Chapter 03.2
Soon she's riding me like a whore, and not the lifeless sex doll she's been most of the week. I'm not ashamed to say I only last ten minutes this second time, then I dump another load into her, which is exactly what she wanted of course. The more cum the better. But she got more from this fuck than my seed. She came hard. What a feeling it was making this babe climax on my cock.
As I pump her full of cum this second time, Pippa leans forward bringing her face inches from mine. Her hazel colored eyes looking directly into mine as she feels my sperm gush into her as she milks it out of me with her amazing cunt.
"Drop me home," I tell Cindy when we get to her car.
I'm totally wiped, and I need to rest. Plus, I'm not sure Cindy wants me back at hers tonight anyway. She seems a little annoyed that she was surplus to requirements this evening. I hope this hasn't ruined things between us, but what did she expect would happen.
The drive back to my house is a quiet one, but when Cindy pulls up down the street from my parents' house in the usual spot, I lean across and give her a kiss on the lips. I know immediately we'll be OK with how she kisses me back.
When Cindy calls me one evening after work, I assume it's just to arrange our almost nightly hook-up, we've been at it like rabbits since that last night at the hotel. But this evening is a different conversation.
"It worked," she says, the excitement showing in her voice.
"What worked? What are you talking about?" I reply.
"Pippa is pregnant!" she says. "It worked, in the first month of trying too. You're a fertile young man, aren't you!"
It's been three weeks since that Friday night with Pippa. Of course I knew this news was a possibility, maybe even a likelihood. But it's still a shock to hear you've made someone pregnant. Suddenly it seemed very real.
"Wow, that's great," I say, trying to sound enthusiastic, but in reality I don't know how to feel. Cindy picks up on my reaction.
"You did a good thing Tony. You've made someone very happy. Try not to overthink it."
"Yeah I know, you're right. It's just weird hearing it I guess. I'm happy for Pippa," I say honestly.
"Do you want to come over tonight? It will be just the two of us," Cindy says.
"It's tempting, but I think I'll stay at home. Is that OK?"
"Of course sweetie, I understand," she replies.
"I just need an early night. I'll talk to you tomorrow," I say, and then we say our goodbyes.
I go to bed early, but I don't sleep for a long time.
It takes me a couple of days, but I manage to get my head around getting Pippa pregnant. She called me herself to thank me, and also to reassure me this would remain a secret between the three of us forever. Hearing the happiness in her voice snapped me out of my anxiety. I had done a good thing.
By the following Wednesday night, I'm back in Cindy's bed drilling her hard. She's told Paul to get lost this evening, and he obliged, happily I assume. I need this time alone with Cindy without an audience.
"Did you like having Pippa on top of you, her sexy little body all yours," Cindy says as she rides me in the same position as Pippa did, and fucking two loads out of me too. She likes reliving that last night in the hotel. I think she gets off on her jealously while we fuck.
"I fucking loved every second of it, having my hands all over her. She's such a hot little slut," I say, giving Cindy exactly what she wants. Also being completely honest.
"I bet you did, you little fucker," she says, groaning now as she grinds down on me with her eyes closed, probably imagining me and Pippa together.
"The horny bitch knows how to screw," Cindy says panting. "You were probably the first proper fuck she's had in years."
"That's a shame, someone who looks like her not getting it on the regular. I'd never get off her if she was my wife," I say, purposely trying to make her even more jealous.
Then she soaks me as she cums on top of me. I've already fired a load into her soon after she got up on me, so I'm able to keep going. I take over now, and start fucking up into Cindy as she keeps cumming while on top of me.
This has been a regular little game we've been playing the last three weeks, so it's nice to get back to it after my little anxiety driven hiatus.
I spend the night in Cindy's bed and I get my first good sleep since finding out about the pregnancy. Maybe I am cut out for this after all.
I settle back into a nice routine of work and Cindy Smith over the next few weeks, I can't get enough of her. I've practically moved into her house at this stage, I spend so many evenings and nights with her.
We let Paul watch us some nights, but being honest, Cindy and I get as much from it as him. It can be very exciting having her powerful husband there looking from the shadows.
When I stay over, Paul sleeps in a spare room without even having to be asked, even the nights we let him join us while we have sex. Brian spends most nights with his girlfriend, but we still need to be careful in case he comes home unexpected.
It's an arrangement that works, and the sex is unbelievable. Sometimes we like to role play when we're alone. Cindy really likes to pretend she's Pippa, or my Mom. It can get pretty weird, but amazing. But she doesn't need to pretend to be anyone else for me, it's Cindy I'm addicted to fucking.
"So, you've probably guessed I sorta like the idea of sharing you with other women," she says to me after sex one night, and she seems a little embarrassed about this admission.
"I've noticed," I say with a grin. "You did pimp me out to your friend after all."
"Oh Tony, you make it sound so seedy," she says, but then smiles and adds with a whisper "I love it."
"I know you do."
"I love imagining you making several women pregnant," she says. "I think about you breeding hundreds of women, God it's so hot."
"I think one was enough," I say, not admitting that the idea turns me on too.
"We'll see," Cindy says, then snuggles backwards into me and falls asleep.
I decide to postpone my final year of college. Mom and Dad are not very happy about my decision, to put it mildly. But when I explain my plan to work for the year and get as much savings together as possible to maybe have enough for a down payment on an apartment when I start working after finishing my Senior year, they see I've thought this through.
And I have thought this through, I'm only 90 percent thinking with my cock. No fucking way can I give up nailing Cindy on a daily basis.
When I tell Cindy, she doesn't even pretend to hide that she's delighted. The woman can't get enough of me.
