Prom Queen Ch. 02


Last night was a blur. I was shaking in disbelief of the things I had done. I actually kissed another guy, on the mouth, for over an hour. I had his cock in my mouth and sucked him. I swallowed his cum. I looked in the mirror at the small, frail young man that faced me and still could not believe what I had done. Maybe I was in shock but I was hard as a rock too. I had morning bone many times before, in fact it was very frequent at that age but I had spent half the night masturbating and had cum five or six times. Sleep was out of the question when I went to bed the night before. The taste of Andy’s cum was fresh on my lips and the vivid memory of my seduction dressed as Mary prevented that. Even after one orgasm, fatigue did not set in. The image was too intense. I could still feel his tender hands roaming over my body, holding my head while his tongue invaded my mouth. I could still picture his bright blue eyes looking at me with lust as I sucked up and down on his shaft. The soft feel of my silk dress on my smooth thighs and light caress of my long tendrils of hair on my back was also vivid. It took several hours of stroking and two worn out wrists to wear myself out. Now it was 10:30 AM, I was awake, and I was hard again.

I began to wonder how Andy felt today; he had a couple drinks but was sober enough to know what he had done. Would he regret it? Would he cop out and claim too much booze on his actions. What would his frat brothers say to him? Most importantly however; would he follow through with his promise of taking me out on a date? My mind was a fog, I had been drinking too at that party and my head had felt better. I had to ask myself, “Would I be able to follow through with my promise if Andy called?” I looked down at my stiff, purple, straining erection and answered my own question with an explosive burst on my hand.

As I licked up the remains of my morning orgasm the phone rang. I raced to it. “Hello?”

“Hi, can I speak with Mary?” replied Andy’s voice. Mary? It seemed silly that this charade was necessary at this point but it was okay with me, I liked the sound of it.

“Sure! Just a second,” I answered. I swallowed deep and adjusted my voice to the higher pitch I used the night before. “Hello? Who is this?” I asked coyly trying not to laugh at the same time.

“Hey babe, it’s me Andy, just calling to how you are after last night.”

“I’m great. I had a really nice time with you. I was wondering how you were feeling about everything?” I inquired.

“No worries, I had the best time with you. You were unbelievable. I have never been with a prettier or hotter girl than you and was wondering if we are still on for tonight?”

My heart was racing. This is what I had hoped for. There was no sound of rejection in his voice at all. I was very pleased and relieved. “So where are you taking me?” I asked.

“Pizza and a movie okay with you?” Andy hesitantly asked. I smirked at Andy’s nervous response. It was nice to know I wasn’t the only one. After agreeing to his invitation it dawned on me for the first time that I was drastically unprepared.

I quickly scanned my female wardrobe. It just wouldn’t do. Almost everything I had, other than the gown, was fine for flitting around my apartment but I nothing suitable for a date in public. I had seven hours until my date and would need most of that to prepare. I had a quick shower and shave. I assessed that my legs were alright for right now, so I did a quick makeup job, put on my wig, my stuffed black bra and panties from the night before, a black turtle neck sweater, grey skirt, black panty hose and my low heel black granny shoes, tucked away any sign of a bulge and got ready to go shopping. I felt confident from the reactions I got the previous night that I could pass in public for a woman. At that point, even I was spotted I wouldn’t care. It was only Mary’s second public appearance but weeks of private practice paid off.

I strutted with confidence through the university neighbourhood. In fact I turned many heads along the way. It was a different feeling, being looked at like a piece of meat. I now understood what girls meant when they talked about that. I found a nice boutique with trendy clothes. Even the sales lady didn’t give me a second look. She helped me pick out a soft, peach coloured cashmere sweater and a pleated, plaid baby blue and peach miniskirt. I imagined my white pearls would look nice with it. I then went to the lingerie store and picked out some white lace panties, bra and camisole. I decided on white stay up stockings to top it off. At the shoe store I picked out a pair of peach pumps and a matching clutch. I figured my dad would have a heart attack when he gets the credit card bill. I made one more stop at the drug store to pick up some makeup as well as some lubricant and an enema kit. While I was there I picked up a pamphlet on hormone therapy.

