Note: totally fictional, made up fantasy of mine. Descriptions of people are real, however, just with changed names.
Following my divorce from my now ex-wife, it took a few months to get back to the single life. Threw myself into my work, working crazy hours, while also picking up a few hobbies, both old and new. But, the social part of life was throwing me for a loop. Luckily, I had a few longer coworkers that would invite me out on the weekends, and when I didn’t have my kids, I would gladly join them at a bar for a couple hours. I didn’t drink, but still enjoyed being with them, and even trying to remember how to flirt.
One such Friday night, hanging out at a bar none of us had ever been to, I was surprised to see my ex-wife’s youngest sister at, hanging out with her friends. Katie was almost the black sheep at the family. She married young, was divorced within a year due to her cheating, and was going out drinking and partying on a weekly basis, much to the distant of her LDS parents. Despite a ten year age difference in me and her, we got along well, since I tried my best not to judge her, and just let her be herself around me.
When she looked around the bar area and spotted me, she waved to get my attention before walking over and giving me a hug. “I honestly never thought I would see you in a bar. What are you drinking?” She asked me. I replied back, “just a Pepsi. Here with some co-workers, just hanging out.” We talked for a few more minutes, catching up a bit before she went back to her friends.
A few hours later, as I was thinking about leaving for the night, Katie stopped me on the way back from the bathroom. “So, why are you really here? Looking for a hook up? I’ve seen you trying to flirt over there” I laughed, telling her, “if it happens, cool. But I’m not trying as hard as I could be.” She wrapped one of her arms around my shoulders, turning me to look at her friends, and pointed at one of them. “You see that girl there?” I shook my head yes, wondering where this was going. “Her name is Megan. She wants to get laid. Only had sex with one guy a couple of times and he had a tiny dick. She’s practically begging guys to take her home. I won’t let her leave with somebody unless I feel like they will treat her right. I know you will treat her right.”
I looked at her friend and said, “sorry, Katie, if I’m taking a girl home tonight, it wouldn’t be your friend.” Katie removed her arm from me and said, “is it because she’s bigger? She’s willing to let you do whatever you want to her. She’ll make it worth your while. Hell, I’ll pay you to do it.” I told her, “no, it’s not that. She’s too drunk for me. And I’m definitely not letting you pay me to sleep with one of your friends.”
“Fine,” Katie said, “then sleep with her tomorrow night. And I never said I would pay with cash. I can find other ways to pay you. Maybe I’ll sleep with you too.”
I told Katie, “Whatever, you’ve always had a crush on me, you would sleep with me anyway.”
She blushed, saying, “so? Fine. I would find some way to pay you back for it.”
I told Katie that I would think about it and said goodbye to her, hoping she was too drunk to remember. I said goodbye to my friends before heading home for the night.
The next day, I received a text from Katie saying, “did you think about it yet? I think I know how to pay you back.” I replied back, “a bit. How would you?” A few minutes later, her text said, “Whatever you want.”
“Gotta be more specific then that.” I told her. “I’ll do whatever you ask of me for a weekend. Sex. Cooking. Blowjobs. Whatever.”
That actually didn’t sound too bad. I had already slept with one girl since my divorce, and was looking to expand my horizons, so having a girl do whatever I want for a weekend sounded like a good time to me. Or maybe longer?
“I like the sounds of that. But, how about for a month instead?” I didn’t get a reply for about ten minutes, figured that she figured out it wasn’t worth it. Oh well, no big loss for me. Instead, her next text read, “you were right at the bar the other night. I’ve always had a crush on you. When I cheated on my husband, I was half wishing it was with you. And when you divorced my sister, I got excited that I might be able to sleep with you some how. If you fuck Megan for me, I’ll be available to you whenever, wherever, until you tire of me.”
Damn. Before I could respond, she sent me another text that said, “hell, if you don’t sleep with Megan tonight, I might just show up at your doorstep and take my chance. But, I did promise my friend that I would help her get laid, no matter what it took.”
I told her to tell Megan to be at my house after 8 PM tonight.
When Megan showed up just shortly after 8 later that night, I could tell that she was nervous. After introducing ourselves, I tried my best to make her comfortable. Megan was on the bigger side and also a few inches shorter then me and I stood around 5 feet 9 inches. She had a round face, brown hair that fell just below her shoulders, and big breasts that she was showing off with a low cut shirt. She actually had a decent singing voice, one I heard at the bar the other night, and told her that she sounded good.
“Oh, thanks. I’ve always had a dream of being a singer.” She told me. Knowing that if we didn’t get things started, it was going to be a really awkward night, I said, “Hopefully I hear it again tonight when I make you moan.” She laughed and blushed, saying back, “me too. That would be nice. I’ve never moaned before.” “Never?” I asked, “Katie did tell me a little about your past, one guy with a tiny dick?” Megan said, “yeah, my first boyfriend. Tiny dick, big belly, would pump three times and be done.”
