As Kayli and I planned out the weekend that my wife would be gone, we knew that we wanted a night together and that I wanted a day with a Jennifer. Of course, that day with Jennifer would turn into a full night with her. But, as Kayli and I talked about what we would do with our night together, we started to realize that this might be the last time we did anything together. As much fun as we were having, we felt like we were growing too close to each other, and didn’t want anything to happen to our families. So, we decided to enjoy the night we had, and go out with a bang.
By the time I had dropped my family off at the airport and got back home that Friday, it was mid-afternoon. Kayli had been working me up all week, as I had to her, and I couldn’t wait for her to come over. When she finally texted that she was on her way, I started to think of all the things I wanted to do to her, starting as soon as she walked through the door, getting myself turned on. When she arrived, I watched from my living room window as she got out of her car. She had a couple plastic containers in her hands, most likely with food in them, a black duffel bag on her shoulder, and was wearing her typical black leggings and a gray tank top. Her black hair was pulled up into a messy bun on top of her head, and I couldn’t want to pull on it while pounding her from behind.
She let herself inside, locking the door behind her. She dropped the duffel bag at the top of the stairs before placing the food containers in the kitchen. When she turned to greet me, I wrapped her in my arms, my mouth landing on hers before she could say a word. She instantly wrapped her arms around me, kissing me back, pressing her body against mine. When her hand slipped down and started rubbing my groin, I spun her around, pressing her up against the counter. I grabbed onto her leggings, pulling them and her thong down in one quick motion. After helping her get her feet free of them, I kneeled next to her pussy, spreading her legs to give me access. I licked the outside of her pussy, confirming that she was already wet before standing up behind her. I pulled my shorts and underwear down, lined myself up with her entrance, pushing her over on the counter a bit, and slide in, bottoming out when my balls hit her. I placed my hands on her hips, using them to pull her on and off me, as my hips bucked forward. Sliding in and out of her, watching her hold herself off the counter, I started to slam into her harder and faster with every thrust. As I got closer, I pulled out of her, spun Kayli around to face me, then pushed her down onto her knees. Grabbing the base of my cock, I placed my tip on Kayli’s lips, and she opened her mouth as I pushed myself into her. With her back against the cabinets, she didn’t have much room to bob her head, so I took over after a couple tries, instead thrusting my hips back and forth, causing my hard cock to slide in and out of Kayli’s mouth. With her beautiful eyes staring up at me, I quickly built back up and warned her, pushing myself deep into her throat as cum started to shoot out of my cock. When I was done, I pulled out of her mouth, and gave her a hand up, watching as she licked her lips clean.
“Hi,” she said, “I brought dinner for us.” I pulled up my shorts and replied back, “sorry, I think I gave you dessert first.”
Kayli laughed as she got herself dressed, saying, “that’s OK. Probably the best Hello I’ve ever gotten. You hungry now?” I told her I wasn’t quite hungry, so she put the food in the fridge and we went into my living room. We cuddled together on the couch, spending some time talking, but I was having a hard time keeping my hands off her body. If my hand wasn’t rubbing her back, it was caressing her breasts. If it wasn’t on her breasts, it was grazing pass her groin. Once away from her groin, it was squeezing her ass. “You know, when you licked me down there earlier, I was pretty close already,” Kayli said as I kept rubbing my hands over her body. Getting the hint, I started to move my body down hers, as she shifted to laying her back down on the couch. Once I was between her legs, I again pulled her leggings and thong down and off. I grabbed onto her right leg, kissing it from the ankle up to her inner thigh, leaving a little peck on her pussy. I grabbed her left leg, kissing it from her ankle to her inner thigh, this time ending with a lick from the bottom of her pussy to the top. I continued to lick it, using my tongue to pull her pussy lips to the side, softly flicking my tongue to her insides. Once I exposed her clit, I started to lick and suck around that and brought two of my fingers up, inserting them into her pussy. Glancing up at her face, she was watching my every move, her hands hovering above my head. I continued to lick, suck, and finger her until she finally placed her hands on my head, and started to grind herself on my face, covering it in her juices. When she released her grip on me, I finally sucked her clit into my mouth, making little circles around it with my tongue, my fingers making a “come here” motion on the inside of her pussy. She quickly had her hands back on my head, her legs trying to clinch close, but being blocked by my head. She was moaning out, only being interrupted to tell me when she was cumming. After the fourth orgasm, she grabbed my hair, using it to pull me off her. I released her clit from my mouth, still continuing to slowly finger her, as I moved up, kissing her lips, letting her taste herself on me. After one final orgasm brought on by my fingers, she pushed me off her, saying, “Jesus, I needed that.” I laughed, handing her leggings and thong back to her. She grabbed them, tossing her leggings to the side, but sliding her black thong on.
