The Sissy of Hawthorne Ch. 01

I pulled on the plug. The pain was intense as the bulb started to come out. It came out with a plop and I pushed it back in. Back and forth I worked that little plug into my ass until it didn't hurt anymore. I was so caught up with the motions of the stretching that I actually wasn't aroused. My little cock was flaccid as I worked my hole open. I learned to push a little to help relax on entry.

I then grabbed the bigger plug. It was as thick as a nice sized cock. I lubed it and pushed it in me. I felt really tight as first, even when I pushed on my backdoor, but I was able to work it in. It took some time to adjust to it. It was more uncomfortable inside me fully inserted than the small plug. I stood up and did squats and stretches with it inside me. That helped with the discomfort.

I did errands around the house. I washed and folded the laundry. I was happy that all of the cum stains washed out of my uniform and slutty clothes. I cleaned the kitchen. I vacuumed the apartment, and put all the toys and DVDs into my hiding spot. All the toys except for the large plug, which was still inside me. I put on a thong, that's all I wear, and some jogging shorts. I left the apartment and went for a jog. The plug felt tight in me. I had to stop and do some squats every now and then to move things around a little. I saw my neighbor, Brad, out for a jog. He saw me and matched pace.

Brad and I jogged around the neighborhood. We passed Frank's house. He was outside in the front yard. His kids were loading their luggage into the house. Frank waved at me. I waved back. He grabbed his dick through his shorts and gave me a wink.

Brad and I made it to the Sunoco down the street where we usually stopped for water or Gatorade. We both grabbed a water. Brad was a few years older than me. He was five feet and eleven inches tall, athletic, and kind of had a Kennedy look to him. I thought he was pretty hot, he seemed to be pretty lucky with the ladies.

"Hey," Brad said, "want to run back on some trails I found that go behind Hawthorne? It will get us off the hot pavement."

"Sure!" I said. I was dying of both the heat and the buttplug stuck in my ass.

I followed Brad through the woods. It was a cleared trail, but still pretty rough. The uneven ground played hell on my ass. Brad was ahead on the trail and stopped.

"What's up?" I asked, secretly happy to have a break so I could do some stretches to shift things around.

"You remind me of this friend I had growing up," Brad said, "well, he was much bigger and looked nothing like you, but we would hang out all the time. We had a spot behind our neighborhood in the woods. It's where we hung out. This place reminds me of it."

"That's cool." I said, still fidgeting with the pressure on my backside.

"The reason you remind me of him is he used to walk around with my cum glazed all over his face like you walked back to your apartment last night. Though, he never wore cutoffs, a crop top, or high heels." Brad said.

I was in shock. Brad was pretty much the only friend I had and he caught me dressed last night, like an idiot. I then thought to myself, though, "I thought he was straight."

"You keep doing squats and looking uncomfortable. You were carrying bags from that sleazy shop out of town. Are you trying out a new toy right now?" Brad asked.

I looked at Brad like a deer in headlights as he placed his hands on me, turned me around, and bent me over. He pulled down my shorts. Underneath was my thong and my buttplug, with the T Bar sticking out.

"You are a fucking slut, Jim!" Brad laughed as he spanked my ass a few times.

"You got a boyfriend, or is this ass up for grabs?" Brad asked.

"No boyfriend." I said.

"What about that older guy that you waved to back there. The one who eye fucked you and grabbed his dick as you passed by?" Brad asked.

"I gave him a blowjob yesterday." I said bent over, looking at the ground.

Brad tugged on the buttplug. He pulled it out too fast and it hurt a little, but the pain was only for a second.

"Fuck, Jim, you're a tight little slut. You only fuck pencil dicks?" Brad asked.

"I'm a virgin. I just started to stretch myself today." I answered.

Brad got behind me and stuck his tongue up my ass. It felt amazing. He licked all around the hole and then fucked the hole with his tongue. I moaned loudly as he rimmed me for what felt like an eternity.

"Let's go back and let you get cleaned up and dressed. See how sexy you can get. Then we will work on the stretches. You need to stretch that pussy out more before you can take some real dick." Brad said.

He put the plug back in me and pulled my shorts back up. We jogged back to the apartments. The trails led right there.

Brad and I walked to his apartment first. He grabbed some clothes and a few other things. Afterwards we went over to my apartment.

"We need to wash your sexy body off in the shower." Brad told me as he got undressed.

We went into the bathroom and he started the shower. We both got undressed and inside. Brad wasn't hard yet, but he was semi hard. What most guys would say is he had a little chubby. He was pretty big, even when not hard. His dick hung low enough to brush against my dick as he stood in front of me. He held me and kissed me as our bodies pressed together and our cocks rubbed together. Brad started to get hard. I reached down and grabbed his cock. I slowly jerked it as we made out in the shower. Brad washed me all over. He rimmed me again when he got to my ass. He removed the plug gently and licked my crack up and down before he darted the tongue up my hole.

