Brianna
I travel alot for work and this last weekend I had to drive about 8 hours from my house. I got to town just before noon and decided to stop and grab some food. I stopped in at a little dive restaurant. I sat myself and was going through emails when my waitress walked up. She was super attractive, looked like a porn star no joke. She was in her late 20s, platinum blonde hair, quite a bit of makeup, very pretty, tight black leggings which cupped her nice ass and a work polo. She introduced herself as Brianna. She handed me a menu and smiled at me. I'm sure she could tell I was giving her the once over and she probably got it all the time. I put in my order and she smiled and walked away. She had a very nice walk and her sexy ass swayed as she did. Brianna brought my food out a short time later and said she would check back in a bit. I had just started to eat when she came back. I ended up striking up a conversation with her about things to do in the area. Brianna laughed and said she honestly didn't do much other than work and go home. I asked if she would want to grab dinner later with me. She asked if I was from around town and I told her I was just in town for a couple days. Brianna smiled at me said things were kind of complicated at the moment but said she appreciated the offer. I was just finishing up my food when Brianna dropped off the bill. She had wrote thank you and then below that she was working tomorrow morning until noon. I left a $20 on the table and went up and paid my bill. I didn't see Brianna before I left but decided I would swing in for lunch tomorrow again. I woke up early in the morning and did some work on the computer from the hotel. It was around 11 when I headed to the diner and walked in. I didn't see Brianna but I went and sat at the same table. Brianna walked up with a big smile on her face and said hi again stranger. She told me she never got my name and I introduced myself to her. She handed me a menu and said she would be back. She had on black leggings again and her work polo. Brianna came back a short time later and grabbed my order. She stood there for a moment and asked if that offer was still available for dinner. I told her yes it was. She smiled and asked for my number and would text me after she was done. I gave her my number and she walked away with a smile. She brought my food out a short time later and let me know she was leaving. I asked if she wanted to join me and she said she needed to get home. I was just leaving when I got a text from her. She asked if she could call me in a bit and we could talk, I said sure. Brianna called me a short time later. She told me she wanted to talk about somethings before we met. She told me that she was currently married but her husband was in prison for drugs. She told me she had 2 kids at home and that's why she never went out. She told me she would like to go out to dinner with me but it would have to be just as friends. I agreed to that and she told me her mom was going to watch her kids and that she would have to be home by at least 10. I asked when she wanted to meet and she said how about 6 and she sent me a link to a bar/restaurant outside of town a bit. I told her I would meet her there at 6. I got cleaned up and put on some cologne and aftershave and headed to the restaurant. I got there early in case I needed to get a table. As I was walking to the door Brianna walked up to me. She had on a pair of tight jeans and a low cut cammy and had done her makeup nice and smelled amazing. I maybe was reading things wrong but she sure seemed dressed up for us just grabbing food as friends. We both said hi and went and found a table. As we were walking in it felt like all the guys were starring at her. We sat down and our server came over. We both ended up just ordering water and some food. Brianna went into more detail about her husband being in prison and about her kids. She also shared how she was currently in out patient treatment for drugs, trying to get clean for her kids. She didn't go into detail which drugs though. She asked what I was doing in town for only a couple days. I explained what I did for work and she seemed pretty interested. Our food came out shortly after that and we continued to talk and eat. It was shortly after 730 when we done eating. Brianna thanked me and said she had not been out to do anything in almost 2 years. I was surprised to hear that. Brianna said she was glad she had come out with me as she had a good time. It sounded to me like she was ready to head out. I told her I had a good time and got up, expecting her to do the same. She looked at me kind of confused. I apologized and said I thought she was hinting she wanted to leave. She said no she didn't want to go and was able to stay out until 10. I sat back down and we talked for another half hour. I asked if Brianna would want to go sit at the bar with me and grab a drink or two. She had a kind of half smile on her face. She said she wasn't sure but said she also never gets to go out. Brianna said sure let's have a couple. I left some cash on the table for our bill and we went and sat at the bar. We