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My First Time Dressed As A Girl (PT 3) (Consequenc free porn video
Well. I had written a follow up to ‘My First Time as a Crossdresser, PT 2” but Microsoft decided that the moment I attempted to upload was the perfect moment to update and erased the whole story, which means I had to rewrite the whole thing. So...
After I dressed in the schoolgirl outfit that Gunther had put out for me, I pulled my hair into a high ponytail and put on makeup emphasizing my eyes and lips without going overboard. I walked out into the living room to discover that Tracey had left and Gunther was dressed in a pair of slacks and a very expensive looking Cashmere cardigan. He smiled broadly and said he knew I’d make the right choice. Then he pulled a long tweed ladies coat out of the hall closet and handed it to me. It was a little big but fit fairly well; I assumed it was from one of his previous gurls. “Put it on we’re going out for dinner and then maybe some dancing.” He grabbed a coat for himself and we headed out after I snatched up the purse with my borrowed ID in it.
We went out to the parking lot and Gunther walked over to one of the few garages at the complex and punched a code into the keypad which opened the garage door to reveal a bright yellow Porsche 911SC Convertible. He laughed as I gaped at his ride. “What can I say? I prefer German engineering I brought it over from Stuttgart last year. Much cheaper in Germany!”
We got in and Gunther drove us to The Grotto, one of the nicest restaurants in town. We were seated at a secluded booth where Gunther ordered dinner for both of us. While we ate he asked me questions about my life quickly ascertaining that I had a lot of freedom to do as I pleased with little in the way of parental supervision because I didn’t cause much trouble at home. My Father traveled a lot and after the hell my older sister put my Mother through she was pretty content to give me free reign as long as I didn’t get into any trouble and kept my grades up. I quite often spent the night at a friend’s place so I knew I could get away with sneaking over to Gunther and Tracey’s pretty much whenever I wanted. He discussed the need for absolute secrecy with me because I was still only s*******n which could get him tossed in jail if my parents ever found out. He didn’t’ think my conservative father would take kindly to his teenage son being used as a sissy slut by an older man. Gunther explained that he traveled a lot so I would still have a lot of free time but that I was his little sissy when he was in town. I was to maintain my life as normal as possible so as not to arouse suspicion, even continue dating Mikki (which I was relieved at because even though I reveled in my newfound role as Gunther’s sissy, the thought of not hooking up with Mikki was torture even though I knew I’d quit seeing her if he ordered me too.) Furthermore I was to keep myself hairless at all times from the eyebrows down. He also explained that he had an account at a local salon and I was to go there every week on Friday after school to get my nails manicured and my toes pedicured. Once a month I was to get a facial to keep my skin soft and flawless and get my brows waxed along with a full body wax to remain as smooth and hairless as possible. He knew I was on the swim team and raced bicycles so being hairless wouldn’t be a problem but he thought that my team mates might question it if I shaved my pubic hairs although he preferred it. I said I would just tell them that Mikki hated pubes in her teeth ;-). He asked if I had enjoyed it when both he and Tracey used me together. I replied that I loved it and hoped to do it again. He said that it probably would but he had some friends who enjoyed sissies and If I was okay with it maybe he’d set something up in the future. I thought about it for a moment and the idea was really exciting. I told him so and said he was my master and I would be happy to obey any request and that it was my duty to service him and his friends whenever he wanted. He beamed at this and said I was a quick study, pulling me closer and kissed me deeply, grabbing my ass and squeezing it in his strong hands. Of their own volition, my hands found their way to his crotch where I was delighted to find his cock was swelling rapidly and soon became rock hard under my tender ministrations. I was feeling hot and bothered and perhaps the wine we had been drinking lowered my inhibitions; as I mentioned earlier we were in a very secluded part of the restaurant which was dimly lit and the circular booth was recessed so very private, additionally the table was covered in a very long white tablecloth which fell nearly to the floor. A very naughty thought stole into my head and I broke off the kiss long enough to whisper into his ear “I want to feel you in my mouth!”
Gunther pulled back and looked around to assure himself that nobody was watching us an and put his hands atop my shoulders gently pushing me down between his knees where his throbbing crotch was level with my eyes. I unzipped his slacks and unbuttoned his silk boxer to reveal his magnificent throbbing cock. I started licking it slowly at first teasing him before I engulfed the head between my pretty painted lips. I started slowly at first increasing the tempo as his cock became even harder, gradually forcing it further down my throat. It was hard because of the size but I felt a growing pride as I realized I was surpassing my previous attempts. Of course during this time the busboys and water boys who had been checking me out all night decided it was time to clear dishes and refill water glasses. My nervousness and excitement made me graze Gunther’s dick with my teeth, causing his hips to buck, which hit the back of my head against the bottom of the table making all the dishes left rattle slightly. No doubt the busboy knew what was going on which I am sure he communicated to our waiter who showed up moments later asking if we needed any dessert. Gunther replied that he was fine and his date was presently enjoying her dessert (I certainly was!) while gently bucking his hips a few times to make my head collide with the bottom of the table making it shake and rattle, ensuring that the waiter knew what was going on… Moments later I felt his cock spasm between my lips as he blew his load down my throat. Greedily I swallowed every drop and used a cloth napkin to wipe away any remaining traces of his orgasm. I was humiliated yet thrilled when we walked out together with the waiter and staff leering at us knowing our “secret”.
