Business Trip Fling – Part 1

I had to go out of town for two weeks to San Antonio and I wasn’t looking forward to it. I knew it would be two long weeks of no sex. I arrived on a Sunday night and was feeling a little down and decided to check out Craig’s List to see if I could arrange for some company. I had heard there were listings for prostitutes on there and I was curious. I didn’t want to pay for sex; I just wanted to see what was out there in case I needed some later. I didn’t see anything that appealed to me so after about an hour I just gave up and went to bed. A few days later, I tried again and was fascinated by one of the postings. The lady on there said she was a single mom who needed some help with her rent. She didn’t have a picture posted so I was hesitant but I called her anyway.

Her name was Lisa and we talked on the phone for about 20 minutes and she seemed pretty cool. She agreed to come to my hotel room the next day around 9PM – she had a sitter for her son. The next day I thought about cancelling but my hard cock talked me out of it. Right at 9 there was a knock on the door. I opened it and Lisa walked in. She was fairly good looking…dark hair, late twenties, big boobs and nice legs and ass. I offered her a beer and she thanked me and finished it quickly. I gave her another one and soon after that she relaxed and became more talkative. We talked for about half an hour and got along very well. During a lull in the conversation, I gestured toward the envelope I had placed on the TV. She took it and placed it in her purse. Lisa apologized to me saying that she had never done this before and that I was the only person who responded to her ad. She also went on to tell me that her husband had left more than a year ago when she became pregnant with their first child and she had not been with a man since he left.

I stood up and took Lisa’s hands in mine and we began to kiss. Her mouth opened and our tongues danced together. We kissed for quite a while and the passion of the moment had me rock hard. Lisa slid her hand down to my cock and I heard her moan softly. We continued kissing while she undid my belt and unbuttoned my pants. She slid them down as she dropped to her knees. I looked down at her as she slowly stoked my cock while she stared at it. Then she licked the tip of my cock and took the head into her mouth. She was tentative at first but after a slow start, she really got into it. Her head was bobbing furiously on my cock as her hand stroked my cock. Soon she removed her hand took more of my cock into her mouth. I grabbed the back of her head and started riding my cock into her mouth. Lisa started sucking my cock faster as I ran my fingers through her hair.

After a few minutes of furious sucking, Lisa stopped to catch her breath. Then she moved down and took my balls into her mouth and began sucking on them and I could feel her tongue as it massaged my balls. It was the most awesome feeling and I knew I was close to cumming. She stopped licking my balls and immediately started stroking my cock with her hand as she looked up at me. I pulled her up to a standing position and we began kissing passionately. She was so damn hot; I couldn’t believe my luck. I told Lisa it was my turn my take care of her and she quickly stripped out of her clothes and lay back on the bed. I got rid of my clothes as well and planted my face in her pussy. I spread her lips and thrust my tongue into her pussy as far as it would go. Lisa was very wet and I loved the taste of her juices. I began licking her from the top of her pussy to the bottom lapping up as much pussy juice as possible. Then I concentrated on her clit and she began to moan and grab my head. I worked a finger into her pussy and began to rub her g-spot while still working her clit with my tongue. She grabbed my head even harder and then she had her first orgasm.

I felt every moment of it with the finger that was deep in her pussy and was rewarded with a warm rush of pussy juice that flowed into my mouth. I knew her pussy would be sensitive for a while so I moved up to lay beside her on the bed. “That was awesome” she said as she put her arms around me. “Now fuck me!” Lisa rolled onto her back and took me with her. Now I was on top of her and between her legs with my raging boner resting on her hot and soaking wet pussy. Lisa reached her hand down and grabbed my cock and ran the head up and down sliding my cock between her pussy lips. I pulled away from her for a moment and rolled a condom onto my cock and thrust into her wet pussy and she wrapped her legs around my waist. I began slamming my cock into her pussy and I could feel the back of her pussy with each deep stroke. I hate condoms and I definitely didn’t want to wear one. It took every bit of willpower for me to pull my cock away from her pussy and put on a condom. Lisa’s pussy felt so good – I could only imagine how good it would feel if I was bareback inside her. Lisa wrapped her legs even more tightly around my waist and we began kissing passionately. Soon she was kissing my neck and working her tongue into my ear. Then she whispered “Don’t stop…I haven’t been fucked in almost a year and a half….Oh God baby, please don’t stop….Just fuck me!” I picked up my pace and my cock was slamming into Lisa – I could feel my balls slapping her ass on each thrust.

