My Journey Ch. 01

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npanxx
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As is usual, life got in the way of life and I was unable to see Trish for several days. Between kids, work, and taking care of repairs and maintenance around the house I found I rarely had time for even a quick whack-off session. Tina and I were mired in a decade long sexual rut that consisted of a once-a-month-quickly-before-the-kids-wake-up-pity-fuck. I did manage to get Tina to peg me for the first time in 18 months, and even though the pleasure was intense and the end result a satisfying orgasm for me, I thought about Trish the entire time, and wished it was her that was fucking my ass.

I now knew that I needed Trish to have her way with me.

Tina and the kids were to leave on their annual weeklong end of summer timeshare vacation with her family. I never joined them for this excursion. There was a "personality conflict" between me and some of her family. It was best that I stayed at home, went to work, and not ruin everyone else's vacation.

This time, I had an alternative reason for not going.

It was my chance to be with Trish.

My e-mail to Trish read "I'm available all weekend. I would like to see you. Interested?"

About an hour after I sent the e-mail my phone rang. It was Trish.

The first thing Trish said after I answered was "How much?"

"I really want to see you." I said.

She laughed.

"No silly. How much of me do you want to see?"

She had caught me off guard. I paused, trying to catch my breath and figure out what to say.

"All of you" I managed to croak, my throat dry.

"Say it. Tell me. Tell me what you want to see."

Finally, finding a little courage, I blurted "I want to see all of you Trish. I want to see every inch of your glorious naked body."

"There. That wasn't so hard, was it?" her tone chiding me. "Friday night, my place, say... eight o'clock?"

"Nine would be better. Tina always calls the first night."

"I'll text you my address. Be ready!" she exclaimed, obviously excited about our pending rendezvous.

The next thirty-six hours were torture.

Friday finally arrived, and Tina and the kids left for their vacation first thing in the morning. I went to work, unable to focus on a single task. My thoughts singularly focused on what might happen, what would happen, later tonight.

On the way home from work, I picked up a bottle of wine for Trish and me. Flowers had crossed my mind, but I decided such a thing would be cliché.

Once home I began to prepare for my evening with Trish. I took a shower and used that time to make sure I was completely clean inside and out. I shaved my cock, balls, and ass as I have been doing for years. After drying off, I applied some lotion to the areas I had shaved. (I love the feeling of all my parts being lubricated after I shave.)

I made sure my closely cropped hair was closely cropped, shaved my face, and put on some cologne and deodorant. I looked at myself in the mirror and began to wonder if Trish would find me attractive.

A typical middle aged man, I carry a little too much weight, but I think I carry it pretty well. I have broad shoulders and powerful arms. My hairy chest isn't well defined, but it doesn't sag either. The biggest issue is my stomach and love handles. No matter what I did I have never able to turn my abs into the proverbial six-pack, and the love handles never go away. I learned to just accept it.

Now that I was as clean as I was going to get, I dressed in my typical summer garb of cotton sport shorts and a plain T-shirt. A pair of deck shoes completed the casual summer look.

Tina called at 8:20 to let me know they arrived safely, and that the kids had a ball at the pool. Her sister had prepared a feast for supper, and they were just getting around to eating so she had to run.

"Love you!" she chirped.

"Love you too sweetie."

It was time for me to leave, so I grabbed the wine out of the refrigerator, jumped in my Camry and drove to Trish's suburban home.

She lived in a quiet residential neighborhood surrounded by attractive little homes with tidy, well cared for exteriors and yards. Trish's place was a modest structure, probably constructed in the '50s following the war when so many cities saw explosive growth, and neighborhoods like this became common place.

I wrapped on her front door and waited for her to answer. When Trish greeted me, I was glad I decided to go casual. She was dressed in a pair of loose cutoffs and a red tank top that hugged her perfectly proportionate C cup breasts. Nothing fancy, she looked like a typical suburban housewife, her hair hanging loosely around her face.

"Right on time!" she said, a warm, welcoming smile stretching across her face. "Come on in."

I followed her bare footed form into her house. Trish took the bottle of wine from me, opened it, and poured us two glasses. "Let's go sit on the patio."

