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Business Trip Fling - Part 2

2022-06-03 00:00:03

This is a continuation of my story. You don't need to read part 1 first, it just puts the events into perspective.

Since the next day was Friday, the plan sounded good to me. I’m not sure why but I realized that after last night I was on a mission to get Lisa pregnant. It was something primal. I had to do it because I knew I shouldn’t. My wife and I were trying for another baby as well and I knew that she would be ready for some hard loving when I got home. I also knew that subconsciously, Lisa wanted it too. This very hot woman talked me out of wearing a condom and let me cum inside her pussy and down her throat. From the looks of it, we would be hitting it like that for the next week until I returned home next Saturday. The odds of accomplishing my mission were pretty solid.

I arrived at Lisa’s house around 7 on Friday and she greeted me wearing jeans shorts and a tee-shirt with no bra. She was barefoot and I could tell she had just had a pedicure. Her ass looked so good in those tight shorts and I thought about sucking on those toes if I got a chance. Lisa kissed me and said it would be great if we could go out – maybe dinner and a few drinks. “I’m going to jump in the shower to freshen up a bit before we go. Do you want to join me?” Lisa smiled at me and turned to head to the bathroom. I watched her sweet ass as she walked away and I was right behind her. We got to the bathroom and we kissed and stripped off our clothes. Lisa looked so good naked as she leaned into the shower to turn on the water.

As she finished, I came up behind her and rubbed my quickly stiffening cock into her ass crack and squeezed her fantastic milk-filled breasts. “They are refilled and ready for you, whenever you are.” Lisa moaned as she turned around. “Is this refilled and ready for me?” she said as she gently stroked my cock. “Absolutely,” I said as I began sucking on her breast. Immediately, warm milk gushed into my mouth. I filled my mouth with milk from each breast and then Lisa dropped to her knees. She took my cock in her mouth and bobbed furiously for about 30 seconds. I pulled her up and kissed her and then we got into the shower.

The feeling of her naked body rubbing against mine in the hot water was incredible. We kissed as she stroked my cock and then she turned me around so that she was behind me. She soaped up my back and then my ass paying special attention to my ass hole. She eased her finger into my ass with her left hand while stroking my soapy cock with her right. “What do you think about that, baby?” Lisa asked. “That is fucking awesome.” I replied. “I was hoping you would say that. Maybe we can try that out a little more later.” Now it was my turn soap up Lisa. I lathered up her entire body and then slid my soapy cock between her sweet ass cheeks. Lisa pulled her ass cheeks apart as I continued to slide my cock between them. Suddenly she pressed back as my cock was near her asshole and the head just teased her anus. It didn’t penetrate but I could feel her anus part slightly. I knew she was up for some ass play and I took the shower head and rinsed her ass thoroughly. I bent Lisa forward at the waist and dropped to my knees behind her. With the water running down her ass, I spread her ass cheeks and rammed my tongue as far into her ass as far as it would go. “Oh my God!” Lisa gasped as I continued to tongue fuck her ass. I pushed 3 fingers into her pussy and finger fucked her as I ate her ass. Lisa soon came and I could feel it as her ass spasmed on my tongue.

Lisa was still bent over and leaning on the wall so as I stood up I rammed my rock hard boner into her wet pussy. I grabbed her hips and fucked her hard for about two minutes until I came deep inside her. It was another powerful orgasm and yet another full blast of my seed into her fertile pussy. As I pulled my cock from Lisa’s pussy, she turned off the water. We dried off and went to her bed and got under the covers. Lisa was on her side and I snuggled up right behind her. She gently pushed her ass against me and I squeezed her tit making a little milk spray out. “You know I went more than a year without having sex and since I met you, it’s been almost non-stop” Lisa said. “I put that ad on Craig’s List thinking I would get some and make a little money too. I never dreamed we would be going at it like teenagers.” Lisa kissed my hand and continued “I really like this...I’ve never been with a man who took the time to make sure I came while we were having sex. Just so you know, I’m not on the pill or anything. I was pregnant and then when my son was born 6 months ago, I was pretty sure I wouldn’t meet anyone.” She kissed me again and her tongue slid softly into my mouth. “Are you OK with that?” I shook my head yes and kissed Lisa then she continued “I made an appointment to see the doctor next week to get on the pill. Of course, that won’t do anything for us now.” Lisa rolled over and put her arms around me. “I think we’ll be OK...they say you can’t get pregnant while you’re breastfeeding.” I clamped my mouth onto her nipple and began sucking her warm milk into my mouth. I stopped for a moment and looked into her eyes and said “I hope they’re wrong.” Lisa kissed me and whispered “Me too.”

