Prom Virgin

Losing my virginity on prom night to an older guy

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.

I loved my boobs. I loved them even more now. I couldn’t believe I hadn’t learnt to get this excited with them before. I thought I knew my body better than anyone. Turns out an experienced old man knew more about my boobs capabilities than I did.

When Lewis finally used his mouth he gently traced little circles around my areola with his tongue. I was breathing so heavily and stroking my belly I thought I was going to climax. He flicked my nipples with the tip of his tongue and gave my boobs another little squeeze.

Forget the Southern Comfort, I was spinning out on nipple and breast sensory overload, as Lewis progressed to nibbling on my nipples. If that wasn’t enough, he progressed even further by gently sucking a nipple into his mouth. The sensitivity increased and then he sucked on the other nipple. I wondered if he’d heard it screaming not to be left out.

The entire time I had been moaning and writhing beneath this forty-five-year-old railway worker, as he pleasured my eighteen-year-old boobs. I was then starkly reminded of my virginity.

Lewis held, squeezed and kissed my boobs before kissing his way down my belly. Just when I thought he was going to cross down over my shaven pubic mound, he moved left and kissed along my thigh. He then moved inside my thigh and crossed over the left. All this teasing was torture. Amazing, but torture.

“Mmmmmm!” Lewis moaned, with his head between my legs. “You have a very beautifully neat pussy, Pippa,” he said, before his tongue the flat of his tongue licked right up the centre of it.

As soon as I felt him lick the soft folds around my vaginal opening, I arched my back and sucked a deep breath into my lungs. I then started moaning uncontrollably when his tongue pushed inside and licked my inner folds. It felt amazing. Truly amazing.

Lewis moved his tongue up and down a few times, and I instinctively opened my legs a little wider to give him more access. My eyes were closed but I felt his tongue slide up higher. It reached and spread my clitoral hood before it started flicking my favourite part of my body. My clit. My bud. My best friend before bedtime.

By now I was groaning and gasping. Lewis was making slightly different noises. It sounded like hungry moans and grunts. His hands moved from my thighs up my body to my boobs. He cupped and caressed my curves for a while, stimulating two of my most sensitive parts of my body. It definitely felt better having a man doing it to me. Especially one who knew what he was doing.

My hips started to buck and I was suddenly panting. Hoarse cries of ‘yes’ breathed from my lungs over and over again. The heavier I breathed the faster Lewis licked my pussy and flicked my clit. His hands pushed my boobs together and then he started playing with my nipples. They were still hard and aching from when he last touched them. It added to the powerful sensations engulfing my body.

I suddenly became aware of some deep feeling sneaking up on me, and then on impulse, I gripped the bed covers and shuddered the words ‘I’m gonna cum’. I could feel the rose petals in my hands as Lewis groaned into my pussy and sent me on my way.

Then bam! My body exploded and I experienced a powerful climax. It came in tremendous waves, which travelled through my body. “Fuuuuck!” I gasped.

“That’s next,” Lewis chuckled, before grinning a little arrogantly and asking if I had enjoyed the orgasm. I smiled shyly and whispered ‘yes’ nervously. He then pressed his lips against mine and kissed me.

I winced at the thought that I was kissing him straight after his mouth had been down there, but I didn’t taste anything on his mouth or tongue, so I relaxed and found it actually turned me on even more.

Once my intense orgasm subsided, I could have quite happily rolled over and gone to sleep, keeping my virginity for the next ‘someone special’. That was just fantasy thinking, and I knew it. Lewis was ready to claim my virginity, and I was ready to give it to him.

“Do you have a condom?” I whispered, still recovering my breathing.

“I don’t sorry. Do you?”

“No.” I suddenly felt uncomfortable.

“But you set all this up to have sex tonight?”

“Yeah, with my ex-boyfriend, not some guy I met in a bar,” I laughed, before a fleeting moment of guilt containing Alex whizzed through my mind.

Lewis chuckled and lay between my legs. “So, you’re on the pill?” he asked, rubbing his cock over my clit.

I gasped and nodded, about to say I’d rather we still used a condom as well, but the sensations he was causing with his cock, stopped the words from coming out.

“You’ll be fine, Pippa. I’m clean and you’ll enjoy it more without a condom. We both will.”

I wasn’t sure I agreed, but all I could think about was the feelings pulsating between my legs. I moaned and my body started moving again.

“It feels good, doesn’t it,” he smirked, pressing into my vagina.

Whether or not his cock was big in comparison to other men didn’t matter, he was big for me, too big, I thought, as I felt him pushing into my vaginal opening, letting me know I was about to become a woman.

Perhaps sensing my anxiety was on the rise again, Lewis tried to assure me that everything was going to be ok, before kissing me softly. It was a nice distraction for my mind. I was able to relax into all of my sense pleasures which were being triggered simultaneously for the first time.

