My Journey Ch. 01


I found myself in a midsized college town working on a problem that didn't want to be resolved. With assistance from my co-workers two and a half hours away I was finally able to correct the issue, and system operation was restored.

It was late, I was more than three hours from home, and decided I did not want to make the drive. Instead I chose to spend the night where I was, and drive to work from there in the morning. But what was I going to do for the evening? I had never been to this town before, and I knew no one.

Or did I?

I recalled that a girl I had dated in High School was going to college here. We had enjoyed each other's company on numerous occasions. On our first date, following a trip to the county fair, we skinny dipped in the moonlight at a city beach. On our second date she gave me a hand job in the front seat of my Datsun. Whenever we got together we ended up having some form of sex. Once, I ate her delicious pussy for hours at the top of a ski hill. Another time she let me do her in the ass on a dead end road. Yep, Jenna liked sex in all forms.

A check of the local directory revealed her phone number (this was in the days prior to the proliferation of the cell phone) and a call to her resulted in an excited acceptance of my offer for dinner.

I picked her up at her place in my Chevy Cavalier, and let her decide where she wanted to go. She looked wonderful, just as I had remembered: large, firm breasts, full lips, curly hair, and big, beautiful blue eyes. I might have gotten stiff just remembering how good her luscious body felt against mine.

Jenna decided that a local pizza place would be a great place to have a couple of beers, chat, and get reacquainted

I can't remember the details of the meal, but we enjoyed each other's company and the conversation was not at all labored.

When we were done with our meal and had our fill of beer, Jenna surprised me by saying "My roommate is going to be home, would you like to get a room?"

Now I was not expecting this offer, but I was certainly hoping for it!

Jenna suggested a local hotel, one of those cheap national chains, so I drove there and checked in.

All of the details of what transpired are not important. I recall showering together, our soapy hands roaming each other's bodies, arousing each other, alternating soft, intimate kisses with deep, probing, sensual exchanges of our tongues. Unlike some women I have been with, Jenna loved to stick her tongue deep in my mouth, licking my tongue and teeth. And she loved having me do the same. It seemed to be an extremely intimate act for her; another way for a man and a woman to join as one.

She knew how to kiss, and how I loved kissing this woman.

After drying off we retreated to the bed where gentle caressing and playful touching eventually transformed to passionate sex.

We were enjoying the usual missionary position with Jenna's legs spread wide while I drove into her. Jenna rolled us over into a cowgirl position, raising and lowering herself on my extremely hard cock. I loved fucking her in this position as I could look at her voluptuous body, gorgeous breasts, and tantalizing eyes.

It was while we were in this position that things changed for me.

As Jenna rode me she reached behind herself and inserted the middle finger of her right hand into my virgin asshole.


She thrust her finger in and out of me, bending her finger up to caress my prostate each time she sank her finger into my rectum.

I did not fight it, I simply went along with the wonderful sensations she was bringing to my body. This assault on my ass felt so incredible, so kinky, so naughty that it greatly diminished my ability to delay my impending orgasm.

I came.

I came harder than I ever recall cumming before.

We fell asleep in each other's arms, satiated.

I dropped her off the next morning, and I am embarrassed to say I have never seen her again.

So what does that brief story have to do with anything? Well, it was Jenna's digital invasion of my ass that changed the way I would think about sex.

I loved the feeling of being penetrated. I loved having my asshole touched and massaged. It got to the point that I would frequently touch myself there when I masturbated.

Years later I married. Like most marriages our sex life was regular, and routine, for the first few years. Then kids came, and the frequency of our intimacies dwindled. At one point we went over six months without sex of any flavor. I was ready to cheat, but simply could not bring myself to do it.

Not only did the frequency drop, so did the overall intimacy of our marriage. My wife, Tina, would not kiss me the way I wanted, the way I needed. Deep, intimate, crushing, passionate tongue kisses like those I shared with Jenna.

Something had to change.

I decided to spice up our sex lives by introducing toys to the bedroom. I started by obtaining a "Purple Missile" dildo and a small bullet vibrator.

Getting the toys was easy, but how would I introduce this new bedroom twist to my wife? I decided that I would blindfold her and simply have my way with her. Once I was sure she was unable to see, I ravished her, licking her tits, sucking her nipples, massaging the wonderful globes of her ass, ultimately tonguing her wet slit and clit for all I was worth, making her cum all over my probing tongue.

