OK…..this I have to tell. I can’t believe I actually did this.
The other night my wife had to be at her office at 11PM and since I had the next day off I figured I’d spend most of the night on the computer jerking off to porn since she would be gone to at least 9 the next morning, so I was looking for at least a 3 load night. I took her to her office and dropped her off and headed home. I got back to our apartment and stripped nude and got my lubes and laptop ready. I logged onto my usual sites first, checking for messages, friend requests and comments but as I did something in the back of my mind told me to look at Craigslist. I got onto the site and went to the "casual encounters" section and started looking at the ads. We all know most of the W4M are spam and links to viruses so I skipped most of them. Nearly all the T4M ads on Mobile’s CL are transsexuals, but they want "generous men"—-I hope you know what that means. Then I refined the search to M4M and got rid of most of all the garbage and spam posts. My phone’s message notification musci went off and it was my wife telling me that her and her group were leaving and they had a 2 hour ride. I looked through the ads for men that were over 35 and withing 15 to 20 miles of my apartment. I had just aboout given up when I found an ad that caught my attention. His ad said he was 50, a top, not fat but not shape and had a 5" cock. He was looking for a bottom 40-55, body size didn’t matter as long as you could suck a cock and wanted to get fucked and liked playing outside. I answered him, telling him about myself, my situation and sent him a few pictures {all are on my profile}. I looked for a few more minutes but gave up and went back to the porn sites. Yes…..one of the ones I check is xhamster….in fact it’s the first one I check. I looked around for a few minutes then went to my next "usual" stop. I had left my email up in a background tab so I caould if the guy answered. I was half-way through the notifications on this site when I saw I had a new email. I checked……it was junk, so I went back to the notifications. I had finished with them and was watching (and jerking off to) some videos when I noticed another new email. I checked and it was the man answering me. He said he understood my situation and was interested in meeting me in person. I gave him my number and he called. We exchanged the usual nervous first pleasantries and then after a couple minutes got down to the real subjet of the call. I told him I couldn’t leave until I had heard from my wife letting me know she was at her job site in New Orleans and that she had already been gone for an hour. He said that it wasn’t a problem. He told me that he was on disability for an injury he had had on the job and was usually up most of the night anyway so late night playing was fine with him….in fact he said he preferred it. While we were on the phone he emailed me a couple pics of his cock and 1 full body. I sent the same to him but he let me know that he wasn’t interested in my cock…..only my mouth and asshole. He said he really like the pic I had sent him where I’m wearing a pair of my wife’s panties and cami top and asked if I still had it and if I could meet him later coudl I wear it. I told him that if I could find it I would wear it. We talked about what all we were into and not into and what we wanted to do and all that. My phone beeped for an incoming call so I hung up with him and answered it. It was my wife, they had made it and said they were short-handed so it would take them a couple more hours than they had planned. I told her it was OK and I’d see her later. We hung up and I went to the bedroom and started digging through boxes and bags that we never unpacked when we moved in the apartment months before. I found the outfit, stripped and then put it on. I used the camera in my laptop and took a couple pics to show him I had gained a few pounds since the last pics and sent them to his email. He answered saying my ass looked better with a little more meat on it and then asked if I had access to a skirt. I called him back and told him that my wife owned 3 dresses, a denim thigh-length, a calf-length formal and her wedding dress. He asked me that if he brought one and if fit would I consider wearing it and I told him sure. We made plans to meet at the WaffleHouse that was just down the road in 30 minutes for a face-to-face meeting to make sure we wanted to go further. I hung up and jumped in the shower and then did a "clean out". I put on the cami top and panties on under my jeans and the t-shirt I told him I’d be wearing. I passed one WaffleHouse to get to the one we agreed to meet at…..about 3/4 of a mile from the other one. I pull in the lot and see that other than him standing in the parking lot and the 3 employees inside it was desserted. Even though I don’t have a conceal