I looked into her eyes and she looked so hot on her back taking my cock deep inside her. Lisa looked up at me and said “Cum for me baby!…Fuck me!” Before the words had faded I exploded inside Lisa. I could feel my cum as I filled the condom in her wet pussy. I came harder then I had ever cum before and Lisa and I began kissing again and I kept working my still hard cock into soaking wet pussy. After a few minutes, I slid my cock out and rolled onto my back. Lisa lay with her head on my chest and we kissed softly. Lisa reached down and pulled the condom off of my cock and rolled onto her back. She then squeezed the condom and drained my cum onto her breasts and stomach. She took two fingers from her right hand coating them in cum and began to work her clit with her cum covered fingers. She did this three more times and on the last time, her fingers went into her pussy instead taking my cum with it.

Then Lisa moved down and she took my semi-hard cock into her mouth moving her head up and down greedily licking the cum that remained on my cock. Soon I was rock hard again and Lisa got up into the doggy position. I got behind her and rubbed my cock into the crack of her ass. Lisa had a fantastic ass and I knew I would have to fuck it soon. Lisa changed position slightly and the head of my cock slipped into her wet and wide open pussy. She pushed back and my cock went in about half way before I pulled it out. I quickly rolled another condom on and rammed my cock back into her pussy and began slamming into her. I fucked her like that for at least 10 minutes. I loved the sight of my cock working in and out of Lisa’s hot pussy and the way my hips slapped up against her ass. I could feel another huge orgasm building inside me. Lisa reached her hand back between her legs and squeezed my balls. Just then, I felt Lisa’s pussy spasm as it squeezed my cock as she came. “Oh Godddddddddddd” Lisa moaned as her orgasm continued. That pushed me over the edge and I filled another condom in her pussy.

We both lay back on the bed and looked into each other’s eyes. I couldn’t believe what had just happened…how damn hot it just was. Lisa pulled me close and put her leg over mine and her arms around me. “That was the first time I ever had an orgasm from sex…you were awesome.” Lisa whispered. “I’m staying in San Antonio for another week. Will I be able to see you again?” Lisa looked at me and said “How about every night?” “That sounds good to me” I replied. Lisa got up out of bed and got dressed. We shared one final kiss and she headed home.

The next day, Lisa called me and I agreed to go to her house at around 9PM when her son would be asleep. Lisa greeted me at the door and wrapped her arms around me and we kissed. Her tongue was in my mouth and her hands were all over my body – it was if she was possessed by lust. Once again I was amazed by my luck because not only did I hook up with a hot chick but she is incredibly horny and I didn’t even know her last name.

Lisa was wearing only a silk night shirt that barely covered her ass and she looked just awesome. As we kissed by the door I couldn’t keep my hands off of her ass and it was then that I realized she wasn’t wearing any panties. We sat on the couch and continued kissing like love struck teenagers. My hand went into her silk nightshirt and I began to fondle her awesome breasts. I didn’t get a chance to enjoy them the night before so now was my chance. Her nipples were fully erect and stuck straight out and I started to suck on the right one. Lisa began to moan softly and I was really getting into it when I felt a gush of milk in my mouth. Lisa said “I’m sorry babe…I’m breastfeeding my baby. I hope you don’t mind. I should have said something.” I couldn’t believe how hot it was to suck milk from her tits and I didn’t even budge. I sucked her right tit dry and moved to her left and did the same thing. Her milk was warm and sweet and I slid a finger into her pussy as I continued to suck on her left breast. Her pussy was soaking wet; she was obviously as turned on as I was. When her left breast was empty, I sat back and said “That was so hot. You taste so awesome.”

Lisa was stroking my cock through my jeans and looked into my eyes and replied “I bet you do too. It’s my turn to find out.” With that, I quickly took down my pants and underwear and Lisa began stoking my raw cock with her bare hand. She continued kissing me as she stroked my cock and it felt so good. Soon a good amount of pre-cum leaked from the head of my cock and Lisa moved down to her knees on the floor in front of me on the couch. She grabbed my cock with her hand and gently licked all of the pre-cum from the tip and swallowed it. Then she licked the bottom of my cock from the head down to my nuts. She did this a few times and then slid the head into her mouth and began to swirl her tongue around it. I grabbed the back of her head and rammed my cock in as far as it would go. I then held her head firmly in my hands and began to fuck her face. Lisa pulled her mouth off of my cock and moved down and took my balls into her mouth. She sucked hard on them and I could feel her mouth squeezing them and she stroked my cock with her hand. I was getting close because she was giving me the best blowjob I had ever had.