Moving up her body I spread her legs and plunged my dripping cock into her well lubricated pussy. It felt so good slipping my cock into that wet, warm, sucking sanctuary. I thrust into her, pulling my cock out now and then to tease her by rubbing the length of my cock against her clit, only to plunge back into her to the hilt, my balls slapping against her ass.

Holding the dildo in my right hand I once again disengaged my cock from her body, and raising my hips slightly, pushed the purple toy into her while rolling off of her to my left.

I was now lying by her side, sucking her right breast while I jabbed the dildo mercilessly into her dripping hole.

She was shocked.

"What are you fucking me with!?" she exclaimed.

I didn't answer, continuing my assault on her sex with the rubber phallus. Over and over and over I pushed the synthetic intruder into her yielding body. She slowly began lifting her hips, meeting each thrust of the dildo with her ass off the bed. The initial shock of being penetrated by something other than her husband's cock was wearing off, and the physical pleasure of being mercilessly fucked by a dildo was taking over.

Tina is slow to cum when being penetrated and I usually cum before I can get her across the finish line. Not so with the nerveless dildo. I fucked her pussy with that toy until her body convulsed and she let go with a very intense orgasm.

Despite the pleasure she received from being fucked with a dildo, she never really 'got into' the whole sex toy thing. That didn't stop me. I loved it. The sight of her pussy being filled with a dildo was an incredible turn on for me, and I loved the feeling of fucking her sloppy pussy with my cock after I had fucked her with a dildo.

So I bought two more dildos. One was a semi-realistic, deeply veined, black vibrating cock. The other was a long, thick, pink jelly dong. The new toys were much larger than the "Purple Missile" she had been introduced to. These two new toys were beautiful, and taking them out of the package I could not wait to use them to drive Tina over the edge of sexual bliss.

But just looking at them and handling them would make me hard. I could not push the thought of testing them on myself out of my mind. Thoughts of that fateful night with Jenna would flood back and I would remember the pleasure I experienced when she had penetrated me with her finger. "If one finger felt that good, how good would a cock feel?" I asked myself.

I decided I had to find out. Before ever using the new toys on Tina, I tested them on me.

In the shower I gave myself an enema and loosened my ass with the missile. Next, I lubed my ass and the new pink jelly dong, and slowly slid the toy cock into my ass.

I thought it was going to tear me apart! It was so thick! But I couldn't stop. The pain was minor compared to the incredible pleasure of being filled with cock. Why had I waited so long to explore this side of me? I continued to push this invader into my ass and before long the entire cock was inside me. I felt so full! What an erotic sensation!

I held the base of the dildo, letting my body adjust to its presence. Once acclimated, I pulled on the base, slowly sliding it out of my ass. I could feel the molded veins as they rubbed against my opening. The sensation was amazing, and I was as hard as a rock! I slid the dildo almost all the way out, leaving just the flared head inside of me. The dildo narrowed just behind the head, and my sphincter closed around the narrowing cock.

Reversing direction the dildo spread me out again as the thicker shaft spread me open. This was amazing! I pushed and pulled that thick pink cock in and out of my ass until I came all over the wall of the shower. The feeling of my asshole squeezing a cock as I came was beyond description. Never had I imagined that I would enjoy being fucked in the ass that much! Hell, never had I imagined that I would enjoy being fucked in the ass period! My knees were weak and I could barely stand. I pulled my new toy all the way out and was overwhelmed by the sensations I was feeling. It was apparent to me that this exercise in self anal pleasuring was going to have to happen again. And again. And again.

I didn't want this new pleasure to become routine, so it became a treat I gave myself only after I achieved a milestone in my workouts. (If I completed a 5K training run without stopping, for example.)

As good as this self pleasuring was, I needed more. Fucking your own ass with a dildo lacks intimacy, and I realized I needed the intimacy.

I needed my wife to do this to me.

But how?

One night while we were in bed, enjoying one of the increasingly rare moments of intimate sex, I pulled my cock out of her pussy and positioned it at her asshole.

