Note: This story was dynamically reformatted for online reading convenience. ï>¿Bob And The Girl Next Door by Octave888888 Bob And The Girl Next Door Ch. 05 Dating leads to jealousy. "You're dating my mom?" Anna exclaimed, a little louder than necessary. Other people at the restaurant turned to look. "I'm not dating her yet," I said, trying to de-escalate the situation. "We're going out on Friday." Anna frowned. "Honey, is there a problem with me going on a date with Grant?" Olivia asked her daughter. Anna started to say something, but I gave Anna a sharp look. Anna realized that any protest would reveal our secret voyeurism relationship. "No, just, took me by surprise, that's all." Anna sat back down. Olivia looked temporarily satisfied, but Anna sent me a look that said she wasn't happy. ***** That night, there was no show. Anna's blinds were closed. The night after that, same thing. Anna also hadn't been out in the back yard. I was fairly sure she was upset. Wednesday, I texted her around noon, 'Are you coming outside today?' It was a beautiful day, so it was conspicuous that Anna wasn't out getting sun. I sat out, eating my lunch, watching Bob run around the yard, until Anna finally came out around 12:30. She came over and sat with me, but didn't say anything. Also, she was wearing a long-sleeve shirt and gym pants, hiding her body from my view, despite the warm weather. Yup, clearly upset. "You don't like that I'm going out with your mom," I said, breaking the silence. Anna just looked at me and rolled her eyes, then looked over at Bob in the yard. "She is closer to my age," I pointed out. "She's 38, and I'm 32." No response from Anna. "I still think you're sexy," I whispered. "Tell me something," she finally said, "do you really think my mom is attractive?" "Well, yes," I answered honestly. "Is she hotter than me?" That was a harder question. "Well, she's..." Anna cut me off. "Yes or no. Is my mom hotter than me?" "It's not a fair question, Anna. She's twenty years older than you. You're both hot for your respective ages." "Hmph." Anna huffed and looked away again. "What do you want me to say?" I asked. "Did you want me to tell your mom, 'no, I can't date you, I'm into your eighteen-year-old daughter, whom I've seen naked?' Is that what you want?" Anna's rigid indifference melted. "No, you can't say that. She'd fucking flip out." "Exactly. And, besides physical attraction, it's kind of nice to get to know your mom. We've both been divorced, and came out winners. She got you, and I got Bob." "I guess so." "Speaking of, what do you remember of your dad?" "Not much," Anna answered. "Mom said he was charming at first, then it gradually wore off. Then she found out he cheated on her." She looked at me. "You better not hurt my mom, too. I'm glad she's decided to date again. I just didn't expect it to be you." "Honestly, I didn't expect it either," I said, "but I'm looking forward to it." Anna got up and left, maybe a little less upset than before. She turned around before she got to her door, and told me, "My mom might like you, but I'm not giving up." Then she went inside. That was interesting. Apparently, it sounded like Anna had a plan. ***** Friday night, I knocked on Olivia's door, dressed in khaki pants and a nice shirt. Anna answered the door with a stern look on her face. "Sir, can I ask what are your intentions with my mother?" I laughed, but Anna maintained her serious face. So I answered, playing along, "Just dinner and drinks tonight. I promise to have her back by 11:00." Olivia came into the room, wearing a purple summer dress that complimented her figure. "Only 11:00? Can we have 11:30?" she begged her daughter sarcastically. Anna harumphed and said, "11:15. Not a second more." She was playing the part of an angry parent perfectly. I wondered how often she'd been on the receiving end of it from Olivia. "Shall we?" I offered my arm. "Yes, let's," Olivia took it and we moved for the door. "Have a good time, you two," called Anna. I looked back at her as I closed the door behind Olivia, and I swear I saw a wink from the teenage girl. ***** Dinner went really well. Olivia and I have a lot in common, and not just divorce. We both enjoy some of the same bands, including one that was on tour this summer, coming to town next weekend. When we realized it, we got tickets so we could go together, as a second date. When we'd finished eating, we gave up our table and headed for the bar. Olivia was a wine drinker, while I had a whiskey on the rocks. It was just enough to give me a slight buzz, but still drive us home safely. We pulled into the driveway around 11:10. I pointed out that we only had five minutes before her curfew, which made Olivia laugh. I escorted her back to her door, and wondered if she'd kiss me goodnight. It was a good date, but I didn't want to presume. She leaned in, and we kissed. It wasn't a big deal, but it was a nice, tender moment. Her lips were soft and tasted like her wine. Just then, the front door flew open, and Anna stood there in her pajama shorts and t-shirt. "Ahem," she said, to get our attention. I thought the "overprotective" routine was cute when we'd left earlier, but now it was going too far. It seemed like Olivia agreed with my thought. "Anna, go to bed," she told her daughter. Anna huffed, and said "Fine," then shut the door. Olivia looked back at me. "Where were we?" I asked. "Right here," she said, kissing me again. We didn't kiss for very long, but it was nice. Very appropriate for a successful first date between two grown adults. When Olivia went inside, we wished each other good night, and I walked back to my house. My phone buzzed in my pocket as I let Bob out. 