My First Experience with a Man

[mj206]

It was around 2005, I was a junior at a northeastern college and I was doing ROTC as well. My sexual experiences with other people had been limited to women (dating as well), but my solo exploration was quite adventurous. As soon as I hit puberty and started masturbating I started playing with my ass. I don't know what inspired it, but I had progressed through the years from fingering myself and just generally exploring, to intentionally stretching my hole with whatever I could get my hands (ass) on. Over the years I had used markers, bananas, vegetables, shampoo bottles, water bottles, and finally, once I was older, dildos that I had purchased online. (I had also had quite a bit of experience with solo piss and scat play.) Of course, as I had a roommate at college, my ass-play and exploration was quite infrequent so it wasn't like my boy-hole was a gaping mess or anything, but I knew that I would be able to comfortably take a thick cock - if the time came.

I had been reading the Craigslist ads for a year or so and found myself really turned on by the idea of playing with an older guy. I don't know exactly why, but my interest has always been in older guys that were looking for a wet mouth and a tight ass to fuck. I've never been interested in topping a guy, and I wasn't then, and still am not very interested, in having an orgasm myself actually. If it happens at the end that's fine, but I prefer to play for a while before I have my own orgasm as I tend to lose interest after I cum. So I was 21 years old, reading the M4M section, and getting a feel for what was available in the area. I can't remember if I posted an ad or if I responded to an ad (I probably posted it) but I eventually settled on a guy in a town about 30 minutes away from school. He was a white guy, married, tall beefy but out of shape in an old man sort of way, and probably in his late 50s.

After a couple of emails and probably a few picture trades we made plans to meet a few days later in the week. That whole week I was perpetually boned and both excited and extremely nervous. Not only was this my going to be my first M4M experience, but I was also a little concerned about the CL sketchy-ness of it all. So on...let's say Friday...I ditched my friends, walked to my car, and started driving to this guy's town. He had given me an address and told me to meet him at some sort of historic building in his town. Apparently he was the town historian or had some sort of role that gave him access to the building at night and he thought it would be a good location for a private rendezvous. I drove to the given address and parked on the street. To my left was an old church or train depot or something (it's crazy how the years have dulled the memory that seemed like such a big deal at the time). As I parked I saw a door open and there was a man silhouetted in the doorway. I got out of my car and walked across the street and up the stairs to him.

At this point my heart was absolutely pounding from excitement and apprehension. We probably shook hands awkwardly and then he ushered me inside. His physical appearance was true to his pictures and he seemed like a nice enough guy. He was also obviously a little nervous, but seemed to be in better control of himself than I thought I was at the time. I remember walking through several rooms and hallways filled with simple little display cases and framed pictures until we came to a back room. While we were walking he explained his role in town and the significance of the building, but I doubt I even processed any of what he said. All I could think about was the throbbing erection I had in my pants and the pounding heart I had in my chest.

Once we were in the back-room he closed the door and motioned to some blankets he had arranged on the floor. The room had that cheap kind of industrial-grade carpet and smelled of dust. He stepped close to me and asked "Are you okay with this?"

Nervously, I answered 'yes'.

Then he put a hand on my crotch and remarked on my hard on. He didn't say anything further but he began to unbuckle my belt and unbutton my pants. He pulled my pants and underwear down and my hard cock bounced right up to attention. He cupped my balls with his big hand and began to caress my cock. I distinctly remember almost cumming right then, and so I quickly (and so nervously/excitedly) pushed myself away and said, "Can I see your cock?"

Of course he replied 'yes' and then stepped back to unbuckle his pants.

As he was doing that I finished taking off my pants and then dropped to my knees in front of him. At this point his pants were down and his briefs were exposed with an obvious erection inside. I reached up and slowly pulled his waistband down allowing his fairly large and thick cock to spring out. I pulled his briefs down to his knees and slowly began to grip and stoke his cock, which was the first cock I had ever touched...other than my own. He just stood there silently smiling and staring down at me. I remember desperately wanting to just gobble his cock, but knowing that with this being my first time that I should take it slowly in order to fully appreciate the moment.

