The week dragged by and, as expected, Katherine was against Gia going to the conference with me and my boss, Ray. The boss is the one that actually talked her into it in the end. He insisted, actually, stressing that this conference was an excellent networking opportunity for Gia and her getting a foot in the door this early could mean the difference in a long job search after college or having offers waiting on her to graduate.
Katherine talked to Gia, who basically said she was either going with her sister’s permission or without it, and Katherine relented. My wife pulled me aside and said, “Don’t leave Ray alone with her, at all, or I will castrate you when you get home.”
I promised Ray would not be left alone with her, even for a minute. I sat between Gia and Ray the whole trip. It clearly annoyed Ray, but I bluntly told him my wife’s ultimatum and he backed down and gave up on his hopes of more than a professional experience with her on this trip.
When we got to the hotel we found they were overbooked and Gia’s single room had been given away as it was the last room booked. So I called Katherine and told her of the situation. I had a room with two beds, Ray had a single bed in his suite, either Ray and I could bunk together, leaving Gia alone on a separate floor from me, or Gia and I could bunk together, putting Ray about two floors away from both of us. She went with the second option after talking to Gia and finding out she was nervous about the idea of me not being close enough to keep Ray in check should he decide to go to the desk for an extra key to the room booked under his name.
Gia and I unpacked and I taped a large black cloth to the wall behind the bed then stripped off the bedding and replaced it with a set I’d bought before we left. Trying to make the room look like anything but our hotel room. We did the conference shit, went to meetings and mingled. I made the effort to get Gia actually networking with people, then we decided to head up to our room to get room service, call Katherine, and let Gia rave about the experience so far.
I gave her a little wine with her dinner, just enough to calm her nerves about what was going to happen. After dinner I pulled out the lingerie I bought for her. It was a long red negligee with cap sleeves, a built in push up bra that laced up the center, and a white silk hip-hugger-style panty. She looked stunning as she walked out of the bathroom. I stopped setting up the camera and stared at her. The negligee split down the center of the front, so every time she moved I caught a glimpse of her beautifully pale skin.
Then it was time to get Gia’s computer and the cameras I bought for the occasion. I was going to take off my wedding band, but she asked me to leave it on. We had one of the cameras to the side of us, angled towards the bed. The other was on the bed angled towards us, giving the viewers both shots in a split screen.
She started the stream and, while she was perfectly in frame, I was mostly cut off as I stood at the foot of the bed, which was very much intentional. She introduced me as someone she considers family, almost like a brother and the requests for me to fuck her started rolling in, some with money attached to the requests.
She laughed and nodded, “Patience, my friends,” she cooed to them.
Gia knelt down in front of me and I watched the comments fly across the screen. I wanted to ask her if I was the first guy she’d been with on her stream, but me talking would be detrimental to keeping my identity a secret. Instead, I stood there as she pulled my clothes off of me. My dick was already hard and she enthusiastically took it down her throat, letting her viewers watch her opening the back of her throat up to try and avoid the audible gags as my dick became saturated in her spit. I rubbed the side of her jaw and tangled my hands up in her hair.
I could tell she was about to pull back for a break. She pulled back enough to catch her breath then looked up at me as I pulled her head down onto my cock until her lips were flush against my base. I moved her head very slightly and rocked my hips against her lips, a wet gagging noise as I rocked the tip of my dick in her throat made it difficult to not cum right then. I pulled her back off of my cock quick. She drooled and gasped, but managed a smile as she looked up at me.
Pulling her up to her feet, I guided her onto the bed, pushing for her to bend over the end of it. Then I gently slid her panties down and lifted the negligee up over her hips to expose her ass, though I left them both on her as I wanted her to look a little like a fallen angel. I spanked her ass, fully exposing her ass to her viewers. I pulled the camera behind her and I stood to the side slightly. I spanked her perfectly rounded ass again, this time rubbing down her cheek until my fingers could feel between her legs.
I spanked her again and she whimpered, lifting her ass to my hand as I soothed the ache on her cheek. I spanked her one more time and dipped my fingers between her legs. They came back out soaking in her fluids, she liked a good spanking, it seemed.
Requests of an ass fucking scrolled through the chat. That was the plan as it was. Her asshole was dry and I didn’t want to hurt her, so I spread her pussy fluids around her asshole with my fingers. She still wasn’t lubed up enough, so I ignored the fact that my face would be seen and lowered my mouth to her hole, licking and probing her ass with my tongue, lapping up the remnants of water from her shower before dinner.
I made sure there was a thick coating of my own saliva making her ass glisten in the soft lighting we’d set up for the show then I spread lube on my dick and and started pushing myself against her asshole. She cried out and I stopped, grabbing her laptop and putting it in front of her. I quickly typed a message to her viewers, ‘Tell her how good her asshole looks with my dick stretching her open and I promise to make her virgin pussy squirt when I tear into it.’
