My Time With Char

Friday’s meeting with the Big Credit Card company’s bosses was long and drawn-out, keeping all of us nervous about the end results, but we got through it. It was excruciating, rather stupid and ridiculous for lack of better words.

What kept me smiling through it was knowing the fact that tomorrow night I was going to be with Char for dinner and for our first overnight at my place.

Saturday morning, I got up and started cleaning up and making sure everything was perfect. I ran to the drug store and got lube and condoms in case we went further than we had before. We were planning on going out for a romantic dinner and during I was going to ask Char to date me exclusively. I was ready for this. Over the past few weeks, I had grown even more fond of him and moreover, I couldn’t get enough of his dick. All I watched was gay porn, dreamt of dick, would fall asleep thinking of him and realized how bad I wanted, needed and desired anal sex.

After dinner we had spoken about going for a round of mini–golf, or a walk along the beach, something fun for us to do as a couple before heading back to my place at the night ended for a sleep over. I was extremely nervous and rattled, but yet excited and looking forward to it. I had never spent the night with a man at my house. Hell, I have never even dated a man before him. This was my first true homosexual experience. And based on our Thursday nights — heat of the moment conversation – about anal sex, I was really concerned, panicked and yet overly excited about fucking him, or him fucking me. I was a bag of mixed emotions. But I was ready. No matter what happened, I was ready.

Char made his way over to my place right at 6:30, bringing a bag of clothes and his toiletries with him. He’s never been to my place, so after he arrived, I gave him the grand tour of my three bedrooms, two bath condo. He liked it and said, “It was decorated like he would’ve expected. Somewhat more modern, big large TV’s, a sexy big bed, with long deeply dark drapes with my bedroom balcony off of it.”

I wanted to take Char to the local Chop House, near me where I have eaten many times before. I drove to the restaurant, as we passed comfortable conversation. As we sat during dinner, having wine and our steaks, Char leaned over and began a deep and meaningful conversation.

“Danny,” he spoke. I appreciate all your time, energy, at work. You are one of my best guys. But more importantly, I am falling for you and I haven’t cared for a man the way I do you in a long time.”

“Do you think we could make this more permanent.” He asked.

“Permanent?” I asked.

“Yeah,” he replied. “Just you and I. Maybe monogamous, would have been a better word. I don’t want you dating anyone else but me and I don’t want to be dating anyone buy you.”

I was glad he asked, because I was planning on bringing it up to him. I just didn’t know how.

“Yes.” I replied. “I think that’s a great idea and I was having the same thoughts.”

“Good.” He spoke, as he smiled at me.

Char waived the waiter over and asked for more wine and two deserts to go. I was actually surprised because I thought maybe we were going to go out after. But now, I think he had other plans.

We finished our dinner, sipping our wine and toasting to our new dedication to each other. We couldn’t stop staring into each other’s eyes, as we finished up. It was about 8:30 when we left the restaurant. He held the bag of deserts as I drove us home. We made a pit stop at the liquor store, grabbing a bottle of wine, finally arriving back at my place.

We were both dressed very businesslike and he wanted to change into something more comfortable, as I popped the wine open. Char retuned wearing a pair of tight silky pajama pants, with matching shirt, only buttoned up about half way showing his upper chest. We raised our glasses and sipped our wine. We cuddled on the couch for a while watching TV, until we both wanted to eat our deserts. Char went to the fridge and grabbed the platters and forks and we sat eating and feeding each other the tiramisu. It was a wonderful, warming romantic evening.

Of course, we finished off that bottle of wine and we both were a bit buzzed when that first kiss of the night came. He was lying up against me, watching the TV when he looked up, as I looked down, and leaned in to kiss his lips.

“I am glad I am here with you Danny.” He softly whispered.

“Me too.” I replied.

We began kissing deeply and softly, just slowly getting more and more involved with each other. His kiss wet, warm and soft; almost feminine and I was loving every minute of it. I was starting to get hard and thoughts crossed my mind of his cock buried deep in his PJ’s and how bad I wanted it out. It wasn’t long into our kiss that I looked down to see that his cock was hard as a rock, because it was making the pajama bottoms poke outwards. I slid my hand down in between his legs and felt the soft silky pajamas, with a bulging cock sticking straight up inside of them. He moaned in pleasure as I caressed and cupped the tip. I wanted him and I wanted him even more now that I was buzzed and all my inhibitions were gone.

“Suck me, Danny.” He moaned out as my hand continued rubbing up and down on his hard dick.