'Come to the window,' beckoned Anna. 'One minute,' I responded. I got Bob back inside, fed him quickly, then went upstairs. My blinds were closed, as usual, but when I peeked through at the usual spot, I saw Anna's blinds were open again. She stood there topless, in front of her bed, wearing panties I'd not seen before. They weren't cute teenage girl panties, they were plain adult woman panties. I bumped the blinds, indicating I was there, and Anna smiled. She texted me again, 'These are my mom's panties. Are you sure you want to be with an old lady like her?' She danced around in her mother's underwear, swaying to music I couldn't hear. I texted back, 'Not nice to call your mother an old lady.' 'I bet you want me to take them off. You want to see my little girl pussy.' I didn't respond. I didn't need to. She took them off anyway, showing her tight, shaved pussy. Her next text came in. 'I bet you like my hairless teen pussy. My mom's got a big bush. You won't like that.' She texted as she shimmied her body. I did respond to that. 'Not nice to talk like that. Your mom and I aren't there yet.' 'She's not as sexy as me.' I couldn't think of how to respond, but before I could, Anna's head whipped around towards her door. She quickly threw on a robe and sat on her bed. Olivia came into her room and sat on the bed with her. She'd changed out of her dress and was wearing a robe herself. I could barely make out the outline of her nipples through the material. They sat for a few minutes, talking. I kept my eye on them, interested. I couldn't read lips, but my guess was it was kind of a heart-to-heart between mother and daughter. Possibly about me. Anna occasionally glanced out the window. I was pretty sure she could see my eyeball in the peeking hole. When they were done, Olivia hugged her daughter and left. Anna went to turn out the light. As she settled into her bed, she sent one more text. 'Mom says you're going out again. But this isn't over.' ***** I realized, when I used my video evidence in court, that I was revealing the locations of the other cameras in my house. Anna hadn't been in the courtroom at the time, but I wondered if she'd realize it. She did, a few days after my date with Olivia. I was sitting out in the garden when Anna strolled up. As usual for her sun-bathing days, she was wearing her short shorts and a sports bra. "I've been wondering something, Grant. You told the court you had a camera in your living room, watching the front door." "That's right." "And you had a camera upstairs." "Yes." "Where upstairs?" she asked. We both knew that she knew of only one. "In the hallway," I told her, "If you're asking what I think you're asking, the answer is yes, I saw you." She gave me a sheepish grin. "Well, it's not like you haven't seen me already." "Right," I nodded, then added in a quieter voice, "But, it was smoking hot, watching you when you didn't know it." She didn't move, so I came closer and whispered in her ear. "Your naked body on my bed turned me on." She shuddered at my dirty talk. Then she turned it back on me. "Do you still have the videos?" I nodded. "Maybe we can watch them together." She put her hand on my thigh, under the table, and rubbed my leg, very close to my crotch. "Maybe we can do other things while we watch." I watched her get up and leave. It seemed like a battle now, like a tug-of-war. We were both trying to get a leg up on each other. But not in a negative way. It was more about who can turn on the other one more, who can make the other one more desperate. I thought for a minute and came up with my next play. I found my tablet and pulled up the first video I had of Anna on my bed. I made a copy of just the first few seconds of it, and sent that to Anna. It was enough to just see her enter the room and lay on the bed, before any of her clothes came off. I added the text, 'Remember that night?' She responded a minute later, 'Of course. And I bet you do too.' ***** Olivia and I were going on our second date Saturday night. We were seeing a band called the Good Times, at a little club downtown. We agreed to dress casually, in jeans and band t-shirts. It was Wednesday evening when I found out that Anna had a date as well. I had been chatting with Olivia, and she told me her daughter was going out with a guy named Ricky on Friday night. Late that night, I saw Anna through my window. She was wearing her robe, and I hoped there was nothing underneath. I texted her: 'Who's Ricky?' 'Football player. Big muscles. Jealous much?' 'I was only asking. Do you want me to be jealous?' She read my text and frowned. Then she put her phone down and crossed her arms, showing she didn't want to respond to that. So I texted again. 