BFF's Dad

Story Info
Young divorced MILF always wanted her friend's dad.
7.6k words
4.73
31.4k
36
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Leader12
Leader12
980 Followers

I was three years old when we moved to our new house. Although I was too young to remember, the story I've heard many times is that it took my mother less than an hour to introduce herself to neighbors, find someone whose child was the same age as me, and set up a play date. And that's how I met Lindsay. She lived three houses away, and she was the first person I met in the new neighborhood. We quickly became best friends, and thirty-three years later, we're still best friends.

Lindsay and I did EVERYTHING together. We went to the same pre-school. We obviously went to the same schools, living on the same block. We took gymnastics classes together; she was better than me. We played soccer together; I was better than her. When one of us excelled in a sport, the other became her world's biggest fan.

I've never figured out if we got along so well despite the huge differences in our families or because of them. I was the youngest of five girls; Lindsay was an only child. My parents didn't get married until they were almost thirty, and they didn't have me until they were both 42. Lindsay's parents got married right out of college and had her a year later. Lindsay's parents were much closer in age to my sisters than to my parents.

I spent a lot of time at Lindsay's house growing up. As an only child, she was happy to have someone over to play with her. On the other hand, sometimes my house had a lot of drama. Although I loved all my sisters and was very close to the two nearest in age to me, five girls meant there was always someone going through wild teen hormones and having normal teenage fights - sorry, I mean loud discussions - with sisters and parents. By the time I hit my teenage years, my parents were in their mid-fifties. Honestly, I'm not sure people in their mid-fifties should HAVE to put up with teenage kids. In general, I was a good kid, but hormones are hormones. I don't know the name of it, but I'm sure there's an explicit hormone that FORCES you to think your parents are out to ruin your life.

Not only was it good to get out of my house, but I also always loved being at Lindsay's house. Her parents, Beth and Barry, were so cool. They were young. They played with us. They took us on adventures. I spent so much time there, I sometimes thought they were more responsible for my upbringing than my parents. Of course, that wasn't the case, but sometimes I think I wanted to believe they were my parents. Don't get me wrong - I LOVED my parents. I'm just not sure they were still into the role of parent by the time I came along.

Once we learned about where babies come from, Lindsay and I used to wonder if she was a mistake. We were pretty sure her parents always planned to have kids, but we weren't sure they planned on having her as early in their marriage as they did. And I don't mean to imply they TREATED her like a mistake. Quite to the contrary, they doted over her. They were loving, involved, wonderful parents.

But don't go thinking Lindsay always got her way. Her parents were known as some of the strictest when it came to certain things. If there was a party in high school, her parents would call the hosting-kid's parents to make sure they were going to be home and to figure out their attitude toward teen drinking. And Lindsay always had to be home by the legal curfew. Besides the fact that teen's driver's licenses aren't valid after curfew, her parents just thought midnight was late enough to get home. They occasionally made an exception for special nights, like homecoming or prom, but they always made sure they knew where Lindsay was going to be.

Although Lindsay frequently complained about her parents' strictness, we both knew it was because they loved her. Frankly, it made me think even more of her parents, not less. And even though I thought both of her parents were great, once I got to high school, I had different thoughts about Barry. Yeah, I definitely had a crush on him. He was handsome, had a great smile, and just seemed like the perfect guy. Of course, I never let Lindsay know how I felt; I think she would have been grossed out.

Sometimes, if I was going to Lindsay's, I'd change clothes to look better for Barry. I had a pretty nice body, and I wanted to show it off to him. And when I say 'show it off', I don't mean I'd wear low-cut tops and show a lot of skin. No, I was much more subtle than that. Sometimes I'd put on yoga pants over a thong and a stretch top that made my small-C cup boobs look as good as possible. And I'd find reasons to give him a hug and press my boobs against him.

But for all my efforts, Barry never acknowledged my attempts to get him excited. I never once saw his eyes drop below my neck to check me out. I was never sure if he never looked at ANY other women's bodies or if he just didn't look at MY body. Maybe he didn't look because I was, in his mind, a kid. Maybe he didn't look because he thought of me as a daughter. Maybe he didn't look because he didn't want to look like a pervert who was checking out his daughter's best friend. Whatever the reason, he never, ever looked at me that way. And it pissed me off.

