Why is it when people share stories about losing their virginity, it sounds like a fucking fairy tale? If you just dig a little deeper and you learn the truth is nowhere near close. Oh, and don’t get me started on the bullshit stories people write about how when a girl is deflowered by the man of her dreams, making it sound like a loving gesture of passion and romance. Ugh!
It’s said you remember the first and you remember the worst. Well, I will never forget my first or my worst. It definitely wasn’t the event that I had planned, but I’m getting ahead of myself. To tell this story right, I must begin at the proverbial beginning.
It all started at the Halloween party ... no, that’s not right. I guess it really started almost a year before that fateful night when I started dating my then boyfriend, Dwight. I graduated high school at seventeen and went straight to community college. I got a job at the school’s bookstore which got my mom off my ass and took classes three days a week.
It was during my first semester in Speech class where I met Dwight. Dwight was a tall, handsome sophomore with thick black hair, big brown eyes, and a panty-melting smile. We got paired up in a debate about private businesses using their religious beliefs and if they should be allowed to not provide birth control to their female employees. He argued for the businesses; I argued for the women.
I researched my ass off, but in the end, he beat me out and I was pissed. I mean, how could anyone side with those religious nuts? Didn’t they understand how it was more than just birth control pills to prevent unwanted pregnancy? Oh, and did I mention this was also my eighteenth birthday? Yeah, like that fucking helped my mood. It felt like my professor was saying, “Happy birthday Avery! You just lost the biggest debate of your young life on an issue that could affect you and millions like you.”
After class, I was really upset for losing the debate to Dwight. Part of me felt it was because I was overwhelmed by his good looks. Part of me felt it was because my professor was a misogynistic ass. Either way, I was not happy. I decided to get a soda in the Student Union and calm down before my next class.
“That was a hell of a fight you put up in there,” I heard him say as I entered the Student Union.
I bit my lip, then said, “You really think so?”
I turned to see him sitting at a table with books spread all over. “Your arguments were sound, and to be honest, if the professor wasn’t already on my side you might have won.”
“Bullshit.” Was he confirming my thought that the professor was a misogynistic ass?
“It’s true,” he said, flashing that sexy as fuck smile at me. “It’s why I volunteered to take that side. My buddy took his class last spring and gave me the 411.”
I couldn’t help but smile at that. I mean, as underhanded of a move that was, he was pretty clever on his part too. “You did make good counter-arguments.”
“Thanks. And for the record, Avery, you’re much prettier when you smile.”
I felt my cheeks burn. I hate it when I blush. “Thanks.”
“Buy you a drink? I can only offer you a coffee, though.”
“Would a soda instead of coffee be a reasonable request?” I asked.
“Sure, sit down,” Dwight said, stood up and gestured to the empty chair, then got me a soda.
We sat and talked about the debate, our classes, and so much more. Before long, we made plans to have dinner later that week and started dating. What started off as a shitty birthday ended well with me getting a new boyfriend my mom tolerated at best. We took things slow. I made it clear that not only was I a virgin but that I wanted to stay that way until I was married.
The winter break wasn’t too tough as we were both tied up with family obligations. At spring break, neither of us went anywhere. I had inventory at the bookstore and he had to do something for his family. Every night we went out ended in much the same way, lots of kissing and top of clothes touching, but we never went any further.
The summer break aided in preserving my virginity since Dwight left for a month on a preplanned vacation with his family that included his cousin’s wedding. As much as I wanted to join him, it wasn’t an option. The night before he left, Dwight got his hand into my jeans and made me cum hard simply by touching my pussy and clit through my panties. I spent the summer reliving that night in my bedroom using my own hand and fingers, with my face buried in my pillow so my mom wouldn’t hear me moan.
With the start of the fall semester, Dwight and I had one class together which sucked. I was pretty head over heels in love with him and the hope of us having more than one class was quickly lost. Dwight had already taken all the classes I needed, except the one we were in. The other classes he was taking were just to give him a full-load so his financial aid would cover his costs and keep his folks off his back. Dwight had plans to transfer to the university over the winter and thus our schedules quickly limited our time together. Even our dates were slowly becoming more touch and feel sessions leaving me very sexually frustrated and horny as hell.
