This is a quick story about how my other side, I call her Stephanie got fucked by two guys.
If you’ve read my stuff, you know that I have two very different sides to my sexual identity. My bisexual side that is full of testosterone and manhood and Stephanie. My cross dressing, cum swallowing whore that just wants to be a lady.
When I was 18 I was fairly open about my cross dressing. I had a couple straight friends that knew and didn’t care but that was because they didn’t know the whole of it. I had also made friends with a couple of gay guys that knew about it as well.
One particular night I was having a party at my apartment and Jeff, one of the gay men I knew and I were talking. He was what would be called a bear I guess. He had a hairy chest and was more often than not a top.
I had never had sex with Jeff at this point but that was about to change. The subject of sex came up in our chit chat, not about us having sex, just generic sex talk and suddenly something changed inside me. I felt this overwhelming urge to let Stephanie out. There were a few people at this party that I didn’t want to know about her so I suppressed it as best I could.
Jeff knew I cross dressed and was bisexual but had never seen me dressed up and as I said had never had sex with me. I told him if he stuck around for a while I’d dress up for him once some of the people left.
About an hour goes by and things are settling down and most of the guests have left, the others are preparing to leave. Now it’s just down to Jeff and I so I tell him to wait in the living room while I retreat to my bedroom and get dressed. I didn’t have a whole lot of womenswear yet so I just threw on what I had. I put a pink tank top on with a fishnet long sleeve shirt over it. I had a black skirt that went halfway down my thighs, a pair of black stockings that went just below the knees and for some reason I had huge strippers platform heels that I put on. I had grown my hair long now so I didn’t have to wear a wig. I brushed it up a bit, threw in some lipstick and eyeliner and boldly walked into the living room.
Jeff smiled and his jaw dropped at the same time as he complimented me on how well I looked for only being in there for 15 minutes. I sat next to him on the couch and we started talking. Talking lead to kissing and kissing lead to me blowing him before he left.
Jeff’s cock was average size but his cum tasted amazing and made me hornier than I had been in a long time. I had hoped that he’d stick around and fuck me by this point but shortly after he came in my mouth, he left. He was nice enough to kiss me goodnight though. I immediately retreated to my room, stuck one of my dildos to a chair and ride it for a good while thinking of Jeff.
A few days passed and I got a call from Jeff. He asked if I wanted to hangout with him sometime. It was obvious what he wanted so I agreed and steered the discussion towards sex. To my surprise he brought up that he had a straight friend, Colton, that had been claiming he was into trans girls and whatnot. Long story short, I told Jeff to invite him over as well.
That entire day all I could think about was “am I gonna get doubled up on by two guys?!” Jeff had told me to wear the exact same outfit I wore for him. I agreed! Not that I had much choice, I only had 3 outfits and 3 lingerie pieces at the time.
There was a knock on my door and I opened it. Jeff stood there with a smile on his face and behind him was this adorable shy guy that I could tell was nervous as fuck. That instantly made me nervous as well because he was super cute. Truthfully I wasn’t feeling Stephanie much that day but when I opened the door and saw them both standing there, my boy pussy got drenched!
I lived in a 2 bedroom apartment at the time and it worked out great. The extra room allowed me to have one room for me and one for Stephanie. I did my best to make it look like an 18 year old girls room but yeah, that didn’t work out lol.
We didn’t bother to make small talk, I just closed to apartment door and grabbed them both by the hand and lead them to Stephanie’s room. I closed the door behind me and walked towards Jeff and wrapped my arms around him. I thought it’d make Colton feel more comfortable if he saw the two of us get things started.
Jeff and I began to make out. As we did I reached out my hand and took Colton’s hand and pulled him closer to us. Now with one arm around the waist of each of them I slowly leaned in and gave Colt a kiss and a soft squeeze of his butt. Then returned to kissing Jeff with more passion and intensity. This time when I went to kiss Colt, I put my tongue in his mouth. He was beginning to relax more and more now.
As Colt and I continued to make out, Jeff began kissing my neck and squeezing my ass. I could feel each of the hard cocks press against each of my legs through their blue jeans.
I couldn’t take anymore foreplay, so I got down on my knees in front of them and unbuttoned both of their jeans and yanked them down to their ankles. Jeff’s cock I had seen before so my eyes went more towards Colt’s. His was a little bigger, at least 8” despite him being a little shorter than Jeff, he was bigger than him down there.
I began with Colt’s cock but didn’t ignore Jeff. My mouth was going back and forth between their cocks. I had never been with two guys at the same time before!
Both of them had now removed their shirts and kicked their jeans off into a pile on my floor. I joined them and removed my tops, skirt and panties leaving my stockings and heels on. I told Colt to lay down on the bed. I crawled between his legs on all fours and began sucking his cock again. I stuck my ass up and told Jeff to fuck me. I felt Jeff spit on my asshole and then press his cock against it. I was so into Colt’s cock in my mouth that I didn’t even notice that Jeff had popped his tip inside my ass. As he began to slowly thrust though I began to moan. All I could think about was, “I have a cock in my mouth, and a cock in my ass! Oh my god!!”
I began to think I was doing a bad job sucking Colt’s cock because he hadn’t came yet. A few nights earlier I blew Jeff and he came within 2 minutes. It had been almost 10 minutes since Jeff started fucking me and neither of them had cum yet. I felt like I was in a porn movie!
“Oh shit I’m. Gonna cum!” I hear Jeff moan from behind me.
He begins to thrust as hard as he can and it’s an intoxicating mix of pain and pleasure. He’s thrusting very hard, fast and deep and it’s a bit painful and there’s no way to make it go away but also incredibly pleasurable because I knew I was making him cum!
