My Journey Ch. 01

I couldn't get over how much I liked this. I was on my knees, with a woman behind me feeding her cock into my ass, hoping this would never stop.

"Pull it all the way out." I said.

She did.

"Ram it all the way back in!"

She did.

I repeated that request several times and she complied.

"Pull it all the way out."

She did.

"Just put the head in."

That request was also repeated, and each time Tina did as she was told.

I was taking an incredible pounding from behind and was enjoying it immensely, but I needed to see her do it to me. I needed to be on my back while she was on top of me, pounding her cock into my willing ass.

She pulled out and I lay on my back, pulling my knees toward my chest like some wanton whore. I was completely exposed to her. She leaned in, holding one of my legs in her hand and her cock in the other. She guided her plastic pole into me again, hooking my legs in the crook of her elbows.

I was pinned to the mattress and I loved it.

She sawed her cock in and out of me, her whole body moving back and forth. I could see I needed to teach her how to roll her hips to do a better job, but that would come later. Right now I wanted to cum. I wanted to cum with my wife's dick in my ass.

I didn't need to help things along or wait either. The screwing she was giving me was perfect, and this position intensified the stimulation of my prostate. The head of my cock was leaking pre-cum like a faucet, and my lower abdomen was slick with it. I knew I was close.

"Harder!" I begged.

"Harder! Deeper! Fuck me!" I cried

And then it happened. Semen rushed out of my clock and splattered all over my hairy chest. Shot after shot. Gob after gob. I couldn't remember ever coming like that, and having my wife's cock in my ass was the cause.

She pulled out of me, my ass instantly wanting her back inside. Tina couldn't get out of the harness fast enough, so I helped her take her equipment off and put it in my closet. "I'll clean it tomorrow" I said to myself. We joined each other in bed, the space between us and her body language was telling me she enjoyed fucking me far less than I enjoyed being fucked.

Only time would tell.

And it most assuredly did.

I enjoyed my first pegging so much I wanted to do it again and I did not want to wait. Unfortunately each time I broached the subject with her, Tina would ignore me or become defensive and hostile.

Weeks passed. I was becoming desperate. I needed to be pegged.

Begging and pleading made me look desperate. A horny, middle-aged, anal slut.

I reasoned with her. "Baby, you get sex the way you want (none) more than 340 days a year. Is it too much for me to ask for sex the way I want it the other 25 days?" This also made me look like a horny, middle-aged, anal slut.

Around six months after my initial pegging I was somehow able to convince Tina to do me again. I got her into the harness and attached her cock. I had her lay on her back on the bed and I again gave her a thorough foot massage. The visual I had was surreal. Tina's cock sticking straight up, legs spread, and her pussy clearly visible through the open crotch of the harness.

I was so hard, so turned on by what I was seeing, and by the anticipation of what would soon happen, that when I finished rubbing her feet I snaked up her body and licked her cock.

I loved it.

Wrapping my hand around the base of her artificial boner I placed the head in my mouth and sucked. Instinctively my head began to bob on her cock and I took more and more of her into my mouth, twirling my tongue around the head as I did. I'm not going to tell you I was immediately a cock sucking professional, but I did do my best to swallow her whole.

Never in my wildest dreams would I have imagined that I would be on my knees, between my wife's legs, sucking her cock and loving every minute of it! (The funny thing is, I don't know if Tina ever looked to see what I was doing.)

As much of a turn on sucking cock was, it wasn't what I needed, at that moment. I needed to be fucked.

I grabbed the lube off the nightstand, squirting the cool gel onto my fingers. I reached behind me and applied a generous amount to my asshole and crack. Another dose of the gel was slathered on Tina's cock from the head, all the way down the shaft to the balls.

Straddling her, I reached behind me, gripped her cock, and aimed it at my waiting hole. The head of Tina's cock pressed against my entrance and I relaxed my sphincter, allowing it to enter. I slowly lowered my weight onto the intruder until the entire mass of rubber was buried in my rectum, and Tina's balls were firmly pressed to my crack.

I sat straight up, allowing her faux penis to touch the deepest recesses of my ass. I was in sexual heaven. I leaned forward, my chest pressing on Tina's wonderful breasts. We kissed. I began rocking my hips causing Tina's cock to slide in and out of me. My own rock hard cock was firmly pinned between our bodies, the copious amount of pre-cum oozing from my dick allowed it to slide back and forth between us, almost as though it was inside a pussy.

