Any comments from Guys With Similar Encounters are most welcome.
This happened some years ago. But then it was a special because it was my first time at anal sex.
I was already aware that I was aroused by macho looking guys though I chose to get married. When the mood struck me every once in a while, I just had to go down to a park to check out the guys cruising there. I was usually too shy to approach anybody and if I found a nice looking guy I will watch him from a distance hoping he would notice me. That usually got me nothing or if I was lucky, some quick mutual jack off or oral services. It felt great and then I thought I got enough of gay sex and so will probably resist the urge to cruise again.
Well that promise soon got broken after a period of about a month when for some unexplained reason, I just felt the urge to get close to another man. So there I was again. This time I was cruising around the dim parts of the park and feeling quite helpless to resist the urge. Something was compelling me to seek out a mate. Somehow, this mating instinct was quite selective because I don't find myself being attracted to most of the men I saw. The urge subsided a little and I was hopeful that without any attractive guy of my liking, I will just call the whole thing off.
The night seemed bright with the full moon. Then I saw him out of the corner of my eyes. Somehow, his confidence attracted my nervousness as opposites usually do attract. I stood a distance away from him and he noticed my presence. He waved at me with his index finger and I nervously sat on his bench in a dim corner. He was a big man of stocky built with muscular arms unlike those of gym bunnies. He looked naturally macho that probably came from some manual occupation.
So we chatted. He was married as I was. We found a nice common topic to bitch about wives and families. I felt like I had found a soul mate who understood what I felt doing that at the park. The sexual tension of wondering if we will be doing it kept the chat fun and sometimes raunchy. We joked about our bedroom sex and how it was similar or different to gay sex. My view was that it was different because I get oral services that I don't get from home. His view was that it was still basically similar because one has to be the male/top role and the other the female/bottom role. Being bi-males, we both were relating how we were the tops for sex.
After chatting for almost an hour, we suddenly fell silent. The sex question was hanging unsaid but could not be postponed any further. I took the bold initiative to rub my hand up his thick thighs. He put his hands behind me and caressed near my buttocks. That somehow broke the awkwardness. He said, "Let's get down to it as grown men and quit the small talks. I don't mean to be rude but I've got to get home as soon as I could."
I suggested we get to the dark bushes and we could jack off or oral each other.
He said, "Sorry pal but I want to fuck you tonight."
I said that since we got on so well, we could be good friends and we need not have hard-core anal sex between friends. He laughed wickedly, saying that he was not there looking for friendship. If I was looking for one, he was not it.
The bluntness of his rejection hurt my feelings. He sensed my hurt and said that he couldn't believe I fell for that kind of touchy feely bullshit, for crying out loud. Being both married men, I should also know that it's all quickie sex and we both had to go home. All this touchy feely was gonna hurt me more. If I wanted that I should go home to my wife get it from her.
What about all that talk about top and bottom roles and how he lose respect for those married guys who get it up their backend? Moments ago, he was just saying that it probably would not happen to both of us. Now I felt awkward that he wanted to get it up my backend.
"Well, I am sorry honey but that is how it's gonna be," he replied in a demanding tone. " I got the goods you need and the only way you gonna get it, is up your nanny hole. Don't tell me you don't because I noticed your breathlessness when you feel up my body. You want it bad, so admit it. It's not so bad, you will probably recall this moment when you fucked your wifey. It will help you to understand how she felt. Haha, I'll probably remember how I made you feel soon. "
"Well are you coming or going?" as he led me by the hand to the deeper bushes with a nice open patch. " Christ, this ain't the end of the world," as he noticed my silent reluctance. " Tell you what, you can choose to go now or you can get me naked to sample the goods that you lusted after. Okay? "
There he stood with feet and arms apart and waiting. Such a fine specimen of a man and he was waiting for me to unwrap. With a long resigned sigh, I reached out and unbuttoned and removed his clothes till he was only in his underwear. Then he stopped me.
" Well, if you want more of me you gotta take off all of yours and let me examine your virginity." With a few quick moves, I was out of my clothes and buck naked in front of him.
