I’ve told this story a number of times to different people; the first time I hooked up with a guy in real. There had been other times where I had talked about it on the phone with someone or was actually half naked with another guy in my bedroom but nothing ever happened from that. This was the time I had actually went far enough to meet with another guy and have him put his mouth around my cock and have my mouth around his cock. This is the story of my first time actually enjoying another man’s cock.
It was a few years ago, probably closer to 5 years now if not slightly longer. I had thought about men in a sexual way off and on since I was in my teens but it had been quite dormant before flooding back due to some other events in my life at the time, mainly my realization of my cuckold fetish and my wife fucking a man she works with. I, as we know if you’ve followed along, have no issues with this now and didn’t at that time when she told me. It was a surprise but a nice one, better than the alternative anyways. Since that was discovered I did a little bit of sexual soul searching and my bisexual desires kind of crept up and started to reinsert themselves in my mind. This coincided with my wife actually going away on a trip with her friends and was the perfect time to see if I could wrestle something up and make it happen.
I had no idea if I would actually do it but I wanted to put feelers out and see if I could form a connection with a guy so when the time came we could do something together if we hit it off. It was then that I decided to make a secret PlentyOfFish account. At that time the site was really the dregs of society where only the desperate looked for relationships but actually had a good amount of married men looking for other closeted men for hook-ups and I took advantage of it. I put a profile out and received a number of interested men and had gone the next few weeks talking through email with them. There was one man in particular that seemed pretty like-minded with me and in the fit of arousal he persuaded me to turn on my webcam when I was home alone so we could do some face to face talking. In an odd bit of luck my webcam wasn’t working but his was. He wasn’t ugly but he also did nothing for me mentally or physically. I told him I was sorry but my webcam seemed to be broken and we didn’t really continue talking after that. Yes I am horrible.
There were others but none were really interesting to me. I was looking for my clone but with a more aggressive and dominating nature. I wanted someone who could spit out a few hundred word emails with his eyes closed and be the dominant yin to my submissive yang. I wanted my ideal fantasy of a man to overtake me and make me fall in lust. I never found him to this day, however I did come close.
I was randomly emailing with a man while at work one day. There was nothing extraordinary about him. He was hitting a few of the sweet spots to turn me on and that was the only thing keeping me in contact with him. He was dominant but not pushy. He gave me the right amount of degrading talk and calling me names, even participating in talking about my wife and feeding my cuckold/humiliation fetish. The issue was that he would barely write more than twenty words in an email and if I had written anything at length he would only respond to the first idea and completely forget about anything beyond that. It was extremely frustrating but it was all I had going so I let myself continue.
It was a random weekday and he and I were going on throughout the day in between my daily tasks when I told him I had to get going for lunch. This is where he took off for me and reached my next level of interest, he asked where I was going. I was confused at first and asked, simply, why? He replied that he wanted to watch me.
This sent electricity through my body. I think if anyone had been staring at me during that moment they would have seen my entire face become flush with red. My heart was beating quickly along with my breathing. He had me and I told him without thinking of the possible repercussions. He upped the ante a bit further and told me to leave for lunch and get out of the car. Then I was to pretend I dropped something and face the open parking lot and bend over at the waist to pick up the imaginary object and show him my ass. I was sold.
I emailed him back enthusiastically and hurried to my car. I was very aroused and my chest was still pumping at the thought of being looked at like a piece of meat for another man. To imagine this guy sitting in his car stroking his cock as he stares at me gave me chills I never knew I had. It was no time before I reached the parking lot and I took a quick spin around looking for him. There were a few cars but I couldn’t tell if anyone was in them or not. I did as I was told though and got out of the car and bent over like I was trying to pick something up that fell out of my car door. I quickly when in and ordered my food and hurried back to work.
When I got to work I wasn’t even hungry anymore. I threw my food down and logged into my email and asked if he saw me. He didn’t. He didn’t get out of his house in time.
“Could you come back out,” he asked.
