The Deep End

Hi JJ! Can you write a story for me about an older man who becomes a "daddy" to a twenty something girl? I would like it to have her being afraid to try something but then learning she likes it. It doesn't have to be anything too crazy just something she's afraid to try. Also can you make the man's name Sam? Thanks JJ you are the best.

The Deep End

I never had a father growing up. I used to wish that I did and wonder what it would be like to have a man that loved me the way a father would have. My mother was always there for me, and she had me convinced that I didn't need a father. I was relatively content about it, especially since the story she told me about my father was when my mom was left pregnant and alone.

"He's a drifter. That's all. He never wanted to stay in one place long enough to raise a child," my mother explained to me.

"That makes sense," I told my mother, but there was always a part of me that wondered what it would have been like growing up with a dad. I wondered why my father had left me behind and why I wasn't enough to make him want to stay. I wished that I could have a dad almost every day of my life. I never told my mother about this wish, knowing that it would hurt her feelings if she thought I didn't appreciate her and what she did for me. She was a great mom, but no matter what she did, she couldn't fill the void inside of me where a father should have been.

I stayed close to home for college, knowing that my mother would have a hard time if I moved too far away. I still lived at home with her, but she didn't mind if I spent the night at a friend's house, and she was cool with my first college boyfriend, Javier. I wasn't sure if she would be cool with my second boyfriend, though. His name was Sam, and he was a lot older than me.

I met Sam at the campus bookstore one day when I was buying my books. I wasn't sure what he was doing there at the time, but later I found out that he was buying books for his daughter, who was starting at the college that term. I wasn't really looking at him as a potential boyfriend, but he struck up a conversation when he saw me. Somehow, we ended up going out for lunch at the Burger King right next door to the bookstore.

He bought me lunch and hung on my every word in a way no boy my age ever had. Sam had dark hair and a goatee, and he wore a full suit, which made him look important. He was about 5'9, and he had a way about him that was happy and delightful. I knew that he was interested in me sexually, but there was something about his age that made him desirable to me. I liked the idea of having a father, even if it wasn't in the traditional sense. Sam's attention made me feel desirable and full of life. We sat in a small booth, and as I ate, I could feel myself falling for Sam.

"Do you have a boyfriend?" Sam asked me as I took a bite of my burger.

"No. I broke up with my boyfriend a few months ago. I found out he was cheating on me with this girl from his econ class. I didn't really care that much about him, anyway, but that was it for me."

"I would never cheat on you if I was your boyfriend," Sam said smoothly.

"You're old enough to be my father," I laughed as I popped a few fries into my mouth.

"I'm into that. I like young women, and I don't mind playing the role of daddy. You seem like the type of girl who would like that. Am I right?"

"What?" I cried, buying myself some time to think about this. I had always wanted a daddy, and here was an older man willing to play the role. I knew that I shouldn't be too hasty, but I also knew I had been thinking about something like this for my entire life. "I'm not sure how I feel about it."

"Well, there are a lot of young women with daddy issues," Sam said slowly. "I tend to gravitate toward those women because I feel I can offer a corrective emotional experience."

"A what?"

"An experience where they are loved and cherished by a father figure. I treat them like my special princess, which is what a lot of girls need. They need to be loved and cherished."

"How do you know if you would be able to love and cherish me? We just met?" I took a sip of my Coke and stared Sam down.

Sam remained composed. "I know because I think you are beautiful, and I can sense that you have some major daddy issues that I could help you correct."

"You can correct my daddy issues? How?"

"By loving you."

"What kind of love are we talking about?"

"The kind that makes you feel secure. You can trust me, Shelby." The way he said my name made me weak. I had given him my name back in the bookstore, but he actually remembered it. That was a lot more than I could say for the boys my own age.

"I do trust you so far, but you could still be a serial killer, so that's the thing."

"Would a serial killer buy you Burger King?" Sam asked with a bit of a laugh. I laughed with him.

"I'm not sure."

"What would make you feel better about me? How can I prove to you that I mean you no harm?"

"I don't know," I said honestly. "I guess we can keep hanging out and see how it goes."

"Fair enough." Sam looked at me with concern, "Are you full? Do you need anything else?"

"I'm good," I said agreeably.

"Want to go back to my place?"

"Wait. Are you married?" I asked him.

"I'm divorced. My daughter, Madison, lives in the dorms now, which is why I'm on campus. I'm visiting her. You can come to my house. There's no one there."

"Um... okay," I finally agreed. I was a little nervous about going with Sam to his house, and looking back, maybe I should have been a bit more cautious. We got into his Audi and drove about six blocks North of the campus before he pulled into a long, skinny driveway that led to a house removed from the street.

"Wow, you live close to campus."

"Yeah, you could even walk here," Sam smiled. I waited for him to walk around to my side of the car and open the door before getting out. He held the front door of his house open for me as well, and I walked in, amazed by all of the art that hung from the walls. There was a statue of a mermaid in the entryway that made me smile with delight. What kind of man had a mermaid statue?

