My Real First Experience With A Man

My Second Time With A Man

As I was sitting in my office on Friday getting ready for the weekend, sex with David started to get stronger and stronger on my mind. It was Friday jean day at my office. I was wearing the same jeans that I had on when David last made love to me. My first encounter was everything a man could want with sex. The problem was and is, I am married to a woman. I have been married for 15 years. The other problem is, at 46 years old, I had incredible sex with a man and I never really thought that would happen for me. Since then, I kept thinking it was the last time. I convinced myself that I had sewed my wild oats and that was it...a fond memory.

Then there was my wife, unfortunately the opportunity to have sex with her did not present itself this week. I thought, perhaps if I just had sex with my wife I would forget about the experience with David or lessen its impact in my mind. I even jerked off this week, at least a few times. After each time, I would tell myself, I didn't really need to see David again. I didn't need to find out what more there was sexually with man, as David told her there was. For a day or two, I forgot. I put my time into my work, wife and kids, and that was it. But here I was on Friday, thinking of being fucked, thinking of the smell of man, thinking of a cock in my mouth and remembering what it felt like for a man to climax in me. I could not concentrate at work.

Since we parted on last Friday in Winter Park, David texted me. David even called me. I spoke to him a few times. David asked me to come to his house in Palm Beach for lunch. David asked me to meet him after work for a drink...if I could get away from the family. David even said he would play tennis with me, despite that he was not really a tennis player. David was not aggressive and really did not say "Hey, let's play tennis and then fuck." However, we both knew where a second encounter could lead. He told me his husband was still away on business, so he wanted us to hang out, even just for an hour. For him it was probably no big deal. For me, I was conflicted. Big time.

What gay people my not understand is that some straight people, or maybe bi people, like myself, really rather not fulfill fantasies. I was a business lawyer, with a pretty wife, with great kids, great friends and everything was working out how my parents, their parents and the world told me things needed to work out with my life. In all honesty, before David, having sex with another man really never crossed my mind. It was not a fantasy. I suppose I thought the male form could be attractive or sexy. But I didn't dwell on it. When I somehow stumbled into having sex with David, all of the sudden I was conflicted. Now I was fantasizing. I even fingered myself while jerking off, gently finding my prostate and loving how my man hole felt while being penetrated. I even used more than one finger, wanted to stretch my hole imagining how a hard cock would feel. Regardless of what I did at home, there was that orgasm, the one that came from inside. I have come to believe that no man should go to his grave without having the ecstasy of a prostate orgasm, and have the semen literally fucked out of you. Despite all of this, I found every excuse up until Friday to stay away from David.

David picked up the phone at 2:15 pm on Friday, almost as if he was expecting my call. David said he was in his office, in West Palm Beach but asked if I wanted to hit happy hour somewhere. I told him I could not. I did not want to drink since I was going home. David asked, "What's wrong, what's going on?" I closed my own office door, lowered my voice and said, "I want to see you, but I have to go home tonight. I have to probably cook dinner, do the kid and wife thing. Plan for the weekend." I was clearly placating him and, in hindsight, avoiding him. David said, "Jack, I get it. I have never really done much with a married straight guy and my husband and I don't keep secrets. I get your secret though. You do and I respect that. Your problem is that you don't trust me. You don't trust yourself." I said, "What do you mean?" David, in a sort of frustrated way said, "If your secret was going to be told, it would have been. I know where you work, I know you and I am fine with being your secret. This is not going to lead to the demise of your marriage or mine." I said, "David, I don't think that. That's not what is going on." David then replied, "Then it's that you don't trust you. If you were telling me that the reason we cannot hang out is that you are worried about your religion or some other moral conflict, I get that. But I don't think that is the issue. You are scared that you'll like it again or that it will change you." David left it there with some uncomfortable silence. He was not a person who really expressed his opinions and I could sense his frustration in me.

