Note: As per my other stories, the character names are all changed on the off-chance that there is someone who recognizes any of the descriptions of living arrangements or furniture. If this is the first story of mine that you are reading, I have stories before this - while the other stories are not necessary to read, they do help to build up some backstory to where I was in my life at the time. Once again, while the verbal interaction may not be accurate, the physical interaction is to the best of my recollection. I've edited the titles of my other stories to include numbering in case anyone is confused. I apologize that the site doesn't list them in publishing order, but I can't really do anything about that - doing what I can. Enjoy!
My first few months of college were over, and it was time to head home for Thanksgiving. I had been having a blast at college. I was getting better grades than I got in high school (putting in more work, of course), having sex with any woman who wanted it, and partying harder than I had ever tried when I was in high school. I was actually kind of thankful for the break from dorm life more than anything. It would be nice to see my family and friends from back home whom I wasn’t living with. I got home and had a nice dinner with my family, which was great – I hadn’t seen my sister in half a year, and hadn’t seen the rest of my family since they dropped me off at college three months earlier. We had a big turkey dinner, did the usual Thanksgiving stuff, and then I went to bed early. It was weird how a bed that had been my own for almost nineteen years was suddenly almost weird and foreign.
The next day I helped out around the house, assisting my mom with some yard work and changing burnt out bulbs that they just hadn’t cared enough to replace. After studying a fair amount during the day, I got a call from Bill. He was having a party that night since his parents would be out late, and anyone from our graduating class was invited, as well as people from our dorm that we met who lived near enough. Unfortunately, Alexa and her dad had decided to go visit her aunt for the holiday, so she was on the other side of the country. I was bummed about that, but at least I would get to see some of my friends that I hadn’t seen since various points of the summer. I had dinner with my parents and then it was off to Bill’s.
“Your parents got you a keg?”
“Two kegs, actually,” Bill bragged.
“Dude, that’s kinda fucked up.”
“Whatever, I’m not complaining,” he laughed.
“So how many people are coming anyway?” I didn’t think we would get enough people to show up in order to polish off both kegs.
“I dunno, man. I invited everyone that we hang out with and told them all to get the word out.”
Get the word out. That is the phrase that turns a good party into an out-of-control-cops-get-called kind of party. I have never been one to like big parties. When I went to keggers in high school, I hung out with my group of friends, we drank, and then usually ended up leaving to go hang out somewhere else. I went inside and began to put things I knew to be valuable in a basket.
“What are you doing?” Bill asked, joining me inside.
“Moving all this shit up to your parents room so they don’t kill you when someone breaks it.”
He started grabbing other things, and we put them all upstairs out of harms way before carrying a couch upstairs from the living room and putting it at the top of the stairs with a paper sign on it reading ‘STAY DOWNSTAIRS’.
“Alright man, people are probably gonna start showing up in an hour or two, so I’m gonna get ready. You cool just chilling while I shower and stuff?”
“Of course,” I told him, going back downstairs and doing one last look around to see if we had missed anything important.
“Hey, can you go buy some ice,” Bill yelled down from upstairs.
“Alright,” I yelled back up, going out the door.
I dumped the ice in the giant bucket the first keg was sitting in, before lugging the rest into the Deepfreeze in Bill’s basement. Coming back upstairs, I saw a face I had rarely seen over the last few years.
“Oh my god, Rob!” Lisa yelled, running across the hall to hug me.
“How’s it going, Lisa?” I laughed. She was as hot as ever, and dressed to kill.
“I’m good. How’re you liking college? Bill said you guys are having a ton of fun!”
“It’s not bad,” I answered. “I didn’t know you were going to be here tonight.”
“I wasn’t supposed to be,” she sighed. “My plans fell through, so I invited some people over to join Bill’s party.
“Does Bill know?” I laughed.
“Not yet. He just got in the shower a couple minutes ago.”
“It should be fine. Man it’s great to see you. You look phenomenal,” I complimented her.
“You look great yourself. I talked to Bill last night… he said you’re getting around at college,” a grin spread on her face.