'Are you dating Ricky because you're jealous of your mom?' That only made her mad. Her lights turned off. I sighed, knowing I'd hit the nail right on the head. Anna was trying to make me jealous by going out with someone else. The problem was, it was working. ***** Jealous as I was, I watched on Friday night when Ricky arrived. He did look muscular, and somewhat handsome, but he still looked like a dufus to me. I couldn't tell if that was more due to his chowder-head looks or my prejudice. I saw him enter Olivia's house, but only briefly, as Anna came out with him a minute later. I whistled to myself at Anna's outfit. She wore a mini-skirt, showing off her pretty legs. Her top ran just to the hem of the skirt, so if she moved at all, like when she bent to get into Ricky's car, she showed off skin. As they drove away, Anna looked over at my house, saw me in the window, and waved. I sat in my living room, stewing about Anna with another guy. No moron jock could be as good as me, I thought. Anna had succeeded in making me properly jealous. Well, two could play at that game. I texted Olivia, asking if she wanted company, and she responded that she did. Before I went over, though, I repointed my newest camera out the window at their driveway, and set it up to alert my phone. I'd know the instant that Anna and Ricky got home. I went over and sat with Olivia in her living room, sipping wine and talking about how excited we were for tomorrow night. We also talked about Anna, of course. Olivia told me this was Anna's first date since they'd moved to the neighborhood, so she was happy Anna was getting out there, although she wasn't too impressed by Ricky. "What's wrong with Ricky?" I asked, fully agreeing that Ricky wasn't good enough. Olivia said, "He's kinda... stupid." I laughed, and she continued. "I don't mean it to be mean. I just think he's not very bright." She sipped her wine, then told me, "To be honest, before we moved, she and I had very similar tastes in men. I liked the boys she dated before. They were all very sweet and nice. Ricky seems to be an extreme outlier to that trend." I nodded, "I see." But inside I was thinking about what Olivia just said. Similar tastes in men? Maybe that's why Olivia and Anna both seem interested in me. I put out a suggestion. "Maybe she's using Ricky? She seems way smarter than he is." Olivia pondered it, but asked, "Using him to do what?" I shrugged. "Not sure. Is he popular at school? Is Anna looking to move up the social ladder?" Olivia chuckled. "Maybe that's it. Anna hasn't had a lot of friends over since we moved." We enjoyed our evening together, and were just starting to cuddle together on the couch when my phone dinged in my pocket. "What's that?" asked Olivia. I looked at my phone. It was an alert, letting me know that Ricky's car was back in the driveway. "It's nothing," I lied. "Just an alarm to remind me to let Bob out." I stood up. "It's late, I should get going anyway." "Okay. I'll see you tomorrow," Olivia said with a big smile. "You bet. I can't wait." I leaned in and gave her a little peck on the cheek. I let myself out the back door, so I wasn't seen by Anna and Ricky in the darkness. But I could see them. They weren't doing anything physical yet. By the time I made my way back into my house, Anna was beckoning Ricky to kiss her. The instant their lips touched, I became angry. I knew it was for no reason - I had no right to claim Anna, and I hadn't kissed her myself - but it still made me mad. Worse still, Ricky's hand moved up Anna's body and cupped her breast. That broke me. I texted Olivia a simple, naive-sounding message to get her attention. 'Is that Ricky's car in your driveway?' A second later, Olivia came flying out of the house to catch her daughter getting groped by Ricky. She made Anna get out of the car and into the house. With my windows shut, I couldn't make out all of what they were saying, but it was clear that Olivia disapproved of Ricky's hands on her daughter's bosom. I smirked to myself and left the window, to go upstairs and get ready for bed. Olivia and Anna both texted me at nearly the same time. Olivia thanked me for my alertness, and briefly explained she'd caught Ricky 'getting fresh' with Anna. Anna's text carried a very angry tone. 'What's the matter? You can go on dates with my mom, but I can't have my own fun? Asshole!' I peeked through the blinds to see Anna's window, but it confirmed what I knew was true. Anna's blinds were closed, sending me the clear message that she was cutting me off. ***** That Saturday night was my second date with Olivia. We were going to see the band Good Times at a local club. When I had knocked on the door for our first date, Anna had answered quickly. This time, however, she was no where to be seen. Olivia answered, wearing jeans and a black band shirt, almost copying my own outfit, but my shirt was for a different band. "No Anna to give me the third degree this time?" I joked. "She's been grumpy all day," Olivia said. "Ever since I caught her getting felt up by that boy last night, she's barely come out of her room." So she was in her room, I thought. The blinds had been closed all day. I'd checked. But I did my best to put her out of my mind. Tonight was about having fun with Olivia. ***** The band was great that night. Olivia and I were both drinking and having a great night. I excused myself for the restroom right before the end of their first set, hoping to beat the crowd. While I was there, I checked my phone. There were a few texts from Anna. I saw the timestamps on each one. Twenty minutes ago: 'I'm in your house'. Ten minutes ago: 'Found your tablet. 