First Time Anal

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This is an anal sex fantasy.
2k words
4.12
29.1k
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I am riding my bike home from a long day at work. I'm really pumping hard working to get to the top of the hill I am climbing. I am enjoying the feeling of my legs screaming at me and the pulse of pleasure each time my asshole and taint rubs against my seat. As I turn the corner I spot two older men on the outside of their van setting up a parasail. I stop my bike, get off of it, and as I am removing my headphones they stop what they are doing and check me out from top to bottom, stopping at my crotch for just a second before saying hello.

We made small talk about parasailing for a few minutes and I asked if it was difficult to do. The first man, Bill, said no, it's very simple and asked if I would like to try it out. I quickly responded that I would. Bill then responded that I could if I wouldn't mind his cock in my ass. I looked at him with a curious look and replied you mean go tandem? No, I wouldn't mind that at all. He and his friend, Joe, both laughed and then he told me, that if I wanted to go up, his cock would have to go up my ass. As payment for the use of his equipment.

I'm not into men, I don't find them attractive and could never kiss or snuggle one. But I do have several fantasies, most of which revolve around sucking, stroking, and fucking a real cock. The rest are about sucking cum out of a just used pussy. I also love things in my ass and love to have my ass is played with. I wasn't certain if these guys were serious or not, but I was very curious as to where this would go. As I was imagining his hard cock oozing pre-cum as I stroked it and sucked it, getting it ready for me, and then fantasizing that I could feel it pulsating between my cheeks, my cock started to twitch. At that time, both Bill and Joe cleared their throats and recommended that we continue the conversation inside the van.

Now I am not a fool. I knew that if I went into that van I was going to have both of those cocks in me, whether or not I wanted it. So, I stalled. I asked if they were a couple, to which they both laughed and commented that just like me they were married to women, showing me their ring fingers complete with wedding bands. They explained to me that while they love their wives, and are faithful to them, sometimes they need to get some cock. I chuckled and admitted that I have been having similar thoughts for years, I had just never been close enough to a like-minded man or brave enough to take the chance. After a few more minutes of banter, Bill one told me if I didn't get in the van I wasn't going to ride his parasail. So, I looked him in the eye, then down to his bulge and said let me see what I'm going to get to fill me up. Joe smiled a knowing smile and adjusted his crotch while Bill pulled his sweat pants open for me to take a look inside of them.

Poking out of a really cute pink lacy thong was a decent, 7 Ā½ inch cock that looked like I could get my hand around and touch my fingers without squeezing. The head was purple and very wet. I smiled, licked my lips and then told Bill that it looked like he really wanted my ass. He nodded his head and moved into the van. I looked at Joe and said, you too. Joe was wearing red boy-short panties. I could see the shape of Joes cock through his panties and by the shape of Joes cock his head was a lot fatter than his shaft. While still decent in girth, his shaft was a bit narrower than Bills. It was also shorter, being well contained in the panties, I guessed it was 6 Ā½ to 7 inches long. He was excited, but not wet like Bill was. So, I reached my hand down into his sweat pants and grabbed his cock through his panties just below his cock head. I then rubbed his head with my thumb, enjoying the way his cock twitched in my hand each time I rubbed it.

I led Joe by his cock to the van and pushed him in backwards. As I climbed in Bill pulled the door shut. I immediately asked about my bike. We were on the side of a bike and hike trail and there was a lot of traffic. They assured me that it would be ok and the only thing that was going to be taken away was my "virginity".

I turned my attention to Joe who had already pulled his sweats down and was rubbing his cock through his panties. I crawled up to him placing my mouth over the head of his cock and blew hot air through his panties. I then gently nibbled his cock along his shaft before returning to his head, sucking it and his panties into my mouth. He replied with a groan of pleasure.

While I was playing with Joe, Bill had removed his sweats and was rubbing and grabbing at my hips while thrusting his partly panty clad cock against my shorts. I was enjoying the sensation so kept pushing my hips back and grinding my ass onto his cock getting his precum all over my shorts. I took my mouth off of Joes panties and told Bill to lay down next to Joe. I moved over to Bill and sucked his wet head into my eager mouth with a loud slurp. The taste of his precum and slightly sweaty, salty cock was as wonderful. I was instantly hornier than I have ever been in my life.

