My Path to Feminization...Ch. 02

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An effeminate male's transition to a submissive sissy slut!
1.4k words
4.45
25.7k
14

Part 2 of the 2 part series

Updated 06/10/2023
Created 03/29/2021
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Within a couple of weeks I came home from work one day to find my young wife Sondra waiting at the door. She was wearing a silky running outfit consisting of a loose fitting tank top, and very short shorts. When she moved, her breasts were clearly visible from the side and her nipple rings shown through the sheer, silky fabric from the front.

She instructed me to remove my clothes and go to the bathroom window and wait there, which I promptly did. This side of our house faced our neighbors Dave and Laurie. We had socialized with them on several occasions, and Sondra thought Dave was hot. I saw Dave working on a retaining wall in his backyard behind his house. He had his back toward me and his shirt off digging furiously.

As expected my wife came strolling around the side of his house. She looked over and gave me a little wink as she headed to where he was working. She sat down on the top of a picnic table directly in front of him, facing me. She leaned back on her hands and crossed her legs.

He kept on working but would stop and look up when my wife said something to him. Although I could see them clearly I could not really hear what they were saying. Each time she spoke she uncrossed her legs and sat with her knees far apart. From my vantage point I could clearly see that her shaven pussy was on full display, glistening in the warm afternoon sun.

My little dick was getting hard and oozing pre-cum. Dave had ceased his digging now and was giving her his complete attention. Sondra's sheer tank top did nothing to hide her obviously erect nipples, not to mention those oversize nipple rings. My wife, while continuing to speak, brazenly ran her finger from her knee to her exposed pussy and inserted a finger deep inside. She withdrew the finger and seductively put it in her mouth closing her lips around it, then stood up and said something to him to which he immediately responded. Briefly glancing up at me peering out the window, she spun around and headed back toward our house.

Upon her return she headed straight for the bedroom, and called to me;

"Get in here and lick my pussy."

As soon as she slipped out of her shorts I began to lick her already sopping wet pussy. She told me how Dave's dick had swelled in his jeans while staring at her exposed pussy. Sondra told me their verbal exchange was short and to the point;

"I want to fuck you."

"Laurie will be away overnight on Saturday."

"I'll be over at eight."

It was obvious to me she was very excited, trembling actually. This would be the first real mans cock she was going to enjoy in many months. I have to say that I was extremely excited also, it turned me on to know in four days my wife would be fucking someone else, someone I know, someone that knows me!

This was going to be something new for us, I was not going to be present to watch. In the past we had some same room sex with our friends, Steve and Dianne. We had even swapped with them, which my wife enjoyed tremendously. Dianne really enjoyed my oral skills and I did attempt to fuck her but she was disinterested at best. My tiny thing did not please her. The turn on for me was all about watching my wife with another man. Seeing how much she enjoyed being fucked hard by a cock that could make her orgasm prompted me to cum embarrassingly on Dianne's leg.

Unfortunately our escapades with them ended when I acted on my long time bisexual urges and attempted to give Steve head. In retrospect, we probably should have discussed boundaries first. He was so offended that they left immediately. My wife was pissed off and didn't speak to me for weeks despite my apologies.

By early Saturday evening Sondra was primping and fussing already. The anticipation of getting the cock she craved was making her noticeably nervous. Heavy makeup, bright red nails and lips. Hoop earrings to match her nipple rings, an ankle bracelet, and several toe rings. This girl could dress like a slut, but she had outdone herself this time. A loose fitting crop top barely long enough to cover her tits, a hip hugging denim skirt that exposed a glimpse of ass cheeks when she walked, and a pair of five inch platform mules that matched her lips and toes.

My little dick was straining in the clear chastity device she had put me in four days earlier. She glanced at my purple genitals momentarily and then ordered me to lick up the juices already flowing from her exposed pussy.

"Clean me up, I want to be ready to fuck as soon as I get there" she said.

I did as I was told until she pushed me away, gave me a kiss, and sauntered out the door.

It was only an hour or so later when I saw her coming up the drive, heels in hand, looking a bit disheveled.