This time he wanted me to grab my crotch while facing him too.
I replied, “Absolutely!”
We agreed on a neutral place not far from my work and not too much further for him to drive. It was a big parking lot that was fairly empty to one side of it. I carelessly told him what I would be driving and he told me to do the exact same thing.
I rushed out and was at the empty parking lot in no time. I parked in the middle but far enough away from cars that he could easily tell it was me. I got out of my car and I saw him, or what I believed to be him. There was a man sitting in his truck far away from any other car and pointing directly at me. I couldn’t see anything specific about him except that he was staring directly at me. I got out of my car and decided to kick it up a notch and walked to my trunk and opened it. I bent over as far as I could inside and pretended to reach in the back for something and gave him a good look at my ass bouncing up and down. I turned around and did a quick glance around to see if anyone else was staring at me and when I was satisfied there was nobody I grabbed my cock and gave it a squeeze while facing his truck. I slipped back in my car and drove away in a dizzying high. I logged onto my email as soon as I got back and he told me he liked what he saw and he would email me later.
I’m a bit loose on some of the specifics but I don’t believe he took more than a day to email me back at any time when we were in contact. It was a high, meeting him. I wanted it again. He did too.
He emailed me back and within a day or two he gave me an assignment. He told me to wear a pair of my wife’s panties to work and meet him at lunch again in the same spot. I was on edge with the idea. I had been playing around with wearing my wife’s panties off on and for a few years. I was getting kinkier and kinkier and was exploring a variety of different avenues. With her newfound adventures in fucking another man at work the idea of her panties having his cum on them excited me to no end. When she was at work I would find the pair she had worn the day before and replace them with whatever I had been wearing then lay in bed and masturbate to finish and orgasm in them. It was a sticky, wonderful, dirty mess.
I knew just the pair too. I wanted something bright and colorful, like a peacock flaunting himself to a mate. My wife had a bright pastel pink pair of panties and I slipped them into my pocket that morning while she was getting ready. Before leaving the house I ducked into the bathroom and exchanged my ugly boxer-briefs for her cute, tight panties. My cock was hard and being held snug to me making it feel even harder.
When I arrived at work I felt extremely self-conscious and thought that everyone could tell. Nobody could, I was just projecting but it felt like it. I barely got up out of my chair for the few hours until lunch. I spent my time refreshing my email and sending him short lust-filled notes of how hard I was and how I couldn’t wait to see him.
Lunchtime arrived in a hurry and he had an added task for me. He said we were to park in the exact same spots and his instructions were very clear:
- Get out of my car and face him
- Undo my pants and flash him my panties
- Get back in my car and leave my pants undone
- Unlock the passenger door.
He told me he would come over to my car and get in if everything looked okay. He finished at the end with four words: “don’t say a word.”
Something about that made me giddy. The erotic feeling of a a strong-willed man handling me and giving me orders. Controlling me. It was a dream come true. My fantasies were going to finally be answered. Being told to obey and be a quiet little submissive while a strong dominant man had his way with me; I could have cum right then but knew better. If I did I would have never gone through with it.
At lunch time he emailed and told me he was there waiting. I bolted for my car and was there within a few minutes and parked facing the familiar truck as it sat three parking lanes away. I got out of the car and faced him and took a nervous look around. The busy street behind me was oblivious to a random man standing in a half empty parking lot. I discreetly undid my pants and unfolded them to show my pink panties to the man in the truck a couple hundred feet away. I left them undone and got back in my car and sat and waited, my eyes locked on his truck.
At this point I had only seen him from a distance. He was a fuzzy image with no specifics. I watched him exit his car and stroll across the parking lot to me. As the specifics came into focus I found something very surprising happening with the two thoughts running through my head, they were at odds with each other.
