this is the story of how lost my virginity and began my journey to be the goddess I am today!
I have always known, even as a small child, that I was unlike other boys. I started stealing my sister’s clothing at the age of the eight. My parents caught me numerous times dressed as a girl, always telling me it was wrong and trying to discipline me. I enjoyed wearing her dresses, underwear and especially her shoes. My sister Kara was 18 at the time and rather promiscuous.
She would dress very provocatively, wearing high heels, and very short tight skirts. The only thing I ever wanted to be was her. She was absolutely beautiful, with long straight light blond hair and piercing light blue eyes. Her body was unbelievable, perfectly proportioned for a woman of 5 ft. 5. I remember seeing all the boys she would bring home when my parents were working, and take up to her room. I could hear them having sex. It sounded like great fun, and I wanted to try. After they would leave, I would sneak into her room and try on her clothing, looking at myself in the mirror and thinking what a pretty young girl I was .
Fast forward 10 years, my parents are dead. I received a substantial sum of money from their life-insurance, but promised to stay with my sister through high school, so I’m living with her family. I am an 18 year-old virgin transsexual. My sister has some suspicions about my unique needs, but can’t find a way to talk to me about them. As a boy I am unremarkable appearing, but as a girl I’m stunning. At 5 ft. 6 and 126 lbs., I have a similar build to my sister before she had her children. My hair is the same light blond and my eyes are the same light blue.
I have not had a haircut since my parents died three years ago, and it is now halfway down my back. I have very shapely legs that are topped off by a small tight ass. I have slender hips and a nice flat stomach. My shoulders are slight and my arms are thin and end in long thin fingers. Half of my closet is devoted to women’s clothing. The tighter and shorter the better. I also have an extensive collection of stiletto heeled shoes and boots. And I want to get laid. I dress in my bedroom every night, practicing walking in my heels and talking in a baby doll voice, trying to make myself the perfect girl. I didn’t have breasts yet, but I also looked five years younger than I was, so it didn’t bother me. I fantasize about being taken the way my sister was when she was a teenager, jerking off constantly.
I decided that Memorial Day weekend I would lose my virginity. I would travel to the gay barin the town next to ours, the Homestead, and find a man to fuck me. I would go on Friday, when my sister and her family left for the weekend to go to the shore, that would leave me the weekend with my new lover. The week passed excruciatingly slowly, I began to plan out and fantasize about what was going to happen on Friday. I chose the perfect outfit, the perfect fuck me shoes and continued to work on my makeup. High-school was the last thing on my mind all week, as an honor roll student my graduating was all but guaranteed, but that didn’t stop some of my teachers for making life miserable. Especially Mr. Booth the gym teacher.
He was a legend at our high school, Mr. All -State basketball and football who went off to college and would have gone pro but was injured. His playing days over, he returned home to begin teaching at his alma mater. It was as if he was put together by committee, picking the perfect parts for him. He was six-foot six, jet black hair and light brown eyes, perpetually tan and very well muscled, but not a body builder type. All of the girls lusted after him, and all the boys wanted to be him. He was friendly to the jocks, but enjoyed picking on the less athletic students in his classes. That included me, and at times I thought it was only me. I hated him.
Friday night finally arrived. My sister and her family left shortly after 3:30 which left me five hours to get ready for my big night out. I first took a shower and shaved my entire body so that I was silky smooth. Then I took a long hot bath with scented oil to give my body a lovely scent. I put on my sister’s silk robe and went to do my makeup and hair. The makeup was easy, and the blush, mascara, eyeliner and lipstick went on quickly. I knew how I wanted my hair it was only a matter of getting it done. It took almost an hour but finally the single braid down the middle of my back was perfect, with a white bow tied at the end. Now it was time to get dressed.
There was a problem, I had a raging hard-on. Taking care of that did not take very long. I pulled on the smallest pair of black lace panties I had and tried to snuggle my still semi-hard cock down between my legs. A black leather micro mini skirt that sat nice and low on my hips was next, followed by a loose white silk blouse which I tied off halfway down to show off my flat mid-riff. I chose a black leather choker to adorn my neck, and large gold hoop earrings. When I thought I was ready I added the finishing touch, 5 in. black leather ankle boots. I looked at myself in the mirror and was amazed. I was now a beautiful young woman who any man would want to have. My cock was straining against my panties. I was ready.
The drive to the bar took about 25 minutes, but it felt like two hours. As I pulled into the parking lot of the Homestead, the butterflies in my stomach nearly made me turn around and go home, but my lust and need for a man gave me the courage to go inside. It was like walking into a candy shop, about 80 men of all ages and sizes milling about a dimly lit room. The small dance floor in the middle of the bar was crowded with shirtless men gyrating to the disco beat. The smell of leather, denim, sweat, smoke and cologne filled the air. I could feel a hundred eyes watching me as I moved across the room. The butterflies returned, so instead of going to the bar I went to the ladies room. I ran into the third stall and sat on the toilet, my mind racing. What was I doing here?
