u/superdupernick121

Hey everyone, I’m back with another update. It’s kind of a big one, so I’ll get right into it.

A quick recap for anyone new: A few weeks ago, my family friend Bri slowly started flirting/teasing me, which resulted in us having a conversation where we agreed to lose our virginities to each other. We’re taking it slow: until today, we only made out and did hand stuff. You can read those stories in my profile if you haven’t already. Now onto the update:

Everyone in this story is over 18.

Like we do every year, Bri and I’s families celebrated the 4th of July together. She and I texted beforehand about laying low, since neither of us wants our parents to know about our arrangement. Since they talk often, we figured it was best to avoid any suspicion at all, which meant largely ignoring each other throughout the weekend. It was hard, since all I wanted to do was grab her and start making out. But i guess there’s something kind of fun about pretending, too.

Then today, we’d made plans with our friends to meet at Bri’s to swim. It sucked to still not be alone with her, but i thought it would be nice to hang out with everyone (and see her in a swimsuit again, lol). For context, our core group is five people: Brianna and I, her friend Ruby, and my two friends Stevie and Rich. We have a few other mutual friends who sometimes join us too, but this time it was just gonna be the five of us.

But then this morning, both guys texted saying they had to cancel for work/family stuff. I kind of hoped that Ruby would cancel too, so it’d just be Bri and I. But she said she’d still come if we were down, and we said that worked for us. Bri’s mom would be home, so it’s not like we could’ve done anything anyway. Or so I thought…

When I showed up, Ruby was already there, and both girls were laying on the loungers beside the pool. Bri wore her orange one-piece again, and Ruby had on a white bikini. I said what’s up, and maybe stared a second too long cause Ruby asked jokingly if I was enjoying the view. 

A bit of background: I mentioned in my earlier parts that I had only kissed one other girl. That was Ruby, although it was literally a nothing kiss. One time at a party, Rich brought a joint that he got from his older brother and we all sat around and smoked it. Someone suggested we play spin the bottle, Ruby went first, landed on me, and we literally pecked each other on the lips for one second. Then Rich went next, landed on another guy, and said he didn’t want to play any more. That was it. 

Ruby and I never talked about it (there was nothing really to talk about), but she did occasionally give me shit or joke about me liking her. If only she knew the truth! I brushed it off and got in the pool, and they joined me shortly after.

It was a nice day so we just chilled and splashed around. At one point I went up to the house to grab some chips, and bumped into Bri’s mom and said hi. Back in the pool, Ruby Bri and I didn’t really talk about anything specific, just shot the shit. I remember wondering the whole time when Ruby was going to leave. I felt a little bad about that. After all she was my friend too, and Bri and I couldn’t really have sex anyway, but it was just hard to think about anything else. I’m sure you know the feeling.

Eventually at like 2 or 3ish, Ruby said she should prolly go home and help her mom. I had to try not to sound excited lol. She grabbed her stuff and left to drive home, leaving Bri and I there alone. We immediately started grinning at one another, and just floated around like that for a while. We didn’t need to even say anything, the tension was there.

Of course Bri’s mom was still up in the house. Granted it was a bit of a walk from the pool, but she still could’ve seen us from the upstairs windows if she tried. It would’ve sucked to get caught, but in that moment I was pretty ready to risk it. And it sounded like Bri was too!

She swam up close to me and whispered, “I’m gonna go into the pool house.”

“Okay.”

“Meet me in there in a minute?.”

“Okay.”

That was maybe the longest minute of my life. The moment I watched her climb out of the pool, swimsuit sticking tightly to her ass, I was instantly rock hard. I didn’t have my phone in the water, so I wasn’t sure exactly how much time passed. I just bobbed there alone and took the moment to readjust my cock from sticking straight out. Then finally I waded towards the stairs and headed for the pool house.

I knocked on the door, which I guess was stupid. But Bri’s voice from inside, “come in,” was so sexy that I was glad i did it. I slowly pushed the door open, and could hear the shower running, so I assumed she was in there. But nope. Instead I found her standing in the middle of the room, waiting for me, completely naked.

My jaw literally dropped. I worked my eyes down her body, from her wet hair, blushing face, and little breasts, down to her naked vagina. It was my first time seeing it. It was perfect, an ‘innie,’ with a little patch of black hair just above it. It seemed like she had shaved a bit, but I wouldn’t have minded if she hadn’t. Hell I wouldn’t have minded anything, I was just so happy to see her like this. She was amazingly sexy, with an absolutely perfect body. I wanted so badly to run up and work my hands all over her, but I was so astounded I couldn’t move an inch.

Bri didn’t move either, just asked “what do you think?”

The words poured from my mouth “I think you’re amazing.”

“Let me see you.”

I did as I was told, dropped my wet shorts down to my ankles and stepped out of them. Normally my dick would have shrank a bit from the pool, but this was the opposite. I was rock fucking hard, and my cock pointed straight out at her, balls clinging snugly at the bottom.

She smiled and looked me up and down, admiring my package. We just stood there, eyeing each others bodies. If you had told me a few weeks ago we would be here, I wouldn't have believed you. And yet there she was, naked for my viewing pleasure. 

Finally she broke the silence. “Let’s take a shower.” I nodded and followed her in.

Eager to make up for my awkwardness last time, I lunged for her body the second she closed the glass door. I pulled her into a kiss, pressing our bodies together and squishing my dick up against her pelvis. I could feel her giggle, and then she locked our mouths together, kissing me back with passion. Then I separated a bit and reached for both her breasts, rubbing them and squeezing her nipples in my fingers. She gasped and reached for my cock, slowly running her hand along its length. Then I took one look at her for confirmation, and reached my hand between her legs.