After dinner we went to a local disco and we danced and partied for a couple hours. Gunther was well known there and I was introduced to several of his friends who often smiled as Gunther would introduce me as his latest “discovery”. Dancing with him was fun but a little weird as I was used to leading and it took some adjustment to get used to following his lead. Slow dances were much easier as he would simply pull my tiny (comparative to his) body into his arms and physically lead me while making out with me. This caused me to just melt and let him lead me about the dance floor while I let the pleasure build within me. By the time we left I was totally aroused and ready to let him fuck me at a moment’s instance. We left the club and soon I figured out why we had parked more than two blocks away in a dark and secluded alley. We got to the car and he told me it was time to pay for my dinner, putting his hands atop my shoulders and pushing me down to my knees. I complied eagerly …sucking his magnificent cock between my lips and doing my very best to deep throat it. It was too big and I couldn’t do it but I obviously pleased him as his huge cock remained stiff the entire time. Eventually he decided he wanted more and pulled me up and bent me over the hood of his Porsche He spit into his palm and lubed up his cock, entering me roughly and fiercely. The pain was intense and it took a couple of minutes to adapt to his large cock but within a few minutes I was feeling nothing but pleasure. After several minutes of fucking we both came together.
After he was done fucking my tender ass I pulled up my panties and we got in the car and drove back to his apartment and I fondled his cock the whole time, occasionally leaning over to lick or suck on it. When we pulled into the garage he pushed his seat back and grabbed the back of my head pushing my mouth down onto his cock, forcefully fucking my mouth and throatfucking me until I would have to gasp and come up for air, saliva running from my mouth in long ropy strands, tears streaming down my face. I looked quite the mess with my mascara running and lipstick smeared all over and I gagged several times, but it just seemed to make him even harder and he would push himself even deeper into my throat, holding my head down until the gag reflex subsided. While he throatfucked me he kept up a very dirty dialog telling me what a dirty little slut I was and how he was really going to enjoy being my master as I was born to be a sissy cockcraving slut. Eventually after what seemed like an eternity he erupted violently and shot his load down my spasming again and again, both hands clasped to my head like a vice while he emptied his sperm into me. "Mein Gott Bobbi that was incredible!" I was exhausted from the strenuous activities and my knees were wobbly so he scooped me up in his massive arms and carried me to the apartment setting me down to open the door. I staggered over to the couch and collapsed there while Gunther went into the bathroom to relieve himself and clean up his crotch with a hand towel. Once he was done he tossed the towel to me and told me to get cleaned up and that he was going to take a quick nap while I did so. Then I was to pick out something sexy from his walk-in closet and get myself ready for more fun. He warned me that I had half an hour to do so and that I would receive another spanking if I was late, 1 swat for every minute late! Then he stripped naked and went into his bedroom to lie down.
I took off the high heels I was wearing as I didn’t trust my ability to walk in them in my present state and wobbled into the bathroom. God my makeup was a total mess with mascara running down my face and lipstick saliva and tears covered my face in a glaze. My eyes were red and my lips were raw and puffy from the brutal facefuck I had just received. I knew there was no way I could get myself presentable in just thirty minutes so I figured an hour would be appropriate and figured I could handle thirty swats as long as Gunther wasn't too brutal. I took a shower letting the hot water wash away the makeup saliva and tears that covered my face neck and chest. The warmth of the water felt heavenly on my sore little body which ached all over from the weekends activities, especially my tender buttocks which I knew were about to receive more punishment. I finished my shower and dried myself off. Then I applied lotions al over my skin and walked naked into Gunther's bedroom hoping he was asleep. I was reassured by the sound of his soft snoring. I went into the walkin closet on my right and was confused because there weren't any gurl clothes in the closet. I walked out and looked around and noticed another door in his room and opened it. Surprise, another walkin closet that was almost twice as big as the first one.This was an amazing closet which obviously had been professionally designed. It was filled with dresses, lingerie and girl clothes of all sorts. There were also several mannequins with wigs on them in several different colors and styles. Additionally there was also a small makeup table and lighted mirror where I could apply my makeup and tall chest of drawers with various bras, panties, and hosiery. There were also several racks of shoes with a large variety of heels in different styles and colors. As I explored the large Captains chest I found some drawers with things in them that I didn’t even know existed. There were some foam breast forms (unfortunately silicone ones didn't exist back then) Along with some bondage Items, various restraints, lengths of soft rope, something that looked like a ping pong paddle but was made