I [M] 31 at the time hooked up with a family friend's [F] daughter who was 22 at the time.

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This happened a few years ago now. Some back story first, my parents have some good friends that have 2 kids, a daughter and son. I was 19 at the time and our families took a joint camping trip to the beach for a week. I thought their friend's wife was kinda hot so 19 year old me was pretty happy about being at the beach with them. I ended up mostly hanging out with the kids since I was cooler to be around than their parents.
Fast forward 12 years. The same family is having a college graduation party for the daughter and we're invited. The party started around 6 but I didn't drop by until about 8 and by that time the alcohol was flowing and everyone was having a good time. I chat a bit with everyone since I know practically everyone at this party outside of the daughter's friends and talk a little bit with her brother who's now heading into his senior year of high school.
Up until this point, I hadn't seen their daughter in quite a few years, we'll call her Brooke. Brooke had grown up to be a 5'7 blonde that really resembled her mom but was a few inches taller. I get up from around the campfire they have going to get something to drink and sit down at the picnic table to check some stuff on my phone when out from the house comes Brooke and a few of her friends. She sees me and says "Hey! Thanks for coming!" and gives me a hug. We make small talk for a bit but I'm kind of distracted by her friends. Brooke and her friends played on the college volleyball team and were all very attractive. If you've ever watched women's volleyball, I'm sure you can figure out their body type. Brooke was no different with thick muscular thighs and a nice round bubble butt.
I think she noticed me trying to covertly check out her friends because she kinda stops mid sentence, grabs my bicep and says "You've been working out huh?" I really wasn't outside of doing some sit-ups and pushups and going for runs when I felt like it. I respond to her by saying "Sometimes. I have trouble getting motivated to do it consistently though." So she replies "You should come over and work out with me, we practically have a Planet Fitness in the garage." They really did, both her and her brother were athletes and so was their dad back in the day and he still liked to keep in shape. I kinda laugh and say "Maybe I will sometime."
Right about this time, someone accidentally lets the dog out of the house and he starts running around like a madman. He runs over to us and jumps up on me so I pet him some and she tells him to calm down. I mention something about my dog and she asks me if I have any pictures of him. So I pull my phone out and my gallery is pretty much 90% pictures of the dog. I hand the phone to her and say something along the lines of start here. I don't have any lewd photos on my phone so no concern handing it to her. Right about this time, Brooke's grandpa had walked over and started talking to me about his classic cars. I'm a car guy myself so I enjoy these conversations. Somewhere during that conversation, Brooke lays my phone on the table and says she's going to head inside for a bit with her friends, thanks me for coming and says it was nice seeing me again. I finish up my conversation with her grandpa, head back over to the campfire for a bit before heading home for the night.
A few days later I get a text from an unknown number with a message that says "Heyyy! When are you coming over to work out with me?" Apparently while I was talking to her grandpa, Brooke had somehow gotten my number while she had my phone. I tell her I'm pretty busy with work this week but I'll probably go for a run a time or two. She replies with "Well let me know when you want a real workout ;-)" The wink kind of throws me off because of course being a guy you know right where my mind went but I had never thought of Brooke that way and there's no way an attractive 22 year old that I've known since she was a kid would be hitting on me, right? So now I'm scrambling for a response because I don't want to leave her hanging and potentially make things awkward but I'm not sure if I should try to push it or not. So I played it safe to see what she'd say by responding with "I might be able to swing a half day Friday, how does that sound?" Brooke replies, "Sounds great, you better bring your A game for the workout I'm gonna give you :-P" That response didn't really clear anything up for me. I could interpret it as just her being playful and joking or hinting at something else if I sat there and obsessed over it.
So Friday rolls around I'm kind of second guessing this whole thing because I'm not really sure what her parents would think of me spending time with their daughter. Our families have been friends for a long time but that seems a bit suspicious. It's about 11:30am and I get a text from Brooke that says, "Don't forget about our workout :)." I've gotten cold feet after thinking about it and reply to her, "I don't know if I can make it." She replies, "Whaatttt??? Why not?? :(" I tell her I'm not sure your parents would be ok with me just showing up and using all their expensive equipment. She quickly responds with "Well they're gone for the weekend for their anniversary and Blake is going to a concert with his buddies and won't be back until sometime tomorrow so it'll be just us." Before I can reply she adds, "I can keep a secret if you can ;-)" Now my mind is racing and I'm filled with this electric nervous energy, she's definitely hinting at being into me right? I thought about it for probably less than a minute and responded back with, "How does 3 sound?" She replies, "Don't be late or I'll work you even harder!"