1234 isn't a very safe passcode, Grant.' I kicked myself. My tablet was always in my house or with me, so I really didn't think about securing it. Eight minutes ago: 'Found your videos. Didn't know you had an extra camera in the bedroom. Nice hiding place.' Seven minutes ago: 'So the last time, when I was pretending you were watching, you were actually watching?' I was really busted now. If Anna wanted, she could show those to her mother and I'd probably go to jail. She had me over a barrel and she knew it. The second half of the show, I tried to relax and enjoy the music and Olivia's company. But I kept thinking about Anna and her videos. She hadn't texted any more after that last one, so she was either planning nuclear revenge, or she was entranced in watching them. With any normal girl, I'd bet on the first one, but I knew Anna was pretty kinky, so I bet my odds were about 50/50. ***** Arriving home, I walked Olivia to her door. "Thanks for the date, Grant," she said. "This was really fun." "You're a fun date, Olivia," I told her. "I'm glad we got to know each other." I leaned in, and she came the rest of the way to meet our mouths together. The kiss was really nice. Any other time, any other woman, I'd think about inviting her into my place for more. But thoughts of Anna lurked in the back of my head, and now was not a good time. Especially tonight, where Anna was in Olivia's house, and I had no idea what havok Anna had performed in mine. We bid each other good night, and I watched Olivia enter her house before returning to mine. Thankfully, there was no havok or mess. Anna could have trashed the place in anger, but that wasn't her go-to. Bob was there, happy as normal. The only thing out of place was that my tablet was gone. I peeked from my bedroom window. Anna's blinds were closed, but her light was on, so I texted her. 'Where's my tablet?' 'Here with me. Say hi to the camera.' I turned to face the camera on my dresser. She'd pulled the photo frames apart, exposing its lens a little more. 'If you want your tablet back, you need to earn it. Undress for me.' That's what she wanted. I'd watched her many times, with and without her knowledge. Now she wanted to even the score. 'I could just ask your mom to get it from you.' I pointed out. 'You could, but then I'd show her what's on it.' There it was, the blackmail element. Do it, or else. Another text immediately followed. 'Come on Grant, it's only fair.' I spoke aloud, knowing she could hear me. "I do this, and I get my tablet back, and things go back to normal?" 'Yes. I promise,' came the texted reply. I really had no alternatives. If Anna showed Olivia the videos, I'd probably get arrested. Anna would turn on some tears and I'd get arrested, even though it was her who was naked in my house. She'd play up the fact that I was a full-grown adult and she was a barely-legal teen girl. I took off my shirt and looked at the camera. I unbuckled my pants and let them fall to the floor. It was a weird feeling, being watched, but it was strangely erotic. I started to understand why Anna got off on it. I got out of my clothes down to my boxers. My phone dinged again, another text from Anna. 'Nice bod. But nothing seems to be at attention.' I looked down. She was right, I was nervous, and wasn't erect. It was starting, but not yet half-way there. I said aloud, "I don't have anything sexy to look at." There was a minute of delay before I got a response. It was a picture of Anna on her bed, from her neck down, wearing only pink panties. Her legs were bent, and my tablet sat on her lap. I saw an image of me on the screen. 'Try this,' was the caption. Bob And The Girl Next Door Ch. 06 A shower, and a date. It was hard to get work done that Monday. Mid-day, I couldn't take it anymore. I grabbed my tablet and pulled up the last few videos of Anna. The most recent one was of yesterday afternoon, when Anna and I masturbated in my bedroom together. I watched the videos and gave myself a little relief, just so I could calm my mind and get back to work. That night, I was outside watching Bob do his business when Anna texted me. 'Mom's gone to work. Come over?' It was followed by the peach emoji, which even an older guy like me recognized as a sexy signal. I looked up at her window. She was standing there, watching me. She waved, and I waved back. I gave her a hand signal, indicating her to give me five minutes, and she nodded. She pointed downwards, towards the back door of her house, then disappeared from view. Four and a half minutes later, I was entering her house via the unlocked back door. Anna was nowhere in sight. I looked around the first floor quickly, but I knew she'd be upstairs. I jogged up the stairs and called for her, "Anna?" "In here," she said with a giggle. The voice didn't come from her room. Then I heard a shower start. The bathroom door was open just a crack. I peeked inside. Anna stood there, completely naked, not looking at the door at all. Then she started speaking to herself, pretending I wasn't there. "I've been such a dirty girl lately. I need a shower. I just hope Daddy's not spying on me while I'm naked and wet." Just like that, she had established the game she wanted to play tonight. I stood in the hall, simply watching as she rubbed her hands over her breasts, then down her stomach, and around her hips to grab her own ass. The bathroom mirror helped me see all of her body at the same time. Then she stepped under the shower's spray, wetting down her lithe teen body. I watched, enraptured by the vision before me, and I quietly unbuckled my pants to free my erection from its prison. I had resolved that I wanted to fuck Anna, but she seemed perfectly content with keeping me as her voyeur. In fact, that was what really got her off: knowing she was being watched. Anna actually did bathe. She used her body wash and soaped herself up. I caught a whiff of the scent, registering flowers