The last guy I played with a couple of years ago. Yeah I really liked him. Kind of the one that caused trouble. Trouble with a capital T. I knew him from real life not someone you get to chatting with online which can be complicated. He also was even more of a flirt than I am. For those of you that have gotten to know me you may find that unbelievable but I swear its true. So along with the flirting and both of us being like totally attracted to each other and his head games it was a fun fling but did cause some problems. Anyway on to the story.
He had been flirting with me for probably a year every time we ran into each other. I would probably see him at least a couple of times a month so it was fun. Around my birthday time he texted me and as usual was his flirtly self. Keith knew about it and he was like call his bluff see if he will bite. So i texted back something not overly suggestive but something if he was interested could make it a bigger deal. He did. So then we started texting more. He was much more assertive in his flirting and I suggested he come by the office so he could give me a kiss.
So first time we got together was on a Monday night in July. He came by it was after hours, we chatted for about 30 minutes, he was kind of stalling but I don’t think he really knew what to do so we walked to the door and he was about ready to leave. So I just kissed him. Then it was another and another and we went back to my office and laid down on a couch and had a hard core make out for like another hour. It was so awesome. Keith had texted me a time or two and wanted to know what was going on I said I would be done in a few minutes but you know when your having fun time passes pretty fast. I finally got home around 8 and he wanted to know all about it. Shaun had no idea Keith knew so when he was texting me he was a little freaked out.
Shaun wanted to get together the next night but it was my birthday. So we agreed to meet on Wednesday night. Same place after work and we were on the couch, then cushions on the floor, Then him between my legs grinding. Him touching everywhere, He really was a great kisser and the texting we had been doing and him wanting me so bad was very hot. He wanted to go further but I kind of had to be like I can’t, which was true, but I couldn’t really tell him about Keith and my rules so just had to play like the making out was hot and I liked it but we couldn’t do more. So after a couple of hours of making out and petting and a little touching under clothes. He actually totally got undressed…I mean naked undressed and I got to stroke his cock. That was hot. But i kept my clothes on but had a dress on so the grinding was nice. 🙂 Anyway it was fun and I lost track of time but it was a couple of hours like I said.
Went home and OMG Keith was all over me. It was really hot sex. Foreplay with someone else always makes for incredible sex with Keith later. Anyway Keith was like how far do you want to go? I was fine with what we had done but I think Keith wanted me to do more. Husbands can really get daring when they are turned on. So I won’t bore you with details but Shaun and I didn’t get together for like another month because he wanted more and I didn’t really have a good excuse not but finally around my anniversary Shaun texted me again and was like 15? I was like 15 what does that mean? Shaun was like lets just get together for 15 minutes I want to kiss you again. So you know that kind of melts a girls heart being wanted so I mentioned it to Keith and he was like when? So we changed our plans and went home and I went to meet Shaun. On the way out the door Keith was like at least let him see your tits naked and give him head. I wasn’t really planning on it we only had like 15 minutes. He texted me about 8 pm so by the time I met up with him it was close to 8:45. So I had till 9. lol. Well we played until nearly midnight.
Keith was starting to get worried and had texted me several times and I kept telling him soon but we were having so much fun. In hindsight Keith was turned on but there is a fine line between lust and jealousy and with him knowing Shaun it definitely blurred. He told me later he was pacing the house, jacking off, and almost drove down to the office a few times. Anyway that was a fun night. We made out with me on top, took off my shirt, garments, and bra. He has great hands and my breasts and nipples got a lot of attention. I almost came just from that. He had never had oral and I gave him head for the first time. He was soooo hard. He begged me to let him take me but I wasn’t on the pill and that would have been really dangerous at that time. He didn’t have any condoms either and I was really worried if we went that far as to dip he would fuck me. I did get him off though and he came a ton. like 3 times.
Went home and Keith wanted to know all about it. Like every detail. So we spent an hour with me telling him all about it. He was drooling cum and I sat down on him asking if he liked it. He did and when I told him Shaun asked to take me he shot his load but didn’t even go down. The whole lust thing is crazy. Even though he totally doesn’t want me to fuck his cock sure thinks it was a hot idea. He was like you should get together again but I felt that was a bad idea. Things seemed to be progressing further each time and I wanted more to. Shaun was texting me like crazy wanting to get together again as well so between the two of them begging about two weeks later we planned another make out. Problem is with it getting further each time this time we were like at 2nd base to start. Within 30 minutes he had my pants down to my ankles and my garments down as well and was grinding his cock head around my slit and teasing my clit. I was so wet and horny and he was throbbing hard. I was on the desk with my legs spread and he was definitely giving me some pleasure. He started to poke at my hole but we weren’t in a great position. Keith texted and wanted to know what was going on I laid back a bit and his head kind of slipped in just a little. I was like no deeper he just was kind of rocking a little. Keith wanted to know what we were doing and I was like he is trying to get his cock in me. He was like really? I was like really he is going to fuck me if I don’t stop this. Keith was like let him dip. I responded this is dangerous. He was like you can handle it.
So we ended up on the couch. I spread my legs and told him just a little like before. he couldn’t really get in at all so I pushed my pants off my one leg and bent my knees a little more and he slipped in. I gasped. it surprised me but as horny as I was it shouldn’t have. He was in a couple of inches and it felt soooooo good. Definitely deeper than other guys had been. I was like wait you can’t fuck me. I think it surprised him because he was actually in me. so we were kind of just rocking a little and kissing. Every movement you can feel pleasure. So we wanted more but both too scared to go further other than not pulling back. He slipped in probably another inch just being on top of me and moving and he was like i’m going to cum. I’m like pull out! He took a couple short strokes at that point I didn’t care I wanted him to fuck me and I looked in his eyes and I whispered to him just fuck me but he couldn’t hold it and pulled out and shot all over my pussy and stomach. He barely got out. Probably was very lucky but God that felt good. He wanted to do it again but I wouldn’t. Already knew we had gone too far. That was Keith’s fault for encouraging it if I did it again it would be my fault. We made out a bit more and I tried to stroke him but he kept trying to get me to straddle him on the couch. I let him rub it in my lips but I wouldn’t let him put it in again. Even just a dip because I knew we would fuck. He was frustrated and stopped kissing and was like I better leave. So he left. I was like why isn’t making out enough but he wanted sex. So that was the last time we made out.
A couple of times he texted again and wanted to play and offered to bring a condom. Once I almost went and Keith was pretty jealous about it by then. I think he knew I really liked Shaun and with as close as it came Keith freaked just a little. We argued a bit about it because I was like I was fine with what we had been doing you were the one that wanted to walk the edge. He admitted to it that he liked me to push the boundaries but yeah when you get that close to getting burned it scares you a little. It did him. Shaun finally stopped texting I think he was mad. We have started texting again lately but I still haven’t gotten with him again. Keith said if I wanted to and he was okay with just a make out that would be fine but I don’t think he could handle it. I have my eyes on a couple of other guys that might be fun. Just not pushing my luck yet. It takes time. But that was probably the closest I have ever gotten to actually going all the way. I so would have let him and may still if I ended up with him naked between my legs again. Dangerous waters but so fucking fun.