I spent most nights of my senior year in high school babysitting. It was my parent’s fault, really. Apparently having a real job would affect my grades too much, so I was stuck earning my money by spending my nights in various houses, feeding Kraft Dinner and hot dogs to hyper-active kids while their parents took a night off.
It wasn’t terrible, by any means. In fact, I took it quite seriously. I don’t mind children, and at most places I had full access to the fridge while I finished off my homework after putting the kids to bed. The pay wasn’t bad, either. I liked to play games with the kids and most of the time, the kids asked for me back before their parents did. I had a pretty steady clientele, most within walking distance of my house. It was convenient for me — I had procrastinated getting my driver’s license so long that I was 18 and still only had my learner’s license.
It was late February when Mr. Riley called the first time. I gave my cell phone number out to my clients, and he was lucky enough to call me on one of my nights off. I was in the bathtub when I answered.
“My name is George Riley. I’m looking for Anna Marchand,” replied the person on the other end. I immediately liked his voice. It wasn’t too deep, but it was soft and smooth. I was almost tempted to consider it calming, but he sounded slightly stressed.
“You’ve reached her,” I said.
“Oh, hi Anna. I’m a friend of the Anderson’s, and they recommended you as a babysitter. I’ve got a few late meetings next Friday, and my regular sitter isn’t available. I was wondering if you’d be available to watch my son.”
I shifted in the tub, hoping he didn’t hear the water splash. “I usually take Friday nights off, but it sounds like you could use the help.”
“I really could,” he said. “I’m afraid I can’t offer you more than your regular rate or anything…”
“It’s fine,” I interrupted. “I don’t mind, sir, really. I’d love to babysit for your son.”
“Thank you so much,” he said, sounding thoroughly relieved. “His name is Kyle, and he’s three. I would need you from around five until pretty late.”
“Not a problem,” I said. I got the rest of the details from him, and made a note of his address. He lived on the other side of town, but I was sure my mom would be okay with driving me.
Friday came along and I went home after school. I had worn a cute skirt to school and debated on wearing it to the Riley’s, but decided against it — three year olds could be really active and I didn’t want to deal with the skirt. Instead I put on my favourite pair of jeans, dark blue and fitting snugly, with a tight blue scoop neck t-shirt. I never tried to dress provocatively when I went to babysit, but I did try to look fairly nice. I rarely got to go out with friends or boys, because I always seemed to be taking care of someone else’s kids. Usually I was alright with it — not dating just meant I didn’t have to deal with all the drama my friends did, and there were very few guys I knew that I was really interested in, anyway.
I knew there was a reason for it. I would never tell any of my friends, but I found a lot of the men I babysat for much more appealing than any guy my age. I babysat for a lot of babies and toddlers, so their parents tended to be either late twenties or early thirties — not that much older than me, at any rate. A lot of the men were good-looking, and more than once I found my mind fixed on one of them while I got off before falling asleep.
I didn’t know about Mr. Riley, though. The Anderson’s were a couple in their early forties, and since they had referenced me, I figured Mr. Riley might be a bit older than the usual men I babysat for. Even still, I put a little bit of effort into my outfit. The t-shirt clung nicely to my breasts, which were a nice size — 36C, and fairly firm. I had a push-up bra underneath, which showed just a hint of cleavage. It fit slightly looser around my stomach. While I would never consider myself fat, I didn’t have the hard, flat tummies that all my friends seemed to work towards. I didn’t mind, though. It was a small price to pay for having great hips and a round ass. I knew that if I tried to lose any weight, I’d lose those curves, and that was not something I was willing to give up to have a flat stomach. After putting on just a bit of makeup and brushing my long hair off my face, I grabbed my backpack and went to ask my mom to drive me over.
My mom dropped me off at quarter to five. I walked up the driveway. The house was in a fairly good neighbourhood and looked pretty nice. I rang the doorbell and waited patiently.
The door was opened a few moments later by a man who, I was surprised to see, looked to be in his early thirties. He was good looking, about 6’2” and fairly toned, with deep brown eyes and dark brown hair. He was wearing a nice suit, but looking slightly frazzled.
“Mr. Riley?” I asked.
“Yeah, you must be Anna?”
I smiled. “Nice to meet you, sir.”
