My Beginning Pt. 01-07

Quivering, I sat up and swung my leg over his hips. Straddling his waist, I could feel his cock press against the length of my bottom. I leaned forward and kissed him passionately! My hands caressed his face as our lips and tongues met. I slowly rocked my hips, feeling his cock, feeling mine rub his abdomen. I sat up, gave my cock a slow stroke while I reached behind me and held his manhood against my bottom. The feeling was terrific! I rolled my ass further back to feel him more.

He handed me the bottle of lube he used earlier. Putting a fair amount on my fingers, I rubbed my loose hole, surprised by how my fingers felt across it. More lube was placed in the palm of my hand, I stroked his cock, feeling his excitement. My cock was throbbing now, it was the hardest I had ever been. His hands running up my thighs he said, "Go slow, breath deep breaths and relax. It's a lot to take for your first time Ash."

I nodded, biting my bottom lip. I lifted myself up and guided the head to my hole. The tip felt soft and warm pressed against me. I lowered, slowly, feeling the resistance against me. My body tensed, worried about my next move. Taking a deep breath, I relaxed and tried again. POP! His head was in! Slight lightning strikes of pain shook me. {So much larger than two fingers!} I halted, waiting for the pain to subside.

Once I was comfortable, I lowered again. This time there was no pain. I could feel the space within me filling up, the desire rising! Lowering myself again, I felt the head finally all the way inside! I couldn't believe I could feel that! I had no idea I could have so much sensation back there!

I held myself in that position, thinking about everything that had transpired. He rubbed my face and smiled. "You're doing wonderful, Ash!"

That name. Why Ashley? Why did I agree to wearing this? What possessed me to be a girl at this moment?

I snapped out of my questioning. My feelings can wait, I'll sort them out later. I needed him, I wanted him inside of me.

Due to my inexperience and my lust, I lowered myself faster. Pain shot through my spine, I gasped and whimpered. I bit my lip so hard I was shocked I didn't draw blood!

He held me up, and smiled. His hands on my bottom felt calming and reassuring. My pain dissolved little by little with every tap of his playful fingers. I lowered again, this time with no pain, only pleasure and excitement!

"Halfway there baby girl." He said with a slight laugh.

Halfway. Dear lord, I'm only half way!? The desire was killing me, the anticipation was overwhelming. If I just endure the pain, he will be all the way inside. I can handle it, right?

Yes, yes I could. I slammed my hips down onto his legs, forcing all of his cock deep into me. The pain was excruciating {Bad idea Ash!} but I gripped his chest and sat there, all eight inches inside. My cock twitched and slapped his belly button, oozing more of my precious fluid. To distract myself from the pain, I rubbed my tip with a finger and licked it off. It tasted wonderful! I had never tasted myself, precum or cum. Shocked I did that, the pain was a footnote. I felt his hands firmly run up my corset, thumbs rubbing my nipples through the soft fabric.

I rocked my hips forward and back, feeling his cock inside me, pressing against my prostate. I started to bounce up and down, only millimeters at a time, feeling his girth loosening me up.

Feeling more confident and more comfortable, I started going for longer strokes. The pain was still present but nothing near what it had been. I did this for a few minutes before going half way up his shaft and back down.

Pain was replaced with pleasure! My legs were quivering and my arms were shaking. My hands on his chest to get leverage, his hair felt so wonderful pressed against my fingers!

My man's hands went to my hips, forcing my bottom down onto him. I leaned in to kiss him as he rolled me over onto my back! I giggled out of excitement! The smile coursing through my smooth body, I felt wonderful! Why does this feel so right!?

He sat up on bent knees, lifting me up with his cock still inside. Placing a pillow underneath me, just in the small of my back, he smiled! "You are gorgeous, sweet heart." He said between kisses.

His hips pulled back, slowly exiting me. He pulled my legs up around his neck and pushed back into me! Slowly he exited and entered my bottom, sending jets of pleasure through me! My hand found my balls but went past and down to his shaft. Reaching between my legs a placed my fingers on either side of his cock thrusting into me! My other hand pinching my nipple!

His hands gripped my thighs as he slowly thrust into me! His firmness stretching me open. His pace quickened! The sounds of his hips smacking my thighs was intoxicating! My face flushed, I couldn't believe you could experience this much pleasure!

