Daughters Friend Needs Help

"You are so bad," I overheard my daughter say lightheartedly as I walked by her bedroom. Unbeknownst to her and her bestie Cassandra, I had come home from running errands.

"I don't want to college a virgin. Statistics say that if you wait until college, it's more likely that you lose your virginity after getting drunk, to some random guy you just met, instead of having it be something special," I heard Cassandra say. I leaned forward to peek inside the room. By my shifting of my weight, I caused the floor to creak a little, but the girls did not seem to notice. I held my breath momentarily, thinking that would help for some reason.

"You and your stats, nerd," my daughter replied. "Why didn't you hook up with David before you guys broke up?"

"Well, the first time I touched his penis he came, like literally came within a few seconds. He was so embarrassed that he ran home," Cassandra explained.

I was curious to hear if my daughter Beth would talk about her experience, but something popped up on their phones that made them change topics. I took a couple of steps back and then pretended to walk by for the first time. I knocked on the cracked door and pushed it open a bit more.

"Hey girls. Are you guys hungry? I was about to make dinner. You are welcome to stay Cassandra," I said.

"That would be great Mr. Dan," the eighteen-year-old brunette said. She and my daughter were sitting on the bed with their legs crisscrossed. Cassandra wore denim shorts that seemed to show her thighs in their entirety. The white crop top also made it hard not to admit that she was gorgeous.

I went into the kitchen and began to grill some chicken and vegetables. I was a single dad. My ex-wife had various mental health issues that she was never willing to work on. When she caused a severe car accident with Beth in the backseat, I had enough. Her BAC was 1.40 and she showed no remorse for hurting a family of three.

That was four years ago, and I never really regretted my decision to file for the divorce. Cassandra joined me in the kitchen and sat down on the barstool. I could not help but scan her long tanned legs before making eye contact.

"Where is Beth?" I asked.

"Taking a shower. I told her she stinks."

"Ready for college?" I asked.

"Kind of. I am a bit nervous."

"That's normal. You will be fine. Your 4.0 GPA means that you have the smarts and work ethic to succeed for sure," I explained.

"I know. I am not worried about the academic part," she said.

"Worried about them frat boys?" I joked.

"Weren't you one in college?"

"Yes, and I don't recommend it."

"Why is that?"

"Took me two years to realize that getting drunk nearly each night would not get me very far," I said.

"I am afraid of having fun like that because the next thing you know, you end up in a dark basement making out with a guy you just met, and all you taste is beer," Cassandra said.

"That's a bleak expectation you set there. Don't ever let some guy make you do something that you don't want," I said firmly.

"I know, I know," she replied. She began to scroll through her phone, so I took another look at her legs. The way she had her feet propped up on the stool caused her calves to be flexed, making them look even more toned.

I think she noticed me staring so I quickly turned and asked if she wanted to help me set the table.

"You got it!" she said enthusiastically. I did not pay attention to her as she grabbed the plates and silverware.

"Mr. Dan," she said with a groan, "can you lend me a hand?" I looked over and she was trying to grab a wine glass from a high shelf. She was on her tiptoes and barely preventing the glass from falling. I quickly stepped up behind her and grabbed the glass, but not before the front of my pants made contact with her butt.

"That was close," she said after I stepped away. Seconds later, I noticed her blushing.

"Let's get rid of the mister part when you say my name, ok?" I said.

"Sure...Dan. Might take me a while to remember and get used to."

I tried to give more fatherly advice during dinner since Cassandra has been raised by a single mom since she was born. I had known her for ten years and seeing her as a young woman made me look at her a bit differently.

The girls decided that they wanted to go hot-tubbing and insisted that I should join them. I loved the fact that our home had become a second home for Cassandra. She had a couple of bathing suits and other clothes kept at our house since she often spent the night. When they outgrew Beth's bed, Cassandra would often sleep on the couch in the living room. I barely spoke to her mom, but I knew the lack of a father was not the only thing missing at home.

I tried to excuse my way out of joining them in the hot tub but ended up agreeing. Beth was already in the water with me when Cassandra finally came out in a bikini I had not seen on her before. It barely covered anything and accentuated her young fit body.