Brad's long tongue was the most amazing feeling that I had ever felt in my life. I had no idea that my ass could feel this much sensation. My little cock stuck out, raging hard as the water rained over it. Brad grabbed it and stroked it. I could feel my orgasm build up, and it was a big one. I tensed and Brad stopped. He denied me my orgasm.

"Not yet baby, not yet." Brad said.

My little cock leaked from being edged. I grabbed the body wash and washed Brad all over. I got to his ass and he stopped me.

"That's just an exit, baby." He said.

I washed his crack and taint and worked myself over to his cock. I stuck my tongue out and licked him all over. His cock grew rapidly. I swirled my tongue all over his head. Brad was circumcised and was impressive. He wasn't as thick as Frank, but he was still thick and about seven or eight inches long. He had a slight banana bend up. I licked all over his cock head and took him inside my mouth.

Brad moaned as I worked his tool with my mouth. I was careful with my teeth and worked him to my throat easily. Brad looked down at me with lust. I grabbed his waist and pulled him towards my face. His cock pushed down my throat.

Brad stood still with his hand on my head. He moaned as I sucked and throated him. I slurped on his cock. His cock felt so good in my throat and tasted good as well. He moaned loudly as I worshipped his tool on my knees. I could feel him tense up. I knew it would be soon so I worked him just in my mouth. I didn't want to choke on cum again today. Brad grabbed my head and shot streams of cum that filled my mouth. I swallowed as fast as I could. I sucked on Brad's cock gently for a minute after he came. I didn't want to miss any of his cum. Brad looked at me, very pleased.

"You give one helluva blowjob, Jim." Brad said.

"Ashley," I said, "My name is Ashley."

"Fuck yeah, Ashley. You like that cock?" Brad asked.

"I love it." I said.

"I usually cum three times a day. Sometimes more. We can still have plenty of fun today." Brad said.

I smiled at Brad. The only friend I had in the area turned out to have a yummy cock. Brad let me flush myself out again. I then dried and ironed my hair. I put on foundation, concealer, eyeliner, and lipstick. Just liked I had secretly practiced for years. Brad wore a pair of pink shorts and a blue polo shirt. I put on a black thong with a garter and fishnet stockings. I then put on the shortest black skirt that I had with a matching crop top. The skirt was so short that my ass cheeks were exposed when I walked. I wasn't passable enough to interact with people in public. I could maybe get away with a quick walk to the car. The adult store was a place where a crossdresser wouldn't be a big deal, that's what gave me the courage to go there dressed last night. Anywhere else in public was risky.

Brad and I made out again. He put on a porn that he had brought over. Two guys and a girl had a picnic in a field. The guys started to make out as the girl started to suck their dicks. The girl had a strap on. The guys alternated between each other's ass and her pussy. She pegged them both.

Brad bent me over his lap and said, "I'm going to take your virginity today, but we have to get you ready first."

Brad had my toys that I bought last night. He took the small dildo and lubed it up. He pushed my thong out of the way and pressed it up against my hole.

"Just relax Ashley." Brad said softly.

Brad pushed it forward into me. It was tapered so the pressure increased as Brad pushed it in further. Brad pushed it all the way in and then pulled it out. He lined it back up and pushed it back in.

"I can't wait to feel your ass, Ashley." Brad said, and continued, "Your starting to loosen up, but I can tell your ass is going to grip a dick. A girl's pussy feels like a jar of mayonnaise after you plow it for awhile. A nice ass feels amazing compared to a pussy. I would fuck my girlfriend more than once a month if she let me fuck her ass. She is too uppity to take it in the ass. She won't even suck it. I was looking for a friend like I used to have. I had actually been hoping that it would be you, then I saw you last night. I knew then that it was on."

Brad stroked me with the toy now. I wiggled in his lap as he probed my ass as deep as the toy could go. If felt hard and sharp inside me. I wondered what a real dick would feel like. Would it be softer or harder? Would it feel better or worse?

"I think you need the bigger one." Brad said as he lubed up the bigger toy. He pulled out the smaller dildo and put in the larger one. It was about seven inches long, it started out about an inch in diameter and went up to a little bigger than Frank's dick.

I squirmed more as I adjusted to the size.

"Just relax Ashley, you're going to enjoy this, I promise you." Brad said.

I could feel Brad was aroused again. His cock twitched as he played with my backdoor. He worked it deeper each stroke. I felt like I had a log shoved up my ass when he got to part that was the size of Frank. "I don't know if I could ever take Frank's cock." I thought.

Brad reinserted the large plug back in me.

"I'm going to order some Chinese. I brought over a few DVDs I got from Netflix. Let's watch Little Miss Sunshine." Brad said.