So, I was on my knees with his meaty cock in my hands. I looked-up and made eye contact with him, and then I lower my mouth towards his inflated cock head. As soon as my lips touch his cock I felt a wave of relief and pleasure wash over me. I remember that it felt like I had finally found something important that had been missing for far too long. I popped his head fully into my mouth and swirled my tongue around once or twice, and then lifted his cock towards his belly and began to his and lick his shaft, and then tipped my head to the side a bit so I could get my tongue on his heavy balls. My hand gripped his shaft and my tongue lightly licked his sack. I can still remember realizing that my nose was tightly pressed up in his sack and that his scent was incredibly sexy. After that I began to fully suck and lick him in a way that I'm sure was truly amateur.

After doing that for what seemed like forever, but I'm sure was only minutes, he sat on the ground and told me to get between his legs and keep sucking. He was not at all too dominant, but I do remember feeling like he was the one that was obviously in charge and knowing that I really wanted to keep pleasing him. I knelt on the floor and leaned forward on my stomach as I continued to suck him. At some point he began to pat and squeeze my ass, tracing his fingers over my hole. After a minute or so, he reached back further, and seriously played with my hole.

At this time in my life I was 5'9" and in good military shape, but I had the lean body of a runner and not a thickly muscled frame. I was probably about 145 or 150 lbs of lean muscle. I like to think that my ass was pretty cute and bouncy. My body hair is naturally light except for my legs, pubes, and ass, but I used an electric trimmer to keep my leg and ass hair down, and my cock and balls were shaved smooth with my pubes being trimmed close. After a few minutes of me sucking and him touching he pulled me off his cock and told me that he wanted to fuck my ass. As absolutely great as sucking his cock was, a proper ass-fucking was what I had been waiting for so I eagerly agreed to his request.

He had me turn around in the doggystyle position and gently rubbed some lube into my virgin (technically) hole. While doing this I asked him if he had brought a condom. He said that he hadn't because he was allergic to latex and that he hadn't used a condom with his wife in over a decade. He then asked me if I had fucked any other guys to which I said that I had only been fucking one girl (my girlfriend) for the past couple of years and that I was sure I was clean. He assured me that he was as well. I had gone into this thinking that a condom was going to be absolutely necessary, but in the heat of the moment I gave in. All I knew was that I wanted his big daddy cock in my horny hole.

He lubed his cock and then gently pressed his fat head against my tight (from nervousness) hole. His hands gripped my side and his greasy cock began to fill me. It felt fucking incredible. The physical sensation and the psychological sense of fulfillment were amazing. As my hole warmed to his cock he began to pick up speed. At some point his hands reached down and began to jerk me off in rhythm to his thrusting and in just a few jerks he had my formerly straight cock spurting while my ass clamped down on his big dick. I was totally lost in the moment but at some point he told me that he was going to pull out and that he wanted to finish in my mouth. I pulled myself off his cock and spun around toward his cock. He sat back on his ass and once again I knelt/leaned forward to take his cock in my mouth. A few bobs of my head and a few pumps of his hips and he told me he was going to cum. Regretfully, (very regretfully) I remember jerking his cock furiously with my hands while hovering my mouth just above his cock-head. His manly cock shot a big load of cum up toward the roof of my mouth. The taste was both familiar (I had tasted my own spunk a few times) yet different and I loved it. My supremely over protective fear of STDs kept me from doing what was right and swallowing his manly gift, but I turned my head a little so the hot spunk could cover my face. As he grunted and basked in the glory of his orgasm I gingerly cleaned his cock and slowly sucked on his shrinking member.

After a few moments of that we both got up, put our clothes on, and awkwardly said something like, "That was great. I'd love to do it again. Let me know if you ever want to do that again" and then we walked out and went our separate ways. I remember that on the drive home my ass was deliciously greasy and wet and that my cock just wouldn't go down. I never saw that guy again, but that encounter did launch a trend of playing with older married men about twice every year.

The end. That's a totally true personal story and I'd love to hear what you guys have to think. I can't claim to have had as wild a sex life as all of the men here, but your experiences definitely feed my fantasies.

Edited July 31, 2014 by Hotload84

[i69nwind]

so hot, I loved hooking up with guys in college from a bathroom to an empty classroom. I wish I would have been fucked then

[MAIKOL20]

I enjoyed your experience and am glad you enjoyed and keep at it. I love to please older men as a bottom boy too. It's easy to get used to.

[Guest Lempriere]

Great story -- I especially like your description of your apprehension and nerves about doing something you had never done before -- a feeling I can well identify with.