"I thought this was just a summer fling Tony," Cindy says. "I can't believe I get this all year round," she groans while cupping my package through my jeans, in public!
We're on a date, by the way. At the movies. A bit risky, but we went into the city instead of the local theater, so a much lesser chance of being seen by anyone that knows us. We decide to throw caution to the wind and hold hands as we walk around. The looks we get from strangers, the age difference catching people's eye.
But it's worth it. It's exciting being together out in the open. And I can't deny it's turning me on seeing how men look at Cindy with pure lust, and then enviously glance at me.
The movie theater is almost full, but Cindy and I can't keep our hands off each other. We make out like teenagers, and knowing people can see us is adding to the excitement.
Cindy is to my left, and a couple are sitting to my right. I can almost feel the woman's eyes on us for the entire movie. I had never been into voyeurism before, but maybe having Cindy's husband watch us turns me on more than I have been admitting to myself.
At one stage during the movie, Cindy is kissing and licking my neck as I sit back and look at the screen. I notice the woman to my right tilt her head in our direction several times. I steal a glance at her, and I catch her eye. She's hot, and I can tell she's enjoying our little show when she gives me a hint of a smile.
"Naughty boy," Cindy whispers into my left ear, her hot breath making me tingle, then she sticks her tongue into my ear before nibbling on my earlobe. Knowing we're being watched, she reaches down and grabs my rock hard cock through my pants. I look to my right again and see the sexy stranger stare at where Cindy's hand is.
I had actually been looking forward to seeing this movie for months before it was released last week, but I've missed most of it. I don't know if I'm disappointed or relieved when the end credits roll, because I honestly don't think Cindy would have gone much longer without pulling my stiff cock out right here surrounded by all these strangers.
As we shuffle out our row of seats, I feel a tap on my shoulder.
"Um, hi," my seat neighbor says.
"Hello," I reply, a bit taken aback. Cindy looks back and stops.
"Sorry for disturbing you, but, em, we couldn't help but notice how much you guys are into each other," she says.
I look over her shoulder at her date, and I see he's staring at Cindy.
"No problem," I say. "We're on our first date." Cindy squeezes my hand when I say that.
"Aw, that's so sweet. Look, this is really awkward so I'm just gonna come out and say it. Would you guys like to come back to ours for a drink? We're not weirdos or anything. It's just, well we think you're both really hot, and well, we'd like to get to know you better," she says. "We live just around the corner."
I look at Cindy, who has stepped up close to me now and is pushing her tits against my arm. She makes a face that tells me she's not completely opposed to the idea.
"I'm Isla," the woman says reaching out her hand for me to shake, "and this is my husband Liam." He nods and smiles, then his eyes to go Cindy's tits.
"I'm Tony," I say as I take her hand. It feels delicate and soft in mine. "This is Cindy."
Isla is even better looking than I suspected.
"So, what do you think? About that drink?" Isla says, breaking the momentary silence.
"Sure, that sounds like fun. What you think?" I say to Cindy.
"Why not," she replies.
"Wow, so exciting," Isla says, and claps her hands together.
We walk with Isla and Liam back to their apartment, mostly in silence which feels strange. But thankfully it's not far.
Their apartment is really nice, with an amazing view of the city lights.
"We've never done anything like this before," Isla says. "Bring strangers back I mean. Bring anyone back."
"It's a first for us too," Cindy says.
"We've talked about it for a while now," Isla says. "But the opportunity never really happened. But when we saw how you two were with each other, well we couldn't pass up on the chance you might want to, you know..."
"Here buddy," Liam says, handing me a beer. "Cindy, we have wine, beer, whatever you want."
"I'll take a white wine, please," Cindy says to him, and I see her giving him a lingering look. I can tell she thinks he's attractive.
Liam turns on some music, and we all take a seat on their comfortable sofa and armchairs. Cindy and I sit beside each other on the large sofa, Isla takes an armchair across from us and Liam sits on the cushioned arm beside her.
Isla tells us she is 29, and Liam is 32. They've been married four years. She works in marketing, and Liam is in IT. They don't have any kids.
Cindy tells our story, but leaves out the part about cuckolding her husband. Now we're the ones who don't want to scare the new people away!
The more I see of Isla, the more attractive I find her. She's 5'4" I would guess, very dark brown hair, almost black, blue eyes and pale skin. She looks very well in her skin tight jeans and black tank top.
Liam is about 6'1", and he keeps himself in good shape. He's a good looking man, so I can see why Cindy would be interested. When Cindy tells them she's 51, they're shocked. But I see Liam fix his pants to make room for a boner, he must have a thing for mature ladies.
Both of them seem turned on by the age difference between me and Cindy, and seeing their reaction has an immediate effect on me. I was already carrying a semi since we got into the apartment and I got a proper look at Isla, glancing at her ass every chance I got. But now, the four of us are openly eyeing each other up, and it's turning into a very arousing scenario. We all know why we're really here, and knowing something is going happen is exciting.
Cindy sees my cock bulging in my pants, and of course she can't resist stroking her fingers up my leg and wrapping them around my shaft. She doesn't even break her conversation with Isla and Liam.
As usual, Cindy is dressed to kill, even for a date at the movies. She's wearing a short black skirt, and a white thin strapped tank top. She would make any man on earth hard in a heartbeat.
I lean back on the sofa taking a swig of beer, and let Cindy feel me up in front of these strangers. Isla and I lock eyes, and she doesn't look away for a long time, only when I feel Cindy let go of my cock and reach for my belt buckle. She's really going to do this in front of them!
