Category: Hookup Lifestyle

I had just given this 18 year old girl her very first orgasm and it felt great. I made sure to do everything slowly so she could pay attention to what I was doing and learn from it. It was more than I had ever expected to do with this girl. She was my friends’ daughter and I was just supposed to be watching their house. I didn’t even know she was going to be here, but here I was. I didn’t want to go any further than necessary to help this young girl out.

I made my way out

I leaned in and kissed her on the forehead. I wanted to do a whole lot more, but I had to control myself.

“Now you can practice on your own.” I said.

I slid out from behind her and stood over her. Her hand was already on her pussy and exploring. She smiled up at me and tried grab onto my shirt with her free hand. I caught it before she was able to and smiled down at her.

“Oh, no. You have to do it yourself now. That’s how you learn.”  I bent down and kissed her on her lips. “Have fun, sweetie. I’m going to get ready for bed.”

“Okay.” She smiled at me and closed her eyes against the pleasure that she was giving herself with her fingers. She moaned sweetly and arched her back as I turned away and walked out of the room. I completely forgot about closing her door as I made my way to the bathroom. I needed to be away from her or I was going to fuck the shit out of her and that would have just been inappropriate and unfair to her parents.

I took a long shower

My underwear was sticky with precum. I tossed all of my clothes onto the bathroom floor and turned on the water for the shower. My cock was hard and throbbing. I really thought about jerking off when I stepped into it. It would have relieved me of a lot of sexual energy, but I just couldn’t bring myself to do it. Having sex in someone else’s house is one thing, but jerking off in their shower is completely another. I just took a shower for as long as it took for me calm down. It took a while, but it worked. I stepped out and dried off with a towel. It was at that point that I realized I didn’t have any clothes to put on. I sighed and tossed my dirty laundry into the nearby hamper and opened the bathroom door. The air was cold compared to the shower but I stepped out into the hallway nonetheless. I guessed I just had to walk down the hall naked. It’s not like it was anything worse than what I had already done in this house. Of course, it was walking to the room that I realized I had forgotten to do something else.

She was definitely practicing a lot

I walked by her room and realized that I had left her door wide open. It was impossible not to look in on her. I saw right away that she was doing what I told her. Her legs her spread wide and she was still completely naked. She had the laptop on the side of the bed watching a porn star give a blowjob to someone. She was looking away from her door and at the laptop while her right hand worked feverously on her pussy. Her entire body was moving and she was really pulling on her nipple with her left hand. I just stood there for a minute and watched her make herself cum again. I got the sense that it wasn’t the first orgasm she had given herself since I left. She was sweaty and exhausted at this point and her arms just fell down to the bed on either side of her. She laid her head back and closed her eyes while the guy in the video came all over the porn stars face. My cock was once again fully erect and I couldn’t help but smile as I stepped back and made my way into the master bedroom.

I was pretty exhausted as well

I sat down on the bed, still completely naked. Being so worked up had taken its toll and I was just too tired to put anything on. I just laid back on top of the comforter and tried to relax. I was looking forward to sleeping when I opened my eyes and realized that, once again, I had forgotten to close the damn door. This was getting to be a real issue for me. I was tired, but it had to be down. I sighed dramatically to myself and sat up in the bed. I was just about to stand up when she moved into the doorway. She looked even more exhausted than I was. Her hair was messy again and her face was glowing a healthy pink. She had a tired smile on her face as she walked into the bedroom and sat down next to me. She was still completely naked and she put her head on her shoulder with a yawn.

“I don’t think I can cum anymore.” She said. She wrapped her arms around me and rested against me.

“That just means that you’re doing it right.” I said with a laugh.

She was watching the porn for a reason

“I want to thank you for helping me, but I don’t know if I can do it right.” She said as she opened her eyes and looked up at me.

“Oh, you don’t have to thank me. I did it for you.”

“No, but I want to. I was watching videos for it and I want to try it.”

