My Real First Experience With A Man

I am a straight male who is 46. I’m 6 foot 2 inches and I am athletic. I am masculine and have never considered myself attractive to anyone but women. I have been married for 15 years to a woman and never questioned that until a recent business trip.

Last week I kissed my wife goodbye and traveled to Orlando for business. I am a lawyer, and my business there was the typical…long depositions and back to a nice hotel. I had no plans to do anything the evening after my depositions, other than have a nice dinner at the hotel bar and hit the hay early. After all, I had to drive in the morning to get home West Palm Beach.

I was staying at a nice hotel in Winter Park. It was the Alfond Inn, not 5 star, but nicely appointed and quaint. It was a Friday night and the restaurant was busy as was the bar. So, I sat at the end of the hotel bar, ordered an Old Fashioned and started going through work emails. I was tired and asked the bartender for the menu. As he brought it over, he said, “That man wanted to buy you a drink. He picked up your tab.” I looked down the bar and thin man in his 50s with dark brown hair, with some grey waved. I was dressed in a suit and so was he. I figured maybe he was another lawyer or someone I knew.

So, I went over to thank him and tell him it’s not necessary. I am truly not into people buying me anything. So, in a way, I was annoyed. I sorta just wanted to check my emails, have dinner and go to sleep. Now this guy was forcing me to be cordial. And I was. I thanked him and asked “Do I know you?” He smiled, and said “Hi, I’m David, we don’t know each other but you are the best dressed at the bar, so here’s to you.” He held up what appeared to be a martini and I toasted. I gave him my name, told him I’m here on business and I slid my way out of the conversation. I started suspecting that he was gay.

I sat at my place at the bar and went back to ordering dinner and returning emails. As my dinner arrived, so too did David. He said “Do you mind if I sit?” I told him “No, no, just don’t buy me anything.” He laughed, and said “That’s a deal.” He sat down, ordered his own food and we started chatting.

David told me he was gay. He lived in Palm Beach, not far from where I lived. We talked about food, tennis, restaurants and he told me about his husband. He was married for 10 years. And then we got into taking about sex. That made me horny a bit….which was strange.

Admittedly, I never really discussed sex with a gay man. David had a husband who was more effeminate and David was more the guy in the relationship. I told him about my wife, my kids and by the time I looked at my watch I realized we had finished dinner and were on our third drink. I had a good buzz.

David then asked me, “Have you ever done anything with a guy?” I responded, “No, why would you think that?” David said, “Well, I’ve been with girls in my early life, so I just wondered. I told him, “No, but I never really was in that position to be with a guy.”

The minute I said that, I knew I was leading him on. I was here at this hotel, this gay man was asking me a question that I could have closed the subject on. But, my cock started to get hard in my pants. I started to feel butterflies. It was like I was in high school with my first female sexual partner, yet this was a guy. I had to lead him on. At that moment I was confused but attracted. I liked where this was going and wanted to keep it going.

David took the bait, and he asked “Well, what would you do if you could experiment with a guy?” I responded, now nervously, “I, I uh…well I am married so…”. David then said, “Yes, we are both married. But I’m on Prep and I’m going to be honest, I’d like to help you experiment. I like you. “. I asked him what Prep was. He told me it was a medication that made him resistant to HIV. Without him telling me, I gathered that he and his husband permissively ventured off to have their own affairs. David then said, “We are both here, I just got tested for every disease on Earth yesterday. You can experiment with me and there is no risk. Worst case scenario, you realize men are not for ou.”

I did not know how to respond. Every part of me wanted to say “Yes!” But, I couldn’t. However, I couldn’t stop leading him on. I didn’t want to commit but I didn’t want to turn him down either. So, I said, “You, for whatever reason have me reeling and I’m flattered. But, I am married. My relationship would be over if I cheated.” I was so hard at this point and my cock was even dripping with precum in my underwear. I so wanted to experiment, but I was so nervous and not wanting to at the same time.

