The Journey to Satisfaction

The Journey to Satisfaction

Act 1 - Start of the Affair

When I was 19 I started an affair with an older married man. He was in his late 30s and a perfect match for me. Buff, hairy, square features, 6 feet 2 inches tall. He also had the perfect cock that was banana shaped, six-inches long with nice thickness. As a submissive I loved how he would physically dominate me. This was easy for him because I was a skinny, 5 feet 7 inches, and kept myself fully shaved hairless. I had been with guys my age and had been doing anal masturbation. But sex for me was always about making my partner happy. It didn't matter to me if I came or not. But I always longed for someone who could satisfy me naturally.

Our affair started randomly at a conference. I was doing a business internship and he was a successful corporate executive. I felt a twinge when we met and he felt the same as he exchanged his number. For many months we texted and got to know each other. Then one day he suggested we meet and I was happy to agree. It was at this date that I realised how hot he actually was. He was a plain black T that showed his muscular physique. I struggled to control my arousal. The next week he invited me over to one of his apartments and I knew that we going to have sex.

So I prepared myself thoroughly. Made sure I was totally smooth. Had an enema to make sure everything was clean. Kept a small bottle of lube and some condoms. I put on a simple pair of jeans and a white T. But underneath I had on silk boxers and I wore an anklet.

Our date went well. We had a few drinks, listened to music, chatted. He told me that he had always been bisexual but didn't have the confidence to act on it till recently. I told him that I had always been submissive towards men and had never even really thought of women sexually. Even when I started masturbating I didn't stroke but used to rub my small cock on a pillow. At this he said to me: "I'd love to see you demonstrate this."

I got up from the couch, took off my shirt. Dropped my pants. Then my shorts. I stood naked in front of him except for my silver anklet. I took a cushion from the couch. Tucked it between my legs. And started rubbing my small cock into it.

I could see the bulge in his pants and so I threw away the cushion. Dropped to my knees. And gently unzipped his pants. Soon his beautiful cock was in my face. I hungrily sucked and licked the tip and gripped the shaft gently tugging it up and down. He gently held the back of my head and guided my movements. I kept going and I was hungry for his cum. I kept up the rhythm and soon he gripped my head firmly and began fucking my mouth. I knew he was getting close and I got ready. I did not want to spill a drop.

"Oh my God!" He groaned as his cum shot into my mouth. I greedily devoured all of it. And as his cock withdrew I opened my mouth and showed him the full load before gulping it down. It was slightly salty in taste and thick. Much more cum than I had ever got in a single load.

"Thank you" he said in a relaxed voice. "No one has sucked me like that before."

I really enjoyed satisfying him too. I quickly went to the bathroom and gargled before coming back. I was naked and he had pulled his pants back up. I asked him if he wanted me to leave.

"Of course not. Please stay. The night is still young."

I sat down next to him on the couch and placed my hand on his thigh. I leaned in and we kissed each other on the lips. Soon we were passionately making out. After some time fooling around I felt that bulge in his pants. I didn't think he would be ready again so soon. But I was very happy.

"Why don't we move to the bedroom" he said. I got up from the couch holding him by the hand and asked him to take me there.

This he did. He told me to lie down on the bed on my stomach.

I happily did so.

I heard him taking off his clothes.

The tearing of a condom packet.

The pop of a lube bottle.

And then I felt him climb onto the bed. I moved my legs apart to make way for him.

He mounted me. I loved being enveloped by his macho body. His hair and muscles felt lovely against my smoothness. And I felt his cock against my butt cheeks.

I arched my back to match his movement and soon I felt the head of his cock at my entrance.

He gently but firmly pushed the head in.

I moaned half in pain and half in pleasure and my boy pussy adjusted to his man cock.

He held the head in till I was good and then pushed further opening me up.

I moaned and whimpered and my little cock went limp as he thrust past my inner gate.

I then felt his balls on my ass cheeks and knew that I had taken his length and girth fully inside me.

