Prom Virgin

All characters in this story are eighteen years of age and older

My school prom was supposed to be the night I lost my virginity to my boyfriend Alex. Stereotypical, I know, but it's the truth. I'd only turned eighteen a couple of months before the prom, so I thought it would make it that little bit extra meaningful. I even used some of my savings to book a cheap hotel for the occasion, not far from the school..

However, my boyfriend Alex would not only ruin everything for us at the prom, but he would also devastatingly break my heart. Alex wasn't a virgin, so he was often frustrated at my reluctance to sleep with him until the prom. We were the same age and we attended the same school, and naively, I believed we would be together forever.

For the prom, my mother took me shopping to buy a dress. I was so excited trying on lots of fancy frocks, before eventually settling on a red, floor length, satin, v-neck, pleated dress. It even had a built in bra, giving me a sassy cleavage and one less item of clothing to stress about.

On the day of the prom I checked into the hotel at 2pm, dropping off my overnight bag and setting up the room for mine and Alex's much later anticipated arrival. I then went back home to begin getting ready.

At 6pm, one hour before the prom started, Alex arrived at my parents house to pick me up. He was so hot and handsome wearing a tuxedo, even my dad was impressed. My boyfriend commented how hot and beautiful I was, and my mother crooned over us.

I'm 5ft 5' and I have long, naturally waved, dark-brown hair and eyes. I'm also slim and busty, which I am grateful for. My mother is English and my father is Maltese, so I'm also blessed with an olive skin tone. By no means do I think I'm better than anyone else though. I just appreciate how God and my parents created me.

Finally arriving at the prom, full of nervous excitement, for many reasons, Alex and I mingled with our friends and soon-to-be former teachers, just having a good time. We danced a few songs together before sharing some of the alcohol that had been sneaked on site.

Some time around 9.30pm I went in search for my boyfriend. He'd gone off with some of his friends to vape, but I hadn't seen him in awhile. I checked inside and outside, then asked the guys leaving the boys room if Alex was inside, but he wasn't. My friends helped me search but my boyfriend was nowhere to be found. I was then reluctantly told to go and take a look inside the boys changing rooms. I thought all other areas would have been secured as no access during the prom.

I became anxious, feeling something terrible awaited me. Turning the corner in the hallway towards the boys changing rooms, I was greeted by a lad called Marcus, who was hanging around.

"Ohhhh fuck!" he cursed, as soon as he saw me. "What are you doing here, Pippa?"

"Where the fuck is Alex? Is he in there? I was tamping, dreading the worst by now.

Marcus tried to stop me entering the changing rooms but I was in no mood. I pushed him out of the way and then threw open the doors. Darkness and sexual groans greeted me.

"ALEX! YOU CHEATING BASTARD!" I screamed, then suddenly more people came running through the corridor towards the changing rooms.

"Shit! Pippa!" my boyfriend panicked, letting go of some girl bent over a bench with her green prom dress up her back. "I can explain!" he dared to try, quickly pulling his trousers up. "It's not what it looks like!"

I couldn't talk. My body was shaking with rage and I had tears streaming down my face. My breathing came quick and I just had to get out of there and run away from the prom. Total humiliation. Alex tried to chase after me but was instantly halted by two other boys. My friends rallied around me and a couple of teachers tried to get involved, but all I wanted was to get out of the building and as far away from my now ex-boyfriend as possible.

I found myself being too angry to cry for long. I wanted to punch Alex and the skank he was shagging in the boys changing rooms. Marcus could have a punch to, but violence and aggression wasn't in my nature, so I would start crying hopelessly again. My virginity couldn't have been further from my mind if I tried. Perhaps the girl in the green dress had done me a favour, I told myself.

Eventually, I got into a taxi and went to the hotel. I reassured my friends I would be fine. I was going to pack up the romantic candles and rose petals then call my dad to come pick me up. However, when I got to the hotel I couldn't bring myself to mess everything up. I broke down on the bed and cried some more. The entire evening and my relationship had just been ruined by my selfish ex-boyfriend. We should have been there in the hotel together, kissing on the bed and slowly undressing each other to have sex for the first time.

Knowing I had to pull myself together, I decided a drink in the bar was in order. I did consider changing out of my extravagant prom dress and into my going home clothes. The prom dress was too posh but the denims and hoodie in particular were too casual for my liking. So, I remained dressed as I was, and sorted out my car-crash of a face. I had mascara everywhere and my eyes were red and puffy.

