Shark Tank

(via sissyorgasm)

I crave for my sissy holes to be stretched

(via sissyorgasm)

I crave punishments when I am bad. I need to be spanked and bruised like the naughty little whore I am.

(via sissyorgasm)

I crave to be tied down and used like the sissy slut I am

(via sissyorgasm)

I crave for you to spread my legs and force me to sissygasm and then clean up the mess I made

100% true story, as I remember it.  I think this is where it all started for me.  Allowing myself to be dominated, and knowing that I could make another guy as hard as a rock. My next door neighbor was a year older, and one of my closest friends.  We would hang out at his place most summer afternoons since both his parents were at work during the day.

The house was ours to hang out, play Sega Genesis, watch Saved by the Bell re-runs, etc. We were both extremely horny guys, but really what teenage boy isn’t?  Many afternoons were spent in his living room watching whatever Skinamax shows his dad had taped on VHS.  Although we would often settle for scenes with only a few fleeting glimpses of beautiful women with their tops off.  Random “B” movies like Nowhere to Run or The Hollywood Knights.

Sharing the couch we kept pillows over our laps to hide our excitement.  Side by side, our legs would often touch.  At first it was an accident, it just happened and we would kind of jump back into position.  Over time though, I actually found myself initiating the contact.  Subtle movements like my knee resting against his.  Or going to the bathroom and then sitting down even closer to him when I got back so our thighs would touch.  

I didn’t think I was gay or even bi, I was just a teenager who was too shy to actually engage with a girl.  Watching sex scenes with him him was the closest thing I had experienced to sex.  It didn’t take long before I started gently pushing my feminine side onto him.  I didn’t even know I had it in me, or exactly what I was even doing.  I would push him with flirty hands, saying things like “Oh stop it!” to him, as if I was making fun of the way real girls would do it. Once I started, these feminine outbursts just wouldn’t stop.  In fact they began escalating every time we were alone.  I took my pillow, climbed on top and began riding it.  I’m sure I looked like I had no idea what I was doing at first, because the truth is I didn’t!  He looked at me confused the first time and asked, “Uh what the hell are you doing?”  So I went home and practiced.  Every day I got a little bit better, and I would sneak it in while we were hanging out.

His confused glances began turning into curious ones.  I arched my back, stuck out my chest and pulled my shoulders back.  My hips rocked and swayed, while my ass circled as it grinded into the pillow.  I was putting the pillow first and not letting my cock be the center of attention, rather imagining that my pleasure was coming from the one I was riding.  Soon, my friend also began thrusting his hips into his pillow.  However, he was treating his as if it was the female.  It was in his lap while he rocked into it with gentle ease at first.  He must have quickly realized how good it felt, because it wasn’t long before he was pushing it to the next level.  He put the pillow on the couch, and came at it from behind with even more ferocity. I wondered, had he been practicing at night too?

While he pretended he was going at it with Kelly Kapowski (seriously, he started telling me that’s who he was imagining while he thrusted), I decided to get vocal also.  Although, I didn’t have any girls in mind to mention since I was imagining myself in that role.  So I began moaning, at first kind of loudly and comically just in case it wasn’t well recieved.  Then it became more sensual and honest.  My voice cracking slightly as I went falsetto and girly. Now he was riding his pillow like a man, next to me riding mine like a woman while we both moaned passionately.  I was so hard, so confused, and turned on like a mother fucker!

Unable to control myself any longer, I rolled onto my back and pretended the pillow had taken over me.  I spread my legs wide while pillow took control on top.  I was getting more animated now, panting, breathing loudly, eyes closed in a passionate rage!  I couldn’t control the words that came out next, I was totally in the moment.  "Give it to me, come on, don’t stop!  Pound me harder you hunk!“  (Dumb line, I know… but I remember saying exactly that.)  It was in that exact moment, that something snapped!  He lunged over toward me, threw his pillow on top of mine and grabbed my left leg as it stood straight up over his shoulder.  I let out a light laugh, just to make sure he understood that I was on board.  He smirked and squinted his eyes while he began pushing his hard dick into his pillow.  He started immediately at a slightly frantic pace.  He couldn’t control his teenage lust.  Even if he didn’t think he was gay, he now thought of me as feminine enough to dominate.  There were two pillows between us, but with each thrust I let my pillow slide further away until it was off the couch.  