I broke the silence, "What do you suggest then? I want to hang out with you. That's why I called." David sighed, "Look, I'm sorry I was being judgmental. Let's do this. I'll head out of my office, you head out of yours. There is a beach near my house. Let's meet near Worth Avenue, walk the beach and talk. We can go to my house afterward and do whatever it is we might want to do." I did as David asked. Then the butterflies started again. What was wrong with me? I was turning into a teenager again. I got into my car, left my office and headed to see David. I had made excuses to not see him. I tried to jerk off to get him off my mind earlier in the week. It did not work. Rather, the thought came back and were hard to resist.

As I walked down to the beach sidewalk, there was David in shorts and t-shirt. He was pale skinned. He lived here near the beach and I realized he was not a person who was tan at all. In fact, when he was naked, I realized now that he did not even have tan lines. David had sunglasses on, he was clean shaved and looked like an attractive 50 year old man. I noted, David did not look gay. I envisioned him as a gay man in my mind, but in person one would never know.

The strange thing was, seeing David did not make me horny immediately. It was not like my sexual attraction with females. With females, I saw the face, the breasts and the skin...all of which made me attracted instantly. With my male sexual attraction, it was not at all similar. Rather, it was not until David and I were walking and talking that I thought of him sexually or really was turned on.

We talked about how I was dealing with getting home after our affair. He told me that he told his husband and he joked that his husband said "Don't leave me for a straight guy." Then we started to talk about my second orgasm that he made me have that evening. As David and I continued to talk, everything about him became sexy. HIs lips, his hands, his pale skin. I thought about his dark nicely trimmed pubic hair and his thick, veiny and shapely hard cock. I even liked his ass and his asshole. I loved putting my tongue in him that evening. By the time we reached David's house, my cock was hard and I again felt precum in my underwear. While my initial sighting of David did not turn me on instantly, I was more attracted to him than any woman by the time I reached his house.

David lived in a smaller Palm Beach home. It was nicely appointed, but dated on the inside. David walked in, locked the door behind us and said, "Do you want to try something dirty and something you've never tried before?" I had already fucked David, so I didn't know why my stomach had butterflies and I was so nervous. This was going to happen again, and I was really here with him. This was something I wanted so bad all week, and here I was. For whatever reason, I was still nervous, almost to the point of having cold hands. I did not get cold feet though. I was determined to find out what David had in mind.

David walked up to me, and this time I opened my mouth and began kissing him immediately. His lips were soft and inviting. I felt David's warm tongue and lips rhythmically tangling with my tongue. His face was smooth this time, and as we broke away we kissed, rubbed our lips gently together and then went back to having our tongues slashing together. It was hard to stop, even making out with David was sheer pleasure. I gently reached down and felt David's hard cock through his shorts. He had a nice cock that was just the right size and girth. David grabbed my ass as we kissed passionately. David pulled my cock into him, where he began rubbing his hard on into mine. David then began kissing my neck and he whispered lustily in my ear, "I want you to swallow my cum." David brought his lips back to mine and he bit at my bottom lip teasing me in sexy way. "If you swallow my cum, you'll be mine. Do you want to be mine?" David whispered. I nodded my head, "Yes." David continued kissing my neck, causing my entire body to be covered with goosebumps. I never thought of swallowing a man's cum, but David made it sound enticing.

David broke apart our kissing at the front of his house in the foyer, he grabbed my hand and led me to his bedroom. David had a nice modern bedroom, with a low platform bed. The best thing was that he had a beautiful on suite bathroom that was fully updated and somewhat lavish. While David did not look gay, his bedroom and bathroom appeared to have had a woman's touch. There were pinks and reds, with flowers and other nice pillows everywhere. David led me into the fully marbled bathroom. We kicked off our shoes and began making out by the sink counter. David pushed me up against the counter and whispered, "If we are going to fuck, let's be clean."