“Uhh, I guess,” I stammered.
“It’s ok. It’s college – you’re supposed to have fun, remember? Besides, if I were at college with you, I’d be on that dick every night,” she bit her bottom lip. “Come on,” she told me, grabbing my hand and running to the basement.
Closing the door behind her, she pushed me onto the bed in the spare bedroom.
“I don’t know if we have time for this,” I told her, sitting up on my elbows. “And what if Bill comes down looking for me?”
She left the room again for a minute, before returning.
“I told him you had to go home for a bit to help your dad with something and you’d be back.”
Wasting no time, she was naked in under a minute. Jumping onto the bed, she didn’t even bother with foreplay, pulling my jeans and boxers off, and sliding herself down my already hard cock.
“Fuck, I missed this,” she told me, putting her hands on my chest and bouncing gently up and down.
I let her ride me for a couple minutes before grabbing her and flipping her over, her legs over my shoulders. I started to fuck her hard and fast – we didn’t have a lot of time, and Bill would surely hear her moaning if he happened to come down to the basement. She let out a small squeak each time my cock buried itself in her velvet sheath, sounding like a dog’s toy.
“Fuck me, fuck me, fuck me,” she moaned, rubbing her clit while I continued to thrust into her.
Her legs kicked into the air, wrapping around me as her pussy started to squeeze my cock hard. I waited for her small orgasm to pass before lifting her off the bed and spinning her over again to fuck her from behind. I shimmied up her back so I was fucking her from above, my cock eliciting a small shriek every time it rubbed into her g-spot. Her pussy wasn’t incredibly tight, but I could still feel myself about to cum.
“I’m gonna cum,” I told her, continuing to fuck her hard.
“Ok, in me,” she squealed.
I took a few last thrusts before I began to empty into her. I pulled out and my cock oozed a bit more cum on her leg.
“Holy shit,” I panted. “That was great.”
“I know,” she gasped, catching her breath and rolling onto her back.
I leaned over and kissed her gently on the lips.
“This was way better without Charlotte around,” she smiled up at me.
“Is she gonna be here tonight?” I laughed, getting a punch in the arm for my lack of sensitivity.
“She is,” Lisa answered. “But she’s been dating a guy for like three years now. She actually hasn’t cheated on him once.”
I was kind of surprised, but thought better of pursuing the matter.
“Alright, Rob. I need to go retouch my makeup now. But I just want you to know that my panties are gonna be soaked in your spunk for the rest of the night,” she kissed me again softly before leaving me alone in the basement.
“Where the hell did you come from?” Bill asked, as I walked outside.
“I was just checking for more shit to put away downstairs,” I lied to him. What was I going to say? That I had just fucked his sister, and not for the first time?
“Alright, well people are showing up. Let’s get this keg flowing,” he told me.
The party was going on for a while. It was actually a pretty good time, even with the probably one or two hundred people crammed into his backyard and house. It was nice to catch up with people I hadn’t seen, especially all my good friends. It felt like no time had passed at all, and we were joking just like normal within seconds. There was one small downside – Emily was at the party. I had done a pretty good job avoiding her, but people kept telling me that she wanted to talk to me. Whatever it was, it couldn’t be good. Seeing her coming my way from across the backyard, I ducked inside and ended up in the basement with Lisa and some of her friends.
“Hey, loser,” Charlotte teased as I walked in.
She had apparently gotten kind of fat since I last saw her, and I wasn’t going to let her comment slide. “Damn, I’ve heard of the freshman fifteen, but I never knew about the jumbo junior,” I slapped her with my words.
All the guys in the room started to howl with laughter. Some of the girls were laughing too, while a couple were scowling at me for my rude retort.
“Rob, that’s not cool,” Lisa told me, grabbing me and escorting me from the room.
“Sorry, Lisa,” I offered once we had left the room.
“It’s fine, I just wanted to show you something,” she told me, pulling me into the bathroom.
Locking the door behind her, she reached her hand down the front of her pants and scooped out some of my cum and her juices that had mixed together in her panties. Looking me in the eye, she licked her fingers clean, before smirking and rinsing her hand off. This girl was something else.
