I always found my sister-in-law, Cara, kind of attractive, even as my girlfriend and I were dating at the time. She was already married when I started dating, but I was already mesmerized by her beauty. At my wedding, Cara wore a beautiful strapless turquoise dress that rivals my wife’s white wedding dress. I would have been fine if they had switch places that night.
However, my wife never truly got along with her sister. Cara was…careful with their money with her own family, but freely spend it with friends and her husband’s family. She would also spend time with her friends weekly, but only went to her parent’s house once or twice a month for dinner. My wife has always taken care of her parents better than Cara did. The animosity between them was obvious though, and if they weren’t siblings, they would’ve never spoken to each other. Lucky for me though, they were.
After four years of marriage, my wife is now pregnant with our first baby. It’s not that we tried for four years; we just put it off for 3.5 years so we were more financially stable. I was 29 when she got pregnant, and now that I’m 30, our bank accounts gave us the confidence to finally allow us to have children. My sister-in-law, Cara, turns 36 this year, a mom to a beautiful teenage daughter and a 10 years old autistic son. She looks like she’s in her late twenties/early thirties though; she was almost as tall as me at 5’6” and weight…probably 115 lbs or so. I would’ve like to see what she would look like with longer hair, but she always kept it on the shorter side, her hair falling about an inch below her chin.
Our family was all Chinese, so that meant I wasn’t big, standing at 5’8”, at 130 lbs. But my good uncircumcised 6 inches kept my wife happy. Like I said, my wife is currently pregnant, and while we still had sex once a week or so, her growing stomach made it hard for love-making. My horny penis meant jerking off a couple times a week, just to relieve some tension.
One summer Sunday, my parents-in-law visited me and my wife after attending church. Along with them were my sister-in-law and her two children. They were visiting the almost-completed baby’s room and see how their daughter was doing. Sitting around eating snacks, my pregnant wife crave for some ice-cream. This made Cara’s two kids hungry for ice-cream too. Since we didn’t have any at home, I offer to take them all out to a local ice-cream store.
Once we got to the garage, I found out my father-in-law had park his car right in the middle of our two-car driveway, essentially blocking both of my cars. My wife asks her mom for keys to the car so I could move it, when my father-in-law offered to drive instead. I was fine with that as there was a baseball game on TV that I wanted to watch. Realizing the six of them couldn’t fit into my in-law’s Prius, my mother-in-law offered to stay behind. Instead, Cara said she’ll stay, I assume so she wouldn’t have to pay for her kid’s ice-cream. So they left, leaving me and Cara alone.
I sat in the middle of my sofa, shorts and a t-shirt partially watching the game on TV. My attention was split between the game and Cara. Sitting at the long end of my L-shape sofa, she was wearing knee-length blue jeans and a Bebe blue-green shirt. She had worn that shirt before, and I love how those colors mix together, the Bebe words that glitter on her chest.
She was playing around on her iPod Touch, as I look at her body out of the corner of my eye ever few seconds. Her smooth legs, her two breasts pushing at the front of her shirt. I would watch the baseball game, but occasionally glance over at her, admiring how beautiful she looked in that shirt as she sat on the sofa, her long legs on the sofa…She must’ve saw me sneaking peeks at her, and saw my obvious erection in the thin fabric.
“You like watching men?” She asks out of the blue.
“What?” I turn to look at her weird question.
“You…” her eyes fell to my erection, her head nod in that direction too, “like men in uniform?”
Looking down and seeing my erection making a tent-pole in my shorts, I shift my torso so it wasn’t as obvious. An embarrassing shiver fell across my body, my face turning red. I couldn’t tell her that my hard-on was from her, my brain tries to find a reasonable excuse for her.
“No…I uh….it’s just hot out.” Was the best I could come up with.
“It’s okay, you can tell me.” She says as she moves right next to me, her arm around my shoulder.
I could feel more blood rushing to my penis, stiffening it further. My earlier attempt to hide my erection succeeded for only few seconds, but now, it was poking up right at my shorts. Since Cara was at my right, I turn to my left to grab a pillow to cover it.
My hand was on the pillow, I was just about to grab and pull it when I felt something grab my penis tightly. My head immediately turn to my crotch, as her right hand had grabbed my erection in my shorts tightly. I look at Cara with embarrassment; my body frozen at what to do next.
“It’s okay,” her grip was tight on my cock, “tell me what’s making you horny.” She whispers in a sultry voice.
I let out a groan as she slowly moves her hand up and down just a little bit. “You look…so good in that shirt. Your big breasts…” I admitted as my heart beats faster.