He then pulled out nearly fully and pushed back in a few times.

By now all the pain was gone and I felt only pleasure as his cock massaged my male g spot. My little cock got hard again.

He then started to fuck me at a steady pace. Since he'd already cum once I figured it would take him time to get release again.

I told him how much I was loving his cock and good it felt and he told me that he had never had a better pussy. It was so tight and firm like my boy pussy was a glove made for his cock.

It was after he kept up the fucking that I felt a sissy orgasm start to build inside me. Till then I had only had sissy orgasms from anal masturbation. But here was this man leading me to one. As I felt the pressure building inside me I moaned in pleasure like a cheap whore.

And then I came. Not like a macho guy who shoots his load. But my boy cum started to drip out of my small cock. He kept fucking me through that which was ecstasy for me. I came four times in the next five minutes. And then I was completely spent. This man had fucked all the cum out of my 19 year old gay bottom ass.

But here is the thing. Sex ends when the top is done. I had never been fucked to the point where I lost my mood for sex. But as the last drops of cum leaked from my cock I started to feel something different.

When his cock went in I felt full and when it went out it felt empty. I could now fully focus on the strength and dominance of my lover. I was now a chaste boy - purely giving pleasure to my lover and feeling the sensation of fullness and emptiness. I lay under him until he came again and collapsed on top of me. The bed now a mess of my cum in the sheets and his sweat.

It was at that moment I realised how submissive I actually am.

My partner and I had found a perfect companion on the journey to satisfaction.

Act 2 - First Weekend Together

After our first night together we managed to meet at least once a week. I told him that I was going to be exclusive with him and it was okay with me that he was married. He was happy to hear this and told me that he had no other gay relationships. I understood that he had a wife and family but it was only with me that he could be himself.

It so happened that he texted me one day that his family was going to be out of the country for two weeks on a vacation. He wanted me to spend a weekend with him. I was excited and happy at this. I had never spent a weekend with anyone before and I wondered how it would be. Different and better I hoped than having to shower and leave after a hot date.

What excited me the most was that we would be living together for a few days. So I thought I should prepare and be a good boy mistress to my man. I packed my small suitcase with a few things. Lots of lube, condoms, my enema kit, a butt plug. Then my favourite short shorts and sleeveless tops. And all the regular stuff you bring if you are staying overnight.

When I got to his apartment at 6 PM on Friday there was a slight drizzle. He buzzed me in and after I entered the door we kissed passionately. I hadn't seen him all week but now I had him to myself till Monday morning.

He had already set out some drinks for us and a stupid horror movie was set up on the TV. I realised that since we had the whole weekend we could just spend time together and relax. There was no urgency to anything.

I did slip into my shorts and sleeveless and we settled down on the couch with wine. He wrapped his arms around me and I moved my legs over his thighs and we made out while the movie played.

He moved his hands up and down my smooth legs and I felt his bulge. I gently massage his bulge with my butt as we continued to kiss. I then felt his hand undoing the button and zipper of my shorts. Underneath them I was wearing a thong with the exposed butt. Without warning he picked me up in his arms and put me face down on my stomach on the couch. He started to kiss and lick by butt cheeks and stroke my legs.

I wanted him inside me so badly that I begged him to fuck me.

He took off his pants and shirt and pulled off my top so we were now naked except for my thong.

I heard the familiar tear of the condom wrapper and the opening of the lube bottle.

And just a few moments later his cock was at my boy pussy's door.

He pushed inside me with no difficulty. My hole was now well-adjusted to his cock.

And after a few long slow thrusts he increased his pace. He told me he really needed release as he banged me hard and fast. I begged him to cum for me. And after a few minutes to hard fucking he groaned and came filling up the condom deep inside me. He gently embraced me and said "Fuck that was good. Just what I needed after a long week." As his cock withdrew from my hole I turned around and gently removed the condom making sure we didn't stain the couch. I wrapped it up in tissues and tossed it into the bin. He was impressed by my cum tissue basketball skills.