“Thanks again,” she winked, leaving me alone in the bathroom.
I was about to leave as well when Emily walked in.
“There you are,” she smiled at me.
“What’s up Emily,” I answered politely.
“Nothing, I’ve been looking for you.”
“Oh, really? I’ve been around all night,” I told her, wanting to get to the point.
“How’s college going for you?”
“It’s good, Em,” I sighed. “What do you want?”
“I just wanted to talk to you. It’s been hard, ya know.”
“What do you mean? What’s been hard?” I asked her.
“College. I mean the classes are fine, but I just haven’t had an easy time making friends.”
I felt a little bad for her – she had had a pretty rough adolescence being shipped off to boarding school for a couple years, and now this.
“What’s going on? You’ve never had a problem with people,” I replied.
“I miss you a lot,” she started to cry. “I thought we were going to be together when we went to college, and we’d live together after our freshman years.”
I didn’t know what to say. I didn’t want to be a complete asshole, and there was definitely no way she was ready to hear that I had been dating her best friend behind her back for over half a year.
“Don’t you miss me?” she asked, looking through tear-filled eyes.
“Honestly? No, Em. I’m sorry, I just… I moved on a while ago.”
I heard her breath catch in her throat.
“You don’t think about me?”
“Not really, no. Sorry, but it’s probably better to be honest and kind of blunt than to lead you on. I haven’t thought about you or us in that way since prom.”
“Can’t we just… once more?”
I thought back to my arrangement with Alexa. The only person she had forbade me from ever having sex with was the girl who had locked herself in the bathroom with me moments ago.
“No, Em. I’ve moved on. I’ve been seeing someone,” I explained.
I didn’t have the balls to tell her the truth.
“No, I’ve been dating a girl I met at college since the first week I got there.”
“Is she here tonight?”
“No, but that doesn’t matter,” I sighed. “Look, Em… it’s over. Do what you gotta do, but don’t do it with me.”
I tried to gently move her out of the way of the door, but she tried to slap me.
“You’re never going to find someone as good as me,” she screamed at me, as I managed to push past her and open the door.
She kept trying to smack me in the side of the head when Lisa came out of the room her friends were in.
“What the fuck are you doing?”
“Lisa, this is Emily, my ex-girlfriend.” I had managed to grab Emily’s wrists, but she was still trying to knee me.
“Stop trying to hit Rob, or get the fuck out of my house,” Lisa grabbed Emily’s hair, yanking her back.
Emily turned to try and swing at Lisa, and I took this opportunity to grab her and pin her arms to her body, dragging her slowly upstairs. Lisa followed behind from a safe distance, lest she get a foot in the face. I carried and dragged Emily to the front door and took her outside when Lisa opened it.
“Stop, alright?” I told her.
There was a few people standing in the doorway, shocked at what was going on.
“Go home, Em.”
“You’re not welcome in this house,” Lisa added.
I let the other people inside, before closing the door behind me and locking it. Looking through the peephole, I waited until Emily eventually started to walk down the street. Turning around, I saw a bunch of my friends laughing and slow clapping at what I had just done. I didn’t smile, pushing my way through them to get something to drink.
The rest of the evening passed without incident. People were being respectful of the house, nothing was getting broken, and most people had started to leave once the second keg went dry. Despite there being nothing broken, there was still a lot to clean up. There was no way Bill would spend his whole night policing people to take off their shoes when they went inside, so there was a lot of dirt on the floor. Fortunately it was mostly hardwood, though there was some carpet that would need cleaning.
As the last of our friends disappeared into the night, Bill went upstairs and passed out on his bed. Lisa and I were getting a head start on cleaning up when her parents walked in. I apologized for the dirt on the carpet, but told them I would have it cleaned up before I left.
“You can stay over, Rob. You can always stay here if you need to,” she told me, hugging me hello.
“Alright, well I’m still gonna try to clean it tonight.”
“Don’t worry about it, kiddo,” Roger laughed. “I’m beat, and I don’t need that damn machine keeping me up.”