The sensation of Tina's dildo inside of me and the stimulation my own cock was receiving quickly brought me to the edge. I sat up, raising and lowering my hips onto Tina's pelvis and the cock that was attached there, fucking myself like some kind of slut.

I took Tina's right hand in my left, and wrapped it around my straining erection. As I bounced on her cock, my own cock slid in and out of her petite hand. The sensation of the anal penetration and the hand on my cock was too much for me to endure, and I came all over Tina's belly, my ass squeezing her cock like a vice as I continued to pump it in and out of me, prolonging the amazing sensations I was experiencing.

My orgasm left me light headed, sweaty, and very satisfied. I disengaged myself from Tina's cock and immediately wanted it back inside me. God how I loved the sensation of my ass being filled with a woman's cock! I wanted that feeling all of the time!

Over the course of the next couple of years I was able to persuade Tina to peg me a handful of times, but on those rare occasions when she did it was always reluctantly, and with a palpable air of disgust. When it did happen though, the results were consistent; I always had a powerful orgasm.

My desire to have my ass filled did not wane. I searched for other avenues of satisfaction for my kinky desires. I realized that if Tina would not help to satisfy my desires, I would satisfy them myself. I purchased a suction cup base for our Vac-U-Lok dildo which would allow me hands free operation of the toy.

Whenever I was confident I had sufficient privacy I would attach that like-like dildo to one of the dining room chairs, impale myself on it, and search the internet for pegging videos. I derived great pleasure from having my ass fucked while watching couples partaking in female to male strap-on sex, and would inevitably deposit a load of cum on the computer table.

However, good pegging videos were hard to come by. A majority of them involved humiliation or sissification of the man, or the man would be bound in some demeaning way while a latex (or leather) clad woman degrade and/or rape him. This was not what I considered to be good strap-on porn. (Don't get me wrong. I appreciate a woman in sexy latex, leather, Spandex, or fishnet as much as the next guy!) I believe that pegging is a beautiful act of surrender by the man, and that female to male strap-on sex could be portrayed in a way that was loving and caring while still being extremely erotic.

My search for a means of satisfying my desires continued. I considered placing an ad on Craig's List seeking a woman to peg me, but after reviewing the number of ads by other men seeking the same thing, I knew my ad would just disappear in the sea of ads by men curious to experience pegging for the first time.

"Back to self-impaling and bad pegging videos" I told myself.

During one of my "bad pegging video" sessions, I stumbled onto a video that featured something I had never seen before. There was an attractive woman with a strap-on, the ubiquitous tattooed male, and a shemale.

A pre-op male-to-female transsexual.

Shemale.

Tranny.

The shemale was gorgeous. She had very feminine facial features, wonderful curves, surprisingly natural looking breasts, and a beautiful, shaved, rock hard cock.

I was smitten. I watched the entire video. The man got his butted filled with a strap-on while he sucked tranny cock. He got his ass filled with tranny cock while he fucked the woman's pussy. The tranny rode his dick while he ate the woman, and the woman and tranny made out. He got his ass filled with shemale cock again. The shemale pulled her cock out of his ass and jerked herself off until she finished on his chest and stomach.

We came together, the shemale and I. Her with her dick in her hand all over a guy's torso, me with a rubber dick in my ass, cock in hand, and cum all over my chest and belly.

As I replayed that video in my head, the smoking hot shemale pounding the guy's ass, I kept thinking to myself "Lucky guy."

Lucky guy? What was that about? Is that what I wanted, a beautiful transsexual having her way with me? I came to the conclusion that it was indeed what I wanted, what I yearned for, though I was certain I could never experience it.

Needless to say I was hooked. I had found a new genre of porn that satisfied my need of seeing a man fucked in the ass by a woman, and there was plenty of it. The only difference being these women didn't need a harness and dildo. They were packing their own hardware.

My fascination did not diminish. I sought out videos of shemales fucking men, or of shemales fucking other shemales. Whenever I was alone I would surf my favorite porn site in the shemale category looking for those videos.

