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“Ken” and I had another get-together the other night and since everyone wants to hear more…..here’s what happened.
My wife had to work a late night possibly over night job so I emailed “Ken” just after she left and asked if he was free for the evening. He answered an hour or so later saying he was as long as i brought ‘something extra to wear’. We agreed to meet at his house after I got the “clearance text” (a text from my wife letting me know that she and her co-workers had made it to their job location). While I waited for her to text I got ready. I was just getting out of the shower when the message came in and after answering her I sent a message to “Ken” and let him know I was on my way. I got to his house and he met me at the door and we went in. “There are some things on the bed, you choose which you like,” he told me as he directed me to the guest bedroom. I walked into the room and shut the door behind me. Lying on the bed was 3 different complete outfits. One was a white one-piece sundress, white stockings and white lace panties; the next was a denim miniskirt, a sleeveless navy blouse, with tan panties and stockings; the last one was a black, thigh-length nightgown with matching stockings and panties. I chose the sundress and after stripping out of my jeans and t-shirt put on the outfit. As I was adjusting the stockings I happened to notice that there were also shoes to go with the outfits. The sundress combo had a pair of sandals, the denim miniskirt appropriately had a pair of cowboy boots and the nightgown had a pair of 2″ heeled house slippers. Everything fit like I had ordered it for myself, the sundress hung 4″ below my ass and the sandals were only a tad too big. The stockings were the correct ones for my height and the panties fit like a second skin. I walked out of the bedroom to the living room and “Ken” was sitting on the couch. Without a word said I walked over, straddled his hips and we began making out. As we kissed and our tongues explored the other’s mouth his hands explored my legs and ass. He put his hands under the hem of my skirt and caress and massage my thighs but didn’t go higher than my stocking tops and when he rubbed my ass he never went under my skirt. I began to rock my hips and I could feel his cock getting harder and harder. I pulled away from him and turned on his lap and ground my ass against his cock. I could feel it pulsing through his khaki pants and he reached around me and put one hand on my chest pinching a nipple through the dress and the other hand was on my crotch rubbing my cock through the dress and panties. We ground at each other for a few minutes then he had me get up and we headed out the back door into the yard. We didn’t stop at the swing or bench, he led me to the edge of the bushes and led me down a little path. We walked for couple minutes until we came to a clearing that was about 8′ square. There was no tree or bushes in the middle of the clearing and the grass had been put down as sod and carefully maintained. There was a small plastic container in one corner. “Ken” walked over to it, opened it and took out a thick, king-sized blanket. He carefully laid the blanket out and then lay down on his side. I lay down facing him and we started making out again. We kissed and ran our hands over each other for a while then he grabbed me around the waist and rolled over, pulling me on top of him. I ground my ass on his cock while I unbuttoned his shirt. Then I turned around and helped his slip off his shoes and socks. I slid off his hips and had him stand in front of me. I unbuttoned and unzipped his khakis and slid them down his legs. He wasn’t wearing underwear so his cock sprang out of his pants and was standing straight out. I took his ass in my hands and pulled his cock to my mouth and started sucking his cock. I moved one hand to the front and gently massaged his balls as I sucked him. I decided to take a chance and as I massaged his balls I let my middle finger slip across his asshole. I heard him inhale sharply and felt his cock twitch in my mouth. I kept sliding my finger across his asshole every time I took his cock all the way in my mouth and after a few passes I felt him relax and I pushed the tip of my finger into him. He tensed up briefly but a few flicks of my tongue on the head of his cock relaxed him enough for me to slide more of my finger into him. I pulled my finger out long enough to wet it with some of my spit and his pre-cum and slide it back in him as I continued to suck his cock. I didn’t push hard or deep, just steady and matching rhythm with my sucking. He pulled my mouth off his cock and lay down on his stomach and asked if I would use my tongue instead of my finger. He spread his legs enough for me to lie down between them and I spread his asscheeks and teased his hole with my tongue. “Ken” was moaning and rolling his hips around and when I pushed my tongue into him he let out a long, low “Ohhhhhhhhhh”. I thought he had cum, but he hadn’t so I kept tonguing his ass, then He raised his hips enough for me to get my hand under him and stroke his cock. He had me stop after a few minutes and had me lie next to him. “I’m too close,” he panted, “I want to last a while.” We rested a few minutes then he was ready again. He had me turn my back to him and he snuggled up behind me. I felt his cock against my ass so I started slowly rotating my ass against him. I felt him lift the hem of the sundress and lay his cock on my ass and could feel it throbbing against me. He slid his cock on my panties and I pushed back against him. I then felt his hands go under the dress and then he pulled my panties off my ass and rubbed his cock against my bare ass. I felt him shift his weight but not enough