Lisa excused herself, following her dad upstairs, while I continued to clean the hardwood floor.
“Rob, relax. We can clean it in the morning.”
“Are you sure, Hailey?”
“Ya it’s fine,” she smiled.
I walked outside with her so she could survey the damage done to her backyard.
“This isn’t so bad. Some people walked through my garden, but there’s nothing growing right now anyway,” she shrugged.
“We already cleaned up a lot of the cups,” I explained why it didn’t look bad.
We were walking back inside when Hailey stumbled a bit, grabbing my arm for support.
“Woo,” she laughed. “I guess I had more wine than I thought. Rob, could you help me downstairs?”
“Ya, I snore when I’ve had too much to drink. My husband won’t be too thrilled if I keep him up all night.”
Walking downstairs with her, we opened the door to the bedroom to find a couple girls asleep in it. We closed the door, and Hailey led me to the playroom.
“I didn’t know Lisa’s friends were staying over. I’ll just sleep on the couch.”
I had been planning on sleeping in that bed myself – now that the couch was no longer an option either, I stood there looking around, while Hailey laid on the couch, pulling a blanket over herself.
“Rob, can you close the door and come over here for a moment?”
“Sure thing,” I told her, doing as she asked.
“You know, you’re such a great guy. I remember when you started staying over here all the time, you were a chubby little thing. You’ve really grown up and gotten to be a very good-looking young man.”
“Uhh… thanks,” I blushed.
“You know, I saw you once.”
“I saw you once. You and Lisa and Charlotte.”
My eyes went wide with horror.
“It’s fine, sweety, really. My daughter is a bit of a slut, I’m well aware.”
“Well, that was,” I began to explain before she cut me off.
“Rob. It’s fine.” She sat up. “I’ve thought about that night often. You had your hands full with those two girls,” she said, emphasizing the word ‘girls’.
“Ya, well. It was a couple years back. Sorry.” I didn’t know what to say.
Hailey grabbed my hand, pulling me to sit down beside her.
“You know, Rob… I’ve never been able to get the sight of you out of my head. You were young then, and it was inappropriate… but you’re older now, and I find myself following my body’s urges.” She gently stroked my cheek.
I had obviously thought about Hailey in a sexual way at some point in my past – she’s a pretty good-looking woman, and I was at her house all the time. I had never seriously thought about it, though.
“When I saw you in bed at college with…”
“Ashley,” I provided the name for her.
“With Ashley… I couldn’t help but think how great it would feel to be that dumb girl on the bed, instead of the neglected woman waking you up. Do you know the last time my husband fucked me when it wasn’t my birthday?”
“Hailey, this is… weird.”
“Am I making you uncomfortable?”
“Kind of,” I answered honestly.
She pushed on, ignoring me.
“We’ve fucked maybe three times in the last two years, Rob. Three times. Do you know how hard it is for a woman my age to see attractive young men at the gym? They flirt with me, but I don’t do anything.”
“Maybe you should talk to your husband about this,” I offered, standing up.
“We’ve talked about it for years, Rob. We’ve seen marriage counselors, we’ve tried spicing things up in the bedroom… nothing seems to work. He can barely get hard for me anymore.”
This was way too much information for me to know about my best friend’s parents.
“Please… sit down, Rob. I just need to talk about this.”
I hesitated momentarily, before complying, although I tried to sit with a bit of distance between us.
“When I saw you in bed with… Ashley? I couldn’t help but think about that night a couple years ago. I masturbate to the thought of you all the time now, Rob.” She grabbed my wrist to discourage me from standing up again. “I can’t get you out of my head. I snuck off to the bathroom at the restaurant we were at tonight and touched myself to this,” she flipped open her phone to show me a picture of me in bed with Ashley. “Thinking about me being the woman beside you.”
I was stunned. She had managed to take a picture of me in bed without her husband noticing, and before I had woken up. Not only that, but my best friend’s mom had just confessed that she was fingering herself to this picture, and the thought of having me as a sexual partner, for the past three months.
