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I had finally done it! I stopped fantasizing and started doing. I had placed an ad on a gay dating website and took the leap. I had been with two guys now, one my age, "Joe" and one younger, "Kimmy." I meet them both on the website. Kimmy reached out to me the next day after I had picked him up and we parked. We ended up kissing and sucking each other to orgasm in my car. Joe was a regular guys guy but Kimmy was my feminine, so when Kimmy wrote that he would like to see me again and dress up for me I wasn't that surprised.

Two nights later, I picked him up at arpund the same place as last time. He got in the back seat with a bag and said he had to get ready and not to look. I was driving back to our secluded spot when he asked me to drive to different part of the town. When he was ready he said, "ok stop, let me out then come back and pick me up" I turned to ask, "What?" when I saw that Kimmy had dressed up like a girl, dress and all and was wearing a wig. Now, I wasn't really ready for this, but decided to go with it. Besides, he looked beautiful. I circled the block and pulled up to him as he was walking down the street. I thought Kimmy would like some roll play so I asked if she needed a lift. Kimmy fell right into character, acting like a girl in distress who needed a lift and would be most grateful. I'll be honest, my cock hardened in my pants. I drove around the corner to a dark parking lot and Kimmy said, "let me thank you" and put his/her head in my lap and began to undo my pants. My cock sprang out and Kimmy went down on me. His wet mouth devoured my horny cock and it felt amazing. I reached over pulled up the dress and slide my hands down he back of his thong. When my finger found his hole he moaned loudly, even with my cock in his mouth. He was letting me know he liked it I think. His little ass felt great in my hand and I loved rubbing his little hole. Kimmys mouth felt so good on my cock, this was obviously a fantasy for him so I wanted him to enjoy it also. I pulled him up from my cock and said, "baby that feels so good" then drew his mouth to mine and kissed me deeply and passionately. I said, "baby, you're so fucking hot!" then pushed his head back down on my cock. Kimmy sucked wildly on me and siliva dripped down my balls. I rewarded him, I mean "her" with an explosive orgasm for his efforts. Kimmy swallowed my cum and made loud gagging and gulping sounds. After my orgasm subsided, I said, "baby, let me lick your pussy" still into the roll play. Kimmy got a big smile and quickly spun around in the seat and arched his back, offering me his ass. I pulled down the panties just enough to expose his tight little asshole and began to lick it. Kimmy cooed and moaned like a girl. It was so sexy and hot! I licked at his asshole and fucked him with my tongue. My cock was hard again! I wanted to fuck his ass right there and then, but Kimmy swung back around to sit down and flung back the dress to show me his hard, throbbing cock. "Suck my clit, baby!" Is all he said as I dove forward and took his cock into mouth hungry, wet mouth. I was so turned on and so was Kimmy. He reached up and pulled my head down onto him and then without warning released his cum into my mouth. Oh, I loved the taste of him, the force of his orgasms shook his whole body and I soon found myself having to swallow again and again as his cum filled my mouth over and over. The flavor and texture coated my lips, tongue and mouth. His cock was thick at the base but pointed and skinny at the head, he fit in mouth mouth perfectly and I continued to savor his cock and cum long after his orgasm and erection subsided. Kimmy said, "mmmmm, baby that was amazing and lifted my head up. Holding my face in his/her hands, he kissed me slow, soft and lovingly. Jeez, I thought, I could fall for this one. As we kissed, his hand reached down and felt my aching, raging cock again and began to stroke me. Now I moaned and kissed him back deeply. "Baby, we have to save this for another time" he said. I lust was overwhelming and boiling over, I said, "Baby, baby I have to cum again, please" Kimmy got a huge smile and asked if I wanted to jerk off really quick on her face. Oh my gosh yes, I thought and quickly sat up and bEgan stroking myself to orgasm. I came on Kimmys beautiful face as he moved from side to side. "Thank you, baby" Kimmy said, but of course I thanked her back! Kimmy wiped the cum from her face and chin with the back of her hand and sensually licked it off. " fuck baby, you are so hot" I said and Kimmy just smiled. "I better get back" Kimmy said and then got back into the back seat. I drove him back to his drop off spot and when he got out he was back in his regular boy clothes. Hope to see you again soon, he said as he walked off towards his house.

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CynthiaChapter 15 Bradford

Sarah and I communicated well when she had time for conversation, often after her shift was over. She made it clear that she liked me as more than just a patient, and in addition to liking her, I found myself lusting for her constantly. It wasn't so bad in the mountains when there were no distractions, but to see it around me every day flamed my desire. She caught up with me while I was in physical therapy. After a couple of cheers, she said, "I got her cell phone. I'll see you...

