My Transition Pt. 01

It was late in the 1990's when the internet opened the door for porn on demand. I never spent a lot of time on the porn channels, but when I did, I loved watching two women together. On occasion, I would imagine being with them, watching and joining in. Typical of most males, if being in bed with one female is fantastic, what heights can be reached with two women.

Occasionally, my wife and I watched porn together, and unfortunately, she let me know that watching two girls together did nothing for her. Watching a guy fucking a female and watching her suck him was arousing for me and thankfully for my wife as well. Many times we would be nude and masturbating each other while watching a couple on the screen have sex.

The best blow jobs I ever received occurred after my wife watched a female suck a male porn star to completion. Most of the guys had long, thick cocks, but at just over six inches, I didn't feel mine to be inadequate.

It seemed that in porn videos, most guys didn't cum inside their partner, but would pull out and cum on their pussy or in their mouths. Although I loved the look of a soaking wet pussy, watching a guy spurt became more arousing and there were times when I imagined him spurting on me.

One evening I came across a short anal sex video. It seemed impossible for something so big to go into something so small. Who knows what was going on before the video, but she seemed to be enjoying the intrusion and a week later I played the video for my wife.

After weeks of begging, my wife agreed to do it, but with one condition; that first, I let her put her dildo in me. Thoughts of her seven inch dildo going inside me was not a welcome thought, but I had always dreamed of taking her sexy ass and if that's what it took, I would do it.

Saturday evening arrived and my wife suggested I shower...everywhere, until I was squeaky clean. After showering and snuggling on the bed, my wife parted my legs, dripped lube on her hands and fingers and touched between my legs.

The lube was cool and her fingers circled my entrance, sending shiver after shiver from head to toe. Her index finger went round and round my hole and then she inserted it to her first knuckle. I clamped tight and when I relaxed, she slipped her whole finger inside me.

My body shook, the most incredible wave washed over me and precum flowed from my slit. She wiggled her finger and the urge to pee rocked my body, but pee didn't flow, it was my sweet nectar.

Teasingly, she withdrew her finger, only to join it with another and wiggle them both inside me. The moan that escaped my lips were identical to the moans she made when her G-spot was touched. In less than a minute, my whole body tightened and the orgasm that rocked me was one that I had never felt before.

I was still trying to catch my breath when her fingers slipped out and the head of her rubber cock was pressing in. I was stretched and soaking with lube and it felt that my anal ring was going to split. I was about to beg her to stop, but the head popped in and the slight pain vanished.

She held it still and only pushed when my hips rose and a whimper escaped my lips. The feeling of fullness progressed as inch after inch invaded my body. I arched higher and higher until the full length was in me.

My cock had been rock hard, but had deflated to an embarrassingly small size. Jody moved her fake cock in and out and two of her fingers stroked me. The urge to cum gripped me and my fingers curled onto the sheets.

Instead of explosive spurts, my cum pulsed out, wetting my pubic hair. The feeling so different, one I hoped would happen again and again. She scooped the wetness onto her fingers and slipped them past my lips and into my mouth.

I'd tasted my precum hundreds of times, but never this. The consistency was not appealing, but I licked her fingers and wanted more. Jody slid her fingers through more and I greedily lapped it up. For the first time in my life, I wondered what it would be like to have another man spurt directly in my mouth.

A week later my fingers were circling around my wife's anus, preparing her for my cock. She was nervous and I did my research, discovering how important it was to prepare the recipient. The butt was designed for exit, but there was no denying the pleasure of entrance.

One, two and then three fingers slid in easily and I added more lube as she relaxed her private hole. I moved over her and guided my cock to her small entrance. Plenty of lube had been added and as I increased pressure, Jody tightened, making it difficult to breach her hole.

Kissing her neck had the desired effect and her sphincter relaxed slightly and the head of my cock slipped past her elastic ring. I held there, seeing her wince and bite her lower lip. Moments later, my hips moved and half my cock was inside her.

The thought of finally being in her ass pushed me over the edge and I began unloading my seed into her. Her fingers flew over her clit and within moments she was cumming and my cock was being treated to a fantastic massage of her rippling muscles.