I stood up and she stayed on her knees and the angle was perfect for my cock to go down her throat. I held her head and pushed my cock in and felt the back of her throat. She gagged a bit but I kept going and then it went further and down her throat. It was the most amazing feeling. I pulled my cock from her throat so she could breathe and then pushed it back down in. We repeated this a few more times until I was on the verge of exploding. “I’m going to cum…Oh God, Lisa, here it comes!” With those words I rocketed five huge squirts of jism into her warm and waiting mouth. She moaned as I drained my seed into her mouth. I pulled my spent cock from her mouth and she looked up at me and I could see her swallow and lick her lips. She stood up and straddled me, sitting her bare ass on my lap. I could feel her wet pussy on my cock and we began to kiss. The taste of my own cum in her mouth turned me on a lot more than I would have ever thought and I felt my cock stirring back to life.

We kissed for quite a while and then she moved onto the couch next to me and we turned the TV on for a bit of a breather. I still had my pants off and Lisa stroked my cock slowly. We began to kiss again, much more passionately this time. I thought to myself that based on my experience last night that Lisa would be up for trying a little bare back. I really wanted to but my cautious side was in control and I put those thoughts out of my mind. My cock was rock hard and Lisa read my mind. She laid on her back on the floor with her legs spread and her wet pussy ready to be pounded. I climbed on top of her and ground my cock onto her pussy but was very careful not to penetrate her. Lisa began to moan and move her hips and the head of my cock slipped in for a moment but I pulled out of her quickly. I put a condom on and slid my cock back into her fertile snatch. Last night was about lust; tonight was much slower and more loving. Lisa put her feet on the back on my legs and her arms around my neck.

We kissed and looked deeply into each other’s eyes. She looked so hot. I began kissing her neck and sucking on her ear and telling her how good she looked and how hot she was making me. I fucked her for about five minutes and then she whispered in my ear “Baby I want you to take off your condom. I need your raw cock inside of me.” My cock was definitely in control of the situation and there was no way I could refuse because it was exactly what I wanted to do. I pulled out of her and slid the condom off of my cock and rode my bare cock back inside her. Her pussy was so hot and wet…I couldn’t believe I was barebacking her. I didn’t know if she was on the pill or not but I assumed she wasn’t because she didn’t say anything about it. She had me really revved up and I know I was close to cumming so I stopped and pulled my cock out so that lust the tip of the head was still inside her. At that same moment, I felt a large gush of precum pump out of my cock and into Lisa. It was too late to do anything about it so I just rammed my cock back into her and kept fucking her raw pussy. The precum made her pussy even wetter than before and the feeling was awesome. I picked up my pace and Lisa started moaning “Don’t stop….Don’t stop” and I knew I was ready to explode inside her. Just then Lisa wrapped her arms around my neck and pulled my face to her and pushed her tongue into my mouth. I felt myself cumming and broke the kiss and pulled my cock out of her pussy and exploded onto her chest. The first blast landed on her tits and the second and third on her stomach and the last squirt of cum went into her belly button. I don’t know why but I slid my cum soaked cock back into her pussy and we began kissing passionately as I continued to fuck her. I felt my cock softening and I pulled my cock out of her. I rolled onto my side and Lisa did so as well so that she was facing me. “I really liked that. My pussy is really wet – thanks to you.” I kissed Lisa gently and asked her “Is it OK if I cum inside you? Are you on the pill?” Lisa rolled me onto my back and climbed on top of me and began kissing me again. Then she said “Yes to the first question and you’ll have to find out about the second.”

Lisa’s wet pussy on my cock and her teasing got my cock rock hard again. Lisa began rocking her hips back and forth and grinding her pussy onto my cock. Lisa lifted her hips and reached her hand back and worked the head of my cock into her pussy. Then she slammed down onto my cock burying it deep into her pussy. She began bouncing up and down on my cock and I could feel her cervix with the head of my cock every time she came down on me. Knowing she was probably unprotected pushed me close the edge. I knew I was going to cum inside her so I rolled her onto her back so I could look into her eyes. I pushed my cock in as far as it would go and felt her cervix once again. I continued this for a few more seconds before I erupted inside. I didn’t move my cock until the last squirt shot out of my cock. I left my cock inside Lisa for another minute and pulled it out slowly so only a little would leak out. We laid there on the floor – Lisa was still on her back and I was on my side with my head on her chest. I listened to her breathing and her heart beating thinking about my seed swimming inside her. I began to flick her nipple with my tongue and sucked gently on it. I was rewarded with just a few drops of breast milk. My hand slid down to her pussy and I felt my cum inside her. I worked two fingers into her pussy and then moved them to her mouth. Lisa opened her mouth and licked my cum clean off of my fingers. “Can I see you tomorrow?” Lisa said. “What time do you want me to come by?” Lisa replied “I’ll have my mom watch the kids. Come over around 7 and plan on staying the night.”

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