Now, I confess that I knew this was not going to be permitted. There was no way she was going to let me fuck her in the ass. She didn't even like a finger tip in there. (I did. I loved putting my finger in a woman's ass. The smoothness and tightness of a sphincter muscle clamping on your finger is a very erotic feeling.)

As I pressed the head of my cock against her wrinkled asshole she shook her head and said "Uh-uh".

I knew I had to do it now. I knew it was do or die. Holding my cock where it was, I gazed into her eyes and whispered "I want you to do that to me."

There. I had said it. I had openly confessed that I wanted my wife to play with, and fuck, my ass. It was time to formulate a plan on how to make it happen.

It is in situations like this that the internet is your friend. I investigated the act I was hoping to perpetuate and learned I was not the only one who liked being penetrated that way. I learned that many women like to fuck their man that way, and that there was a name for it: Pegging.

I read everything I could find on the internet about pegging. I investigated what devices people used to peg and read the consumer reviews. I searched sex toy sites for a set up that would be functional for the planned activity, yet would not be too expensive if this wound up being a onetime deal.

The Doc Johnson Vac-U-Lok system appeared to be exactly what was needed, and I ordered a kit along with a bottle of cherry scented anal lube.

Valentine's Day was when the deed would take place.

We had a romantic dinner (I cooked) and after we were sure the kids were asleep we retired to our bedroom.

Smelling like smoke from the grill, I used it as an excuse to shower before we began our activities. I needed to get in the shower to clean myself out. The last thing I wanted was gross her out with "matter" coming out while she fucked me. If that did happen, there would not be a second time.

The strap-on was out of sight, but easily accessible for when the time came. Again I blindfolded her, both to heighten her arousal and to keep my actions secret. We climbed into bed, and I sat myself between her legs near her feet. Squirting a generous amount of hand lotion on my palm I took hold of one of her feet and began massaging it. Tina may not be all that keen on sex, but a good foot massage usually gets her in the mood, and letting my eyes wander over her naked form while rubbing her feet and sucking her toes would make me very hard and cause my pre-cum to ooze and drip onto the sheets, leaving visible evidence of my arousal.

After expending ten or fifteen minutes of effort on each foot Tina was very relaxed. From my position between her legs I could clearly see she was aroused. Her lips were swollen and beginning to spread, her pussy opening like a dew covered morning flower.

I went down on her. With a bullet vibrator on her clit, I licked her pussy, and grazed her asshole with my tongue. The blindfold appeared to be working because she seemed to be more receptive of my oral assault than was typical. Maybe it was the vibrator. I don't know and I don't care. All that mattered at that point was that she was cumming on my face.

Still blindfolded I directed her out of bed and had her stand with her knees against the side of the mattress. I bent her over at the waist making sure her face and tits were firmly planted against the mattress. Being bent over in that manner, coupled with her spread legs, her butt cheeks were spread wide, exposing her crinkled brown hole to my view.

I attacked it. I attacked her asshole like a man who had not eaten for days. I kissed it, licked it, sucked it. I stuck my tongue in it as deep as I could. For a woman who adamantly said she did not like having her asshole played with, she sure seemed to enjoy having a tongue in it!

God did I love eating my wife's ass! The feeling of her tight ring on my tongue cannot be described. Knowing I was doing something so perverted only made me harder. I licked her crack from top to bottom, alternating between her gorgeous asshole, her dripping wet pussy and all points in between.

Once I was sure she was adequately aroused again I stood her up, and, still blindfolded, lifted one foot at a time and placed them in the leg holes of the strap-on harness. After I pulled the harness up over her hips I tightened the straps to keep the harness firmly in place. Her repeated questions about what I was doing were met with silence. I almost came when I looked at her with just the harness and blindfold on. The dildo wasn't even fastened to the harness yet!

With the harness securely positioned, I retrieved the dildo from it's hiding spot and, with trembling hands, placed it on the Vac-U-Lok attachment. I took a step back and marveled at the site before me: The woman I loved more than my own life, her womanly curves, D-cup breasts, erect nipples, and a six inch life-like cock protruding from her crotch.

If you have never witnessed such a sight in real life, you need to. It is so different, so erotic, so... contradictory. You can not believe how absolutely fucking HOT it is until you see it for real.

My mouth was dry. My cock was so hard it ached.

I took off her blindfold.

The response was not what I had hoped.