At this point, David was paying and I think he knew how conflicted I was. He put his hand on my thigh under the bar. His touch felt good and I wanted to feel more of it. He looked at me and wrote his room number 302, on the hotel receipt for the bar tender. David said, “I have a bottle of wine at the room, and two glasses. If you want to join me, you don’t have to cheat. But what happens at the Alfond stays at the Alfond.” David said goodbye, left his card on the bar and then it was up to me. I knew my life might change if I went to Room 302.

I went back to my room, called my wife, tucked my kids in via phone and tried to shower without thinking of David. I started looking at gay porn , just to see what I could be getting into. I decided I was going to do it. I put on jeans and tshirt. I walked out of the room and made it to David’s door. There was nobody in the hall, I was shaking nervous and I knocked. There was David. He came to the door, opened it and let me in. He closed the door behind us and locked it.

David was still in his suit pants. He smiled and said, “So, you showered and changed? You look good in jeans.” I responded “Thanks, so I’m sorry I’m nervous. I have never thought of this before.” David looked at me, handed me a glass of wine and said, “Lets try something.” I sipped the wine and looked at him intently. “Let me kiss you. I mean really kiss you. Like French kissing. I know that’s foreign to you. But let me do that for 30 seconds, I’ll feel your cock through your pants, and if you’re hard we will do other things.” “If not”, he continued, “There’s a nice porch overlooking the street. We can finish our wine and you’ve had your first and only secret gay experimentation. I will never tell a soul.” I agreed. I sipped my wine, put it down. Before I knew it, David was moving in to kiss me. This was going to happen….

I felt his lips gently kiss mine. Immediately I could feel the stubble, which was not my favorite. However, my cock sprung to life as I opened my mouth letting in his tongue. I reciprocated and our tongues danced slowly together. I could smell his breath, feel his stubble and with every thrust of his tongue precum edged from my hard cock. David took my head in his hand and grabbed my cock through my jeans with his other hand.

David broke away, breathing heavy. I realized that I too was breathing heavy. We were connecting. David was about to say something as held my cock through my jeans. He didn’t even have to say a word. I pulled him by his shirt and he gently pushed me up against the wall kissing me with intense passion. I had never made out with a man and now I was. It was intense.

David pushed his hard cock through his suit pants against mine. He wa rubbing his dick rhythmically against mine. My cock was wet with precum and now I was moaning in pleasure.

David broke away again. He began undoing my pants. I allowed it. He looked me in the eyes with a grin as my hard 6.5 inch cock pushed out of the jeans with only my boxer shorts separating it from David, David pulled it from my boxers and whispered “Nice.” As I feared, my cock and boxers were wet with cum. David took the precum on his pointer finger and licked it. Then he took out his own cock. It was bigger than mine, it was cut and veiny. He had trimmed pubic hair and precum glistening from the tip of his mushroom head. David dabbed his finger on his precum and put it in my mouth before I could object. It was salty, smelled sort of different but I accepted it. David whispered in my ear, “You are mine.” I felt him gently kissing my neck. I was so turned on, I knew I couldn’t stop. It was like a drug.

David led me to the bathroom. He brought out lubrication and what I discovered was an enema kit. David ran warm water and explained that if I wanted to really experience tonight, he would make love to me. But, he was not into surprises. I understood. As he closed the bathroom door, for the first time, I used a warm water enema…twice. I flushed anything and everything from me. As I was doing so, I was wondering if anal sex would hurt? David had a big cock, how would I ever enjoy this? But, I was in a trance. I was so sexually excited by David that I would do anything to feel the next rush. And so, I was naked and cleaned out as I exited the bathroom.

David led me to the bed. He took off all of his clothes, shut the curtains and put my hand on his erect large 7 inch penis. He stood before me, now moving between my legs. His beautiful cock was in my face.