We laid there quietly looking into each other’s eyes and kissing. I felt my cock beginning to grow again as I kissed this beautiful woman. We got dressed and went out and had a nice dinner and afterward went to a bar for a few drinks. We came back to Lisa’s house and watched TV in the living room just holding hands. Lisa got up and changed into a skimpy pair of pajamas and motioned to me from her room. “Why don’t we watch TV in the bedroom?” I stripped off my clothes and got into bed with Lisa. “Are you up for something different? Lisa said with a little smile as she stroked my cock. I nodded my head and she took out a tube of lube from the nightstand and began to lube up my ass. Then she pulled the covers back and moved down to the end of the bed as she started sucking my cock. Soon she was working a finger into my ass as she blew me. “What do think?” she asked. “Keep going, baby” I replied. Soon she had two fingers in my ass and I could feel an intense but awesome pressure from inside. Lisa was massaging my prostate. I had heard about this but never experienced it. Soon she was hitting just the right spot while she continued to suck my cock. I felt the most intense orgasm building inside me and Lisa knew I was getting close. She increased the pace with her mouth and pushed hard on my prostate. In a wave of pure ecstasy, I exploded in Lisa’s mouth with a force that startled her. She quickly recovered and swallowed every drop before taking her mouth off of my cock.

Lisa moved back up to lay next to me in bed and said “I never had so much cum in my mouth. That was awesome. I just wish it was inside me.” I worked a finger into her pussy as we began to kiss. “I think after a good night’s sleep, I can certainly take care of that.” We fell asleep holding each other. When I awoke early in the morning, I felt Lisa’s warm mouth gently sucking my cock. I moved my hands down and gently held the back of her head as I thrust my hips upward. What a beautiful sight as my cock disappeared into Lisa’s mouth. I pulled her up and rolled her onto her side and I moved right behind her into the spoon position. There was no foreplay this morning as she began grinding her ass back onto my cock. I reached down and moved her panties to the side and spread her cheeks and pulled my cock out of my boxers and pushed it deep inside her. Her pussy was still very wet with my cum from last night. I began slowing working my cock in and out of her and Lisa began to moan softly.

“You know I had your cum inside me all night” Lisa whispered as I continued to fuck her. “That felt so good. I want you to cum inside me. I need to feel you cumming inside me again.” I lifted Lisa’s ass cheek a bit so I could get deeper insider her and I really started fucking her. I was slapping against her ass and I could smell her cum filled pussy. “Oh God baby, please cum inside me” Lisa said as she pushed her ass back into me. The sound of Lisa begging me to fill her pussy had me on the edge and with a loud grunt I emptied my balls inside of her. As I pumped my seed into her she moaned “Oh God I can feel it. Don’t stop!” I continued sliding my cock in and out of her for another minute or so before I stopped and just held her. Lisa slipped her hand down and started working her clit. After a few minutes she reached orgasm and I could feel her pussy pulsating - squeezing my cock and pulling my seed deeper inside her. My cock stayed semi-erect was still inside her as we fell back to sleep. We slept for a few more hours and woke up around 10AM. I kissed her and got out of bed to take a shower. Lisa headed to the kitchen to make breakfast. After my shower, I walked to the kitchen and watched her from the doorway for several moments before she noticed me. She looked so good in her pajamas, barefoot and cooking me breakfast with millions of my potent sperm swimming inside her fertile pussy.