Was I really ready to go through with my fantasies and lose my virginity? I looked around the stall, seeing the graffiti written on the tan walls all offering a good time if I would simply call this number. And I noted a hole about 3 in. wide in both the door and wall, next to the toilet paper dispenser. Glory holes, I had read about these in the magazine’s I’d bought . I had been in there for about five minutes staring at my well manicured hands, trying to drum up the courage to step out and live my fantasy when something caught my eye. Someone entered the stall next to me and had put their cock through the glory hole. I was mortified, with feelings of lust and revulsion fighting in my body. A voice from the other stall prodded me into action.
” Why don’t you just stroked it little girl. It won’t bite. ” it said.
I reached a tentative hand out and touched another’s cock for the first time. It felt hard and soft at the same time and it was incredibly hot. It wasn’t any longer than my own 7 in. member, but it was thicker than mine. I wrapped my fingers around the shaft and slowly started to jerk off my visitor. I heard a groan and then the voice returned.
” Your doing beautifully, that feels fantastic. Why don’t you kiss it?”
He was prodding me into giving him a blow job. I didn’t know what to do, but lust was beginning to take hold of my body. I knelt on the dirty bathroom floor and stared at the cock in front of me. I brought my lips to its head and gave it a light kiss. Another groan empowered me. I was in control of giving this man pleasure. My lips parted and I started taking his cock into my mouth. Having never given a blow job before, I didn’t really know what I was doing. I alternated sucking as much of him into me as I could with concentrating solely on his head and jerking him off with my hand. My other hand was under my skirt and inside my panties tugging my own cock. I came quickly, shooting cum all over my thighs. All the while I continued to blow my anonymous visitor. I was in heaven and my excitement and joy only increased when he screamed.
“I’m cumming!!!!”I wanted to watch this happen, so I pulled his cock from my mouth and jerked him off furiously. With my face only inches away the first blast of cum hit me right on the cheek. It was quickly followed by four more from the bucking , spasming cock in my hand. They all hit my face. I let go and reached for some toilet paper to wipe the cum from my face, and licked my lips tasting some of his seed. It was delicious, and I knew I had to have more.
” Thank you sweetheart, that was incredible. When you decide to come out to the bar I’ll buy you a drink . ” and with that my visitor left.
I finished wiping the cum from my face and legs and stood up. As I picked up my hand bag another cock, smaller than the first, appeared in the glory hole. I reached out and gave it a quick tug saying in my sweetest voice
” The lady needs to have a drink, but thank you for the offer lover. ”
And with that I stepped out of the stall and went to the mirror. My makeup was a mess. A handsome middle-aged man, obviously the owner of the second cock, stepped out of the stall and smiled gently as he walked out the door. It took about five minutes to fix my makeup and clean the dirt off of my knees. Finally I stepped out of the ladies’ room and went to the bar.
I found a seat near the end of the bar and waited for the bartender, an older woman, to arrive. She was talking to a heavyset man at the other end of the bar when I caught her eye. She came with a warm smile and a glass of white wine and introduced herself as Meg, telling me the gentleman at the far end of the bar had bought me the drink.
“That’s some way to introduce yourself to the regulars. ” Meg said.
“What do you mean?”
“Blowing the first man you meet 10 minutes after arriving here.” she smiled.
I was shocked at what she was saying, and it was obviously showing on my face.
“Don’t worry sweetheart.” Meg rested a hand on mine” It was just an unusual thing for a first timer to do. Usually they just stand in the corner looking like a deer caught in headlights. And Scott down there always tries to get to them early. What’s your name honey?”
” Shawna” I answered in an wavering voice.
” Well Shawna, welcome to my second home. I know your young, probably too young to be drinking in my bar, but you look like a sweet little thing, I like you and you obviously have big balls to do what you did. “she winked at me. I blushed.” So consider me your guardian angel for tonight.” Meg gave me an easy smile”I’ll keep an eye on you and give you the skinny on any one you’d like to know about. ”
Taking a drink of wine to steady my voice I said” Thank you Meg, I really appreciate it.” and with that she left to help some other customers. I looked in the mirror behind the bar and scanned the crowd looking for the middle-aged man from the bathroom. That was when I saw him. Mr. Booth, my sadistic gym teacher. He was standing in the middle of the dance floor, taller than everyone else in the room, wearing a skintight white T-shirt that showed off his beautiful chest and large arms. My mind began to race, did he see me? If he did would he recognize me? What would happen if he did? With my mind occupied with these questions, I reached into my hand bag and retrieved my cigarettes. With a shaky hand I pulled one out and went back again to look for my lighter. And that was when it happened.
” Tom Shaw” the voice said quietly into my right ear”fancy meeting you here.”
I looked into the mirror to see Mr. Booth standing directly behind me with an evil grin on his face. I was horrified and didn’t know what to do when I was rescued, at least momentarily, by Meg.
” Michael” she said” I want you to leave this little girl alone. Shawna, are you okay honey?”
Before I could answer, Mr. Booth answered for me.
“Shawna’s fine Meg, we’ve known each other for almost four years. “he said as he rested a large hand on my shoulder. “I was just surprised to see her here.”
Meg gave us a very hard look before turning to leave, and said”Honey, you just let me know if you need my help, okay?”
I nodded dumbly, too shocked to answer. Mr. Booth slid into the empty seat next to me and fixed a with his gaze.