I took a brief pause to run my fingers along her patch of public hair. It was soft like the rest of her. I like a little bush, so this was a welcome surprise. Then I moved lower and began gently stroking her pussy lips, feeling their softness. I made a slight move to work my finger between them, but it was hard with the water and the angle, and I didn’t want to hurt her. So really I just rubbed my hands along her, sometimes reaching behind to grab a handful of her ass. We kissed and touched each other like that for a while.

Then she said “can i try something?” and I replied “yes, anything.” She took my hand and pulled me out of the water, then lowered down to her knees. Holy shit, this was actually happening. With another grin, she leaned forward and took my penis into her mouth. I couldn’t believe my best friend was actually sucking my dick!

I’ve seen plenty of porn where the woman ‘deepthroats,’ but this wasn’t anything like that. It didn’t need to be. She bobbed forward and back, only taking about the first third or so of my dick, but let me tell you it felt so fucking good. She pulled my foreskin all the way back and worked her tongue around my head, and reached up to feel my balls as she stroked me in front of her mouth. For someone with no experience, she sure knew how to suck a dick!

I could have cum right there, but I didn’t want to just yet. Instead, I asked if I could taste her first. She said yes, but she wasn’t sure if we could do it standing. Then she offered “maybe the stall?” We turned off the shower and made our way through the stall door.

Bri sat on the toilet lid and I knelt down on a towel in front of her. Not exactly the nicest spot, but it didn’t matter to us. I pushed her knees apart and got my first close-up look at her pussy. It was so beautiful, small and cute. A little bit of pink labia poked free from her pale lips, and I could just make out (what I think was) her clit. I wasted no time, and dove between her legs to finally taste her.

Now obviously I’m no expert. I had done a bit of googling, learned some tips (doing the alphabet with your tongue, lol), but in the moment I just did what felt right. I licked up and down, careful not to go too deep. At one point I brought my hand in and rubbed her in various places while licking her in others. I didn’t have an exact plan, but her breaths and laughs told me she was enjoying herself. She even put her hand on the back of my head, which I loved.

Then she told me to stand up. I wasn’t sure what she had planned, but I was excited to find out. Unfortunately I never did, because as soon as I got to my feet, we heard a knock at the door and Bri’s mom call her name from outside. 

Fuck. For a moment, we exchanged a look. We were caught, that’s it. Neither of us breathed, Bri silently gestured for me to get against the wall, hoping her mom couldn’t see my feet from beneath the door. Then she coughed and managed to shout “in here!”

I could hear her mom open the door and walk in. “Did Nick and Ruby leave?”

“Yeah they went home. Is everything okay?”

“I was just gonna ask your plan for dinner. Are they coming back?”

“No, but I’ll be up in a sec.”

“Okay. Love you.”

“Love you too.”

Then she left. When I heard the door close, I could finally breathe again. Bri and I looked at one another, half laughing and half horrified. It was pretty clear the moment had passed, so we scrambled out of the stall to get dressed.

That’s when I realized: In my excitement, I had left my bathing suit on the floor, completely out in the open. Oh shit, I thought. It was pretty unlikely that her mom hadn’t noticed it. I guess she could’ve assumed it belonged to Bri’s brother? But I’m not confident in that. Fuck, I really wish I had been more careful. I pointed it out to Bri, who seemed a little nervous, but said she would think of something.

Bri pulled her suit back on, then said to wait in the house and she’d text me when the coast was clear. I told her I left my phone by the pool, and she said to just wait a few minutes then. Then she left, no kiss goodbye this time. Cearly we were preoccupied. After a few minutes passed, I darted out of the house, grabbed the rest of my shit, and ducked out through the neighbor’s yard.

After like an hour, I texted Bri and asked how things were going. She said things were fine, and her mom didn't seem THAT suspicious, although she DID ask about the swimsuit. Bri just said I must have forgotten it by mistake. Who knows if her mom actually believed her, but at least she isn’t asking any questions for the time being.

Then Bri apologized for us getting interrupted, and that she kind of kicked me out. I said it was no problem, I understood. But we didn’t really text much beyond that. I can tell she’s kind of embarrassed about what happened. I apologized too, and she said it was fine, that it was both our faults. But honestly, I’m still really kicking myself.

Her parents have a habit of getting involved in her personal life, which I know she’s always hated. That’s why it’s been so nice to have something just us. So even though we both went in to shower together, I still should’ve known not to leave my suit out. Especially with the conversation we JUST had over the weekend, it was a really stupid mistake on my end.

So yeah, I kind of feel like shit right now. I’m praying that things cool down, and we can get back to our plan. But that might mean going even longer without seeing each other, which really sucks. 

If anyone has any ideas, I’m happy to hear them. Otherwise keep crossing your fingers for us.

Everyone in this story is 18 years old.

Small update today, but still wanted to share:

Things have been awesome between Bri and I. We’ve been texting nonstop, mostly about how excited we are to see each other next. I’m trying to play it cool, but it’s tough!

If I had it my way, we’d be hanging out every day. But I don’t want to seem too pushy, or give away the fact that we’re hooking up to our friends or parents. It’s not that I’m embarrassed to be with her (actually the complete opposite, I’m ecstatic about it lol). But like a lot of you have said, the build up and exploring together is the fun part. I really like how things are progressing, and I really want things to remain fun and casual. And if that means waiting a few extra days, then I’m happy to do it.

We briefly planned on getting together Tuesday, but then our friends suggested we go out to dinner, and we figured we should go. It was fun and normal, with the exception that Bri and I had to stifle our smiles and pretend nothing was going on between us. I think we did okay. Obviously our friends would have been fine with it, but we both agreed to not tell anyone until we were ready. It was actually pretty fun, like we had a secret life that no one could know about. 

Then yesterday morning I texted her, kind of cheeky. I said it was great seeing her last night, I only wished I could have seen MORE of her, with a winky emoji. She laughed at the message and said I would just have to wait. I liked her message and went about my day, then a few hours later, I got another text from her that read “...but not too long.” I saw there was a photo attached and tapped on it.

