This story was written as a reader request for forum member (and big fan) first time sissy bitch> Please check tags before reading to make sure story will be to your liking
For what had to be the third time since I sat there my body shifted in my seat trying to remain comfortable. As I did my eyes stayed focused on your house but as of yet there were no changes. Finally what I’d been waiting for occurred as I watched the downstairs light go out and the windows turn black.
The engine comes to life as I turn the ignition and switch on the headlights. It takes less than five minutes driving and I’m parked in my driveway. Checking my pockets I insure that nothing is forgotten in my zeal to begin the night’s activities.
Though it is only September the night is cool as I zip my light, black jacket to my neck as rain falls lightly like heaven’s tears. With my hands jammed into my pockets and my head down I appear like anyone who is trying to get to where they are going before the rain becomes heavier. Only after I reach your street do I cautiously observe all around me but as it is past 11:00 P.M. there is no traffic to speak of and the majority of the well kept houses appear dark.
Right before I pass by your home I pivot quickly and walk up the side path and quietly move past your house. The fence with the privacy slats shields me from view as I reach the backyard. It is landscaped elegantly with just the right amount of vegetation balanced with the lawn I notice as my feet bring me to the sliding doors. Even better for my purpose is the window located right next to them. I slip my thin leather gloves on my hands before I remove the screwdriver from my pocket.
It takes only a moment to force the old window open allowing me to reach in and unlock the slider. My body slips inside your house where I relock the door and close the window. Waiting a few minutes for my heart to stop racing my hand rubs my large growing bulge thru my black jeans as I swell in anticipation. Satisfied that I’m in control I slip the ninja mask over my face while I glide from room to room until I reach the bottom of the stairs.
Keeping my feet to the edge of the carpeted stairs I minimized any chance of creaks as I crept upstairs. When I reached the landing my eyes observed a dim light filtering around a door left ajar at the end of the hallway. Noiselessly my body moves forward and as I get close to the door I hear soft singing or humming and I realize it must be you.
For a moment I had to wait until I got hold of myself so I didn’t just burst in the room wild eyed. Noticing that the door had an old fashioned knob and keyhole I knelt down and placed my eye to the keyhole and beheld you. It must have been your humming that prevented you from hearing the gasp that escaped my lips when I saw you sitting at the vanity. The angle I beheld you from was from the side and I saw your profile as you sat brushing your long blonde hair. You were wearing what looked to be a pink silk robe and your legs from the little I saw that the robe didn’t cover were covered in black stockings and you also had on black stiletto heels.
Unconsciously my hand ran along my leg where my fully hard erection was trapped beneath the denim material and I knew that waiting further was not an option. With a final stroke of my covered cock I rise to my feet and take a couple of deep breaths as my mind prepares for what will follow. My hand grips the edge of the door and moves it slightly and when it makes no noise I continue until it is open wide enough for my muscled body to slip through.
There were only a few feet separating us as my hand reaches out and you turn in my direction at the same time. That image of your face when you first saw me will always be burned into my mind. Your mouth opened in an “o” like you wanted to speak or scream or make some kind of noise but you were unable to. I saw you had pink lipstick on your pouting mouth and I read the fear in your big brown eyes which were framed by whorish makeup that you had recently applied. Your body attempted to rise but your knees must have gone weak as you staggered and as your hand clutched at the vanity table for support I was upon you.
My large gloved hands spun you so that your back was to me and my arm went around your slender neck while my other hand seized one of your arms and pulled you against me. Your body struggled to free itself but I easily pulled you close where you felt my hardness press into your soft ass. For a moment you were paralyzed by a combination of fear and awakened desire but by then it was too late. My hand yanked the sash from your robe and wrapped it around first one of your wrists and then the other as you belatedly tried to escape.
“Don’t move” I hissed in your ear “I’m not going to hurt or rob you but I’m just going to have my way with your sexy body that you so love to flaunt.”
All the fight went out of you after I said that and I ground my erection against your round ass for a minute making my lust very apparent to you in a physical sense. Once I sat on the vanity seat I pulled you down with one hand over my knee with your ass turned up facing me. One hand placed firmly in the small of your back held you in position allowing my other hand to roam freely across your captive body.