from leather. Mmmm, evidently Gunther was even kinkier than I thought. I also so found several dildoes and butt plugs of various sizes. I was a little freaked out and wondered what I'd gotten myself into but hey, in for a dime in for a dollar. As I looked through the clothes I realized that most of the items were a little bit large for me, which really limited my choices. I settled upon a white satin and lace corset with a matching set of white lace panties and bra with matching garter belt suspender thigh highs and white high heels with a gauzy see through sheer babydoll negligee over it all. The bra was a bit large but when I put the breast forms in and pushed and taped my pecs to create cleavage it totally looked like I had nice c or even d cup titties! Long hours cycling under the sun had given me a bit of a farmers tan so I covered my arms in long satin gloves that came up to the middle of my biceps covering the tan lines nicely. The panties were French style and had satin ribbon ties on the side so I could adjust them to my smaller waist and could also be taken off by yanking the bows out without having to take off the garters or stockings I didn’t feel like doing my hair so I picked out a blonde wig that was styled in an updo with a French twist topped by artfully placed curls with a few curly tendrils hanging down and with a soft fringe that framed my face and wispy bangs that highlighted my eyes. Then I sat down at the makeup station and started applying my girl face. I was in the theater program at my high school and was the makeup artist for all of our theatrical productions and often did the girls makeup for them so I was pretty good at applying mine. I tweezed my brows a little bit to give them more of an arch but not so much that it would be really obvious at school. The blonde wig really changed my look so I opted for a brighter more glamorous look with my eye shadow in subtle shades of blue and silver and I opted for a paler foundation that more closely matched my torso. I used pinker rouge than I had before to accentuate my cheekbones and applied a shimmering pink gloss to my pouty lips. Once I was all ready I went back out to the kitchen poured myself a drink and popped a xanax. I loaded up a bowl and smoked it feeling very mellow and horny in short order. Glancing at the clock I noticed it was almost an hour so I went into the bedroom to wakeup Gunther. First I admired myself in the large full length mirror noticing that I looked like a young bride on her honeymoon night wearing her bridal trousseau. Gunther had moved the video camera back into his room so I checked to make sure it was positioned correctly on its tripod to get a good view of the king sixed bed and turned it on. I spent a moment admiring his Adonis like physique before I crept up on to the bed and took his cock between my lips, licking and sucking it to full erection. Slowly Gunther came awake and noticed the blonde wig." Mmmm, that looks good on you my little slut!
He let me suck his cock for few minutes before he made me stop. "That's a very nice way to wake your Master sissy gurl. But surely you don't think it will get you out of your punishment?"
"No Sir, I've been a very bad gurl and I took me thirty minutes longer than you gave me to get ready."
“And what did I tell you would be your punishment if you took too long to get ready?"
"One swat for every minute I went over Sir."
Sighing reluctantly I crawled over his body and positioned myself ass up over his thighs.
"What are you doing Sissy?" He asked
“I’m ready for my spanking Master" I replied uncertainly.
"Nice try but that's not how this is going to go down. You were a bad little girl and disobeyed my orders to be ready in thirty minutes. Not only that but you were a full thirty minutes late. Disobedient little bitches need to be properly punished so they learn the error of their ways... Don't They?"
I realized that was my cue and simpered "Yes Master, I've been very disobedient and I need to learn how to be a better Sissy. Please punish me properly Sir" wondering what I was about to endure.
He told me to go stand at the foot of the bed facing toward the bed and to wait for him
I did so and he got off the bed and walked into the closet where I heard him rustling around for a couple minutes. Then he came out to the bedroom and placed several items on the black lacquered dresser that stood opposite the bed. There was a large mirror over the head of the bed as well as a large mirror over the dresser so I could see what he was putting on the night stand. There were three butt plugs of various sizes lined up from smallest to largest, the leather ping pong paddle I had noticed earlier. A short whip made of many long strips of leather, and a black riding crop. There was also a ball gag and a black leather blind fold along with several short lengths of the soft silk rope I had seen earlier and several white satin strips of cloth. You may wonder why a 17 year old knew what these items were so I’ll explain. My best friend and next door neighbor (yes that one) had an older brother who had quite the collection of dirty magazines. Occasionally when he’d go over to his brothers place he’d swipe a couple and share them with me. One time there was a bondage magazine in his haul and we spent a lot of time perusing its naughty pages. One of the scenes involved a transvestite being tortured by a Dominatrix and he/she was wearing a ball gag. I was horrified, mortified and yet thrilled to realize I was going to be living out that scenario with some minor changes to the script. If it hadn't been for the Xanax I probably would have bolted and run.