I pulled out and tried to stay awake as Jody went to the bathroom to clean up. The battle was lost and before she returned, my eyes closed and I was in dreamland.

At breakfast, Jody sipped her coffee and I knew the wheels were turning and she had something to say.

"Sweetie, about last week and last night. I wanted to do that for you so that your fantasy thoughts would come to life, but I don't want to do it again. It was awkward last night and last week was way beyond my comfort zone."

I tried to mask the look of disappointment, thinking of the pleasure her dildo had given me and if it ever went inside me again, it would be at my own hand.

Our sex life continued as in the past, but the frequency began to recede. Before I knew it, our lovemaking had become once a month and then once every few months.

As sex with my wife decreased, porn watching and masturbation increased. Like many mature men, I loved my wife, but became incredibly frustrated at the lack of sex and touching. I didn't want to cheat on my wife, but I didn't want a life without sex either.

Over time, thoughts of my wife's dildo and the taste of my seed began to increase. Instead of imagining sex with my wife or another woman, I imagined sucking and anal sex with another man.

I began watching gay porn, especially homemade ones where gay partners were having sensual anal sex. A search with 'gay..breeding..homemade' showed hundreds of videos of men breeding men and whenever I thought of that, it was me being on the receiving end. After years and years of fucking my wife and enjoying it, I wanted a man to be over me or behind me.

If a toy felt good, how incredible would it be to have strong hands grip my hips, a stiff, hot cock enter me and spurt seed into me. When I wasn't thinking of being fucked, I was imagining a cock, spurting cum in my mouth and on my face.

It was over six months since I had sex with my wife and after several discussions it was clear that her desire for sex was gone. I was in a Catch-22; become celibate or cheat. Either one was a horrible option and I didn't want a sexless life.

One afternoon, I was doing a web search for massages in the local area and one advertised a tantric massage. It strongly hinted of a happy ending and had a price tag of 250 for an hour.

Out of curiosity, I searched for gay tantric massage. One ad in my area appeared and it left no doubt that a happy ending was guaranteed. At 120 per hour, my interest and my imagination went into overdrive.

I sent an email to him, asking several questions, including - "Is mutual touching allowed?"

His positive response made my cock twitch and I sent another email asking if touching went beyond fingers and hands. He wrote back that evening, stating that all doors were open and could be discussed at the time of the appointment.

It took weeks and several emails to build up the courage to make an appointment with Ken for my first, gay tantric massage and at one on a Thursday afternoon, I walked up the steps to his house and pressed my finger on the doorbell.

Ken was exactly as advertised; mid 40s, six feet tall, 195 pounds, short sandy hair, brown eyes, broad shoulders and a warm, friendly appearance.

"Come in," he said.

I was in my late 50s, 5' 11", 205 pounds, light brown hair with touches of grey at the temples, grey/blue eyes, broad shoulders and a deer in the headlights look.

He laughed gently. "Sit down and relax. Would you like a glass of water?"

"Please," I said and sat down on the sofa.

The house was pleasantly decorated; not feminine and not masculine either. The art work was tasteful and there were several photos of Ken and a man similar in age to him.

"That's my partner, John. He's a pilot and right now should be somewhere between Toronto and Vancouver."

"Have you been together long?" I asked.

"Next month it will be fifteen years."

"Its been 30 years for me," I said.

We spent a bit of time chatting and getting to know each other better.

He slapped his leg. "Okay, first things first. Work is one part of my life and my goal is to treat my customers with professionalism and respect. Everything I do is done safely, with medical gloves if and when required. My partner and I don't cheat and we are both STD free."

"STDs scare the hell out of me and that's why I've never tried hooking up with a guy," I admitted.

Ken nodded. "I always assume my customers may have an STD, I never give oral and if a customer desires a prostate massage, a glove is always worn. This protects me and eases the customers fear that I may have an STD and pass it onto him."

My body began to relax and a second sip of water helped.

"In your e-mails, you stated you believe you are a bottom and a submissive."

I nodded.

