Secret Sissy - Ch. 01

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Straight guy becomes a raging sissy.
889 words
4.21
44.6k
25

Part 1 of the 4 part series

Updated 10/25/2023
Created 08/27/2023
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My name is Joe and I was a straight married man, married to my wife Bonnie who I met 18 years ago and we fell head over heels in love and we were married within 1 year of our first date. While life has been good and we have had what most people would call a "good" marriage, Bonnie has never been very sexual and our sex mainly consisted of the traditional "missionary" position once-a-week. Once a week eventually became one every-other-week and so on until it eventually became 3 weeks and sometimes once-a-month. As a result, I found myself spending more and more time watching porn, masturbating to gorgeous girls with perfect breasts who loved sex in every position and who were always glad to suck on the massive cocks of the buff, muscle-bound men. Over time, I began to notice that black men had the biggest cocks and found myself gravitating to cock sucking videos and anal sex with anal cream pies featuring big black cocks, understanding for the first time the term "BBC".

The proverbial switch came about 10 years ago when my wife and I went to the community pool on a Sunday afternoon, which is our weekly ritual. We plopped our towels and stuff in one of the shaded cabanas by the pool and jumped in to cool off from the hot Arizona sun. As usual, in the our wealthy, high-end, community, there is a good mixture of young hot couples and singles ranging in age up to about 50, or so. Of course, most of the women have had plastic surgery and breast implants with very tiny bikinis to show off their gorgeous tanned bodies. Most of the guys are young and buff who I see lifting weights every week in the gym -- I work-out a bit and cycle a lot so I have very fit legs and I am medium height so I don't stand out much with the buff guys and gorgeous ladies.

Our Sunday at the pool usually consists of my wife lounging on a chair in the sun, reading a book, and then cooling off from time-to time in the pool. I typically try to find a shady spot out of the sun and sit in the pool taking in all the gorgeous bodies and discreetly listening to the surface conversations about the local clubs and who is dating who. I typically wear sunglasses and a baseball cap so that no one can tell that I am staring at the nice round butts in skimpy bikinis and large tanned breasts that have been carefully created by skillful doctors.

As the day ended, I began gathering up our towels and pool items in the cabana, checking to make sure I didn't leave any keys or wallet under any of the cabana pillows. That's when it happened.... there underneath one of the cabana pillows was a blue pair of sexy lacy panties which I knew were not my wife's -- she had started wearing granny panties lately because I guess they must be more comfortable or something. That is when the curiosity hit me -- I wonder if they would fit me? I quickly looked around, somewhat nervous that someone would see me, and then grabbed them in the ball of my hand and stuffed them in my jeans pocket.

Next thing I remember, I was in the men's bathroom stall where I usually go to change in and out of my bathing suit and as I take off my wet bathing suit I pull the newly found panties out of my jeans pocket and try them on. The panties were dark blue lace and definitely tighter than my boxers but the elastic waistband expanded nicely and I pulled them all the way up. I managed to point my cock upward toward my belly and keep it completely inside the panty -- I think my cock has shrunk a bit over the past couple years, from lack of use, as my sex drive has really fallen off and I rarely have sex with my wife anymore.

I can't forget that first feeling of wearing panties, I was excited and somewhat scared as I pulled my jeans up and stuffed my boxers into my pocket, creating a good-sized bulge in my jean's pocket which I hoped my wife wouldn't notice. I carried my towel close to my body to hide the pocket bulge until we loaded our gear into the trunk of the car and I quickly hid my boxers in my computer bag I had brought along in case I wanted to surf the internet.

When we got home, I went into the bathroom and stripped off my jeans so I could check out how I looked in the blue lace panties and I fantasized about which of the young ladies at the pool with huge breasts had inadvertently forgotten her panties which I now owned and she would never see again. I proceeded to wear the panties the rest of the day and had to strip them off before getting into bed and discreetly wash them in the bathroom sink as my cock had precum all over the place from my excitement of wearing panties..... where can I hide these these panties so they can dry?

...to be continued

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14 Comments
AnonymousAnonymous7 months ago

Dry? They will never dry. Destined to be moist and sticky for eternity.

AnonymousAnonymous7 months ago

You go Terri!..sissygasms are just totally beyond hot..love the anticipation I feel just before it happens..the straps of the lacy bra digging into me..fondling my ass in satiny panties..so hot to feel it actually happening..sometimes right then I think, what if I get caught?…that thought just sometimes pushes me over…and….mmm..

JT

4Leather4Leather7 months ago

You never know was there a girl watching them ? Setting the bate with putting her panties under the pillow knowing he would find them, The hook was set at that point. Next chapter please love to see we’re you take this.

TeriLeighTeriLeigh8 months ago

You go girlfriend! JT and Robin are soooo fight. Wearing panties and bras is so much fun and sexy. Having sex as the girl and in lingerie is so much fun. I love to sissygasm!!!! Keep writing Jo. 💋🏳️‍⚧️🏳️‍🌈👍

Robincd1126Robincd11268 months ago

Great first chapter. TY. Also, I love the comment from JT! All of his comments are so true! I got caught by my much younger roommate! (him-23, me 51) He had noticed lipstick stained cigarettes on the back deck and then looked through my bedroom window one weekend and watched me for about an hour. The next weekend he knocked on my bedroom door about 1am, and said "Let me in, I know what you are doing!". He took my V card three times that night. We were together every weekend until he went back to college. Best thing that could have happened to me.

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