Caught by my Best Friend

Caught by my best friend

A little about me, my name is Lee, I'm 26 years old, 5ft 10, well built, not fat, but not particularly toned, still muscular with a feminine round ass.

I have been a closet crossdresser for almost my entire life with very few people knowing my secret. I'm also bisexual which more people knew about than the crossdressing, one of those people was my best friend Danny, this will come into play later!

Danny lived in Nottingham, 2 and a half hours from my place in Essex, we rarely saw each other but always made a point to keep in contact since he moved away 7 years ago. We have been best friends as long as I can remember and I secretly always had a bit of a crush on him and fantasised many times about him admitting a secret desire to fuck me.

We had arranged for me to stay at his place for a couple of days during the summer, he said he would show me some of the local pubs and clubs while I was there. He lived with his girlfriend, Coral, who was 6ft 2 and around a size 14, attractive and feminine but very tall with a great hourglass figure. Danny was 6ft 4, slim with toned muscles and a short, well kept beard.

Coral would be away with her family the weekend I'd be visiting, so it would be just me and Danny. Well I arrived around mid day, unpacked (I kept my stash of womens clothing and lingerie tucked away in my bag incase he went through the drawers for any reason while I was staying) we spent most of the day just playing PlayStation and chatting as we usually do, we had a few drinks as the evening went on and I asked if I could go for a quick bath as I was aching a little from the drive, he said sure and he would put on dinner while I bathed.

I went into the bathroom and started running the bath, with some bubbles and lavender essential oil I found in the bath caddy, excited to make myself smell sweet and feminine while staying with Danny. I got into the bath and washed my smooth, clean shaven body, after about 10 minutes I started looking around the bathroom and something in the wash basket caught my eye, it was a pleated red tartan mini skirt, I had to have a better look at it, so I quietly got out of the bath, leaving the plug in so Dan wouldn't know I was out yet, quickly dried off and started rummaging through the basket.

Along with the skirt I found what appeared to be the rest of a slutty schoolgirl outfit, white stockings with lace tops, and a matching suspender belt, and a blouse with a small tie loosely wrapped around the neck. As I took it all out and laid it on the side I noticed something else, a beautiful underwear set. Soft, red lace Brazilian style panties and a matching soft cup bralette. I picked up the panties and examined them, noticing obvious cum stains around the crotch and ass area.

My mind raced with images of how these stains might have occurred, but I was sure of one thing, it was Danny's cum and I needed to put these dirty panties on right now!

I first put on the stockings and suspenders, slowly sliding them up my smooth silky legs and clipped the suspender straps to the lace tops. Then it was time for the panties, I slid them on and noticed the stark contrast between the soft stretchy lace and the slightly hardened patched where his cum stained them. My cock was now getting seriously hard but I resisted touching myself as I wanted the whole outfit on!

So next I fastened the bra round my chest and then buttoned up the blouse, noticing how obvious the red bra was under the almost see-through white blouse and slid the tie over my head, leaving it loose to make it look even sluttier.

Finally it was time for the skirt, just as I slid it all the way on and zipped it up and fastened the single button, I heard Danny knock on the door, as it was just the 2 of them living in the flat they didn't see the need to have a lock on the door. "I'm coming in, I need to grab something out of the cabinet, cover your dick up" Danny shouted in a mocking tone.

I froze, looking around frantically for something to cover myself with as the door swung open, it was too late, he barged in the room covering his eyes half heartedly so as not to see me naked in the bath, he must have seen my stocking clad feet because he suddenly stopped dead in his tracks, slowly moving his had away from his face as his eyes gradually made their way up my stocking covered legs. I was painfully aware at this point that my cock was not only rock hard in his girlfriends panties, but also barely covered by the tiny mini skirt!

His eyes lingered a few seconds on my cock, then he carried on, until our eyes met, I couldn't look at, so I dropped my gaze to the floor, ashamed, excited and so horny I could explode!

"What. The. Fuck. Do you think you're doing?!" He said, with a slightly angry, but obviously confused tone to his voice.

"I... uh... I just.... Sorry" was all I could manage to say.

"Sorry? You're sorry??" He said still sounding angry. "Sorry for what? Say it!"

