My Roommate's Loving Family Pt. 01

"Wait, you're a virgin?!"

Dave couldn't believe his new roommate, Brian, would just blurt that out so loud. He quickly looked around to make sure nobody was there to make him even more embarrassed.

"Yeah, dude what the fuck! Keep it down!"

"Oh shit, sorry man. Why, though? There had to be some sluts in high school or some chicks on Tinder or something?"

Dave shrugged and said, "Yeah, I've had some chances but I just get kinda freaked out. Honestly I just puss out when I've had the chance."

"Why?"

"I don't know, man, it's really embarrassing and personal."

"Dude, this is our first year of college, I can't have my roommate afraid to get pussy with me! I know we've just been here together for a couple months, but I think I might be the most chill person you'll ever meet about sex. Just tell me, I won't be a dick about it."

Dave's stomach was tight with embarrassment, but some part of him was all too eager to get this off his chest.

"My dick, I don't know, I'm just pretty insecure about the size."

Brian looked at him with sympathy instead of ridicule, making Dave feel a bit more comfortable. "Well, is it like a micropenis?"

"No, it's like 5, 5 and a half inches on a good day. And it's not very thick, I don't know I just feel, like, terrified of pulling it out for a girl and she's expecting some porno cock to tear her pussy up or something."

"Ahh, ok. I can understand that. Honestly though, that's not super small, that's pretty much average. Porno isn't average, the only people that feel compelled to show themselves fucking on camera are super hot people with huge cocks and amazing bodies. It's all skewed."

"Yeah I guess, I just still feel super insecure about it."

Brian felt bad for him. He had only known Dave a few months but he was a super good guy, and they always had a good time together.

"Listen man, I'm going home for the weekend, just come with me and talk to my sister about it."

Dave looked up at him with total disbelief. "What?"

"Yeah man, my older sister Dani is super cool about that shit, she's a Junior over at DePaul."

Dave still couldn't believe what he was hearing. "So I tell you I'm insecure about the size of my dick and that's why I'm still a virgin... and your next thought is for me to go tell your big sister about it?"

"No dude, she's not a therapist. I mean just come fuck her, she'll definitely be down, you just gotta ask."

Dave's mouth dropped open and he stared at Brian like he just saw a leprechaun. "Am I hearing you correctly or am I going insane?"

"Listen man, my family's just really open about sex, and Dani is definitely down. Just come over this weekend, you can crash at my parents place."

"Are you fucking with me right now? Am I going to humiliate myself in front of your family?"

"No, man, trust me! Jesus, I know my own family! I'll ask her for you, she's done this before for some of my dad's friends."

~~~~~

Dave drove out to the suburbs with Brian after class that Friday. Brian told him stories about growing up, and how his parents were always really open about sex.

"I think they just didn't want us to have any weird ideas or misconceptions, and they didn't think it was anything to be ashamed about. So we always asked questions, and they always answered honestly. When Dani and I started becoming more sexually active in high school, we would just tell the stories at the dinner table and my parents were super chill about it."

"Holy shit, man. My family is so thoroughly the opposite of that, I couldn't imagine it..." Dave had seen enough stepmom porn on the internet to think he knew where this was leading. "But you guys don't... like -"

"No! Jesus dude, come on! No, we don't fuck each other, we're not fuckin cave people or something," Brian said, looking disgusted.

"Well shit, I don't know! This is so... odd. I've never heard of a family like this."

"You'll have a good time, relax. They're sweet as can be."

~~~~~

They pulled into the driveway and rang the doorbell. Brian's mom answered the door, "Hi, you must be Dave! Brian told me he'd be bringing over his roommate for the weekend, so glad to meet you! My name is Stacy, come on in." Stacy was a natural blonde with a warm smile in her mid-40s and clearly took care of her body. She had the figure of someone who was just getting out of her fit soccer mom years. She hugged Brian and Dave, who felt her large, soft breasts press against him in her low cut v-neck t-shirt. Dave could see her shapely ass jiggling in her yoga pants as she led them into the house.

They walked into the kitchen and Dave and Brian put their bags down.

"So Dave, it's so nice to finally meet you! I'm so glad you guys get along, it can be such a pain when you have roommates you don't like."

Dave smiled at her and said, "yeah we've had a lot of fun so far. Thanks so much for having me, Mrs. Gray, I'm excited to meet all of you."