As Cindy pulls down my zipper, a rush of excitement courses through my body and my cock strains upwards against my pants. When she reaches her hand inside, she gently wraps her fingers around my throbbing pole, and carefully pulls up out of my pants and into the open. The conversation has fallen silent, all eyes are on my crotch.
She strokes me up and down slowly, and she's looking at the couple across from us while doing it. Isla might have been the one who plucked up the courage to ask us back, initiating this whole thing, but Cindy is the one controlling what's happening right now.
Both of our hosts are getting visibly excited as they sit in silence watching Cindy handle my cock. Liam leans down closer to his wife, and cups her ample tit in his hand, squeezing it, and then slips his hand down her top to get a better feel of the other one.
I'm staring into Isla's eyes, but she can't resist looking down at my lap again and licks her lips. When Cindy lowers her head down taking my full length into her mouth and throat, Isla looks up at me again. Her chest is heaving with her deep breaths, and suddenly she reaches for her husband's belt, not breaking eye contact with me as she pulls his cock out of his pants. I hope this night goes where I think it is, I really want to get my hands on her.
Cindy moves down onto the floor, keeping my cock in her mouth as she slides down between my legs onto her knees. Isla sees this and does the same. Now both women are on their knees, their asses almost touching, giving their men blowjobs, filling the room with sucking and slurping noises. Liam smiles at me then raises his bottle, and I return the gesture.
"You want to join me over here," Cindy says in a husky voice, looking back over her shoulder towards Isla.
When she immediately lifts her mouth off her husband and turns around on her knees, Isla lets us all know exactly what she wants. She didn't need a second invitation.
Then seconds later, I'm living every man's dream. My stiff pole is standing proudly, throbbing, between two beautiful women's faces, as they slowly bring their lips to my cockhead. They reach it together, and both of them flick out their tongues simultaneously, swirling either side of my engorged head. I notice their tongues meet and dance together as they lick around my pisshole, and they end up kissing with my tip between their mouths. I just about manage to find the strength to not cum right there and then.
Liam is still sitting on the armchair, stroking himself as he looks on at his wife take my cock into her mouth. She softly takes hold of my shaft in her hand too, and then jerks and sucks me off at the same time. I see Liam stir, then kneel down onto the ground himself, and reach his hand down behind Cindy towards her ass. I can't see what he's doing, but I can guess. Cindy moans and throws her head back.
Things move quickly after that.
"Get up here," I say to Isla, and within seconds she's stripped off and is sliding her wet cunt down my pole.
Before long, I'm looking over Isla's shoulder at Cindy on her hands and knees wearing only her black mini-skirt, her tits swinging up towards her face as Liam rails her from behind. She's loving it, and he's giving her a good seeing too in fairness. I had a sneaky look at his cock before he buried it into my woman - he's big, but mine is a little bigger, I note happily.
Isla is riding me like a woman possessed. I'm guessing she likes getting some fresh cock that isn't attached to her husband. As good a fuck as Cindy is, no woman has ever rode me as hard as Isla is right now. This woman likes a good fuck, that's certainly clear.
"I'm close," I whisper into her ear as she continues bucking on top of me. A little friendly warning before I spray my load into her cunt, it's nice to be nice.
"Do it inside me," she grunts back quietly.
I reach around and grab hold of her firm ass with both hands, slamming her down on me even harder than she's managing on her own. Her toned ass feels so good in my hands, I can't resist giving it a few slaps as she continues to bounce on my cock.
Cindy is receiving similar treatment from Liam. It's hard to tell the difference between the noise of his hand reddening her ass cheeks, and his thighs slapping against the back of hers as they fuck hard.
Then I unload deep into Isla, pulling her down by the ass onto my root, holding her there as I fill her up. Her pussy muscles contract, squeezing my cock tighter than it's ever been squeezed before. But it's the milking motion that feels most unbelievable. I don't even notice Liam and Cindy finish.
"That was pretty wild, with Isla and Liam," I say to Cindy. We're in bed back in her house, naked. We have the house to ourselves, Paul is away on a work trip, and Brian is staying over with his girlfriend as usual.
"I feel like I'm living, for the first time in years," she says. "But I never thought I would do something like that. I mean, they were total strangers! I enjoyed seeing you with her."
"I could tell," I say grinning. "You look so hot when you fuck, you know."
"Aw, you say the sweetest things," Cindy says, and play punches my arm.
We're getting very comfortable around each other. More so all the time.
"I wasn't sure you would go for it, hooking up with them I mean," I say.
"It was a spur of the moment thing. If I thought about it I probably wouldn't have. But I'm sure glad now, it was crazy," says Cindy.
"It makes me wonder what else you're into," I say coyly, looking at her suggestively.
"Wouldn't you like to know," she says, giving nothing away.
"You can tell me, whatever your fantasies are. No judgement here," I say.
"Eh, some things are better off staying private," she says.
"We've come this far Cindy, what else could possibly shock me. Besides, I want to explore all our fantasies together. You're not the only one having the time of your life. Every second I'm with you is me living my fantasy out in real life," I say.
"Really? How?" she says.
"Where do I start! You're the hottest milf imaginable. I used to jerk off looking at you on TV when I was young, and now here I am in your bed. We're having a full blown affair, right under your husband's nose, literally! Then you loan me out to your friend. To knock her up. Fucking hell, I'm in heaven Cindy," I say, and even I can't believe what my life has become. "The least I can do is help you out with any desires you might have in mind. Why stop now."
She stays silent for a long time, and I can see she's building up to something. I wonder what she has in mind.
"Well, there is something else that really turns me on," Cindy says finally.
"Lots of things turn you on Cindy," I say, and she punches me on the shoulder again.
"One thing in particular. Look, I'm just going to say it and you can say no of course," she says, then pauses again.
