The First Time With A Man

As a teen I fooled around with boys but this was my first man.

This is kind of a long story so I’ll do my best to keep it as short as possible. If you finish reading it I think you’ll like it.

As I mentioned in previous posts, I am an overweight man in my mid forties. I am bisexual. Mostly women but once in a while I find myself craving a man. When I am with a man I am almost always dressed up like a woman. I’m into a just about anything in the bedroom but truth be told nothing turns me on like getting dolled up and being taken by a man.. or two.. or five lol.

By the time I was 16 I was full on bisexual. I knew it. My friends knew it. And my mom knew it. What my mom didn’t know was that I had been dressing up in her clothes almost every single day. Both of us being overweight , her clothes fit me better than I expected. She had a bag in the closet full of old bras and underwear that she didn’t wear anymore and I had swiped most of them. I would wear panties under my boxer shorts everyday to school.

Another thing my mom didn’t know about was I would masturbate with her dildos and vibrators. I had gotten comfortable with a silicone dick in my ass.

When I was 18 and done with high school, my dreams of being a professional football player were quickly shattered. I had gained even more weight and become more and more out of shape. While my dreams outside of the bedroom were being crushed, my dreams inside the bedroom got more and more real. The added weight meant my breasts grew and I was able to wear a bra.

Finishing high school without a plan for my future lead me to a dreadful job in an office. I had been working there for almost 3 months completely unnoticed when one day a woman approached me and asked if I was interested in attending a company meeting. I had no clue what she meant but I agreed just because it got me out of my regular routine for an hour.

I sat in board room surrounded by people I had never met, talking about things that were way above my pay grade and trying to stay awake so I didn’t get fired. When the meeting finally ended and everyone got up and left, a man that was sitting next to me grabbed my arm and asked me if I’d stay behind a moment. I agreed and we began to talk. It started off as just chit chat, getting to know each other on a very basic level. He asked if I’d like a better job and if I’d like to help him out with this project they were just discussing. After admitting I didn’t pay attention during the meeting, he laughed and admitted the same thing.

He told me his name was Dave and over the course of the next month, I worked closely with him on this particular project. When it was all said and done, we did a pretty good job and got handsomely rewarded for our efforts.

Dave was an executive guy, 42, stood about 6’2”, was in good shape, had black hair with a few gray strands. He also had a thick black mustache that I kind of thought was hot. As an 18 year old kid working ha first job in the city, having him take me under his wing for a while kind of made me enamored with him.

I found myself going home in the evenings, retreating to my room, dressing up in some lingerie and masturbating thinking about Dave. I couldn’t get him out of my head!

One day Dave called me into his office. He asked me if I’d like to go out after work to celebrate our recent success on that project we worked on. Even if I wasn’t fantasizing about him I would have said yes. It was a free meal!

He took me to a really nice restaurant I had never been to before. Very nice, very classy and very expensive. Dave asked me question after question about myself. Did I have a girlfriend? What did I like to do? What kind of music did I listen to? It started to feel like a date. Even if that wasn’t his intention, I treated like we were on our first date.

When we were done eating, he drove me home. I started getting a little vibe from him but nothing happened and he dropped me off and went home. Incredibly turned on, I raced to my room, threw on my sexiest outfit, grabbed my favorite dildo and pleasured myself while thinking of Dave. I came so hard that I got a little lightheaded. I slept in the lingerie that night cuddled up with a pillow still pretending it was Dave.

The next day at work, I wore the sexiest lace and satin panties I had with no boxers over them. The whole day I thought about him but he didn’t speak to me at all. Finally as the day was wrapping up, most of the staff had left or was about to, Dave called me into his office. I was incredibly nervous!

Dave started by closing the door behind me and ushering me to a chair in front of his desk. He sat on the edge of his desk and began talking to me. He asked if I had a nice time the night before. Then he said it!

“I really like you. I thought there was some connection between us last night.” Dave said

My chest began pounding like crazy!

“Yeah, I completely agree!” I said perhaps a bit overzealous.

“That’s great!” He said extending his hand

I took his hand and he pulled me up to my feet and then pulled me towards him. We were nose to nose now. He put his hands on my hips and kissed me. First just a few soft pecks and then he slid his tongue in my mouth. We made out for a few minutes. He nibbled on my neck and ear. His hands were all over me! He was squeezing my ass cheeks the most.

“I was so scared you wouldn’t be interested in me.” Dave said “…wasn’t sure if you were gay or not.”

