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AUTHOR’S NOTE: This is a work of fiction. All characters are over the age of 18. This is the final chapter of an ongoing series. It’s been real fun getting back into the habit of writing regularly. There will be more stories in the future, but probably not any more with these characters. Feedback in the comments would be greatly appreciated and if there’s anything in particular you’d like to see, let me know, I might make that the next short story I write.
A quick recap of the characters:
Me: First person narrator/main character. 57, white guy, works from home, fit for an older guy, but with stamina issues.
Becca: My wife. 55, black woman, works in an office downtown. Large breasts and a big round ass. Has a condition called vaginismus which can cause severe cramps when she attempts vaginal penetration.
Sasha: My daughter. 20, mixed race, currently on summer break from college. Similar body to her mother. Has recently discovered she has the same condition as her mother and is struggling with it.
Ashleigh: My daughter’s friend. 20, white, also on summer break, skinnier than Sasha, comes from a wealthy family.
Andrew: Ashleigh’s brother. 23, white, works with his father, in great shape
*
It was the morning after my daughter Sasha and her best friend Ashleigh had seduced Ashleigh’s brother Andrew with a threesome. My wife Becca and I had watched the whole thing happen through a hidden camera, so we knew it was time to let Andrew in on the family secret. I awoke earlier than the rest, so I quietly put on some jeans and slipped down the hall to Andrew’s room. The door had been left open a crack by Ashleigh the night before, so I managed to sneak up to the bed without waking anyone up. Andrew, a tall young man in excellent shape slept between Ashleigh, a slender brunette, and Sasha, my gorgeous, curvy, caramel skinned daughter. Not one of them had bothered to put any clothes back on after their threesome, though at some point one of them had pulled a sheet up over the lot of them. I stood up straight, folded my arms, scowled, and cleared my throat. “WHAT’S GOING ON HERE!”
All three of them jumped with a start but Andrew started quickly trying to stammer out excuses. I frowned and locked eyes with him. “Quit lying Andrew. I’d hope you’re a better man than that.”
Andrew looked around desperately for another moment before he finally took a deep breath and met my gaze. “You’re right Sir. Sorry Sir. Last night Sasha and I, um, we didn’t exactly have sex, but we did, um, go down on each other.” I pointedly looked at his naked sister lying in bed next to him. “Yeah… Not sure what to say about that except it’s what it looks like. I’m still not entirely sure how or why it happened but Ashleigh and I had sex last night. I don’t really know what to say.”
I shifted my weight but kept my eyes locked with his. “Was everyone sober and using protection?”
Andrew looked guiltily away for a moment before meeting my gaze again. “Sober yes, protection no. I- I didn’t exactly think to bring any with me.”
I huffed through my nose. “Fair enough. I can see that everyone seemed to be consenting and enjoyed themselves.” Sasha and Ashleigh played along, nodding, Andrew was still to frozen to react. “Now the big question. What, exactly, are your intentions towards my daughter and your sister?”
Andrew looked back and forth between the girls before he straightened back up. “I honestly don’t know. I like Sasha. A lot. If she’ll have me, and if you won’t kill me for what just happened, then I would like to date her. As for Ashleigh, she’s still my sister and I’ll always love her, and I won’t deny that I had fun. But if I’m with Sasha I wouldn’t do anything with her without Sasha’s permission.” Andrew looked down and clenched his jaw. “I can see though that I’ve fucked up your vacation, and probably also my chances with Sasha. I’ll get my things and leave.”
I held out my hand. “Hold on Andrew. We need to have a talk. First thing’s first though. Sasha?”
“Yes Daddy?”
“Suck my cock.”
“Mmm, yes Daddy.”
“Ash, give her a hand.”
“Yes Sir!”
Sasha and Ashleigh got on their hands and knees, crawled to the edge of the bed, pulled out my cock and started sucking it, all the while I kept looking at Andrew. Andrew sat, shocked as he watched me slowly fuck my daughter’s face. I softened my expression and chuckled. “Sorry for scaring you there. I wanted to make sure you were on the level.”
Andrew watched, dumbfounded as Sasha and Ashleigh worked in tandem to suck and lick my cock to a full erection. “Y-you’re fucking your daughter?” I nodded. “How long has this been going on?”
I sighed. “Ok girls, we made our point. Move over so I can get on the bed.” I sat on the edge of the bed and Sasha got off the bed, putting her head between my legs. Ashleigh started to join her, but I pointed her towards the tent Andrew was making in the sheets. Obligingly she sprawled out on the bed, pulled the sheets down and popped his cock in her mouth. I looked down and met my Lefkoşa Escort daughter’s eyes as she lovingly ran her tongue along my shaft, lost in her own little world. “Alright, I suppose you deserve the whole story.”