He smiled and opened the door. I turned around and waved at my mom, who had been waiting to make sure we had the right address. Mr. Riley led me into the house and offered to take my jacket. I smiled and gave it to him, looking around the house as he put it away. It was nice, but a little messy. There were toys everywhere and I could hear a TV playing a kid’s show in the next room.
“Sorry about the mess,” Mr. Riley said, returning without my jacket. “I haven’t had time to clean anything up.”
“It’s fine,” I said, smiling.
“No, it’s embarrassing.” He smiled at me apologetically. I grinned. He was very attractive, especially when he smiled. I was glad I had put a bit of effort into my outfit, and briefly let myself wonder what he was like in bed.
My thoughts were interrupted by a little boy rushing into the front hall. Mr. Riley turned and lifted the boy.
“This is Kyle,” he said. Kyle looked at me shyly, but he was smiling. He was absolutely adorable, with big brown eyes just like his father’s, and lighter brown hair that fell in his face. He had a smudge of dirt across his cheek and his father wiped it off tenderly.
“Hi Kyle,” I said. “I’m Anna. I’m going to be here with you tonight.”
“Say hi, Kyle,” Mr. Riley said, nudging the little boy.
“Hi,” Kyle said quietly.
Mr. Riley put him down and Kyle ran back into the other room.
“I’ve got to finish getting ready for my meetings,” he said. “If you wouldn’t mind watching Kyle?”
“Of course,” I replied, “that’s what I’m here for.” I walked into the other room and sat on the couch. Kyle looked up from the floor, where he was playing with some cars. I smiled at him, and he stood up, picking his toys up and walking over to the couch.
“Wanna play?” he asked softly.
By the time Mr. Riley poked his head in to tell me he was leaving, Kyle and I were playing cars. Kyle hardly noticed his father leaving, making my job easier. Kids always hate it when their parents go.
He was a good kid, and very talkative. We played cars until I decided it was time for him to eat. Over dinner, Kyle told me about his mom. I wasn’t exceptionally surprised to find out that his parents were divorced, but I was shocked to find out how much Kyle knew about it — especially how easily he told me about how his mother just walked out. It’s surprising how much information kids can absorb, and I felt so bad for the poor kid that I gave him an extra scoop of ice cream for dessert.
It was probably a bad decision on my part — the extra sugar hyped him up so much that I had trouble getting him to bed. By the time he finally fell asleep, it was an hour and a half past his bedtime, and I was exhausted from chasing him around. I felt bad for disobeying what Mr. Riley had asked, but figured I could explain it when he got home.
After Kyle was asleep, I tidied up the den and kitchen before settling myself on the couch. I turned the TV on and started studying. It didn’t take me long to finish my homework, so I spent some time channel surfing and reading some magazines that Mr. Riley had on the coffee table, checking on Kyle every once in awhile. I was so tired that I must have fallen asleep at some point, because I was startled awake when I heard the front door open.
I sat up and a magazine fell off my lap just as Mr. Riley entered the room. He smiled at me. “Did I wake you up?” he asked.
I yawned. “I guess so,” I answered, laughing. “I didn’t even realise I had fallen asleep.”
He laughed and entered the room, bending down to pick up the magazine I dropped. “Did Kyle wear you out?”
I smiled at him. “Well, it’s my fault, really.” I blushed. “I felt kind of bad for him, so I gave him a little extra ice cream after dinner. He went to bed a little later than you said. I’m sorry.”
“Oh, that’s fine,” Mr. Riley said. “It’s rare that he likes babysitters, so a little extra ice cream might have been okay.” He frowned for a moment. “Why did you feel bad for him?”
I bit my lip nervously. “Well, he just started talking about… about his mom… and I just…”
Mr. Riley smiled, holding a hand up to cut me off. “I understand.” I took a good look at Mr. Riley. He had a young-looking face, but he looked tired and really tense. His tie was loosened slightly and he had taken off his jacket, rolling the sleeves of his shirt up. He caught me looking at him and laughed a bit. “I’m a mess, I know,” he sighed, sitting on the couch. “It’s been hard since… well… she just left. I love my son but she was the one who stayed home with him. I’m still trying to figure out how I’m supposed to balance him and my job.”
I smiled, a little unsure of what to say, and he seemed to notice. “Sorry,” he said.
“It’s okay,” I answered. “Well, you know, if you need help I can always come over and babysit.”