Gunther finished putting everything in its proper order and then turned to me. “Put your right foot there" he commanded, pointing to a spot on the floor. Next he told me to put my left foot at a spot parallel to my right but about 30 inches away. Next he pulled up two small squares of carpet next to my feet that were Velcroed so as to stay down unless you knew they were there, this revealed two recessed D rings that were anchored to the floor by screws. he pulled the D-rings up so they were vertical. Then he took satin strips and bound them loosely around my ankles before he used short lengths of the silk rope to bind my feet securely to the D-rings in the floor. While he was doing this he explained that the satin he had wrapped my ankles in first would help prevent bruising and ligature marks. Next he had me bend at the waist and reach forward and grab the rail of his bed with both hands spaced at 30 inches also. Then he used the same technique with the satin cloth and silk rope to bind my wrists securely to the bed rail.This left me in a very vulnerable position as I was bent at the waist at a nearly 90 degree angle with my cute panty covered ass as the focal point. Then he picked up the camera and tripod and moved it so it would be better focused on me fiddling with the zoom and focus until he was satisfied. The fear and anticipation continued to build inside me as I wondered what was next. What ever it was I knew it couldn't be good but that it would also be a incredible new experience . He sauntered over to me and casually removed my panties with a quick jerk on both bows with a flourish like he was yanking a table cloth out from under a formal dinner setting. then he stuffed the panties in my mouth "Hold these Slut!"
He opened on of the drawers and pulled out some lube and drizzled some onto my exposed gurl-pussy. Then he took the smallest butt plug and stuffed it deep inside me. I gasped at the pain and Gunther chuckled "Oh ya!, That reminds me the walls on this apartment are a little thin" with that he yanked the panties out of my mouth and grabbed the ball gag off the top of the dresser and held it near my face. "Last chance Slut! Beg for mercy now and I'll let you go home now but that means our little game is over. But once this goes in you can't talk and I am going to do whatever I want with you. You'll still be able to nod yes and shake your head no. but you wont be able to talk until I take this off" I've always been pretty stubborn and defiant so I guess my next words were kind of a dare. (I Know...Right?) I looked him in the eye and said "Go ahead! Do your best!" He chuckled and roughly forced the ball gag into my mouth, buckling it tightly into place. Now I was bound and helpless without even the ability to beg for mercy, Gods! I had never felt so aroused in my short little life!
Next he held the various instruments of pain deliverance in front of me, starting with the paddle "This is a Swat!" Next he showed me the whip " This is a lash!"... then the crop "This is a stroke!"... "Remember this!" He commanded.
Then he put the blindfold over my eyes and walked out of the room. he let me stew there for several minutes, blind helpless and scared, while uncertainty and fear built up within me. " Oh My God! What had I gotten myself into?" I seriously wondered if I was going to live through the experience or if I had hooked up with a total psycho and my body would simply disappear, never to be seen again. A few minutes later I felt a painful slap against my ass, jolting me out of me reverie. Funny thing was I could tell it was the leather paddle so it was a "Swat" Then he walked out of the room and left me standing there wondering when the next blow would land. I stood there for several minutes waiting for the next painful blow. Suddenly electric fire erupted on my sissy ass cheeks and i knew i had just been stuck by the leather whip. That was a lash. Moments later I heard a whirring sound as he swung the crop through the air a few times before applying it to my exposed ass. My world exploded in fire and pain as it definitely hurt far more than the others. That was a stroke."You have earned yourself an additional ten lashes with the whip and five strokes with the crop"
With that he began to slowly and methodically administer my thirty swats with the paddle, alternating between cheeks varying the spot and angle of approach so that after thirty swats I was sure my entire ass was cherry red.After he was done with the paddle he removed my butt plug and inserted a larger one. Next came the whip, he toyed with me dragging the whip slowly down my back caressing my ass cheeks with the soft leather strands before each brutal lash. when he was done with that he removed the second butt plug and replaced with an even larger one. I was really stretched to the limit and the pain was pretty intense. He played with the crop for several minutes running over my legs,caressing my inner thighs and balls with it, running it over my back stomach and arms making me tingle all over in anticipation until my world exploded in pain as he brought the crop sharply against my ass cheeks with considerable force. I screamed but the ball gag reduced it to a gurgle.He continued on in the same vein until he had administered all five stokes. then he yanked the large but plug out of me and shoved his huge cock up my tender ass. The punishment he had given me must have really turned him on because he was rock hard and attacked my tender gurl pussy with a vengeance, ramming his cock into me all the way to the hilt, tied to the floor and bed rail as I was I was completely helpless and his to use any way he wanted. Every time his hips slammed up against my sensitized ass it was like getting spanked again. My world dissolved into a frenzy of pain and lust and I felt an orgasm building deep within me. When he finally came and blew his load deep within me it was too much and I had an incredible orgasm, cum shooting out of my little sissy clitty onto the floor below me. I would have collapsed but tied as I was and impaled on Gunther's huge cock I couldn't move. Sensing my weakness he leaned over me and untied my hands with a deft yank on the silk ropes. next he freed my feet allowing me to slide off his cock and collapse in a limp heap on the floor at the foot of the bed moaning softly in pain. He gently removed the ball gag and picked me up and laid me on the bed. I heard him rustling about as he put everything away and turned off the video camera then he turned off the lights and got into bed beside me and was snoring softly within minutes. The pain from my tortured backside kept me up for awhile but eventually exhaustion claimed me and I dozed off into oblivion.
