My First time with a man

by Bob Long

2 Feb 2020 6605 readers Score 8.4 (81 votes) PDF Mobi ePub Txt


This happened a few years back when well we shall say I was sexually frustrated when my wife hung up the temporarily closed sign and sex at home was nonexistent that damned women’s issues, but I still had and have a very strong sexual appetite. Searching around on the net I came across a site that listed hookup places around the country and without even a second thought clicked on not only my state but same gay encounters. My experiences with the men were limited  to back when I was into cross dressing and living with my girlfriend where I lived as a woman nights and weekends, vacations etc. I missed those days I found a cruisy park not far from where I lived but far enough where I wasn't afraid of running into anyone I know, kind of dumb thinking back as it's where a big mall is where everyone shops and is a local historical park so the likelihood of seeing someone I know was better than my sexually motivated mind had thought.

So the deal is you pull into this country park and go to the first rest area and back into a parking spot this indicates to others in the know that you're there looking for a hookup, so armed with the knowledge of fully knowing what I was doing I backed into a spot and noticed there were several other vehicles in the parking lot most of which were not occupied. Just in case I had a backup plan. I grabbed an item from home a car part actually so that if questioned by the police I could simply say hey I was here to meet a guy to sell him this and not have anything in my hand except my cock..

When I finally got there after drinking a large coffee I really needed to go empty my bladder and felt a little relief when I entered the men's restroom and was alone. I stepped into a stall that only had sides and no privacy door behind me, I was engrossed in the pleasurable experience of relieving myself a pleasure all men know when I heard this voice say very nice looking cock, I turned to see this athletic younger man with his hand holding what looked like the cock of a porn star, awesome looking actually maybe 4 inches around and about 8 inches flaccid, I stared at it and barely was able to mutter the words thanks. Even though that’s exactly why I was there the hetero part of me was telling me to naturally zip up and flee I stood there admiring his member and just looked at his cock and said wow nice, very nice. He smiled and took my returning compliment as his que and began stroking his cock, he asked me first time here I nodded yes well not first time here but first and before I could get the words out he said first time seeing a cock I must have turned red with embarrassment indicating myself as a newbie and he said it's cool you've got a very looking nice penis I thanked him again and hadn't realized that I had been getting aroused as it was quickly going from flaccid to erect, I should have been embarrassed but instead I just did as he was doing and began to stroke it.
We stood facing each other and he took a few steps closer and the heads of our cocks were almost touching, when he politely asked do you mind and extended his other open hand palm up and I didn't need to be told that he wanted to touch my cock, without realizing it or even recalling whether I said yes or not my facial expression must have given him the go ahead and he reached out and took hold of my cock and began slowly stroking me. It was euphoric to say the least my cock finally had human contact with someone other than myself, I just closed my eyes a bit and enjoyed the touch of this strangers’ hand on my ever-growing hard cock. I opened my eyes and instinctively reach out for his and felt his cock in my hand it was a surreal feeling and his cock grew to what I only estimate to be at least 12 inches and was hard as a rock and some weight to it was actually heavy, dam I said a smile and I slowly stroked it pulling it toward me gently milking it. He let out a soft moan and asked if I was sure this was my first time. I trembling voice I said yes I'm sure, well you’re a natural at this for sure and quite good too.

He said come with me before we get interrupted and we headed out the exit door and he stopped and looked I'm guessing for park rangers or whomever and I followed him for maybe 20 or 30 yards to a secluded picnic table behind some trees yes secluded from behind but you could see clearly across the field in front which I hadn't realized until after we were done. We sat down on the bench and he pulled his cock out and pulled down my shorts and gasped and said oh my! you have the biggest balls I've ever seen! I proudly said yeah, I've been told that before. We sat next to each other and softly rubbed and stroked each other’s cocks well he was apparently more excited than I was and I heard his breathing increase and his body tense up I instinctively know that he was going to cum but he was doing his best to hold back and was softly saying oh yes, yes, yes do it please and without a chance to utter another word I had picked up my pace and was feverishly pumping his hard cock determined to make my new friend cum. Within seconds his head spurted out a gusher of cum and I kept pumping it and cum kept spurting with every stroke until he was empty, he was panting and breathing heavy my hand was now full of another man’s cum, and in between breaths said thank you my friend he seemed to gather up his cum with his hand and licked it. He looked down at my still rock hard cock with his hand still holding it but not moving and said ok your turn and he started pumping my cock just like I did to him, he now starts talking to me so how does it feel having your cock stroked by a strange man you love t don't you, all I could do was mutter oh yeah I love it. He said I am going to make you cum baby I'm happy I was your first. He continued stroking and he reached down with his free hand and cupped my balls and said my god you have a pair of cannon balls here. He held onto my balls as he increased his stroking and feverishly pumped my swollen cock