to pull completely away then he moved his cock. He was only away for a few seconds then I felt his lubed cock sliding between my asscheeks. I ground back against him, feeling his cock slide from the tip of the head to his balls over my hole. He was moving a little faster and with more power, and I thought he was going to keep on until he shot his load on my ass, so I took control. Just as I felt the head of his cock slide past my asshole, I arched my back and when he pushed back the head of his cock was aimed right at my asshole and he pushed into me. We both let out a deep sigh as his cock slid deep into me and continued his long, slow deep pushes. We fucked like that for almost 10 minutes, every time he would feel his orgasm building, he would slow down. He had one arm laying across me and was holding me tight and would pull me back against him as he pushed into me. Then he rolled onto his back taking me with him so that I was sitting on his cock. I lay back on him and raised and lowered my ass on his cock. He told me to turn facing him so even though it took a minute, I managed to turn facing him and his cock never came out of me and I started riding him with the same pace he had used. “Ken” was moaning and saying how good my felt and much he liked fucking me and I answered by telling him how good his cock felt in my ass and that I loved having him fuck me. He had me ride him for a long time and then he pulled me to him in a bear hug and rolled us over. I spread my legs to let him on top of me, I wrapped my legs around his waist as he guided his cock back into me and continued to fuck me. “Ken” was arching his back, pushing his cock deep into me and I was raising up to meet his hips. He leaned down and as his lips touched mine, his tongue pushed into my mouth and he shoved his cock as deep as he could and shot his cum into me. My cock was throbbing and just as I started to jerk off, he stopped me. First he moved to my ass and licked his cum up as it leaked out of my ass then he stood up and asked, “How much time so we have?” I told him I had most of the night because of where my wife was working. “Good…..let’s go inside. We have a little more time to play.” So we gathered up the blanket and packed it back into the case, picked up his clothes and shoes and my panties, walked back through the trail to his house. We stopped in the kitchen long enough for a beer and to let my cock rest so my orgasm wasn’t too quick. “Ken” led me back to the guest room and asked that I put on the denim miniskirt, blouse, panties and stockings but wait to put on the boots. “Ken” wanted to ‘help’ me change. He got behind me and slowly lifted the sundress up and over my head, pressing his body close as he did. Then he had me sit on the edge of the bed, he kneeled down in front of me and slid each stocking slowly off my legs. He liked doing it because his cock was slowly getting hard again. Then he got up and say in the chair that was in the corner of the room and told me to dress. I picked up the panties and after stepping into them, slowly slid the up my legs and turned my back to him so he could see them covering my ass. I sat on the edge of the bed and slowly pulled the stockings on, taking my time, making sure they were even and high enough. Then I pulled up the skirt and zipped it, it was an inch or so shorter than the sundress then I put on the blouse. “Ken’s” cock was hard by now and so was mine. “Ken” got up and went to the dresser and took out a 7″ dildo with a suction cup base and after moistening it, stuck it to the full-length mirror on the back of the door. He looked at me and said, “Can you help me with a little fantasy?” I said of course, and he continued, “I’ve always wanted to get my dick sucked while watching the person sucking get fucked. Since we’re the only 2 people here, would you mind using the dildo while you sucked me?” I answered him by walking to the mirror, reaching under the skirt and pulling my panties off my ass, bending over and taking half the dildo’s length into my asshole and saying, “Bring that cock over here so I can suck it.” “Ken” stood in front of me and I took his cock into my mouth and started moving back and forth, taking the dildo into me and letting his cock slide to the head in my lips then moving the opposite way, taking his cock deep into my mouth and letting the dildo slide out of my ass. “Ken’s” cock was hard and throbbing again, and it only took a couple minutes before he had me stop and move off the dildo. He had me get on my knees and positioned the dildo at ass level and then got on his knees in front of me and we started the routine over again. For some reason, anything bigger than about 6″ (cock, vibrator or dildo) hurts if I try to take it too deep, but I surprised us both by taking the dildo all the way into me, sliding my ass along its length until my ass was pressed against the mirror. “Ken” couldn’t hold back and he gave me a mouthful of cum. I was so close to cumming if I had breathed hard on my cock I was going to shoot. AS I swallowed his cum, “Ken” watched as I slowly moved forward and the dildo slowly came out of me. I told “Ken” to get on his knees and he did so thinking I was going to lick his ass, but instead I got behind him and pushed my cock into his asshole. He resisted a little but gave in and I pounded him, all the while he was watching in the mirror. I didn’t last long, I grabbed his hips, got every inch of my cock I could into his ass and shot my load into him. When I stopped cumming, I bent down and licked my cum from his ass. As we were sitting on the floor recovering, “Ken” said that was the first time another man had fucked his ass, and with me dressed it looked like he was being fucked by a woman with a strap-on which is something he always wanted to try.