After I dressed in the schoolgirl outfit that Gunther had put out for me, I pulled my hair into a high ponytail and put on makeup emphasizing my eyes and lips without going overboard. I walked out into the living room to discover that Tracey had left and Gunther was dressed in a pair of slacks and a very expensive looking Cashmere cardigan. He smiled broadly and said he knew I’d make the right choice. Then he pulled a long tweed ladies coat out of the hall closet and handed it to me. It was a little big but fit fairly well; I assumed it was from one of his previous gurls. “Put it on we’re going out for dinner and then maybe some dancing.” He grabbed a coat for himself and we headed out after I snatched up the purse with my borrowed ID in it.
We went out to the parking lot and Gunther walked over to one of the few garages at the complex and punched a code into the keypad which opened the garage door to reveal a bright yellow Porsche 911SC Convertible. He laughed as I gaped at his ride. “What can I say? I prefer German engineering I brought it over from Stuttgart last year. Much cheaper in Germany!”
We got in and Gunther drove us to The Grotto, one of the nicest restaurants in town. We were seated at a secluded booth where Gunther ordered dinner for both of us. While we ate he asked me questions about my life quickly ascertaining that I had a lot of freedom to do as I pleased with little in the way of parental supervision because I didn’t cause much trouble at home. My Father traveled a lot and after the hell my older sister put my Mother through she was pretty content to give me free reign as long as I didn’t get into any trouble and kept my grades up. I quite often spent the night at a friend’s place so I knew I could get away with sneaking over to Gunther and Tracey’s pretty much whenever I wanted. He discussed the need for absolute secrecy with me because I was still only s*******n which could get him tossed in jail if my parents ever found out. He didn’t’ think my conservative father would take kindly to his teenage son being used as a sissy slut by an older man. Gunther explained that he traveled a lot so I would still have a lot of free time but that I was his little sissy when he was in town. I was to maintain my life as normal as possible so as not to arouse suspicion, even continue dating Mikki (which I was relieved at because even though I reveled in my newfound role as Gunther’s sissy, the thought of not hooking up with Mikki was torture even though I knew I’d quit seeing her if he ordered me too.) Furthermore I was to keep myself hairless at all times from the eyebrows down. He also explained that he had an account at a local salon and I was to go there every week on Friday after school to get my nails manicured and my toes pedicured. Once a month I was to get a facial to keep my skin soft and flawless and get my brows waxed along with a full body wax to remain as smooth and hairless as possible. He knew I was on the swim team and raced bicycles so being hairless wouldn’t be a problem but he thought that my team mates might question it if I shaved my pubic hairs although he preferred it. I said I would just tell them that Mikki hated pubes in her teeth ;-). He asked if I had enjoyed it when both he and Tracey used me together. I replied that I loved it and hoped to do it again. He said that it probably would but he had some friends who enjoyed sissies and If I was okay with it maybe he’d set something up in the future. I thought about it for a moment and the idea was really exciting. I told him so and said he was my master and I would be happy to obey any request and that it was my duty to service him and his friends whenever he wanted. He beamed at this and said I was a quick study, pulling me closer and kissed me deeply, grabbing my ass and squeezing it in his strong hands. Of their own volition, my hands found their way to his crotch where I was delighted to find his cock was swelling rapidly and soon became rock hard under my tender ministrations. I was feeling hot and bothered and perhaps the wine we had been drinking lowered my inhibitions; as I mentioned earlier we were in a very secluded part of the restaurant which was dimly lit and the circular booth was recessed so very private, additionally the table was covered in a very long white tablecloth which fell nearly to the floor. A very naughty thought stole into my head and I broke off the kiss long enough to whisper into his ear “I want to feel you in my mouth!”
Gunther pulled back and looked around to assure himself that nobody was watching us an and put his hands atop my shoulders gently pushing me down between his knees where his throbbing crotch was level with my eyes. I unzipped his slacks and unbuttoned his silk boxer to reveal his magnificent throbbing cock. I started licking it slowly at first teasing him before I engulfed the head between my pretty painted lips. I started slowly at first increasing the tempo as his cock became even harder, gradually forcing it further down my throat. It was hard because of the size but I felt a growing pride as I realized I was surpassing my previous attempts. Of course during this time the busboys and water boys who had been checking me out all night decided it was time to clear dishes and refill water glasses. My nervousness and excitement made me graze Gunther’s dick with my teeth, causing his hips to buck, which hit the back of my head against the bottom of the table making all the dishes left rattle slightly. No doubt the busboy knew what was going on which I am sure he communicated to our waiter who showed up moments later asking if we needed any dessert. Gunther replied that he was fine and his date was presently enjoying her dessert (I certainly was!) while gently bucking his hips a few times to make my head collide with the bottom of the table making it shake and rattle, ensuring that the waiter knew what was going on… Moments later I felt his cock spasm between my lips as he blew his load down my throat. Greedily I swallowed every drop and used a cloth napkin to wipe away any remaining traces of his orgasm. I was humiliated yet thrilled when we walked out together with the waiter and staff leering at us knowing our “secret”.
