Family with Benefits Ch. 01

Hi! My name's Stephanie, but all my friends call me Steph. I'm 21 and live at home with my Mom. I know what you're thinking, you're thinking, "Another Gen Z kid who'll never grow up and stop mooching off their parents." That's not the case, though. Mom and I have a great setup; I help around the house, we keep each other company and are super close. It'd be impossible for a Mother and daughter to be any closer!

My Mom raised me on her own after my Dad died. I was really young, when Dad went to the store because I wanted ice cream. Some asshole went to the store because they ran out of beer and crossed the center line, hitting Dad head on. Naturally the asshole walked away with some scratches and bruises; Dad died on the scene.

My grandma, on Mom's side, helped Mom a lot while I was growing up, though I didn't realize how much until much later. They arranged their schedules so that Mom could be there to get me off to school and grandma was able to come by not long after I got home from school. Grandma would help me with my homework and make dinner. When Mom got home, we'd have dinner, spend a couple of hours talking, then she and grandma would put me to bed. I never knew how much longer grandma stayed, but she was always gone when I got up, because she had to go to work, too. Grandma usually stayed over on the weekends, though. Our sofa wasn't particularly comfy, so she stayed in Mom's room.

You may have the wrong idea about my grandma. She wasn't a little old lady. She had Mom when she was 16, so she was only in her 40s, but had been a widow for quite a few years. My grandpa was a banker, working at the World Trade Center on 9/11. He left her a nice little nest egg, but she kept working to make sure she didn't run out in retirement. Grandpa's death also left Mom with a strong need for life-affirming experiences. One of those experiences resulted in me.

Mom was lucky in that my Father wasn't some douchebag fuckboy. He was about 10 years her senior, and worked for a big tech company. They actually liked each other and, when he found out she was pregnant, he promised to take care of us. They got married and fell in love with each other. They had some good years together before the drunk driver took my Dad. Dad's parents weren't able to help much after Dad died, because they were in their 70s, not in the best of health and lived halfway across the country.

Grandma spent less time at our place as I got into my mid-teens and Mom started going to parties. I was glad that Mom started going out a bit, because she hadn't dated at all since Dad died. Mom's drop-dead gorgeous and could've had any man, or woman, that she wanted, but she stayed single. Mom always looked so gorgeous when she went to those parties, her hair done perfectly, her makeup flawless and the clothes accentuated her curves wonderfully. The day after, Mom was always in such a great mood, she must've had a great time.

One weekend, Mom said she was going to one of her parties. I didn't have school the next day, so I asked if I could join her. Mom and I have always had a policy of total honesty, so she told me the whole story. The parties that she was going to were sex parties and I was too young to attend. She did promise that she'd bring me to one when I turned 18 if I was still interested.

For my 18th birthday, Mom threw a party for me and a few of my friends. There was pizza, cake, ice cream and embarrassing singing. After everyone left, Mom said she had a couple more gifts for me. She gave me a very pretty, lacy pair of panties, a blouse that was just a front with a very low neckline, and a tiny miniskirt. I thanked her and then she gave me another surprise. She said there was going to be a party the next evening if I wanted to attend. I had been way too curious, for way too long to pass up the opportunity.

The next day, Mom woke me up early. She had a plan for our entire day, we'd get our hair and makeup done, get mani-pedis and look absolutely resplendent for my debut. When we got home, I got dressed in the outfit Mom gave me. I don't want to sound conceited, but I looked ridiculously hot and felt super sexy.

On the way there, Mom laid out the ground rules. First, consent is mandatory; no one touches anyone without their consent. Second, badgering someone until they give in is not consent; I shouldn't let anyone pressure me to do anything. Third, what happens there stays there. Fourth, as long as those rules are met, absolutely anything goes.

We were greeted by a gorgeous woman in a luxurious purple silk robe, who looked to be in her 40s. She embraced me warmly, then held me at arm's length to look at me. "Your Mother told us you were beautiful, but words fall far short of doing you justice. You are nothing short of exquisite. I do so hope I can get to know you better tonight." I was more than a little surprised. Had this woman just implied that she wanted to have sex with me? I got my answer when she turned and kissed Mom. And holy shit did she kiss Mom! I had been on quite a few dates and kissed quite a few boys, with their raging hormones, and I gotta say, all of them together weren't half as passionate as that kiss.