He smiled at me again. “I’ll keep it in mind. And thanks for cleaning up, you didn’t have to do that.”
I smiled back. “It wasn’t a problem.”
“Well, thanks. It really helped.”
I picked up my bag. “Would you mind if I used your phone to call my mom?”
“Yeah, go right ahead. It’s in the kitchen.” He leaned back against the couch as I walked away.
I walked into the kitchen and picked up the phone, dialling my mom’s cell number. My mom picked up after a few rings.
“I’m ready to come home now,” I said.
“Sweetie, I’m so sorry!” she answered. “Haven’t you looked outside? It’s a blizzard out there.”
I glanced out the window, surprised to see a ton of snow and the wind howling. “I fell asleep, I hadn’t noticed.”
“That explains why you didn’t answer your cell phone. I keep telling you not to have it on silent. Hon, the car won’t start in this weather and it’s snowed in the driveway.”
“It’s fine, Mom, I’ll call a cab,” I told her.
“Okay, well let me know when it picks you up.”
I assured her I would, and hung up. I walked back to the living room, where Mr. Riley was still sitting on the couch.
“Do you have a phone book?” I asked. “My mom’s car won’t start, I need to call a taxi.”
“Of course,” he said, standing up. We walked back to the kitchen and he grabbed it out of a drawer, leaning against the counter as I dialled.
The phone rang once before a recorded message picked up.
“Thank you for calling Yellow Cab Company,” said a woman’s voice. “Because of the storm in your region this evening, we are unable to provide taxi service. If you are calling in regards to anything else, please press zero to speak with an operator.”
I hung up slowly, turning to Mr. Riley. “The cab company shut down,” I told him.
He nodded. “I thought they might have. The roads are awful.” He thought for a moment. “If it’s alright with you, you’re welcome to spend the night here. We have an extra room. I’d drive you but I don’t want to wake Kyle.”
I considered it for a moment. “It really seems like the only option,” I said quietly. “If you don’t mind, of course.”
He smiled at me. “Not at all. You were so helpful tonight, it’s the least I can do. Call and tell your mother, I’ll go get the guest room ready.”
I called my mom back, telling her I would be staying at the Riley’s.
“Well, alright,” she said, thought slightly reluctantly. “Remember to help Mrs. Riley make breakfast tomorrow.”
I pursed my lips, thinking it would be best if I didn’t tell her that there was no Mrs. Riley. “Alright, Mom, see you tomorrow.”
I hung up the phone and walked down the hallway, where a light was coming from the room next to Kyle’s. Mr. Riley came out as I was walking towards it.
“There’s fresh sheets and everything in there,” he whispered. “But I’m afraid I don’t have anything for you to wear.”
“That’s fine,” I replied quietly. “I can just sleep in this.”
He blushed. “Well, my wife left some of her things… I haven’t cleared them out of our room yet. If you’d like you can grab something of hers.”
I blushed in reply, but nodded, seeing as sleeping in my jeans would be kind of uncomfortable. Mr. Riley quietly moved past me and motioned for me to follow him down the hall.
We entered a big master suite, and I bit my lip a bit when I saw it. Not only had Mr. Riley referred to it as “our room,” as though his wife was still there, half the room looked like it hadn’t be touched since she left. His side had clothes on the floor and papers on the wardrobe, but hers was completely clean. There were even bottles of perfume still sitting on the vanity.
He turned around and smiled apologetically. “I should clean up, huh,” he said in a bit of a louder voice, obviously trying to joke a bit.
I laughed softly. “It’s fine.”
He motioned to the closet. “You can pick whatever you’d like. I’ll grab you a toothbrush.” With that, he turned and walked into the ensuite bathroom.
I opened the closet door. It was all woman’s clothes, organized by what must have been occasion, and then by colour. I couldn’t help but laugh a bit when I saw it.
There was a section specifically for pajamas. Mrs. Riley had a lot of matching lingerie sets, garters and see-through teddies, and I blushed looking at them. No doubt that she had worn them for Mr. Riley, and I wondered what kind of things they had done after he had slowly pulled them off her. I rifled through her clothes looking for something a bit less revealing. They felt musty, as though she hadn’t even moved them around for ages, even before she left. Dust bounced into the air as I rifled through the clothes. After looking through everything, I finally decided on a pair of shorts and a pink tank top. I pulled it out reluctantly, having hoped for at least a t-shirt, but deciding it would have to do.