I shit you not, it was a photo of her tits. It looked like she was at work, in the locker room, red lifeguard one-piece pulled down, boobs fully out. Her face wasn’t in it, but obviously it was her. I’d recognize those nipples anywhere.

My dick almost shot right through my pants. I had been scared to even propose the idea of sending nudes, and here she was sending one completely unprompted. I immediately darted to my room and pulled my cock out to start jerking.

I texted her back “holy fuck,” and loved the message a hundred times. Following yall’s advice, I asked if I could send her a photo back. I knew she was at work, so better to ask. She just wrote back “Maybe later. Have fun!” Obviously she knew I’d be jacking off to it, and she was right. I stared at the photo and came hard within minutes.

So yeah, just a small story from yesterday! I was happy as you can imagine to receive the photo, but also that she was feeling confident enough to send it in the first place. Last time she had seemed a little shy about her boobs, so I was glad that I made it clear how much I loved them and clearly wanted to see them again lol. Hoping this is the first pic of many!

Everyone in this story is 18 years old.

Hey all, sorry it’s been so long since my last update: Brianna and I didn’t get to see each other at all last week. She works most days, and my parents have me busy with some college prep stuff (shopping, signing up for stuff). Our friends were busy too, and schedules just didn’t line up.

It was total agony waiting to see her again. I even debated sending her a photo of my dick and asking her to send one back, but it felt too soon and I didn’t want to mess things up when they were just getting started.

Then today (Sunday), we FINALLY got our first chance to be alone in the house. This morning I was supposed to see a movie with my parents, but then Bri texted me saying she had the day off. I immediately told my parents I didnt feel like going anymore, and thank god they decided to still go without me. The literal second they were gone, i texted Bri and told her to run over. She sent “on my way!” with a winky emoji.

Like I said in my previous post, I really wanted to make sure I focused on her. I was nervous to see and touch a vagina for the first time, but I read all your comments and did a bunch of research on the internet. I actually feel like I learned a lot, lol.

Once Bri got here, I explained the situation: that my parents were at the movies, so we only had maybe 2-3 hours. I even checked the runtime and the Google Maps estimate for the drive there and back. I didn’t want anything left to chance. I was a little nervous cause I know how important foreplay is, but we only had so much time. I asked if she was okay with going right up to my room, and she smiled and said she was.

Another thing I felt nervous about was kissing her. Even though she had literally jerked me off last time, kissing her still felt more intimate, almost wrong. Like it was reserved for dating, and we weren’t. I didn’t know if it was her first kiss, would she regret it being with me over an actual boyfriend? Plus I had only ever kissed one girl myself, was I even any good at it?

But then we got into my room, closed the door, and sat on the bed together. And holy shit, I wanted to kiss her so bad. Like, NEEDED to kiss her. She was wearing these tight yoga shorts and a hoodie from our high school swim team. It was literally the most casual outfit on the planet, and yet she looked spectacular in it. 

I was nervous as always, but our last conversation had filled me with the confidence to actually go for it this time, and I was excited to prove that to her. I smiled and asked, “Can I kiss you?”

She smiled back at me, “okay.”

This was it. We leaned in and our lips met. First just a peck, then back in, deeper and longer. Pretty soon we were making out, and holy shit did it feel good. She put her hands on my shoulders, and I moved mine onto her back. She was so warm, so sweet. It was like our lips fit perfectly into one another. If that was all we had done, I would have been fine with it. But luckily we still had ample time.

I broke free for a moment and pulled my tee off so I was shirtless, then went back in to kiss her more. Her hands moved along my chest, so small and delicate. My chest is hairless, except for a dark happy trail that keeps annoyingly coming back. I had shaved it for this occasion, in fact I shaved my whole junk just in case. As she caressed my chest and back, I started to work my hands down her body and underneath her hoodie. I had only just met her skin when she broke our kiss and pulled back from me a bit.

At first I was scared that I fucked up. “Is everything okay?” I asked.

“Yes, it’s great. It’s just that… I didn’t wear a bra today.”

“Oh, that’s okay. I don’t have to…”

“No, I want to. It’s just… I know guys like big boobs, and mine aren’t really like that.”

I couldn’t believe what I was hearing. “Bri… I don’t care about that. You’re beautiful.” I really meant it.

She smiled at me, so cute. “Okay.” She raised her arms and kind of puffed her chest out, waiting for me to take control. I reached for the bottom of her hoodie and started pulling it up and off. I swallowed hard. I was finally seeing her boobs!

I can still see her nipples poking free from the fabric for the first time. It’s completely etched into my mind. I rose the sweatshirt the rest of the way off, helping pull her arms free, then dropped it onto the bed beside her. Then she sat back, a nervous smile on her face, and I took in her topless body in its entirety.

She was so beautiful. It was true, her breasts were small, almost not even there. Like two points sticking out of her chest, rather than heavy sacks hanging off it. I’m not the expert, but she must be an A cup. But I didn’t care, I love them. Her nipples were tiny, like two pennies, stiff and pointing straight out at me. I was in awe, and whispered to her “You are so amazing.” She blushed and leaned back in to kiss me.

We made out some more, our bare chests pressing against one another. We were sitting up, but I tried a move I had seen: cradling her back, I lowered her flat onto the bed, and hovered myself over her. I propped myself up with one hand, and let the other feel her body. I started at her cheek, then worked my way down her neckline and cupped her bare breast. Laying down, there wasn’t much to grab onto, but it still felt soft and warm. I lightly pinched her brown nipple, then the other, which caused her to gasp lightly.

We kept kissing like that, and I felt her hand feeling for my dick through my shorts. It felt good even through the fabric, and I let her rub it for a few seconds, but then lifted off and looked at her. I told her I really wanted to touch her, if that was okay. She smiled and said it was.

