I dressed up as a girl and let a stranger with a girlfriend and a [m]assive cock fuck [m]e raw for my first time.

[Picture from the night](https://imgur.com/a/ktlqweH)

This is a long one but I promise you, it’s worth it.

So bit of background: I am, for the most part, a straight man. I’ve never really liked gay porn and have only ever had heterosexual relationships – all of which have been really healthy.

However, ever since I was young, I have had a fascination with woman’s clothes. I’m not sure why, but it started out as sneaking into my sisters room and wearing her underwear and liking the way it made me feel. The strange thing though was that when I dressed up I started to feel like a woman, which in turn made me think sexually as a woman. So naturally, it wasn’t long before the whole thing snowballed into me being a full time closet crossdresser whose favourite thing in the world was his sisters dildo that he discovered in one of her drawers. I also discovered crossdresser, sissy and trap porn which basically became my staple. My ultimate fantasy was to be fucked senseless while dressed like a slut by a big strong man. Of course I have never told a single person any of this out of fear of what they’d think.

My ritual was basically this; I’d get into a relationship and forget about my urges, then when it ended they’d come flooding back so I would go out again and buy all the clothes and sexy things I’d thrown out last time. The furthest I’d go to act out the fantasy would be to take some sexy pictures, put up an ad on Craigslist (when that was a thing) with a link to my Kik account and make empty plans with strangers that I was too scared to carry through.

Flash forward a couple years and I’d just gotten out of a 6 month relationship and was rediscovering my independence. As usual, the urges came back, but this time they came with a vengeance. During a particularly horny stage I went out and bought myself a sexy schoolgirl outfit and a 7” dildo, but it wasn’t enough. I needed to feel a man inside of me. I knew I just needed to live out the fantasy or I would die wondering.

With that in mind, I walked into the bathroom and for the first time in my life shaved my entire body from the head down, save for a cute little landing strip. My head hair is naturally long, about nipple length, so I combed and straightened it so it looked feminine. I couldn’t believe what I saw in the mirror. I was hot. I would definitely have fucked me.

My next move was to go and get dressed up to get me in the mood. I started with some thigh high black fishnets and coupled that with a black lacy bra and matching lacy thong. It was one of those thongs that had two strings that ran up the bum which could be moved aside to expose my ass. On top of all this I popped on a white blouse and short red plaid schoolgirl skirt and topped it all off with a black choker necklace.

I jumped on kik and started talking to every guy I’d connected with (literally hundreds of guys) to try and sort something out.

There was a lot of people who were obviously just time wasters or who wanted pics. That was until I got chatting to Jay.

Jay wasn’t like the rest. He could hold a conversation and seemed to exude a confidence I found very sexy. He told me he had a big thing for sissies and had wanted to fuck one for a long time. The mutual first time was reassuring.

I took the dive and just asked him if he wanted me to come over. To which he replied yes and gave me his address.

Before I could stop myself I threw a tracksuit over my getup and jumped in the car. His place was a 20 minute drive away, which was 20 of the most conflicted minutes of my life. The male voice in the back of my head was screaming that I didn’t want this, whilst the soft feminine voice hushed it and swam my mind with images of my tongue tasting dick for the first time and being fucked like a woman.

I got to his house and knocked on his door. He opened and I got my first look at Jay. He was about my age, maybe a little older, tall, probably about 6 foot 2, compared to my 5 10 and he had muscular broad shoulders. If I had a pussy it would have been dripping.

He ushered me inside and told me I can get ready in the bathroom and that he has a surprise for me in there. I was half frozen with fear so I just smiled and said okay and let him lead me there. It’s worth mentioning that at this stage Jay is relatively shy, which actually makes me feel a lot better.

Inside the bathroom was a collection of shoe boxes and a makeup case. He explained that they were his girlfriends. Okay Jay. That’s a development. Now in hindsight I probably should have called it there but I was so turned on and so mentally committed that, if anything, it only turned me on further. He explained that she was out for a girls weekend and won’t be back until Sunday night (it was Saturday night).

I closed the bathroom door, got out of my tracksuit, selected a pair of heels which were a perfect fit (I have small feet for a guy) and applied some light makeup – lipstick, mascara, blush.

I look myself over and then stride out to the living room in my heels. Jay had turned the lights down, put some music on and had a beer in his hand. I put on my best feminine voice and presented my body to him “do you like it?” He said yes, passed the beer to me and awkwardly motioned over to the couch and mumbled something about having a drink and playing some video games. At this point I realise jay must be equally as conflicted as me, if not more and that’s probably why he’s so shy. We play a game or two of COD and then I sum up the courage to make a move.