“It all started one night after a bad date with Sasha’s ex Brian. She had tried to give him her virginity, but it was too painful for her to continue. It turned out she had a rare condition called vaginismus. The short version is that if something triggers it, then her pussy clenches shut causing her a lot of pain and making penetration essentially impossible. When she told her mom and I what happened we told her about how her mom has the same condition. Unfortunately for Becca, she had spent years just trying to endure the pain and it had only made the condition worse to the point that when I met Becca, it took us years before penetration was even a possibility for us. And honestly, due to my size even then penetration was a rare thing until after she gave birth.”
Andrew groaned, trying to focus on the story while also enjoying Ashleigh’s enthusiastic blowjob. “Does that- unnh- mean that you and Becca spent years not having sex?”
I reached down and ran my fingers through Sasha’s hair. “Sex is about a lot more than just penetration. I was more than happy with everything else Becca and I did, there were just a few things off limits for a while.” I pushed Sasha’s head down, feeling my cockhead hit the back of her throat. “Mmmmm. Anyway, after Brian showed his true colors and was an asshole to Sasha just because he couldn’t get what he wanted, Sasha asked Becca and I if we could help her overcome her condition. One thing kinda led to another and pretty soon Sasha, Becca, and I were regularly ‘exploring’ together. We weren’t as cautious as we thought though, and Ashleigh found out about us. Thankfully, she didn’t want to expose us, she just wanted in.” Ashleigh responded by moaning and moving to suck on Andrew’s balls. I pulled Sasha’s head off my cock and helped her to her feet. “All in all, it’s been about three weeks. Three weeks of incredible sex with three gorgeous women. I think you can see where my exhaustion came from.”
Andrew laughed and moaned, throwing his head back as Ashleigh slipped a finger into his ass. “Yeah, I can see why that might put a man into the hospital.”
I pulled Sasha forward and she straddled me, sitting on my lap, my hard cock rubbing along her dripping slit. We kissed passionately for a minute before I broke the kiss. “Here’s the deal Andrew, I have no problem with you dating my daughter, so long as you can keep our secret. If you’re ok with sharing her with the rest of us, and you treat her right, then it’s all good with me. Becca’s onboard too.”
Andrew opened his eyes and looked at me. “I can fuck Becca too?!”
I chuckled and slid a finger in Sasha’s ass. “I only said she knows about everything. I didn’t say you could fuck her. That’s her choice. I know my wife pretty well and I think she’ll be more than happy to have some fun with you too, but you’ll still have to ask her.”
“Yeah.” Said Becca from the doorway. She had come in while the rest of us were distracted, wearing nothing more than a shirt, though I noticed her pajama bottoms were discarded in the hall. “Aren’t you going to ask, Andrew?”
Andrew looked between the rest of us before locking eyes with Sasha, who nodded and smiled. “Please, Becca, can I fuck you?”
Becca’s eyes narrowed. “Get over here.” Andrew hopped off the bed and crossed over to Becca. “You haven’t earned a fuck yet, little man. Get on your knees.” As if in a trance, Andrew dropped to his knees, still maintaining eye contact with Becca. “Eat that pussy. Eat it good and make me cum.” Andrew leaned in and began desperately licking at my wife’s dripping slit. Becca gave a gentle sigh and gripped Andrew’s hair. “You’re going to be my little pussy eating bitch. Do you understand that?” Andrew nodded as he continued to lick. “You’re going to make me cum whenever I want. Do that and maybe one day I’ll let your cock in one of my sweet holes. Is that what you want, little man?” Andrew groaned into Becca’s pussy and nodded again. Becca gripped the doorframe as a jolt of pleasure ran through her. She smiled at me. “Well hon’ he’s not as good as you but he’s enthusiastic and I’m sure he’ll get plenty of practice.”
Ashleigh grinned and got on the floor next to Andrew, whispering in his ear. “I love when she gets all dominant like this. You should see when she fucks my ass with a strapon.” Andrew groaned again and Ashleigh smiled, leaning back to play with her pussy and enjoy the show.
I grinned and turned back to Sasha. I kissed her gently and held her close. “You’re ok with all this babygirl?”
Sasha smiled and a tear rolled down her cheek. “Oh daddy, I can’t think of anything that would make me happier.”
I lifted her hips up and let my cockhead slide against her clit. “I can think of one thing.” Sasha ground her hip down and nodded. “But you’re not ready yet.” She bit Girne Escort her lip and shook her head. “Don’t worry babygirl. We’ll keep working at it. Some day you’ll get me inside you. Until then let’s have some fun.” Sasha smiled and kissed my neck as she rubbed her slit along my shaft, the wet heat of her pussy lips enveloping my cock. We groaned together as the rest of the world fell away and the only thing in my world was my sweet daughter hugging me closely and giving me everything she could. “You feel so good babygirl, you’re going to make me cum.”