He pulled out, "Get on all fours baby girl." He said with a stern tone. My eyes widened and I quickly rolled over. Arching my back to tease him, I slowly shook my ass on all fours. He laughed a hearty laugh.

He pulled me to the edge of the bed, standing on the floor. I instinctively guided his cock to my ass as he thrust into me, hard this time. I was expecting pain but only experienced pleasure and excitement! His massive cock was pounding me, hands gripping my hips, pulling me into him! All I could do was bury my head into the mattress, eyes rolling! My hand found its place, fingers caressing his cock while he fucked me. My cock swinging from his motion, dripping onto the bed sheets!

For an eternity he sent intense emotions through my body before I felt him slow up. His cock swelled and shook inside of me! Warm streams of cum shot inside of me, giving me the experience I had so desired! He stood there for a minute, cock softening inside of my ass. His ass now.

I collapsed onto the bed, he laid down next to me, running his finger playfully up my spine. Lying there, I thought of everything that happened. Talking online, the drive here, tea in his kitchen and flirting. Then the outfit. Why compelled me to do this? I had always been curious, deep down. I had always wanted this. To be cute and pretty.

"Stay the night, Ash. I'll make breakfast in the morning." He said as he kissed my bottom and gave me a good smack!

The daylight peeked through the blinds, directly into the pillow I was resting my head upon. I awoke to the smell of lavender and old spice again, the candles had long since gone out. The sheets felt wonderful against my skin, soft and smooth, cool and relaxing. I stretched my arms above my head and felt the tug of my bustier along my sides. I didn't realize I fell asleep with it on.

Last night rushed back to me. The pleasurable sensations I experienced, the deep emotions I felt... what am I doing? I felt shame and guilt. Why did I do this? My life had been turned upside down last night. I felt concerned about what I felt was right, what was right for me.

I sat up and looked around slowly, taking in the sight. Charles wasn't in the bedroom, I could hear him outside in the kitchen. Pots and pans banging, dishes clanking and what sounded like a percolator going. I smiled and let out a small laugh. My mind eased a bit, I felt right. I felt good. Why did I feel this way!?

My feet touched the hardwood floor and I stood up, feeling the soreness of my bottom for the first time. It wasn't a painful soreness but a good soreness, like that which you feel after a good workout. My clothes were neatly folded on the top of his dresser. I didn't want to put this on, I didn't want to let this side of me go. I walked over to the corner of the room and picked the cheekies up I had worn briefly last night. Feeling the fabric on my fingers, I liked this side of myself. My mind was ablaze with thoughts of how deranged this was but I wanted it.

Slipping the cheekies on, I looked around, hoping he had something else for me to wear laying out. I cracked the bedroom door a little and asked, "Charles, do you have... umm... do you have..."

"In the closet, West side of the room, Travis." He interrupted.

He used Travis instead of Ashely.

Shame and embarrassment rose from my stomach to my head. I felt the heat of my blushing. Disappointment, sadness, confliction, anger all riled inside! {What am I doing!? I'm not a girl, I'm not Ashley. I'm just a pervert!} I sat on the side of the bed, my eyes wide open, mind racing, questions buzzing around. I was a man, not a woman. My heart ached. I didn't want these emotions. I cupped my face in my hands and felt the moistness of my eyes.

I walked over to the dresser and picked my clothes up. The coarseness of the material made me feel worse. Slipping the bustier off, I slipped into my t-shirt. I hated it. I despised the feeling of, not only the material, but going back to being who I was born as. He had a full length mirror in the corner of his room. Looking at the reflection made me sick.

Happiness left me, the room seemed to grow dank and weary. NO! I'm not going back to this, not here!

I threw the t-shirt off and put the bustier back on. Went to the closet and opened it. To my surprise, he had so many women's clothes! I perused the selection and laid a burgundy sundress onto the mattress. I strapped the heels back on and slipped the dress over my head, placing the wig back on afterward.

Strutting to the mirror, I felt my joy return! The reflection showed a cute woman with a smile on her face! My heart skipped! I smoothed the skirt out across my legs! I wish I had hips for this dress.

The kitchen smelled of coffee and sausage. He was by the stove, scrambling eggs and stirring grits. I walked over to him and placed my hand on his shoulder, "Sit down, hun. I'll finish up." I said with a large smile. He looked at me and nodded.