I reached out for her, squeezing her leg, “well, let’s go into the bedroom and give you a good time.” We left the living room and she followed me into the bedroom. Once there, she sat down on the bed and I sat down next to her. Still sensing some nervousness, I told Megan, “if you don’t want to do this, we don’t have to.” She replied back, “no, I do want this. I’m craving it. I’ve been turned on most of the day, hell, I even had to play with myself earlier because I was going crazy. Guess I just don’t know how to start.” I wrapped my arm around her, pulling her close and started to kiss her neck. In between kisses, I said, “before we get too far, is there anything that’s off limits? And anything you really enjoy having done to you?”
As I continued to kiss around her neck, softly sucking on her skin, Megan said, “I love my tits to be played with. I’m not very good at blowjobs, but will try them. Honestly, I just want a man to touch me.”
As she said this, I moved my hand over to her breasts, cupping them on the outside of her shirt and squeezing them as I kissed down her exposed cleavage. As I got closer to her breasts, I noticed that she had freckles on them that matched the freckles on her face. I kissed away from her breasts, up her chest, back to her neck, and finally to her lips. As my lips touched hers for the first time, I slipped one of my hands down her shirt, grabbing her bare breast, finding my way to her nipple. As we made out, I took her nipple in my fingers, rolling and pinching it. I moved to her other breast, doing the same thing to that nipple.
Megan broke our kiss, moaning out “Oh my God,” as I played with her nipples, her body almost starting to shake. “You weren’t kidding when you said you loved having your nipples played with.” In between moans and trying to breath, Megan told me, “no, I wasn’t. I’ve made myself orgasm just by playing with them.” I replied back, “that’s awesome. What happens when somebody sucks on them?”
She said, “I go crazy.” Wanting to see this, I removed my hand from her shirt, then pulled her shirt off over her head. She was wearing a sports bra and she helped me take it off her, freeing her massive breasts, with very large nipples. Her right breast was closer to me, so I leaned down, taking it in my hand, and squeeze it as I licked around her nipple. Taking it in my mouth, I gently bent down on it before sucking it. I used my left hand to pinch her left nipple, before I moved over and started to suck and lick that one.
“Oh my god!” Megan moaned, her hips bucking up towards me as she had an orgasm. She laid down on the bed, causing me to let go of her breasts. I helped her slide up to the top of the bed, kissing her as we went. I hurried and pulled off my shirt, leaning down to kiss her again, feeling her nipples on my chest. As we kissed, I worked my hand down to her pants, unbuttoning her jeans, then started to pull them down. She lifted up her hips to help, and we tossed her pants and underwear off the bed. Leaning down to kiss her again, I used my hand to spread her legs, then rested my palm on her groin. I could feel her wetness and started to rub my finger in her pussy lips, slowly pushing inside her. I had to lift myself up a bit to give my hand the correct angle to finger her, and glanced down at her, a look of pleasure on her face. “So, if you orgasm just from having your nipples played with, what happens if they’re sucked on while I’m fingering you?” She opened her eyes and said, “I’ve never had that done before.” I smiled at her, leaning down to take her nipple on my mouth, licking, biting, and sucking on it. I started to make a “come here” motion with my finger inside her pussy and could immediately feel her getting wetter, her body tensing up, and finally heard her scream, “OH MY God!” As she squirted all over my fingers and my hand. I kept going, wanting to drive her crazy, she had another orgasm before she finally pushed my hand away saying, “I think I’m going to pass out.”
I went back to kissing her neck, softly squeezing her breasts as Megan caught her breath. “This is already the best night of my life,” she said. Looking up at her, I asked, “are you ready for more?” She shook her head yes, saying, “please. Please give me more.” I said OK, sitting up enough next to her to pull my shorts and underwear off, my hard cock springing out of them. When she saw it, her eyes went wide and she said, “Wow. Umm…I don’t think that will fit in me.” I glanced down at my just under six inch, thick cock, then said, “we’ll take it nice and slow and if it’s too much, we’ll stop.”
She agreed, not taking her eyes off my cock. I finally said, “you know, you are allowed to touch it.” She slowly reached out her hand, wrapping it around my base. She started to stroke me, slowly at first, but going faster and faster. Her head was leaning toward me and she finally stuck out her tongue, licking the pre-cum off my tip. She then looked up at me and said, “sorry, I told you I don’t really give good blowjobs and you’re just so big. I don’t even know what to do.” I asked if she wanted me to help guide her or if she wanted to move on and she replied back, “you made me feel so good, I want to at least try to return the favor.” I told her to not jack me off so fast, to take it nice and slow, a steady rhythm, and she did so. “When you’re ready, I do like to be licked. You can start at the base, almost like a lollipop, going right from the base, to the tip, then pop the tip of me into your mouth. You can then swirl your tongue around the top, that’ll drive me crazy. Being careful not to graze me with your teeth, start to slide more of me into your mouth, taking in as much as you can.”