“I’ll be gentle, Pippa.”

“Uhhhh… ow! Ow! It’s too big! Ow! Your too big! Shit! Ow!”

“Relax, I’m almost inside you.”

“Ow! Shit! Uhhhh! It’s too big! Ow! Fuck!” I winced, then something popped. It wasn’t my hymen, I’d previously broken that all by myself. It was something big pushing inside me.

“Mmm, fuck! Uhhhhhh! I’m in, Pippa. Relax, sexy.”

Lewis was inside me. An actual real man was inside my vagina for the first time in my life. He pushed a little further inside before pulling back, only slightly. As he stared deep into my eyes I felt him moving backwards and forwards. It was only tiny movements but my opening still felt too stretched, before suddenly, the pain started gradually turning into something wonderful.

“Ah… ah… ah… ah… uhhhh… ah… uhhh…” I whimpered as the sensation pushed deeper into my and stretched my insides wider.

“Uhhhh… that’s it, Pippa. Ahhhh… you’re so tight.”

“Ah… ah… sorry… ah… ah…”

“Don’t be sorry… uhhh… damn… you’re perfect… you feel amazing…”

“Ah… so do… ah… you… ahhh…”

“You’re definitely on the pill, yeah?”

“Ah… yes…”

“Ok, that’s good… how do you feel now?”

“Ah… amazing… don’t stop…”

“You’ve taken it all. I’m all the way inside you,” he beamed.

My eyes rolled around. I felt so good. So happy. So full. Were we fucking or making love? I wondered blissfully. I didn’t have a clue. All I cared about was for the first time in my life I had a man inside me. I felt no shame right then about how he came to be inside me. I blamed the events that led up to it. All that mattered to me now was I was finally having sex.

Lewis continued to move slowly and deeply. He then kissed me again, probing inside my mouth as I kissed him back. Physically it felt very real, mentally it felt like a wet, erotic dream. Like one of those rare times I’d read erotica before bed but didn’t treat myself to an orgasm. I’d fall asleep unbalanced, only for my mind to take me some place like this in my dreams.

I felt the weight of Lewis pressing down on my body. He was gentle but heavy. I put my hands on his back, not quite wrapping my arms around him, just lightly placing my hands on his back as he continued to penetrate me slowly and gently. My moans became louder and I opened my legs a little bit wider, relaxing as best I could.

Then, something happened. I knew immediately what it was but it seemed to come out of nowhere.

“Ah… ah… I’m coming… ah… yes… I’m coming! Uhhhhh… uhhhh… Uhhhh!”

“Do it, Pippa! Let it go! Uhhh… shit that’s tight! You feel amazing!”

I’d lost count of how many orgasms I’d experienced at my own hands. I now had the one from Lewis’ oral skills in my memory to, but what I experienced with a cock inside me… a big cock inside my tight vagina… was something else…

Muscles throughout my body began to spasm rhythmically and uncontrollably, especially those in my vagina and pelvic floor. Something was going on in my brain before suddenly pleasant sensations began to ripple throughout the body. I felt so warm and giddy. I was flushed, breathless… I was happy and content. I’d just experienced my first orgasm from the big D! Wow! More please, I thought.

“Was that nice?” Lewis sighed, slowly moving in and out of me as my heart rate began returning to some sort of normality.

“I feel amazing,” I swooned beneath him, and for the first time I realised, I intuitively kissed him, slipping my tongue into his mouth.

“Would you like to change positions?” Lewis whispered, slowly pushing himself deep inside me. I could have stayed like that forever.

“I don’t know,” I smiled shyly. I’d read the Kama Sutra before, out of excited curiosity, but I had neither the confidence or experience to say ‘yeah, let’s try this or that’.

“I want you to go on top, Pippa,” he sighed, deep inside me.

Lewis’ suggesting triggered my nervousness. The thought of getting on top of him and being in control was too great to comprehend. As exciting as being on top appeared in movies and porn, there was no way I could take the lead.

“Don’t be scared. You’re so sexy, Pippa. I’ll guide you. Just do as I say and you’ll enjoy it.”

“Can’t we just stay like this?” I giggled.

“I need to see your sexy body on top of me. You’ll be fine.”

With that, Lewis pulled out of me and lifted himself off my body. I felt so nervous now, extremely lacking in confidence.

“What if I do it wrong? I’m too embarrassed,” I complained.

“Don’t be embarrassed, and trust me, you won’t do anything wrong. You couldn’t if you tried. Just follow my instructions. I’m not going to get you to do anything weird.”

“Ok,” I reluctantly agreed, tense and nervous.

