Confessions tagged with 'crossdressing'.

#5872

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I am a crossdresser. I will wear a skirt, pantyhose, and high heels and with these new policies of trans able to use the women's restrooms, I will sit in a stall and jack off while i listen to the women pissing, farting, and shitting.

I get really excited when I hear her make a huge fart that resonates in the toilet bowl, or when I hear her turd drop in the water, I usually cum at that point.

#5656

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So I've secretly been crossdressing since 12 years old (I'm 41 now). For a few years I dated someone from high school and she learned of my crossdressing, bisexual kinks and embraced them. We split up eventually and now I'm engaged to a great woman who has no clue about my kinks. My ex is now an escort and at least once a week she pimps me out to a few customers and/or we go play with randoms at the porn theater. My current fiance has no clue I am a sissy whore pimped out by my ex gf.

#5177

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I am actually grateful to this site for saving my sex life, My wife and I have lost all interest in each other sexually but are still very happily married.

We began reading some of the stories and confessions on this and other sites to see what got each of us turned on and then set about helping each other experience what we wanted to try.

We found a local swingers group and were easily able to organise a large group of men to gangbang my wife, as she had gotten turned on by reading about such things so over the course of a weekend she was railed in all holes repeatedly by ten younger men who were very well hung in comparison to myself.

My own desire was a little harder to sort out due to location but I was recently made over at a cross dressing salon before going to a local area known for prostitutes, I spent a night being paid to suck and get fucked in the ass while dressed as a whore and I loved every minute.

My wife has now expressed the desire to be fucked by a horse cock which is proving difficult to sort out without involving a family friend who has a male horse, what I haven't told my wife is that I really want to lick and suck both the horse's cock and her pussy when it has pumped her full of cum.

My second desire is somewhat easier to organise as it is something I did before we got married the only difference is I want her to film it, I'm not sure she will though as I am planning to again get cross dressed and then get used by my two brothers and their friends which last time meant I had six cocks to use for a whole weekend, My brothers are good to go but will she be?

Lastly we both share the same idea and again it is going to be easy to arrange, we both got extremely turned on by tales of being knotted by large dog breeds, we already have access to a very large Bull-Mastiff owned by my oldest brother but the list of breeds we want to try is quite long she wants to try Great-Dane, Rottweiler and Doberman cocks and I want to try Alsatian, Malamute and Pit-Bull Terrier as well.

Hopefully we can get something sorted out soon as we have had such huge smiles and are way Happier as a couple, so grateful to this site and those who post such perverse things for us to try and copy

#4479

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For as long as I can remember my father has been playing with my cock. My mother watches him and gives encouragement He sucks me and makes me suck him until he has an orgasm. By the time I was 4 he decided that I should be dressed up as a little girl and the sex games continued so I, of course, began to associate crossdressing with pleasure and would put on girls panties and a dress whenever I could. One day when I was six he pulled my panties down, lubed his cock and eased it into me. It hurt like hell at first but I became accustomed to it. He took to making me say things like "Oh Daddy, I am your filthy little sissy faggot and I love it when you fuck my bum and shoot all your sperm inside me" or" Please make me pregnant, Daddy". He really is into this crossdressing business and now we both dress up and he fucks both me and Mummy while he is in girl mode. When he is fucking Mummy I have to stand in front of him with my skirt raised while he sucks my cock. Now that I am getting more grown up I would like to fuck my Mummy and my Daddy.

#4045

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on Friday twenty second of October I had an amazing night with my wife's family.

My wife had arranged for her and her female relatives to go out to the cinema for the night and for the male members to visit me, There was my father in law, two brothers in law and several of her cousins.

I was waiting for them to arrive wearing a black lacy bra suspender belt and knickers with seamed stockings and 4inch black patent high heels, I had very well done makeup and a dark rooted blonde wig that looked awesome.

As soon as they arrived I had a cock in my mouth which was very soon joined by a cock in my ass, time went by and I sucked and was fucked by all present when the doorbell rang, I answered the door myself and invited the two delivery drivers (pizza and curry) in to join us so they could give me more than just the tip if you know what I mean.

I soon had them both in me and was pleasantly surprised at the size of the brown cock in my mouth, after a good fucking by both I was positioned over the pizza guy and the Indian driver pushed himself into my ass alongside him, this left my mouth free to suck some of my wife's family back to life.

I soon had both drivers pumping spunk into my ass, they let me suck them clean before leaving, I soon had two of the cousins cocks buried deep in my ass and my father in laws balls were touching my chin as I deep throated him, now my wife had told her female relative what would be happening at our house and invited them back to watch, this was positively encouraged by my mother in law who had watched me before so most were up for it and came back to our house,

they watched me suck and get fucked by all the males present which included our dog which my wife brought in the room.

I while knotted by our dog I got to lick my sister in laws arse while she sucked her husband back to life.