Sam led me to his living room which housed a plush beige sofa and huge seventy-inch flatscreen television. The coffee table also had a mermaid statue as the base and a glass top that looked like it was resting on the mermaid's arms and tail. He grabbed a remote control, and music came on with the press of a button.

"What's with all the mermaids?" I asked, looking around at the paintings and knick-knacks, all with a mermaid theme.

"They are my favorite mythical creature," Sam answered with a thin-lipped smile. "I don't know why I'm so fascinated with them, but I wish that mermaids really existed. You look a lot like a mermaid with your long hair and your innocent-looking features. If you had a tail, you would be the most beautiful mermaid in the lagoon."

I swooned a bit at Sam's words, and it wasn't a shock when he kissed me. We were both still standing in front of the coffee table, but Sam's kiss made me so weak that I felt my knees beginning to buckle.

"Let's sit down," Sam suggested. "But I want more of those mermaid's lips."

"Okay," I said stupidly. I allowed Sam to kiss me, his tongue delving into my mouth with expertise that boys my age just didn't have. Sam's hands knew where to go and how to rub my legs in just the right way so I would open them a bit more for him. I had never been kissed like this, and I allowed the beauty of the moment to permeate my brain. I wasn't thinking. I was enjoying Sam's attention, and I never wanted it to end.

"May I go down on you?" Sam asked as his hands moved up my legs even further.

"I don't know..." I wasn't sure about this. I usually didn't move this fast with guys, but Sam was so much older, and he was probably used to going all the way with women he barely knew. I wasn't sure if I could do that, but my body was aching to let Sam do it.

"I promise I'll make you feel so good," Sam added.

"Okay," I breathed.

"Take off your skirt and your panties for me, Shelby." The way he said my name made it easier to give in and open my legs for Sam. I sat on the couch with my legs spread, my full pussy lips on display for a man I had met only hours earlier. I kept my top on, not willing to show my entire naked body at once.

"Your pussy is exquisite," Sam said, examining it. "I can't wait to try it." Sam situated himself between my legs and began to work his magic. I had never felt anything so perfect before. I didn't even realize how close to cumming Sam had made me until it felt almost uncomfortable. When I finally came, my moans were so intense that I could barely keep myself together. My body exploded with pleasure, reaching into every nook and cranny of my being. My screams punctuated every contraction of my orgasm. I clawed at Sam's couch, my spine arching, then straightening in a convulsive uproar.

"Oh my God! Fuck!" I screamed as the final moments of my orgasm gripped my soul. Sam looked down on me with a satisfied smile. I was surprised that he hadn't kept going and tried to fuck me. Most of the guys my age would have tried to fuck me by this point. It was refreshing that Sam wasn't pushy.

"How was that?" he asked.

"That was amazing!" I was slumped down on the couch, my legs still spread open. I felt dazed in the most perfect sort of way. "It's hot in here."

"I'm glad you enjoyed yourself. Would you like to go swimming? I have a pool in the backyard."

"A pool! That sounds great, but I didn't bring my suit."

"It's private. We can skinny dip," Sam suggested.

"I'm not comfortable like that. Sorry," I apologized, knowing I wouldn't feel right without a bathing suit on.

"My daughter has a bunch of bikinis in the spare bathroom. Maybe one of hers would fit you?"

"What size is she?"

"About your size. Let me go grab one of hers for you."

"Okay," I said slowly, trying to sit up. I felt a bit dizzy after cumming so hard. By the time Sam returned, my legs were closed, and I was starting to feel a bit more normal.

"Here you go, this should fit." Sam handed me a bikini cut a bit more liberally than I would like, but it looked like my size.

"Where can I change?" I asked.

"You could change right here, but there is a bathroom this way," he motioned for me to follow him. The bathroom also had a mermaid theme, which I loved. There were tiny soaps in a dish shaped like shells and towels in a sea-green that had a mermaid applique on each one. I put on the striped bikini and looked at myself in the mirror. I had just let an older man eat me out. I felt a bit slutty, but I liked Sam. It was strange that he had a daughter about my age, though. It was weird wearing her bikini.

I walked out of the bathroom to find Sam waiting for me by the door that led to the backyard. He had a pile of beach towels in his hand, and I noticed that he had put out some lemonade for us to drink. He led me to the small table where he deposited the towels.

"You want to go in the pool?" he asked.

"Yes!"

"Okay, let's go! Are you the kind of woman who jumps straight into the deep end, or do you prefer to dip a toe in and go slowly?"

"I'm definitely a toe dipper," I said quickly.

"Funny, I'm more of a deep-end diver," Sam laughed. "But you already know that don't you?"

"I guess I do," I said, blushing heavily.

"That's okay. Go ahead and dip your toes in, and I'll dive right into the deep end."

"Okay," I agreed, and I watched Sam do precisely what he promised. I waded into the shallow end, sticking close to the steps as my body adjusted to the water.