“Hailey…” I began, collecting my thoughts. “You’re Bill’s mom. You’ve looked after me so much over the last ten years.”
“I know, so I think you kind of owe me,” she laughed.
She crossed her leg over mine, straddling me on the couch.
“I need this, Rob. Please.”
“Hailey,” I tried to stand up, but she wouldn’t allow me. “This is just weird. It’d be like I was fucking my own mother.”
“Don’t talk like that,” she was breathing heavily now. “How many other women have you fucked, Rob?”
“I don’t know.”
“Guess,” she told me.
“Maybe like… forty?”
“Am I not attractive enough?”
“No, you’re plenty good-looking,” I looked her in the eyes.
“Rob… I know things will never be the same. But they won’t be the same already, anyway. After what I’ve told you, things are already permanently different between us.”
“So you might as well fuck me while you have the chance,” she finished my thought.
“This is a one-time thing?”
“It’s a right now thing. If it happens again, it happens again,” she smiled at me, realizing that she was finally winning me over.
“Do you have a condom?” I asked her. I didn’t happen to have one.
“I had my tubes tied after Bill,” she told me.
“I’ve fucked a lot of girls with no rubber,” I explained. “I got tested when I first got to college, but I’ve fucked girls since then.”
“I’m sure it’ll be fine. Get that cock out for me.”
I was still shocked by this situation. I had never heard Hailey talk this way, and it was definitely arousing to be with a woman I had jerked off to a few times over the years. Never did I think this would be a reality, though.
I pushed her off of me, standing up and dropping my jeans to the floor.
“Hang on,” she said, going over the door.
She pushed a chair under the doors so no one would be able to get in on the off chance someone tried. Coming back over to me, she slipped her dress off her shoulders, letting it join my clothes on the ground.
“You’re such a lucky boy,” she told me, referring to my size. “You’ve got those girls at school lined up down the hall for a chance at this, don’t you?” She grabbed my length, tugging me roughly a few times. “Sit down, Rob. It’s been a while since I did this,” she told me, taking me into her mouth.
It may have been a while since she blew her husband, but she was damn good at it. Her hand stroked the base of my cock while her mouth swallowed me until it met her hand. Every time her mouth reached the end of my cock, she swirled her tongue delicately over my bulbous head, like it was her art project. Her other hand lightly rolled my balls back and forth, gently pulling on them as she continued to expertly fellate me.
“Oh my god, that’s amazing,” I moaned, as she stood up to slip her bra and panties off.
Her breasts sagged a little, but they were still reasonably firm and her nipples stood out from her breasts like two little nubs. I noticed some razor burn around her pussy.
“Did you just shave recently?” I asked, standing up and taking her ass cheeks, one in each hand.
“I’ve been thinking about you coming home for the holiday for months, Rob,” she moaned, stepping onto her tiptoes as I squeezed her ass.
I suddenly realized that she had probably convinced her husband to buy kegs for her son in order to set this entire plan into motion.
“You set this whole thing up?”
“I need you,” she moaned, grabbing my cock again and rubbing it against her belly.
I lay her on the couch, kneeling between her legs.
“Do you… do you do oral, Rob?”
I sat back and laughed.
“It’s ok… you don’t have to,” she shied away.
“It’s not that… Of course I ‘do oral’.”
I put my face between her legs, slightly wrinkled and stretched with age, and began to kiss her inner thighs. Her hand reached down, grabbed the back of my head, and pulled me to her pussy.
“Eat me,” she moaned, as I tongued her labia.
I stabbed at her pussy a few times with my tongue, before sucking and licking her lips and clit, adding fingers inside her to increase the stimulation. Her pussy was tight, I assume from years of neglect, and she had a death grip on my fingers. Fucking her was going to be a treat. I continued to suck on her clit until I felt a smell tremble with my fingers and heard her moans catch in her mouth with each shuttered breath from her orgasm. Scooting up the couch, I quickly rubbed my cock around her pussy for lubricant, before gently pushing it in.
