitely wanted to plant my seed though, and she had not mentioned it.
“What about deep in your ass?” I asked as I slipped a finger between her crack and rubbed her ass hole.
“Oh fuck. No, not there. I’ve only done anal once and I didn’t like it.”
I knew she was desperate though and would give in. “Well, you said ‘wherever’ and that’s where I want to cum. Either you let me cum in your ass or we will stop right now before you get any cum. You will have to go all day without fulfilling your craving. And who knows whether Jason will be too tired when he gets home from working all day after being up late last night …”
Now I had her! “OK, you can cum in my ass. But later. I want to feel it in my pussy first. Then I want to feel it shoot either on my face or tits. Then you can have my ass. Deal?”
Jenny then picked up the pace. She started moving up and down my cock faster, determined to now get the first of what was going to be many loads today.
I reached up and for the first time felt the weight of her large breasts in my hands. I squeezed them, fondled them, and then brought them to my mouth.
I ran circles around her nipples with my tongue and then bit her nipple. I then sucked her breasts into my mouth, trying to suck in as much as I could.
“Oh fuck, yes!” Jenny moaned, “Suck my nipples. Bite them, pull on them, lick them, suck them! Yes! I love it.”
I went back and forth sucking one breast before moving to manipulate the other one. Jenny kept fucking me. We had fucked so long that I couldn’t believe she hadn’t gone dry, but the anticipation of the cum that was about to fill her kept her soaked.
I was finally about to cum and so was Jenny. She took her breast from my mouth and sat back into the position she was in when I woke up. She put her hands back on my chest for balance and I grabbed her hips, helping pull her on my cock faster. She was bouncing up and down on my cock and I watched her supple breasts bounce with the same rhythm.
Finally, I reached the point of no return. “Jenny, I’m going to cum. Fuck, fuck, fuck, I’m about to cum. You want to feel me cum inside of you?”
“Oh yes, fucking give it to me! I want to feel it shoot inside of me! Give it to me now!”
And I did! I thrust up as she pushed down on my cock and I shot deep inside of her, filling her with every ounce of warm cum I had.
As I finished shooting and the last drops oozed out, Jenny just sat there, as if she were waiting for something. Eventually, after a minute or two, I could feel my own cum run back down onto the head of my cock.
“There it is,” she said. I wasn’t sure if she was talking to herself, me, or both of us. She raised off of my lap, my shrinking cock popping out of her pussy, and she hovered for a minute. She looked down with intent and we both watched as my sperm slid out of her pussy and dripped onto my cock. I could see her trying to push more out and covered my cock with my own cum.
“Oh I love feeling it slide out of me. That feels so good!”
“Are you ready to start building up your second load?” she asked me.
“Sure,” I replied simply. Jenny then lowered her head into my crotch and swallowed my cum covered cock. I could feel her sucking up as much cum as possible into one mouthful, and then she looked up at me, took her closed mouth off my cock and then opened it to show my load on her tongue. She closed her mouth and swallowed.
“Yum that’s good!” Jenny exclaimed and then went back to sucking my cock, still with a bit of cum on it, to get me hard and ready for round two.