"Come" she demanded.

I followed her to the bedroom where she promptly flopped on the bed, hiked up her skirt, and spread her legs.

"I want you to clean up a real mans cum from my pussy."

I proceeded to position myself between her legs, and began to do as I was instructed. There was cum glistening on her inner thighs where it had leaked out of her during the short walk home. I had seen her freshly fucked pussy before but never immediately after she fucked someone when I was not present. It was flushed, quite swollen, and was gaping open. As my tongue and lips touched it she gasped, and Dave's cum appeared in the opening. I eagerly began to lick her pussy and as his cum flowed into my mouth I swallowed every drop I could.

She began telling me the details of their encounter;

"As soon as I got there he began kissing me, he forced me against the wall and massaged my tits with his rough hands, tugging on my nipple rings."

"He said he watches me sometimes, and loves how I always dress like such a slut."

"He has even stroked his cock while watching me in our backyard."

"Looking me up and down he told me how much my pierced nipples and bald pussy turned him on."

"He pulled me close and kissed me deeply while slipping a rough finger into me."

"I got so hot from his touch, I dropped to my knees and unzipped his jeans, slowly pulling his briefs down allowing his cock to flop out in front of my face."

She told me how huge it was, thick and uncut, and how she rolled back his foreskin and wrapped her lips around it. I was extremely turned on by this as she had not sucked me in so very long. My little dick was rock hard and straining in my chastity device. She continued to describe how she enjoyed his huge cock;

"He grabbed me by the hair and began fucking my mouth, I gagged several times, but I loved it and wanted it in me."

"Pulling his rock hard cock out of my mouth, he forced me down on my hands and knees. When he saw my tramp stamp, started to call me a tramp, slut, and whore."

"He entered my pussy in one swift motion, his cock was so thick and long it stretched out my hole like never before, not like your little pin dick."

I was licking her and savoring every drop of his cum getting more and more turned on with every word.

"I could feel his balls slapping my clit as he fucked me and I started to cum. I came so hard, maybe three times I can't remember. When he finally started to cum I could feel his cock swell, and his cum exploding deep in me."

I could hold back no longer and started to cum myself, even in chastity my tiny dick was cumming! She noticed this and berated me for it;

"You pathetic little cum-eater, I was even thinking about letting you fuck me but I guess you have become too much of a sissy for that anymore."

"There are going to be more changes around here" she continued;

"If big cocks and eating cum are what turns you on, then I am going to make sure you look like what you are, a fem boy cock slut!"

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TFSallyAnneTFSallyAnneover 1 year agoAuthor

So very much more to come Subbytubby, please be patient...

subbytubbysubbytubbyover 1 year ago

I gave it a dislike. It was hard for me to rate it this, but the category and title was "feminization" leading me down a wrong path. What I mistakenly thought was going to happen was her feminization of him into a cuck then a participating cuck. Into her panties and makeup then after body hair removal into slutty clothing. Ultimately even using him as part of her strategy with him caged up and his "pussy" becoming part of the sexual escapades. Licking the cream was but a part of it. Bringing in a team of men, a literal softball team of men that her neighbor played with as amateurs, a college baseball team, and a group of baseball players from the bar on different nights, the local university frat teams, and the like. All making use of his, now her pussy, their pussy's and mouth's. The parties lasting sometimes Friday 8:00 PM until Sunday morning, 3:00 to 4:00 AM. That is where the story took my mind. This was feminization to me. This story was more of a loss of interest cuckhold story. It had good plot, and it had good flow. Other good factors were that it made me desire more which could complete those gaps, either this way or with divorce and him doing something about the problem of submission himself. Good job in those aspects.

lostopportunitylostopportunityover 1 year ago

the third installment came out today sweetie enjoy our story XOXO

lostopportunitylostopportunityover 1 year ago

I finished your story "Sally Anne" comes out tomorrow enjoy inspired by your picture wink

goodsonformomgoodsonformomabout 2 years ago

Awesome story. Chapter 3?

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