“Oh fuck, that’s good,” she moaned, pinching her nipples while her shoulders writhed around on the couch.
I slowly pumped in and out of her, trying not to elicit too much noise.
“Kiss me,” she demanded, pulling my face to hers.
Our tongues danced in the chasm between our mouths as our bodies became one mass of rhythmic fornication. I reached under her armpits, grabbing her shoulders for leverage and began to pump into her harder and deeper, masking her moans with my mouth. Pulling my mouth away, I clamped a hand over hers as she cried out with another orgasm. Her hand reached up, taking mine and pointing my fingers into her mouth, sucking on them with as much intensity as her pussy was emitting during her climax. I waited until her pussy stopped its spasms before continuing to fuck her deeply.
“Can you cum in me, Rob? It’s been so long,” she begged me with her eyes.
“Whatever you want, Hailey,” I told her, picking up speed as my own orgasm approached.
I grunted my climax into her, her legs wrapping tightly around me to encourage the release of my seed deep inside her. Her hand rubbed gently on my cheek, as she caught her breath and thanked me again and again.
I woke up a few hours later to Hailey sucking on me again.
“Just enjoy this,” she told me, pushing me back when I tried to sit up.
She tried her hardest to take as much of me in her mouth as she could, but couldn’t get much more than halfway down before she gagged.
“Sorry,” she wiped the spit from her chin. “I can do this… it’s been a while.”
I laid back and relaxed, watching this mature woman do her best to reassure herself that she still had her skills. It took a few minutes, but she managed to get about six inches in before she had to pull off for air.
“I need you to help me,” she told me, grabbing my hands and helping me to my feet.
She laid on the couch, her legs going up the back of it and her head hanging over the edge. I knew exactly what she wanted to me to do, so I pushed my cock into her mouth, and asked if she was ready. She mumbled yes around the invader in her mouth, and I gently pushed. Her throat wasn’t opening up to me, so she grabbed my hips and pushed and pulled on me, encouraging me to do what I had to. I grabbed her head with both of my hands and started to fuck into her throat. I could feel her gagging and trying to force me out, but it was just her natural reaction – the rest of her body gave no indication that she was in trouble. I pulled out, let her catch her breath, and then pushed back in.
“Here we go,” I told her, before pushing all the way until my balls rested against her nose.
I rested there for a few seconds, enjoying the feeling of her throat squeezing my head and cock, trying to milk me. She tapped my thighs and I pulled out, and she flipped over, sitting up.
“I knew I could do it,” she laughed. “Are you gonna cum?”
I wasn’t close, and told her so. She thought it was a bad idea to keep going, since her husband would probably be awake soon, and she apologized repeatedly for leaving me with an erection. I told her it was fine and that last night was amazing.
“It was. Thank you so much, Rob.” She gently kissed me on the lips, her hand robotically finding its way back to my cock and stroking it lightly. “Oh my god, I’m sorry. I can’t get enough,” she laughed again. “I’m going to make pancakes – are you going to stay for breakfast?”
“Sounds good,” I told her, watching her get dressed and quickly sneak upstairs.
I waited for my cock to deflate before dressing myself fully and going upstairs.
“Good morning, Rob,” Hailey ‘greeted’ me, in her housecoat now.
“Morning,” I answered cheerfully.
“What are you up to this weekend, Rob?” Roger asked me, his paper lifted in front of his gaze.
Hailey rubbed her ass against me, winking at me over her shoulder, as I replied that I didn’t have anything going on and was probably just going to study and then take the train back to school early the next day.
“Oh, well Hailey is driving Bill back tomorrow. Give him a ride, sweetheart – save the kid some money,” he suggested.
“I’d be fine with that,” Hailey answered happily.
Reaching behind herself, she squeezed me through my jeans. I closed my eyes and swallowed the moan that was trying to escape. Keeping my eyes on her husband, I reached up, my hand snaking its way into her housecoat and squeezing her naked breast.
“That would be great,” I smiled, breathing in the smell of her hair.
We heard footsteps on the stairs, and separated from each other with the memory of a few hours earlier fresh in our minds.