My Beginning Pt. 01-07

-Who should I expect? Travis or Ash?-

-Travis. I'm not sure I would be the slightest bit comfortable in public as Ash.- I hadn't gone out in public dressed.

-I look forward to seeing you Travis-

It stung more and more each time he called me that. For the most part, it didn't bother me when everyone called me Travis but it always hurt when he did it. Maybe it was because he introduced me to this, he brought this now dominating personality out of my deeper psyche. Perhaps it was that I cared for him as Ashley, and she wanted the affection and attention to herself.

My first day in my dorm was quiet. My dormmate didn't move in until Monday the following week. I had four full days to myself, I was more than ecstatic! After the welcoming pleasantries from the other dorm rooms, I settled in for the night. Laying out my clothes and makeup that I had so enjoyed putting on.

Amazon was a wonderful thing, once you figure out your sizes. I now had almost three full wardrobes. Tonight was a black knee length skirt with black pantyhose. I bought cotton hipster panties that were white, the cotton always felt wonderful! My bra was a Victoria secret white lace that I was quite proud of, both the fit and the fact that it was Victoria secret. My blouse was a red v-neck that complimented my brunette wig. I had been practicing my makeup when I could but was still an amateur.

After donning my alter ego, I looked in the mirror. Happiness washed over me, I looked stunning! The heels were only two inch open toes, perfect for.my height. I was looking forward to the evening as Ashley! Just a girl in her apartment.

I snapped several pictures, several different poses, taking in the woman in the reflection. My life had been turned around. I adored Ashley, truly happy as this feminine persona. My life as Travis was boring and unhappy. Trudging along putting this image forward that was false wore down on the soul.

I sat down with my laptop and perused the internet, looking at feminization tips, clothes, lingerie, makeup tutorials. My messenger went off, it was Charles.

-Hope your move went well- he sent.

-Indeed it did! I'm all settled in, no roommate yet. Supposed to be here Monday.-

-What are you up to?-

I hesitated, I wanted to tell him I was looking at clothes as Ashley, to hopefully prevent the pain of being Travis in this moment, but I didn't -Just researching my classes-

We messaged back and forth for an hour before I said I had to turn in. I shut my messages down and went back to browsing. There were so many things I wanted to try on, so many styles to go for. Then I found a thread on what was called a "sissygasm." I was intrigued! The author described their experience, riding their dildo until they came! Can I do that!?

I read more and more into it; positioning, mindset, toys to use, the world changing orgasm! I had to do this! I hadn't masturbated since that night, so I was pretty tense! I grabbed my keys and went to my car. Driving to the sex shop it hit me, I was still dressed! My stomach rolled, I was beginning to perspire! My hands were trembling! The first time I go out dressed as Ashley, I go to a sex shop!? Really!?

I sat in the car, parked in front of the shop for ages, waiting for it to die down. Finally, there were only two cars in the lot. Mine and what I assumed to be the cashier. I swallowed and went inside.

I opened the door and was met with a wonderful smell! Cherry and vanilla! Looking around, I was amazed by the number of different toys, plugs, lingerie, slutware and knik-knacks there. In the back was a massive wall covered in dildos. All shapes, sizes and colors! My eyes gravitated to a wonderfully veiny purple one. It was seven inches long and thick! I grabbed it. As I was walking to the counter I saw a beautiful red lingerie set with a garter belt! I found my size and proceeded to the checkout.

The man behind the counter was roughly my age, perhaps in his twenties and incredibly handsome! His skin was a wonderfully middle-eastern bronze. He wore a tight fitting polo that showed off his incredible physique! Leather pants that left very little to the imagination and a pleasant smile adorned his rugged, bearded face. I found him troublingly attractive. I could feel myself harden and my face blush. He obviously noticed me, looking me up and down, I could feel his gaze undressing me!

He made small talk as he rang me up. When he asked for my license I froze! He laughed and said, "It's fine, doll!" His smile calmed me a bit. I paid him and he took the receipt and wrote something on the back of it. I looked and it was his number!

"I...I'm sorry sir, I'm not that kind of girl." I said with a nervous voice.

"Don't worry baby, I know what kind of girl you are sweet cheeks." He replied as he bit his bottom lip.

I melted! My nerves went through the roof! Was I that obvious!? I thought I was fairly convincing! I let out a little laugh and walked out. I could see him staring at my ass as I walked away. For whatever reason I emphasized the sway of my hips and looked back to give him a flirty smile. I could see him mouth the words, text me.

I sat in my car with my bag of goodies, trying to decide what to do. Should I text him? I'll decide once I'm back.

I walked the hall of the dorm slowly, afraid of people seeing me. I made it to my door when I heard footsteps further down the hall. My heart raced as my hand fumbled for the keys. I unlocked it and stepped through, I heard a cat whistle as I shut the door behind me. I don't know if that was for me or someone else, but I wasn't about to find out.