"Just to make sure," he said, "a Top inserts his cock into a bottom's ass and a submissive submits to a Dominant in a BDSM relationship."

"That's how I would define it as well."

"I'm a Top and a Dominant and my partner John is a sexual bottom, but not submissive. For the past few years, we've talked about including a third person, one who is older, in a committed relationship, submissive and a bottom," Ken said.

"I've never been with another male, so I can't really say for certainty what I am."

"Based on your emails, the fact you are here and your mannerisms suggests you are a bottom and quite submissive. During the next hour, you'll have a better idea of who you really are."

Ken led the way to a room lit with candles and the scent of lilacs. A table stood in the corner, the top filled with lotions and potions.

"I'll step out for a few moments and you can strip nude or leave your underwear on, either is fine. Lay on your front and I will knock before entering."

He closed the door and I thought it was now or never. I unbuttoned my shirt, slipped it off and rested it on the door hook. My socks were next, followed by my pants. It took several moments of consideration and I slipped my underwear down.

The bed was comfortable and I pulled the cover far enough up to cover my bare bottom.

Hundreds of thoughts crossed my mind, but suddenly stopped when a light tapping sounded.

Ken had changed into a white t-shirt and loose cotton, white shorts.

"I'll start with your shoulders and your back."

He rubbed oil on his fingers and his touch was warm and light. He followed the curves of my body and I couldn't believe that a touch from another man could feel so good.

He said softly. "Tell me if any touch makes you feel uncomfortable and I will stop. Certain parts of my body may come close to or touch yours, but I ask that you not move to or touch me. Okay?"

I had thought mutual touching was acceptable, but he may be testing my ability to do what he said.

"Yes, that's fine," I said.

My head was turned to the left and he stood in front of me, reaching down from my shoulders to my lower back. His crotch was close enough that I felt the material of his shorts and possibly, his manhood.

His hands reached the bottom of my back and there was no doubt that his cock was pressed against the top of my head.

"How's that?" he asked.

"Fantastic," I whispered, tempted to turn my head and let his cock touch my face.

His scent was fresh, but there was a slight hint of musk that drifted through me. It made my heart flutter and my cock became semi-stiff.

He moved from one side of me to the other, touching every inch of my back and at times shivers ran up and down from head to toe. He wasn't only good, he was fantastic.

My arms rested at my sides and at one point he pressed his cock to my hand and left it there for what seemed to be minutes. He did this to my other hand and as tempted as I was, I never moved my hand to touch or squeeze his cock and balls.

He moved to the side that my face was turned towards.

"I'm proud of you. I think it took a lot of willpower not to move your hands. Good behaviour leads to a reward."

He lifted the right leg of his shorts, exposing almost all of his cock. His head was completely covered with foreskin that puckered at the very tip. To my surprise, a moan escaped my lips, making my cheeks blush red. A natural cock was so, so hot.

"Lean in and kiss it."

It didn't matter if it was an order, a demand or a request, I leaned, closed my eyes and shivered when my lips touched the skin covering his cock head.

It seemed unreal, dream like. Time stood still as tingles washed over me and I wanted to keep this connection forever.

He pulled back and let his fingers slide through my hair.

"Greg, you are in your mid-50s and have no idea who you really are."

He lifted the blanket and moved to my left side, exposing my leg and parting it slightly away from my right leg. Ken began rubbing and lightly squeezing each toe, then the arch of my foot and up to my ankle and knee. He worked the hamstrings lightly, moving up until he was at the bottom of my butt.

My cock was under my pubic hair, but the cool air over my sac let me know that it was exposed to him.

He moved that blanket further to the side, and my whole bottom was exposed. Ken rubbed and lightly kneaded my cheeks and brushed over my sac. He circled each ball with the tips of his fingers and then gently squeezed both. I was at his mercy, and felt perfectly safe.

Without a thought, I raised my hips slightly.

A light spank greeted my cheek.

He laughed. "That's nice, but somewhat slutty. With the wrong guy you could have gotten yourself into a bit of trouble with a bare cock being thrust inside you."