It's not often I feel self-conscious when I enter a room, but seeing everyone dressed as casual as you like, I did feel ridiculous walking up to the bar with my long, satin dress, sweeping along the floor behind me. The jeans and hoodie would not have looked out of place here.

Of course everybody looked to see who the lost princess was, but I quickly let go of the sudden tension and ordered a Southern Comfort. As I sat at the end of the bar deleting Alex and his saved messages of love from my phone, I noticed there were a lot of men around. Workmen. Like my dads age. Forty and older. There were groups of them dotted around the tables wearing florescent clothing while they drank pints of lager and relaxed loudly.

Some of the men gawked and smiled at me. One or two even smiled and winked. It was like being in a nightclub, only it wasn't a nightclub. I couldn't imagine what they thought I was doing there, dressed as I was, looking angry on my own whilst getting drunk on Southern Comfort. I must have spent half an hour messaging my friends when a man approached me. He gave me an excuse to put my phone down and order my second Southern Comfort.

"That's a beautiful dress you're wearing. Not something you expect to see in a place like this though. Apologies for poking my nose in where it's not wanted, but are you ok?"

The man, if I had to guess, was around my parents age, maybe a bit older. Mid to late forties perhaps? It didn't matter. He sounded genuinely concerned for my well-being, nodding at the Southern Comfort in my hand. He was wearing those fluorescent work trousers I mentioned, and a black t-shirt that clung to his body. He had a dad-bod belly but his chest, shoulders and arms were thick a muscular.

"I'm cool," I replied sarcastically, as if it were all his fault.. "I'm cool like your trousers," I then rudely and needlessly mocked him.

The man laughed, took a seat beside me and asked the barmaid for two more Southern Comforts. I watched him as he ordered them. He was ok looking for an older guy. Ruggedly handsome with short dark hair and a clean shaven but weather worn face.

"I work on the railways. I head up the crew that just left. We work all sorts of hours and shifts," he explained. "So what's your excuse?"

"Excuse?"

"Looking so beautiful in a dress like that, in a bar like this," he smiled.

"It's a long, boring, complicated story," I shrugged and rolled my eyes.

"If I guess what it is you have to have another drink with me?" he grinned, sliding a Southern Comfort in front of me.

I laughed. "This will be interesting!"

The man sat upright in his seat and cupped his chin, pretending to be deep in thought. I laughed again. It felt good to laugh after everything that had happened.

"I'd start with your boyfriend." My eyes glanced up to the left revealing anger again. "I wouldn't like to guess what he has, or hasn't done, but the guys an idiot if you ask me."

"He's a guy, what do you expect?" I took a swipe at the male species.

"I'm Lewis, and I say forget any guy who doesn't treat you right," he smiled and we toasted glasses.

"I'm Pippa, and you were right," I told him, before knocking back another Southern Comfort.

"I was only playing with you, Pippa," he said respectfully. "Relationships are no joke when one messes the other about. It was a wild guess because you look great in that dress, but so pissed off at the same time."

I knew I was drunk when I felt the need to tell Lewis, this complete stranger, all about the prom. He laughed, frowned, cringed and then laughed again, but he only laughed when I did.

He then told me all about the time he caught his ex-wife in bed with another man. He was able to joke and laugh about it but I saw the hurt and regret in his eyes when he mentioned his young children.

Having consumed four Southern Comforts by now, the alcohol escalated things when I tried to joke through my explanation for being in that particular bar. As soon as I mentioned the words 'virgin' and 'virginity', Lewis started looking around us worried.

"How old are you, Pippa?" he asked, concerned all of a sudden.

"I'm eighteen!" I laughed, opening my purse to show him my barely a month-old driver's license.

"It's ok," he smiled, putting his hand over mine to close my purse. "I believe you. I just thought you were like... twenty-one!" I blushed and giggled, feeling flattered. If I was twenty-eight and he said I looked thirty-one I might have been offended.

From there Lewis rolled out the red carpet of compliments and I absorbed every single one of them into my drunken, scorned mind. Whilst we chatted I replied to a few messages from my friends whilst ignoring several calls and twenty messages from Alex, telling me how sorry he was. Lewis was aware of when it was my friends and when it was Alex contacting me. My whole demeanour changed between the two from happy to angry.

