Paulo Uses Anna All Night & Jason Waits Outside

I fumble with my keys as I try to unlock my apartment door. I’ve never been so nervous. The last time I was with Paulo I was nervous too, but I’d had a few drinks to release my inhibitions and I didn’t quite know what was going to happen. I thought we might just make out a little bit. I’ve been insisting in my head that tonight is not a done deal, that I’m not a slam dunk kind of girl for guys, but I know the truth. I know I’m sleeping with Paulo tonight.
The lock yields and I push inside, followed by the tall, swarthy groomsman from Dora’s wedding. I’m petite, only about five and a half feet tall and slender, and he towers over me. He’s even taller than Jason, my boyfriend. I’m trying not to think about him as I do this, even though it feels like he’s with us. It feels wrong to bring Paulo home when I have a boyfriend, even if Jason encouraged me to do it. The door thumps close behind us like it’s sealing my fate. I flick on the hall light and Paulo follows me into my living room.
“Nice place. It’s great having a balcony,” he says, looking around.
“It’s convenient to work. There’s only the one bedroom, but that’s enough for me,” I reply, feeling like I’m babbling. Why did I need to bring up my bedroom? The small talk at the bar felt awkward enough, but this is cringy. I’m waiting for Paulo to kiss me — it’s all I can think about — but he just hangs back, examining my bookshelf. It feels like he’s teasing me. He must sense how nervous I am. I feel wired, like one of those yippy little dogs.
I feel so immature. A twenty-eight-year-old woman should not be so anxious about having a man back to her apartment. But I missed out on a whole normal part of my life because I married my high school sweetheart. And I barely dated in high school before him because the idea of it left me anxiety-ridden. I’ve felt the same way about dating since the divorce and took meeting guys very slowly, which meant there have only been a handful of dates in those couple of years — certainly no one-night stands. I’m not a casual hookup girl, but here’s Paulo standing in my living room.
“That’s nice. I have to take the train into the city for work. It’s a pain in the ass.”
The awkward silence stretches to eternity. Internally I’m screaming that I need to fill it, to say something, but I have no idea what to say. I have no plan for this. Paulo and I met for drinks at the bar, and I asked him home. I assumed he would take it from there. He followed me in his car, and I spent the whole drive over talking to Jason. I kept telling him I didn’t think this was a good idea and he kept telling me it would be great. I told Jason I didn’t think I could do it, and he told me he knew I wanted it — I just had to allow myself to let go and enjoy it. Jason was right, but I was not about to admit it. It felt too slutty to tell my boyfriend I want to hook up with another guy. I still don’t understand how he’s okay with that. More than okay with it.
Paulo smiles. He has a cocky smile, but a guy that hot should be cocky. It would be weird if he wasn’t. He has thick black hair, which he wears slicked back, and a jaw so square it looks literally chiseled. His black t-shirt is stretched across a chest I know is rock hard. Paulo looks like a guy in a European cologne ad. Women probably throw themselves at his feet. I don’t know why he’s here with me, but I’ll take it. Should I throw myself at his feet? If I were more daring, I’d drop to my knees and suck him. I wish I was more daring.
“Why are you so tense, Anna? I’m not going to bite you, unless that’s what you want,” he says.
It’s like I can feel his mouth on me when he says it and warmth floods me, concentrating to a tight point between my legs. Can he see the effect his words have on me? “Sorry, I’m not used to this,” I confess. “I don’t invite guys back to my place.”
“But you did tonight.”
“I did.”
Another awkward pause and now I’m sure Paulo isn’t just being a good guy. He’s toying with me. I should be angry, but I think I like being toyed with. I ask, “Can I get you anything?”
Paulo’s cocky smile widens. “You’ve got everything I need right there, Anna.”
“Oh.” It sounds so silly when it slips out, like I’m a little girl being given a surprising treat. I cross to him. If Paulo’s been waiting for me to come to him, I’m ready. His arms enfold me and I’m pliant, the heat of our kiss melting the tension from my body. His kiss is soft, almost chaste, but I go for it, pressing my tongue between his lips. A good girl shouldn’t be so eager, but I’m far from a good girl tonight. His hair is stiff with product when I try to run my fingers through it. I’ve never felt that before, but I don’t care. I love his hair, and I rake my nails over his scalp. Jason’s handsome, but he has fine, light brown hair. Paulo’s mane feels so masculine.