I moved over so I was still ‘on top,’ but had better access to her body. Like she had to me, I slowly worked my hand away from her breasts, down her stomach, past her waistband, and then finally onto her crotch. I gently rubbed her crotch over her shorts, taking a moment just to feel her. She made these quiet, breathy gasps the whole time. “Can I take these off?” I asked, and she nodded.

I started taking her shorts off, careful to leave her underwear in place for the time being. They were tight so it was kind of tough, but she helped me roll them down and her panties came into view. They were pink with a little bow in front. I laughed and said they were like a present. She giggled and whispered “for you.” My entire body fluttered when she said that.

Once her shorts were off, I leaned in and kissed her underwear at the front of her pelvis. Then I moved my head down and kissed between her legs, right where her vagina was. It was soft and just the slightest bit wet.

She asked if it was okay to leave her underwear on? I said of course. Then I asked if everything was okay, if I had done anything? She said everything was great, she just wanted to keep them on. I figured she was just nervous, like I had been. Honestly I was perfectly fine with waiting.

I started touching her through the fabric. I knew not to rub too hard or quickly, especially with her panties still on. If she were naked, I know I should have tried to find her clit. But this time, I just focused on feeling her, being in the moment, making her feel good. I figured she probably wouldn’t cum, which was also fine. 

Her panties started to feel really wet where her vagina was, which I took as a good sign. I didn’t really have an agenda, I just glided my fingers up and down, back and forth, sometimes taking a break to reach back up and grab her breast or kiss her.

I was fully hard for pretty much all of it, and at one point she reached her hand into my shorts and felt me through my underwear. “Will you take these off?” she asked.

“Oh, yeah I can. But I don’t mind just touching you.”

“That’s okay, I want to touch you too.”

“Okay.”

I turned to the slide and slid off my shorts, then looked back at her. “Those too,” she instructed me, and so I pulled off my underwear too. Now I was fully naked, and she was just in panties. She reached for my dick again and tried to stroke me, but it was tough with the angle. We moved so we were both laying on our sides facing one another, her jerking me off and me rubbing her vagina as best I could. 

Holy shit, it felt so intimate. Last time it was dark, sat feet apart in the car, looking over our shoulders to make sure no one caught us. This time we were alone, inches away from one another, completely lost in the moment. We would lean in and kiss, and I’d move down to take her nipples in my mouth. At one point she kind of looked down, and cradled my balls with her other hand, just to see what it felt like. We just kept on smiling and giggling at one another, we couldn’t help it. She was so freaking sexy.

After a while, I felt myself getting close. I realized that I hadn’t checked the time in ages, and apologized and checked my phone quick. Luckily it had only been like an hour. I told her I was starting to get close, but we still had time and could slow down if she wanted. She said no, that she wanted to watch me cum. I asked if she’d be able to cum? She said probably not, but it felt so good.

Then she asked me to get back on top of her. She moved flat on her back again, and I did. As I moved, she reached down and kind of positioned my dick right on top of her vagina. Still a layer of fabric in between us, but my shaft was just in between her lips. She told me to move up and down on her. It was like we were fucking, dry humping I guess. Occasionally I’d feel the little bow on her panties rub against my shaft, but it didn’t bother me.

It felt amazing. From her face, I could see it was good for her too. Our eyes locked, smiling and faces red, small beads of sweat forming. This is what it would be like to fuck Bri, I thought, except obviously she’d be naked and I’d be inside her. I felt my orgasm build, and I warned her I was going to cum.

She whispered, “Yes, I want you to. Cum on me.”

I never thought I would hear her say those words. It was too much to bear, and within seconds I started grunting and shooting my hot cum all over her body. I kept grinding against her, and watched as white spurts shot up and landed across her stomach, and even up over her breasts and neck. I can’t tell you how beautiful she looked in that moment, grinning ear to ear, topless and covered in my cum.

As I finished and lifted off of her, I noticed that some of my cum had indeed gotten on her panties. I apologized, but she said it was fine. She rose up and kissed me on the mouth, and we made out for a second more. Then I told her I would go grab her a towel.

I left to the bathroom, still naked, hard cock swinging as I walked. I grabbed a small towel from the closet and wet it in the sink. When I returned, she was still in my bed, covered by the top sheet from the waist down. Immediately, I noticed her panties resting on the nightstand. She had taken them off, and was now fully naked under the covers.

“Is everything alright?” I asked.

“Yes. Just didn’t want to make a mess.”

We exchanged a grin, and I walked over and sat on the bed beside her with the towel. She started to reach for it, but I told her “that’s okay, let me.” She lifted her chest, and I wiped the cum away from her stomach, tits, and neck. Then she asked for the towel, and wiped her lower body beneath the blanket. I guess she wasn’t ready for me to see her there yet, but that was fine. She handed the towel back, and I took it and her panties back to the bathroom. I wasn’t sure exactly what to do, so i just rinsed them both and hung them to dry. I figured I’d hang onto them and do a load of laundry next time my parents were gone.

When i returned again, she was still in my bed waiting for me. My dick was fully soft now, which she pointed out. I said “oh yeah, it does that,” and she asked me to come closer so she could see. I stood at the edge of the bed, and she reached over and felt my soft penis, lifting it up and wiggling it, which made her laugh. It actually started to get a little hard again, and she asked me if I wasn’t finished? I said no, I was, then asked if I could lay with her. She said yes. I climbed under the sheet with her, careful not to expose her lower half.

We laid facing each other, and spent the rest of the morning just talking. Of course we started by talking about sex, but quickly moved on to other things: our friends, plans for college, etc. It was like it was the most natural thing in the world. At one point she turned around and asked me to hold her again, just like the first time. I scooted closer, not hesitating at all, and pressed my naked body against hers. Her ass pressed against my crotch, and I felt the warmth of her bare butt on my penis. It did start to get hard again, but neither of us minded. This time I reached my arm around her and grabbed a handful of her tiny breast. She asked again if they were okay, and I said they were the best I ever saw.

