My fiance and I live in different cities currently. We are about 2 hours apart and drive to see each other all that we can. We have plans of moving together once I start my new job next year. This last week I went up her way to spend the holidays with her. I arrived on Wednesday and stopped at the gym down the road from her place to lift. After I was done I stopped down the street at the subway there to grab something to bring to her place. I walked inside and was met by a worker named Jami. I ordered my food and she seemed overly friendly to help me out. She looked to be in her late 40s, brown hair in a ponytail, very petite frame, pert little lips, brown eyes, a couple little tattoos on her fingers and a little homly looking. When we got to the register she rang me up and asked if I wanted anything else. The way she said it caught my attention like she was flirting with me. I paid her and thanked her. She said she hoped to see me again tomorrow and to have a nice day. I brought my food to my gfs and spent the rest of the night with her. I woke up early in the morning and helped her get things together for food platters and gifts. She had to work 10 to 8 so we just hung out until she had to leave. I hung out at her place for a bit, took a nap and then made some lunch. I ended up heading out to the gym shortly after lunch. Once I was done I decided to stop at subway again as it was close by. I walked in and didn't see anyone behind the counter. I went up and waited and a guy came up and took my order. I was just starting to pay when Jami came walking out the back with her jacket on. She seen me and stopped. She made a comment jokingly that she thought I wasn't coming in today. We shared a little laugh and she said well I just missed her as she was leaving for the day. She shot me a smile and walked out the door. I went and sat down at the table. I had just started to unwrap my sandwich when Jami came back in the door and came and sat across from me. She had her jacket unzipped down which it wasn't before. Her cami she had on under it had buttons and they were all undone. It seemed she intentionally had done this to get my attention but I didn't bring it up. I looked at Jami who smiled at me. She said she has never done this before but she said she thought she felt a connection and wanted to ask if we could maybe go out on a date. I really weighed out the options here but told her I was dating someone and I was sorry. She had a look of dissappointment on her face when I said that. She apologized for interrupting me. I told her she didn't at all and that she did nothing wrong and that I was impressed with her confidence and how she handled herself. She got that smile back on her face. She said thank you and stood up. She stood there for a moment and told me she was working tomorrow until 2 if I wanted to stop by she would buy me a sub for the hassle. I said it wasn't a hassle and that I probably would be over tomorrow around that time. She got another smile on her face. She then left. I finished my food and did the same. The next day my gf had to work again 8 to 6. We ate breakfast together and she left for the day. I did some yard work for her and then went inside and got changed. I headed to the gym around 1230. I lifted quick. I decided to stop by and get the free sub she offered me as it was close to 2. She was at the counter when I walked in and her face lit up. She had on a noticeable amount of makeup, I she not seen any on her before. She made me a sub and gave it to me for free which I still offered to pay. I went and sat down to eat. I was about half way into it when she came and joined me. She had her jacket zipped down and a different cami on but it was pulled down quite a bit showing her little bit of cleavage that she had. She asked how it was and I said great. She said she realized she had never told me her name. We introduced yourselves to one another. She apologized again for the other day. I again told her not to worry about it. She said she did really feel a connection with me and also thought I was super hot. I don't think she meant to blurt that out as her face got really red after she said it. I smiled and said thank you to her. I was trying to be nice so I mentioned she looked nice today. She had a huge smile on her face and said thank you. I was just finishing up and she said it was nice to see me again today and she was glad she could make up for the other day. She walked out the door with me as we talked a little. I went to get in my car and she walked over with me. She asked if she could run something by me, I said sure. She said she knew I was dating someone and that we couldn't go out on a date or anything like that. Jami then asked me if maybe we could just hang out or something. Before I could even think about it, she said that she was cool with whatever and that she wasn't going to cause problems between me and my gf. I asked what she meant by that. She took a second to think and just said she was down to you know…if