I could smell him. He smelled like man, muskier and sexier than I ever imagined. The smell made me want more. As I felt his spongy cock that was now getting closer and closer to my face, I had no hesitation to put it in my mouth. I could feel his manhood, smell his body and taste his precum. Every drip I tasted made me cup his balls, massage them and put more cock deeper in my mouth. In and out. David was moaning with pleasure. “Are you sure you never did this before?” he moaned. With every bit of approval I then wanted to please him more. I wanted to feel him cum in my mouth. I wanted to feel him cum in my mouth at that moment.

I knew he was close. He knew he was close. “Not yet!” He moaned as he slid his cock out of my mouth. He turned around, and before me was his thin but nice ass. My natural instinct was to kiss it, to lick it and to feel it. David bent over and grabbed onto nearby chair. He exposed his asshole almost like a stripper. It was sexy. I realized that his musky man smell was more evident near his ass. I wanted more, I wanted him badly as the scent drew me in. I licked and probed his asshole with my tongue. As my tongue gently probed his hole, the smell, which was dirty, raw and a sexy good body odor drew intoxicated me. I worked my tongue into his butthole and kissed him passionately. David moaned with pleasure. He then broke away again as I sat there on the bed naked, hard as a rock and ready to do whatever David wanted.

He grabbed lubrication from the bed stand and began working it over his ass crack. He walked over to me and grabbed my hard cock with his lubed hand. He stroked my cock gently lining it up against his asshole. Then he pushed me back, straddled me and we began kissing deeply again. As we made out, David positioned his asshole right against my hard cock. Before I could say or do anything, David bit my lip playfully and I could feel my cock slipping slowly into him. David moaned “Mmmmm, your cock is so hot. Let’s fuck, I want to fuck you,”. I said nothing as my pulsing cock was going deeper and deeper. I slipped every inch of me inside of him and began fucking David’s tight hot asshole.

We unlocked our lips, David sat up and I could see his erect cock now bouncing with streams of precum as I fucked him deeper and deeper while he was on top of me. David could feel my cock tensing and moaned, “Yes! Cum in me, please cum in me!” Whether he liked it or not, my cock exploded in him. I pushed it as far in as possible. I’m certain he could feel the warm cum as I immediately felt it spilling from his ass around my crotch. David kissed me and our tongues met once again as he worked every drop of cum from my cock. We turned onto our sides, sweating and hard breathing. I said to David, “Wow, that was amazing!,”. David smiled and said, “it’s not over, now it’s my turn.”

I had spurted my man seed into David in my first gay experience. Selfishly, after the rush, I just wanted to leave. That is how it is for guys I suppose, particularly when you’re both cheating and with a man. Was I now gay? So many thoughts raced in my mind. But I had to make him cum, I had to let him fuck me. The idea was not a good one to me then. Yet, I stayed and would get this done before going. David saw my soft cock and seemed to understand.

David then changed the mood. “I know you’ve had a great orgasm, but you have to trust me, I’ll make you have another.” I had my doubts. I owed him though. I truly was a good lover, even with a man. I wanted him to cum. So, despite my doubt I began feeling excited to feel him cum.

David had me lay on my chest and began a back massage. He kissed my neck, left saliva trails down the middle of my back and rested his hard clock between my ass cheeks. David grabbed the lube moved his penis up to the small of my back and then began working his finger into my butt hole. David massaged imy hole and I started to get hard again. I couldn’t believe I was starting to feel horny again as David gently played with my ass.

David then worked his finger into my hole. After the massage and probing, I could feel my body accept it. My asshole relaxed and it started to feel sexual. I never used my ass for sex, this was new and enticing. He went deeper and found my prostate.. He rubbed it gently as I moaned. Could this be happening? I was fully erect and now humping the bed as David went in and out of my hole with his finger.