He was older, which didn’t matter because I wanted him to be older. His body type was less than ideal, although I couldn’t truly appreciate how much until a few encounters into the future. He was short with a belly. His scruffy appearance did nothing to further my “dream come true” fantasy and the stench of cigarettes as he entered the care should have nearly fizzled it out completely, but the surprising thing is that it didn’t. Nothing was deterred. This short, old, scruffy, fat and ashy smelling man got in my car and instead of clamming up and shriveling I stayed as hard as I had been. I lifted my hips even and pulled my jeans and panties down to my knees to give him a better view of my hard cock.
He reached his hand over and gripped my cock and started pumping. I heard his voice moan as he squeezed it. Instinctively I reached down and laid the seat back and his body leaned over top of me. His head dove down over my cock and it disappeared into his mouth. My entire body went stiff. I became astutely aware that I was receiving a blowjob in my car in the parking lot in the middle of the day. I looked around and made sure nobody was watching. There were no cars driving towards us. No random people on foot walking towards the car, just a man leaned over my lap sucking on my cock.
It seemed to go on for minutes when it actually only lasted about fifteen seconds. He sucked and bobbed his head up and down. He moaned into it. His moan was wonderful. It was deep and hungry. It vibrated through my cock and made me shiver. I wasn’t quite nearing an orgasm but was well on my way when he stopped and pulled up. He turned and opened the door without saying another word. I was panicked. I had another man sucking my cock. Another man grabbing my bare cock and stroking it and I didn’t even get to grab his through his pants. I was desperate. Would we even be able to get together again? It was likely but not guaranteed.
In a fit of desperation I blurted out one of the most embarrassing things I’d ever said, “can I try you?”
The words stung as he slipped out of the car and walked away. His head swiveled from side to side casually as he made a bee-line towards his truck, hopped in and drove away. I shook off the feeling and put myself back together and drove back to work.
A short while later he emailed. He said we would meet again. My heart began to race again at the thought. I told him I wanted him. I told him I needed him. I told him things that he could have abused right then and there and I meant them. I said I would have done anything for him. He could have given me an address and told me to go there right then and I would have. It could have been a room full of men I didn’t know and I would have serviced every single one of them. He had me wrapped around his finger. Thankfully he either didn’t realize it or simply didn’t abuse it.
I told him I wanted to suck his cock. I told him I wanted him to fuck me. He said I would get all of that when I was ready, but I wasn’t ready yet. He was probably right. I was too eager. We continued meeting like that though. We found a new place nearby that was a bit removed from the busy street next to the parking lot. Still in the same complex but closed off and far away. Two cars parked next to each other look like nothing more than that. He would get into my car and he would stroke and suck me. He gave me my first orgasm from a blowjob ever. He gave me my second through fifth as well. He’s actually been one of two people to suck my cock to finishing, neither being my wife.
After a handful more meetings where he had tended to my cock numerous times it finally came to the time when my wife was going to be away. It coincided perfectly as when I told him that I would have a bit more time away from work because she would be away (hence I wouldn’t have to worry about her calling me wondering where I was) he said that we could plan a meeting then for something a bit more in depth.
We agreed to try something a little further. He told me to make sure I had showered that morning and was clean. He said he would pick me up at lunch in a different parking lot than usual. I would get out of my car and into his truck and he would drive me to a location nearby. Thinking back to this I cannot believe how dangerous it was to do this. Even though I had met this man a few times before I didn’t really know him and it never entered my mind for a second that he could be trying to bring harm to me. I was so lost in my own desire that I was reckless.
He worked in construction and was fixing apartments in an apartment building nearby. He said there would be nobody there as he worked alone and we would have the entire place to ourselves. It really was perfect. He gave me another requirement; wear panties and a bra. Then he said he also wanted me to bring one of my wife’s skirts. I was tingling.
My kinks were all of the hesitant variety. My early bisexual fantasies all revolved around blackmail and being forced to suck another man’s cock even though I didn’t want to. These fantasies of being forced never really went away. They allowed me to revel in the idea of playing a bisexual whore and a cross-dressing sissy without really saying “this is really me and what I enjoy” because all of the fantasies revolved around being forced by another party into it. This scenario was fucking perfect. He was telling me to do something I wanted to do and I didn’t have to ask him to do it first. I didn’t have to hint at it or suggest it. The idea of being able to dress up for him and have him fuck me with women’s clothes on was insanely erotic and I wanted to bask in it.