When all of a sudden he stopped and dropped to his knees and before I realized  what was happening he engulfed my rock hard cock in his mouth and began sucking it feverishly, I am a huge fan of oral sex and loved getting blowjobs since my early awkward teenage years what guy doesn’t but this was strangely super erotic and so different. I just lay my head back and embraced this new-found pleasurable feeling and it was almost like an out of body experience. He continued for a few more minutes and as quickly as he went down on me, he had stopped. I protested a little and said please don’t stop it feels so good, but he just smiled at me and said another time and went back to skillfully stroking my throbbing hard cock. I now could feel my body start to tremble the feeling I knew so well and lived for like most guys 


I could feel the fire in my balls begin to erupt and I couldn't hold back any longer without any warning I just let out a grunt and began to spurt out a stream of cum that must have shot several feet in the air just as I had done to him he kept pumping my cock milking out every last ounce of cum and just looked at my cum covered cock and without hesitation went down on it and licked and sucked every ounce of cum and totally cleaned my cock, being so hyper sensitive as I always am after I cum it felt both electrified almost unbearable but equally erotically pleasurable he even flicked my balls with his tongue and looked up at me and asked if he could please, even though I was spent I just nodded and he sucked on them while holding the shaft of my cock. He tried his best but was not able to fit either one in his mouth.

My phone rang and it shocked us both back to reality, I looked at it but didn't answer it and he got up and started to pull up my short and when I looked at him as if to say he wait he looked towards some voices coming from far across the field, without saying a word we both put our junk away, he asked will I see you here again, I smiled and said you can count on it, driving home I realized I didn't even know his name.



My pursuit of cock 


A little follow up, I did meet him there the following weekend and countless times after for our weekly meetings as we called it, his name turned out to be Brad and the meeting after our first time he smiled and said do I even need to ask for your permission as he pulled down my seat pants no not at all I replied and when he did it revealed that I was wearing a neon pink pair of bikini panties. He gasped and smiled saying well now look at you sexy. He licked the head of my cock through my panties and proceeded to tease the hell out of me and wickedly enjoyed every minute. He finally decided play time was over and got down to business he took my almost fully erect cock in his mouth sucking and bobbing his head up and down on my cock, momentarily  stopping to suck on the head of my cock while pumping my shaft. He went back down on my cock and skillfully sucked on my cock without using his hands.  I moaned I’m cumming baby, I’m gonna cum giving him fair warning as I had it drilled into me by all the women who went down on me over the years all of whom were not cum swallowers. Such was not the case with Brad, he sucked even harder and bobbed his head faster until he brought me over the edge, and I exploded in his mouth. He skillfully did not lose a single drop. I pumped what felt like a quart of cum into his belly and when I finally finished and thought I was going to pass out he just looked up and me with my drained cock still in his mouth smiling, but instead of allowing me to remove my drained now super sensitive member from his mouth his kept his sucking and bobbing his head I started gasping and panting and looked at him as if to say what the fuck are you doing barely muttering holy fuck what and he produced a condom from his pocket handing it to me. I now knew he planned to get me fully erect and when I was, he wanted me to fuck him in the ass. Something I mentioned  to him once about fucking my wife up the ass. So, Bruce continued his masterful and extremely sensual cock sucking he later told me how incredible feeling it was having my cock grow in his mouth back to full hardness. He sucked and licked the shaft of my cock and licked and sucked my balls  and looked up at me and smiled I’m ready was all he said he got up and bent over the picnic table offering me his ass. I tore open the condom wrapper and slipped it over my glistening cock  I rolled it down the shaft  and made sure it was all the way down being a magnum sized condom person Bruce knew his cocks and provided me with the right size rather than some super tight torture device.