“I’m not, I’m bisexual. I was positive you were straight!” I said with a bit of a giggle

We returned to making out. I reached down and felt his massive erection. If it was as big as it felt… WOW!

As soon as my hand got down there, Dave started unbuttoning his slacks and belt. He quickly shoved his pants to his ankles. I felt his big dick flip into my hand. It was huge! I knew what he wanted. I wanted it too!

I dropped to my knees. His impressive manhood stared me right in the face. He was a very thick 9”! He had a nice groomed patch of black pubic hair just above his cock and his balls were clean shaved. I grabbed ahold of his member and flicked the tip of his cock with my tongue. I was incredibly nervous to proceed. I had only done oral sex with my friend John and his dick was no more than 5”. This was the first man’s cock I had ever seen.

After teasing him a bit with my tongue, I took a deep breath and put as much of his dick in my mouth as I could. Dave let out a sigh of relief and sat back down on the edge of his desk. He began running his fingers through my hair and ever so gently thrusting his hips to match the motion of my head bobbing. His cock tasted incredible. It smelled like a man’s cock should smell. It was very soft and delicate but also harder than any cock I’ve ever felt.

“I’ve been fantasizing about this for weeks!” Dave moaned “.. feels amazing!” He added

I continued to bob my head up and down on his beautiful cock. Cupping and occasionally licking and sucking his smooth balls.

Dave’s grip on my hair suddenly tightened. His breathing increased and his body tensed up. I felt his cock swelling in my mouth. Then a huge squirt of hot cum shot down my throat.

“Oh fuck!” Dave groaned

A second and third shot of cum hit the roof of my mouth and I quickly swallowed it. I continued to suck his cock until every drop of cum was in my stomach.

Dave pulled up to my feet. Grabbed ahold of my ass and once again put his tongue in my mouth.

“That was incredible!” Dave whispered

“I thought so too.” I answered

“I really want to fuck you right now.” Dave confessed

I told him that I honestly wanted him to fuck me as well but I was really nervous about that since I had never actually been with a man that way before. Dave was a gentleman about it and didn’t press the issue.

The next morning I got to work and I was so horny. After sucking his cock and him bringing up sex, I went home and couldn’t stop thinking about his impressive dick and I wanted him to fuck me. Dave was already in a meeting when I got there and I left a message with his secretary. When he didn’t respond after an hour or so, I called his desk and left a very brief but very detailed voicemail about what I wanted him to do to me.

Just before lunch, I felt a tap on my shoulder. I turned around and it was Dave. He said he was going out to lunch and wanted me to come. I obviously agreed. When we got out of the building he told me that we were going to his place and he had cleared it with my supervisor that I was leaving early as well.

The drive to his house was only about 10 minutes but as soon as we got on the road, I reached down and began rubbing his cock while he drove. By the time we got to his house we were so worked up we almost started right there in the driveway.

As we entered the house, Dave quickly shut and locked the door behind him. Before he could even let go of the door handle, he had his tongue in my mouth. We aggressively made out in the doorway for a minute or so before he grabbed my hand and lead me to his bedroom. He had a huge king sized bed!

Dave quickly took off his pants, then his socks. I began removing my clothes as well. Now we stood in front of each other naked. He had the sexiest patch of chest hair with a trail that lead to his belly button. I had woken up an hour earlier that morning just so I could take a shower and shave my entire body. Being 18 I hadn’t a ton of body hair but what I had I removed.

Dave’s cock stood straight up and was poking my chubby stomach. His hands had a firm grip on my ass! He nibbles on my neck and ear just like the night before. I reached down and began stroking his throbbing cock. Dave let out a gasp and he bit his bottom lip as my hand slid up and down his shaft. His hands let go of my ass and made their way to my chest. He groped my breasts and began sucking and biting my nipples. That was the first time anyone had done that to me and it sent me to the moon! I had pinched and played with my nipples all the time while masturbating but this was the first time anyone had sucked or nibbled on them. I fucking loved it!

I sat down on the end of his bed and started sucking his cock. It was throbbing! I could feel his pulse beating on my tongue as I ran it up the base of his shaft.

“God I want you so bad!” Dave moaned

“Take me then! Take me!” I cried out

I climbed up on the bed and laid on my back. Dave grabbed his lubricant from the drawer and joined me on the bed. He positioned himself between my legs and squirted a healthy amount of lube on his cock. Then he reached down and wiped his hand on my ass even sliding a finger inside my hole. I let out a little moan as it caught me off guard.