Her left hand takes my hand and puts it on her chest. I was speechless as my hand was feeling, squeezing my sister-in-law’s breast. I angle my body slightly towards hers as my other hand went to her chest too, fondling her boobs.
She closes her eyes and lets out a small moan as my thumbs rubs against her nipples through her shirt and bra. Her hand was now jerking, squeezing more and more as I couldn’t believe my hands were finally feeling her big breasts after all these years.
Her free hand slips under my shirt, her bare hand on my back brought nervous sensations, like the first time I felt her sister up. Her hands slide to my waist band of my shorts, tugging at the sides. A devilish smile from her was all I needed as I shift my butt out to the edge of the sofa. Both of her hands grabs at the sides of my shorts and pushes it down to my knees and to the floor, my underwear going along with it. My erect penis stood straight out, and I could see a little pre-cum and dribble out.
She places her hand back on my penis, and I thought I would cum right then. Her warm hand slowly massages my cock as she repositions her body so that her head was on my thigh. I let her move, and once her head was on my thigh, I nervously pull her shirt up. She didn’t protest as the shirt rose, exposing her white bra. I kept raising her shirt, and then took it off her body.
Once she was lying there in her jeans and bra, all nerves went wayside and I knew I had to have her. For eight years I had wanted to see my sister-in-law naked, and now that she was letting me, I wanted to pound her pussy. I unclasp her bra and take it off. Her shirt had hid her chest marvelously. She was an easy C, maybe even a small D as her nipples were erect from me fondling them. I felt the urge to suck on them, as I feel her hands pushing my shirt up. I quickly grab my shirt and took it off, as I’m now completely naked in front of my sister-in-law.
I wanted to get her pants off, as her hand jerk me faster and faster, her face inches from my cock. I wanted to push her head, but decided to get her pants off first. My hand went to her jeans, undoing the button and sliding the zipper down. Our naked bodies touch as I lean over her, pushing at her pants.
“No…” She said panting as she brought her face up. “Keep it on.”
“Just a little…” I replied, begging, pleading to her. She nods her head with slight hesitation. She sat up at her seat, and I tug her tight pants down. I expose her white smooth panties when her hands stop me. Her jeans sat at mid-upper thigh as her hand grabs at my cock again, my hands to each of her breasts. I lean in, her breasts in my face. Her nipples were stiff and firm in my mouth and every encircling lick elicited a moan of pleasure from her. I continue to kiss and suck her boobs, my hands falling to her panty ass, feeling the top of her panties and naked skin.
I move my hands to her thighs next, feeling her smooth thighs on the outside of both legs. Slowly, I push her jeans inch by inch. I could feel her breath on my penis, hot and heavy. She proceeds to engulf my cock, slowly taking more and more.
My wife was never a fan of blowjobs, and gave me a few licks before wanting me pound her pussy. Her sister though…she was getting my penis slicker and slicker with saliva, running her tongue along my shaft and knob. This is a blowjob! I wish she could teach her sister how to give one…
Her mouth giving my cock great pleasure, I moan loudly when her tongue runs over my sensitive know. I continue to inch her pants down, just reaching her knees. Knowing her arching pussy was now inches from my fingers, I put my hand in her crotch. Her hand immediately grabs mine, her mouth leaving my cock. Her hand props her up.
“That’s off limits.” She scowled.
I nodded, my hands back on her thighs and back, running my hands up and down, creasing her. Waiting for the right opportunity, her legs would spread a little when I massage and fondle her breast. Timing it just perfect, my hand quickly clasps her crotch before they close to feel her wet pussy. Only I didn’t feel a wet spot. Instead I felt a shaft…
She immediately sat up and froze; an embarrassing shock came on her face. I have been intrigued with Transsexuals, as I was a part-time cross-dresser myself, something my wife didn’t know about especially when I borrow her clothes sometimes. So my heart was pounding fast, when I realize she was actually a transsexual. I never thought I could ever meet one, but here’s my sister-in-law, hiding her tiny cock all along.
“It’s ok. I want to see it.” I said to her. A tear starts to form in the corner of her eye. I assure her that I want to do this. She finally gave me the go-ahead, as I slid her jeans off her legs. I assure her again, before I took the helm of her panties and slid it down her legs. She had closed her legs, but her cock came out, resting on her thighs. My eyes immediately glued to what was between her legs. Her little uncircumcised cock was soft, maybe 4 inches, but it look so cute on her hot feminine body, smooth and clean.