She was looking at the screen in front of her and she lifted her ass to me slightly as I stood behind and above her. I started pushing the head of my dick against her ass again. I pushed into her slightly and she shifted her body, her fingers curled into the sheets on the bed. I smiled as she relaxed her muscles and the head of my dick gently spread her open and allowed me entry into her body. She whimpered and her viewers got a good view of her ass being filled with my cock, and her face cringing and moaning as she experienced the fullness of anal sex for the first time.
Slow, gentle movements until I was fully inside her ass as she whimpered kept her viewers on edge. They wanted me to fuck her, not love her. She typed to her viewers as she could, which meant she had her eyes open and wasn’t moaning loudly. I thrust a little harder into her ass and she froze up and whimpered before sending the message. I leaned over her, not caring that I was at risk of being seen again. I wanted to see what she wrote.
‘Guys, you were right, it doesn’t really hurt. Just pressure and fullness and a need for him to fuck my hole harder.’
I pulled back and thrust hard and quick into her. I wanted to grab her hair and pull her head up, whispering ‘Does your asshole feel good, baby girl?’ But I refrained and instead shifted my position so the camera could see her ass puckering in and out with each thrust. I started moving harder and faster in her and she was whimpering and thrusting her ass back to meet my hips.
I really didn’t care if my wife found out at this point, “You gonna cum from my dick in your ass, baby girl?” I cooed to her.
Hearing me speak excited her more. I pulled her up the front of my body and untied the little laces holding the top of the negligee closed, cinching her breasts together and creating ample cleavage. Her tits fell free of the confines of her clothing and I pulled it from her frame. I had meant to fuck her cunt with that still on in order to stain it with her blood. Instead I wanted these perverts to see her petite body convulsing in pleasure from my dick churning up her ass. I grabbed her hair and pulled hard, arching her back into a tight curve as her body started trembling and my cock spurted deep in her bowels.
I pushed her down on the bed and moved the camera so it was right on her hole as I pulled out, the gaping view of her once virgin ass slowly closing back up, holding my seed inside of her, excepting the drips that flowed towards her cunt. I boosted her up onto the bed and finished pulling her panties down her legs and off of her feet. A quick bite to her ass cheek, then I leaned over and whispered to her, “Gonna wash my dick before the main event, you ready?”
She nodded and looked at me sadly, “Hurry, big brother, hurry.”
I obliged her request. When I came back out I turned her over onto her back with her knees bent up on the edge of the bed and knelt down in front of her. I played with her clit and cunt, fingering her and rubbing her gently while working on stretching her hymen a bit. Her cunt was so fucking tight, it was closing back up to almost nothing every time I pulled my finger from her. The goal was to get her to squirt when I broke her.
I sat on the bed and pulled her up onto my lap, her back to my chest so the camera had the perfect view of her perfect body spread wide. I continued to finger her little hole and rub her clit with one hand while my other hand groped and pulled at her beautiful tits. I felt her tightening on my fingers, her breath was rapid and shallow and her hips were rocking on my lap. She was almost over that edge, but I didn’t want her there quite yet.
“Open your legs up wide, baby girl, let’s let them see how big I am and how small you are,” I cooed to her.
She did as she was told. The illusion made it seem my dick would be somewhere above her belly button if I went to the hilt in her. Her pussy spread along the side of my cock and she gently rode me with her slick and wanting cunt. Then I cheated and retrieved the toy I’d bought her as a present earlier that week from the bedside table and brought it up to her.
The powerful wand made her pussy drool from the moment I touched it to her clit, soft whimpers and moans escaped her lips. She was bucking her hips and arching her back, being driven mad with need. I whispered to her, “Put my dick inside of you, baby girl, just work the head in to your tightness and I’ll take care of you.”
She tried to focus on that, but her body was writhing in need. She managed to get the head of my cock lined up perfectly with her hole, I wasn’t quite in her but I knew a hard fucking would send her over the edge.I put my hand on her waist and held her still as I thrust my cock up into her without warning. She screamed and cried out as my dick went straight in.
Her whole body rippled in convulsions, her head leaned back on my chest and her pussy flooded my lap with her fluids in a forceful spray. She was fully broken into adulthood and I whispered to her, “Would you look at that…your little cunt is begging me to fuck you a little harder, right?”
Her cunt was forcing my cock smaller, pushing the excess that didn’t want to fit in her back down to my base and it fucking hurt, but I did what I said I would do for them and I didn’t want to stop.
She whined and reached her arm back behind my neck and started lifting and lowering herself on my dick. A quick glance back to her laptop and I saw her feed was full of money offerings to her if I fucked her deep and rough. They wanted her to cry in pain, I wanted her to cry in pleasure. I won as I fucked her hole and groped her body. The wand lay on the bed beside us, I needed my hands on her tight curves and supple skin.