My successful shopping trip had felt great. Not only was I convincing to the public but I felt very natural as a woman too. At home I stripped down and got to work right away. I used the enema, which felt weird. If that were anything like what sex would feel like I was not looking forward to it. After that, I had a long bath, fixing up my shave on my legs and armpits. I soaped up my fingers and began working on my back door. It had never had anything in it before and my biggest worry was the pain that I might experience. I inserted one finger easily, then another. Not too bad so far. I worked them around trying to stretch the muscle. Then I tried to add a third finger. It was difficult and it hurt. Before I got too frustrated, I calmed down and began thinking about Andy again, imagining it was him behind me. This helped and soon my pain was replaced by a more pleasurable feeling. I worked my asshole with three fingers until the water started getting cold. The ordeal had got me hard again so used my other hand to relieve myself while having three fingers knuckle deep up my ass.

I spent much more time doing my makeup than I did earlier; making sure every detail was perfect. I used a much more subtle shade of coral lipstick this time and my eye shadow matched my sweater. I touched up my finger and toe nail polish and gave myself a nice clean smelling body spray and a touch of perfume on my neck. I put on my white undergarments, skirt and sweater. I used the same white pearl necklace and earrings from the night before. I wore two butterfly clips to keep my long red hair out of my eyes and finally put on white thigh highs and shoes. I took one last look in the mirror. I had again amazed myself. There was a totally different person looking back at me. Who was this girl? She looked part slutty schoolgirl, part virgin debutante. Feeling virginal and yet slutty at the same time I figured the look was appropriate for the occasion.

Andy picked me up right on time. He was wearing a casual polo shirt and dress pants, making him look very sharp. His blond, curly hair was in its usual state of disarray. When I opened the door to greet him his jaw nearly hit the ground. He was speechless. I just gave him a peck on the cheek, grabbed his hand and lead him away.

Andy was very sweet throughout the date and seemed to be able to ignore everyone else around him. He never seemed to look at others to seek their approval or wonder if anyone was suspecting me. He put his strong arm around me while we walked and held my hand while in line waiting for a table. During dinner I asked him about his frat brothers. He admitted that he had not told them anything and they were all so drunk at the party, that few would remember any of the details. He had not decided what he would tell them exactly. All he knew was that he wanted to be with me. He then turned the tables on me and asked if my family or friends knew about my secret. I told the truth too but like him did not worry about that for the moment.

I ate very lady like, even using a knife and fork on my pizza so as not to mess my nails and makeup. Andy couldn’t take his eyes off of me. I started playing footsies with him under the table. I took off one shoe and ran my clad foot up under his pant cuff. He enjoyed the teasing very much as I discovered when I let my foot touch his lap under the table and with my toes felt his throbbing erection.

We then went to the movies. Andy kept his arm around me the whole time. We sat in the back row of the theatre. I don’t remember what was showing, as I was busy the whole time. I started by leaning my head on his shoulder, then gently blowing into his ear. Before long, he pulled me closer and started kissing me. It was just as electric as the previous night, maybe more so since we where one hundred percent sober this time. I could feel his body heat as his passionate kiss consumed me. We made out with complete disregard to all others around us. At one point we noticed several people watching us instead of the movie so we took a break and just snuggled. I looked down to see that ever present bulge on Andy’s lap. I discreetly let my hand fall on it and gently massaged it through his pants. This teasing was driving Andy nuts. He kept on kissing my neck and at one point his hand dropped down to my ass. He cleverly inched up my wool skirt until he could slide his hand underneath it. He grabbed my soft bum and felt my lacy panties. I moaned my pleasure so Andy slipped a finger under my panties and began probing at my bum entrance. As he discretely worked his fingertip inside me I pulled his face to me and started kissing him again very forcefully. The heat from his crotch on my hand was burning hot.