I gathered the goodies in a bag while my wife was doing various things at home. I slipped them under the drivers seat of the car. At work that day I had worn the panties but the rest were stashed away until they were needed. Upon our regular date time he told me to get ready.
He wanted me to get ready for our fuck-date. He wanted me to go put on my bra and wear it through the office and drive with it on to meet him. I put it on secretly in the bathroom and I felt exposed. It was snug, the 38B cup bra was tight. I couldn’t work the hooks around my back so I had to put it on like a shirt and tug it into place. I felt ridiculous. I put on my shirt and then a coat over top to hide the clingy t-shirt material. I was sure everyone could tell. I couldn’t make eye contact but swiftly exited the office and drove to see him. This incredible man who know all of the right buttons to press.
The entire drive I was grabbing and massaging my cock. I was nervous as I had ever been. I was wearing women’s underwear and a bra with a skirt under my seat and going to meet a man to fuck me for the first time in my life. No matter the amount of anal exercises I had done in the shower alone with small brush handles and awkwardly shaped soap bottles this was going to be different then anything I had ever done.
I saw his truck and pulled up along next to him. I grabbed the bag with the skirt in it and got out of my car and into his truck. It was as if he was picking up a shy prostitute on her first job. Neither of us said anything as the country music radio faintly played from the speakers.
It was less than five minutes and he pulled up to the apartment building. Much to my chagrin he parked on the side of the road and got out. I followed as we walked along the street and up the front of the stairs and stood at the door as he fiddled with the keys for the right one. I had hoped we would be parking around back and entering an apartment building where nobody could see me. Instead we were entering an empty half of a duplex in broad daylight. I was terrified someone I knew would drive by right at that moment. Thankfully they didn’t and we were in the door in less than a minute.
It was a small place. The door opened up to a kitchen on the right and the living room further beyond that. He set the keys on the counter and walked down a short hall to the left to a spare room. I followed him in and he closed the door behind us and locked it. I never asked why but I figured he did this in case anybody had decided to come in that might have had a key. It would give us time to get our clothes on before they discovered us. The thought was terrifying but not enough to chicken out and leave.
When he turned around he spoke in a very low voice that lacked the power and confidence of our email exchanges.
“Why don’t you go ahead and get your clothes off.”
I did exactly as he said though. I dropped the bag with the skirt in it on the ground and took off my shoes and pants and kicked them aside. I slipped my shirt over my head and then removed my socks and stood against the back wall of the small empty bedroom in just a bra and a pair of panties.
He walked over to me and grabbed my cock and gave it a little squeeze. He was still fully dressed in his ratty shirt with holes along the side and paint stains on his jeans. He still stunk of cigarettes. I still didn’t care.
“Go ahead and take the rest off,” was the next thing he said in his same weak voice.
I stripped down to nothing and he got on his knees and put my cock in his mouth. He began sucking me and my hands rested on the top of his head. The tip of my cock was extremely sensitive, it always has been. I’ve wondered if every man’s cock was like this but never had someone close enough to ask. I’m curious if its just the blowjobs I’ve received haven’t been done right or my cock is just super touchy. My body was twitching and I was going from feelings of nearing orgasm to pain. Not quite as bad as when my wife had tried to give me head but it surely wasn’t a perfect experience either.
“I’m…I don’t want to finish,” I whimpered as he kept pushing me closer and closer to the edge. I knew once I had cum it would be a miserable experience. This is how it always has been with me and fantasizing about men. No matter how hot I had been and how turned on it all made me whenever I would cum the feelings melted away and were replaced by regret, disappointment and disgust. I hated myself and would thank god that I wasn’t actually with someone.