"I'm sorry for wearing Corals clothes, I'll take them off now and leave if you want me to." Almost hoping he would tell me to get the hell out as the embarrassment started to wash over me.

"Take them off? Not a fucking chance" his tone softened slightly as he calmed down "you look fucking amazing! I knew you were bi, but I never figured you were a sissy faggot!" He laughed

"You mean it? You think I look good?" I asked meekly.

"Ha! Of course that's what you focus on, not the fact I just called you a sissy faggot! Yes you look good, in fact, turn around and let me get a proper look at you."

I did as he said, curious and excited about where this could lead, I turned slowly, and looked down, realising that my cock was still completely solid and stretching the soft lace of Coral's panties.

"Stop!" He ordered as I had my back to him.

I stood there with my back to him as I heard his footsteps grow closer, I felt his body just slightly touching the hem of the pleated skirt, then I felt his hand softly sliding up the back side of my stocking covered thigh, and up to my perfect, round ass.

He rested his head on my shoulder lightly and whispered in my ear "you wanna know what me and coral did while she was wearing this last night? I bet you do, you want every dirty detail don't you!" He said while firmly gripping my ass cheek, his fingers unintentionally teasing my hole.

"Mmmph fuck yes please tell me!"

I said, sounding like a horny slut!

"Hmmm..... nah..." he said, which disappointed me just for a second before he carried on.

"I think it's best I show you instead." He softly kissed my neck, making my knees buckle slightly, he reacted by putting his other arm around my waist, I suddenly felt safe, protected, and most importantly, owned. I was his, there was no doubt in my mind that I would do absolutely anything he wanted me to right now.

He kissed my neck some more before telling me "turn and face me now you fucking slut!" He ordered forcefully.

I slowly turned, keeping my eyes glued to the floor as I faced him.

"Look at me you whore" he ordered as he grabbed my face and aimed it at his, our eyes met, and he leaned in to kiss me, looking up at him from our him eight difference, I leaned in too, as our lips met I felt like his girl, his slut, his property!

We kissed passionately, his hands exploring my body and finding their way to my lace clad ass, squeezing and groping. He teased my hole some more as my hands found their way to his hardening cock through his sweat pants.

He slapped my hands away and told me good girls use their mouths.

I grinned a dirty smirk and dropped to my knees, eager to take him in my mouth!

Kneeling before him I was at eye level with his stiff, throbbing cock, I had imagined what it would be like before, but had never actually seen it, I reached up to the waistband of his sweat pants and slipped my fingers in, being sure to grab his boxer shorts too and slowly pulled them down, noticing his dick straining against the material as it was about to be exposed.

As I pulled down his dick sprung out, very nearly smacking me in the face as it bounced in the air before it settled, pointing right at my face.

It was much bigger than I had ever imagined, at least 7 inches and thick! Uncut, and ready for action.

I smiled as I looked up into his eyes.

"Take it like a good whore" he told me.

That was all I needed to hear, I eagerly started to kiss and lick up and down his red bull can sized shaft before teasing my way to the tip. I paused for just a few seconds with my lips pursed around the tip and with my tongue, teased and tasted the hole, noticing the distinct and familiar taste and texture of precum.

With that I tightened my lips, being sure to get my teeth out the way, and slid it inside my mouth as far down as I could manage, I gagged as it hit the back of my throat and went to pull away, suddenly I felt his hand on the back of my head pushing me further, I panicked for a second as I struggled to breath, and then I relaxed and let it slide down my throat, my tongue massaging the underside of his shaft on the way down until my nose touched his pubic bone and his balls rested on my chin.

Slowly and deliberately I pulled back all the way to the tip and then slammed it back down my throat, he let out groans and moans of pleasure as he called me a good sissy faggot, spurred on by his degrading words I sucked harder and faster before settling around the tip and furiously massaging it with my tongue, slapping around the head and sucking hard. I felt him start to tense up as he told me to stop because he was about to cum! This just made me more hungry as I slurped and throat fucked myself with his cock once again.

To my surprise he pulled away, *POP* as his hard, wet member was released from my suction. He ordered me to stand.