I went to my futon and opened the packages! I was so excited! The dildo looked amazing behind it's wrappings, but it looked far better out in the open! I got up and went to the bathroom to put on my new lingerie. Slipping it on I discovered that the panties were crotchless. My dick just hung there in the open while my ass was snuggly pulled up by the fabric! I snapped the suspenders to the hosiery and adorned the bra. I looked in the mirror and fell in love! I looked like such a slut! I loved the feeling! I put a pair of red heels on, my only other pair. It completed the ensemble!

As I walked back into the living room, I saw the receipt. Perhaps it was the lust welling up inside of me or the loneliness but I grabbed my phone and messaged the man from the toy shop. -How did you know?-

I waited awhile, hoping he would respond quickly but he didn't. I looked at my new toy and my desires took over. I grabbed my bottle of lube and slathered the shaft and head. It had a suction cup so I stuck it to the tile floor. I bent over and toyed my hole for awhile, loosening myself up! My cock dripped all over the floor and my legs. Two weeks of not touching myself had shot my sex drive through the roof!

My phone dinged. My phone dinged! I rushed over to see a reply from him. -Hey baby, name Erin. I can always tell when a there's a cute little ass flauntin' it.-

-Oh hoho! You want this ass big boy?- What am I doing? I'm an idiot.

-I want it all, babydoll. Just you and me.-

I had to admit to myself that I wanted him. He was incredibly handsome and I kind of liked his dominant demeanor.

-When are you free babydoll?-

I wanted to say right now but I didn't. I didn't know him, we had just met is a sex shop. So I played coy and flirted with him. After a bit of this I decided I needed to ride my toy. He asked if I would like to go on a date sometime. I stood there, over my dildo, for a long time, shocked. Perhaps too long, he replied with, -If not, that's cool babydoll.-

-Yes. But only as Ashley.- I replied quickly.

-Im totally down for that babydoll, Ashley is all I want.-

My heart sang! My cock jumped and I felt this euphoric feeling I had never experienced at this level.

-Night baby girl, I'll text you tomorrow.-

First day in college and I had a date as Ashley, with a man! I was so excited! The excitement quickly turned into a strong sexual urge!

I kneeled down until I felt the tip touch my hole. I teased myself a bit, building anticipation and desire! My cock was rock hard and dripping profusely! I ran my finger along the bottom of my shaft, coating it in my juices. I sucked my finger as I forced the dildo into me! It hurt a little but I was enjoying the pain!

I sat there for a minute, slowly working it deeper into me, looking for my prostate. I leaned back and placed my hands on the floor. I worked that dildo until I felt strong jolts of pleasure. There it is! I took a deep breath and rocked my hips up and down in short, quick motions! My cock flopped around, spewing precum all over me! My body coarsed with pleasure, my legs were wobbling badly. I kept this up, this world crumbling experience, going for thirty minutes before I had to stop. I was glistening in the light, sweat rolling off of my hairless, lingerie clad body. I finally lowered myself all the way to the bulge at the bottom of the dildo. My legs outstretched and arms meekly laying at my sides, I gasped for air! My mind couldn't handle the pleasure, my body wanted more!

Laying on the floor, I rocked my hips again. Grinding the dildo deeper into me! I ran my hands along my body, feeling it's warmth and smoothness. I started pinching my nipples and biting my lip. My mind raced back to Erin. I imagined him taking me. Making me feel like a woman, his strong hands grasping my feminine hips and pulling me into him! His big lucious lips teasing my nipples!

My body tensed and began shaking! My cock jumped and twitched on my abdomen! My mind became hazy and my eyesight was awash with colors! I felt the pressure building up as I quickened my pace! Only an inch at a time but my hips bucked up and down, rubbing my prostate with this monster! I looked down to look at my body as my cock erupted! Shooting thick ropes of cum all over me. Some on my face, my legs and chest, she finally settled down onto my stomach and pulsed more white fluid into my belly button and on my abs! I continued to work the dildo, feeling the surge of pleasure overload my senses!

I lifted my hips nearly to the tip and slammed back down! The full length sent more pleasure! My moans were getting louder and feminine, my heart was racing, body shaking, my legs growing weaker and weaker! I wanted more, needed more! My cock was throbbing and bouncing on my waist, I started to rub the base, circling my fingers round and round. I had to keep going! Moans of pure Bliss filled my dorm! I began to scream, "Fuck me!!"

Thoroughly exhausted, I laid on the floor with my new obsession buried inside of me! The lingerie I wore was soaked with my lovely juices! My body was still convulsing from the pleasure I just experienced. It took me awhile to catch my breath and regain the strength to hoist myself off the toy I impaled myself on. As I lifted up, shivers ran up my spine and I felt the head leave my gaping hole. I shook once more and my body collapsed to the ground beside it, jolts of ecstasy pulsing through my body. I looked between my legs to see her there, rock hard, dripping again. I took as much cum as I could gather from my stomach and licked it off of my fingers. The taste triggered my impulses. I was going to do this again. I hope my roommate never showed up.