I began by standing up and moving slowly around the back of the couch. I’m trying my best to walk slow and sexy but secretly I’m freaking the fuck out. From there I put my hands on jays shoulders and run my fingernails over his chest. While I do this, I bend at the waist and nibble on his ear. I can’t believe I’m doing this. But it’s too late to back out. So I trail my hands down further and grab his crotch through his loose gym pants. My hand wraps around his dick and holy fuck.

He. Is. Huge.

Flashback to Jay and I’s kik chat. He’d warned me that he had a big dick but I didn’t really believe him because every guy on there says the same thing. But nope. Jay is the real deal. He’s packing pipe. My fear turns to excitement and in that moment I decided to just let go.

Walking around sensually to the front of Jay, I made sure my hips swung as I passed him. I stopped with my back to him and slowly began to dance to the music. I swayed my hips from side to side and did my best to replicate scenes I’d seen in movies and strip joints. Then I walked over to him, turned around and, using the armrest for support, lowered myself lightly on top of him, wiggling my ass slightly across his dick which, at this point, had gotten even harder. I leaned forward, put my hands on the ground and crawled forward, doing my best to sway my ass as I did. At this point I felt like the sluttiest stripper alive and so I took the next step.

I stopped about 3 feet away from him I lowered my top half onto the ground, keeping my ass high. I slowly reached back and slapped my ass and then, with my hand reached back, pulled my panties to the side and exposed my tight little shaved virgin butthole to him. I moved my hand over and slowly began to play with it before slipping one finger in.

Lifting myself back up I turned around and lifted my head up. Jay was sitting on the couch with his shorts around his ankles, in his hands he held a giant, hard, uncut cock. Without exaggerating I’d say it was about 9 inches and FAT.

At this point, my own little 5 inch dick was poking painfully into the front of my panties and leaking enough precum to soak through my skirt. I crawled on hands and knees over to jay, took his pants all the way off and settled between his legs. I was breathing heavy as I reached up and wrapped my hand around the first ever dick I have touched aside from my own. This was it. I’m a full blown slut now. And I couldn’t be happier. Jay sighed and relaxed into the couch, happy for me to take the lead.

I moved my hand up and down slowly, enjoying the way his giant dick felt in my hand and the way it looked as the foreskin pulled back to expose his massive head, already sticky with his own precum. I needed to taste him, to feel his cock fill my mouth. I’d wanted this for so long and now the moment was finally here. I inched closer and slid my lips over the end of his dick.

It was so warm and hard, yet soft. The only way I can describe it was that it felt really nice. Jay obviously kept good hygiene too because it didn’t smell or taste bad at all. Gaining a little confidence, I pushed it further into my mouth and began to explore him with my tongue. I alternated between sucking his dick, pulling it out and licking it all over. This was my first time aside from a bit of practice on a dildo so I can tell you that it wasn’t amazing but Jay seemed to be enjoying himself which made me feel so sexy. My anxiety was crushed by my desire to try everything so over the next 10 minutes or so I worshipped Jays cock; slapping my lips and face with it, sucking on his balls, deepthroating it, kissing and licking it all over. At some point toward the end Jay leaned forward and reached down to lift my skirt up and play with my ass, rolling it in his hands and occasionally landing a spank on one of the cheeks.

Eventually I couldn’t hold back anymore. I NEEDED him to fuck me. I pulled myself up over his lap and, using my best sultry voice, instructed him to finger me. With one hand he pulled my panties aside and with the other he placed two big fingers into my mouth to wet them and then slowly rubbed them against my asshole. He pushed one inside me which made me release a half whimper, half moan. I needed him inside me so badly. I pushed my ass back against his finger so it could go deeper.

At this point I’m just in full slut autopilot mode and tell him to fuck me. He chuckles, probably amused at my eagerness and tells me we should go to the bedroom.

I stand up, flustered as fuck, and pull my panties back into place. He leads me to the bedroom and I do my best to walk sexily in the heels even though my legs feel weak, either with desire or anxiety, I’m not sure at this point.

We get to his room and sure enough there are signs everywhere that he has a girlfriend. They have a walk in wardrobe full of dresses and skirts and a dresser with jewellery and makeup. I can’t believe that I am “the other woman”. But again, this just makes me feel even sexier.