I had a pretty good idea of what she was talking about but I had no energy to say anything. She slid off of the bed and kneeled on the floor in between my legs. I probably could have stopped her, but I was just too worked up. I lost all control and just leaned back. I closed my eyes when I felt her warm mouth close around my dick. It was soft and felt amazing as she started to slide her head up and down my shaft. I opened my eyes just in time to see her pull me out and run her tongue all around my head and up and down my shaft. She had certainly paid attention to the videos she was watching. I laid back and just let her work.

It was just good enough

She clearly wasn’t any kind of a blowjob expert. What she lacked in experience, she more than made up for with enthusiasm. She sucked my dick just like the porn stars that she had been masturbating to. It felt good but the overall feeling of being her first blowjob made it one of the best that I had ever had in my life. She stroked me with one hand and sucked me for all that she was worth. I figured that I would use this as another learning experience for her. She sucked me off for a good ten minutes before I finally let myself get close to the edge. Then I reached up with one hand and put in on the back of her head. I guided her up and down my cock and followed along happily. I pushed her down further and further to get her used to it. Then I went all in. I pressed her head down hard and let my hot, built up cum shoot right into her mouth. She never stopped for a single second. This girl took my whole load and swallowed as fast as she could while it shot into her mouth. I let the pleasure course through me until every last drop was out, then I let go of her head. She took the cue and stopped sucking at exactly the right second.

She was very proud of herself

Opened my eyes after a few seconds and saw her just smiling up at me. She knew that she did a good job and she was very happy about it.

“Okay, get up here.” I said.

I pulled down the comforter as best I could and laid in the bed. She climbed up and laid next to me. I just spooned her and held her until we both fell asleep.

That wasn’t the end of it

I have to take a break now, but keep in mind that I spent an entire week with this girl in the house. There were plenty of other things that we did together. All in all, it was a really find week long hook up that I’d do again in a second. Maybe I’ll have some more stories about this girl later on.

I don’t know what I expected, but I really didn’t expect her to be naked and waiting for me. Looking back now, it seems pretty obvious that it was about to happen. Either way, my plan completely disappeared. She was sitting on her legs and looked amazing. She was looking up at me with a level of need and submission that’s incredibly difficult to come across. This was a girl who was going to let me do anything I wanted to her. All she needed in return was the experience that I had to offer her. I stepped into the room and closed the door behind me.

I dropped the laptop

I put the computer on her nightstand and sat down on the bed next to her. “Okay.” I said. “Are you sure you want to do this?”

She nodded very decidedly and stared deep into my eyes. “I want you to teach me.”

Having her look up at me was more than I could deal with. I wanted to do things to her that I knew I’d end up regretting later on. I could give her what she needed, but I had to be careful to keep myself under control.

I needed to see her moves

I told her to lie on her back and spread her legs. She followed my instructions right away. I could tell that she was nervous and her body trembled just a little bit. I adjusted myself so I was sitting by her knees and looking at her entire body. I put my hand on her knee to reassure her that I was there to help her. She smiled and shyly told me that my hand was warm and felt nice. I thanked her with a laugh and told her to touch herself like she normally does.

She had no idea what to do

“Like, everything?” She asked.

“Yes, everything. I just want to see.”

I sat back and she nodded and closed her eyes. She slowly started to run her fingertips up and down her entire body. She was very gentle with herself and I could see her skin break out in goose flesh. It was clear that she was trying to send tingles up and down her spine. She was a girl who liked sensuality and it was no surprise why she wasn’t able to get it from anyone in her age group.

“That’s good, keep going.”

She nodded with her eyes still closed and ran her palms over her perfect boobs. Her nipples were already erect, but I could imagine her trying to get them hard when she was alone. She started squeezing and pinching her nipples. She even stretched them a little bit. It made her moan quietly and her back arched under her. That was how she got herself wet when she tried to masturbate. It’s a trick that a lot of women use and she had already found it on her own. It was obvious that she had tried this many, many times in this room.

