My Neighbor Jim Ch. 02

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Part 2 of my sissification and feminization.
2.7k words
4.53
15.2k
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Part 2 of the 3 part series

Updated 06/11/2023
Created 09/17/2022
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I was excited to see what Jess was going to do for my makeover. She took me to the bathroom and passed me a tube of hair removing cream. "Here, rub this all over your arms and chest, I'll work on your legs. We need to first clean off all body hair." I was surprised at how easily the hairs came off. Once we were finished I was almost completely stripped of body hair. "Perfect" she said, rubbing her hands over my now silky smooth body. "We also need to shave your balls," she said, picking up my razor. She applied a little foam all around my cock, then carefully shaved my pubic area and balls, until I was baby smooth.

Then Jess turned on the shower, which I was glad to see was not broken. She climbed in and pulled me in behind her. She took a handful of her feminine musk shower gel and rubbed it all over our bodies, including massaging my cock and balls and her pussy. We were smelling like flowers when we got out.

After drying me and herself, Jess sat me on a stool saying, "Let's do some makeup." First she applied a tan foundation. Then she plucked my eyebrows, and used an eyebrow pencil to accentuate the curvy shape. She applied a dark eyeliner and eye shadow to my eyelids and mascara to my lashes, blush to my cheekbones and lightly patted powder all over my face. Then she carefully outlined my lips using a red lip pencil, then filled it with rich crimson red lipstick and applied gloss over it. I had the biggest, reddest, shiniest lips I had ever seen. She stood back and looked extremely pleased with her efforts. "Wow" she remarked, "you are starting to look truly beautiful, we just need to get you some jewellery, then sort out your hair."

She made me wear a wide black choker with a gold loop in the front around my neck, and a pair of large clip-on gold hoop earrings. She selected two rings and put one on each hand and attached false nails on each finger. With the rings and long red nails my hands now looked really feminine. She got a 12" long blonde wig and stretched it over my head, being careful not to mess my makeup. I could feel the hair brushing gently against my shoulders and back as I moved my head. The sensation was pure electrifying.

"Let's get you some fuck-me heels," Jess said and brought a pair of sandals with six-inch heels. "Give these a try," she said. The shoes fit fine but certainly did arch my feet a lot. I stood up slowly trying to keep my balance. "Try walking," she said. I walked across the room with one foot directly in front of the other, just like models do. "You were born for them," Jess gushed. The makeup, the jewelry, the hair and shoes were all was so erotic and I started to feel really sexy and very feminine. I couldn't wait to see myself and slowly walked to the full-length mirror.

When I got to the mirror I was absolutely shocked as I saw myself as a stunning sexy blonde! Looking back at me was a beautiful, flat chested girl with a cock. The sexy image of me caused me to become really aroused. My cock got harder as I gazed at my reflection. Jess saw my erection and called me back to her. I walked back with a little butt wiggle and sway of the hips like a woman. She said admiringly, "This is the hardest I have ever seen your cock. Where was this all these years. Give me that."

She took my little penis in her mouth and started to give me a slow blowjob. I could see how fucking expert she had become in cocksucking in just last month. She was bobbing her head slowly back and forth taking the entire 4 inches completely in her mouth. She sucked real hard and I could hear her slurping. She must have started to taste my pre-cum because she suddenly stopped. Releasing my cock from her mouth, she looked up giving me a sexy wink. "We can't have you cuming sweetie. At least not yet. Wait for tonight."

Jess got dressed herself. She did her own makeup as carefully as she had done mine. She wore a short white dress that barely covered her breasts and ass. She had a beautiful matching white lace choker tightly sitting in the middle of her long neck. She wore four inch heels and did not wear any panties. Instead she wore a gold body chain around her hips, with a small triangular pendent in the front barely covering her pussy slit, enhancing it's beauty immensely.

Finally Jess got some of her perfume and sprayed it on my chest and neck and on herself. "We look like a couple of young street whores hired for a night of debauchery," she laughed jiggling her boobs. "Daddy is going to love us."

#

When the door knocked, I ran to the door almost tripping in my high heels, my cock bobbing up and down with the excitement of presenting myself to Jim. I was completely naked and Jess had attached a puppy chain to my choker.