I became familiar with many of these incredibly sexy creatures and soon had favorites that aroused me beyond belief. Mia Isabella, Aline Santos, and Sarina Valentina just to name a few. Mia has the most incredible cock. Long, thick, hard, and always ready for action. She calls it her 'candy stick'. Aline has the most perfectly augmented breasts I have ever seen (her surgeon deserves a Nobel Prize for the work he did on her!) and tan lines that accentuate her wonderful female form. Sarina is simply a painfully beautiful woman.

I have always thought that it is not solely a person's physical attributes that make them beautiful or sexy. To me, beauty and sexiness are products of belief and attitude. It is the comfort a person has in who they are and the confidence they display that makes a person beautiful or sexy.

These unarguably sexy creatures were secure and confident in their womanhood, and I saw them the same way, despite the indisputably male appendage jutting from their hairless crotches. Nothing about them made them any less than what they were: exceptionally beautiful women. And I wanted one.

My thoughts were continually tortured by visions of these lovely women. Every woman I saw caused me to think "How would she look with a cock?" Sometimes I would even fantasize that the anonymous woman I saw was a shemale, and she was hovering over me, sodomizing me.

I couldn't take it anymore. I had to make this happen soon or regret it for the rest of my life, my marriage vows be damned.

I joined an adult "dating" site (not so much a dating site, more of a cheating site) in search of an area shemale that would be willing to take me the way I longed to be taken. Unfortunately, the results of my search were disappointing. Most of the respondents to my ad were not shemales, but transvestites or cross-dressers. They were men that liked to dress as women, but they did not consider themselves to be women. I was disheartened, and resigned myself to the fact that I would never be able to satisfy my most intimate desire.

In a twist that seemed to be straight out of the pages of Penthouse Forum, I had an opportunity to dine with a high school classmate while I was on a business in the city in which she lived. Through a mutual friend, I knew that Kim and her husband were "in the lifestyle" and were active swingers. Kim and I had been close friends in school, had been on dates together, and even had a couple of heavy petting sessions in the backseat of a friend's car. There had always been a certain level of sexual tension between us, but neither was willing to cross the line and act on our desires for fear of ruining a truly deep friendship.

Through the course of dinner, Kim was open about some of her sexual exploits as a swinger, and I learned she enjoyed intercourse with men and women, which was a surprise for me. She suggested that she would love to experience Tina and me together, but my description of Tina's sexual appetite (little to none) clearly indicated that Kim's desire would remain just that.

In the course of our conversation, I did share that I had truly enjoyed Tina pegging me, but that it did not happen nearly enough. Kim told me that her husband Dan enjoyed it too, and that in "the lifestyle" there were numerous female partners that were eager to satisfy Dan's need, and one of them didn't need a harness.

Did I just hear her correctly?

Did Kim just tell me that her husband had let a shemale fuck him? My interest was piqued.

"Are you saying that you and Dan have had sex with a shemale?"

"You caught that, huh? I'm so embarrassed I let that slip. I shouldn't have said anything. You don't think I'm weird or sick, do you?"

"Not at all!" I said, trying to be reassuring while hiding my excitement at the same time. "What I think is that I would like to hear more about this encounter."

"Oh, it wasn't an encounter. It was a regular thing. Dan and I were both able to satisfy our "bi" sides with the same person. I was able to indulge my lust for a beautiful woman with a great body, and Dan was more than happy to let her fuck him. 'Win win' as they say."

I noticed Kim referred to their shemale friend as "her", which I assumed meant she lived her life as a woman.

"Do you still see her?" I asked.

"She moved away to pursue her career, but we do stay in touch. Why?"

"Well," I began, sheepishly, "the thought of being with a shemale is something I find to be incredibly hot. In fact, I'm getting puffy just knowing you and Dan have been with one."

"Really!? I never would have thought that you would be interested! This is a side of you I never would have imagined! Ooooohhh Clarky Clarky Clarky! (Clarky was her pet name for me) This is so exciting!" Kim was absolutely giddy. School girl giddy, in fact. Her eyes were flashing, and I could almost see the wheels turning in her head. The next thing I knew she was on her cell.

"Trish? This is Kim! Hiiii! Oh my God it's been too long how are you?"

"Dan and I are really good, thanks."