I slid off of the couch as he started pulling down the pajama bottoms, he had no underwear on underneath. I got in between his legs as he spread his legs open. His cock was rock hard sticking straight up and I wanted it. I leaned down, sliding his cock deep in my mouth as he started to unbutton the remainder of his pajama shirt buttons, spreading it open. Char was pulling on his nipples and placing his hands on the top of my head, as I bobbed up and down on his cock. My ass was tingling, my cock was hard and I didn’t know if I just wanted to keep sucking him more; or take int in the ass. But either way his cock was all I desired.

“Danny. I waana fuck you.” He moaned out.

“Oh God Char!” I moaned out as I took his cock from my mouth stroking him.

“I wanna fuck you too!” I replied.

I stood up from my knees and removed my shirt as he sat there staring at me. I pulled down my pants, then my underwear standing naked in front of him. I grabbed my cock and started stroking myself over him, feeling how thick and hearty my bulging head was.

“Common,” I moaned out as I reached out my hand to him.

Char stood up from the couch, taking my hand. We stood there kissing for another minute, both holding onto and lightly stroking each other’s cock. I walked Char to my bedroom, guiding him onto the bed. I went over to my balcony doors and closed the drapes and turned on a soft ambient light at my desk.

“Is this too much?” I asked.

“No, it’s perfect.” He replied.

I climbed onto the bed with him, lying on top of his naked body, his legs wrapping around me. We kissed deeply, as I was panicky and nervous, but so willing to have him slide his cock inside me.

“Do you have protection?” He asked.

“Yes.” I replied.

I reached over to my night stand and grabbed out the new box of condoms and the lube I purchased earlier that day. I rolled off of him and laid next to him. He shifted onto his side and we laid face to face, just kissing deeper. I was fumbling with the condom box and getting the lube open as his hand continued pulling my cock trying to stroke me off dry.

“Have you ever done this before?” Char asked.

“No, I haven’t. Beside toys” I replied.

“It may hurt at first, but I promise it’s so worth it.” He spoke.

I handed Char a wrapped condom and the lube, as I rolled him onto his back. I kissed my way down his chest, past his belly button, until I found his hard cock, poking along the side of my face. I kissed the tip, stared at it, licked it and rolled my tongue all the way around it. I slid him back into my mouth, bobbing up and down, as he opened the condom wrapper.

As I pulled away, he slid the condom over his shaft, rolling it all the way down. He rolled me onto my side next to him again, squirting a large amount of lube on his hand. He started stroking my cock, as my hand reached down grabbing his cock. I stoked him for a minute, just feeling the thin layer of rubber covering his perfect dick. I asked him for some lube and he squirted some out on my hand. I retuned my hand to his cock and I started stoking him again, getting the condom all slippery and wet, as his hand stroked me softly and we kissed deeply.

“Are you ready?” He asked.

“Yes.” I replied.

Char started to get up onto his knees as he started to roll me over. He pulled my hips upwards and that’s when the fear started. My heart raced and my asshole actually tightened, knowing he was climbing in behind me. He edged himself in behind me and slid his body up close and in-between my legs. I felt a drip of lube hit my asshole and his fingers started rubbing up and down my asshole. I was on all fours, panicked at what was about to happen.

Char edged in closer and I felt the tip of his cock, hit my asshole. He adjusted my height a bit and said; “Just relax. It’s all worth it.”

His left hand hit the outside of my left thigh and he began to pull me closer as I felt the pressure of his cock trying to penetrate me. With a few misses, he finally got the right angle and I felt him slide inside of me. It was painful and awkward, feeling something sliding in, instead of sliding out, especially considering I didn’t have control of it.

“There we go.” He mumbled out.

I felt an increase in size and depth as he slid further inside of me. My mouth wide open and light groaning sounds coming from deep inside me as he slid it back out and then back in. I didn’t know how to react. It felt so weird, so unusual, but yet so good to feel his cock in my ass. I went limp, more concerned about his dick in me, than I was about getting off.

Char slid back and forth many times, until he was all the way in. I felt his hips and stomach hit the top of my ass cheeks and I knew he was all the way in. I felt like I was going to explode, thrust his cock out by releasing, but every time he slid it in and out, my muscles relaxed more and I began to understand what he meant by, “It may hurt at first but it’s worth it.”

It was starting to feel good and now that the initial panic was over that he was nuzzled deep inside me and my muscles relaxed I started to get excited that a cock was in me. Char rocked back and forth slowly, just sliding himself in and out of me, as I groaned in pleasure, trying to enjoy it more, than fearing it. Eventually getting there.