"So, what are your plans tonight, Pippa? Now your boyfriend has ruined your original ones."

I had no idea what came over me, well I do, it was everything including the Southern Comfort. I giggled. Southern Comfort, when not consumed responsibly, always made me horny. Up until that night the drink only ever had me masturbating in bed at the end of the night. Not tonight though.

"I'm sticking to my original plan," I giggled again.

"The prom?" Lewis chuckled. "Or your boyfriend?"

"Forget him. I set out tonight to lose my virginity! So that's what I'm going to do!" I laughed.

"Shhhh! Shhhh! Keep it down." Lewis leaned closer. "You'll get yourself thrown out." He then looked around before talking quieter. "And how do you plan on doing that by yourself?" he grinned.

I finished my last Southern Comfort for the night. Anymore and I'd be spending the night with my head in the toilet. It was my turn to talk quietly, or at least try to.

"Do you want to come back to my room with me?" I giggled.

"I couldn't think of anything better, Pippa, but are you sure? You've been drinking and you've had your heart broken. I don't want you thinking I'm taking advantage."

A few moments of silence passed whereby Lewis and I just looked into each other's eyes. It wasn't romantic or flirtatious, it was serious.

"I'm not precious about my virginity. To be honest with you, the sooner I lose it the better. I mean, what's the big deal about it anyway?"

Lewis grinned and put his hand on top of mine in my lap. The barmaid looked at us disapprovingly, but I didn't care.

"Are you sure about this, Pippa? Are you really, really sure about this?"

"It's only sex," I giggled again, as if I knew what I was talking about.

Lewis glanced down into my cleavage before looking into my eyes. "You're stunning, Pippa. Lets go back to your room."

When we stood up I realised how tall Lewis was. He was over six foot, and he was built like a brick shit house, as my dad always says. We then left the bar with me struggling to walk in my heels. As soon as we got outside Lewis wrapped his arm around me as if I were his girlfriend. He walked me from the bar towards the adjoining hotel, where we passed two of his crew smoking cigarettes outside. They nodded and grinned at Lewis, but once inside I heard them laughing. Probably laughing at me.

"Are you ok?" he asked, when the elevator doors closed.

"Yeah," I lied.

I was ok really but I was no longer the silly drunk in the bar. Seeing our reflections in the elevator mirror sobered me right up. Me, a petite eighteen-year-old in her prom dress being held by him, this giant railway worker. How did this happen?

"I'll look after you, Pippa. I won't hurt you. You deserve to be treated with respect," he told me. His eyes suggested otherwise.

The elevator only travelled up two floors, so we were out of it in no time, walking along the corridor towards my room. But in that short period he undressed me several times with his eyes. Outside the room I dropped the electronic key card. I went down on my knees to pick it up and Lewis joked we couldn't do it in the hallway. I looked up and laughed with my head only a few inches from his crotch. I knew what he meant.

Inside the room I immediately felt embarrassed. I'd forgotten about the candles and rose petals. Lewis grinned and told me not to be embarrassed, and to keep everything as it was. I told him I couldn't whilst giggling and blushing as red as my dress. It all looked so silly now. Lewis wasn't having any of it though. He picked up the lighter beside one of the candles and went around lighting them all. As soon as all ten candles were lit he returned to me and put his arms around my body.

My heart fluttered and I had mega butterflies going around inside my tummy. But there was no time to change my mind or ask for things to go slowly. Lewis pulled me tight against him and kissed me. I kissed him back slowly, realising I needed to feel wanted again.

Lewis started breathing heavily through his nose as he kissed me passionately, and I responded by moving my feet closer to him. He then put his hands on my arse and gently massaged my cheeks through the prom dress. I gasped and felt myself melt into him as m y boobs pressed and squashed against his firm body. After a few minutes I was so turned on and ready to be led by this man. Which was insane for every reason I could think of. It was like I'd just snogged one of my dads friends.

Lewis stepped back and asked me again if I was ok. I told him I was. I was a nervous wreck but I didn't lie when I answered this time. He then grabbed and started kissing me again while the candles flickered inside the room.

Lewis ran his fingertips up the full length of my back, brushing my sensitive bare skin. His gentle touch gave me goosebumps and he brushed downwards to the base of my spine again.

