The Sissy Next Door: The Beginning

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Status: Finished  |  Genre: Transgender and Crossdresser  |  House: Abandoned

I find out my neighbor is into cross dressing and just have to have some fun with him.

It was Monday morning but I had the week off so when the alarm went off I quickly shut it off and laid in bed for a little bit. The smell of coffee brewing downstairs finally drew me out of my bed. I took a shower and wandered back to my room naked to find clothes to wear. I settled on a t-shirt and shorts and bare foot went downstairs to get my morning coffee.

I decided I was going to watch the sunrise and headed for the front porch. I had bought this place six months ago and it was just now beginning to feel like home. I had meet most of my neighbors by now and found them to be nice people, the only exceptions were the couple that lived right next door, Chris and Erica.

Chris was not bad but his wife had made a few comments that lead me to believe she was extremely homophobic. Looking at their driveway I saw Erica’s car was gone but she was usually gone before me. Chris would normally be leaving shortly, but he rarely spoke to me.

After watching the sun come up I noticed Chris had not left, but did not thinking anything of it as I headed back inside. I had turned the spare bedroom upstairs into my home office and that was where I headed. I was hoping to get some writing done on my time off. It had been a few months since I had released anything new and my fans were clamoring for a new story.

I pulled the curtains and opened the window. The view was not that great, Chris and Erica’s back bedroom but I wanted the fresh morning air. So with a cool breeze coming in the window I sat down to begin writing.

I happen to glance up just in time to see Chris come into the room across the way. He was naked and his long dark auburn hair was still wet. I could not help but admire his lean body.

I was going to close the curtains when he pulled a box from under the bed and removed a pair of black panties. Now I have many fetishes but voyeurism is not one of them but this intrigued me so I sat back and watched. It was when he slipped the panties on pulling them up his long smooth legs that I turned my webcam towards the window and began to record. I would never out anybody but I thought I could use the video later to help with one of my erotic stories.

He put on a bra next and the way it fit him I knew it was padded. He sat on the bed to put on a pair of sheer black stockings. I was getting excited watching him as I imagined all the things I would love to do to him.

He got a black dress from the wardrobe in the room and put it on. It was short and tight in all the right places. He checked himself in the full length mirror on the back of the door before sitting down to do his hair and makeup.

I continue to watch Chris as he transformed himself from an average looking guy into a beautiful woman. I could not help but touch myself as I fantasize about dominating him. I was engrossed in my daydream and nearly missed him leaving the room.

I sat there trying to decide what to do. Anyone that has read my erotica knows I like to take charge, going after those I was attracted to aggressively. The problem was not him being married, I have had more married lovers then single ones. The fact that he was my neighbor was the problem, when the relationship ended I do not know how it would work with him living right next door.

I finally decided I was going for it mostly because I was turned on but also because I did not like his wife. Once I decided to do it I hurried to my bedroom and throw some toys into a bag. I thought about changing into something sexy but settled on a pair of slippers.

I went out my backdoor and quickly made my way to Chris and Erica’s backdoor. The curtains on the door were thin enough I could see Chris in the kitchen through them. I knocked and Chris looked at the backdoor before freezing.

“Chris it is Anna from next door.”

He ducked down slightly trying to hide.

“Chris I can see you. Open the door now.”

He hurried over and open the door. “I can explain.”

I reached out and ran my finger tips along his smooth cheek. “You really are beautiful like this.”

He blushed and looked away, but I grabbed his chin and made him look at me as I leaned in and kissed him on the mouth.

“Anna I’m married.”

I laughed, “But Erica doesn’t have a clue about this little fetish of yours, does she?”

“You can’t tell her.”

“Maybe you should let me in before somebody sees us standing here especially with the way you are dressed.”

He took a couple of steps back and I came in kicking the door shut behind me. I dropped the bag and took a step closer to him and he scooted backwards until he bumped into the counter behind him. I quickly moved in and grabbed the counter on either side of him trapping him.

“I bet you are disappointed it was me who caught you and not some big musclar man that would bend you over and fuck you hard making you his bitch.”

