I followed my sister in law, Kristin, into her bedroom from the bathroom where she had recently showered, brushed her teeth, and combed her hair. Before ordering her into the bedroom, she had whispered to me, “Fuck me… please? I want you to slowly stretch out my tiny virgin pussy until I can take all of that huge cock.”.

I planned to, but maybe not in the way she expected. This was her first time, and although I had been in control all night, I thought that it might be best if she handled at least the beginning stages of what she had begged me to do.

The problem was our size difference. I was well over a foot taller than she was and over twice her weight. She was definitely under 5’ without an ounce of fat on her, now that I had seen her completely nude I guessed under 90lbs. I weighed about 210 and was 6’4”. I also had an 8” cock, which I was worried might damage her. Sex definitely wouldn’t be comfortable for her, especially because it was her first time. Despite her determination, I didn’t think she would be able to fully take it… or at least not without damaging herself.

She had surprised me with her willpower though… she had, after all, taken me completely down her throat twice tonight, which I had thought would be impossible. I was still astounded she had accomplished that, and the second time she had been almost even adept at it. She wasn’t doing it just to please me, either. She had orgasmed while accomplishing it the first time. Her admission to being addicted to my cum was what amazed me. I think extracting my cum was at the core of her determination to please me. I cared deeply for Kristin, and my wife knew this before giving my blessing to do everything we had done tonight. She clearly had acknowledged her sister’s need and loved her so much, she might have even arranged this, I thought.

Regardless, the next few hours would be interesting. I had avoided intercourse for as long as possible this evening to try and satiate her without it actually coming to this. I was actually nervous for her.

“Get into bed and under the sheets.” I commanded, pulling the comforter off and throwing it into a chair.

“Can I get some lotion first please, Master?”, She asked, and I nodded. She rushed to the closet and grabbed a tube of ointment from a shelf, which I didn’t think much of, but I thought I recognized it from earlier in the night. I sat down on the edge of the bed waiting, and she crawled in behind me and began massaging my shoulders with some of the gel-like lotion. It felt nice.

“I thought the lotion was for you?” I asked with a laugh. “It is for both of us!” She responded musically. I looked over my shoulder and noticed she was applying it to her breasts, kneading it in while playing a bit with her puffy nipples. She went back to massaging me, and after a bit I told her again, “get under the sheets.”

She did and I got in with her. Her bed was a queen size, and was very comfortable. I put my arm around her, pulled her to me, and kissed her, for the first time enjoying fully embracing her, feeling her small tits press against my chest. She tossed her skinny right leg over my abdomen, rubbing it slowly against my cock that was springing back to life, and began moaning and grinding her smooth hot pussy into my hip. I continued kissing her and felt light headed. She tasted amazing. She was tugging at my left shoulder and I finally realized she was trying to get me on top of her, but that wasn’t what I had in mind. Instead I put an arm under her and lifted slightly with my right arm as she groaned in disappointment until she was on top of me with her pussy on my stomach and her little tits were on either side of my face. God damn she was so light.

“Master, I thought you said you were going to fuck me?” She complained as I began sucking her right nipple aggressively causing her to gasp.

“I don’t recall saying that… actually.”, I paused moving to the left nipple sucking for a moment before continuing. “I plan on having YOU do the fucking, at first. But let’s take our time. I want you glide your tiny pussy along the shaft of my cock. You’re not permitted to put it in until I allow it.” I grabbed my hard cock and laid it flat pointing towards my stomach and guided her hips down until her tiny shaved pussy made contact with it for the first time. Holy fuck… she was so small, it looked absolutely massive up against her.

She shivered and let out a long groan as she gently slid herself down the length of my cock until she reached my balls. Her pussy was soaking wet and extremely warm. I pulled her hips back up along the full length and looked down as I pushed her back down hard, gliding her slowly back along my cock roughly until the head became exposed popping out of her cunt lips right at her clit. She inhaled sharply at this and let out a long, “fuuuuuuuuck!” As I guided her down the entire way until she reached my balls again.

“Sit up and continue.”, I commanded as I pushed her up and grabbed her tits roughly. She complied and began gliding along my shaft as she moaned constantly, inhaling with a hiss each time my cock head popped through the top of her slit. Her pussy made squishing sounds each time she reached my balls. Holy fuck she was wet. She increased her pace and moaned, “Please master… please! Please let me put it in? You’ve ALREADY made me cum so many times. Everything is so wet it should be able to go in!”, she paused with the tip of my cock right against her opening, waiting for me to respond.