The lady, whose name I later found out is Sue, gave Mom's backside a playful swat as she closed the door behind us. Entering the living room, we were exposed to a lot of people and no clothes. There were people in their 20s, through their 60s, there were dad bods, Greek gods, heroin chic chicks and voluptuous vixens. Some of the people were in groups, playing, but a large group were gathered around watching a tall, skinny man fuck a short Japanese girl's brains out. It took me a moment to realize that it was Jim and Kimiko, who I'd met a few times at holiday parties.

Mom walked up to a man in his 50s. He had a little bit of a paunch, but was in otherwise decent shape. It was obvious that he'd been a mountain of a man when he was younger, and his forearms still looked like they were made of thick steel cables. Without a word, Mom wrapped her hand around his very impressive cock. "Ah, June, so good to see you!," he exclaimed before pulling Mom in for a brief kiss.

"Dave, I'd like you to meet my daughter, Steph."

"She could be Aphrodite's twin. Truly stunning, just like her Mother. It is a pleasure to meet you, young lady," he said, extending his hand in greeting.

Let me tell you, it's very awkward to have your Mother introduce you to someone while she's jacking him off. The awkwardness was worth it when Dave introduced me to his son, Brian. It was easy to see the man the father had been in his son. Brian looked like his body had been hewn from stone, using Adonis as a model. He noticed that I was a bit nervous with all of the public nudity, and asked if I'd like to go somewhere a bit more private. I looked over at Mom and she just smiled and said, "Have fun, baby."

Brian led me past a couple of open bedroom doors to a closed door, marked "PRIVATE". He led me in and we sat on the bed and kissed. My heart was hammering away. Here I was, about to have sex for the very first time with someone I had just met at a fucking orgy!

I expected Brian to be like the other boys I had dated, rough lips on mine, a tongue trying to use my uvula as a boxing bag, and rabid grasping at my boobs. Instead, I got soft lips and a tongue gently probing, a hand lightly resting on my thigh and one stroking my back. The hand slipped up my thigh to my hip as the other moved up to untie the knot that served as the "back" of my shirt. Of course, now that he had unfettered access to my boobs, Brian would treat my nipples like the knobs of a radio faintly picking up the only signal in a 100 mile radius. Again, I was pleasantly surprised. He covered my breasts in kisses, before circling my nipples with his tongue and sucking on them. It felt so wonderful. He had my dripping wet in no time.

Brian kissed his way down my stomach. When he got to my skirt, he slid down to kiss my inner thighs, then looked up at me, questioningly. What I thought was, "Oh my god, is he going to lick my pussy?" What I said was, "Yes, please yes!" He slipped my skirt down off my hips and down my legs and tossed it aside, Then, he kissed all around my pussy before running his tongue slowly, oh so slowly, up and down my slit. After a few minutes of licking, he moved up to take my clit between his lips, sucking gently. I had never felt anything like that in my life. It was wonderful, amazing, mind-blowing! He kept it up until I was right on the edge of cumming, then he stopped and asked, "Do you want me to fuck you?" What the hell was I supposed to say? "No, I don't want your gorgeous cock, I'd rather lie here dying of frustration?" No way! I begged him to fuck me and fuck me hard and he certainly obliged.

I don't know if Brian somehow knew that I was a virgin or if he was being gentle was just in his nature, but he took it slow when slipping his cock into me. Once he was in me, he started thrusting slowly. Brian kept the pace slow until I was ready and urged him to go faster. I was so turned on that I came almost immediately when he started fucking me in earnest. He slowed briefly to give me a moment to catch my breath, then got back into it. By the time he was done, he had given me another great orgasm.

After we were done, Brian held me, kissed me, stroked my hair. He told me that I was amazing and asked if he could call me later. We ended up dating for a few months before he graduated from college and moved cross-country. Those were good months and losing him hurt, but I managed to get by.

Brian and I walked, hand-in-hand, back to the main room without a stitch of clothing between us. As we entered, we saw that Jim and Kimiko had finished and been replaced with another spectacle. We didn't have a good angle to see what was going on, but we could tell there was a curvaceous blond on a table, a woman with her face buried between the blond's legs, and a man pounding away at her. As we walked around to get a better view, the man finished. Like a gentleman, though, he started fingering and licking his partner. When we got closer and could see the woman in the middle, I learned two things that changed my life. First, my Mom is bisexual. Second, the sight of her pussy turns me on more than I could ever have imagined possible.