It was only about 11:30PM and we decided to rest a while and try playing some more after a recovery period. So after I stripped and we both cleaned up, we grabbed a couple beers each and went out to his back yard and sat on the swing. “Being naked outside has always been a turn-on for me, I told “Ken”, “I remember when I was young, going into the woods behind my house and stripping off my clothes and feeling the breeze on my body. When I was in my teens I’d pack a backpack with water and granola bars and be gone all day and I would ride until I found a secluded, strip off and masturbate. I found a dildo at friend’s house and took it and it would go with me on my rides through the woods. I’d find a nice, quiet spot and start jerking off and then I would use the dildo until I came. I found an old 2″ wide leather belt in the junk my mother was throwing away and an idea came to mind. I took the belt and cut a hole in it big enough for the head and shaft of the dildo to fit through but not the swell of the ‘balls’. I packed it in my backpack the next weekend and headed out. I rode a little further and found a quiet spot by a creek. After siting for a while to make sure there was nobody around I stripped off my clothes. I lay in the sun for a few minutes then got up and looked for a tree that was straight and thin enough for the belt to go around. I found a live oak that was perfect. I hauled my stuff to the tree, just to make sure it wasn’t spotted and took the belted dildo out of my backpack. It was a perfect fit, the tree was just skinny enough to let me snug the belt tight so that the dildo was standing out like a hard cock and not slip and slide. I lubed the dildo and and stood in front of it. I bent over and eased back until I felt the head against my asshole. I relaxed and let the dildo slide into me. The feeling I had was mind blowing. I was naked, in the woods, fucking myself in the ass with a dildo. There was another oak within arms reach so I hugged it as I pushed my ass against the dildo. I stopped when my knees started to get weak so I stood up and lowered the dildo until it was the right height for me on my hands and knees. I always carried an old quilt with me so I’d have something to lay on out in the woods so I got it out of the backpack and after making sure there were no ants around, spread it out best I could around the tree. Then I got on my hands and knees and backed up to the dildo and started fucking myself again. I was moving slow and deep at first but I was slowly speeding up and taking the dildo as deep as I could. I stopped again and lowered the dildo as low as it would go and this time I wrapped my legs around the tree and pulled my ass onto the dildo. It was like the tree was fucking me. I started jerking my cock and it wasn’t long before I was shooting my load onto my stomach. I lay there with the dildo in my ass, my asshole clinching the dildo, my cock throbbing and pulsing and the wind and sun on my body. I got up, cleaned up and got dressed. I had just packed everything up and was just getting back on the trail when some people rode by. I looked back and realized if they had been 3 or 4 minutes sooner they could have seen me. I didn’t check one direction…..I was hidden from people on the creek but not the trail. The spot I picked was only about 15′ from the trail and almost in plain sight.” “Ken” had sat and listened to my story and had his cock in his hand slowly stroking it. It was hard and ready for more. “I’d love to watch you do that,” he said. I told him that if we had a strap-on I would. He said he would look for one if I would show him what I did. I told him that I’d love to and that I used to do that all the time. I had him stand up and we went to the spot in the middle of the yard and I told him to pretend he’s a tree. I bent over and eased my ass back until I felt his cock at my asshole and slowly backed onto his cock. I reminded him not to move to let me do everything. “Ken” stood still as I worked my ass on his cock. After a few minutes I had him get on his knees and after getting his cock in my ass, fucked myself on him. The last part was tricky, but he came up with a solution. He lay on side, pushed his cock between his legs and took it in my ass with my legs on either side of him. I was pushing my asshole onto his cock and stroking mine. I groaned and shot my cum on my stomach and when “Ken” felt my asshole contracting, shot his cum into me. We lay there until we could get up and we both knew we were done for the night and went inside. As I got dressed “Ken” said he would get a strap-on to watch me even though he just had, but he wanted to see it done. He said he would email me when he got it. I left and when I got home, took out my wife’s dildo and used it until I came again.
I got an email from “Ken” just as I was finishing this………let y’all know how it turned out………IF you want to know.
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