Back on my feet he slipped a hand around my throat and squeezed, not too hard, but hard enough to get his point across. "When I tell you to do something, you fucking do it okay? You need to understand that tonight you're not Lee, not a man, not even my friend, you're just a dirty little whore that I own for the night, maybe the whole weekend. You are mine. My property and you will fucking obey me!" His grip got tighter and tighter as he spoke until I couldn't breath anymore. Finally he released me. Catching my breath all I could manage to say was "yes sir, I'm sorry for disobeying you"

"You really think Coral wore that outfit and all she did was suck my cock? Surely you noticed the cum stains around the ass area? Of course you did" he smirked "that's probably why you put them on in the first place isn't it!"

My face reddened as he so accurately narrated. "Yes sir I did notice it"

"Ha! Good girl" he said softly, sending waves of pleasure through my body. Being called a good girl was my number one turn on, especially after being called and treated like a whore! In that moment I wanted nothing more than to be his girl.

"Now, turn around and bend over, show me that sexy arse of yours"

I did as I was told, bending at the waist and arching my back as best I could, resting my hands on the edge of the bath for support. Danny's hands instantly found their way to my eager ass, softly rubbing and gripping my cheeks, spreading them. "Mmmm looks like you've got a tight little pussy, but I bet you've practiced taking cock before haven't you?"

I moaned but didn't say anything.

*SLAP!*

He smacked my right cheek so hard I actually helped.

"HAVEN'T YOU!" He spoke forcefully demanding an answer.

"Yes sir, all the time but never with something as big as your gorgeous dick!" I said trying to sound as feminine as I could.

He chuckled lightly as he continued rubbing and dropped to his knees behind me. He pulled my panties down slowly. I remember being so glad that I'd put them on over the stocking straps for easy removal as they finally dropped to the floor around my ankles.

With one hand on each cheek, he spread them apart and before I knew it his face was buried between them, his tongue delicately dancing over my eager, aching hole, pushing in ever so slightly.

My bodies natural reaction was to push back on him, wanting him inside me. To my surprise and relief, he reacted by pushing his tongue deep into my clean, tight asshole.

My knees started to go weak but I managed to hold myself in place as he tongue fucked my hole for a few minutes of pure, full bodied pleasure. I felt his saliva coating my hole as it relaxed.

"Mmmmmm ohhhh please fuck me daddy!" My words feeling like they weren't coming from my mouth, there's no way I was brave enough to tell him what to do! Knowing full well he would soon be ramming his monster cock into my tight boy pussy.

He stopped just for a moment and told me "that's it Leah, beg for my cock"

Leah? He called me Leah?! My mind raced, Leah was my online persona for when I dressed and posted pictures! Did he know? Had he seen my twitter before?? Or was it just a lucky guess?

It didn't matter, hearing him call me that name sent me into overdrive!

"Yes! Please daddy I need your cock inside me! I've been dreaming about it for years but it's so much bigger than I'd ever imagined! I need it please daddy please fuck your little whore!"

With a menacing chuckle he stood up behind me, letting his cock slide between my now wet ass cheeks, teasing my hole as it glided over the top.

He held his member tight in his hand as he lined it up with my boy pussy, and pushed softly, the head slid in with relative ease though I was a little tense from the anticipation, after the head popped in, he went to town. He grabbed both my hips and rammed himself deep inside me, I felt his balls slapping into mine as he bottomed out inside me!

I was in absolute heaven, panting, moaning and begging for him to fuck me hard. Well he didn't need to be told twice, his grip tightened on my hips as he began his brutal assault on my pussy, my own cock softening but glazed with precum as I focused on the pleasure of his thick, hard rod slamming into and sliding over my prostate.

I went absolutely wild, bucking my hips pushing back on him to get him even deeper, perfectly matching his thrusts as I screamed in pleasure. Danny was also moaning, deep manly grunts through gritted teeth as he fucked me like he hated me, in stark contrast to my own girlish moans of pleasure. All of the sudden he stopped and pulled his cock out. Still bent over I panted as I felt my gaping hole spasm, feeling empty I begged him to keep fucking me "please daddy keep going I want you to fill me with your cum!"

"Soon baby girl, if you keep being a good little slut you will get your reward" he said, catching his breath.

"Come into the bedroom and get on the bed" he ordered.

Wobbling on my weak legs I made my way into his bedroom and laid in the centre of the bed on my front. He followed behind me. "Arms up above your head" he barked. My arms shot up spread as wide as I could manage, trying my best to obey him and please him.