"Did you have to ask? DUH! Of course we are, but we do miss being with you! How are things in St. Louis?"

"Well good. You are so beautiful and talented there's no reason you shouldn't. Are you getting any?"

Kim let loose with a huge laugh, and had a genuinely happy smile on her face. I could only imagine what Trish had said that made Kim react the way she did.

"Oh my God that's too funny! Listen, Trish, the reason I'm calling, I'm having dinner with a very dear friend, and guess what?"

Kim went on to tell Trish about me and my desire to be with a girl like her. As it turned out, we lived less than an hour apart.

Once home, I made contact with Trish. We e-mailed a lot, and spoke on the phone now and then. We just took some time getting to know one another.

I found Trish to be very intelligent and articulate. She worked in the IT department for an insurance company, and had taken the job in St. Louis so she could live full time as Trish, and no one would know about who she was before she decided to transition. That and the compensation offered by the new company for her services was three times what she was making before.

Trish and I were becoming comfortable with each other, and any apprehensions we may have had wore off. We had become friends. I felt I could be open with her. I told her that I wanted to see her in person and she agreed.

We decided that our first meeting would literally be a cliché.

Starbucks. Coffee. Talk.

I arrived early, a habit I had developed in an attempt to offset Tina's propensity to be late. My back was to the rest of the store so I could keep an eye out for Trish to come through the door. We had exchanged pictures during the e-mail introductory phase so I knew what she looked like, well, from the neck up anyway.

When she finally arrived, I was surprised by her appearance. She was much prettier in person, but taller than I had expected. Not freakishly Amazon tall, but taller than me (at least I thought she was, until I realized she was wearing heels). For the life of me I can't understand why I had imagined that a petite, five foot nothing gymnast would come through the door. I should have known better. Her body was very well proportioned and alluring. She was dressed in a knee length skirt that hugged her very womanly hips, pantyhose (a plus. I love legs encased in hosiery), a simple, white button up blouse and a nicely tailored jacket that matched her skirt. She looked like any other professional woman on her way to the office.

Her facial features were very feminine; an oval face with a "pixie-ish" nose, high cheek bones, straight brunette hair that framed her face nicely, falling to just above her shoulders. Her lips were full, and painted a deep, glossy red. Her teeth were white, though the two in front were slightly crooked, which made her look real.

She had a remarkable complexion, flawless skin wherever it showed. Trish's eyes were an almond shape, a sparkling greenish-blue. She had long eyelashes (bonus. I don't know if they were real, but they were a huge turn on). Other than her lip color and mascara, I could not tell if Trish was wearing makeup. She looked very professional, yet on the verge of being sexy. I guess if I had to make a comparison she reminded me of S.E. Cupp from Fox news.

"Hi Clark!" she chimed as she approached my table. "It is so nice to finally meet you!" She gently grasped my shoulders and leaned in, touching her right cheek to my face, a pseudo hug if you will.

If I didn't already know what kind of girl she was I never would have guessed.

"Oh my, Trish. The photos you sent me simply do not do you justice. You are so much more beautiful in person."

"It's so sweet of you to say that, Clark."

"I'm not saying it, I mean it."

I asked her what she would like to drink and went to the counter to order two cups of black coffee.

Back at the table we sat and chatted about everyday things, never broaching the subject of what had actually brought us together. I noticed her feminine hands and manicured nails, and that she was wearing what appeared to be a wedding ring set on her left hand. She must have noticed where my eyes were and stated "It helps to keep the "undesirables" away."

I understood completely. "Smart girl." I said, which brought a broad smile to her lips.

Our conversation was comfortable, undoubtedly due to our previous e-mail and phone exchanges.

I bought another round of coffee and we resumed our conversation. She picked up on the fact I was staring at her, mesmerized by her eyes. She had a way of using her eyes to look shy and demure, while simultaneously giving me a 'come fuck me' look. Well, that's what I saw anyway.

We both had other places we needed to be, and keeping to our agreement that our first meeting would be for coffee and talk only, we said our goodbyes. Completely enamored with her understated beauty and initial cheek to cheek contact, I embraced her close, reveling in the feel of her body against mine. She didn't resist, hugging me back. Having her close to me and feeling her breasts press into my chest caused my cock to stir in my pants. We said our goodbyes and parted ways.