Sam swam across the pool underwater until he was at my feet. He grabbed my ankle before coming up for air. "It feels great today," he said when he finally rose to the surface.

"It sure does."

"Have you ever given a blowjob in a pool before?" he asked me.

"No. I've only given one blowjob ever, and I actually choked really hard, and it freaked me out. I'm not really any good at blowjobs."

"I can coach you. In fact, I'd be happy to teach you how to give a good blowjob. It's a skill every young woman should have, in my humble opinion. Let Daddy teach you. I'm very patient, and I can show you everything you need to know."

"I don't know."

"Take a look at my dick and see what you think," Sam said with a devilish smile. He pulled his swim trunks down to reveal his very hard, very thick penis.

"Oh wow!" I said reflexively. Things were escalating a bit more quickly than I would have liked, but I really wanted to please Sam. I wanted him to like me and keep giving me the attention I had always craved from a father.

"Come here and put your mouth on it, Shelby."

The way he said my name was transfixing. I found myself moving toward his dick. He held it out for me so I could wrap my mouth around it. I did my best to do as he wanted, knowing that I wasn't ready for what was about to happen.

"That's right. Keep your mouth open, and I'm going to fuck your face a bit. Make sure you relax your throat." I held still, trying my best to follow Sam's direction. "You're a good girl. That's right, just keep that mouth open. Relax that throat. Hold still and try not to choke."

I was afraid of choking, but Sam knew what he was doing as he grabbed the sides of my head and tilted my head in just the right way so that he could get his cock down my windpipe.

"Breathe out of your nose. That's good. Hold still," Sam said, and I did my best to not choke. I let his cock rest at the back of my throat, and I felt it move just past my windpipe. That's when I choked hard, coughing as I spit his cock out. A string of drool leaked from my mouth, and I was mortified until Sam assured me it was okay. "You're so sexy, and you're so good at blowjobs. I love how much saliva you have!"

"I'm sorry. I told you I'm not good at this!" I whined. I felt tears spring to my eyes. I didn't want to fail at giving Sam a good blowjob, but that was what was happening, and I was helpless to stop it. I just didn't have the skills.

"You are great at this. You did so well. Let's try it again. Everyone has a gag reflex, and it takes a while to learn how to suppress it. Don't worry. I'm willing to work with you and teach you, Shelby. If you let me." His eyes stared deeply into mine, and I felt like he was telling the truth. It seemed like he wanted to help me, and he wanted this to go well.

"Okay," I agreed, and he put his cock right back down my throat. I tried my best to be good for him and give it to him the way he wanted. His cock was back down my windpipe, and I tried to breathe through my nose like he taught me. I was doing pretty good! He was able to pump his dick in and out of my throat, and he moaned in appreciation.

"You're such a good girl!" Sam exclaimed, and the way he moaned told me that I was doing a good job. I felt good about myself in a way I never had before as Sam used my face until he was ready to cum. "I'm going to cum on your face, Shelby!

I braced myself as Sam pulled his cock from my throat. He sprayed his cum all over my face, which I had never let anyone else do to me. I was helpless to stop him, and I didn't care. He was making me feel wanted and needed. I felt almost like I had a father, and that was good enough for me.

"Wow, that was amazing, Shelby. I think you're a natural at sucking cock."

"You do?"

"Yes. I would love it if you let me be your daddy. I could keep training you to suck my dick and maybe how to have sex too. I think you would have a fantastic time being my little girl. We can pretend and role play."

"You want me to pretend to be your daughter?" I asked, not sure if this sounded like a good idea. It was one thing for me to think of him as a father. It was another participating in sexual scenarios with Sam as my daddy, especially since he had a daughter my age. There was something strange about the situation that made me take pause. In the end, my need to be loved won out over my concerns.

"Yes. Is that so wrong? I told you what I was into at Burger King. I just want to know if you want to go down this path with me. I can take care of you and make you feel good."

"I do have major daddy issues," I said slowly.

"I can tell. That's why I chose you."

"Chose me?"

"Yes, from the moment I spotted you at the student store, I knew that I could help you."

"Help me?"

"Yes. Like what we just did together. I taught you how to take a cock down your throat. Do you want to learn more from your daddy?" he asked, referring to himself.

"Yes. Yes, I do."

"Then say, 'yes, Daddy,'" he prompted me.

"Yes, Daddy."

"That's a good girl." I beamed with pride as Sam showed me that his cock was getting hard again. "Maybe we should try another blowjob lesson."

"Yes, Daddy."

"You're so good at this, Shelby. Come suck on Daddy's dick." I moved to him and wrapped my mouth around his cock, eager to please him. All my life, I had searched for the love of a father, and now I had finally found it. I would suck Sam's dick however he wanted, and I knew it was only a matter of time before he fucked my other holes. Maybe he would teach me how to be better at sex too. Perhaps he would teach me all of the things a father teaches his daughter, too. I'd been missing out, and I was ready to make up for the lost time. I was prepared to dive into the deep end with Sam.