"Yep, that's a keeper," Beth said as we watched her climb into the water. When she turned her butt towards me for a brief moment, I grunted internally, noticing that the black fabric barely covered her tight ass.

I grew hard for a little moment and kept reviving my erection each time Cassandra took a quick break from the hot water and sat on the edge.

"What are you going to do once you are an empty nester, Dan?" Cassandra asked.

"Since when do you just call him Dan?" my daughter asked.

"Tonight. He told me to," she answered.

"That's how it is, huh? My friend turns eighteen and ya'll are just friends now?" she asked sarcastically.

"Not sure what is going to change," I began saying. "Not having Beth around will suck, I am sure."

"We are only an hour away," Beth pointed out.

"Let's be real. You are not gonna come see your old man each weekend. I am sure you will have some guy convincing you to stay there except for major holidays," I said.

"Dad! I am not going there to find some guy," Beth said.

"Yes, Dan. Boys in college are way too immature," Cassandra added.

"So, you are going to be on the lookout for some older, mature men?" I asked, immediately regretting the question.

"Maybe. I would choose you over any young college guy any day," Cassandra answered and also seemingly regretted her response right away.

"CASSANDRA!" Beth yelled. "Are you serious?"

"That came out wrong, sorry," she replied.

The next few minutes were awkward for sure. When it was time to get out, I turned away from them to make sure I did not look at Cassandra climbing out. When both of them walked away though, I turned around prematurely and saw Cassandra walk away with the towel in hand, instead of it being wrapped around her. The way her barely covered ass moved made me hard again.

I could barely fall asleep and woke up twice, each time thinking about Cassandra's comment and body. I woke up way later than I wanted to. I could smell fresh coffee brewing so I made my way into the kitchen. I fully expected Beth to be the one to work on breakfast, instead, Cassandra was the one standing there with a red miniskirt and white tank top.

"Oh hi, is Beth already gone?" I asked, knowing she had to work at Starbucks on Saturday mornings.

"Yeah, her shift started at 5 so she was gone before I woke up. I think I know how you like your coffee though and the cinnamon rolls should be done in ten minutes," she said. I realized that I had stared at her legs for way too long, so I poured myself a cup and went into the living room.

A while later, she walked in with a couple of plates and handed me one. She sat down next to me, took a sip of her coffee and said: "It's ok to look at me, you know?"

I slowly turned my head towards her. "I know," I replied.

"About my comment last night," she began saying.

"It's ok, don't worry about it," I said.

"Well, that's the thing. I cannot help but worry," she said.

"Worry about what?" I asked.

"The issue with living in a small town like ours is that the pool of guys is small. I am terrified about going to college without, you know, experience with guys," she said.

"Meaning that you are a virgin? I don't think that's a big deal. Heck, if you wait until you are ready to settle down with someone seriously, you would give him a very special gift by having waited," I said.

"But I don't want to wait. Heck, I feel like I think like boys do," she responded.

"Meaning?"

"I know boys think about sex all the time. And what I am thinking or feeling about, well, I don't know. I feel like, just touching myself, thinking or wishing that. Ok, I know I am not making any sense," she concluded.

"We don't have to be talking about this," I tried to reassure her. I just realized that her nervousness caused her to adjust her posture and she was now flashing a sliver of her panties. I was certain that she was not doing it on purpose but my staring at it occasionally was.

After a few minutes of additional comments that made little sense, I looked at her crotch far too obviously again.

"Can you admit that you are checking me out at least?" she suddenly asked.

"I mean, you cannot blame me," I said.

"I am not blaming you. I like the attention," she said.

"Cassy, you can get the attention from any heterosexual guy on the street," I said.

"But what if I don't trust any of them?" she added. This time, she opened her legs wider on purpose, giving me a clear view of her white lace thong.

"What are we doing here? I have known you since you were a little girl," I said.

"That is why I trust you. Heck, a perv would have taken advantage of me a long time ago. Your home has always been a safe place for me, because of you," she said emotionally.

"I am glad. I really am. I really care about you and want you to be safe and happy," I said.

"Exactly!" she said excitedly. "You make me feel safe and I know you want what's best for me."