I WAS BEING FUCKED and I FUCKING LOVED IT!!!!

“Ready for a bit faster?” he asked.

“Yes baby.” I replied.

Char picked up his pace a bit and his cock started sliding in and out of me faster and a bit deeper than before. I was moaning out more and more and was feeling sensations and passions I had never had before.

“Oh, it’s so tight.” He moaned out, as he picked up the pace more. I felt my cock start getting hard again and I didn’t know if I would cum by being fucked, or just kneel here until he came in my ass.

That’s when it hit me. This was erotic. It was sexual, it was taboo and I liked it. I absolutely fucking liked it. “Oh, Fuck Char,” I moaned out as his cock was ramming in and out of me. I have been wanting this my whole adult life and now here I am in the ambient lighting of my room, in my condo with his cock deep in my ass.

“Yes baby. Fuck me!” Spewed from my mouth.

I reached with one hand and started stroking myself while I envisioned what it looked like to be behind me, watching his cock sliding in and out. Char accidently pulled to far and slipped out, and he re-adjusted, missing a few times, trying to get back in. But when he did, the tightness of my ass, coupled with him pushing in made me squeal. I chirped aloud as his plump thick cock slid back in.

His motions thrusting back and forth as both hands were on my hips, pulling me backwards to him, “Danny, oh fuck Danny. Your ass is amazing.” Emanated through his heavy breathing.

“Char, I love your cock.” Was the only thing I could think of, so I moaned it out.

The feeling was intense. It hurt. It was odd. It was erotic and it was enlightening. I was being fucked. I had a cock in me. I was partially hard stoking myself and I was ready for more.

Char started thrusting hard, then slowly withdrawing it all the way out. Only to ram it back in hard and deep. He was making me squeal, moan and whimper sending his dick so far up into me that I was almost shaking.

“Do you want me to cum in you, or wait?” He asked.

I didn’t know how to answer. I was speechless, just staggered that I was being fucked. I reached up behind me, reaching back to feel his cock as it slid in and out of my ass. I truly wish I had a mirror on my headboard, to see him on his knees behind me fucking me hard.

“Don’t cum yet baby!” I moaned out. “I like what you’re doing. Just keep fucking me.” Spilled from my lips.

I was truly enjoying this new sensation of having a cock ramming in and out of my ass. The feeling of his meat penetrating me deeply. The thrusting motion of him forwards, while I was being manipulated backwards. The sheer taboo of it. The gayness of it. The whole, “I am being ass fucked” pleasure was turning me on more and more.

“I’m getting close Danny.” He moaned out.

Don’t cum yet baby, I want more of this.” Echoed through my moans.

Char slid his dick out from inside me as I fell face fist onto the pillows. My legs shaking, body feeing nerves firing deep inside of me, that I’ve never felt before. Char laid down next to me and softly kissed me on the cheek. He left me alone for a few minutes to catch my breath, as I saw him strip the condom off of his dick.

“Did you like it, Danny?” He asked.

“Yes.” I said loudly and profoundly.

And I did like it. I had wanted that for so long and even though he was probably inside me for no more than four minutes, I knew I had just got fucked. I had anal sex. I had my boyfriend’s cock inside me. I was going through so many feelings and emotions I didn’t know whether to be happy and scream it out the world and/or cry, because I was finally coming out (in some ways) and was nervous to have been getting cock.

When I finally caught my breath, I rolled over onto my back, feeling my asshole soaking wet, open and full of lube. Char climbed partially on top of me, lying on my side as we kissed deeply. We were falling in love and I was more cock hungry at that moment than I had ever been. Char used his hand and some more lube and started stroking me, getting me rock hard again.

“Do you wanna try on me?” He asked.

Of course, I did. I would have fucked a hole in the wall at that point. I was so hard and so ready.

Char reached for the condom box, and pulled one out. He opened it up and handed it to me as he kissed his way down my body. He slid my partially had cock into his mouth and started sucking me off. Within minutes I was so hard, so ready and so close to cumming, that I had to be in him.

“I’m ready baby.” I moaned out.

Char grabbed the condom from my hand, still lying between my legs and slid it on top of my hard shaft. He used a bit more lube getting the condom slippery wet. He pulled me upwards as he got onto his knees. I slid in behind him, my cock sticking straight out, overly hard. I was still stroking myself as he edged himself backwards towards my cock with his cute little ass.