One pillow separated us. One pillow and some thin shorts between our cocks which were as now hard as rocks!  I let left my leg slip down onto his shoulder.  He bit at playfully it with his teeth while he let out a light roar and laughed.  He was still trying to keep this as "not gay” as possible.  However, I wouldn’t have any of that at this point.  I was exactly where I wanted to be, and could have let this go all night.  I took my right leg and placed it over his other shoulder.  This must havet aken the fantasy up a notch for him, because his smirk went away, and he got the look of a true man nearly ready to pounce.

He started humping faster, harder and with more passion.  His hands slipped from the last pillow between us onto my legs.  He squeezed my hamstrings tight… so tight I opened my mouth wide and let out a loud squeal.  I placed my hand on top of his and rocked my body into his.  We weren’t immediately in sync, our motions were sporadic as we bumped ourselves together. Every time we slapped together awkwardly I let out aloud “OH!”  By now the pillow flew off my lap and onto my face.  I let go of his left hand to remove the pillow from my face.  Suddenly I felt his powerful grip holding the pillow over my head.  It wasn’t over my mouth, thank goodness, but it was covering my nose and eyes.  My panting was now out of control.  Warm breaths poured from my mouth in rapid succession as I could no longer breath through my nose  I didn’t care.  I couldn’t care! Now, he was grinding up against my ass and sweeping up toward my cock with every powerful thrust!  No pillows.  Just uncontrolled teenage lust!

I took his hand from the pillow over my face, and pulled it toward my lips.  After a gentle kiss on the tip of his fingers, I opened my mouth and pulled his pointer and middle fingers in.  I treated them as they were his throbbing unit.  Sucking and licking them while my warm breath panted out like a dog every moment.   How long could this go on??  Was the next step coming??  He was in complete control while I continued to give encouragement.  He was so fucking horny now!  His words set the tone for what he wanted next,  "You want this?!  Huh?!!“ he groaned.  I did want it!  So badly, but before I could even shout it out, he continued, "You’re gonna get it, Kelly, get ready!!!”  (I guess he was imagining that I was Kelly Kapowski while he pounded away at me over my clothes.)

He ripped his hand out of my mouth, and I pulled the pillow off my face!   I didn’t want to miss this!  He reached deep into his pants and whipped out the most beautiful sight I had ever seen.  It was standing up straight and as hard as I imagined.  His shaft was covered in a small patch of brown hair, and it was vainy as hell!  He was larger than I was, but only by an inch or so.  I think it was about 6 ½.

I quickly yanked down my basketball shorts, which rested at my knees.  He leaned in and I felt his warm dick rubbing gently against my balls.  He was actually feeling around for my ass.  He wanted to be inside me.  This man wanted to be inside me!  I had never felt so alive, so feminine, and so turned on!  I arched my back, scooted closer and tried to help him along.  His hands grabbed my hips, strongly and he yanked me right up against him.  His rock hard cock sailed straight at my virgin asshole.   “Ahhh, oooww!!” I yelled out a painful squeal!  I had no idea how this was going to fit, and exactly how this would work.  We had no lube, and I was a virgin.  There was no way he was going to get that beast inside me!

It’s obvious now, but we had no idea then, so we kept trying. He rubbed his gorgeous mushroom inside my ass cheeks, trying to make progress.  He spit on his hand and rubbed it into his meaty cock.  This helped loosen thing a bit, I felt the tip squeezing into my virgin hole.   I wanted it so bad, but it wasn’t going in.  He groaned… he was so turned on, and now i felt like a tease or something.  So I did the only thing I could think of. “Wait!” I said and rose up from my back.