Paulo guides us to the couch, and I move with him. I’m ready to give him whatever he wants. He drops and pulls me onto his lap. We never stop kissing, even when I straddle him. The more we kiss, the hungrier I am for him. I grind into his lap and feel he wants me too. It makes my core throb. Paulo may have played hard to get when we arrived, but he’s in a hurry now. I’m impressed by how quickly he works through the hook-and-eye loops down the front of my red tank bodysuit. Must be all the practice he has unhooking bras.
Jason picked my outfit for Paulo — the red bodysuit and tight black jeans. He wanted a skirt, but I stood my ground. I know it’s dumb, but wearing a skirt just felt too obvious. The bodysuit is tight and shows a lot of skin and isn’t something I would have had the confidence to wear before I met Jason. I wasn’t comfortable with that kind of attention before. He’s taught me to crave it. Jason chose my lacy black bra too, which is exposed to Paulo when he pulls the bodysuit open. Paulo is all over my tits, which feels so good. I’ve always felt like my plump Bs were too small for any guy to notice, but every guy I’ve met since the divorce seems to love them. Especially Jason. He delights in teasing them until I’m begging him to fuck me. It’s crazy that my boyfriend remains in the back of my mind while I’m hooking up with Paulo. Why does knowing he’s watching us turn me on so much?
I was petrified when Paulo was perusing my bookcase. He was going to spot the camera Jason hid among the books and knickknacks. I was sure of it. But he didn’t. I felt weird about it when Jason asked to install the wifi cameras. It felt unfair to Paulo to be secretly watched like that, but Jason pointed out that Paulo was getting what he wanted. The logic was shaky, but I accepted it. The first time Jason watched me with Paulo I didn’t know he was there. I don’t think I could have done anything if I’d known he was there. It still feels creepy to be spied on, but knowing Jason is watching us on an iPad out in the parking lot and getting hard feels incredible. Two men wanting me at once feels impossible. It leads my dirty side to wanting two men at once, but I don’t allow myself to go there.
Jason has tried to explain what he gets out of this and why he’s not jealous or angry, but it’s just illogical. I could never watch my man with another woman. When I found out my ex-husband was carrying on with a woman he met online, it sickened me just knowing about it. But Jason says he loves knowing other men want me and that watching me get off is a massive turn on. I’ve chosen to just accept it since I can’t understand it. But it does nag at me. Does Jason really value me as his girlfriend or am I just a sex doll to him? I guess part of me likes the idea of being a sex doll. We’ve relived my hook-up with Paulo over and over again and whenever Jason tells me how much watching me suck-off Paulo turned him on, I come so hard. I love feeling so dirty and sexy.
Paulo massages my tits with both hands, and I pop open the front clasp of my bra for him, pulling it aside to present my chest to him. He pounces like he’s starving for me, and it makes my body throb. My pale little nips harden to tight diamond points while he licks and sucks them. He pulls them with his teeth, bringing me right to the edge of pain. I cry out in ecstasy, shocked that I like it.
I’m flipped onto my back on the couch and Paulo tosses my low boots aside. He peels down my jeans and unsnaps my bodysuit. My panties follow and it feels like they are just racing off for him. He pauses to kiss my feet — another first for me — before kissing down my leg. I know where he’s going, and I almost stop him out of habit. Having someone go down on me is so intimate and it’s something I’ve struggled to be comfortable with. My ex almost never did it, maybe because he felt me tense when he did, and the first guy I was with post-divorce didn’t even try. Jason has taught me how great it can be if I just relax, so I take a deep breath and let Paulo go for it.
Paulo kissing my soft inner thighs is breathtaking. His stubble tickles, but the firm sucking gives me goosebumps. He has me dying with anticipation. Can he smell how aroused I already am? My petals stick together when he peels them apart. His thumbs stroking me makes me tremble. Paulo keeps sucking on my thigh while he gently teases my flower and I’m afraid he’s going to leave a mark. Would Jason like that, seeing another man mark me? Paulo’s tongue finally slips through my tender, slick furrow and I cry out, stiffening and pushing at him. His hands on my hips control me, keeping me in place. Paulo is in charge right now. His tongue dips inside me and he kisses my pussy full on. I melt and happily surrender to him.

    Paulo explores my sex leisurely like he wants to savor his meal. That wonderful tongue rhythmically slips in and out of me like he’s fucking me with it and my hips move to his beat, slowly fucking his mouth. I see him staring up at me between my thighs, his dark eyes sparkling, but I close my eyes. I can’t watch him while he’s doing something so intimate. How is Jason watching this at all? How does he feel watching another man exploring me so intimately? Is his dick in his hand? I look to the bookshelf, but it’s too much like making eye contact — knowing he’s watching — and my eyes close again.

