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It was late spring and around Jessica’s birthday that I decided when, where and how I wanted to propose to her. We had a time share of a house up north that I wanted to take her to along with her sisters and their husbands to pop the question. The house was a modern two story Victorian complete with a hot tub and pool. Obviously the pool was closed down for the winter, but the hot tub would be fully functional for any sexual trysts that could/would occur.
“Honey, I think we should take a weekend soon up at the house,” I said over breakfast one Saturday. “We could get Lois and Cara up there, make it a family affair.” Ha! Lois was Jessica’s sister that I had secretly impregnated. No one knew besides the two of us that I had cum inside her unprotected pussy about four months ago.
Jessica’s laugh musically resonated to my ears. Her beautiful smile and gorgeous 34D breasts heaved and jiggled with her voice. “A family affair is right.”
It had been almost two months since she had masturbated her brother-in-law Damon. Cara, Jessica’s voluptuous sister, had called in her free chip with me this coming evening. We were going out on a date. The erotic thought of her sister having me all to herself brought out a new animal out of Jessica earlier that morning.
Soon after she’d gotten Damon off, Jess had started fantasizing about taking him in her butt as I took her with my fat cock in her pussy. Her usually powerful and quick orgasms began to come even easier as we started using small dildos in her ass.
This morning was no different, alas for the time of day in which we’d had sex and the fact that she’d started without me.
The only reason I woke up when I did was because I’d felt the bed shift suddenly, aggressively. Then I quickly picked up the scent of the lubricant that we normally used in bed.
“Take my ass, Damon, he’s still asleep, he won’t wake up,” Jessica purred softly to herself. My heart skipped a beat as my dark brain wondered what she was doing. I couldn’t lie; the thought of Jess having taken another man’s cock in her hand and gotten it off caused me to need to be the alpha dog. To be the top massive cock to her that she ultimately needed and desired.
And then the soft, quick breaths of my girlfriend whimpering washed into my ears as my eyes opened in a flash. She lay naked on top of the covers, her beautiful face turned towards me, smiling directly at me.
“I figured that would wake you up,” she said like an angel. “I’m horny!”
Though her perfect breasts and her Amazonian long fat nipples pointed towards me, it was her hand tucked behind her hip that caused me to stare the most. Her wrist flicked sharply but in short thrusts causing her breath to catch and her mouth to open to an “o” shape.
I suddenly knew she had been fucking herself with the “Damon” dildo as I lay next to her asleep. I pounced onto her breasts with my mouth latching onto her deep maroon nipple. My lips kissed the large matching colored areolas right before they closed around the nipple. I sucked each one hard and for a long time as I allowed my thick cock to fill with blood. It wouldn’t take long as I pictured my girlfriend masturbating herself with thoughts of another man.
When she knew I’d be ready, she threw her right leg over me bringing us closer together. I felt her pelvis grind against my girth as our two most sexual places began to reunite. My cock instinctually found where it wanted to be as both of Jess’ hands now found my chest and arms. With her legs spread wide and me being in between them, it was almost impossible for her to keep up the anal penetration with the dildo.
So I took over for her.
We’d found several different positions to use during our new sexual fantasy played out. She loved going reverse cowgirl which allowed me easy access to her ass. And we constantly used my favorite position as it worked well for me to use the Damon on her.
Though it would never work with another man in our bed, my favorite position was similar to doggy style. She’d be on all fours with me behind her, but my legs would be stretched out over top of hers as I almost lay flat behind her. It gave me a great view of the penetration I was giving her that she was controlling.
If Jess was really getting double penetrated, I’d have the fucker’s ass in my face in this position and that wasn’t going to happen.
But since it was just the two of us, I had the Damon dildo in my hand mischievously poking around her asshole. She growled back at me but was soon begging for it as she took my full length deep inside of her. Suddenly when she pushed back on me, she was also getting the anal penetration that she desired.
“Oh fuck!” she whimpered and purred. “Damon, you feel so good back there.”
She had started using his name so freely and easily during our sexual adventures. It turned us both on with thoughts of him being there fucking her. Would it ever happen? I wasn’t sure.
“That little cock fits my ass perfectly, unlike Porno my boyfriend’s humongous cock!”
