My First Time Dressed As A Girl (PT 2) (Aftermath) free porn video

My First Time Dressed as a Girl,(PT 2) Aftermath
Hi Reposting an account of how I got started XXXdressing so that the first month is properly documented because it was what set my behavior for the next three decades).(The events of this story are true and reflect what happened thirty years ago the first time I went all out and dressed as a female. The conversations in it may not be completely accurate, as this was a long time ago, but are as accurate as my memory of these past events can provide. A quick note for those who are coming upon this account for the first time; please read part one first so you will understand how I got to this part in the first place. ;-) There is more to come so lookout for Part 3

Tracey and I laid there in front of the fireplace for a time enjoying the heat of the fireplace and the post coitus glow of my initiation as a ”woman”. After a bit he stirred and got me to my feet and helped me with my wobbly legs into his bedroom and into bed, spooning me as we drifted off to sleep.
I awoke with the feeling of his erection pressed against my backside, he was asleep but had a nice case of “morning wood”. Remembering the pleasure of the night before I realized I wanted him to fuck me again and wiggled my ass against his groin and he came slowly awake. Feeling my cute sissy ass grinding into his crotch was all the signal he needed. He started thrusting his hips back and forth sliding his erect cock back and forth between my cheeks, rubbing against my asspussy making it tingle in anticipation. Eventually he reached over to his night stand and grabbed a condom and some lube. Soon I felt the head of his dick pressed up against my hole and he started pushing it in, he was about halfway in when the pain was a bit much and I had him pull out. He asked if I was okay and I said yes I just need a sec. After a few moments the throbbing subsided and I knew I was ready for him. Wiggling my butt I invited him back inside me. He complied and entered me much more easily this time and my ass accepted his cock eagerly. He started fucking me with long slow languorous strokes which was nice, but remembering last night’s session I wanted more. “Fuck me harder!” I told him “I want you to pound my pussy like a machine!” I was laying on my stomach and he started hammering away at my ass but it only made me want it harder, soon I was up on my hands and knees taking it doggy style thrusting my hips back against him in time with his thrusts. I was in heaven! I loved the way his cock felt in me and the way it made me feel like a total slut. I asked him if I was a good little girl and he replied No, I was a naughty slut, and this made me buck against him harder. He sensed my excitement at his calling me a slut and soon we were engaged in a very verbal and dirty repertoire with him calling me a whore and a slut, dirty little bitch etc. I responded by begging him to fuck me harder and harder telling to fuck my sissy ass like the bitch I was. After about 20 minutes of frenzied energetic fucking he exploded forcefully into me. I could feel his cock spasming inside me as he shot jets of cum into the condom he wore.
We collapsed onto the bed and he slipped his spent cock out of me making sure to hold the condom as he did so. He put on a robe and left me on the bed in a daze saying he was going to make us some coffee. I drifted off for a bit and awoke to the smell of coffee and bacon. It was a bit chilly and I felt a bit exposed dressed in nothing but a crotchless fishnet body suit over a satin leather and lace corset, so I slipped on the panties, jacket, and miniskirt which Tracey had removed the night before. I adjusted my pads so my cleavage was maximized. Then I touched up my makeup in his dresser mirror and smoothed my mussed hair a bit, although it was remarkably intact due to the huge amount of hairspray Mikki had put in it the night before. After I was satisfied with my appearance I wandered out to the kitchen and was surprised to see his roommate Gunther sitting at the counter sipping at a mug of coffee. I was alarmed at first but figured what the hell, obviously he knows I’m here, how could he not given me and Tracey’s vociferous session earlier?
Gunther’s back was turned to me so he didn’t see me come in and Tracey was busy at the stove so he didn’t notice me either. They were talking about me or rather about Tracey’s night of fun.
“So, from the sounds coming out of your room earlier you must have gone out last night after all. I thought you were staying in. I didn’t see you at the Cowpoke (a local gay bar) last night so where’d you hookup with your little bitch?” asked Gunther
My cheeks reddened as I realized he was referring to me, but I wanted to hear what Tracey had to say so I kept quiet.
“Actually I didn’t go out last night. My “little bitch” showed up drunk on our doorstep about 2 am and begged me to take his cherry. It was the shock of my life since I had hit on him before but he’s always got some hot girlfriend and assured me he was straight. I’ve wanted him ever since I met him at Joe’s place about a year ago so how could I resist?” Tracey chuckled.
“One of your cute little twink boys then?”