“I have a feeling those being on would just be a waste.” I agreed with her, and she got up to go warm up our dinner. “You know,” I said, “watching you walk around in a thong and a tank top, you’re going to make it awfully hard to concentrate on anything else tonight.” “Good,” she said, “I want your full attention on me. And wait until you see what outfit I have planned for tonight.” We ate our dinner at the kitchen table, our feet kicking each other under it, before moving back to the couch. I turned on some random movie, but Kayli had other ideas, her hand fishing my soft penis out of my shorts. She started to give it little kisses, watching as it grew at her every touch. When I was semi-hard, she was nice enough to pull my shorts and underwear off, turning her attention to my balls. I was sitting on the couch, and she was laying down, her head in my lap, giving her complete access to my groin. She started to kiss around my balls, softly sucking each of them into her mouth. While squeezing them with her left hand, she took my cock in her right hand, standing it up at attention. She stuck her tongue out, coming into contact with my base, and starting to lick her way up to my tip, finally causing me to be at my full hardness. She swirled her tongue around the tip, before softly sucking me into her mouth. As she begun to bob her head up and down, taking about half of me in each time, she gave my balls a final squeeze, then wrapped her hand around the base of my cock.
With both her hand and her mouth working on me, I had my head leaned up against the couch, my hand softly rubbing Kayli’s head. I grabbed a hold of Kayli’s phone, opened it up, and started to record a snapchat of her blowing me. I ended the snap, sending it off the Jennifer and Tara, who were out enjoying a night at the spa, telling them there was more to come. Kayli bobbed her head a few more times before she removed her mouth from me, laying her head down next to my cock, as her hand took over, rubbing my full length.
“What’s the most you’ve cummed in a single night? She asked me. I answered back, “three. What’s the most you’ve made a guy cum in a single night?” She thought about it before saying, “one guy? Twice. But, I once made two guys cum twice each in the same day.”
She watched the movie for a few seconds, her hand still jacking me off, edging me closer and closer. I wrapped my arm around her, squeezing her breasts on the outside of her tank top, and attempted to slide my hand down her tank top. She stopped me and said, “I’m surprised it taken you that long to touch them. They were starting to feel left out.” As she let go of my cock and pulled her tank top off, I said, “the nights still young. I was going to make sure they got plenty of attention.”
Kayli stripped her bra off and kneeled down on the ground in front of me. She grabbed onto my penis again, gave it a little peck on the top, then covered it with her massive breasts. She pushed her breasts together with her hands, using her hands to move them up and down, the tip of my cock attempting to poke up. When it did appear, she was quick to give it a lick. She released her breasts from around me when my cock started to twitch, and engulfed my entire member in her mouth, taking all of my nearly six inches inside her. When my cock hit the back of her throat, I filled her with my cum for the second time that night. She used her hand, this time, to pump out every last drop, causing me to fall back on the couch when she was done. She licked both her lips and her hand clean, as well as the tip of my cock, before standing up from the floor. She gave me a kiss on the forehead, before walking away. Kayli picked up her duffel bag, and said, “I’m going to go change. I’ll call you when you can come in to the bedroom. You better get that big boy ready for round three.’
I watched her walk away, her ass swaying in her thong, then tried to figure out how to get ready to go again. I found a wet wipe, and cleaned myself off. I tried to think of her naked, wondering what she had planned, I even looked at some of the pictures I had hidden of her on my phone. I knew that as soon as I saw her, was touching her body, and she was touching mine that I would be fine, but damn if I didn’t want to go walking in there with a hard on, just to impress her.
When Kayli finally told me that I could come into my room, I made my way over there, and entered into the room. Kayli was laying in the middle of my bed. She had on a pink, lacy, lingerie set. Her nipples were visibility hard under it, her pussy moist under the thing piece of fabric covering it. She had let her black hair out of its bun, it falling down almost to her waist, the red streaks visible around her face. She had placed a few toys next to her, mainly a dildo and a pair of handcuffs. She beckoned me forward but I shook my head no, instead pulling out my phone and taking a picture. I then joined her on the bed after I took my shirt off. I leaned over the top of her, bending down to kiss her lips. She wrapped her arms around me, pulling me down close to her. As we kissed, I laid my body on top of her, she spread her legs to welcome me in. Feeling her nearly naked body on mine, I knew I was correct, that it wouldn’t take long to work up again. I kissed all over her face before settling on her neck, bringing one of my hands up to squeeze her breasts through the sheer fabric of the night teddy. I kissed my way down to them, slowly peeling the fabric away, and quickly dove in, licking, pinching, and sucking on her nipples. I switched back and forth, make sure they both had the same amount of attention. I was starting to grow hard again and started to push my groin into hers.