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Adventures of a Greenie Off Planet Vol 2Chapter 27 Forbidden Forrest

Lamax system was only 61 lightyears distant to Faysummit system. Meaning the superfast Colt reached Faysummit only 136 minutes. Roy was getting more anxious by the moment. The closer he got the more he felt convinced that his mother was close and that she was in great peril. The Colt was brand-new and by law, it was his ship. The Phantasian who piloted the ride was an employee or more precise a contractor. Tanya was right, this passenger cabin was not big enough for Partner, but then this...

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Michigan Snowmobile Adventure

My buddy Brandon and I had planned our snowmobile trip to the upper peninsula of Michigan for weeks in advance. We planned to drive to the upper peninsula of Michigan and be there a week. I had reserved six nights at a small bed and breakfast complete with a guide to take us for some off trail riding and we were eagerly looking forward to a great time. But three days before we were to leave Brandon came down with the flu. This posed a dilemma as I put a non-refundable deposit down on the room...

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Creampie Snowballing Try It

Dusty and his wife Christy are an average couple with not-so-average sexual tastes. You see, in this relationship cum is shared by both! Hers or his! They have been snowballing cum kisses throughout their relationship, in fact it was a key ingredient in the entire courting process.Christy considers herself a cum addict or a cum slut since she loves cum and wants it in her mouth every single day! First thing every day when she wakes up is to coax a nice warm load out of her husband. Of course he...

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Being a slut Thetford forest

This is a true story and happened recently. I am bi and enjoy sucking and being sucked by guys occasionally. But on the odd occasion I het so horny that I need fucking. A couple of weeks ago it was early evening and I found myself heading to a cruising spot where I have met guys before. I parked up in a layby. it was stil light, and it was quiet. Eventually a white van came slowly driving by, as he passed I flashed my indicators a few times. He pessed his break lights a few times and we had an...

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Lucknow Lady Comes To Bangalore For A Massage

Hey, folks, it took a while to pen down my experience. Busy office schedule, appointments, travel had kept me busy. A quick intro about me. Nishant (Nish) here from Bangalore. Working in an IT firm. Have been offering massages to females and couples for over 6yrs now. Have traveled across India only for massages and on a couple of occasions have offered massages during my business trips overseas as well. You can check the author page for my other experiences submitted on ISS. There are many...

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Lucknow Saharaganj

(The Names in this story have not been published as it’s a true story and privacy is required) Lucknow, Nov 2010: I am a 26 years old married guy, 5 feet 11 inches, very fair and smart as most people say, working at managerial level in a multinational bank. Simple fact about me. I simply love married women. After being happily married for 2 years, I have developed a strange fascination and attraction towards married women! And it all started on that evening of 25 Nov 2010 in Saharaganj,...

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Snowy and the Seven Petites

Snowy and the Seven Petites by captv8td [email protected] 1She couldn’t tell if the woman was dead or merely unconscious.? Either way, it was clear that she was not a willing participant in the activities taking place in the glen.? She watched as the man’s massive cock slid out of the woman’s body, glistening with juices, only to be rammed deep back into the still body.? Hippy thought it was disgusting that the male would take advantage of the motionless body.Hippy pulled an arrow...

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A white rich bitch falls for a well endowed black forklift operator who works at one of her husband8217s warehouses

Hello, my name is Charlotte. I know you won’t believe this and normally I wouldn’t admit to it, but I am Otis’ cock slave. There really isn’t any other way to put it. And the really strange part, the really, really strange part, is that I come from a straight-laced New England family and Otis is barely educated and was just a worker in one of my husband’s warehouses. This is a strange tale, one that I find hard to believe even though I am living it. I first met...

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Snowys Visit Ch01

“Do we need something from the store?” I asked Lydia while standing on the doorstep.“Sure. Get some bread. Oh, and get a bottle of coke,” she answered while approaching me. She kissed and hugged me, then continued: “When will you be coming back?”“I dunno… Around eight, maybe? Let’s say eight-ish,” I answered, already closing the door.“Cool. Oh, and I forgot to tell you – Snowy’s coming over sometime before eight o’clock,” Lydia announced casually. Snowy – or Snoween (yeah, really) by her full...

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Snowys Visit Ch 03

“Just to go over it again – what you’re saying is that you…” Swan pointed at Snowy “…had sex with her…” he pointed at Lydia “…and him...” he pointed at me “…one night when you got drunk and played strip poker?” he finally finished.“Yep,” Snowy replied casually as if the question was about the weather.Well, it turned out to be a peculiar last few hours in our little apartment in Zuljana, in southern Croatia. After an incredible morning, topped off by brazen displays of sexual affection between...

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