“Actually not, you know that’s my preference but this one is different and special. Wait till you see him. I think you’ll find him very tasty. Right down your alley so to speak. Actually you’ve met him before”
I swallowed nervously as I realized Tracey was probably right. Months earlier one night after our Dungeons and Dragons session had wrapped up and everyone else had headed home Gunther had arrived at the apartment back from a trip to Thailand. Tracey asked him if it was a good trip and Gunther had smiled broadly and told us all about, even showing us some Polaroids he had taken of the Thai Ladyboys he had gone to Bangkok to have fun with. At the time I had been secretly intrigued by how pretty they were and maybe even a bit aroused, but I had no idea that I would wind up all dressed up and pretty like them begging for a guy to fuck me months later.
About then Tracey turned and noticed me. Grinning broadly he said to Gunther ”Looks like my “little bitch” is awake now. Gunther I’d like to introduce you to Miss Bobbi.”
Gunther turned around and his eyes lit up like a k** in a candy shop. He eyed me up and down taking in every inch of me. “I don’t recognize this one, Tracey she is way to pretty to be one of your little boyfriends in a dress! You are sure I have met her?’”
I blushed furiously, secretly pleased that he hadn’t recognized me, and enjoying his references to me as a female. “Umm, actually we’ve met a few times, I’m Rob. But I guess I go by Bobbi dressed like this. It’s kind of my first time.” I was a little nervous, given the way he eyed me like a wolf sizing up a succulent lamb. Gunther was quite tall at 6’4” and weighed about 250 lbs. all of it lean muscle on an Adonis-like physique. He had ice blue eyes with a strong jaw line and a slightly crooked nose that had gotten broken during a Tae Kwon Do match years earlier. He reminded me a lot of Dolph Lundgren and his noticeable German accent only heightened that impression.
Gunther took a closer look at me, recognition slowly dawning “I wouldn’t have made you as a boy on the street, that’s for sure. You are very passable as a girl and a pretty one at that. You look as good as the Ladyboys in Thailand. Do you suck cock as good as them?”
“Wouldn’t you like to know?” I shot back, strutting over to the coffee pot and pouring myself a mug. I added some sugar and asked Tracey if he had any cream. Gunther couldn’t resist the opening and offered his own creamy sperm as a joke. I said he probably didn’t have a big enough stir stick which he laughed at and assured me his stick was plenty big. We bantered back and forth like this while we ate breakfast. I asked Tracey if he had any painkillers as I had a bit of a hangover. Tracey asked what my plans were for the day, and if I needed to be home anytime soon. I replied that I had told my parents I was spending the weekend at my friend Tyler’s house as we had an epic gaming session planned and were designing a new Dungeon for our group to explore. (I did this a lot, so Mom had just said okay and told me to call home if I wasn’t going to be home Sunday night since she knew Tyler lived about a block from school and that I would probably want to stay the whole weekend.) Tracey walked to his cupboard and grabbed a bottle of brandy and prescription bottle opened it up and took out a little pink pill. He handed it to me and poured a large dollop of brandy in my coffee saying something about the hair of the dog that bit you.
I didn’t know what he gave me but it sure did the trick and soon I was feeling very mellow and dreamy (later I found out it was a vicoden). I pulled a joint out of Kayla’s purse and lit one up offering it to Gunther. “I’m not sure I should” he said “ Smoking weed gets me horny as hell. And as good as you look I’m not sure I can keep my hands off of you.”
“Maybe you won’t have to” I teased, a little shocked at the words coming out of my mouth. Last night was the first time I had ever dressed up completely as a girl and I had sucked Derek’s cock and Tracey’s as well and gotten fucked twice by Tracey. Wasn’t that enough? Yet here I was flirting with a guy twice my size who looked like he could snap me like a twig! Then I started thinking about the rather large and noticeable bulge in his pants and wondered if I could even handle it. I decided I might as well find out.
Standing up I walked over to him and sat on his lap and put the joint to his lips, looking over to Tracey to see if he was getting upset. I didn’t want to start a fight between roommates but whatever was in that pink pill had totally relaxed any inhibitions I might have had and I was feeling very randy and naughty. Tracey was grinning and apparently had no problem with the situation, motioning for me to go ahead. Gunther took a deep drag and held it for a moment and then pulled my lips to his shotgunning the smoke into my mouth. I inhaled it and held it for a moment before releasing. We traded a few more hits this way and then he started to kiss me. Gently at first and then more passionately, his hands roaming over my body, squeezing my ass and generally making quite free with the goods if you know what I mean!.