I knew what he meant. I thought he wanted a shower. But rather he pulled out the enema kit and placed it neatly on the counter. I looked at him with a bit of surprise. I sort of thought maybe we were not going to do that. David obviously had other plans it seemed. I thought I was just going to give him a blow job, making him cum and seeing what it was like to swallow his seed. This turn of events made me excited. I wanted David to fuck me again and if this was how it had to be, I would do it for him. After all, I didn't want to have something gross during sex. David said, "I am sorry, I'm OCD...this is my only hang up, I promise. I will do me in the guest bathroom and we will both be ready. I don't like surprises." David kissed me on the neck and then the lips and said, "I will see you in a few."

And so, for the second time in my 46 year history I found myself doing a warm water enema. This time, in one of the nicest bathrooms I've ever been in...ever. He even had a bidet in his bathroom. I was not really sure how to use a bidet, but I figured it out. I actually found the bidet to be quite useful and nice.This ritual was foreign the last time. This time it turned me on. I was readying myself to be penetrated and filled by a cock. Sliding the enema kit into my ass and flushing myself out actually had me hard. Was it the anticipation or what I was preparing for? I am not sure. But, after that was over I stood there in his room in only a towel with a massive and aching hard on. David came down the hall with no clothes on and grabbed my hand leading me to his bed.

David and I laid on the bed, immediately kissing. He pinned me under him and had my hard cock against his. He straddled me and began jerking both of our cocks together as he moaned with pleasure. David was sweaty from the hot Florida sun. While he was OCD about hygiene with sex, I was thankful David did not shower. His male body odor that came from his armpits and body smelled musky, sweet and like a drug to me. I immediately had the urge to lick and suck his small nipples. I began kissing, licking and sucking his nipples fervently. This seems to have driven David wild. He pushed his chest out, and I sucked his left nipple open mouthed to where my nose was right in his hairy armpit. The smell was that of a days old wearing off deodorant and his sexy man smell. As he jerked our cocks together, I could feel precum coming from my cock. As I lay there, I was free, free to indulge, free to love and free to do whatever David wanted. It was an incredibly sexual and liberating moment.

David then released our hard cocks and asked me to get on my hands and knees. I complied. David pushed the small of my back down and motioned to be push my ass out. David kneeled behind me and said, "You have a sexy hot ass." Then I felt his tongue diving into my asshole and rimming around it. As he pushed his tongue in, my instinct was to push may ass further into his face. He grabbed my cock underneath and was jerking me while putting his tongue in and out of my hole. I looked over in the mirror and saw us having sex. It was beautiful, it was sexy and I felt my female side as I watched me pushing my ass out and David's face buried in my ass. I liked my female side, I felt sexy and I felt vulnerable. Most of all, I wanted David to fuck me, to make love to me and to do me doggy style like I was a woman. As David continued to dive his tongue as deep as he could into my hole, I moaned. I could not wait for David to fuck me. I moaned, "David, fuck me please. That feels so good."

David paused and then said, "I am and we are going to do something hot. You are going to love this." David plunged his tongue in my ass as deep as he could. He left as much saliva down there as he could. David continued lubing up my asshole with his saliva and nothing but his saliva. Without any lubrication other than his saliva and whatever natural lubricant was near the ass, David slowly pushed his beautiful chiseled and veiny cock head between my cheeks. I was hesitant since I really thought lubricant was necessary. Regardless, I looked in the mirror and could see his hot cock between my cheeks. The sight of David's cock entering my ass crack made me trust whatever he had in mind. My hole was tight, and I rubbed it against his soft mushroom head as David moaned. "Yes, baby, let me fuck you." As he pushed forward, it felt better and better. Soon, the mushroom head broke through the tight opening of my anus and he pulled it out quickly. He then pushed it in slowly, this time breaching my hole easier. He continued teasing my hole, loosening it up and making me moan with anticipation.