A few of my classmates who knew Dwight kept telling me he was only interested in me as a conquest and nothing more. Many were shocked he stayed with me so long, especially since I shared my virgin status. I really thought Dwight felt about me the same way I felt about him, and he was willing to be patient for when I was truly ready. Though I didn’t want to believe them, truth be told, I was starting to have my doubts.
Early in October, Dwight wrangled us invitation to a huge Halloween party that was to be held at a rumored haunted house. I asked around and found out the so-called haunted house was just an old house that had secret rooms and may or may not been the site of a murder. A bit a research proved that last part to be untrue, but it made for a wicked Halloween party theme.
After a bit of hunting, I found a sexy angel costume with a strapless bustier, gold hearts like buttons, a white fur and lace collar, furry halo, faux sleeves with gold bows that were more like garter belts for my arms, a short skirt, and white wings with gold trim and more gold hearts. I added a white mini-skirt petticoat, a white and gold mask, and found a pair of white thigh-high stockings with golden bows at the top to go with it. Since I already had a pair of white heels at home, I was set. Being a natural blonde meant no need for a silly wig.
Halloween was on Saturday that year, so I didn’t have to worry about missing class or work. College bookstores are only open on Saturdays during the first two weeks of school so I could spend the day styling my hair, fixing the makeup on the part of my face not covered by my mask, and making sure everything was perfect. I also decided that if Dwight and I could sneak off someplace, I’d finally give him my virginity. I knew he could get me off with his hands, so I was sure his cock could do an even better job.
Seriously ... what the fuck was I thinking? But again, I’m getting ahead of myself.
Dwight promised he’d get a devil costume so we’d be the perfect couple, an angel and a devil, but for some reason, he showed up at my door wearing a black tuxedo and a Phantom of the Opera mask that covered most of his face.
“What happened to your devil costume?” I asked, not hiding my annoyance.
“Easy Avery,” he said in a soothing tone. “Let me explain.”
“Okay, explain,” I snapped.
“My idiot brother didn’t buy a costume because he thought he had to work, but dumbass got fired for smoking a joint in the break room with some girl. Thus, he stole my costume. My dad had this mask left over from last year when he took my mom out. The tux was left over from my cousin’s wedding and I had promised you we’d go to this party.”
Dwight’s younger brother Jeremy could be a real jerk and was not someone I was real crazy about. I often felt sorry for Dwight’s parents until I realized they were in part the reason he was the way he was. For as pissed off as I was, I was happy Dwight didn’t just bail out on me, and he did look so handsome.
“I feel silly in my costume now,” I said.
“Why?” he asked. “To me, you look as sexy as fuck.”
“You really think so?”
Dwight leaned down and kissed my neck, then purred in my ear, “Very much so, and tonight, you’re all mine.”
I blushed hard, then said, “As promised.”
Dwight and I left and drove to the party. The valet took our car and a mad scientist driving a golf cart took us up to the house. I could hear the music from the party before we saw the house. The place was packed with lots of college students in all kinds of crazy costumes. The punch was spiked and rather strong; it wasn’t long before I had a healthy buzz. Of course, I didn’t have much experience with alcohol so I reminded myself to not drink too much. Advice I failed to take later ... oh shit ... I’m getting ahead of myself again. Dwight and I danced with each other, as well as with other guests, and had a great time.
You know how some women get all freaked out about someone else wearing their dress. Well, guess what I saw? We’d been there about an hour or so when I saw her. She wearing the exact same costume as I had on, gold hearts, mask, and all, and I swear she wore it better. The only real difference was she was wearing a blonde wig. The freaky part was when I thought I was looking in a mirror until she moved and I stayed still. Only on Halloween could this happen.
When Dwight slipped off to the bathroom, I got myself another drink. There were so many different costumes and several other Phantoms of the Opera, some with the half mask and a couple with a mask like Dwight’s. Then Jeremy showed up wearing what I assumed was Dwight’s devil costume, if you could call it that. Jeremy was in a red three piece suit with a black shirt, red mask, and the red devil horns.
“Hey Avery,” he said. I wondered how he knew it was me.
“Jeremy.” Mask or no mask, I knew his voice.
“Where’s my idiot brother?”