"Come on, the suspense is killing me," I say, urging her to tell me.
"When you were with Pippa I got a little jealous," she says.
"Eh, yeah, I remember," I say.
"Let me finish," she says.
"OK, sorry," I say, holding my hands up.
"I got jealous, but it turned me on too. And the more I thought about it afterwards, the more turned on I got. Then seeing you with Isla tonight, that's what made me cum, not Liam. Yeah I enjoyed the sex, but it was looking at you and her that was the best part," Cindy says.
"What are you getting at?" I ask.
"I think things are getting kinda serious between us," she says, and looks at me, waiting for a response.
"Yeah, they are, I feel the same," I say honestly.
"You have reignited my life Tony. You've opened me up to a whole new world where I've explored sex, fantasies, things I haven't even dreamed of before. And I feel alive for the first time in decades," she says, then pauses. "I'm trying to say, I want you to be with other women. You're my bull Tony, but a bull needs more than one cow. Jesus, I can't believe I'm calling myself a cow! Even saying stuff like that turns me on now. And I know you don't judge me."
"Of course not, never. Everything you do amazes me," I say, looking into her eyes.
"I want you to be with other women, but I want to know about it. See you with them if possible. The way you took control of Pippa, and me, and then with Isla earlier tonight, it's made me realize that I want to share you. Anyway, I don't think I have a choice, an animal like you won't be tamed for long."
"Cindy, as nice and all as this is to hear, I think you're talking absolute crap. I'm not the stud you think I am," I say.
"Oh Tony, if you only knew the effect you have on women. It's adorable how oblivious you are to what you have. Trust me Tony, there aren't many women that could resist you," Cindy says, then continues, "And when you fuck, my God, you bring me to places I didn't even know were possible. It's not just me, I could see it in Pippa's eyes, and Isla's too. The things you can do with this fuck stick between your legs," she says, grabbing hold of my rod.
Hearing her say this has had an effect on me. I'm hard as fuck again. I'm not fully sure where all this is headed, but it's sure as hell turning me on.
"So what do you have in mind?" I ask her.
"I want to share you with some of my friends," she says quickly, like she's already thought this through. "And my sister Molly."
My cock twitches when she mentions Molly.
"Hmmm, do you like Molly? Tony junior seems to like her," she says, stroking my cock gently.
I would love a shot at Molly. She's a hot piece of ass. A younger version of Cindy. But I ignore her question.
"Who else?" I say, playing along.
"We'll see," she says. "I was thinking maybe we could set up a profile on a dating app if you wanted, but we can talk about that."
"It sounds like you want to see me with quite a few women," I say.
"I want you to fuck hundreds of women Tony," she says. "And make more babies with them too, if that's what they want. You making Pippa pregnant has turned me on more than anything."
I may have reignited Cindy's sex life, but she has turbocharged mine. I want, no, I need sex all the time now. I simply cannot get enough. Luckily Cindy is the perfect fuck buddy, but even she can't satisfy my urge to spread my seed. What man doesn't want as much new pussy as possible. But I'm still finding it hard to see this as anything more than pillow talk.
"How do you know your friends, and Molly, would definitely be into me?" I ask, still not believing this will come to anything. "What if they gossip about us, you and me, everyone could find out about us."
"Us women talk Tony, but we are discreet," says Cindy cryptically. "Women want sex too you know, but our husbands' can barely get it up anymore. Us women of a certain vintage have needs too. The sheer stamina you have alone is eye-watering, but you know how to use this thing too."
"OK," I say as Cindy continues with her leisurely handjob. "I'm in." I was in from the first second she brought this up.
"That's my man," she says with a smile, then in one fluid motion swings a leg across my chest and sits her bare pussy down on my face, while at the same time I feel my cock enter her warm, wet mouth. I really am the luckiest man alive, I think to myself, as I plunge my tongue into Cindy sopping wet cunt as far as I can reach.
Now that Pippa is pregnant, I've served my purpose for her. I understand that, and I'm OK with it, even if it is tough to accept I won't get to be with her again. I probably got more out of the deal than I could have hoped for, and it was an amazing week while it lasted. What I wouldn't give for one last hour with her, no holds barred. Tasting a sip of a fine wine like her only leaves you wanting more. But I should be grateful for what I got, I guess.
It's a quiet Tuesday morning at work, giving me plenty of time to daydream about the last few months. Cindy and I did something kinda crazy last night. We went ahead and set up the dating profile she mentioned. She found a website that catered for more alternative kinds of hook-ups, such as a 51 year old cougar and her 21 year old sex toy who are looking to meet women that might be interested in joining them. No head-shots in the pictures of course, but it sure was fun posing for some x-rated photos together.
My phone vibrates in my pocket, so I pull it out to take a look. It's a text from Cindy.
We got a hit stud, she writes. Can you believe it, so quick. We only set it up last night.
No way! Wow. So what happens now? I write back.
Already arranged. Tomorrow night. Same hotel as with you know who... asked for the same room too on the booking. Thought it would be kinda cool going back there, she texts back.
Ha, amazing. But what if she's, you know, not our type, I write, meaning what if I don't find her attractive, but trying to not be cruel.
I think you'll be satisfied, your highness, Cindy texts back, then attaches a photo. It's a picture of a woman, difficult to guess her age, but I definitely am satisfied, or I will be tomorrow night. No face in the photo of course, but her body is amazing.
Get over here as soon as you finish work, Cindy texts then. I think we should get some practice in before our hot date tomorrow.
You better be ready when I get there, I write back, smiling to myself as I think about the night ahead, imagining what sexy little outfit Cindy will be waiting for me in, if she's wearing anything at all.