From time to time I would glance at Tracey, and I could see he was enjoying the show. I could feel Gunther’s cock swelling up against my panty clad asscheeks. My hands roamed over his chest and shoulders and I marveled at the hardness of his physique. I was incredibly aroused yet still had no sign of an erection. I was glad for that because I didn’t want one. I just wanted to be the perfect naughty lil slut for Gunther and suck his cock like his Ladyboy friends in Thailand. Gunther must have been thinking the same thing as pushed me off his lap and onto the floor “Enough” he said “It’s time to find out if you are as good as a real Ladyboy.” With that he dropped his pants to the floor and I could see his cock was sticking out well past the waist band of his boxers. He motioned me closer and told me to take his boxers off, I did so nervously wondering what I had gotten myself into but feverish with anticipation to see how big it really was.
His cock sprang forward as I pulled down his boxers and struck me in the face. Startled I pulled back and stared at it for a moment. It was quite large, at least 9 inches long and very thick, much bigger than Tracey or Derek! Also it was uncircumcised, the first one I’d ever seen. “Are you going to suck it or stare at it slut?” asked Gunther with a note of impatience.
Feeling a bit intimidated I took the shaft in one hand and started to stroke it. It was really thick, my fingers couldn’t even wrap all the way around it. I had to use both hands to encircle it. Feeling like I needed to work my way up to actually sucking it I started to lick the head of it like a lollipop pushing back his foreskin to expose the smooth head. A drop of precum glistened at the end of it and I licked it off, savoring the taste. For some reason this got me even more excited and I began to lick up and down his shaft, bathing it with my tongue. Gunther seemed to enjoy this and started to slap his cock against my face and my lips. “Open up” he commanded. I opened my mouth as wide as I could and he pushed his cock past my lips into my wet warm mouth. He let out a moan of pleasure and started to push it deeper. I gagged and realized there was no way I could deepthroat him like I had Derek and Tracey. Even though he was only about an inch longer than my best friend whom I had learned to suck dick on he was much thicker and I knew he would wreck my throat if he shoved it all the way in. Still I was feeling the effects of the vicoden, alcohol and weed and took him as deep as I could gagging a bit as I did so.
I must have sc****d his cock with my teeth then because he pulled his cock out of my mouth roughly and growled “No teeth Bitch!” and slapped me across the face, not too hard but hard enough to sting a bit and shock me. I must have looked hurt because he chuckled a bit and said “Don’t worry slut, you are going to suck it like the good little cockwhore you are. You’re not as good as a ladyboy yet, but you’re going to learn” I glared at him, face stinging from the slap and my pride hurt at being found inferior. I looked over to Tracey for support who simply shrugged as if to say “You got yourself into it!”
Gunther barked at me “Oh don’t look so offended Bobbi! I heard you in there with Tracey earlier and its time you learn how to be a true sissy slut. You’re not really his type after all, he prefers twinks. Young guys not little gurls who can’t get an erection and fuck him back. Him fucking you was a mercy fuck because he’s been dreaming about fucking you as Rob for over a year now. Transvestites really aren’t his thing. But they are mine so I guess it’s up to me to teach you how to be a proper sissy bitch. I have to say you’ve got the look down pretty well, none of the TV’s in this town are as pretty as you but you need to learn a few things like how to suck a really big cock without scr****g it with your teeth and how to take one in your pussy without crying.”
Then he grabbed me by the hair and pulled my mouth to his cock. I was still pissed so I pressed my lips together and resisted as he tried to force his cock into my mouth. He slapped me again “Open up slut!” I glared back at him defiantly. “Last warning Bobbi…1…2…3” I smiled and flipped him the bird, I heard Tracey mutter “Oh Shit! Now you’ve done it Bobbi!”