I adjusted my clothes. Brad ordered some food and paid for it over the phone. We lounged around and watched TV. Brad would occasionally bend me over his knee so he could pull the plug out and push it back in. He would give me a few firm spankings each time and then rub my cheeks.

"How big is that dude in the neighborhood?" Brad asked.

"He is huge. His cock is a tree trunk." I told Brad.

Brad laughed and said, "We need to get ole' Tree Trunk over for a threesome."

Brad spanked me some more. I moaned.

"You like that, huh?" Brad said, "You are a freak, Ashley!"

Brad swat me again with his hand, this time much harder. And again. I kicked my legs a little, he adjusted me over one knee and held my legs down with his right leg. He started to spank me hard and quickly. He alternated cheeks on each swat. He also spanked me in the center. It started to hurt, but I felt him grow hard as he spanked me. My little cock started to grow hard too. He felt it on his knee.

"You fucking slut!" He said, "You really like this!"

"I've been so bad," I said, "I was on the clock when I sucked Frank's cock. I got paid just like a cheap whore."

"Really!" Brad said.

"I went to the Adult Store later that night and sucked three cocks in the theater and let other guys cum on me." I said between swats.

Brad spanked even harder and said loudly, "You have been a very bad girl!"

Brad spanked me harder and harder. I moaned and cried. There was a knock on the door. Brad stopped. He stood me up, walked me over to the end of the couch that faced the door, and bent me over the armrest. He flipped my skirt up. My bright red ass in a tiny black thong faced the door, just ten feet away. He went to the door and opened it. The delivery driver handed Brad the food.

"Holy shit, dawg. I thought I heard some crazy shit when I knocked on the door. Great job man, put that bitch in her place. She has to know who's in charge?" The delivery driver said. He high fived Brad and said, "Keep it up man and thanks for the tip."

Brad closed the door. He walked over to me and stood next to me. He placed the food down and took off his belt. It was a brown leather belt. He folded it in half and spanked me hard with it. The sound cracked through the room. Brad rubbed my cheek where it landed while I whimpered. Brad whipped me again with his belt. Harder than the last time. I cried and sobbed, by stayed still. Brad whipped my poor ass again. And quickly again. I cried uncontrollably but my little cock was rock hard.

"Last one, Ashley." Brad said before he whipped me on the ass as hard as he could. I covered my ass with my hands and cried.

"You learn your place yet?" Brad said with a laugh.

"No sir, I think I need another lesson." I said as I composed myself. It fucking hurt, but I was hot as hell.

"Let's eat," Brad laughed, "There is always tomorrow."

I stood up and Brad kissed me. He went to my bathroom and got some lotion to rub on my cheeks. The lotion felt cool on my burning cheeks. My little cock strained against my panties. "When is he gonna let a girl get her rocks off." I wondered.

We ate our food. Brad put on another movie. He toyed and played with me the entire time. I laid across his lap for most of the day. My cheeks were too sore to sit down normally.

"Get on your knees, Ashley." Brad instructed.

Brad took his hard cock out and started to slap my face with it. I opened my mouth and Brad aimed for my tonsils.

I sucked Brad's cock as if my life counted on it. Brad pulled out of my mouth and carried me to my bedroom and threw me on my bed on my tummy.

"You're going to get fucked now." Brad said as he crawled over my legs, "I don't wear condoms so I'm going to breed you."

He put some lube on him and added some lube to me. He lined up his cock at my pussy and pushed hard. His cock felt massive as he slid in. It felt like he ripped me in half as he pushed in.

"Fuck yeah, Ashley." Brad moaned, "You feel amazing."

Brad humped me in prone. He worked his big cock in deeper as he fucked me.

I moaned and gasped as he fucked me. His cock filled me completely. It felt so much better to have a real dick in me than a piece of hard rubber. Brad's dick felt amazing. It took awhile to adjust to him, but I didn't experience any pain after awhile. Brad buried himself inside me and laid on my back, he grabbed my face and turned it to the side so he could kiss me as he turned me out.

"Take that fucking dick, you video booth whore." Brad said as fucked me harder and harder.

Brad pulled out, grabbed my waist and picked me up so I got on my knees. He lined back up and pushed back into me, all the way. My cock was hard again and he reached around to grab it. He fucked me harder and harder. My little cock banged back and forth in his fist as he pumped my ass with his hard cock. I couldn't take anymore and came in his hand. He caught all of it and took his hand up to my mouth.

"Eat your cum." Brad said.

I licked all of my cum off his hand. Brad continued to fuck me. He started to tense up and fucked me in short pumps deep in my ass. I felt him explode and fill my bowels with his seed.

Brad pulled out of me and put the small plug back inside of me.

"Keep that in there tonight." Brad said.

Brad rubbed more lotion on my sore ass. His girlfriend would be back early tomorrow, so he went back to his apartment.