We decided mutually to not wait for the end of the movie. We got up and walked out half way through. We almost ran to the car. Once inside, Andy pinned me to the seat and kissed me harder than ever. His tongue felt halfway down my throat. I sucked on his tongue just as I had his cock less than twenty-four hours earlier. He was on top of me with my one leg wrapped around his waist. My skirt was hiked up to my waist and Andy had a handful of my ass. The gentleman had given way to the animal. I thought he was ready to fuck me right there. I reached for his pants and undid his belt, button and zipper. His raging hard-on pushed its way out of his underwear. Anyone walking by could have seen us, maybe they did. I grabbed hold of his big cock and could feel the strain and the pre cum starting to ooze from the head. Andy backed off our kiss for a second as I fell to his lap. My lips immediately encircled his bulbous cock head. My tongue tasted the dollop of cum as I sucked it down my throat. Andy quickly scanned around to make sure we were alone. He was breathing was heavy and laboured as he fucked my face. He pulled my face off his erection for a second. “Baby, I’m on the edge, you’ve got ready to explode.”

I grinned, licked my lips, and said, ”Just go for it lover.” With that I opened my mouth wide and engulfed his member taking it deep into my throat. He had no choice but to let it go, sending a torrent of molten hot cum deep inside my stomach. Andy came and came for what seemed an eternity. I swallowed the now familiar tasting sperm with relish. When he had finished I eased off of his pole and raised my head without spilling a drop save a light glaze on my lips. As we recovered I accidentally let out a very un-lady like burp. We both broke out in hysterics, laughing uncontrolled.

“Take you home princess Grace?” he asked. We drove back to my place still laughing our asses off. By the time we arrived we had both calmed down. Reality had reasserted itself. We walked to my door hand in hand. I unlocked the door and asked Andy in. He seemed nervous but was eager as well. Once inside Andy again pulled me to him and kissed me passionately. We made out standing up while his hands once again found their way under my skirt to my pert bottom. I slowly eased back eventually breaking our kiss and took Andy by his hand to my bedroom.

Once inside the room, I started slowly peeling off Andy’s clothes. I kissed areas of skin as they became exposed. When he was finally naked, I marvelled at his masculine swimmers body. It was the first time I was truly excited to look at a man’s body. His cock was already semi erect and ready for more action. I felt flattered. We were standing next to the bed, and Andy softly kissed me on the mouth while holding my head. As we necked, he undid my sweater and pulled it off. He then undid my skirt and it fell to the floor. I stepped out of my shoes and Andy leaned me back onto the bed. I was still wearing my panties, bra, camisole and stockings. He jumped onto the bed beside me and we resumed kissing. I had a hold of his dick again and was caressing it with my soft hand. I instinctively kissed my way down his hard body until I came to face his crotch. I gently sucked his shaved balls giving each a tongue bath. I held onto his tight buns while licking his shaft like a popcicle. It felt so good in my mouth and I knew I was ready for him to fuck me with it.

Andy was ready too and he pulled my face to his, softly kissed my lips and turned me onto my side. He kissed my neck lovingly then my shoulders. His hands glided softly over my skin. Andy’s kisses traced a path down my arm to my hip. Once there he started kissing my hip and my ass cheek, it so sensual. His tongue traced the line separating my bum cheek from my thigh. Soon his tongue was licking the panties along my crack. Very slowly he began lowering my pretty white panties down my hips until they reached my stocking tops. He left them there and bean licking my bare ass. It felt so soft and sweet. When his tongue travelled between my cheeks I thought I had gone to heaven. He eventually got to my rim and began licking faster. I could feel his hot saliva wetting my hole. Next his tongue stiffened and penetrated my asshole. I loved the feel of his wet tongue inside me and began writhing with ecstasy. Next a finger joined his tongue and soon he took his tongue out and placed a second finger in. I reached over to the nightstand and handed him the lubricant. He made good use of it and eased my little hole open very carefully.

“Have you done this much before?” he whispered in my ear.

“I am a virgin,” was my reply much to his pleasure. “ Have you fucked many girls in the ass before?” I added.