“So you call yourself Shawna do you Mr. Shaw?” it sounded more like a hiss then a voice. ” I’ve always thought you were a little to effeminate, but I never thought you wanted to be a girl. ” He took my lighter from my hand and lit my cigarette for me. “If you want to be a girl, why don’t you let me treat you like one.” he said and put a hand on my thigh, just below the hem of my skirt.
“Mr. Booth” I stammered”please. If anyone found out about this I’d be ruined.”
“I know Shawna, that’s the beauty of the situation I find myself in. I have a male student who wants to be a girl, and is blowing men in the bathroom of the local gay bar.” How did he know that? “I think that you and I should get better acquainted. ” he smiled and I saw how beautiful his face really was. I could feel how hard my cock was underneath my skirt with his hand only inches away.
“Okay” I said numbly, transfixed by the rampaging lust I was feeling for him.
“So,” he said” should we stay and have a drink together, or should we go someplace a little more intimate and get to know each other much better?” his eyes were positively afire.
Again I could only answer weakly “okay” and with that he stood. My eyes were at his crotch level and I saw a very large bulge in his tight jeans. I wanted to reach out and grab it, but Mr. Booth took my hand and began to gently pull me off my bar stool. I stubbed out my cigarette, picked up my hand bag, allowing Mr. Booth to direct me towards the door. He walked behind me, and slid his large hands down to rest on to my slender hips. More than once I felt that large cock of his brush my ass. Again I felt the eyes of the men in the bar on me, but I was more worried by my high-school teacher, who knew my secret, directing me out into the parking lot.
The night air was warm and smelled of blooms when we reached the parking lot. Mr. Booth informed me that we would be taking my car back to his house. He opened the passenger’s door and told me to get in, then walked around and climbed in the driver’s side. If I thought the ride to the bar was long, the ride to Mr. Booth’s house seemed an eternity. He lived only a few blocks from my sisters’, but it felt like we drove for hours. The entire ride was silent except for the radio.
As we pulled into his driveway Mr. Booth looked directly at me and said ” Mr. Shaw, from now on you are my whore. I will call you Shawna, and you will service me whenever I want. In return I will protect your secret, understood?”
“Yes” I said weakly” thank you Mr. Booth. ”
“Don’t thank me yet” he said as he stepped out of the car. I started to open my door when Mr. Booth opened it completely and offered me his hand. I took it, was helped out of the car and led to his house. It was small but nicely appointed. I was directed to the living room where Mr. Booth motioned to me to sit on the couch. I sat down and crossed my legs still feeling confused and mortified by what was going on. I didn’t know what to do, but I also knew that my cock was rock hard and had been from the moment he put his hand on my thigh. He left the room and I could hear some shuffling from the kitchen. I went into my hand bag and pulled out a cigarette and lit it. He returned with a glass of wine and a beer and sat down next to me. He handed me the wine and his now his empty hand came to rest on my thigh again.
“How long have you been dressing Shawna?” he asked.
“For about four years” I said” but I’ve always wanted to be a girl. For as long as I can remember”
He took a drink of his beer and looked at my legs before asking ” And how long have you been sexually active?”
What could I say? I didn’t think, I just answered” Today was the first time I’ve ever been with anyone. “I took a large drink of wine
“Really! You are a virgin? So you’ve never been with anyone before you blew Scott tonight? Excellent. You and I are going to have so much fun together. When I’m done with you, you’re not going to want to fuck anyone else. ” and with that he stood up. He stripped off his shirt, turned to face me, and stepped right up to me. He put his hands behind my head and pulled me to his smooth chest.
“Ready to begin?” he said.
A wave of lust swept over me as I smelled him, my lips surrounded one of his nipples and I let my tongue flick back and forth over it. My hands stroked his back and slid down to cup his ass. He simply stood with his hands on the sides of my head and let me play. I could feel his cock, its heat and size against my stomach, growing. I reached for his zipper and found buttons. With my hands undoing the buttons of his fly, I began to kiss lightly down his stomach. My right hand went into his pants while my left pulled them down. I grabbed his cock as his pants slid by it. It was massive and it wasn’t even fully erect. 10 in. long and too wide for my fingers to encircle it completely . His balls were large and hanging loosely below his huge dick. It was beautiful.
“Little girl, I want you to meet my friend.” M. Booth said. “He may hurt you a little, but it’s a pain you will love. ”
What a smile crossed his face. I had both hands wrapped around his dick and a slowly stroking it. It was incredibly hot and even more heat was coming out of its head.
” Teach me how to suck your cock Mr. Booth.” I said as I went to my knees.
” Open your sweet little mouth Shawna,” he moved a hand to the side of my face and lightly pulled me forward ” and let him in. ”
I felt the huge head press against my lips, and I opened them. His cock head almost filled my mouth completely. Then he pushed in more until my mouth was completely full of cock.
“Relax your jaw little bit sweetheart, and this will be easier for both of us. ” he instructed.
I tried to loosen my jaw, to free up space in my mouth for him. I still had both of my hands wrapped around the shaft and was slowly pumping him. He was rocking his hips back and forth and I began to match his rhythm. I was a learning quickly because more and more of that gorgeous cock was sliding over my lips and into my mouth. Mr. Booth reached over the top of my head to grab my braid, using it to push my mouth further down his fuck pole. I looked up at his face and saw he was staring intently at me taking his member.