Gunther smiled at me before he looked over at Tracey and said “Yes she has, hasn’t she? Give me your belt Trace! I think it’s time Bobbi learns a lesson.” Tracey looked at me as if to say “I’m sorry” while he removed his belt and handed it to Gunther but I could see excitement in his eyes as he handed it over. “Go get the Polaroid and my toolkit from my room. There’s a couple fresh packs of film in my nightstand, bring them both” Tracey left the room and Gunther turned his attention back to me. I was trembling with fear now, my Dad had beat me with a belt whenever I got into trouble up until I was thirteen and I was terrified of what Gunther intended to do with it. “Please Gunther…” I begged but was cut short by another slap in the face. Then he grabbed my hair and pulled me to me feet, and dragged me over to the couch. He turned me around and grabbed both my wrists forcing them back behind me. I tried to struggle but at 5’7” and a slender 130 pounds against his size and strength it wasn’t much of a struggle. He tied my wrists with the belt binding them together tightly. Then he sat on the couch and pulled me down across his lap holding me by the hair with his left hand while yanking up my denim miniskirt with his right to reveal my satin covered ass. ‘Oh yes I’m going to enjoy this. “ He murmured. I was in great shape back then as I raced bikes competitively and was on the swim team as well. Girls told me all of the time what a cute ass I had and how they were jealous, so I was pretty proud of my derriere and got a little thrill from Gunther admiring it even if I was scared and angry at him. Slowly he edged my panties down revealing my baby smooth hairless ass. He caressed it for a bit then lifted his hand in the air and paused. I saw a flash of light and heard the distinctive sound of a Polaroid ejecting a picture. Oh god, I realized Tracey was taking pictures of the whole thing, I was so humiliated. Then SMACK! Gunther’s hand on my ass stung like crazy and I jerked in his grasp. He laughed and tightened his grip on my hair and started wailing away with a vengeance. I bucked and struggled to no avail; he was way too strong for me and had total control of my body. Soon I was crying and sobbing uncontrollably. I was also starting to realize that I was getting aroused by the total domination and humiliation I was going through. Gunther was obviously very aroused as I could feel his rock hard erection pressing up against my belly. This further heightened my arousal and it combined with the pain of his hand cracking against my ass so that soon every slap was like a mini orgasm shooting through my body. Gunther spanked me nonstop for several minutes and I could tell Tracey was taking pictures with the Polaroid the whole time.
Eventually he stopped and I gasped for breath in long shuddering breaths as I fought to gain control over my crying. “So, have we learned our lesson Bobbi?” he asked, almost tenderly.
“Yes” I gasped
SMACK! “Yes What? Bobbi?”
“Yes Gunther?”
SMACK!SMACK!SMACK! “That’s Yes Sir, got it Bobbi?”
“Yes Sir!” I wailed
“Are you my little bitch now Bobbi?” he asked, self satisfaction evident in his voice
“Yes Sir”
SMACK! “Yes Sir What!?!”
“Yes Sir I’m your little bitch now!’ I cried hating myself for saying it but afraid of further punishment and also realizing it was true. With his huge cock pressing up against me, my tender flaming asscheeks exposed and with Tracey taking pictures of the whole thing I knew there wasn’t anything I wouldn’t do for him or let him do to me.
“Are you going to suck my dick like a good little slut?”
“Yes Sir, I’ll suck your dick like a good little Slut…No Teeth!” I added, hoping to please him
Smack. Lightly this time. “Damn Straight. “ he chuckled “Are you going to beg me to let you suck my cock like a good little whore?
“Yes Sir, I will beg to suck your cock like a good little whore”
“After I‘m done letting you suck my dick will you beg me to fuck your pussy like the little cumslut you know you are?”
I hesitated, fearing the size of his huge cock…
SMACK! SMACK! SMACK! SMACK! SMACK!
“Yes Sir!” I cried “I’m a little cumslut and I will beg you to fuck me when you’re through letting me suck your huge cock!”
“Good, I think you’re ready to learn how to suck my cock. Get on your knees bitch!” He commanded, letting go of my hair. I complied, sliding off his lap onto the floor. It was difficult to get into the right position with my derriere on fire and my hands tied behind my back. Gunther took the camera from Tracey and snapped off a couple quick pics. I looked quite the sight with eyeliner and mascara streaming down my cheeks from the tears I had shed and my lipstick smeared from him rubbing his cock against my lips and face when I had tried to resist him earlier. “Oh, don’t you look adorable!” He remarked “You look like a good little whore who just got dumped by her boyfriend and balled her eyes out.” I nodded my agreement, my eyes locked on the huge erection bobbing just inches in front of my face. All I knew at that moment was I simply had to feel it in my mouth. I was so turned on I felt like my brain was boiling. I could feel precum leaking from my penis even though I wasn’t hard at all. In fact it seemed to have shrunk a bit from its usual flaccid state to a little nub less than an inch long, and my testicles had receded into my body and there was only a small empty void where my proud nutsack had once been. All in all I felt like a total girl and a slutty one at that! At that moment I wished I had a real pussy so that “SIR” could enjoy it . Anyways…
Gunther told me to open up and I readily obeyed his order. I opened my mouth as wide as I could, accepting his uncircumcised cock deep into my mouth. I used my tongue and lips on it trying to get him as hot as I could. He began to instruct me exactly as how he liked his massive dick sucked. Slow down, go faster, more tongue, stroke it, suck harder, lick the head more, beg more. Eventually he told Tracey “Give me the poppers, Trace!” I heard him sniff deeply twice before he stuffed a little brown bottle under my nose and told me to inhale. I did as I was ordered to and immediately felt a rush surging through my brain and my body. After that all of my existence was focused upon his huge cock in my mouth. I worked back and forth upon it feverishly, my only thought was about making Gunther shoot his load down my throat! Later I when I saw the Polaroids I was shocked to see how far I had gotten his huge dick inside my throat but ultimately I couldn’t deepthroat it all the way.