Ken was right. I was in a vulnerable position and wouldn't have resisted if he got on top of me and shoved his cock into my ass. Condom or no condom; at that point it didn't matter. I don't know what a bitch in heat feels like, but it had to be similar to how I felt right now.

A burning desire to be penetrated flooded over me and I felt so completely and utterly empty.

"Flip over Greg, I want to see your cock."

I should have been embarrassed, even just a little, but I wasn't. In fact, it was quite the opposite. I felt comfortable exposing myself to him and before our eyes, my cock expanded to its six inch length and full thickness. Unlike the man before me, I was circumcised.

"Rub your balls and squeeze them for me."

I did as asked, rubbing my balls and squeezing them, watching precum flow onto my tummy and down my sides.

"Now jerk yourself, but don't you dare cum."

The lust in his eyes thrilled me and I rubbed until I was close and whimpered as I stopped my own release. I did this several times as more precum dripped from me.

Finally, his lubed fingers replaced mine and three strokes later rope after rope of my essence spurted to my nose, lips, chest and tummy.

"Lick it from your lips," he said.

The consistency was gross, but I did as asked, tasting all of my seed.

"Babe, gather it up and eat it," he requested

I hesitated as the post erotic lust left me.

"Now," he commanded.

I hadn't cum with such volume since I was a teen and the seminal fluid looked so unappealing, but I did as asked, scooping and eating the cum that had been expelled from my body.

He smiled. "Do you now have an inkling of who you really are?" he asked.

My cheeks warmed as thoughts of being a real bottom and a real submissive dawned on me.

"Slide off the table and kneel before me."

My cock had stayed hard and wiggled to and fro as I slid off the table and onto my knees.

"You were correct. You are a bottom and you are submissive. You're also going to be my cocksucker and my bitch."

Years ago I would have laughed at something so ludicrous, but the whimper and need rushing through my body told me other wise.

"Will you allow me to teach you how to pleasure my cock?" Ken asked.

"Yes," and I nodded.

"Do you want to be my cocksucker?" he asked.

I nodded.

"Say it."

"I want to be your cocksucker."

"Do you want to be my bitch?" he asked.

"Yes, I want to be your bitch."

"At his whim, a Master fucks his bitch. Are you sure?"

"Yes, I'm sure."

With a slight grin. "Sure of what?"

"I'm sure that I want to be your cock sucker and your bitch."

He petted around my ear and then lowered his shorts.

"Kiss the head and put it in your mouth."

I was so light-headed and felt like I was having an out of body experience. Foreskin had struck me as so erotic and kissing Kens' was heavenly. He pushed gently and my lips parted wide to accept him.

My body shook and once again, I spurted over and over as cum exploded out of me.

"Lick it up."

How inconceivable; a mature married man, licking his own cum from his younger Master's floor.

"I can't wait to tell John that you not only met my expectations, but exceeded them."

Ken insisted I shower and meet him in the living room.

"You did things today that were new to you and for the next few days your mind is going to be in a jumble. Don't be hard on yourself, just be honest. A door was opened today and you could step in or step back. Give yourself a week to ponder your feelings and at the end of the week, feel free to relate your feelings to me."

My mind was tumbling, believing and not believing the things I had said and done.

"Take all the time you need. Although I'm a dominant, you as a submissive hold the power. Your submission to me would be such a special gift and I would be honored to guide you along your path."

He stood and I did the same.

"Now for the final test of the day. Will you allow me to kiss you?"

The look in my eyes, the slight tilt of my head and my tongue wetting my lips was the answer he needed.

Seeing two men kiss was as gross as the consistency of cum and although I had imagined tasting cum, I'd never imagined kissing another man.

Was I a man being kissed by another man or was there a feminine side in me that was attracted to a cock, to penetration and to a man's lips.

Letting the kiss linger didn't surprise Ken, nor did the swirling of my tongue when his tongue slid into my mouth.

Up until this point, I was certain how great a kiss could feel, but never had a kiss felt so right, so good and so sweet. He pushed me onto the couch and we didn't stop until the sun was about to set.

I left his house a man, but not as the same man who had entered it.