I get off work and stop at home first to take care of the dog and change. I figure I'll go over and we'll work out, if anything happens, she'll have to be the one to make a move. I'd love for something to happen since I'm in a bit of a dry spell (ended a serious relationship about 5 months prior and mainly just focused on my work since) but if I try to make a move and I'm wrong about her intentions, I'm sure it will do a lot of damage to both of our families. Not to mention the damage her dad would probably do to me. The nervous energy comes back as I text her that I'm on my way. She says to just come in the side door to the garage when I get there.
I pull up the driveway and turn the car off. The nervousness is in full force as I take a deep breath and start heading for the door. I walk in as she's entering the garage from the house. She's wearing a bright pink sports bra and those really short fabric shorts with white going around the edges and drawstring in the front. I practically froze when I saw her because it wasn't leaving much to the imagination and I'm thinking there's no way I'm going to be able to hid the inevitable erection I'm going to get in the mesh shorts I'm wearing. She puts on some top 40 station and asks me what I normally do to warm up. I mumble something about stretching and she says "Let's get to it!" I start stretching out my arms and shoulders while she's a few feet in front of me bending over stretching out. Her shorts rode up and the bottoms of her ass cheeks hung out when she stood back up. I half-heartedly stretched for about 5 minutes while watching the show she was putting on in front of me. I know she saw me watching as I saw her glance back at me and smirk a time or two.
Next she asked me if I would help her stretch her hamstrings which meant both of us getting on the floor. I say "sure" all while I'm thinking, fuck, touching those tight, toned legs is totally going to get me hard. I get down with her on the mat and try to not think about what I'm doing but it's not working. We start with her left leg and then move to the right. I'm holding it together so far, until I look down and her shorts have moved just enough to show me that she's not wearing any panties under them. Her tight, cleanly shaven 22 year old pussy is right there on display for me. I look back up and Brooke locks eyes with me, smiles and says, "Your turn." I know my cover is about to be blown here but I'm just gonna roll with it since I'm positive she's about to make a move and take that burden off of me.
I lay on my back and bend my right leg so my knee is in the air. Brooke gets into position but instead of bringing my leg up to stretch it, she slides her hand down my thigh, leans forward over me and says, "I've fantasized about you ever since that trip to the beach". I'm instantly fully erect at hearing those words. Brooke crawls forward a little further, my tip just brushing against her bare midsection, and presses her soft, full lips against mine. The intensity of our kissing quickly increases with our tongues exploring each other's mouths. I grab her ass with both hands as she lets out a soft moan. Brooke sits up, grabs my hand and says, "come with me." She leads me into the house and upstairs to her bedroom.
We no sooner get though the door to her room and she's pulling my shirt off of me. We're making out heavily, hands all over each other. I slide my hands up her sides and under her sports bra and she happily lifts her arms to help me slide it off of her. I paused for a second to take in the view of her tits, they're about a handful in size but very perky with small pink nipples. I slide my hands from her waist, up over both tits and play with her hard nipples with my thumbs. She lets out a moan and pulls me in to kiss her. She quickly grabs my hand and leads me over to the bed. On the way over we both kick our shoes off and I about trip which gets a laugh from her. She pulls my shirt off, then lays back and pulls me on top of her. We make out a little more before I start kissing my way down her body. I get just below her belly button when I slide my fingers under the waistband of her shorts, she lifts herself up slightly to help me pull them off.
I took another second to just take in her beautiful, tight, naked body for the first time. I slowly kiss my way up her left thigh before teasing her glistening pussy with my tongue followed by diving between her dripping wet lips. I hear her let out a mmmmmm as I work her clit with my tongue while teasing her nipples with my fingers. Brooke starts letting out small moans and gasps as she rocks her hips, grinding her pussy into my face until she reaches orgasm. She pulls me back up to her to taste herself on my lips before rolling over to her stomach and giving me my first full view over her perfect round ass. I'm 100% and ass man and hers is my definition of perfect. I slide my shorts and boxers off and position myself behind her. I run my fingers between her lips and I don't know what came over me but I decide that I just have to lick her ass. It's right there just begging for it. So I just dive right in which catches her off guard. She pulls away a little bit before I guess realizing I'm doing it intentionally and relaxes back toward me again. I slide a finger inside her to massage her g-spot while my thumb circles her clit and my tongue works her little pink asshole. She starts getting noticeably louder, moaning and breathing heavily before I feel her start to tense up. She breathlessly exclaims "Oh fuck!" as she collapses into her pillows with her second orgasm. I rub her back while she comes down from her orgasm.