I wanted to and that she wouldn't say anything to anyone about it. From what I was gathering it sounded like she was down to hook up on the down low. I wanted her to say it though so I didn't just assume something and say it and offend her. I again asked what she meant and nicely said to just tell me flat out what she was meaning and don't be shy. Jami played with her jacket some and started to talk but stopped. She was red in the face again and seemed lost for words. She finally spoke and said if I wanted to, we could go back to her place and chill. She said she knew I was in a relationship and that I would never date someone like her. Jami then said what she was trying to say was she thought I was hot and then she trailed off. She looked at me and said maybe I could fuck her. She was super red in the face and it sure seemed that was out of character for her to say thay. She apologized if that was too much but again said she was super attracted to me and wouldn't say anything if we did or didn't hook up. I was actually really turned on after hearing what she just said. All I said was I had to leave by 5. Jami got a big smile on her face. She said she lives just down the road and usually walked to work. She came over and hopped in with me. I drove her to her place and we both went inside. She had me sit on her couch, she said she needed to shower quick and change. She went off down the hallway and I heard the shower start a short time later. Her house was super small but looked well kept and was nice. I heard the shower turn off about 20 minutes later and then the blow dryer going. I checked my phone and it was already just after 3. She yelled down the hallway she was just about done. A few minutes later she came walking down the hallway in a silky robe and had her hair in a ponytail. She had done her makeup again and looked pretty cute. She apologized for taking so long. She seemed super nervous. She asked if I wanted to come to the bedroom with her. I said yes and followed her to the bedroom. She stopped me at the door and said not to judge her please. Her room was a mess to say the least. Her bed was a mattress on the floor with no box spring. She led me over to her mattress and we both sat down. She seemed super nervous still. I asked if she was ok. She said she was, it's just she was nervous. She said she didn't want to go into to much detail but said she had not had sex in quite a while. I asked why. She said she had been married and her husband had passed away a couple years ago. She said I reminded her of him and hoped that didn't sound creepy. I said no it wasn't and asked what she wanted to do. I said if she didn't want to do anything at all that was ok too. She sat there for a moment and then got up and turned off the light. I heard her walk over towards me and got down on the bed with me. She pushed me back on the mattress and I felt her hands pulling at my belt and jeans. I felt my hard cock spring out of my boxers. A moment later I felt her warm mouth wrapped around it. She slowly stroked me as she moved her lips up and down my just past the head of my cock. She actually gave really good head and it felt fantastic. I was little worried she was going to be terrible in bed. I just laid there and enjoyed it. After a few minutes I could feel her climbing ontop of me. She moved her way up and sat down on my lap. I wrapped my hands around her waist and I swore my hands almost were touching her waist was so tiny. She reached down and grabbed my cock. She positioned me at her hole and started to press down. I could feel she was wet and it only took a couple tries to go in all the way. Once I fully inside of her she let out a slight gasp and just sat there. She was tight as fuck and it felt so damn good. She reached down and put her hands on my chest. She just grinded on top of me for about a minute before I heard her start to moan and I could feel her tighten up even more. She came super hard from what it seemed. She leaned over onto me. I grabbed her sides and guided her pace of riding me. I then cupped her little ass and just enjoyed how tight she was. She leaned down and we began to kiss. I didn't mind as we were having sex. I was actually getting close already from how tight she was. I told her I was going to cum soon and asked if I should pull out. She told me I could do it inside of her if I wanted to. I cupped her ass and pulled her down deep on me as I shot my load inside of her. Her pussy felt like it was sucking the load out of me it felt great. She sat on top of me for a minute and then rolled off. She went and turned the light on. She came over and sat next to me and put her head on my shoulder. She said that felt great and she had forgotten how it felt to have a man inside of her. I seen her alarm clock next to the mattress. It wasnt even 430 yet, we had both came pretty quick. She said she was going to go get cleaned up if I wanted to leave I could. I asked if we could go a second round. She looked at me supsirsed and then