After dinner we went to a local disco and we danced and partied for a couple hours. Gunther was well known there and I was introduced to several of his friends who often smiled as Gunther would introduce me as his latest “discovery”. Dancing with him was fun but a little weird as I was used to leading and it took some adjustment to get used to following his lead. Slow dances were much easier as he would simply pull my tiny (comparative to his) body into his arms and physically lead me while making out with me. This caused me to just melt and let him lead me about the dance floor while I let the pleasure build within me. By the time we left I was totally aroused and ready to let him fuck me at a moment’s instance. We left the club and soon I figured out why we had parked more than two blocks away in a dark and secluded alley. We got to the car and he told me it was time to pay for my dinner, putting his hands atop my shoulders and pushing me down to my knees. I complied eagerly …sucking his magnificent cock between my lips and doing my very best to deep throat it. It was too big and I couldn’t do it but I obviously pleased him as his huge cock remained stiff the entire time. Eventually he decided he wanted more and pulled me up and bent me over the hood of his Porsche He spit into his palm and lubed up his cock, entering me roughly and fiercely. The pain was intense and it took a couple of minutes to adapt to his large cock but within a few minutes I was feeling nothing but pleasure. After several minutes of fucking we both came together.
After he was done fucking my tender ass I pulled up my panties and we got in the car and drove back to his apartment and I fondled his cock the whole time, occasionally leaning over to lick or suck on it. When we pulled into the garage he pushed his seat back and grabbed the back of my head pushing my mouth down onto his cock, forcefully fucking my mouth and throatfucking me until I would have to gasp and come up for air, saliva running from my mouth in long ropy strands, tears streaming down my face. I looked quite the mess with my mascara running and lipstick smeared all over and I gagged several times, but it just seemed to make him even harder and he would push himself even deeper into my throat, holding my head down until the gag reflex subsided. While he throatfucked me he kept up a very dirty dialog telling me what a dirty little slut I was and how he was really going to enjoy being my master as I was born to be a sissy cockcraving slut. Eventually after what seemed like an eternity he erupted violently and shot his load down my spasming again and again, both hands clasped to my head like a vice while he emptied his sperm into me. "Mein Gott Bobbi that was incredible!" I was exhausted from the strenuous activities and my knees were wobbly so he scooped me up in his massive arms and carried me to the apartment setting me down to open the door. I staggered over to the couch and collapsed there while Gunther went into the bathroom to relieve himself and clean up his crotch with a hand towel. Once he was done he tossed the towel to me and told me to get cleaned up and that he was going to take a quick nap while I did so. Then I was to pick out something sexy from his walk-in closet and get myself ready for more fun. He warned me that I had half an hour to do so and that I would receive another spanking if I was late, 1 swat for every minute late! Then he stripped naked and went into his bedroom to lie down.
I took off the high heels I was wearing as I didn’t trust my ability to walk in them in my present state and wobbled into the bathroom. God my makeup was a total mess with mascara running down my face and lipstick saliva and tears covered my face in a glaze. My eyes were red and my lips were raw and puffy from the brutal facefuck I had just received. I knew there was no way I could get myself presentable in just thirty minutes so I figured an hour would be appropriate and figured I could handle thirty swats as long as Gunther wasn't too brutal. I took a shower letting the hot water wash away the makeup saliva and tears that covered my face neck and chest. The warmth of the water felt heavenly on my sore little body which ached all over from the weekends activities, especially my tender buttocks which I knew were about to receive more punishment. I finished my shower and dried myself off. Then I applied lotions al over my skin and walked naked into Gunther's bedroom hoping he was asleep. I was reassured by the sound of his soft snoring. I went into the walkin closet on my right and was confused because there weren't any gurl clothes in the closet. I walked out and looked around and noticed another door in his room and opened it. Surprise, another walkin closet that was almost twice as big as the first one.This was an amazing closet which obviously had been professionally designed. It was filled with dresses, lingerie and girl clothes of all sorts. There were also several mannequins with wigs on them in several different colors and styles. Additionally there was also a small makeup table and lighted mirror where I could apply my makeup and tall chest of drawers with various bras, panties, and hosiery. There were also several racks of shoes with a large variety of heels in different styles and colors. As I explored the large Captains chest I found some drawers with things in them that I didn’t even know existed. There were some foam breast forms (unfortunately silicone ones didn't exist back then) Along with some bondage Items, various restraints, lengths of soft rope, something that looked like a ping pong paddle but was made