Your body squirmed a little and you kicked your feet helplessly in the air which I found charming and girlish. Meanwhile my hand traced a pattern up your stocking clad leg and the higher I went the more you trembled. When I reached the band of skin between your stocking top and your pink panties you gasped as the feel of the leather glove caressed your soft, tender skin. My fingers rubbed along the outside of your panties and I could feel your excitement in the front of your panties so I gave you a gentle squeeze there.
My gloved hand yanked your panties down enough to expose your white, round ass to my burning gaze as I picked up the brush you had recently been using and without warning I delivered a sharp blow to your buttocks. You shrieked in pain and again began to struggle but you were no match for my strength as I continued to rain blows incessantly on your exposed ass. The fair white skin had taken on a rosy glow from my ministrations which I continued to apply lovingly.
Only when I felt fatigue creep into my arm did I relent from chastising you further at which time I rolled you off my knee and onto the floor on your side. You seemed to be in shock from what had happened to you but it was just the beginning of your ordeal. I stood and positioned myself in front of you where I casually undid my pants and pushed them down enough that my hardness was free and rampant.
You looked up with a clearly shocked expression on your face as you saw my erect weapon dripping with anticipation for what was to come. Dragging you to a kneeling position first I then started to slap your face hard with my erect cock. The slapping sounded loud in the stillness of the room as I noticed tears running down your cheek.
“Open your mouth wide bitch and start sucking” I ordered you gruffly and as soon as your lips parted I forced my head into your wet mouth.
Now it was my turn to groan as you continued taking me deeper until my head reached the entrance to your throat. You pulled back a bit then began to bob your head up and down my shaft driving me crazy with pleasure. You released my head with a plopping sound but immediately started to lick my length as if in a frenzy. As your hands were secured by your sash you could only use your mouth but you were not to be denied. At first you concentrated your attention on the sensitive spot just below my head but soon you had worked your way down to where you licked my full balls, which you tickled with the tip of your tongue.
“Those balls are ready to give you a treat little sissy slut, do you want what’s in them?” I asked you.
Without stopping what you were doing you managed to nod your head yes at me while you looked at me with a wide eyed expression on your face. I grabbed your face and jammed my cock back in your mouth and began to face fuck you hard. More than once you almost gagged but as my orgasm neared I showed no mercy and when you tilted your head and my head slipped into your throat I knew I couldn’t last. With only seconds to spare I pulled from your hungry mouth and aimed my cock at your face.
The first rope of thick cum hit you in your eye and my next two coated your high cheekbones before you managed to wrap your lips around my spurting shaft and you greedily swallowed the remaining discharge down your throat. My hand squeezed my hardness forcing whatever was left onto your grateful pink tongue.
Though I had just blown a good load my prick was harder than ever and I was far from satisfied.
I reached down and released your hands from the sash that restrained them and slid your robe from your shoulders revealing your pink frilly baby doll and matching pink panties. When you attempted to rise my hand held you in place firmly and I shook my head no.
“Don’t you think it’s better if you stay on your knees at least for now? It is the proper place for a submissive sissy slut such as yourself. I’m going to go sit on the bed and I want you to crawl after me once I’m sitting.”
Once I sat at the bottom of the bed you crawled toward me on your hands and knees. You made sure your round ass stuck up higher in the air than the rest of you and your head was tilted enough that you could gaze up at me. When you reached my feet I lifted a foot from the floor.
“Sissy bitch, first I want you to remove my socks and shoes. Now be quick about it, no dawdling please.”
You removed my footwear as fast as you could though I felt your hands trembling with excitement as you did so. When you finished I raised my hips from the bed slightly.
“Come on Sissy, next I want you to take off my pants and I want them folded neatly. As a reward for that I’ll deign to allow you to kiss my feet. Do you understand bitch?”