Sasha slid her hands under my ass and held me tightly. “I want to make you cum daddy. Please cum all over me.” I groaned into her mouth as she kissed me passionately and felt my cock began to pulse. A massive orgasm washed over me as I shot stream after stream between us, my cum smearing all over both of our fronts. Sasha pulled back, strands of cum hanging off her tits and dripping down my chest.
As I caught my breath, I became aware again of the other people in the room. Andrew was gasping for breath on the floor as Ashleigh rode him. Becca had slipped back into her clothes and smiled at the four of us. “I’m going to get some breakfast started loves. Don’t take too long.”
I laughed and helped Sasha off my lap. “Give me a minute to wash up and I’ll be right out to help.”
—–LATER THAT WEEK—–
With Andrew now a part of our “family”, Sasha and him had been spending more time together romantically. It was a rare moment that they weren’t chatting, flirting, cuddling, or sneaking off to make out alone. Ashleigh still got plenty of time with her brother, but she was fine so long as someone was pounding her pussy into the floor at least a couple times a day. Becca found that she never got tired of forcing one or both siblings to service her in one way or another.
It was the second to the last night that we had at the cabin when Sasha sat us all down for a talk. “I- I think I’m ready.” Becca and I looked at each other concerned. Sasha held up one of her toys. “I know I’m not ready for dad, but I’ve been working steadily with the dilators. I’m able to take one that’s almost as big as Andrew without any pain now. I think I’m ready to try penetration again.”
Becca and I shared a look that contained a whole conversation before I turned back to Sasha. “I trust you babygirl. Just remember to go slow, use lots of lube, and be careful. If you trust Andrew to follow your lead and to be slow and patient, then I’m sure it’ll be ok. And if not then it’s not the end of the world.”
Sasha smiled and took a deep breath. “I do trust him, but I’d feel better if you two were there.”
Becca sat back, silently. “I love you Sash’ but I don’t think I should be there. I have a feeling I’ll be too worried about you to stay out of things. I don’t want to take away from what should be a special moment for you.”
Sasha nodded, looking downcast. “What about you daddy?”
I smiled and kissed Sasha on the cheek. “Of course I will, so long as you and Andrew are both ok with it.” Sasha kissed me back and ran off to tell Andrew. I turned back to Becca and held her hand. “Are you going to be OK babe?” Becca squeezed my hand and nodded. “I’m not going to blame you if you want to watch from our room. You know, just to make sure everything is going well.” Becca looked back up and grinned, obviously liking the idea.
—–LATER IN ANDREW’S ROOM—–
Sasha and I were laying on Andrew’s bed, I had remained dressed, but she had stripped down to her underwear. We were cuddling as I stroked her hair when we heard a knock on the door. Sasha propped herself up on her elbow. “Come in.” The door swung open to show Andrew, freshly showered, and nervously rubbing his neck. Sasha and Andrew locked eyes and I felt her breath in sharply. “Hi.”
Andrew stepped in and closed the door behind him. “Hi.” He looked to me and back to Sasha. “I, uh, I knew your dad would be here, but I didn’t think he’d be joining in.”
I squeezed Sasha’s shoulder and got off the bed. “Don’t worry, I was just helping her relax. She’s a little nervous. I’m guessing you are too. Just do your best to follow my guidance and she should be fine.”
Andrew nodded and sat on the bed next to Sasha, placing his hand on her thigh. “Sasha’s going to need a lot of time to warm up, so be gentle and kiss her.” Andrew took a deep breath and crawled up over her, before leaning down to kiss her. Sasha and Andrew’s hand roamed over each other as their tongues danced. Soon they were laying next to each other, their arms and legs wrapping around each other as they giggled. Andrew began to slip his hand down Sasha’s panties. “Not yet! Let her guide you there. For now, just focus on other areas, like her thighs, breasts and ass.”
Andrew looked up, apparently having forgotten I was here, and nodded. He slid his hand along Sasha’s back and fumbled with her bra for a moment before managing to unhook it. Andrew kissed Sasha’s neck and brought his hand under her loose Magosa Escort bra to her breast, running his fingers across her nipples. Sasha gasped and looked up, locking eyes with me before she moaned at his touch. Sasha ran her fingers through Andrew’s hair and pushed his head down further, guiding it to her breast. As Andrew licked and sucked her nipple, she arched her back and awkwardly slipped her bra off. Andrew switched over to suck the other nipple and Sasha moaned, taking his hand and guiding it to her thigh.