Just as I stick my phone back into my pocket, it vibrates again. I assume it's Cindy replying.
Hi Tony. We need to talk, the message reads...from Pippa.
As I pump her full of cum this second time, Pippa leans forward bringing her face inches from mine. Her hazel colored eyes looking directly into mine as she feels my sperm gush into her as she milks it out of me with her amazing cunt.
"Drop me home," I tell Cindy when we get to her car.
I'm totally wiped, and I need to rest. Plus, I'm not sure Cindy wants me back at hers tonight anyway. She seems a little annoyed that she was surplus to requirements this evening. I hope this hasn't ruined things between us, but what did she expect would happen.
The drive back to my house is a quiet one, but when Cindy pulls up down the street from my parents' house in the usual spot, I lean across and give her a kiss on the lips. I know immediately we'll be OK with how she kisses me back.
When Cindy calls me one evening after work, I assume it's just to arrange our almost nightly hook-up, we've been at it like rabbits since that last night at the hotel. But this evening is a different conversation.
"It worked," she says, the excitement showing in her voice.
"What worked? What are you talking about?" I reply.
"Pippa is pregnant!" she says. "It worked, in the first month of trying too. You're a fertile young man, aren't you!"
It's been three weeks since that Friday night with Pippa. Of course I knew this news was a possibility, maybe even a likelihood. But it's still a shock to hear you've made someone pregnant. Suddenly it seemed very real.
"Wow, that's great," I say, trying to sound enthusiastic, but in reality I don't know how to feel. Cindy picks up on my reaction.
"You did a good thing Tony. You've made someone very happy. Try not to overthink it."
"Yeah I know, you're right. It's just weird hearing it I guess. I'm happy for Pippa," I say honestly.
"Do you want to come over tonight? It will be just the two of us," Cindy says.
"It's tempting, but I think I'll stay at home. Is that OK?"
"Of course sweetie, I understand," she replies.
"I just need an early night. I'll talk to you tomorrow," I say, and then we say our goodbyes.
I go to bed early, but I don't sleep for a long time.
It takes me a couple of days, but I manage to get my head around getting Pippa pregnant. She called me herself to thank me, and also to reassure me this would remain a secret between the three of us forever. Hearing the happiness in her voice snapped me out of my anxiety. I had done a good thing.
By the following Wednesday night, I'm back in Cindy's bed drilling her hard. She's told Paul to get lost this evening, and he obliged, happily I assume. I need this time alone with Cindy without an audience.
"Did you like having Pippa on top of you, her sexy little body all yours," Cindy says as she rides me in the same position as Pippa did, and fucking two loads out of me too. She likes reliving that last night in the hotel. I think she gets off on her jealously while we fuck.
"I fucking loved every second of it, having my hands all over her. She's such a hot little slut," I say, giving Cindy exactly what she wants. Also being completely honest.
"I bet you did, you little fucker," she says, groaning now as she grinds down on me with her eyes closed, probably imagining me and Pippa together.
"The horny bitch knows how to screw," Cindy says panting. "You were probably the first proper fuck she's had in years."
"That's a shame, someone who looks like her not getting it on the regular. I'd never get off her if she was my wife," I say, purposely trying to make her even more jealous.
Then she soaks me as she cums on top of me. I've already fired a load into her soon after she got up on me, so I'm able to keep going. I take over now, and start fucking up into Cindy as she keeps cumming while on top of me.
This has been a regular little game we've been playing the last three weeks, so it's nice to get back to it after my little anxiety driven hiatus.
I spend the night in Cindy's bed and I get my first good sleep since finding out about the pregnancy. Maybe I am cut out for this after all.
I settle back into a nice routine of work and Cindy Smith over the next few weeks, I can't get enough of her. I've practically moved into her house at this stage, I spend so many evenings and nights with her.
We let Paul watch us some nights, but being honest, Cindy and I get as much from it as him. It can be very exciting having her powerful husband there looking from the shadows.
When I stay over, Paul sleeps in a spare room without even having to be asked, even the nights we let him join us while we have sex. Brian spends most nights with his girlfriend, but we still need to be careful in case he comes home unexpected.
It's an arrangement that works, and the sex is unbelievable. Sometimes we like to role play when we're alone. Cindy really likes to pretend she's Pippa, or my Mom. It can get pretty weird, but amazing. But she doesn't need to pretend to be anyone else for me, it's Cindy I'm addicted to fucking.
"So, you've probably guessed I sorta like the idea of sharing you with other women," she says to me after sex one night, and she seems a little embarrassed about this admission.
"I've noticed," I say with a grin. "You did pimp me out to your friend after all."
"Oh Tony, you make it sound so seedy," she says, but then smiles and adds with a whisper "I love it."
"I know you do."
"I love imagining you making several women pregnant," she says. "I think about you breeding hundreds of women, God it's so hot."
"I think one was enough," I say, not admitting that the idea turns me on too.
"We'll see," Cindy says, then snuggles backwards into me and falls asleep.
I decide to postpone my final year of college. Mom and Dad are not very happy about my decision, to put it mildly. But when I explain my plan to work for the year and get as much savings together as possible to maybe have enough for a down payment on an apartment when I start working after finishing my Senior year, they see I've thought this through.
And I have thought this through, I'm only 90 percent thinking with my cock. No fucking way can I give up nailing Cindy on a daily basis.
When I tell Cindy, she doesn't even pretend to hide that she's delighted. The woman can't get enough of me.
"I thought this was just a summer fling Tony," Cindy says. "I can't believe I get this all year round," she groans while cupping my package through my jeans, in public!
