[M]y [F]riend Holly in the Hot Tub

As promised, this is the story of how my friend Holly became my one night stand Holly. She then became my FWB Holly, but those are other tales. In my previous story, I noted that Holly was my ex’s younger sister. Five years younger than my ex, and 7 years younger than me. I became something of a mentor to her – got her a job, helped her apply for college, etc. And she had also grown into a really beautiful young woman. Holly was thin and waify with few curves, prominent hip bones, and boobs a little bigger than you’d expect on a frame like that. A brunette with long straight hair and huge blue eyes; I’ve always been a big fan of that combination.

I’d visit Holly when I was back in town to see my parents. Or, she’d visit me at my parents house, which had a really sweet hot tub. I didn’t know then just how far a hot tub goes to setting the scene with a girl. It’s actually crazy.

About the third time she came over, it was unplanned. She texted me just because she was close by and I invited her over. She was there in ten minutes, and I got her a drink right away. Normal visit so far. Then I told her I’m heading in to the tub, and invite her in with me. “cardinallines, I didn’t bring a bathing suit. You didn’t tell me you were going in!”

“Holly, when have we ever not gone in?! We have extra bathing suits downstairs, grab one.”

I jumped in the tub with my drink. She came back a few minutes later, still in her black jeans and matching tank top, looking a little defeated. Everything we had was too big for her. “Nothing fits; this sucks! I really want to be in there with you.” I started teasing her a little, about how great the water felt, how the jets were massaging me all over, and she got really jealous, really fast.

“I could just come in in my bra and underwear, is that OK?” Unexpected turn of events.

Now, this was a turning point. I either say no and potentially ruin the evening. Or I say yes, and try not to stare. I had no plans to exploit our relationship, but shit, I had to admit that Holly was really hot. I wanted her company in the hot tub, and was definitely OK to see her in her underwear. So I said “It’s basically the same thing as the bikini you normally wear, go for it.”

Without a word, she starts to strip down, and doesn’t go anywhere private to do so. She strips right in front of me, in the middle of a conversation. We were looking right at each other when she undid her jeans and unzipped. I caught a hint of black panties. Then she hooked her thumbs into her belt loops and yanked down as she started shimmying the jeans over her ass. I was making no effort to hide my gaze. Holly turned around as her jeans got down to her ankles and bent over to get them off. Such a hot moment in my life. It was kind of the first time I had thought of Holly in ‘that way’, and was getting a great view of her ass in little black boy cut panties. Still turned away from me, she pulled up her black t-shirt and showed off the most impressive back dimples I have ever seen. Fuck what is so hot about those?

Holly is standing there in matching black bra and panties, not hiding anything from me, and certainly not bashful. “Can I come in? It’s cold out here!”, she said, so I motioned to the seat next to me. She jumped in quickly, and sat right next to me. Very close. I took a sip of my drink and that made her realize that she forgot hers over by her pile of clothes. So she pushed over to the far side of the tub and reached as far as she could for her beer. Her soaking wet ass was just above water level, and that’s exactly where my eyes were. Then Holly turned around, fully caught me staring at her perfect little ass, and smirked.

“I can’t reach, I need your help cardinallines, pleeaaaase”. I went over and playfully picked her up and out of the way. As I reached for her beer, Holly ‘playfully’ pulled down my boardies and ‘playfully’ smacked my ass. I really didn’t see it coming, and kind of didn’t know what to do about it. It looked like she was looking for a reaction, waiting for me to proceed. I handed her beer to her and told her I wanted her to drink it all. To chug it. She was a couple drinks behind me and I told her she needed to catch up. Holly stood up and started chugging as best she could. Beer was spilling out of her mouth, down her chin, and dripping onto her tits and bra. I got a good look at them for the first time ever, and they were tight, perky, round perfection (maybe to be expected for an 18 year old?).

“You’re dripping, Holly. Be more careful. No more spilling”.

“Yes, cardinallines.” In two words, Holly revealed her submissive tendencies that I didn’t know existed.

“What was that?” I asked, trying to pry a little.

“I’ll be more careful for you. I won’t spill any more.” Careful…*for me*.

“Good. Now finish your beer, next round is yours.” Holly finished up and popped up out of the tub and gave her ass a little shake while she looked over to me. Fuck. My cock was so hard – I was happy the water was hiding it. Although the flirting was getting pretty crazy, there was a line between us that would need to get crossed if we went any further. I was conflicted.

Holly came back with our drinks. She passed mine over the side of the tub, but I told her I wanted her to bring it all the way to me. Clearly, I was exploring her. She protested a little, saying she needed to hold on while she got in and needed a free hand. I told her to figure it out. So Holly cradled our drinks in her cleavage, gasping the whole time because they were so cold against her wet skin. When she got in, she immediately went under to warm up, holding the drinks above water.

“That was cold on my boobs, I have goose bumps now, you dick!” I stared right down at her tits and the little pink bow on her soaking wet black bra.

“Yes you do, I can tell how cold you are.” Holly giggled a little and pushed over to me.

“This is your fault, you have to warm me up now. ” She came in and wrapped her arms around me under the water. I was trying to hide my raging cock, but boardies don’t offer much resistance, so her arms grazed my cock that was standing straight up.