“Ok… but we’re going back to doing this at the first hint of trouble.” Adding, “are you…? Is… umm… your hymen still intact?” I asked.

“Yes it is… I’m sorry Master.”, she replied, not making eye contact. I reached up and pulled her head close to mine, forced her to make eye contact, and replied, “I love that I’m your first… but I’m sorry that it will hurt.” I paused and then gave her permission. “You can try to put it in now. Get into a squating position with your feet on either side of my hips so you can control how much goes in. Go slow.”

She moaned and moved her feet under her as I instructed. I pushed my cock straight up in the air, and she lower a bit. As she did I flicked the head on her clit a few more times rubbing it back and forth. This caused her to gasp and jolt back up slightly away from me as I did it unexpectedly. Then I grabbed my cock at the base and steady it for her approach. She lowered until the tip was at her opening and started allowing it to push in.

It felt like trying to jam my cock into a closed fist with 85 pounds of weight slowly sinking onto it. She wasn’t just tight… her soaking wet cunt wasn’t even opening for me. She kept pushing down while grunting, and it felt like the shaft of my cock was trying to push down into my body. I thought it was going to hurt HER, but this was also definitely uncomfortable for ME.

“Slow down!” I hissed, suddenly grabbing her ass with both hands from under her thighs and taking some of her weight off of my cock to relieve some pressure. She shrieked, “I’m… sorry… master!” And made a whine of frustration. I allowed some slight weight back down and she made a frustrated moaning sound. “Ok just hold it there, and breathe… try to relax your muscles…” she was very tense and that wasn’t helping the situation. She began breathing in with her nose, and out with her mouth. Her eyes were closed and her brow was furrowed in concentration.

Suddenly, her eyes went wide in surprise as the head of my cock began slipping into her vice like opening. “Ooooooooohhhhh!”, She moaned as my cock stopped just at her hymen. The feeling was breathtaking and I grunted at the sensation. “Soooo much pressure!”, she moaned. She looked down, “it’s… not… even… in! Shit! I already feel it stretching me!”

“We can stop if you want.”, I grimaced through gritted teeth.

“Nooo!! I can do it! I just need time… to adjust!” Her breathing was labored, but thankfully she WAS breathing, which would make things easier since she was determined to proceed.

“Your hymen is going to break, it is going to hurt. You’re in charge though… take your time.” She was already bearing down as I finished speaking. It was tighter than anything I’d ever experienced, even anal with my wife, Kristin’s sister, Kellie.

Kristin began moving slightly up and down, squeezing the tip of my cock again the opening of her extremely tight and wet cunt. Each time she let gravity take it’s effect and my cock pressed against her hymen a bit harder. It was like fucking just a half inch of my cock in repeatedly, and unfortunately it was the most sensitive inch. I wasn’t exactly close to cumming, but there was an excruciating mix of pleasure and discomfort. “Uhn. Uhn. Uhn! UHN! UNH! UHHHNNN!!” Suddenly she pressed down hard in an attempt to get it further in. The attempt failed. She whined loudly and then grunted in frustration each time she pounded down, “Fuuuuuck!! Go! In! Go! In!” She hammered herself down. I could feel her pussy stretching in response. She kept at it. “Fuck! Fuck! Fuck!! FUCK ME! FUCK ME!!!!” With an audible squishing sound her hymen tore away and like a slow motion scene from a movie, my cock sank 3-4 inches in. “AAAAGGGHHH!!!”, she screamed as it did, her entire face contorted as she was racked with pain. I pulled her to me and kept her as still as possible. She made blowing sounds as she exhaled repeatedly keeping her breathing steady against the pain. Finally she whispered against my ear, “So much pain… But I… did it! I feel more full than I ever could have imagined.” The reality was I wasn’t even half way in. I hoped that would be good enough for her. The tightness was indescribable now that I was in. I did my very best to not let my cock twitch or flex, it took a lot of concentration.