We're on a date, by the way. At the movies. A bit risky, but we went into the city instead of the local theater, so a much lesser chance of being seen by anyone that knows us. We decide to throw caution to the wind and hold hands as we walk around. The looks we get from strangers, the age difference catching people's eye.
But it's worth it. It's exciting being together out in the open. And I can't deny it's turning me on seeing how men look at Cindy with pure lust, and then enviously glance at me.
The movie theater is almost full, but Cindy and I can't keep our hands off each other. We make out like teenagers, and knowing people can see us is adding to the excitement.
Cindy is to my left, and a couple are sitting to my right. I can almost feel the woman's eyes on us for the entire movie. I had never been into voyeurism before, but maybe having Cindy's husband watch us turns me on more than I have been admitting to myself.
At one stage during the movie, Cindy is kissing and licking my neck as I sit back and look at the screen. I notice the woman to my right tilt her head in our direction several times. I steal a glance at her, and I catch her eye. She's hot, and I can tell she's enjoying our little show when she gives me a hint of a smile.
"Naughty boy," Cindy whispers into my left ear, her hot breath making me tingle, then she sticks her tongue into my ear before nibbling on my earlobe. Knowing we're being watched, she reaches down and grabs my rock hard cock through my pants. I look to my right again and see the sexy stranger stare at where Cindy's hand is.
I had actually been looking forward to seeing this movie for months before it was released last week, but I've missed most of it. I don't know if I'm disappointed or relieved when the end credits roll, because I honestly don't think Cindy would have gone much longer without pulling my stiff cock out right here surrounded by all these strangers.
As we shuffle out our row of seats, I feel a tap on my shoulder.
"Um, hi," my seat neighbor says.
"Hello," I reply, a bit taken aback. Cindy looks back and stops.
"Sorry for disturbing you, but, em, we couldn't help but notice how much you guys are into each other," she says.
I look over her shoulder at her date, and I see he's staring at Cindy.
"No problem," I say. "We're on our first date." Cindy squeezes my hand when I say that.
"Aw, that's so sweet. Look, this is really awkward so I'm just gonna come out and say it. Would you guys like to come back to ours for a drink? We're not weirdos or anything. It's just, well we think you're both really hot, and well, we'd like to get to know you better," she says. "We live just around the corner."
I look at Cindy, who has stepped up close to me now and is pushing her tits against my arm. She makes a face that tells me she's not completely opposed to the idea.
"I'm Isla," the woman says reaching out her hand for me to shake, "and this is my husband Liam." He nods and smiles, then his eyes to go Cindy's tits.
"I'm Tony," I say as I take her hand. It feels delicate and soft in mine. "This is Cindy."
Isla is even better looking than I suspected.
"So, what do you think? About that drink?" Isla says, breaking the momentary silence.
"Sure, that sounds like fun. What you think?" I say to Cindy.
"Why not," she replies.
"Wow, so exciting," Isla says, and claps her hands together.
We walk with Isla and Liam back to their apartment, mostly in silence which feels strange. But thankfully it's not far.
Their apartment is really nice, with an amazing view of the city lights.
"We've never done anything like this before," Isla says. "Bring strangers back I mean. Bring anyone back."
"It's a first for us too," Cindy says.
"We've talked about it for a while now," Isla says. "But the opportunity never really happened. But when we saw how you two were with each other, well we couldn't pass up on the chance you might want to, you know..."
"Here buddy," Liam says, handing me a beer. "Cindy, we have wine, beer, whatever you want."
"I'll take a white wine, please," Cindy says to him, and I see her giving him a lingering look. I can tell she thinks he's attractive.
Liam turns on some music, and we all take a seat on their comfortable sofa and armchairs. Cindy and I sit beside each other on the large sofa, Isla takes an armchair across from us and Liam sits on the cushioned arm beside her.
Isla tells us she is 29, and Liam is 32. They've been married four years. She works in marketing, and Liam is in IT. They don't have any kids.
Cindy tells our story, but leaves out the part about cuckolding her husband. Now we're the ones who don't want to scare the new people away!
The more I see of Isla, the more attractive I find her. She's 5'4" I would guess, very dark brown hair, almost black, blue eyes and pale skin. She looks very well in her skin tight jeans and black tank top.
Liam is about 6'1", and he keeps himself in good shape. He's a good looking man, so I can see why Cindy would be interested. When Cindy tells them she's 51, they're shocked. But I see Liam fix his pants to make room for a boner, he must have a thing for mature ladies.
Both of them seem turned on by the age difference between me and Cindy, and seeing their reaction has an immediate effect on me. I was already carrying a semi since we got into the apartment and I got a proper look at Isla, glancing at her ass every chance I got. But now, the four of us are openly eyeing each other up, and it's turning into a very arousing scenario. We all know why we're really here, and knowing something is going happen is exciting.
Cindy sees my cock bulging in my pants, and of course she can't resist stroking her fingers up my leg and wrapping them around my shaft. She doesn't even break her conversation with Isla and Liam.
As usual, Cindy is dressed to kill, even for a date at the movies. She's wearing a short black skirt, and a white thin strapped tank top. She would make any man on earth hard in a heartbeat.
I lean back on the sofa taking a swig of beer, and let Cindy feel me up in front of these strangers. Isla and I lock eyes, and she doesn't look away for a long time, only when I feel Cindy let go of my cock and reach for my belt buckle. She's really going to do this in front of them!
As Cindy pulls down my zipper, a rush of excitement courses through my body and my cock strains upwards against my pants. When she reaches her hand inside, she gently wraps her fingers around my throbbing pole, and carefully pulls up out of my pants and into the open. The conversation has fallen silent, all eyes are on my crotch.
