Oedipal Odyssey

He kept looking in my eyes as he kept pushing his dick inside me ever so slowly. Although I wanted it for so long, a thing that size would get some time to get used to. And he seemingly read my mind. Once he was halfway in, he started to pull out. He stopped right when only just the tip was inside me.

This went on for I don't know how long, but he was taking his time with me. And I felt like melting in pleasure on the bed. With every slow hump, he kept pushing more and more of his cock inside. That is when my semi hardened dick started leaking out cum.

"Daddy," I manage to say, out of breath. "Cum inside me."

"Oh we're not there yet." Was his response as I stared wide eyed at him.

As I felt daddy's balls resting against my ass, he stayed inside like that for a minute.

"Do you feel it inside?" He asked. "Daddy's all the way in."

"Oh daddy, I feel so full. Please keep fucking me."

And keep fucking me he did. As soon as he started picking up pace, I turned into an incoherent ball of mess from all the pleasure I was getting from my ass. Even after ejaculating so recently, the pleasure I was receiving did not diminish. The man knew what to do, and how to bring the most pleasure to his partner.

He kept deep dicking me for what felt like fifteen minutes more before he declared he was about to cum. I begged him to finish inside my ass and this time, his whole upper body collapsed onto mine. He put his arms under my armpits, his face was against mine as his final thrusts were slower than before. When he stopped moving his body, I could feel the tip of the dick pulsing inside, discharging semen deep inside my intestines.

Daddy then started kissing my neck and cheeks, but did not move his body at all. His dick was still lodged deep inside of me. The weight of his body was something I still had to get used to. After a while, I could feel the dick inside of me calming down, but it did not shrivel down to its flaccid state. My body felt like it was burning when daddy got up. He slowly took the cock out of my hole in its entirety. Even the act of taking the cock out felt ecstatic. My cock was now rock hard again, and daddy started to slowly play with it.

I was at a loss of words. For a moment I felt like I had to say something to the man that brought me such immense pleasure, but I couldn't figure out what to say, how do I tell him how much this meant to me.

"Oh, I love you daddy." Was the words that came out of my mouth. "I want to be with you forever."

He looked at me, my cock still in his hands. "I love you too baby." There was something in his eyes. Kindness? Regret?

I hope daddy didn't start having second thoughts after such an amazing experience.

"What's wrong daddy?" I had to ask. "Did you not like it?"

"Oh don't be silly." Daddy replied. "Of course I loved it."

I let out a sigh of relief.

"But," Daddy hesitantly looked down at his crotch. "You see, I was worried about not lasting long enough for you tonight. I wanted your first time to be a wonderful experience."

"You were everything I ever hoped you would be." I told him, thinking about how silly of him it was to think he wouldn't be enough.

"But that's the thing." He said as he looked worried. "I'm not as young as you, and being this hard is not easy ..."

"Oh daddy," I stopped him. "It was wonderful as my first time. I wouldn't mind if you finished in a couple of minutes."

"That's not it." Daddy said. "Ryan, would you let me finish. You are exquisite, and your body would turn me on anytime and anywhere."

I took a mental note of that.

"But I did something stupid, thinking I might not be able to give you what you deserve." Daddy sighed before continuing. "So, I took some pills that would keep me hard for a long time."

"Oh." I said as I looked down at his crotch.

The magnificent cock was as hard as ever.

"And it seems like it will stay hard for a while." Daddy said as he kept fiddling with my dick. "Now, I might have to go to the doctors."

"Nonsense!" I said. "You'll go to the doctors if you stay hard for more than six hours." I sat up and held his dick as I said that. "In the meantime," I got up on his lap. "I'll have to try to calm this monster of yours."

As his dick was now rubbing against my ass cheeks, he held me by the waist and said, "This is your first night, I don't want you getting hurt."

"Nobody's getting hurt!" I said. "Besides, I'll let you know if I'm at my limit."

Still well lubricated with added sperm, I slowly lowered my body on top of daddy's dick. Holding his shoulders, I started bouncing up and down on the dick. I was able to keep it up for five minutes before we switched positions. This time he fucked me sideways. The sensation was slightly different as it was much harder to kiss him from this position. This time both of us came together. He finished inside me as my cum dripped on the bedsheet.