I don't even know what I hoped would happen. Did I just want him to tell me how hot I was? Did I think he was going to pull me against him to feel my boobs against his body? Did I think he was going to sweetly fondle my breasts? I guess at a minimum I thought I'd get him excited and maybe even see a bulge in his pants. Yeah, teenage girls can be really stupid.

Besides being hot, Barry was incredibly sweet. And you could talk to him about anything. I clearly remember the day my boyfriend broke up with me. I was devastated. I went to Lindsay's house, and her dad opened the door. I was still crying, and as soon as he saw me, he wrapped his arms around me.

"Cassy, what's wrong?"

Through my tears, I managed to cry, "Brian broke up with me!"

He pulled me in the house, closed the door, and just held me for five minutes while I cried. He stroked my hair a few times, which somehow got me excited while I was still crying. When I calmed down a bit, he pushed my shoulders back so he could look at me.

"I don't know anything about what happened, but if someone is stupid enough to break up with YOU, he's not good enough for you," he said as he softly smiled.

I couldn't help but smile just a bit.

"Why are all guys assholes?" I whimpered through my tears.

"I beg your pardon, young lady! I'd like to think you know at least ONE guy - perhaps named Barry - who is not an asshole," he said.

I started laughing.

"Oh, yeah, I know that guy. You're right, he's not an asshole. Actually, he's a great guy. I wonder if he'd be my boyfriend."

Now Barry laughed.

"Well, I know he already loves you, but I think he's involved with another girl right now."

"Okay. I guess I'll have to see if I can find one other guy who's not asshole until Barry is available."

I laid my head back on his shoulder, and he continued hugging me. I pushed my body against him, just enjoying the comfort he was providing, and then I felt it: Barry was starting to get hard. Maybe I accidentally rubbed against his dick. Maybe I pushed my boobs against him too hard. Maybe it was just the tender moment of him giving me comfort, but I definitely felt it. After just a couple of seconds, Barry pushed my shoulders back again as he stepped back.

"Feeling better?" he asked.

"I suppose a little," I said. "Thank you."

"Hey, you know I'm always here for you, Cassy."

"I know. Thanks." Then I started laughing. "Um, I'm guessing Lindsay's not here, right? Or did she just not want to deal with me if I was crying?"

Barry laughed.

"No, she and Beth went shopping. They should be home soon if you want to wait."

"Yeah, if that's okay. I don't want to go home right now."

We sat on the couch in the living room. He made the usual post-breakup comment about there being lots of other guys and I'll find the right one, and any guy would love me, blah, blah, blah. Truth was, at this moment, I was thinking about how great HE was. And when I thought about him getting hard before, I knew who I'd be thinking about that night when I lay in bed alone.

Twenty minutes later, Lindsay and Beth walked in from the garage.

"Oh, hi," Lindsay said, surprised to see me. "What are you doing here?"

"I was listening to your dad try to convince me that it wasn't the end of the world that Brian broke up with me," I said fairly calmly.

"Oh, no, Cassy!" she said as she ran toward me and hugged me. "Let's go to my room."

When we got to her room, I told her what happened with Brian and how wonderful her dad was, trying to make me feel better. I decided not to tell her about him getting hard while we were hugging. We talked for a long time, and Beth invited me to stay for dinner. By the time I went home that night, I was feeling much better. But as expected, when I got into bed and slipped my hand into my panties, I thought about Barry climbing into my bed and fucking me. I probably moaned a little louder than intended when I came, but it felt SO good. I fell asleep immediately afterwards.

By the time we graduated, I had given up on my fantasies of Barry being my first lover. Lindsay and I were both still virgins as we started planning our first year at college. We were going to be roommates, and we spent the summer planning our room, picking out items, and just having a good time.

One evening I was at Lindsay's. We were in her bedroom with the door closed when there was a knock on the door.

"Come in," Lindsay said.

Her dad opened the door and started to walk in.

"Oh, hi Cassy. I didn't realize you were here. I'll talk to Lindsay later."

"What's up, Dad?" Lindsay asked.

Barry paused for a couple of seconds and then let out an audible sigh.

"I guess Cassy might as well hear this, too. I was going to give you some fatherly advice, but Cassy's almost my daughter, right?" he said with a smile.

Lindsay and I both giggled.

Barry came in and sat in Lindsay's desk chair. He looked at both of us for a minute without saying anything.