During breakfast, Lisa rested her beautiful, soft bare feet on mine as we talked about our plans for the day. When we finished eating, I reached down and pulled one of her feet up into my lap and started to rub and massage it. I could tell Lisa really liked it because stopped talking and put her other foot in my lap. I spent about 20 minutes massaging every part of her sexy feet. I know I really liked it because my cock was pitching a tent in my boxers. I couldn’t take it any more and I pulled my cock out through the fly of my boxers and placed it between Lisa’s feet. I squeezed her feet on my cock and began to stroke my cock between them. I started to moan as I got closer to orgasm and Lisa quickly got up and took off her panties and straddled me lowering her pussy onto my cock. I couldn’t last long and within a minute, I came inside her. Lisa kissed me gently and I could feel cum running out of her pussy and onto my balls. We kissed for several minutes until Lisa finally stood up and my cock slid out of her. She stroked my cock with her hand and said “ummmmm...now that’s the way to start the morning.” We shared one last kiss and she headed to the bathroom. Lisa took a shower and got dressed and we spent the day doing some errands and ended up at a diner around 7PM for dinner. During dinner, Lisa asked if I would be up for something a little different. I thought to myself that this would probably be pretty hot and readily agreed.

We arrived back at her place around 8:30 and I noticed a car in her driveway. “I asked my friend Trina to come over and hang out this evening. I told her all about our last few days and she really wanted to meet you. She broke up with her boyfriend a few months ago. Is that OK?” Once again my luck was awesome and I quickly agreed and we headed inside. Trina was in the living room and was fairly attractive and every bit as pretty as Lisa. She was a little heavier and had very large breasts. She was wearing an oversized men’s t-shirt and probably nothing underneath. When she saw Lisa, she got up and walked across the room and gave her a big hug and a deep kiss. I could see their tongues in each other’s mouths and I realized they were more than friends. “Trina and I became close a few months ago when her boyfriend left.” Trina came over to me and gave me a big hug as well “Hi Paul, I’m so glad to meet you.” I could feel her fantastic tits on my chest as she squeezed me tight and she gave me a quick kiss and then another that lasted a few seconds longer.

When the second kiss ended, we looked into each other’s eyes and I kissed her one more time and pushed my tongue into her mouth. Trina’s mouth opened and our tongues wrapped together as my hands explored her plentiful ass. She wasn’t wearing any panties and I knew this was going to be a night to remember. I slipped my hands under her shirt and put the fingers of my right hand into the crack of her ass moving them up and down teasing her pussy and ass. “I was hoping you would be up for some fun tonight” Trina said. Just then I spun Trina around and bent her forward at the waist so she was leaning on the dining room table. I went to my knees, spread her ass cheeks and thrust my tongue into Trina’s ass. I pushed it in as far as it would go and then back out as I fucked her sweet puckered asshole with my tongue. “Ohhhhhhhhh My Goddddddddd!!” Trina kept moaning as I worked her ass. I love eating a sweet ass and I was really getting into it. Trina was pushing two of her fingers into her pussy and working her clit too. I worshipped her ass for about ten minutes. Her moaning got louder and she reached back and pulled my face into her ass as she came. I could feel her orgasm as her asshole spasmed while I continued to lick her ass.

I stood up and went over to the couch where Lisa was sitting naked and working her clit. “That was the hottest thing I’ve ever seen” Lisa said as she reached up to unbutton my pants. I pulled off my shirt as she got my pants off and pulled me to the couch so I was sitting next to her. Lisa stroked my cock slowly and kissed me while Trina sat down on the other side so I was between them. Trina started squeezing my balls while Lisa continued stroking my cock. I went back to kissing Lisa and Trina moved from the couch and down onto her knees in front of me. Trina’s mouth replaced Lisa’s hand and she began to suck my cock like a woman possessed. I thought Lisa gave great head but Trina was even better. Trina’s tongue wrapped around the underside of my cock as her head bobbed up and down and the feeling of a new mouth on my cock was awesome. Her eyes locked onto mine as she sucked my cock and that almost made me pop in her mouth.