I whirled around, suddenly hearing a small voice behind me. Kyle’s head was poked through the slightly ajar door, looking at me. I smiled at him.
“No, Anna. Remember me, Kyle?” I asked softly.
His face welled up immediately, and I looked at him helplessly for a moment. At that point, Mr. Riley came out of the ensuite.
“Shouldn’t you be in bed, buddy?” he asked.
“Want Mommy!” Kyle shouted, then began to wail.
Mr. Riley glanced at me. “Go ahead and change in there,” he said, pointing to the ensuite bathroom. “He doesn’t usually take long for me to calm down, but I’ll need to take him to the washroom.”
I watched as Mr. Riley picked Kyle up and began to walk down the hall. I walked slowly into the ensuite. It was nicely decorated, with a lot of men’s toiletries on the counter. I slowly stripped out of my jeans and t-shirt and took of my bra before pulling on the pajama set.
I immediately regretted choosing to wear Mrs. Riley’s pajamas. She must have been much skinnier than me, and a lot shorter. I pulled the tank top over my breasts with a lot of effort. The material was stretched across my chest and the hem ended a few inches above my naval. The shorts were a little easier to get into, but were still fairly tight, and a lot shorter than I thought they would be — they were practically briefs. I couldn’t do up the drawstring, so I just left it undone.
I stared in the mirror for a few minutes, nervously appraising my appearance. I glanced around the bathroom, looking for a robe of some sort, but found nothing.
“Anna?” I heard Mr. Riley call softly. I opened the door and poked my head out to see Mr. Riley standing in the center of the room. He smiled. “You found something, then?”
I blushed. “Ermm… sort of.” He looked at me, confused. “I found something, but I didn’t realise… well, it’s just that… I guess she was a bit smaller than me?”
He nodded quickly. “I didn’t think of that,” he admitted, but then shrugged. “It’s just for sleeping, though, it shouldn’t matter.”
I glanced in the mirror again. I had a feeling that Mr. Riley wouldn’t think the same thing after he saw his wife’s clothes on me, but I shrugged. “I guess you’re right,” I said, turning and opening the door.
When I stepped into the room, Mr. Riley’s mouth dropped open and I blushed immediately. He looked me up and down, staring at my body, and primarily at my tits.
Normally, I would have been embarrassed and slightly uncomfortable, being looked at like. I would have been even more uncomfortable noticing the sudden bulge in his pants. I mean, I wonder sometimes, but thinking about the men I babysit for and actually have them stare at me are two very different things. Mr. Riley, however, was a very good-looking man. I guess my next few actions I blame on that, and the fact that as someone who babysat nearly all the time, I hardly ever got the opportunity to get laid. I let Mr. Riley stare at me for a good minute before I giggled a bit.
“So, it’s not too small then?” I said, blushing as he tore his eyes off my body and looked up at me before glancing back at the floor.
“I’m sorry,” he said quietly, his voice breaking a bit. “No… it’s fine…” I couldn’t help but grin as his voice cracked a bit more and he held his hand out. “Your toothbrush?” he offered, still not looking at me.
I don’t know what possessed me to do it, but I walked towards him, swaying my hips a lot more than I usually would. I grinned as I stepped closer than I needed to, letting my fingers brush against his as I gently pulled the toothbrush from his hand. He was staring hard at the carpet, a muscle in his jaw twitching slightly.
“Thanks,” I said softly. “Is Kyle okay?”
He nodded. “Just misses his mom sometimes,” he said, still staring at the floor. “He should sleep through the rest of the night though. Usually only wakes up the one time.”
I smiled, staying quiet. After a moment, Mr. Riley’s gaze shifted. Only slightly, but I knew his eyes were back on my tits.
“You can touch if you want,” I whispered.
I nearly expected him to back away from me, the way his eyes shot up and looked at me. I looked back at him, still smiling.
He reached out tentatively and put his hands on my hips, looking nervously into my eyes. I bit my lip softly and stepped forward, nearly pressing against Mr. Riley. I reached up and placed my hands on his shoulders.
“This is wrong…” he muttered, pulling me a bit closer and pressing me against the hard bulge in his pants.
I grinned at him again. “It’s okay if I want to, too,” I whispered.
“You’re the babysitter. You… I just met you…”
“We both want it…”
“You’re so young…” he continued, nearly pulling back.