And that was the second half of our new sexual role playing. She always reminded me through ridiculing Damon’s small stature how big my cock really was. My male ego was getting stroked as my cock did too. I sighed and growled my satisfaction upon hearing how big I was from Jess.
The sensation of getting fucked in this position was like none other I’d ever felt. Usually the cock got fucked straight, either getting ridden or doing the fucking in the missionary or doggy style position. But in this configuration, Jessica was taking me with my cock almost pointing towards my feet. It felt amazing and I showed her as such by meeting her backwards thrusts with the Damon dildo.
When I felt she needed more, I’d push in the dildo as she shifted off of my cock. So when she moved back onto my cock, the dildo was full into her ass causing her back to arch and her head to get thrown back.
“Yessss give it to me Damon!” she whimpered. My left hand pawed at her hip and ass cheek as I felt my balls begin to tighten. I knew she could feel my cock begin to swell more when she said, “My boyfriend is about to cum in my pussy. Fuck me hard in the ass while he does!”
When I came, my toes curled into a cramp as Jess continued her assault on my cock as I filled her up. We both lay exhausted right after, trying to recover. Then we went downstairs for breakfast.
“Maybe Cara wants to take me and Damon,” I said into my bowl of cereal. “Beat her sister to the punch.”
Jessica laughed and said, “I don’t know if I really have a thing for Damon or if it’s just a wonderful fantasy I like to think about. Besides, I don’t think my sister is going to take her husband and boyfriend out on a date together.”
I shrugged at the thought as my phone vibrated next to me.
“I wonder what lady wants some of Thumper’s attention now,” Jessica purred. After we’d come down after sex that morning, she’d thrown on a shirt but that was all. No bra, no underwear as I watched her free perky breasts as the nipples poked through the material.
Though the possibilities were truly endless, I ran through the possibilities in my head.
It could be Aunt Janet wanting to know when we and Cara could get together again. My cock twitched with those thoughts.
It could be Nikki, Jessica’s cousin, wondering when we were going to have our threesome with her mom. This thought made me want to stroke myself until I came. God what I wonderful adventure that would one day hopefully be.
Of course it could be Cara giving me details for tonight.
Or maybe it was Anderson wanting to know when we could get together to do his wife again. Also a very interesting thought I’d want to think more about.
But nope, it was none of the above. And this one made me stiffen to full attention.
The first message simply read “Hi Daddy”. It could only be from one person. My eyes bugged out and stared with thirsty desire at the second message.
I must have been drooling or Jessica was just curious enough about my reaction that she came around behind me to look at what I was reacting to.
“HOLY. SHIT!” Two words separated into two sentences by my girlfriend as we both stared at her almost naked pregnant sister Lois.
She had taken a selfie in only her forest green matching bra and panties. If you weren’t staring at her obviously swollen breasts, you were looking at her pregnant belly. When my eyes tore away from those two areas, they turned towards Lois’ eyes. They twinkled devilishly at me with her first message resounding in my head. “Hi Daddy.”
She was showing me our growing baby in her growing belly wearing her most intimate attire.
Then a third message came to my phone from her. “I need something big and hard in me. Tomorrow night. See you then.”
What the…???
“Oh yeah, we’re having dinner with Lois and Sean tomorrow night,” Jessica said still unable to take her eyes away from the picture of her sister. “We’re picking Lo up and Sean’s going to meet us at the restaurant.”
Lois’ husband wasn’t having sex with her while she was pregnant. He thought he’d be hurting the baby if he did. Because of that, she needed someone to fulfill her cravings and Thumper was what she thirsted for.
I saved the picture to my phone as Jessica’s hand kneaded my cock through my shorts. “Mmmmm,” she purred. “You’re all warmed up for Cara.” Except she wasn’t picking me up until five that afternoon and I’d need some relief long before then.
“OH no you don’t,” Jessica said suddenly reading my mind. “My sister got you worked up, Thumper’s her problem now.” She tore off playfully up the stairs and to our room. I chased slowly behind her as my engorged cock swayed against the material of my shorts.
When I caught up to her, Jess was already on the bed, lying on her back waiting for me. I dove/knelt between her legs and eagerly ate her Altyazılı Porno out. I did so sloppily lapping at her sex flavored labia and pussy as our juices still lingered from earlier. I dipped a finger into her before I brought it up to her mouth to lick knowing she’d enjoy our mixed flavors just as much.