noticed I was still rock hard. She said yes we could. She went to get up and I pushed her down lightly. I got between her legs and pressed back inside of her. I slid right in with her juices and my cum inside her. She felt so good to be back inside of. She wrapped her legs around me. I leaned down and we kissed. I couldn't get my full length inside of her due to her hips being so close together. I sat up, pulled out my cock and then put her legs up on my shoulders. I pushed back inside of her and it felt even tighter now. I pushed her legs back towards her head and pushed all the way inside of her. Her eyes got really big as I went in super deep. She gasped and put her hand on my chest. I asked if she was okay. She said she had never done this position before. She said she could feel me super deep inside of her it just startled her but felt amazing. I grabbed her sides and started to slowly and deeply fucked her like this. She was moaning and shaking as we did. I then started to slam into her hard over and over. She was biting her bottom lip and moaning. After a few minutes of slamming inside of her she said she was going to cum. I kept going and felt her pussy clench around me as she came. Once she was done I pulled out of her and rolled her over. I pulled her into doggystyle. I was amazed at her body. I hadn't seen her ass naked yet. It was super tiny and toned and her waist was super small. I pushed back inside of her and gripped her sides as I started to pound inside of her. She arched her back up alot which I could tell she hadn't done this position much. I pulled her legs apart some and pushed her chest down. She put her face into a pillow and I grabbed her ass and started to pound her hard. She was moaning and screaming into the pillow as I did. I was getting close again and slowed down some. I made long, slow strokes in and out of her. I told her I was going to cum. She said ok. I was hoping for more of a response than that but still shot my load inside of her. I pulled out of her and laid down. She got up and went to the bathroom. I noticed it was after 5 so I got dressed quick and gave her a hug on the way out. I asked if she would be available tomorrow. Jami said she had to work late but I could swing by around 4 for her lunch if I wanted to. I said ok and left. I got home about 10 minutes before my gf. I jumped in the shower and got all cleaned up. We stayed in for the night. The next day she only had to work a half day and asked if it was okay if she hung out with one of her friends for dinner and then we could go out to a movie. I said sure that would work. She went to work and was back home by 1. We ended up just hanging out at the house for a while and I attempted to intiate sex but she said no. She got ready around 330 and left. I jumped in the shower and got changed. I grabbed my gym bag to go lift. I went in and did a quick lift. I didn't bother changing before I left. It was close to 430 when I was done. I decided to stop by subway and see if Jami was on break yet. I walked in and Jami was behind the counter. She lit up when she seen me walking in. Jami met me at the end of the counter and said she hadn't taken her break quite yet and could go. She said she got a half hour break and was going to eat quick. I went and sat down at a table. She came out and joined me. She had made herself a small sandwich. She ate it down in a couple minutes. She asked if I wanted to go outside to my car and talk some, I said sure. We got in my car that was parked on the side of the building. She told me she had a great time the other night and knew it was just a one time deal. I said I had fun too and said maybe we could find time on the weekend before I left to hook up again if she wanted to. She had a big smile and said she would very much like that. She said she really liked that I showed her new things and took control. I really wanted to take her back to her place and have sex with her but I knew she couldn't because of work. She checked her phone and then apologized she said she just wanted to check how much time she had left on her break, she said she had just over 20 minutes. We sat and talked a little bit more. She asked me if I enjoyed having sex with her, she had a very worried look on her face. I said yes it was great and was exciting to show her new things and how receptive she was to it all. She blushed a bit and said yes she was open to knew things and liked to be told what to do. I asked that she be more vocal and tell me what she wanted next time, she said she would do that. I was super horny after being turned down from my gf at home. I looked at her and she was smiling at me. I said I wonder if we had enough time for her to give me head. Her eyes got a little wide. She then got a smile on her face and kind of laughed. She said she didn't know if we did or not while still giggling. She looked at my crotch and licked her lips. She asked if I wanted her to try, I just shook my head yes. She pulled her hair back into a ponytail and