My Path to Feminization...Ch. 01

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An effeminate male's transition to a submissive sissy slut!
1.5k words
3.75
34k
32

Part 1 of the 2 part series

Updated 06/10/2023
Created 03/29/2021
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It all began innocently enough, we had both recently turned nineteen. I was a bit of a skirt chaser willing to fuck anything with open legs. She was a trim, small breasted nymph, proud of her young body and liked to show it off. A bit of a slut actually as I would come to learn later (most likely the reason she caught my eye in the first place). She was prone to wearing loose silky or gauzy tops, never a bra. Slinky dresses, extremely short skirts and shorts, and very revealing bathing suits be they one piece or bikini.

During the first years of our marriage we had a very active sex life. We fucked anywhere and everywhere on a regular basis. Myself, having unusually small genitalia, had become quite skilled at giving women oral sex and my wife enjoyed my skills often.

Over time she became somewhat aloof during sex, then demanding and bossy. I was ok with that, I enjoyed the subservient role. She began to make me beg to lick her pussy till she came and then allowed me to jack off on her feet or tits instead of fucking her.

Eventually when I asked her why, she took a deep breath and told me; "your little dick just doesn't do it for me anymore so you should not complain and just do as you're told." I had heard things like this from women in the past so I was not surprised,

"Are you in me yet?"

"Is that your finger?"

"It's so small, does it cum?"

Not long after expressing this revelation she refused to perform oral on me stating that it was "like sucking on some ones finger." She soon accumulated a vast array of vibrators and dildoes. Watching her ramming those large toys in and out of her pussy bringing herself to thundering orgasms really turned me on. I would watch her intently while stroking my little dick, cum on her toes and immediately lick my cum off of them much to her delight.

During our courtship prior to marriage we had broken up and got back together so many times I lost count. Each time we split up we were both prone to jump into the first persons bed we came across.

When reunited she loved to tell me in great detail about her sexual exploits. Whom she had fucked and how thick and long his cock was. How it felt sliding in her pussy, the size load he had left in her. How she sucked his huge balls, or how she begged him to fuck her in the ass. But she always made a point to compare them to me. Me and my "worthless sissy dick" as she referred to it.

But humiliating as it was, I enjoyed listening to her tell of her sexual encounters with others. I would beg her to tell me the intimate details of her sex with real men. How it felt to have his cock fucking her mouth, his balls slapping at her chin, the explosion of his hot cum in the back of her throat. The sensation of his large hard cock first entering her, then repeatedly ramming his entire length into her. She enthusiastically told of him fucking her violently culminating in an intense orgasm when she felt his seed injected into her.

If I licked her pussy and made her cum as instructed, I was rewarded with more explicit accounts of her sex with other men, and allowed to masturbate my now rock hard little dick and cum on her feet, as long as I cleaned them after.

Her exhibitionism continued and became more brazen with time. She took to wearing only thong underwear under very short skirts. A tramp stamp tattoo along with a butterfly just above her pussy were next. Had her nipples pierced, making her braless little breasts even more of an attraction to men. She delighted in taking every opportunity to display to anyone willing to look.

I had become quite used to her flirting with men on our many nights out at the local dance club. I was allowed to accompany her only until we were inside, then was told to keep my distance and watch. Always attracting attention in her very revealing outfits, there was often a line of guys waiting to dance with her. She took great pleasure flashing her thong covered, clean shaven pussy by crossing and uncrossing her legs while seated on a bar stool.

I often tried to position myself within earshot of the guys ogling her to hear their lurid comments. I found it to be very exciting and knew my wife would be extremely turned on later to hear what they had said about her. After her shameless flirting she would dance with several that she found attractive. Her dancing was more like a sex act than a dance, she would place their hands on her ass then slowly grind her pelvis on theirs.

One particular evening she seemed to be focusing most of her attention on just one particularly attractive guy. When they danced she was kissing him deeply which was something she normally didn't do. When the music ended I saw her go towards the ladies room and emerge moments later. Walking straight towards me she stopped, leaned in and whispered in my ear, "hold these for me." Placing her soaking wet thong in my hand then returning to her dance partners table sitting down facing me.

Her new friend slid his chair in front of hers and placed a hand high on her thigh. As they began to kiss again I watched as her legs slowly parted and his hand moved closer and closer toward her now bare pussy. Although I couldn't see well in the dark club, I could tell by the look on her face that he was fondling my wife's soaking wet pussy right here in front of everyone! This made my little 4" dick rock hard and as I tried to adjust it in my pants I almost made myself cum. My wife was now rocking gently and biting her lower lip, a sure sign she was about to orgasm. She then closed her eyes, opened her legs wide, slid forward in her chair, and rocked violently for several seconds while kissing her friend passionately.

The next thing I know she is pulling me to the door and telling me "we have to go home, NOW!" When we arrived home my wife was out of the car and in the house in seconds. When I came in she ordered me to "get in here and lick my pussy." She was whimpering something about needing a real cock as I lapped at her erect clit when she suddenly pushed my head away and instructed me to put on one of her strap on dildoes. "The big one," she demanded "I need a cock in me and your little thing is not going to do it." I quickly stripped and did as she instructed and climbed on her. She helped guide the huge 10" silicone cock deep into her sloppy pussy and within minutes was bucking and shuddering with an intense orgasm.

My wife now lay limp as I withdrew the big cock from her gaping pussy. She looked up and noticing my hard little dick said "come here, I am going to let you jack off on my pussy tonight." I scrambled up between her legs and began to stroke myself. She told me how attracted to her friend she had been earlier. When they danced he had played with her nipple rings which really turned her on. While she was grinding on him dancing she could feel his cock growing larger in his pants. As he kissed her she felt her pussy juices begin to flow, and that's when he told her "go to the ladies room and take off your panties." She continued, "when I came back he was kissing me and started finger fucking me." "It felt so good, I didn't care that everyone was watching." "The next thing I knew he had three or four fingers in me and I was cumming."

I started stroking myself furiously and began to cum all over her gaping pussy. I didn't need to be told what to do next. I dropped down and began to lick the cum from her freshly dildo fucked pussy. When finished licking and swallowing every bit of my own cum she said to me, "I am so glad you like eating cum from my pussy." "I am tired of dildoes and vibrators, I need a real man's cock." "I want to to start fucking other men."

I have to admit it's not like I hadn't fantasized about this. I thought I had a pretty good idea of where we were headed, but I did not fully realize at this time I was to become my wife's little sissy toy, and love every humiliating moment!


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lostopportunitylostopportunityover 1 year ago

I wrote your story be published tomorrow enjoy

TSTGDreamsTSTGDreamsabout 2 years ago

Thanks for writing this!

AnonymousAnonymousover 2 years ago

Thanks for the hot story, Seeing the pictures of SallyAnn made the story even better for me. Thank You.

missybaby57missybaby57almost 3 years ago

A great start SallyAnne.

AnonymousAnonymousabout 3 years ago

Fun to read and active all the way through. Well written and edited! I like dpt 1

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