I worked hard to keep to myself

It was getting harder and harder not to touch her. I knew that I had to hold myself back, though. I gave in a little bit and leaned in to kiss her knee. She shivered and smiled as soon as she felt my lips touch her body. That was when she brought things to the next level. She ran the fingers of her right hand town her stomach and over her pelvis. The other one stayed on her left nipple to pinch and stretch it.

She was close

Her right hand got her to her virgin pussy and I immediately saw were the problems were coming from. She started rubbing her entire pussy with her fingers. She kept them straight and just ran them up and down her pussy lips. Her back arched over and over again as she worked. She started to grind her hips against her hand and pressed it in more and more. I watched her for a few minutes when I felt her eyes on me again. She was looking at me with doubt all over her face.

“This is how far I always get. It feels really good, but that’s it. I just get frustrated after a while and stop. I don’t know why I can’t cum.”

“I think I know.” I said as caringly as possible.

I took over

I moved around on her bed and put my hand under her shoulders. I made her sit up and slid in behind her. Then I pushed her shoulders back from the front so she was lying back against my chest. Her arms fell to either side of my legs and I reached forward with my right hand. I used my left hand to cup her breast and pinch her nipple, just like it seemed she liked. Her skin was soft and warm. I could feel her heart pounding in her chest under my palm. She closed her eyes on her own and started breathing hard. She was heaving and she clenched her fingers around my calves. I kissed her on her forehead and slid my middle finger in between her pussy lips. She was soaking wet and felt amazing. She bent her head back as far as she could and I kissed her on her lips.

I got to work

It wasn’t difficult to find it, but I could see why she had missed it. She was a girl who was cursed with a small clit and she had no idea about it. I slid my finger up her pussy and ran it in circles under her clitoral hood. It was swollen and I could almost feel it throbbing under my fingertip. As soon as I found it, she jumped and moaned loud. She strained to kiss me again. I rested my head against hers and just worked her clit as gently as I could manage. I worked it in circles and I rubbed it. I pressed against it and slid my finger over it. Each move elicited a whole new reaction from her. It was clear that I was making her feel things that she had never experienced before. Her entire body moved and shuddered under my touch. I could feel sweat break out on her forehead. She started moaning louder and louder. The last thing I heard from her was a soft and shy “Oh, my God!” Then she exploded in orgasms in my arms. She shook violently in her very first orgasm and I let her cum for as long as she possibly could. It was extremely hard to keep her slippery clit under my finger but I worked as hard as hard as I possibly could to make it happen. I was going to give her the best orgasm that I possibly could. It was my gift to her and my way of introducing her to the world of pleasure that lay in front of her. I kept working her clit until her legs started to buck, then I stopped. I wrapped my left arm around her heaving chest and pressed my right hand into her pussy. That’s the best way to help a pussy relax after and orgasm.

It took a long time for her to come down

I held her for what seemed like hours. She was breathing more regularly as the waves of pleasure stopped coursing through her young body. She finally opened up her eyes again and looked into mine. A wide smile broke out over her face. She reached up and put her hand on the back of my head to push me in for another kiss. I totally gave in this time and slid my tongue into her mouth. She responded by sucking on it and giggling. I pulled back and just enjoyed the look of totally satisfaction and pleasure on her face.

“I had no idea that it could feel that good. Thank you, so much!”

“You’re welcome. Did you pay attention to what I did?”

She nodded with another smile and closed her eyes with a long sigh. She rubbed her palms against my knees in total happiness. It seemed like I had taught her everything that she needed to know on top of giving her her very first orgasm. I couldn’t have been any prouder of myself.

More next time

That wasn’t then end of my special time with this girl. I had an entire week in this house and it felt like things were just starting. I’ll tell you more next time. It turned out that it wasn’t even over for the first night. This was as very special girl and I was lucky to meet her. She still had a lot to learn and she was more than willing to ask someone to teach her. It happened to be me that she was asking and I wouldn’t have traded it for anything.