I thought Jason was good with his tongue — he is — but Paulo is magical. Paulo explores my sex leisurely like he wants to savor his meal. That wonderful tongue rhythmically slips in and out of me like he’s fucking me with it and my hips move to his beat, slowly fucking his mouth. I see him staring up at me between my thighs, his dark eyes sparkling, but I close my eyes. I can’t watch him while he’s doing something so intimate. How is Jason watching this at all? How does he feel watching another man exploring me so intimately? Is his dick in his hand? I look to the bookshelf, but it’s too much like making eye contact — knowing he’s watching — and my eyes close again.
Paulo locks onto my clit and it’s nearly too much. I moan and gasp in ragged breaths. My body shakes and undulates. The pleasure is sharp — too sharp. It burns like a bright sun when he sucks on my button and then I go supernova.
“Oh…oh…OH GOD! Paulo! Ohmygod!” I cry, shamelessly thrusting my hips at his mouth. Paulo locks on, sucking all my juices. I hear him slurping down there and wonder if I’ve ever been so wet.
I’m still trembling and riding my high when Paulo pushes my legs back against my chest. It tilts my hips up and his tongue tickles down below my pussy. It feels weird and I squirm, even though I’m still riding my high. I don’t stop him because I’m distracted, and he moves lower. My cheeks are spread and his tongue darts right in. What is he doing? Why is he licking me there?
“Paulo! Oh god! What are you…doing…to…me…”
His tongue rims all around my tight knot and I don’t know whether or not I like it. It’s just too weird. It tingles. It makes me feel a lot of things. It’s not unpleasant. It seems to make the afterglow of my orgasm burn brighter. And then he pushes. Gently at first, and then harder. Paulo narrows his tongue and pushes until it pops past my knot. His lips are pressed to my cheeks and his tongue slips inside me.
“Ahh…what…Paulo…don’t…don’t…”
I’m about to push him away when he applies his thumb to my still-buzzing clit, and I melt all over again. The weird, burning, tingling sensation of his tongue in my ass mixing with the throbbing of my teased button creates a heady, orgasmic cocktail. I’m suddenly twisting all over the couch, shrieking and begging, even though I don’t know what I’m begging for.
“Don’t…don’t…don’t stop! God…please…don’t stop…ohmygod…”
My second climax slams me like a tidal wave and I’m gasping for air. No man ever gave me a good, solid orgasm before Jason, but I don’t know if he’s ever made me come so fast, so hard, and so quickly all at once like Paulo does. Paulo has turned me into an oozing puddle of bliss. He can do as he pleases with me now.
“Please,” I pant. “Take me to bed.”
I don’t believe my eyes. I tilt my head and look down at the iPad in my lap askew. My view from the camera in the bookcase isn’t perfect. I only really see Paulo’s well-coiffed head buried between Anna’s legs, which are pushed hard back against her chest. He held them there at first, but then she wrapped her arms behind her knees and kept them there. Her ass is tilted in the air, and if I squint I can see he’s too low to still be licking her pussy. That fucker is licking her asshole! Holy shit! I can’t believe Anna is letting this guy lick her asshole!
To be fair, I don’t know if she’d let me do that because I haven’t tried. It’s not something I’d do. But Paulo has no trouble pulling that out on the second hookup. He hasn’t even fucked her yet, and he’s shoving his tongue up her asshole. That’s a real fucking man. He’s got confidence for days. I’m still shocked Anna’s letting him do it.
It took everything I had to resist rubbing one out when he made her come the first time. I’m trying to save it for Anna the way I did when I watched them together at the wedding reception. I don’t really know if that’s for her or if I’m just torturing myself. But it’s nearly possible to hold back when I hear the way Anna shrieks while he’s eating her ass. I see he’s playing with her clit too and Anna comes so hard she screams like she’s being murdered. Her usual fears about the neighbors overhearing seem to have evaporated. Anna is still panting when she tells him to take her to the bedroom.
If encouraging Anna to hook up with Paulo at the wedding was stupid, talking her into meeting him for drinks was insane. Turning your girlfriend over to such a stud once is a huge risk. Why did I need to go back for more? Anna tried to tell me it was a bad idea. She told me she didn’t need to see Paulo again, and I believed her. But I also saw that look in her eyes, and I knew she wanted to. And I wanted to see her with him again, and I couldn’t help myself. I had to talk Anna into it, but I didn’t have to work that hard.