looked around to make sure no one was around. She then leaned down and undid my belt, unzipped my pants and I helped her get them down. She wrapped her hand around my cock and gave me a couple strokes before she wrapped her lips around me. She slowly and deeply sucked my cock. I wrapped my hand around her ponytail and guided her pace. She was super good at sucking dick and her lips were super soft. I told her to play with my balls too. She softly rubbed my balls while she sucked me. She sucked my dick for just over 10 minutes before I started to get close. I told her I was going to cum. She pulled her mouth of me and kept stroking me. I told her put it back in her mouth. She said she had never had a guy cum in her mouth. She said she would for me if I wanted. I said I would love her to do that for me. She went back to sucking me and got me close again. I started to cum and she just held my cock in her mouth and slowly stroked me. I emptied a huge load into her mouth. She sat up and held her hand to her mouth. I told her to swallow it down. She swallowed it down and wiped the cum on her lips and swallowed that too She said it was actually not bad at all and she liked it. I put my cock back in my pants and zipped them back up. She said that was a lot of fun. I asked for her number and said I would get a hold of her on Sunday if she would available before I left to go home. She said she would let me know. She went back inside and I went back home. My gf and I went and did holiday stuff with her family through Saturday night. We went back to her house and ended up falling asleep on the couch together. The next morning flew by and I was planning on leaving by 2pm. It was close to 11 when I sent a text to Jami. She text me back right away and said she would be off by 4. I said I woukd meet her at her place just after 4 if that's ok. She said that would be perfect. I packed up by bags at 2 and headed over to the gym. I did a workout until just about 4 and then showered quick. I headed over to Jamis. She met me at the door in a long t shirt that just barely covered her butt. She had done her makeup up and looked really good. She gave me a hug at the door and invited me in. We walked in together and she walked into the kitchen. I walked up behind her and grabbed her from behind. I pulled her to me and ran my hand up her leg and under her shirt. She didn't have any panties on and I ran my hand over her pussy. I grabbed her by her ass and lifted her up on the counter. Jami wrapped her legs around me as we kissed. I pulled down my pants and boxers. I pulled Jami to the end of the counter. I spit into my hand and rubbed it on my dick and ran a finger along her pussy again. I pressed up against her hole and after a few pushes I slid inside of her. Damn she was so tight it felt so good. She kept her legs wrapped around me pulling me in deeper every time I entered her. I grabbed her by her throat and pushed her back against the cabinet. She had a little smile on her face and I could tell she liked that. I picked her up and carried her to the living room. I sat down on the couch with her on top of me. She put her feet on my sides and started to ride me. She made sure to pull almost all the way to the tip and then slowly press back down. She did this for a few minutes before she leaned against me and bit me on my shoulder and said she was going to cum. She started to grind on top of me as she came and her pussy clenched hard on my cock. She just sat there and leaned against me when she was done and was breathing hard. I stood up with her wrapped around my waist still. I brought her to the kitchen again and set her down. I grabbed her and turned her around and bent her over the counter but realized that wasn't going to work due to her being shorter. I then had her get on her kitchen chair in doggie. I got behind her and pushed inside her wet pussy. I grabbed her hips and started out slow and then picked up speed. Eventually I was pounding into her super hard. She was moaning very loudly and I got close pretty quick. I kept slamming as I shot my load inside of her. I enjoyed how tight she was and how it felt like her pussy was sucking me dry when I came. I pulled out of her slowly and stepped back. I could see cum dripping out of her pussy. She put her hand over her crotch and walked to the bathroom. She came back a little bit later and joined me on the couch. She leaned against me and said she was glad I could make it before I left. My cock was still out and somewhat hard. I was still pretty horny and wanted to go another round with her. I asked if she could suck on my dick for a bit. She smiled and said gladly. She leaned over and took me in her mouth. Her soft wet mouth got me hard again really quick. Jami kept sucking on me for a while still though. I was playing with her pussy as she was sucking me and started to rub her asshole too. She jumped a little bit at that. I asked if she wanted to have anal sex. She stopped sucking me and said she had only done it