" My oh my, what happened to the shy daddy of just now huh? You certainly wasted no time do you? Ohh nice tits you have," as he grabbed my chest. As my heart pounded faster, he said, " Good god, breathe easy will ya. Your heart beats so hard you might get a heart attack or something. "
With a hard push, he bent me over and his warm sweaty fingers groped for my hole. It tickled good and I groaned a little. He tried to push in and I gasped in pain. "Well such a nice tight ass, you could pass for a virgin."
"I am a virgin!" I just had to let him know for sure that I am offering up my precious cheery and he should not belittle what he would take from me that will forever be lost.
" Alright, I know you are. Haha, lucky me then. Okay I am sorry. I will be gentle to break you in. Look, I know it will not be nice if I fuck you in this manner since you will need careful attention and comfort. Why don't we move to that patch where someone had placed a nice cover of newspapers and you could lie down a bit."
There he gently laid me down on my back. " Okay sports, here's what you wanted", as he stripped off his last underwear to reveal a nice tool that was not too thick. " You have fun while I get you ready down there," as he took up the 69 position beside me. I could sense his cock throbbing as I gagged to get it all in my mouth while I ran my hands around his solid body.
Those hard smooth muscles were so sexy. When I got to the mid area, his small tummy still has the abs muscles as I pressed in. I wonder if he would still be so hot looking when that tummy started to get noticeable? Will he lose it and end up being the one on the receiving end as I was now? I sighed a little as he rubbed his saliva-wetted fingers around my ass rim. It felt good as I opened wider for him to get better access.
" That's right girl, open up for daddy", he cooed. What's all this putting down remarks that he liked to use on me ?
" Yeah right daddy, you go ahead now cause one day you too gotta be on the receiving end too," I blurted out subconsciously what had crossed my mind.
" What did you say ?", he stopped dead with what he's doing. " Good god, I sure hope I ain't as nanny as you now when taking it up my rear end. Yeah I know you feel my tummy coming out a little. Christ, it ain't easy to keep it down as I used to. "
" Like now? " as I gently rubbed his accessible hole with my sweaty fingers.
" For christ sake, don't do that," as he pushed my fingers away.
" What's the matter, afraid you might like it?" I teased back. I felt a sharp jab as a finger forced into my hole. Ahhhh!!
" That's for being a naughty girl," he laughed. " Could you stop protesting too much? You are the noisiest bottom I ever get to fuck you know", he scolded.
I gasped in joy as his searching finger hit my prostate. His experienced finger immediately went for more such hits. It sent an electric tingle up my body. My quiet gasps told him that he had his finger on my control trigger and he was firmly in control. I was all quiet as I tried to follow his finger and wanting more. He fell silent as he worked more spit on my hole and tried another finger in. I felt confusion as I wanted his fingers in but the pain was too much that I tried to stop him with my hand.
" Okay baby, I know it's painful," he reassured me.
He left my hole alone and started to pump his cock in my mouth. His other hand pinched my now sensitive nipples. Ohh, such strong hand! I was trying to breathe as his cock stuff my mouth full. I could taste the unmistakably ammonia smelling precum as my saliva started to drip down the side of my mouth. He forced my mouth open and told me to spit the excess saliva in his hand.
With it, he smeared my hole and tried to finger me again while pumping my mouth. With his cock distracting me, he got 2 fingers inside me and I felt full and very stretched. But with the extra lubrication, it was feeling better so I relaxed and let him pumped my ass slowly.
"Alright baby, you are doing good. Just relax and let me get your legs up on my shoulders. I need to see your face so I know what you are feeling. You look at my naked body and recall how you lusted to have me fuck you in your wet dream."
Yeah I told him that before but I did not know that he would use it as the key to unlock my inner secrets. Too late. This was to be it. My secret dream was going to be happening soon.
Scenes of pass sexual encounters flashed passed me where I had stopped before the anal actions and wondered if I would ever do it.
Familiar voices of my kids and wife ringed in my mind. I knew why. The stupid sex lessons I had to go through with them. " Man, woman, penis, vagina, baby comes when penis goes into vagina." "Yes daddy has penis and mommy has vagina, you silly tud." The hurried embarrassment to end the lesson quickly.
"Daddy has vagina and I am going to be entered by a stranger", I sighed to myself in a confused daze from the agony and ecstasy as he fingered me faster as my legs dangled over his shoulders.