“You sound pissed.”
“Why shouldn’t I be? You stole Dwight’s costume.”
Jeremy laughed. “Is that what he fucking told you? Damn Avery, I thought you were smarter than that.”
“Excuse me?” I snapped.
“Please tell me that you’re not a bottle blonde and that you actually have a brain in that pretty little head of yours.”
“Look here asshole,” I snapped, “I don’t fucking know what you’re playing at, but I don’t have time for it.”
Jeremy leaned down and said, “Dwight forgot all about this party until you told him he could pop your cherry.”
I swallowed hard. “You ... you’re lying.”
“Am I? I’ll bet he’s off right now banging some bitch so he won’t do a three-second cum dump with you later.”
See what I mean about what the hell was I thinking? Dwight had no intention of taking me to this party until I was willing to give him what he always wanted. I was crushed. I ran off the bathroom to pull myself together, but not before I slapped Jeremy as hard as I could.
Maybe it was the fact I wasn’t fully sober, but I didn’t want to believe Jeremy. I’m serious about that punch being pretty strong. Maybe it’s because I’m just an idiot that caused me to do what I did next, but it wasn’t my finest moment. I made sure my breasts were pushed up, my hair was perfect, and my skirt was a bit higher, then walked out.
I made it to the end of the hall when I saw someone in a Phantom of the Opera costume with a mask like Dwight’s. At first, I wasn’t sure if it was him or not, but he put his hands on my shoulders and seemed to apologize though he wasn’t talking.
I looked into his eyes through the mask and was about to tell him what Jeremy had said when he put his fingers against my lips. I scowled as he took my hand with his free hand and led me back down the hallway to what looked like a library. He pulled a book and a nearby bookcase slid open exposing a staircase. He gestured for me to follow him up the stairs to a bedroom.
The room was a bit of a contradiction with cobwebs on the walls and in the windows, but the bed in the center was made with clean sheets. I was about to say something when my mask was removed and a silk scarf was placed over my eyes.
I asked, “What are... ?” but he gagged me with another scarf.
My heart raced in my chest as he proceeded to remove my wings and bind my wrists together. I bit on my gag as I was led to the bed and put on it with my hands tied over my head. My body trembled and shook as I felt the bindings tied to the wrought iron headboard. I couldn’t believe it, he was going to make this night unforgettable after all. I started to think Jeremy was a plant to wind me up.
Remember when I mentioned the bullshit stories people write? Well, I must admit that I found great enjoyment reading them, especially when the girl was tied up and fucked silly. Of course, it wasn’t a virgin who was bound, but I wasn’t about to argue with him. Dwight knew how much I enjoyed these stories, so I just figured he was trying to make up to me for being such a prick. I mean, if you were in my position, would you have thought anything different?
I was pushed onto my side and felt my bustier release as it was untied and unhooked, freeing my breasts. I won’t lie, it felt great and terrifying at the same time. Slowly my costume was erotically removed once piece at a time until I was naked except for my shoes and stockings. Then I was moved until my body was centered on the bed and one ankle at a time was tied so I was in a spread-eagle position.
There I was, tied to a bed, blindfolded, gagged, and naked except for my shoes and stockings. I was at the mercy of a man about to take my virginity and make this night the most memorable in my life. I felt him climb onto the bed and push something into my face. It only took a moment to realize it was his dick and he wanted to put it into my mouth.
I hesitated for a moment, then opened wide. My gag was removed as he slid his penis in and I began sucking. It was my first time sucking a man’s cock and I knew it wouldn’t be my last. His large cock filled my mouth as I licked and sucked. There was a salty taste that coated my tongue and I realized it was his precum. It was rather intoxicating and it made me want more. I licked and sucked as he fucked my mouth, pushing his cock deeper with each thrust until it entered my throat. How I didn’t gag I’ll never know.
‘Was this what he was going to do to my pussy?’ I thought.
Having my mouth fucked was driving me wild with desire. I felt moisture under my ass from my pussy leaking between my legs. I never wanted this moment to end, but then felt a series of pulses as my mouth was filled with a sticky, salty substance. I swallowed my new treat greedily and moaned. This was a true treat and one I knew I wanted again.