He blushed and looked away even as he mumbled, “No. I’m not gay.”

“It isn’t gay since you are clearly a sissy.”

“No I’m not.”

I laughed. “Look at yourself, you are dressed like a woman. The only thing you are missing is the heels.”

“Erica’s shoes are too small.” He looked like he was about to burst into tears.

I reached up and caressed his cheek. “It is ok cutie, we will buy you some and keep them over my house.”

He tried to look away as his cheeks became even redder, but I did not let him turn away. I kissed him again and he responded by parting his lips slightly so I pushed my tongue into his mouth as I reached down and rubbed the front of his dress. He was clearly turned on by my attention or maybe it was the way I was taking charge of the situation.

I broke off the kiss but continue to rub his through the dress and panties. “Do you want me to leave or do you want me to take you upstairs and fuck you?”

He hesitated for the briefest of moments. “Stay.”

“Ok, but I want our first time to be special. Are you willing to do something for me, something very naughty?”

He nodded as he moaned.

“Go upstairs and find the lingerie your wife wore on your wedding night and put it on. I’ll be up in just few minutes cutie and then we will make love.”

“If Erica finds out she will kill me.”

I laugh. “She won’t ever know, she probably hasn’t even looked at that stuff since she packed it away with her wedding dress.”

I could see it in his eyes, his lust and desire as he nodded. “I’ll do it, but promise you will never tell her.”

“I promise cutie.” I kissed him again before stepping back.

He hurried from the kitchen with a quick glance back at me from the doorway. I spent a few minutes looking around until I found a bottle of wine and two glasses. I stuck the bottle in my bag with the toys and carrying it and the glasses I headed upstairs.

“Are you ready cutie,” I called when I reached the top the stairs.

“Almost,” he called back from the spare bedroom.

“Stay there I’ll be in as soon as I freshen up,” I told him as I stepped into the bathroom.

I quickly undressed and pulled out the strap-on from the bag of toys. I put it on adjusting the straps before stuffing my clothes into the bag. I looked at myself in the mirror and stroke the nine inch dildo. He was in fro a big surprise, but I was pretty sure he would enjoy it.

Stepping into the room I saw him laying on the bed on his right side propping his head up with his hand. His cock was hard and sticking a little out of the top of the white lace panties he was wearing, a bead of pre-cum glistening at the tip. He looked shocked as he saw the big dildo.

“What is that?”

“My cock cutie. I’m going to use it to make you my sissy.”

“I don’t know, I’ve never done that before and it looks really big.”

I laughed as I sat down the bag and moved over to the bed. I remembered at that point I had not shut off the webcam and it was recording everything. I reached down and stroked the dildo slowly watching his eyes follow my hand moving along the length of it.

“It will be ok cutie, you aren’t the first virgin I have broken in. I have lube and will go easy if you are a good little sissy.”

He swallowed and nodded not looking up at my face.

“Now I need you on your knees like a good sissy, right here in front of me.”

He slid off the bed and knelt quickly in front of me his eyes never leaving the big rubber cock.

“Maybe I will find you a real one to suck later, but for now I want you to suck my cock cutie, get it nice and wet.”

When he did not move I thought he was going to refuse. I could force him, but I wanted him to do it willingly. I was about to threaten to leave when he finally leaned forward and licked the tip. He opened his mouth and slowly let the tip slip inside. He finally looked up at me as he slowly let his mouth slid down the shaft of the dildo. Less then half of it was in his mouth when he gagged and began to slid off of it, but I moved quickly to grab his hair and hold his head in place. He had taken the first step, now I would make him go further.

I pushed the dildo further into his mouth causing him to choke and gag. I thrust my hips fucking his mouth at a slow steady pace, giving him time to recover before I pushed it back in. He knelt there tears filling his eyes at first but soon he reached out and began to caress my legs, his hands slowly moving up towards my ass. He grabbed my ass and pulled me into his mouth further as he gagged more. I let him gag and choke himself with the dildo for a few more seconds then stepped back.

“Good sissy, but now I have something else for you.”

He looked up at me panting and nodded.