It wasn’t that I didn’t want to do it, I just didn’t know what to do once I was on top. Did I bounce? Gyrate? Wait to be told what to do? What if it hurt? Lewis was too big for me to do cowgirl. I went from extremely horny to tremendously nervous as Lewis laid down and I got on top.

“You’re too big,” I squirmed, intimidated and exhausted by the long, thick muscle sticking straight up in the air.

“Relax, Pippa, you’ve already taken it once. Forget what you think you know about going on top. Just relax and straddle my hips. I’ll guide you.”

“I don’t know anything!” I laughed, blushing terribly.

“Then you have nothing to fear and everything to learn. Come on, straddle my hips.”

With Lewis lying on his back, I eventually straddled his hips and positioned myself over his throbbing erection. I tensed, taking it in my hand for the first time. I’d performed a few handjobs and a couple of blowjobs on Alex, but Lewis was so much bigger. He was also far more controlled, which I found equally intimidating and hot.

“Mmm, yes, Pippa. Now smear the head between your pussy lips and line me up.” I followed his instructions and triggered us both into moaning. “Fuck, which feels so good. Now slide down onto my cock. Take it slow. You’re in complete control. I’m not going to do anything.”

Holding and rubbing something so thick against my vulva, created another sensation I felt I could enjoy forever. However, after a while I felt a need to lower my body and impale my vagina on Lewis’ cock.

“Uhhhhh, that’s so good, Pippa. Take it easy and take your time. Uhhhhhh!”

I only went so far down before I came back up again. I was so tight and he so thick. Despite how wet I was, I had to hold Lewis steady in my hand while I gradually fed him into my vaginal canal. The muscles inside were contracting in anticipation, calling for more cock to enter, but knew I had to be patient to avoid hurting myself.

Encouraged by Lewis’ soft groans and whispers of support, I eventually let go of his cock and sat down on him. I gasped at how deep he was inside me. I knew vaginas stretched to be able to bring babies into this world, but holy cow, I thought, gasping with wide eyes as I sat still with my vaginal muscles contracting greedily around the throbbing insertion.

Forget the Venus fly trap, I felt like a Venus cock trap. I didn’t want to move. I wanted to remain sitting upright on top of Lewis with his big cock throbbing inside me. But something instinctively had me leaning forward over him. I realised it was Lewis pulling me towards him.

“Just because it’s called the cowgirl position, Pippa, it doesn’t mean you have to ride like a rodeo,” he smiled. “You can if you want to, but just do whatever feels right. Whatever feels natural to you.”

I nodded and placed my hands on his muscular, hairy chest for support. Lewis looked so happy as my well-endowed boobs swung away from my body to hang just in front of his face. Realising Lewis had a spectacular view of my naked body and face, gave me a sense of power and confidence.

It was conditioned confidence of course, and a borrowed power. I believed Lewis was the one who was really in control. He had the size, strength, experience and real power to do whatever he wanted with me. I was just an inexperienced, fragile, petite eighteen-year-old girl. Barely out of high school. Barely a woman.

I was very naïve and stupid with my openness in the bar. Naively careless inviting a stranger to my hotel room, but also fortunate it was Lewis I had met, and not a sadistic psychopath.

“Take your time, there’s no rush, and remember to do what feels natural,” he breathed excitedly.

So I did, I took my time and did what felt natural. I came out of my head and into my body once more. Moving away from the nerves and tension, away from the anxiety and fear, I moved my hips slowly and sensually, finding the tempo that felt right for me.

“That feels so good, Pippa. Just focus on yourself. Whatever you do, it will feel fucking amazing,” Lewis chuckled, which then made me giggle. “You have control, so be selfish. Don’t worry or think about me.”

Was this guy even real? Be selfish? But I realised he was right. I had full control of the penetration, the movements, the depth and rhythm. Years of dance classes had prepared me for this. Not directly, but as a byproduct. It was time to move my dancers hips and get jiggy again.

As Lewis held and squeezed my swollen boobs together, I slowly moved my hips. When he started sucking on my hard, sensitive and excited nipples, I involuntarily flicked my hips.

His cock was so big, so deep inside me, and my movements so slow, I began to feel great and truly in control. Randomly, Alex popped into my head again. The thought didn’t come with guilt this time. It came with a satisfying sense of revenge taking place.

I smiled with my eyes closed, imagining the pain and anguish on his face, as he watched me riding a real man. He’d be horrified at how old the guy was, old enough to be my father. He would burn with rage, too weak himself to slash out at Lewis for shagging ‘his girlfriend’.

Then, Alex drifted from my thoughts, replaced with another of me telling my friends all about the night I lost my virginity to a stranger in a hotel. They’d ask for all the juicy details I was experiencing right then, and I’d giggle and blush, before coming alive as I told them all about the experience.

Lewis was groaning and grunting into my cleavage. He had his face buried between my boobs, kissing, licking and biting them playfully. My body was driving him crazy before I fully understood why.