Jeff let out a loud groan as he pushed his cock as deep as he could inside me. His hands squeezed my hips so hard it left nails marks. I felt his cum spurt inside me tickling the inner walls of my ass. As he pulled out, I felt his cum begin to push its way out of my stretched hole and dribble down my leg.
“Your turn!” I said looking up at Colt
I rolled onto m my back for Colt. I wanted to see him fuck me. I was unbelievably attracted to him and I just wanted to see him fuck me.
Colt positioned himself between my legs and lifted them upwards holding my ankles. He ran his tongue up my stocking and kissed my high heel. I could feel Jeff’s cum still oozing out of my hole. I saw Colt’s cock bob up and down with anticipation. Jeff took some initiative and grabbed a hold of Colt’s cock and pressed it against my hole. Colt squeezed my ankles and pulled them to his shoulders as he thrusted his cock inside me. Even though I was stretched out by Jeff, Colt had a longer and noticeably thicker cock and as it slid inside me, I let out a loud moan. A larger trickle of pre cum squirts from my cock onto my stomach as Colt begins to slowly thrust into me.
As Colt continues to fuck me, Jeff positions himself next to my head and puts his cock in my face. I took a hold of his shaft with my hand and began stroking him. I knew he wanted me to suck him but I had never done ass to mouth before and was super nervous. I did a pretty good job of cleaning myself up before hand, enema and stuff but still nervous. Plus I was lost in watching Colt’s facial expressions as he grinding into me.
Jeff still had a small trickle of cum on the tip of his cock and I was so turned on that I couldn’t take it anymore and I put his dick in my mouth and began sucking. If it tasted like shit, I didn’t notice because once again, all I could think about was “I have a cock in my ass and a cock in my mouth!!”
I tried my best to keep an eye on Colt as he pushed his cock in and out of my loose ass. I kept my other eye on Jeff as he started fucking my mouth. My hand was now up to his chest running my fingers thru his chest hair. I was so turned on by it all that I emptied my balls all over my stomach. I hadn’t cum like this in a long time! There was cum all over my stomach and chest and it dripped down my side and onto my bed.
Colt then pushed my legs off his shoulders and leaned down almost on top of me. I wrapped my legs around his waist as he began grinding his big dick deeper and deeper inside me. I could feel his balls slapping my ass cheeks and knew that his entire manhood was now inside me.
Then, maybe the weirdest thing to ever happen to me happened and I reacted completely different than I would’ve ever imagined I would.
As Colt kept thrusting in and out of me, my left hand was digging my nails into his back hoping he’d never stop fucking me. My right hand sifted thru Jeff’s manly chest hair and his cock still in my mouth.
Suddenly Jeff stopped fucking my mouth and sat still, cock still in my mouth. Then I felt a wet burst hit the back of my throat. I thought I had made Jeff cum again. I soon realized it wasn’t cum, but piss. I spit Jeff’s cock out and gagged a bit as I swallowed his unexpected piss. As I tried to catch my breath what was left of his burst of piss hit my face. As soon as it started though, it stopped.
“What the fuck was that?!” I asked
“Sorry!” Jeff said noticeably uncomfortable “I just got lost in the moment. I’m so sorry!” He continued
“All you had to do was warn me and we could’ve been fine” I explained
“I know, I know, I’m so sorry!” He once again professed
“I didn’t tell you to stop!” I said looking up at Colt
Colt cracked a little smile and resumed fucking me. I have no idea why I said and did what I did next but I just did. I guess I was also lost in the moment as well.
“I didn’t tell you to stop either!” I exclaimed looking up at Jeff and grabbing a hold of his dick.
“Wait, what? Seriously?” He asked confused
“Why not?” I said out loud. I was definitely thinking it but didn’t think I had the courage to say it out loud.
I had never been pissed on or pissed on anyone before, nor did I ever think I would. I had never thought of it. I knew it was a thing people did but I never thought about it. Not even for a split second. However, the theme of the night seemed to be “there’s a first time for everything”. I had never been with 2 guys at the same time, I had never done ass to mouth, and I had never been pissed on. Well, check them all off my list. Besides, he had already pissed in my mouth unannounced anyways and I wasn’t as disgusted as I thought piss tasted.
As Colt continues to thrust in me, and oh my god, I had been sucking his cock for almost 10 minutes and now he’s been fucking my ass for another 10 and still hasn’t came yet! What a fucking machine! I held onto Jeff’s cock and pointed it at my mouth. I waited for a few seconds and saw a small amount of pee dribble out and onto my hand.
“Oh fuck! Oh fuck! OH FUCK!!!” Colt groaned out.
I could feel his cum pumping into my ass. I couldn’t believe that I felt it as much as I did. Just seconds later a warm blast of piss hit my face. I immediately pointed Jeff’s cock toward my mouth. His warm piss bounced off my tongue and drooled down my chin onto my chest. I thought to myself, “this isn’t so bad. It’s not all that different from cum.”
Then a second wave of Jeff’s piss shot in my mouth. This time I relaxed my tongue a bit and it hit the back of my throat. I swallowed as much of it as I could but it was a lot of pee and most of it drooled down my chin and everywhere else. Jeff pushed out the last of his pee and then he laid down next to me. Colt slid his meaty hog out of me and laid down on the other side of me. I was absolutely covered in sweat, cum and piss and I fucking loved it! We laid there exhausted for almost an hour just talking, never bothering to clean up the utter mess we had made.
“Sooo.. this is gonna be a regular thing with us right?” I asked them
They both laughed and agreed that this was NOT a one time thing. Something about guys that are sweet and respectful and treat me like a woman turns me into such a filthy whore! And I fucking love it!!!!
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