There had been numerous times where I had planned to taste my cum to see what it was like and I chickened out after finally producing it because I no longer wanted anything to do with bisexuality. If I was going to cum with his man it was going to be at the end or not at all because I couldn’t have taken being fucked by him after I had orgasm-ed.
He took my cock out of his mouth and moved back.
He stood up and said, “on your knees.”
It was simple and to the point. We were getting back on track.
“Now take out my cock.”
Again, straight to the point and I was excited. I undid his belt and let his jeans fall to his feet. I pulled his boxers down and let them pile up with his pants as he kicked them aside. I didn’t have to wait for the next instruction. I was close enough to another man’s cock for the first time that I could reach out and touch it so that’s what I did. I took his cock in my hand and began to pump it and get it hard. Shortly after that I let instinct take over and for the first time in my life I put another man’s cock in my mouth and began sucking it.
All the while he was taking pictures with his flip phone camera. It wasn’t so long ago that flip phones were the only thing available but its all that he had. I only had a shared phone between my wife and I and there was no way I was putting pictures like that on it. He had taken a picture of my cock in my panties, of me in my bra and now of me sucking his cock. He would take a couple more and send them to me. I was very disappointed with how they turned out. They were blurry and so out of focus I deleted them. I guess it was the thought that counts.
While having a cock in my mouth for the first time I wanted to do everything because I didn’t know when the next time I would have one in my mouth would be. I sucked and bobbed my head on it. I pumped him into my mouth. I tried to deep throat him and press my lips all the way against the base of his cock. It all seemed quite easy and I didn’t know what the big deal was about. It wouldn’t be until after meeting some other men and playing with them that I realized my first time with a guy was with a guy who had a very small dick.
I’m not a size-ist at all. I do love the idea of a huge cock and have actually had one, and been disappointed that I couldn’t really do anything with it. I, myself, have a very average 5 inch penis when fully erect but mine has, what I’ve been told, is an above average thickness to it that helps with its shortness in length. His was as long as mine, maybe a tad shorter, and lacked girth. But at the time I didn’t know this and was impressed with my own ability to do all of the various cock-tastic things with him.
After a short while of being on my knees and sucking his cock, a few minutes at most, he pulled away and laid down. I was a tad confused as to why he was doing this but he didn’t say anything else so I knelt over him and continued sucking his cock. I heard the occasional moan and satisfied sound from him but over the next few minutes it really felt like it was beginning to drag on with nothing happening.
Finally, at a point when I had come up for air he moved away from me.
“Lay on your stomach”
I, again, didn’t quite know what was going on but I did exactly as he said as a good slut should. I watched him grab a bottle of something and heard a squirt then the sound of lotion being rubbed in. Then another squirt between my ass cheeks and the cold sensation of gel and then his rough hands forcing his thumb into my tight asshole. I jumped forward and gritted my teeth.
Then the second most awkward moment of experience happened, he mounted me like that as I lay flat on the floor. He climbed on top of me and laid his stomach flat on my back. His cock slipped into my ass fairly easily with the heavy amount of lube he used. His weight pressed down onto me and it didn’t feel too bad at that point. That is, until he started.
The only way I could accurately describe the next feeling would be to say it was as if he was jack-hammering his pelvis into my ass with every ounce of energy he had in him. It was an onslaught that I had not expected and did not prepare for. I thought he would slide into me on my knees and slowly introduce his cock to the insides of my asshole. Instead he decided to plow his way through me in his deep desire to fuck the floorboards.
I was tense. My entire body went stiff and it made everything much worse. It hurt a lot. I went from my eyes being wide open and gritting my teeth to my eyes being shut tight and my mouth agape. My moans were uncomfortable and my breathing was sporadic. I can’t remember for sure but I faintly recall him grunting like an animal as he rapidly fucked my ass.
The only thing I could do was try and catch my bearings. While my eyes were closed I took a deep breathe and tried to regain my composure. I slowly tried to relax in between his bucking hip thrusts and finally was able to make the pain subside and actually have it feel good. It even went from feeling kind of good to feeling amazing.