At the end of the night it was organised for another night out in November with the action taking place at her cousins place as they have some large out buildings so everyone who wants too can bring a friend and even their dogs, I am hoping that when the time is right I will be able to suck and get fucked by my wife's aunties horse as well.

#3965

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Well I just had the best burger ever! I went to a late opening McDonalds and jokingly asked for the "special sauce" on my burger. for a bit more context I am a crossdressing slut who loves cock.

Anyway the manager on duty knows me and convinced every male member of staff on duty to wank onto my burger while I sucked him off in the office, my burger had more spunk than meat and I loved it. xxx

#3778

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Weekly confession number 3.

Well this week has been fun but it all came about from something that happened 3 years ago.

So 3 years ago I was at a friends house and the conversation got a bit spicy and I told her quite a few things about myself and my pervy side, I told her about my crossdressing and about my love of cocks of any type (human, dog, horse, dildo)

She to my surprise was quite turned on and actually asked to see me sucking a cock while dressed as a woman, The next time I went to hers I arrived at her back door which was out of sight of the main road and before I went in I stripped off to my Lingerie (black lacy suspenders with a matching bra and crotch-less panties) and put on my heels before putting my male clothes into a bag which I left outside.

In I went and surprised her with my appearance which made her splutter as she was taking a sip of her coffee, She was on a video call to her brother but made her excuses and hung up the call.

I simply asked if she had a dildo I could use as my ass was aching to be fucked, she looked me up and down and said "WOW" before leaving the room to go and fetch a dildo from her bedroom.

When she returned downstairs she was greeted by the sight of me on all fours sucking on her German shepherds cock, I reached back and patted my ass cheek and said "put that dido in me" she was a bit hesitant but soon had the dildo deep in my ass and was pushing and pulling it in and out at a steady pace.

I was making a lot of noise as I was being so well fucked that I took her by surprise when I turned and pushed the dogs cock into my ass, She was sat there with the dildo in one hand and her phone in the other videoing the scene.

I soon repositioned the dog onto my back and he went for it humping his cock and knot into me and before long his knot swelled and he locked into me With his rather large and hot cock and knot stretching deep into my bowels I could feel his cum flooding into me.

The dog repositioned himself so he was ass to ass with me and anyone who has seen dogs fucking will know this usually means they will be knotted for some time, well I wasn't disappointed as he was locked into me for around thirty five minutes during which time I happily conversed with My friend between moans of pleasure as the dogs cock twitched and pumped more cum into me.

I gave my friends pussy a good licking as well and she climaxed onto my face which she told me was the first time she had ever squirted like that, The dog pulled from my ass soon after and I greedily sucked and licked his cock clean before simply getting up and letting my friend watch as the spunk flowed out of my ass.

I left soon after and other than being allowed to go and get fucked by Danny (the dogs name) from time to time we never really talked about it until Monday twelfth of April.

I was asked by my friend if I would put on a show as she called it for her and a couple of her friends, as I didn't know them and am quite an extroverted pervert I agreed, so on Friday morning the sixteenth of April I went to her place and found Her with her brother, mother and sisters as well as a couple of her friends, I was only surprised by her family being there and was told they had only just arrived and she hadn't had chance to warn me before I arrived through her back door again dressed in just my lingerie and heels ready to get well and truely fucked.

I decided to just carry on and she informed her family why I was there, to her surprise they were all excited at the idea and asked if they could stay and watch! I said ok and got into a position on the floor where I had enough room and was soon being probed with the dildo which was being used on me by my friends Mom! My friend went to fetch the dog and returned with Danny who took his usual position for being sucked off, as I sucked something felt different about being dildoed so I turned to see my friends brother being cheered on as he was humping my ass with his own cock. (he is gay)

I was soon eager to be fucked by the dog and turned so the dog could mount me while I sucked her brothers cock, I soon had a mouthful of warm sticky cum which I played with for a while before swallowing.

The dog was now well and truly knotted into me and I was really happy to be getting used like this, My friends sister lifted her skirt and gat on all fours so I could lick her ass and pussy and soon had four fingers in her pussy and my tongue up her ass when she pulled forward and convulsed into an epileptic seizure.

I had to try and move myself and the dog into the kitchen so they could call an ambulance for her, As the paramedics arrived the dog finally pulled free and was licked an sucked clean.

I was soon sat in the living room having a conversation with everyone and was soon sucked off by my friends brother while I was talking to his mother who informed me she had often walked in on him being gangbanged by up to six men.

I emptied my load into his mouth and he swallowed it all then to my surprise and delight he was ready for round two and gave me a really good rough fucking which lasted longer than the first one before he pulled out and sprayed his spunk onto my face. It all went quiet while we waited for news of the sister who was kept in over night due to bashing her head as she went into the fit. but it has been agreed that when covid restrictions are fully over we are having a larger get together as in more males and more dogs for me! yummy

Now I know this will look like a work of fantasy but all I can do is say this is a TRUE account of what happened but its up to you whether or not you believe it, Bye for now xxx