He used me like this for about twenty minutes before he yanked my hair back and pulled his cock out of my face and started jacking off, his beautiful cock hovering inches from my face. After an eternity he erupted, shooting huge jets of sperm all over my face and breasts. This wasn’t the first time I had sucked a cock to completion but definitely the most exciting! Knowing I had made a handsome stud cum with my looks and my skills as a cocksucker totally got me off., and I nearly came right then.
Fortunately for me Gunther wasn’t nearly done with me, he had Trace take a few more pics of me with my face and décolletage covered in his cum and even snapped off a couple himself. Then he told me I looked like a disgrace and I needed to clean myself off. He ordered me off to Tracey’s room to clean myself off and repair my makeup. This took awhile and it was a bit before I felt pretty enough to face my new master. I just knew if I wasn’t presentable I’d find myself across his lap again. Not that that was the worst thing I could imagine, but after having sucked him off and having been rewarded with my first facial, I found myself eager to feel him inside me despite my trepidation about his size. I was involved with the theater department at my school and specialized in theatrical makeup and often did the girls makeup for them for sexy roles such as dancers and molls in plays like “Guys and Doll”, in fact I often practiced on myself so I I would be better at their makeup (or so I told myself!), so I was able to make myself up pretty well, and was looking quite sexy after about 15 minutes. Admittedly, it was a bit heavier than what Mikki had done, but I liked what I saw in the mirror of Tracey’s bathroom and felt ready to go face my new master. At this point Tracey walked in holding a red rubber bag with a thin white plastic hose attached to it with a long thin nozzle at the other end. Handing it to me he said “Gunther wants you clean down there” and indicated I should go into his bathroom and give myself an enema. I did as I was told, enjoying the feeling of the warm water cleaning out my tushy and cleaned myself carefully with tissue and dried off my ass with a towel. A quick glance in the mirror showed my hair was a bit of a mess but it only made me look like more of a slut so I smoothed it a bit and walked out to the living room to face Gunther and what I knew would be his taking of my sweet lil asspussy.
When I walked into the living room I noticed a set of lingerie lying upon the coffee table along with some various toys and sundries. Tracey sat in a Laz-E-Boy recliner nearby, Polaroid in hand, an obvious look of enjoyment on his face. I looked to Gunther, obviously awaiting further instructions.
“Strip Bitch!” he ordered.
Reluctantly, I complied. Stripping off my Jacket, then my skirt and panties, fish net bodyhose and corset. It was the last that I was most reluctant to take of as I felt it did the most to help accentuate my figure and was also the most work to take off. Although after nearly a whole day of being cinched tightly at the waist my torso retained the shaped forced upon it by the corset, narrowing at the middle and flaring out at the hips and chest. Oddly it was at this point that I was the most completely humiliated, standing there naked without any girl clothes on. I knew what he wanted me to do so I indicated the pink lingerie on the coffee table and begged to put it on. Gunther laughed and said “You didn’t think I’d fuck you without being dressed like a proper sissy gurl did you? By all means, get dressed and do it quickly!”
I obeyed with alacrity crossing over to the table and began putting on my new outfit. Gunther told me it had belonged to his last bitch. But that she had left it there when she graduated college and moved away last year, although I was gratified when he told me that she wasn’t as pretty as me and he looked forward to seeing how pretty I looked in her gurl clothes.