David worked a second finger in. I could feel my hole stretching, but David was gentle. It took time but as my hole and muscles loosened, my ass accepted two fingers. At first there was nothing sexual about this. What surprised me is that I felt his fingers going I and out and the area around my ass felt awesome. I liked the feeling of the in and out. As he continued to go in and out I wanted more. I wanted David’s dick.

I turned over and pushed David off me. He was surprised and I think he thought I was mad or not liking it.. I grabbed David by the shoulders and said “Please fuck me,”. David immediately kissed me, his tongue darting into my mouth. He grabbed more lube, put it on his cock and pushed my knees up to my shoulders exposing my now opened asshole. I felt David gently use his hand to guide his hard cock at the entryway of my hole. He looked at me in the eyes as he moved slowly in and out with his mushroom head. The head popped in and out, not going too deep. It started to feel nice, it started to accept David’s large cock. David was working up a sweat, I could smell different smells, musky and sexy. Within a minute, I felt the tip slip deeper into the hole and David left it there. I shuddered and moaned softly.

There was pain, there was stretching but I looked down and I knew my cock and my whole body wanted him in me. As David entered his tongue in my mouth and kissed me deeply, his cock slid slowly and deeply into me further. David and I made out and I pulled his hips closer, as he got deeper. I could feel his cock filling me, stretching me. His balls rested against my ass. I was penetrated, I felt like a woman and it felt good to be fucked. I could feel his cock pressing on my prostrate another experience that drove me wild.. Being fucked by David was feeling better and better.

David began getting harder. I could hear his balls slapping into me, the pressure was getting more intense. I could feel his cock hardening and getting tight. David was now moaning and fucking me hard. He was going to cum. I spread my legs more, I whispered, “Oh yes, fuck me, cum in me David.” Suddenly David’s tongue was, again, tangled with mine as his seed sprayed into my asshole. I could feel the bursts, his cock contracting as he pushed his seed deep into me. It felt warm, it felt amazing and David grabbed my cock making the experience better.

As David came in me, David”s cock slammed into my prostate driving me wild with pleasure. This was pleasure I never thought was possible. It was an orgasm coming from a place I never knew. He was jerking my cock at the time in the same rhythm as his dick pounded sperm into me. I could smell him, taste him and feel his pleasure. It was all too much, it was utter extract. My dick exploded with cum rushing over David’s hand and I let out a deep moan. The movement of his cock caused stream after stream of semen to flow out. David smiled and said “yes, let it out, I love your cum.” I came more than I’ve ever know possible.

After we both were exhausted. We both sat there looking at one another. David smiled and said, “That was good sex, you had an experience like no other for your first.” As David slid off me, semen ran over my pubic hair. His cum, my cum and the smell of sex was everywhere. I said, “I don’t know what to say. I cannot believe what we did.” David looked at me in a disappointing way, “Are you okay?”

I told him, “I’m fine, I just never thought about being with a guy. I can’t believe I came like that twice. I suppose I got the whole experience in my first time.” David smiled and said to me “Not the whole experience…I could show you things. We definitely need to do this again. It’s great that you live close by. I don’t want to be a home wreaker and I won’t, but I really like you. Having sex like that is not everyday. We should do it often. Your wife won’t know., I promise..” I told him I would, but really wasn’t sure.

As the night went on, we both cleaned up and I went back to my room. David wanted me to stay since he thought we could fuck in the morning before I left. I couldn’t. I had just fucked a guy and kissed and sucked a guy. I liked it. I was not supposed to like it. I had too much going through my head to stay. David and I exchanged contact info and I was back to reality in my room. I got up early and went home. I had hours to think about what happened. How would this affect me was my concern.

It is now a week later. David has reached out to me several times. I have not been able to get together with him, mostly because I make up reasons not to. He lives near me and I don’t know what to do. My wife has no idea, my kids have no idea but I have this memory and this urge. I keep arguing with myself. On the one hand I need to see David so I can get the full experience, on the other I’m a straight married man.

This was my first gay sexual experience