Brian smirked and said, "he's especially excited to meet Dani."

Dave looked at Brian with horror and rage, but Brian and Stacy just laughed.

"Ahh, I see," Stacy said. "She sure will be busy tonight, I think she has a friend from class over right now." Stacy turned to Dave with her warm, motherly smile. "I'm sure Dani will be delighted to meet you, you guys can go see if she's free now."

Dave still couldn't handle the innuendo in the air. He stayed silent, still weary of this whole situation turning into an elaborate and devastating prank.

"C'mon Dave, I'll take you upstairs," Brian said as he motioned for Dave to follow.

"Have fun!" Stacy said with a giggle.

Brain and Dave walked up the stairs and down the hall towards Dani's bedroom. The door was half open and the lights were on inside the room. As they got closer they heard the sound of someone spitting, and then Brian pushed open the door.

There was a man standing at the foot of her bed with his pants around his ankles. In front of him was Dani, topless and sitting at the foot of her bed, sucking and stroking the man's cock.

"Ah shit, at least shut the door! I don't wanna see this shit," Brian said with feigned disgust as he put a hand in front of his face to block his eyes.

Dani reached her head around the man's thigh and laughed. "Stop being a fuckin prude, you're in college now." She sucked the man a few more times and looked back up. "What's up?" she asked the boys.

Dave stared at Dani wide-eyed as she stroked the man's glistening cock and looked at them, waiting for an answer.

"This is my roommate, Dave, I told you he was coming this weekend."

"Oh my God, that's right!" Dani said and got off the bed. She walked towards them in the doorway and Dave tried his hardest not to stare at her tits as they swayed back and forth with each step she took. She had a big, welcoming smile on her face and gave Dave a warm hug. "So nice to meet you, Dave!" She turned to her brother and said, "I guess it's good to see you too, Bri" and giggled as she hugged Brian. She stood in front of them and asked, "so what's up guys?"

Dave struggled to contain his arousal as he saw the man behind Dani stroking his cock, waiting for her to return, and as she stood in front of them topless, lips still wet with spit.

"Dave wants to fuck you," Brian said casually as he pointed to Dave with his thumb.

Dave's stomach twisted with embarrassment and he slapped Brian's arm. "What the fuck, man!" Dave turned to Dani, who was giggling at his embarrassment, and stuttered "I'm-I'm-m sorry, he's just being a dick."

Dani kept snickering with a cute smirk on her face. She put her hands on her hips, pretending to be offended, and said, "Oh, so you don't want to fuck me?"

Dave was completely dumbfounded. "Uh, uh, uh, only if, uh, you would want to..."

Dani perked up immediately and said, "Hell yeah! Let's have some fun!" She pointed to the guy jerking off behind her and said, "Are you cool if I finish off Matt here?"

Matt waved at Dave with his free hand.

"No, not at all, sorry I can come back later," Dave stuttered, totally stupified by the absurdity of this situation.

"No, I mean are you cool to just fuck me while I finish blowing him?"

"Welp, that's my cue, I'm going downstairs," Brain said immediately after hearing Dani's proposal. "Come to the basement whenever you're done, Dave," Brain said as he turned around and left Dave alone.

Dani turned back to Matt. "Are you cool with it?"

Matt gave them both a smile and a thumbs up.

"Perfect!" Dani said as she grabbed Dave's hand and led him into her room. She took her sweatpants off and Dave noticed she wasn't wearing anything underneath. He saw her trimmed landing strip above her pretty pussy before she turned around to get back on the bed. Her ass was perfect, cheeks swinging with every movement, just as her tits did.

She hopped up on the edge of the bed and got on all fours in front of Matt, sticking her ass out in the air aimed at her headboard. "I'm already pretty wet, so you can just go ahead whenever you're ready," she said before putting Matt's cock back in her mouth.

Dave nervously pulled his pants down, revealing the outline of his boner in his underwear. He was trying everything to overpower his insecurity and his fear that she wouldn't enjoy it, or even worse, that she might laugh at it. He noticed Matt's cock was slightly longer than his, but was about the same thickness, and she seemed to be having a grand ole time polishing it off with her tongue. "Fuck it, here goes nothing," he thought to himself before pulling his briefs off.

Nothing happened.