Eventually I checked the clock again, and realized my parents would be getting out of the movie soon. I guess it wouldn’t have been THAT suspicious for them to come home and find her there, but we figured it was better to avoid the thought entirely. I stood to get dressed and passed her her shorts, which she slid on beneath the covers. Then she stood up to grab her hoodie and put that on too. That was the first time I saw her topless standing, and I realized that her boobs did have a little weight to them, and she must have just been leaning before. They really are so incredible.

I walked her downstairs and to the back door. Before she left, she kissed me one more time, and we made out for just a moment. Then she left. I retreated right back to my room and jerked off again, then went to the bathroom to clean up. And thank god I did, because I realized I had left her panties just hanging on the towel rack. I quickly scooped them up and hid them in my room, just minutes before my parents returned.

It was such an amazing morning, probably one of the best of my life so far. We’ve texted a little since then, I told her how much fun I had, and she thanked me for making her feel special. I asked “same time next week?” and she sent back “hopefully sooner!!”

I do admit, this whole thing has got me thinking about how Bri and I would work as a couple. Maybe it’s just because she’s made me cum twice now, but I can’t stop thinking about her. Just the thought of her makes me smile, and I can’t wait to see her again. I know we said this didn’t make us “a thing,” but it’s hard not to imagine. I don’t think I’ll say anything right away, since I don’t want to ruin what we have, but I’m considering saying something at some point. Guess I’ll see if I find the right time.

Hi everyone. Huge update here, gonna jump right in. If you haven’t read my first two stories, definitely check those out in my profile. As always, everyone is over the age of 18.

On my last post, you guys offered a lot of advice and a lot of tough love. And you were right: clearly Bri was trying to start something, and it’d be a huge mistake to ignore it any longer. Now it was my turn to make a move. So, determined not to make her wait, I sent her a text Sunday morning.

I asked if she was free to hang later, and she said she was. Normally we would go to one of our houses, but for obvious reasons, I preferred not to have any parents around. So I offered to pick her up and go get some food instead. It’s stupid, but my heart was pounding the whole conversation. Part of me hoped I wasn’t being too obvious, while the other hoped she knew exactly what I was getting at. She texted back and said that sounded great.

Later that night I picked her up and we went to the Wendy’s drive through. THere’s this big field nearby where they closed one of the middle schools, so sometimes we’d go there with our friends and chill and play spike ball or whatever. This time we just parked at the top of the cliff and ate our food, talking about our summers so far.

I’d debated whether I wanted to kiss her spontaneously, or ask permission first. I still wasn’t sure, but either way, I needed her looking at me & without a mouthful of food. So I started saying “Hey, Bri…” 

Then, to my surprise, she cut me off. Before I could even finish my sentence, she began apologizing for the way she’d been teasing me lately. She explained how at first, it felt like harmless fun. But clearly she had made me uncomfortable, and promised to stop.

I wanted to let her finish, but holy shit I couldn’t wait to tell her how wrong she was. When she started talking about how important our friendship was, I knew I had to interrupt her.

First, I apologized for how weird and awkward I had been. I told her the truth: that I WAS having fun, and ever since that first night in her bed, she’d been on my mind non-stop. She kind of lit up when I said that, and I felt this huge wave of relief over me. She asked if I really meant it, and I said 100%.

We talked for a long time. I won’t go into detail about everything, but the important parts were: like me, she’s still a virgin, and was feeling nervous about going to college without any experience. She first thought of me as someone she trusted, but didn’t really know how to broach the topic, and read online that teasing might be a good way to go. In retrospect she said that was probably fueled more by porn and fan fiction than real life, and she wished she had just talked to me instead. I said that was okay, and I did have fun, but obviously I was glad we were talking now.

We talked a lot about us: if this meant we were dating, or we had romantic feelings for one another. We decided no, not necessarily, and that we shouldn’t feel pressured to get into a relationship. We agreed it wasn’t smart to risk our friendship, or the relationship between our families. She said we could take things slow, and could stop any time if we wanted to.

I told her that sounded perfect to me. She grinned and said “good,” then cleared her throat and asked me point-blank: was I interested in starting right now?

I nearly choked. “What did you have in mind?” I asked.

“Well, I mean…” then she smiled, the same smile she’d given me that first night in her bed. It was like a smirk, but with a wildness behind her eyes. Then she pointed down at my crotch and offered with a hushed whisper, “maybe you could show it to me?”

My whole mouth went dry instantly. I feel like an ass for how awkward I was still being, but truth be told I was freaking out. I had never been in this position with anyone before, and neither had she. But somehow she was so confident and self-assured, it was electric seeing her like that. I still found it hard to believe that she wanted me, but the proof was right there. 

Looking back, I guess that’s when I should have kissed her. But apparently she wanted to see my dick first. And let me tell you: that’s a tough offer to turn down.

The problem was that for once, I wasn’t getting hard. My mind was running a mile a minute and I could barely focus. I managed to stammer out, “okay yeah. But I think… I’m not really, at the moment…”

She smiled knowingly and said “don’t worry. Here.” She checked the windows to make sure the coast was clear, then in an instant, reached for the bottom of her t-shirt and pulled the whole thing off. Holy shit. Suddenly she was sat there in the passenger seat, wearing no shirt, in just a black bra. Obviously I had seen her in a swimsuit before, but this was on another level.

She dropped the shirt to her feet and relaxed her arms, allowing me to take in the sight of her. She was beautiful. It was dark, but I could just make out the shape of her tight body and tiny breasts in the moonlight. Her bra was dark, lacy, the same color as her hair, at least in the lighting. The reflection off her pale skin and glasses was enchanting. Then, as if it couldn’t get any better, she reached for my right arm, took my hand, and placed it over her left bra cup. My mouth must’ve been hanging open, as I felt her breast for the first time. I was fully hard in seconds.