“Your doing wonderfully Shawna, try using more tongue. ” he smiled.
The tempo of my blow job was increasing. Mr. Booth was pushing my head down more quickly to meet his hip thrusts. I stroked with both hands and let my tongue tease the head of his cock every time he let it come to my lips. I was in ecstasy, my cock was rock hard under my skirt and I started to cum. Mr. Booth was not far behind me. His pace was increasing and I felt the second hand grab the side of my head. He was holding me tightly and began to pump his cock in and out of my mouth. I gagged a few times, but that didn’t slow him down, in fact his speed seemed to increase. He was fucking my face and I loved it. The speed, the power, the heat and the raw pleasure of the length man meat going in and out of my mouth was more than my mind could take. I reached around, grabbed his powerful thighs and pulled him into me. I needed more of that cock in my mouth. I needed it all, I needed it down my throat, I needed to feel his balls against my chin, I needed to feel his pubic hair on my nose. Most of all I needed to feel his cum in my mouth, I needed to taste him. He obliged, pulling his cock out of my mouth and while still holding my braid, jerking off in my face.
“Open that pretty little mouth of yours wide baby, I want you to drink my load. ”
I opened my mouth and stared up at him, my school teacher and my lover, to see his face filled with pleasure. He was breathing in short, rasping breaths, and his eyes were squeezed shut. His gorgeous chest was rising and falling rapidly. His cock head was just pushed into my mouth when he shot his first load. The taste was intoxicating and he kept pumping more into my mouth. I was drinking it like it was water and I was dying of thirst. He was spent. I grabbed his cock and took it back into my mouth, trying to suck as much cum out of it as I could. Mr. Booth let go of my braid, and stepped back out of his jeans to slump into the couch.
“We are going to have to work on your deep throat abilities before this is all done.”
Mr. Booth patted the cushion next to him telling me to come over and sit with him. I got up and went to him, snuggling in tightly to his chest and letting my hands come to rest on that glorious cock of his.
“That was only your second blow job? You really are quick study aren’t you. ” he stroked my hair and caressed my cheek with the back of his hand. All the while I was gently stroking his meat with both hands, occasionally squeezing his balls and licking his chest. I felt him begin to harden and I knew what I wanted.
” Mr. Booth,” I said sweetly,looking up into his eyes”would you please fuck me?”
“Of course I will Shawna. Repeatedly. Stand up and take your clothes off. But leave on the boots,they really make your ass look great. ”
I did what I was told, quickly losing my blouse and unzipping my skirt and letting it fall to the floor. I slid my cum soaked panties down and stepped out of them. My cock was hard, standing straight out. I looked at Mr. Booth and saw him smiling easily, right hand stroking his hardening cock, his left making a circular motion telling me to turn around. I did and let him see my smooth, small virgin ass. I felt his hand caressing my thigh and then my ass. I heard him stand and walk up behind me. I could feel his giant tool pressed against the small of my back. This was pleasure. I knew what was going to happen and I wanted it badly. He reached down and opened a drawer in the coffee table and pulled something out.
With his hips still pressed against my ass, he put a hand on my back and pushed me forward. I was standing bent over with my hands on the arm of the couch. He used his legs to push my legs apart, exposing me to him. I felt his fingers, lubricated with some sort of gel, opening my ass cheeks. It was wonderful, I felt tingles shoot down my legs to my toes and up my spine to the top of my head. He was very gentle, rubbing back and forth slowly, then inserting one finger into me. It sent a shock of pleasure all across my body. He started pushing the finger in and out, then inserted a second. My eyes rolled back in my head, and I came all over his floor. I heard him laugh as he felt my convulsions on his fingers.
“Your ready for your deflowering sweetheart, so spread those legs at a little further. ”
I felt the weight of his body leave me for just a moment, then the steaming hot head of his cock pressed against my ass, past my cheeks and pushing against my anus. His hands grabbed my hips firmly.
“This is going to hurt, but only for little while. I’ll go slow and make this the most pleasurable experience of your young life.”and with that he pushed, hard. I couldn’t pull away, his hands held me in place. I felt the head opening me up. It burned and hurt and I screamed for him to stop. It kept getting wider and wider, I knew how big his cock was and now it was invading my ass. I screamed again as the head finally passed through and some of the pain subsided. Mr. Booth didn’t move for a long time, then he slowly started to push forward again. The searing pain returned immediately and I felt my knees buckle. His strong arms held me up and he continued to push into me. I could feel him deep inside me and he still kept pushing more in. I was out of my mind to think I could handle this cock . I was screaming when I felt his hips hit my ass. He was all the way in, I couldn’t believe it. The pain was still unbelievable, but there was now something else, a huge pleasure, a warm wave that continually swept over my body and began to drown out the pain. Mr. Booth must have felt something because he started to withdraw his cock. The warm wave was now red hot and racing through my body.
