Outdoor Liberation and Cuckolding

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Crossdressing risky and cuckolding.
1.7k words
4.13
16.1k
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After very nearly getting caught indulging my secret little hobby when my next door neighbour's daughter decided to step over the fence into my garden to look for her lost rabbit, I decided to renew the fence.

I remember the feeling of horror realising what she'd have seen if she'd have turned around.

A new fence has given me almost complete privacy and yesterday was my first full day of having the house entirely to myself so I'd planned for a little treat.

After showering and shaving, the first thing I did was slowly insert my butt plug and make sure it was comfortable and then hook up my waist cincher, loop the laces around a door handle and pull against it to get a beautiful, curvy figure.

Next was the cleavage enhancer bra, silicone boobs, black lace basque and matching lace panties which struggled to contain my swelling cock as I opened a new pair of sheer lace top stockings, ran them high up to the top of my thighs and attached the suspenders.

After a quick inspection in the mirror to make sure everything was perfectly straight and my boobs looked full, I slipped on my satin maid's uniform, four inch high patent heels and sat in front of the mirror to apply my false, french manicure nails, rings, necklace and clip on earrings.

I then took quite some time to perfectly apply my makeup with thick false lashes, heavy in mascara and sexy pink lipstick. On with the medium length wispy highlighted wig and then a final inspection in the mirror.

The sound of my heels clicking, the tight corset and the sensation of my now long hair was incredible and I had to resist the urge to masturbate every time I caught a reflection of myself.

I did some chores to add to the feminine feeling and then heard voices from next door's conservatory.

Knowing I couldn't be seen, I gingerly tiptoed outside and sat at my patio table, fully crossdressed and my heart pounding, just a few feet away from unsuspecting neighbours.

Eventually I started to relax into my new scenario, the wind on my stockings and through my long hair making for an incredible experience.

I crept back into the house with my cock straining at my panties, removed my butt plug, selected a much larger one, picked up my lube and iPad and headed back outside.

Once seated and careful not to make a noise with my heels, I set the iPad camera to record a video of me. I did a quick test to make sure my neighbours could be clearly heard on the audio and then videoed myself very femininely lubing myself and my plug up and then gently lowering myself onto it.

It was difficult to stay silent as I felt it slide right into me but the look on my face gave it away!

Next I quietly slipped my maid's dress over my head so I was completely exposed in my lingerie.

The liberating feeling was unbelievable! I slipped my cock out of my panties and recorded myself silently massaging my rigid cock with nothing to hear but my oblivious neighbours chatting.

I then read some erotic stories online, trying desperately not to cum.

Next I tiptoed back inside, admired myself in my sexy lingerie, straightened my stockings and touched up my makeup.

I then selected grabbed my long, realistic dildo with a suction cup and headed outside again. This time I walked confidently and let my heels click for all to hear, sat down, lubed up and videoed myself holding onto the arms of the chair and slowly lowering myself onto the full length of the dildo. How I kept quiet I'll never know.

I gradually got quicker until I was taking the whole length deep inside me, sliding it as deep as I could manage and holding it there while I shuddered to a massive orgasm, biting my lip to stay silent as streams of cum shot from my tightening balls all over the table.

Almost immediately I realised how lucky I'd been to get away with my risky orgasm so I quickly gathered my things and sneaked inside.

I couldn't wait to watch the videos back and my cock got immediately hard again watching myself perform and my massive cum shot coincided with the neighbours laughing in the background, the fake humiliation made me even more horny.

I felt the need for some reason to have a costume change so I rooted through my huge lingerie collection and noticed a huge pair of silicone boobs that I bought a long time ago but tried on once and thought they were way too big so put them away in their box, besides, I only had one bra which would accommodate them.

I strapped them on and couldn't believe how sexy the bounce felt so I dug out the huge black lace bra that fitted them, stripped off down to my waist cincher, strapped on my huge boobs nice and securely and fastened my bra over them. They felt and looked fantastic as I ran my hands over them, my cock stiffening every second.

Next, I tightened my waist cincher incredibly tightly until it felt unbelievably restrictive, put on a black lace high-waisted Rago suspender belt, put my stockings on again, pulling them up really high before carefully making sure my sexy French manicure nails didn't ladder them before attaching my suspenders and sliding up my matching black lace panties.