We lay side by side on the couch as the movie continued to play. I felt happy and satisfied that I made my man cum. We talked about the week and joked around sipping more wine. He praised my beauty and I praised his muscles and strength. It was so nice to just laze around with this hunky macho stud and feel his hairy body against my smoothness. I noticed that his hands were calloused from working out and I loved how his rough hands felt against my boyishly silky skin.

Once the movie ended we started fooling around again. This time he pulled my thong off and went down on me as I sat back on the couch.

Now my cock at fully erect is just 3 inches long. Its straight and not very thick. It is useless for penetration and it is good that I never use it that way. In fact I only touch it to keep it clean and moisturised. Also I'm anxious so if my little cock is touched or sucked I cum very quickly. I was so horny from the earlier fucking that when he sucked on my cock I came hard almost instantly. My boy juice flooded his mouth and I moaned in pleasure.

Then my man put on another condom and spat out my cum using it as lube. He raised my legs over his shoulders and entered me with a smooth thrust. Having cum already I got no pleasure from this but enjoyed the feeling of my ass being full. My cock lay limp and lifeless as he pounded my hole. I moaned because of his thickness and power and a feeling that doing this would make him cum faster. You see, when a man is fucking you he will fuck you till he is done. As a bottom your orgasm is a happy byproduct but it really doesn't matter to the top's pleasure. So being fucked like this after I had cum was a new experience I was still getting used to.

As he pounded my sissy boy hole I encouraged him not to hold back. And soon I had my reward as he came once more with his cock buried deep inside me. He fell on top of me and we kissed deeply as his cock gently withdrew from my hole.

After this he led me to the shower for clean up. He gentle soaped me up and rinsed me off and I did the same for him. Our cocks were both soft now having spent their loads.

As we dried off he told me that we would head out for dinner. I was surprised because did not want to cause any problems for him. But he was keen to go. So we headed to this Italian place and enjoyed a nice dinner together. I tried hard to pretend to be his nephew but I am sure the gay waiter knew what was going on.

After we got home it was late and we were both tired. So we got ready for bed. I had never slept over like this before. So I wore a small pair of silk boxers and hopped into bed. He was shirtless but wore pyjamas. I nestled up on his chest and stroked his hairy stomach enjoying the feel of his bulk and muscles.

We got to talking again and he shared some intimate details of his life. He had met his wife at college and they got married in their early 20s. He always fantasised about boys and girls but had never explored his gay side. With the kids growing up and busy life his wife and him had grown apart. And he found himself being excited more and more by young guys like me.

I told him that I had a very different experience. I was lucky to be younger and my parents were always supportive. I think everyone knew I was gay. But I was so good at school that I always gave my parents lots to boast about. For me going to college and moving to another city let me finally explore. And I was lucky to have someone like him so soon. College gay sex is really weird because half the guys run for the door as soon as they shoot their load. So it is just mindless banging.

We soon fell asleep in each other's arms. And it is the following morning that I encountered the morning wood of a virile man. I woke up before him and saw a tent in his pyjamas. I went to the bathroom and got myself ready and lubed up my holed. I then got back into bed and gently tugged his pyjamas down exposing his cock. I started to suck the tip and he woke up saying

"Now that's a good morning!"

I hummed good morning as best as I could with my mouth full of his cock. He held my neck and got rid of his pyjamas. I ran my hands over his buff hairy legs enjoying the way they felt. He gently pulled me away from his cocked and lay me down sideways by butt facing his cock. In that side position he caressed me as I handed him a condom and whispered that I was fully lubed.