I laughed. “You seem to be enjoying it so far,” I teased, rolling my hips a bit, rubbing against him.
He groaned and roughly pulled my hips, pushing me against him before he stooped down a bit and kissed me hard. I kissed him back, my hands resting loosely around his neck. I ran my tongue along his lip and he groaned again, his hands trailing around from my hips to my ass, rubbing up along my back and shoulders, and then finally cupping my breasts. I moaned softly against his mouth, biting down softly on his lip.
“I wanted to fuck you the second you walked in the door,” he said gruffly, his lips suddenly on my neck as he fondled my breasts. My nipples hardened under his palms, the cotton of the tank top rubbing against me. “I thought about you my entire meeting. Jerked off in the bathroom before I drove home.”
I moaned when he said that, my hands trailing down to rub his hard cock through his pants. He groaned and pressed into my hands. He was sucking on my neck, one hand on my breast and the other rubbing up and down my hip and stomach. I tilted my head back, moaning as he touched me.
Without warning, he put his hands on the back of my thighs and nudged my legs apart. In a single, swift movement, he lifted me off the ground. I squealed, shocked, and wrapped my legs around his waist. I could feel his hard cock pressing against me as he turned, carried me over to the bed, and gently set me down on the edge, his lips pressed against mine the entire time.
He pulled away from me gently, grinning for a moment before he went to the door, shutting it completely and locking it. I grinned at him as he turned back to me, leaning back on my arms and spreading my legs a bit.
“Fuck,” he said, looking at me. I giggled and he walked back, sitting next to me on the bed. I leaned forward and kissed him again. Each time his lips touched mine I felt a tiny shock shoot through my body, nearly leaving me short of breath. I let one leg rest across his lap, and he ran his hand up my soft, smooth leg. I shivered as he touched me, his hands leaving a trail of goose pimples behind them as I felt what seemed like surges of electricity run through my body.
His hand trailed up my leg and hip, along the bare skin on the side of my stomach, and finally stopped on my breast, overtop the pink tank top. My nipples were already hard, and he pinched the left one lightly through my top. I gasped when he did and he kissed me harder.
My nipples are incredibly sensitive, and each time he rolled one between his fingers, my clit throbbed. I moaned against his mouth and he reached up with his other hand, cupping my other breast and pinching that nipple, too.
I could hardly take it, and I broke the kiss suddenly. He looked up at me, slightly alarmed, but I just giggle and pushed him back on the bed. I straddled his lap, leaning down to kiss him against as I started to unbutton his shirt. He flicked his tongue against my mouth, his hands reaching up to rest on my ass.
As I finished unbuttoning his shirt, I gently rubbed my covered slit against the bulge in his pants. He groaned loudly and thrust up, grinding his hard cock against my clit. I moaned and pushed his shirt off. The second he shrugged it off his arms, he started to pull on the hem of the tiny tank top I was wearing.
I let him push it up a bit before I leaned back a bit, grabbing the hem myself and pulling the tight material over my head. My breasts bounced out of the shirt as I pulled it over them, and I heard Mr. Riley inhale sharply as I finished pulling it over my head and drop it on the floor. When I looked at him, his eyes were wide as he stared at my breasts.
“Everything okay?” I asked. I looked down at my body. My nipples were dark pink, medium size, and incredibly hard. My breasts seemed to be swollen from just the little bit of kissing and touching we had done. I was getting so hot, and I knew my skin was flushed, the pink tone spreading from my cheeks to the base of my neck. Mr. Riley seemed to be enjoying it, at any rate, and he stared at me for a long moment before saying anything.
“Your tits are fucking amazing,” he gasped. He gently pushed me off him so I was lying on my back, then immediately pressed his mouth to my breasts. I moaned as he licked and sucked them. He lavished attention on one before switching sides, cupping my other breast with his hand as he rolled his tongue around my nipple.
My legs were spread and he was lying between them, and before long my cunt was throbbing so much that I had to arch my back and grind against him, needing some friction on my clit. Without moving his lips from my breast, he reached down with one hand and gently rubbed my slit through the shorts.
It felt amazing. His fingers were skilled and felt so good against my throbbing pussy. It still wasn’t enough, however, and I gently pulled his head off my tits, kissing him hard as I reached up to unzip his pants. I undid them quickly and he let me push them down and throw them to the floor. He was wearing boxers, and I could see his cock straining against them, the bulge enticing me. I ran my hands along his chest and stomach, before sliding one under the waistband and wrapping it around his cock.