His cock was pulled from my mouth with a pop and my gag was replaced. I felt him move on the bed and between my legs. ‘This was it, he is going to take my virginity, ‘ I thought.
He didn’t though, not yet anyway. He touched my clit with something soft and I realized it was his tongue. Aside from some through clothing touching and that one time Dwight made me cum when he had his hand on the outside my panties, this was the furthest I had ever gone. I mean, I knew about oral sex, but until now I never experienced it. It was clear this was a give and receive experience.
His tongue danced on my clit, then slid a finger inside my pussy. I felt my body explode from the inside out as I experienced my first penetration orgasm. Even though there was a blindfold over my eyes, I swear I saw stars. My body shook violently, my toes curled, and I was gasping for air that smelled and somewhat tasted like my pussy through my gag. In all my masturbation sessions I never experienced an orgasm like this, and all I wanted was more.
There was a strange sound that followed with foil tearing and I realized it was a condom wrapper. I felt the thick head push against my lower lips. This was it and I was nervous. The head of his cock slid between my labia and moved until I felt my hymen give way as he tugged hard on my nipples. I cried out from the pain that was just as quickly replaced by pleasure as we fucked.
I can’t even begin to explain just how long I fantasized about boring, vanilla, missionary style sex for my first time. I mean, that is the way we are prepared for such an act. Instead, I was bound and gagged to this bed in this old house experiencing a mixture of pleasure and pain with my first real sexual experience. I felt him untie my left ankle and my legs were moved together so I was now on my side with his cock still in my pussy as he fucked me. He put his hand on my ass and his thumb touched my anus. This caused a second orgasm that raged through my body. Had I known this was how great sex was, I would never have waited.
My right ankle was untied, I was moved onto my back, and my legs were pushed up his bare chest so my knees were on his shoulders as he pounded me with a ravenous force. The sounds of my moans through my gag, the squeaking of the bed beneath us, the banging of the headboard, and the squishy sound of my pussy as his cock pounded me filled my ears. In this moment, I was his fuck toy, my pussy was his and his alone, and I was loving it.
I felt him pull the gag from my mouth as his lips clamped onto mine as I came a third time and it was then I realized, this wasn’t Dwight fucking me. I didn’t know who it was, but it sure as hell wasn’t Dwight. Had I not been so caught up in the moment of my first real passionate sexual experience I might have said something, but I didn’t. Instead, I savored the feeling of a real cock buried deep in my pussy and the new thrill of being fucked by a total stranger.
He pounded my pussy harder and faster, we were both close to another orgasm. We moaned, kissed, and fucked. I tugged at my restraints wanting to touch this man as my pussy exploded again and I came with a force so violent I thought my nipples would fly off, causing me to scream. I felt his cock pulse as he filled the condom, then he collapsed on top of me.
It took me a few minutes to catch my breath before I asked, “Who ... who ... who are you?”
He pulled my hair making me cry out a bit, then said, “Oh fuck! You’re not Candice.”
“No, I’m Avery,” I replied. “Now please take off this blindfold and tell me who you are.”
“I’m Henry,” he said as the blindfold was removed from my eyes.
Henry was so handsome with piercing light brown eyes and black hair like Dwight. I mean, in my defense, he was wearing a mask. “Who’s Candice?”
“The other girl wearing your costume. I’m sorry.”
Henry untied my wrists and started to rise when he paused and said, “What the fuck? Are you a virgin?”
I looked down at the red on the condom and the huge stain on the bed. “I was.”
“Oh fuck! And you’re a fucking squirter as well!” he exclaimed as he removed the condom from his dick. I could smell the aroma of sex mixing with the spermicide and latex.
“Why are you so upset?” I asked. “I always thought it was a guy’s major fantasy to fuck a virgin.”
Henry sighed. “I don’t like taking virgins. I’m always afraid they’ll say I forced them.”
“Don’t worry, I won’t.”
“Thanks. I hope you enjoyed your first time.”
Henry helped me off the bed and back into my costume as we continued to talk. “Very much so.” What was I supposed to say? Oh, that I fucking loved it?! I mean, it wasn’t as horrid as it could have been, but it sure wasn’t the first time I was expecting either. I mean, he did make me cum three times and I was already wanting more despite being sore.