The moment was nearly gone, but I didn’t want it to end! I shoved him back against the couch, forcing him to lay down.  This was the first time I took control.   Now I was calling the shots. I was a woman in control!  I didn’t even think, I leaned in quickly over him and opened my mouth.  His manhood smelled of a slightly spicy sweat.  A fantastic manly scent built up over the early moments of pillow humping.   I kept my eyes open, not wanting to miss a moment of this.  My lips met the head of his cock, and I used my tongue to lightly lick the hole right at the tip.  He let out a moan, “Oh, Oh, Kelly, wow! Yes, ohh!”  I leaned in further, and brought his shaft deeper into my throat.  His body started to tremble and he slapped his hand on my head, grabbing a fistfull of hair.  He thrust himself deeper, and I began gagging.  I was not ready for penetration this deep.  He squirmed randomly, and the screamed, “Ohhhhhh, ohhhhhh!!”

Something warm hit the roof of my mouth, and I knew instantly that I was receiving his tasty sticky load.  I had tasted my own cum while masturbating, so I already had an idea what I was in for.  His cum was different, I can’t even explain exactly how… just different.  Three more pumps of juice, and his load was dripping out of my mouth now, and onto his pubes around his shaft.  I didn’t know what to do exactly, so I leaned in and started licking cum off his pubic hair.

I licked twice, and then stopped to look at him. I wondered, what do we do now? I hadn’t finished yet.  I was now harder than I had ever been in my life!  This was my first sexual experience, and I hadn’t cum yet.  Then, the scariest moment of my life happened… I heard a squeak of the garage door opening!

FUCK!  We were one room away from his Mother who was getting home from work!  It was 5pm!  He and I shared the same look and jumped to our feet.  His cum still on my face, and both of us with our pants down!  we darted over to his room, which was thankfully in the other direction away from the garage.  We  leaped through his door and swung with forcefully.  It hit with a crash!  Shit, that sounded suspicious!  We pulled up our pants, and I reached to wipe his sperm from my mouth when the door opened.  

His mom was pretty strict… More strict than my parents at least.  "You know better than to slam this door.  What are you boys doing?“ she asked. "Nothing really”, he said nervously.  I responded, “Yeah, I’m um just leaving.”  I had just lied to his mom with her sons cum still on my breath.  I could taste him, and I was still panting.  I was in heaven.  I hunched over as I walked out of the room to help hide my still throbbing erection.

I wanted to go out and show off my new tits and the slim figure I’d been working so hard for. I decided to go to the mall and browse around in the lingerie section and see if I could turn any heads. I put on one of my thin sundresses, no bra and a pair of my sluttiest panties. I have my panties specially made to help to hide my gurl cock and keep it from showing itself at inopportune times. I put on my high heels to accent my legs and my ass, they made me feel like such a hot little tramp. 

I got to the mall and the cold air hardened my nipples and they poked desperately at my dress to get free. I perused the little kiosks and had my nails buffed, my eyebrows threaded and my bracelet polished. I had a couple of young hunks looking my way, but they looked too shy. I needed a man that was bold and takes what he wants. I stopped by the food court to get an ice cream from the Dairy Queen. Men’s attention is drawn to a woman’s mouth when she eats, puts on lipstick and it makes them think of having their cock sucked. My confidence in myself had grown infinitely as I would pass by couples and the man would turn and look me up and down while holding his wife/girlfriend’s hand, followed by a slight smile and I’d flash one back at them while slowly and deliberately licking my ice cream. 