As I worked over her already worked over pussy, I began having thoughts about the unnatural occurrence of me being able to ejaculate while I licked Lois’ pussy. She was the only one it happened with as I always filled my boxer briefs with cum while I was between her legs. At first it had irritated Jess that her sister did something to me that she couldn’t. But it soon turned into a tiny fantasy that she could get me off just like her sister.
“Are you cumming for me baby?” Jessica purred. We both knew she’d be too sore to take me again as I started to think about where I was going to get my relief.
So I stood up, my face wet from my slobber and her pussy. My cock pitched its tent in my shorts as I stood in front of her. I pulled them down, not wearing any underwear, and showed Jess my hardness. My cock was deep red and veiny but was still full of cum.
I stood at the foot of the bed for only two seconds before Jessica whipped around and was on me with her mouth. If I didn’t cum while eating her out, she’d be sure to by other means that I did. I had thoughts about pulling out Damon dildo but decided the angles wouldn’t work. Thinking about Jess taking one while I filled her mouth caused me to erupt earlier than either of us imagined.
Catching her off guard, she wasn’t ready to receive my seed, instead choking on it as it erupted out her mouth and down onto the bed. To her credit she didn’t stop her actions but refocused her efforts to empty my balls.
“Maybe I won’t leave anything for Cara if I keep this up,” Jessica said smiling.
I started getting ready shortly before Cara was due later that day. Occasional glances at my phone and at the picture Lois had sent me told me I still had something left for Cara if she wanted it.
“You’re looking good stud,” Jessica said sitting on the bed, on the spot where my cum had dripped earlier in the day. “Cara won’t be able to keep her hands off of you.”
With that came a knock on our front door. It was definitely backwards in how society usually views dating, but it wasn’t like I’d be able to go to Cara’s house and tell Damon I was there to pick up his wife for the evening. There was probably a well thought out plan by Cara where Damon wasn’t concerned about her whereabouts.
But how he let her leave the house the way she was dressed, left little to the imagination what she was up to.
When I opened the door, Cara stood in front of me wearing a black and beige patterned dress that hung tightly to her large 40DDD breasts and her thick sexy midsection. The dress was off her shoulders, revealing the bare spots that I knew she loved kissed. Her stocking covered thick calves met a pair of black high heeled shoes. I wondered if she was wearing a garter belt.
With a hand on her hip she looked at my seductively with her long brunette hair falling down her pretty face. “Hi handsome.”
Her large breasts swayed seductively as she walked. The material of her dress started just at the tops, fully covering them. I wanted to put my hands on them, to squeeze them and feel their weight in my grasp.
We kissed on the lips as Jessica looked on in awe. “Damn, sister, you look amazing.” Cara wore very little make-up and her hair was recently cut and styled.
Cara slowly spun to give us the full show. The dress showed off her ample ass in an inviting way that men would find irresistible. I came up behind her and placed a hand on her rump, pulling her closer to me.
“I hope you enjoyed jacking off my husband, sis. I’m here to collect what you owe me.” Cara smiled devilishly before leaning in and giving Jessica a full kiss on the mouth. When her hands crept down to Jess’ ass, I thought for sure we weren’t going to make it out of the house. And I knew by Jess’ reaction, that she didn’t want us to go anywhere either.
“I won’t keep him out too late, baby,” Cara whispered into Jessica’s ear.
Outside I couldn’t help but stare. Cara’s confidence was as sexy and tempting as her big tits and beautiful plump ass. “So where does Damon think you are tonight dressed like that?” I asked getting into her car.
Closing her door, Cara moved into me and we kissed again. This time slower and deeper as my hand found her kneed and began working its way up. She stopped me before I got too far. “He thinks I’m having drinks with some friends. And I’m dressed this way as punishment for letting my slut of a sister get him off!”
We both laughed as she drove, her right hand slipping down to my thigh and holding tight. She drove expertly with one hand as I wondered what the night had in store for us.
“So what are we doing?”
Cara took a deep breath, Brazzers grinned, and let it out. “We, my dear, are playing husband and wife with our favorite new double date couple Melissa and Brandon.”