A moment later he thrust inside me. I enjoyed every second as my sex had recharged overnight. This was the third fucking I was getting in about 12 hours and I had a dull ache in my boy pussy as he pounded it once again. It was a sweet slight pain with more pleasure. As he fucked me deep his cock stimulated my prostate causing my little cock to become fully hard. I was truly in heaven as I felt my sissy orgasm building. He too was getting closer to release. As he thrust repeatedly it I felt a deep pulse emanating from my prostate. I was going to come and a few moments later my boy juice started dripping from my cock. I made sure it fell into my hand and ate it. Seeing me orgasm and eating my own sissy juice pushed him over the edge and he increased his pace and shot his load while his cock was buried deep in my ass. We again kissed passionately as his cock slid out of my aching hole. I gently took the condom full of his sperm off his dick and licked his cock clean as he moaned due to his post-orgasm hypersensitive tip.

We cuddled for some time and then got ready for breakfast. At breakfast he said that he'd like to take me shopping. I was happy to go along and we had a great day out. I felt really comfortable with him but I didn't let him buy me anything expensive. It wasn't like that between us. But I did understand that as a dominant older top he wanted to pamper his young bottom mistress.

After we got home on Saturday we spent the evening making love. I realised at this point that bottoming for such an active and energetic top was not easy. Getting fucked four or five times a day by a thick cock with good endurance is deeply satisfying but it is tough on your boy hole. By the time we said goodbye on Sunday I was sore, stretched, and tired. I imagined what it would be like being married to such a real man. I also felt an incredible desire to have him fuck me with no condom. I wanted his cum inside my boy pussy. I soon found out he was thinking the same thing and wanted to fill me with his seed.

Act 3 - First Bareback

In the weeks after our first weekend together I developed a longing for having my first bareback experience with my boyfriend. But this came with a lot of responsibility. It meant being tested for STDs/STIs. It also meant I had to make sure my boy hole was squeaky clean. And it meant that we would be committing to each other and not having any other partners. For me it was clear it was what I wanted to do. Nothing would please me more than have my lover's cum inside me. After making love one night I broached the topic with him.

"Listen. Don't freak out. But you are the only one I want to be with. I'm okay with your marriage situation. But I'd like to be your boy and I don't like the idea of you getting with any other boys. I want to do this because I want to have bareback and I want to feel your cum inside me."

There was a long pause. Or at least it felt long.

He said: "I've been thinking the same thing. So there's some things we need to do first."

I was ecstatic. And once our tests came back all clear, I got ready for our first bareback encounter.

I took extra care to clean myself, and showed up at the apartment on the Saturday morning we'd set.

As soon as the door closed behind me my man pinned to the wall and we kissed passionately. He took my clothes off right there in the corridor and pushed me down onto the carpet. He took off his clothes in an instant and pounced on me from behind. He was so firm and eager and I naturally submitted to him. I had lubed and wore a butt plug which he pulled out.

And then it happened. His raw cock entered my hole.

I had felt him so many times before. But feeling his skin against my insides was just so much better.

It was also much more pleasurable for him for as he plowed me I felt he would come quickly.

Here I was lying in the corridor on a carpet while a hunk pounded my hungry boy hole with his perfect cock. I also felt my orgasm starting to build as he hit my prostate and sent waves of pleasure through me.

Before I could come he shot his load deep inside me. I arched to make sure none of it dribbled out and he put the butt plug in as soon as his cock slid out of me.

I had my first bareback cream pie. And the butt plug kept it all inside me.

It was so warm and squishy. I found it something that I enjoyed to no end. My only regret was that I would eventually have to take my butt plug out and that his seed would drain out of me. Even so my dream had been fulfilled.

We got up from the floor and kissed each other. He noticed that I hadn't come. So he dropped to his knees and sucked my small 3 inch boy clit. Between the squishy butt plug and his sucking I came in no time. He stood up and we shared a cum filled kiss.

Here I was my butt full of his cum while his mouth was full of mine and we were sharing and swapping.

Not a drop was wasted. He was my macho king and I was his boy queen.

And when he wanted to go again it was super easy because his cum was already in my hole. The sloppy seconds and sloppier thirds that followed were perfect. Just what we both needed.