Then David backed up and began tonguing my ass again. It felt absolutely incredible. Every nerve in my body was relaxed and brought to pleasure with each tongue probe David gave me. He then left more of his saliva in my ass, got back behind me and this time his cock slid effortlessly into my ass, stretching me, filling me and causing me to shudder under him. David moaned loudly, "You are so fucking tight and hot. Oh my God, you're going to make me cum so hard." David grabbed my ass cheeks and pulled me into him sliding his entire cock into me. He moved his hips in a circular pattern as he held his cock deep in me. The movement stretched my hole and allowed me to feel his pubic hair grinding into my ass. I looked in the mirror and as I pushed my ass out in an attempt to open my ass hole to every bit of David's cock that I could get. David began fucking me harder and harder. I could see his hard veiny cock going in and out. He would fully pull out and then slide it in with no resistance. My entire hole was loosened and accepting of David's cock. I was craving his cock. I started to moan louder when he would fully pull out and then plunge quickly into my hole slamming into my prostate. Underneath me, there were streams of my semen flowing out of my hard cock. I was literally dripping with cum and I had not even achieved an orgasm.

David's balls were slapping against my ass, now he was going in and out, deeper and deeper. At times, he was going very deep, he would leave it in and moan loudly. "Oh fuck, I love fucking you. Oh God, I want to fuck you every day." With that, David's hard cock began hammering my prostate deeply and David was going to explode. I could feel it. David was right on the verge of coming in me. Then suddenly, David pulled out and quickly turned me around. David said, "Finish me, finish me. Let me cum in your mouth. I want you to swallow my cum. Take very bit of me." I quickly turned around, laid David down and began taking his hard cock into my mouth.

Everything about this moment was erotic, so dirty and so wonderfully perverted. I could barely stop myself from climaxing as I licked, sucked and took David's cock in my mouth. David was fucking me with his own saliva. His cock was in my ass. He was about to have his cock explode in my mouth. This was so deeply erotic and taboo, but I loved it. I could literally taste, smell and feel David's essence in my mouth. While swallowing cum yesterday would have been a concept that disgusted me, in this moment I wanted David's semen in my mouth badly. I would definitely swallow it. It felt sexy and sexually dirty to want his semen filling my mouth and then swallowing it. It was like I would be part of him. I would be his.

I knew exactly how to make David cum. I knew what I liked in a blow job. I worked his cock as deep into my mouth as I could. I gently cupped his balls and began allowing his soft mushroom head to hit the back of my throat as I worked the base of his hard veiny cock with my tongue. I got him into a rythm. I could feel David's cock getting tighter and harder in my mouth. I could feel his balls contracting and moving as I coaxed them of their semen. David was moaning and almost yelling, "Yes, yes, yes...suck me, suck me. Oh God baby. Suck me." At this point, I was able to get almost all of his 7 inch cock into my throat to where I could smell the anal sex we were having on his trimmed pubic hair. The taste of cum was starting to fill my mouth and the smell drove me into a frenzy of sucking his cock as deeply and sensually as I could. I could feel that I was about to cum without even touching my cock. And then, I started to taste and feel streams of his liquids deep in my mouth. It was salty, it was sweet and it was nothing like I expected. The taste matched the sounds, the scents and the excitement of David deeply moaning as he pumped stream after stream of cum in my mouth. David was having an intense orgasm and he grabbed my head gently face fucking me. I swallowed and sucked each stream as he forced it into me. It felt like his orgasm was never going to end or that the more I coaxed his balls and sucked his cock, the longer it would last. I wanted this to last as long as it could.

As David's climax ended, I could feel him lay there seemingly lifeless, breathing, his penis was still rock hard and glistening with my saliva. David pulled my shoulders gesturing that he wanted me to kiss him. Without any hesitation, David opened his mouth and fully kissed me, ignoring that I just consumed his seed. I straddled him as I kissed him, rubbing his now semi-erect cock against mine. David stopped our sensual kiss, and said, "I want to feel you cum in me. I want you to fuck me and kiss me." David looked me in the eye and pulled my neck to him kissing it and sucking it. David motioned to the nightstand where there was lubricant. I said, "I could do what you did? With going down on you?" David said, "No, fuck me. I want you in me now."