I was sitting on the bench, my tongue curling around my cone when I caught the eye of a young hunk, he appeared to be around college age, and I was definitely interested in him as well. His Ambercrombie like haircut and attire was definitely my type. His form fitting t-shirt, showing off his young muscles and thick chest made my mouth drool and got my gurl cock warm. Our eyes locked and he shot me an innocent, boyish charming smile and I sent one back to him with the look of shyness, yet, I’m also a bad girl. I stood up, making sure to lean over enough for him to catch a glimpse of my tits. When I looked up, I could see that he liked what he saw. I picked up my purse and raised an eyebrow as to say, “…follow me.”. I saw his reflection in the windows of the stores and he was just behind me, following closely, but not too closely. 

I slipped into Macy’s and slowly fingered the silky tops in the women’s section, sporadically looking over my shoulder to make sure he was still with me. I made my way through to the lingerie section and picked up a naughty little outfit, and looked to him for approval, to which he slowly nodded. I smiled and turned and made my way to the dressing room, making sure to stop just inside the doorway to shoot him an inviting glance. I slowly walked to the furthest dressing room and hung the outfit on the outside of the door so that he would know which room I was in. I was bent over and searching for my lipstick in my purse when I heard the dressing room door gently close and felt a hard cock pushing up against my ass. I stayed bent over, but moved my hands from my purse to the bench to give him a better look at what I was offering, and I glanced over my shoulder at him. He was staring at my ass and was just about licking his lips at the sight before him. He reached down and squeezed his cock over his jeans and when I saw the outline of his fat cock, I said, “Is that for me?” “Do you want it?” he asked coyly. “Mmmmm, yeah, I do.” I said as I spread my legs ever so slightly. He reached out and put his hand on my ass, caressed it and then squeezed. 

He dropped to his knees and put his hands underneath my dress and his fingers felt like silk on my freshly shaved legs, and they were covered in goosebumps. I looked in the mirror and his head disappeared underneath my dress and I felt his lips kissing the backs of my thighs. His kisses were so gentle and delicate, he was teasing me…and I was eating it up. I felt him grab the back of my thongs and push them to the side and his tongue pushed its way into my gurl pussy and I let out a slight cry of pleasure. His hands reached around and grabbed firmly to the front of my hips and pulled my ass towards him, his tongue burying itself further into my hole. I could feel his tongue dancing around inside of me and I thought that I was going to scream. It felt so fucking good. As he continued to tongue fuck my hole, one of his hands began to wonder about and happily found my gurl cock. He stroked it on the outside of my panties, his fingers tracing the shape of my clitty. He reached his hand inside and he got a handful of smooth gurl cock and my precum. My panties were soaked in my precum and he used it to rub the tip of my clitty. 

I wanted his cock buried deep inside of me so badly, I was aching for it. “Fuck me.” I whispered. He stood up and I heard his belt loosen and his zipper go down. His pants were around his ankles and I felt the tip of his cock slapping my tight hole. He spit in his hand and then rubbed his tip with his hand before slowly pushing the tip of his cock inside of me. “Ohhhhhh!” I cried. “Yes, give me more.” I begged. He slowly pushed inches and inches of his cock inside of me, my hole stretching and I felt my hole open wide, like his cock had pulled the switch on a trap door and my ass took the rest of him in. I felt his balls hit my ass and I knew that he was all the way in. I heard him gasp and then begin to push in and out of my ass. With my left hand, I reached down into my purse and my hand blindly searched inside. I pulled out my little bottle of lube, reached behind myself and let the lube drizzle down the crack of my ass and onto his cock. “Oh yeah. That’s better. You like that?” he asked with more confidence. “Yes Daddy, I do. Your cock feels so good inside me.” I replied. My knees were shaking from pleasure and I spread my legs further apart. His cock was pushing its way in and out of me, his balls slapping my ass and his hands firmly planted on my tits. He was pulling me backwards as he slammed his cock into me. I pulled my gurl cock out and was stroking it feverishly, aching to cum. His strokes became shorter, but quicker. I knew he was about to cum. “Yes Daddy, fuck me Daddy, fuck me.” I cheered.