Pushing myself off her, I pushed my shorts and underwear off with her help. She grabbed a hold of my cock, pulling and tugging it until it was fully hard. Kayli set up on the bed and I laid down to watch as she peeled the lingerie set off her body. When she was fully naked, she grabbed her breasts, squeezing them with her hands, then ran her fingers down to her pussy, lightly rubbing it as her other hand reached out for my cock. She gripped it in her hand, stroking me before she straddling me with her legs. Kayli reached down, pointing my member straight up in the air before sitting down, impaling herself on it. She placed her hands on both sides of my head, leaning down to kiss me as she started to rock her hips. I reached forward with my hands, grabbing onto Kayli’s massive breasts, squeezing them as I worked my way to her nipples. Still kissing, Kayli still rocking her hips back and forth, I took her nipples in my fingers, gently rubbing them, pinching them, twisting them lightly. We broke our kiss as Kayli pushed herself up higher. I was able to lift my head up a bit off the bed, taking her nipples in my mouth. After I sucked and licked them both, Kayli set straight up on me, and started to bounce on my cock. Throwing her head back, her breasts bouncing along with the rest of her body.
“Fuck. Fuck. Fuck yes. Oh God.” Kayli moaned out as she bounced on my cock, finally leaning down to kiss me again, shoving her tongue in my mouth as she moaned out that she was cumming. When her orgasm was done, she pushed herself back up, slowly rocking her hips back and forth. I looked up at her and asked, “so, what are the toys for?” She glanced over at the dildo and handcuffs and said, “you’re going to bend me over backwards, handcuff so I can’t resist, fuck me from behind, while shoving the dildo in my ass.”
As she climbed off me, I replied back, “Sounds like you’ve thought that one through.” She laughed and said, “it’s been a fantasy of mine. You don’t want to do it?” Instead of saying anything, I picked the handcuffs up from the bed, and pulled Kayli’s arms behind her back. I kissed her lips as I slipped the handcuffs over her wrists, shutting them with a click. I helped her gently lay down on the bed, her face on a pillow, kneeling down so her ass was in the air. She looked back at me and said, “I expect you to take full advantage of me now. This is your chance to do whatever you want to me.” I kneeled behind the real estate agent, picking up the dildo in my hand. It was slim, maybe five inches longer, with a purple head on it. I ran it down her butt crack, then slapped her cheeks with it, getting a small “oh!” from Kayli’s mouth.
I took the head of the dildo, and placed it on Kayli’s pussy lips. I pushed it into her pussy, pulling it back out, then pushing it back in. I begun fucking her with her dildo, spanking her ass with my free hand. I tried to time it every time I pulled the dildo out, I spanked her ass, causing Kayli to moan constantly. “Do you like me fucking you with your toy?” I asked her, getting a yes in response. “Don’t you wish you had the real thing in you?” She said yes again and I responded, “then beg for it. Tell me how much you want it.” She looked back at me and said, “please fuck me with your hard cock.” I spanked her, telling her to try again. “Please, I’m begging, I need your hard, thick cock inside me. Please.” I pulled her dildo out, tossing it on the bed, and kneeled down behind Kayli. I placed the tip of my cock on her entrance, telling her to beg again. She tried to push back with her hips, but I grabbed onto her trapped arms, not letting her move. “Fuck me. Fuck me with everything you go. Fuck me until I can’t move. I need you!” With that, I pushed all the way in, not giving Kayli any time to get used to my thickness, I started to pound into her, going harder and faster with every thrust.
I slowed down a bit to grab the dildo again. It was still wet from being inside Kayli, but I put it next to her mouth, telling her to open up. When she did, I shoved the dildo in, and pulled it out again, leaving it coated in her saliva. I lined the head of it up with the entrance to her butt, and as I pushed my cock into her pussy, I pushed the dildo into her ass. “Oh fuck, that feels amazing,” Kayli moaned as I held myself and the dildo in place. Keeping hold of the dildo with one hand, I started to thrust my hips back and forth again, pulling the dildo out and pushing it back in even time I pounded into her. I used my free hand to grab her phone, opening it up, and started recording a video. After recording the dildo going in and out of her ass, I pushed it in and let go of it, instant focusing on just pounding into her pussy, making sure to record Kayli’s face. Slowing down a bit, I found a spot on the bed that I could prop the phone up, and placed it there.
Grabbing onto Kayli’s handcuffed arms, I used to help me pull it on and off my cock, thrusting my hips as I did so. She was talking dirty to me, so i reached back with one hand and spanked her ass. When she told me to fuck her harder, I let go of her arms, grabbing onto her hips and using them for leverage to give her my full length. With a primal grunt and a loud moan, I orgasmed again, pushing deep into Kayli with everything I had. When I was done, I pulled out of her, leaving her to fall on the bed, and reached for the phone. I ended the recording with a shot of Kayli’s face, then sent it off to Tara and Jennifer.