As I walk I unbutton my top and drop it to the floor. Again, I make the first move, crawling onto the bed, heels still on, into doggy position and unbutton my skirt, letting it fall below me to expose my feminine bum underneath. I pull both strings of my thong to each side, turn around to him and just say “come and fuck me Jay”. I think about that a lot these days when I masturbate. It was very, very hot.

Jay reaches into a side drawer and grabs some lube. I remember thinking that he must have to use it with his girlfriend because of his massive dick.

He squirts it about 4 or 5 times into his palm and then works it all over his giant meaty cock. My own dick is still poking aggressively into my panties, I haven’t even really thought about it. This is all about Jay and his beautiful cock.

Jay approaches me and clumsily rubs a very lubricated thumb over my asshole and pushes it inside for a few seconds before pulling it out. I stare straight ahead, heart in my chest with anticipation. I bit my lip as I felt something very large, hard and wet rub up against my little asshole.

At that point I panicked slightly. In my horniness I completely forgot about safe sex. And that’s when I really thought about my situation. Here I was, completely shaven, wearing nothing but black lacy underwear and fishnets, in a random girls heels while I’m about to get fucked raw by her boyfriends massive cock, who is also a complete stranger. And in light of that the next words out of my mouth were “Jay, please just put your fucking cock inside me”.

That seemed to be the only encouragement he needed. Because the words had only just left my mouth when I felt a hand grab my waist and a pressure on my butthole. I tried to relax and let him in. I’d used quite a few dildos but this was different, the warmth, the skin, the size – my god the size (the biggest dildo I ever bought was about 7 inches). He kept pushing, and I could feel my butthole slowly stretching around the huge head of his cock. I couldn’t believe the pain, it felt like I was going to split in two. And then, just when I thought I was going to wimp out completely and ask him to stop, something changed, the pressure got less and then with a rush he slid past the head and buried about 4 inches into my ass.

I have never felt pain like it.

In the shock, I collapsed into a prone position with my arms in front of me. The fall pulled Jay with me which resulted in him landing on top of me, which in turn drove his giant cock completely into my ass. All 9 inches. The air left my lungs and all I could do was whimper. The head of his cock was smashed right up against my prostate, and I could feel his big balls resting against my taint. It felt like someone had shoved a baseball bat up my ass.

After a moment, Jay places one hand on the bed next to me and another on the small of my back to lift himself up. Dick still deep in my ass, he places my legs together with his on the outside of mine and then lays his chest back down on top of my back. With arms on either side of my head he slowly begins to pull his hips upwards. The pressure on my prostrate disappears and is replaced with the feeling of his dick sliding out of my stretched butthole. He gets a few inches out and then slams himself down again. This is it. I’m getting fucked by a man. And holy fucking shit, it hurts. The only thing keeping me going was just how turned on the whole situation was making me.

My dick is basically tearing at the front of my panties so I arch my back and try to push my ass up. I reach down and touch my panties, they are literally soaked with precum. I pull them to the side, releasing my erect little dick into my skirt. I try and and hold it together as Jay builds himself into a bit of a rhythm. In his excitement Jay picks up speed quickly, basically just slamming his meat pole straight into my prostate. I reach around and place my hand on his thigh to slow him. “Please. A little gentler”. I softly squeeze his balls before bringing my hand back around and try to get comfy as I can whilst it feels like I’m being split in half.

At first he slows down, but it’s only a matter of time until he’s picking up speed again. “Jay please, I can’t.” I was disappointed in myself but I thought I had to call it. I cant take it. It’s just too big. I thought that maybe I’d just blow him to finish it off – it wasn’t great but it’s better than nothing.

Up until this point Jay had been quite shy, reserved and happy for me to take the lead. Hell, he’d hardly even said a word. Which is why I was so shocked to feel a hand push my head down as another one connected with my ass. Hard. I winced in pain. I felt hot breath on my ear and Jay says in a coarse whisper “yes you can bitch”. At this point I kind of freaked out inside my head. This guy was a lot bigger than me and I was in a pretty vulnerable position (he was literally on top and inside of me) and he was basically refusing my request to stop. I didn’t really have time to ponder my choices though because he then proceeded to absolutely slam into me.

I cried out. To which he told me “shut the fuck up slut, the neighbours will hear you” as he shoved my head into a pillow.