Gia arched and whimpered, panting as I put the wand in her hand, “Get yourself off on my dick, while I use your cunt to get my cum deep so I can breed you, baby girl,” I cooed.
She worked her clit, her pussy was almost constantly contracting on my dick as I fucked her hard. She sobbed and kept begging for more, “Harder, Dean, please fuck me harder. Yeah, like that,” she said as I bit her neck and used her tits as a hand hold to guide her cunt down to my thrusting hips.
The wand and my dick hitting her deep brought her to another intense orgasm as her hips bucked on my lap and her eyes rolled back in her head. She dropped the wand. And I felt her entire body tense from her toes curling and her back arching, to her cunt violently contracting on me, milking my dick for every ounce of cum it had, and I gave it all to her with my dick nestled tightly against her cervix.
I collapsed back onto the bed with her laying on top of me, her blood smeared on both of our thighs and my dick locked my cum deep inside of her. I whispered as I stroked and soothed her tense body, “Are you on birth control?”
She turned her head towards me, maneuvering herself so she could kiss me deeply, teasing my tongue and almost making me forget what I’d asked, “No, I’m not on birth control, now fuck me again please.”
I kissed her tenderly, trailing my fingers down her arms and over her body, “Are you okay with having my baby, Gia?” I asked.
She nodded, “Please fuck me again?” she begged.
I laughed and pulled her off of me, pink-tinged cum tried to leak in a deluge, but she closed up quick and just a little trickle with a few pumps of cum left her. I lay her on the bed and shut down the feed, kissing her softly as I hovered above her body. “I need a few minutes to get going again, but I promise you won’t go to bed tonight until I’ve pumped at least two more loads into you,” I said.
She smiled and swayed her hips, “Thank you, big brother,” her voice was saccharine and I needed to hear her begging me to make her a mommy.
I kissed her hard and ran my hands over her tits, “Tell me you want it, Gia,” I whispered.
She looked me in the eye and lifted her upper body, resting on her elbows and pushing her tits up slightly, “Dean…I need your cock in me again and I want you to record it just for us?”
I smiled and nodded, “We can do that, baby girl,” I said softly.
She spread her legs and looked me in the eye, “Good. And, just so you know, Sunday’s the end of my most fertile period for this month.”
I groaned as she rubbed my cock with her hand, “Seems like you’re ready for another go, daddy,” she whispered.
My hands gripped her hips and she guided the head of my cock into her again. This time I wanted to look into her eyes as I fucked her and the way her face contorted in pleasure just pushed me closer. “Gia, baby, I need you to not pout like that.”
She smirked and quickly pouted more, adding in a soft whimper. I grabbed her hair at the back of her head and pulled it hard. Each thrust hit deep inside of her and bounced her tits rhythmically. I was ready to blow but she hadn’t gotten off yet.
I pulled out and she whined, but I quickly got her onto her stomach and pushed my dick back into her pussy from behind. She whimpered and arched her back. My hands grabbed her tits, lifting and squeezing them as I pounded her cunt. Gia was squirming and I whispered, “Can you reach the wand baby girl?”
She looked to the side and stretched for it, barely pulling it over so she could grab it. I kissed the back of her neck and shoulder, letting go of her tits to push her hair over one shoulder and groaned, “Feels like you’re gonna cum again without even using that.”
Gia nodded and turned the wand on anyways, putting the foam head right on the edge of her hole as my dick pushed in, “Fuck, Gia,” I groaned. “Fuck yeah, baby, just like that.”
I moved my hands to her hips and pulled her back onto me hard enough to make her gasp and cry out. She looked back at me and turned up the power on the toy. Her eyes were watering and so were mine, “Harder, Dean,” she whispered.
Her pussy clenched on me and her body convulsed. I pushed deep and she rocked her contracting pussy on my dick, “Oh, god, Dean, more, please, more.”
I came in her cunt and pulled my dick from her and worked it into her ass again as she cringed and whimpered. I was only mostly hard, but something about her ass squeezing me got me going right away. She was crying and squirming in my grip and I fucked her hard as she used the toy on her clit. “Dean!” She screamed, “harder, please, harder.”
I couldn’t go harder, I wasn’t certain if the blood on her was from her virginity being taken or from me fucking her ass so roughly. I didn’t want to damage her and her need for me to go rougher was a little concerning. She squirted hard on the bed and I came in her ass as she sobbed and trembled. I pulled myself out of her and wrapped my arms around her, holding her tightly and soothing her. I may have actually broken her.
Source: reddit.com/r/Erotica/comments/i2yfr6/careless_whispers_part_five_first_time_anal