Then both of us decide we needed a break. We went downstairs in the kitchen for some snacks and drinking water. We were on the verge of fucking ourselves into dehydration. After drinking lots of water, both of us had yogurts. I kept some of it in my mouth and pretended it to be his cum as I opened my mouth and showed it to him. That seemed to have awakened something in him as I saw his expression change a little. The animalistic lust was apparent; and I kept poking the beast in him. I knew I was about to get it when he slammed his cup down on the table. He stood up and got close to me.

His dick was now right in front of my face. I leaned forward to take it in my mouth when he told me to stand up. As soon as I stood up, daddy had me bending over the table. He pushed two of his fingers inside me to see if I need any more lube or not. Seemingly satisfied with the wetness of my hole, he entered me.

This time, he forced the tip in a single push. I gasped out loud at the sensation. He then started going in and out with a force I never would have thought he possessed. It was absolutely electrifying as he kept fucking me like a cheap whore. There were no tender kisses, no sweet talk, just grunts and moans as a man was getting the pleasure he desired. I loved every single moment of it.

After a while, I realized daddy had one foot up one the table as he kept going at it.

"Get on your knees baby." Daddy commanded.

"Yes daddy." Weak in my knees, I went down on them.

I didn't hesitate for a moment before taking the cock in my mouth. This time I didn't have to work too hard to get him to finish in my mouth. But right before cumming, daddy pulled his cock out and sprayed the spunk all over on my face.

I looked up in his eyes, content with the amount he was able to spurt out despite it being his third load in an hour. Daddy then leaned over and started picking up some semen from my face with his thumb and lathered it all over my lips.

"You look so beautiful, Ryan." Daddy said.

I had my eyes closed as I thanked him. I licked my lips after he was done and then he rubbed all of the semen on my face like a moisturiser. The smell should have been unappealing, but at the moment, it was fuel for my never ending libido.

After I got up, daddy led me to my own bedroom, the one where I grew up, discovered myself, and spent countless nights pining for the man that just came on my face. As we were walking upstairs, the thought of ass to mouth came to mind. I had just taken a dick right out of an asshole straight to my mouth. There was a thorough cleaning process, sure, but the act still seemed pretty gross. I then looked up at the man holding my hand, the expression of utter bliss, faint smile, as he held my hand tight. I would do anything he wanted me to and more. If it means the happiness of this man.

My own bed was not large enough for two people to sleep comfortably. You could sleep, but your bodies would be rubbing together, and it would be impossible without an air conditioner. Daddy fucked me on my bed next. It was as passionate as ever. Then he lifted me up and had me lay down on the table. On that position, he started playing with my cock as he kept pounding my hole. I came before daddy this time. He once again finished in my ass.

Both of us were spent. We knew we had to take some time out. Daddy decided to lay down on my bed next to me. He started spooning me from behind. The massive dick was still hard. I controlled myself from rubbing my ass against it. His heavy breathing was turning me on like crazy. Then he started whispering sweet nothings into my ear.

"Baby you've made me the happiest man ever." Daddy said. "To think I could have been doing this for more than a year ago," He kissed my neck. "Your entire body is a work of wonder."

I didn't know mere words can have effects like this, but my dick was hard again and my entire body felt like it was on fire.

"Such a beautiful ass," He groped my behind. "So soft, and juicy. This body," His hands started caressing my belly and chest. "So soft and tight at the same time. Your lips," One of his fingers came near my lips, and I started sucking on it. "So full, so eager!"

My mind was a blur. He turned me around and started kissing me. Eyes closed, I was enjoying the onslaught of his tongue inside my mouth. Then, for the first time that night, I took initiative and turned into the 69 position. His dick in front of my face, my only intention was to provide him with as much pleasure as I could.

I started slowly licking the tip of his cock when daddy surprised me once again. He took my own dick in his mouth and was going hard at it. I had some trouble concentrating on the dick in front of me given the pleasure coursing through my body. I refrained from taking the dick in my throat, afraid I might lose control with the pleasure. Nobody likes teeth on their dicks! So I just kept the tip in my mouth and worked on the rest of his cock with my hands.