So, I was stuck in this very sexual conversation with an 18 year old girl who also happened to be my friends’ daughter. I was watching their house and had no way out of it. I didn’t just want to tell her to stop talking to me. That would be rude, but I had to do something. That’s why I escaped into the kitchen and opened the fridge. I just stared into it for a few minutes and break the tension and hopefully get her mind off of the subject. Then I found out what it’s like to be stalked.

She was right there

I closed the door and she was right there standing behind it with a big smile on her face. I jumped a little and took a step back. I could see that her excitement was rising and there was nothing I could do to slow it down. I just moved to the kitchen island and sat down. I smiled at her and exhaled as she sat right down next to me. She crossed her legs and made sure that our knees were extremely close to touching.

She pressed on

“I bet you’ve had a bunch of sex, huh?” She asked, bubblier than ever.

“I guess I’ve had the usual amount.” I answered and turned my body so I was facing the kitchen and not her. It didn’t stop her, though. She just moved in closer to make sure that I couldn’t ignore her, no matter how hard I was trying to.

“Do you just have sex without making the girl cum? Like, is that a normal thing for guys to do?”

“No, of course not.” I shook my head. I had to at least give her some real advice here. I could tell that she was in a place that wasn’t good for her. If she learned that women never have orgasms when they have sex then she could end up spending a big chunk of her life without ever experiencing actual, good sex. “It’s not normal for guys who know what they’re doing. The ones who do it that way are just selfish and not the ones that you want to get involved with.”

“I didn’t think so!” She yelled. “My friends all act like it’s normal, and I’m like, ‘no it’s not!’” She laughed.

That’s when it hit me. This was a girl who needed help, just like all of the others. She was stuck in a world where she wasn’t getting the kind of sexual pleasure that every person on the planet should be able to enjoy. I slipped deep into the mindset that I usually inhabit. She was suddenly an inexperienced girl who had no idea about how good she could feel with another person. It was quickly becoming my problem just as much as it was hers. I started to feel like it was my duty to give her what she was missing and that was a very dangerous place for me to be in. Even so, I turned back to her.

I opened up to her

“Look, if a guy can’t get you off then he might just not know how. Sometimes you have to tell him what feels good and what you like. If he doesn’t put in the effort to give you all of the pleasure that he can, then he’s selfish and you shouldn’t involve yourself with him. There are much better guys out there.” I was pointed and told it like it was. That small act made most of the tension pour out of my body and I relaxed a little bit more.

“But, like, what if the girl doesn’t know what feels good? Like, I was with a guy once and I didn’t know what to tell him. It was just super awkward and I stopped talking to him after that.” She said with real confusion on her face.

“You just have to pay attention to how it all feels. Just tell the guy to do the same things you do when you masturbate. The rest will work itself out.” I sat back in the chair and hoped that this would take care of everything and we could end the conversation.

She was extremely inexperienced

She kind of looked down in embarrassment at that. I immediately felt bad about bringing it up.

“Oh, I don’t do that. I don’t know how to.”

“You don’t know how?”

“No, I’ve tried, but it never works. I’ve watched videos on how to do it and even asked my friends how they do it. I try it and nothing ever happens. It just kind of starts to feel really good, but that’s it. I’ve never had an orgasm and I don’t know how to make it happen.” She was extremely embarrassed and I could just tell that she was really opening up to me for some reason.

She put both of her hands on my knee and looked up into my eyes. She was pleading with me at this point and I could feel all of my resolve disappearing.

“Do you think you can help me? I mean, you have a lot more experience than me! You know what to do! Do you think you can just tell me or something? Like, seriously, I feel like I need help or I’m going to be weird for the rest of my life!” She bit her lower lip and her fingers tightened around my knee.

Now it was my problem

That was the real turning point. Now this whole thing was my issue. This young girl was honestly begging me to help her learn her own body. It was obviously that it was a real point of stress in her life. It was on her mind and it was something that was holding her back. If I didn’t help her with this then no one would. The people around her had no ability to make any of this right for her. It was me or it was no one.