“You look so hot and beautiful.” I said to her, still staring at her cock. That elicits a smile from her as I move closer to her sexy body, my hands run up and down her thighs, trying to relax her and open her legs.
I lean my head down, kissing her breast, taking as much as I could into my mouth. I lick and suck each of her globes, as she relaxes more and more. My hand then came up to her penis. I wrap my fingers around her soft shaft, my palm cupping her warm balls; I jerk her penis back and forth. I could tell she was enjoying this, as I could hear her moan above, her cock slowly becomes erect.
“It’s been a while since I’ve had a cock inside. I want you to fuck me.” She says. She doesn’t need to tell me twice as I got up to get into position. She positions herself in the corner of the L-shape sofa, spreading her legs with her feet on the couch, she leans back, her head prop up by a pillow. Her butt is at the edge of the sofa, her cock pointing up; it was a very inviting sight.
“Wait, you have some lotion and condom?” She asks. I nod, and quickly ran to my bedroom to grab the bottle of moisturizing lotion and a condom from the drawer. I ran back to the living room, tearing the packaging apart and slide the condom on my penis. I put some lotion on the condom and fingers, slipping a finger into her tight asshole and slowly finger fuck her. Adding more lotion to my fingers, I continue to lubricate her tiny asshole.
Her head fell back, her eyes closed as she moans. I couldn’t wait as her asshole seems to beg to be filled. I quickly position myself between her legs, my cock right at her entrance. Her hands held her ass cheeks apart, exposing her hole, pleading to be fucked. I look up at her, and she nods for me to go ahead.
I push my cock in when I felt a sensation like something pushing back against my tip. I ease off a little, and then pressed again. Cara groaned softly, the pressure against the head of my cock increases. Pushing slowly, the pressure slowly spread around the head of my dick. My penis was going in!
Then she clamped up on me and I almost came right there. After a second she relaxed again, and I felt my cock pushing a little deeper inside. I was in heaven. Her butthole kept clenching at my dick like it didn't want it there. Cara was gasping and pulling her fingers into the sofa. For a second I wondered if it hurt, but then I felt my pubic bone come to rest against the soft skin of her butt and realized that I was all the way inside. My six inches had disappeared into my sister-in-law’s ass.
Instinct took over, and I grabbed her by the waist and started fucking her. It was so intense that I forgot about being gentle or anything else, the only thought in my head was the feeling of her butt squeezing up around my cock. I increase my rhythm, sliding my cock in and out of her tight ass. My balls slap at her ass cheeks as I keep burying my penis fully into her. Cara squealed and squirmed underneath me, her voice alternating from low grunts to high-pitched squeaks. I pounded her ass, her breathing became rapid, her breasts juggling back and forth as I ram my penis into her, her chest rising and falling as her breathing got heavier. I felt her ass grabbing at my dick and her body shuddering underneath me. Her sphincter tightens its grip on my cock, and I grab both of her thighs, pulling her towards me while with a final thrust, I pushed in as deep as I could and started cumming harder and harder than I ever had before in my life.
I shuddered, my cock jerking spastically in the tight grip of her butt as I flood the condom with my sperm. As the last pulses faded I fell to my knees, my head spinning. She was panting and groaning softly, the muscles in her ass still trying to push me out. I carefully pulled out of her, the tip of the condom loaded with white liquid. I pulled it off, dropping it on the coffee table sat up next to my sister-in-law. She hadn't moved much, her legs still open wide on the sofa, her arms at each side as she was in a state of ecstasy as she continues to breath hard.. I started rubbing her breast a little, when I saw that she had cum all over her stomach. Her cum wasn’t as much as mine, and it was clear instead of white. I grab my t-shirt and wipe it off of her body.
“You ok?” I ask.
She could only nod in response, her chest rising and falling as she tries to get air back into her lungs. Then I heard a faint sound of the garage open.
“They’re back!” I said loudly. Her head props up as she realizes what I said, and I grab our clothes off the floor. I gave her her clothes as she throws me some of mine. I almost forgot the condom and lotion, running back to the coffee table to grab it, before running to the master bathroom. Cara had already gone into the other bathroom to clean herself up.
I quickly dress, and came out just as they reach the top of the stairs. My heart still pumping fast, I led the way, seeing if there was any other evidence of our sexual romp. Cara steps out, and without missing a beat, asks how the ice-cream was to her kids. We didn’t speak a word to each other the rest of the day, which was ‘normal’ between us.
They left a few hours later, and I stood there waving goodbye, smiling as I had buttfucked my sister-in-law.