“Kneel down” I heard him say. I did. He moved with me, his cock never leaving my ass. I was now on my knees with my chest on the seat of the couch, legs spread wide and a giant dick in my upturned ass. Mr. Booth kept a hand on my hip and grabbed my braid again. I felt him push forward again. The pain was much less intense and the hot wave much stronger. Now he started to really fuck me. I could feel his poweful hips slamming my ass on each down stroke, he was driving harder and harder. He was using my braid to get me to match his rhythm so I began to rock back into him, meeting his thrusts. I was lost in an ocean of pleasure. I could hear him “That’s it, take it bitch. Take that big cock. You know you love it. Fuck my cock.” I knew I had never felt this good in my life. But I wanted to watch him, so I put my hand back to stop him.
“What’s wrong?” he said .
“Nothing” I replied as I pulled myself off his gorgeous fuck stick and stood up on shaky legs. I turned and laid down on my back on the couch spreading my legs wide. ” I just want to watch you fuck me. ” I smiled.
He smiled as he moved forward and grabbed my ankles, pulling my legs as far apart as they would go. I felt his cock head push against me and slowly open me up again. There was more pain, but not nearly as much as the first time. And he didn’t wait, but pushed his entire cock into me in one strong stroke. I gasped for breath, overcome with pleasure. When my eyes opened again I saw the most beautiful sight, a giant cock fucking me nice and hard. He was a machine, pounding away as wave after wave of pleasure washed over me. I came again, shooting all over my stomach. I looked at his face and then down at his cock, which was moving with unnatural speed in and out of me. I tried to tighten my ass muscles, which I obviously did by the surprised look on his face. He let go of my ankles, and I wrapped my legs around his waist, locking my heels together and using my stilettos as spurs . That seemed to change the angle, and he pushed even more cock in to me. Heat was building in my crotch as Mr. Booth increased the speed of his pumping. He was breathing rapidly, and fucking me even faster. His hands were on my hips again and he was driving into me faster and deeper when he suddenly stopped and grunted. I could feel a mammoth load being shot deep inside me. A groan escaped his lips and then he started to pump me again. I was in heaven, with his cock buried inside me. I put my hands around his neck and started riding back into him trying to coax more cum out of him. His eyes fluttered and he put a hand against the wall to keep from collapsing on top of me . He was exhausted. He pulled his softening dick out of my stretched asshole and laid down next to me on the couch. I wrapped my arms around his chest kissing his sweat soaked face, whispering thank yous softly. And I dozed off.
When I woke up, the sun was up and I was in a bed. I could hear water running and knew that Mr. Booth was in the shower. I climbed out of bed and saw myself in the mirror. Did I look as different as I felt? My fantasy had come true, I had been fucked beautifully by a gorgeous well hung man. But I also felt ashamed because this was one of my teachers, and he could destroy my life. I sat down on the edge of the bed and began to cry. I didn’t hear Mr. Booth as he entered his bedroom.
“Feeling a little guilty Shawna? Don’t. It something you wanted to do, and I’m glad that I was the one you got to do it with.” He was standing in front of me with a towel wrapped around his waist, beads of water glistening on his sculpted chest, his brown eyes looking softly at me. “Does your family know where you are?”
“They have a shore house, so I’m all alone at home this weekend. ” I sobbed.
“Great. Why don’t we drive to your place, you can change your clothes, we’ll go and do some shopping!” he was trying to cheer me up and it was working.
“Okay” I said” where are my clothes?” I couldn’t remember anything beyond the tremendous fucking I had taken last night.
“Everything is down on the couch. I couldn’t find your panties . ” he smiled. He turned around and went to the closet dropping his towel to the floor. His body was beautiful, he had a massive back and his ass looked like it was hard as rock. He had thick, toned thighs, between which I could see his big balls and the head of his cock. The power of lust is hard to explain, but it was driving me again. I dropped to my knees and crawled until I was right behind him. I slid my hand between his legs and grabbed his cock.
“Ah, the morning quickie, that’s what you need. ”
That was exactly what I wanted. He spread his legs slightly to allow me greater access to his dick. I didn’t waste the opportunity, squeezing his balls with one hand while I slowly jerked him off with the other. I started to kiss his chiseled ass, letting my tongue taste him. He was getting hard and his balls were tightening. I knew what I wanted and that was him in my ass again. I released his tool and stood up, turned and walked back to his bed. I climbed on and got down on all fours, pointing my sweet little ass directly at him. It was an invitation he didn’t miss.
“You have the dirty little mind, don’t you?” I looked over my shoulder and saw him stroking his cock while reaching into his bed stand drawer. He pulled out some lubricant and smeared it up and down his shaft. I wiggled my ass invitingly as he knelt behind me. His knees push my legs further apart as he moved in behind me, and I felt his cock enter me again. It hurt intensely and I bit a pillow to keep from screaming. He never stopped pushing until he was deep in me. He grabbed my hips and began to fuck me. There was no slow build up, just an intense ,deep, hard and fast fucking. I came immediately, shooting my load all over his comforter. Mr. Booth came quickly also, riding my tight ass until he shot another load of cum in me.