I switch to the camera I stuck in the ceiling fan over the bed. Paulo tosses Anna onto her bed and strips for her. She watches like it’s the greatest show on earth. The guy is an Adonis. He’s built like a superhero. I swear I hear Anna gasp. I’m surprised Anna doesn’t just flop onto the bed and spread her legs. But my sweet, normally shy girl is not passive with Paulo like she typically is with me. She crawls to the edge of the bed and grabs that thing confidently. It looks like a third arm jutting out of him. Anna flips back her hair and smiles up at him and takes it in her mouth. Because her head is tilted back, I see it perfectly. Anna’s lips stretch obscenely wide and her cheeks bulge. She’s doing all she can to suck that thing. She slowly bobs and takes more, but she only manages to get about half in. Sucking my average dick hasn’t prepared her for this monster. My view was imperfect the last time I watched Anna blow him, so I didn’t see her struggle. She grips what she can’t swallow and sucks the rest. She finally pulls back with a gasp when she needs air.
“Oh, baby, that’s so fucking good. Most girls can’t suck me like that. Come on now and show me what you can really do,” he coos.
Anna licks all around his shaft and head like it’s an ice cream cone and I see her beaming at his compliments. She takes him back into her mouth and it looks like her jaw unhinges. When I think that’s all she can handle, Paulo laces his fingers in her pretty chestnut hair and pushes more cock into her mouth. Her face turns red and her eyes water while he slowly fucks it into her throat. Anna doesn’t try to push away. She grabs his ass and pulls, like she wants him to feed it all to her. Anna does love sucking dick — she’s a people pleaser — but this is ridiculous. Crazy sounds come out of her as he fucks her throat. She’s a drooling mess when he finally releases her. She gasps for air and falls back onto the bed. Paulo chuckles and it makes me want to punch him. I’m angry at myself for setting my girlfriend up to be used like that.
“You did so good, baby. Damn, I love your mouth,” he tells her. Anna smiles dreamily and reaches up for him when he leans in to kiss her.
They make out while Paulo slides her to the middle of the bed. Is she even thinking about the fact that he just ate her ass with that tongue? She throws herself into that kiss like. Anna is all in. He’s on top of her and he’s so massive I can barely see Anna underneath him. But I know when he stabs it into her because she cries out.
“God…yes! Oh god…Paulo…” she moans, voice deeper than I’ve ever heard it.
Anna’s arms and legs wrap around him when he starts pumping her. He moves so fluidly, like he was built for fucking. It’s truly impressive. He fucks like a pornstar, and I understand why Anna is making those noises. This is the way every woman should be fucked. He’s not taking her violently, but deep and steady, giving her the chance to savor every inch of that magnificent cock. He grunts with every thrust, but it doesn’t look like he’s exerting himself. Anna howls and she’s coming again. This god just made my girlfriend come three times like it’s nothing.
Anna’s still moaning when he flips her around onto her belly. He tosses her around like a doll and I love seeing her manhandled. I bet she loves experiencing it. Paulo hoists her cute ass into the air and pushes it back in. Anna whimpers like she can’t believe he’s still going. I would have come already when I felt her climax like that around my dick. He holds her slender waist and goes to work.

    Paulo doesn’t take it slow this time. He holds her slender waist and pounds his cock down into her. Anna screeches like she’s losing her mind. Her pussy has never been punished like this. It’s like his cock is telling her, I own you. You’re mine now. She buries her face in the mattress to muffle her screams and surrenders her pussy to him. But Paulo wants to hear Anna. He fists her hair and jerks her head back. She screeches even louder.

Paulo doesn’t take it slow this time. He holds her slender waist and pounds his cock down into her. Anna screeches like she’s losing her mind. Her pussy has never been punished like this. It’s like his cock is telling her, I own you. You’re mine now. She buries her face in the mattress to muffle her screams and surrenders her pussy to him. But Paulo wants to hear Anna. He fists her hair and jerks her head back. She screeches even louder.
“You needed this, didn’t you?” he taunts.
“Yeah…”
“Fuck that’s a tight pussy. I know you needed a proper fucking, Anna.”
“Yeah…yeah…oh god…” Every word is a stab in my gut because I know it’s true. I could never fuck Anna like this.
“Don’t worry, Anna. I’ll open you up, good. You needed a real man, didn’t you?” he growls.