As I opened the door, Jess came behind me, wrapping her arms around my stomach, resting her head over my right shoulder, and rubbing her hands all over me, as if to show me off to Jim. Jim's mouth dropped open when he saw me. "Is that Ashley! Wow you look so fucking gorgeous. Just like a princess." He felt me all over my smooth naked body with his strong hands, as if I was a new toy. "Jess baby, you are a miracle worker. What an amazing transformation."

"Thank you daddy!" Jess beamed with pride. "I did what you asked me to. She is all yours," she said wagging my cock obscenely, "ready in every way."

Jim led me like a puppy by the chain, through the bedroom door, over to a chair next to the bed. He kissed me gently and instructed, "Sit down and watch. No touching yourself, no playing with that little girl pee-pee. Watch and learn how a slut should fuck grown men."

Jim walked to Jess and with one hand held the front of her neck and with the other hand grabbed a handful of her hair. He brought his beard covered lips over her soft red lips and kissed her hard, making it very clear how badly he wanted her. They kissed like lovers. Just watching them I almost came. Jess was gasping for air when they finally separated.

Jim slid the thin straps of Jess's dress from her shoulders revealing her heaving boobs. He slowly let the loose dress fall to the floor and stepped back. Jess stood naked in her high heels, her hands behind her back, proudly jetting out her tits for Jim. Her nipples were engorged with blood, standing up pertly, and begging for attention.

"Baby you have such an exquisite body," Jim said taking her aroused nipples between his fingers and pulling on them cruelly. "I have a hard-on just looking at you. Tonight I am going to ravish your body like a whore at a gang bang."

Jess reached out and grabbed hold of Jim's crotch and felt his hardness. She unzipped his pants and pulled out his cock and started jerking it. Then slowly dropping to her knees, she pulled his pants all the way down to the floor so he could get out of them. Jim took off his t-shirt revealing his strong muscles. Now they were both naked and their electrified bodies two feet in front of me.

Jim sported a giant nine inch penis with massive scrotum, which looked like it was filled with gallons of baby making juice that Jess told me about. What shocked me the most was that it was enhanced by a thick silver metal cock ring that made the whole package so powerfully masculine. Seeing his beautiful cock just an arm reach away made me want to touch it and just put it in my mouth. So many thoughts went through my mind about all the dirty things I would do with that thick cock just on my own.

Jim saw me staring at his penis in awe and said, "You see this cock. That's what a real man's cock looks like. That's what your wife needs."

Jess took his cock in her hands stroking it while moving her tongue up and down the majestic shaft. She licked all around the tip and worked her way down to his cum filled balls. She took a mouthful of balls while continuing to stroke the hard penis. I had a close-up view as Jess moaned with every suck. She finally let out one big suck and pulled back and the balls popped out of her mouth. She looked up at Jim and said, "I'm am going to take your cock in my mouth, daddy. Gag me like a whore."

Jess wrapped her sexy lips around Jim's penis and slowly worked her way down until it couldn't go any further. She started to suck and gag on it. Jim grabbed the back of her head and shoved the last few inches down her throat. Jess's body started to jerk due to the gagging. He slid in and out deep in her mouth and down her throat. Slobber ran out with every thrust, down her chin onto her breasts. Jim had his hands tangled in her hair pinning her down so she couldn't move. She had to take everything he gave her.

Concern and excitement went through my body as Jess started to push Jim back slapping on his thighs. But he didn't let go and held her down on his cock. At the end moment, before she was about to throw up, he slid his cock out of her mouth. Jess gasped frantically for air. Jim then rubbed his gloopy cock on her face, smearing his pre-cum and her spit all round her pink lips.

"Good job, baby. See how far you have come along with my training in sucking a man's cock. Tonight you have graduated and I am happy to say you have become my favorite slut," Jim said approving of her blowjob. He pulled her up by her hair off her knees onto her feet and said, "Look at that filthy mouth."

"Let me get it cleaned for you daddy," said Jess. She walked over to me with a big smile. "This is a gift for you," she said and bent down and kissed me. I was thrilled that she was kissing me at that moment. I could taste Jim's cum on her lips and I kissed her back like mad.

"Now watch daddy fuck me the way you only wish you could." Turning her back to me she walked over to the bed to Jim. "Do what you want and take no mercy on me," she said putting her arms around him and placing her lips on his.

I saw Jim's big hands rub all up and down her body grabbing her juicy ass and then pushing her down onto the bed. He spread those sexy legs revealing that slutty pussy of hers. He got on his knees and put his head between her legs and started kissing and licking her cunt. She let out big moans as he licked her clit faster and harder.