from leather. Mmmm, evidently Gunther was even kinkier than I thought. I also so found several dildoes and butt plugs of various sizes. I was a little freaked out and wondered what I'd gotten myself into but hey, in for a dime in for a dollar. As I looked through the clothes I realized that most of the items were a little bit large for me, which really limited my choices. I settled upon a white satin and lace corset with a matching set of white lace panties and bra with matching garter belt suspender thigh highs and white high heels with a gauzy see through sheer babydoll negligee over it all. The bra was a bit large but when I put the breast forms in and pushed and taped my pecs to create cleavage it totally looked like I had nice c or even d cup titties! Long hours cycling under the sun had given me a bit of a farmers tan so I covered my arms in long satin gloves that came up to the middle of my biceps covering the tan lines nicely. The panties were French style and had satin ribbon ties on the side so I could adjust them to my smaller waist and could also be taken off by yanking the bows out without having to take off the garters or stockings I didn’t feel like doing my hair so I picked out a blonde wig that was styled in an updo with a French twist topped by artfully placed curls with a few curly tendrils hanging down and with a soft fringe that framed my face and wispy bangs that highlighted my eyes. Then I sat down at the makeup station and started applying my girl face. I was in the theater program at my high school and was the makeup artist for all of our theatrical productions and often did the girls makeup for them so I was pretty good at applying mine. I tweezed my brows a little bit to give them more of an arch but not so much that it would be really obvious at school. The blonde wig really changed my look so I opted for a brighter more glamorous look with my eye shadow in subtle shades of blue and silver and I opted for a paler foundation that more closely matched my torso. I used pinker rouge than I had before to accentuate my cheekbones and applied a shimmering pink gloss to my pouty lips. Once I was all ready I went back out to the kitchen poured myself a drink and popped a xanax. I loaded up a bowl and smoked it feeling very mellow and horny in short order. Glancing at the clock I noticed it was almost an hour so I went into the bedroom to wakeup Gunther. First I admired myself in the large full length mirror noticing that I looked like a young bride on her honeymoon night wearing her bridal trousseau. Gunther had moved the video camera back into his room so I checked to make sure it was positioned correctly on its tripod to get a good view of the king sixed bed and turned it on. I spent a moment admiring his Adonis like physique before I crept up on to the bed and took his cock between my lips, licking and sucking it to full erection. Slowly Gunther came awake and noticed the blonde wig." Mmmm, that looks good on you my little slut!
He let me suck his cock for few minutes before he made me stop. "That's a very nice way to wake your Master sissy gurl. But surely you don't think it will get you out of your punishment?"
"No Sir, I've been a very bad gurl and I took me thirty minutes longer than you gave me to get ready."
“And what did I tell you would be your punishment if you took too long to get ready?"
"One swat for every minute I went over Sir."
Sighing reluctantly I crawled over his body and positioned myself ass up over his thighs.
"What are you doing Sissy?" He asked
“I’m ready for my spanking Master" I replied uncertainly.
"Nice try but that's not how this is going to go down. You were a bad little girl and disobeyed my orders to be ready in thirty minutes. Not only that but you were a full thirty minutes late. Disobedient little bitches need to be properly punished so they learn the error of their ways... Don't They?"
I realized that was my cue and simpered "Yes Master, I've been very disobedient and I need to learn how to be a better Sissy. Please punish me properly Sir" wondering what I was about to endure.
He told me to go stand at the foot of the bed facing toward the bed and to wait for him
I did so and he got off the bed and walked into the closet where I heard him rustling around for a couple minutes. Then he came out to the bedroom and placed several items on the black lacquered dresser that stood opposite the bed. There was a large mirror over the head of the bed as well as a large mirror over the dresser so I could see what he was putting on the night stand. There were three butt plugs of various sizes lined up from smallest to largest, the leather ping pong paddle I had noticed earlier. A short whip made of many long strips of leather, and a black riding crop. There was also a ball gag and a black leather blind fold along with several short lengths of the soft silk rope I had seen earlier and several white satin strips of cloth. You may wonder why a 17 year old knew what these items were so I’ll explain. My best friend and next door neighbor (yes that one) had an older brother who had quite the collection of dirty magazines. Occasionally when he’d go over to his brothers place he’d swipe a couple and share them with me. One time there was a bondage magazine in his haul and we spent a lot of time perusing its naughty pages. One of the scenes involved a transvestite being tortured by a Dominatrix and he/she was wearing a ball gag. I was horrified, mortified and yet thrilled to realize I was going to be living out that scenario with some minor changes to the script. If it hadn't been for the Xanax I probably would have bolted and run.