I helped Kayli off the bed, uncuffing her as I did so. “Was that everything you hoped your fantasy would be?” I asked her to which she replied, “Even better.” We kissed again before we went into the bathroom to get cleaned up. She asked if she could take a quick shower so I went into the bedroom to wait for her. When she came back out, she had pulled her hair back into a messy bun, and was wearing her lingerie set again. As she climbed into my bed and cuddled next to me, we made out for a few minutes before falling asleep in each other’s arms.
When I woke up the next morning, the sun hadn’t risen up but I noticed that Kayli was no longer in bed with me. I found her sitting on my couch, fully dressed with her duffel bag sitting next to her. When she saw me, she said, “Good morning. I had every intention of waking of today and having sex with you one more time. But, the more I thought about last night, I kinda want that to be our memory of the final time. I knew that if I stayed in bed with you, I wouldn’t be able to resist, so I got dressed and came out here. Please don’t be mad at me. Also, this way, you’ll have more saved for Jennifer.” I sat down next to her and said, “I could never be mad at you. I understand and agree that last night was a perfect ending. I’m not going to lie, I was looking forward to it this morning, but I’m just happy to see you the morning after and know that I get to give you a proper goodbye.”
With that, we both stood up and hugged. The hug lingered for a few minutes before she ended it by kissing my cheek. Kayli left my house and I watched from the window as she got in her car and drove away. With it still being dark out, and knowing I had until the afternoon to wait for Jennifer, I decided to go back to sleep. It felt like no time had past at all when I heard a knocking at my door. Wondering if Kayli had told Jennifer she could come over earlier, I got up to answer it. Much to my surprise, Kayli was on the other side and quickly walked into the house, jumping onto me and shutting the door behind me. Her jump caused me to fall backwards on the stairs but her lips kissing me all over made up for the pain. In between kisses, she was saying, “I drove around for an hour trying to get you out of my mind. All I did was turn myself on. I need you one more time. Now!”
We made our way up the stairs, stripping each other naked as we walked to my room. Once there, she laid down on the side of the bed, and wrapped her legs around my body. I grabbed a hold of my cock, lined it up with her entrance, and pushed in, me still standing on the side of the bed. With her arms above her head, there was nothing to stop her breasts from bouncing as I thrust into her over and over. I reached out with my hands, cupping her breasts in them, squeezing them as I pounded into her. Letting go, I pulled out of her and went to climb up on the bed, but Kayli stopped me and pointed to the other side of the bed. She moves until her head was hanging off the side and opened up her mouth. I quickly ran to the other side, smacking Kayli in the face with my cock as I tried to get it in her mouth.
Kayli could already take me all the way down her throat with no problem, but having her like this felt even better. With my cock all the way down her throat, her head leaning over the bed, I reached forward to grab her breasts, pinching her nipples as I started to buck my hips back and forth. I watched as Kayli moved her hands to her shaved pussy, rubbing her clit with one hand and fingering herself with the other hand. I continued to slide my cock in and out of her mouth until I watched and felt her body tense up, and felt her moan on my cock as she had an orgasm.
I pulled out of her mouth with a pop and she scooted to the middle of the bed. I joined her, laying down in between her spread legs. I started to kiss her neck as I felt her reach down, grabbing my member and pulling me into her. I kissed down to her breasts, taking her nipples into my mouth as I slowly started to thrust in and out of her. After licking both of her nipple I laid down fully on top of her, pressing her chest into mine, wrapped my arms around me as she wrapped her legs around me, and started to really pound into her. Every thrust I was going harder and faster until I felt myself building up. I released my grip on her, pushed myself up, and moan as I pushed deep inside her, my cock twitching as cum begun to shoot out of it. I kept slowly pumping in and out, feeling her pussy clinching around my cock as she orgasmed again.
I pulled out of her, rolling off her as I did. When I caught my breath, I said, “I’m glad you came back.” “Me too,” Kayli said, rolling over into my arms. “That was worth it. Feeling you down my throat like that was even better then the way Jennifer described it.” I replied back, “that was unexpected, but I’m glad we did it.”
We laid in silence for a few minutes until Kayli asked me. “Do you regret any of this?” I replied back no, and asked if she did. “No, and I’ll never forget it. Hopefully you sell this house again in a few years so we can work together again. Is there anything you wish we had done that we didn’t?”
I thought for a moment before saying, “nope. Just more times but, like you, I’ll never forget any of this.”
We got off the bed together, going off to find our clothes. We kept stealing each other’s clothes, trying to kiss each other as we did get dressed. I picked up her thong, pretending to pocket it before handing it to her. Instead of putting it on, she stuffed it into her pocket. We made again, sharing a passionate kiss before she left again, this time waving to me as she drove away.
Source: reddit.com/r/eroticliterature/comments/wl81g7/my_favorite_realtor_part_13_m33f28_penetration