carry permit, my 9mm pistol was in the waistband of my jeans……just in case. I pulled in next to him and we introduced ourselves and went inside. We both ordered coffee and after the waitress poured us some and left we talked. It turned out he lived just down the road next to the WaffleHouse and could have walked. We had one last cup of coffee and we each left a $5 and left. I followed him to his house. I had driven by his house dozens of times over the years. He told me he grew up there and moved back in after his parents died. His wife died of cancer a few years ago and they had played together with men, women and other couples until she got sick. He stopped playing for a few years and he said I was only the second person he’d met with since she died. He said the first sounded promising, but when he met the guy…..k** actually……22 years old and was looking for a sugar daddy….knew it wouldn’t work. Fortunately they never got to where he invited him to his place. We went in his house and then after an offer of a beer or something stronger we went out the back door to the back yard. The house sits on about an acre maybe a bit more and is surrounded on 3 sides by thick woods and the house blocks the back yard from prying eyes on the road. We sat down on the large swing he has back there and talked a few more minutes. I reminded him that if my wife called or sent a text I’d have to take it, he said it was OK and said that I could go inhis shed to talk so there would be no outside noise. I decided to get things started, so I stood up and pulled my t-shirt off letting him see the cami top. I told him not to get excited or get the wrong idea and took my pistol and holster off my jeans and laid it on my shirt on the ground. He smiled and took his off too. We laughed and agreed it was only smart to do it because you never knew. I kicked off my shoes and took off my jeans making sure I had my back to him so he could watch me bend over. I heard him say "mmmmmm…..nice" and then felt his hand on my ass. I asked him about the skirt and he said he’d be right back and ran to the house and went in. He came back a few minutes later and handed me a black nylon miniskirt with elastic in the waist. I stepped into in and pulled it up, it was a little tight but it fit and came to about midthigh. He had something else in his hand and showed me what it was….a pair of black thigh-high stockings. I sat down and pulled them on. He asked if I minded wearing the things and I told him that I actually enjoyed dressing up once and a while and that I used to do it all the time. He asked if I had a problem playing sub….again….I told him it was OK. {For some reason, when I’m with another man I get submissive…..not femme….just submissive} We moved from the swing to bench that was by a fire ring and he sat down. I straddled his hips and leaned down and started kissing him. {yes….we had discussed these things on the phone……and no……I have no problem kissing another man}. As we kissed I felt his hands on my outer thighs and then on my ass. He was massaging my ass and I could feel his cock getting hard. I moved to my knees in front of him and unzipped his pants and took out his cock (no underwear) and started licking it from the head to his balls. I licked around the head then down the shaft and teased the hole with the tip of my tongue. "Ken" was moaning and saying how good my tongue felt on his cock. I teased him a little more then I took his cock in my mouth and started sucking, taking it all in my mouth and throat. He put a hand on my head and would gently push me down whenever I came up. After a few minutes he stopped me saying he wasn’t ready to cum yet and had me stand up. He stood up and took off his shirt and then after kicking off his deck shoes, stepped out of his pants. He took my hand nd led me to a large magnolia tree in the back corner of the yard. It was fairly dark, the only light was the half moon. He had me lean against the tree facing it and then he pressed up against me. I could feel his cock on my ass and he very gently ground it on my ass. He leaned down and started kissing my neck just under my ears {anybody…..man or woman does that to me it drives me crazy} and I pushed my ass back against him. He moved down…..kissing my back and then moved down and kissed the backs of my thighs. I felt his hands go under the skirt and lift it up and then felt his lips on my ass as he kissed each cheek. I then felt his fingers tracing the leg holes of my panties and when his fingertip brushed my asshole I shiveered and moaned. He then found the waist elastic and pulled my panties off my ass and continued kissing my asscheeks. He had me bend over a little and then he spread my asscheeks and teased my hole with his tongue. I was moaning and grinding my ass in his face and finally I felt his tongue push into me. He probed