Brooke rolls over to her side to face me and says "I need you inside me, now." She pushes my shoulder down and climbs on top of me. Now it's her turn to tease me as she brushes her pussy lips over my hard cock, rocking back and forth and slowly putting more and more pressure down on me. Once she's satisfied that she's teased me enough, she grabs my now lubricated cock and guides it into her. She starts rocking her hips back and forth on me and I can tell I'm not going to last long in her tight pussy. I sit up and grab her ass to allow her to grind her clit on me for more stimulation while this position also lessens the sensation for me and helps me last longer. I start licking and sucking on Brooke's nipples as we work together toward orgasm, me helping Brooke to work back and forth on my cock. Luckily my position works out for me as she cums again before I do. Brooke wraps her arms around me and we kiss deeply for a minute before I pivot to put her on her back again.
I grab one of her pillows and slide it under her to help get a good angle and position myself with her thighs against my chest because let's be honest, you can't be an ass man and not appreciate nice thick, muscular thighs. I slide myself back into her, starting to work back and forth slowly using all of my length. Brooke holds onto her tits and plays with her nipples as I start to pick up speed. I can feel myself getting close when Brooke locks eyes with me and bites her bottom lip. That's all it took to push me over the edge, I quickly pull out and cum harder than I can ever remember cumming before. The first few shots make it up just short of her chin with the rest coating her toned stomach and one last little drip falling just above her pussy. I lay down beside her and catch my breath for a second while I watch Brooke start playing with my cum, rubbing it on her nipples before scooping some from her stomach to take a taste. Never would I have expected to have an experience like this, let alone with a girl like her.
We laid there and talked a little bit about what had just happened and try to wrap our heads around it when Brooke says to me, "I loved getting to taste your cum but I was hoping you would cum inside me." I'm a big fan of creampies and tell her I obviously didn't have a condom to wear (left them in the center console of my car) and didn't know if she was on birth control. She leans over and kisses me before saying, "You can fill me all you want, I'm on the pill." I smile and laugh a little and reply, "Noted." We chat for a few minutes before Brooke asks me if I want to join her in the shower. Obviously we were both in need of cleaning up so I agreed and Brooke led me across the hall and into the bathroom. It was a little cramped with both of us in there but it was manageable and we had a few laughs while cleaning up. We get about to the end of it and I can't help but watch the beads of water run down Brooke's body and I start to get hard again.
I put my hands on her shoulders and run them down her sides and to her waist. I press my hard cock between her ass cheeks as she looks over her shoulder at me and smiles. "Ready for round two huh?" she asks. Without saying a word I rub my cock between her lips to get some lubrication before pressing into her from behind. This time I didn't need to worry about lasting and just started pounding Brooke, the sound of me slapping against her ass echoing through the room as she braces herself against the back wall of the shower. Round 2 is a blessing and a curse, after pounding away for a few minutes, I had to stop and take a quick break but I wasn't done yet. Brooke spins around and laughs asking if I'm alright. I smile and say, "you're quite a workout." After catching my breath, I tell Brooke to put her leg on the edge of the tub and slide into her from the front. Luckily we line up pretty well for this with her height. I grab onto her ass and thrust in and out of her as she matches my rhythm and fucks me back. I pull Brooke's face to mine and kiss her deeply as I unload inside of her. She shudders as she feels me pulsing and digs her fingers into my back. "Thanks for giving me my first creampie" she says followed by another kiss. I found out later that she had always made the two guys she hooked up with in college use condoms and I was the first she took bareback. The water is cold by this point so we quickly finish up and get out.
By this time it's about 5 and we're getting hungry so Brooke gets a pizza delivered and we talk about numerous different subjects for an hour or so while eating. The conversation eventually dies off and she asks if I want to watch a movie with her. I figure why not, I didn't really have anything else planned for the evening. I probably should have asked what movie we were going to watch because she decided to put in a DVD of The Notebook. Not my kind of movie at all but it gives me an excuse to cuddle up with her on the couch. I'm laying behind her not really paying attention to the movie but replaying the events of the last few hours over in my mind. She must have felt me getting hard because she rocked her ass back into me and starts slowly working it back and forth on me. This of course leads to me sliding both of our shorts down and slowly cuddle-fucking while watching the movie. Eventually I fill her with a second load and we finish watching the movie while my cum slowly leaks out of her.
After the movie ends I tell her I should probably get home and let the dog out, she walks out to the car with me gives me a nice deep passionate kiss before saying, "best workout I ever had." We hug and I head home. We had a few more encounters spread out through the summer that year until she got a job out of state. We still text sometimes but nothing sexual since she met someone out there not real long after moving and is very happy. It will always be a great memory for me.

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from Gonewild Stories https://www.reddit.com/r/gonewildstories/comments/lslvys/i_m_31_at_the_time_hooked_up_with_a_family/

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