I couldn't help myself. I slid a hand down to play with myself. My mouth was watering, my pussy was dripping and my mind was racing with conflicting thoughts. "She's a woman! If Mom is bi, maybe I am too. But she's my Mother! And she's so fucking sexy." I was knuckles-deep with two fingers in myself when I heard a sultry voice purr in my ear, "Do you really want to do that yourself? I'd love to use my tongue to help you out." This was a day of new experiences, and I wasn't going to pass on this one, so I nodded assent. A gorgeous Latina with flawless bronze skin and shimmering black hair knelt in front of me and immediately started eating me out. That partially answered my question; I definitely enjoyed a woman's touch. I still wasn't sure if I enjoyed sex with women or just enjoyed having my pussy licked, though.

I was in heaven. I was getting to watch as a stranger played with my Mother, and I had an unparalleled beauty between my legs. The woman that Mom was licking was thrashing and babbling incoherently, clearly having a mind-blowing orgasm. That seemed to push Mom over the edge. Mom's moans grew louder and louder, and soon her cum was running down the man's hand.

Mom came over and started stroking my hair with one hand, while tracing lines across my chest and stomach, avoiding my breasts, with the other.

"Are you having fun, baby?"

"Uh, uh, mmm, yes," I stammered.

"Good. I'm glad you're enjoying yourself. Did you just watch Mommy cum?"

"Oh fuck, um, y-yes," it was getting harder to talk.

"Oh, I hope you enjoyed seeing that. Are you going to let Mommy watch you cum, now?"

I could only nod, as I was right on the edge. Seconds later, I was weak in the knees and shaking uncontrollably. Mom held me to keep me from falling and the smell of her was strong in my nostrils. The smell of her, her shampoo, her perfume, her arousal, was intoxicating.

Mom cooed, "Good girl. Mommy's baby girl has grown to such a beautiful woman."

It felt so nice being held by Mom. Nice in a very different way than when I was a kid. My skin thrilled to feel her pressed against me. When I regained my strength, Mom said, "Why don't you come help me thank our hostess properly?"

"Um, sure. How?"

"I think she'd enjoy having a mother/daughter duo eating her out. And it'll give you a chance to taste pussy, and a particularly delicious pussy at that."

With a mix of excitement and trepidation, I agreed. Mom put her arm around my waist and we walked around, looking for Sue. When we found her, she was still in her robe, on her knees in a corner sucking Dave's dick and jacking off two other men. Mom and I stood back, giving her time and space to finish the task at hand. The two men getting hand jobs shot their loads on Sue's face and Dave finished in her mouth. The men thanked Sue and hugged her, before stumbling away. She stood and was using a wet wipe to clean her face as she turned to see us.

"Ah, there you are! I've been hoping I'd get to see you both again. Based on the goofy grin on Brian's face, I take it the two of you had fun?"

I blushed bright red and stared intently at my feet. "Yes, ma'am."

"Oh, don't be so formal, love. Please call me Sue."

"Sue, Steph and I would like to thank you for hosting us. Would you mind if we eat your delicious pussy?"

"A mother/daughter duo? How could I possibly turn that down? Let's go over to the sofa."

Mom untied the sash holding Sue's robe together, letting it fall open to reveal her body. Mom walked behind Sue and slipped the robe off her shoulders. Cupping Sue's breasts, Mom asked from over her shoulder, "Isn't she sexy, baby? Come here and give Sue a kiss."

I'd be lying if I said Sue's kiss didn't curl my toes. When we finally broke our kiss, Sue sat on the sofa with her legs spread wide and her hips off the edge. As Mom lavished love on Sue's breasts, I put my face between her legs. I kissed both of her outer lips, then extended my tongue to run it through her slit. After I got my first taste, Mom moved down to lick Sue's clit. My tongue reached the top of its up and down journey in Sue's slit, meeting Mom's flicking tongue. Holy shit, that was electrifying!

I'm sure we were at it for several minutes, but it felt like we only got to lick Sue for the tiniest fraction of a second before she was cumming. Her cream was like nothing I'd ever tasted before and I licked as fast as I could, not wanting to miss a drop. The last remaining question was answered, I must be bisexual, because I definitely loved licking pussy. A vision of Mom's cream running down that man's hand suddenly popped into my mind and I wondered if she tasted this good.