my ass with his tongue and licked me deep…..my legs were shaking and my cock was so hard I thought I could stab the tree with it. He stood up and went back to kissing my neck, letting his cock rest between my asscheeks. "Don’t move," he whispered and left me leaning against the tree. He came back and just before he leaned against me I heard a clicking sound. When I felt something cool and wet between my asscheeks I realized what it was….him closing the lid to a bottle of lube. He started kissing my neck again but this time his cock slid between the cheeks of my ass. I could feel him getting harder and harder everytime it slid up and I felt his balls against my ass. He pulle back a little and with his next push slid into my ass. He stopped half way in to let me get used to it and that only took a few seconds. When he felt me push back towards him he pushed the rest of the way in. He reached around and under the cami top and picnched my nipples. I was groaning and moaning asking hime to fuck me harder. He increased his thrusting a little but he still wasn’t doing it very hard, but everytime he went balls deep. Suddenly he stopped and pulled out. I was just about to ask if there was something wrong when he took my hand and led me to a spot of short, manicured grass and lay down on his back. He had me pull my panties back up then pull the crotch to the side and sit on his cock. I straddled his hips and after getting the panties to co-operate eased my ass onto his cock. He didn’t want me bouncing hard…..just a slow, deep, gentle ride. I moved my ass up and down on his cock, taking it from the head then slowly going all the way down. He reached under the cami top and played with my nipples again making move up and down a little faster. He then grabbed my hips and rolled us over and he was on top of me, my legs over his arms and he was pushing seep into me. My cock was hard and throbbing…..if I had touched it I would have shot my load. He never sped up or got in any hurry, he just fucked me slow and seep…..and I loved it. After about 5 minutes he stopped and got up on his knees and said, "You’ve been fucked like a woman…..now it’s time to get fucked like a slut. Get on your hands and knees." I rolled over and got on my hands and knees, I had barely gotten into the position when "Ken" yanked my panties down to my thighs, grabbed my hips and drove his cock balls deep in one hard push. I moaned louldly and he started fucking my ass like a jackhammer. He took long, hard, fast and deep thrusts into me…..my cock was getting harder than I ever thought it could. He paused long enough to get my panties off one leg and then had me open my legs and went back to fucking me hard. He put his hands on my shoulders and was pulling me back to meet his forward thrusts. He asked things like "You like it like this, don’t you?" and "You like my cock in your tight little ass, don’t you?" Of course I answered yes to it all. All of a sudden he pushed me down and he was on top of me drilling my asshole. It felt like he was trying to drive me into the ground and of course I was pushing my ass up to meet his thrusts. He had raised himself up onto his hands and toes and was pounding me, making sure every possible inch of his cock went into me. Then he took one last stroke, burying his cock in my ass and I felt his cock pumping his cum into me. I could feel it shooting out of his cock. His body tensed everytime his cock pumped. Then he pulled out and I felt his tongue on and going into my asshole…..he was eating his own cum as it oozed out of my ass. He told me to push as much out as I could and as I pushed he lapped up every drop. Then he turned me over and took my cock in his mouth. He sucked hard and it only took about a 5 count and I was cumming in his mouth. When I was done he helped me up and we walked back over to the swing, gathered our clothes and went inside where I tok him up on his offer of a beer. While we recovered he explained to me that he usually told guys he was only interested in getting sucked and fucking ass so when he did suck a cock the results were usually like mine…..a hard, intense orgasm. He also said he liked being outside listening to the night sounds as he fucked and I had to agree…when I was standing against the tree it was very erotic. He also admitted that because he usually came so hard he was a one shot deal, and I told him it wasn’t a problem because I was the same way. We laughed and agreed…..getting older is a royal pain in the ass bitch. I took off the skirt and put my jeans and t-shirt back on and he walked me out to my car. I put my pistol in the trunk after taking out the clip and ejecting the chambered round. Before I left we made a tenetative "date" for next week……..so check back around next Friday (05/29/15) and if anything happened and you want to read about it…..I’ll post it.