“OMG! cardinallines, are you hard under there? I felt it!”

I had to fess up. “Holly I’m SO hard. Turns out bra and panties aren’t the same as a bikini. I can’t stop staring.”

“You don’t have to stop. I like when you look” With that, I knew we were about to cross the line to being more than friends.

“I liked it when you were standing up before. Stand up again.” She did, and even looked directly into my eyes a couple of times. She was so sexy in that moment. She got cold in less than a minute. Her goose bumps grew thicker.

“I’m cold again. I want to go under again!”

“Not yet. I like this view. Stay standing, or you get punished” She did as she was told. She stood there and took in my gaze, shyly looking away when our eyes met. She even turned around when instructed – and arched her back show off. When I absolutely couldn’t handle starting at her any longer, when I had to feel her touch, I stood up and came up to her from behind. One hand went to her bra, one onto her tight stomach. Our first sexual touch. It lasted forever. She was tilting back to moan into my ear and kiss my earlobe while pushing her ass into my cock. I was exploring her body and couldn’t decide which part my hands liked the most. Every single part of her that I touched felt perfect to me, and goddam she was so tiny in my arms.

I turned her around and kissed her deeply. She showed a little inexperience in kissing but caught on quickly. As much as I was feeling around her body, Holly was doing more with her hands. After kissing for less than one minute, she had both hands in my boardies; one holding my balls while the other jerked me off.

I pulled her bra strap and the weight of the water soaked into it dropped it right off her tits that were just a little less tanned that the rest of her. Her nipples were close to the same colour as her skin. Super hot. I then pulled the string on the side of her bottoms and stared as they fell away to show a waxed pussy that looked like it had never been touched. Holly undid my shorts and taking them off gave her more freedom to continue her hand job. Now, I don’t want to complain about a hot 18 year old jerking me off, but I think almost every guy would agree that a handjob is just kinda OK. It’s a thing that guys can do better if they do it themselves. I wanted more than her hands. I picked Holly up and sat her on the edge of the hot tub and then lifted her legs up onto my shoulders. Shit was escalating quickly – it was only about 5 minutes ago that we first learned of our mutual attraction – and now I was about to taste her perfect little pussy.

She was SO wet. Her pussy tasted amazing and she was dripping down my face within seconds. I focused on her clit while I fingered her, trying to hit her G spot my my fingers, which seemed huge compared to her. Holly came all over my mouth and fingers not long after, and I felt her pussy convulse on me. I loved it. I didn’t stop, actually putting in another finger. It barely fit. It took her a few seconds to get used to two fingers, but once she did, she wrapped her legs around my head and pulled me in so tight. I could barely breathe, but that didn’t stop me from kissing and licking her pussy. I looked up at her and told her how hot it was when she came for me. She smiled down at me, but her attention was clearly taken by my fingers. She pulled my head down further, really forcing it into her pussy, and then came for me again.

I pulled Holly by the hand into the hot water to let her warm up. Then I pushed her into the edge of the tub facing away from me. I took her arms and put them behind her back and sternly told her to keep her arms there.

“Yes, cardinallines.” I loved her compliance.

Her pussy was barely above the water line, and I pushed my cock head to it, which was soaking wet and sensitive. Holly pushed back into me, telling me she wanted to be fucked. I pushed into her, and Holly pushed back further, but my cock didn’t slide in. She was too tight! I grabbed her forearms for leverage, and pushed harder, then harder, then harder. To her credit, Holly kept her back arched and ass in the air while I coaxed my cock into her. When she was able to take my cock, we didn’t really fuck each other for the longest time. She was squeezing and releasing my cock in pulses without moving in and out of her. It was a great sensation for me, and I could tell Holly really loved being as full as she was.

I began to slowly pull out of Holly’s tight pussy, but it did *not* want to let me go. I started with a slow rhythm and Holly was a perfect good girl for me: back arched, arms where I instructed, ass in the air. She moaned and gasped with my movements, but clearly wanted me to use her pussy. I know that because she said “cardinallines, fuck my pussy.”

I really wanted to feel my cock hit the back of Holly’s little pussy so I thrust in hard and fast. Her pussy resisted as much as it could but eventually I made it all the way inside her and was really pushing in hard. I wanted to watch my cock fuck her so I told her to spread her ass for me. She did. I stared down at her asshole and pussy while I pushed in as far as I could go before I hit bottom. I could feel myself getting close, and wanted to hear Holly’s answer to the question “Where do you want me to cum?”

“On my face, cardinallines. I want to taste your cum like you tasted mine.” It’s the hottest possible answer, I think.

I pulled out of her pussy and she turned around and got down further in the tub. Only her head was above the water. I alternated jerking myself off and fucking her mouth until I shot a gigantic load all over her face. One eye looked glued shut. I properly covered her. She coughed a little when I shot cum down her throat, but sucked my cock clean and swallowed what made it into her mouth.

“Thank you, cardinallines. Your cum tastes so good!”

That was the first time with Holly, who became a great submissive FWB for me for about a year. Her sister, who was my girlfriend for years, still has no idea that I pounded her little sister dozens of times. I love that.

Source: reddit.com/r/gonewildstories/comments/4imq30/my_friend_holly_in_the_hot_tub