“Yeah…yeah…I need it…please Paulo…don’t stop…I need it…”
Anna comes again while she begs him to fuck her. It’s a sight to behold. I wanted to save myself for later with Anna, but I can’t resist. Watching him effortlessly make Anna come is horribly beautiful. Paulo drills her from behind until he’s taken his fill and then he shanks it deep inside her and pumps her full of his huge load. She moans AHHH… as she accepts it. It’s shocking that careful Anna didn’t make him wear a condom, but I’m glad she didn’t. I enjoy the sick feeling of watching another man pump his load into my girlfriend.
I want him to go as soon as they’re done. I want that bastard gone so I can go up there and reclaim my girlfriend. But he stays and snuggles her. And then he fucks her again. Or, I should say, she fucks him. Anna bounces on his cock like it’s a pogo stick. I get hard again, but it’s too much for me. I love it, but it’s too much all at once. As amazing as Anna looks with her back arched and her tits thrust at the ceiling when she comes, I want her to myself. I’m recording it all, of course, so I’ll watch it all again later when I can really enjoy it.
It’s after midnight when Paulo leaves and I’m exhausted and sore. I just want to burrow into the covers and sleep. I don’t even care how huge the wet spot is. I don’t know how much of that was me or him. Paulo made my juices flow like a waterfall, but his cream was endless. He’s still seeping from me. I should have made him pull out, but he made me crave his come. When he came inside me, it felt like he was pumping life essence into me.
I think Jason went home. He must have. I don’t believe he would have stayed outside my apartment all this time. It’s kind of sad, thinking of him out there alone, waiting for Paulo to be done with me. He put himself in that position, but I still feel bad. I’m about to crawl out of bed for the shower when I hear the door. Jason knows there’s a spare key in the fire extinguisher box at the end of my hallway.
Jason strips as he comes into the bedroom. Honestly, I’m fucked out. Paulo rode me hard and put me up wet. But Jason looks so eager I can’t deny him. I open my arms and he slips right into me. It feels different. I try to tell myself it’s because I’m such a mess down there with Paulo’s cum, but that’s not really it. Paulo is huge. I didn’t know guys were really that big and I thought something like that would really hurt, but he is amazing with it. He wasn’t kidding when he said he’d open me up. It’s not like I can’t feel Jason — he’s not small. But his dick just doesn’t hit me the same. It still feels good. Every nerve in my pussy still tingles from Paulo.
“Was it good, Jas? Did you like watching?” I encourage, wrapping my arms around him. It’s so different, not feeling Paulo’s muscular back flexing.
“Yeah…oh fuck…you were incredible Anna…”
“It felt so good. He fucked me so good, Jas…” Saying things like fuck during sex still feel weird, but it’s what Paulo did to me. He fucked me good.
“I saw…you came so hard Anna…oh fuck…”
“I did Jas…I came so hard…so many times…” Paulo made me come more times than I could count. I came so hard when he fucked me from behind, I thought I would pass out.
“Ahh…Anna…”
Jason comes inside me and I’m glad he’s quick this time. He’d joked last time about how two men had come inside me in the same night, and it was true. But that was Paulo in my mouth and Jason in my pussy. This time both men had had my pussy and it feels so much dirtier. So very wrong. I don’t know what I’m turning into and I don’t know if I like it, but I love how it feels. He finishes adding his seed to Paulo’s and rolls off of me.
“Sorry you didn’t…” he says.
I rub his chest. “It’s okay. I came plenty tonight. I don’t know if I even could have done it again.” That might have been true, but I know Paulo could have made me come again. Paulo can make me come whenever he wants. I ask, “Are you okay with everything?”
“Yeah, you were incredible, Anna. It was an amazing show. Everything you did… You blew my mind tonight.”
I feel weird that he sees me having sex as a show. It gives me a deep, forbidden thrill, but it still makes me feel like an object in a way that’s uncomfortable. We need to have a conversation about it, but not tonight. I really need sleep.
“Are you good with it, Anna? I know you had fun, but do you feel okay about it?”
“I’m good, Jas. He was great, you were great. I just really need sleep, okay? I’m going to grab a quick shower first, though.”
I kiss his cheek and hop out of bed. I can’t put my finger on it, but something has changed between us. It’s not like I don’t still have feelings for Jason or want to break up because of this road we’ve gone down, but I don’t know how we can be the same after my night with Paulo. I’ll keep an open mind. I’m curious what we’re becoming. What I’m becoming.