The name Melissa hit me all at once. She was the store worker Cara and I, well mostly Cara, had seduced into a little three way action a few months back. I distinctly remembered the rabid animal Cara had been between Melissa’s legs. It had been where Cara had discovered her liking for the taste of pussy.
“We’ve been texting back and forth. She’s been drooling over Thumper for some time now,” Cara smiled. “Like an obedient little wife, I finally gave in and we’ll see where the night takes us.”
We drove for another twenty minutes or so with Cara’s hand remaining on my thigh where it hadn’t wondered. I told Cara about my plans for Jessica’s birthday up at the house.
“That sounds fantastic,” Cara said with a dazzling smile. “What could possibly happen with three very horny women and one massive cock?”
“Don’t forget the hot tub,” I added definitely. My mind wondered with visions of Cara and Jessica in bikinis while the cool spring air bit at their exposed skin.
“You’re thinking about us in the hot tub,” Cara said bringing me out of my trance.
I told her about my plans to propose to her sister while we were up there. Then I saw Cara in a bikini and my head got fuzzy. Then I thought about me and Damon with Cara in the hot tub. Oh the possibilities.
We were not the first to arrive at the restaurant. I held the door for Cara as I watched her walk ahead of me, her ample ass swaying for my benefit. We stopped just in the door where I placed my hand at the small of Cara’s back before slowly letting it drift to the mound of her ass. Cara pushed back into me as my hand found the crevice between her cheeks.
Melissa and her boyfriend Brandon stood at the bar with drinks. They were a cute couple, obviously deeply in love with each other by the affectionate way they stood so close to each other. Melissa was as gorgeous as ever with her petite lithe body and a long blonde pony tail. She wore a tight black dress they came half way down her thighs.
Her boyfriend was just so that he was bigger than her. He probably weighed about 40 pounds more but was only two or three inches taller. He was a good looking guy, probably a pretty boy from the looks of him but friendlier and less self-centered.
When Melissa spotted us her face started to light up and it seemed like she had to hold herself back from prancing over to us. But she caught herself before her boyfriend could see her reaction, which would have been very suspicious to him. When I looked at her face, I could tell she was remembered and replaying our day in the dressing room.
Her boyfriend looked at us as she brought us to his attention while she bit her lower lip and smiled at us knowingly.
I began to wonder what Melissa and Cara had planned for the evening. Were they going to push something erotic like partner swapping to happen, or were they going to let things roll to see what happened?
As we got closer, Melissa broke off and headed towards us. I watched Brandon as he first eyed up Cara and then looked over at me. It was no surprise that his eyes stayed affixed to Cara’s chest a few moments longer than what a casual look should have been. After he glanced at me his eyes went back to her probably taking in her size. Cara ran about 155 or 160 pounds with curves in all the right spots. Like I had said many of times, it was her confidence with her body that made her so tempting.
The girls hugged like long time friends to the casual onlooker. But the embrace told me something completely different as they tightly held each other. The oppositeness of the two was so remarkably evident as their bodies pressed together. Cara being large breasted and fairly tall blanketed the much smaller and petite Melissa.
I shook Brandon’s hand and introduced Cara and I. I had thoughts about hugging Melissa but thought better of it since I was playing the part of never having met her before. But when I looked at her, it was hard not to remember seeing her with my cock in her mouth. I looked at Brandon and instantly knew he had no idea that we had been with his girlfriend.
I got a dirty martini for Cara and a Johnnie Walker Black for myself as the four of us stood at the bar getting to know each other while waiting for our table. When I handed Cara her drink, she winked and gave me her most dazzling devilish smile.
Cara stood close enough to me so that her right breast pressed into my side as my left arm wrapped around her. I stood talking to Brandon, who I discovered was mature for his age, my attention fully on our conversation but I allowed my hand to wander slowly down Cara’s back until I felt the rise of her ass against the satin feel of her dress. I dropped my hand further until I was on the downward slide, gave her ample cheek a squeeze before heading back up, rubbing her ass along the way.
Melissa saw what I was doing and smiled. When I looked at her mouth, I couldn’t help but remember my cock sliding in between her lips as Cara ate her out. That plus the sensation I felt from Cara’s ass caused my cock to begin to twitch.
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