I put the tip of my cock at his asshole and squirted his asshole with some lube as his fingers worked his asshole, getting it ready. I leaned downwards pushing hard, missing numerous times trying to get inside of him, but we were so lubed up that it just kept slipping away.

Finally, with him pushing backward and me trying to push forwards to get it in, I slid deep inside him. He gasped in pleasure as I realized I was deep inside his asshole.

“There ya go baby.” He moaned out.

I started pumping back and forth feeling the warmth of being inside him as my hard cock was inside someone again. I was so excited and so aroused; I was inside him. I placed my hands on his hips and started thrusting backwards and forwards as he was shifting his hips backwards. He’s been fucked before and knows what he likes, but this was new to me. He was moaning and whimpering with each thrust and I was an absolute awe of being inside of him. Just like in the office the other day when I wanted to be fucking him, now I was.

The sounds of slapping skin filled the room, with the echoes of him whimpering as I continued sliding back and forth looking down watching my cock slide in and out of his ass.

“Danny, Fuck Danny.” He moaned out time and time again. As I continued ass fucking him.

I was so excited, so horny, so turned on and so alive that I started getting harder and harder. I was going to cum; and it wasn’t going to be long. But that’s when I heard the hottest words, he ever said to me.

“Danny I’m going to fucking cum.”

He was going to cum with my cock in his ass. I was in sheer heaven, I started pumping fasten and harder. I had fucked a host of women from behind, but now I was deep inside my man’s ass and bringing him to orgasm.

“Danny, don’t stop,” he cried out. “Don’t stop, I’m going to cum!”

Fuck Danny!” I am fucking cumming.” He cried out.

He started shaking and releasing like he had before when I’ve made him cum. His cock was shooting cum all over bed as my cock was buried deep in his ass. Char was squealing and chirping loudly as my cock kept ramming in and out, as he came all over my sheets. Knowing I had made him cum while fucking him, fucking a man in the ass; and after losing my anal virginity, sent me into overload. I felt my cock seconds away from exploding.

“Char, I am going to cum.” Slipped from my lips.

“Cum in me Danny!” He cried out. “Fucking cum.”

I picked up my pace, his hips still thrusting backwards, hearing his moans; “Oh, oh, oh, oh, oh, fuck, Danny, Danny, Danny, escaped his lips every time I pushed my cock deep inside of him.

About a minute later, I blasted my load deep inside his ass. I groaned in a high-pitched moan as I started shooting my load. I looked down to see my condom covered cock, slowly sliding in and out of his ass, as my cock was shooting cum

“Char! Char! Char!” Spewed from my mouth. “Holy fuck!”

I leaned down on top of his back lacing my chest onto him, we both were sweating and breathing heavy, as I felt the last bit of my throbbing cock, release my cum.

His legs shaking, his arms trembling as he was trying to hold up my weight as well as his.

When I finally withdrew my cock, the tip of the condom was full of cum. His asshole still wide open as if he was waiting for more. He rolled onto his back, as I came to rest on top of his body, the wet spot of his cum right under my left hip.

We kissed deeply and passionately as we settled down from our first anal sex experience. “Did you like it, Danny?” He asked.

“More than liked it baby. I loved it.” Was my reply.

I slid off the condom as we laid in the ambient light kissing and holding each other. His naked body up against mine. His breath as thick and as heavy as mine.

His cock slowly softening as was mine.

“Char,” I spoke. “That was fucking amazing.”

And it was… Even though he was only in me for a few minutes it was a great experience to be in him and to make him cum while fucking him was sensory overload.

Char and I spent the remainder of the night lying around naked. We sucked each other off again until we both fell asleep, spent and relieved.

Waking up next to a man, was different, but hey, I was ready for this relationship and being gay. The next morning, we went out for breakfast and then back to my house for a long afternoon of sleeping on the couch, with heated make out sessions and me fucking him again.

After he left that day, I sat in the quiet of my condo deep in thought. I realized I liked sucking dick. I liked the feeling of his cock inside me last night. I liked being in him. I was nervous about it, but excited when I was doing it. Over the next eight months, Char and I dated exclusively. We hid our relationship from co-workers, but not from his family or friends; and even some of mine. I realized through it all he liked being blown and fucked. And when I needed his cock back inside me, he went along. But we realized in our relationship as time went on, he was more of the “girl” than the boy, so I would fuck him more than he would fuck me. But when he wanted to be in me, I was always a willing participant.