He groaned again, leaning down to resume sucking on my tits as I started to stroke his cock. It was smooth and throbbing in my hand, and bigger than I expected. I rubbed it gently and he pushed forward in my hand, his moans stifled by my tits as he pressed his face against them.
I stroked a bit harder and he thrust into my hand again, moaning. He pulled his head from my breasts and kissed me, still rubbing my clit through the shorts.
“Keep doing that and I’m gonna cum way too fast,” he gasped. I giggled and he shook his head. “I’m not joking. I haven’t gotten anything near this since Kyle was born.”
I raised an eyebrow and he blushed a bit. “My wife…” he started to say.
I kissed him quickly and giggled again. “You don’t need to explain,” I said quietly, stroking his cock lightly. He groaned and rubbed my clit again.
“So good…” he mumbled, and I moaned as touched me. I started stroking his cock a bit faster and he groaned.
After a moment he reached down and grabbed my wrist gently, stopping my movements. He kissed me hard, on the lips and then along my jawbone before trailing his lips down my neck, sucking gently. He pulled my hand out of his boxers as he kissed my neck. He licked down my chest and gently ran his teeth on my nipples, making me gasp. I felt his lips trail down my breasts and onto my stomach, where he licked and kissed down to the waistband of the shorts. He then started to pull on them, sliding them down my hips, his lips trailing along behind them and gently kissing my pussy as he slipped the shorts off.
He sat up and just looked at me for a moment. I blushed a bit when he didn’t say anything, and he noticed, laughing a bit.
“You’re fucking gorgeous,” he whispered, leaning forward to kiss my inner thigh. “My wife was nowhere near as sexy as you. She had no tits, no hips.” He kissed up my thigh, spreading my legs a bit more and kissing my pussy lips. “You have such a hot body.” He reached up and cupped one of my breasts as he kissed my pussy, touching everything but my clit. “Big, firm tits.” He reached under me with his other hand, cupping my ass. “Nice, round ass.” He finally kissed my clit, sucking on it gently. I cried out, arching my back against him. “Sweet, tight pussy.” He plunged his tongue into my cunt and I moaned loudly, reaching down to press his head harder against me.
He licked my pussy and then moved his mouth to my clit, sucking on it as he pushed two fingers into my cunt. I moaned and couldn’t keep myself from grinding against his mouth and fingers, panting as I wound my fingers in his hair. He licked eagerly, biting gently on my clit as he thrust his fingers inside me.
“M-mr. Riley…” I panted a few moments later. “I’m gonna… oh God gonna c-cum…”
He responded simply by sucking harder on my clit and pushing his fingers faster. I came hard, moaning loudly as I felt my orgasm crash through my body. My toes curled and I arched my back. I wasn’t sure if I had shut my eyes or just temporarily blinded myself from the amount of pleasure I felt.
When I came down a bit, I could feel Mr. Riley still licking my pussy, lapping up my juices. I was panting as he did so, and he finally moved his head away and crawled up, laying down beside me. I looked over at him and he grinned. I couldn’t help but laugh.
“My wife hated that,” he said.
“What was wrong with her?” I gasped.
He laughed and leaned over, kissing me hard. I kissed him back, tasting myself on his lips.
“You’re so fucking young,” he murmured as he kissed me, gently rubbing my breasts. “This is so wrong.”
I laughed. “I don’t see you complaining.”
“I’m not,” he replied, rubbing my nipples lightly. “Just can’t believe how hot this is.”
“Can’t believe you’re fucking a young little high school babysitter?” I asked teasingly. He groaned and kissed me, flicking his tongue against mine. I reached down and pulled his boxers off, sliding them down and pulling his cock out.
He was uncut, his cock a bit longer than usual, and very thick. I licked my lips as I looked at it, and he laughed.
“I’d ask you to suck it,” he said, “but I want to fuck you. I can’t wait any longer.”
He rolled onto his back and pulled me on top of him so I was straddling his lap. I slowly lowered myself onto his cock, moaning as I felt him enter me. His cock felt huge inside my cunt. I hadn’t had anything but my fingers in there recently, and the only guy I’d been with previously had a much smaller cock than Mr. Riley’s.