I began to moan pleasurably and even let out, “fuck yes, fuck me harder.”
And shortly after that it was done. As long as it felt in the beginning the entire process was over in a matter of two minutes. I pulled himself up off of me and I was extremely disappointed. I didn’t know if he had cum or not but I didn’t feel anything. I was just starting to enjoy it and wanted him to keep going but he had again laid on his back and motioned me over to him. He wanted me to suck his cock after he had been fucking me in the ass. I obliged because I’m such a kind soul.
I crawled over his body in an off kilter 69 position. My cock was positioned at the right side of his chest and my legs were off to the right of his head. My mouth had gone back to giving his cock attention and his hands began to play with my cock. I wanted him to stop but I didn’t want to say it. He was bringing me closer and closer to orgasm and I couldn’t do anything to stop him. My mouth dove deep down on his cock and as mine erupted all over his chest. Fuck.
At this point everything slowed down. I don’t know if its because I had cum and I just wanted it to finish or if it actually took as long as I thought it took. His cock was like a bendable rubber and never felt like it was extremely stiff. I figured afterwards it was because he was older and had a hard time getting it up, which also lent to why it took him so long to cum. My jaw was getting sore and my wrist was getting tired. I feverishly tried to pump him into my mouth and play with his balls to aid him on his way. Nothing seemed to help.
There was one point where I remember thinking about what I had to do at work when I got back to finish up before the end of the day. That led into me wondering if there was a baseball game on TV tonight. I caught myself thinking these thoughts and then wondered if this is what women feel like when they are fucking a man and it just isn’t going to happen for them and they are merely waiting for him to hurry up and cum. It felt like it was become a parody of an actual sexual encounter rather than my first male on male sexual experience.
As the time droned on I wondered if he would ever cum. I was trying to think of an exit strategy because it didn’t appear like he was going to give up. He was making no sounds of pleasure to let me know he was close. I decided to take a long break when coming up for air and tell him, if he asked, that my jaw was getting sore. When I pulled off of his cock I swallowed my saliva and tasted a saltiness to it. I looked down and saw his cock oozing out cum slowly. He was cumming, but not the long shots of ejaculate that I did when I cum but instead a slow tepid rise to the top.
I took the opportunity to move off of him and grab my clothes. I don’t know if he was completely finished or not but he followed suit and we both dressed. Not another word or sound was spoken. I put the bra and panties into the bag with the skirt that was never worn and followed him outside and back to his truck. I had a mild panic attack as we drove back to my car as I noticed a police car driving slowly down the street while we pulled away but nothing happened. He dropped me off and I got in my car and went back to work and that was it. That was my first experience with another man where we did everything.
I continued to meet him. Not because I was impressed but because I wasn’t satisfied with my idea that I had either enjoyed it or not. I was still in the middle. There were things about it that I wanted to experience more of and I didn’t have anyone else. He was safe now, to me. I could trust him that we could meet and nothing would happen. We continued to meet in the car where he would give me head. We met another time in another apartment that was even less satisfying than the first time. I could barely feel his cock in me and it seemed to be for an even shorter duration. Shortly after that we stopped getting together and I would make up excuses why I couldn’t meet.
He actually came to work at the place I worked at but in a different department. It was physically demanding so he didn’t last long but it was kind of funny. He only held onto me because of the attitude he exuded online. He only kept me because he was the only thing I had and I wasn’t ready to give it up yet. I stopped doing things with him because I was convinced it wasn’t just something I thought I liked, I did like it. It was something I wanted to keep trying but I wanted someone better. I wanted someone who I enjoyed and made me feel the way he did but have it also carry over in person as well as online. Nobody ever got that close. There were two men who had the physical aspects but not the mental dominant side I wanted. I’ve never been able to find a balance of both that made me want to risk anything again. I’m still looking but I’ll hold my standards a little higher this time.
Feel free to ask any questions or make any comments about the experience. I don’t mind answering anything and everything for those who want.