Sitting at the table, I brought him a cup of coffee, asking if he needed cream or auger. "No, thank you though." A kind smile crossed his face. I went back to the stove and tasted the food. I seasoned everything, he said he didn't know how I liked it so i could just season it at the table.

"Did you enjoy last night, Travis?"

I felt the twinge of sadness creep back from earlier. He noticed and quickly looked away.

"I rather enjoy being Ashley, Charles. Please just call me Ashley." I replied with a confidence that startled me.

"Okay." He said quietly. His reservation confused me. I didn't understand what was going on. He was the one who steered me down this path and then threw it away just as quickly? I felt wonderful, truly happy as Ashley. I thought that's what he wanted from this, both of us to be happy with last night and this journey of exploration.

Plating the meals, I brought them to the table and sat down. I looked at him, hoping to make eye contact but he looked off through the window into the distance. Silence sat uncomfortably in the room for a long while before I spoke up. "Do you not like this?" Brash and insensitive question but I had to ask.

He sighed and finally looked at me. "I like both sides of you. Travis and Ashley, but you seem to have fallen in love with Ashley."

"What do you mean?"

"You are a charming young man and a beautiful crossdresser. I was hoping you would like being both."

"Well... it's new to me. I kind of delve into new things pretty hard, try to learn as much as I can. Maybe... maybe it's that part of my personality. I guess I'm just wanting to learn as much as I can before going back to my old self. You know?" Deep down, I felt hurt by my own statement. I didn't quite know why though.

He sat there, looking at me, processing what I said. After a short time, he seemed to accept that, I wasn't certain if I did or not.

We finished breakfast and I went and changed back to my guy clothes after a shower. He asked if I wanted to spend more time together and I enthusiastically said yes. He walked me to my car and I backed out to drive home.

The drive home seemed to take a long time. My mind processed everything that had happened and how I felt about it all. I struggled with my new found desires, wondering why they were still there. Why am I so depressed now? Why do I miss the long hair, the dress? My mind drifted away from the sexual pleasure and focused on the euphoria I felt this morning, slipping on the dress and looking at the girl in the mirror.

Before I went home, I stopped in a town close by that had a Target. I was nervous but I walked to the women's section. It was a college town, so more open minded than the small adjacent towns, shouldn't be a problem. I grabbed a skirt, stockings and panties, bra and blouse. I decided to go to the CVS to get lipstick. I didn't want to draw too much attention to myself. The girl behind the register made small talk.

"I wish my boyfriend would go shopping for me!" A smile crossed her face.

"Hehe... yeah!" I could feel my hands trembling!

I paid the total and bolted! I sat in my car for a while, waiting for my nerves to settle down before walking to CVS next door. I grabbed dark red lipstick and matching nail polish. This time the cashier paid no attention to me or what he rang up. Too busy texting someone.

When I got home, I rushed to my room and shoved everything into the back of my closet, underneath a tote of old models I had neglected. My mom came in soon after and asked how Matt was (he was the friend I told her I was hanging out with). Told her he was fine and started getting ready for work. She asked if I needed anything from the store, she was heading in to get some new clothes for Dad. I thought about it, "No, I'm fine mom. Thank you though!"

She pecked my cheek and patted my face. "My handsome boy! Have a good night at work. Work hard hun."

Her parting statement stung this time. A thousand times before she had said that, it never hurt. This time, it felt foreign to me. I sat on the side of my bed running these new thoughts through my head. Trying to figure out what was wrong with me. Mom was gone, Dad was in bed (he worked the night shift) so why not try on those stockings?

I dug them out of the closet and slipped them on. They felt wonderful! My legs looked even better! I felt happy with myself. "They're just clothes..." I murmured to myself. I put my jeans on over them and went to work.

The store wasn't all too busy, it never was on Friday nights when there was a tractor pull going on. (Yep! Small, rural town!) I stocked shelves and faced them, cleaned the floor to a shine, all the while lost in my thoughts. The cashier I worked with regularly was an older lady. She was the director of the local library during the day. We always discussed anything that came to mind. I trusted her, more than most people I knew.

"Stacy, I... I have a question." My voice was shaking a little.

"What's wrong my dear?" Her smile on tone always put me at ease.

I knew no one was in the store but I looked around regardless. "What umm... what do you know about... about ummm..." I trailed off.