I began with a pair of satin and lace French pink panties that tied at the hips on both sides. Next came a pair of pink silk stockings with a seam up the back that felt absolutely marvelous as I pulled their sheer silky smoothness over my bare toned legs. Then I donned a pair of long lacy pink fingerless gloves that had a little loop at the end to put my middle finger through but otherwise left my hands open. Basically they looked kind of like a pair of lacy pink stockings for my arms coming up to mid bicep and accentuated them in a very feminine way. Lastly there was a pink lacey corset like top that laced up the back with pink ribbon. It wasn’t as sturdy as the corset I had been wearing with no boning or ribbing but was definitely more comfortable and had attached garters to hold up my pink silk stockings. Tracey helped me with the garters and cinched up the waist of the corset. The bra cups of the corset were padded so when I added the pads I’d been wearing earlier it pushed up the flesh on my chest so I looked like I had a very respectable set of boobs with nice deep cleavage that made me feel very sexy and gurly. ( My ability to “fake” a set of titties has ever since been one of my favorite talents and many men have asked if I was a real TS or on hormones over the years.) I finished the look with a pair of patent leather pink pumps that had to have at least a five or six inch stiletto heel to them, and a strap that buckled around the ankle. They were slightly too big but that was okay with me as the heels I had been wearing were about a half size too small and pinched my feet terribly. The height of the heels made walking rather difficult, but that was okay as I figure they weren’t really designed for walking in anyways!
After I had finished dressing I looked to Gunther for approval and the lust in his eyes was quite evident. “You look fucking Hot Bobbi! Go in the bathroom and see what a sexy little slut you are” Dutifully I did so excited to see how I looked and tottered off to the bathroom with short mincing steps, handicapped by the extreme height of the heels I was wearing.
When I got to the bathroom I was stunned at what I saw and thrilled at the same time. I looked like a model in a Fredericks of Hollywood catalog. Long slender toned legs accentuated by the stilettos and pink stockings on my legs. A tight toned, still slightly red, ass with creamy pale smooth skin encased in pink satin and lace. Prominent ersatz titties were jutting proudly from my chest with cleavage that invited a cock to rest there. Sexy smoky eyes with long dark lashes and pouty sexy red glossy lips that were obviously just made for sucking cock, all framed by a soft cloud of curly brown hair that reached past my shoulders. If I could have cloned myself I would have fucked me right then and there! I must have admired myself for too long because Gunther yelled from the living room to quit fawning over myself and get my ass in there to take care of his dick.
I walked out to the living room to see him standing naked in the middle of the room with his large semi erect cock dangling down invitingly. I started to walk over to him but he held his hand up in a fist, extended his fore finger and pointed down at the floor “Crawl!” I dropped to my hands and knees and crawled across the floor to him while Tracey snapped off a couple more Polaroids of me. He was smoking a clawed meerschaum pipe packed with some potent smelling weed and handed it to me so I took it and took several tokes before he stopped me and handed me a couple pills (another vicoden and a valium this time) saying “Here take these, you’re going to need the for what comes next” and then gave me a snifter of brandy to wash it down with.
I was already feeling the buzz again from the weed and salivating at the sight of his large cock dangling in front of my face so I reached up for it and was rewarded by another slap to my face. Not too hard but enough to sting a little and get my attention. I looked up t see him slowly wagging his finger back and forth in front of my face in a gesture of negation. I remembered my place and begged him “Please Sir may I suck your cock?” Smiling he nodded his assent shifting his hips forward to my face and I took his cock eagerly into my mouth, marveling at how eager I was to do so. I used all of the talents he had taught me and all of my limited experience with previous attempts at sucking dick and he was rock hard in short order. Meanwhile Tracey had run out of Polaroid film so Gunther told him to get more at the camera shop about a block away. I was a little disappointed to be losing my audience and photographer for a bit but knew he’d be back soon. I started stroking Gunther’s cock with both hands, realizing as I did so what a great design the fingerless lace gloves were, they were very feminine but didn’t cover my palms and fingers with lace which surely would have chafed his cock as I stroked it. Also they didn’t cover up my red fake nails that Mikki had applied the night before so my small hands looked very feminine and sexy wrapped around his rigid member.