With a clear eyed expression you nodded yes and after which you removed and carefully folded my pants before placing them on the bed. You wasted no time in claiming your reward but bent low and began to smother my feet with kisses. Your hot lips eagerly left their mark as you performed your proper obeisance. I couldn’t help but notice as you did your ass wiggled in the air invitingly and I found myself stroking my rigid erection before leaning forward and swatting your white ass.
Your body almost came off the ground when I did this but you didn’t pause in your duties but continued to know your place and to serve. Now both my hands grabbed a cheek of yours and squeezed hard while also separating them giving me a view of your tiny hole which I planned to fill shortly. I’d permitted you to grovel over my feet not for my physical pleasure but because I knew you’d enjoy the experience. It was a weakness of mine, being too kind for my own good but what can I say? I also removed my jacket and shirt leaving me wearing just my mask and gloves.
“That’s enough for now Sissy, you can stop. Now get up and I want you to face away from me while you bend over and spread your big ass cheeks as wide as you can” I instructed you.
Your face reflected the excitement you felt for what was about to happen to you. It didn’t take long before you were inches from my face bent at the waist with your slim white fingers prying your butt wide open. My hands dug into your smooth thighs hard making you wince from the pain when my tongue zeroed in on your tight puckered hole. You sighed with pleasure as I coated your crack and hole with my saliva while running my tongue up and down.
It was so tight that I was unable to work my tongue deeper so I spit right on it then I pushed my middle finger to the entrance before forcing it in. You moaned in a low tone as I drove it past my second knuckle until it was buried all the way in you. Your back channel was very tight on my finger which made me wonder how snug and pleasurable it would feel on my thick hardness. I was dripping pre-cum in anticipation of plunging balls deep inside your sissy bitch ass.
“Relax Sissy” I commanded “you have to open up as soon I’m going to force my big, beefy cock in you all the way and it will feel better for you if you relax.”
Next I squeezed a second finger in you which almost made you lose your balance and your stilettos didn’t help but my hand on your leg kept your body standing. Now I jammed them in and out of you trying to loosen your incredibly tight hole some but my patience waned quickly as my cock went unattended. As soon as you pushed your ass back to me it signaled that you were ready to go. Pulling my fingers out I stood and stepped in front of you where I pushed my two fingers into your slutty mouth. Eagerly you sucked on them and when I placed my cockhead by your pink lips your mouth opened as wide as it could to receive my thick prick in there as well.
“Get it nice and wet Sissy as you know where it’s going next” I told you.
You removed your mouth from my shaft just long enough to say “Yes sir, thank you sir” before you again took me into your wet orifice. Your lips slobbered on me as your saliva escaped the corners of your mouth and ran down my erection. When I felt I was sufficiently lubricated I withdrew from you and turned your body so you faced the bed with your waiting ass facing my impaler. My patience was already worn thin so I stepped forward as my jutting weapon brushed against the hot flesh of your buttocks.
My hands spread your white cheeks wide and I observed that your hole was now open slightly from the assault of my fingers. I pushed forward and my head grazed your hole.
“Sissy reach back and guide me to your hole and don’t delay.”
“Yes sir” you answered and your hand clutched my shaft just below the head as you placed it right against your opening.
With one smooth motion I pushed forward and my thickness parted your entrance and sank almost half its impressive length inside you. Holding you tightly I continued forcing myself deeper ignoring the whimpers that escaped your mouth. Not until every inch was buried and my hairy balls rested against your soft skin did I pause giving you time to adjust to this welcome invasion. Your panties still sat just below your ass so my hands pushed them down below your knees allowing them to fall to your ankles.
Snaking my hand around your hip I reach between your legs and gain confirmation of your arousal as I touch you there. Your gasp is instantaneous when I graze your sensitive flesh and you try to push your body closer to me but I’m already as close as I can be.
Releasing you there I again grasp your hips and I rock backwards pulling partially out of you but before you can miss the feeling I drive back in again. My hips start to build a rhythm of pulling halfway back before slamming you hard on the return trip. With each thrust I hear our flesh slap as we increase the tempo with you pushing back as I move forward. Suddenly I catch you off guard and when I thrust forward harder than before you lose your balance and topple forward onto the mattress disengaging my cock from your ass.