each ordered a beer and kept talking. We ended up having 2 beers each and it was about 20 to 10. I paid our tab and we started to walk to the door. She thanked me again for tonight and said she had a lot of fun. We got just outside the door and she came in close and gave me a hug. She smelled so damn good and I thought about moving my hands down her back to her ass but I didn't. She said she wished we didn't have to call it a night as she really enjoyed hanging out with me. She asked me if I would want to hang out again before I left town. I told her I was only staying in town through tonight and would be leaving around noon the following day. She had a kind of sad look on her face and said oh. She asked if I would stop in for lunch tomorrow on my way home and I said I would. She came in and gave me another hug. She smiled at me and walked off and i could help but check out her ass. I walked over to my car and left the parking lot. I was about half way to my hotel when she called me. She said she really wanted to hang out some more and had called her mom who said she could watch her kids until midnight. Brianna asked if I wanted to hang out some more and I said that would be great. I asked what she had in mind and she suggested maybe grab another drink. I asked where she wanted to meet and she asked me to choose. I wasn't super familiar with the area but suggested maybe we grab drinks at the small bar in my hotel or I could pick up some drinks for us. I wasn't sure how she was going to take the suggestion. She said drinks at my hotel sounded great and asked where I was staying. I let her know and she said she would meet me there in about 20 minutes or so. I got to my hotel put on some more cologne and headed down to the lobby. I stopped at the front desk and asked how late the bar in the hotel was open until. The desk clerk told me the bar closed at 11 and last call was 1050. It was close to 1030 currently. I was going to call Brianna and update her but she walked in the lobby doors. She walked over to me and gave me a small side hug. I told her what was going on and she said it was okay we could grab a drink at least. Brianna and I walked into the hotel bar and sat down. We were the only ones in the bar. Brianna ordered a mixed drink this time so I did the same. She sat a bit closer to me this time so much that our legs were touching. The bartender informed me it was last call and that we would have to leave by 11. The bartender did say we could order drinks and take them to the pool area which was open until midnight or back to our room. I asked what Brianna would like to do. She seemed to be thinking about it quite a bit. She finally said we should order another drink and just chill in my room if that was cool. I said I was down with that. We each ordered another mixed drink and I paid the tab. We walked upstairs to my room and went in. Brianna set her drinks down and said she needed to use the bathroom quick. I sat down at the small table in the room. Brianna came out and grabbed her drinks and set them down on the nightstand next to the bed and sat down on the bed and leaned against the headboard. We talked for a bit and she patted the bed next to her. I grabbed my drink and joined her on the bed. She leaned her head on my shoulder as we talked and gently stroked my arm. She changed our conversation to her husband in prison again. She told me he had been in there almost a year already and had around 5 years still to go unless he was released early. I told her I was sorry and she said yeah. She then pulled her head off my shoulder. She asked if she could tell me something and I said sure. She told me she had not been with a man since her husband was arrested and she was honestly very attracted to me. She said she wasn't sure what to do with how she felt. I asked what did she want to do. She gave me a very sexy look and took the hint. I leaned towards her and she met me half way and we kissed. She was really great at kissing and had super soft lips. She pulled away from me and I thought maybe I messed up. Brianna told me she had a confession to make. I was a little worried but listened. Brianna said she wasn't fully honest with me. She said she had called her mom after we left the bar and asked her mom to watch the kids until the following night. Brianna said she really wanted to have sex with me and she could stay the night too. I just told her how attractive she was and leaned back over. We started to kiss again. This time she got a bit more aggressive and bit my lip. She climbed over ontop of my lap. I reached down and cupped her ass as we kissed and it was super nice. She got off of me and stood up. She pulled off her top and pulled down her pants. She had an amazing toned body. She had on a matching white silky thong and bra. She crawled under the bed sheets and asked me to turn off the light. I was really hoping to keep it on and see her body but I wasn't about to argue. I walked over and turned off the lights and stripped down naked as I made my way to the bed. I climbed under the sheets and she scooted over to me. She reached over and ran her hand across my