“Okay, I’ll tell you what; I’ll try to help you.” Her entire body tensed with excitement and she smile wide. “I don’t want to do it down here, though. Go head up to your bedroom and I’ll be up in a few minutes. I’ll find something to show you what to do, then I’ll just leave you to do it. No one can ever know about it, though. I don’t want your parents to think that we did anything. I’ll just show you what to do and leave, okay?”

“Okay!” She jumped up with a giddiness that I had never seen in my life before. She turned and ran up to her bedroom, happier than I had seen her all day.

Once I heard her door close, I got up and fell onto the sofa in the living room. My plan was simple. I’d find a few porn videos where the girls actually walk you through the masturbation experience. I knew they existed because I had come across them before. I’d bring them up to her, put the laptop on her bed, then just walk right back out and close the door. I wouldn’t have to actually do anything with her and I’d be helping her out at the same time. It was the perfect plan and I felt brilliant for coming up with it. All I had to do was make my way upstairs and I could go back to not fighting against the urge to have sex with my friends’ daughter.

It didn’t take long to find the videos that I was thinking of. There were plenty of visuals and the women were being honest about what they like. They were real instructional videos and they would do the job. I got up and immediately felt the sudden cold of precum against my dick. I guess I was more into this idea than I was letting myself believe. I walked up the stairs and go to her door. I knocked a few times and opened it right up. That was when I knew that this plan had some flaws in it. What I hadn’t expected was to walk into her room and see her totally naked and sitting on her bed, waiting for her. That feeling of cold precum vanished and was immediately replaced by the feeling of my cock exploding into a full erection in my pants. Her body was absolutely perfect and I’d really have to do some thinking to come up with a sexier one.

More next time

I don’t know why I wasn’t expecting that, but I just wasn’t. I have to keep going with this story and I’ll get right back to it next time. There was a lot going on in my mind but I still felt it was my duty to help this poor, young girl out. I’ll let you know what happened on my next post.

I talk a lot about helping out older women and married women. I just feel like these girls need something that can be very difficult to get. It doesn’t mean that I don’t realize the younger girls need help just as much. Sometimes you just have to do what it takes to make a young girl happy and give her the experiences that she’s missing. When a girl is going through college, she’s going to be coming across other girls with much more experience than they have. It can lead them down a path of constant lowered self-esteem and no one should ever have to deal with that. All it takes is one good sexual encounter to put them on the same footing as the other girls. That’s why I make it my business to take care of them whenever I find one and that’s exactly what happened a few years ago when I was paid to house sit for a couple that was going out of town for a week. They had an 18 year old daughter who was going to be in and out of the house while I was there. She was a college student, but her school was close by and she didn’t always want to stay in her dorm. If I had known just how much she was going to be around, I probably would have taken the job for free. As it turned out, her being there was just a tip on top of the money that my friends were already paying me to watch their house.

She was surprised as well

I got there early on the morning that they were taking off for the week. We were sitting in the kitchen and going over all of the details for the time that they were to be away. I should probably mention that this was a very wealthy family. Everything about the house was fancy and I was pretty much in awe of it. it was more or less a mansion and I was getting to spend a whole week there. I think we were going through the security codes when the daughter walked into the kitchen. She was a total, sleepy mess. Her hair was in knots and she was wearing a pair of pajamas that had definitely seen better days. She just looked up, saw a stranger with her parents, looked like I had just walked in on her in the bathroom, and yelled “Mom!” She ran out of the kitchen in embarrassment and her parents just started laughing. It wasn’t mean spirited at all, just funny. She certainly wasn’t expecting anyone to see her like that, let alone an older guy who was going to be staying in her house for the next few days.