I paid close attention to Andrew’s hand but thankfully he had taken things slow and only gently stroked her inner thigh as he focused on her breasts. Sasha moaned and looked at me and I nodded. She pushed his head further down her body and he shifted to kiss his way down her navel. Andrew slipped his fingers under the waistband of Sasha’s panties, lifting her hips gently to slip them down off her feet. He was about to dive back in to start eating her pussy when he looked back at me for approval. I chuckled. “She’s the one in control here.” Andrew looked back at Sasha who just grinned and pushed his head back down.
Becca had apparently been doing some training with Andrew because he made sure to take his time teasing Sasha’s outer lips with long slow licks instead of diving straight towards her clit. Sasha gasped and gripped his head tighter with one, the other reached out for me. I took my daughter’s hand and squeezed it reassuringly. Andrew slid a finger into Sasha’s pussy as he continued to lick, and Sasha groaned. “Hey, give her some warning before you do that.”
Andrew pulled back, apologizing. I pulled a bottle of lube out of my pocket and handed it to him. “It’s alright, just remember that you need to be careful. Use that.” Andrew poured a dollop of lube on his finger and locked eyes with Sasha. She gently nodded and Andrew began to slowly trace her inner lips with the tips of his lubed-up fingers. Sasha’s breathing quickened and she nodded again. Andrew pushed his finger in again up to the second knuckle. I stepped over to get a better look. “Alright, you feel her clenching right?” Andrew nodded and licked his lips. “Just hold your finger there and lick until you feel her relax. Then try for a second finger.”
Andrew leaned in and gingerly licked Sasha’s clit as he held his hand as steady as he could. Sasha squeezed my hand and moaned, her hips gently moving as she took his finger deeper. Andrew slid a second finger in and instead of freezing Sasha only moaned harder and gyrated her hips harder. Sasha gripped Andrew’s head and pulled him away, guiding him back up to her face. She and Andrew kissed again before she broke the kiss, breathing heavily. “I’m ready.”
Andrew hurriedly stripped his towel off and started to climb between Sasha’s legs, and I cleared my throat, gesturing towards the lube. Andrew gave a sheepish grin and squirted a generous glob along his cockhead and shaft. Rubbing it around he got his six-inch cock good and slick before wiping the excess on the towel. Andrew started to press his cockhead against Sasha’s pussy, and I squeezed Sasha’s hand again. “Just like last time Andrew. Get the tip in, wait for her to relax and take control, then let her let you in.” Andrew, breathing quickly now, nodded and looked back at Sasha.
Their eyes were locked as he slipped his cockhead in with surprisingly little resistance. Another couple inches and Sasha winced. Andrew froze in place and left his cock half buried in Sasha’s pussy. Sasha’s eyes clenched shut, she gripped my hand tightly and dug the nails of her other hand into Andrew’s shoulder. I leaned down and kissed Sasha on the forehead. “It’s ok babygirl, just relax, I’m here.” Almost immediately her expression softened and with another few deep breaths she opened her eyes and looked at Andrew.
Sasha pushed up off the bed and kissed Andrew, wrapping her arms around him and laying back to guide him the rest of the way in. “OoooOOOOOHHHHHH!” Andrew kissed Sasha’s neck and mouth as she groaned, feeling a real cock in her for the first time. “It’s so good! Oh FUCK! It’s so fucking GOOD!” Andrew grinned and started to pull out a few inches. “Ooh, ooh! Please be gentle.” Andrew nodded and kissed her again, slowly fucking Sasha’s pussy.
I smiled to myself. “Looks like you two have got things under control. I’ll leave you alone.” Sasha began to say thanks before she gasped in pleasure. I quietly slipped out of the room and went back to the master bedroom. Becca had been watching the other bedroom on the screen while she fucked a bound and gagged Ashleigh with a strapon. I smiled and started stripping off my clothes “Hey babe, having fun?”
Becca grinned and pulled her “cock” out of the young woman. “Lots of fun. Want to help me fuck this little bitch? I’ll take the ass and you get her cunt?” Ashleigh groaned around the gag. I nodded enthusiastically and kissed Becca before we untied Ashleigh’s wrists and I got on the bed. Ashleigh still gagged and wearing a set of leather cuffs on her wrists and ankles moaned and drooled on my chest as she lowered herself onto my throbbing cock. Becca lubed her strapon and slid it into Ashleigh’s ass, rubbing against my cock through the thin membrane. I locked eyes with Becca, and we smiled as we found a good rhythm. Yet again I found myself wondering how I got to be so lucky.
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