I don’t know how much time passed, it felt like forever, just sitting there with my hand on her chest. I finally got snapped out of my trance by her asking “are you ready now?” I guess I was.

I pulled my hand away and undid my shorts, shimmying them down to my thighs. It was a little cramped in the drivers seat, so i adjusted it quick, which made her laugh. Now my underwear was the only thing between Bri and my fully-erect dick. I hoped she couldn’t see the visible dark spot at the tip where my precum soaked through. Although I suppose she was about to see much more than that anyway…

I looked at her, her eyes locked in on my crotch. ‘Now or never’ I thought, and in one rapid motion, pulled down my underwear to reveal my dick to her.

Once it cleared my waistband, it snapped to attention, pointing straight up. Bri’s eyes widened. I guess she had never seen one in-person before. Her jaw opened a bit, and I felt happy to not be the only one leering. She whispered under her breath, “wow…” then said more directly to me, “why does it look like that?”

I wasn’t sure what she meant at first, but she explained and I realized: I’m not circumcised, I guess all the dicks she had seen online were. If I knew this was happening, I probably would have shaved, too. But luckily I’d done it a few weeks ago and wasn’t too hairy. I’ve always been happy enough with my size, and from the look on her face, so was Bri.

We didn’t say much at first, just admired each others nudity (I guess in her case, partial, but I’m not complaining). Then she asked what I’d been waiting to hear all along: “Is it okay if I touch it?” I nodded. Absolutely.

I held my breath as she reached her tiny hand towards me. Then she did it. She wrapped her fingers around my shaft, and I nearly came as soon as she did. Her hand was warm, and it felt amazing having someone else touch me like that. She whispered again “wow. It’s so soft!” I kind of laughed and nodded, mostly focused on not cumming instantly from her touch. 

She grazed her hand up to the top, then placed one finger on the head poking out of my foreskin. “Is that sensitive?” She asked. I nodded. Still smiling, she moved back to the center and gripped me more firmly. “So you just… is this right?”, and started slowly jerking me up and down

“Oh my god,” I whispered. It felt insane.

She kept going, pulling the skin and causing the head to peek out and in. “Does that feel good?”

“Holy shit Bri, it’s so good.” I really meant it. In fact, it didn’t take long until I was ready to cum. I tried to warn her, “oh my god, wait. Okay, if you keep going I’m gonna…”

“Should I stop?”

“No, I mean… you can if you want.”

She didn’t reply, just flashed me that wild grin and kept pumping my shaft. She had no interest in stopping. That look on her face was enough to do me in.

Again, if I had known, I would have come prepared with some tissues or something. Instead, it was too late. With Bri’s hand still working my cock, I started to cum. “Holy shit!!”

Pumps of cum exploded from my tip and onto Bri’s hand. I had no idea where the rest was landing. Bri squealed with (what I hope was) delight and started jerking me even faster, giggling as I nutted. She kept going until I was fully drained & had to tell her to stop. I leaned back in my seat and threw both hands up over my face.

“That was amazing,” she smiled and examined the cum on her hand. “Was it good for you?”

“Oh my god… it was so good.”

“Okay good. I’m glad. I had fun too.”

It was hot in the car, so we rolled down the windows to let some air in. Bri put her shirt back on, and we searched with our phone flashlights to find where my cum had ended up (mostly back onto my legs and balls).  We both laughed about it, which was nice, having clearly broken the tension between us. I mopped myself up with some napkins from dinner, and she took a few for her hand.

I asked what she wanted to do next, and she said we should probably go home. As much as I hated to end the night, she was right. We’d been out for a while, and didn’t want to raise any alarms with our parents (at least not until we’re ready, if we ever are). So I dropped her off, then went home myself. I texted her thanking her for a great night, and she sent back a smiling emoji.

Anyway, that was my night! I feel a little bad that I never kissed her, but I’m actually not sure she wanted me to. We agreed that this didn’t make us “a couple,” so I’m hesitant to try anything too “romantic.” If she’d rather just stay casual, then that’s fine with me. Either way, it sounds like we’ll figure it out together!

I can barely describe how great I feel, and how excited I am for whatever comes next. I feel like the past few times have been focused on me, so I’d really like to try making her cum next time. Keep the comments coming, and I’ll be sure to provide another update soon. 

Everyone in this story is 18 years old.

First off, thanks to everyone for their comments on my last post! You guys gave me a lot to think about

A lot of you encouraged me to pursue a sexual relationship with Brianna, which I guess makes sense since this is Gonewildstories. I’ve been a fan of this sub for a while, and was really excited to finally have a story worth sharing . I guess if I wanted something more objective, I should’ve posted on a relationship advice sub haha. 

Since that night, I started thinking about Bri in a way that I hadn’t before. After all she is attractive, single, and we get along great. On paper there’s no reason that I shouldn’t be interested in her, it’s really just our past that complicates things in my head. And the consequences of handling the situation wrong made me nervous to fully try. 

So I’m embarrassed to say, but I did chicken out a little. Even though you all agreed she was into me, I just couldn’t wrap my brain around it. We’ve known each other since birth, and have NEVER had any attraction to one another. It felt like a lot of history to all be undone in a single night.

And even if she DID want my dick that night, I somehow got it in my head that it was just a random whim, and she was probably already regretting it. So when I saw her earlier this week, and neither of us said a word about it, I figured my suspicions were correct, and we were just going to move on from it.

But of course I’m back, so obviously that’s not what happened. So here’s the story:

This past Friday, me and some friends went over Bri’s house to swim. Her family has this awesome in-ground pool with chairs, floats, firepit, and a little house connected with a shower and stall. Naturally her backyard is always the hot spot in the summer.

As the night wound down, our friends started to pack up and leave, meaning Bri and I would be alone. Trying to avoid an awkward situation, I quickly said that I should head out too, and dashed into the pool house to rinse off.