I sucked his head so hard, he told me to let off, just a bit, I did and also allowed his cock to fill my mouth, bobbing my head up and down on him like my wife does on me. I kept working at it until I was able to get my nose burred into his pubic hair. While I was working on my oral skills, I was playing with his balls which were on one side of his thong. I was massaging them while rubbing my finger along his puckered asshole and taint. With all my drool running down his balls it was not long before my finger was wet enough that I was able to push the tip into his sphincter. I continued doing this for a few minutes before moving my hand off of his balls and onto his shaft. I wrapped my hand around it and stroked up and down in unison with my mouth. As I came up, I looked over and noticed Joe was stroking his cock. I released Bills cock and grabbed Joes in my hand and then transitioned over Joe and sucked his cock into my mouth. It took some effort to get his fat cock head into my mouth but once I got it in, I started working his shaft with my hand while I enjoyed the taste of his precum.

Bill moved behind me and pulled my shorts down. He grabbed my dripping cock and used my precum to lube up his hand and then rubbed it up and down the crack of my ass. He then spit on his hand and started diddling my ass with his finger working one in before swapping it for another. After he had placed them in individually, he started working two at a time in and out. Each time he pushed into me I engulfed Joes cock. As he pulled them out, I came up for air.

I wiggled my ass to let Bill know I was ready for his meat. I then pulled Joes cock from my mouth and turned to Bill and once again engulfed his cock with my mouth. Once I got it really wet with spit I again turned around and wiggled my hips at him. He moved in close to me and placed his cock head against my asshole. I pushed into him and relaxed, allowing my ass to open up and take his cock. Just as his head was about to pop into my ass, Joe grabbed my face with one hand and his cock with the other. He rubbed his slick head against my mouth. I opened my mouth and took him in right as Bills cock entered my ass.

The sensation was unlike anything I have ever felt before. When I am playing with a dildo, it's just a cool, hard object. When I'm being pegged, it's not smooth nor easy, as we both have to work at it and there is never enough lube so it quickly begins to burn. This was totally different. His head was hard, but spongey. His shaft was veiny and hard, but it also had just enough "give" to make the sensation very comfortable, if not pleasing. When I flexed my anus, I could feel his heart beat in his shaft, and really feel the heat of his cock inside of me that put the sensation over the top! His breathing and the experienced way he thrusted into me and then slowly pulled gave me sensations that were unlike anything I have ever felt. As Bill pushed into me he forced my body forward into Joe. With Joes helping hands my nose was buried into his pubic hair as his cock slammed into the back of my throat. Then Bill would pull out and pull on my hips while Joe pushed my head back up and off of his cock. Then they would both push into me again. They were fucking both my holes at the same time, and I was really liking the feelings. Every time Bills cock went past my prostate, my cock jumped. I could feel my precum splash against my thigh as each thrust made my cock swing wildly. I wanted to touch myself, but the way Bill and Joe were using me, it was everything I could do to stay balanced on my hands and knees.

It felt like I was just getting into the swing of things, when Bill grabbed my hips with intensity and grunted as he thrust into me harder than before. Then he held my ass as close to his cock as possible. I could feel his cock pulsating in my ass, so I flexed it a few times which finished Bill off. Hearing Bill cum must have put Joe over the top as he grabbed my head and rammed his cock as far down my throat as he could. He buried my nose into his pubic hair and as I gagged he came. I felt his cock twitch at least 4 times before he finally pulled out enough for me to choke, cough, and gag. As his cum covered cock slid out of my mouth he told me I better not let waste any cum. Since I wasn't being rocked back and forth any more I was able to grab his cock and quickly went to work licking the cum that I had failed to swallow from around the base and up his shaft. I have to admit, it tasted wonderful and I really enjoyed licking his fat head.

As I finished cleaning Joes cock, Bill pulled out of me and then pulled my pants back up, covering my ass. He jokingly told me to enjoy the wet ride home. I pulled Joes cock out of my mouth and told him we had a deal and I was going to get my ride on his parasail! After the ride we all exchanged numbers and I rode home. My ass felt wonderful as Bills cum oozed out of it and into my underwear. It felt even better each time I allowed it to rub against my bike seat, especially so because I hadn't cum yet.

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AnonymousAnonymousover 5 years ago
No difference

Butt fucking is butt fucking.Would love to hear more about the adventures of our cyclist .

AnonymousAnonymousover 5 years ago

Wrong category.

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