We walked out the patio door from her dining area onto a small paver patio that was nestled between two "wings" of the house, and plopped ourselves into a cushioned porch swing, the only place to sit. It was a very private setting, with a small backyard stretching out in front of where we sat.

We each took a sip of our wine and Trish started the conversation.

"Listen, Clark. I want to tell you how much I have enjoyed getting to know you. You are a nice guy. I like spending time with you."

I knew there was going to be a 'but', there had to be. I braced myself for the inevitable disappointment.

"Most guys I let know about me are after one thing. They want the conquest, that walk on the wild side. They see me as a device they can use and toss aside."

I started to speak but she shushed me.

"Let me finish. You're not like that. I know what you wanted when Kim got us together, but you took the time to get to know me as a person before trying to know me as a lover, and that is going to make tonight extra special. For both of us."

She leaned over and kissed me. On the lips. Not merely a peck, and not a kiss of two lovers. Still, it was a kiss that spoke volumes.

"Let's grab a bite, I hope salad is okay. A girl needs to watch her figure you know" giving me a wink.

Trish took our glasses and headed back into the house. I followed, allowing my eyes to take in her form. It occurred to me then just how much of her body had been hidden by the business suit she wore at our first meeting.

Trish went into the kitchen. Setting our glasses down on the counter that separated the kitchen from the dining area, she refilled them. She then turned to the fridge. Bending slightly at the waist she took two bowls of prepared salad from the fridge. When she stood and turned around, Trish could obviously see where my gaze was focused.

"Like what you see?" she teased.

"I'm sorry, I didn't mean to stare. But your ass is gorgeous!"

"Thanks! I think it's pretty nice too. Ready to eat?"

We spent the next half hour at the table munching a delicious Romaine and vegetable salad, sipping wine, and laughing at the stories of my wild youth, and the stupid things I did.

I helped her clear the table, she emptied the bottle of wine into our glasses, and I followed her into her tastefully decorated living room and sat on the couch. I sat at the end, with Trish on my right, her legs comfortably tucked under her as she pressed into my side.

She placed her glass on the coffee table, reached to my chin with her right hand and turned my face to her. And then she kissed me. The same kiss she gave me on the porch swing. She pulled away slightly and we looked into each other's eyes. I don't know what she saw in mine, but I saw desire in hers and leaned back in, kissing her deeply with my tongue exploring her mouth. It was like kissing Jenna. Trish was a passionate kisser too, and wrestled my tongue with hers. My right hand rested on her thigh, and as we kissed I realized I was squeezing it. I was becoming very, very aroused.

Trish pulled away, got off the couch, and pushed me onto my back. She then lay down next to me, so I scooted up a little so I was laying somewhat on my left side. Trish took a position that was partially on me, partially on the sofa, with her left leg between my legs basically straddling my left thigh. Her left arm was against my chest as she stroked my neck and face, moving her sweet to mine for another round of kissing.

Having her body pressed to mine felt wonderful. I could feel her breasts mashed against my chest and her left thigh against my maddeningly hard cock. My right arm was tenderly stroking her back, ever so slowly migrating south to where I could finally touch her ass. It was marvelous. I decided then and there her back had had enough attention, so I focused on her sorely neglected ass. I stroked it. I groped it. I massaged it. Then my pinky slipped into the cleft of where her ass met her legs. In my opinion this is the sexiest part of a woman's body, and I loved the way that cleft enclosed my finger as I gripped her butt cheek. I couldn't wait to see her backside without the shorts.

Trish apparently liked the treatment she was getting because she began to slowly rock her hips, and I could feel the stiffening rod in her shorts pressing against my upper thigh. I reluctantly let go of her butt so I could reach between us and reposition my cock, now rock hard, and pointed it straight up at my belly button. I was now able to comfortably press my dick against her, and I too started rolling my hips while resuming my manual assault on her ass. We kissed, groped and dry humped each other for over a half hour. We were both incredibly aroused and I think the desire to get out of our clothes was mutual.

"Should we take this to the bedroom?" she asked.

I gave her a quick kiss on her lips and said "I'd like that."

Trish rolled off the sofa, took my hand and led me to her bedroom. I followed her down the short hall admiring her ass the whole way. The way her butt swayed made me think she was giving me a show. Totally unnecessary, but appreciated nonetheless.

Once in the room, she closed the door, turned to me and embraced me again for a long, deep, wet kiss.

Trish broke the kiss and took a step away. She grabbed the bottom of my T-shirt and lifted it over my head. I raised my arms so she could take it all the way off. I grabbed the bottom of her tank top and did the same, revealing to me a sexy little black satin bra. She then took hold of the drawstring of my shorts, gave it a yank and untied them. She took hold of the side of the legs and pulled them down, bunching them around my feet. I stepped out of the shorts and heard a very small whimper escape her lips. I looked down and noticed there was a large wet spot on the front of my boxers, the pre-cum stain giving indication of the extent of my arousal. Once she stood, I unbuttoned her shorts all the way down to the crotch, the back of my right hand feeling her hardness as I did. I slid her shorts down her athletic legs and she stepped out of them, revealing black satin 'boy shorts' that matched her bra.

She was a vision of loveliness in her black underwear. Her bra held her breasts firmly, squeezing them together and displaying her very nice cleavage. My eyes wandered down her body, past her stomach to her boy shorts. The glossy satin/spandex material clung to her womanly hips, accentuating the cock that stretched up to the left with the head near the waist band of her panties.

I'm a sucker for satin, spandex, any kind of lingerie really, and the way her undergarments hid, and yet accentuated, her charms drove me crazy with desire. I took her in my arms and tongue kissed her deeply, pulling her body to mine and pressing my cock against her lower belly. I slowly lowered both of my hands to her ass and cupped a cheek in each hand, fingers gliding back and forth in the cleft. I removed my lips from hers and kissed her cheek as I moved my mouth to the junction of her neck and torso. I gently kissed and licked her neck and shoulders. While I mauled her ass cheeks, Trish reached up behind her and unclasped her bra. She threw her arms back around me, her mouth near my right ear, and released a sigh of pleasure. Her warm breath made it's way to my ear causing me to arch my back and pressed my groin into her even harder.

Noticing my reaction, Trish placed her lips right to my ear and in a very low, breathy voice whispered "Ooooh, baby liked that didn't he?" and without waiting for a response she stuck the tip of her tongue in my ear.

I melted.

She had found my weak spot. I was putty in her hands and she knew it.

I was hers.

Trish bathed my ear with her talented tongue like she was licking a pussy, alternating between licking the outer flesh and probing the canal with her pointed tongue. It felt so good I stopped kissing her neck as I could only moan and gasp while she loved my erogenous zone.

She broke our embrace and took a step back, her unfastened bra falling to our feet, revealing a pair of beautiful breasts with large, dark areola and very erect nipples. I reached for them, but Trish was quick to gently bat my hands away with a devilish little grin on her face. "Not yet baby."

Trish knelt in front of me, pulling the waist band of my boxers out and down revealing my hard, oozing cock. She didn't touch it, but pulled my boxers down to my ankles. She lifted each of my feet gathering my shorts as they were freed. She tossed them aside and stood. For the first time in nearly twenty years I was completely naked in front of someone other than my wife.

Moving a couple of steps away, Trish turned her back to me and swung her head around to look at me over her right shoulder, causing her hair to flair out and cover her face briefly. Her back was arched, her ass sticking out and she had a look on her face that was a mixture of shy and sexy at the same time. She had a finger pulling down on her lower lip that seemed to say "I'm a demure little school girl. What are you going to do to me?" When Trish saw the look on my face she broke out in a huge smile.

Trish brought her legs close together and slowly bent over at the waist, her knees locked straight making her legs appear impossibly long. Once she was bent all the way over, her glorious ass pointing to the heavens, she looked at me around her right arm making sure she had my full attention. She slid a hand up each of her legs, eventually hooking her thumbs in the waist of her boy shorts and teasingly slid them down. When the garment reached the cleft just below her ass cheeks she stopped, and gently ran the fingers of her left hand through her crack, briefly pressing on her bud, closing her eyes and exhaling in pleasure. She resumed the removal of her undies eventually stepping out of them. She remained bent over and slowly moved her hands up her legs, across her hips, up her stomach until she was cupping her breasts, all the time looking at me around her arm, gauging my reaction.

But my eyes were focused on her backside and her puckered asshole. It was simply beautiful. More attractive than Tina's. God I wanted to lick it so bad!

Trish stood, still cupping her breasts and still with her back to me. It was like I was riveted to the floor, unable to move regardless of how badly I wanted to.

She started to turn towards me, lowering her hands from her breasts as she did. Time stood still as this very beautiful woman teasingly rotated, slowly revealing that which she had been keeping hidden from my lusting eyes.

Then she was facing me. My eyes were immediately drawn to hers. They held so many emotions, her eyes. There was desire and excitement while at the same time there was worry and fear. I suppose that for women like Trish, this moment of revelation is fraught with the reality of rejection or physical harm. That wasn't going to happen here. I knew all along that Trish was special, and had things to offer that a genetic woman couldn't. I hoped that my eyes were expressing desire, lust, and acceptance. I hoped my eyes were telling her I wanted her.

I broke our eye contact, letting my eyes take in the whole of her beauty. Her breasts were perfect. They were firm, but sagged just a little, much as you would expect of a woman in her thirties. I could not tell if they were enhanced or natural. Her tummy was flat. Not rock hard, but flat. Her waist was narrow, with just a little extra cushion. Her hips were wide, womanly, and melded into a pair of very nice legs. She had painted toenails, and her feet were very normal. I wondered if I'd be sucking her toes.

And then there was her cock. It was proud and hard, saluting me from her hairless crotch. Unlike many of the shemale stories you may have read, Trish did not have a python capable of splitting a man in two between her legs. She had a very normal length, very average thickness cock, similar in size to the strap-on dildo I had been using. It was, however, topped with a large bulbous head that made my mouth water.

My eyes again met hers, and after a couple seconds of an expressionless stare, my lips broadened into a wide smile. Trish's did the same, and the fear and worry in her eyes were quickly replaced with relief and joy.

We moved toward each other, our naked bodies touching each other for the first time in a loving embrace and deep passionate kiss. Our cocks touched sending an electric jolt through my whole body. We pressed our crotches together, reveling in the eroticism of the moment.

Trish broke our embrace and sauntered to the foot of the bed. She raised a knee to the bed and, like a leopard on the prowl with her back arched and ass raised, crawled up the bed until her head reached the pillows where she languidly rolled onto her back. Her legs were slightly spread, her head resting on the pillows. Trish had one arm over her head while the other slowly stroked her cock with her finger tips.

I was in a trance, mesmerized by her wares, as I climbed onto the bed and instinctively positioned myself between her legs. I was on my hands and knees hovering over her feminine form as I lowered my lips to hers for a tender kiss. Trish lowered the arm that was over her head, and took my hand in hers. She stopped the gentle stroking of her cock and took my other hand in the same way. This tender act told me that I was in for a night of passionate lovemaking. The wild fucking would wait until another time.

I lowered my body to hers and felt the heat of her hard cock against my abdomen. My cock had been drooling for a long time, and hers was leaking now, too. Our fluids combined to create a slippery environment, allowing our appendages to slide between our bodies. We made out like that for several minutes, kissing deeply and allowing our cocks to frot.

Trish's magnificent breasts beckoned, so I lowered my head to her succulent tits sucking her left breast into my hungry mouth. It felt and tasted so good. I tried to swallow her entire breast and felt her hard nipple at the back of my mouth. I released her breast, and began to focus on her areola and nipple; sucking, licking, and nibbling at the rubbery flesh all the while we ground our cocks against each other. I didn't want her other breast to feel left out so I worshipped that one the same way.

We held hands the entire time I loved on her tits.

Trish then rolled me onto my back and straddled my lower body. I looked down to where our bodies met. I was unprepared for the erotic sight presented to me; two glistening, rock hard cocks rubbing against each other. I thought I was going to cum right there.

Trish took my hands in hers, pinning them next to my head. She lowered her upper body as if to kiss me, but stopped as soon as her nipples contacted my chest. She swung her dangling boobs up and down, back and forth, dragging her rubbery nubs against my hairy chest. It felt wonderful. She lowered herself the rest of the way to me, squashing her breasts against my chest while she hungrily tongue kissed me and really began to buck her cock between us. I thrust my hips against hers, maximizing the slippery contact between us.

npanxx
npanxx
385 Followers