"What the hell is this?" she asked with a measure of irritation.

I paused, disheartened by what I had heard, and searched my mind for how to answer.

"Do you remember when I told you I wanted you to 'do that to me'? This is what I meant. I want you to fuck me." I replied.

The look in her eyes spoke volumes. She was trying to digest a lot of information in a very short time. I guess I did drop a bombshell on her. It dawned on me that in her naiveté or willful ignorance, she didn't understand what it was I had wanted her to do when I had told her I wanted her to "do that to me".

"So you're gay?" she asked.

"No, I'm not. I have no interest in being with a man. I want the most beautiful woman in the world, who I love with all my being, to fuck me with a strap-on. I need you to fuck me with your strap-on."

"I don't understand. Why?"

"It's a huge turn on for me. My ass is one of my erogenous zones. I want to know what it's like to be fucked there." (Of course, she had no idea I had been pleasing myself that way for a couple of years.)

"Why can't I just use my fingers?" she asked.

"Would you really stick a finger in my ass?" was my rhetorical reply.

"No, I guess not. Can't I just use one of the other toys?"

"What's the difference between using a toy you hold in your hand and using a toy that's attached to you in your pelvic area so your hands are free to do other things?"

"I guess there isn't a difference." she resigned. "Do I really have to do this?"

The discussion continued like that, her questioning and me explaining, for a few minutes until she dropped her arms to her side and reluctantly asked "What do you want me to do?"

I rubbed my rock hard cock against her dildo as I embraced her and kissed her. The sensation of rubbing my cock against hers while her hard-nippled tits pressed against my chest was better than I could have imagined. I reached down, grabbed her cock and began stroking it. Stroking someone else's cock was a very foreign feeling, yet it was very erotic and exciting.

But it was time for the main event.

It was time for me to get fucked.

Grabbing the lube, I applied a generous amount to the life-like appendage protruding from her pubis and also applied a dollop of the gel to my waiting asshole. (In my research on pegging, I had learned that "too much lube is just enough".) Bending over the side of the bed I rested my forearms on the mattress and spread my legs, opening my ass for her to see for the first time.

The February air was cool on my lubed asshole and added to my anticipation of what was coming.

She strode up behind me and placed the head of her cock against me. I felt it touch just below my longing hole so I bent my knees a little, allowing her cock to line up with my brown eye.

When the helmet of her cock finally touched my asshole, I jumped a little. Partly because of the unexpected feeling, and partly because of the anticipation. I was only six inches away from fulfilling a desire I had basically had since Jenna stuck her finger inside me some twenty years before.

I relaxed my ass while I pressed my torso and forearms into the bed so as not to get pushed over. Tina held her cock in her right hand while she spread my ass cheek with her left.

She started to push.

My asshole began to yield as the very tip of her cock wedged it's way inside of me. The initial penetration was all it took for me to open all the way and accept her gorgeous cock inside my forbidden place.

Once the head was in the remainder of the shaft followed easily, and in a matter of seconds my bottom was filled with my wife's cock and her balls were firmly pressed against mine.

She was all the way inside me! My wife had her cock in my ass!

The guttural, almost animal moan that escaped from me was one of delirious pleasure and relief.

The feeling was delicious.

"How's that?" she inquired.

"Oh my God, it's better than I had imagined!"

"Now what do I do?"


And then she was fucking me. Sawing her cock in and out of my ass. The feeling was indescribable. The head brushing my prostate. The veins rubbing my stretched sphincter. Her balls slapping the back of mine, sticking slightly because of the lubricating gel... Her thighs pressed against mine.

It was more than I had imagined it would be.

I let her fuck me like that, bent over the side of the bed, and enjoyed every second of it. The amount of lube we used made our coupling very slippery and comfortable. But I wanted to feel her closer. I had her pull out of me. The feeling of emptiness was immediate. I needed her cock back in me, and fast! Climbing onto the bed, I got on my knees and had her get behind me. I arched my back and stuck my ass out like a bitch in heat. She slipped her cock back into me much easier this time, and started to fuck me again. I had her lean over my back, so I could feel her nipples scrape my back as her tits swayed from her thrusting into my willing body. Wow. The sensation of being fucked in the ass while two pendulous breasts rub against your back is amazing.

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