After a few minutes Gunther ordered me to stop and put my face on the floor while on my knees and to spread my asscheeks with my hands. Trembling, thinking he might be ready to fuck me with his huge cock I did so. He noticed my trepidation and said “Don’t worry Bobbi, you’re not ready for this yet. First we have to prepare your pussy for my cock. He pulled my panties to the side and then he applied a lubricant to my butt that had a numbing agent in it and I felt a mild buzzy feeling as my sphincter began to go numb and relax. He eased a finger inside me probing my insides, then he slipped another in, then a third. By this point the valium and vicoden had kicked into full effect so I was feeling very buzzed and enjoying his probing quite a bit. I heard Tracey come back in and he told Gunther he’d decided to rent a video camera while he was there and Gunther said it was a great idea. I remember being vaguely appalled, but the d**gs were doing their job and kept me submissive and compliant, focused on the wonderful feeling of his fingers sliding in and out of me. Tracey busied himself setting up the video camera and tripod which took some time as video cameras back in the eighties were large, clunky, and complicated. Meanwhile, Gunther withdrew his fingers and inserted a fairly large butt up my ass. It hurt a bit but then I heard a click and the plug started vibrating sending electric tingly feelings throughout my body. It felt great and waves of pleasure were coursing through my body!
He told me to get to my knees and beg Tracey to let me suck his cock as he was taking a break and wanted to watch me suck cock like a good little whore. I did as I was told and soon Trace had his cock buried down my throat fucking my face like a girls pussy. I loved it and have always loved a good dominant face fuck since then but I can only do it with cocks that are the right size as my mouth is only so big. Gunther was obviously enjoying the show and egged Tracey on telling him to fuck my mouth like it was one of his little twinks’ boypussies. Tracey had been watching me be Gunther’s little bitch for hours now and was obviously very turned on as he only lasted a few minutes and came deep in my mouth holding my head still so I could feel his hot cum hitting the back of my throat, coating my tongue. “Don’t you dare swallow yet!” ordered Gunther so I held it in my mouth while Tracey squeezed the last few drops into my open mouth and on my lips. Gunther took more pictures of me on my knees with cum in my mouth and the buttplug in my ass driving me crazy and had me face the video camera to show my mouthful of cum. Eventually I swallowed reflexively and it must have been too soon. Gunther told me I was a very bad girl and must be punished again, pulling me across his lap and spanking me. It wasn’t as brutal as before and I thoroughly enjoyed it with the vibrator humming away inside me while he worked my tender ass with his bare hand.
After my ass was pink and tender again, he stood up and I could see that the spanking had gotten him as excited as me as his cock was rock hard. I begged him to let me suck it and he consented but only for a moment. After a few minutes he pulled his cock away from me and told me it was time, leading me to the middle of the room he instructed me to get on all fours, doggystyle. He eased the vibrator from my ass and I felt a little pop as it came out; I squirmed and wiggled my ass a bit missing the feeling of it inside me.
“Don’t worry slut, I’ve got something even better than that for you.” He paused for a moment to put on a condom and I idly wondered where he found condoms big enough to fit him. He must have guessed what I was thinking and he told me they were special order from a company in Europe. Then he applied more desensitizing lube to my hole and started working his fingers into me using them to stretch and widen his target. I was moaning in pleasure from this when he asked if was ready. I knew what he wanted from me so I wiggled my ass invitingly abegged him to fuck me like a good little whore.
I felt the head press up against my waiting hole and he started to push it in. Even with the desensitizing cream and having been stretched by the vibrator and his fingers it was a tight fit and the pain was pretty intense he paused for a moment with just a few inches inside me to let me get used to his girth. Then slowly and inexorably he began working it deeper inside me with slow back and forth strokes, pushing it a little deeper each time. Despite his gentleness I gasped in pain a few times and was tearing up a bit. Tracey suggested to Gunther that he pull out for a moment and let me catch my breath as it had seemed to work earlier. He did so and after a couple of minutes the throbbing pain inside me subsided and I wiggled my ass suggestively begging him to put it back in me. It went in much easier this time and he slid further into me getting about seven inches deep before coming up against stiff resistance from the muscles deep inside me. I pushed back against him and he grabbed me by the hips and pushed forward harder, I could feel the clenched muscles starting to yield when all of a sudden I felt a sharp tearing pop and he thrust all the way inside me to the hilt. The pain made me cry out and he stopped just resting there with his huge cock buried in my ass and let me get used to the pain while my body adjusted to the intruder inside of it. After a bit he pulled back some and began thrusting back and forth slowly moaning as he did so. “ Gottdam your pussy is so tight Bobbi, it’s the tightest pussy I’ve ever had.” He exclaimed. “I should think so! “ I thought to myself, given the fact that until about twelve hours ago I had been a total virgin in this area and that Tracey’s cock wasn’t nearly as big as Gunther’s! I glanced over and saw that Tracey had taken the video camera off of the tripod and was moving about the room shooting the action from different angles. Somehow knowing that I looked like a little porn starlet and was being filmed like one got me even more aroused at that moment and I began bucking back onto onto the huge dick inside me, crying out at the sharp stab of pain I got every time he bottomed out deep inside my bowels. Gunther picked up his tempo fucking me harder and faster and I fucked him back. Soon he was pistoning in and out of me like a well oiled machine, calling me all sorts of names like slut, cunt and bitch. Telling me I was his sissy whore and he was going to use me like this all the time. I loved it and begged him to fuck me harder, saying I was his little sissy bitch and I loved having his cock in me and that I would do anything for him if he would just keep fucking me please! I could feel an orgasm building deep inside me and came violently, cum flowing out of my limp clit and my ass twitching around the cock buried deep within me.