We were working on each other's cocks for a long time, slowly and gently bringing each other closer and closer to the edge. I lost and came first again. But if it was with my daddy, I would love to be the loser like this all the time. I took a couple of minutes to recover before going down on daddy for real. My entire body seemed way too fitting inside my daddy's legs. I didn't go slowly this time. Looking up at him, I noticed he had his eyes closed.

I then brought one hand up and started playing with his left nipple first. He had the expected reaction, looking down at me with shock. Taking his cock out of my mouth, I asked, "Do you like it daddy?"

"Oh yes." He then closed his eyes again and started playing with his other nipple by himself.

It didn't take him too long to cum down my throat after that. After cumming, he told me to get on top of him. I got up and put my entire body all over his hairy body. My flaccid dick was now rubbing against his belly. His still hard dick was rubbing against my ass.

"Is it bad, daddy?" I asked, holding the life giving dick with my right hand.

"It's starting to hurt, just a little bit." Daddy said. "But we'll see how far we can go."

"We don't have to go any farther daddy." I kissed his cheek. "This was the best night of my entire life."

"Oh I might just have some more in me." Daddy kissed my cheek back. "And I'll keep trying to make every single night of your life better than before."

"Oh daddy." We started kissing each other again. This time I tried to be more dominant with my tongue, and daddy reciprocated. I tried exploring his mouth and get any remnant of my own cum inside.

He soon grabbed and parted my ass cheeks as I was playing with his hair. Breaking off from the kiss, I got up and quickly ran to daddy's bedroom to get the lube back. Daddy already started hurting, so I wanted him to be thoroughly lubed up before going inside again.

I massaged his cock or a while before getting on top of him again. This time, I was not able to stay on top for a long time. Fatigue was getting to me and daddy sensed it. He held me in place and ever so slowly kept going in and out of me. I then fell on my back, with daddy's dick still inside of me. We stayed there, with minimal motion for a couple of minutes before daddy got on top of me again.

It was missionary again as he kept working on my ass and face at the same time. As he came inside me, his body collapsed on top of mine.

Both of us were tired beyond anything and despite the discomfort of having the 200 pound man on top of me, both of us were able to fall asleep.

It was nearly morning when I fell off from the bed onto my ass. Daddy must have rolled over in his sleep and the minimal space of my bed had me slowly slipping away as I eventually landed on the ground. Sunlight was creeping in the room as I felt the pain in and outside of my ass.

I must have overestimated my own strength as my ass didn't feel like it could take a single finger in it. as I stood up, I winced in pain. Then I saw the magnificent body of the man that turned my ass that way. He was peacefully sleeping. I marvelled at the glistening body as the now flaccid cock rested against his thigh. The pain in my ass was real, but the cock in front of me was just calling out to me. I could easily bring it to life and bring him another orgasm using my mouth only.

Leaning over, I started working on the cock with my mouth, licking it all over from the base to its tip. As it started coming back to life, daddy groaned in his sleep. It didn't sound like a groan of pleasure. After taking a ball in my mouth to suckle on, daddy woke up.

"Ryan," He was still sleepy as he held my face. "I love you, but you have to get your hands off my dick."

I understood and sat up straight after kissing the tip one last time.

"Maybe for a week or so." Daddy added.

"I'm sorry daddy."

"There's nothing to be sorry about." He said as he widened his arm. "Come here, we can sleep in late today."

I crawled onto his loving embrace as both of us fell asleep after he kissed me on the forehead.I was so glad i waited for him and resisted any available dick around.

That first night was too much for both of us. Maybe it was harder on daddy than me. I did have trouble sitting down properly for a couple of days, but daddy could easily sweet talk his way in my ass; if he wanted to. But he didn't want to. And instead, it was torturous for me as he decided to let the dick hang around bare as even clothes hurt!

We slept in our separate rooms for a couple of days, me on my front, constantly rubbing my dick against the bed, imagining when daddy would be on my back while I was like that. And the first thing daddy did was just that. He kissed me goodbye before leaving for work on the third day. There were no talks about sex on that morning as well. We had our dinner and went to separate bedrooms.

I was laying on my front for a little more than five minutes before daddy entered the room. After questioning me about my well-being for a brief moment, and me begging him to fuck me; daddy brought the lube.

He had me laying down in the prone position as he kept deep dicking my ass. It was bliss, and both of us could not keep our hands to ourselves at all.