No laughs, no stares, no humiliation. "Off to a good start," he thought.

He climbed on the bed by her pillows and stared into her pussy, swaying side to side while she wiggled her ass in the air for him. "Can I taste it?" he asked, cock throbbing in his hand.

"Whoa, we've got a gentleman over here!" she laughed. "Sure thing, cowboy, I'd love that."

He pushed his head in between her cheeks, nose nuzzled into her taint as he licked her wet pussy. Dani started moaning onto Matt's cock, and Matt said "oh shit, that feels so good." Dave kept eating her pussy from behind as she moaned with Matt's cock in the back of her throat.

Dani reached back between her legs and grabbed Dave's cock. Dave's eyes got wide and he lifted his head from her pussy. Dani began lightly tugging at his cock, and Dave followed her lead. She guided him into her warm, slick pussy and he pushed the rest of his way in.

"Ooh, there we go honey, that's better," Dani said while bouncing her ass cheeks around his cock. Dave held her hips and slowly began fucking her, pulling all the way out slowly and returning back into her until his balls graze her wet lips.

"Oh shit, you are really hitting a great spot for me, Dave." His confidence boosted hearing that and he began fucking her a bit harder. "Holy shit, does your dick have a little curve to it? That feels amazing!" she said, moaning and helping Dave fight off his insecurity.

She started to suck Matt's cock again, her throat vibrating around his shaft as Dave made her moan. "Oh fuck that feels good, I'm gonna cum soon," Matt said as his body began to clench up.

"Sorry, Dave. One sec," Dani said. She pushed off of Dave's dick and twisted herself onto her back so Matt's cock was above her eyes and Dave was kneeling in between her open legs. She opened her mouth and Matt bent his knees and dropped his balls onto her tongue while he jerked his load out onto her jiggling tits.

Dave watched as she put her tongue and lips to work around Matt's scrotum as he groaned, shooting long, thick ropes across her perfect tits right in front of him. When Matt finished, he let go of his cock and stood up, slouched and spent. Dani reached up with one hand, squeezed the base of his cock and pushed out one last drop that plopped onto her forehead. She laughed when it hit her forehead, and the boys giggled with her.

"Alright, you all good, Matt?" Dani asked as he started to pull his pants up.

"Yeah thanks, Dani, I really needed that."

"My pleasure! Do you want to stay and watch Dave's wonder cock fuck new parts of my pussy or are you heading out?"

Dave smiled wide as Matt said "Nah, I gotta head home to finish some homework, thanks though."

"Ok cool, see you in class!" Matt walked out of the room and she turned to Dave. "Alright mister, just you and me now. Do you mind if I stay on my back?"

"Uh, yeah whatever you're comfortable with."

Dani grinned. "You are so accommodating, I love it! Now put that beautiful thing back inside me, I want to see where else it hits."

Dave kept smiling and held his cock as he pushed it into her pussy. "Oh fuck, Dave that feels so good! Your cock is hitting my spot every time!" He looked down and couldn't believe how sexy this situation was. He was fucking this beautiful girl with jiggilng cum-splattered tits while she was rubbing her clit because of how much she loved his cock. He wasn't sure if this was real life or not but he was loving it either way.

Her mouth opened up and her eyes started to open wide. "Fuck, Dave, I cannot contain myself, I'm gonna cum soon. Just fuck me harder Dave, you're fucking my pussy so good."

Dave started fucking her harder and harder as he cherished every moan she let out.

"You like fucking my tight pussy while I'm covered in cum, huh Dave? You want to feel me cum on your fucking perfect cock?" she said aggressively, carnal passion in every word of her voice.

Dave had never been so turned on, he knew she was going to make him cum soon. He just needed to try to last long enough to make her finish.

Her eyes began to open wide and her body started to shake, the cum on her tits dripping off her nipples and onto the bed underneath her. "Oh FUCK!" she said as her pussy began to throb around Dave's cock, squeezing around his shaft and bringing him to his peak. He began to shudder as he came deep inside her hungry pussy. "Oh fuck yes, Dave, fill me up," she encouraged him as he shot rope after rope inside her.

Dani laughed and said "Wow, that was SO good! I love it when I can share an orgasm with somebody, that was so fucking hot," Dani said enthusiastically as she layed back on the bed, limp and exhausted.