"I agree," I said. I did not realize that my response would trigger what was about happen next. She put her plate down, leaned over, and without saying a word, straddled me. I was speechless as she took my plate and cup and put it behind her.

She stared at me with her beautiful hazel eyes for what seemed like eternity. I began to wonder if she was about to change her mind and get up. Instead, she pulled up her top, showing off her perky breasts wrapped in a black pushup-bra.

"Cassandra, think about this," I said. I wanted to continue for sure, but still felt I had some responsibility to be the level-headed adult in the room.

"I have. All last night, the past couple of weeks. Please Dan, I cannot think of anyone else I'd rather do it with."

My erection hit its zenith, and so did my hormonal levels. But there was still some responsibility left in my conscience.

"What about protection?" I asked.

"I have been on the pill since last year," she said. Though I knew I had no STDs, the fact that she didn't mention that part showed me how naïve teens can be.

Cassandra leaned in, and in that moment, I was done trying to be the responsible adult. I leaned forward and met her lips. My hands naturally landed on her thighs, hers held that back of my head. After a few seconds of just our lips kissing, she opened her mouth and darted her tongue towards mine. I felt her legs flexing as she began to rock her hips up and down, her crotch still only hitting air.

Sliding my hands forward, I reached her tight ass and pulled her closer to me. When I felt her pressing against my erection, I heard a subtle moan amongst the sounds of our kissing. She hastily pulled up my t-shirt and briefly kissed my neck, her hands running along side my pecks.

"Do you want to take off my bra?" she asked.

"Take out your hair first," I said. Even though she looked beautiful with her dirty blonde hair in a bun, her wavey, long hair was meant to flow freely. With her hands behind her head, her perky tits stood even taller and her ribs protruded against her skinny torso momentarily.

Just as she was about to let her hair fall down, I unclasped her bra in the back. She quickly chuckled as she began pulling down the straps.

"What?" I asked with a smile.

"You undoing my bra that easily is a good sign. Let's just say I had to be the one doing that after a few failed attempts," she said right before my eyes got a clear view of her tits. Her nipples were already erect but I wanted to make sure they were ready to be stimulated aggressively. I cupped her right breast and slowly moved the tip of my tongue against her nipple.

After licking it slowly, I began to suck it gently. Cassandra was unable to sit still and gyrated her crotch against my thigh.

"Shit, I am so wet for you," she said. I wanted to find out for myself so I ran my other hand along her toned abs, causing her to flinch. I found no pubic hair when I slid underneath her thong. Her clit was already swollen and right beyond it, I was met by her wet sex.

"Can I ask for a favor?" she suddenly asked.

"Yeah, sure," I said.

"Can we go to your bedroom? I don't want to lose my virginity on a couch."

"Lead the way," I said. She stood up, grabbed my hand and pulled me behind her quickly. Even the sight of her fair flailing turned me on. Once inside my bedroom, she jumped onto the bed and turned onto her back. Her hands were cupping her breast and she began playing with her nipples.

I watched her, as she watched me, take off my pants. When I pulled down my underwear, her eyes opened wide.

"Shit, that's bigger than I expected," she said. Maybe I should have said something reassuring in return, but instead, I climbed on top the bed and began to kiss her left foot, than her calf and kept kissing my way upward until I got within an inch of her pussy. I sat up and reached for the waistband of her thong and pulled it towards her knees. She let me pick up her feet so I could pull it off completely.

Now only dressed in a skimpy red skirt, I began to kiss her outer lips but quickly moved onto her clit. The fast that she had seemingly shaved her entire private area that morning, made it clear that she had this planned all along.

I stuck my index finger into her pussy, clearly recognizing that it was one innocent tight hole. I only wanted to stimulate her for a few seconds, but the way she responded to it, made me keep going. She was thrusting her clit against my mouth, was still playing with her tits and kept moaning and telling me how good it felt.

"Yes, Dan, lick my teen pussy," she suddenly said and turned me on even more. Then, she began to cum out of nowhere. Instead of continuing her vulgar comments, she came in near silence, only her body doing all of the talking. The moment I could tell that her clit could not take any more stimulation, I hurried towards her mouth and began to kiss her hard, hoping she would not mind tasting herself.

"That was the best orgasm ever," she said, breathing hard. "I am ready for him."