After a few minutes of staying still, she began moving her hips. Slightly at first, followed by a slight undulating, testing the experience for the first time. “Oh my god… it feeels gooood…”, she moaned. “Really good…” she began tentatively allowing about 2 or so inches to slide in and out. She tested pushing in a bit more which was breathtaking. Eventually I felt the tip of my cock hitting her cervix and realized we were at her limit. I guessed about 3 inches of my cock were left.

She had done an amazing job taking it. She began grinding onto me at a steady pace while I hugged her close to me. She was actually fucking me now and it felt really good. She was wet as fuck but still as tight as a vice. After several minutes of this, she began going an deeper, sliding about 3-4 inches of the shaft of my cock in and out, tentatively grinding the tip against her cervix every 6-7 seconds. Her breathing was getting shallow and she began whimpering.

Suddenly she pushed herself up, placing both hands on my shoulders, hunching her back and pushing her head down, trying to get the best view of the exact spot where we were joined. Her long hair covered my face and it smelled wonderful. She gasped and then snapped her head up with a shocked look. “It’s not even CLOSE to all of the way in!”, she complained. “I’m too small! No more will fit!”

“It doesn’t need to!” I practically shouted. “It feels amazing… just keep going. NOW.”

She stopped complaining, threw her head back, arched her back and continued. She kept at it in long strokes, squeaking a bit each time she bottomed out. I placed my hands on her chest completely covering both tiny tits and let her nipples pass through the area between my thumbs and my hand, squeezing slightly and applying a little pressure. She dropped her back down and I noticed her brow was furrowed in what looked like concentration.

“Soooo close…” she gasped. “Me too…” I replied through clinched teeth.

Her mouth was slightly open so I took two fingers on my left hand and pushed them into her mouth which she immediately began sucking. She began making high pitched yipping sounds around my fingers while fucking me faster and faster. I pressed my right hand at the back of her head for leverage and began pushing the two fingers of my left hand down her throat. She made moaning and gagging sounds and I suddenly felt a stream of fluid leaking out of her as she rose almost completely off of me before sliding back down to start grinding again.

She was still so tight it was almost painful. Her tight little cunt felt like a vice that was trying to milk all of the cum out of my cock. It was proving to be very effective. I felt my balls tingling and knew I was close. “Fuuuuuck…” I groaned. “I’m going to cum.”

She turned her head to the side to get my fingers out of her throat. Saliva and drool dripped down her chin onto her chest and I spread my wet fingers all over her left nipple. “Spray all of your cum inside me!! I want it all!!!” She shrieked as she bottomed out and stayed there, shivering as all of the muscles in her body tensed suddenly. I began grunting and spurting pulse after pulse of hot cum directly into her. As I did, she let out a long, low groan as she began spasming and finally collapsed on me. “I can… feel… it… So hot and wet. I’ll need to taste it… once I can move…” she finished.

It took her a while to catch her breath. It took ME a while to catch mine, too. Finally she looked up at me and gave me a long, passionate kiss that seemed to last forever. She then lifted herself up and off my cock and straddled herself close to my navel and stayed there for a while as my cum poured out of her with her small tits directly over my face which I began sucking eagerly.

She carefully rose herself up further and moved her head down to the puddle of cum on my stomach and began slurping up and swallowing every bit she should find, making whining and mewling sounds while she did. I was completely covered in both of our juices and she spent the next several minutes lapping up everything until she was completely satisfied. “We taste amazing…” she announced as she finished and laid down on her back in the crook of my arm and closed her eyes with a content smile.

After a minute or so she asked, “Is there any way… you could…”, and then stopped.

“Could what?” I asked, confused.

“I’m sure there is still some inside me… could you finger me and feed me any that might still be in there?” She finally asked.

My exhausted cock twitched. Jesus. “Yes.” I replied. “You’re not too tender?”

“I am, but it doesn’t matter. Feed me please, master.” She said as she lifted her knees up next to her little tits. I got up on my knees and spent the next 5 minutes or so alternating between dipping my middle finger into her tight pussy and allowing her to lick it clean. She stayed wet the entire time, and by the end I had no idea how much of what I was feeding her was my cum or her own juices. She finally let her knees down and seemed like she was fully relaxed for the first time since I had arrived. She was falling asleep.

“Promise you’ll make me take it all when we wake up?” She said drowsily.

“I will.” I replied.

I looked at the clock and it was 4am. I laid down next to her and pulled the covers over us and drifted to sleep after pulling her close to me.

To be continued in chapter 6?