Dave pulled his limp cock out of Dani's dripping pussy, still slightly panting. "That was amazing, Dani, thank you so much."

"No need to thank me, you've got a hell of a cock there! I'm yours any time you come to visit. Fuck, I might have to come visit you!"

She gave Dave a warm smile, then she looked down at herself and laughed. "Have you ever seen such a hot mess? Jesus, I'm dripping cum all over the bed!" She turned her head around and faced the door, still half open. "Mom! Can you please grab me a paper towel?" she shouted out to her mother, downstairs.

Dave panicked and said, "whoa, hand me my underwear!"

Dani laughed. "Don't worry about it, she's seen a cock before."

Her mom poked her head through the doorway and saw them both naked, Dani laying on the bed looking at her mom upside down with cum on her tits, while Dave was kneeling between her spread legs, his cock still glistening and dripping semen. Dave looked horrified and Stacy just giggled. Dani reached out for the paper towel and Stacy handed them to her and left the room.

Dani began wiping the cum off her tits, and then got up on her knees to push Dave's cum out of her pussy. Dave still couldn't believe what just happened. "Wait, so your mom obviously doesn't care that you just got spitroasted in the house, but you don't care if she sees you covered in cum?"

Dani shrugged. "I mean, it's not like she walked in here and licked it off my tits, or watched me while I got spitroasted. She just handed me a paper towel! What's there to care about?"

Dave was completely stunned by this family, but he wasn't going to complain about any part of what just happened.

Dani crawled closer to Dave until they were both facing each other on their knees. She wiped off the last bit of cum from her nipple and gave him a long, loving hug. Dave could feel the warmth radiate from her body and his heart felt full. She looked at him and said "I loved that, thank you Dave."

Dave smiled and she gave him a kiss goodnight. He put his pants on and walked downstairs and grabbed his bag from the kitchen. Stacy was sitting at the kitchen counter and looked up at Dave. "Did you have a good time, Dave?"

"Uhh, yeah," Dave said, unsure of how to respond. "Dani's really nice."

Stacy smiled and said, "my girl is very sweet, I'm glad you got a chance to connect with her. You don't have to feel uncomfortable, honey. We're very open about these kinds of things."

The tension in Dave's shoulders eased a bit. "Yeah I can tell," he said with a nervous chuckle. "It's very cool, my family was always so uptight about... you know, sex."

"Yes, most families are. Their father, Frank, and I grew up in similar households and just agreed we wanted to be different. Sex is a part of life, and it's a great part of life! We would never want to rob our kids of that great pleasure. Sure, we have our boundaries, we're not going to end up on Jerry Springer anytime soon, but sex is a beautiful way to connect with others and with yourself, so if our kids are having adventurous sex lives and they're enjoying it then we would only encourage that."

Dave smiled and felt her warmth when she spoke. "Do you think Brian feels a little strange though? That I'm here to... connect with his sister?"

"Not at all, honey. I think we all enjoy playing matchmaker a bit. He knows his sister loves to please just about anybody who asks, and he must have figured you would have a good time! We tried to raise our kids to be generous, this is just one way we like to share."

Dave felt a bit of relief, though he was still struggling to process all that had happened in the last few hours.

"Anyway, I'm glad you had fun. Brian's downstairs and your bed is ready there," she said to him, sensing his conflicting emotions. "Please, let me know if there's anything... anything at all... that you need while you're here." She winked at him. "Or anything you want."

Dave could feel his cock getting hard again. "Uh, thanks so much, Mrs. Gray. See you in the morning."

"Sweet dreams, honey," she said as he walked down the stairs to the basement.

Dave came to the basement and saw Brian playing Halo. "Hey man, what's up," Dave said to him.

"I definitely don't want to hear details, but hope you had a good time up there, man," Brian said sincerely.

Dave laughed and said "yeah, I think shutting up is the least I can do." He took a seat next to Brian. "So your family is really that open, huh?"

"Yeah man, have fun while you're here, they're all pretty open and they love newbies. The first time Dani brought her friend Tina over, my dad and I took turns on her all weekend. She begged us to DP her, but we just couldn't fuck a girl together, felt too weird."

Dave shook his head in disbelief, laughed at what a strange situation he was in, and then picked up the extra controller to fuck up some aliens with Brian before bed.