She listened pretty well, nodding along with my instructions. When I was done, she did as I suggested, licking from the bottom to the top, then took my tip into her mouth. I was a little nervous, because Megan had a tiny mouth, one that she could barely open wide enough just to take the top of me into. Not wanting to hurt her confidence, and because it did actually feel good, I moaned out loud, running my fingers through her hair, gently attempting to push her head down more. She did try to go farther, but couldn’t more then the tip in.
Sensing her frustration, I said, “don’t worry if you can’t do more. Focus your mouth on sucking on the tip, using your tongue. Use your hand to work my shaft, it’ll still feel just as good.” She again was a willing student, doing as I suggested. Before long, I was moaning again, telling her how good it felt. I pulled her head off after a few minutes, asking if she was ready for more. She nodded yes and laid down on the bed.
I climbed in between her legs, using my hand to line myself up with her entrance. When I felt the tip go in, I let go, placing my hands on either side of her head, and started to slowly push in more. Feeling some resistance, I asked if she OK and she said, “it hurts but keep going.” I did as she said, slowly pushing in until I was in all the way. I asked how it felt and she said, “I’m getting used to it, keep going.” When I told her that was everything, she leaned up to kiss my lips. When we broke the kiss, I slowly pulled back out, then pushed back in, picking up my speed every time, going faster and harder, trying to keep my self balanced above her.
Megan was moaning the first few thrusts into but when she stopped, I asked if it still felt good and she said, “yeah, just getting used to it. Feels good but a little uncomfortable.” I pulled myself out of her, standing up off the side of the bed. I grabbed her leg, pulling her to the side of the bed, her butt just barely hanging on the side of it. I had her legs in either side of me, sticking up in the air, and I guided myself back into her pussy. I bucked my hips back and forth, and asked how that was and she said, “that feels amazing. Oh my god.” I smiled at her and begun to thrust into her, giving Megan my full length every time. I watched as her breasts begun to bounce and I reached out with one hand, taking them each in turn in it, squeezing them and pinching her nipples. I felt as her pussy clinched around my cock and she orgasmed again.
Opening her eyes after her orgasm, she said, “how do you last so long?” I just told her, “it’s a gift and a curse.” “Not that I’m complaining, this is amazing. What other positions do you like?” I replied back, “I’m a big fan of doggy, it’s how I usually end up finishing.” She started to scoot back on the bed, causing me to fall out of her. She climbed onto her hands and knees, saying let’s do it. I kneeled on the bed behind her, lined up with her entrance again and pushed deep inside her. “Oh my god, why does it feel like you hit a new spot every time?” Megan moaned out. “I’m just glad you’re enjoying it. Where do you want me to finish at?” She replied back, “I’m on birth control, but if you don’t want to finish in me, just not in my mouth.”
I grabbed onto her hips, using them to hold her steady as I started to pull out of her, then pushed back in. After working up to a steady pace, I started to move her hips forward and backward, pulling her back onto me every time I thrust forward. I told her I was getting close as I pounded into her. When I started to moan, I pushed in deep to Megan, shooting some cum into her. I quickly pulled out finishing on her ass, a couple shots landing on her back.
When I was done, I got up to get her a towel and helped cleaned up her back and ass. Laying down on the bed next to her, I pulled Megan in to cuddle, feeling her naked body pressing against mine. We kissed a few times before Megan got up and begun to get dressed. “Where you going?” I asked her. “Home?” She said “don’t you want me to leave now that we’re done?” I told her, “no, you can spend the night if you want to. I would never just make you leave.” She stopped with her pants half on and said, “but I don’t have anything to sleep in.” “I’m sure I can find something.” She slowly pulled her shorts off and said, “or I’ll just sleep nude, that’s what I normally do.”
I told her that was fine, as I got out of bed and got myself ready. We fell asleep after talking and kissing for a bit, her thanking me for everything and continually asking if I was sure.
I woke up early the next morning when I felt Megan get up out of bed and go into the bathroom. I was falling back asleep when she kissed my forehead, softly whispering goodbye and thank you. When I fully woke up the next morning, I was hoping it was a dream, but she really had left.
Later that day, I got a text from Katie that said, “Sounds like you and Megan had a great time last night. Thanks again for doing that. She told me to tell you that she left this morning because she was sore and didn’t think she could take you again so soon.” I told her no problem, that I enjoyed it and she replied back, “after listening to her describe it, it made me excited.” “Excited for what?” I asked her, her telling me, “to sleep with you, duh. When?”
I texted Katie back, “I’m free now.” A few minutes later, she said, “I’m on my way. Be there in five.” I forgot that since her break up with her first boyfriend following her divorce, Katie had been living with her parents, who only lived a few minutes away from me.
Source: reddit.com/r/eroticliterature/comments/wpavg3/how_my_exsisterinlaw_became_my_fwb_m34f24