“You’ll be my first sweetheart.”

Andy’s hard member was now sliding up and down between my buns. I reached back with a handful of lube and rubbed it all over his erection. I guided the big purple head to my opening and placed it against my virgin rectum. I rolled my hips back a little as my sphincter muscle started to stretch around the massive organ. I started feeling dizzy, and there was a sharp burst of pain; it was too big! I was determined to try again and took a deep breath and exhaled as I eased back onto it. Andy rubbed my shoulders and kissed my neck to help relax me. That felt nice. He was nibbling my earlobe and stroking my legs with his hands too. I was using my hand to pry my ass cheeks open. I soon felt the ring of my hole wrapping around the shaft of Andy’s cock. The head was inside me. Slowly he pushed it in deeper. It hurt but not sharp like before, more of a numb pain. Before long I could feel Andy’s balls touching the back of my thighs meaning he was all the way in. We didn’t move for a while we just lied there enjoying the feeling of being locked together. He was so good to me, taking his time and soothing me throughout the event. It wasn’t long before he couldn’t help but rotate his hips for sensation. It felt okay so I began moving mine too which Andy enjoyed. I let out a low moan and indicated to my lover that it didn’t hurt that much anymore.

Andy slid his dick outward until just the head was inside my bum. I pushed back against it and he buried himself back in again. Fuck that felt so good! He took the hint that I liked it and began a slow but steady fucking rhythm. Andy nuzzled my neck as he fucked my ass. I could see in the mirror a different angle of our coupling. I could see my white panties stretched tight by my legs, my round ass held by Andy’s hands, my sphincter stretched rudely around the thrusting pole of my muscular boyfriend. My own organ was itself hard and standing out to my front. Andy too was enjoying the view of his big dick pounding away at my sweet little bottom.

After a good fifteen to twenty minutes of this bliss, Andy could hold back no longer and launched a good salvo of sperm into the depths of my rectum. I loved the feel of his hot cum flooding my bowels. It was like a dream. Andy was not finished by a long shot. He was still hard inside me and wanted to go again. He rolled me onto my back and put my ankles up on his shoulders. He ground himself even deeper into me. I could feel and hear the jism slopping up out of my butt along his shaft. Although the resistance of my ass had decreased I was still tight around his cock. Andy lunged with deep strokes into me. He was fucking me pretty hard now. It was wonderful. “Yes baby! Fuck me! Fuck me hard stud!” I found myself yelling uncontrolled.

This made him slam into me even harder. He crawled up on top of me and kissed me hard on the mouth. We made out while we fucked like a wild porno movie. My clit was squashed between the two of us and the rubbing motion was getting me close to cumming too. Andy sensed this and flipped me back onto my hands and knees and started fucking my ass doggy style. He reached in front and took hold of my throbbing clit. He stroked it roughly and whispered into my ear, “My my Mary, what a big clit you have.” He kept stroking me while slamming away like a jackhammer on my asshole. I couldn’t hold back any longer and blew my love juice onto Andy’s hand. He promptly brought it up to my mouth where I licked up every last drop from his fingers. He enjoyed watching me eat up all that cum and it wasn’t long after that Andy let go another blast of his cream into my overflowing asshole.

We both past out in each other’s arms after that. In the morning I woke him up with a blowjob, then we made love again. Andy was some lover. He decided that he would like to go out with me as Mary full time. It meant keeping my female persona all the time. I seriously considered the hormone therapy too. I had no idea how to break it to my family that I was a girl now and liked it that way. As for Andy, he decided to leave the frat house and move in with me. He is now talking about a job when he graduates in the spring and having me drop out to be his kept woman. Decisions, decisions, decisions!


Report Story

bytgirl_Mary© 12 comments/ 111836 views/ 31 favorites

Share the love

Also in this series

Report a Bug

1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartLoveSoul, Cadian122 and 29 other people favorited this story! 

by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

There are no recent comments (12 older comments) - Click here to add a comment to this story or Show more comments or Read All User Comments (12)

Add a

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

Refresh ImageYou may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: