My Beginning Pt. 01-07

I had always been curious about men. By fifteen I had been with my first girl but I didn't enjoy it, perhaps it was the fact we were both young and inexperienced but I didn't find myself attracted to her.

The summer I turned eighteen, I had been perusing craigslist awhile but finally decided to post a M4M ad. It was intended to just chat and see how I felt about men, even though I had been sexually curious for a long time.

An older gentleman, 54, messaged me. His name was Charles. He was very sweet, unmarried, just looking for someone to talk to. I had a suspicion that he wanted more but I was young and lonely, and incredibly curious.

Everyday for the next two weeks we messaged one another. He kept an odd schedule as I did, so after work I would send him a message on AOL (I feel old now!) We would stay up until two or three in the morning getting to know one another.

I'm a fairly old soul so the two of us really clicked. Then, one night, we started talking about sex. He asked what I wanted to try, what my boundaries were. I told him I wanted to try bottoming and topping, oral, kissing, most normal things. I wasn't too experienced with kinks yet. We talked about this until daylight. He was gay all his life, which was difficult growing up in the small communities we both lived in. I asked him if he would be willing to teach me a few things. He responded with caution, the age difference. Talk was one thing, actually doing it was another thing entirely.

The next couple days were back to our normal chats; talking about life, politics, our communities. Then he asked if I still wanted to come over. I was shocked! I said that I would adore that! We planned for Thursday night, it was a Sunday night we talked (I believe). I asked if I need to bring anything, a change of clothes if I want to stay the night.

Fortunately he lived close by. A small town to the north about forty miles. That night I was shaking the entire drive up there. What if he didn't like how I looked? (We never exchanged photos, only stats and vague descriptions.) What if I don't find him attractive? Being the first man I will meet as an intimate interest. I can't do this! I froze and drove all the way to his place. I couldn't bring myself to turn around.

I pulled up to his address. It was a cute home in the country. The Blue Bonnets on his front porch were large and well taken care of. I walked up the steps and he was already at the front door to greet me.

I was taken aback. He stood in the doorway with a large, genuine smile and a kind face. Standing at 6'3", he was just a few inches taller than I was. His barrel chest and arms outstretched were so inviting, I instantly went in for the hug he offered. He asked how my drive went. "Good." I replied shakily. At the time, I played football and wrestled. I was thin but muscular and hairy. I was self conscious about my hair.

He invited me in and we sat in the kitchen, talking most of the night. The entire time I took in the figure before me. He was incredibly handsome to me. A kind face with a rugged build. I was attracted to this man. He said multiple times that I was far cuter than he had envisioned. (That made me have butterflies!) Finally, I asked if he wanted to do anything. He said, "Certainly! Only if you are comfortable though." I nervously shook my head yes. What will I do!? Do I make the move, or does he!? I had no idea.

We went into the living room, he put on some music and sat on the couch. I sat next to him and he told me if I wanted to, I can sit closer to him. Of course I moved closer, my hip resting on his. I thought of how my girlfriend used to sit with me, so I went with that. At some point, I had decided that it was his home, he makes the first move. I was too nervous to do so anyway.

There is something about a man, putting his arm around you that makes you feel safe, only that moment matters. His arm was over my shoulder and I was looking at him. He was looking at me, eyes moving up and down my face and body. "You're quite beautiful." He said with gentle smile. Beautiful! I've never been called beautiful before! The feelings were overwhelming! I blushed and said, "You are quite handsome!"

He leaned in, I followed. Our lips met... the feeling was... amazing! I had no words! I could feel his salt and pepper stubble on my clean shaven face! I adored the feeling! That kiss lasted for what felt like a lifetime! I put my hand on his chest and the other on his neck. He pulled me close with his arm around my shoulder and his other hand lifted me but my hip and bottom. I was so aroused I couldn't sense anything else but his touch, his lips, the musky smell of his cologne, the increasing tightness of my pants, the growing bulge in his!

My hands were a dizzying mess as I explored his figure. He pulled me into his lap and I could feel his erection through my jeans and his! He feels... he feels amazing! I got up and startled him. His hands groped my ass while mine cupped his face! I had never felt more attracted and more attractive in my life!

I felt one of his hands go for the buttons on my jeans, the pressure behind them was finally released a little! Then he reached into my pants, under my boxers. I felt his rough, incredibly strong hands grip my firm ass! Then, I felt another new sensation. My cock was oozing, I could feel the slickness of my boxers. Did I cum!? I had never experienced precum before. I stopped him to look, I was embarrassed. He smiled and said, "It's natural baby, you're excited. I am too!" I felt a little better but was still unsure.

He asked if I wanted to go to the bedroom. I shook my head yes as I started to get up. Then his strong hands and legs lifted me from the couch with me still in his lap! I was light headed from the lust I was experiencing. As we went to his bedroom I found myself thinking, I must have him!

His bedroom smelled of lavender and old spice. I hadn't stopped kissing him as he carried me to his bed. Lowering me onto his mattress, I could see the lust in his eyes. He wanted me just as much as I needed him.

He pulled my pants down along with my boxers. I couldn't believe how much I had leaked! The inside of my boxers were slick with a bright sheen of precum. I was still leaking! As I was taking off my shirt, sitting on the edge of the bed, I could feel his thumb caressing the head of my cock. My shirt was off and to my delighted surprise, he was stroking his cock as well.

Now, I've always thought I was fairly well equipped. 6.5" uncut, fairly thick, large balls. I was proud of it. But this man... this man before me... was at least 8" and incredibly thick! I sat there admiring this man for a long time. The veins, my Lord the veins! I was honestly in love.

He guided my hand to his member. I wrapped my fingers around him, hardly touching my finger tips, while he removed his shirt. His chest was well defined and well groomed.

"Aren't you an excitable little boy, or should I call you a girl." He said as he rubbed the slickness off of my cock.

I was taken aback. "Why would you call me a girl?" I was so confused.

"You've been very feminine sense arriving. Hand gestures, overall movement. Did I read that wrong?"

My head was spinning, trying to think back. Perhaps I assumed the role my girlfriend inhabited. Being the only intimate experience I have had, I stepped into her mannerisms. While I was sitting there thinking about everything, he had gone to a dresser drawer and back. He laid a few clothes on the bed.

I look over and see black lace. Black lace cheeky panties with straps and black lace bustier corset. My face gave no deception to my surprise.

"You don't have to wear them, I just thought you may be interested."

Deep down I wanted to wear them, but I didn't want to admit that to myself. "I can't wear those! They are... to cute and I'm manly.." (lame excuse but that is what my teenaged mind decided upon).

He laughed and gave me a big smile. "If you are uncomfortable with it, I still want you. But if you want, we can shave your pretty little body."

I flushed. I was no longer the slight tanned color but a bright red. He wanted this and honestly, so did I. Never had I tried on panties before but I was deeply curious. The fabric was always so smooth and soft.

"I want to. I want you. Let's... let's do it." My heart skipped! We went to the bathroom together. We both climbed into the shower with a razor and lavender shaving cream. He must have planned this.

I had very little to no hair on my legs so he started on my chest. His hands rubbing my body with shaving cream felt wonderful! He was so rugged but so incredibly gentle while doing this simple act. He took the razor and started to shave me. I had never been shaved by someone before!

My chest, arms and my armpits done, he moved to my groin. Lathering up my cock, he kissed me deep, "You look gorgeous baby girl." He whispered as he started removing what little hair I had down there. I was so excited by his tone and the idea of being a girl!

We both cleaned off and stepped out of the shower. As I was drying off he stepped out, returning with a plastic bag. "Put all of it on if you would like. I will be waiting on the bed baby girl."

As he shut the door, I looking in the bag. The same black lace cheekies and corset were on top. Underneath were black strapped open toed heels and a brunette wig.

I was flustered. Have I gone too far? Do I really want this? What if I LIKE it? Oh my god... what if I DO like it!? I've come this far. Just a little further I suppose.

I take the corset out and wrap it around myself. My girlfriend wore them a lot so I had seen how she put them on. I laced it up snug and spun it around. Making slight adjustments to the fit and placement of the cups. It fit quite well. Next were the panties. One leg at a time. I slipped them up, feeling the fabric fit nicely into my athletic butt. The feeling was astounding!

I sat on the edge of the bathtub and put the heels on. Standing was difficult but I caught my balance.

The wig was well made, very smooth fibers, seemed to be real hair. I had short hair so it was easy to slip it on. I brush the hair with my fingers to make some sort of hairstyle and then looked in the mirror.

What stood before me wasn't a highschool jock. The reflection blazing back at me was this cute, sexy brunette in heels. I was turned on and frightened. Why do I feel so comfortable? Why am I not nervous anymore? My mind raced as I paced the bathroom. Both out of worry for what I now know I enjoy and to practice walking in heels.

I swallowed, took a deep breath, adjusted my panties as my cock had now gone soft but still quite drippy. I walked to the bathroom door and with a steady hand, opened the door.

The bedroom was dimly lit with candles. Tis time, the scent of lavender was gone. Replaced with the smell of Rosa centifolia. I knew the smell because of my home economics teacher. And on the bed laid my man. He was sipping a glass of wine and reading. His body was an image to behold. His pecs were massive and well defined, touched with a fair amount of hair. Standing at attention was the masterpiece that I intended to have take my virginity. In all it's veiny, throbbing glory, he gave his cock a good slow stroke. "You look gorgeous, Ashley."

I curtsied and gave a large smile unconsciously! That statement made me feel emotions I had never felt before. {Ashley... I adore that name!} "Why hello, Charles. Fancy seeing you in such a compromising position. Do you need a bit of help, sir?"

He laughed a hearty, warm laugh! "You are enjoying this, aren't you Ash?" His tone was sweet and sincere. I don't believe he thought I would be as into this as I was. Honestly, nor did I, but I felt good, I felt confident in myself. For the first time in my life, I felt right.

As sexy as I could, I walked to the edge of the bed. Swaying my hips, twirling my hair, slowly approaching. I crawled from the foot of the bed up to him, keeping eye contact as much as I could. Laying on the bed between his legs, with my face inches from his manhood, I bit my lower lip.

"How did you know, mister!?" I said as I teased his cock, running my finger along the bottom of it, watching it twitch with anticipation!

He grabbed the base of his cock and gave it a good squeeze, glistening droplets of precum oozed from the tip. "Take it slow, baby girl. I want you to enjoy it."

My nerves spiked! I looked at what I was about to do and the thoughts of what my imagination had dreamt and what I was actually going to do collided. I couldn't believe what my hands were doing on their own. One hand replaced him around the base of his cock, while the other caressed his balls. I thought of what my girlfriend would do to me and thought I would try that.

My lips were resting on his moist tip, his juices covering them. I gave a gentle squeeze and rubbed his cock. More precum! My tongue darted out from behind my lips, the taste engulfing my senses! He let out a gentle moan as my tongue swirled around his head, the thick clear liquid filling my mouth! {I am actually doing this!} His hand reached down and with a finger he pet my cheek. "Take it slow, baby girl. Enjoy yourself. We have all the time in the world Ashley."

I blushed a bright red! A few hours ago I was a college bound football player, straight but curious. Now... now I am Ashley. A sexy girl, in the throws of passion that I had never known. I didn't want to go back. I was happy as Ashley. I like being a girl, these thoughts confused me to no end. Thoughts I had long since buried. Why? Why did I want this!?

I placed my tongue on the bottom of his head and took the tip into my mouth. The throbbing, the size, taste, and smoothness of him overwhelmed me! The sensation sent shivers down my spine and back to my lips! I could feel my own moistness pressed against me as I laid on the bed. My own cock was firm but not fully erect. {What's wrong, little one?}

I took more of him into my mouth, swirling my tongue at the same time. Both hands were busy; one stroking him while the other caressed his balls and teased his thighs! I pushed him deeper into my mouth but gagged on his girth!

"Take it slow Ashley. I don't want you to hurt yourself baby." He said in a gentle, reassuring voice.

I looked up at him while taking a breath, tasting his juices still on my lips. I gave him a coy smile and kissed his groin and rubbed the tip with my thumb.

I wanted him inside of me. I wanted to feel his pleasure, feel the sensation of his pulse rising, hear his moans of pleasure. {I need him, I need him to feel how much I want this.}

My other hand reached back to my bum. Feeling the panties along my inner cheeks felt otherworldly! I ran my fingers up and down my bottom as I took him back into my mouth. {Small gulps Ashley, small gulps.}

For awhile I laid there, slowly working my way further down his cock. Every other stroke was another quarter inch down his manhood! I felt him tense up, I stopped and looked up thinking I did something wrong!

"I'm close, Ash! I don't want to cum yet baby girl." He said as he reached down and lifted me up to his face.

His cock pressed against mine, soaked cheekies separating them. To my surprise he buried his lips into mine! His precum mixing with saliva tasted amazing! He gripped my bottom firmly, I could feel the hand prints forming on my cheeks! The warmth of his touch, the gentle assurances he gave with his fingers. I could feel the fingers teasing under the panties, exploring my bottom, testing my reaction. I thrust my hips into his, grinding into his cock.

He flipped me onto the bed as he got up. Lifting my legs, he pulled me to the edge of the bed and kneeled on the floor. His face peering between my legs, he opened the panties off. Long strings of my juices stretched from my cock and the cheekies. I felt the cool air tease me, she twitched!

He kissed my bottom and inner thighs! My face flushed a deep red, my chest heaving from the deep breaths I had to take. My heart was pounding! It felt as if the only thing keeping my heart in my chest was the bustier! Then I felt it. I felt a wet, soft sensation run up my bottom. I look down to see his tongue caressing and teasing my hole. The feeling was more powerful than anything this far!

My hand reached down, not for my cock but for his head. Running my fingers through his hair, letting out girly moans and rotating my hips! I reached for my nipple and started to tease them, pinch and twist them. I bit my bottom lip hard when he dove his tongue into my hole! Spasms ricocheted through my hips, up my spine and into my head!

The sensation was world shaking! My body invited his pleasure! He twirled his tongue, fingers gripping my hips and pulling me further onto him! Looking down I could see my cock glistening with new juices. His thumb worked it's way to the base of my cock and he began rubbing me. His tongue worked me to exhaustion and his thumb swirling around, I had never been so turned on in my life!

My moans were getting louder. I couldn't believe how feminine I sounded, I felt so pretty and wanted! Then I felt his finger press against me. Slowly working its way into me! I felt his first knuckle go in. I whimpered and moaned, thrusting my hips down onto his finger. I felt a sharp pain rise from within and whimpered louder. He stopped, but left the finger inside of me.

"Relax, Ash." He said softly, "Deep breaths, relax."

My hands ran across my face, I could feel the heat of my cheeks, the pace of my breathing slowed. {Breathe in, breathe out} My mind was racing, I need to calm down. I had never done anything with my bottom before but I wanted nothing more than to feel him.

He pressed a little harder, going deeper. {Second knuckle... oh my god!} I could feel warmth and a strange tingle boiling over in my groin. His thumb still rubbing at the base of my cock, I twitched and oozed more. I couldn't take it, my body was shaking, legs quivering! My hips rotating, he went in further. Moans rose once again! Louder than before! I could feel the heat of my chest as my hands ran down my body! What is this feeling!?

He pulled his finger out and came up to kiss me. I grabbed his neck and pulled him in tightly. I could feel his manhood rub my bottom, the warmth, the wetness, the firmness drove me wild!

We kissed a while longer before he returned to my bottom. Tonguing me again, his finger soon followed. He started rubbing something inside, near my cock, that drove me crazy! Shots of pleasure rocked my body! He pulled out and went to the nightstand. Pulling a bottle of lube from the drawer, he rubbed me and fingered me with it. Then, he tried two fingers! The pain was still there but I could handle it this time.

I rocked my hips, working his finger into me, loosening myself up. I bucked my hips, feeling my cock slap my abdomen with a pleasing moist sound. My hands rubbing my inner thighs, legs squeezing his head between them! He tilted his fingers upwards while I rode them, hitting my prostate!

He pulled out and I could feel the cool areair rush in to fill the gap. Disappointed I looked down to him, biting my lip, rubbing my cock. "Why did you stop honey?" I asked in a surprisingly girly voice. My breaths were ragged, sweat making my smooth body glisten in the candle light.

As he laid on the bed next to me, he said, "I think you are ready, gorgeous. You're on top, baby girl."

My mind was ready for this! My body, an entirely different story! I laid there for a few minutes, kissing his arm, running my fingers through his chest hair, catching my breath. My legs were still shaking from what he had just done. Uncertainty crept in, was I capable of doing this? Not mentally, but physically?

My hand reached down and grasped his manhood; feeling the firmness, the girth, every vein pulsing. I looked into his eyes and saw lust with a hint of patience. This man, lying next to me, was so sweet and charming. He didn't want me to get hurt, he wanted nothing more than to see me experience pleasure. I wanted to give him pleasure.