"What's wrong, Dad?" Lindsay asked.

Barry smiled.

"Wrong? No, nothing's wrong. I guess I just can't believe my little girl - both of my little girls - are going to college."

"Oh, Dad," Lindsay said as she got off the bed and bent down to give him a hug. Then she sat down on the bed again.

"Okay, here goes," he said. "You both are beautiful, young women. Guys are gonna hit on you like crazy."

Lindsay and I looked at each other and giggled. I was not sure where Barry was going with this.

"I expect you to have fun at school. But always remember two things. First, guys lie. They're gonna say stuff just to get in your pants."

I know I was surprised Barry said that, and I'm pretty sure Lindsay was, too. But neither of us said anything.

"But when it comes to sex, you need to be in control. Don't do anything you don't want to do. And always, always, always practice safe sex. The pill isn't 100% effective, and it's zero percent effective in preventing STDs. It doesn't matter what the guy says - always make him use a condom."

I know my face was bright red by now.

"D-A-A-A-A-A-D!" Lindsay yelled.

"I'm not naïve, Lindsay. I was young once. Have fun at school but be safe. I love both of you."

Then he got up and walked to the door.

"Dad?" Lindsay called quietly from the bed.

Barry turned to her. She got off the bed, walked up to him, and wrapped her arms around him.

"I love you, Dad," she said.

"I love you, too, sweetheart."

Although feeling a little awkward, I walked over to him and wrapped my arms around both of them.

"Thank you, Barry." And after a short pause, I continued. "I love you, too."

He kissed each of us on the top of our heads.

"Okay, I'm done," he said. "I'm going to miss both of you."

And then he left. As soon as the door closed, Lindsay and I looked at each other and burst out laughing.

"I'm sorry, Cassy. I'm so embarrassed."

"For what?" I asked. "Your dad loves you and cares about you. And he doesn't have blinders on. I think it's really sweet."

I thought about that conversation many times during my four years at college. Every time a guy tried to do something I didn't want, I thought about it. Every time a guy said, "I don't need a condom, I'll pull out" or "I don't need a condom, I'm safe", I thought about it. And I'm happy to say I got through college without getting pregnant and without getting an STD!

After college, Lindsay and I got an apartment together in the city. We both had good jobs and were having a fun time. A year later, I met David at a party. After dating for almost a year, I moved in with him. Life was great. Two years later, we got married.

At about the same time that I met David, Lindsay met Brandon. They eventually moved in together, and they got married six months after us. I really liked Brandon, and I was glad Lindsay found a good guy. We remained best friends and regularly got together with some close friends we made at college. The guys weren't exactly best friends, but they got along fine when they were together.

Three years later, I got pregnant. Of course, Lindsay was the first person (besides David) that I told. She was so happy for me, she squeezed me so tight it almost hurt. Three months later, I was the one squeezing her when she told me she was pregnant, too.

A year later, we both moved back to the town where we grew up. Our daughters would go to the same schools that we did. I laughed every time I thought about them following in our footsteps. Would they become best friends? Would they go to college together? Life couldn't get any better!

It was about two year later when Lindsay called me crying. She told me her mom had pancreatic cancer. I immediately started crying, too. Her parents were such an important part of my life, I felt like my own mother was sick. I didn't even know what to say or do. I frequently joined Lindsay when she went to the hospital to visit her mom, both to support Lindsay and to see Beth. Six months later, at the age of 56, her mom was gone.

Beth was great, and I was devastated by her death. But I hurt even more for my best friend and her dad. They were a really tight family, and it killed me to see the incredible pain they experienced. I spent a lot of time with Lindsay and Barry over the following few weeks, trying to help them get through all the horrendous activities required for the funeral and burial along with them dealing with the reality of Beth being gone.

After six months, Lindsay was worried about her dad. He was still in such a sad frame of mind that he rarely left the house. As soon as Beth got sick, Barry sold his business so he could spend more time with her. Because of that, he didn't even have the requirement of work to get him out of the house. The only thing that seemed to bring him any joy was his granddaughter.

Not long after Beth died, I had my own crisis. I found out David was cheating on me - with TWO different women at work - and I kicked him out. I went into a pretty dark place myself after the divorce was finalized, rarely leaving the house. Lindsay spent a lot of time trying to cheer me up during that period. She even had her dad call me a few times to help convince me to put the bad stuff behind me and to concentrate on the good - mainly my daughter. Finally, Lindsay convinced me I was still young, and I still had a life ahead. I started dating again, and I decided I deserved to have fun.