and tropical fruits. She washed her small chest, then she bent over and rubbed the soap on her long legs. From that angle, I got a good glimpse of her puffy lips from between her legs. In the rinsing, she abandoned her attempts at cleaning, and just started playing with herself. She leaned backwards against the tiles of the shower wall, spread her legs open, and worked her small fingers inside. "Oh fuck. Oh, I think I'm still being dirty. I'm so naughty," she called out for me to hear. "I just keep thinking about my Daddy, and his big, thick dick." I rubbed myself and listened to her continue. "Sometimes, I think about Daddy putting his dick in Mommy, and me watching them fuck. But even more often, I want Daddy to put his dick inside me. I bet it would make me feel so good. I bet it would feel so big inside my little tight pussy. I wish he was here now, watching me play with myself. He could play with himself too, and spray his cum all over the towel so no one finds out." Towel? What towel? I looked around and spotted a folded-up hand towel on the table nearby. Anna had planned this out pretty well. I took the towel and unfolded it for my use. She was raising her voice now, getting closer to cumming. "If he was there, I could say naughty things out loud, to make him cum too. I could say, Oh Daddy, I'm so close. I want your big Daddy dick in me, please Daddy. I want your big dick fucking my tiny pussy!" That talk was getting me close, though it was a little strange to hear her call me Daddy. She'd only said it once yesterday. Now she was saying it out loud, calling me Daddy while she frigged herself with her fingers. "I want to cum, Daddy, please. I'm, I'm cumming!" she yelled, and nearly collapsed in the tub. Watching her, I also came, catching all of it in the convenient hand towel. I watched her stand up, recovering from her ecstasy, turn the water off, and wrap herself in a towel. I was going to knock on the door and ask her what I should do with the small towel I was holding, full of my spunk, when I heard a rumbling noise. Was that... the garage door opening? Anna heard it too and she started freaking out. "SHIT!" she yelled. "My mom's home!" "What!?" I hissed. "I thought you said she was working!" "Well she's home now. You need to get out of here!" "I can't! She'll see me!" We both looked around frantically, trying to figure out what to do. "Under my bed! Hide!" Anna told me. We both ran into her bedroom, and I dove under the bed. My pants were still unbuckled, and I still held the jizz towel in my hand, but I got myself completely underneath. Anna rearranged her bed sheet to drape over the side, covering me, or so I hoped. A knock on the bedroom door was accompanied by Olivia's voice. "Anna? You still up?" "Yeah mom, just got out of the shower," Anna called back. "Can I come in?" My brain tried to telepathically tell Anna to say no, but she put on her robe, and said, "Yeah, okay, I'm decent now." The door opened and Olivia walked in. "Hi honey," she said to her daughter. I froze, trying not to make any noise at all, or even breathe loudly. "Hi mom, I thought you were working all night." Olivia sat on the bed. I saw her feet near my face. "I was supposed to," she answered, "but it was a really slow night, so they let me go early." "Oh," was Anna's response. "Well, that's good I guess. But I'm really tired, so I think I'm going to get some sleep." "Okay, honey." Olivia kissed her daughter and told her, "I think I'll get my own shower. Sweet dreams," before leaving and closing the door behind her. I didn't move a muscle for several minutes. When I heard the shower water come on again, the sheet was lifted from the bed, and Anna gestured me out. I slid out from under the bed and stood up. Anna was grinning. "That was too close!" I wanted to yell, but I had to whisper instead. "It was fun, though, huh?" Anna was still smiling. "It's fun as long as you don't get caught!" "And we didn't. Good job hiding, by the way." "I need to get out of here, now." I turned and headed for the door, but Anna grabbed my arm and pulled me back. She looked into my eyes. "I hope you enjoyed the show, Daddy," she said. Then she kissed me on the cheek. Another first for us. I considered it ironic that I'd seen her naked a dozen times before she'd done that. I was frozen until she nudged me to move. "Go! Get out!" I left as quietly as I could, sneaking out the back door, while Olivia was in the shower. ---- I made myself scarce the next few days, staying in my house most of the time. I was still paranoid about Olivia almost catching me in her house, watching her naked daughter in the shower. It had been far too close for my comfort. I didn't even look out my bedroom window, even though Anna had texted me to see if I was watching. When I finally emerged days later to eat lunch on my patio, I wasn't surprised when Anna skipped over. Today's sexy outfit was a bikini top and short shorts. Her breasts, though small, gave a little bounce as she skipped. She sat down at the table with me. "Hi Daddy," she cooed at me. I looked around, paranoid that some neighbor would hear, or worse, Olivia. "Don't call me that." "You liked it the other night." "It was hot in the moment, in private. But it makes me nervous when you say it out in the open like this." She patted my knee under the table, making me flinch, but she kept it there. "Don't you want to be my Daddy? Mom wants to go out with you again, by the way." "Really? She said that?" Anna nodded. "Of