I don’t know if it was survival instincts or what, but my body kind of just surrendered and after about a minute or so of receiving an absolute pounding, I began to properly loosen up. Another couple of minutes later and my whimpers and muffled screams turned into soft little moans and eventually cries of pleasure. After my butthole finally relaxed and accommodated his massive girth I was in fucking heaven. I felt so full, so small, so slutty, so utterly slutty. I was his to do with as he wanted and there was nothing I could do to stop him. And I loved that.

I reached back and spread my ass for him to go even deeper. Jay seemed to like that because he let out a sigh and called me a slut. That made me excited so I moaned back at him. I felt Jay shift and he placed one of his big hands around my throat, squeezing lightly. “Do you like that faggot?”

That’s a massive turn on for me. Not that I’ve ever been called that before, but it’s always played a role in my fantasies. I spoke before I had time to think, “y-yes daddy”.

The hand squeezed my throat tightly and in one motion Jay kind of rolled/flipped so as he laid on his back and I was on top of him, with my back to him and my little erect dick poking up at the roof. He caught me by surprise so at first I kind of awkwardly wiggle around, but then I sit up into a comfortable reverse cowgirl. “Ride my dick faggot” Jay’s voice was deep and raspy, I could tell he was liking this.

For the next 5-10 minutes I rode Jays dick like that, just lowering my ass up and down, letting it almost fall out and then enveloping the whole thing. Jay continued to call me things like slut, bitch and whore and would occasionally demand I go faster or slower and slapping my ass. At one point I sunk all the way down and played with his balls – he liked that, so did I.

After a while I want to try something new and let his dick pop out of my ass for the first time. I feel so empty and can’t wait to get it back inside me. “What the fuck are you doing bitch?” I quickly turn around and mount Jay the other way and apologise. He grabs me by the throat and pulls my face down to his and kisses me, deeply and roughly. At the same time I reach between my legs, locate his cock (it’s not hard to find) and place it against my hole. I sink into it, loving the fresh sensation. The way his dick perfectly angles up slightly means that it is pushing even harder on my prostate now. Our kiss breaks and I lean back. My dick and balls are resting on his hairy stomach. They look pathetically small compared to his dick. Jay must have had the same thought because he smirked and scoffed a little bit, then reached out and very roughly gripped my dick. His hand easily wrapped around the whole thing and I could hardly restrain myself – my dick ached for release. “Little dick for a little slut” is all he said before releasing it and grabbing my ass with one hand and pulling me down onto him with the other.

So now I was lying, smooth bra clad chest against his hairy muscular one, as he proceeded to thrust up at me. All I could do was moan into his ear. It was truly incredible.

Another 5 minutes or so of this and he pushed up and forward, driving me into my back. He quickly grabbed both of my fishnetted legs and popped them on his shoulders, while he grabbed my wrists at either side of my body. This position was pretty hot because I could see everything. My smooth lingeried body, his muscular hairy one. The way he just pounded into me.

After only a few minutes of this, he suddenly let’s go of my legs, pulls out and quickly flips me over agin onto my stomach. I cry out in surprise a little, which just morphs into a moan as he puts it back in.

I feel something change, his breathing gets shorter and his dick seems to get warmer. He was going to cum, I knew it.

“I’m going to cum in your ass faggot”.
“Okay” was all I managed to say.

With a few final thrusts Jay drives himself into me fully and begins to grunt. I can feel a warmth begin to spread deep in my ass and I push my bum back and forward to milk it out of him. I can actually hear the squelch of his cum in my ass as I did this which was hella sexy. Jay just drops his whole body weight on top of me and I continue to gradually move my ass up and down around his deflating cock.

Eventually he pushes himself up. As his dick slides out of me, I can feel a slight dribble of cum leak down the backside of my balls. I can also feel that my previously tight little butthole is going to take some time to recover because after his dick left, it stayed somewhat looser than normal. Jay gave me a little spank and admired his handwork before taking himself off to the shower without a word. The moment he was gone I reached down and caught some of the cum leaking out of my ass then proceeded to lick my fingers and jerk myself off (legit took about 30 seconds to cum).

When he came out, Jay looked back to his sheepish self and I could tell he wanted me gone so I quickly thanked him, gave him a kiss, donned my tracksuit and drove home with his cum still leaking out of my ass.

Almost every time I masturbate now I still think of Jays beautiful big cock splitting me open and filling me with cum.

It was the hottest thing I’ve ever done.

Source: reddit.com/r/gonewildstories/comments/ajkhuc/i_dressed_up_as_a_girl_and_let_a_stranger_with_a