We spent a lovely day together, shopping and eating lunch at an outdoor cafe. He even took me to a beauty salon, where my hair was cut and styled into two braided pigtails, and my fingernails were manicured and painted a bright red Mr. Booth was treating me like the woman I wanted to be. At the end of the afternoon, just before we drove home, we stopped at Victoria’s Secret. He bought me all the panties I wanted. Red , blue, emerald and black, all thongs. I was in heaven. The ride home was a dream, Mr. Booth put his arm around me while I rested my head on his shoulder and my hand on his cock. I rubbed him gently through his pants, and I wanted to wrap my lips around him, but he told me to wait. He said that he wanted this evening to be special, so I would have the wait until then to have him. Somewhat dejectedly, I restrained myself, but it didn’t stop me from continuing to jerk him off through his pants. He dropped me off at home and gave me specific instructions on what to wear that evening, and what time to arrive. And he told me to call him Mike when I was dressed as Shawna.
I had four hours before I was supposed to arrive at Mike’s house, so I took a long bath being very careful not to ruin my new hairdo. I went to put my makeup on, finishing this time with lipstick that was bright red to match my new fingernails. My cock was hard, as usual when I was dressing, but I decided if Mike could wait until tonight so would I. I chose a new pair of black underwear and slid them on, the feeling of silk on my cock head almost driving me crazy. Now to get down to finding what Mike wanted me to wear. White thigh high stockings went on first, followed by a tight white cotton blouse, again tied off to show my midriff. My blue plaid pleated mini skirt was next and I made sure to push it down so was riding low on my hips but still showed some thigh below the hem and above the top of my stockings . The shoes were a special request that I was happy to grant. 6 in. black patent leather stiletto heeled fuck me pumps. I slid into them and almost strutted to the mirror to look at myself. I was exactly what Mike had asked for, the schoolgirl whore who wore just enough of the school uniform not to get detention.
I had decided to be fashionably late, so I went downstairs and had a glass of wine and listened to some music. At 8:00 I got in my car and made the 15 minute trip to Mike’s house. There were more cars parked in the street then that morning, but I didn’t take note of them. My mind was focused on the second night of pleasure with Mike. I parked in his driveway and checked my makeup in the review, reapplying my lipstick. I walked to the front door with visions of that big cock sliding into me and rang the doorbell. Mike opened the door and I thought his chin was going to hit the floor.
“Wow” he said with wide eyes taking in the outfit” you look beautiful. That’s just the look I had in mind. ”
I blushed as he took my hand and led me into the house. There was music playing in the background and Mike looked fantastic. I wanted him right then. We entered the living room hand-in-hand and now my jaw hit the floor. There were two men seated on the couch.
“Boys, I told you she was a fucking knockout. Her name is Shawna, and she loves cock. “I tried to back away but Mike held my hand, slid his arm around my waist and wouldn’t let me move. He whispered in my ear”I told you you were going to be my whore, so tonight while your dressed like a whore, my friends and I are going to treat you like one. I hope you enjoy it!”
I almost started to cry. I thought this man cared about me but what he really wanted was to use me, to use my body as his fuck toy. Shattered , I let him lead me into the living room where he introduced me to Chris, a hulking blond man and Bill, a lanky black man. In my heels I was 6 ft. tall, and these three men were all much taller than I was. My mind was racing with visions of the gang bang that I was about to be the center of. And I found that the idea of having these three men was making me hard.
” Michael, may I have a glass of wine please?” I was regaining control of myself. I sat down in a chair and crossed my legs, making sure all three men got a nice look at my exposed thighs and my ultrasexy high heels. My eyes met Mike’s, and in them he saw something that made him turn on his heels and go to the kitchen. It was acceptance, I would be his whore and I would fuck him and his friends tonight. I wanted to do it. I had waited 18 years to lose my virginity, now was going to use these men for my pleasure. It was the genesis of the goddess personality that to this day uses men to fulfill her needs. But that was in the future, I didn’t know that woman yet. Now, I was in a lust driven haze.
Mike returned and handed me a glass of chardonnay. I took a drink and asked” So, what do you boys have in mind?”
” I want to watch these two guys fuck you senseless.” Mike answered wickedly “I want to watch them shoving cock in your mouth and your ass at the same time. I want to hear you scream in ecstasy as we repeatedly fuck you. I want to see you drink enough cum to drown.”
It almost sounded like fun and I could feel how hard my cock was, so after taking another drink I stood up and said”Let’s get started then. ”
Neither Chris nor Bill seemed inclined to be first so I went directly to Mike. I dropped to my knees in front of him and reached for his belt. Soon his pants were off and I was staring at his beautiful cock again. I looked up and met his eyes as I opened my mouth and took him in. He must have enjoyed watching my red lips slide up and down his cock, and my well manicured hand stroking what wouldn’t fit into my mouth because before long he had stopped getting a blow job and started fucking my mouth. With a hand on each pigtail, he was shoving his dick deeper and faster into my face. And then it happened. My throat relaxed and opened up when he thrust forward and I took his cock all the way down. To my amazement and his, I could take him completely in my mouth. With a loud moan he buried his meat in my throat and started cumming. I didn’t lose a drop, discovering that by swallowing I was milking his member of cum. When I released his cock, Michael staggered backwards and collapsed into a chair.