I smiled as I turned around and stuck my ass out. “Eat my ass.”

I thought he would need some encouragement, maybe even a threat to get him to lick my ass, but he quickly leaned forward and started kissing my ass cheeks. He grabbed my ass cheeks and spread them as he kissed my hole and poked it with his tongue. I gasped as he forced his tongue into me and swirled it around. I was amazed at how good he was at this and had to wonder where he had learned to do this so well.

I was getting weak in the knees when I finally stepped away from him. He tried to move, to keep eating my ass when I turned around. I grabbed the base of the dildo and smacked him across the face with it. He looked up, his makeup was a mess and his chin was covered with spit.

“On the bed, it is time to make you into a girl.”

“Yes Ma’am,” he said as he got on the bed laying on his back with his legs in the air.

I smiled and got the lube from the bag. I squeeze some on the dildo and slowly stroked it as I joined him on the bed. “On your stomach ass in the air, like the little slut you really are.”

I continue to stroke the strap-on with one hand as he rolled over. “Spread your ass cheeks like a good little slut.”

He again obeyed without hesitation or speaking sliding his panties aside as he did as I commanded, allowing me to push a finger into his ass. He gasped as I got it in to the second knuckle. I moved it around a little feeling how tight he was. Even with the lube this was going to hurt, but he would have no choice but to let me finish once I got the head in.

“Beg me to make you a slut, sissy.”

“Please Ma’am fuck me, make me your sissy slut,” his voice high and almost girly sounding as I slowly fingered his ass.

I held the strap-on at the base and rubbed it up and down his crack a few times before putting the tip against his hole. He moaned as I teased him, but as soon as the head was against his hole he tried to pull away. Slapping his back with my free hand I pushed forward forcing the tip into him.

He cried out in pain, “Stop, it hurts.”

I ignored his pleas as I grab his hips and pull him back onto the dildo. He resists at first but as more of it slides into him he begins to relax. Soon he is moving his own hips to match my thrusting. That is when I notice him touching himself through his lacy panties. I spanked his right ass cheek hard.

“No touching sissy. You haven’t earned that privilege yet.”

He stopped with a soft whimper. “Yes Ma’am.”

As I continue to thrust into him the base of the strap-on rubbed my pussy making me wet. Between the stimulation of the dildo and the excitement of breaking in a new sissy I was soon on the edge. I could not help but think about having a hard thick cock in me as I fucked my newest sissy hard making him gasp.

I finally pulled out of him and collapsed beside him, pulling his mouth to mine by his hair I kissed him hard. “There is wine in the bag pour us some sissy.”

He moved to obey quickly as I laid back relaxing. There was a puddle of his cum on the sheets from where he had cum from the dildo pressing against his prostrate. He poured the wine and handed me a glass before he joined me. He snuggled against me sipping his wine as he laid in the pool of his own juices. I ran my finger through his long dark auburn hair and smiled. I glanced at the clock on the nightstand and saw it was only a little after ten.

“After we are done with this glass of wine we will go shopping, you should have your own clothes and not borrow your wife’s.”

“I’ve never bought women’s clothes before.”

I laughed, “Don’t worry I’ll help you pick out things that will make you look very sexy and you can try everything on before we buy it.”


“I’m taking my sissy shopping which means you will dress as a girl.”

This was the first of many moments where I found out how far he was willing to go. If he refused then it was over and I would leave with a fond memory and a nice video maybe. If he agreed then he would move one step closer to becoming a complete sissy. His semi-erect penis twitched in his lacy panties as he laid there and I knew he was considering it.

“I have to be home before Erica.”

I turned and kissed him. “Don’t worry sissy, I will make sure you are.”


Submitted: September 19, 2021

© Copyright 2023 Gypsy Rose. All rights reserved.

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Add Your Comments:



Girl power in action here.
He was a lamb to the slaughter haha!!!
Plenty of "she said,he said" made it sexy.

Mon, September 20th, 2021 2:30am


thank you for reading, commenting, and bugging me to reply.

Sat, October 2nd, 2021 9:01am

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