She strokes me up and down slowly, and she's looking at the couple across from us while doing it. Isla might have been the one who plucked up the courage to ask us back, initiating this whole thing, but Cindy is the one controlling what's happening right now.
Both of our hosts are getting visibly excited as they sit in silence watching Cindy handle my cock. Liam leans down closer to his wife, and cups her ample tit in his hand, squeezing it, and then slips his hand down her top to get a better feel of the other one.
I'm staring into Isla's eyes, but she can't resist looking down at my lap again and licks her lips. When Cindy lowers her head down taking my full length into her mouth and throat, Isla looks up at me again. Her chest is heaving with her deep breaths, and suddenly she reaches for her husband's belt, not breaking eye contact with me as she pulls his cock out of his pants. I hope this night goes where I think it is, I really want to get my hands on her.
Cindy moves down onto the floor, keeping my cock in her mouth as she slides down between my legs onto her knees. Isla sees this and does the same. Now both women are on their knees, their asses almost touching, giving their men blowjobs, filling the room with sucking and slurping noises. Liam smiles at me then raises his bottle, and I return the gesture.
"You want to join me over here," Cindy says in a husky voice, looking back over her shoulder towards Isla.
When she immediately lifts her mouth off her husband and turns around on her knees, Isla lets us all know exactly what she wants. She didn't need a second invitation.
Then seconds later, I'm living every man's dream. My stiff pole is standing proudly, throbbing, between two beautiful women's faces, as they slowly bring their lips to my cockhead. They reach it together, and both of them flick out their tongues simultaneously, swirling either side of my engorged head. I notice their tongues meet and dance together as they lick around my pisshole, and they end up kissing with my tip between their mouths. I just about manage to find the strength to not cum right there and then.
Liam is still sitting on the armchair, stroking himself as he looks on at his wife take my cock into her mouth. She softly takes hold of my shaft in her hand too, and then jerks and sucks me off at the same time. I see Liam stir, then kneel down onto the ground himself, and reach his hand down behind Cindy towards her ass. I can't see what he's doing, but I can guess. Cindy moans and throws her head back.
Things move quickly after that.
"Get up here," I say to Isla, and within seconds she's stripped off and is sliding her wet cunt down my pole.
Before long, I'm looking over Isla's shoulder at Cindy on her hands and knees wearing only her black mini-skirt, her tits swinging up towards her face as Liam rails her from behind. She's loving it, and he's giving her a good seeing too in fairness. I had a sneaky look at his cock before he buried it into my woman - he's big, but mine is a little bigger, I note happily.
Isla is riding me like a woman possessed. I'm guessing she likes getting some fresh cock that isn't attached to her husband. As good a fuck as Cindy is, no woman has ever rode me as hard as Isla is right now. This woman likes a good fuck, that's certainly clear.
"I'm close," I whisper into her ear as she continues bucking on top of me. A little friendly warning before I spray my load into her cunt, it's nice to be nice.
"Do it inside me," she grunts back quietly.
I reach around and grab hold of her firm ass with both hands, slamming her down on me even harder than she's managing on her own. Her toned ass feels so good in my hands, I can't resist giving it a few slaps as she continues to bounce on my cock.
Cindy is receiving similar treatment from Liam. It's hard to tell the difference between the noise of his hand reddening her ass cheeks, and his thighs slapping against the back of hers as they fuck hard.
Then I unload deep into Isla, pulling her down by the ass onto my root, holding her there as I fill her up. Her pussy muscles contract, squeezing my cock tighter than it's ever been squeezed before. But it's the milking motion that feels most unbelievable. I don't even notice Liam and Cindy finish.
"That was pretty wild, with Isla and Liam," I say to Cindy. We're in bed back in her house, naked. We have the house to ourselves, Paul is away on a work trip, and Brian is staying over with his girlfriend as usual.
"I feel like I'm living, for the first time in years," she says. "But I never thought I would do something like that. I mean, they were total strangers! I enjoyed seeing you with her."
"I could tell," I say grinning. "You look so hot when you fuck, you know."
"Aw, you say the sweetest things," Cindy says, and play punches my arm.
We're getting very comfortable around each other. More so all the time.
"I wasn't sure you would go for it, hooking up with them I mean," I say.
"It was a spur of the moment thing. If I thought about it I probably wouldn't have. But I'm sure glad now, it was crazy," says Cindy.
"It makes me wonder what else you're into," I say coyly, looking at her suggestively.
"Wouldn't you like to know," she says, giving nothing away.
"You can tell me, whatever your fantasies are. No judgement here," I say.
"Eh, some things are better off staying private," she says.
"We've come this far Cindy, what else could possibly shock me. Besides, I want to explore all our fantasies together. You're not the only one having the time of your life. Every second I'm with you is me living my fantasy out in real life," I say.
"Really? How?" she says.
"Where do I start! You're the hottest milf imaginable. I used to jerk off looking at you on TV when I was young, and now here I am in your bed. We're having a full blown affair, right under your husband's nose, literally! Then you loan me out to your friend. To knock her up. Fucking hell, I'm in heaven Cindy," I say, and even I can't believe what my life has become. "The least I can do is help you out with any desires you might have in mind. Why stop now."
She stays silent for a long time, and I can see she's building up to something. I wonder what she has in mind.
"Well, there is something else that really turns me on," Cindy says finally.
"Lots of things turn you on Cindy," I say, and she punches me on the shoulder again.
"One thing in particular. Look, I'm just going to say it and you can say no of course," she says, then pauses again.
"Come on, the suspense is killing me," I say, urging her to tell me.
"When you were with Pippa I got a little jealous," she says.
"Eh, yeah, I remember," I say.