I stood up and turned around to see both Chris and Bill sitting on the couch naked. Both men were rubbing cocks that were bigger than Mike’s. Bill’s cock was longer than Mike’s, but about the same width, Chris’ however was not only longer but markedly thicker. I reached for my hand bag and reapplied my lipstick so these boys could also have the complete experience. Standing on the far side of the coffee table I reached my thumbs underneath my skirt and found the waistband of my panties. In one smooth motion, my Victoria’s Secret black thong was around my ankles. Stepping out of them, I walked around the table and opened a drawer to find the tube of lubricant. I applied a generous amount to my left hand and tried to make up my mind. Who would I fuck first? Would I be able to handle Chris? And if I couldn’t handle him in my ass, what would I be able to with him in my mouth? I wanted to try, so I reached out and began to lube up his gargantuan tool. It was pulsing heat. When it was completely covered, I turned sideways and bent at the waist so that my skirt rode up on my ass and shoved my middle finger inside me. It felt wonderful and it let me know what pleasures I was about to feel. Both men on the couch were watching me as I fucked myself with my finger. My cock was hard to the point of hurting but I had decided that I would cum only from being fucked, so I didn’t touch it.
In my sweetest little voice I asked” Do you mind if I sit on your lap?” Chris smiled as I turned my back to him, hiked up my skirt, and straddled his thighs. I felt his hands on my hips guiding me down. When his cock head pushed against me, I squirmed to get it in. I started to open up to take him when the pain began. I bit my lip in an effort to suppress a scream and I tried to stop to allow my ass time to adjust to his size but he wouldn’t let me. I was screaming for him to stop but his strong hands continued to pull me onto his member. When I felt I couldn’t take any more I hit his hips. The pain was incredible but I had that huge cock buried in me and now I was going to ride it. I put my hands on Chris’ knees and started to ride up. An intense pleasure gripped my entire body and I started cumming uncontrollably. Riding that cock for the first time was like no experience in my life. I was completely filled and stretched to the limit and feeling of it going in and out of me was indescribable. My eyes squeezed shut but I still saw colors exploding in front of them. My fingers were tingling as were my toes. Every fiber of my being was turned on by this cock in my ass. The strength ran out of my legs and I felt Chris’ hips bucking to push more into me, so I turned to him and said”Put me on the coffee table. ”
In one smooth move Chris had me in the air and then on my hands and knees on the coffee table. His cock never left me. Now I could feel him, all of this mass and bulk focused on the giant man pole fucking me. Each thrust drove me forward and I looked up to see a black cock swinging in front of my face. I couldn’t take my hands off the table or I would fall, so I simply opened my mouth and let Bill step forward and put his cock in. This was heaven. To have two impossibly large dicks working me from both ends, just what Mike had wanted to see, sent me over the edge again. I was cumming all over the coffee table while Chris fucked my ass and Bill began to fuck my mouth and throat. I lost all sense of place and time, it was simply too much pleasure. I could only feel these two cocks working me over and that’s all I wanted to feel. Chris was pounding me harder and harder driving my mouth further down Bill’s member until I felt his balls hit my chin. He grabbed the back of my head to hold me there and I felt his cock spasming in my throat. His cum was shooting into my belly and I could hear him speaking but it made no sense to me. Bill pulled his cock of my mouth and Mike immediately shoved his in. Strong hands holding my pigtails while he again fucked my face. Chris was grunting and swearing behind me. When he was about to cum he pushed me off my knees and on to my belly with his thrust. I felt that giant dick unload deep inside me while he had me pinned to the table. He pulled himself out of me and I felt the huge void left in my behind.
Mike stepped back away from me, put his hands under my shoulders and flipped me onto my back. He pulled me toward him so that my head was over the edge of the table. He walked forward and knelt down in front of me and stuck his meat back down my throat. I was watching his balls going back and forth as he used my mouth for his pleasure. I reached both my arms around and grabbed his ass, trying to pull more of him into me, my throat milking him and my tongue teasing his head at every opportunity . I felt someone caressing my legs and slowly pulling them apart. It had to be Bill. I wasn’t sure he would be able to feel anything after the fucking Chris gave me, but I felt him lift my ankles to his shoulders and impale my ass with his cock. It was bliss, I knew I was being used but I also felt like I was in control, that these men were here to pleasure me. I felt Bill kissing my legs and slowly pushing them forward until I was almost folded in half in an effort to get more of his cock into me. Mike had interlocked his fingers behind my neck giving him extra leverage to fuck my face harder and faster. I let go of his ass and grabbed my ankles to allow Bill the deepest access to me.
I heard Mike say “Get ready bitch, I’m gonna cum all over your face. ” and with that he pulled his cock out of me, shooting a hot load into my mouth, across my chin and onto my chest. His cum tasted both sweet and salty, part of me wished he had just shot in my mouth so I could drink all of it. My eyes found Chris sitting on the couch stroking himself. He smiled and mouthed the words ‘In just a minute you’ll be mine’ . I smiled back at him and looked at Bill. He was a handsome man with a strong lean body. His hands were on my stocking covered thighs, pushing them down and pulling them apart at the same time while he jackhammered my ass. I reached out and let my fingers tweak his nipples, feeling waves of pleasure washing over me again.