Within the first few weeks, we learned about each other's limits and kept pushing it together. Public outings with daddy has been getting more and more interesting but we never had penetrative sex outside our home.

There are some neighbours that still know that we are father and son, and we don't want to cause any commotion in the quaint little area about our taboo relationship. Even holding hands outside drew attention to us, but we were gradually on our way to do more than just hold hands out in public.

Present Day:

I prepared dinner and waited for daddy in just an apron over a jockstrap. I would not have the jockstrap if it wasn't for unexpected boners in the middle of cooking something. After that, I cleaned myself and lubed my asshole for easy access. It had become a routine for me to do this so daddy doesn't have to worry about hurting me. I put on a pair of shorts because I didn't want any outsiders to see me greeting my daddy naked on the entrance.

Daddy arrived a little later than usual. I figured he was out preparing my surprise.

Greeting daddy with a kiss on the doorstep, I noticed him holding a gift bag along with his briefcase. Wondering what could be the surprise considering I was already quite accustomed to a wide variety of sex toys. Daddy gave me a knowing smile understanding my anticipation.

The night progressed like any other, without me pestering him about what was in the bag. I knew I will find out when the time comes.

And before the time came, daddy called on me to have some wine with him. I was only accustomed to beer, but didn't object to daddy's call and liked just having a drink with the man, mostly in silence, talking about almost nothing. After we were finished with our glasses, daddy asked me to guess what was the surprise. I wasn't sure about it, so I guessed it would be some sex toys.

"You can guess again." He said.

"Some ..." I hesitated before saying. "BDSM instruments?"

"Interesting!" Daddy mused before saying. "That's not it. Say, do you know how we figured out you were gay?"

"Oh no!" They saw me somehow trying out mom's lingerie.

"Oh yes," Daddy explained. "We noticed that you were attracted to feminine clothing a lot. And your penchant for some other things." He trailed off before standing up and commanding me to follow him.

As he led me to the master bedroom, I saw a massive collection of feminine clothing, most of them lingerie, laid out all over the king sized bed.

"Take your pick from these," Daddy said. "I hope you'll like them. Next time we can go together for shopping."

The nighties, panties, small bras were all enticing. I noticed a light blue sundress on top of it all. My boner was now straining against the jockstrap. Daddy kissed me on the cheeks before I picked out a mint green nightie and a turquoise panty and went towards the bathroom to get dressed.

I marvelled at myself in the mirror after putting them on. The silk along my skin was having the same effect as a strong aphrodisiac. I had to let my dick out of the top of the panty for comfort. But along the way, I felt conflicted as the idea of where this road might lead was daunting to me.

When I entered the bedroom, daddy was sitting back, leaning against the headboard. The bed was all cleaned up. He complimented on how beautiful I looked and told me to get closer. I got on top of the bed and crawled to him. He saw something in my eyes as he asked if anything was wrong. I told him nothing was wrong.

He then told me to sit on his lap and started probing me with more and more questions; getting to know all of my insecurities. I told him it felt great to wear this, but I didn't want to be turned into a completely feminized person. All the while talking to me, his hands kept gently caressing me all over. Daddy then gently explained the concept of gender fluidity to me and told me I had nothing to worry about. He then asked again if I like the surprise or not. After I replied in the affirmative, he told me that it was completely up to me to dress however I wanted to dress and be whoever I wanted to be. He ended it with saying that as long as he was with me, he was going to be the happiest man ever. He told me I had already made him the happiest since so long for the past six months, and he didn't want this to ever end.

There was something with the words he chose that made me completely melt over him. Then we started passionately kissing each other. After ravaging each other's faces for a while, daddy slowly took the nightie off and started kissing all around my torso. I almost fell on my back as daddy caught me and gently laid me down.

He slid the panty to the side exposing my hole. After fingering me for a while, he spat on his own dick and entered me. The dick that felt uncomfortable the first time it was inside me now feels like a part of me. Daddy held my hands over my head as he kept pounding me. I knew I was close as the panty was still rubbing against my penis, stimulating me. I didn't warn him as I came all over my own belly. Daddy soon finished inside me and we laid down together. I was still wearing the feminine clothing as daddy was completely naked, we drifted off to sleep.