chest and down my torso. Her hand touched my hard cock and she said oh out loud. She laughed a little and said she didn't realize I was completely naked already. She wrapped her hand around my cock and gave it a couple soft squeezes. She said I was so hard and ran her hand from the base to the tip. She said i had a really nice dick. She pulled back the covers and moved down the bed. I felt her run her hand over my dick slow and said again, I had a nice dick. I felt her lips wrap around the head and she began to suck my dick. She definitely knew how to use those soft lips of hers and gently glided up and down. She took me just past my head into her mouth for a couple minutes. I just laid back and enjoyed the feeling. She then started to deepthroat me each time she took me in her mouth. She took almost my full length and didn't gag at all. It felt amazing being jammed down her throat as she played with my balls. She did this for a couple minutes before I gently pushed her back on the bed. I pulled down her panties and kissed my way along her thighs to her pussy. I ran my finger up and down her and slipped it inside of her. She was very wet and fairly tight. I slowly started to rub her g spot and then started to lick her clit. She jumped a little as I started and grabbed my head. I had only just started when she said she was going to cum. She let out a very sexy soft moan and clamped her legs around my head. Once she was done moaning she collapsed back on the bed. I kept licking and fingering her. I made small circles around her clit. I switched out my finger for my thumb inside of her and moved my middle finger down to her asshole. As soon as my finger hit her asshole she gasped and tensed up a bit. She then eased down and I kept licking and using my fingers on both holes. I kept doing this for another 10 minutes before her breathing picked up again and she said she was so close. She clenched down on my head with her legs again as she came. I stuck the tip of my middle finger inside her asshole and could feel her spasm as she came hard. She laid there for a moment and then rolled over. She took off her bra and threw it on the floor. She then crawled up the bed and took me back in her mouth. She sucked me a couple times and then climbed ontop of me. I put my hands on her nice set of round b cups. She leaned down and kissed me. I could feel her hand wrap around my cock and guided me to her pussy. She ran up and down her hole before pushing back and letting me slip inside of her. She was very wet and fairly tight. She let out a soft moan as we kissed and started making slow humping motions until she had my full length inside of her, she then let out a small sigh. She kept me in her deep and kissed me and told me how fucking big I was. She sat up and put her hands on my chest and then began to grind ontop of me. I reached up and played with her nice tits as she did. She grabbed my right hand and brought it to her mouth and started to suck my thumb. She bit down kind of hard and moaned. She then climbed off of me and told me to get behind her. I did as she said and got behind her and pressed back inside of her. I started out slow but picked up my pace. She had some sexy hips and I gripped them fairly tight. She met my pace pushing back hard as I fucked her. She was moaning and whimpering. She said it felt so fucking good and I was in her so deep. I licked my thumb and and gripped her hips. I started to rub her asshole with my thumb and she lost it. She started to shake and clamped down on me and came really hard. I kept slamming her and then felt her hand under us rubbing my balls. I hadn't expected that but it started to push me over the edge. I told her I was close and she told me to pull out. I did as she asked and she pushed me back on the bed. I felt her lay down across my stomach and take me back in her mouth. She started to suck just the head and stroked me. I came almost right away. She just kept sucking me through me shooting my load in her mouth. She sucked me for a while more and then come and laid on me. She said my load was huge and tasted super good. She said she would have loved for me to cum in her but she isn't on birth control at all. She snuggled up with me and i pulled up the covers. We ended up falling asleep together. She woke up close to 5 as she had to work. She got up and said she had to get going so she could get home and change for work as she started at 6. She snuggled with me for a little bit and then said she should go. She got up and headed to the bathroom. I turned the lights on and had some serious morning woof going on. I had just found all of her clothes when she walked out of the bathroom. She had her arm over her tits. She looked at my morning wood and said well good morning. She walked over to me and dropped her arm and hugged me. She gave me a kiss on the lips and squeezed my cock. She ran her hand up my body and said I had such a nice body. I cupped her ass and ran my hand up to her tits. She seemed a little shy but I assured her that her body was amazing. She blushed and said thank you. She said she wished she had more time this morning. She