It felt like I was in a dream, an erotic dream, when his fingertips gently smoothed up my back one last time. We were still kissing passionately, our bodies tight together. His fingertips reached my neck then came across my shoulders to the straps. Shocks of electricity bolted up my spine. Lewis wanted me out of the dress and naked.

I gasped and my stomach felt like it was doing somersaults. With his fingertips moving softly along my shoulders, Lewis picked up the thin straps and kept moving his fingers to the ends of my shoulders. He then groaned into my mouth and I felt his fingers pulling the satin material down my arms.

Lewis then stepped back, leaving me swaying in a dazed bliss of Southern Comfort and heightened arousal. He grinned and told me I was beautiful and sexy. I knew it was coming but nothing could have prepared me for it. He reached for the sides of my dress and pulled it down to my waist. He just exposed my boobs. They dropped and bounced and Lewis groaned. He then tugged the dress over my hips before letting gravity do the rest.

The surge of adrenaline and sexual arousal almost caused me to faint. The dress fell to the floor leaving me standing in the middle of an expensive pool of satin. It no longer looked like a prom dress. It didn't need to.

Lewis took only a few moments to look over my body, he spent most of them looking at my D cup boobs and my mound at the front of the red satin thong. I expected his big hands to reach for my boobs, but instead, he told me how gorgeous and sexy I looked, before hooking his thumbs in at the sides of my thong. It was overkill. His hands looked too big and strong for such fragile underwear.

As soon as he finally had me naked, Lewis walked me out of the prom dress and over to the bed. Is this how a girl should give up her virginity? I questioned myself, as I watched Lewis strip down to his boxers. I might have been a virgin but I wasn't that naïve that I didn't know the bulge inside his boxers was bigger than average. It triggered my nervousness but something else was also triggered. I was soaking wet between my legs.

Lewis didn't say a word. On his hands and knees, he crawled over the top of my body. I shuddered at the size of him compared to me, and then my head start spinning like a washing machine full of thoughts. Lewis was big and heavy. He wasn't suffocating me, but I felt pinned to the bed, not against my will, it was just that having such an older man, an experienced man, in this position with me was overwhelming.

Wondering how, where and when he was going to start, I began to breathe anxiously. I needed to relax into my body and get the fuck out of my head.

"Relax, Pippa. You're gorgeous. I'm only going to make you feel good."

He then started slowly breathing warm air around and onto my left nipples. I suddenly felt stimulation in my boobs that I'd never experienced before, certainly not that level of intensity. With a mind of their own, my hands started stroking my belly, while Lewis continued blowing warm air onto my nipples.

I then felt a hand stroking my rib cage. It wasn't mine, but it felt nice and heightened my arousal, before it stroked around the curve of my boobs and in between them. I gasped as I felt my body break out in goosebumps.

Lewis was attentive, causing my eyes to drift closed as I moaned softly. A warm sensation then spread throughout my body. Lewis didn't know anything about me or what turned me on, he just seemed to know. He wouldn't touch my boobs, even though I wanted him to, he was teasing me, letting the sensations build up.

Then finally, he did touch my boobs. With the lightest of touches he circled them and my areola. I gasped again and moaned a little bit longer. His circles grew larger until his fingers eventually eased into my boobs and into a gentle massage. I began writhe then he gave my boobs a little squeeze and I groaned.

There was so much going on with my boobs and Lewis hadn't even used his mouth yet. The sensations started with the nerve endings, but now the sensations had spread throughout my whole body. Something was building slowly and gradually.

In between massaging and squeezing my boobs, Lewis managed to trace my areola without touching my nipples. I could have screamed. He was so close... so fucking close! I sighed in frustration.

"You have lovely big boobs for an eighteen-year-old, Pippa."

I opened my eyes and blushed. "If you say so."

"Don't be embarrassed. They're awesome. Just like you."

Lewis knew he had me right where he wanted me. Hot and excited, but still shy. He finally moved his fingers over to my erect nipples, and started rubbing them slowly. I gasped and arched my back, closing my eyes and moaning again. He then increased the speed of his fingers and applied a little more pressure.

I was aroused on the highest level possible, or so I thought. Ramping up the pleasure, Lewis pinched and flicked my nipples. It sent an intense rush throughout my body before he twisted and pulled on them. Each time he applied more pressure by either pinching, flicking, twisting or pulling, the more intense the pleasure was.