She was a hottie

It was a few minutes later and my friends had their luggage in hand and were about to walk out the door. They called their daughter down to say goodbye and she practically danced down the stairs this time. She was all dressed up and clearly trying to make a much better impression this time. Believe me when I tell you that this girl was hot! She was wearing a short skirt and short that showed off her mid-drift. Her tits her perfectly perky and her naked legs were amazing. She has her shoulder length hair pulled back into a ponytail and it showed off a pretty face that any man would fall in love with. She kissed her parents goodbye and they told her to be safe while they were gone. A few seconds later, I was alone with their daughter with an entire week of time on my hands.

She tried to get my attention

It was pretty obvious right away that this girl was going to try and get my attention in any way that she could. It’s not like she was being overly obvious about it, but I could tell. She would make sure to bend over in front of me any time she could. There was one point when I was sitting in the kitchen and going over their notes when she opened up the fridge and bent way over to get something. She definitely didn’t have to bend over as much as she did, but she certainly gave me a nice show. We made small talk whenever we were in the same room and she went about her business, walking in and out whenever she needed to. I was sitting in the living room later on when she came in and sat next to me on the sofa.

“What are you watching?” She asked.

“No idea.” The TV was on, but I wasn’t paying any attention to it. I had plenty of my actual work to catch up on with my laptop. “You can put on anything you want, I’m not watching anything.”

Things got sexual pretty quickly

I don’t know what she put on, but I know that it was extremely sexual. It’s not like it was porn, but it was definitely something that you wouldn’t want to watch anyone else. It was essentially a softcore porn movie that you get on the premium channels. I just let her watch it and kept myself focused on my work. Naturally, she had already pretty much decided that I wouldn’t be getting much done.

“Did they tell you about the last guy they had watching their house?” She asked to start up a conversation.

“No, not at all, why?” I guess I took the bait, but I had no choice. I didn’t want to be rude to her.

“They found out that he shot porn while he was here.” She said really matter of factly.

“He what?”

“Yeah, he had a bunch of people come over with equipment and everything. They found a bunch of ads for amateur porn stars online later on. I guess he was planning it for a while.”

“Wow!” I had no choice but to put down my laptop now. That was a hell of a way to get my attention!

She perked up once she got my attention

She turned on the sofa so she was facing me now that she had me. “Yeah, I guess that’s how people shoot porn! They just find a way to get into a big house and shoot as many scenes as they can. They found him online and I guess he does the same thing all over the country! Some of my friends have seen some of it, but my parents keep getting it all taken down as soon as they find out about it.”

“Well, I wasn’t expecting to hear that!” I said. “Why don’t you just watch the house for them?”

“They just want someone to be here every night and I don’t want to have to drive all the way to school every morning. I just stay here when I want to be alone. My roommates always have a bunch of guys over.”  She said with a sigh at the end.

“Don’t you like being around guys?” I asked as gently as I possibly could. I didn’t want to come off as anything other than a person having a conversation with her.

“Not the kind of guys they bring over.” She laughed. “They’re all just douchy and my roommates are sluts. They just let them fuck them for the popularity. I get tired of hearing it through my door.” She smiled.

This was clearly not a conversation that I should have been having with my friends’ 18 year old daughter, but I had no tactful way out of it now. I let her engage me and now I was trapped. My only chance was to brush it off.

“Yeah, I know the type. I can see why you try to get away whenever you can.”

“Yeah, I don’t know why they do it. I don’t see the point of having sex when the guy can’t make you cum. That’s why I don’t bother. None of the guys my age know what to do in bed. That’s why I’m still a virgin.” She smiled sweetly and my discomfort grew.

I just got up

“That’s a good way to be!” I said and stood right up. I had to detach myself from the situation and did it as quickly as I could. I walked to the kitchen and opened the refrigerator door. I just wanted to break her line of sight to me so I could take a breath and get a handle on this situation. Talking about sex with a teenager like this was starting to have an effect on me and I had to calm down.

More next time

I need to take a break from even telling this story. There’s a lot more to it, so I’ll get back to it next time. Just trust me when I tell you that the younger girls need just as much help as the older ones.