In my selfishness, I had unknowingly released a powerful side to my sexual being that I didn’t know existed. As Lewis had insisted upon, and greatly encouraged, I was gradually and shamelessly chasing my own pleasure and gratification. I was undoubtedly using him. His big cock to be accurate.

Being on top felt so good. I was being consumed by triple stimulation. While the thick cock inside me pleasured my pussy and clit, I had Lewis sucking on all the sensitive nerve endings in my boobs, particularly around my areola. So, I continued to be selfish, knowing I wasn’t really being selfish.

Something else I realised; I was raising my body higher than when I started. I was able to lift myself up to the tip of his cock, keeping only the thick, dome-shaped head inside me, before I dropped my body and impaled my soaking wet, stretched vagina over and over.

I was learning more and more about myself as I rode Lewis with all that I had. I was pushing those mental boundaries further away from me until I could longer feel them. I was capable of more than I realised.

Suddenly, I had an intuition to switch things up a little. Removing my hands from Lewis’ chest, I sat upright, leant back, and opened up space to play with my clit. As Lewis fondled my boobs he groaned and told me to make myself cum on his cock.

I gave him a naughty grin and moved my hand into that space. Completely stuffed with cock, I began gyrating my hips and rubbing my clit. As I started, Lewis unexpectedly added the final ingredient. He held my hips and very gently started moving his. We moved together until we naturally found a rhythm which quickly sent me on my way once more.

I leaned right back and put my arm out between his legs to balance myself. Lewis groaned and said we should come together, but all I could do was rub my clit harder as he started thrusting up into me. I stopped moving and handed the control back over to him. I just needed to come again.

Moaning as Lewis started stimulating my g-spot, I knew I was close. I was actually closer than I realised. Holding my hips firmly. Lewis started raising his cock right up inside me. It started me bouncing as I continued rubbing as fast as I could.

“Yes! Yes! Here I go! Ah! Ah! Uhhhhhhhhh!”

“Damn that’s tight! Fuck I’m coming to!”

As soon as my orgasm hit I rubbed my clit for a few more seconds before I had to stop. I flung myself forwards in a daze to meet Lewis sitting up. He wrapped his arms around my body and in a tight grip, he bounced me up and down on his cock,

While my body spasmed uncontrollably, Lewis held me firmly and grunted into my boobs. It felt so good on his cock I started coming again. Either that or I had an amazing double whammy of release from the initial orgasm.

I didn’t care. I wrapped my arms around his head and suffocated him with my boobs. He then stopped bouncing me and everything went quiet and still. Only our deep breathing could be heard now.

“That was fucking amazing, Pippa!” Lewis sighed. “Are you ok?”

“It was amazing,” I agreed. “Did you come?”

“Yeah. I came alright. The hardest for a long time.”

I suddenly screeched and laughed when Lewis very strongly flipped us around, so he was on top and I was on my back again. He then pulled out of me and I cringed at the obvious slurping sound.

“That’s gross,” I commented, embarrassed my body could make such noises.

“Awesome is what it is,” he chuckled, staring between my spread legs.

I felt it and he obviously watched it. Because as I felt slimy fluid slip out my vagina, Lewis’ grin grew wider. He then nodded, showing he was a man after all. His cum made its slimy way down into the crack of my arse before I told him to stop looking and closed my legs.

“How do you feel now, Pippa? Did you enjoy your first time?”

Lewis sat beside me and stroked my leg affectionately. His big cock slowly deflated and I smiled. “It was better than I expected.”

“I know what it feels like after all the excitement and passion has gone. So, would you like me to leave? Or would you like me to stay with you? It’s totally up to you.”

“Would you be offended if I said I want to be alone? I’m ready for sleep now,” I giggled and got under the bed covers.

“As long as you promise me you’ll be ok when I leave. No regrets?”

“I’ll be fine. And thank you, Lewis. Thanking him for an amazing end to a shitty night.”

“You’re welcome, Pippa. You were amazing. I hope you can work things out with your boyfriend. I guess this makes you even?”

I laughed. “He cheated! I didn’t.”

“That’s true,” Lewis chuckled. “Can I be selfish for a moment?”

“Sure.”

“I’m glad he did, because I wouldn’t have got the chance to meet you.”

“Fuck me and take my virginity, you mean!” I laughed again.

“Look after yourself, Pippa,” he said, finally dressed as he kissed my head.

“Goodbye, Lewis.”

As soon as he was out the door I screamed up at the ceiling in sanctimonious joy. “Fuck you, Alex!”

I couldn’t stop grinning and laughing as the full reality of what had just taken place in the hotel room sank in. I picked up my phone and texted my best friend.

“You’ll never guess what just happened to me…? X”

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