a couple times. She said it actually felt good for her but she wasnt sure with me since I was much bigger than she was used to. She said we could try though and see. We walked into the bedroom together and she got some lube out of her drawer. She lubed up her asshole a lot and then out some all over my cock. She climbed ontop of me and straddled me. She braced herself with one hand and guided my cock with the other. It slipped around a couple times and then the tip popped in. She let out a little moan. She started to try and ride me and get inside of her but it wasn't working. She got up and then got into doggy for me and said to try it that way. I grabbed the lube put on some more and then got behind her. I popped the head back in and started to make slow hard strokes into her. She was pushing back at me as we went. I slowly made my way inside of her stretching her asshole apart. I finally did one big push as did she back at me and I was in all the way. She stayed there for a minute and she was definitely stretched out but it felt good. I started to fuck her tight little as and she put her chest down. I grabbed her hips and did full length strokes in and out of her. I seen her hand down below rubbing her pussy as we went. I loved watching her tiny little ass take my cock inside of it. I grabbed under her waist and pulled her with me as I leaned back. She ended up on top of me in reverse cowgirl. She leaned back and started to ride me. I felt super good but I wanted to watch her play with herself some more. I had her turn around and ride me on top facing me. She was bouncing up and down and I reached out and rubbed her clit. She really liked that alot. I told her to play with herself for me. She kept riding me and she started to make circle motions on her pussy with two fingers. She was breathing hard and biting her lip so I figured it must have felt amazing for her. She said she was getting close and it felt really strong. She kept riding me and said she felt like she had to pee she thought. It sounded to me like she was going to squirt and asked if she had ever squirted before. She didn't seem to know what I meant. I told her to just keep doing what she was doing. She kept riding me and playing herself when she said she was going to cum. She started to moan and almost scream as she rode me and rubbed herself. She said there was so much pressure and she was uncomfortable. I told her to just ease up and keep going. She was still moaning and then let out a loud moan as she started to squirt on my chest. She released a lot onto me. She looked horrified as she did. I told her it fine and keep going. She got nervous and hopped off of me and grabbed a towel. I told her it was natural and asked how it felt. She said actually it felt really amazing but made her feel dirty. I told her it was okay and I thought it was hot. She lit up and said really, she said really. Jami stood there for a minute and said she didn't think she could go anymore tonight and she was sorry that she was just embarrassed. I said it was ok. I asked if I could shower quick and she said of course. I walked into the bathroom and just quick showered cleaning up my chest and cock. I came out of the bathroom and grabbed my clothes off the floor. Jami was sitting on the end of the bed in her long shirt. She apologized to me for ruining the night and I said nothing was ruined at all. I got dressed and she walked me to the door. She gave me a big hug and asked when she could see me again. I said I would be back in a couple weeks and we could figure out a time. She pressed up against me and gave me another hug and thanked me for the evening. She looked up at me and we kissed, nothing passionate but just a kiss. She must have felt otherwise because she kept kissing me and pushed a tounge into my mouth. I did the same back and we stood there for a minute kissing. She then pulled away. She stood there looking at me. She said you wanted me to be more vocal and say what I wanted right, I said yes. She walked over to the couch and pulled off her shirt. She bent over the arm of the couch and said she wanted me to come fuck her some more and cum inside of her before I left. That got my attention really quick. I had my pants pulled down by the time I got to her and was fully hard. I got behind her and pressed inside of her pussy. She moaned as I did. I grabbed her hips and started to slam her as I was worked up from not finishing before. She told me to fuck her hard. I slammed her deep and hard for only a couple minutes before I was ready to cum. I said I was close and she said she could tell. She told me to fill her up. She reached back and gently rubbed my balls and I started to cum inside of her. It was one of the most powerful orgasms I've ever had. I pulled out of her and she turned around and stroked me while she kissed me. She said she would text me and we could figure out a time in a couple weeks to meet. She followed me to the door after I got dressed and gave a kiss goodbye.

Share Via...