Gunther finished putting everything in its proper order and then turned to me. “Put your right foot there" he commanded, pointing to a spot on the floor. Next he told me to put my left foot at a spot parallel to my right but about 30 inches away. Next he pulled up two small squares of carpet next to my feet that were Velcroed so as to stay down unless you knew they were there, this revealed two recessed D rings that were anchored to the floor by screws. he pulled the D-rings up so they were vertical. Then he took satin strips and bound them loosely around my ankles before he used short lengths of the silk rope to bind my feet securely to the D-rings in the floor. While he was doing this he explained that the satin he had wrapped my ankles in first would help prevent bruising and ligature marks. Next he had me bend at the waist and reach forward and grab the rail of his bed with both hands spaced at 30 inches also. Then he used the same technique with the satin cloth and silk rope to bind my wrists securely to the bed rail.This left me in a very vulnerable position as I was bent at the waist at a nearly 90 degree angle with my cute panty covered ass as the focal point. Then he picked up the camera and tripod and moved it so it would be better focused on me fiddling with the zoom and focus until he was satisfied. The fear and anticipation continued to build inside me as I wondered what was next. What ever it was I knew it couldn't be good but that it would also be a incredible new experience . He sauntered over to me and casually removed my panties with a quick jerk on both bows with a flourish like he was yanking a table cloth out from under a formal dinner setting. then he stuffed the panties in my mouth "Hold these Slut!"
He opened on of the drawers and pulled out some lube and drizzled some onto my exposed gurl-pussy. Then he took the smallest butt plug and stuffed it deep inside me. I gasped at the pain and Gunther chuckled "Oh ya!, That reminds me the walls on this apartment are a little thin" with that he yanked the panties out of my mouth and grabbed the ball gag off the top of the dresser and held it near my face. "Last chance Slut! Beg for mercy now and I'll let you go home now but that means our little game is over. But once this goes in you can't talk and I am going to do whatever I want with you. You'll still be able to nod yes and shake your head no. but you wont be able to talk until I take this off" I've always been pretty stubborn and defiant so I guess my next words were kind of a dare. (I Know...Right?) I looked him in the eye and said "Go ahead! Do your best!" He chuckled and roughly forced the ball gag into my mouth, buckling it tightly into place. Now I was bound and helpless without even the ability to beg for mercy, Gods! I had never felt so aroused in my short little life!
Next he held the various instruments of pain deliverance in front of me, starting with the paddle "This is a Swat!" Next he showed me the whip " This is a lash!"... then the crop "This is a stroke!"... "Remember this!" He commanded.
Then he put the blindfold over my eyes and walked out of the room. he let me stew there for several minutes, blind helpless and scared, while uncertainty and fear built up within me. " Oh My God! What had I gotten myself into?" I seriously wondered if I was going to live through the experience or if I had hooked up with a total psycho and my body would simply disappear, never to be seen again. A few minutes later I felt a painful slap against my ass, jolting me out of me reverie. Funny thing was I could tell it was the leather paddle so it was a "Swat" Then he walked out of the room and left me standing there wondering when the next blow would land. I stood there for several minutes waiting for the next painful blow. Suddenly electric fire erupted on my sissy ass cheeks and i knew i had just been stuck by the leather whip. That was a lash. Moments later I heard a whirring sound as he swung the crop through the air a few times before applying it to my exposed ass. My world exploded in fire and pain as it definitely hurt far more than the others. That was a stroke."You have earned yourself an additional ten lashes with the whip and five strokes with the crop"
With that he began to slowly and methodically administer my thirty swats with the paddle, alternating between cheeks varying the spot and angle of approach so that after thirty swats I was sure my entire ass was cherry red.After he was done with the paddle he removed my butt plug and inserted a larger one. Next came the whip, he toyed with me dragging the whip slowly down my back caressing my ass cheeks with the soft leather strands before each brutal lash. when he was done with that he removed the second butt plug and replaced with an even larger one. I was really stretched to the limit and the pain was pretty intense. He played with the crop for several minutes running over my legs,caressing my inner thighs and balls with it, running it over my back stomach and arms making me tingle all over in anticipation until my world exploded in pain as he brought the crop sharply against my ass cheeks with considerable force. I screamed but the ball gag reduced it to a gurgle.He continued on in the same vein until he had administered all five stokes. then he yanked the large but plug out of me and shoved his huge cock up my tender ass. The punishment he had given me must have really turned him on because he was rock hard and attacked my tender gurl pussy with a vengeance, ramming his cock into me all the way to the hilt, tied to the floor and bed rail as I was I was completely helpless and his to use any way he wanted. Every time his hips slammed up against my sensitized ass it was like getting spanked again. My world dissolved into a frenzy of pain and lust and I felt an orgasm building deep within me. When he finally came and blew his load deep within me it was too much and I had an incredible orgasm, cum shooting out of my little sissy clitty onto the floor below me. I would have collapsed but tied as I was and impaled on Gunther's huge cock I couldn't move. Sensing my weakness he leaned over me and untied my hands with a deft yank on the silk ropes. next he freed my feet allowing me to slide off his cock and collapse in a limp heap on the floor at the foot of the bed moaning softly in pain. He gently removed the ball gag and picked me up and laid me on the bed. I heard him rustling about as he put everything away and turned off the video camera then he turned off the lights and got into bed beside me and was snoring softly within minutes. The pain from my tortured backside kept me up for awhile but eventually exhaustion claimed me and I dozed off into oblivion.
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