I pulled her mouth off of my cock and had Trina lay on her back on the floor. Her pussy was glistening with juices and her lips were wide open. Trina squeezed her tits and pulled at her nipples and they were rock hard. I climbed on top of her and slid my raw cock into her wet pussy. Trina wrapped her legs around my waist as I began to fuck her harder. Her pussy was so hot and wet. I reached down and worked my index finger into her ass using the juice that leaked from her pussy as lube. I could feel my cock sliding in and out of her pussy with the finger that was in her ass. “Oh God Trina, I’m going to cum soon.” I moaned. “Ohhhhhhh me too but not inside me baby, I’m not on the pill or anything” Trina whispered in reply. Just then I felt Trina’s pussy grip my cock as she came and I just lost control. As her orgasm finished, mine began as my whole body shuddered as my seed was pumped deep inside yet another very fertile pussy. As the last of my sperm left my cock to begin swimming inside her, Trina looked at me and said “It’s been a long time since a man came inside me. I felt it get hot and wet inside me when you came. I love the way it felt when you came inside me. I guess it’s OK to take a chance once in a while.” My cock was still inside Trina as she spoke and I thought to myself how hot both Trina and Lisa would look pregnant with my babies. I slid my cock out of Trina and lay next to her on the floor. I could see my cum in her pussy as she began to finger herself. I sucked gently on one of her magnificent tits and Lisa moved down to the floor on all fours between Trina’s legs.

Lisa spread Trina’s pussy lips with her fingers and began to lick her pussy from asshole to clit. Trina pulled her legs back with her hands to give Lisa better access. Lisa pushed her tongue into Trina’s pussy and licked my cum from her. From my position I could see my cum leak from Trina’s pussy and onto Lisa’s tongue. I got up and sat on the couch to get a better view and just then Lisa stood up as well and came over to me and started kissing me. She still had some of my cum in her mouth and she pushed it into mine. I had never been snowballed before and it caught me by surprise. I swallowed it and went back to kissing Lisa for a few moments before she broke our kiss and went back to Trina. Lisa climbed on top of Trina in a 69 and they both attacked each other’s pussy with their tongues. It was obvious that they had done this before and I just sat back and watched while they went to town on each other. After about five minutes or so I felt my cock begin to twitch and I knew I would be ready to join in soon.

I slipped off the couch and got on all fours behind Lisa so that my face was right in her ass. I spread her ass cheeks and pushed my tongue deep into her ass and she lapped my cum from Trina’s pussy. Trina was really working Lisa’s pussy while I licked and tongue fucked her ass at the same time. By now my cock was rock hard and ready so I slid my cock into Lisa’s wet pussy while Trina licked her clit. Lisa must have really enjoyed the way Trina was eating her out because her pussy was soaking wet and sloppy. I slid right in all the way and I began fucking her nice and slow. My nuts were right in Trina’s face as she continued to eat Lisa’s pussy and soon they were in her mouth as I continued to fuck Lisa. I stopped thrusting so that Trina could work my balls and the feeling was intense. My cock was buried in Lisa’s wet pussy and Trina had both of my balls in her mouth. When Trina sucked hard on my balls I almost lost it and came inside Lisa right there.

I pulled my cock out of Lisa’s pussy so I could compose myself and then pushed it downward and into Trina’s waiting mouth. Trina went to work on my cock and with her warm and wet mouth and after about a minute I pulled out from her and rammed my cock back into Lisa. I went back and forth between mouth and pussy for a few minutes before I had to stop. “Get the lube out of the drawer” Lisa growled as she looked back at me. I found the tube of ID Glide and got back behind Lisa and rammed my tongue back in her ass a few more times. “Oh God babe, put two fingers in my ass NOW!” Lisa grunted at me. I quickly lubed up my fingers and pushed them slowly into her ass. What an awesome feeling, her ass was so hot and tight. It took a bit of pushing for me to get my fingers all the way in. Once I had worked them in, I started finger fucking her ass while Trina kept licking Lisa’s clit. Trina had a perfect view and started moaning as I got into it. Lisa then looked back at me and said “I need your cock up my ass.” I pulled my fingers out and lubed up my cock and squirted some lube onto her asshole. I pushed the head of my cock into her ass and she groaned “Oh God baby, fuck my ass!” I felt the head of my cock penetrate past the sphincter and I was able to push it about half way in. I pulled it out just a little and pushed hard one more time and it went all the way into her ass.