He walked over beside the bed and pulled out a strap, with a cuff at the end, which he fastened around my wrist before walking over the other side and repeating.

"What are you doing daddy?" I asked softly, not really caring what he did because I just needed him to fuck me again.

"Don't ask questions, just enjoy it" he spoke softly, like a boyfriend comforting his girl, well I guess that is wha he was doing after all.

"Yes daddy, I'm enjoying every second" I replied.

"Here let me put this on you" he said as he wrapped a pink leather collar around my neck, with a chain attached to it. He fastened it tight around my neck, just slightly restricting my breathing, but not enough to strangle me.

"One last thing" he said.

Next I felt a blindfold being gently slid over my head to cover my eyes. All of this had made me continue to drip precum and I was now laying in a puddle of my own juices.

Silence befell the room, and then footsteps, next I felt him walking on his knees over the bed, positioning himself infront of me, naturally I opened my mouth ready to accept his cock once more. As it touched my lips I quickly realised it wasn't Danny, this cock was thinner, and cut, the smooth head unmistakably different to Danny's. I don't care though, it didn't matter who's cock this was I wanted to suck it.

My mystery lover started to thrust deep down my throat, he may have been thinner than Danny, but I thought it seemed to be longer, reaching parts of my throat I didn't think was possible, at a guess I'd say 9 inches from the feel of it. He picked up the pace, pulling on the lead hooked to my collar as he fucked my face.

Meanwhile my hips were aggressively lifted up, forcing me onto my knees as Danny lined up behind me once more and rammed his cock back inside me, going to town fucking me harder than ever before, I couldn't handle it anymore, the spit roasting I was receiving was just too much to handle and I felt my body begun to spasm as my limp clit twitched between my legs, streams of hot sticky cum soaking my skirt and the bed beneath me. As I came, my hole tensed tight around Danny's cock, making him moan loudly, and my mouth suctioned harder around my mystery lovers cock, making him moan as well, all of the sudden I heard them both in unison say "oh fuck" as they froze and their cocks both began to tense and pulse inside me, all at once my mouth and my boy pussy were filled with streams of hot cum, I was in heaven, a dream finally coming true as I swallowed all I could and tried to keep Danny's cock inside me just a few seconds longer.

Once they were both finally done the let their now softening cocks slip out of my holes. I felt Danny's cum dribbling out of my hole as he unhooked the straps on my cuffs, and turned me over to lay on my back, then the blindfold was removed.

I looked around the room in total shock, 2 more guys that I didn't recognise stood over me, one either side, hard cocks in their hands stroking themselves, almost on reflex I reached up and took over for them both, stroking hard and fast. At the same time, Danny slid down between my legs and sucked my limp clit as it began to harden. The 2 guys started to moan and groan, I knew they were close, but I couldn't move to take their cum shots in my mouth, in unison they squirted streams of cum all over me, one aiming at my face, the other shooting his load all down my body.

This all sent me over the edge and I came in Danny's mouth, but I had cum so much already that I don't think anything actually came out!

I collapsed onto the bed, drenched in the mens seed, feeling full from all the cum I'd taken and feeling extremely proud of myself. I had been worried about post orgasm clarity ruining the experience as anxiety flooded back, but it didn't happen, I was content, I was happy, I was where I'd always wanted to be.

After a few more minutes the 3 strangers left and Danny told me to go shower and clean myself up. Sheepishly I got up off the bed, pulled my panties back on to stop Danny's cum dripping on the floor and made my way to the bathroom and stepped into the shower before removing my panties. I looked down happy and impressed with myself at the massive load I had taken that now filled the centre of the panties that lay on the shower cubicle floor. I kicked them to the corner and continued peeling off my cum soaked outfit.

Finally naked I turned on the shower, cleaned myself up and relived the events of the evening in my head, smiling uncontrollably as I did. I stepped out of the shower, dried myself and walked out into his bedroom naked.

To my surprise the bed had been made, and laid out on the edge was a black, shiny, stretchy microfibre night dress with lace detaining around the edges, and a pair of black satin panties. Knowing they were obviously for me I put them on. Just as I finished getting dressed Danny walked in, hugged me tight from behind, kissing me on the neck.