Eventually, the party wound down and we went home. A couple of days passed, but I still couldn't get thoughts of Mom's pretty pussy out of my mind. I needed to see it again, so I came up with a plan. I bought a sex toy and played dumb, asking Mom how to use it. I knew she'd see through the act, but I thought she may go along with it anyway. This would give Mom an excuse; she wouldn't be playing with herself for her daughter to watch, she'd be teaching her daughter. I didn't say it was a good plan.

Anyway, my stupid plan worked, maybe too well. Mom lead me to her bedroom and pulled her toy out of her nightstand; it was not an accident that I chose one just like Mom's. Mom took her pants off and sat on the bed, with her back against the headrest. She spread her legs wide and motioned for me to come closer. My face was maybe a foot from her sexy snatch. Mom said it was very important to make sure you were prepared before using the toy, then fingered herself until she was visibly wet. Then she put the dildo in her mouth to lubricate it, before slowly slipping it into herself, inch by inch.

Mom had my complete and undivided attention as she fucked herself. The sight of the dildo sliding in and out of her, the sound of her moans, the scent of her growing arousal, all were conspiring to make me too horny to think straight. Part of me wished she wasn't my Mom, because then she'd let me bury my face in that sexy pussy and spend the rest of my life eating her out.

Like I said, my plan worked a little too well. After Mom brought herself off, she pointed out that being shown how to do something was useless if you didn't practice. She had me take my pants off and fuck myself while she watched. Honestly, I was so horny that I would've been playing with myself anyway, but having Mom watching made it a lot hotter. Mom moaned and said, "You're doing such a good job, baby girl. I bet if you keep fucking your pretty little pussy like that you're going to cum." She was right, and hearing that pushed me right over the edge.

Like I said, my plan worked a little too well. Mom had me "practice" almost every day the following few weeks. It was really hot having Mom watch as I got myself off, but it didn't help me get to see her pussy. Not once after that first time did she play with herself in front of me, though after each session she'd retire for the evening and each time I'd hear moaning coming from her room.

Everything changed when we got hit with a massive snowstorm. At first, I was disappointed because it meant no Brian and the party was canceled. Necessity is the mother of invention, though, and seeing my Mother naked was a necessity, so I came up with another plan. I'd suggest a game of Truth or Date to Mom. If I played my cards right, slowly turned up the heat, I was pretty sure that if I dared her to play with herself, she would.

I suggested to Mom that we kill the time by playing Truth or Dare and she said that sounded fun. It started off slowly, silly dares and inconsequential truths. To my delight, Mom was the one who broached the topic of sex, asking how Brian was in bed. I told her, in very explicit detail, what Brian did to me and how it felt. Mom took a dare, so I dared her to take her top off. She smirked and slowly pulled her shirt up, keeping it close to her body to make sure there was glorious boob-bounce when her breasts finally fell free.

I next chose truth and Mom asked what my favorite part of the party was. I told her the truth, that it was watching her in a threesome, but left out that it was specifically her that turned me on. Mom chose truth, so I asked how she had gotten involved in the parties and she told me, in great detail, about how she ended up fucking Sue at a holiday party. I chose truth.

"Is this getting you wet, baby?"

I nodded and Mom chose truth.

"Who was the first woman that you slept with?"

"Your grandmother. Truth or dare?"

I sat there, momentarily stunned. "Did Dad know you slept with his Mom?"

"That's not how this works, baby. It's your turn. Truth or dare?"

"Um, uh, dare."

"I dare you to show me how wet you are."

I took off my shorts and spread my lips. By this point, I was absolutely dripping. I didn't give Mom a choice of truth or dare, jumping right back to my previous question.

"I never slept with my mother-in-law. Truth or dare?"

"But you said you slept with... oh. Oh!" Right back to shocked. My heart thudded with the thought that this might progress further than I had hoped. "Truth or dare, Mom?"

"Dare"

I was worried that Mom would say no, maybe even stop the game, but I had to take the chance. "I dare you to kiss me."

Before I knew it, Mom was straddling me, her lips locked on mine. I felt her lips part, then her tongue was gliding over my lips. I opened my mouth, accepting Mom's probing tongue. Holy shit, I was french kissing my Mother and it felt so fucking amazing!