stepped over to get dressed and I got a really good look at her body and it was truly amazing. Once she was dressed she came over and gave me a kiss. I walked her to the door and she kissed me again. She asked if I would come see her at work for lunch. She said she was off at noon. I told her I would come see her after I checked out. She gave me a kiss again and headed out. I did some work and then took a shower. I got checked out and headed over to the diner. I walked in and she was at the counter talking and got a huge smile and blush on her face. She had on her work polo and those black leggings again. I went and sat at the table I had been sitting at. She came over still smiling and said hello again. She handed me a menu and then ran her hand across my shoulder and said she would be back. She came back a short time later and took my order. She asked if I would be heading out right after I ate and I said yes. She looked super dissapointed with that response. She brought my food out a short time later and we talked a little before she let me eat. I got done eating and met her at the counter and paid my bill. She was smiling but seemed a little sad too. I asked if she was still getting off at 1 and she said yes. I said I would hang out until she was done to say goodbye to her. She smiled at that and said thank you. I hung out in my car and waited for her to get done. She came out shortly after 1 and I got out and met her halfway. She jumped up into my arms and I cupped her ass as she wrapped her legs around me. She kissed me on the cheek and said she really enjoyed our time together. We stood and talked a while and she said she wished I still had my room at the hotel so we could go have sex quick. I told her that would be nice. She asked if maybe we could go find a spot in my car for a quickie before I left. I was totally down so we got in my car and I let her pick the spot since I didn't know the area. She had me drive to a park not to far down the road. We drove a ways into the park and went to a secluded end of the lot. She practically jumped into the backseat and started to pull down her leggings, i noticed she didnt have underwear on. I crawled back and pulled down my pants. As I was pulling down my boxers, she leaned over and took me in her mouth. I was half hard and she got my rock hard really quick. She spit on her hand and rubbed it all over me and then on herself. She climbed over onto my lap and sank down on my cock. She let out such a cute little moan as she did. She was slow at first but then picked up speed and I met her pace slamming up inside of her. She came only a couple minutes into riding me and gripped me really tight as she came. We repositioned and I had her lay down. I got down in front of her and pulled her to the edge of the seat. I pushed back into her. I gripped her sides and started to slam her deep and hard. She was moaning and telling me to fuck her harder. I started to get close and I told her I was about to cum. She told me not to stop and I asked again. She told me i could cum in her if i got her a plan b. I fucking lost it and pushed in deep and emptied inside of her. She pulled me to her and we kissed. I pulled out and we both got dressed quick. She said that was great. I drove us to the store and went and bought a plan b. We talked on the way back to the diner. She said she wished I lived closer so we could fuck all the time. I told her I wished that too and maybe I could make a trip back this way soon. She said that would be great. We got to the diner and I walked her to her car. She hugged me and then we kissed pretty passionately in the parking lot. I could feel her hand rubbing my dick as we kissed. She got me rock hard again. She snuck her hand down my pants and gently stroked me. We were in between two cars and in the back of the lot but I was still looking around. She gave me a look and then lowered herself down in front of me. She unzipped my pants and pulled my dick out through my boxers. I was really watching around me but also really turned on. She took me in her mouth and just starred up at me as she sucked my dick. It felt fucking fantastic. She used a lot of spit and just sucked the tip. She told me we had to hurry as she didn't want to get caught. She spit on my dick and then started to rub just the head fast and light. I fucking loved that and it made my dick twitch alot. I could feel my balls getting tight and she must have seen it too and told me to cum for her. I told her to lean across the hood quick. She jumped up, pulled down her leggings and bent over the hood. I got behind her and slipped right in. I only made a couple hard pumps in her before I tensed up and shot another load inside of her. I pulled out slow and she turned around and took me in her mouth. She then put my cock away gently and pulled up her leggings as she stood up. She gave me another hug and kissed me on the cheek. I gave her ass one little squeeze before we said our goodbyes. On my drive home she sent me a couple nudes to think of her and a picture of all my cum that had pooled in her leggings. She told me to come back soon, which I plan to.