This put Gunther over the edge and he exploded, slamming me back on his cock with each spurt. The pain/pleasure and the realization that he was cumming inside me had me delirious and drove me over the edge. I think I passed out for a moment, when I came to I was laying face down on the carpet with a deep but strangely pleasant aching within my bowels. I was exhausted and felt thoroughly used up. Tracey was sitting in an easy chair smoking a joint and Gunther was nowhere to be seen.
“He’s in his bedroom sleeping like a baby. I think you wore him out” Tracey said “Quite the feat, you should be proud of yourself. I’ve seen him wreck two gurls in one session and go back for more.”
“I feel wrecked” I grunted and tried to stand but my legs were like jelly so I crawled over to the couch and forced myself up on it with some assistance from Tracey. I took the joint from him and toked up. There was a pile of Polaroids featuring yours truly on the coffee table and I picked some up and started looking through them. the first few I looked at were just of me dressed up in the pink lingerie that I was now wearing and I admired them thinking how sexy and cute I looked. There were several more of me laying across Gunther’s lap while he wailed on my bottom. I was shocked to see how red my ass had gotten under his hand. I was also a little shocked to feel the beginnings of an erection while looking at pictures of me dressed as a sissy. As I went through the pictures I got harder and harder and soon my cock was straining against my cum soaked panties. I thought it was odd because I hadn’t gotten an erection yet, even when I came while Gunther was fucking me. I asked Tracey about it and he told me a lot of sissies were wired that way and that it was pretty normal, at least as far as being a boy who likes to dress up in girls clothes and act like a total slut for men can be considered normal. I threw him a dirty look and turned back to the fascinating pictures in my hand. The pictures of me sucking his cock and of his cum all over my face soon had precum leaking out the tip of my rock hard erection and I started to stroke it absentmindedly and the pictures of him fucking me were about to drive me over the edge when Tracey cleared his throat , startled I looked up having totally forgotten he was there. He reminded me that there was video and asked if I wanted to see it? Oh God yes! He took the vhs tape out of the camera and put it in the video player and pressed play. Soon I was watching myself suck Tracey to completion like I was a teenage porn slut working a dick in Southern California. The shot of me holding his cum in my mouth was extra slutty and I started rubbing my boyclit again really enjoying the show. I nearly came several times but held back until the end when Gunther and I came together. Watching him slam himself into me as he shot his load sent me over the edge and I exploded with one of the best orgasms I’ve ever had even to this day. My sperm shot high into the air and fell back on me with a few drops spattering onto my face neck and breasts. I snapped out of my reverie and realized Tracey was standing next to me jerking his cock furiously, I could tell he was about to come and I leaned forward with my mouth open tongue out greedily awaiting my reward. He came in seconds coating my face and tongue with drops of salty jizz. There wasn’t much and I was a little disappointed but figured what the heck it was his fourth load in less than 24 hours!
I was still quite buzzed from the d**gs and the alcohol and the weed and it was around 6pm so I figured there was no way I was going home. I was sticky all over from their jizz and so I asked Tracey if I could borrow his shower. He said yes and I spent like an half an hour under the steaming water. When I got out of the shower and finished toweling myself off I came out into the bedroom and saw two full sets of clothes on the bed. One was a pair of jeans, tshirt, and hoody with a pair of vans skateboard shoes; the other was a sexy version of a catholic schoolgirls oufit, red plaid pleated miniskirt, white silk blouse, White lacy padded bra, white lacy panties, white kneehigh stockings and high heeled oxford shoes. I realized I was being given a choice, stay dressed as a gurl, which meant Gunther would probably make me suck him again and maybe even fuck me again. Or I could put on the male clothes and play time would be over. I looked at the long red nails still attached to my fingers, gave a little sigh and started putting on my new school girl outfit.