I can’t help from bursting out with laughter from that but I’m already moving to adjust. Taking a pillow from the bed I notice that its pillowcase is made of silk before I slide it under your hips as you lie on your stomach with part of your legs hanging off the bed. Spreading your legs wider I put my knees on the edge of the bed as I guide my erection back into your welcoming ass. You moan with desire as it again slides deep in you filling you up while making my senses reel from the feeling of pleasure.
Once it’s all the way in your hot hole I place one hand on your lower back and the other on the bed next to your body and begin to slam you forcefully now. My body drives into yours with full force with each thrust as my hand keeps you helplessly in place. You’re making whimpering sounds as I pound your ass with no mercy but it is obvious that none is needed as you are greatly enjoying yourself. My thrusts become even more rapid and whether it’s that which causes it or the silk pillowcase you’re rubbing against the reaction comes quickly.
You moan louder than before and gasp “I’m cumming” and seconds later I feel your sphincter clamp on my thickness like a soft vice. It is literally impossible for me to move my cock as your climaxing body tightens every muscle on your sexy body but especially your ass. My cock can feel you cumming and I experience each spurt as you climax on the pillow. Only after you finish do I move but I manage to stand while staying buried in you and bringing you off the bed as well. The pillowcase is covered with your sticky, white cum making a big mess.
“Sissy don’t leave that there. A cum swallower like you should lick up every drop.”
Even though it is your cum you go to town scooping each drop from the pillow and bringing it to your hungry mouth where you swirl it around before gulping it down. After you lick up every drop I push you back on the bed on your belly while staying in you the whole time.
“What do you say Sissy for me letting you cum like that?’
“Oh thank you sir, that was very kind of you but now fuck me with no mercy until you cum please. Don’t hold back from using my body as you see fit.”
“I didn’t plan on it though it is nice to see we are in agreement Sissy.”
With that I started fucking as hard and fast as before. The only difference from before was my body rested on my elbows keeping me closer to your body as we fucked. Your ass still felt incredibly tight and now you started to clench and unclench you posterior as I sodomized you. Our bodies dripped with sweat as they moved in unison and soon I found myself getting close.
“Sissy reach back and fondle my balls as they have a present for you” I managed to gasp out as my orgasm rapidly approached.
Your hand managed to work under your body and between both our legs and then caress my testicles. My teeth clamped on your neck as I exploded deep in you. It was a true la petite mort moment for me as I collapsed on you as my balls fired spurt after spurt and I almost blacked out from the intensity. It took me a full three minutes before I could move but slowly I revived although I stayed in you as my spent penis shrank toward normal size.
“That was incredible Sissy” I whispered in your ear “and I knew it would be. From when I saw you that first time while I was jogging I had to have you and I decided nothing would stop me. And this morning when I saw you saying good bye to your wife as she got in that taxi with her suitcase I figured tonight would be the night that we met.”
After saying that I pushed one more time with my shrinking cock giving you one more jolt before rolling off your soft, willing body. You didn’t wait but rolled to your side where you could clean off my prick. You licked and sucked it lovingly but I resisted allowing it to grow again. Only after you finished cleaning it did you turn your face toward me.
“Sir you said that were watching me. That makes me feel very special and desired and I thank you. Not many can see what is before them but you can see below the surface even and I’m grateful.”
Realizing my time was short tonight I sat up and started to dress as you gazed at me with a strange expression. When I finished you stood up and I saw a tear in your eye.
“Don’t cry my little bitch” I told you “as I plan on seeing you again. That is what you want too, is it not?”
Wordlessly you nodded as you fought from smiling broadly and revealing how smitten you had already become. Proving to you I meant what I said I removed my mask exposing my face to you and causing you to gasp.
“I’ve seen you before sir and I thought that you were very handsome and athletic but I doubted you ever noticed me. I guess I was wrong about that.”
“Yes you were but no need to worry about the past. Now you rest and I’ll let myself out but be assured we will see each other again and I have plans for you.”
When I said this you couldn’t help but to smile as I headed out the bedroom door.