course. She thinks you're cute, just like me." She dropped her voice to a whisper. "I even found out a secret you'd like to know." Her hand inched up my thigh. "Is it a secret if you tell me?" I asked. "It is if you don't tell her you know. Remember a little while ago, I told you she's got a big bush?" I nodded, remembering Anna taunting me, comparing her mother's down-there hair to her own clean-shaved pussy. Anna whispered into my ear. "Apparently she only did that 'cause she wasn't dating. She told me she trimmed it back now. You know, just in case she wanted to show it to a certain cute, friendly neighbor." I was getting hard, thinking about Olivia's potential desires, and listening to Anna's breathy voice in my ear, and feeling Anna's hand getting close to my crotch. "She did that?" Anna nodded, then her hand started rubbing over my rock-hard dick through my pants. "Yup. If you fuck my mom, can I watch?" Her voice was oozing sex. That thought was too much; any more and I might cum in my pants. I picked up my dishes and dashed inside. "I gotta go." Anna smirked at me as I tried to hide my erection as I left. ---- I did take Olivia out again that weekend. Anna wasn't mad at us this time, so she gave me a friendly wave when I left with her mother, and told me she'd take care of Bob that night. This was a pretty normal date. I took her to dinner, then we walked around park, taking advantage of the warm summer night. I held her hand as she walked. Somehow, despite the fact that we'd already kissed before, holding her hand in a public place felt slightly more intimate. "So," Olivia started as we sat on a bench for a little rest. "I've noticed something between you and Anna recently." My heart jumped. "Yeah?" I said, not knowing what she meant. "Yeah. Sometimes it seems like you're friends, and other times it's a little awkward." I wasn't sure where this was going. "Well, she's really nice. And she likes Bob. But she's a teenager, so we don't have much in common." That wasn't really true. When I'd had the occasional lunch with Anna, I'd found that we had more in common than one would expect from a 14-year age gap. She liked a lot of the same bands and movies that I liked. She considered my words. "Well, you have me in common. And if you and I continue to date, I don't want things to be weird. So, I had a thought." "Okay?" "I think you and Anna should go on a date." "A date?" It was a weird thought. I tried to make light of it, like a joke. "Don't you think she's a little young for me?" She punched my arm at my joke. "You know, time to get more comfortable with each other. Like a daddy-daughter thing." I winced when she said 'daddy', thinking about Anna's use of the term, and Olivia saw it. "Not comfortable with the term daddy-daughter?" she asked. "Just getting used to dating someone with a daughter, I guess," I told her. "I guess that's to be expected at our age." Then I spun the argument. "Let's say for a minute we get more serious," I said, and she nodded her understanding. "Would Anna call me dad? Would she listen to me if I told her dad things, like 'put on more clothes' or 'go to bed' or 'you can't date that boy'?" Olivia was chuckling. "I don't know that she listens to me when I say those things, so no, I can't guarantee that. But I think she likes you, and I want to make sure all three of us get along." She squeezed my hand. "Please? Do this for me? If nothing else, for my own peace of mind?" I sighed. "Okay. For you, I'll take Anna out." "You can't be any worse than that Ricky boy," she said. "At least I know you won't feel her up in your car." I thought about that situation. I'm not sure that I wouldn't do it. I bet Anna might want it. When we got home, Anna was waiting for us. She was dressed for bed, wearing a long t-shirt. I guessed there were panties underneath, but couldn't tell for sure. Olivia led me inside. "Anna, Grant has a question for you." She motioned me towards her daughter. I walked closer to Anna. "Your mom wants to make sure that we're getting along, so she wants us to spend more time together. Anna, would you go on a date with me next weekend?" Anna's smile nearly exploded her face. "Yes, Grant. I would like to go out with you," she answered politely. Olivia nodded her approval. But I could see the look in Anna's eyes. In her mind, this was no normal daddy-daughter outing. This was a real date with the man she wanted. ---- I was torn on deciding what to do with Anna on our date. I could play it safe and do something active and public, like bowling. That would certainly please Olivia. Or, I could go more intimate and private, like a quiet, isolated dinner. I'm sure Anna would love that. In the end, I tried to put together a compromise. I told Anna I was taking her to a diner for burgers and fries and milkshakes. It was non-romantic, as it was a family-friendly place. Then we'd do a round of mini-golf. Olivia was satisfied with the appropriate plans. I knocked on Olivia's door to pick up Anna. Anna came out wearing a cute pink t-shirt and a denim skirt that reached just above her knees. Her blonde hair cascaded past her shoulders to her back. Olivia saw us off, wishing us a nice time. When we got to the diner, I slid into a booth, and to my surprise, Anna slid in beside me. "Thanks for taking me out, Grant," she said. That statement was for the public ears, I realized, as her hand patted my knee below the table. The restaurant was generally loud enough, and our booth walls were high enough, that