“Come on baby, fuck me harder. I need it bad.” I whispered. I looked down to watch his big black cock rolling in and out of me while my cock stood straight up and brushed his belly on each down stroke. I grabbed my dick and jerked it, shooting my cum up my stomach and onto my blouse. That was enough for Bill. He pulled out of me and moved forward to straddle my chest. He grabbed my head and pulled my mouth onto his cock just in time for me to receive his juice. My mouth was filled completely with cum, I couldn’t drink fast enough and some slid down my chin. I wanted to suck him but he stood up and simply said” Beautiful . ”
I was absolutely sated. I don’t know how long I laid on the table, my legs spread, eyes closed, feeling the cum drying on my chin, neck and belly. When I open my eyes Chris’ face was hovering just above mine, smiling.
“Did you enjoy that?”
“Immensely” I replied in a weak voice.
“Then you’re really going to love this” he said “I want you to stand up and take off your skirt and blouse. ” I did is I was told, rising onto shaking legs. I left my clothes in a pile on the table and stood in front of him in just my shoes and stockings.
“How do you feel whore?” Chris asked as he began to run his large rough hands over my body . “My bottom is a little sore from the workout you boys gave it, but I feel great.” I smiled back him.
“Good .” His hands were on my thighs, gently rubbing and kneading them. I was getting hard again! “You like this, don’t you? You like feeling me rub you, almost touching that little dick of yours. But I won’t touch it. If you want to get off, you can get yourself off. ” I wasn’t disappointed because I knew these men would only pleasure me with their cocks. “I want you to grab the back of that chair, we’re going to put on a show for Mike and Bill. ” They were both smiling, Mike in the chair at the foot of the table and Bill from the far corner of the couch. Chris turned the chair so that when I grabbed it the other two men would see me from the side. I grabbed both corners of the back to the chair and looked at Chris, still seated on the couch and said “Well?”
He stood up and I got my first look at how absolutely huge his dick was. It was as thick as a beer can and at least twice as long. He dropped the tube of lubricant on the coffee table and greased his cock head with his right hand. His left hand grabbed my hip and pulled me back until my torso was parallel with the floor. He pried my legs further apart with his knee and rubbed some lubricant on to my asshole.
“Ready?” he asked. Before I could answer he had driven that immense tool all the way into me. I screamed in pain, my eyes snapped shut and my fingers dug into the chair. It felt like I was going to split in two. I tried to relax but it did no good. It was just too damn big. And he gave me no time to get used to it, fucking me immediately with powerful strokes. It took a long time for the pain to recede even a little, but when it did the feeling of pleasure was incredible. I opened my eyes and looked at the other two men who were obviously enjoying the show. Both were smiling broadly so I smiled back at them and began to ride back into Chris, meeting his thrusts. I came on the floor again, the spasms of my orgasm tightening my asshole around Chris’ cock. His pace never changed, just a strong, hard and deep fucking. My legs were going weak as waves of pleasure crashed through my body, so I pulled myself to the chair and bent my waist over the back. With my face on the cushion, my feet dangling in the air and my ass poined towards the ceiling Chris went even deeper into me. He grabbed my shoulders and pummeled my little ass. The faster he went the bigger the pleasure.
“That’s it Chris, fuck that whore good!” I heard Mike screaming.
“Yes, please, fuck me good. ” I mumbled. He was. It felt amazing to have that big cock using me. I had no strength left and I felt my body go limp but he just increased the speed of the fucking he was giving me. He finally pulled out and I waited to feel his cum on my back but it never happened. Then I heard him.
“Open wide bitch and get your reward. ”
He was standing right in front of me jerking off, his giant cock pointed at my forehead. I lifted myself up off the seat and opened my mouth. He pushed his dick in, it was so big only the head would fit, and blew his load. It felt like gallons of cum were filling my mouth. I gagged as I tried to swallow as fast as I could. And the more I swallowed the more there was. There was no room between my lips and his shaft for any to escape, and his spasming cock just kept shooting. After an eternity I had taken it all, so I let my tongue dance across his cock head.
“You’re done.” he said as he yanked his cock head out of my mouth.
I laid exhausted over the chair for a few minutes, snapped out of my daze by hard slap on my exposed ass. It was Mike.
“Put your clothes on and go home” he sneered ” we’re done with you.”
I watched as the three men collected their clothes and left the room, exchanging high fives and handshakes as they left. I was still very weak, so I pulled myself offthe chair and onto the floor. I got my knees and tried to stand up. I was so wobbly on my heels that I had to kick them off. I found my skirt and blouse and pulled them on quickly. I picked up my shoes, and grabbed my hand bag to fish out the keys. As I stumbled for the door I heard Mike behind me.
” I hope you enjoyed that bitch, because next weekend we’re going to do it again. And I think I may invite a few more guys over.”he smiled that evil smile again.
I got in my car and drove home, smiling the entire way. I started to replay the entire night in my head. I had been ravaged, taken in every possible way, used and I loved every minute of it. Mr. Booth had betrayed me, but I didn’t care. The decision was so easy. I would continue to fuck him and his friends, to protect my sister and her family’s reputation, until school was out. Then I would leave this town forever.