I let it enter me slowly, allowing myself adjust to his thick meat. He moaned as my tight pussy inched down on his cock, until he was finally buried hilt-deep in my cunt. I stopped for a moment, letting myself get used to the foreign feeling in my pussy. Mr. Riley reached around me and put his hands on my ass, pushing me down even harder on it. I moaned when he did, and slowly started moving myself on top of his cock. The feeling was amazing, and I moaned as I let his cock slide in and out of my pussy.
“Fuck…” he groaned, and his hands slide to my hips, guiding my movements on top of him. I started to ride him a bit faster, panting as he thrust up into me. My breasts started to bounce as I moved faster, and he reached up with one hand to cup them as I rode his cock. I moaned as he pinched my nipples, moving faster and harder on top of him, and moaned even louder as he used his other hand to rub my clit. I loved the feeling of his cock moving in and out of my tight, stretched hole, and before long I could feel myself nearly ready to cum. My hips bucked and he pressed on my clit and pinched my nipple at the same time, and I came again with a loud moan, tilting my head back as he thrust himself up into me. I rode my orgasm out, before nearly collapsing on top of him. He pulled out for a second and pushed me gently onto my stomach.
“Get on your hands and knees,” he said softly. I obeyed immediately and he moved behind me. He reached one hand under me and gently stroked my dripping pussy, and with his other he reached over to the bedside table. He grabbed something – I didn’t know what until I felt a hand spreading my ass cheeks and a gentle, slippery finger probing at my hole.
“Mr. Riley?” I asked nervously.
He pressed a soft kiss on my back. “It’ll be okay,” he whispered. “Please, Anna. I love doing this and my wife never let me.” He kissed me again, reassuringly. “It might hurt a little, I’m not going to lie, but it feels really good after a bit.”
I hesitated at first. “Okay,” I finally said.
He slipped a finger into my hole, and the feeling wasn’t bad. He wriggled it around a bit and I even moaned softly. After a moment he took it out and when he put his finger back, it felt even better. This time, he slowly added a second finger. I moaned and pressed back against him as he repeated his movements from before.
He laughed softly and I could hear him using a lot of the lube. His tip pressed against my hole. He pushed with a bit of force and I felt his tip slide into me. My asshole stretched around it and I started to breathe a bit harder. He pushed his cock into my ass slowly, letting me adjust to the size. It was uncomfortable at first, but before I knew it his entire cock was buried in my ass. He pulled out slowly and pushed back in. It didn’t hurt as much that time, and the next time he did it, I moaned.
He was moaning as he started to thrust a bit harder into my ass, though nowhere near as hard as if he had been fucking my pussy. It still felt amazing, and by the sounds he was making, I was guessing he thought so, too. He reached around me and gently stroked my clit with one hand. The other was braced on my hip as he pushed his cock inside me.
“Fuck, Anna,” he groaned, “this is… fucking amazing… you don’t know how fucking good this is…” He moved a bit faster, not too quickly, and I moaned as I felt his balls slap against me as he fucked my ass.
He kept talking, though I couldn’t really understand what he was saying. Mostly things like “so good” and “so tight” and “fuckfuckfuck.” But I did understand when he cried out “Fuck, Anna, I’m gonna cum!”
His body shuddered against me and I felt his hot load shooting into my ass. He was leaning against my body, supporting himself as he moaned and came hard. Panting, he finished, holding his cock inside my ass for a few moments before he gently pulled out.
I practically collapsed on the bed, and he fell right next to me. We lay there, and I listened to him pant for a minute or two before he said anything.
“I haven’t cum like that in years,” he finally murmured, sitting up. I watched him move off the bed and walk, naked, across the room. He flicked the light off and walked back, pulling the covers up. I pulled myself under them and he lay down beside me, reaching over and wrapping his arms around me.
“So it was good?” I asked, giggling.
He laughed. “Good? It was fantastic. Amazing. Fucking… wonderful.” He held me close to him and I could hear his heart pounding. “Just what I needed.” I sighed contently. “I can’t thank you enough for this, Anna. For everything.”
“I enjoyed it too, Mr. Riley,” I replied.
He laughed again. “You don’t have to call me Mr. Riley,” he said, yawning at the end of his sentence. I agreed silently, starting to fall asleep as our warm, naked bodies pressed together.