our quiet conversations would not be overheard. The waitress came to our table, and looked at us a little funny while we ordered. "We're on a date," Anna blurted out excitedly. "Yeah, a daddy-daughter date," I clarified. That seemed to mollify the waitress' thoughts, and she left. "You're going to get me in trouble," I told Anna quietly. She shrugged. "She doesn't know us. I could be twenty-five." "No one thinks you're twenty-five," I said to the pretty, petite teenager. "You're eighteen and you look it. I'm lucky if she doesn't think you're sixteen." "You don't think I look older?" Anna said with a small pout. "Don't worry, I like you at your real age," I said. "To me, you're the prettiest eighteen-year-old I've ever seen." Anna blushed. "You're just saying that. I still think my boobs are too small." "I like your boobs. Perfect little handfuls." "You've never actually had your hands on my boobs," she pointed out. "Are you aiming to change that tonight?" "Do you know what your mom said about that?" I asked, and Anna shook her head. "She said at least I won't feel you up like Ricky." Anna laughed her cute little head off. ---- I had thought dinner would be awkward, but it turned out to be really nice. We ate and talked, and I realized I had even more things in common with the young beauty that I didn't think I would. Then she smiled at me. Like, really smiled. Not a sexy, come-hither smile. It was a kind, glad, friendly smile. It was at that moment I realized that it wasn't just a sexy fling for me. I was starting to fall in love with Anna, and I suspected she felt the same for me. After dinner, we went off to the mini-golf course. Here, I realized that Anna's skirt seemed slightly shorter than it had when I picked her up. It looked like she had hiked it up a little, showing more of her thighs. I looked around. This hot little girl I was with had attracted a few looks from other guys. I felt a little possessive. "Did you raise your skirt?" I asked. "Why?" she responded. "Are you paying close attention?" On the first hole, she sunk her ball in the very first shot. While she did a little celebratory dance with her club, I thought I might be in serious danger of losing this game. Then I watched Anna bend over to retrieve her ball from the hole, and her skirt raised to show the bottoms of her bright yellow cotton panties. She slowly straightened up, then turned back around to confirm that I'd seen her. "Your turn," she said, giving me a knowing smile. It was hard to play with Anna's distractions. Every time she bent over, I saw her cute little pantied ass. To make it worse, she tended to brush past me when I was trying to shoot. Nevertheless, I did fairly well, and was only one stroke behind her after the first nine holes. At that point, Anna excused herself to use the restroom, and I sat on a bench, waiting for her to return. When she returned, she was grinning. "What's with that smile?" I asked. "Nothing. Just thinking about how I'm going to beat you." I found out very quickly why she was grinning so much. When she sunk her ball on the 10th hole, she bent over to retrieve it, and I saw no flash of yellow cotton this time. It was all skin now. Her cute little ass was visible for me, and probably anyone behind me. She'd probably stuffed her panties in her pocket. "You're being naughty," I warned her. "Who, me?" she said with a cute innocent face. I had to step up my game to keep up despite her distractions. I also did some distracting of my own. While she was trying to shoot, I would stand behind her, toying at the hem of her skirt with my club. "Now who's being naughty," she said, then sank her putt like an expert. When we got to the 18th hole, we were tied. "Want to make things interesting?" she asked me slyly. "I think things are pretty interesting already." "I was thinking about making things interesting in your car," she clarified. "If I win, which I will, I want your fingers inside me." "Sounds like that's a win for me too," I admitted. "What happens when I win?" "If you win," she emphasized the first word, "I'll give you a blowjob." "Have you ever given one before?" I wondered aloud. "No, but how hard can it be?" She said, rubbing her hand on my crotch, emphasizing her double entendre. I was already hard. "I think I have an advantage," I told her as she prepared her shot. "Why's that?" I leaned in to whisper in her ear. "You're trembling inside," I said breathily, meaning to turn her on. "I bet you're so wet, leaving your pussy exposed like that." My putter stroked upwards on her leg. "You're so wet, you're dripping." She moaned. My distraction worked. Then I stood back and watched. She tried to calm her mind and focus, but it wasn't working. She took her shot, and missed. "Damn you," she muttered. She sunk her second shot. I stepped up and prepared to putt. "Sink this shot, and I'll take care of you, Daddy," she called out. She thought it would mess me up, but now I'd gotten used to her saying it. I hit the ball, and it was dead straight for the hole. Then it stopped on the edge. I hoped a stray wind would blow the ball in, but no luck. "Oh man!" I said. Anna whistled. "That was really close." "So we tied. What happens now?" Anna thought for a second. "You could argue we both won." I nodded. "I can see that. And if we both won, we both get rewarded." Anna smiled. "I think that's very fair." ---- I had not fooled around in a car since I was a teenager myself. But I remembered where I used to do it. I drove us