“Is this your first time?” Dave asked

“Mhmm.” I replied

“I’ll be gentle.” He said

“Be a man and take me!” I cried as the anticipation had become unbearable

I never wanted anything more in my 18 years than to have this 42 year old man assert himself on me. I wanted every inch of his cock inside me. I wanted to pleasure him like no one has before.

Dave lifted my legs in the air and placed my feet on his shoulders. I felt a cold drop of lube hit my hole just before he pressed his cock against it. He pushed. Then he pushed some more.

“Relax. Let your breath out.” Dave encouraged me

I did as he said. I let out the breath I was holding in and when I did, he pushed his cock inside me.

“Oh fuck that’s big!” I cried

“If…” Dave said before I cut him off

“I want you to fuck me! Take me! Take me deep, Dave!” I cried

Dave slowly began thrusting his manhood in and out of my tight asshole. My legs dropped from his shoulders and I wrapped them around his waist.

“Yes! Yes! Take me deep!” I cried out

Waves of pleasure cascade over my body, filling every pore of my being like ocean water through hot sand. More! I want more! How long I waited to feel his breath on my neck, his hands wrapped around my waist, his fingers caressing my lips, and his manhood deep inside of me. Our bodies are entwined in my primal dance, moving faster and faster to the rhythm of the creaking bed springs. Our skin bathed in flickers of sunlight through the window. I can’t hear myself moaning, but I must be because my throat is dry. I can’t feel what my hands are doing but the blood under my fingernails means I’m digging into his back. He’s no longer kissing me, but nibbling, biting, pulling himself toward me harder and harder. His control over me untamed, animalistic. It’s so hot in the room that we can barely breathe. The bed sheets clinging to our sweat soaked bodies. Beads of sweat drip from his nose and land on my sweaty chest. Dave looks up! We make eye contact. He stares into my soul for more than a standard moment. He bites his bottom lip and makes one last thrust.

“Take me deep I scream!” Pulling him as close to me as I can with my legs.

Our eyes remain locked on each other as he releases himself inside me. He silences my screams by shoving his tongue in my mouth. We’re now screaming into each other’s mouth’s. As I tighten my hole I feel his cock pulsing as it squirts shot after shot of hot cum deep inside me! I was so fixated on pleasuring him that I didn’t even notice that I had an orgasm all over my stomach.

Dave finally pulls his manhood from my ass and he collapses on top of me. Our sweat mixes with semen but neither of us cares. We are exhausted. I can’t believe what just happened. We only just met but I think we’re in love.

Dave and I fall asleep having said nothing since. Dave spoons me as we sleep off our exhaustion. I awake to Dave kissing my shoulder, his hand groping my breast and his erect cock pressed against my ass.

“Mmm.. hey.” I say reaching back and feeling his hard cock.

“I’m so hot for you!” Dave whispers in my ear “..I want you so bad!”

“Then take it!” I urged him

Still spooning me, I feel Dave press his cock against my hole. I’m shocked at how easy it slid in this time.

“Oh, fuck yes!” I cry out

Dave grinds on me for a minute or so thrusting his cock deeper and deeper inside me.

“I thought you wanted to fuck me?” I ask

“Mhmm” Dave grunts

“Then do it! Fuck me! Make me your bitch!” I demand

Dave pulls his cock from my ass and sits up. He positions me on my hands and knees and gets behind me. Once again he slides his massive erection inside my ass. I let out a scream of pleasure. Dave’s hands firmly gripping my fat ass cheeks. He begins thrusting harder and faster. Occasionally smacking my ass.

“Yes! Do it! Fuck me! Smack my ass! Come on! Fuck me like a man fucks!” I scream into his pillow

Dave is thrusting himself inside me as hard as he can!

“I’m gonna cum so hard!” Dave grunts

“Do it! Cum for me!” I demand

Dave pulls his cock from my ass and turns me over. He shoves his dick in my mouth and releases another batch of hot cum down my throat. I was so hot and turned on by the entire situation that I didn’t care that his cock was just in my ass. It still tasted like him and it was one of the hottest things I’ve ever had done to me. He did exactly what I wanted him to in that moment. Asserted himself and took me like a man.

Afterwards we both took showers and had dinner together. We talked about what we had done and I thought it was weird how the first time we did it, it was like we were making love and the second time we were just fucking! Not sure what that meant at that moment. I ended up spending the night with him. We had sex 3 more times before he drove me home in the morning. Dave and I saw each other for almost 3 years. I’ll probably write about some of our other escapades. There were a lot of them! Thanks for sticking this long ass story out.

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