Blog : Skinny dipping

93 posts
9/7/2022 11:57 am

Skinny dipping

Nobody was at a friend's house it was 90-something degrees and they always said any time you want to use the pool come on over and jump in. I was working outside in the yard started early in the morning. It was around lunch time decided to call my friend to ask if could jump in their pool, he said " nobody will be home and the company that takes care of the lawn came yesterday instead of today. I thanked him for the use of the pool ahead of time after cutting the lawn and picking weeds need to be refreshed and cold drinks are not doing the job.
I grab a couple of towels and go over to their place a few houses away. I place the first towel on the ground outside of the pool so when I come out do not burn my feet then lounge chair on top of it so it does not blow away if a wind should come. Second towel, hat, and sunglasses on the lounge chair, leaving my clothes underneath the lounge chair.I step into the pool the same way would step into the shower or bathtub step onto the shallow end floor and allow myself to sit on the shallow end floor then start swimming. Time has passed fingers are looking like raisins, my sack shriveled as well as penis decides it's time to get out get the second towel to dry off, and leave it under my body so bare skin does not touch their lounge chair. I place sunglasses on and hat lay on the lounge chair and fall into a deep sleep.
I wake up to a shadow standing over me and see Betty who lives across the street from my friends who gave me permission to use their pool. Betty looks down at me and says "Wow you must have been exhausted while you were sleeping I painted your toenails and locked your penis in a cage. Now if you do not want our friends to find out you were skinny dipping in their pool and laying naked on a towel on their lounge chair you will get the woman bathing suit that is on the ground by your sandals and I have a wig in my beach bag for you to put on and walk with me back to my place".I am speechless as I see the toenails on a bright sunny yellow almost neon-like and see Betty had put a metal cage on my penis that also has an X on top leaving tan lines on the head. I say nothing as know the longer in the sun the worse the tan lines will get so put on the one-piece woman bathing suit. The woman's bathing suit is so tight that feel it flattening my stomach while my chest fills the cups. I tell Betty it is tight and cannot breathe. Betty says instead of breathing in and out as you do normally breathe up and down. I do as she says and notices the skin that filled the cups are breasts and the cleavage is more than could of thought a guy can have. Betty takes off my baseball cap and tells me to put on shoes and let us go before the wife comes home from work. I say home from work what do you mean then look at my watch it is after 5 already.
She takes my hand as two women walk hand and hand talking and catching up on things bathing suit getting tighter and tighter breathing up and down as told noticing cleavage increasing it even seems the bathing suit is pushing my skin together for the appearance of me having larger breasts. She looks behind us and says " Amazing never seen a male with such a feminine-looking ass and we need to get rid of the pubic hair you have hanging out of the bathing suit that is not lady like it is more like and I have no intention of pimping you out for money at least". She opens the front door to her house and tells me to step in before the traffic increases we would not want people living on the block seeing a strange-looking woman standing outside of my house having them stop and ask if everything is all right embarrassing you when they find out you enjoy cross-dressing. I quickly enter her place and the door closes behind me. She walks me to a full-length mirror to the first time seeing myself fully mouth drops open in shock. She says perfect stay like that puts lipstick on my lips, and an eye shadow on the bottom of my eyes tells me to close my eyes, and puts more eye shadow and then eyeliner.
She says " I always wanted dolls but we were to poor growing up and when I followed you walk into our neighbor's backyard watched you strip and knew with the extra body fat you could be transformed into a girlfriend and our friends told me you were on vacation all week which means since it is only Monday you will be my play doll for the entire week and no need to go back to your place for clothing I got you covered and will call you Manni and by the way, Manni I am not all woman pulls her skirt back to show a 9-inch long cock that is thick with veins showing hanging telling me she is not even hard at this moment. I admit to her that I do enjoy dressing in women's clothing especially corsets, tummy tuckers, and tight things that give me a feminine-looking body, and have a sissy name of Chelsea but never thought of buying a cage for my penis.
The neighbor places her hands on my shoulders pushing me to my knees so my face is now even with her 9-inch-long thick cock and says " Well sissy Chelsea you know what to do start or photos from the ring doorbell will be posted along with video. Opens lips and begins sucking on the tip with hands being on her thighs, neck slowly bending side to side getting the full head in mouth, and feels clitty straining in its cage. Betty slowly moves her hips forcing sissy Chelsea to take some shaft a little more each time increasing her hip motions and tasting the dripping of precum mixing with her own saliva. Betty places her hands on the facial cheeks of sissy Chelsea getting Betty's cock to harden by f cking Chelsea's mouth. Chelsea cannot help herself and finds her hands slipping back to Betty's hips till Chelsea's hands rest on Betty's ass cheeks as her nipples are pressing against the female bathing suit.
Betty pushes Chelsea backward forcing Chelsea's legs to swing out from underneath her till Chelsea is flat on her back being forced to swallow her first load of cum from Betty. it is past dinner time and Chelsea is saying she is hungry, Betty looks at her well Chelsea it is time you go to sleep so places a collar and leash on Chelsea leading her to a large cage and ordering Chelsea to crawl in and curl up and fall asleep as Betty closes and locks the cage then covering it with a dark sheet so no daylight will wake up Chelsea.
The cover is taken off but it is still dark Chelsea is pulled out by the leash attached to the collar around her neck and told to "look down at the cleavage and breasts the bathing suit has created from the skin of your own body. Crawl into the kitchen and put your hands on the table so can paint your fingernails to match your toes sissy old woman Chelsea. Look at how slutty you look and how easy it was to have you suck my 9-inches swallowing loads of cum all night. You have a bowl of cum to lick up and swallow. Then we will go fix your makeup and you will learn how to fix it yourself you slut Chelsea as that was your first time swallowing but will have some shorter and some much longer this weekend and its only Saturday morning.


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