I ran the water for a second to heat up, then jumped in (still wearing my swim shorts). About thirty seconds later, I hear the door creak open and Bri walks in. I wasn’t naked or anything, so it wasn’t that weird. But then she walks up to the shower, taps on the glass, and says: “hey mind if I join you?”

So yup, you guys were right. Clearly I hadn’t misread her at all, and that night in her bed was most definitely on purpose. So now I’m stood in the shower, basically freaking out. I instantly feel my dick stiffening under my shorts, and I became fully aware of how badly I wanted her in there with me. Every thought went through my head, including ripping off her suit and fucking her right there in the shower. But apparently I’m a coward, because thinking about it was all I could do.

Instead I stuttered through the glass, “isn’t your dad home?”

“I think he went out, his car’s not here.”

“Oh, uh, okay.”

“Thanks.”

She opened the door and gave me a quick smile, then stepped in with me. It was tight with both of us, so I stepped back against the wall so she could have more room. I can only imagine how fucking stupid I looked. 

Bri on the other hand looked incredible. I had never thought of her sexually before last week, but lately that’s all I’d been thinking about. And now here she was, standing in the shower with me. She had on this orange one-piece that I’d seen before, but never this close. I couldn’t help but stare at her body as she rinsed it under the water.

I’d describe her as medium height, small boobs, but with a good body. She’s always been pretty skinny, so her ass isn’t huge or anything, but it sure looked good in that moment. She has black hair down past her shoulders and a cute, round face. She usually wears glasses, but wasn’t then.

Meanwhile I’m 5’10, average build, but actually in better shape than I used to be. I’ve been trying to exercise more recently, and have been pretty happy with the results, but I’m by no means an athlete or anything.

I always thought of us as both pretty normal. But right then, Bri may as well have been a greek goddess. She pushed the water away from her face, causing it to stream down her tight body. She would turn to get both sides, giving me a chance to see her backside, suit stretching against her ass and pulling ever so slightly up her crack. At one point she turned to me and smiled, and I could just make out two little points where her nipples were. Holy shit it made me hard.

Once again, I had pretty much no shot at hiding my erection. I literally just stood frozen against the wall with my hand hovering over my crotch.

Then she turned to me and asked “don’t you want to come under the water?”

Of course I fucking did, but all I could get out was “uh that’s okay I’ll get in after.”

She just laughed “don’t be silly,” and reached for my arm to pull me towards her. Just like in bed, I inched a little bit forward, and she stepped in to get closer. Now we were only inches apart, this time facing eachother.

“The water feels nice,” she said.

“Yeah.”

“Aren’t you gonna rinse off too?”

I realized I hadn’t moved a muscle since she got in. I nodded and started awkwardly scrubbing my chest with one hand, the other still covering my dick. Then, I shit you not, she looked directly at my crotch and started smiling.

She whispered “it’s okay. You don’t need to hide. I know it happens with guys.”

Holy shit. I stammered back, “Oh. Yeah, okay.”

I couldn’t believe what I was hearing. But sure enough, I dropped my hand and uncovered my crotch. My dick sprung up like one of those door stoppers and tented straight out in my shorts, pointing right at her. She gave me one last grin, then went back to washing her hair, like it was no big deal. Part of me was disappointed that she didn’t reach for it. But it she had, I’m pretty sure I would have cum all over myself.

We stood like that for another few minutes, inches apart but not quite touching. I had been trying not to poke her with my dick, worried that would be too far. But at one point we both turned our bodies at the same time, and my whole dick pretty much dragged along the side of her body and against her ass. It was brief, but unmistakable. I apologized, but she just smiled and said it was okay. 

After a little longer, she said “Well, I’m gonna get out.” I just nodded, unsure if I was meant to ask her to stay. Instead she laughed again “do you need a minute to take care of that?”, clearly gesturing down to my ‘situation.’

I choked out, “Oh, uh yeah. That’d be good.”

She took one last look at the tent in my shorts, then giggled and stepped out, grabbed a towel, and left the pool house. I couldn’t help it: As soon as the door closed, I pulled down the front of my shorts, gave my dick two strokes, and came right down the shower drain.

As the post-nut clarity hit me, I realized I had just cum to the thought of Brianna while standing in her family’s shower. I admit, I kind of panicked, and decided to get out of there before her dad got back. I don’t think I would have been able to look him in the eye. So I dried off, grabbed my stuff, and crept up the side yard to walk home. I texted Bri that I was heading home, and she wrote back “okay no problem.” We haven’t spoke or texted since then, but fuck me if I’ve thought about literally anything else in that time.

So yeah, sorry if that was less than the update you hoped for. It’s honestly kinda tough to read back. Rest assured I’m still kicking myself for not being braver. But at least now I know FOR SURE that she’s into me! If something happens again, I’m determined not to let it pass me by.

Of course I’m also trying to be cautious, since it’s tricky with our families. But I gotta at least see where this goes, right?

I’ll try and post another update the next time something happens, which will hopefully be very soon. In the meantime, keep it up with the advice/support, cause god knows I could use it right now. Thanks!

Everyone in this story is over 18 years old.

Hi everyone. Sorry in advance if this isn’t the longest orraunchiest story out there, but I really wanted to share and maybe even get some advice. This happened over the weekend between myself and my longtime family friend, Brianna.

Some background: Brianna and I’s parents are best friends from before we were born. When Bri and I were in preschool, our families moved into the same neighborhood, so from that point on we pretty much grew up together. We’re only a few weeks apart in age. I’m an only child, she has one older brother (who graduated college and is living on his own).

Bri and I have always been close, not exactly like brother and sister but maybe cousins. We were really close as kids, but stopped hanging out for most of middle school. Back then our parents made a lot of jokes, asking if she was my girlfriend, if we were gonna get married, etc. It made us kind of uncomfortable and so for a while, we didn’t really see each other outside of family events.