I grabbed the lubricant, and David pushed his legs back to his shoulders and he shoved a pillow under the small of his back. I saw his asshole and before using lubricant I could not resist kissing his hole, smelling his hole, rimming him and teasing my tongue into his hole. David did not object. Instead, I could tell he was in ecstasy from this. As I worked his hole , with as much passion as I was kissing him, I could see his cock becoming erect. David was enjoying it. I just wanted to please him more, so I did as he did. I left my saliva in and around his hole and I even used a finger to get inside of him. David moaned loudly as my saliva lubricated finger went in. I could not take much more of this. At this point, my cock was about to explode. As such, I pushed it up against David's man tunnel and with barely any resistance it slipped in. David pulled me by the back of my neck and kissed me. Our tongues then met and swirled together as my hard cock slid deep into David. "David smiled and said, fuck me. I want you to come inside me. Fuck me Jack." Sliding my slick saliva covered dick into David's tight ass almost made me cum right at that moment. But I held off.

I fucked David in missionary position and cannot properly describe how sexy and different this was. As I fucked him, I could feel through his cock that he loved it. As my penis drove deep into him and as I handled his cock, I could often feel the reaction in his hard on. It was not very long though as I need to let go of my orgasm. I was slipping in and out of David's soft hot ass, when my cock exploded with cum. David knew I was coming. He grabbed me and said "Kiss me...let me fuck it out of you." David's body was now writhing under me, his hole tightening as he was moving his body and grinding me dick around inside of him. As my hot semen filled his asshole, it became evident as there was less friction. I was now pounding his prostate directly. As each wave of my orgasm poured into David, David yelled, "Oh God, I'm coming!" As I fucked him and pounded his prostate David let out what little was left of his semen onto his stomach as I stroked his cock gently. I took his semen on my hand and smelled it. It smelled wonderful and sexual. David pulled me to him and we fell on our sides looking at one another. We were breathing heavy, our bodies were glistening with sweat and semen.

It was this, the first time that I had an orgasm with a gay man that I did not want to run after having the climax. Last time, I craved the smell, taste and feel of man sex. Yet, when it was over I wanted to run. This time, I stared into the mirror at the two of us laying naked and spent and all I wanted to do was fall asleep...and be wakened by a hot cock fucking me. Like David, I wanted him and I wanted to make sure this happened again. I was getting comfortable with it.

I looked at my watch and checked my silenced cell phone. I had missed several calls from my wife and one from my office. It was 4:30 pm. David and I made love for about one hour. It seemed like our sex was so short, yet time flew by. I had to pick up my children and say goodbye. As I lay there, David said, "Wow, that was incredible sex once again. Are you sure you've never been with a guy?" I responded, "No. But I now regret that. I really like being with you and this fucking sex with a man is addicting." David smiled, "Well, it's our secret. I am okay with you having a second life. I have a second life. Let's make love, let's have fun with it. Who knows, I might even convince my husband to do a threesome." I didn't know what to say about that. I never had a threesome with anyone. I smiled and got up. "I have to go," I said to David. He got up and began getting dressed as I started getting my clothes on. He picked my underwear off the floor. They were tighter, longer underwear made by Polo. I liked them, they were blue and showed my cock nicely. David threw them on the bed. "Do you mind if I keep these?" I looked at him awkwardly. His underwear were nicer than mine. David then picked them up and smelled them, "When I jerk off, I would love to smell you." It was a sexy and deeply dirty request...but that was David.

David walked me to his door and asked when I could see him again. I said, "I'm not sure, but I will see about doing it soon. I can't always just walk out of my office to have an affair." David said in seriousness, "Don't look at this as an affair Jack, look at it as friends. Friends with benefits." David sighed, "I know, cliche." David kissed me at the door, a kiss that led into making out, which led me to wanting to walk back to his bedroom. I did not have time. We broke it off and I went back into life as usual, a straight family life.

This is Sunday, and as I write this, I realize that I am hooked and that I really like David. I don't think anything in the future with David could be nearly as exciting or erotic.  As I read stories, I feel glad to have such great experiences for my first and second time. So, I may or may not document my future with David.  Now, I know there will be more encounters with David and I know that, despite how David wants me to see this, I am having an affair.