" Tell kiddy that daddy's vagina is nice and tight", he caught on to my thoughts by the instincts of a married closeted bi.
Quickly, he replaced his fingers with his hard cock. With the suddenly feeling of a vacuum where his fingers were, his cock quickly enlarged my hole and sent a searing pain where it forced its way in. I looked at him with pain in my eyes and groaned. He grinned, stopped and leaned forward to kiss me hard.
" Come on baby, it only gonna hurt for just a while. Hang in there. Remember your wedding night when you deflowered her? Didn't she like it when the pain is over?"
In my confused state, I could not figure out if that was a put down or encouragement.
" Oh please, I don't want to do this any more", I cried out. All that internal phobia and the pain made me felt it was not worth it. " You win, you win. I am hurting. This is not right. Just say you already fucked me with your mighty fingers and let me go."
Without a word of reply, he kissed me hard to stop my pleading. His probing eyes looked straight into my inner soul. It was an order to put up and shut up. I struggled within myself. The pain below grew as though he was using an axe to split me open. He put my hands up his chest and his eyes commanded that I felt the man that I had wanted to deflower me. I grabbed his straining muscles hard. The pleasure gave him strength for one hard push and I gave a muffled scream of pain as it pushed in. I held him to stop further penetration so he stopped.
With a satisfied smile, he lifted himself off of me and we both inspected the point where our bodies had joined in sexual union. We were both sweaty all over in musky sweat that glistened in the moonlight. His body was an object of beauty as the moonlight highlighted his ample muscles. Where his muscles ended, his cock has disappeared under the cover of my now limp cock. He pushed my balls aside to let me see where his cock was still not fully inserted into me. Then as I watched, it slowly glided into my deeper self as it sent a feeling of fullness with soreness.
"It's in". I muttered to myself wondering if I should be happy for that.
" Yeah baby, the worst is over. You shall enjoy me as I promised. I will take you where you want only in your secret dreams."
The promise was not to be for the few moments that the pain was residual. But as his cock head hit my prostate and the shaft doing the sliding massages, the feeling was much more intense than just using his fingers. Every part of my ass was full of intense sensations. The sore and sensual ass rim wanted to feel his cock pop in and out every few moments. The prostate was pushing my aching balls to leak joy juices. His hands were kneading my sensitive nipples.
All that dirty talking was still spilling from his mouth. Where I had been offended before, now I joined in, encouraging him to fuck me like a bitch. Everything that flashed before me was now all swept away by the ecstasy. I would not care if they had known I was being used as I was then.
Everything will never be the same again. I had given in to my phobia and conquered it. I had given in to a worthy man and he was now in control of me completely. It felt liberating to be taken like this. No more inner phobia. No more cringing when someone mentioned "he does it with legs up in the air". It was great and nobody else needed to know. My sluttishness was safe with this stranger.
The highly erotic moment was too much for him and he erupted inside me after what seemed a timeless moment. When he pulled out his softened member, I felt some strange emptiness within. With his expert fingers and his oral manipulation, he brought me to a satisfying orgasm too.
We exchanged phone numbers and managed to keep in touch for a while. In spite of my better judgment, I was his willing whore. Ours was an unequal sex buddy relationship where he pulled all the strings. He enjoyed his powers over me and fucked me silly when he felt like it. True to his prediction, I will always remember him as my special someone. "That," he said, "made you too clingy and uncomfortable for me." He got tired of me when the novelty wore off but I still missed him so.
To prove his point, he called me up in the middle of one night and ordered me to meet him at the park. I had to invent some fantastic lies to get out to meet him. He was shaking his head when he met me. Do I realize what I am doing? I was making life difficult for him so he was making it difficult for me back.
" Think back about what lies you told your wife just to meet me. How much more do you want to go on ? If you want to come out to your wife, please don't include me. You have no right to do that for me. What we had was not love and never love. You scared the shit out of me by introducing your family to my family at the shopping mall. I know you don't shop there. You had gone too far. What happened to you? "
From that night on, it was over. I was tempted to call him at times but he was right. I was getting from one phobia to a worse malice of infatuation. It made matters worse to sometime bump into him at the park and seeing him with someone else. We still talked on occasions but it was more to ease me further away from him. Till one day he moved away for business reason.