And I had LOTS of fun. Or, more explicitly, I had lots of sex. I slept with almost every guy I went out with, often never having a second date with them. Looking back, I'm not proud of it. But at the time, it was a lot of fun. After six months, Lindsay convinced me to look for a relationship, not just sex. So, I tried the crazy concept of going out with a guy but not ending up in his bed. I started feeling pretty good about myself.

Time has amazing healing power. Not long after I started feeling like my old self, Lindsay said her dad was doing much better, too. Of course, they both still missed Beth, but Barry started living a semi-normal life. He went out to lunch with Lindsay more often, and she actually encouraged him to start dating. He objected, of course, but Lindsay reminded him he was still young and had a lot of life to live.

One Saturday morning, I was running some errands, with my daughter in her car seat behind me. We were singing songs as I drove to the coffee shop for my morning hit of caffeine. I pulled into the curbside parking spot and indicated my arrival in the app. While I was waiting for my coffee, I saw Barry sitting at one of the outdoor tables having coffee with a good-looking woman. I opened my window and called out to him, but he didn't hear me. I got out of the car and called his name, but he still didn't hear me. So, I walked a few steps away from the car and tried one more time. The woman sitting with him pointed to me as she said something. He turned his head, finally saw me, and flashed me a huge smile.

"Cassy!" he shouted as he walked over to me and gave me a huge hug. "What a pleasant surprise."

"Hi, Barry, nice to see you. I can't walk away from the car - Sophie's in there."

Barry walked over to the car and looked in through the window.

"Hi, sweetheart," he said to Sophie. She smiled and waved.

"Everything good with you guys?" he asked.

"Yep. No complaints. Just running some errands this morning."

"Okay. Good to see you, Cassy."

We hugged again, and he walked back to the table where the woman was sitting. Just then, they brought out my coffee, and I was on my way.

As soon as I got a block away, I pulled to the curb so I could text Lindsay.

Me: "Just saw your dad having coffee with a hot woman. Is he dating?"

Lindsay: "Ha. Pretty blond? Thin? Blue eyes?"

Me: "I couldn't see her eyes, but yes to others"

Lindsay: "Probably Sara. Good friend he met at work years ago. Definitely not a date."

Me: OK. TTYL

A few days later, I drove over to Barry's house before lunch. I rang the doorbell, and when he opened the door, he gave me a huge smile.

"Cassy! What's going on?"

I walked in and we gave each other a big hug, as we always did. I was wearing a backless halter top, and I liked feeling his hands on my bare back.

"Am I disturbing you?" I asked.

"You're NEVER disturbing me, Cassy. C'mon in."

We walked into the living room. He sat on the couch, and I sat next to him, tucking one leg under me and sitting sideways.

"Do you remember, in high school, when Brian broke up with me and I showed up here crying?"

Barry smiled just a bit.

"I sure do."

"You made me feel good that day. And do you remember, the summer before we went to college, when you gave me and Lindsay 'the talk'," I said, using air quotes around 'the talk'.

Barry smiled again.

"Uh, yeah. Lindsay was appalled I even said that to her, let alone to you," he said with a little laugh.

"I thought it was sweet. And I gotta tell you, I thought about that talk a lot in college. And I always took your advice."

Barry smiled. He seemed a little embarrassed.

"So, can you give me some more advice?" I asked.

He looked confused.

"What do you mean?"

"Well, you know, after my divorce, I went through a phase. I'm sure Lindsay told you about it. She told me I was slut."

Barry smirked.

"I'm not sure she used that word, but, yes, she did say you had lots of fun."

"Yeah, sometimes it was fun; sometimes it wasn't. But I always made guys use condoms. And when a guy was reluctant, I always thought about your speech."

Barry smiled just a little.

"But after a while, I decided I WAS being a little slutty. So, I quit sleeping with every guy I went out with. And I got tested to make sure I hadn't picked up anything during that time period. I really haven't been feeling very good about myself. And now there's a guy I'm interested in, and I know he likes me, but I'm not sure if he wants to sleep with me."

Leader12
Leader12
980 Followers