She leaned forward onto the counter, resting her head on her chin. "What's bothering you dear?" She said with concern.

"I'm having a difficult time with... with myself."

"Girl trouble?"

"Ha... I suppose you could call it that." I said running my hand through my hair roughly.

"Well, what's wrong? You've never been one to be shy around anyone." Her face revealed her thoughts, she knew it was deeper than her first assumption.

"Have you... have you ever questioned who you are? Whether you were right... as who you are?"

She looked at me. Staring into the soul. "Are you questioning your personality, your future... your gender?"

My reaction to the latter gave myself away. My eyes bolted open and lost my color. She looked at me with an understanding that I didn't quite know. "After work, we will talk after work dear. I'll make tea." Her smile reassured me of any doubts I may have had going to her about this.

The hour or so before we closed dragged on. I was anxious about our talk later. I shouldn't have said anything. I should just go home. She lived next door to the store, so it was too easy to go over. We closed and ended up going to her place.

She lived alone. A widow of twelve years. Her house was filled with books and antiques. I always enjoyed going over there to play chess or discuss books with her. She brought a couple cups over and the teapot. Earl Grey, as always. Sitting across from me, she waited for me to start talking.

I took a deep, long breath and told her about the previous night. She was shocked and concerned about my well being. Not that I dressed, but that I went to a strangers house.

"Do you feel happier as Ashley?"

"I'm not sure. I don't know if it was the experience of last night, something new, or what it is."

" How did you feel this morning, dressing up, after you woke?" Her tone was very analytical, courteous, and sincere.

I told her about the feelings that rushed over me; happiness, fear, confusion, disgust and conflict. On one hand, I was a guy who played football, in good shape, masculine, outgoing, charming and (now) unsure. On the other hand, well, I had on red nail polish and was questioning the other.

"Why do I feel this way? I didn't want to leave that. I didn't want to stop looking in the mirror. I felt joy and I felt... pretty and wanted. I didn't want to go back to being Travis, I wasn't happy there. My body was telling me to stay in that state. To stay as Ashley, that that felt right. I've never felt that way, not as a guy. I've always felt I have had to force myself to be this person that everyone looks to me to be. When I was in that dress and wig, I felt... genuine." My tears finally broke the dam holding the rushing torrent back.

She came over to my side and rubbed my back, not saying a word. My entire life was a lie to make everyone else happy. I kept thinking back to when I was a small child, memories I had blocked, buried deep inside. I grew up in a fiercely republican, devoted catholic area. This wasn't who I was supposed to be, this wasn't how I was supposed to grow up.

"Honey, I want you to look at me. Okay?"

Tears running down my face, I looked up. She had kind eyes, now more than ever.

"You're scared. Heck, I'm scared for you! But I know that you will make the right decision and if there is anyone who can handle this, it is you. You have always been a good kid; smart, curious, always asking the hard questions. I will support you regardless of what you decide. You are the child I never had. I've always seen you that way dear."

She went on, talking about looking for books to get into the library about the subject. Gender identity, crossdressing, transitioning, what have you. My mind was calming down as she poured more tea.

"You're going to college in August, correct?" I nodded yes. "Good. That town is far more open minded than this backwards, hillbilly, one horse town. You will be on your own and can discover yourself. Now, which do I call you; Travis or Ashley?"

I looked at her, she was too kind to me. Always had been. She had always pushed my interests when it came to my reading habits. Now, it seems, she is supporting me with this issue. I could never thank her enough, never show her how much I appreciated her. "Let's try Ashley." I said as I cleared my throat and wiped the tears away.

She patted my hand. "Okay, Ashley." A smile tightening her wrinkled face.

A couple weeks had passed since I had my adventure with Charles and break down in front of Stacy. College was about to start and all of my belongings were packed. I had built up my female wardrobe quite a bit since those few days. I was surprised by how confident I was in buying women's clothes and makeup.

Charles and I had talked quite a bit since then. He wanted to make sure I was alright but was still concerned about my obsession with being Ashley. I alleviated his thoughts as best I could, despite feeling the opposite of what I was saying to him. He had explained that he didn't mind that I liked being Ashley, just that he likes the duality. His previous partner of fourteen years had been a crossdresser but transitioned to female full time without discussing anything with him. Charles would have been fine with it if he had just said something about it. We made plans to go out the week after I moved into my dorm.