With my cock now fully protected I slowly slid the tip of my cock into Bruce’s ass which by the way was absolutely perfect, round full and firm the ass of one who took very good care of himself. With one hand holding my shaft and the other on his ass cheeks I slowly slipped the head of my rock hard cock I entered him, he let out a soft moan, oh yes! he cried that’s it, yes that’s it fill my ass with your cock. I had both hand on his hips as I pushed my cock deep into his ass until I was balls deep. He lets out a moan saying oh my God you fill me up with your cock now fuck me please fuck me. I started to slowing pump my cock in and out of his ass as I had done with numerous women before but never with a man and never with such a nice ass. As I fucked his ass, I could feel my balls slapping his against his ass. As I fucked him, he was encouraging saying oh yes that’s it you feel so good, show me how you pounded all those bitches in the ass give me your load. I started to respond  telling him I was going to rip the rubber off and fill his tight little ass with cum. Oh yes give it to me please give me your load he begged. I was ready to pull out and tear it off but without even giving a though to why he wanted me to wear a condom I just kept fucking his ass. I could feel myself getting ready to explode and I blurted out fuck I’m cumming and just let out a grunt as mu cum started filling up the condom I kept pumping  until I had nothing left and just stood there with my drained dick in his ass. We both caught our breath for a moment when he said ok take it out. I slapped his ass pretty hard saying when I’m good and ready bitch. He laughed saying no seriously please take it out. I did as he requested and when the head reached the opening, we both heard a popping sound. He laughed and turned around got on his knees pulled the condom off and licked my cock he then took the condom and squeezed its contents into his mouth. He smile and said much to yummy to waste. Enjoy was all I said.





My conquest of his cock


As he stood up, I said I have a favor to ask, he looked at me replying name it. I want to suck your cock. He looked at me saying well we don’t have a lot of time but are you sure you want to. I nodded and went down

on my knees and tugged at his shorts until I pulled them down and then pulled his underwear down as well exposing his glorious cock.  I put this massive cock to my lips and began to suck on the head of his cock I slowly took on more and more of it filling my mouth. His cock was enormous porn star quality without a doubt. Thankfully he wasn’t fully erect I kept sucking and stroking his cock and moaned saying there is no way this is your first time, afraid that if I pulled his cock out of my mouth to answer him I wouldn’t be able to get it back in so I just muttered ahh hmm for a yes. He had his hand on my head saying you’re a natural. His compliment made me more determined than ever to see this through, so I attempted to get more of his massive now fully erect 12 inch cock into my throat. If I had to guess I’d say I maybe got half of it in as there was still plenty of shaft to stroke. I resided myself to the fact that this was as much as I was going to be able to handle so I sucked and pumped my head bobbing up and down on his shaft. I was so focused on my cock sucking that I hadn’t realized that two other lovers happened to come down the path from deeper in the park. When Brad noticed them, it was too late, but he said when he saw them holding hands his fear left him and he didn’t feel the need to have me stop. The two guys stopped and observed, Brad placed a finger to his lips to indicate that I had no clue, so they made a point of being quiet as they stood there watching me go down on him. One of them mouth wow to him and Brad gave him a thumbs up and mouthed back first time. This must have been extra titillating for them as Brad told me within seconds, they had both their cocks out stroking. Here I was a newbie and I had an audience.


 I feverishly continued sucking and slurping and forcing his cock as far into my mouth as I could. I could feel his legs tense up along as he began to meet my sucking with his hips. I knew the signs this was it my very first load of cum I was bound and determined to swallow his entire load. Brad let out a loud grunt that probably could be heard across the park and he began to spew a monstrous load from the head of his cock that was now as deep in me as I could manage I actually felt the first spurts of his load shoot right down my throat if my gag reflexes were better I would have been able  to just keep him in my mouth as his cock emptied his balls not missing a drop but alas  I was not that talented and as I pulled his cock from my mouth he was still spurting hot jizz like a firehose. I quickly opened my mouth to catch it, but he unintentionally or maybe intentionally shot cum all over my face. I just held his cock and let him finish. When I regained my composure, I happened to notice our two admirers one of whom had his dick flailing and almost ready to cum and stepped towards me, but I turned my head away, Brad said no! and he backed off with cock in hand. The other guys said I’m really impressed. Brad thanked him and told me we had better get you cleaned up as he extended his hand to help me up from my knees and we walked to the bathroom I soaked some paper towels and washed the cum from my face and rinsed my T-shirt in the sink, I looked at him and simply said well?

His response not too bad for a rookie actually pretty damned good. I thanked him and said I think I need to go put some ice on my jaws which got a laugh out of him. As we walked to or cars, I said you know there’s one more thing I am going to ask you to do but. He laughed and said I know don’t think the thought hasn’t crossed my mind, but I’d say we need to slowly work up to that. I agreed and we parted ways the entire ride home I relived the experience. When I walked in my wife greeted me and asked where I had gotten off to? I chuckled inside to myself gotten off means a lot more than you think. Went to the park for a run stopped off and had a smoothie. She replied oh was it good you should have bought me one, sorry maybe next time was all I said.

by Bob Long

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