"I have a suggestion. You get on top so you can be in control," I said.

"Ok," she simply said and let me roll off her.

Once she climbed on top of me, I pulled the elastic band of her skirt to give me an unobstructed view of her pussy. She grinned nervously from ear-to-ear as she grabbed my cock.

"He is so thick," she said and placed the tip against her entrance. She took in a deep breath simply went for it, fully lowering herself on top of my shaft.

"Ahh fuck," she cried out, possibly surprising herself. This teen was as tight as I had expected, but wetter than I could ever recall a woman being. I wanted her to begin riding me, but she allowed herself to somewhat relax around my cock.

She breathed deeply but rapidly, smiled at me, and raised her sex away from me and slowly came back down. A painful grimace covered her face.

"Sorry, I need to go slowly," she said.

"Don't be. I could do this all day," I said honestly.

"I don't think she can take another minute, fuck this hurts," she said, nearly angrily.

"You can pull out if want," I said. I stroke her hair, trying to be as reassuring as possible.

"It's ok. I read that it takes time. It's hard to describe, it hurts, but my pussy is also asking for more," she said. "It's like my body doesn't let me move because of the pain, you know?"

"It's ok, go at your pace," I said.

She tried to descend on me a couple more times before she suddenly pulled out.

"That was just inside of me. Holy crap," she said. "I want you to take me."

She proceeded by laying on her back and open her legs for me. I took my soaked cock in my hand and got into position to penetrate her. I sat on my heels and bent my cock downward.

"You are so fucking hot," she said. I had not felt that confident about myself in years after that comment.

"Keep going even if it seems like it hurts too much, ok?" she said as I slowly reentered her.

"I have a feeling you are someone that is going to like it hard once you get used to this," I said.

"You got that right, fuck, it's stretching me so much. Take me please," she said.

I began to increase my pace and could not decide that to focus on. Right below, I saw my shiny shaft disappear inside a teen's tight body. Right above, her arched back caused her to portray her tits and abs perfectly. Her facial expression made me believe that I was the most gifted lover in the world.

"I am gonna cum," I groaned.

"Yes, Dan, please, cum for me," she moaned. I could not help but think that she was relieved that I was finally done. It seemed as if she was trying her best not to show how much pain she was feeling.

"Fuck," I groaned. I began to empty my balls straight into a woman's womb for the first time in years. Cassandra only felt tighter as my cock spasmed until the last drop came out. I held her petite body, stroking her legs as I could not get enough of them and continued doing so after I finally pulled out.

"You ok?" I asked.

"That was perfect. I wished I could brag to Beth about it," she said with a smile.

"Yeah, let's not mention that. You ok though?" I asked again.

"Yes, no regrets. Are you ok?" she asked and began to stroke the top of my hand.

"We might need to be careful. I know you wanted this to be a one-time thing, but it might be hard to stay off of you if you continue to spend the night," I said.

"Give me one good reason why we shouldn't do this again," she said and winked at me.

I smiled back. I noticed she began to leak cum on my sheets.

"I will clean those sheets for you," she said. "How much did you cum?" she asked and wiped some of it with her hand. She looked at her slimy hand and almost seemed to play with it.

"Have you ever tasted cum?" I asked.

"No, is that your way of telling me that you want to see me taste it?"

"You can see right through me," I replied.

Instead of tasting what was already on her hand, she scooped up more cum and slowly sucked some of the cum off her index and middle finger.

"Satisfied?" she asked.

"Are you?" I asked in return.

"Only if you come take a shower with me."

She did not have to ask me twice. Cum began to run down her leg as soon as she stood up, so she began to run and laugh. I was right behind her. Even though she was twenty years younger than me, it felt natural being around her, touching her naked body and kissing her occasionally.

Since Beth was not to return until 1 pm, we ended up having sex one more time before she got home. We figured it would make sense for Cassandra to go home for a little bit. Beth noticed some awkwardness despite my attempt to act as normal as I could.

I was glad when Cassandra decided not to spend that night at our place. Beth ended up going to the movies with some other friends and I found myself home alone, replaying the two sexual encounters from earlier in the day.

"Cassandra is acting weird," Beth said the following morning.