"Let me finish," she says.
"OK, sorry," I say, holding my hands up.
"I got jealous, but it turned me on too. And the more I thought about it afterwards, the more turned on I got. Then seeing you with Isla tonight, that's what made me cum, not Liam. Yeah I enjoyed the sex, but it was looking at you and her that was the best part," Cindy says.
"What are you getting at?" I ask.
"I think things are getting kinda serious between us," she says, and looks at me, waiting for a response.
"Yeah, they are, I feel the same," I say honestly.
"You have reignited my life Tony. You've opened me up to a whole new world where I've explored sex, fantasies, things I haven't even dreamed of before. And I feel alive for the first time in decades," she says, then pauses. "I'm trying to say, I want you to be with other women. You're my bull Tony, but a bull needs more than one cow. Jesus, I can't believe I'm calling myself a cow! Even saying stuff like that turns me on now. And I know you don't judge me."
"Of course not, never. Everything you do amazes me," I say, looking into her eyes.
"I want you to be with other women, but I want to know about it. See you with them if possible. The way you took control of Pippa, and me, and then with Isla earlier tonight, it's made me realize that I want to share you. Anyway, I don't think I have a choice, an animal like you won't be tamed for long."
"Cindy, as nice and all as this is to hear, I think you're talking absolute crap. I'm not the stud you think I am," I say.
"Oh Tony, if you only knew the effect you have on women. It's adorable how oblivious you are to what you have. Trust me Tony, there aren't many women that could resist you," Cindy says, then continues, "And when you fuck, my God, you bring me to places I didn't even know were possible. It's not just me, I could see it in Pippa's eyes, and Isla's too. The things you can do with this fuck stick between your legs," she says, grabbing hold of my rod.
Hearing her say this has had an effect on me. I'm hard as fuck again. I'm not fully sure where all this is headed, but it's sure as hell turning me on.
"So what do you have in mind?" I ask her.
"I want to share you with some of my friends," she says quickly, like she's already thought this through. "And my sister Molly."
My cock twitches when she mentions Molly.
"Hmmm, do you like Molly? Tony junior seems to like her," she says, stroking my cock gently.
I would love a shot at Molly. She's a hot piece of ass. A younger version of Cindy. But I ignore her question.
"Who else?" I say, playing along.
"We'll see," she says. "I was thinking maybe we could set up a profile on a dating app if you wanted, but we can talk about that."
"It sounds like you want to see me with quite a few women," I say.
"I want you to fuck hundreds of women Tony," she says. "And make more babies with them too, if that's what they want. You making Pippa pregnant has turned me on more than anything."
I may have reignited Cindy's sex life, but she has turbocharged mine. I want, no, I need sex all the time now. I simply cannot get enough. Luckily Cindy is the perfect fuck buddy, but even she can't satisfy my urge to spread my seed. What man doesn't want as much new pussy as possible. But I'm still finding it hard to see this as anything more than pillow talk.
"How do you know your friends, and Molly, would definitely be into me?" I ask, still not believing this will come to anything. "What if they gossip about us, you and me, everyone could find out about us."
"Us women talk Tony, but we are discreet," says Cindy cryptically. "Women want sex too you know, but our husbands' can barely get it up anymore. Us women of a certain vintage have needs too. The sheer stamina you have alone is eye-watering, but you know how to use this thing too."
"OK," I say as Cindy continues with her leisurely handjob. "I'm in." I was in from the first second she brought this up.
"That's my man," she says with a smile, then in one fluid motion swings a leg across my chest and sits her bare pussy down on my face, while at the same time I feel my cock enter her warm, wet mouth. I really am the luckiest man alive, I think to myself, as I plunge my tongue into Cindy sopping wet cunt as far as I can reach.
Now that Pippa is pregnant, I've served my purpose for her. I understand that, and I'm OK with it, even if it is tough to accept I won't get to be with her again. I probably got more out of the deal than I could have hoped for, and it was an amazing week while it lasted. What I wouldn't give for one last hour with her, no holds barred. Tasting a sip of a fine wine like her only leaves you wanting more. But I should be grateful for what I got, I guess.
It's a quiet Tuesday morning at work, giving me plenty of time to daydream about the last few months. Cindy and I did something kinda crazy last night. We went ahead and set up the dating profile she mentioned. She found a website that catered for more alternative kinds of hook-ups, such as a 51 year old cougar and her 21 year old sex toy who are looking to meet women that might be interested in joining them. No head-shots in the pictures of course, but it sure was fun posing for some x-rated photos together.
My phone vibrates in my pocket, so I pull it out to take a look. It's a text from Cindy.
We got a hit stud, she writes. Can you believe it, so quick. We only set it up last night.
No way! Wow. So what happens now? I write back.
Already arranged. Tomorrow night. Same hotel as with you know who... asked for the same room too on the booking. Thought it would be kinda cool going back there, she texts back.
Ha, amazing. But what if she's, you know, not our type, I write, meaning what if I don't find her attractive, but trying to not be cruel.
I think you'll be satisfied, your highness, Cindy texts back, then attaches a photo. It's a picture of a woman, difficult to guess her age, but I definitely am satisfied, or I will be tomorrow night. No face in the photo of course, but her body is amazing.
Get over here as soon as you finish work, Cindy texts then. I think we should get some practice in before our hot date tomorrow.
You better be ready when I get there, I write back, smiling to myself as I think about the night ahead, imagining what sexy little outfit Cindy will be waiting for me in, if she's wearing anything at all.
Just as I stick my phone back into my pocket, it vibrates again. I assume it's Cindy replying.
Hi Tony. We need to talk, the message reads...from Pippa.