I couldn't help running my hands all over myself as I looked in the mirror, the look of my feminine, sexy nails on my beautiful lingerie and the sight of my sexy tiny little waist accentuating my curves ensured my cock wouldn't be fitting inside my panties any time soon!

I wiped a drop of pre-cum from the end of my bulging cock and watched myself sexily lick it from my finger in the mirror.

It was SO sexy!

I decided that my massive, jiggly boobs didn't match my sexy "less is more" makeup so I decided to make myself look more tarty. My dusky brown eyeshadow became much more pronounced, as did my eyeliner and I put many layers of thick mascara on until my lashes couldn't hold any more.

I enlarged my lips with lip liner and filled them out with a darker pink lipstick and very shiny lip gloss and my blusher became more pronounced too.

I decided to keep the same wig as I felt very feminine and sexy wearing it and I swished it around in the mirror making sexy poses as I did, hand on hips, pouting and pushing out my huge boobs.

Eventually I managed to fold my cock back into my panties by doing a couple of chores to take my mind off what I was doing and watching TV.

I was aching to go for a drive somewhere quiet and take pictures of myself but decided against it as I'd had a glass or two of wine and it wouldn't be a good idea so I decided to stay put.

Next on my agenda was to try my new butt plug called the "hitch". It's rather large and very uncomfortable to put in but I decided to give it a go. Adequately lubed, I sat on the bed, slowly easing my weight onto it as it entered me. After a while I could feel it going past the point of no return so I gritted my teeth and ignored the discomfort as the thick ball found its way inside and pulled itself up to the hilt inside my ass. Words cannot describe the feeling of it being fully inside me, pressing and pushing in every perfect place.

I composed myself, stood up, straightened my lingerie and admired myself in the mirror again, looking like a slut with a full ass.

I quietly went outside again to where I was before, my neighbours enjoying themselves a few feet away and oblivious to my perversions. I set my iPad to record again and adjusted it so I was perfectly framed, my stocking clad leg over one arm of the chair, one hand massaging my swollen cock, nails dragging sexily on my balls through the lace and the other caressing my lingerie and huge boobs.

Eventually I started to tense against my corset, my balls tightened and I shot another load of cum vertically up in front of me. I wished I could've taken the load in my mouth and savoured the taste.

That was the end of my sexy and risky evening and on to tonight's fun.

My ex girlfriend from many years ago is staying over for a few days to visit her daughter. We stayed good friends after the split but she never really enjoyed my crossdressing, more tolerated it.

I know she's been dating a guy down here and has gone out with him tonight. The thought of her getting fucked and returning here afterwards when I'm asleep drives me wild.

From before she arrived I was wearing stockings, suspenders, panties and a butt plug under my jeans and waited for her to shower before she left.

As soon as I heard the bathroom door lock, I went straight to her room to go through her bag.

My cock throbbed as I picked up her vibrator and ran my tongue over it to taste her juices.

She's packed black hold-up stockings, normal stockings, a black basque, matching lace panties and a beautiful floral bra set. I carefully replaced them as I found them and went back to the lounge.

I was squeezing my cock as I heard her go into the spare room to change, not knowing which outfit she'll choose for her date.

When she left I pretended I wasn't bothered and just said "bye" but as soon as I saw her car leave I raced to her bag. She was wearing the basque and her vibrator was missing. I immediately found the panties she'd been wearing all day, put them over my face and came while I was licking her juices.

It's now 10pm, I'm in bed wearing white lace lingerie, black sheer stockings, silicone boobs in my bra and a fat plug in my ass waiting for her to come home and listen to her masturbate her cum-filled pussy.

Tomorrow I'm going to suck the cum out of her used panties.

I'll let you know how I get on. X

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AnonymousAnonymousover 1 year ago

That was both ugly and nasty and NOT in a good way. Promotes sneaking around instead of honesty.

cdCindy1cdCindy1about 4 years ago
please continue

I would love to hear what happens next. Also, does the neighbor's daughter catch you? That would be so hot and make me really hard. I would love for my next door neighbor's daughter to catch me crossdressing. She is 22 years old, very pretty, and has nice tits. I would love for her to fuck me with a big strap-on cock while her tits hang down over me so i can play with them and nibble on her nipples. I want to be her bitch.

I can't wait to read more of your stories.

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