She moaned as I had never heard before so I knew how much she was enjoying her pussy eaten. Moaning louder and louder I could tell she was about to cum with Jim's tongue deep inside her pussy. He worked her pussy hard with his mouth and she started to shake. "I'AM CUMIIIIIIING!" she screamed.

"OH MY GOD DON'T STOP. THAT FEELS INCREDIBLE." Her pussy unleashed her sweet juices all over Jim's tongue and beard. She was at the point of almost squirting because she had so much inside her that needed to come out.

"FUCK ME WITH THAT COCK DADDY. I can't stand it any longer. I want you to fuck me and show me how a real man fucks. Prove to my Ashley that I need this. Show her how I should be satisfied."

Jim climbed on top of Jess bringing his cock just at the slit of her opening. Jess started to beg, "Slide it inside me daddy. Please don't tease me anymore. I want to feel your cock inside my pussy. FUCKING FUCK ME ALREADY." She had her hands wrapped around Jim's ass and with one deep thrust of his hips he was deep inside her. She let out a loud cry of satisfaction.

All I could do was sit there and watch Jim destroy my wife. She was letting out loud moans while telling him to do things I have never heard her say. "FUCK ME HARDER! Go as deep as possible and hurt me." With every slap of his body against her she let out a louder moan each time. Finally, not being able to take any more, she wrapped her legs around his body so he couldn't pound anymore. She froze till the tremors of her orgasms passed.

"I want to be on top now," Jess declared and climbed onto Jim's stomach. She scooted back sliding her pussy down onto his cock. She started grinding back-and-forth as they intertwined their hands together so she could get more leverage. I had never seen my wife have so much raw passion during sex before. She looked at me with a smile showing me how much she was enjoying herself. At that moment I truly realized how much of a disappointment I was to her when it came to having sex.

Jess let out another moan as she came once again on Jim's cock. She had never cum that much before. I noticed her cream running out of her onto Jim's cock making me want to lick his cock even more.

"Get on all fours facing your husband," Jim ordered. "I am going to fuck you like a bitch in front of him." Obeying every word he said Jess faced me on all fours looking me straight in the eyes. Working his way behind her, Jim grabbed her hips and slowly started sliding his cock deep inside her. I saw the expression of greed, satisfaction, and lust all in her bambi blue eyes as she felt his cock penetrate her.

"Are you are enjoying the view of daddy using mommy, sweetie?" Jess asked me as Jim slammed his cock in her pussy. "I told you how beautiful it will be. Just sit there with that cute little penis and watch daddy wreck my pussy."

Then turning her head back, Jess looked at Jim and screamed out, "FUCK ME HARDER DADDY. Use me like your little slut and show my sweet Ashley how you have been fucking me since the day we met."

Hearing her say those words I felt my cock squeeze as it tried to grow past the point of no return. It started to hurt but I couldn't dare touch it. All I could do was watch with no release for my cock.

Jim was pulling back on Jess's hair and slapping her ass until it was blood red. She kept telling him not to stop and to fuck her hard. I was surprised to hear the filth that was coming out of her mouth. Looking straight at me with a smile on her face she said, "I want you to come inside me daddy. I want you to fill up my pussy so I can stand over my husband and have him eat me clean."

The sound of that drove me nuts. The more Jim pounded her the more I saw the pleasure on her face. I just wished I had the power to ease the pain my cock was in.

Jim also looked at me. "I am about to unload inside your wife so it won't be much longer before you can clean her," Jim warned me. Letting out a loud groan, Jim clutched Jess's hips tightly and thrust one last time dumping every bit of his hot creamy load inside my adoring wife's pussy.

Jess collapsed onto the bed exhausted.

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5 Comments
AnonymousAnonymousover 1 year ago

Jess needs a baby bump from Jim!

AnonymousAnonymousover 1 year ago

Feeding time next!

Great story.

AnonymousAnonymousover 1 year ago

Very much not to my tastes so I did not rate you as my bias would have forced me to give you one star.

Firsttimeforevery1Firsttimeforevery1over 1 year ago

I enjoyed both of these stories A LOT.

Please ignore the negative comments and continue

AnonymousAnonymousover 1 year ago

That is so sexy I love it I can't wait for the next chapter x sissy Lucy

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