to an isolated spot in a park, then parked the car and turned out the lights. "Lesson number one," I said to Anna. "If you're going to fool around in a car, you don't do it in your mom's driveway." Anna laughed. "I never said Ricky was smart." "Admit it, you only went out with him to make me jealous." "It worked didn't it?" "It did." I shifted my weight a little closer to her. "All this time, all we've seen of each other, I've never kissed you." Then I cupped her face in my hand and brought it to mine. Our lips connected. Her soft mouth moaned against mine. "God, Grant, why did we wait so long for that?" she asked, then kissed me again. Her hand went to my chest, then down my stomach, and rested in my lap. "I think we have a bet to settle up." "I think you're right," I responded. I continued kissing her as I placed my hand gently on her knee, then slid it upwards, into her skirt. When I reached the forbidden fruit between her legs, she whimpered. "Am I the first man to touch you there, baby?" I asked. She nodded. "I'll be gentle," I assured her. I reached into my back seat and found a towel. I always kept one there for emergencies; it was something my dad instilled in me. I unfolded it onto my lap. Then I gently pulled Anna's little teen body into my lap, so her back was against my door. I pulled her skirt up to her waist, giving me full access to her. I could barely see her perfect pussy in the dark. Then I stroked her there, and she parted her legs wider, displaying her desire for more. I kissed her as I played with her, teasing her, spreading her wetness all over. She whimpered again as I slipped just one finger past her labia, just barely inside her. I pushed it all the way in, so slowly, and she moaned into our kiss. I moved my kiss to her neck, and I slid a second finger inside. "Oh, Grant, oh my god," she whispered into my ear. "Call me daddy," I groaned. "Oh, yes Daddy!" She was excitedly trembling in my arms. I worked my fingers in and out of her virgin pussy. "You're so tight on my fingers, baby girl," I told her. "Do I make you feel good?" "Yes, Daddy, so, so good." I held her tight with my left arm. My right thumb found her clit and I stroked it as I continued to thrust my fingers in. She gasped at the contact on her sensitive spot. "Do you like your little clit rubbed?" "Yes, Daddy. Please rub my clit." I looked down and saw that the towel was a good choice. She was so wet, but the towel was soaking it up. Without it, I'd have her wetness all over my pant leg. I worked my fingers in faster, deeper, faster. "I want you to cum for me, baby," I said to her. Anna gasped again. "I'm so close Daddy, I'm close, I'm... I'm... cumming!" She came hard, and I held her close to me, feeling her muscle convulse. It was a magical moment, and it felt so good to have this beautiful young woman, shaking in euphoria, wrapped in my arms. When Anna started to relax, she looked into my eyes dreamily. "Thank you Daddy." Just then, her phone rang in the car's cup holder. "Shit, it's my mom," she said. She answered it, and crawled off my lap. "Hi mom. Yes, we're on the way back. We'll be home in just a few minutes. Yup, see you soon, bye." I looked at my watch. It was getting a little late. I put the car in gear and started the drive home. We drove for a minute before she spoke again. "Sorry I didn't get to complete my end of the bet." I smiled. "I'm not sorry. I wanted to make you cum. Even more than getting my own attention." "It was so amazing, Grant, I mean, Daddy. It's so much better than when I do it myself." "I'm glad. But now that you've found that out, just don't let Ricky or any other boys do that to you." "I won't, Daddy. Only you," she told me. ---- When we got home, Anna fixed her hair and makeup, making it look like she didn't just get a mind-blowing orgasm from my fingers. I also made sure I wasn't wearing any of Anna's lipstick. "Stop here," she suddenly requested, about a block from home. I pulled over. "Why?" Anna took a deep breath, and let it out. "I wanted you to know I really enjoyed myself tonight." "So did I." Her hand was on the arm rest, and I put my hand on top. She looked into my face, and I think we had the same thoughts at the same time. Our faces came together and we kissed. It was wonderful, and I felt more love for this beautiful creature than I had felt for anyone since my wedding day. I felt more in sync with Anna after one date than I had with Olivia after three, and it wasn't just a horny man's fantasy. This was a real connection. We broke the kiss, and all Anna could say was "Wow." "Yeah." "Grant, I..." she started, then stopped. "I know." I told her. "I feel the same." "You do?" "Yeah." "It's... this is crazy, right? I mean, I just started flirting with you..." I nodded. "I know. I don't think we meant for this to happen. But it did." "Yeah." There was an awkward pause, then, "What... how... what are we going to tell my mom?" That was the most difficult question. "I don't know." "We'll figure it out together?" "Absolutely," I answered, and she smiled and kissed me again. I brought Anna back to Olivia, where we gave our brief report of our fun night. Anna told her mother about our tie at mini-golf, implying we needed a rematch sometime to settle the score. Thankfully, she didn't mention the bet, or the sexy results that ensued, or the kissing. When I returned to my car to put it in the garage I spotted Anna's yellow panties in the cupholder. This was a message: thanks for a great night. ----