Lisa’s ass was just fucking amazing – so hot and so tight. She flexed her ass muscles while my cock was inside her and it was like she was trying to milk my cock. I started stroking in and out of her ass but it was so tight I couldn’t go very fast. When I pulled all the way out, I squirted some more lube on my cock and in her gaping asshole and pushed back into her. Trina was moaning as she watched me ass fucking Lisa so after a few minutes I pulled my cock out of Lisa’s ass and into Trina’s mouth. I didn’t know if she would go for it but she didn’t hesitate and opened her mouth wide and my cock slipped right in. She began sucking and licking my cock that just moments before was buried deep in Lisa’s rectum. Trina’s mouth felt great and I was getting very close to cumming but I knew I wanted to cum in Lisa’s ass so I pulled out of Trina’s mouth and pushed back into Lisa. Trina went back to work on Lisa’s clit and within a minute Lisa came and her ass grabbed my cock as she had her orgasm. I couldn’t hold out any more and pushed deep into Lisa’s ass and pumped all of my cum inside her. I didn’t think I would stop cumming as this was one of the most intense orgasms I ever had. When I finally finished, I kept pumping slowing in and out of Lisa’s ass enjoying the sounds of my cock in her sloppy cum-filled ass. “I want to taste it!” Trina said as I pulled out of Lisa’s ass. Trina’s mouth replaced my cock as she went to work cleaning my spunk out of Lisa’s ass. I moved to the couch – I was spent and needed a break – but I still wanted to watch. The hottest part was when Lisa flexed her ass and pushed a good amount of cum out of her ass and into Trina’s waiting mouth just below.

When Trina and Lisa were finished, they moved to the couch next to me, one on each side and we just collapsed for a few minutes holding each other. “Let’s take a shower and go to bed” said Lisa and we all walked to the bathroom. We all soaped each other up and enjoyed the hot water. At one point Trina was behind me stroking my cock while Lisa and I were kissing. It was awesome. We got out and dried off and got into bed naked. Lisa was in the middle and both Trina and I gently sucked on her milk-filled breasts. I love the taste of her milk and after a few minutes Trina and I had drained her breasts. We all fell into a deep sleep and I did not wake up until around 8AM the next morning.

When I woke up in the morning, only Trina and I were in bed. She snuggled up next to me and we were facing each other and hugging and gently kissing each other. “I have to go soon baby” she said as she slowly rubbed my cock and we continued kissing. I pushed her onto her back and rolled on top of her. “You need a refill for the road before you go” I said as my cock rubbed on her wet pussy. “Oh yeah?” she whispered “than sounds good but you need to pull out this time. I’m pretty sure I’m ovulating today or tomorrow.” I pushed my cock into her wet and fertile pussy and said “I’ll do my best...but a little might leak inside you.” Trina just looked into my eyes and moaned as we began to kiss passionately. She wrapped her legs and arms around me and I began to pump faster and harder. We stopped kissing for a moment and I said “I’m going to cum soon. I really want to finish deep inside you.” Trina kissed me and shook her head no and moaned as I kept fucking her. I was on the edge and about to cum. Trina sensed it and shouted “Oh God baby, shoot it inside me!” That was all I needed to hear and I exploded into her waiting snatch. I kept my cock inside her and she kissed me and said “That felt awesome...but I wish you hadn’t done that. You may a daddy in about 9 months.” I slid my cock out and lay next to Trina. She reached over and put two pillows under her hips and I said “I was picturing what our baby would look like the whole time I was fucking you.” Trina started working her clit and whispered “Me too.”

After a few minutes Trina got up and got dressed and kissed me before she left. Lisa came in and said that her Mom would be able to watch her son for another day so that we could spend Sunday together. We went to lunch and then to a movie and then went to have a few drinks at a local bar. It was really nice just spending time together like that. We arrived back at her house around 10PM and we were both very tired. Lisa put her arms around me and said “I want to sleep holding you in my arms.” I thought that sounded great and we went to bed. It was great just holding her and soon we were both fast asleep. I woke up early on Monday and had to get to work so I kissed Lisa and headed back to my hotel to get cleaned up and into my work clothes. The workday went by quickly and I called Lisa at lunch and left a message on her cell phone. Lisa called me around 7PM and told me that her son was sick and that she was going to be home with him tonight. We chatted for a while longer and then hung up. I didn’t think anything of it and just spent the evening watching TV and went to bed early.