Then in high school, we ended up in the same friend group and started talking again. Since we live in walking distance from each other, we would often share rides or be the first two to arrive somewhere, which led to us hanging out and reconnecting more. I gotta say, it was really nice having her around again. Her parents like me, so I’m always welcome at her place, and vice versa. Bri and I even hang out just the two of us sometimes, and watch movies or play video games when nobody else is free. 

Despite what everyone thought, I never really had romantic feelings for her. Like I said, she’s more like family. I guess she is attractive, but not like that. We’re both normal looking, neither of us is super popular, and it never felt like we were in some teen movie where the main characters fall in love or anything like that. 

Of course, if that was the whole story, then I wouldn’t be writing this. So you tell me what you think:

Last week, Brianna and I graduated high school with plans to go to the same college in the fall (state school not too far from our houses. Neither of us is 100% sure what we wanna do for work yet). Our parents threw a graduation party, but other than that the summer was off to a normal start: just starting our jobs and hanging with friends like always.

That is, until this past weekend. My parents were away, and so I went to stay overnight with Bri’s family. Obviously I’m old enough to be home alone, but this was a tradition from when we were younger. We’d always get pizza and watch a movie at the other’s place whenever our parents weren’t home. Her parents are pretty rich and live in this really nice house, furnished basement, inground pool, the works. It’s not uncommon for me to stay in their guest bedroom, which was my plan for that night.

She suggested we watch this scary movie I’d never heard of. I don’t remember the name but it was actually pretty scary considering it was just on Netflix. We watched the movie downstairs, and when it was over we got up to go to bed.

Bri said she was scared from the movie, which was silly cause she had a blanket in front of her face the whole time, but she asked me to go up first and turn the lights on. I gave her shit for it, but I did it, and she ran up the stairs behind me. After I brushed my teeth, I was heading towards the guest bedroom when she stopped me, and asked if I would stay with her until she fell asleep. I laughed at her again but agreed, and followed her into her room.

She shut the door behind us and told me to get into bed with her. I guess that should’ve tipped me off, but I didn’t think much at the time. When our families traveled together growing up, Bri and I usually shared a room and sometimes a bed. We always just slept, no funny business. Granted we were younger then, but I just assumed this was the same deal. So I said okay and climbed into bed next to her.

At first I just laid there and went on my phone. But then she poked me, and quietly asked if I would cuddle her. I was a little surprised, cause the movie was scary but not THAT scary. I started wondering if she was actually scared, or just making an excuse. Idk if I should have done it, but I did. She lifted the covers so I could get in, then turned on her side away from me. I inched forward so we were almost spooning, but with a good few inches between us.

I’ve never actually done more with a girl than kiss before. And that was only as a dare at a party. I never really dated in high school (and as far as I knew, neither had Bri). I was worried if I got too close to her, my dick would take notice and I wouldn’t be able to control it. So I tried to keep my distance. But then she whispered to come a little closer.

I did as I was told, and scooted forward a literal centimeter. But I guess that wasn’t good enough, cause then she pressed her back into me and closed the distance. Now our bodies were right up against each other. 

She asked “will you hold me?” I could barely think at this point, and just said “okay.” I lifted my arm and brought it around her so we were fully cuddling. I clenched my hand in a fist in front of her, careful not to touch her breasts. Luckily they’re pretty small, so it wasn’t too difficult. But sure enough, my body was freaking out being this close to a girl for the first time, and I could feel my dick starting to grow.

I tried to back away, and Bri asked “what’s wrong?”

I wasn’t sure how to respond. “Nothing.”

“Come back.”

“Uh… I know, but my…”

We’ve never really talked about sex stuff before, so i wasn’t sure how to explain. Thank god she caught on, and just whispered “Oh…” I figured that was it, but then to my surprise, she goes “that’s okay. Come back.” I asked if she was sure, and she said yes. I think my dick got fully hard when I heard that.

Once again, I scooted an inch closer and she moved back into me, pressing her ass directly into my crotch. She was only wearing athletic shorts and a t-shirt. My erection was pointing up into my waistband, and there’s no way she didn’t feel it. I was petrified, almost worried I was gonna cum from just this.

She thanked me for staying, and I told her it was no problem. Then she looked back and smiled with the slightest hint of mischief. She said goodnight and turned away, but then I swear to god, pushed her ass even harder into my crotch.

At first I thought it was a dream. But nope. She was definitely rubbing herself on me, almost like she was trying to feel my dick. For maybe 30 seconds, she sort of wiggled herself on me until my shaft was just nestled between her cheeks. Then she slid ass up-and-down its length, maybe 3-4 times, before finally stopping. Holy shit I nearly busted!

We laid like that for a while, my boner right up against her. I didn’t dare move. Eventually it started to die down, thank god. I guess she fell asleep, and I didn’t want to wake her, so I ended up just staying in bed with her. I was a little worried cause I knew her parents were asleep downstairs, but it would be fine as long as I got up before them and ran back to the guest room. I fell asleep holding her and feeling plenty confused.

Bri was still there when I woke up, laying on her other side facing me. She smiled and said goodmorning. I said it back, then pretty much leapt out of bed and ran to the guest room. I laid in there for another 30 minutes wondering wtf just happened, then went down and said hi to her parents, and left. When I got back home I couldn’t help it, and jerked off while I took a shower. And even though I never had before, i found myself thinking of her as I came.

Later that day, she texted me saying thanks again for staying with her. Other than that we haven’t spoken at all. I’m still reeling from the whole thing.

Obviously it felt amazing, definitely the closest I’ve ever been to a girl. I just never thought that girl would be Bri. Anyway, I’m starting to rethink our relationship a bit and hoping I didn’t fuck things up. Any advice is welcomed if y’all have it. Thanks!